TREA

Piperazine Compounds with a Herbicidal Action

Follow

Information

  • Patent Application
  • 20090137396
  • Publication Number
    20090137396
  • Date Filed
    January 04, 2007
    18 years ago
  • Date Published
    May 28, 2009
    15 years ago
Information
Abstract
The present invention relates to the use of piperazine compounds of the formula I
Description

The present invention relates to the use of piperazine compounds of the formula I







or of the agriculturally useful salts of piperazine compounds of the formula I as herbicides, where in formula I the variables are as defined below:

  • R1 and R2 independently of one another are:
    • cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C8-alkenyl, C3-C8-cycloalkenyl, C3-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl; or
    • COR21, where
      • R21 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C3-C6-alkenylamino, C3-C6-alkynylamino, C1-C6-alkylsulfonylamino, N—(C2-C6-alkenyl)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkyl)amino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkenyl)-N—(C1-C6-alkoxy)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkoxy)-amino, phenyl, phenylamino, phenoxy, naphthyl or heterocyclyl; or
    • NR22R23 where
      • R22 and R23 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-cycloalkenyl, C3-C6-alkynyl, C3-C6-cycloalkynyl or C1-C6-alkylcarbonyl; or
    • OR24, where
      • R24 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-cycloalkenyl C3-C6-alkynyl, C3-C6-cycloalkynyl, phenyl or phenyl-(C1-C6)-alkyl; or
    • SO2R25, where R25 is C1-C6-alkyl or phenyl;
    • where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents of R1 and R2 may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C4)-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy;
    • and where R1 may additionally be hydrogen;
  • R3 is hydrogen, halogen, cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl; or a radical COR26, NR27R28, OR29, SO2R30 or N(OR31)R32, where
    • R26 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C3-C6-alkenylamino, C3-C6-alkynylamino, C1-C6-alkylsulfonylamino, N—(C2-C6-alkenyl)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkyl)amino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkenyl)-N—(C1-C6-alkoxy)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkoxy)-amino, phenyl, phenylamino, phenoxy, naphthyl or heterocyclyl;
    • R27 and R28 independently of one another are hydrogen, C1-C6-alkyl, aryl or heteroaryl;
    • R29 is C1-C6-alkyl;
    • R30 is C1-C6-alkyl or phenyl;
    • R31 is hydrogen, C1-C10-alkyl, phenyl or phenyl-(C1-C6)-alkyl;
    • R32 is C1-C6-alkyl, phenyl or phenyl-(C1-C6)-alkyl;
    • where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents of R3 or R26, R27, R28, R29, R30, R31 and R32 may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C4)-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy;
  • R4, R5, R6 independently of one another are hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy,
    • where the abovementioned aliphatic moieties of the substituents of R4, R5 or R6 may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C40-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy;
  • A1 is aryl or heteroaryl;
  • A2 is aryl or heteroaryl, except for indolyl;
  • Ra is halogen, cyano, nitro, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C4-C10-alkadienyl, C2-C6-alkynyl, [tri-(C1-C6)-alkylsilyl]-(C2-C6)-alkynyl, C3-C6-cycloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, aryl, phenyl-(C1-C6)-alkyl, phenyl-(C2-C6)-alkenyl, phenylsulfonyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl or phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl,
    • Z1P(O)(OR9)2, Z2B(OR10)2, where
      • R9 and R10 are each hydrogen or C1-C6-alkyl and the radicals R10 in Z2B(OR10)2 together may form a C2-C4-alkylene chain; or
    • Z3COR11, where
      • R11 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C1-C6-alkoxyamino, [di-(C1-C6)-alkoxy]amino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6)-alkylamino]sulfonylamino, C3-C8-alkenylamino, C3-C6-alkynylamino, N—(C2-C6-alkenyl)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkyl)amino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)amino, N—(C2-C6-alkenyl)-N—(C1-C6-alkoxy)-amino, N—(C2-C6-alkynyl)-N—(C1-C6-alkoxy)amino, phenyl, phenoxy, phenylamino, naphthyl or heterocyclyl; or
    • Z4NR12R13, where
      • R12 and R13 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-cycloalkenyl, C3-C6-alkynyl, C3-C6-cycloalkynyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, [di-(C1-C6)-alkylamino]carbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, C1-C6-alkylsulfonyl, C1-C6-alkylaminosulfonyl, [di-(C1-C6)-alkylamino]sulfonyl, phenylcarbonyl, phenylaminocarbonyl, phenylsulfonyl, phenylsulfonylaminocarbonyl or heterocyclylcarbonyl; or
    • Z5CH═N—O—R14, where R14 is hydrogen or C1-C6-alkyl; or
    • Z6OR15, where
      • R15 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-cycloalkenyl, C3-C6-alkynyl, C3-C6-cycloalkynyl, C1-C6-alkylcarbonyl, C1-C8-alkoxycarbonyl-(C1-C6)-alkyl, [di-(C1-C6)-alkoxycarbonyl]-(C1-C8)-alkyl, phenyl or phenyl-(C1-C6)-alkyl; or
    • Z7SO2R16, where R16 is C1-C6-alkyl or phenyl; and where
    • Z1, Z2, Z3, Z4, Z5, Z6, Z7 independently of one another are a bond, —CH2—, —CH2—CH2—, —O—CH(R17)—, —S—CH(R18)—, —S(O)—CH(R19)— or —SO2CH(R20)—, and
    • where R17, R18, R19 and R20 independently of one another are hydrogen or C1-C6-alkyl; and
    • where the abovementioned aliphatic, cyclic or aromatic moieties of the substituent Ra may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C4)-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy; and
  • Rb, Rc, Rd, Re and Rf are each independently of one another hydrogen or have one of the meanings given for Ra; and


    where two radicals Ra, Rb or Rc attached to adjacent ring atoms of A1 or two radicals Rd, Re or Rf attached to adjacent ring atoms of A2 may also be straight-chain C3-C6-alkylene which may be partially or fully halogenated and which may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C4)-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy, where one CH2 group in C3-C6-alkylene may be replaced by a carbonyl group, thiocarbonyl group or sulfonyl group and in which one or two non-adjacent CH2 groups in C3-C6-alkylene may in each case be replaced by oxygen, sulfur or a group NR34, where R34 has one of the meanings given for R12.


The thaxtomins A and B produced by the plant pathogen S. scabies (King R. R. et al., J. Agric. Food Chem. (1992) 40, 834-837) are natural products having a central piperazine-2,5-dione ring which carries a 4-nitroindol-3-ylmethyl radical in the 3-position and an optionally OH-substituted benzyl radical in the 2-position. Owing to its plant-damaging action, this compound class was also investigated for a possible use as herbicides (King R. R. et al., J. Agric. Food Chem. (2001) 49, 2298-2301).


In the context of synthetic studies about the preparation of thaxtomin A and B, J. Gelin et al., J. Org. Chem. 58, 1993, pp. 3473-3475, and J. Moyroud et al. Tetrahedron 52, 1996, pp. 8525-8543 describe dehydrothaxtomin derivatives. Described are, inter alia, compounds of the formula







in which R is hydrogen or NO2.


N. Saito et al., J. Chem. Soc. Perkin Trans 1997, pp. 53-69 describe, inter alia, compounds of the formula below







in which Ry is hydrogen or benzyl and Rx is hydrogen, acetyl or isopropyloxycarbonyl as precursors for preparing ecteinascidins.


In the context of synthetic studies about the preparation of phthalascidin, Z. Z. Liu et al., Chinese Chem. Lett. 13(8) 2002, pp. 701-704 describe an intermediate of the formula below in which Bn is benzyl:







J. Bryans et al., Journal of Antibiotics 49(10), 1996, pp. 1014-1021 describe the compound of the formula below:







WO 99/48889, WO 01/53290 and WO 2005/011699 describe 2,5-diketopiperazine compounds which have a 4-imidazolyl radical attached via a methylene or methyne group in the 3- or 6-position and in the other 3- or 6-position a benzyl or benzylidene radical. These compounds are antitumor compounds.


It is an object of the present invention to provide compounds having herbicidal action. In particular, the intention is to provide compounds having high herbicidal activity, in particular even at low application rates, and whose compatibility with crop plants is sufficient for commercial use.


This and further objects are achieved by the compounds of the formula I defined at the outset and by their agriculturally useful salts.


Accordingly, the present invention relates to the use of piperazine compounds of the general formula I or of the agriculturally useful salts of piperazine compounds of the formula I as herbicides, i.e. for controlling harmful plants.


The invention also relates to compositions comprising a herbicidally effective amount of at least one piperazine compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for formulating crop protection agents.


Moreover, the invention relates to a method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one piperazine compound of the formula I or an agriculturally useful salt of I to act on plants, their seeds and/or their habitat.


The piperazine compounds of the formula I are novel and also form part of the subject matter of the present invention,

    • except for compounds of the formula I in which A1 is phenyl and A2 is 4-imidazolyl or A1 is 4-imidazolyl and A2 is phenyl,
    • furthermore except for the compound of the formula I in which R1 is hydrogen and R2 is methyl, R3, R4, R5 and R6 are hydrogen and the group A1(RaRbRc) is 4-methoxyphenyl and the group A2(RdReRf) is phenyl.
    • furthermore except for compounds of the formula I in which A1 is phenyl, R1 and R2 are methyl, R3, R4, R5 and R6 are hydrogen, Ra is benzyloxy which is attached in the 3-position, Rb and Rc are hydrogen and the group A2(RdReRf) is phenyl or 3-nitrophenyl,
    • furthermore except for compounds of the formula I in which R1 is hydrogen, acetyl or isopropyloxycarbonyl, R2 is hydrogen or benzyl, R3, R4, R5 and R8 are hydrogen, the group A1(RaRbRc) is a radical of the formula









    • where # indicates the attachment to the methyne carbon which carries R3 and the group A2(RdReRf) is 3-methyl-4-methoxyphenyl,

    • furthermore except for the compound of the formula I in which R1 is isopropyloxycarbonyl and R2 is benzyl, R3, R4, R5 and R6 are hydrogen, and the groups A1(RaRbRc) and A2(RdReRf) are each 3,4,5-trimethoxyphenyl.





Moreover, the invention relates to processes and intermediates for preparing compounds of the formula I.


Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.


Depending on the substitution pattern, the compounds of the formula I may comprise one or more centers of chirality, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.


With respect to the exocyclic double bond, the compounds of the formula I can be present as E isomer or as Z isomer. The invention provides both the pure E isomers and Z isomers and mixtures thereof.


The compounds of the formula I may also be present in the form of their agriculturally useful salts, the nature of the salt generally being immaterial. Suitable salts are, in general, the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action of the compounds I.


Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium or potassium, of the alkaline earth metals, preferably calcium or magnesium, and of the transition metals, preferably manganese, copper, zinc or iron. Ammonium can likewise be used as cation, where, if desired, one to four hydrogen atoms may be replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium may be mentioned.


Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.


The organic moieties mentioned for the substituents of the compounds according to the invention are collective terms for individual enumerations of the specific group members. All hydrocarbon chains, such as

    • alkyl, haloalkyl, and also the alkyl moieties in cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, dialkylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, dialkoxyalkyl, alkylthioalkyl, dialkylaminoalkyl, dialkylhydrazinoalkyl, alkyliminooxyalkyl, alkylcarbonylalkyl, alkoxyiminoalkyl, N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, alkoxycarbonylalkyl, dialkylaminocarbonylalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl and alkoxyalkoxy moieties


      may be straight-chain or branched. The prefix Cn-Cm— indicates the respective carbon number of the hydrocarbon moiety. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.


The term halogen denotes in each case fluorine, chlorine, bromine or iodine.


Examples of other meanings are:


alkyl and also the alkyl moieties, for example, in alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl, alkylcarbonyl, alkylamino, alkylsilyl, phenylalkyl, phenylsulfonylalkyl, heterocyclylalkyl: saturated straight-chain or branched hydrocarbon radicals having one or more carbon atoms, for example 1 to 2, 1 to 4 or 1 to 6 carbon atoms, for example C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodiment according to the invention, alkyl denotes small alkyl groups such as C1-C4-alkyl. In another embodiment according to the invention, alkyl denotes relatively large alkyl groups such as C5-C6-alkyl.


Haloalkyl: an alkyl radical as mentioned above whose hydrogen atoms are partially or fully substituted by halogen atoms such as fluorine, chlorine, bromine and/or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl.


Cycloalkyl and also the cycloalkyl moieties, for example, in cycloalkoxy or cycloalkylcarbonyl: monocyclic saturated hydrocarbon groups having three or more carbon atoms, for example 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.


Alkenyl and also alkenyl moieties, for example, in phenyl-(C2-C6)-alkenyl or alkenylamino: monounsaturated straight-chain or branched hydrocarbon radicals having two or more carbon atoms, for example 2 to 4, 2 to 6, or 3 to 6 carbon atoms, and a double bond in any position, for example C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-tri-methyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl.


In one embodiment according to the invention, alkenyl groups such as C2-C6-alkenyl are employed. In another embodiment according to the invention, use is made of alkenyl groups such as C3-C6-alkenyl.


Cycloalkenyl and also cycloalkenyl moieties: monocyclic, monounsaturated hydrocarbon groups having three or more carbon atoms, for example 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.


Alkynyl and also alkynyl moieties, for example, in [tri-(C1-C6)-alkylsilyl-(C2-C6)-alkynyl or alkynylamino: straight-chain or branched hydrocarbon groups having two or more carbon atoms, for example 2 to 4, 2 to 6, or 3 to 6 carbon atoms, and one or two triple bonds in any position, but not adjacent to one another, for example C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.


Cycloalkynyl and also cycloalkynyl moieties: monocyclic hydrocarbon groups having three or more carbon atoms, for example 3 to 6, preferably 5 to 6, carbon ring members and one triple bond, such as cyclohexyn-1-yl, cyclohexyn-3-yl, cyclohexyn-4-yl.


C4-C10-alkadienyl: doubly unsaturated straight-chain or branched hydrocarbon radicals having four or more carbon atoms and two double bonds in any position, but not adjacent to one another, for example 4 to 10 carbon atoms and two double bonds in any position, but not adjacent to one another, for example 1,3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, hexa-1,4-dien-3-yl, hexa-1,4-dien-6-yl, hexa-1,5-dien-1-yl, hexa-1,5-dien-3-yl, hexa-1,5-dien-4-yl, hepta-1,4-dien-1-yl, hepta-1,4-dien-3-yl, hepta-1,4-dien-6-yl, hepta-1,4-dien-7-yl, hepta-1,5-dien-1-yl, hepta-1,5-dien-3-yl, hepta-1,5-dien-4-yl, hepta-1,5-dien-7-yl, hepta-1,6-dien-1-yl, hepta-1,6-dien-3-yl, hepta-1,6-dien-4-yl, hepta-1,6-dien-5-yl, hepta-1,6-dien-2-yl, octa-1,4-dien-1-yl, octa-1,4-dien-2-yl, octa-1,4-dien-3-yl, octa-1,4-dien-6-yl, octa-1,4-dien-7-yl, octa-1,5-dien-1-yl, octa-1,5-dien-3-yl, octa-1,5-dien-4-yl, octa-1,5-dien-7-yl, octa-1,6-dien-1-yl, octa-1,6-dien-3-yl, octa-1,6-dien-4-yl, octa-1,6-dien-5-yl, octa-1,6-dien-2-yl, deca-1,4-dienyl, deca-1,5-dienyl, deca-1,6-dienyl, deca-1,7-dienyl, deca-1,8-dienyl, deca-2,5-dienyl, deca-2,6-dienyl, deca-2,7-dienyl, deca-2,8-dienyl.


Alkoxy or alkoxy moieties, for example, in phenylalkoxy, alkoxyamino, alkoxycarbonyl: alkyl, as defined above, which is attached via an oxygen atom: for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.


In one embodiment according to the invention, small alkoxy groups such as C1-C4-alkoxy are employed. In another embodiment according to the invention, use is made of relatively large alkoxy groups such as C5-C6-alkoxy.


Alkenyloxy: alkenyl as mentioned above which is attached via an oxygen atom, for example C3-C6-alkenyloxy, such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-1-propenyloxy, 1,2-dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy, 3-methyl-1-pentenyloxy, 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-1-butenyloxy, 1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-1-butenyloxy, 1,3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-1-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3-dimethyl-2-butenyloxy, 1-ethyl-1-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-1-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy, 1-ethyl-2-methyl-1-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy. In one embodiment according to the invention, small alkenyloxy groups such as C3-C4-alkenyloxy are employed. In another embodiment according to the invention, use is made of relatively large alkenyloxy groups such as C5-C6-alkenyloxy.


Alkynyloxy: alkynyl as mentioned above which is attached via an oxygen atom, for example C3-C6-alkynyloxy, such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy. In one embodiment according to the invention, small alkynyloxy groups such as C3-C4-alkynyloxy are employed. In another embodiment according to the invention, use is made of relatively large alkynyloxy groups such as C5-C6-alkynyloxy.


Alkylthio: alkyl as defined above which is attached via a sulfur atom.


Alkylsulfinyl: alkyl as defined above which is attached via an SO group.


Alkylsulfonyl: alkyl as defined above which is attached via an S(O)2 group.


Alkylcarbonyl: alkyl as defined above which is attached via a (C═O) group, for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2,-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl.


Alkenylcarbonyl: alkenyl as defined above which is attached via a (C═O) group, for example 1-ethenylcarbonyl.


Alkynylcarbonyl: alkynyl as defined above which is attached via a (C═O) group, for example 1-propynylcarbonyl.


Heterocyclyl: a mono- or bicyclic saturated, partially unsaturated or aromatic heterocyclic ring having three or more, for example 3 to 10, ring atoms, for example a monocyclic 3-, 4-, 5-, 6- or 7-membered heterocyclic ring which contains one to four identical or different heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which may be attached via carbon or nitrogen, for example

    • 3- or 4-membered saturated or unsaturated rings attached via carbon, such as 2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thiethanyl, 1-azetidinyl, 2-azetidinyl.
    • 5-membered saturated rings attached via carbon, such as tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 1,3,2-dioxathiolan-4-yl.
    • 6-membered saturated rings attached via carbon, such as: tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl.
    • 5-membered saturated rings attached via nitrogen, such as: tetrahydropyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl.
    • 6-membered-saturated rings attached via nitrogen, such as: piperidin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl.
    • 5-membered partially unsaturated rings attached via carbon, such as: 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ3-1,2-dithiol-3-yl, Δ3-1,2-dithiol-4-yl, Δ3-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, 1,2,3-Δ2-oxadiazolin-4-yl, 1,2,3-Δ2-oxadiazolin-5-yl, 1,2,4-Δ4-oxadiazolin-3-yl, 1,2,4-Δ4-oxadiazolin-5-yl, 1,2,4-Δ2-oxadiazolin-3-yl, 1,2,4-Δ2-oxadiazolin-5-yl, 1,2,4-Δ3-oxadiazolin-3-yl, 1,2,4-Δ3-oxadiazolin-5-yl, 1,3,4-Δ2-oxadiazolin-2-yl, 1,3,4-Δ2-oxadiazolin-5-yl, 1,3,4-Δ3-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,4-Δ4-thiadiazolin-3-yl, 1,2,4-Δ4-thiadiazolin-5-yl, 1,2,4-Δ3-thiadiazolin-3-yl, 1,2,4-Δ3-thiadiazolin-5-yl, 1,2,4-Δ2-thiadiazolin-3-yl, 1,2,4-Δ2-thiadiazolin-5-yl, 1,3,4-Δ2-thiadiazolin-2-yl, 1,3,4-Δ2-thiadiazolin-5-yl, 1,3,4-Δ3-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,2,3-Δ2-triazolin-4-yl, 1,2,3-Δ2-triazolin-5-yl, 1,2,4-Δ2-triazolin-3-yl, 1,2,4-Δ2-triazolin-5-yl, 1,2,4-Δ3-triazolin-3-yl, 1,2,4-Δ3-triazolin-5-yl, 1,2,4-Δ1-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl.
    • 6-membered partially unsaturated rings attached via carbon, such as: 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydrothiopyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydrothiopyran-3-yl, 2H-3,4-dihydrothiopyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6-yl.
    • 5-membered partially unsaturated rings attached via nitrogen, such as: 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-5 imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, 1,2,4-Δ4-oxadiazolin-2-yl, 1,2,4-Δ2-oxadiazolin-4-yl, 1,2,4-Δ3-oxadiazolin-2-yl, 1,3,4-Δ2-oxadiazolin-4-yl, 1,2,4-Δ5-thiadiazolin-2-yl, 1,2,4-Δ3-thiadiazolin-2-yl, 1,2,4-Δ2-thiadiazolin-4-yl, 1,3,4-Δ2-thiadiazolin-4-yl, 1,2,3-Δ2-triazolin-1-yl, 1,2,4-Δ2-triazolin-1-yl, 1,2,4-Δ2-triazolin-4-yl, 1,2,4-Δ3-triazolin-1-yl, 1,2,4-Δ1-triazolin-4-yl.
    • 6-membered partially unsaturated rings attached via nitrogen, such as: 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-1,2-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl.
    • 5-membered heteroaromatic rings, attached via carbon, having generally 1, 2, 3 or 4 nitrogen atoms or a heteroatom selected from oxygen and sulfur and, if appropriate, 1, 2 or 3 nitrogen atoms as ring members, such as: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl, tetrazol-5-yl.
    • 6-membered heteroaromatic rings, attached via carbon, having generally 1, 2, 3 or 4 nitrogen atoms as ring members, such as
    • pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,4,5-tetrazin-3-yl.
    • 5-membered heteroaromatic rings, attached via nitrogen, having generally 1, 2, 3 or 4 nitrogen atoms as ring members, such as:
    • pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl.


      or a bicyclic heterocycle which comprises one of the abovementioned 5- or 6-membered heterocyclic rings and a further fused-on saturated, unsaturated or aromatic carbocycle, for example a benzene, cyclohexane, cyclohexene or cyclohexadiene ring, or a further fused-on 5- or 6-membered heterocyclic ring, where the latter may likewise be saturated, unsaturated or aromatic.


A sulfur atom in the heterocycles mentioned may be oxidized to S═O or S(═O)2.


Accordingly, hetaryl and/or heteroaryl are a 5- or 6-membered heteroaromatic radical which has 1, 2, 3 or 4 identical or different heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members, which may be attached via carbon or nitrogen and which, together with a further fused-on benzene ring or a 5- to 6-membered heteroaromatic may form a bicyclic ring system. Examples of hetaryl are the abovementioned 5- and 6-membered heteroaromatic rings attached via carbon, the abovementioned 5-membered heteroaromatic rings attached via nitrogen and bicyclic heteroaromatic radicals such as quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, indolyl, benzothienyl, benzofuryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzopyrazolyl, benzotriazole, indolizinyl, 1,2,4-triazolo[1,5-a]pyrimidinyl, 1,2,4-triazolo[4,3-a]pyridinyl, pyrazolo[3,4-b]pyridinyl, 1,2,4-triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridyl, imidazo[3,4-a]pyrimidinyl, and the like.


Aryl: a mono- or polycyclic aromatic carbocycle, for example a mono- or bicyclic or a mono- to tricyclic aromatic carbocycle having 6 to 14 ring members, such as, for example, phenyl, naphthyl or anthracenyl.


Arylalkyl: an aryl radical attached via an alkylene group, in particular via a methylene, 1,1-ethylene or 1,2-ethylene group, for example benzyl, 1-phenylethyl and 2-phenylethyl.


Heterocyclylalkyl and also hetarylalkyl: a heterocyclyl or hetaryl radical attached via an alkylene group, in particular via a methylene, 1,1-ethylene or 1,2-ethylene group.


In a particular embodiment, the variables of the compounds of the formula I have the meanings below, these meanings—both on their own and in combination with one another—being particular embodiments of the compounds of the formula I:

  • R1 is hydrogen, amino, cyano, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl-(C1-C6)-alkyl, heterocyclyl-(C1-C6)-alkyl or COR21, where R21 is as defined above and is in particular C1-C6-alkyl, C1-C10-alkoxy, phenyl, phenylamino or heterocyclyl; where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents may be partially or fully halogenated. With particular preference, R1 has the meanings hydrogen or C1-C6-alkyl, in particular methyl.
  • R2 is amino, cyano, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl-(C1-C6)-alkyl, heterocyclyl-(C1-C6)-alkyl or COR21, where R21 is as defined above and is in particular C1-C6-alkyl, C1-C6-alkoxy, phenyl, phenylamino or heterocyclyl; where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents may be partially or fully halogenated. With particular preference R2 has the meaning C1-C6-alkyl, in particular methyl.
  • R3 is hydrogen, halogen, C1-C6-alkyl or halo-C1-C6-alkyl.
  • R4, R5 and/or R6 are hydrogen.
  • A1 is aryl or heteroaryl selected from the group consisting of phenyl, naphthyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl or tetrazinyl.
    • In particular, A1 is selected from the group consisting of phenyl, furyl, thienyl, triazolyl, tetrazolyl or pyridinyl.
    • With particular preference, A1 has the meaning phenyl or pyridinyl, in particular phenyl.
    • In another preferred embodiment, A1 is a bicyclic aromatic radical, in particular napthyl or one of the bicyclic heteroaromatic radicals mentioned above, such as quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, indolyl, benzothienyl, benzofuryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzopyrazolyl, benzotriazole, indolizinyl, 1,2,4-triazolo[1,5-a]pyrimidinyl, 1,2,4-triazolo[4,3-a]pyridinyl, pyrazolo[3,4-b]pyridinyl, 1,2,4-triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridyl, imidazo[3,4-a]pyrimidinyl, especially indolyl, very especially 3-indolyl.
  • A2 is aryl or heteroaryl selected from the group consisting of phenyl, naphthyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl or tetrazinyl, in particular selected from the group consisting of phenyl, furyl, thienyl, triazolyl, tetrazolyl or pyridinyl. Particularly preferably, A2 has the meaning phenyl or thienyl, in particular phenyl.


According to the invention, A1 carries a radical Ra different from hydrogen, as mentioned above. Preferably, this radical is attached in the ortho-position to the point of attachment of A1 to a nitrogen or in particular to a carbon atom of A1; this ortho-position is preferred independently of whether A1 is a mono- or polycyclic aromatic or heteroaromatic ring.


In an alternatively preferred embodiment of the invention, if A1 is a polycyclic aromatic or heteroaromatic ring, the radical Ra is preferably not attached to the cycle of the polycyclic ring system which comprises the point of attachment of A1, i.e. via which A1 is attached to the exocyclic double bond which leads to the piperazine ring (=“linking cycle”). In a ring system with three or more cycles, Ra is preferably attached to a cycle which is directly adjacent to the “linking cycle”. With particular preference, Ra is attached as closely as possible to the point of attachment of A1. Here, Ra is in particular in the α-position to the bridgehead atom which is closest to the point of attachment of A1 to the exocyclic double bond.


If Ra is attached to a nitrogen atom, Ra is preferably different from halogen, C1-C6-alkylthio, C1-C6-alkylsulfinyl, Z1P(O)(OR9)2, where Z1 is a bond. In a preferred embodiment of the invention, Ra is attached to a carbon atom.


Ra has preferably one of the following meanings:

    • halogen, cyano, nitro, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, [tri-(C1-C6)-alkylsilyl]-(C2-C6)-alkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, aryl, heterocyclyl, in particular 5- or 6-membered heterocyclyl, where aryl and heterocyclyl are unsubstituted or may have one or 2 radicals selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, CN and halogen;
    • Z1P(O)(OR9)2, where Z1 is a bond or —CH2— and R9 are each hydrogen or C1-C6-alkyl;
    • Z3COR11, where Z3 is a bond and R11 has the meanings mentioned above and in particular is hydrogen, C1-C6-alkyl, hydroxyl, C1-C10-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C10-alkylamino, [di-(C1-C6)-alkyl]amino, C1-C6-alkoxyamino, N—C1-C6-alkoxy-N—C1-C6-alkylamino, [di-(C1-C6)-alkoxy]amino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6)-alkylamino]sulfonylamino, phenyl, phenoxy, phenylamino, naphthyl or heterocyclyl, especially 5- or 6-membered heteroaryl attached via carbon;
    • Z4NR12R13, where Z4 is a bond or —CH2— and R12 and R13 have the meanings mentioned above and in particular independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, [di-(C1-C6)-alkylamino]carbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylaminosulfonyl, [di-(C1-C6)-alkylamino]sulfonyl, C3-C6-cycloalkylcarbonyl, phenylcarbonyl, phenylaminocarbonyl, phenylsulfonyl, phenylsulfonylaminocarbonyl or heterocyclylcarbonyl, especially 5- or 6-membered heteroarylcarbonyl attached via carbon;
    • Z5CH═N—O—R14, where Z5 is a bond and R14 is hydrogen or C1-C6-alkyl; or
    • Z6OR15, where Z6 is a bond or —CH2— and R15 has the meanings mentioned above and in particular is C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, di-(C1-C6-alkoxycarbonyl)-C1-C6-alkyl, phenylcarbonyl or phenyl, R15 may also be hydrogen, C1-C10-alkyl or phenyl-C1-C6-alkyl; or
    • Z7SO2R16, where Z7 is a bond or CH2 and R16 is C1-C6-alkyl or phenyl;


      and where the abovementioned aliphatic, cyclic or aromatic moieties of the substituents Ra may be partially or fully halogenated.


If Ra is attached to a nitrogen atom, Ra is preferably different from halogen, C1-C6-alkylthio, C1-C6-alkylsulfinyl, Z1P(O)(OR9)2, where Z1 is a bond. In a preferred embodiment of the invention, Ra is attached to a carbon atom.


Ra has in particular one of the following meanings:

    • halogen, cyano, nitro, C1-C6-alkylthio, C1-C6-alkylsulfinyl, aryl, heterocyclyl, where the two last-mentioned radicals are unsubstituted or may have one or 2 radicals selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, CN and halogen,
    • C2-C6-alkenyl, C2-C6-alkynyl,
    • Z1P(O)(OR9)2, where Z1 is a bond or —CH2— and R9 is in each case hydrogen or C1-C6-alkyl; or
    • Z3COR11, where Z3 is a bond and R11 is hydrogen, C1-C6-alkyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C1-C6-alkoxyamino, N—C1-C6-alkoxy-N—C1-C6-alkylamino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6)-alkyl-amino]sulfonylamino, phenyl, phenoxy, phenylamino, naphthyl or heterocyclyl, especially 5- or 6-membered heteroaryl which is attached via carbon; or
    • Z4NR12R13, where Z4 is a bond or —CH2— and R12 and R13 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, [di-(C1-C6)-alkylamino]carbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, phenylcarbonyl, phenylsulfonyl, or heterocyclylcarbonyl, especially 5- or 6-membered heteroarylcarbonyl which is attached via carbon; or
    • Z5CH═N—O—R14, where Z5 is a bond and R14 is hydrogen or C1-C6-alkyl; or
    • Z6OR15, where Z6 is a bond or —CH2— and R15 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy-carbonyl-(C1-C6)-alkyl, phenyl or phenyl-(C1-C6)-alkyl; or
    • Z7SO2R16, where Z7 is a bond or CH2 and R16 is C1-C6-alkyl or phenyl;


      and where the aliphatic, cyclic or aromatic parts mentioned of the substituents Ra may be partially or fully halogenated.


Very particularly preferably, Ra is a radical selected from the group consisting of halogen, cyano, nitro, C2-C4-alkenyl and C2-C4-alkynyl, NH—C(O)—C1-C6-alkyl, NH—S(O)2—C1-C6-alkyl and 5-membered heteroaryl, for example oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, where the heteroaryl radicals mentioned above may have one or 2 radicals selected from the group consisting of C1-C2-alkyl, C1-C2-haloalkyl and halogen, and which is in particular attached in one of the ortho-positions of A1.


Rb, Rc, Rd, Re and Rf are preferably hydrogen or independently of one another have one of the meanings mentioned as being preferred or particularly preferred for Ra.


In particular, the radicals Rb, Rc, Rd, Re and Rf independently of one another are selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl and C1-C4-haloalkoxy, where two groups Rb, Rc, Rd, Re or Rf attached to adjacent carbon atoms of A1 or A2 may also be a group O—CH2—O.


Rb is in particular a radical different from hydrogen. Preferably, Rb is a radical attached in the ortho-position of A1, i.e. if Ra is likewise attached in the ortho-position, Rb is in the second ortho-position.


If one or both radicals Rb, Rc are substituents different from hydrogen, they are selected in particular from among the substituents stated as being preferred, and especially from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and C1-C4-haloalkoxy, or Rb and Rc together are a group O—CH2—O.


A2 is in particular unsubstituted, or one or two of the substituents Rd, Re and Rf are substituents different from hydrogen. If 1 or 2 of the substituents Rd, Re and Rf are different from hydrogen, they are selected in particular from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl and C1-C4-haloalkoxy.


The meaning that a substituent may assume in the context of the invention is completely independent of the meaning which another substituent may assume in the context of the invention. However, particular preference is given to compounds of the formula I in which a plurality or in particular all variables have a meaning given as being preferred or particularly preferred.


Furthermore, it has been found to be advantageous for the exocyclic double bond at the piperazine ring to have the Z-conformation, i.e. the group A1(RaRbRc) and the ring nitrogen which carries the group R2 are in a cis arrangement with respect to this double bond. Accordingly, a preferred embodiment of the invention relates to piperazine compounds of the formula (Z)-I in which the variables A1, A2, R1-R6 and Ra-Rf are as defined above, and also to mixtures of the Z-isomer (Z)-I with the E-isomer of the formula (E)-I, where the E/Z ratio is <1:1, in particular <1:2, particularly preferably <1:4 and especially <1:10. In formula (E)-I, the variables A1, A2, R1-R6 and Ra-Rf are also as defined above.







Furthermore, it has been found to be advantageous for the carbon atom which carries R4 to have the S-configuration. Accordingly, a preferred embodiment of the invention relates to piperazine compounds of the formula I-S in which the variables A1, A2, R1-R6 and Ra-Rf are as defined above, and also to mixtures of the S-enantiomer (S)-I with the R-enantiomer of the formula (R)-I in which the R/S ratio is <1:1, in particular <1:2, particularly preferably <1:4 and especially <1:10. In formula (R)-I, the variables A1, A2, R1-R6 and Ra-Rf are also as defined above.







Preference is given in particular to compounds of the formula I in which both the exocyclic double bond has the Z-conformation and the carbon atom which carries R4 has the S-configuration. Hereinbelow, these compounds are also referred to as compounds (Z,S)-I.


Preference is given in particular to the compounds of the formula I.1 in which R1, R3, R4, R5, and R6 are hydrogen and R2 is CH3, particularly preferably the compounds (Z,S)-I.1 which have the Z- or S-configuration at the indicated positions (1) and (2). Examples of preferred compounds I.1 and (Z,S)-I.1 are those in which A1, Ra, Rb and Rc are as defined in Table 1:







The compounds I.1.1 to I.3434 listed below are per se preferred embodiments of the invention.













TABLE 1





Comp. No.
A1
Ra
Rb
Rc







I.1.1
phenyl
2-NO2
H
H


I.1.2
phenyl
2-NO2
3-Cl
H


I.1.3
phenyl
2-NO2
4-Cl
H


I.1.4
phenyl
2-NO2
5-Cl
H


I.1.5
phenyl
2-NO2
6-Cl
H


I.1.6
phenyl
2-NO2
3-F
H


I.1.7
phenyl
2-NO2
4-F
H


I.1.8
phenyl
2-NO2
5-F
H


I.1.9
phenyl
2-NO2
6-F
H


I.1.10
phenyl
2-NO2
3-CH3
H


I.1.11
phenyl
2-NO2
4-CH3
H


I.1.12
phenyl
2-NO2
5-CH3
H


I.1.13
phenyl
2-NO2
6-CH3
H


I.1.14
phenyl
2-NO2
5-vinyl
H


I.1.15
phenyl
2-NO2
6-vinyl
H


I.1.16
phenyl
2-NO2
5-CF3
3-Cl


I.1.17
phenyl
2-NO2
5-CF3
4-Cl


I.1.18
phenyl
2-NO2
4-CF3
5-Cl


I.1.19
phenyl
2-NO2
5-CF3
6-Cl


I.1.20
phenyl
2-NO2
5-CF3
3-F


I.1.21
phenyl
2-NO2
5-CF3
4-F


I.1.22
phenyl
2-NO2
4-CF3
5-F


I.1.23
phenyl
2-NO2
5-CF3
6-F


I.1.24
phenyl
2-NO2
5-CF3
3-CH3


I.1.25
phenyl
2-NO2
5-CF3
4-CH3


I.1.26
phenyl
2-NO2
4-CF3
5-CH3


I.1.27
phenyl
2-NO2
5-CF3
6-CH3


I.1.28
phenyl
2-NO2
4-CF3
5-vinyl


I.1.29
phenyl
2-NO2
4-CF3
6-vinyl


I.1.30
phenyl
2-NO2
3-Cl
4-F


I.1.31
phenyl
2-NO2
3-Cl
5-F


I.1.32
phenyl
2-NO2
3-Cl
6-F


I.1.33
phenyl
2-NO2
3-Cl
4-Cl


I.1.34
phenyl
2-NO2
3-Cl
5-Cl


I.1.35
phenyl
2-NO2
3-Cl
6-Cl


I.1.36
phenyl
2-NO2
3-Cl
4-CH3


I.1.37
phenyl
2-NO2
3-Cl
5-CH3


I.1.38
phenyl
2-NO2
3-Cl
6-CH3


I.1.39
phenyl
2-NO2
3-Cl
5-vinyl


I.1.40
phenyl
2-NO2
3-Cl
6-vinyl


I.1.41
phenyl
2-NO2
3-F
4-F


I.1.42
phenyl
2-NO2
3-F
5-F


I.1.43
phenyl
2-NO2
3-F
6-F


I.1.44
phenyl
2-NO2
3-F
4-Cl


I.1.45
phenyl
2-NO2
3-F
5-Cl


I.1.46
phenyl
2-NO2
3-F
6-Cl


I.1.47
phenyl
2-NO2
3-F
4-CH3


I.1.48
phenyl
2-NO2
3-F
5-CH3


I.1.49
phenyl
2-NO2
3-F
6-CH3


I.1.50
phenyl
2-NO2
3-F
5-vinyl


I.1.51
phenyl
2-NO2
3-F
6-vinyl


I.1.52
phenyl
2-NO2
3-CH3
4-F


I.1.53
phenyl
2-NO2
3-CH3
5-F


I.1.54
phenyl
2-NO2
3-CH3
6-F


I.1.55
phenyl
2-NO2
3-CH3
4-Cl


I.1.56
phenyl
2-NO2
3-CH3
5-Cl


I.1.57
phenyl
2-NO2
3-CH3
6-Cl


I.1.58
phenyl
2-NO2
3-CH3
4-CH3


I.1.59
phenyl
2-NO2
3-CH3
5-CH3


I.1.60
phenyl
2-NO2
3-CH3
6-CH3


I.1.61
phenyl
2-NO2
3-CH3
5-vinyl


I.1.62
phenyl
2-NO2
3-CH3
6-vinyl


I.1.63
phenyl
2-NO2
4-Cl
5-F


I.1.64
phenyl
2-NO2
4-Cl
6-F


I.1.65
phenyl
2-NO2
4-Cl
5-Cl


I.1.66
phenyl
2-NO2
4-Cl
6-Cl


I.1.67
phenyl
2-NO2
4-Cl
5-CH3


I.1.68
phenyl
2-NO2
4-Cl
6-CH3


I.1.69
phenyl
2-NO2
4-Cl
5-vinyl


I.1.70
phenyl
2-NO2
4-Cl
6-vinyl


I.1.71
phenyl
2-NO2
4-F
5-F


I.1.72
phenyl
2-NO2
4-F
6-F


I.1.73
phenyl
2-NO2
4-F
5-Cl


I.1.74
phenyl
2-NO2
4-F
6-Cl


I.1.75
phenyl
2-NO2
4-F
5-CH3


I.1.76
phenyl
2-NO2
4-F
6-CH3


I.1.77
phenyl
2-NO2
4-F
5-vinyl


I.1.78
phenyl
2-NO2
4-F
6-vinyl


I.1.79
phenyl
2-NO2
4-CH3
5-F


I.1.80
phenyl
2-NO2
4-CH3
6-F


I.1.81
phenyl
2-NO2
4-CH3
5-Cl


I.1.82
phenyl
2-NO2
4-CH3
6-Cl


I.1.83
phenyl
2-NO2
4-CH3
5-CH3


I.1.84
phenyl
2-NO2
4-CH3
6-CH3


I.1.85
phenyl
2-NO2
4-CH3
5-vinyl


I.1.86
phenyl
2-NO2
4-CH3
6-vinyl


I.1.87
phenyl
2-NO2
5-Cl
6-Cl


I.1.88
phenyl
2-NO2
5-Cl
6-F


I.1.89
phenyl
2-NO2
5-Cl
6-CH3


I.1.90
phenyl
2-NO2
5-Cl
6-vinyl


I.1.91
phenyl
2-NO2
5-F
6-Cl


I.1.92
phenyl
2-NO2
5-F
6-F


I.1.93
phenyl
2-NO2
5-F
6-CH3


I.1.94
phenyl
2-NO2
5-F
6-vinyl


I.1.95
phenyl
2-NO2
5-CH3
6-Cl


I.1.96
phenyl
2-NO2
5-CH3
6-F


I.1.97
phenyl
2-NO2
5-CH3
6-CH3


I.1.98
phenyl
2-NO2
5-CH3
6-vinyl


I.1.99
phenyl
2-NO2
5-vinyl
6-Cl


I.1.100
phenyl
2-NO2
5-vinyl
6-F


I.1.101
phenyl
2-NO2
5-vinyl
6-CH3


I.1.102
phenyl
2-NO2
5-vinyl
6-vinyl


I.1.103
phenyl
2-CN
H
H


I.1.104
phenyl
2-CN
3-Cl
H


I.1.105
phenyl
2-CN
4-Cl
H


I.1.106
phenyl
2-CN
5-Cl
H


I.1.107
phenyl
2-CN
6-Cl
H


I.1.108
phenyl
2-CN
3-F
H


I.1.109
phenyl
2-CN
4-F
H


I.1.110
phenyl
2-CN
5-F
H


I.1.111
phenyl
2-CN
6-F
H


I.1.112
phenyl
2-CN
3-CH3
H


I.1.113
phenyl
2-CN
4-CH3
H


I.1.114
phenyl
2-CN
5-CH3
H


I.1.115
phenyl
2-CN
6-CH3
H


I.1.116
phenyl
2-CN
5-vinyl
H


I.1.117
phenyl
2-CN
6-vinyl
H


I.1.118
phenyl
2-CN
5-CF3
3-Cl


I.1.119
phenyl
2-CN
5-CF3
4-Cl


I.1.120
phenyl
2-CN
4-CF3
5-Cl


I.1.121
phenyl
2-CN
5-CF3
6-Cl


I.1.122
phenyl
2-CN
5-CF3
3-F


I.1.123
phenyl
2-CN
5-CF3
4-F


I.1.124
phenyl
2-CN
4-CF3
5-F


I.1.125
phenyl
2-CN
5-CF3
6-F


I.1.126
phenyl
2-CN
5-CF3
3-CH3


I.1.127
phenyl
2-CN
5-CF3
4-CH3


I.1.128
phenyl
2-CN
4-CF3
5-CH3


I.1.129
phenyl
2-CN
5-CF3
6-CH3


I.1.130
phenyl
2-CN
4-CF3
5-vinyl


I.1.131
phenyl
2-CN
4-CF3
6-vinyl


I.1.132
phenyl
2-CN
3-Cl
4-F


I.1.133
phenyl
2-CN
3-Cl
5-F


I.1.134
phenyl
2-CN
3-Cl
6-F


I.1.135
phenyl
2-CN
3-Cl
4-Cl


I.1.136
phenyl
2-CN
3-Cl
5-Cl


I.1.137
phenyl
2-CN
3-Cl
6-Cl


I.1.138
phenyl
2-CN
3-Cl
4-CH3


I.1.139
phenyl
2-CN
3-Cl
5-CH3


I.1.140
phenyl
2-CN
3-Cl
6-CH3


I.1.141
phenyl
2-CN
3-Cl
5-vinyl


I.1.142
phenyl
2-CN
3-Cl
6-vinyl


I.1.143
phenyl
2-CN
3-F
4-F


I.1.144
phenyl
2-CN
3-F
5-F


I.1.145
phenyl
2-CN
3-F
6-F


I.1.146
phenyl
2-CN
3-F
4-Cl


I.1.147
phenyl
2-CN
3-F
5-Cl


I.1.148
phenyl
2-CN
3-F
6-Cl


I.1.149
phenyl
2-CN
3-F
4-CH3


I.1.150
phenyl
2-CN
3-F
5-CH3


I.1.151
phenyl
2-CN
3-F
6-CH3


I.1.152
phenyl
2-CN
3-F
5-vinyl


I.1.153
phenyl
2-CN
3-F
6-vinyl


I.1.154
phenyl
2-CN
3-CH3
4-F


I.1.155
phenyl
2-CN
3-CH3
5-F


I.1.156
phenyl
2-CN
3-CH3
6-F


I.1.157
phenyl
2-CN
3-CH3
4-Cl


I.1.158
phenyl
2-CN
3-CH3
5-Cl


I.1.159
phenyl
2-CN
3-CH3
6-Cl


I.1.160
phenyl
2-CN
3-CH3
4-CH3


I.1.161
phenyl
2-CN
3-CH3
5-CH3


I.1.162
phenyl
2-CN
3-CH3
6-CH3


I.1.163
phenyl
2-CN
3-CH3
5-vinyl


I.1.164
phenyl
2-CN
3-CH3
6-vinyl


I.1.165
phenyl
2-CN
4-Cl
5-F


I.1.166
phenyl
2-CN
4-Cl
6-F


I.1.167
phenyl
2-CN
4-Cl
5-Cl


I.1.168
phenyl
2-CN
4-Cl
6-Cl


I.1.169
phenyl
2-CN
4-Cl
5-CH3


I.1.170
phenyl
2-CN
4-Cl
6-CH3


I.1.171
phenyl
2-CN
4-Cl
5-vinyl


I.1.172
phenyl
2-CN
4-Cl
6-vinyl


I.1.173
phenyl
2-CN
4-F
5-F


I.1.174
phenyl
2-CN
4-F
6-F


I.1.175
phenyl
2-CN
4-F
5-Cl


I.1.176
phenyl
2-CN
4-F
6-Cl


I.1.177
phenyl
2-CN
4-F
5-CH3


I.1.178
phenyl
2-CN
4-F
6-CH3


I.1.179
phenyl
2-CN
4-F
5-vinyl


I.1.180
phenyl
2-CN
4-F
6-vinyl


I.1.181
phenyl
2-CN
4-CH3
5-F


I.1.182
phenyl
2-CN
4-CH3
6-F


I.1.183
phenyl
2-CN
4-CH3
5-Cl


I.1.184
phenyl
2-CN
4-CH3
6-Cl


I.1.185
phenyl
2-CN
4-CH3
5-CH3


I.1.186
phenyl
2-CN
4-CH3
6-CH3


I.1.187
phenyl
2-CN
4-CH3
5-vinyl


I.1.188
phenyl
2-CN
4-CH3
6-vinyl


I.1.189
phenyl
2-CN
5-Cl
6-Cl


I.1.190
phenyl
2-CN
5-Cl
6-F


I.1.191
phenyl
2-CN
5-Cl
6-CH3


I.1.192
phenyl
2-CN
5-Cl
6-vinyl


I.1.193
phenyl
2-CN
5-F
6-Cl


I.1.194
phenyl
2-CN
5-F
6-F


I.1.195
phenyl
2-CN
5-F
6-CH3


I.1.196
phenyl
2-CN
5-F
6-vinyl


I.1.197
phenyl
2-CN
5-CH3
6-Cl


I.1.198
phenyl
2-CN
5-CH3
6-F


I.1.199
phenyl
2-CN
5-CH3
6-CH3


I.1.200
phenyl
2-CN
5-CH3
6-vinyl


I.1.201
phenyl
2-CN
5-vinyl
6-Cl


I.1.202
phenyl
2-CN
5-vinyl
6-F


I.1.203
phenyl
2-CN
5-vinyl
6-CH3


I.1.204
phenyl
2-CN
5-vinyl
6-vinyl


I.1.205
phenyl
2-ethynyl
H
H


I.1.206
phenyl
2-ethynyl
3-Cl
H


I.1.207
phenyl
2-ethynyl
4-Cl
H


I.1.208
phenyl
2-ethynyl
5-Cl
H


I.1.209
phenyl
2-ethynyl
6-Cl
H


I.1.210
phenyl
2-ethynyl
3-F
H


I.1.211
phenyl
2-ethynyl
4-F
H


I.1.212
phenyl
2-ethynyl
5-F
H


I.1.213
phenyl
2-ethynyl
6-F
H


I.1.214
phenyl
2-ethynyl
3-CH3
H


I.1.215
phenyl
2-ethynyl
4-CH3
H


I.1.216
phenyl
2-ethynyl
5-CH3
H


I.1.217
phenyl
2-ethynyl
6-CH3
H


I.1.218
phenyl
2-ethynyl
5-vinyl
H


I.1.219
phenyl
2-ethynyl
6-vinyl
H


I.1.220
phenyl
2-ethynyl
5-CF3
3-Cl


I.1.221
phenyl
2-ethynyl
5-CF3
4-Cl


I.1.222
phenyl
2-ethynyl
4-CF3
5-Cl


I.1.223
phenyl
2-ethynyl
5-CF3
6-Cl


I.1.224
phenyl
2-ethynyl
5-CF3
3-F


I.1.225
phenyl
2-ethynyl
5-CF3
4-F


I.1.226
phenyl
2-ethynyl
4-CF3
5-F


I.1.227
phenyl
2-ethynyl
5-CF3
6-F


I.1.228
phenyl
2-ethynyl
5-CF3
3-CH3


I.1.229
phenyl
2-ethynyl
5-CF3
4-CH3


I.1.230
phenyl
2-ethynyl
4-CF3
5-CH3


I.1.231
phenyl
2-ethynyl
5-CF3
6-CH3


I.1.232
phenyl
2-ethynyl
4-CF3
5-vinyl


I.1.233
phenyl
2-ethynyl
4-CF3
6-vinyl


I.1.234
phenyl
2-ethynyl
3-Cl
4-F


I.1.235
phenyl
2-ethynyl
3-Cl
5-F


I.1.236
phenyl
2-ethynyl
3-Cl
6-F


I.1.237
phenyl
2-ethynyl
3-Cl
4-Cl


I.1.238
phenyl
2-ethynyl
3-Cl
5-Cl


I.1.239
phenyl
2-ethynyl
3-Cl
6-Cl


I.1.240
phenyl
2-ethynyl
3-Cl
4-CH3


I.1.241
phenyl
2-ethynyl
3-Cl
5-CH3


I.1.242
phenyl
2-ethynyl
3-Cl
6-CH3


I.1.243
phenyl
2-ethynyl
3-Cl
5-vinyl


I.1.244
phenyl
2-ethynyl
3-Cl
6-vinyl


I.1.245
phenyl
2-ethynyl
3-F
4-F


I.1.246
phenyl
2-ethynyl
3-F
5-F


I.1.247
phenyl
2-ethynyl
3-F
6-F


I.1.248
phenyl
2-ethynyl
3-F
4-Cl


I.1.249
phenyl
2-ethynyl
3-F
5-Cl


I.1.250
phenyl
2-ethynyl
3-F
6-Cl


I.1.251
phenyl
2-ethynyl
3-F
4-CH3


I.1.252
phenyl
2-ethynyl
3-F
5-CH3


I.1.253
phenyl
2-ethynyl
3-F
6-CH3


I.1.254
phenyl
2-ethynyl
3-F
5-vinyl


I.1.255
phenyl
2-ethynyl
3-F
6-vinyl


I.1.256
phenyl
2-ethynyl
3-CH3
4-F


I.1.257
phenyl
2-ethynyl
3-CH3
5-F


I.1.258
phenyl
2-ethynyl
3-CH3
6-F


I.1.259
phenyl
2-ethynyl
3-CH3
4-Cl


I.1.260
phenyl
2-ethynyl
3-CH3
5-Cl


I.1.261
phenyl
2-ethynyl
3-CH3
6-Cl


I.1.262
phenyl
2-ethynyl
3-CH3
4-CH3


I.1.263
phenyl
2-ethynyl
3-CH3
5-CH3


I.1.264
phenyl
2-ethynyl
3-CH3
6-CH3


I.1.265
phenyl
2-ethynyl
3-CH3
5-vinyl


I.1.266
phenyl
2-ethynyl
3-CH3
6-vinyl


I.1.267
phenyl
2-ethynyl
4-Cl
5-F


I.1.268
phenyl
2-ethynyl
4-Cl
6-F


I.1.269
phenyl
2-ethynyl
4-Cl
5-Cl


I.1.270
phenyl
2-ethynyl
4-Cl
6-Cl


I.1.271
phenyl
2-ethynyl
4-Cl
5-CH3


I.1.272
phenyl
2-ethynyl
4-Cl
6-CH3


I.1.273
phenyl
2-ethynyl
4-Cl
5-vinyl


I.1.274
phenyl
2-ethynyl
4-Cl
6-vinyl


I.1.275
phenyl
2-ethynyl
4-F
5-F


I.1.276
phenyl
2-ethynyl
4-F
6-F


I.1.277
phenyl
2-ethynyl
4-F
5-Cl


I.1.278
phenyl
2-ethynyl
4-F
6-Cl


I.1.279
phenyl
2-ethynyl
4-F
5-CH3


I.1.280
phenyl
2-ethynyl
4-F
6-CH3


I.1.281
phenyl
2-ethynyl
4-F
5-vinyl


I.1.282
phenyl
2-ethynyl
4-F
6-vinyl


I.1.283
phenyl
2-ethynyl
4-CH3
5-F


I.1.284
phenyl
2-ethynyl
4-CH3
6-F


I.1.285
phenyl
2-ethynyl
4-CH3
5-Cl


I.1.286
phenyl
2-ethynyl
4-CH3
6-Cl


I.1.287
phenyl
2-ethynyl
4-CH3
5-CH3


I.1.288
phenyl
2-ethynyl
4-CH3
6-Cl


I.1.289
phenyl
2-ethynyl
4-CH3
5-vinyl


I.1.290
phenyl
2-ethynyl
4-CH3
6-vinyl


I.1.291
phenyl
2-ethynyl
5-Cl
6-Cl


I.1.292
phenyl
2-ethynyl
5-Cl
6-F


I.1.293
phenyl
2-ethynyl
5-Cl
6-CH3


I.1.294
phenyl
2-ethynyl
5-Cl
6-vinyl


I.1.295
phenyl
2-ethynyl
5-F
6-Cl


I.1.296
phenyl
2-ethynyl
5-F
6-F


I.1.297
phenyl
2-ethynyl
5-F
6-CH3


I.1.298
phenyl
2-ethynyl
5-F
6-vinyl


I.1.299
phenyl
2-ethynyl
5-CH3
6-Cl


I.1.300
phenyl
2-ethynyl
5-CH3
6-F


I.1.301
phenyl
2-ethynyl
5-CH3
6-CH3


I.1.302
phenyl
2-ethynyl
5-CH3
6-vinyl


I.1.303
phenyl
2-ethynyl
5-vinyl
6-Cl


I.1.304
phenyl
2-ethynyl
5-vinyl
6-F


I.1.305
phenyl
2-ethynyl
5-vinyl
6-CH3


I.1.306
phenyl
2-ethynyl
5-vinyl
6-vinyl


I.1.307
phenyl
2-COOCH3
H
H


I.1.308
phenyl
2-COOCH3
3-Cl
H


I.1.309
phenyl
2-COOCH3
4-Cl
H


I.1.310
phenyl
2-COOCH3
5-Cl
H


I.1.311
phenyl
2-COOCH3
6-Cl
H


I.1.312
phenyl
2-COOCH3
3-F
H


I.1.313
phenyl
2-COOCH3
4-F
H


I.1.314
phenyl
2-COOCH3
5-F
H


I.1.315
phenyl
2-COOCH3
6-F
H


I.1.316
phenyl
2-COOCH3
3-CH3
H


I.1.317
phenyl
2-COOCH3
4-CH3
H


I.1.318
phenyl
2-COOCH3
5-CH3
H


I.1.319
phenyl
2-COOCH3
6-CH3
H


I.1.320
phenyl
2-COOCH3
5-vinyl
H


I.1.321
phenyl
2-COOCH3
6-vinyl
H


I.1.322
phenyl
2-COOCH3
5-CF3
3-Cl


I.1.323
phenyl
2-COOCH3
5-CF3
4-Cl


I.1.324
phenyl
2-COOCH3
4-CF3
5-Cl


I.1.325
phenyl
2-COOCH3
5-CF3
6-Cl


I.1.326
phenyl
2-COOCH3
5-CF3
3-F


I.1.327
phenyl
2-COOCH3
5-CF3
4-F


I.1.328
phenyl
2-COOCH3
4-CF3
5-F


I.1.329
phenyl
2-COOCH3
5-CF3
6-F


I.1.330
phenyl
2-COOCH3
5-CF3
3-CH3


I.1.331
phenyl
2-COOCH3
5-CF3
4-CH3


I.1.332
phenyl
2-COOCH3
4-CF3
5-CH3


I.1.333
phenyl
2-COOCH3
5-CF3
6-CH3


I.1.334
phenyl
2-COOCH3
4-CF3
5-vinyl


I.1.335
phenyl
2-COOCH3
4-CF3
6-vinyl


I.1.336
phenyl
2-COOCH3
3-Cl
4-F


I.1.337
phenyl
2-COOCH3
3-Cl
5-F


I.1.338
phenyl
2-COOCH3
3-Cl
6-F


I.1.339
phenyl
2-COOCH3
3-Cl
4-Cl


I.1.340
phenyl
2-COOCH3
3-Cl
5-Cl


I.1.341
phenyl
2-COOCH3
3-Cl
6-Cl


I.1.342
phenyl
2-COOCH3
3-Cl
4-CH3


I.1.343
phenyl
2-COOCH3
3-Cl
5-CH3


I.1.344
phenyl
2-COOCH3
3-Cl
6-CH3


I.1.345
phenyl
2-COOCH3
3-Cl
5-vinyl


I.1.346
phenyl
2-COOCH3
3-Cl
6-vinyl


I.1.347
phenyl
2-COOCH3
3-F
4-F


I.1.348
phenyl
2-COOCH3
3-F
5-F


I.1.349
phenyl
2-COOCH3
3-F
6-F


I.1.350
phenyl
2-COOCH3
3-F
4-Cl


I.1.351
phenyl
2-COOCH3
3-F
5-Cl


I.1.352
phenyl
2-COOCH3
3-F
6-Cl


I.1.353
phenyl
2-COOCH3
3-F
4-CH3


I.1.354
phenyl
2-COOCH3
3-F
5-CH3


I.1.355
phenyl
2-COOCH3
3-F
6-CH3


I.1.356
phenyl
2-COOCH3
3-F
5-vinyl


I.1.357
phenyl
2-COOCH3
3-F
6-vinyl


I.1.358
phenyl
2-COOCH3
3-CH3
4-F


I.1.359
phenyl
2-COOCH3
3-CH3
5-F


I.1.360
phenyl
2-COOCH3
3-CH3
6-F


I.1.361
phenyl
2-COOCH3
3-CH3
4-Cl


I.1.362
phenyl
2-COOCH3
3-CH3
5-Cl


I.1.363
phenyl
2-COOCH3
3-CH3
6-Cl


I.1.364
phenyl
2-COOCH3
3-CH3
4-CH3


I.1.365
phenyl
2-COOCH3
3-CH3
5-CH3


I.1.366
phenyl
2-COOCH3
3-CH3
6-CH3


I.1.367
phenyl
2-COOCH3
3-CH3
5-vinyl


I.1.368
phenyl
2-COOCH3
3-CH3
6-vinyl


I.1.369
phenyl
2-COOCH3
4-Cl
5-F


I.1.370
phenyl
2-COOCH3
4-Cl
6-F


I.1.371
phenyl
2-COOCH3
4-Cl
5-Cl


I.1.372
phenyl
2-COOCH3
4-Cl
6-Cl


I.1.373
phenyl
2-COOCH3
4-Cl
5-CH3


I.1.374
phenyl
2-COOCH3
4-Cl
6-CH3


I.1.375
phenyl
2-COOCH3
4-Cl
5-vinyl


I.1.376
phenyl
2-COOCH3
4-Cl
6-vinyl


I.1.377
phenyl
2-COOCH3
4-F
5-F


I.1.378
phenyl
2-COOCH3
4-F
6-F


I.1.379
phenyl
2-COOCH3
4-F
5-Cl


I.1.380
phenyl
2-COOCH3
4-F
6-Cl


I.1.381
phenyl
2-COOCH3
4-F
5-CH3


I.1.382
phenyl
2-COOCH3
4-F
6-CH3


I.1.383
phenyl
2-COOCH3
4-F
5-vinyl


I.1.384
phenyl
2-COOCH3
4-F
6-vinyl


I.1.385
phenyl
2-COOCH3
4-CH3
5-F


I.1.386
phenyl
2-COOCH3
4-CH3
6-F


I.1.387
phenyl
2-COOCH3
4-CH3
5-Cl


I.1.388
phenyl
2-COOCH3
4-CH3
6-Cl


I.1.389
phenyl
2-COOCH3
4-CH3
5-CH3


I.1.390
phenyl
2-COOCH3
4-CH3
6-CH3


I.1.391
phenyl
2-COOCH3
4-CH3
5-vinyl


I.1.392
phenyl
2-COOCH3
4-CH3
6-vinyl


I.1.393
phenyl
2-COOCH3
5-Cl
6-Cl


I.1.394
phenyl
2-COOCH3
5-Cl
6-F


I.1.395
phenyl
2-COOCH3
5-Cl
6-CH3


I.1.396
phenyl
2-COOCH3
5-Cl
6-vinyl


I.1.397
phenyl
2-COOCH3
5-F
6-Cl


I.1.398
phenyl
2-COOCH3
5-F
6-F


I.1.399
phenyl
2-COOCH3
5-F
6-CH3


I.1.400
phenyl
2-COOCH3
5-F
6-vinyl


I.1.401
phenyl
2-COOCH3
5-CH3
6-Cl


I.1.402
phenyl
2-COOCH3
5-CH3
6-F


I.1.403
phenyl
2-COOCH3
5-CH3
6-CH3


I.1.404
phenyl
2-COOCH3
5-CH3
6-vinyl


I.1.405
phenyl
2-COOCH3
5-vinyl
6-Cl


I.1.406
phenyl
2-COOCH3
5-vinyl
6-F


I.1.407
phenyl
2-COOCH3
5-vinyl
6-CH3


I.1.408
phenyl
2-COOCH3
5-vinyl
6-vinyl


I.1.409
phenyl
2-COOH
H
H


I.1.410
phenyl
2-COOH
3-Cl
H


I.1.411
phenyl
2-COOH
4-Cl
H


I.1.412
phenyl
2-COOH
5-Cl
H


I.1.413
phenyl
2-COOH
6-Cl
H


I.1.414
phenyl
2-COOH
3-F
H


I.1.415
phenyl
2-COOH
4-F
H


I.1.416
phenyl
2-COOH
5-F
H


I.1.417
phenyl
2-COOH
6-F
H


I.1.418
phenyl
2-COOH
3-CH3
H


I.1.419
phenyl
2-COOH
4-CH3
H


I.1.420
phenyl
2-COOH
5-CH3
H


I.1.421
phenyl
2-COOH
6-CH3
H


I.1.422
phenyl
2-COOH
5-vinyl
H


I.1.423
phenyl
2-COOH
6-vinyl
H


I.1.424
phenyl
2-COOH
5-CF3
3-Cl


I.1.425
phenyl
2-COOH
5-CF3
4-Cl


I.1.426
phenyl
2-COOH
4-CF3
5-Cl


I.1.427
phenyl
2-COOH
5-CF3
6-Cl


I.1.428
phenyl
2-COOH
5-CF3
3-F


I.1.429
phenyl
2-COOH
5-CF3
4-F


I.1.430
phenyl
2-COOH
4-CF3
5-F


I.1.431
phenyl
2-COOH
5-CF3
6-F


I.1.432
phenyl
2-COOH
5-CF3
3-CH3


I.1.433
phenyl
2-COOH
5-CF3
4-CH3


I.1.434
phenyl
2-COOH
4-CF3
5-CH3


I.1.435
phenyl
2-COOH
5-CF3
6-CH3


I.1.436
phenyl
2-COOH
4-CF3
5-vinyl


I.1.437
phenyl
2-COOH
4-CF3
6-vinyl


I.1.438
phenyl
2-COOH
3-Cl
4-F


I.1.439
phenyl
2-COOH
3-Cl
5-F


I.1.440
phenyl
2-COOH
3-Cl
6-F


I.1.441
phenyl
2-COOH
3-Cl
4-Cl


I.1.442
phenyl
2-COOH
3-Cl
5-Cl


I.1.443
phenyl
2-COOH
3-Cl
6-Cl


I.1.444
phenyl
2-COOH
3-Cl
4-CH3


I.1.445
phenyl
2-COOH
3-Cl
5-CH3


I.1.446
phenyl
2-COOH
3-Cl
6-CH3


I.1.447
phenyl
2-COOH
3-Cl
5-vinyl


I.1.448
phenyl
2-COOH
3-Cl
6-vinyl


I.1.449
phenyl
2-COOH
3-F
4-F


I.1.450
phenyl
2-COOH
3-F
5-F


I.1.451
phenyl
2-COOH
3-F
6-F


I.1.452
phenyl
2-COOH
3-F
4-Cl


I.1.453
phenyl
2-COOH
3-F
5-Cl


I.1.454
phenyl
2-COOH
3-F
6-Cl


I.1.455
phenyl
2-COOH
3-F
4-CH3


I.1.456
phenyl
2-COOH
3-F
5-CH3


I.1.457
phenyl
2-COOH
3-F
6-CH3


I.1.458
phenyl
2-COOH
3-F
5-vinyl


I.1.459
phenyl
2-COOH
3-F
6-vinyl


I.1.460
phenyl
2-COOH
3-CH3
4-F


I.1.461
phenyl
2-COOH
3-CH3
5-F


I.1.462
phenyl
2-COOH
3-CH3
6-F


I.1.463
phenyl
2-COOH
3-CH3
4-Cl


I.1.464
phenyl
2-COOH
3-CH3
5-Cl


I.1.465
phenyl
2-COOH
3-CH3
6-Cl


I.1.466
phenyl
2-COOH
3-CH3
4-CH3


I.1.467
phenyl
2-COOH
3-CH3
5-CH3


I.1.468
phenyl
2-COOH
3-CH3
6-CH3


I.1.469
phenyl
2-COOH
3-CH3
5-vinyl


I.1.470
phenyl
2-COOH
3-CH3
6-vinyl


I.1.471
phenyl
2-COOH
4-Cl
5-F


I.1.472
phenyl
2-COOH
4-Cl
6-F


I.1.473
phenyl
2-COOH
4-Cl
5-Cl


I.1.474
phenyl
2-COOH
4-Cl
6-Cl


I.1.475
phenyl
2-COOH
4-Cl
5-CH3


I.1.476
phenyl
2-COOH
4-Cl
6-CH3


I.1.477
phenyl
2-COOH
4-Cl
5-vinyl


I.1.478
phenyl
2-COOH
4-Cl
6-vinyl


I.1.479
phenyl
2-COOH
4-F
5-F


I.1.480
phenyl
2-COOH
4-F
6-F


I.1.481
phenyl
2-COOH
4-F
5-Cl


I.1.482
phenyl
2-COOH
4-F
6-Cl


I.1.483
phenyl
2-COOH
4-F
5-CH3


I.1.484
phenyl
2-COOH
4-F
6-CH3


I.1.485
phenyl
2-COOH
4-F
5-vinyl


I.1.486
phenyl
2-COOH
4-F
6-vinyl


I.1.487
phenyl
2-COOH
4-CH3
5-F


I.1.488
phenyl
2-COOH
4-CH3
6-F


I.1.489
phenyl
2-COOH
4-CH3
5-Cl


I.1.490
phenyl
2-COOH
4-CH3
6-Cl


I.1.491
phenyl
2-COOH
4-CH3
5-CH3


I.1.492
phenyl
2-COOH
4-CH3
6-CH3


I.1.493
phenyl
2-COOH
4-CH3
5-vinyl


I.1.494
phenyl
2-COOH
4-CH3
6-vinyl


I.1.495
phenyl
2-COOH
5-Cl
6-Cl


I.1.496
phenyl
2-COOH
5-Cl
6-F


I.1.497
phenyl
2-COOH
5-Cl
6-CH3


I.1.498
phenyl
2-COOH
5-Cl
6-vinyl


I.1.499
phenyl
2-COOH
5-F
6-Cl


I.1.500
phenyl
2-COOH
5-F
6-F


I.1.501
phenyl
2-COOH
5-F
6-CH3


I.1.502
phenyl
2-COOH
5-F
6-vinyl


I.1.503
phenyl
2-COOH
5-CH3
6-Cl


I.1.504
phenyl
2-COOH
5-CH3
6-F


I.1.505
phenyl
2-COOH
5-CH3
6-CH3


I.1.506
phenyl
2-COOH
5-CH3
6-vinyl


I.1.507
phenyl
2-COOH
5-vinyl
6-Cl


I.1.508
phenyl
2-COOH
5-vinyl
6-F


I.1.509
phenyl
2-COOH
5-vinyl
6-CH3


I.1.510
phenyl
2-COOH
5-vinyl
6-vinyl


I.1.511
phenyl
2-CON(CH3)2
H
H


I.1.512
phenyl
2-CON(CH3)2
3-Cl
H


I.1.513
phenyl
2-CON(CH3)2
4-Cl
H


I.1.514
phenyl
2-CON(CH3)2
5-Cl
H


I.1.515
phenyl
2-CON(CH3)2
6-Cl
H


I.1.516
phenyl
2-CON(CH3)2
3-F
H


I.1.517
phenyl
2-CON(CH3)2
4-F
H


I.1.518
phenyl
2-CON(CH3)2
5-F
H


I.1.519
phenyl
2-CON(CH3)2
6-F
H


I.1.520
phenyl
2-CON(CH3)2
3-CH3
H


I.1.521
phenyl
2-CON(CH3)2
4-CH3
H


I.1.522
phenyl
2-CON(CH3)2
5-CH3
H


I.1.523
phenyl
2-CON(CH3)2
6-CH3
H


I.1.524
phenyl
2-CON(CH3)2
5-vinyl
H


I.1.525
phenyl
2-CON(CH3)2
6-vinyl
H


I.1.526
phenyl
2-CON(CH3)2
5-CF3
3-Cl


I.1.527
phenyl
2-CON(CH3)2
5-CF3
4-Cl


I.1.528
phenyl
2-CON(CH3)2
4-CF3
5-Cl


I.1.529
phenyl
2-CON(CH3)2
5-CF3
6-Cl


I.1.530
phenyl
2-CON(CH3)2
5-CF3
3-F


I.1.531
phenyl
2-CON(CH3)2
5-CF3
4-F


I.1.532
phenyl
2-CON(CH3)2
4-CF3
5-F


I.1.533
phenyl
2-CON(CH3)2
5-CF3
6-F


I.1.534
phenyl
2-CON(CH3)2
5-CF3
3-CH3


I.1.535
phenyl
2-CON(CH3)2
5-CF3
4-CH3


I.1.536
phenyl
2-CON(CH3)2
4-CF3
5-CH3


I.1.537
phenyl
2-CON(CH3)2
5-CF3
6-CH3


I.1.538
phenyl
2-CON(CH3)2
4-CF3
5-vinyl


I.1.539
phenyl
2-CON(CH3)2
4-CF3
6-vinyl


I.1.540
phenyl
2-CON(CH3)2
3-Cl
4-F


I.1.541
phenyl
2-CON(CH3)2
3-Cl
5-F


I.1.542
phenyl
2-CON(CH3)2
3-Cl
6-F


I.1.543
phenyl
2-CON(CH3)2
3-Cl
4-Cl


I.1.544
phenyl
2-CON(CH3)2
3-Cl
5-Cl


I.1.545
phenyl
2-CON(CH3)2
3-Cl
6-Cl


I.1.546
phenyl
2-CON(CH3)2
3-Cl
4-CH3


I.1.547
phenyl
2-CON(CH3)2
3-Cl
5-CH3


I.1.548
phenyl
2-CON(CH3)2
3-Cl
6-CH3


I.1.549
phenyl
2-CON(CH3)2
3-Cl
5-vinyl


I.1.550
phenyl
2-CON(CH3)2
3-Cl
6-vinyl


I.1.551
phenyl
2-CON(CH3)2
3-F
4-F


I.1.552
phenyl
2-CON(CH3)2
3-F
5-F


I.1 553
phenyl
2-CON(CH3)2
3-F
6-F


I.1.554
phenyl
2-CON(CH3)2
3-F
4-Cl


I.1.555
phenyl
2-CON(CH3)2
3-F
5-Cl


I.1.556
phenyl
2-CON(CH3)2
3-F
6-Cl


I.1.557
phenyl
2-CON(CH3)2
3-F
4-CH3


I.1.558
phenyl
2-CON(CH3)2
3-F
5-CH3


I.1.559
phenyl
2-CON(CH3)2
3-F
6-CH3


I.1.560
phenyl
2-CON(CH3)2
3-F
5-vinyl


I.1.561
phenyl
2-CON(CH3)2
3-F
6-vinyl


I.1.562
phenyl
2-CON(CH3)2
3-CH3
4-F


I.1.563
phenyl
2-CON(CH3)2
3-CH3
5-F


I.1.564
phenyl
2-CON(CH3)2
3-CH3
6-F


I.1.565
phenyl
2-CON(CH3)2
3-CH3
4-Cl


I.1.566
phenyl
2-CON(CH3)2
3-CH3
5-Cl


I.1.557
phenyl
2-CON(CH3)2
3-CH3
6-Cl


I.1.568
phenyl
2-CON(CH3)2
3-CH3
4-CH3


I.1.569
phenyl
2-CON(CH3)2
3-CH3
5-CH3


I.1.570
phenyl
2-CON(CH3)2
3-CH3
6-CH3


I.1.571
phenyl
2-CON(CH3)2
3-CH3
5-vinyl


I.1.572
phenyl
2-CON(CH3)2
3-CH3
6-vinyl


I.1.573
phenyl
2-CON(CH3)2
4-Cl
5-F


I.1.574
phenyl
2-CON(CH3)2
4-Cl
6-F


I.1.575
phenyl
2-CON(CH3)2
4-Cl
5-Cl


I.1.576
phenyl
2-CON(CH3)2
4-Cl
6-Cl


I.1.577
phenyl
2-CON(CH3)2
4-Cl
5-CH3


I.1.578
phenyl
2-CON(CH3)2
4-Cl
6-CH3


I.1.579
phenyl
2-CON(CH3)2
4-Cl
5-vinyl


I.1.580
phenyl
2-CON(CH3)2
4-Cl
6-vinyl


I.1.581
phenyl
2-CON(CH3)2
4-F
5-F


I.1.582
phenyl
2-CON(CH3)2
4-F
6-F


I.1.583
phenyl
2-CON(CH3)2
4-F
5-Cl


I.1.584
phenyl
2-CON(CH3)2
4-F
6-Cl


I.1.585
phenyl
2-CON(CH3)2
4-F
5-CH3


I.1.586
phenyl
2-CON(CH3)2
4-F
6-CH3


I.1.587
phenyl
2-CON(CH3)2
4-F
5-vinyl


I.1.588
phenyl
2-CON(CH3)2
4-F
6-vinyl


I.1.589
phenyl
2-CON(CH3)2
4-CH3
5-F


I.1.590
phenyl
2-CON(CH3)2
4-CH3
6-F


I.1.591
phenyl
2-CON(CH3)2
4-CH3
5-Cl


I.1.592
phenyl
2-CON(CH3)2
4-CH3
6-Cl


I.1.593
phenyl
2-CON(CH3)2
4-CH3
5-CH3


I.1.594
phenyl
2-CON(CH3)2
4-CH3
6-CH3


I.1.595
phenyl
2-CON(CH3)2
4-CH3
5-vinyl


I.1.596
phenyl
2-CON(CH3)2
4-CH3
6-vinyl


I.1.597
phenyl
2-CON(CH3)2
5-Cl
6-Cl


I.1.598
phenyl
2-CON(CH3)2
5-Cl
6-F


I.1.599
phenyl
2-CON(CH3)2
5-Cl
6-CH3


I.1.600
phenyl
2-CON(CH3)2
5-Cl
6-vinyl


I.1.601
phenyl
2-CON(CH3)2
5-F
6-Cl


I.1.602
phenyl
2-CON(CH3)2
5-F
6-F


I.1.603
phenyl
2-CON(CH3)2
5-F
6-CH3


I.1.604
phenyl
2-CON(CH3)2
5-F
6-vinyl


I.1.605
phenyl
2-CON(CH3)2
5-CH3
6-Cl


I.1.606
phenyl
2-CON(CH3)2
5-CH3
6-F


I.1.607
phenyl
2-CON(CH3)2
5-CH3
6-CH3


I.1.608
phenyl
2-CON(CH3)2
5-CH3
6-vinyl


I.1.609
phenyl
2-CON(CH3)2
5-vinyl
6-Cl


I.1.610
phenyl
2-CON(CH3)2
5-vinyl
6-F


I.1.611
phenyl
2-CON(CH3)2
5-vinyl
6-CH3


I.1.612
phenyl
2-CON(CH3)2
5-vinyl
6-vinyl


I.1.613
phenyl
2-I
H
H


I.1.614
phenyl
2-I
3-Cl
H


I.1.615
phenyl
2-I
4-Cl
H


I.1.616
phenyl
2-I
5-Cl
H


I.1.617
phenyl
2-I
6-Cl
H


I.1.618
phenyl
2-I
3-F
H


I.1.619
phenyl
2-I
4-F
H


I.1.620
phenyl
2-I
5-F
H


I.1.621
phenyl
2-I
6-F
H


I.1.622
phenyl
2-I
3-CH3
H


I.1.623
phenyl
2-I
4-CH3
H


I.1.624
phenyl
2-I
5-CH3
H


I.1.625
phenyl
2-I
6-CH3
H


I.1.626
phenyl
2-I
5-vinyl
H


I.1.627
phenyl
2-I
6-vinyl
H


I.1.628
phenyl
2-I
5-CF3
3-Cl


I.1.629
phenyl
2-I
5-CF3
4-Cl


I.1.630
phenyl
2-I
4-CF3
5-Cl


I.1.631
phenyl
2-I
5-CF3
6-Cl


I.1.632
phenyl
2-I
5-CF3
3-F


I.1.633
phenyl
2-I
5-CF3
4-F


I.1.634
phenyl
2-I
4-CF3
5-F


I.1.635
phenyl
2-I
5-CF3
6-F


I.1.636
phenyl
2-I
5-CF3
3-CH3


I.1.637
phenyl
2-I
5-CF3
4-CH3


I.1.638
phenyl
2-I
4-CF3
5-CH3


I.1.639
phenyl
2-I
5-CF3
6-CH3


I.1.640
phenyl
2-I
4-CF3
5-vinyl


I.1.641
phenyl
2-I
4-CF3
6-vinyl


I.1.642
phenyl
2-I
3-Cl
4-F


I.1.643
phenyl
2-I
3-Cl
5-F


I.1.644
phenyl
2-I
3-Cl
6-F


I.1.645
phenyl
2-I
3-Cl
4-Cl


I.1.646
phenyl
2-I
3-Cl
5-Cl


I.1.647
phenyl
2-I
3-Cl
6-Cl


I.1.648
phenyl
2-I
3-Cl
4-CH3


I.1.649
phenyl
2-I
3-Cl
5-CH3


I.1.650
phenyl
2-I
3-Cl
6-CH3


I.1.651
phenyl
2-I
3-Cl
5-vinyl


I.1.652
phenyl
2-I
3-Cl
6-vinyl


I.1.653
phenyl
2-I
3-F
4-F


I.1.654
phenyl
2-I
3-F
5-F


I.1.655
phenyl
2-I
3-F
6-F


I.1.656
phenyl
2-I
3-F
4-Cl


I.1.657
phenyl
2-I
3-F
5-Cl


I.1.658
phenyl
2-I
3-F
6-Cl


I.1.659
phenyl
2-I
3-F
4-CH3


I.1.660
phenyl
2-I
3-F
5-CH3


I.1.661
phenyl
2-I
3-F
6-CH3


I.1.662
phenyl
2-I
3-F
5-vinyl


I.1.663
phenyl
2-I
3-F
6-vinyl


I.1.664
phenyl
2-I
3-CH3
4-F


I.1.665
phenyl
2-I
3-CH3
5-F


I.1.666
phenyl
2-I
3-CH3
6-F


I.1.667
phenyl
2-I
3-CH3
4-Cl


I.1.668
phenyl
2-I
3-CH3
5-Cl


I.1.669
phenyl
2-I
3-CH3
6-Cl


I.1.670
phenyl
2-I
3-CH3
4-CH3


I.1.671
phenyl
2-I
3-CH3
5-CH3


I.1.672
phenyl
2-I
3-CH3
6-CH3


I.1.673
phenyl
2-I
3-CH3
5-vinyl


I.1.674
phenyl
2-I
3-CH3
6-vinyl


I.1-675
phenyl
2-I
4-Cl
5-F


I.1.676
phenyl
2-I
4-Cl
6-F


I.1.677
phenyl
2-I
4-Cl
5-Cl


I.1.678
phenyl
2-I
4-Cl
6-Cl


I.1.679
phenyl
2-I
4-Cl
5-CH3


I.1.680
phenyl
2-I
4-Cl
6-CH3


I.1.681
phenyl
2-I
4-Cl
5-vinyl


I.1.682
phenyl
2-I
4-Cl
6-vinyl


I.1.683
phenyl
2-I
4-F
5-F


I.1.684
phenyl
2-I
4-F
6-F


I.1.685
phenyl
2-I
4-F
5-Cl


I.1.686
phenyl
2-I
4-F
6-Cl


I.1.687
phenyl
2-I
4-F
5-CH3


I.1.688
phenyl
2-I
4-F
6-CH3


I.1.689
phenyl
2-I
4-F
5-vinyl


I.1.690
phenyl
2-I
4-F
6-vinyl


I.1.691
phenyl
2-I
4-CH3
5-F


I.1.692
phenyl
2-I
4-CH3
6-F


I.1.693
phenyl
2-I
4-CH3
5-Cl


I.1.694
phenyl
2-I
4-CH3
6-Cl


I.1.695
phenyl
2-I
4-CH3
5-CH3


I.1.696
phenyl
2-I
4-CH3
6-CH3


I.1.697
phenyl
2-I
4-CH3
5-vinyl


I.1.698
phenyl
2-I
4-CH3
6-vinyl


I.1.699
phenyl
2-I
5-Cl
6-Cl


I.1.700
phenyl
2-I
5-Cl
6-F


I.1.701
phenyl
2-I
5-Cl
6-CH3


I.1.702
phenyl
2-I
5-Cl
6-vinyl


I.1.703
phenyl
2-I
5-F
6-Cl


I.1.704
phenyl
2-I
5-F
6-F


I.1.705
phenyl
2-I
5-F
6-CH3


I.1.706
phenyl
2-I
5-F
6-vinyl


I.1.707
phenyl
2-I
5-CH3
6-Cl


I.1.708
phenyl
2-I
5-CH3
6-F


I.1.709
phenyl
2-I
5-CH3
6-CH3


I.1.710
phenyl
2-I
5-CH3
6-vinyl


I.1.711
phenyl
2-I
5-vinyl
6-Cl


I.1.712
phenyl
2-I
5-vinyl
6-F


I.1.713
phenyl
2-I
5-vinyl
6-CH3


I.1.714
phenyl
2-I
5-vinyl
6-vinyl


I.1.715
phenyl
2-Br
H
H


I.1.716
phenyl
2-Br
3-Cl
H


I.1.717
phenyl
2-Br
4-Cl
H


I.1.718
phenyl
2-Br
5-Cl
H


I.1.719
phenyl
2-Br
6-Cl
H


I.1.720
phenyl
2-Br
3-F
H


I.1.721
phenyl
2-Br
4-F
H


I.1.722
phenyl
2-Br
5-F
H


I.1.723
phenyl
2-Br
6-F
H


I.1.724
phenyl
2-Br
3-CH3
H


I.1.725
phenyl
2-Br
4-CH3
H


I.1.726
phenyl
2-Br
5-CH3
H


I.1.727
phenyl
2-Br
6-CH3
H


I.1.728
phenyl
2-Br
5-vinyl
H


I.1.729
phenyl
2-Br
6-vinyl
H


I.1.730
phenyl
2-Br
5-CF3
3-Cl


I.1.731
phenyl
2-Br
5-CF3
4-Cl


I.1.732
phenyl
2-Br
4-CF3
5-Cl


I.1.733
phenyl
2-Br
5-CF3
6-Cl


I.1.734
phenyl
2-Br
5-CF3
3-F


I.1.735
phenyl
2-Br
5-CF3
4-F


I.1.736
phenyl
2-Br
4-CF3
5-F


I.1.737
phenyl
2-Br
5-CF3
6-F


I.1.738
phenyl
2-Br
5-CF3
3-CH3


I.1.739
phenyl
2-Br
5-CF3
4-CH3


I.1.740
phenyl
2-Br
4-CF3
5-CH3


I.1.741
phenyl
2-Br
5-CF3
6-CH3


I.1.742
phenyl
2-Br
4-CF3
5-vinyl


I.1.743
phenyl
2-Br
4-CF3
6-vinyl


I.1.744
phenyl
2-Br
3-Cl
4-F


I.1.745
phenyl
2-Br
3-Cl
5-F


I.1.746
phenyl
2-Br
3-Cl
6-F


I.1.747
phenyl
2-Br
3-Cl
4-Cl


I.1.748
phenyl
2-Br
3-Cl
5-Cl


I.1.749
phenyl
2-Br
3-Cl
6-Cl


I.1.750
phenyl
2-Br
3-Cl
4-CH3


I.1.751
phenyl
2-Br
3-Cl
5-CH3


I.1.752
phenyl
2-Br
3-Cl
6-CH3


I.1.753
phenyl
2-Br
3-Cl
5-vinyl


I.1.754
phenyl
2-Br
3-Cl
6-vinyl


I.1.755
phenyl
2-Br
3-F
4-F


I.1.756
phenyl
2-Br
3-F
5-F


I.1.757
phenyl
2-Br
3-F
6-F


I.1.758
phenyl
2-Br
3-F
4-Cl


I.1.759
phenyl
2-Br
3-F
5-Cl


I.1.760
phenyl
2-Br
3-F
6-Cl


I.1.761
phenyl
2-Br
3-F
4-CH3


I.1.762
phenyl
2-Br
3-F
5-CH3


I.1.763
phenyl
2-Br
3-F
6-CH3


I.1.764
phenyl
2-Br
3-F
5-vinyl


I.1.765
phenyl
2-Br
3-F
6-vinyl


I.1.766
phenyl
2-Br
3-CH3
4-F


I.1.767
phenyl
2-Br
3-CH3
5-F


I.1.768
phenyl
2-Br
3-CH3
6-F


I.1.769
phenyl
2-Br
3-CH3
4-Cl


I.1.770
phenyl
2-Br
3-CH3
5-Cl


I.1.771
phenyl
2-Br
3-CH3
6-Cl


I.1.772
phenyl
2-Br
3-CH3
4-CH3


I.1.773
phenyl
2-Br
3-CH3
5-CH3


I.1.774
phenyl
2-Br
3-CH3
6-CH3


I.1.775
phenyl
2-Br
3-CH3
5-vinyl


I.1.776
phenyl
2-Br
3-CH3
6-vinyl


I.1.777
phenyl
2-Br
4-Cl
5-F


I.1.778
phenyl
2-Br
4-Cl
6-F


I.1.779
phenyl
2-Br
4-Cl
5-Cl


I.1.780
phenyl
2-Br
4-Cl
6-Cl


I.1.781
phenyl
2-Br
4-Cl
5-CH3


I.1.782
phenyl
2-Br
4-Cl
6-CH3


I.1.783
phenyl
2-Br
4-Cl
5-vinyl


I.1.784
phenyl
2-Br
4-Cl
6-vinyl


I.1.785
phenyl
2-Br
4-F
5-F


I.1.786
phenyl
2-Br
4-F
6-F


I.1.787
phenyl
2-Br
4-F
5-Cl


I.1.788
phenyl
2-Br
4-F
6-Cl


I.1.789
phenyl
2-Br
4-F
5-CH3


I.1.790
phenyl
2-Br
4-F
6-CH3


I.1.791
phenyl
2-Br
4-F
5-vinyl


I.1.792
phenyl
2-Br
4-F
6-vinyl


I.1.793
phenyl
2-Br
4-CH3
5-F


I.1.794
phenyl
2-Br
4-CH3
6-F


I.1.795
phenyl
2-Br
4-CH3
5-Cl


I.1.796
phenyl
2-Br
4-CH3
6-Cl


I.1.797
phenyl
2-Br
4-CH3
5-CH3


I.1.798
phenyl
2-Br
4-CH3
6-CH3


I.1.799
phenyl
2-Br
4-CH3
5-vinyl


I.1.800
phenyl
2-Br
4-CH3
6-vinyl


I.1.801
phenyl
2-Br
5-Cl
6-Cl


I.1.802
phenyl
2-Br
5-Cl
6-F


I.1.803
phenyl
2-Br
5-Cl
6-CH3


I.1.804
phenyl
2-Br
5-Cl
6-vinyl


I.1.805
phenyl
2-Br
5-F
6-Cl


I.1.806
phenyl
2-Br
5-F
6-F


I.1.807
phenyl
2-Br
5-F
6-CH3


I.1.808
phenyl
2-Br
5-F
6-vinyl


I.1.809
phenyl
2-Br
5-CH3
6-Cl


I.1.810
phenyl
2-Br
5-CH3
6-F


I.1.811
phenyl
2-Br
5-CH3
6-CH3


I.1.812
phenyl
2-Br
5-CH3
6-vinyl


I.1.813
phenyl
2-Br
5-vinyl
6-Cl


I.1.814
phenyl
2-Br
5-vinyl
6-F


I.1.815
phenyl
2-Br
5-vinyl
6-CH3


I.1.816
phenyl
2-Br
5-vinyl
6-vinyl


I.1.817
phenyl
2-Cl
H
H


I.1.818
phenyl
2-Cl
3-Cl
H


I.1.819
phenyl
2-Cl
4-Cl
H


I.1.820
phenyl
2-Cl
5-Cl
H


I.1.821
phenyl
2-Cl
6-Cl
H


I.1.822
phenyl
2-Cl
3-F
H


I.1.823
phenyl
2-Cl
4-F
H


I.1.824
phenyl
2-Cl
5-F
H


I.1.825
phenyl
2-Cl
6-F
H


I.1.826
phenyl
2-Cl
3-CH3
H


I.1.827
phenyl
2-Cl
4-CH3
H


I.1.828
phenyl
2-Cl
5-CH3
H


I.1.829
phenyl
2-Cl
6-CH3
H


I.1.830
phenyl
2-Cl
5-vinyl
H


I.1.831
phenyl
2-Cl
6-vinyl
H


I.1.832
phenyl
2-Cl
5-CF3
3-Cl


I.1.833
phenyl
2-Cl
5-CF3
4-Cl


I.1.834
phenyl
2-Cl
4-CF3
5-Cl


I.1.835
phenyl
2-Cl
5-CF3
6-Cl


I.1.836
phenyl
2-Cl
5-CF3
3-F


I.1.837
phenyl
2-Cl
5-CF3
4-F


I.1.838
phenyl
2-Cl
4-CF3
5-F


I.1.839
phenyl
2-Cl
5-CF3
6-F


I.1.840
phenyl
2-Cl
5-CF3
3-CH3


I.1.841
phenyl
2-Cl
5-CF3
4-CH3


I.1.842
phenyl
2-Cl
4-CF3
5-CH3


I.1.843
phenyl
2-Cl
5-CF3
6-CH3


I.1.844
phenyl
2-Cl
4-CF3
5-vinyl


I.1.845
phenyl
2-Cl
4-CF3
6-vinyl


I.1.846
phenyl
2-Cl
3-Cl
4-F


I.1.847
phenyl
2-Cl
3-Cl
5-F


I.1.848
phenyl
2-Cl
3-Cl
6-F


I.1.849
phenyl
2-Cl
3-Cl
4-Cl


I.1.850
phenyl
2-Cl
3-Cl
5-Cl


I.1.851
phenyl
2-Cl
3-Cl
6-Cl


I.1.852
phenyl
2-Cl
3-Cl
4-CH3


I.1.853
phenyl
2-Cl
3-Cl
5-CH3


I.1.854
phenyl
2-Cl
3-Cl
6-CH3


I.1.855
phenyl
2-Cl
3-Cl
5-vinyl


I.1.856
phenyl
2-Cl
3-Cl
6-vinyl


I.1.857
phenyl
2-Cl
3-F
4-F


I.1.858
phenyl
2-Cl
3-F
5-F


I.1.859
phenyl
2-Cl
3-F
6-F


I.1.860
phenyl
2-Cl
3-F
4-Cl


I.1.861
phenyl
2-Cl
3-F
5-Cl


I.1.862
phenyl
2-Cl
3-F
6-Cl


I.1.863
phenyl
2-Cl
3-F
4-CH3


I.1.864
phenyl
2-Cl
3-F
5-CH3


I.1.865
phenyl
2-Cl
3-F
6-CH3


I.1.866
phenyl
2-Cl
3-F
5-vinyl


I.1.867
phenyl
2-Cl
3-F
6-vinyl


I.1.868
phenyl
2-Cl
3-CH3
4-F


I.1.869
phenyl
2-Cl
3-CH3
5-F


I.1.870
phenyl
2-Cl
3-CH3
6-F


I.1.871
phenyl
2-Cl
3-CH3
4-Cl


I.1.872
phenyl
2-Cl
3-CH3
5-Cl


I.1.873
phenyl
2-Cl
3-CH3
6-Cl


I.1.874
phenyl
2-Cl
3-CH3
4-CH3


I.1.875
phenyl
2-Cl
3-CH3
5-CH3


I.1.876
phenyl
2-Cl
3-CH3
6-CH3


I.1.877
phenyl
2-Cl
3-CH3
5-vinyl


I.1.878
phenyl
2-Cl
3-CH3
6-vinyl


I.1.879
phenyl
2-Cl
4-Cl
5-F


I.1.880
phenyl
2-Cl
4-Cl
6-F


I.1.881
phenyl
2-Cl
4-Cl
5-Cl


I.1.882
phenyl
2-Cl
4-Cl
6-Cl


I.1.883
phenyl
2-Cl
4-Cl
5-CH3


I.1.884
phenyl
2-Cl
4-Cl
6-CH3


I.1.885
phenyl
2-Cl
4-Cl
5-vinyl


I.1.886
phenyl
2-Cl
4-Cl
6-vinyl


I.1.887
phenyl
2-Cl
4-F
5-F


I.1.888
phenyl
2-Cl
4-F
6-F


I.1.889
phenyl
2-Cl
4-F
5-Cl


I.1.890
phenyl
2-Cl
4-F
6-Cl


I.1.891
phenyl
2-Cl
4-F
5-CH3


I.1.892
phenyl
2-Cl
4-F
6-CH3


I.1.893
phenyl
2-Cl
4-F
5-vinyl


I.1.894
phenyl
2-Cl
4-F
6-vinyl


I.1.895
phenyl
2-Cl
4-CH3
5-F


I.1.896
phenyl
2-Cl
4-CH3
6-F


I.1.897
phenyl
2-Cl
4-CH3
5-Cl


I.1.898
phenyl
2-Cl
4-CH3
6-Cl


I.1.899
phenyl
2-Cl
4-CH3
5-CH3


I.1.900
phenyl
2-Cl
4-CH3
6-CH3


I.1.901
phenyl
2-Cl
4-CH3
5-vinyl


I.1.902
phenyl
2-Cl
4-CH3
6-vinyl


I.1.903
phenyl
2-Cl
5-Cl
6-Cl


I.1.904
phenyl
2-Cl
5-Cl
6-F


I.1.905
phenyl
2-Cl
5-Cl
6-CH3


I.1.906
phenyl
2-Cl
5-Cl
6-vinyl


I.1.907
phenyl
2-Cl
5-F
6-Cl


I.1.908
phenyl
2-Cl
5-F
6-F


I.1.909
phenyl
2-Cl
5-F
6-CH3


I.1.910
phenyl
2-Cl
5-F
6-vinyl


I.1.911
phenyl
2-Cl
5-CH3
6-Cl


I.1.912
phenyl
2-Cl
5-CH3
6-F


I.1.913
phenyl
2-Cl
5-CH3
6-CH3


I.1.914
phenyl
2-Cl
5-CH3
6-vinyl


I.1.915
phenyl
2-Cl
5-vinyl
6-Cl


I.1.916
phenyl
2-Cl
5-vinyl
6-F


I.1.917
phenyl
2-Cl
5-vinyl
6-CH3


I.1.918
phenyl
2-Cl
5-vinyl
6-vinyl


I.1.919
phenyl
2-COOCH2CH3
H
H


I.1.920
phenyl
2-COOCH2CH3
3-Cl
H


I.1.921
phenyl
2-COOCH2CH3
4-Cl
H


I.1.922
phenyl
2-COOCH2CH3
5-Cl
H


I.1.923
phenyl
2-COOCH2CH3
6-Cl
H


I.1.924
phenyl
2-COOCH2CH3
3-F
H


I.1.925
phenyl
2-COOCH2CH3
4-F
H


I.1.926
phenyl
2-COOCH2CH3
5-F
H


I.1.927
phenyl
2-COOCH2CH3
6-F
H


I.1.928
phenyl
2-COOCH2CH3
3-CH3
H


I.1.929
phenyl
2-COOCH2CH3
4-CH3
H


I.1.930
phenyl
2-COOCH2CH3
5-CH3
H


I.1.931
phenyl
2-COOCH2CH3
6-CH3
H


I.1.932
phenyl
2-COOCH2CH3
5-vinyl
H


I.1.933
phenyl
2-COOCH2CH3
6-vinyl
H


I.1.934
phenyl
2-COOCH2CH3
5-CF3
3-Cl


I.1.935
phenyl
2-COOCH2CH3
5-CF3
4-Cl


I.1.936
phenyl
2-COOCH2CH3
4-CF3
5-Cl


I.1.937
phenyl
2-COOCH2CH3
5-CF3
6-Cl


I.1.938
phenyl
2-COOCH2CH3
5-CF3
3-F


I.1.939
phenyl
2-COOCH2CH3
5-CF3
4-F


I.1.940
phenyl
2-COOCH2CH3
4-CF3
5-F


I.1.941
phenyl
2-COOCH2CH3
5-CF3
6-F


I.1.942
phenyl
2-COOCH2CH3
5-CF3
3-CH3


I.1.943
phenyl
2-COOCH2CH3
5-CF3
4-CH3


I.1.944
phenyl
2-COOCH2CH3
4-CF3
5-CH3


I.1.945
phenyl
2-COOCH2CH3
5-CF3
6-CH3


I.1.946
phenyl
2-COOCH2CH3
4-CF3
5-vinyl


I.1.947
phenyl
2-COOCH2CH3
4-CF3
6-vinyl


I.1.948
phenyl
2-COOCH2CH3
3-Cl
4-F


I.1.949
phenyl
2-COOCH2CH3
3-Cl
5-F


I.1.950
phenyl
2-COOCH2CH3
3-Cl
6-F


I.1.951
phenyl
2-COOCH2CH3
3-Cl
4-Cl


I.1.952
phenyl
2-COOCH2CH3
3-Cl
5-Cl


I.1.953
phenyl
2-COOCH2CH3
3-Cl
6-Cl


I.1.954
phenyl
2-COOCH2CH3
3-Cl
4-CH3


I.1.955
phenyl
2-COOCH2CH3
3-Cl
5-CH3


I.1.956
phenyl
2-COOCH2CH3
3-Cl
6-CH3


I.1.957
phenyl
2-COOCH2CH3
3-Cl
5-vinyl


I.1.958
phenyl
2-COOCH2CH3
3-Cl
6-vinyl


I.1.959
phenyl
2-COOCH2CH3
3-F
4-F


I.1.960
phenyl
2-COOCH2CH3
3-F
5-F


I.1.961
phenyl
2-COOCH2CH3
3-F
6-F


I.1.962
phenyl
2-COOCH2CH3
3-F
4-Cl


I.1.963
phenyl
2-COOCH2CH3
3-F
5-Cl


I.1.964
phenyl
2-COOCH2CH3
3-F
6-Cl


I.1.965
phenyl
2-COOCH2CH3
3-F
4-CH3


I.1.966
phenyl
2-COOCH2CH3
3-F
5-CH3


I.1.967
phenyl
2-COOCH2CH3
3-F
6-CH3


I.1.968
phenyl
2-COOCH2CH3
3-F
5-vinyl


I.1.969
phenyl
2-COOCH2CH3
3-F
6-vinyl


I.1.970
phenyl
2-COOCH2CH3
3-CH3
4-F


I.1.971
phenyl
2-COOCH2CH3
3-CH3
5-F


I.1.972
phenyl
2-COOCH2CH3
3-CH3
6-F


I.1.973
phenyl
2-COOCH2CH3
3-CH3
4-Cl


I.1.974
phenyl
2-COOCH2CH3
3-CH3
5-Cl


I.1.975
phenyl
2-COOCH2CH3
3-CH3
6-Cl


I.1.976
phenyl
2-COOCH2CH3
3-CH3
4-CH3


I.1.977
phenyl
2-COOCH2CH3
3-CH3
5-CH3


I.1.978
phenyl
2-COOCH2CH3
3-CH3
6-CH3


I.1.979
phenyl
2-COOCH2CH3
3-CH3
5-vinyl


I.1.980
phenyl
2-COOCH2CH3
3-CH3
6-vinyl


I.1.981
phenyl
2-COOCH2CH3
4-Cl
5-F


I.1.982
phenyl
2-COOCH2CH3
4-Cl
6-F


I.1.983
phenyl
2-COOCH2CH3
4-Cl
5-Cl


I.1.984
phenyl
2-COOCH2CH3
4-Cl
6-Cl


I.1.985
phenyl
2-COOCH2CH3
4-Cl
5-CH3


I.1.986
phenyl
2-COOCH2CH3
4-Cl
6-CH3


I.1.987
phenyl
2-COOCH2CH3
4-Cl
5-vinyl


I.1.988
phenyl
2-COOCH2CH3
4-Cl
6-vinyl


I.1.989
phenyl
2-COOCH2CH3
4-F
5-F


I.1.990
phenyl
2-COOCH2CH3
4-F
6-F


I.1.991
phenyl
2-COOCH2CH3
4-F
5-Cl


I.1.992
phenyl
2-COOCH2CH3
4-F
6-Cl


I.1.993
phenyl
2-COOCH2CH3
4-F
5-CH3


I.1.994
phenyl
2-COOCH2CH3
4-F
6-CH3


I.1.995
phenyl
2-COOCH2CH3
4-F
5-vinyl


I.1.996
phenyl
2-COOCH2CH3
4-F
6-vinyl


I.1.997
phenyl
2-COOCH2CH3
4-CH3
5-F


I.1.998
phenyl
2-COOCH2CH3
4-CH3
6-F


I.1.999
phenyl
2-COOCH2CH3
4-CH3
5-Cl


I.1.1000
phenyl
2-COOCH2CH3
4-CH3
6-Cl


I.1.1001
phenyl
2-COOCH2CH3
4-CH3
5-CH3


I.1.1002
phenyl
2-COOCH2CH3
4-CH3
6-CH3


I.1.1003
phenyl
2-COOCH2CH3
4-CH3
5-vinyl


I.1.1004
phenyl
2-COOCH2CH3
4-CH3
6-vinyl


I.1.1005
phenyl
2-COOCH2CH3
5-Cl
6-Cl


I.1.1006
phenyl
2-COOCH2CH3
5-Cl
6-F


I.1.1007
phenyl
2-COOCH2CH3
5-Cl
6-CH3


I.1.1008
phenyl
2-COOCH2CH3
5-Cl
6-vinyl


I.1.1009
phenyl
2-COOCH2CH3
5-F
6-Cl


I.1.1010
phenyl
2-COOCH2CH3
5-F
6-F


I.1.1011
phenyl
2-COOCH2CH3
5-F
6-CH3


I.1.1012
phenyl
2-COOCH2CH3
5-F
6-vinyl


I.1.1013
phenyl
2-COOCH2CH3
5-CH3
6-Cl


I.1.1014
phenyl
2-COOCH2CH3
5-CH3
6-F


I.1.1015
phenyl
2-COOCH2CH3
5-CH3
6-CH3


I.1.1016
phenyl
2-COOCH2CH3
5-CH3
6-vinyl


I.1.1017
phenyl
2-COOCH2CH3
5-vinyl
6-Cl


I.1.1018
phenyl
2-COOCH2CH3
5-vinyl
6-F


I.1.1019
phenyl
2-COOCH2CH3
5-vinyl
6-CH3


I.1.1020
phenyl
2-COOCH2CH3
5-vinyl
6-vinyl


I.1.1021
phenyl
2-COOCH2CH3
H
H


I.1.1022
phenyl
2-COOCH2CH3
3-Cl
H


I.1.1023
phenyl
2-COOCH2CH3
4-Cl
H


I.1.1024
phenyl
2-COOCH2CH3
5-Cl
H


I.1.1025
phenyl
2-COOCH2CH3
6-Cl
H


I.1.1026
phenyl
2-COOCH2CH3
3-F
H


I.1.1027
phenyl
2-COOCH2CH3
4-F
H


I.1.1028
phenyl
2-COOCH2CH3
5-F
H


I.1.1029
phenyl
2-COOCH2CH3
6-F
H


I.1.1030
phenyl
2-COOCH2CH3
3-CH3
H


I.1.1031
phenyl
2-COOCH2CH3
4-CH3
H


I.1.1032
phenyl
2-COOCH2CH3
5-CH3
H


I.1.1033
phenyl
2-COOCH2CH3
6-CH3
H


I.1.1034
phenyl
2-COOCH2CH3
5-vinyl
H


I.1.1035
phenyl
2-COOCH2CH3
6-vinyl
H


I.1.1036
phenyl
2-COOCH2CH3
5-CF3
3-Cl


I.1.1037
phenyl
2-COOCH2CH3
5-CF3
4-Cl


I.1.1038
phenyl
2-COOCH2CH3
4-CF3
5-Cl


I.1.1039
phenyl
2-COOCH2CH3
5-CF3
6-Cl


I.1.1040
phenyl
2-COOCH2CH3
5-CF3
3-F


I.1.1041
phenyl
2-COOCH2CH3
5-CF3
4-F


I.1.1042
phenyl
2-COOCH2CH3
4-CF3
5-F


I.1.1043
phenyl
2-COOCH2CH3
5-CF3
6-F


I.1.1044
phenyl
2-COOCH2CH3
5-CF3
3-CH3


I.1.1045
phenyl
2-COOCH2CH3
5-CF3
4-CH3


I.1.1046
phenyl
2-COOCH2CH3
4-CF3
5-CH3


I.1.1047
phenyl
2-COOCH2CH3
5-CF3
6-CH3


I.1.1048
phenyl
2-COOCH2CH3
5-CF3
5-vinyl


I.1.1049
phenyl
2-COOCH2CH3
4-CF3
6-vinyl


I.1.1050
phenyl
2-COOCH2CH3
3-Cl
4-F


I.1.1051
phenyl
2-COOCH2CH3
3-Cl
5-F


I.1.1052
phenyl
2-COOCH2CH3
3-Cl
6-F


I.1.1053
phenyl
2-COOCH2CH3
3-Cl
4-Cl


I.1.1054
phenyl
2-COOCH2CH3
3-Cl
5-Cl


I.1.1055
phenyl
2-COOCH2CH3
3-Cl
6-Cl


I.1.1056
phenyl
2-COOCH2CH3
3-Cl
4-CH3


I.1.1057
phenyl
2-COOCH2CH3
3-Cl
5-CH3


I.1.1058
phenyl
2-COOCH2CH3
3-Cl
6-CH3


I.1.1059
phenyl
2-COOCH2CH3
3-Cl
5-vinyl


I.1.1060
phenyl
2-COOCH2CH3
3-Cl
6-vinyl


I.1.1061
phenyl
2-COOCH2CH3
3-F
4-F


I.1.1062
phenyl
2-COOCH2CH3
3-F
5-F


I.1.1063
phenyl
2-COOCH2CH3
3-F
6-F


I.1.1064
phenyl
2-COOCH2CH3
3-F
4-Cl


I.1.1065
phenyl
2-COOCH2CH3
3-F
5-Cl


I.1.1066
phenyl
2-COOCH2CH3
3-F
6-Cl


I.1.1067
phenyl
2-COOCH2CH3
3-F
4-CH3


I.1.1068
phenyl
2-COOCH2CH3
3-F
5-CH3


I.1.1069
phenyl
2-COOCH2CH3
3-F
6-CH3


I.1.1070
phenyl
2-COOCH2CH3
3-F
5-vinyl


I.1.1071
phenyl
2-COOCH2CH3
3-F
6-vinyl


I.1.1072
phenyl
2-COOCH2CH3
3-CH3
4-F


I.1.1073
phenyl
2-COOCH2CH3
3-CH3
5-F


I.1.1074
phenyl
2-COOCH2CH3
3-CH3
6-F


I.1.1075
phenyl
2-COOCH2CH3
3-CH3
4-Cl


I.1.1076
phenyl
2-COOCH2CH3
3-CH3
5-Cl


I.1.1077
phenyl
2-COOCH2CH3
3-CH3
6-Cl


I.1.1078
phenyl
2-COOCH2CH3
3-CH3
4-CH3


I.1.1079
phenyl
2-COOCH2CH3
3-CH3
5-CH3


I.1.1080
phenyl
2-COOCH2CH3
3-CH3
6-CH3


I.1.1081
phenyl
2-COOCH2CH3
3-CH3
5-vinyl


I.1.1082
phenyl
2-COOCH2CH3
3-CH3
6-vinyl


I.1.1083
phenyl
2-COOCH2CH3
4-Cl
5-F


I.1.1084
phenyl
2-COOCH2CH3
4-Cl
6-F


I.1.1085
phenyl
2-COOCH2CH3
4-Cl
5-Cl


I.1.1086
phenyl
2-COOCH2CH3
4-Cl
6-Cl


I.1.1087
phenyl
2-COOCH2CH3
4-Cl
5-CH3


I.1.1088
phenyl
2-COOCH2CH3
4-Cl
6-CH3


I.1.1089
phenyl
2-COOCH2CH3
4-Cl
5-vinyl


I.1.1090
phenyl
2-COOCH2CH3
4-Cl
6-vinyl


I.1.1091
phenyl
2-COOCH2CH3
4-F
5-F


I.1.1092
phenyl
2-COOCH2CH3
4-F
6-F


I.1.1093
phenyl
2-COOCH2CH3
4-F
5-Cl


I.1.1094
phenyl
2-COOCH2CH3
4-F
6-Cl


I.1.1095
phenyl
2-COOCH2CH3
4-F
5-CH3


I.1.1096
phenyl
2-COOCH2CH3
4-F
6-CH3


I.1.1097
phenyl
2-COOCH2CH3
4-F
5-vinyl


I.1.1098
phenyl
2-COOCH2CH3
4-F
6-vinyl


I.1.1099
phenyl
2-COOCH2CH3
4-CH3
5-F


I.1.1100
phenyl
2-COOCH2CH3
4-CH3
6-F


I.1.1101
phenyl
2-COOCH2CH3
4-CH3
5-Cl


I.1.1102
phenyl
2-COOCH2CH3
4-CH3
6-Cl


I.1.1103
phenyl
2-COOCH2CH3
4-CH3
5-CH3


I.1.1104
phenyl
2-COOCH2CH3
4-CH3
6-CH3


I.1.1105
phenyl
2-COOCH2CH3
4-CH3
5-vinyl


I.1.1106
phenyl
2-COOCH2CH3
4-CH3
6-vinyl


I.1.1107
phenyl
2-COOCH2CH3
5-Cl
6-Cl


I.1.1108
phenyl
2-COOCH2CH3
5-Cl
6-F


I.1.1109
phenyl
2-COOCH2CH3
5-Cl
6-CH3


I.1.1110
phenyl
2-COOCH2CH3
5-Cl
6-vinyl


I.1.1111
phenyl
2-COOCH2CH3
5-F
6-Cl


I.1.1112
phenyl
2-COOCH2CH3
5-F
6-F


I.1.1113
phenyl
2-COOCH2CH3
5-F
6-CH3


I.1.1114
phenyl
2-COOCH2CH3
5-F
6-vinyl


I.1.1115
phenyl
2-COOCH2CH3
5-CH3
6-Cl


I.1.1116
phenyl
2-COOCH2CH3
5-CH3
6-F


I.1.1117
phenyl
2-COOCH2CH3
5-CH3
6-CH3


I.1.1118
phenyl
2-COOCH2CH3
5-CH3
6-vinyl


I.1.1119
phenyl
2-COOCH2CH3
5-vinyl
6-Cl


I.1.1120
phenyl
2-COOCH2CH3
5-vinyl
6-F


I.1.1121
phenyl
2-COOCH2CH3
5-vinyl
6-CH3


I.1.1122
phenyl
2-COOCH2CH3
5-vinyl
6-vinyl


I.1.1123
pyridin-2-yl
3-NO2
4-Cl
5-F


I.1.1124
pyridin-2-yl
3-NO2
4-Cl
H


I.1.1125
pyridin-2-yl
3-NO2
5-Cl
H


I.1.1126
pyridin-2-yl
3-NO2
6-Cl
H


I.1.1127
pyridin-2-yl
3-NO2
4-F
H


I.1.1128
pyridin-2-yl
3-NO2
5-F
H


I.1.1129
pyridin-2-yl
3-NO2
6-F
H


I.1.1130
pyridin-2-yl
3-NO2
4-Br
H


I.1.1131
pyridin-2-yl
3-NO2
5-Br
H


I.1.1132
pyridin-2-yl
3-NO2
6-Br
H


I.1.1133
pyridin-2-yl
3-NO2
4-CH3
H


I.1.1134
pyridin-2-yl
3-NO2
5-CH3
H


I.1.1135
pyridin-2-yl
3-NO2
6-CH3
H


I.1.1136
pyridin-2-yl
3-NO2
4-CF3
H


I.1.1137
pyridin-2-yl
3-NO2
5-CF3
H


I.1.1138
pyridin-2-yl
3-NO2
6-CF3
H


I.1.1139
pyridin-2-yl
3-NO2
4-vinyl
H


I.1.1140
pyridin-2-yl
3-NO2
5-vinyl
H


I.1.1141
pyridin-2-yl
3-NO2
6-vinyl
H


I.1.1142
pyridin-2-yl
3-NO2
4-Cl
6-F


I.1.1143
pyridin-2-yl
3-NO2
5-Cl
6-F


I.1.1144
pyridin-2-yl
3-CN
4-Cl
5-F


I.1.1145
pyridin-2-yl
3-CN
4-Cl
H


I.1.1146
pyridin-2-yl
3-CN
5-Cl
H


I.1.1147
pyridin-2-yl
3-CN
6-Cl
H


I.1.1148
pyridin-2-yl
3-CN
4-F
H


I.1.1149
pyridin-2-yl
3-CN
5-F
H


I.1.1150
pyridin-2-yl
3-CN
6-F
H


I.1.1151
pyridin-2-yl
3-CN
4-Br
H


I.1.1152
pyridin-2-yl
3-CN
5-Br
H


I.1.1153
pyridin-2-yl
3-CN
6-Br
H


I.1.1154
pyridin-2-yl
3-CN
4-CH3
H


I.1.1155
pyridin-2-yl
3-CN
5-CH3
H


I.1.1156
pyridin-2-yl
3-CN
6-CH3
H


I.1.1157
pyridin-2-yl
3-CN
4-CF3
H


I.1.1158
pyridin-2-yl
3-CN
5-CF3
H


I.1.1159
pyridin-2-yl
3-CN
6-CF3
H


I.1.1160
pyridin-2-yl
3-CN
4-vinyl
H


I.1.1161
pyridin-2-yl
3-CN
5-vinyl
H


I.1.1162
pyridin-2-yl
3-CN
6-vinyl
H


I.1.1163
pyridin-2-yl
3-CN
4-Cl
6-F


I.1.1164
pyridin-2-yl
3-CN
5-Cl
6-F


I.1.1165
pyridin-2-yl
3-Br
4-Cl
5-F


I.1.1166
pyridin-2-yl
3-Br
4-Cl
H


I.1.1167
pyridin-2-yl
3-Br
5-Cl
H


I.1.1168
pyridin-2-yl
3-Br
6-Cl
H


I.1.1169
pyridin-2-yl
3-Br
4-F
H


I.1.1170
pyridin-2-yl
3-Br
5-F
H


I.1.1171
pyridin-2-yl
3-Br
6-F
H


I.1.1172
pyridin-2-yl
3-Br
4-Br
H


I.1.1173
pyridin-2-yl
3-Br
5-Br
H


I.1.1174
pyridin-2-yl
3-Br
6-Br
H


I.1.1175
pyridin-2-yl
3-Br
4-CH3
H


I.1.1176
pyridin-2-yl
3-Br
5-CH3
H


I.1.1177
pyridin-2-yl
3-Br
6-CH3
H


I.1.1178
pyridin-2-yl
3-Br
4-CF3
H


I.1.1179
pyridin-2-yl
3-Br
5-CF3
H


I.1.1180
pyridin-2-yl
3-Br
6-CF3
H


I.1.1181
pyridin-2-yl
3-Br
4-vinyl
H


I.1.1182
pyridin-2-yl
3-Br
5-vinyl
H


I.1.1183
pyridin-2-yl
3-Br
6-vinyl
H


I.1.1184
pyridin-2-yl
3-Br
4-Cl
6-F


I.1.1185
pyridin-2-yl
3-Br
5-Cl
6-F


I.1.1186
pyridin-2-yl
3-Cl
4-Cl
5-F


I.1.1187
pyridin-2-yl
3-Cl
4-Cl
H


I.1.1188
pyridin-2-yl
3-Cl
5-Cl
H


I.1.1189
pyridin-2-yl
3-Cl
6-Cl
H


I.1.1190
pyridin-2-yl
3-Cl
4-F
H


I.1.1191
pyridin-2-yl
3-Cl
5-F
H


I.1.1192
pyridin-2-yl
3-Cl
6-F
H


I.1.1193
pyridin-2-yl
3-Cl
4-Br
H


I.1.1194
pyridin-2-yl
3-Cl
5-Br
H


I.1.1195
pyridin-2-yl
3-Cl
6-Br
H


I.1.1196
pyridin-2-yl
3-Cl
4-CH3
H


I.1.1197
pyridin-2-yl
3-Cl
5-CH3
H


I.1.1198
pyridin-2-yl
3-Cl
6-CH3
H


I.1.1199
pyridin-2-yl
3-Cl
4-CF3
H


I.1.1200
pyridin-2-yl
3-Cl
5-CF3
H


I.1.1201
pyridin-2-yl
3-Cl
6-CF3
H


I.1.1202
pyridin-2-yl
3-Cl
4-vinyl
H


I.1.1203
pyridin-2-yl
3-Cl
5-vinyl
H


I.1.1204
pyridin-2-yl
3-Cl
6-vinyl
H


I.1.1205
pyridin-2-yl
3-Cl
4-Cl
6-F


I.1.1206
pyridin-2-yl
3-Cl
5-Cl
6-F


I.1.1207
pyridin-2-yl
3-ethynyl
4-Cl
5-F


I.1.1208
pyridin-2-yl
3-ethynyl
4-Cl
H


I.1.1209
pyridin-2-yl
3-ethynyl
5-Cl
H


I.1.1210
pyridin-2-yl
3-ethynyl
6-Cl
H


I.1.1211
pyridin-2-yl
3-ethynyl
4-F
H


I.1.1212
pyridin-2-yl
3-ethynyl
5-F
H


I.1.1213
pyridin-2-yl
3-ethynyl
6-F
H


I.1.1214
pyridin-2-yl
3-ethynyl
4-Br
H


I.1.1215
pyridin-2-yl
3-ethynyl
5-Br
H


I.1.1216
pyridin-2-yl
3-ethynyl
6-Br
H


I.1.1217
pyridin-2-yl
3-ethynyl
4-CH3
H


I.1.1218
pyridin-2-yl
3-ethynyl
5-CH3
H


I.1.1219
pyridin-2-yl
3-ethynyl
6-CH3
H


I.1.1220
pyridin-2-yl
3-ethynyl
4-CF3
H


I.1.1221
pyridin-2-yl
3-ethynyl
5-CF3
H


I.1.1222
pyridin-2-yl
3-ethynyl
6-CF3
H


I.1.1223
pyridin-2-yl
3-ethynyl
4-vinyl
H


I.1.1224
pyridin-2-yl
3-ethynyl
5-vinyl
H


I.1.1225
pyridin-2-yl
3-ethynyl
6-vinyl
H


I.1.1226
pyridin-2-yl
3-ethynyl
4-Cl
6-F


I.1.1227
pyridin-2-yl
3-ethynyl
5-Cl
6-F


I.1.1228
pyridin-2-yl
3-I
4-Cl
5-F


I.1.1229
pyridin-2-yl
3-I
4-Cl
H


I.1.1230
pyridin-2-yl
3-I
5-Cl
H


I.1.1231
pyridin-2-yl
3-I
6-Cl
H


I.1.1232
pyridin-2-yl
3-I
4-F
H


I.1.1233
pyridin-2-yl
3-I
5-F
H


I.1.1234
pyridin-2-yl
3-I
6-F
H


I.1.1235
pyridin-2-yl
3-I
4-Br
H


I.1.1236
pyridin-2-yl
3-I
5-Br
H


I.1.1237
pyridin-2-yl
3-I
6-Br
H


I.1.1238
pyridin-2-yl
3-I
4-CH3
H


I.1.1239
pyridin-2-yl
3-I
5-CH3
H


I.1.1240
pyridin-2-yl
3-I
6-CH3
H


I.1.1241
pyridin-2-yl
3-I
4-CF3
H


I.1.1242
pyridin-2-yl
3-I
5-CF3
H


I.1.1243
pyridin-2-yl
3-I
6-CF3
H


I.1.1244
pyridin-2-yl
3-I
4-vinyl
H


I.1.1245
pyridin-2-yl
3-I
5-vinyl
H


I.1.1246
pyridin-2-yl
3-I
6-vinyl
H


I.1.1247
pyridin-2-yl
3-I
4-Cl
6-F


I.1.1248
pyridin-2-yl
3-I
5-Cl
6-F


I.1.1249
pyridin-2-yl
3-COOH
4-Cl
5-F


I.1.1250
pyridin-2-yl
3-COOH
4-Cl
H


I.1.1251
pyridin-2-yl
3-COOH
5-Cl
H


I.1.1252
pyridin-2-yl
3-COOH
6-Cl
H


I.1.1253
pyridin-2-yl
3-COOH
4-F
H


I.1.1254
pyridin-2-yl
3-COOH
5-F
H


I.1.1255
pyridin-2-yl
3-COOH
6-F
H


I.1.1256
pyridin-2-yl
3-COOH
4-Br
H


I.1.1257
pyridin-2-yl
3-COOH
5-Br
H


I.1.1258
pyridin-2-yl
3-COOH
6-Br
H


I.1.1259
pyridin-2-yl
3-COOH
4-CH3
H


I.1.1260
pyridin-2-yl
3-COOH
5-CH3
H


I.1.1261
pyridin-2-yl
3-COOH
6-CH3
H


I.1.1262
pyridin-2-yl
3-COOH
4-CF3
H


I.1.1263
pyridin-2-yl
3-COOH
5-CF3
H


I.1.1264
pyridin-2-yl
3-COOH
6-CF3
H


I.1.1265
pyridin-2-yl
3-COOH
4-vinyl
H


I.1.1266
pyridin-2-yl
3-COOH
5-vinyl
H


I.1.1267
pyridin-2-yl
3-COOH
6-vinyl
H


I.1.1268
pyridin-2-yl
3-COOH
4-Cl
6-F


I.1.1269
pyridin-2-yl
3-COOH
5-Cl
6-F


I.1.1270
pyridin-2-yl
3-COOCH3
4-Cl
5-F


I.1.1271
pyridin-2-yl
3-COOCH3
4-Cl
H


I.1.1272
pyridin-2-yl
3-COOCH3
5-Cl
H


I.1.1273
pyridin-2-yl
3-COOCH3
6-Cl
H


I.1.1274
pyridin-2-yl
3-COOCH3
4-F
H


I.1.1275
pyridin-2-yl
3-COOCH3
5-F
H


I.1.1276
pyridin-2-yl
3-COOCH3
6-F
H


I.1.1277
pyridin-2-yl
3-COOCH3
4-Br
H


I.1.1278
pyridin-2-yl
3-COOCH3
5-Br
H


I.1.1279
pyridin-2-yl
3-COOCH3
6-Br
H


I.1.1280
pyridin-2-yl
3-COOCH3
4-CH3
H


I.1.1281
pyridin-2-yl
3-COOCH3
5-CH3
H


I.1.1282
pyridin-2-yl
3-COOCH3
6-CH3
H


I.1.1283
pyridin-2-yl
3-COOCH3
4-CF3
H


I.1.1284
pyridin-2-yl
3-COOCH3
5-CF3
H


I.1.1285
pyridin-2-yl
3-COOCH3
6-CF3
H


I.1.1286
pyridin-2-yl
3-COOCH3
4-vinyl
H


I.1.1287
pyridin-2-yl
3-COOCH3
5-vinyl
H


I.1.1288
pyridin-2-yl
3-COOCH3
6-vinyl
H


I.1.1289
pyridin-2-yl
3-COOCH3
4-Cl
6-F


I.1.1290
pyridin-2-yl
3-COOCH3
5-Cl
6-F


I.1.1291
pyridin-2-yl
3-COOCH2CH3
4-Cl
5-F


I.1.1292
pyridin-2-yl
3-COOCH2CH3
4-Cl
H


I.1.1293
pyridin-2-yl
3-COOCH2CH3
5-Cl
H


I.1.1294
pyridin-2-yl
3-COOCH2CH3
6-Cl
H


I.1.1295
pyridin-2-yl
3-COOCH2CH3
4-F
H


I.1.1296
pyridin-2-yl
3-COOCH2CH3
5-F
H


I.1.1297
pyridin-2-yl
3-COOCH2CH3
6-F
H


I.1.1298
pyridin-2-yl
3-COOCH2CH3
4-Br
H


I.1.1299
pyridin-2-yl
3-COOCH2CH3
5-Br
H


I.1.1300
pyridin-2-yl
3-COOCH2CH3
6-Br
H


I.1.1301
pyridin-2-yl
3-COOCH2CH3
4-CH3
H


I.1.1302
pyridin-2-yl
3-COOCH2CH3
5-CH3
H


I.1.1303
pyridin-2-yl
3-COOCH2CH3
6-CH3
H


I.1.1304
pyridin-2-yl
3-COOCH2CH3
4-CF3
H


I.1.1305
pyridin-2-yl
3-COOCH2CH3
5-CF3
H


I.1.1306
pyridin-2-yl
3-COOCH2CH3
6-CF3
H


I.1.1307
pyridin-2-yl
3-COOCH2CH3
4-vinyl
H


I.1.1308
pyridin-2-yl
3-COOCH2CH3
5-vinyl
H


I.1.1309
pyridin-2-yl
3-COOCH2CH3
6-vinyl
H


I.1.1310
pyridin-2-yl
3-COOCH2CH3
4-Cl
6-F


I.1.1311
pyridin-2-yl
3-COOCH2CH3
5-Cl
6-F


I.1.1312
pyridin-2-yl
3-CONHCH3
4-Cl
5-F


I.1.1313
pyridin-2-yl
3-CONHCH3
4-Cl
H


I.1.1314
pyridin-2-yl
3-CONHCH3
5-Cl
H


I.1.1315
pyridin-2-yl
3-CONHCH3
6-Cl
H


I.1.1316
pyridin-2-yl
3-CONHCH3
4-F
H


I.1.1317
pyridin-2-yl
3-CONHCH3
5-F
H


I.1.1318
pyridin-2-yl
3-CONHCH3
6-F
H


I.1.1319
pyridin-2-yl
3-CONHCH3
4-Br
H


I.1.1320
pyridin-2-yl
3-CONHCH3
5-Br
H


I.1.1321
pyridin-2-yl
3-CONHCH3
6-Br
H


I.1.1322
pyridin-2-yl
3-CONHCH3
4-CH3
H


I.1.1323
pyridin-2-yl
3-CONHCH3
5-CH3
H


I.1.1324
pyridin-2-yl
3-CONHCH3
6-CH3
H


I.1.1325
pyridin-2-yl
3-CONHCH3
4-CF3
H


I.1.1326
pyridin-2-yl
3-CONHCH3
5-CF3
H


I.1.1327
pyridin-2-yl
3-CONHCH3
6-CF3
H


I.1.1328
pyridin-2-yl
3-CONHCH3
4-vinyl
H


I.1.1329
pyridin-2-yl
3-CONHCH3
5-vinyl
H


I.1.1330
pyridin-2-yl
3-CONHCH3
6-vinyl
H


I.1.1331
pyridin-2-yl
3-CONHCH3
4-Cl
6-F


I.1.1332
pyridin-2-yl
3-CONHCH3
5-Cl
6-F


I.1.1333
pyridin-2-yl
3-CON(CH3)2
4-Cl
5-F


I.1.1334
pyridin-2-yl
3-CON(CH3)2
4-Cl
H


I.1.1335
pyridin-2-yl
3-CON(CH3)2
5-Cl
H


I.1.1336
pyridin-2-yl
3-CON(CH3)2
6-Cl
H


I.1.1337
pyridin-2-yl
3-CON(CH3)2
4-F
H


I.1.1338
pyridin-2-yl
3-CON(CH3)2
5-F
H


I.1.1339
pyridin-2-yl
3-CON(CH3)2
6-F
H


I.1.1340
pyridin-2-yl
3-CON(CH3)2
4-Br
H


I.1.1341
pyridin-2-yl
3-CON(CH3)2
5-Br
H


I.1.1342
pyridin-2-yl
3-CON(CH3)2
6-Br
H


I.1.1343
pyridin-2-yl
3-CON(CH3)2
4-CH3
H


I.1.1344
pyridin-2-yl
3-CON(CH3)2
5-CH3
H


I.1.1345
pyridin-2-yl
3-CON(CH3)2
6-CH3
H


I.1.1346
pyridin-2-yl
3-CON(CH3)2
4-CF3
H


I.1.1347
pyridin-2-yl
3-CON(CH3)2
5-CF3
H


I.1.1348
pyridin-2-yl
3-CON(CH3)2
6-CF3
H


I.1.1349
pyridin-2-yl
3-CON(CH3)2
4-vinyl
H


I.1.1350
pyridin-2-yl
3-CON(CH3)2
5-vinyl
H


I.1.1351
pyridin-2-yl
3-CON(CH3)2
6-vinyl
H


I.1.1352
pyridin-2-yl
3-CON(CH3)2
4-Cl
6-F


I.1.1353
pyridin-2-yl
3-CON(CH3)2
5-Cl
6-F


I.1.1354
pyridin-3-yl
2-NO2
4-Cl
5-F


I.1.1355
pyridin-3-yl
2-NO2
4-Cl
H


I.1.1356
pyridin-3-yl
2-NO2
5-Cl
H


I.1.1357
pyridin-3-yl
2-NO2
6-Cl
H


I.1.1358
pyridin-3-yl
2-NO2
4-F
H


I.1.1359
pyridin-3-yl
2-NO2
5-F
H


I.1.1360
pyridin-3-yl
2-NO2
6-F
H


I.1.1361
pyridin-3-yl
2-NO2
4-Br
H


I.1.1362
pyridin-3-yl
2-NO2
5-Br
H


I.1.1363
pyridin-3-yl
2-NO2
6-Br
H


I.1.1364
pyridin-3-yl
2-NO2
4-CH3
H


I.1.1365
pyridin-3-yl
2-NO2
5-CH3
H


I.1.1366
pyridin-3-yl
2-NO2
6-CH3
H


I.1.1367
pyridin-3-yl
2-NO2
4-CF3
H


I.1.1368
pyridin-3-yl
2-NO2
5-CF3
H


I.1.1369
pyridin-3-yl
2-NO2
6-CF3
H


I.1.1370
pyridin-3-yl
2-NO2
4-vinyl
H


I.1.1371
pyridin-3-yl
2-NO2
5-vinyl
H


I.1.1372
pyridin-3-yl
2-NO2
6-vinyl
H


I.1.1373
pyridin-3-yl
2-NO2
4-Cl
6-F


I.1.1374
pyridin-3-yl
2-NO2
5-Cl
6-F


I.1.1412
pyridin-3-yl
2-Br
4-vinyl
H


I.1.1413
pyridin-3-yl
2-Br
5-vinyl
H


I.1.1414
pyridin-3-yl
2-Br
6-vinyl
H


I.1.1415
pyridin-3-yl
2-Br
4-Cl
6-F


I.1.1416
pyridin-3-yl
2-Br
5-Cl
6-F


I.1.1417
pyridin-3-yl
2-Cl
4-Cl
5-F


I.1.1418
pyridin-3-yl
2-Cl
4-Cl
H


I.1.1419
pyridin-3-yl
2-Cl
5-Cl
H


I.1.1420
pyridin-3-yl
2-Cl
6-Cl
H


I.1.1421
pyridin-3-yl
2-Cl
4-F
H


I.1.1422
pyridin-3-yl
2-Cl
5-F
H


I.1.1423
pyridin-3-yl
2-Cl
6-F
H


I.1.1424
pyridin-3-yl
2-Cl
4-Br
H


I.1.1425
pyridin-3-yl
2-Cl
5-Br
H


I.1.1426
pyridin-3-yl
2-Cl
6-Br
H


I.1.1427
pyridin-3-yl
2-Cl
4-CH3
H


I.1.1428
pyridin-3-yl
2-Cl
5-CH3
H


I.1.1429
pyridin-3-yl
2-Cl
6-CH3
H


I.1.1430
pyridin-3-yl
2-Cl
4-CF3
H


I.1.1431
pyridin-3-yl
2-Cl
5-CF3
H


I.1.1432
pyridin-3-yl
2-Cl
6-CF3
H


I.1.1433
pyridin-3-yl
2-Cl
4-vinyl
H


I.1.1434
pyridin-3-yl
2-Cl
5-vinyl
H


I.1.1435
pyridin-3-yl
2-Cl
6-vinyl
H


I.1.1436
pyridin-3-yl
2-Cl
4-Cl
6-F


I.1.1437
pyridin-3-yl
2-Cl
5-Cl
6-F


I.1.1438
pyridin-3-yl
2-ethynyl
4-Cl
5-F


I.1.1439
pyridin-3-yl
2-ethynyl
4-Cl
H


I.1.1440
pyridin-3-yl
2-ethynyl
5-Cl
H


I.1.1441
pyridin-3-yl
2-ethynyl
6-Cl
H


I.1.1442
pyridin-3-yl
2-ethynyl
4-F
H


I.1.1443
pyridin-3-yl
2-ethynyl
5-F
H


I.1.1444
pyridin-3-yl
2-ethynyl
6-F
H


I.1.1445
pyridin-3-yl
2-ethynyl
4-Br
H


I.1.1446
pyridin-3-yl
2-ethynyl
5-Br
H


I.1.1447
pyridin-3-yl
2-ethynyl
6-Br
H


I.1.1448
pyridin-3-yl
2-ethynyl
4-CH3
H


I.1.1449
pyridin-3-yl
2-ethynyl
5-CH3
H


I.1.1450
pyridin-3-yl
2-ethynyl
6-CH3
H


I.1.1451
pyridin-3-yl
2-ethynyl
4-CF3
H


I.1.1452
pyridin-3-yl
2-ethynyl
5-CF3
H


I.1.1453
pyridin-3-yl
2-ethynyl
6-CF3
H


I.1.1454
pyridin-3-yl
2-ethynyl
4-vinyl
H


I.1.1455
pyridin-3-yl
2-ethynyl
5-vinyl
H


I.1.1456
pyridin-3-yl
2-ethynyl
6-vinyl
H


I.1.1457
pyridin-3-yl
2-ethynyl
4-Cl
6-F


I.1.1458
pyridin-3-yl
2-ethynyl
5-Cl
6-F


I.1.1459
pyridin-3-yl
2-I
4-Cl
5-F


I.1.1460
pyridin-3-yl
2-I
4-Cl
H


I.1.1461
pyridin-3-yl
2-I
5-Cl
H


I.1.1462
pyridin-3-yl
2-I
6-Cl
H


I.1.1463
pyridin-3-yl
2-I
4-F
H


I.1.1464
pyridin-3-yl
2-I
5-F
H


I.1.1465
pyridin-3-yl
2-I
6-F
H


I.1.1466
pyridin-3-yl
2-I
4-Br
H


I.1.1467
pyridin-3-yl
2-I
5-Br
H


I.1.1468
pyridin-3-yl
2-I
6-Br
H


I.1.1469
pyridin-3-yl
2-I
4-CH3
H


I.1.1470
pyridin-3-yl
2-I
5-CH3
H


I.1.1471
pyridin-3-yl
2-I
6-CH3
H


I.1.1472
pyridin-3-yl
2-I
4-CF3
H


I.1.1473
pyridin-3-yl
2-I
5-CF3
H


I.1.1474
pyridin-3-yl
2-I
6-CF3
H


I.1.1475
pyridin-3-yl
2-I
4-vinyl
H


I.1.1476
pyridin-3-yl
2-I
5-vinyl
H


I.1.1477
pyridin-3-yl
2-I
6-vinyl
H


I.1.1478
pyridin-3-yl
2-I
4-Cl
6-F


I.1.1479
pyridin-3-yl
2-I
5-Cl
6-F


I.1.1480
pyridin-3-yl
2-COOH
4-Cl
5-F


I.1.1481
pyridin-3-yl
2-COOH
4-Cl
H


I.1.1482
pyridin-3-yl
2-COOH
5-Cl
H


I.1.1483
pyridin-3-yl
2-COOH
6-Cl
H


I.1.1484
pyridin-3-yl
2-COOH
4-F
H


I.1.1485
pyridin-3-yl
2-COOH
5-F
H


I.1.1486
pyridin-3-yl
2-COOH
6-F
H


I.1.1487
pyridin-3-yl
2-COOH
4-Br
H


I.1.1488
pyridin-3-yl
2-COOH
5-Br
H


I.1.1489
pyridin-3-yl
2-COOH
6-Br
H


I.1.1490
pyridin-3-yl
2-COOH
4-CH3
H


I.1.1491
pyridin-3-yl
2-COOH
5-CH3
H


I.1.1492
pyridin-3-yl
2-COOH
6-CH3
H


I.1.1493
pyridin-3-yl
2-COOH
4-CF3
H


I.1.1494
pyridin-3-yl
2-COOH
5-CF3
H


I.1.1495
pyridin-3-yl
2-COOH
6-CF3
H


I.1.1496
pyridin-3-yl
2-COOH
4-vinyl
H


I.1.1497
pyridin-3-yl
2-COOH
5-vinyl
H


I.1.1498
pyridin-3-yl
2-COOH
6-vinyl
H


I.1.1499
pyridin-3-yl
2-COOH
4-Cl
6-F


I.1.1500
pyridin-3-yl
2-COOH
5-Cl
6-F


I.1.1501
pyridin-3-yl
2-COOCH3
4-Cl
5-F


I.1.1502
pyridin-3-yl
2-COOCH3
4-Cl
H


I.1.1503
pyridin-3-yl
2-COOCH3
5-Cl
H


I.1.1504
pyridin-3-yl
2-COOCH3
6-Cl
H


I.1.1505
pyridin-3-yl
2-COOCH3
4-F
H


I.1.1506
pyridin-3-yl
2-COOCH3
5-F
H


I.1.1507
pyridin-3-yl
2-COOCH3
6-F
H


I.1.1508
pyridin-3-yl
2-COOCH3
4-Br
H


I.1.1509
pyridin-3-yl
2-COOCH3
5-Br
H


I.1.1510
pyridin-3-yl
2-COOCH3
6-Br
H


I.1.1511
pyridin-3-yl
2-COOCH3
4-CH3
H


I.1.1512
pyridin-3-yl
2-COOCH3
5-CH3
H


I.1.1513
pyridin-3-yl
2-COOCH3
6-CH3
H


I.1.1514
pyridin-3-yl
2-COOCH3
4-CF3
H


I.1.1515
pyridin-3-yl
2-COOCH3
5-CF3
H


I.1.1516
pyridin-3-yl
2-COOCH3
6-CF3
H


I.1.1517
pyridin-3-yl
2-COOCH3
4-vinyl
H


I.1.1518
pyridin-3-yl
2-COOCH3
5-vinyl
H


I.1.1519
pyridin-3-yl
2-COOCH3
6-vinyl
H


I.1.1520
pyridin-3-yl
2-COOCH3
4-Cl
6-F


I.1.1521
pyridin-3-yl
2-COOCH3
5-Cl
6-F


I.1.1522
pyridin-3-yl
2-COOCH2CH3
4-Cl
5-F


I.1.1523
pyridin-3-yl
2-COOCH2CH3
4-Cl
H


I.1.1524
pyridin-3-yl
2-COOCH2CH3
5-Cl
H


I.1.1525
pyridin-3-yl
2-COOCH2CH3
6-Cl
H


I.1.1526
pyridin-3-yl
2-COOCH2CH3
4-F
H


I.1.1527
pyridin-3-yl
2-COOCH2CH3
5-F
H


I.1.1528
pyridin-3-yl
2-COOCH2CH3
6-F
H


I.1.1529
pyridin-3-yl
2-COOCH2CH3
4-Br
H


I.1.1530
pyridin-3-yl
2-COOCH2CH3
5-Br
H


I.1.1531
pyridin-3-yl
2-COOCH2CH3
6-Br
H


I.1.1532
pyridin-3-yl
2-COOCH2CH3
4-CH3
H


I.1.1533
pyridin-3-yl
2-COOCH2CH3
5-CH3
H


I.1.1534
pyridin-3-yl
2-COOCH2CH3
6-CH3
H


I.1.1535
pyridin-3-yl
2-COOCH2CH3
4-CF3
H


I.1.1536
pyridin-3-yl
2-COOCH2CH3
5-CF3
H


I.1.1537
pyridin-3-yl
2-COOCH2CH3
6-CF3
H


I.1.1538
pyridin-3-yl
2-COOCH2CH3
4-vinyl
H


I.1.1539
pyridin-3-yl
2-COOCH2CH3
5-vinyl
H


I.1.1540
pyridin-3-yl
2-COOCH2CH3
6-vinyl
H


I.1.1541
pyridin-3-yl
2-COOCH2CH3
4-Cl
6-F


I.1.1542
pyridin-3-yl
2-COOCH2CH3
5-Cl
6-F


I.1.1543
pyridin-3-yl
2-CONHCH3
4-Cl
5-F


I.1.1544
pyridin-3-yl
2-CONHCH3
4-Cl
H


I.1.1545
pyridin-3-yl
2-CONHCH3
5-Cl
H


I.1.1546
pyridin-3-yl
2-CONHCH3
6-Cl
H


I.1.1547
pyridin-3-yl
2-CONHCH3
4-F
H


I.1.1548
pyridin-3-yl
2-CONHCH3
5-F
H


I.1.1549
pyridin-3-yl
2-CONHCH3
6-F
H


I.1.1550
pyridin-3-yl
2-CONHCH3
4-Br
H


I.1.1551
pyridin-3-yl
2-CONHCH3
5-Br
H


I.1.1552
pyridin-3-yl
2-CONHCH3
6-Br
H


I.1.1553
pyridin-3-yl
2-CONHCH3
4-CH3
H


I.1.1554
pyridin-3-yl
2-CONHCH3
5-CH3
H


I.1.1555
pyridin-3-yl
2-CONHCH3
6-CH3
H


I.1.1556
pyridin-3-yl
2-CONHCH3
4-CF3
H


I.1.1557
pyridin-3-yl
2-CONHCH3
5-CF3
H


I.1.1558
pyridin-3-yl
2-CONHCH3
6-CF3
H


I.1.1559
pyridin-3-yl
2-CONHCH3
4-vinyl
H


I.1.1560
pyridin-3-yl
2-CONHCH3
5-vinyl
H


I.1.1561
pyridin-3-yl
2-CONHCH3
6-vinyl
H


I.1.1562
pyridin-3-yl
2-CONHCH3
4-Cl
6-F


I.1.1563
pyridin-3-yl
2-CONHCH3
5-Cl
6-F


I.1.1564
pyridin-3-yl
2-CON(CH3)2
4-Cl
5-F


I.1.1565
pyridin-3-yl
2-CON(CH3)2
4-Cl
H


I.1.1566
pyridin-3-yl
2-CON(CH3)2
5-Cl
H


I.1.1567
pyridin-3-yl
2-CON(CH3)2
6-Cl
H


I.1.1568
pyridin-3-yl
2-CON(CH3)2
4-F
H


I.1.1569
pyridin-3-yl
2-CON(CH3)2
5-F
H


I.1.1570
pyridin-3-yl
2-CON(CH3)2
6-F
H


I.1.1571
pyridin-3-yl
2-CON(CH3)2
4-Br
H


I.1.1572
pyridin-3-yl
2-CON(CH3)2
5-Br
H


I.1.1573
pyridin-3-yl
2-CON(CH3)2
6-Br
H


I.1.1574
pyridin-3-yl
2-CON(CH3)2
4-CH3
H


I.1.1575
pyridin-3-yl
2-CON(CH3)2
5-CH3
H


I.1.1576
pyridin-3-yl
2-CON(CH3)2
6-CH3
H


I.1.1577
pyridin-3-yl
2-CON(CH3)2
4-CF3
H


I.1.1578
pyridin-3-yl
2-CON(CH3)2
5-CF3
H


I.1.1579
pyridin-3-yl
2-CON(CH3)2
6-CF3
H


I.1.1580
pyridin-3-yl
2-CON(CH3)2
4-vinyl
H


I.1.1581
pyridin-3-yl
2-CON(CH3)2
5-vinyl
H


I.1.1582
pyridin-3-yl
2-CON(CH3)2
6-vinyl
H


I.1.1583
pyridin-3-yl
2-CON(CH3)2
4-Cl
6-F


I.1.1584
pyridin-3-yl
2-CON(CH3)2
5-Cl
6-F


I.1.1585
pyridin-3-yl
4-NO2
2-Cl
5-F


I.1.1586
pyridin-3-yl
4-NO2
2-Cl
H


I.1.1587
pyridin-3-yl
4-NO2
5-Cl
H


I.1.1588
pyridin-3-yl
4-NO2
6-Cl
H


I.1.1589
pyridin-3-yl
4-NO2
2-F
H


I.1.1590
pyridin-3-yl
4-NO2
5-F
H


I.1.1591
pyridin-3-yl
4-NO2
6-F
H


I.1.1592
pyridin-3-yl
4-NO2
2-Br
H


I.1.1593
pyridin-3-yl
4-NO2
5-Br
H


I.1.1594
pyridin-3-yl
4-NO2
6-Br
H


I.1.1595
pyridin-3-yl
4-NO2
2-CH3
H


I.1.1596
pyridin-3-yl
4-NO2
5-CH3
H


I.1.1597
pyridin-3-yl
4-NO2
6-CH3
H


I.1.1598
pyridin-3-yl
4-NO2
2-CF3
H


I.1.1599
pyridin-3-yl
4-NO2
5-CF3
H


I.1.1600
pyridin-3-yl
4-NO2
6-CF3
H


I.1.1601
pyridin-3-yl
4-NO2
2-vinyl
H


I.1.1602
pyridin-3-yl
4-NO2
5-vinyl
H


I.1.1603
pyridin-3-yl
4-NO2
6-vinyl
H


I.1.1604
pyridin-3-yl
4-NO2
2-Cl
6-F


I.1.1605
pyridin-3-yl
4-NO2
5-Cl
6-F


I.1.1606
pyridin-3-yl
4-CN
2-Cl
5-F


I.1.1607
pyridin-3-yl
4-CN
2-Cl
H


I.1.1608
pyridin-3-yl
4-CN
5-Cl
H


I.1.1609
pyridin-3-yl
4-CN
6-Cl
H


I.1.1610
pyridin-3-yl
4-CN
2-F
H


I.1.1611
pyridin-3-yl
4-CN
5-F
H


I.1.1612
pyridin-3-yl
4-CN
6-F
H


I.1.1613
pyridin-3-yl
4-CN
2-Br
H


I.1.1614
pyridin-3-yl
4-CN
5-Br
H


I.1.1615
pyridin-3-yl
4-CN
6-Br
H


I.1.1616
pyridin-3-yl
4-CN
2-CH3
H


I.1.1617
pyridin-3-yl
4-CN
5-CH3
H


I.1.1618
pyridin-3-yl
4-CN
6-CH3
H


I.1.1619
pyridin-3-yl
4-CN
2-CF3
H


I.1.1620
pyridin-3-yl
4-CN
5-CF3
H


I.1.1621
pyridin-3-yl
4-CN
6-CF3
H


I.1.1622
pyridin-3-yl
4-CN
2-vinyl
H


I.1.1623
pyridin-3-yl
4-CN
5-vinyl
H


I.1.1624
pyridin-3-yl
4-CN
6-vinyl
H


I.1.1625
pyridin-3-yl
4-CN
2-Cl
6-F


I.1.1626
pyridin-3-yl
4-CN
5-Cl
6-F


I.1.1627
pyridin-3-yl
4-Br
2-Cl
5-F


I.1.1628
pyridin-3-yl
4-Br
2-Cl
H


I.1.1629
pyridin-3-yl
4-Br
5-Cl
H


I.1.1630
pyridin-3-yl
4-Br
6-Cl
H


I.1.1631
pyridin-3-yl
4-Br
2-F
H


I.1.1632
pyridin-3-yl
4-Br
5-F
H


I.1.1633
pyridin-3-yl
4-Br
6-F
H


I.1.1634
pyridin-3-yl
4-Br
2-Br
H


I.1.1635
pyridin-3-yl
4-Br
5-Br
H


I.1.1636
pyridin-3-yl
4-Br
6-Br
H


I.1.1637
pyridin-3-yl
4-Br
2-CH3
H


I.1.1638
pyridin-3-yl
4-Br
5-CH3
H


I.1.1639
pyridin-3-yl
4-Br
6-CH3
H


I.1.1640
pyridin-3-yl
4-Br
2-CF3
H


I.1.1641
pyridin-3-yl
4-Br
5-CF3
H


I.1.1642
pyridin-3-yl
4-Br
6-CF3
H


I.1.1643
pyridin-3-yl
4-Br
2-vinyl
H


I.1.1644
pyridin-3-yl
4-Br
5-vinyl
H


I.1.1645
pyridin-3-yl
4-Br
6-vinyl
H


I.1.1646
pyridin-3-yl
4-Br
2-Cl
6-F


I.1.1647
pyridin-3-yl
4-Br
5-Cl
6-F


I.1.1648
pyridin-3-yl
4-Cl
2-Cl
5-F


I.1.1649
pyridin-3-yl
4-Cl
2-Cl
H


I.1.1650
pyridin-3-yl
4-Cl
5-Cl
H


I.1.1651
pyridin-3-yl
4-Cl
6-Cl
H


I.1.1652
pyridin-3-yl
4-Cl
2-F
H


I.1.1653
pyridin-3-yl
4-Cl
5-F
H


I.1.1654
pyridin-3-yl
4-Cl
6-F
H


I.1.1655
pyridin-3-yl
4-Cl
2-Br
H


I.1.1656
pyridin-3-yl
4-Cl
5-Br
H


I.1.1657
pyridin-3-yl
4-Cl
6-Br
H


I.1.1658
pyridin-3-yl
4-Cl
2-CH3
H


I.1.1659
pyridin-3-yl
4-Cl
5-CH3
H


I.1.1660
pyridin-3-yl
4-Cl
6-CH3
H


I.1.1661
pyridin-3-yl
4-Cl
2-CF3
H


I.1.1662
pyridin-3-yl
4-Cl
5-CF3
H


I.1.1663
pyridin-3-yl
4-Cl
6-CF3
H


I.1.1664
pyridin-3-yl
4-Cl
2-vinyl
H


I.1.1665
pyridin-3-yl
4-Cl
5-vinyl
H


I.1.1666
pyridin-3-yl
4-Cl
6-vinyl
H


I.1.1667
pyridin-3-yl
4-Cl
2-Cl
6-F


I.1.1668
pyridin-3-yl
4-Cl
5-Cl
6-F


I.1.1669
pyridin-3-yl
4-ethynyl
2-Cl
5-F


I.1.1670
pyridin-3-yl
4-ethynyl
2-Cl
H


I.1.1671
pyridin-3-yl
4-ethynyl
5-Cl
H


I.1.1672
pyridin-3-yl
4-ethynyl
6-Cl
H


I.1.1673
pyridin-3-yl
4-ethynyl
2-F
H


I.1.1674
pyridin-3-yl
4-ethynyl
5-F
H


I.1.1675
pyridin-3-yl
4-ethynyl
6-F
H


I.1.1676
pyridin-3-yl
4-ethynyl
2-Br
H


I.1.1677
pyridin-3-yl
4-ethynyl
5-Br
H


I.1.1678
pyridin-3-yl
4-ethynyl
6-Br
H


I.1.1679
pyridin-3-yl
4-ethynyl
2-CH3
H


I.1.1680
pyridin-3-yl
4-ethynyl
5-CH3
H


I.1.1681
pyridin-3-yl
4-ethynyl
6-CH3
H


I.1.1682
pyridin-3-yl
4-ethynyl
2-CF3
H


I.1.1683
pyridin-3-yl
4-ethynyl
5-CF3
H


I.1.1684
pyridin-3-yl
4-ethynyl
6-CF3
H


I.1.1685
pyridin-3-yl
4-ethynyl
2-vinyl
H


I.1.1686
pyridin-3-yl
4-ethynyl
5-vinyl
H


I.1.1687
pyridin-3-yl
4-ethynyl
6-vinyl
H


I.1.1688
pyridin-3-yl
4-ethynyl
2-Cl
6-F


I.1.1689
pyridin-3-yl
4-ethynyl
5-Cl
6-F


I.1.1690
pyridin-3-yl
4-I
2-Cl
5-F


I.1.1691
pyridin-3-yl
4-I
2-Cl
H


I.1.1692
pyridin-3-yl
4-I
5-Cl
H


I.1.1693
pyridin-3-yl
4-I
6-Cl
H


I.1.1694
pyridin-3-yl
4-I
2-F
H


I.1.1695
pyridin-3-yl
4-I
5-F
H


I.1.1696
pyridin-3-yl
4-I
6-F
H


I.1.1697
pyridin-3-yl
4-I
2-Br
H


I.1.1698
pyridin-3-yl
4-I
5-Br
H


I.1.1699
pyridin-3-yl
4-I
6-Br
H


I.1.1700
pyridin-3-yl
4-I
2-CH3
H


I.1.1701
pyridin-3-yl
4-I
5-CH3
H


I.1.1702
pyridin-3-yl
4-I
6-CH3
H


I.1.1703
pyridin-3-yl
4-I
2-CF3
H


I.1.1704
pyridin-3-yl
4-I
5-CF3
H


I.1.1705
pyridin-3-yl
4-I
6-CF3
H


I.1.1706
pyridin-3-yl
4-I
2-vinyl
H


I.1.1707
pyridin-3-yl
4-I
5-vinyl
H


I.1.1708
pyridin-3-yl
4-I
6-vinyl
H


I.1.1709
pyridin-3-yl
4-I
2-Cl
6-F


I.1.1710
pyridin-3-yl
4-I
5-Cl
6-F


I.1.1711
pyridin-3-yl
4-COOH
2-Cl
5-F


I.1.1712
pyridin-3-yl
4-COOH
2-Cl
H


I.1.1713
pyridin-3-yl
4-COOH
5-Cl
H


I.1.1714
pyridin-3-yl
4-COOH
6-Cl
H


I.1.1715
pyridin-3-yl
4-COOH
2-F
H


I.1.1716
pyridin-3-yl
4-COOH
5-F
H


I.1.1717
pyridin-3-yl
4-COOH
6-F
H


I.1.1718
pyridin-3-yl
4-COOH
2-Br
H


I.1.1719
pyridin-3-yl
4-COOH
5-Br
H


I.1.1720
pyridin-3-yl
4-COOH
6-Br
H


I.1.1721
pyridin-3-yl
4-COOH
2-CH3
H


I.1.1722
pyridin-3-yl
4-COOH
5-CH3
H


I.1.1723
pyridin-3-yl
4-COOH
6-CH3
H


I.1.1724
pyridin-3-yl
4-COOH
2-CF3
H


I.1.1725
pyridin-3-yl
4-COOH
5-CF3
H


I.1.1726
pyridin-3-yl
4-COOH
6-CF3
H


I.1.1727
pyridin-3-yl
4-COOH
2-vinyl
H


I.1.1728
pyridin-3-yl
4-COOH
5-vinyl
H


I.1.1729
pyridin-3-yl
4-COOH
6-vinyl
H


I.1.1730
pyridin-3-yl
4-COOH
2-Cl
6-F


I.1.1731
pyridin-3-yl
4-COOH
5-Cl
6-F


I.1.1732
pyridin-3-yl
4-COOCH3
2-Cl
5-F


I.1.1733
pyridin-3-yl
4-COOCH3
2-Cl
H


I.1.1734
pyridin-3-yl
4-COOCH3
5-Cl
H


I.1.1735
pyridin-3-yl
4-COOCH3
6-Cl
H


I.1.1736
pyridin-3-yl
4-COOCH3
2-F
H


I.1.1737
pyridin-3-yl
4-COOCH3
5-F
H


I.1.1738
pyridin-3-yl
4-COOCH3
6-F
H


I.1.1739
pyridin-3-yl
4-COOCH3
2-Br
H


I.1.1740
pyridin-3-yl
4-COOCH3
5-Br
H


I.1.1741
pyridin-3-yl
4-COOCH3
6-Br
H


I.1.1742
pyridin-3-yl
4-COOCH3
2-CH3
H


I.1.1743
pyridin-3-yl
4-COOCH3
5-CH3
H


I.1.1744
pyridin-3-yl
4-COOCH3
6-CH3
H


I.1.1745
pyridin-3-yl
4-COOCH3
2-CF3
H


I.1.1746
pyridin-3-yl
4-COOCH3
5-CF3
H


I.1.1747
pyridin-3-yl
4-COOCH3
6-CF3
H


I.1.1748
pyridin-3-yl
4-COOCH3
2-vinyl
H


I.1.1749
pyridin-3-yl
4-COOCH3
5-vinyl
H


I.1.1750
pyridin-3-yl
4-COOCH3
6-vinyl
H


I.1.1751
pyridin-3-yl
4-COOCH3
2-Cl
6-F


I.1.1752
pyridin-3-yl
4-COOCH3
5-Cl
6-F


I.1.1753
pyridin-3-yl
4-COOCH2CH3
2-Cl
5-F


I.1.1754
pyridin-3-yl
4-COOCH2CH3
2-Cl
H


I.1.1755
pyridin-3-yl
4-COOCH2CH3
5-Cl
H


I.1.1756
pyridin-3-yl
4-COOCH2CH3
6-Cl
H


I.1.1757
pyridin-3-yl
4-COOCH2CH3
2-F
H


I.1.1758
pyridin-3-yl
4-COOCH2CH3
5-F
H


I.1.1759
pyridin-3-yl
4-COOCH2CH3
6-F
H


I.1.1760
pyridin-3-yl
4-COOCH2CH3
2-Br
H


I.1.1761
pyridin-3-yl
4-COOCH2CH3
5-Br
H


I.1.1762
pyridin-3-yl
4-COOCH2CH3
6-Br
H


I.1.1763
pyridin-3-yl
4-COOCH2CH3
2-CH3
H


I.1.1764
pyridin-3-yl
4-COOCH2CH3
5-CH3
H


I.1.1765
pyridin-3-yl
4-COOCH2CH3
6-CH3
H


I.1.1766
pyridin-3-yl
4-COOCH2CH3
2-CF3
H


I.1.1767
pyridin-3-yl
4-COOCH2CH3
5-CF3
H


I.1.1768
pyridin-3-yl
4-COOCH2CH3
6-CF3
H


I.1.1769
pyridin-3-yl
4-COOCH2CH3
2-vinyl
H


I.1.1770
pyridin-3-yl
4-COOCH2CH3
5-vinyl
H


I.1.1771
pyridin-3-yl
4-COOCH2CH3
6-vinyl
H


I.1.1772
pyridin-3-yl
4-COOCH2CH3
2-Cl
6-F


I.1.1773
pyridin-3-yl
4-COOCH2CH3
5-Cl
6-F


I.1.1774
pyridin-3-yl
4-CONHCH3
2-Cl
5-F


I.1.1775
pyridin-3-yl
4-CONHCH3
2-Cl
H


I.1.1776
pyridin-3-yl
4-CONHCH3
5-Cl
H


I.1.1777
pyridin-3-yl
4-CONHCH3
6-Cl
H


I.1.1778
pyridin-3-yl
4-CONHCH3
2-F
H


I.1.1779
pyridin-3-yl
4-CONHCH3
5-F
H


I.1.1780
pyridin-3-yl
4-CONHCH3
6-F
H


I.1.1781
pyridin-3-yl
4-CONHCH3
2-Br
H


I.1.1782
pyridin-3-yl
4-CONHCH3
5-Br
H


I.1.1783
pyridin-3-yl
4-CONHCH3
6-Br
H


I.1.1784
pyridin-3-yl
4-CONHCH3
2-CH3
H


I.1.1785
pyridin-3-yl
4-CONHCH3
5-CH3
H


I.1.1786
pyridin-3-yl
4-CONHCH3
6-CH3
H


I.1.1787
pyridin-3-yl
4-CONHCH3
2-CF3
H


I.1.1788
pyridin-3-yl
4-CONHCH3
5-CF3
H


I.1.1789
pyridin-3-yl
4-CONHCH3
6-CF3
H


I.1.1790
pyridin-3-yl
4-CONHCH3
2-vinyl
H


I.1.1791
pyridin-3-yl
4-CONHCH3
5-vinyl
H


I.1.1792
pyridin-3-yl
4-CONHCH3
6-vinyl
H


I.1.1793
pyridin-3-yl
4-CONHCH3
2-Cl
6-F


I.1.1794
pyridin-3-yl
4-CONHCH3
5-Cl
6-F


I.1.1795
pyridin-3-yl
4-CON(CH3)2
2-Cl
5-F


I.1.1796
pyridin-3-yl
4-CON(CH3)2
2-Cl
H


I.1.1797
pyridin-3-yl
4-CON(CH3)2
5-Cl
H


I.1.1798
pyridin-3-yl
4-CON(CH3)2
6-Cl
H


I.1.1799
pyridin-3-yl
4-CON(CH3)2
2-F
H


I.1.1800
pyridin-3-yl
4-CON(CH3)2
5-F
H


I.1.1801
pyridin-3-yl
4-CON(CH3)2
6-F
H


I.1.1802
pyridin-3-yl
4-CON(CH3)2
2-Br
H


I.1.1803
pyridin-3-yl
4-CON(CH3)2
5-Br
H


I.1.1804
pyridin-3-yl
4-CON(CH3)2
6-Br
H


I.1.1805
pyridin-3-yl
4-CON(CH3)2
2-CH3
H


I.1.1806
pyridin-3-yl
4-CON(CH3)2
5-CH3
H


I.1.1807
pyridin-3-yl
4-CON(CH3)2
6-CH3
H


I.1.1808
pyridin-3-yl
4-CON(CH3)2
2-CF3
H


I.1.1809
pyridin-3-yl
4-CON(CH3)2
5-CF3
H


I.1.1810
pyridin-3-yl
4-CON(CH3)2
6-CF3
H


I.1.1811
pyridin-3-yl
4-CON(CH3)2
2-vinyl
H


I.1.1812
pyridin-3-yl
4-CON(CH3)2
5-vinyl
H


I.1.1813
pyridin-3-yl
4-CON(CH3)2
6-vinyl
H


I.1.1814
pyridin-3-yl
4-CON(CH3)2
2-Cl
6-F


I.1.1815
pyridin-3-yl
4-CON(CH3)2
5-Cl
6-F


I.1.1816
pyridin-4-yl
3-NO2
2-Cl
5-F


I.1.1817
pyridin-4-yl
3-NO2
2-Cl
H


I.1.1818
pyridin-4-yl
3-NO2
5-Cl
H


I.1.1819
pyridin-4-yl
3-NO2
6-Cl
H


I.1.1820
pyridin-4-yl
3-NO2
2-F
H


I.1.1821
pyridin-4-yl
3-NO2
5-F
H


I.1.1822
pyridin-4-yl
3-NO2
6-F
H


I.1.1823
pyridin-4-yl
3-NO2
2-Br
H


I.1.1824
pyridin-4-yl
3-NO2
5-Br
H


I.1.1825
pyridin-4-yl
3-NO2
6-Br
H


I.1.1826
pyridin-4-yl
3-NO2
2-CH3
H


I.1.1827
pyridin-4-yl
3-NO2
5-CH3
H


I.1.1828
pyridin-4-yl
3-NO2
6-CH3
H


I.1.1829
pyridin-4-yl
3-NO2
2-CF3
H


I.1.1830
pyridin-4-yl
3-NO2
5-CF3
H


I.1.1831
pyridin-4-yl
3-NO2
6-CF3
H


I.1.1832
pyridin-4-yl
3-NO2
2-vinyl
H


I.1.1833
pyridin-4-yl
3-NO2
5-vinyl
H


I.1.1834
pyridin-4-yl
3-NO2
6-vinyl
H


I.1.1835
pyridin-4-yl
3-NO2
2-Cl
6-F


I.1.1836
pyridin-4-yl
3-NO2
5-Cl
6-F


I.1.1837
pyridin-4-yl
3-CN
2-Cl
5-F


I.1.1838
pyridin-4-yl
3-CN
2-Cl
H


I.1.1839
pyridin-4-yl
3-CN
5-Cl
H


I.1.1840
pyridin-4-yl
3-CN
6-Cl
H


I.1.1841
pyridin-4-yl
3-CN
2-F
H


I.1.1842
pyridin-4-yl
3-CN
5-F
H


I.1.1843
pyridin-4-yl
3-CN
6-F
H


I.1.1844
pyridin-4-yl
3-CN
2-Br
H


I.1.1845
pyridin-4-yl
3-CN
5-Br
H


I.1.1846
pyridin-4-yl
3-CN
6-Br
H


I.1.1847
pyridin-4-yl
3-CN
2-CH3
H


I.1.1848
pyridin-4-yl
3-CN
5-CH3
H


I.1.1849
pyridin-4-yl
3-CN
6-CH3
H


I.1.1850
pyridin-4-yl
3-CN
2-CF3
H


I.1.1851
pyridin-4-yl
3-CN
5-CF3
H


I.1.1852
pyridin-4-yl
3-CN
6-CF3
H


I.1.1853
pyridin-4-yl
3-CN
2-vinyl
H


I.1.1854
pyridin-4-yl
3-CN
5-vinyl
H


I.1.1855
pyridin-4-yl
3-CN
6-vinyl
H


I.1.1856
pyridin-4-yl
3-CN
2-Cl
6-F


I.1.1857
pyridin-4-yl
3-CN
5-Cl
6-F


I.1.1858
pyridin-4-yl
3-Br
2-Cl
5-F


I.1.1859
pyridin-4-yl
3-Br
2-Cl
H


I.1.1860
pyridin-4-yl
3-Br
5-Cl
H


I.1.1861
pyridin-4-yl
3-Br
6-Cl
H


I.1.1862
pyridin-4-yl
3-Br
2-F
H


I.1.1863
pyridin-4-yl
3-Br
5-F
H


I.1.1864
pyridin-4-yl
3-Br
6-F
H


I.1.1865
pyridin-4-yl
3-Br
2-Br
H


I.1.1866
pyridin-4-yl
3-Br
5-Br
H


I.1.1867
pyridin-4-yl
3-Br
6-Br
H


I.1.1868
pyridin-4-yl
3-Br
2-CH3
H


I.1.1869
pyridin-4-yl
3-Br
5-CH3
H


I.1.1870
pyridin-4-yl
3-Br
6-CH3
H


I.1.1871
pyridin-4-yl
3-Br
2-CF3
H


I.1.1872
pyridin-4-yl
3-Br
5-CF3
H


I.1.1873
pyridin-4-yl
3-Br
6-CF3
H


I.1.1874
pyridin-4-yl
3-Br
2-vinyl
H


I.1.1875
pyridin-4-yl
3-Br
5-vinyl
H


I.1.1876
pyridin-4-yl
3-Br
6-vinyl
H


I.1.1877
pyridin-4-yl
3-Br
2-Cl
6-F


I.1.1878
pyridin-4-yl
3-Br
5-Cl
6-F


I.1.1879
pyridin-4-yl
3-Cl
2-Cl
5-F


I.1.1880
pyridin-4-yl
3-Cl
2-Cl
H


I.1.1881
pyridin-4-yl
3-Cl
5-Cl
H


I.1.1882
pyridin-4-yl
3-Cl
6-Cl
H


I.1.1883
pyridin-4-yl
3-Cl
2-F
H


I.1.1884
pyridin-4-yl
3-Cl
5-F
H


I.1.1885
pyridin-4-yl
3-Cl
6-F
H


I.1.1886
pyridin-4-yl
3-Cl
2-Br
H


I.1.1887
pyridin-4-yl
3-Cl
5-Br
H


I.1.1888
pyridin-4-yl
3-Cl
6-Br
H


I.1.1889
pyridin-4-yl
3-Cl
2-CH3
H


I.1.1890
pyridin-4-yl
3-Cl
5-CH3
H


I.1.1891
pyridin-4-yl
3-Cl
6-CH3
H


I.1.1892
pyridin-4-yl
3-Cl
2-CF3
H


I.1.1893
pyridin-4-yl
3-Cl
5-CF3
H


I.1.1894
pyridin-4-yl
3-Cl
6-CF3
H


I.1.1895
pyridin-4-yl
3-Cl
2-vinyl
H


I.1.1896
pyridin-4-yl
3-Cl
5-vinyl
H


I.1.1897
pyridin-4-yl
3-Cl
6-vinyl
H


I.1.1898
pyridin-4-yl
3-Cl
2-Cl
6-F


I.1.1899
pyridin-4-yl
3-Cl
5-Cl
6-F


I.1.1900
pyridin-4-yl
3-ethynyl
2-Cl
5-F


I.1.1901
pyridin-4-yl
3-ethynyl
2-Cl
H


I.1.1902
pyridin-4-yl
3-ethynyl
5-Cl
H


I.1.1903
pyridin-4-yl
3-ethynyl
6-Cl
H


I.1.1904
pyridin-4-yl
3-ethynyl
2-F
H


I.1.1905
pyridin-4-yl
3-ethynyl
5-F
H


I.1.1906
pyridin-4-yl
3-ethynyl
6-F
H


I.1.1907
pyridin-4-yl
3-ethynyl
2-Br
H


I.1.1908
pyridin-4-yl
3-ethynyl
5-Br
H


I.1.1909
pyridin-4-yl
3-ethynyl
6-Br
H


I.1.1910
pyridin-4-yl
3-ethynyl
2-CH3
H


I.1.1911
pyridin-4-yl
3-ethynyl
5-CH3
H


I.1.1912
pyridin-4-yl
3-ethynyl
6-CH3
H


I.1.1913
pyridin-4-yl
3-ethynyl
2-CF3
H


I.1.1914
pyridin-4-yl
3-ethynyl
5-CF3
H


I.1.1915
pyridin-4-yl
3-ethynyl
6-CF3
H


I.1.1916
pyridin-4-yl
3-ethynyl
2-vinyl
H


I.1.1917
pyridin-4-yl
3-ethynyl
5-vinyl
H


I.1.1918
pyridin-4-yl
3-ethynyl
6-vinyl
H


I.1.1919
pyridin-4-yl
3-ethynyl
2-Cl
6-F


I.1.1920
pyridin-4-yl
3-ethynyl
5-Cl
6-F


I.1.1921
pyridin-4-yl
3-I
2-Cl
5-F


I.1.1922
pyridin-4-yl
3-I
2-Cl
H


I.1.1923
pyridin-4-yl
3-I
5-Cl
H


I.1.1924
pyridin-4-yl
3-I
6-Cl
H


I.1.1925
pyridin-4-yl
3-I
2-F
H


I.1.1926
pyridin-4-yl
3-I
5-F
H


I.1.1927
pyridin-4-yl
3-I
6-F
H


I.1.1928
pyridin-4-yl
3-I
2-Br
H


I.1.1929
pyridin-4-yl
3-I
5-Br
H


I.1.1930
pyridin-4-yl
3-I
6-Br
H


I.1.1931
pyridin-4-yl
3-I
2-CH3
H


I.1.1932
pyridin-4-yl
3-I
5-CH3
H


I.1.1933
pyridin-4-yl
3-I
6-CH3
H


I.1.1934
pyridin-4-yl
3-I
2-CF3
H


I.1.1935
pyridin-4-yl
3-I
5-CF3
H


I.1.1936
pyridin-4-yl
3-I
6-CF3
H


I.1.1937
pyridin-4-yl
3-I
2-vinyl
H


I.1.1938
pyridin-4-yl
3-I
5-vinyl
H


I.1.1939
pyridin-4-yl
3-I
6-vinyl
H


I.1.1940
pyridin-4-yl
3-I
2-Cl
6-F


I.1.1941
pyridin-4-yl
3-I
5-Cl
6-F


I.1.1942
pyridin-4-yl
3-COOH
2-Cl
5-F


I.1.1943
pyridin-4-yl
3-COOH
2-Cl
H


I.1.1944
pyridin-4-yl
3-COOH
5-Cl
H


I.1.1945
pyridin-4-yl
3-COOH
6-Cl
H


I.1.1946
pyridin-4-yl
3-COOH
2-F
H


I.1.1947
pyridin-4-yl
3-COOH
5-F
H


I.1.1948
pyridin-4-yl
3-COOH
6-F
H


I.1.1949
pyridin-4-yl
3-COOH
2-Br
H


I.1.1950
pyridin-4-yl
3-COOH
5-Br
H


I.1.1951
pyridin-4-yl
3-COOH
6-Br
H


I.1.1952
pyridin-4-yl
3-COOH
2-CH3
H


I.1.1953
pyridin-4-yl
3-COOH
5-CH3
H


I.1.1954
pyridin-4-yl
3-COOH
6-CH3
H


I.1.1955
pyridin-4-yl
3-COOH
2-CF3
H


I.1.1956
pyridin-4-yl
3-COOH
5-CF3
H


I.1.1957
pyridin-4-yl
3-COOH
6-CF3
H


I.1.1958
pyridin-4-yl
3-COOH
2-vinyl
H


I.1.1959
pyridin-4-yl
3-COOH
5-vinyl
H


I.1.1960
pyridin-4-yl
3-COOH
6-vinyl
H


I.1.1961
pyridin-4-yl
3-COOH
2-Cl
6-F


I.1.1962
pyridin-4-yl
3-COOH
5-Cl
6-F


I.1.1963
pyridin-4-yl
3-COOCH3
2-Cl
5-F


I.1.1964
pyridin-4-yl
3-COOCH3
2-Cl
H


I.1.1965
pyridin-4-yl
3-COOCH3
5-Cl
H


I.1.1966
pyridin-4-yl
3-COOCH3
6-Cl
H


I.1.1967
pyridin-4-yl
3-COOCH3
2-F
H


I.1.1968
pyridin-4-yl
3-COOCH3
5-F
H


I.1.1969
pyridin-4-yl
3-COOCH3
6-F
H


I.1.1970
pyridin-4-yl
3-COOCH3
2-Br
H


I.1.1971
pyridin-4-yl
3-COOCH3
5-Br
H


I.1.1972
pyridin-4-yl
3-COOCH3
6-Br
H


I.1.1973
pyridin-4-yl
3-COOCH3
2-CH3
H


I.1.1974
pyridin-4-yl
3-COOCH3
5-CH3
H


I.1.1975
pyridin-4-yl
3-COOCH3
6-CH3
H


I.1.1976
pyridin-4-yl
3-COOCH3
2-CF3
H


I.1.1977
pyridin-4-yl
3-COOCH3
5-CF3
H


I.1.1978
pyridin-4-yl
3-COOCH3
6-CF3
H


I.1.1979
pyridin-4-yl
3-COOCH3
2-vinyl
H


I.1.1980
pyridin-4-yl
3-COOCH3
5-vinyl
H


I.1.1981
pyridin-4-yl
3-COOCH3
6-vinyl
H


I.1.1982
pyridin-4-yl
3-COOCH3
2-Cl
6-F


I.1.1983
pyridin-4-yl
3-COOCH3
5-Cl
6-F


I.1.1984
pyridin-4-yl
3-COOCH2CH3
2-Cl
5-F


I.1.1985
pyridin-4-yl
3-COOCH2CH3
2-Cl
H


I.1.1986
pyridin-4-yl
3-COOCH2CH3
5-Cl
H


I.1.1987
pyridin-4-yl
3-COOCH2CH3
6-Cl
H


I.1.1988
pyridin-4-yl
3-COOCH2CH3
2-F
H


I.1.1989
pyridin-4-yl
3-COOCH2CH3
5-F
H


I.1.1990
pyridin-4-yl
3-COOCH2CH3
6-F
H


I.1.1991
pyridin-4-yl
3-COOCH2CH3
2-Br
H


I.1.1992
pyridin-4-yl
3-COOCH2CH3
5-Br
H


I.1.1993
pyridin-4-yl
3-COOCH2CH3
6-Br
H


I.1.1994
pyridin-4-yl
3-COOCH2CH3
2-CH3
H


I.1.1995
pyridin-4-yl
3-COOCH2CH3
5-CH3
H


I.1.1996
pyridin-4-yl
3-COOCH2CH3
6-CH3
H


I.1.1997
pyridin-4-yl
3-COOCH2CH3
2-CF3
H


I.1.1998
pyridin-4-yl
3-COOCH2CH3
5-CF3
H


I.1.1999
pyridin-4-yl
3-COOCH2CH3
6-CF3
H


I.1.2000
pyridin-4-yl
3-COOCH2CH3
2-vinyl
H


I.1.2001
pyridin-4-yl
3-COOCH2CH3
5-vinyl
H


I.1.2002
pyridin-4-yl
3-COOCH2CH3
6-vinyl
H


I.1.2003
pyridin-4-yl
3-COOCH2CH3
2-Cl
6-F


I.1.2004
pyridin-4-yl
3-COOCH2CH3
5-Cl
6-F


I.1.2005
pyridin-4-yl
3-CONHCH3
2-Cl
5-F


I.1.2006
pyridin-4-yl
3-CONHCH3
2-Cl
H


I.1.2007
pyridin-4-yl
3-CONHCH3
5-Cl
H


I.1.2008
pyridin-4-yl
3-CONHCH3
6-Cl
H


I.1.2009
pyridin-4-yl
3-CONHCH3
2-F
H


I.1.2010
pyridin-4-yl
3-CONHCH3
5-F
H


I.1.2011
pyridin-4-yl
3-CONHCH3
6-F
H


I.1.2012
pyridin-4-yl
3-CONHCH3
2-Br
H


I.1.2013
pyridin-4-yl
3-CONHCH3
5-Br
H


I.1.2014
pyridin-4-yl
3-CONHCH3
6-Br
H


I.1.2015
pyridin-4-yl
3-CONHCH3
2-CH3
H


I.1.2016
pyridin-4-yl
3-CONHCH3
5-CH3
H


I.1.2017
pyridin-4-yl
3-CONHCH3
6-CH3
H


I.1.2018
pyridin-4-yl
3-CONHCH3
2-CF3
H


I.1.2019
pyridin-4-yl
3-CONHCH3
5-CF3
H


I.1.2020
pyridin-4-yl
3-CONHCH3
6-CF3
H


I.1.2021
pyridin-4-yl
3-CONHCH3
2-vinyl
H


I.1.2022
pyridin-4-yl
3-CONHCH3
5-vinyl
H


I.1.2023
pyridin-4-yl
3-CONHCH3
6-vinyl
H


I.1.2024
pyridin-4-yl
3-CONHCH3
2-Cl
6-F


I.1.2025
pyridin-4-yl
3-CONHCH3
5-Cl
6-F


I.1.2026
pyridin-4-yl
3-CON(CH3)2
2-Cl
5-F


I.1.2027
pyridin-4-yl
3-CON(CH3)2
2-Cl
H


I.1.2028
pyridin-4-yl
3-CON(CH3)2
5-Cl
H


I.1.2029
pyridin-4-yl
3-CON(CH3)2
6-Cl
H


I.1.2030
pyridin-4-yl
3-CON(CH3)2
2-F
H


I.1.2031
pyridin-4-yl
3-CON(CH3)2
5-F
H


I.1.2032
pyridin-4-yl
3-CON(CH3)2
6-F
H


I.1.2033
pyridin-4-yl
3-CON(CH3)2
2-Br
H


I.1.2034
pyridin-4-yl
3-CON(CH3)2
5-Br
H


I.1.2035
pyridin-4-yl
3-CON(CH3)2
6-Br
H


I.1.2036
pyridin-4-yl
3-CON(CH3)2
2-CH3
H


I.1.2037
pyridin-4-yl
3-CON(CH3)2
5-CH3
H


I.1.2038
pyridin-4-yl
3-CON(CH3)2
6-CH3
H


I.1.2039
pyridin-4-yl
3-CON(CH3)2
2-CF3
H


I.1.2040
pyridin-4-yl
3-CON(CH3)2
5-CF3
H


I.1.2041
pyridin-4-yl
3-CON(CH3)2
6-CF3
H


I.1.2042
pyridin-4-yl
3-CON(CH3)2
2-vinyl
H


I.1.2043
pyridin-4-yl
3-CON(CH3)2
5-vinyl
H


I.1.2044
pyridin-4-yl
3-CON(CH3)2
6-vinyl
H


I.1.2045
pyridin-4-yl
3-CON(CH3)2
2-Cl
6-F


I.1.2046
pyridin-4-yl
3-CON(CH3)2
5-Cl
6-F


I.1.2047
furan-2-yl
3-NO2
4-Cl
5-F


I.1.2048
furan-2-yl
3-NO2
4-Cl
H


I.1.2049
furan-2-yl
3-NO2
5-Cl
H


I.1.2050
furan-2-yl
3-NO2
4-F
H


I.1.2051
furan-2-yl
3-NO2
5-F
H


I.1.2052
furan-2-yl
3-NO2
4-CH3
H


I.1.2053
furan-2-yl
3-NO2
5-CH3
H


I.1.2054
furan-2-yl
3-NO2
4-CN
H


I.1.2055
furan-2-yl
3-NO2
5-CN
H


I.1.2056
furan-2-yl
3-NO2
4-CF3
H


I.1.2057
furan-2-yl
3-NO2
5-CF3
H


I.1.2058
furan-2-yl
3-CN
4-Cl
5-F


I.1.2059
furan-2-yl
3-CN
4-Cl
H


I.1.2060
furan-2-yl
3-CN
5-Cl
H


I.1.2061
furan-2-yl
3-CN
4-F
H


I.1.2062
furan-2-yl
3-CN
5-F
H


I.1.2063
furan-2-yl
3-CN
4-CH3
H


I.1.2064
furan-2-yl
3-CN
5-CH3
H


I.1.2065
furan-2-yl
3-CN
4-CN
H


I.1.2066
furan-2-yl
3-CN
5-CN
H


I.1.2067
furan-2-yl
3-CN
4-CF3
H


I.1.2068
furan-2-yl
3-CN
5-CF3
H


I.1.2069
furan-2-yl
3-COOH
4-Cl
5-F


I.1.2070
furan-2-yl
3-COOH
4-Cl
H


I.1.2071
furan-2-yl
3-COOH
5-Cl
H


I.1.2072
furan-2-yl
3-COOH
4-F
H


I.1.2073
furan-2-yl
3-COOH
5-F
H


I.1.2074
furan-2-yl
3-COOH
4-CH3
H


I.1.2075
furan-2-yl
3-COOH
5-CH3
H


I.1.2076
furan-2-yl
3-COOH
4-CN
H


I.1.2077
furan-2-yl
3-COOH
5-CN
H


I.1.2078
furan-2-yl
3-COOH
4-CF3
H


I.1.2079
furan-2-yl
3-COOH
5-CF3
H


I.1.2080
furan-2-yl
3-COOCH3
4-Cl
5-F


I.1.2081
furan-2-yl
3-COOCH3
4-Cl
H


I.1.2082
furan-2-yl
3-COOCH3
5-Cl
H


I.1.2083
furan-2-yl
3-COOCH3
4-F
H


I.1.2084
furan-2-yl
3-COOCH3
5-F
H


I.1.2085
furan-2-yl
3-COOCH3
4-CH3
H


I.1.2086
furan-2-yl
3-COOCH3
5-CH3
H


I.1.2087
furan-2-yl
3-COOCH3
4-CN
H


I.1.2088
furan-2-yl
3-COOCH3
5-CN
H


I.1.2089
furan-2-yl
3-COOCH3
4-CF3
H


I.1.2090
furan-2-yl
3-COOCH3
5-CF3
H


I.1.2091
furan-2-yl
3-COOCH2CH3
4-Cl
5-F


I.1.2092
furan-2-yl
3-COOCH2CH3
4-Cl
H


I.1.2093
furan-2-yl
3-COOCH2CH3
5-Cl
H


I.1.2094
furan-2-yl
3-COOCH2CH3
4-F
H


I.1.2095
furan-2-yl
3-COOCH2CH3
5-F
H


I.1.2096
furan-2-yl
3-COOCH2CH3
4-CH3
H


I.1.2097
furan-2-yl
3-COOCH2CH3
5-CH3
H


I.1.2098
furan-2-yl
3-COOCH2CH3
4-CN
H


I.1.2099
furan-2-yl
3-COOCH2CH3
5-CN
H


I.1.2100
furan-2-yl
3-COOCH2CH3
4-CF3
H


I.1.2101
furan-2-yl
3-COOCH2CH3
5-CF3
H


I.1.2102
furan-2-yl
3-ethynyl
4-Cl
5-F


I.1.2103
furan-2-yl
3-ethynyl
4-Cl
H


I.1.2104
furan-2-yl
3-ethynyl
5-Cl
H


I.1.2105
furan-2-yl
3-ethynyl
4-F
H


I.1.2106
furan-2-yl
3-ethynyl
5-F
H


I.1.2107
furan-2-yl
3-ethynyl
4-CH3
H


I.1.2108
furan-2-yl
3-ethynyl
5-CH3
H


I.1.2109
furan-2-yl
3-ethynyl
4-CN
H


I.1.2110
furan-2-yl
3-ethynyl
5-CN
H


I.1.2111
furan-2-yl
3-ethynyl
4-CF3
H


I.1.2112
furan-2-yl
3-ethynyl
5-CF3
H


I.1.2113
furan-2-yl
3-I
4-Cl
5-F


I.1.2114
furan-2-yl
3-I
4-Cl
H


I.1.2115
furan-2-yl
3-I
5-Cl
H


I.1.2116
furan-2-yl
3-I
4-F
H


I.1.2117
furan-2-yl
3-I
5-F
H


I.1.2118
furan-2-yl
3-I
4-CH3
H


I.1.2119
furan-2-yl
3-I
5-CH3
H


I.1.2120
furan-2-yl
3-I
4-CN
H


I.1.2121
furan-2-yl
3-I
5-CN
H


I.1.2122
furan-2-yl
3-I
4-CF3
H


I.1.2123
furan-2-yl
3-I
5-CF3
H


I.1.2124
furan-2-yl
3-Cl
4-Cl
5-F


I.1.2125
furan-2-yl
3-Cl
4-Cl
H


I.1.2126
furan-2-yl
3-Cl
5-Cl
H


I.1.2127
furan-2-yl
3-Cl
4-F
H


I.1.2128
furan-2-yl
3-Cl
5-F
H


I.1.2129
furan-2-yl
3-Cl
4-CH3
H


I.1.2130
furan-2-yl
3-Cl
5-CH3
H


I.1.2131
furan-2-yl
3-Cl
4-CN
H


I.1.2132
furan-2-yl
3-Cl
5-CN
H


I.1.2133
furan-2-yl
3-Cl
4-CF3
H


I.1.2134
furan-2-yl
3-Cl
5-CF3
H


I.1.2135
furan-2-yl
3-Br
4-Cl
5-F


I.1.2136
furan-2-yl
3-Br
4-Cl
H


I.1.2137
furan-2-yl
3-Br
5-Cl
H


I.1.2138
furan-2-yl
3-Br
4-F
H


I.1.2139
furan-2-yl
3-Br
5-F
H


I.1.2140
furan-2-yl
3-Br
4-CH3
H


I.1.2141
furan-2-yl
3-Br
5-CH3
H


I.1.2142
furan-2-yl
3-Br
4-CN
H


I.1.2143
furan-2-yl
3-Br
5-CN
H


I.1.2144
furan-2-yl
3-Br
4-CF3
H


I.1.2145
furan-2-yl
3-Br
5-CF3
H


I.1.2146
furan-2-yl
3-CON(CH3)2
4-Cl
5-F


I.1.2147
furan-2-yl
3-CON(CH3)2
4-Cl
H


I.1.2148
furan-2-yl
3-CON(CH3)2
5-Cl
H


I.1.2149
furan-2-yl
3-CON(CH3)2
4-F
H


I.1.2150
furan-2-yl
3-CON(CH3)2
5-F
H


I.1.2151
furan-2-yl
3-CON(CH3)2
4-CH3
H


I.1.2152
furan-2-yl
3-CON(CH3)2
5-CH3
H


I.1.2153
furan-2-yl
3-CON(CH3)2
4-CN
H


I.1.2154
furan-2-yl
3-CON(CH3)2
5-CN
H


I.1.2155
furan-2-yl
3-CON(CH3)2
4-CF3
H


I.1.2156
furan-2-yl
3-CON(CH3)2
5-CF3
H


I.1.2157
furan-2-yl
3-CONHCH3
4-Cl
5-F


I.1.2158
furan-2-yl
3-CONHCH3
4-Cl
H


I.1.2159
furan-2-yl
3-CONHCH3
5-Cl
H


I.1.2160
furan-2-yl
3-CONHCH3
4-F
H


I.1.2161
furan-2-yl
3-CONHCH3
5-F
H


I.1.2162
furan-2-yl
3-CONHCH3
4-CH3
H


I.1.2163
furan-2-yl
3-CONHCH3
5-CH3
H


I.1.2164
furan-2-yl
3-CONHCH3
4-CN
H


I.1.2165
furan-2-yl
3-CONHCH3
5-CN
H


I.1.2166
furan-2-yl
3-CONHCH3
4-CF3
H


I.1.2167
furan-2-yl
3-CONHCH3
5-CF3
H


I.1.2168
furan-3-yl
2-NO2
4-Cl
5-F


I.1.2169
furan-3-yl
2-NO2
4-Cl
H


I.1.2170
furan-3-yl
2-NO2
5-Cl
H


I.1.2171
furan-3-yl
2-NO2
4-F
H


I.1.2172
furan-3-yl
2-NO2
5-F
H


I.1.2173
furan-3-yl
2-NO2
4-CH3
H


I.1.2174
furan-3-yl
2-NO2
5-CH3
H


I.1.2175
furan-3-yl
2-NO2
4-CN
H


I.1.2176
furan-3-yl
2-NO2
5-CN
H


I.1.2177
furan-3-yl
2-NO2
4-CF3
H


I.1.2178
furan-3-yl
2-NO2
5-CF3
H


I.1.2179
furan-3-yl
2-CN
4-Cl
5-F


I.1.2180
furan-3-yl
2-CN
4-Cl
H


I.1.2181
furan-3-yl
2-CN
5-Cl
H


I.1.2182
furan-3-yl
2-CN
4-F
H


I.1.2183
furan-3-yl
2-CN
5-F
H


I.1.2184
furan-3-yl
2-CN
4-CH3
H


I.1.2185
furan-3-yl
2-CN
5-CH3
H


I.1.2186
furan-3-yl
2-CN
4-CN
H


I.1.2187
furan-3-yl
2-CN
5-CN
H


I.1.2188
furan-3-yl
2-CN
4-CF3
H


I.1.2189
furan-3-yl
2-CN
5-CF3
H


I.1.2190
furan-3-yl
2-COOH
4-Cl
5-F


I.1.2191
furan-3-yl
2-COOH
4-Cl
H


I.1.2192
furan-3-yl
2-COOH
5-Cl
H


I.1.2193
furan-3-yl
2-COOH
4-F
H


I.1.2194
furan-3-yl
2-COOH
5-F
H


I.1.2195
furan-3-yl
2-COOH
4-CH3
H


I.1.2196
furan-3-yl
2-COOH
5-CH3
H


I.1.2197
furan-3-yl
2-COOH
4-CN
H


I.1.2198
furan-3-yl
2-COOH
5-CN
H


I.1.2199
furan-3-yl
2-COOH
4-CF3
H


I.1.2200
furan-3-yl
2-COOH
5-CF3
H


I.1.2201
furan-3-yl
2-COOCH3
4-Cl
5-F


I.1.2202
furan-3-yl
2-COOCH3
4-Cl
H


I.1.2203
furan-3-yl
2-COOCH3
5-Cl
H


I.1.2204
furan-3-yl
2-COOCH3
4-F
H


I.1.2205
furan-3-yl
2-COOCH3
5-F
H


I.1.2206
furan-3-yl
2-COOCH3
4-CH3
H


I.1.2207
furan-3-yl
2-COOCH3
5-CH3
H


I.1.2208
furan-3-yl
2-COOCH3
4-CN
H


I.1.2209
furan-3-yl
2-COOCH3
5-CN
H


I.1.2210
furan-3-yl
2-COOCH3
4-CF3
H


I.1.2211
furan-3-yl
2-COOCH3
5-CF3
H


I.1.2212
furan-3-yl
2-COOCH2CH3
4-Cl
5-F


I.1.2213
furan-3-yl
2-COOCH2CH3
4-Cl
H


I.1.2214
furan-3-yl
2-COOCH2CH3
5-Cl
H


I.1.2215
furan-3-yl
2-COOCH2CH3
4-F
H


I.1.2216
furan-3-yl
2-COOCH2CH3
5-F
H


I.1.2217
furan-3-yl
2-COOCH2CH3
4-CH3
H


I.1.2218
furan-3-yl
2-COOCH2CH3
5-CH3
H


I.1.2219
furan-3-yl
2-COOCH2CH3
4-CN
H


I.1.2220
furan-3-yl
2-COOCH2CH3
5-CN
H


I.1.2221
furan-3-yl
2-COOCH2CH3
4-CF3
H


I.1.2222
furan-3-yl
2-COOCH2CH3
5-CF3
H


I.1.2223
furan-3-yl
2-ethynyl
4-Cl
5-F


I.1.2224
furan-3-yl
2-ethynyl
4-Cl
H


I.1.2225
furan-3-yl
2-ethynyl
5-Cl
H


I.1.2226
furan-3-yl
2-ethynyl
4-F
H


I.1.2227
furan-3-yl
2-ethynyl
5-F
H


I.1.2228
furan-3-yl
2-ethynyl
4-CH3
H


I.1.2229
furan-3-yl
2-ethynyl
5-CH3
H


I.1.2230
furan-3-yl
2-ethynyl
4-CN
H


I.1.2231
furan-3-yl
2-ethynyl
5-CN
H


I.1.2232
furan-3-yl
2-ethynyl
4-CF3
H


I.1.2233
furan-3-yl
2-ethynyl
5-CF3
H


I.1.2234
furan-3-yl
2-I
4-Cl
5-F


I.1.2235
furan-3-yl
2-I
4-Cl
H


I.1.2236
furan-3-yl
2-I
5-Cl
H


I.1.2237
furan-3-yl
2-I
4-F
H


I.1.2238
furan-3-yl
2-I
5-F
H


I.1.2239
furan-3-yl
2-I
4-CH3
H


I.1.2240
furan-3-yl
2-I
5-CH3
H


I.1.2241
furan-3-yl
2-I
4-CN
H


I.1.2242
furan-3-yl
2-I
5-CN
H


I.1.2243
furan-3-yl
2-I
4-CF3
H


I.1.2244
furan-3-yl
2-I
5-CF3
H


I.1.2245
furan-3-yl
2-Cl
4-Cl
5-F


I.1.2246
furan-3-yl
2-Cl
4-Cl
H


I.1.2247
furan-3-yl
2-Cl
5-Cl
H


I.1.2248
furan-3-yl
2-Cl
4-F
H


I.1.2249
furan-3-yl
2-Cl
5-F
H


I.1.2250
furan-3-yl
2-Cl
4-CH3
H


I.1.2251
furan-3-yl
2-Cl
5-CH3
H


I.1.2252
furan-3-yl
2-Cl
4-CN
H


I.1.2253
furan-3-yl
2-Cl
5-CN
H


I.1.2254
furan-3-yl
2-Cl
4-CF3
H


I.1.2255
furan-3-yl
2-Cl
5-CF3
H


I.1.2256
furan-3-yl
2-Br
4-Cl
5-F


I.1.2257
furan-3-yl
2-Br
4-Cl
H


I.1.2258
furan-3-yl
2-Br
5-Cl
H


I.1.2259
furan-3-yl
2-Br
4-F
H


I.1.2260
furan-3-yl
2-Br
5-F
H


I.1.2261
furan-3-yl
2-Br
4-CH3
H


I.1.2262
furan-3-yl
2-Br
5-CH3
H


I.1.2263
furan-3-yl
2-Br
4-CN
H


I.1.2264
furan-3-yl
2-Br
5-CN
H


I.1.2265
furan-3-yl
2-Br
4-CF3
H


I.1.2266
furan-3-yl
2-Br
5-CF3
H


I.1.2267
furan-3-yl
2-CON(CH3)2
4-Cl
5-F


I.1.2268
furan-3-yl
2-CON(CH3)2
4-Cl
H


I.1.2269
furan-3-yl
2-CON(CH3)2
5-Cl
H


I.1.2270
furan-3-yl
2-CON(CH3)2
4-F
H


I.1.2271
furan-3-yl
2-CON(CH3)2
5-F
H


I.1.2272
furan-3-yl
2-CON(CH3)2
4-CH3
H


I.1.2273
furan-3-yl
2-CON(CH3)2
5-CH3
H


I.1.2274
furan-3-yl
2-CON(CH3)2
4-CN
H


I.1.2275
furan-3-yl
2-CON(CH3)2
5-CN
H


I.1.2276
furan-3-yl
2-CON(CH3)2
4-CF3
H


I.1.2277
furan-3-yl
2-CON(CH3)2
5-CF3
H


I.1.2278
furan-3-yl
2-CONHCH3
4-Cl
5-F


I.1.2279
furan-3-yl
2-CONHCH3
4-Cl
H


I.1.2280
furan-3-yl
2-CONHCH3
5-Cl
H


I.1.2281
furan-3-yl
2-CONHCH3
4-F
H


I.1.2282
furan-3-yl
2-CONHCH3
5-F
H


I.1.2283
furan-3-yl
2-CONHCH3
4-CH3
H


I.1.2284
furan-3-yl
2-CONHCH3
5-CH3
H


I.1.2285
furan-3-yl
2-CONHCH3
4-CN
H


I.1.2286
furan-3-yl
2-CONHCH3
5-CN
H


I.1.2287
furan-3-yl
2-CONHCH3
4-CF3
H


I.1.2288
furan-3-yl
2-CONHCH3
5-CF3
H


I.1.2289
furan-3-yl
4-NO2
5-Cl
2-F


I.1.2290
furan-3-yl
4-NO2
5-Cl
H


I.1.2291
furan-3-yl
4-NO2
2-Cl
H


I.1.2292
furan-3-yl
4-NO2
5-F
H


I.1.2293
furan-3-yl
4-NO2
2-F
H


I.1.2294
furan-3-yl
4-NO2
5-CH3
H


I.1.2295
furan-3-yl
4-NO2
2-CH3
H


I.1.2296
furan-3-yl
4-NO2
5-CN
H


I.1.2297
furan-3-yl
4-NO2
2-CN
H


I.1.2298
furan-3-yl
4-NO2
5-CF3
H


I.1.2299
furan-3-yl
4-NO2
2-CF3
H


I.1.2300
furan-3-yl
4-CN
5-Cl
2-F


I.1.2301
furan-3-yl
4-CN
5-Cl
H


I.1.2302
furan-3-yl
4-CN
2-Cl
H


I.1.2303
furan-3-yl
4-CN
5-F
H


I.1.2304
furan-3-yl
4-CN
2-F
H


I.1.2305
furan-3-yl
4-CN
5-CH3
H


I.1.2306
furan-3-yl
4-CN
2-CH3
H


I.1.2307
furan-3-yl
4-CN
5-CN
H


I.1.2308
furan-3-yl
4-CN
2-CN
H


I.1.2309
furan-3-yl
4-CN
5-CF3
H


I.1.2310
furan-3-yl
4-CN
2-CF3
H


I.1.2311
furan-3-yl
4-COOH
5-Cl
2-F


I.1.2312
furan-3-yl
4-COOH
5-Cl
H


I.1.2313
furan-3-yl
4-COOH
2-Cl
H


I.1.2314
furan-3-yl
4-COOH
5-F
H


I.1.2315
furan-3-yl
4-COOH
2-F
H


I.1.2316
furan-3-yl
4-COOH
5-CH3
H


I.1.2317
furan-3-yl
4-COOH
2-CH3
H


I.1.2318
furan-3-yl
4-COOH
5-CN
H


I.1.2319
furan-3-yl
4-COOH
2-CN
H


I.1.2320
furan-3-yl
4-COOH
5-CF3
H


I.1.2321
furan-3-yl
4-COOH
2-CF3
H


I.1.2322
furan-3-yl
4-COOCH3
5-Cl
2-F


I.1.2323
furan-3-yl
4-COOCH3
5-Cl
H


I.1.2324
furan-3-yl
4-COOCH3
2-Cl
H


I.1.2325
furan-3-yl
4-COOCH3
5-F
H


I.1.2326
furan-3-yl
4-COOCH3
2-F
H


I.1.2327
furan-3-yl
4-COOCH3
5-CH3
H


I.1.2328
furan-3-yl
4-COOCH3
2-CH3
H


I.1.2329
furan-3-yl
4-COOCH3
5-CN
H


I.1.2330
furan-3-yl
4-COOCH3
2-CN
H


I.1.2331
furan-3-yl
4-COOCH3
5-CF3
H


I.1.2332
furan-3-yl
4-COOCH3
2-CF3
H


I.1.2333
furan-3-yl
4-COOCH2CH3
5-Cl
2-F


I.1.2334
furan-3-yl
4-COOCH2CH3
5-Cl
H


I.1.2335
furan-3-yl
4-COOCH2CH3
2-Cl
H


I.1.2336
furan-3-yl
4-COOCH2CH3
5-F
H


I.1.2337
furan-3-yl
4-COOCH2CH3
2-F
H


I.1.2338
furan-3-yl
4-COOCH2CH3
5-CH3
H


I.1.2339
furan-3-yl
4-COOCH2CH3
2-CH3
H


I.1.2340
furan-3-yl
4-COOCH2CH3
5-CN
H


I.1.2341
furan-3-yl
4-COOCH2CH3
2-CN
H


I.1.2342
furan-3-yl
4-COOCH2CH3
5-CF3
H


I.1.2343
furan-3-yl
4-COOCH2CH3
2-CF3
H


I.1.2344
furan-3-yl
4-ethynyl
5-Cl
2-F


I.1.2345
furan-3-yl
4-ethynyl
5-Cl
H


I.1.2346
furan-3-yl
4-ethynyl
2-Cl
H


I.1.2347
furan-3-yl
4-ethynyl
5-F
H


I.1.2348
furan-3-yl
4-ethynyl
2-F
H


I.1.2349
furan-3-yl
4-ethynyl
5-CH3
H


I.1.2350
furan-3-yl
4-ethynyl
2-CH3
H


I.1.2351
furan-3-yl
4-ethynyl
5-CN
H


I.1.2352
furan-3-yl
4-ethynyl
2-CN
H


I.1.2353
furan-3-yl
4-ethynyl
5-CF3
H


I.1.2354
furan-3-yl
4-ethynyl
2-CF3
H


I.1.2355
furan-3-yl
4-I
5-Cl
2-F


I.1.2356
furan-3-yl
4-I
5-Cl
H


I.1.2357
furan-3-yl
4-I
2-Cl
H


I.1.2358
furan-3-yl
4-I
5-F
H


I.1.2359
furan-3-yl
4-I
2-F
H


I.1.2360
furan-3-yl
4-I
5-CH3
H


I.1.2361
furan-3-yl
4-I
2-CH3
H


I.1.2362
furan-3-yl
4-I
5-CN
H


I.1.2363
furan-3-yl
4-I
2-CN
H


I.1.2364
furan-3-yl
4-I
5-CF3
H


I.1.2365
furan-3-yl
4-I
2-CF3
H


I.1.2366
furan-3-yl
4-Cl
5-Cl
2-F


I.1.2367
furan-3-yl
4-Cl
5-Cl
H


I.1.2368
furan-3-yl
4-Cl
2-Cl
H


I.1.2369
furan-3-yl
4-Cl
5-F
H


I.1.2370
furan-3-yl
4-Cl
2-F
H


I.1.2371
furan-3-yl
4-Cl
5-CH3
H


I.1.2372
furan-3-yl
4-Cl
2-CH3
H


I.1.2373
furan-3-yl
4-Cl
5-CN
H


I.1.2374
furan-3-yl
4-Cl
2-CN
H


I.1.2375
furan-3-yl
4-Cl
5-CF3
H


I.1.2376
furan-3-yl
4-Cl
2-CF3
H


I.1.2377
furan-3-yl
4-Br
5-Cl
2-F


I.1.2378
furan-3-yl
4-Br
5-Cl
H


I.1.2379
furan-3-yl
4-Br
2-Cl
H


I.1.2380
furan-3-yl
4-Br
5-F
H


I.1.2381
furan-3-yl
4-Br
2-F
H


I.1.2382
furan-3-yl
4-Br
5-CH3
H


I.1.2383
furan-3-yl
4-Br
2-CH3
H


I.1.2384
furan-3-yl
4-Br
5-CN
H


I.1.2385
furan-3-yl
4-Br
2-CN
H


I.1.2386
furan-3-yl
4-Br
5-CF3
H


I.1.2387
furan-3-yl
4-Br
2-CF3
H


I.1.2388
furan-3-yl
4-CON(CH3)2
5-Cl
2-F


I.1.2389
furan-3-yl
4-CON(CH3)2
5-Cl
H


I.1.2390
furan-3-yl
4-CON(CH3)2
2-Cl
H


I.1.2391
furan-3-yl
4-CON(CH3)2
5-F
H


I.1.2392
furan-3-yl
4-CON(CH3)2
2-F
H


I.1.2393
furan-3-yl
4-CON(CH3)2
5-CH3
H


I.1.2394
furan-3-yl
4-CON(CH3)2
2-CH3
H


I.1.2395
furan-3-yl
4-CON(CH3)2
5-CN
H


I.1.2396
furan-3-yl
4-CON(CH3)2
2-CN
H


I.1.2397
furan-3-yl
4-CON(CH3)2
5-CF3
H


I.1.2398
furan-3-yl
4-CON(CH3)2
2-CF3
H


I.1.2399
furan-3-yl
4-CONHCH3
5-Cl
2-F


I.1.2400
furan-3-yl
4-CONHCH3
5-Cl
H


I.1.2401
furan-3-yl
4-CONHCH3
2-Cl
H


I.1.2402
furan-3-yl
4-CONHCH3
5-F
H


I.1.2403
furan-3-yl
4-CONHCH3
2-F
H


I.1.2404
furan-3-yl
4-CONHCH3
5-CH3
H


I.1.2405
furan-3-yl
4-CONHCH3
2-CH3
H


I.1.2406
furan-3-yl
4-CONHCH3
5-CN
H


I.1.2407
furan-3-yl
4-CONHCH3
2-CN
H


I.1.2408
furan-3-yl
4-CONHCH3
5-CF3
H


I.1.2409
furan-3-yl
4-CONHCH3
2-CF3
H


I.1.2410
thiophen-2-yl
3-NO2
4-Cl
5-F


I.1.2411
thiophen-2-yl
3-NO2
4-Cl
H


I.1.2412
thiophen-2-yl
3-NO2
5-Cl
H


I.1.2413
thiophen-2-yl
3-NO2
4-F
H


I.1.2414
thiophen-2-yl
3-NO2
5-F
H


I.1.2415
thiophen-2-yl
3-NO2
4-CH3
H


I.1.2416
thiophen-2-yl
3-NO2
5-CH3
H


I.1.2417
thiophen-2-yl
3-NO2
4-CN
H


I.1.2418
thiophen-2-yl
3-NO2
5-CN
H


I.1.2419
thiophen-2-yl
3-NO2
4-CF3
H


I.1.2420
thiophen-2-yl
3-NO2
5-CF3
H


I.1.2421
thiophen-2-yl
3-CN
4-Cl
5-F


I.1.2422
thiophen-2-yl
3-CN
4-Cl
H


I.1.2423
thiophen-2-yl
3-CN
5-Cl
H


I.1.2424
thiophen-2-yl
3-CN
4-F
H


I.1.2425
thiophen-2-yl
3-CN
5-F
H


I.1.2426
thiophen-2-yl
3-CN
4-CH3
H


I.1.2427
thiophen-2-yl
3-CN
5-CH3
H


I.1.2428
thiophen-2-yl
3-CN
4-CN
H


I.1.2429
thiophen-2-yl
3-CN
5-CN
H


I.1.2430
thiophen-2-yl
3-CN
4-CF3
H


I.1.2431
thiophen-2-yl
3-CN
5-CF3
H


I.1.2432
thiophen-2-yl
3-COOH
4-Cl
5-F


I.1.2433
thiophen-2-yl
3-COOH
4-Cl
H


I.1.2434
thiophen-2-yl
3-COOH
5-Cl
H


I.1.2435
thiophen-2-yl
3-COOH
4-F
H


I.1.2436
thiophen-2-yl
3-COOH
5-F
H


I.1.2437
thiophen-2-yl
3-COOH
4-CH3
H


I.1.2438
thiophen-2-yl
3-COOH
5-CH3
H


I.1.2439
thiophen-2-yl
3-COOH
4-CN
H


I.1.2440
thiophen-2-yl
3-COOH
5-CN
H


I.1.2441
thiophen-2-yl
3-COOH
4-CF3
H


I.1.2442
thiophen-2-yl
3-COOH
5-CF3
H


I.1.2443
thiophen-2-yl
3-COOCH3
4-Cl
5-F


I.1.2444
thiophen-2-yl
3-COOCH3
4-Cl
H


I.1.2445
thiophen-2-yl
3-COOCH3
5-Cl
H


I.1.2446
thiophen-2-yl
3-COOCH3
4-F
H


I.1.2447
thiophen-2-yl
3-COOCH3
5-F
H


I.1.2448
thiophen-2-yl
3-COOCH3
4-CH3
H


I.1.2449
thiophen-2-yl
3-COOCH3
5-CH3
H


I.1.2450
thiophen-2-yl
3-COOCH3
4-CN
H


I.1.2451
thiophen-2-yl
3-COOCH3
5-CN
H


I.1.2452
thiophen-2-yl
3-COOCH3
4-CF3
H


I.1.2453
thiophen-2-yl
3-COOCH3
5-CF3
H


I.1.2454
thiophen-2-yl
3-COOCH2CH3
4-Cl
5-F


I.1.2455
thiophen-2-yl
3-COOCH2CH3
4-Cl
H


I.1.2456
thiophen-2-yl
3-COOCH2CH3
5-Cl
H


I.1.2457
thiophen-2-yl
3-COOCH2CH3
4-F
H


I.1.2458
thiophen-2-yl
3-COOCH2CH3
5-F
H


I.1.2459
thiophen-2-yl
3-COOCH2CH3
4-CH3
H


I.1.2460
thiophen-2-yl
3-COOCH2CH3
5-CH3
H


I.1.2461
thiophen-2-yl
3-COOCH2CH3
4-CN
H


I.1.2462
thiophen-2-yl
3-COOCH2CH3
5-CN
H


I.1.2463
thiophen-2-yl
3-COOCH2CH3
4-CF3
H


I.1.2464
thiophen-2-yl
3-COOCH2CH3
5-CF3
H


I.1.2465
thiophen-2-yl
3-ethynyl
4-Cl
5-F


I.1.2466
thiophen-2-yl
3-ethynyl
4-Cl
H


I.1.2467
thiophen-2-yl
3-ethynyl
5-Cl
H


I.1.2468
thiophen-2-yl
3-ethynyl
4-F
H


I.1.2469
thiophen-2-yl
3-ethynyl
5-F
H


I.1.2470
thiophen-2-yl
3-ethynyl
4-CH3
H


I.1.2471
thiophen-2-yl
3-ethynyl
5-CH3
H


I.1.2472
thiophen-2-yl
3-ethynyl
4-CN
H


I.1.2473
thiophen-2-yl
3-ethynyl
5-CN
H


I.1.2474
thiophen-2-yl
3-ethynyl
4-CF3
H


I.1.2475
thiophen-2-yl
3-ethynyl
5-CF3
H


I.1.2476
thiophen-2-yl
3-I
4-Cl
5-F


I.1.2477
thiophen-2-yl
3-I
4-Cl
H


I.1.2478
thiophen-2-yl
3-I
5-Cl
H


I.1.2479
thiophen-2-yl
3-I
4-F
H


I.1.2480
thiophen-2-yl
3-I
5-F
H


I.1.2481
thiophen-2-yl
3-I
4-CH3
H


I.1.2482
thiophen-2-yl
3-I
5-CH3
H


I.1.2483
thiophen-2-yl
3-I
4-CN
H


I.1.2484
thiophen-2-yl
3-I
5-CN
H


I.1.2485
thiophen-2-yl
3-I
4-CF3
H


I.1.2486
thiophen-2-yl
3-I
5-CF3
H


I.1.2487
thiophen-2-yl
3-Cl
4-Cl
5-F


I.1.2488
thiophen-2-yl
3-Cl
4-Cl
H


I.1.2489
thiophen-2-yl
3-Cl
5-Cl
H


I.1.2490
thiophen-2-yl
3-Cl
4-F
H


I.1.2491
thiophen-2-yl
3-Cl
5-F
H


I.1.2492
thiophen-2-yl
3-Cl
4-CH3
H


I.1.2493
thiophen-2-yl
3-Cl
5-CH3
H


I.1.2494
thiophen-2-yl
3-Cl
4-CN
H


I.1.2495
thiophen-2-yl
3-Cl
5-CN
H


I.1.2496
thiophen-2-yl
3-Cl
4-CF3
H


I.1.2497
thiophen-2-yl
3-Cl
5-CF3
H


I.1.2498
thiophen-2-yl
3-Br
4-Cl
5-F


I.1.2499
thiophen-2-yl
3-Br
4-Cl
H


I.1.2500
thiophen-2-yl
3-Br
5-Cl
H


I.1.2501
thiophen-2-yl
3-Br
4-F
H


I.1.2502
thiophen-2-yl
3-Br
5-F
H


I.1.2503
thiophen-2-yl
3-Br
4-CH3
H


I.1.2504
thiophen-2-yl
3-Br
5-CH3
H


I.1.2505
thiophen-2-yl
3-Br
4-CN
H


I.1.2506
thiophen-2-yl
3-Br
5-CN
H


I.1.2507
thiophen-2-yl
3-Br
4-CF3
H


I.1.2508
thiophen-2-yl
3-Br
5-CF3
H


I.1.2509
thiophen-2-yl
3-CON(CH3)2
4-Cl
5-F


I.1.2510
thiophen-2-yl
3-CON(CH3)2
4-Cl
H


I.1.2511
thiophen-2-yl
3-CON(CH3)2
5-Cl
H


I.1.2512
thiophen-2-yl
3-CON(CH3)2
4-F
H


I.1.2513
thiophen-2-yl
3-CON(CH3)2
5-F
H


I.1.2514
thiophen-2-yl
3-CON(CH3)2
4-CH3
H


I.1.2515
thiophen-2-yl
3-CON(CH3)2
5-CH3
H


I.1.2516
thiophen-2-yl
3-CON(CH3)2
4-CN
H


I.1.2517
thiophen-2-yl
3-CON(CH3)2
5-CN
H


I.1.2518
thiophen-2-yl
3-CON(CH3)2
4-CF3
H


I.1.2519
thiophen-2-yl
3-CON(CH3)2
5-CF3
H


I.1.2520
thiophen-2-yl
3-CONHCH3
4-Cl
5-F


I.1.2521
thiophen-2-yl
3-CONHCH3
4-Cl
H


I.1.2522
thiophen-2-yl
3-CONHCH3
5-Cl
H


I.1.2523
thiophen-2-yl
3-CONHCH3
4-F
H


I.1.2524
thiophen-2-yl
3-CONHCH3
5-F
H


I.1.2525
thiophen-2-yl
3-CONHCH3
4-CH3
H


I.1.2526
thiophen-2-yl
3-CONHCH3
5-CH3
H


I.1.2527
thiophen-2-yl
3-CONHCH3
4-CN
H


I.1.2528
thiophen-2-yl
3-CONHCH3
5-CN
H


I.1.2529
thiophen-2-yl
3-CONHCH3
4-CF3
H


I.1.2530
thiophen-2-yl
3-CONHCH3
5-CF3
H


I.1.2531
thiophen-3-yl
2-NO2
4-Cl
5-F


I.1.2532
thiophen-3-yl
2-NO2
4-Cl
H


I.1.2533
thiophen-3-yl
2-NO2
5-Cl
H


I.1.2534
thiophen-3-yl
2-NO2
4-F
H


I.1.2535
thiophen-3-yl
2-NO2
5-F
H


I.1.2536
thiophen-3-yl
2-NO2
4-CH3
H


I.1.2537
thiophen-3-yl
2-NO2
5-CH3
H


I.1.2538
thiophen-3-yl
2-NO2
4-CN
H


I.1.2539
thiophen-3-yl
2-NO2
5-CN
H


I.1.2540
thiophen-3-yl
2-NO2
4-CF3
H


I.1.2541
thiophen-3-yl
2-NO2
5-CF3
H


I.1.2542
thiophen-3-yl
2-CN
4-Cl
5-F


I.1.2543
thiophen-3-yl
2-CN
4-Cl
H


I.1.2544
thiophen-3-yl
2-CN
5-Cl
H


I.1.2545
thiophen-3-yl
2-CN
4-F
H


I.1.2546
thiophen-3-yl
2-CN
5-F
H


I.1.2547
thiophen-3-yl
2-CN
4-CH3
H


I.1.2548
thiophen-3-yl
2-CN
5-CH3
H


I.1.2549
thiophen-3-yl
2-CN
4-CN
H


I.1.2550
thiophen-3-yl
2-CN
5-CN
H


I.1.2551
thiophen-3-yl
2-CN
4-CF3
H


I.1.2552
thiophen-3-yl
2-CN
5-CF3
H


I.1.2553
thiophen-3-yl
2-COOH
4-Cl
5-F


I.1.2554
thiophen-3-yl
2-COOH
4-Cl
H


I.1.2555
thiophen-3-yl
2-COOH
5-Cl
H


I.1.2556
thiophen-3-yl
2-COOH
4-F
H


I.1.2557
thiophen-3-yl
2-COOH
5-F
H


I.1.2558
thiophen-3-yl
2-COOH
4-CH3
H


I.1.2559
thiophen-3-yl
2-COOH
5-CH3
H


I.1.2560
thiophen-3-yl
2-COOH
4-CN
H


I.1.2561
thiophen-3-yl
2-COOH
5-CN
H


I.1.2562
thiophen-3-yl
2-COOH
4-CF3
H


I.1.2563
thiophen-3-yl
2-COOH
5-CF3
H


I.1.2564
thiophen-3-yl
2-COOCH3
4-Cl
5-F


I.1.2565
thiophen-3-yl
2-COOCH3
4-Cl
H


I.1.2566
thiophen-3-yl
2-COOCH3
5-Cl
H


I.1.2567
thiophen-3-yl
2-COOCH3
4-F
H


I.1.2568
thiophen-3-yl
2-COOCH3
5-F
H


I.1.2569
thiophen-3-yl
2-COOCH3
4-CH3
H


I.1.2570
thiophen-3-yl
2-COOCH3
5-CH3
H


I.1.2571
thiophen-3-yl
2-COOCH3
4-CN
H


I.1.2572
thiophen-3-yl
2-COOCH3
5-CN
H


I.1.2573
thiophen-3-yl
2-COOCH3
4-CF3
H


I.1.2574
thiophen-3-yl
2-COOCH3
5-CF3
H


I.1.2575
thiophen-3-yl
2-COOCH2CH3
4-Cl
5-F


I.1.2576
thiophen-3-yl
2-COOCH2CH3
4-Cl
H


I.1.2577
thiophen-3-yl
2-COOCH2CH3
5-Cl
H


I.1.2578
thiophen-3-yl
2-COOCH2CH3
4-F
H


I.1.2579
thiophen-3-yl
2-COOCH2CH3
5-F
H


I.1.2580
thiophen-3-yl
2-COOCH2CH3
4-CH3
H


I.1.2581
thiophen-3-yl
2-COOCH2CH3
5-CH3
H


I.1.2582
thiophen-3-yl
2-COOCH2CH3
4-CN
H


I.1.2583
thiophen-3-yl
2-COOCH2CH3
5-CN
H


I.1.2584
thiophen-3-yl
2-COOCH2CH3
4-CF3
H


I.1.2585
thiophen-3-yl
2-COOCH2CH3
5-CF3
H


I.1.2586
thiophen-3-yl
2-ethynyl
4-Cl
5-F


I.1.2587
thiophen-3-yl
2-ethynyl
4-Cl
H


I.1.2588
thiophen-3-yl
2-ethynyl
5-Cl
H


I.1.2589
thiophen-3-yl
2-ethynyl
4-F
H


I.1.2590
thiophen-3-yl
2-ethynyl
5-F
H


I.1.2591
thiophen-3-yl
2-ethynyl
4-CH3
H


I.1.2592
thiophen-3-yl
2-ethynyl
5-CH3
H


I.1.2593
thiophen-3-yl
2-ethynyl
4-CN
H


I.1.2594
thiophen-3-yl
2-ethynyl
5-CN
H


I.1.2595
thiophen-3-yl
2-ethynyl
4-CF3
H


I.1.2596
thiophen-3-yl
2-ethynyl
5-CF3
H


I.1.2597
thiophen-3-yl
2-I
4-Cl
5-F


I.1.2598
thiophen-3-yl
2-I
4-Cl
H


I.1.2599
thiophen-3-yl
2-I
5-Cl
H


I.1.2600
thiophen-3-yl
2-I
4-F
H


I.1.2601
thiophen-3-yl
2-I
5-F
H


I.1.2602
thiophen-3-yl
2-I
4-CH3
H


I.1.2603
thiophen-3-yl
2-I
5-CH3
H


I.1.2604
thiophen-3-yl
2-I
4-CN
H


I.1.2605
thiophen-3-yl
2-I
5-CN
H


I.1.2606
thiophen-3-yl
2-I
4-CF3
H


I.1.2607
thiophen-3-yl
2-I
5-CF3
H


I.1.2608
thiophen-3-yl
2-Cl
4-Cl
5-F


I.1.2609
thiophen-3-yl
2-Cl
4-Cl
H


I.1.2610
thiophen-3-yl
2-Cl
5-Cl
H


I.1.2611
thiophen-3-yl
2-Cl
4-F
H


I.1.2612
thiophen-3-yl
2-Cl
5-F
H


I.1.2613
thiophen-3-yl
2-Cl
4-CH3
H


I.1.2614
thiophen-3-yl
2-Cl
5-CH3
H


I.1.2615
thiophen-3-yl
2-Cl
4-CN
H


I.1.2616
thiophen-3-yl
2-Cl
5-CN
H


I.1.2617
thiophen-3-yl
2-Cl
4-CF3
H


I.1.2618
thiophen-3-yl
2-Cl
5-CF3
H


I.1.2619
thiophen-3-yl
2-Br
4-Cl
5-F


I.1.2620
thiophen-3-yl
2-Br
4-Cl
H


I.1.2621
thiophen-3-yl
2-Br
5-Cl
H


I.1.2622
thiophen-3-yl
2-Br
4-F
H


I.1.2623
thiophen-3-yl
2-Br
5-F
H


I.1.2624
thiophen-3-yl
2-Br
4-CH3
H


I.1.2625
thiophen-3-yl
2-Br
5-CH3
H


I.1.2626
thiophen-3-yl
2-Br
4-CN
H


I.1.2627
thiophen-3-yl
2-Br
5-CN
H


I.1.2628
thiophen-3-yl
2-Br
4-CF3
H


I.1.2629
thiophen-3-yl
2-Br
5-CF3
H


I.1.2630
thiophen-3-yl
2-CON(CH3)2
4-Cl
5-F


I.1.2631
thiophen-3-yl
2-CON(CH3)2
4-Cl
H


I.1.2632
thiophen-3-yl
2-CON(CH3)2
5-Cl
H


I.1.2633
thiophen-3-yl
2-CON(CH3)2
4-F
H


I.1.2634
thiophen-3-yl
2-CON(CH3)2
5-F
H


I.1.2635
thiophen-3-yl
2-CON(CH3)2
4-CH3
H


I.1.2636
thiophen-3-yl
2-CON(CH3)2
5-CH3
H


I.1.2637
thiophen-3-yl
2-CON(CH3)2
4-CN
H


I.1.2638
thiophen-3-yl
2-CON(CH3)2
5-CN
H


I.1.2639
thiophen-3-yl
2-CON(CH3)2
4-CF3
H


I.1.2640
thiophen-3-yl
2-CON(CH3)2
5-CF3
H


I.1.2641
thiophen-3-yl
2-CONHCH3
4-Cl
5-F


I.1.2642
thiophen-3-yl
2-CONHCH3
4-Cl
H


I.1.2643
thiophen-3-yl
2-CONHCH3
5-Cl
H


I.1.2644
thiophen-3-yl
2-CONHCH3
4-F
H


I.1.2645
thiophen-3-yl
2-CONHCH3
5-F
H


I.1.2646
thiophen-3-yl
2-CONHCH3
4-CH3
H


I.1.2647
thiophen-3-yl
2-CONHCH3
5-CH3
H


I.1.2648
thiophen-3-yl
2-CONHCH3
4-CN
H


I.1.2649
thiophen-3-yl
2-CONHCH3
5-CN
H


I.1.2650
thiophen-3-yl
2-CONHCH3
4-CF3
H


I.1.2651
thiophen-3-yl
2-CONHCH3
5-CF3
H


I.1.2652
thiophen-3-yl
4-NO2
5-Cl
2-F


I.1.2653
thiophen-3-yl
4-NO2
5-Cl
H


I.1.2654
thiophen-3-yl
4-NO2
2-Cl
H


I.1.2655
thiophen-3-yl
4-NO2
5-F
H


I.1.2656
thiophen-3-yl
4-NO2
2-F
H


I.1.2657
thiophen-3-yl
4-NO2
5-CH3
H


I.1.2658
thiophen-3-yl
4-NO2
2-CH3
H


I.1.2659
thiophen-3-yl
4-NO2
5-CN
H


I.1.2660
thiophen-3-yl
4-NO2
2-CN
H


I.1.2661
thiophen-3-yl
4-NO2
5-CF3
H


I.1.2662
thiophen-3-yl
4-NO2
2-CF3
H


I.1.2663
thiophen-3-yl
4-CN
5-Cl
2-F


I.1.2664
thiophen-3-yl
4-CN
5-Cl
H


I.1.2665
thiophen-3-yl
4-CN
2-Cl
H


I.1.2666
thiophen-3-yl
4-CN
5-F
H


I.1.2667
thiophen-3-yl
4-CN
2-F
H


I.1.2668
thiophen-3-yl
4-CN
5-CH3
H


I.1.2669
thiophen-3-yl
4-CN
2-CH3
H


I.1.2670
thiophen-3-yl
4-CN
5-CN
H


I.1.2671
thiophen-3-yl
4-CN
2-CN
H


I.1.2672
thiophen-3-yl
4-CN
5-CF3
H


I.1.2673
thiophen-3-yl
4-CN
2-CF3
H


I.1.2674
thiophen-3-yl
4-COOH
5-Cl
2-F


I.1.2675
thiophen-3-yl
4-COOH
5-Cl
H


I.1.2676
thiophen-3-yl
4-COOH
2-Cl
H


I.1.2677
thiophen-3-yl
4-COOH
5-F
H


I.1.2678
thiophen-3-yl
4-COOH
2-F
H


I.1.2679
thiophen-3-yl
4-COOH
5-CH3
H


I.1.2680
thiophen-3-yl
4-COOH
2-CH3
H


I.1.2681
thiophen-3-yl
4-COOH
5-CN
H


I.1.2682
thiophen-3-yl
4-COOH
2-CN
H


I.1.2683
thiophen-3-yl
4-COOH
5-CF3
H


I.1.2684
thiophen-3-yl
4-COOH
2-CF3
H


I.1.2685
thiophen-3-yl
4-COOCH3
5-Cl
2-F


I.1.2686
thiophen-3-yl
4-COOCH3
5-Cl
H


I.1.2687
thiophen-3-yl
4-COOCH3
2-Cl
H


I.1.2688
thiophen-3-yl
4-COOCH3
5-F
H


I.1.2689
thiophen-3-yl
4-COOCH3
2-F
H


I.1.2690
thiophen-3-yl
4-COOCH3
5-CH3
H


I.1.2691
thiophen-3-yl
4-COOCH3
2-CH3
H


I.1.2692
thiophen-3-yl
4-COOCH3
5-CN
H


I.1.2693
thiophen-3-yl
4-COOCH3
2-CN
H


I.1.2694
thiophen-3-yl
4-COOCH3
5-CF3
H


I.1.2695
thiophen-3-yl
4-COOCH3
2-CF3
H


I.1.2696
thiophen-3-yl
4-COOCH2CH3
5-Cl
2-F


I.1.2697
thiophen-3-yl
4-COOCH2CH3
5-Cl
H


I.1.2698
thiophen-3-yl
4-COOCH2CH3
2-Cl
H


I.1.2699
thiophen-3-yl
4-COOCH2CH3
5-F
H


I.1.2700
thiophen-3-yl
4-COOCH2CH3
2-F
H


I.1.2701
thiophen-3-yl
4-COOCH2CH3
5-CH3
H


I.1.2702
thiophen-3-yl
4-COOCH2CH3
2-CH3
H


I.1.2703
thiophen-3-yl
4-COOCH2CH3
5-CN
H


I.1.2704
thiophen-3-yl
4-COOCH2CH3
2-CN
H


I.1.2705
thiophen-3-yl
4-COOCH2CH3
5-CF3
H


I.1.2706
thiophen-3-yl
4-COOCH2CH3
2-CF3
H


I.1.2707
thiophen-3-yl
4-ethynyl
5-Cl
2-F


I.1.2708
thiophen-3-yl
4-ethynyl
5-Cl
H


I.1.2709
thiophen-3-yl
4-ethynyl
2-Cl
H


I.1.2710
thiophen-3-yl
4-ethynyl
5-F
H


I.1.2711
thiophen-3-yl
4-ethynyl
2-F
H


I.1.2712
thiophen-3-yl
4-ethynyl
5-CH3
H


I.1.2713
thiophen-3-yl
4-ethynyl
2-CH3
H


I.1.2714
thiophen-3-yl
4-ethynyl
5-CN
H


I.1.2715
thiophen-3-yl
4-ethynyl
2-CN
H


I.1.2716
thiophen-3-yl
4-ethynyl
5-CF3
H


I.1.2717
thiophen-3-yl
4-ethynyl
2-CF3
H


I.1.2718
thiophen-3-yl
4-I
5-Cl
2-F


I.1.2719
thiophen-3-yl
4-I
5-Cl
H


I.1.2720
thiophen-3-yl
4-I
2-Cl
H


I.1.2721
thiophen-3-yl
4-I
5-F
H


I.1.2722
thiophen-3-yl
4-I
2-F
H


I.1.2723
thiophen-3-yl
4-I
5-CH3
H


I.1.2724
thiophen-3-yl
4-I
2-CH3
H


I.1.2725
thiophen-3-yl
4-I
5-CN
H


I.1.2726
thiophen-3-yl
4-I
2-CN
H


I.1.2727
thiophen-3-yl
4-I
5-CF3
H


I.1.2728
thiophen-3-yl
4-I
2-CF3
H


I.1.2729
thiophen-3-yl
4-Cl
5-Cl
2-F


I.1.2730
thiophen-3-yl
4-Cl
5-Cl
H


I.1.2731
thiophen-3-yl
4-Cl
2-Cl
H


I.1.2732
thiophen-3-yl
4-Cl
5-F
H


I.1.2733
thiophen-3-yl
4-Cl
2-F
H


I.1.2734
thiophen-3-yl
4-Cl
5-CH3
H


I.1.2735
thiophen-3-yl
4-Cl
2-CH3
H


I.1.2736
thiophen-3-yl
4-Cl
5-CN
H


I.1.2737
thiophen-3-yl
4-Cl
2-CN
H


I.1.2738
thiophen-3-yl
4-Cl
5-CF3
H


I.1.2739
thiophen-3-yl
4-Cl
2-CF3
H


I.1.2740
thiophen-3-yl
4-Br
5-Cl
2-F


I.1.2741
thiophen-3-yl
4-Br
5-Cl
H


I.1.2742
thiophen-3-yl
4-Br
2-Cl
H


I.1.2743
thiophen-3-yl
4-Br
5-F
H


I.1.2744
thiophen-3-yl
4-Br
2-F
H


I.1.2745
thiophen-3-yl
4-Br
5-CH3
H


I.1.2746
thiophen-3-yl
4-Br
2-CH3
H


I.1.2747
thiophen-3-yl
4-Br
5-CN
H


I.1.2748
thiophen-3-yl
4-Br
2-CN
H


I.1.2749
thiophen-3-yl
4-Br
5-CF3
H


I.1.2750
thiophen-3-yl
4-Br
2-CF3
H


I.1.2751
thiophen-3-yl
4-CON(CH3)2
5-Cl
2-F


I.1.2752
thiophen-3-yl
4-CON(CH3)2
5-Cl
H


I.1.2753
thiophen-3-yl
4-CON(CH3)2
2-Cl
H


I.1.2754
thiophen-3-yl
4-CON(CH3)2
5-F
H


I.1.2755
thiophen-3-yl
4-CON(CH3)2
2-F
H


I.1.2756
thiophen-3-yl
4-CON(CH3)2
5-CH3
H


I.1.2757
thiophen-3-yl
4-CON(CH3)2
2-CH3
H


I.1.2758
thiophen-3-yl
4-CON(CH3)2
5-CN
H


I.1.2759
thiophen-3-yl
4-CON(CH3)2
2-CN
H


I.1.2760
thiophen-3-yl
4-CON(CH3)2
5-CF3
H


I.1.2761
thiophen-3-yl
4-CON(CH3)2
2-CF3
H


I.1.2762
thiophen-3-yl
4-CONHCH3
5-Cl
2-F


I.1.2763
thiophen-3-yl
4-CONHCH3
5-Cl
H


I.1.2764
thiophen-3-yl
4-CONHCH3
2-Cl
H


I.1.2765
thiophen-3-yl
4-CONHCH3
5-F
H


I.1.2766
thiophen-3-yl
4-CONHCH3
2-F
H


I.1.2767
thiophen-3-yl
4-CONHCH3
5-CH3
H


I.1.2768
thiophen-3-yl
4-CONHCH3
2-CH3
H


I.1.2769
thiophen-3-yl
4-CONHCH3
5-CN
H


I.1.2770
thiophen-3-yl
4-CONHCH3
2-CN
H


I.1.2771
thiophen-3-yl
4-CONHCH3
5-CF3
H


I.1.2772
thiophen-3-yl
4-CONHCH3
2-CF3
H


I.1.2773
phenyl
2-CF3
H
H


I.1.2774
phenyl
2-CF3
3-Cl
H


I.1.2775
phenyl
2-CF3
4-Cl
H


I.1.2776
phenyl
2-CF3
5-Cl
H


I.1.2777
phenyl
2-CF3
6-Cl
H


I.1.2778
phenyl
2-CF3
3-CF3
H


I.1.2779
phenyl
2-CF3
4-CF3
H


I.1.2780
phenyl
2-CF3
5-CF3
H


I.1.2781
phenyl
2-CF3
6-CF3
H


I.1.2782
phenyl
2-CF3
3-F
H


I.1.2783
phenyl
2-CF3
4-F
H


I.1.2784
phenyl
2-CF3
5-F
H


I.1.2785
phenyl
2-CF3
6-F
H


I.1.2786
phenyl
2-CF3
3-CH3
H


I.1.2787
phenyl
2-CF3
4-CH3
H


I.1.2788
phenyl
2-CF3
5-CH3
H


I.1.2789
phenyl
2-CF3
6-CH3
H


I.1.2790
phenyl
2-CF3
5-vinyl
H


I.1.2791
phenyl
2-CF3
6-vinyl
H


I.1.2792
phenyl
2-CF3
5-CF3
3-Cl


I.1.2793
phenyl
2-CF3
5-CF3
4-Cl


I.1.2794
phenyl
2-CF3
4-CF3
5-Cl


I.1.2795
phenyl
2-CF3
5-CF3
6-Cl


I.1.2796
phenyl
2-CF3
5-CF3
3-F


I.1.2797
phenyl
2-CF3
5-CF3
4-F


I.1.2798
phenyl
2-CF3
4-CF3
5-F


I.1.2799
phenyl
2-CF3
5-CF3
6-F


I.1.2800
phenyl
2-CF3
5-CF3
3-CH3


I.1.2801
phenyl
2-CF3
5-CF3
4-CH3


I.1.2802
phenyl
2-CF3
4-CF3
5-CH3


I.1.2803
phenyl
2-CF3
5-CF3
6-CH3


I.1.2804
phenyl
2-CF3
4-CF3
5-vinyl


I.1.2805
phenyl
2-CF3
4-CF3
6-vinyl


I.1.2806
phenyl
2-CF3
3-Cl
4-F


I.1.2807
phenyl
2-CF3
3-Cl
5-F


I.1.2808
phenyl
2-CF3
3-Cl
6-F


I.1.2809
phenyl
2-CF3
3-Cl
4-Cl


I.1.2810
phenyl
2-CF3
3-Cl
5-Cl


I.1.2811
phenyl
2-CF3
3-Cl
6-Cl


I.1.2812
phenyl
2-CF3
3-Cl
4-CH3


I.1.2813
phenyl
2-CF3
3-Cl
5-CH3


I.1.2814
phenyl
2-CF3
3-Cl
6-CH3


I.1.2815
phenyl
2-CF3
3-Cl
5-vinyl


I.1.2816
phenyl
2-CF3
3-Cl
6-vinyl


I.1.2817
phenyl
2-CF3
3-F
4-F


I.1.2818
phenyl
2-CF3
3-F
5-F


I.1.2819
phenyl
2-CF3
3-F
6-F


I.1.2820
phenyl
2-CF3
3-F
4-Cl


I.1.2821
phenyl
2-CF3
3-F
5-Cl


I.1.2822
phenyl
2-CF3
3-F
6-Cl


I.1.2823
phenyl
2-CF3
3-F
4-CH3


I.1.2824
phenyl
2-CF3
3-F
5-CH3


I.1.2825
phenyl
2-CF3
3-F
6-CH3


I.1.2826
phenyl
2-CF3
3-F
5-vinyl


I.1.2827
phenyl
2-CF3
3-F
6-vinyl


I.1.2828
phenyl
2-CF3
3-CH3
4-F


I.1.2829
phenyl
2-CF3
3-CH3
5-F


I.1.2830
phenyl
2-CF3
3-CH3
6-F


I.1.2831
phenyl
2-CF3
3-CH3
4-Cl


I.1.2832
phenyl
2-CF3
3-CH3
5-Cl


I.1.2833
phenyl
2-CF3
3-CH3
6-Cl


I.1.2834
phenyl
2-CF3
3-CH3
4-CH3


I.1.2835
phenyl
2-CF3
3-CH3
5-CH3


I.1.2836
phenyl
2-CF3
3-CH3
6-CH3


I.1.2837
phenyl
2-CF3
3-CH3
5-vinyl


I.1.2838
phenyl
2-CF3
3-CH3
6-vinyl


I.1.2839
phenyl
2-CF3
4-Cl
5-F


I.1.2840
phenyl
2-CF3
4-Cl
6-F


I.1.2841
phenyl
2-CF3
4-Cl
5-Cl


I.1.2842
phenyl
2-CF3
4-Cl
6-Cl


I.1.2843
phenyl
2-CF3
4-Cl
5-CH3


I.1.2844
phenyl
2-CF3
4-Cl
6-CH3


I.1.2845
phenyl
2-CF3
4-Cl
5-vinyl


I.1.2846
phenyl
2-CF3
4-Cl
6-vinyl


I.1.2847
phenyl
2-CF3
4-F
5-F


I.1.2848
phenyl
2-CF3
4-F
6-F


I.1.2849
phenyl
2-CF3
4-F
5-Cl


I.1.2850
phenyl
2-CF3
4-F
6-Cl


I.1.2851
phenyl
2-CF3
4-F
5-CH3


I.1.2852
phenyl
2-CF3
4-F
6-CH3


I.1.2853
phenyl
2-CF3
4-F
5-vinyl


I.1.2854
phenyl
2-CF3
4-F
6-vinyl


I.1.2855
phenyl
2-CF3
4-CH3
5-F


I.1.2856
phenyl
2-CF3
4-CH3
6-F


I.1.2857
phenyl
2-CF3
4-CH3
5-Cl


I.1.2858
phenyl
2-CF3
4-CH3
6-Cl


I.1.2859
phenyl
2-CF3
4-CH3
5-CH3


I.1.2860
phenyl
2-CF3
4-CH3
6-CH3


I.1.2861
phenyl
2-CF3
4-CH3
5-vinyl


I.1.2862
phenyl
2-CF3
4-CH3
6-vinyl


I.1.2863
phenyl
2-CF3
5-Cl
6-Cl


I.1.2864
phenyl
2-CF3
5-Cl
6-F


I.1.2865
phenyl
2-CF3
5-Cl
6-CH3


I.1.2866
phenyl
2-CF3
5-Cl
6-vinyl


I.1.2867
phenyl
2-CF3
5-F
6-Cl


I.1.2868
phenyl
2-CF3
5-F
6-F


I.1.2869
phenyl
2-CF3
5-F
6-CH3


I.1.2870
phenyl
2-CF3
5-F
6-vinyl


I.1.2871
phenyl
2-CF3
5-CH3
6-Cl


I.1.2872
phenyl
2-CF3
5-CH3
6-F


I.1.2873
phenyl
2-CF3
5-CH3
6-CH3


I.1.2874
phenyl
2-CF3
5-CH3
6-vinyl


I.1.2875
phenyl
2-CF3
5-vinyl
6-Cl


I.1.2876
phenyl
2-CF3
5-vinyl
6-F


I.1.2877
phenyl
2-CF3
5-vinyl
6-CH3


I.1.2878
phenyl
2-CF3
5-vinyl
6-vinyl


I.1.2879
phenyl
2-CH3
H
H


I.1.2880
phenyl
2-CH3
3-Cl
H


I.1.2881
phenyl
2-CH3
4-Cl
H


I.1.2882
phenyl
2-CH3
5-Cl
H


I.1.2883
phenyl
2-CH3
6-Cl
H


I.1.2884
phenyl
2-CH3
3-CF3
H


I.1.2885
phenyl
2-CH3
4-CF3
H


I.1.2886
phenyl
2-CH3
5-CF3
H


I.1.2887
phenyl
2-CH3
6-CF3
H


I.1.2888
phenyl
2-CH3
3-F
H


I.1.2889
phenyl
2-CH3
4-F
H


I.1.2890
phenyl
2-CH3
5-F
H


I.1.2891
phenyl
2-CH3
6-F
H


I.1.2892
phenyl
2-CH3
3-CH3
H


I.1.2893
phenyl
2-CH3
4-CH3
H


I.1.2894
phenyl
2-CH3
5-CH3
H


I.1.2895
phenyl
2-CH3
6-CH3
H


I.1.2896
phenyl
2-CH3
5-vinyl
H


I.1.2897
phenyl
2-CH3
6-vinyl
H


I.1.2898
phenyl
2-CH3
5-CF3
3-Cl


I.1.2899
phenyl
2-CH3
5-CF3
4-Cl


I.1.2900
phenyl
2-CH3
4-CF3
5-Cl


I.1.2901
phenyl
2-CH3
5-CF3
6-Cl


I.1.2902
phenyl
2-CH3
5-CF3
3-F


I.1.2903
phenyl
2-CH3
5-CF3
4-F


I.1.2904
phenyl
2-CH3
4-CF3
5-F


I.1.2905
phenyl
2-CH3
5-CF3
6-F


I.1.2906
phenyl
2-CH3
5-CF3
3-CH3


I.1.2907
phenyl
2-CH3
5-CF3
4-CH3


I.1.2908
phenyl
2-CH3
4-CF3
5-CH3


I.1.2909
phenyl
2-CH3
5-CF3
6-CH3


I.1.2910
phenyl
2-CH3
4-CF3
5-vinyl


I.1.2911
phenyl
2-CH3
4-CF3
6-vinyl


I.1.2912
phenyl
2-CH3
3-Cl
4-F


I.1.2913
phenyl
2-CH3
3-Cl
5-F


I.1.2914
phenyl
2-CH3
3-Cl
6-F


I.1.2915
phenyl
2-CH3
3-Cl
4-Cl


I.1.2916
phenyl
2-CH3
3-Cl
5-Cl


I.1.2917
phenyl
2-CH3
3-Cl
6-Cl


I.1.2918
phenyl
2-CH3
3-Cl
4-CH3


I.1.2919
phenyl
2-CH3
3-Cl
5-CH3


I.1.2920
phenyl
2-CH3
3-Cl
6-CH3


I.1.2921
phenyl
2-CH3
3-Cl
5-vinyl


I.1.2922
phenyl
2-CH3
3-Cl
6-vinyl


I.1.2923
phenyl
2-CH3
3-F
4-F


I.1.2924
phenyl
2-CH3
3-F
5-F


I.1.2925
phenyl
2-CH3
3-F
6-F


I.1.2926
phenyl
2-CH3
3-F
4-Cl


I.1.2927
phenyl
2-CH3
3-F
5-Cl


I.1.2928
phenyl
2-CH3
3-F
6-Cl


I.1.2929
phenyl
2-CH3
3-F
4-CH3


I.1.2930
phenyl
2-CH3
3-F
5-CH3


I.1.2931
phenyl
2-CH3
3-F
6-CH3


I.1.2932
phenyl
2-CH3
3-F
5-vinyl


I.1.2933
phenyl
2-CH3
3-F
6-vinyl


I.1.2934
phenyl
2-CH3
3-CH3
4-F


I.1.2935
phenyl
2-CH3
3-CH3
5-F


I.1.2936
phenyl
2-CH3
3-CH3
6-F


I.1.2937
phenyl
2-CH3
3-CH3
4-Cl


I.1.2938
phenyl
2-CH3
3-CH3
5-Cl


I.1.2939
phenyl
2-CH3
3-CH3
6-Cl


I.1.2940
phenyl
2-CH3
3-CH3
4-CH3


I.1.2941
phenyl
2-CH3
3-CH3
5-CH3


I.1.2942
phenyl
2-CH3
3-CH3
6-CH3


I.1.2943
phenyl
2-CH3
3-CH3
5-vinyl


I.1.2944
phenyl
2-CH3
3-CH3
6-vinyl


I.1.2945
phenyl
2-CH3
4-Cl
5-F


I.1.2946
phenyl
2-CH3
4-Cl
6-F


I.1.2947
phenyl
2-CH3
4-Cl
5-Cl


I.1.2948
phenyl
2-CH3
4-Cl
6-Cl


I.1.2949
phenyl
2-CH3
4-Cl
5-CH3


I.1.2950
phenyl
2-CH3
4-Cl
6-CH3


I.1.2951
phenyl
2-CH3
4-Cl
5-vinyl


I.1.2952
phenyl
2-CH3
4-Cl
6-vinyl


I.1.2953
phenyl
2-CH3
4-F
5-F


I.1.2954
phenyl
2-CH3
4-F
6-F


I.1.2955
phenyl
2-CH3
4-F
5-Cl


I.1.2956
phenyl
2-CH3
4-F
6-Cl


I.1.2957
phenyl
2-CH3
4-F
5-CH3


I.1.2958
phenyl
2-CH3
4-F
6-CH3


I.1.2959
phenyl
2-CH3
4-F
5-vinyl


I.1.2960
phenyl
2-CH3
4-F
6-vinyl


I.1.2961
phenyl
2-CH3
4-CH3
5-F


I.1.2962
phenyl
2-CH3
4-CH3
6-F


I.1.2963
phenyl
2-CH3
4-CH3
5-Cl


I.1.2964
phenyl
2-CH3
4-CH3
6-Cl


I.1.2965
phenyl
2-CH3
4-CH3
5-CH3


I.1.2966
phenyl
2-CH3
4-CH3
6-CH3


I.1.2967
phenyl
2-CH3
4-CH3
5-vinyl


I.1.2968
phenyl
2-CH3
4-CH3
6-vinyl


I.1.2969
phenyl
2-CH3
5-Cl
6-Cl


I.1.2970
phenyl
2-CH3
5-Cl
6-F


I.1.2971
phenyl
2-CH3
5-Cl
6-CH3


I.1.2972
phenyl
2-CH3
5-Cl
6-vinyl


I.1.2973
phenyl
2-CH3
5-F
6-Cl


I.1.2974
phenyl
2-CH3
5-F
6-F


I.1.2975
phenyl
2-CH3
5-F
6-CH3


I.1.2976
phenyl
2-CH3
5-F
6-vinyl


I.1.2977
phenyl
2-CH3
5-CH3
6-Cl


I.1.2978
phenyl
2-CH3
5-CH3
6-F


I.1.2979
phenyl
2-CH3
5-CH3
6-CH3


I.1.2980
phenyl
2-CH3
5-CH3
6-vinyl


I.1.2981
phenyl
2-CH3
5-vinyl
6-Cl


I.1.2982
phenyl
2-CH3
5-vinyl
6-F


I.1.2983
phenyl
2-CH3
5-vinyl
6-CH3


I.1.2984
phenyl
2-CH3
5-vinyl
6-vinyl


I.1.2985
pyridin-2-yl
3-CF3
4-Cl
5-F


I.1.2986
pyridin-2-yl
3-CF3
4-Cl
H


I.1.2987
pyridin-2-yl
3-CF3
5-Cl
H


I.1.2988
pyridin-2-yl
3-CF3
6-Cl
H


I.1.2989
pyridin-2-yl
3-CF3
4-F
H


I.1.2990
pyridin-2-yl
3-CF3
5-F
H


I.1.2991
pyridin-2-yl
3-CF3
6-F
H


I.1.2992
pyridin-2-yl
3-CF3
4-Br
H


I.1.2993
pyridin-2-yl
3-CF3
5-Br
H


I.1.2994
pyridin-2-yl
3-CF3
6-Br
H


I.1.2995
pyridin-2-yl
3-CF3
4-CH3
H


I.1.2996
pyridin-2-yl
3-CF3
5-CH3
H


I.1.2997
pyridin-2-yl
3-CF3
6-CH3
H


I.1.2998
pyridin-2-yl
3-CF3
4-CF3
H


I.1.2999
pyridin-2-yl
3-CF3
5-CF3
H


I.1.3000
pyridin-2-yl
3-CF3
6-CF3
H


I.1.3001
pyridin-2-yl
3-CF3
4-vinyl
H


I.1.3002
pyridin-2-yl
3-CF3
5-vinyl
H


I.1.3003
pyridin-2-yl
3-CF3
6-vinyl
H


I.1.3004
pyridin-2-yl
3-CF3
4-Cl
6-F


I.1.3005
pyridin-2-yl
3-CF3
5-Cl
6-F


I.1.3006
pyridin-2-yl
3-CH3
4-Cl
5-F


I.1.3007
pyridin-2-yl
3-CH3
4-Cl
H


I.1.3008
pyridin-2-yl
3-CH3
5-Cl
H


I.1.3009
pyridin-2-yl
3-CH3
6-Cl
H


I.1.3010
pyridin-2-yl
3-CH3
4-F
H


I.1.3011
pyridin-2-yl
3-CH3
5-F
H


I.1.3012
pyridin-2-yl
3-CH3
6-F
H


I.1.3013
pyridin-2-yl
3-CH3
4-Br
H


I.1.3014
pyridin-2-yl
3-CH3
5-Br
H


I.1.3015
pyridin-2-yl
3-CH3
6-Br
H


I.1.3016
pyridin-2-yl
3-CH3
4-CH3
H


I.1.3017
pyridin-2-yl
3-CH3
5-CH3
H


I.1.3018
pyridin-2-yl
3-CH3
6-CH3
H


I.1.3019
pyridin-2-yl
3-CH3
4-CF3
H


I.1.3020
pyridin-2-yl
3-CH3
5-CF3
H


I.1.3021
pyridin-2-yl
3-CH3
6-CF3
H


I.1.3022
pyridin-2-yl
3-CH3
4-vinyl
H


I.1.3023
pyridin-2-yl
3-CH3
5-vinyl
H


I.1.3024
pyridin-2-yl
3-CH3
6-vinyl
H


I.1.3025
pyridin-2-yl
3-CH3
4-Cl
6-F


I.1.3026
pyridin-2-yl
3-CH3
5-Cl
6-F


I.1.3027
pyridin-3-yl
2-CF3
4-Cl
5-F


I.1.3028
pyridin-3-yl
2-CF3
4-Cl
H


I.1.3029
pyridin-3-yl
2-CF3
5-Cl
H


I.1.3030
pyridin-3-yl
2-CF3
6-Cl
H


I.1.3031
pyridin-3-yl
2-CF3
4-F
H


I.1.3032
pyridin-3-yl
2-CF3
5-F
H


I.1.3033
pyridin-3-yl
2-CF3
6-F
H


I.1.3034
pyridin-3-yl
2-CF3
4-Br
H


I.1.3035
pyridin-3-yl
2-CF3
5-Br
H


I.1.3036
pyridin-3-yl
2-CF3
6-Br
H


I.1.3037
pyridin-3-yl
2-CF3
4-CH3
H


I.1.3038
pyridin-3-yl
2-CF3
5-CH3
H


I.1.3039
pyridin-3-yl
2-CF3
6-CH3
H


I.1.3040
pyridin-3-yl
2-CF3
4-CF3
H


I.1.3041
pyridin-3-yl
2-CF3
5-CF3
H


I.1.3042
pyridin-3-yl
2-CF3
6-CF3
H


I.1.3043
pyridin-3-yl
2-CF3
4-vinyl
H


I.1.3044
pyridin-3-yl
2-CF3
5-vinyl
H


I.1.3045
pyridin-3-yl
2-CF3
6-vinyl
H


I.1.3046
pyridin-3-yl
2-CF3
4-Cl
6-F


I.1.3047
pyridin-3-yl
2-CF3
5-Cl
6-F


I.1.3048
pyridin-3-yl
2-CH3
4-Cl
5-F


I.1.3049
pyridin-3-yl
2-CH3
4-Cl
H


I.1.3050
pyridin-3-yl
2-CH3
5-Cl
H


I.1.3051
pyridin-3-yl
2-CH3
6-Cl
H


I.1.3052
pyridin-3-yl
2-CH3
4-F
H


I.1.3053
pyridin-3-yl
2-CH3
5-F
H


I.1.3054
pyridin-3-yl
2-CH3
6-F
H


I.1.3055
pyridin-3-yl
2-CH3
4-Br
H


I.1.3056
pyridin-3-yl
2-CH3
5-Br
H


I.1.3057
pyridin-3-yl
2-CH3
6-Br
H


I.1.3058
pyridin-3-yl
2-CH3
4-CH3
H


I.1.3059
pyridin-3-yl
2-CH3
5-CH3
H


I.1.3060
pyridin-3-yl
2-CH3
6-CH3
H


I.1.3061
pyridin-3-yl
2-CH3
4-CF3
H


I.1.3062
pyridin-3-yl
2-CH3
5-CF3
H


I.1.3063
pyridin-3-yl
2-CH3
6-CF3
H


I.1.3064
pyridin-3-yl
2-CH3
4-vinyl
H


I.1.3065
pyridin-3-yl
2-CH3
5-vinyl
H


I.1.3066
pyridin-3-yl
2-CH3
6-vinyl
H


I.1.3067
pyridin-3-yl
2-CH3
4-Cl
6-F


I.1.3068
pyridin-3-yl
2-CH3
5-Cl
6-F


I.1.3069
pyridin-3-yl
4-CF3
2-Cl
5-F


I.1.3070
pyridin-3-yl
4-CF3
2-Cl
H


I.1.3071
pyridin-3-yl
4-CF3
5-Cl
H


I.1.3072
pyridin-3-yl
4-CF3
6-Cl
H


I.1.3073
pyridin-3-yl
4-CF3
2-F
H


I.1.3074
pyridin-3-yl
4-CF3
5-F
H


I.1.3075
pyridin-3-yl
4-CF3
6-F
H


I.1.3076
pyridin-3-yl
4-CF3
2-Br
H


I.1.3077
pyridin-3-yl
4-CF3
5-Br
H


I.1.3078
pyridin-3-yl
4-CF3
6-Br
H


I.1.3079
pyridin-3-yl
4-CF3
2-CH3
H


I.1.3080
pyridin-3-yl
4-CF3
5-CH3
H


I.1.3081
pyridin-3-yl
4-CF3
6-CH3
H


I.1.3082
pyridin-3-yl
4-CF3
2-CF3
H


I.1.3083
pyridin-3-yl
4-CF3
5-CF3
H


I.1.3084
pyridin-3-yl
4-CF3
6-CF3
H


I.1.3085
pyridin-3-yl
4-CF3
2-vinyl
H


I.1.3086
pyridin-3-yl
4-CF3
5-vinyl
H


I.1.3087
pyridin-3-yl
4-CF3
6-vinyl
H


I.1.3088
pyridin-3-yl
4-CF3
2-Cl
6-F


I.1.3089
pyridin-3-yl
4-CF3
5-Cl
6-F


I.1.3090
pyridin-3-yl
4-CH3
2-Cl
5-F


I.1.3091
pyridin-3-yl
4-CH3
2-Cl
H


I.1.3092
pyridin-3-yl
4-CH3
5-Cl
H


I.1.3093
pyridin-3-yl
4-CH3
6-Cl
H


I.1.3094
pyridin-3-yl
4-CH3
2-F
H


I.1.3095
pyridin-3-yl
4-CH3
5-F
H


I.1.3096
pyridin-3-yl
4-CH3
6-F
H


I.1.3097
pyridin-3-yl
4-CH3
2-Br
H


I.1.3098
pyridin-3-yl
4-CH3
5-Br
H


I.1.3099
pyridin-3-yl
4-CH3
6-Br
H


I.1.3100
pyridin-3-yl
4-CH3
2-CH3
H


I.1.3101
pyridin-3-yl
4-CH3
5-CH3
H


I.1.3102
pyridin-3-yl
4-CH3
6-CH3
H


I.1.3103
pyridin-3-yl
4-CH3
2-CF3
H


I.1.3104
pyridin-3-yl
4-CH3
5-CF3
H


I.1.3105
pyridin-3-yl
4-CH3
6-CF3
H


I.1.3106
pyridin-3-yl
4-CH3
2-vinyl
H


I.1.3107
pyridin-3-yl
4-CH3
5-vinyl
H


I.1.3108
pyridin-3-yl
4-CH3
6-vinyl
H


I.1.3109
pyridin-3-yl
4-CH3
2-Cl
6-F


I.1.3110
pyridin-3-yl
4-CH3
5-Cl
6-F


I.1.3111
pyridin-4-yl
3-CF3
2-Cl
5-F


I.1.3112
pyridin-4-yl
3-CF3
2-Cl
H


I.1.3113
pyridin-4-yl
3-CF3
5-Cl
H


I.1.3114
pyridin-4-yl
3-CF3
6-Cl
H


I.1.3115
pyridin-4-yl
3-CF3
2-F
H


I.1.3116
pyridin-4-yl
3-CF3
5-F
H


I.1.3117
pyridin-4-yl
3-CF3
6-F
H


I.1.3118
pyridin-4-yl
3-CF3
2-Br
H


I.1.3119
pyridin-4-yl
3-CF3
5-Br
H


I.1.3120
pyridin-4-yl
3-CF3
6-Br
H


I.1.3121
pyridin-4-yl
3-CF3
2-CH3
H


I.1.3122
pyridin-4-yl
3-CF3
5-CH3
H


I.1.3123
pyridin-4-yl
3-CF3
6-CH3
H


I.1.3124
pyridin-4-yl
3-CF3
2-CF3
H


I.1.3125
pyridin-4-yl
3-CF3
5-CF3
H


I.1.3126
pyridin-4-yl
3-CF3
6-CF3
H


I.1.3127
pyridin-4-yl
3-CF3
2-vinyl
H


I.1.3128
pyridin-4-yl
3-CF3
5-vinyl
H


I.1.3129
pyridin-4-yl
3-CF3
6-vinyl
H


I.1.3130
pyridin-4-yl
3-CF3
2-Cl
6-F


I.1.3131
pyridin-4-yl
3-CF3
5-Cl
6-F


I.1.3132
pyridin-4-yl
3-CH3
2-Cl
5-F


I.1.3133
pyridin-4-yl
3-CH3
2-Cl
H


I.1.3134
pyridin-4-yl
3-CH3
5-Cl
H


I.1.3135
pyridin-4-yl
3-CH3
6-Cl
H


I.1.3136
pyridin-4-yl
3-CH3
2-F
H


I.1.3137
pyridin-4-yl
3-CH3
5-F
H


I.1.3138
pyridin-4-yl
3-CH3
6-F
H


I.1.3139
pyridin-4-yl
3-CH3
2-Br
H


I.1.3140
pyridin-4-yl
3-CH3
5-Br
H


I.1.3141
pyridin-4-yl
3-CH3
6-Br
H


I.1.3142
pyridin-4-yl
3-CH3
2-CH3
H


I.1.3143
pyridin-4-yl
3-CH3
5-CH3
H


I.1.3144
pyridin-4-yl
3-CH3
6-CH3
H


I.1.3145
pyridin-4-yl
3-CH3
2-CF3
H


I.1.3146
pyridin-4-yl
3-CH3
5-CF3
H


I.1.3147
pyridin-4-yl
3-CH3
6-CF3
H


I.1.3148
pyridin-4-yl
3-CH3
2-vinyl
H


I.1.3149
pyridin-4-yl
3-CH3
5-vinyl
H


I.1.3150
pyridin-4-yl
3-CH3
6-vinyl
H


I.1.3151
pyridin-4-yl
3-CH3
2-Cl
6-F


I.1.3152
pyridin-4-yl
3-CH3
5-Cl
6-F


I.1.3153
furan-2-yl
3-CF3
4-Cl
5-F


I.1.3154
furan-2-yl
3-CF3
4-Cl
H


I.1.3155
furan-2-yl
3-CF3
5-Cl
H


I.1.3156
furan-2-yl
3-CF3
4-F
H


I.1.3157
furan-2-yl
3-CF3
5-F
H


I.1.3158
furan-2-yl
3-CF3
4-CH3
H


I.1.3159
furan-2-yl
3-CF3
5-CH3
H


I.1.3160
furan-2-yl
3-CF3
4-CN
H


I.1.3161
furan-2-yl
3-CF3
5-CN
H


I.1.3162
furan-2-yl
3-CF3
4-CF3
H


I.1.3163
furan-2-yl
3-CF3
5-CF3
H


I.1.3164
furan-2-yl
3-CH3
4-Cl
5-F


I.1.3165
furan-2-yl
3-CH3
4-Cl
H


I.1.3166
furan-2-yl
3-CH3
5-Cl
H


I.1.3167
furan-2-yl
3-CH3
4-F
H


I.1.3168
furan-2-yl
3-CH3
5-F
H


I.1.3169
furan-2-yl
3-CH3
4-CH3
H


I.1.3170
furan-2-yl
3-CH3
5-CH3
H


I.1.3171
furan-2-yl
3-CH3
4-CN
H


I.1.3172
furan-2-yl
3-CH3
5-CN
H


I.1.3173
furan-2-yl
3-CH3
4-CF3
H


I.1.3174
furan-2-yl
3-CH3
5-CF3
H


I.1.3175
furan-3-yl
2-CF3
4-Cl
5-F


I.1.3176
furan-3-yl
2-CF3
4-Cl
H


I.1.3177
furan-3-yl
2-CF3
5-Cl
H


I.1.3178
furan-3-yl
2-CF3
4-F
H


I.1.3179
furan-3-yl
2-CF3
5-F
H


I.1.3180
furan-3-yl
2-CF3
4-CH3
H


I.1.3181
furan-3-yl
2-CF3
5-CH3
H


I.1.3182
furan-3-yl
2-CF3
4-CN
H


I.1.3183
furan-3-yl
2-CF3
5-CN
H


I.1.3184
furan-3-yl
2-CF3
4-CF3
H


I.1.3185
furan-3-yl
2-CF3
5-CF3
H


I.1.3186
furan-3-yl
2-CH3
4-Cl
5-F


I.1.3187
furan-3-yl
2-CH3
4-Cl
H


I.1.3188
furan-3-yl
2-CH3
5-Cl
H


I.1.3189
furan-3-yl
2-CH3
4-F
H


I.1.3190
furan-3-yl
2-CH3
5-F
H


I.1.3191
furan-3-yl
2-CH3
4-CH3
H


I.1.3192
furan-3-yl
2-CH3
5-CH3
H


I.1.3193
furan-3-yl
2-CH3
4-CN
H


I.1.3194
furan-3-yl
2-CH3
5-CN
H


I.1.3195
furan-3-yl
2-CH3
4-CF3
H


I.1.3196
furan-3-yl
2-CH3
5-CF3
H


I.1.3197
furan-3-yl
4-CF3
5-Cl
2-F


I.1.3198
furan-3-yl
4-CF3
5-Cl
H


I.1.3199
furan-3-yl
4-CF3
2-Cl
H


I.1.3200
furan-3-yl
4-CF3
5-F
H


I.1.3201
furan-3-yl
4-CF3
2-F
H


I.1.3202
furan-3-yl
4-CF3
5-CH3
H


I.1.3203
furan-3-yl
4-CF3
2-CH3
H


I.1.3204
furan-3-yl
4-CF3
5-CN
H


I.1.3205
furan-3-yl
4-CF3
2-CN
H


I.1.3206
furan-3-yl
4-CF3
5-CF3
H


I.1.3207
furan-3-yl
4-CF3
2-CF3
H


I.1.3208
furan-3-yl
4-CH3
5-Cl
2-F


I.1.3209
furan-3-yl
4-CH3
5-Cl
H


I.1.3210
furan-3-yl
4-CH3
2-Cl
H


I.1.3211
furan-3-yl
4-CH3
5-F
H


I.1.3212
furan-3-yl
4-CH3
2-F
H


I.1.3213
furan-3-yl
4-CH3
5-CH3
H


I.1.3214
furan-3-yl
4-CH3
2-CH3
H


I.1.3215
furan-3-yl
4-CH3
5-CN
H


I.1.3216
furan-3-yl
4-CH3
2-CN
H


I.1.3217
furan-3-yl
4-CH3
5-CF3
H


I.1.3218
furan-3-yl
4-CH3
2-CF3
H


I.1.3219
thiophen-2-yl
3-CF3
4-Cl
5-F


I.1.3220
thiophen-2-yl
3-CF3
4-Cl
H


I.1.3221
thiophen-2-yl
3-CF3
5-Cl
H


I.1.3222
thiophen-2-yl
3-CF3
4-F
H


I.1.3223
thiophen-2-yl
3-CF3
5-F
H


I.1.3224
thiophen-2-yl
3-CF3
4-CH3
H


I.1.3225
thiophen-2-yl
3-CF3
5-CH3
H


I.1.3226
thiophen-2-yl
3-CF3
4-CN
H


I.1.3227
thiophen-2-yl
3-CF3
5-CN
H


I.1.3228
thiophen-2-yl
3-CF3
4-CF3
H


I.1.3229
thiophen-2-yl
3-CF3
5-CF3
H


I.1.3230
thiophen-2-yl
3-CH3
4-Cl
5-F


I.1.3231
thiophen-2-yl
3-CH3
4-Cl
H


I.1.3232
thiophen-2-yl
3-CH3
5-Cl
H


I.1.3233
thiophen-2-yl
3-CH3
4-F
H


I.1.3234
thiophen-2-yl
3-CH3
5-F
H


I.1.3235
thiophen-2-yl
3-CH3
4-CH3
H


I.1.3236
thiophen-2-yl
3-CH3
5-CH3
H


I.1.3237
thiophen-2-yl
3-CH3
4-CN
H


I.1.3238
thiophen-2-yl
3-CH3
5-CN
H


I.1.3239
thiophen-2-yl
3-CH3
4-CF3
H


I.1.3240
thiophen-2-yl
3-CH3
5-CF3
H


I.1.3241
thiophen-3-yl
2-CF3
4-Cl
5-F


I.1.3242
thiophen-3-yl
2-CF3
4-Cl
H


I.1.3243
thiophen-3-yl
2-CF3
5-Cl
H


I.1.3244
thiophen-3-yl
2-CF3
4-F
H


I.1.3245
thiophen-3-yl
2-CF3
5-F
H


I.1.3246
thiophen-3-yl
2-CF3
4-CH3
H


I.1.3247
thiophen-3-yl
2-CF3
5-CH3
H


I.1.3248
thiophen-3-yl
2-CF3
4-CN
H


I.1.3249
thiophen-3-yl
2-CF3
5-CN
H


I.1.3250
thiophen-3-yl
2-CF3
4-CF3
H


I.1.3251
thiophen-3-yl
2-CF3
5-CF3
H


I.1.3252
thiophen-3-yl
2-CH3
4-Cl
5-F


I.1.3253
thiophen-3-yl
2-CH3
4-Cl
H


I.1.3254
thiophen-3-yl
2-CH3
5-Cl
H


I.1.3255
thiophen-3-yl
2-CH3
4-F
H


I.1.3256
thiophen-3-yl
2-CH3
5-F
H


I.1.3257
thiophen-3-yl
2-CH3
4-CH3
H


I.1.3258
thiophen-3-yl
2-CH3
5-CH3
H


I.1.3259
thiophen-3-yl
2-CH3
4-CN
H


I.1.3260
thiophen-3-yl
2-CH3
5-CN
H


I.1.3261
thiophen-3-yl
2-CH3
4-CF3
H


I.1.3262
thiophen-3-yl
2-CH3
5-CF3
H


I.1.3263
thiophen-3-yl
4-CF3
5-Cl
2-F


I.1.3264
thiophen-3-yl
4-CF3
5-Cl
H


I.1.3265
thiophen-3-yl
4-CF3
2-Cl
H


I.1.3266
thiophen-3-yl
4-CF3
5-F
H


I.1.3267
thiophen-3-yl
4-CF3
2-F
H


I.1.3268
thiophen-3-yl
4-CF3
5-CH3
H


I.1.3269
thiophen-3-yl
4-CF3
2-CH3
H


I.1.3270
thiophen-3-yl
4-CF3
5-CN
H


I.1.3271
thiophen-3-yl
4-CF3
2-CN
H


I.1.3272
thiophen-3-yl
4-CF3
5-CF3
H


I.1.3273
thiophen-3-yl
4-CF3
2-CF3
H


I.1.3274
thiophen-3-yl
4-CH3
5-Cl
2-F


I.1.3275
thiophen-3-yl
4-CH3
5-Cl
H


I.1.3276
thiophen-3-yl
4-CH3
2-Cl
H


I.1.3277
thiophen-3-yl
4-CH3
5-F
H


I.1.3278
thiophen-3-yl
4-CH3
2-F
H


I.1.3279
thiophen-3-yl
4-CH3
5-CH3
H


I.1.3280
thiophen-3-yl
4-CH3
2-CH3
H


I.1.3281
thiophen-3-yl
4-CH3
5-CN
H


I.1.3282
thiophen-3-yl
4-CH3
2-CN
H


I.1.3283
thiophen-3-yl
4-CH3
5-CF3
H


I.1.3284
thiophen-3-yl
4-CH3
2-CF3
H


I.1.3285
phenyl
3-methylisoxazol-5-yl
H
H


I.1.3286
phenyl
3-methylisoxazol-5-yl
3-Cl
H


I.1.3287
phenyl
3-methylisoxazol-5-yl
4-Cl
H


I.1.3288
phenyl
3-methylisoxazol-5-yl
5-Cl
H


I.1.3289
phenyl
3-methylisoxazol-5-yl
6-Cl
H


I.1.3290
phenyl
3-methylisoxazol-5-yl
3-F
H


I.1.3291
phenyl
3-methylisoxazol-5-yl
4-F
H


I.1.3292
phenyl
3-methylisoxazol-5-yl
5-F
H


I.1.3293
phenyl
3-methylisoxazol-5-yl
6-F
H


I.1.3294
phenyl
3-methylisoxazol-5-yl
3-CH3
H


I.1.3295
phenyl
3-methylisoxazol-5-yl
4-CH3
H


I.1.3296
phenyl
3-methylisoxazol-5-yl
5-CH3
H


I.1.3297
phenyl
3-methylisoxazol-5-yl
6-CH3
H


I.1.3298
phenyl
3-methylisoxazol-5-yl
5-vinyl
H


I.1.3299
phenyl
3-methylisoxazol-5-yl
6-vinyl
H


I.1.3300
phenyl
2-furyl
H
H


I.1.3301
phenyl
2-furyl
3-Cl
H


I.1.3302
phenyl
2-furyl
4-Cl
H


I.1.3303
phenyl
2-furyl
5-Cl
H


I.1.3304
phenyl
2-furyl
6-Cl
H


I.1.3305
phenyl
2-furyl
3-F
H


I.1.3306
phenyl
2-furyl
4-F
H


I.1.3307
phenyl
2-furyl
5-F
H


I.1.3308
phenyl
2-furyl
6-F
H


I.1.3309
phenyl
2-furyl
3-CH3
H


I.1.3310
phenyl
2-furyl
4-CH3
H


I.1.3311
phenyl
2-furyl
5-CH3
H


I.1.3312
phenyl
2-furyl
6-CH3
H


I.1.3313
phenyl
2-furyl
5-vinyl
H


I.1.3314
phenyl
2-furyl
6-vinyl
H


I.1.3315
phenyl
2-thienyl
H
H


I.1.3316
phenyl
2-thienyl
3-Cl
H


I.1.3317
phenyl
2-thienyl
4-Cl
H


I.1.3318
phenyl
2-thienyl
5-Cl
H


I.1.3319
phenyl
2-thienyl
6-Cl
H


I.1.3320
phenyl
2-thienyl
3-F
H


I.1.3321
phenyl
2-thienyl
4-F
H


I.1.3322
phenyl
2-thienyl
5-F
H


I.1.3323
phenyl
2-thienyl
6-F
H


I.1.3324
phenyl
2-thienyl
3-CH3
H


I.1.3325
phenyl
2-thienyl
4-CH3
H


I.1.3326
phenyl
2-thienyl
5-CH3
H


I.1.3327
phenyl
2-thienyl
6-CH3
H


I.1.3328
phenyl
2-thienyl
5-vinyl
H


I.1.3329
phenyl
2-thienyl
6-vinyl
H


I.1.3330
phenyl
2-oxazolyl
H
H


I.1.3331
phenyl
2-oxazolyl
3-Cl
H


I.1.3332
phenyl
2-oxazolyl
4-Cl
H


I.1.3333
phenyl
2-oxazolyl
5-Cl
H


I.1.3334
phenyl
2-oxazolyl
6-Cl
H


I.1.3335
phenyl
2-oxazolyl
3-F
H


I.1.3336
phenyl
2-oxazolyl
4-F
H


I.1.3337
phenyl
2-oxazolyl
5-F
H


I.1.3338
phenyl
2-oxazolyl
6-F
H


I.1.3339
phenyl
2-oxazolyl
3-CH3
H


I.1.3340
phenyl
2-oxazolyl
4-CH3
H


I.1.3341
phenyl
2-oxazolyl
5-CH3
H


I.1.3342
phenyl
2-oxazolyl
6-CH3
H


I.1.3343
phenyl
2-oxazolyl
5-vinyl
H


I.1.3344
phenyl
2-oxazolyl
6-vinyl
H


I.1.3345
phenyl
4-methyloxazol-2-yl
H
H


I.1.3346
phenyl
4-methyloxazol-2-yl
3-Cl
H


I.1.3347
phenyl
4-methyloxazol-2-yl
4-Cl
H


I.1.3348
phenyl
4-methyloxazol-2-yl
5-Cl
H


I.1.3349
phenyl
4-methyloxazol-2-yl
6-Cl
H


I.1.3350
phenyl
4-methyloxazol-2-yl
3-F
H


I.1.3351
phenyl
4-methyloxazol-2-yl
4-F
H


I.1.3352
phenyl
4-methyloxazol-2-yl
5-F
H


I.1.3353
phenyl
4-methyloxazol-2-yl
6-F
H


I.1.3354
phenyl
4-methyloxazol-2-yl
3-CH3
H


I.1.3355
phenyl
4-methyloxazol-2-yl
4-CH3
H


I.1.3356
phenyl
4-methyloxazol-2-yl
5-CH3
H


I.1.3357
phenyl
4-methyloxazol-2-yl
6-CH3
H


I.1.3358
phenyl
4-methyloxazol-2-yl
5-vinyl
H


I.1.3359
phenyl
4-methyloxazol-2-yl
6-vinyl
H


I.1.3360
phenyl
2-thiazolyl
H
H


I.1.3361
phenyl
2-thiazolyl
3-Cl
H


I.1.3362
phenyl
2-thiazolyl
4-Cl
H


I.1.3363
phenyl
2-thiazolyl
5-Cl
H


I.1.3364
phenyl
2-thiazolyl
6-Cl
H


I.1.3365
phenyl
2-thiazolyl
3-F
H


I.1.3366
phenyl
2-thiazolyl
4-F
H


I.1.3367
phenyl
2-thiazolyl
5-F
H


I.1.3368
phenyl
2-thiazolyl
6-F
H


I.1.3369
phenyl
2-thiazolyl
3-CH3
H


I.1.3370
phenyl
2-thiazolyl
4-CH3
H


I.1.3371
phenyl
2-thiazolyl
5-CH3
H


I.1.3372
phenyl
2-thiazolyl
6-CH3
H


I.1.3373
phenyl
2-thiazolyl
5-vinyl
H


I.1.3374
phenyl
2-thiazolyl
6-vinyl
H


I.1.3375
phenyl
2-pyridinyl
H
H


I.1.3376
phenyl
2-pyridinyl
3-Cl
H


I.1.3377
phenyl
2-pyridinyl
4-Cl
H


I.1.3378
phenyl
2-pyridinyl
5-Cl
H


I.1.3379
phenyl
2-pyridinyl
6-Cl
H


I.1.3380
phenyl
2-pyridinyl
3-F
H


I.1.3381
phenyl
2-pyridinyl
4-F
H


I.1.3382
phenyl
2-pyridinyl
5-F
H


I.1.3383
phenyl
2-pyridinyl
6-F
H


I.1.3384
phenyl
2-pyridinyl
3-CH3
H


I.1.3385
phenyl
2-pyridinyl
4-CH3
H


I.1.3386
phenyl
2-pyridinyl
5-CH3
H


I.1.3387
phenyl
2-pyridinyl
6-CH3
H


I.1.3388
phenyl
2-pyridinyl
5-vinyl
H


I.1.3389
phenyl
2-pyridinyl
6-vinyl
H


I.1.3390
phenyl
3-pyridinyl
H
H


I.1.3391
phenyl
3-pyridinyl
3-Cl
H


I.1.3392
phenyl
3-pyridinyl
4-Cl
H


I.1.3393
phenyl
3-pyridinyl
5-Cl
H


I.1.3394
phenyl
3-pyridinyl
6-Cl
H


I.1.3395
phenyl
3-pyridinyl
3-F
H


I.1.3396
phenyl
3-pyridinyl
4-F
H


I.1.3397
phenyl
3-pyridinyl
5-F
H


I.1.3398
phenyl
3-pyridinyl
6-F
H


I.1.3399
phenyl
3-pyridinyl
3-CH3
H


I.1.3400
phenyl
3-pyridinyl
4-CH3
H


I.1.3401
phenyl
3-pyridinyl
5-CH3
H


I.1.3402
phenyl
3-pyridinyl
6-CH3
H


I.1.3403
phenyl
3-pyridinyl
5-vinyl
H


I.1.3404
phenyl
3-pyridinyl
6-vinyl
H


I.1.3405
phenyl
2-pyrimidinyl
H
H


I.1.3406
phenyl
2-pyrimidinyl
3-Cl
H


I.1.3407
phenyl
2-pyrimidinyl
4-Cl
H


I.1.3408
phenyl
2-pyrimidinyl
5-Cl
H


I.1.3409
phenyl
2-pyrimidinyl
6-Cl
H


I.1.3410
phenyl
2-pyrimidinyl
3-F
H


I.1.3411
phenyl
2-pyrimidinyl
4-F
H


I.1.3412
phenyl
2-pyrimidinyl
5-F
H


I.1.3413
phenyl
2-pyrimidinyl
6-F
H


I.1.3414
phenyl
2-pyrimidinyl
3-CH3
H


I.1.3415
phenyl
2-pyrimidinyl
4-CH3
H


I.1.3416
phenyl
2-pyrimidinyl
5-CH3
H


I.1.3417
phenyl
2-pyrimidinyl
6-CH3
H


I.1.3418
phenyl
2-pyrimidinyl
5-vinyl
H


I.1.3419
phenyl
2-pyrimidinyl
6-vinyl
H


I.1.3420
phenyl
2-pyrazinyl
H
H


I.1.3421
phenyl
2-pyrazinyl
3-Cl
H


I.1.3422
phenyl
2-pyrazinyl
4-Cl
H


I.1.3423
phenyl
2-pyrazinyl
5-Cl
H


I.1.3424
phenyl
2-pyrazinyl
6-Cl
H


I.1.3425
phenyl
2-pyrazinyl
3-F
H


I.1.3426
phenyl
2-pyrazinyl
4-F
H


I.1.3427
phenyl
2-pyrazinyl
5-F
H


I.1.3428
phenyl
2-pyrazinyl
6-F
H


I.1.3429
phenyl
2-pyrazinyl
3-CH3
H


I.1.3430
phenyl
2-pyrazinyl
4-CH3
H


I.1.3431
phenyl
2-pyrazinyl
5-CH3
H


I.1.3432
phenyl
2-pyrazinyl
6-CH3
H


I.1.3433
phenyl
2-pyrazinyl
5-vinyl
H


I.1.3434
phenyl
2-pyrazinyl
6-vinyl
H









Preference is likewise given to the compounds of the formula I.2, particularly preferably the compounds I.2.1-I.2.3434, in particular the compounds (Z,S)-I.2.1-I.2.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorophenyl.


Preference is likewise given to the compounds of the formula I.3, particularly preferably the compounds I.3.1-I.3.3434, in particular the compounds (Z,S)-I.3.1-I.3.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chlorophenyl.


Preference is likewise given to the compounds of the formula I.4, particularly preferably the compounds I.4.1-I.4.3434, in particular the compounds (Z,S)-I.4.1-I.4.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorophenyl.


Preference is likewise given to the compounds of the formula I.5, particularly preferably the compounds I.5.1-I.5.3434, in particular the compounds (Z,S)-I.5.1-I.5.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylphenyl.


Preference is likewise given to the compounds of the formula I.6, particularly preferably the compounds I.6.1-I.6.3434, in particular the compounds (Z,S)-I.6.1-I.6.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylphenyl.


Preference is likewise given to the compounds of the formula I.7, particularly preferably the compounds I.7.1-I.7.3434, in particular the compounds (Z,S)-I.7.1-I.7.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylphenyl.


Preference is likewise given to the compounds of the formula I.8, particularly preferably the compounds I.8.1-I.8.3434, in particular the compounds (Z,S)-1.8.1-I.8.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxyphenyl.


Preference is likewise given to the compounds of the formula I.9, particularly preferably the compounds I.9.1-I.9.3434, in particular the compounds (Z,S)-I.9.1-I.9.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxyphenyl.


Preference is likewise given to the compounds of the formula I.10, particularly preferably the compounds I.10.1-I.10.3434, in particular the compounds (Z,S)-I.10.1-I.10.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxyphenyl.


Preference is likewise given to the compounds of the formula I.11, particularly preferably the compounds I.11.1-I.11.3434, in particular the compounds (Z,S)-I.11.1-I.11.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-1.1.1-I.1.3434 in that A2RdReRf is 2-fluorophenyl.


Preference is likewise given to the compounds of the formula I.12, particularly preferably the compounds I.12.1-I.12.3434, in particular the compounds (Z,S)-I.12.1-I.12.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorophenyl.


Preference is likewise given to the compounds of the formula I.13, particularly preferably the compounds I.13.1-I.13.3434, in particular the compounds (Z,S)-I.13.1-I.13.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorophenyl.


Preference is likewise given to the compounds of the formula I.14, particularly preferably the compounds I.14.1-I.14.3434, in particular the compounds (Z,S)-I.14.1-I.14.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methylphenyl.


Preference is likewise given to the compounds of the formula I.15, particularly preferably the compounds I.15.1-I.15.3434, in particular the compounds (Z,S)-I.15.1-I.15.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methylphenyl.


Preference is likewise given to the compounds of the formula I.16, particularly preferably the compounds I.16.1-I.16.3434, in particular the compounds (Z,S)-I.16.1-I.16.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methylphenyl.


Preference is likewise given to the compounds of the formula I.17, particularly preferably the compounds I.17.1-I.17.3434, in particular the compounds (Z,S)-I.17.1-I.17.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-3-methylphenyl.


Preference is likewise given to the compounds of the formula I.18, particularly preferably the compounds I.18.1-I.18.3434, in particular the compounds (Z,S)-I.18.1-I.18.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-4-methylphenyl.


Preference is likewise given to the compounds of the formula I.19, particularly preferably the compounds I.19.1-I.19.3434, in particular the compounds (Z,S)-I.19.1-I.19.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-5-methylphenyl.


Preference is likewise given to the compounds of the formula I.20, particularly preferably the compounds I.20.1-I.20.3434, in particular the compounds (Z,S)-I.20.1-I.20.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-6-methylphenyl.


Preference is likewise given to the compounds of the formula I.21, particularly preferably the compounds I.21.1-I.21.3434, in particular the compounds (Z,S)-I.21.1-I.21.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,3-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.22, particularly preferably the compounds I.22.1-I.22.3434, in particular the compounds (Z,S)-I.22.1-I.22.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,4-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.23, particularly preferably the compounds I.23.1-I.23.3434, in particular the compounds (Z,S)-I.23.1-I.23.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,5-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.24, particularly preferably the compounds I.24.1-I.24.3434, in particular the compounds (Z,S)-I.24.1-I.24.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,6-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.25, particularly preferably the compounds I.25.1-I.25.3434, in particular the compounds (Z,S)-I.25.1-I.25.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-3-fluorophenyl.


Preference is likewise given to the compounds of the formula I.26, particularly preferably the compounds I.26.1-I.26.3434, in particular the compounds (Z,S)-I.26.1-I.26.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-4-fluorophenyl.


Preference is likewise given to the compounds of the formula I.27, particularly preferably the compounds I.27.1-I.27.3434, in particular the compounds (Z,S)-I.27.1-I.27.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-5-fluorophenyl.


Preference is likewise given to the compounds of the formula I.28, particularly preferably the compounds I.28.1-I.28.3434, in particular the compounds (Z,S)-I.28.1-I.28.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-6-fluorophenyl.


Preference is likewise given to the compounds of the formula I.29, particularly preferably the compounds I.29.1-I.29.3434, in particular the compounds (Z,S)-I.29.1-I.29.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,3-difluorophenyl.


Preference is likewise given to the compounds of the formula I.30, particularly preferably the compounds I.30.1-I.30.3434, in particular the compounds (Z,S)-I.30.1-I.30.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2 is 2,4-difluorophenyl.


Preference is likewise given to the compounds of the formula I.31, particularly preferably the compounds I.31.1-I.31.3434, in particular the compounds (Z,S)-I.31.1-I.31.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,5-difluorophenyl.


Preference is likewise given to the compounds of the formula I.32, particularly preferably the compounds I.32.1-I.32.3434, in particular the compounds (Z,S)-I.32.1-I.32.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,6-difluorophenyl.


Preference is likewise given to the compounds of the formula I.33, particularly preferably the compounds I.33.1-I.33.3434, in particular the compounds (Z,S)-I.33.1-I.33.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-3-chlorophenyl.


Preference is likewise given to the compounds of the formula I.34, particularly preferably the compounds I.34.1-I.34.3434, in particular the compounds (Z,S)-I.34.1-I.34.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-4-chlorophenyl.


Preference is likewise given to the compounds of the formula I.35, particularly preferably the compounds I.35.1-I.35.3434, in particular the compounds (Z,S)-I.35.1-I.35.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-5-chlorophenyl.


Preference is likewise given to the compounds of the formula I.36, particularly preferably the compounds I.36.1-I.36.3434, in particular the compounds (Z,S)-I.36.1-I.36.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,4-difluorophenyl.


Preference is likewise given to the compounds of the formula I.37, particularly preferably the compounds I.37.1-I.37.3434, in particular the compounds (Z,S)-I.37.1-I.37.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,5-difluorophenyl.


Preference is likewise given to the compounds of the formula I.38, particularly preferably the compounds I.38.1-I.38.3434, in particular the compounds (Z,S)-I.38.1-I.38.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,4-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.39, particularly preferably the compounds I.39.1-I.39.3434, in particular the compounds (Z,S)-I.39.1-I.39.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,5-dichlorophenyl.


Preference is likewise given to the compounds of the formula I.40, particularly preferably the compounds I.40.1-I.40.3434, in particular the compounds (Z,S)-I.40.1-I.40.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoro,4-chlorophenyl.


Preference is likewise given to the compounds of the formula I.41, particularly preferably the compounds I.41.1-I.41.3434, in particular the compounds (Z,S)-I.41.1-I.41.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoro,3-chlorophenyl.


Preference is likewise given to the compounds of the formula I.42, particularly preferably the compounds I.42.1-I.42.3434, in particular the compounds (Z,S)-I.42.1-I.42.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoro,5-chlorophenyl.


Preference is likewise given to the compounds of the formula I.43, particularly preferably the compounds I.43.1-I.43.3434, in particular the compounds (Z,S)-I.43.1-I.43.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-2-yl.


Preference is likewise given to the compounds of the formula I.44, particularly preferably the compounds I.44.1-I.44.3434, in particular the compounds (Z,S)-I.44.1-I.44.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chloropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.45, particularly preferably the compounds I.45.1-I.45.3434, in particular the compounds (Z,S)-I.45.1-I.45.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chloropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.46, particularly preferably the compounds I.46.1-I.46.3434, in particular the compounds (Z,S)-I.46.1-I.46.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chloropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.47, particularly preferably the compounds I.47.1-I.47.3434, in particular the compounds (Z,S)-I.47.1-I.47.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-chloropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.48, particularly preferably the compounds I.48.1-I.48.3434, in particular the compounds (Z,S)-I.48.1-I.48.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylpyridin-2-yl.


Preference is likewise given to the compounds of the formula I.49, particularly preferably the compounds I.49.1-I.49.3434, in particular the compounds (Z,S)-I.49.1-I.49.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylpyridin-2-yl.


Preference is likewise given to the compounds of the formula I.50, particularly preferably the compounds I.50.1-I.50.3434, in particular the compounds (Z,S)-I.50.1-I.50.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylpyridin-2-yl.


Preference is likewise given to the compounds of the formula I.51, particularly preferably the compounds I.51.1-I.51.3434, in particular the compounds (Z,S)-I.51.1-I.51.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-trifluoromethylpyridin-2-yl.


Preference is likewise given to the compounds of the formula I.52, particularly preferably the compounds I.52.1-I.52.3434, in particular the compounds (Z,S)-I.52.1-I.52.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxypyridin-2-yl.


Preference is likewise given to the compounds of the formula I.53, particularly preferably the compounds I.53.1-I.53.3434, in particular the compounds (Z,S)-I.53.1-I.53.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxypyridin-2-yl.


Preference is likewise given to the compounds of the formula I.54, particularly preferably the compounds I.54.1-I.54.3434, in particular the compounds (Z,S)-I.54.1-I.54.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxypyridin-2-yl.


Preference is likewise given to the compounds of the formula I.55, particularly preferably the compounds I.55.1-I.55.3434, in particular the compounds (Z,S)-I.55.1-I.55.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-methoxypyridin-2-yl.


Preference is likewise given to the compounds of the formula I.56, particularly preferably the compounds I.56.1-I.56.3434, in particular the compounds (Z,S)-I.56.1-I.56.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.57, particularly preferably the compounds I.57.1-I.57.3434, in particular the compounds (Z,S)-I.57.1-I.57.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.58, particularly preferably the compounds I.58.1-I.58.3434, in particular the compounds (Z,S)-I.58.1-I.58.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluoropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.59, particularly preferably the compounds I.59.1-I.59.3434, in particular the compounds (Z,S)-I.59.1-I.59.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-fluoropyridin-2-yl.


Preference is likewise given to the compounds of the formula I.60, particularly preferably the compounds I.60.1-I.60.3434, in particular the compounds (Z,S)-I.60.1-I.60.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-3-yl.


Preference is likewise given to the compounds of the formula I.61, particularly preferably the compounds I.61.1-I.61.3434, in particular the compounds (Z,S)-I.61.1-I.61.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.62, particularly preferably the compounds I.62.1-I.62.3434, in particular the compounds (Z,S)-I.62.1-I.62.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chloropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.63, particularly preferably the compounds I.63.1-I.63.3434, in particular the compounds (Z,S)-I.63.1-I.63.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chloropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.64, particularly preferably the compounds I.64.1-I.64.3434, in particular the compounds (Z,S)-I.64.1-I.64.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-chloropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.65, particularly preferably the compounds I.65.1-I.65.3434, in particular the compounds (Z,S)-I.65.1-I.65.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylpyridin-3-yl.


Preference is likewise given to the compounds of the formula I.66, particularly preferably the compounds I.66.1-I.66.3434, in particular the compounds (Z,S)-I.66.1-I.66.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylpyridin-3-yl.


Preference is likewise given to the compounds of the formula I.67, particularly preferably the compounds I.67.1-I.67.3434, in particular the compounds (Z,S)-I.67.1-I.67.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylpyridin-3-yl.


Preference is likewise given to the compounds of the formula I.68, particularly preferably the compounds I.68.1-I.68.3434, in particular the compounds (Z,S)-I.68.1-I.68.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-trifluoromethylpyridin-3-yl.


Preference is likewise given to the compounds of the formula I.69, particularly preferably the compounds I.69.1-I.69.3434, in particular the compounds (Z,S)-I.69.1-I.69.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxypyridin-3-yl.


Preference is likewise given to the compounds of the formula I.70, particularly preferably the compounds I.70.1-I.70.3434, in particular the compounds (Z,S)-I.70.1-I.70.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxypyridin-3-yl.


Preference is likewise given to the compounds of the formula I.71, particularly preferably the compounds I.71.1-I.71.3434, in particular the compounds (Z,S)-I.71.1-I.71.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxypyridin-3-yl.


Preference is likewise given to the compounds of the formula I.72, particularly preferably the compounds I.72.1-I.72.3434, in particular the compounds (Z,S)-I.72.1-I.72.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-methoxypyridin-3-yl.


Preference is likewise given to the compounds of the formula I.73, particularly preferably the compounds I.73.1-I.73.3434, in particular the compounds (Z,S)-I.73.1-I.3.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.74, particularly preferably the compounds I.74.1-I.74.3434, in particular the compounds (Z,S)-I.74.1-I.74.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.75, particularly preferably the compounds I.75.1-I.75.3434, in particular the compounds (Z,S)-I.75.1-I.5.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluoropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.76, particularly preferably the compounds I.76.1-I.76.3434, in particular the compounds (Z,S)-I.76.1-I.76.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-fluoropyridin-3-yl.


Preference is likewise given to the compounds of the formula I.77, particularly preferably the compounds I.77.1-I.77.3434, in particular the compounds (Z,S)-I.77.1-I.77.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-4-yl.


Preference is likewise given to the compounds of the formula I.78, particularly preferably the compounds I.78.1-I.78.3434, in particular the compounds (Z,S)-I.78.1-I.78.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoropyridin-4-yl.


Preference is likewise given to the compounds of the formula I.79, particularly preferably the compounds I.79.1-I.79.3434, in particular the compounds (Z,S)-I.79.1-I.79.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoropyridin-4-yl.


Preference is likewise given to the compounds of the formula I.80, particularly preferably the compounds I.80.1-I.80.3434, in particular the compounds (Z,S)-I.80.1-I.80.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxypyridin-4-yl.


Preference is likewise given to the compounds of the formula I.81, particularly preferably the compounds I.81.1-I.81.3434, in particular the compounds (Z,S)-I.81.1-I.81.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxypyridin-4-yl.


Preference is likewise given to the compounds of the formula I.82, particularly preferably the compounds I.82.1-I.82.3434, in particular the compounds (Z,S)-I.82.1-I.82.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylpyridin-4-yl.


Preference is likewise given to the compounds of the formula I.83, particularly preferably the compounds I.83.1-I.83.3434, in particular the compounds (Z,S)-I.83.1-I.83.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylpyridin-4-yl.


Preference is likewise given to the compounds of the formula I.84, particularly preferably the compounds I.84.1-I.84.3434, in particular the compounds (Z,S)-I.84.1-I.84.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloropyridin-4-yl.


Preference is likewise given to the compounds of the formula I.85, particularly preferably the compounds I.85.1-I.85.3434, in particular the compounds (Z,S)-I.85.1-I.85.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chloropyridin-4-yl.


Preference is likewise given to the compounds of the formula I.86, particularly preferably the compounds I.86.1-I.86.3434, in particular the compounds (Z,S)-I.86.1-I.86.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is thiophen-2-yl.


Preference is likewise given to the compounds of the formula I.87, particularly preferably the compounds I.87.1-I.87.3434, in particular the compounds (Z,S)-I.87.1-I.87.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chlorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.88, particularly preferably the compounds I.88.1-I.88.3434, in particular the compounds (Z,S)-I.88.1-I.88.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.89, particularly preferably the compounds I.89.1-I.89.3434, in particular the compounds (Z,S)-I.89.1-I.89.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.90, particularly preferably the compounds I.90.1-I.90.3434, in particular the compounds (Z,S)-I.90.1-I.90.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylthiophen-2-yl.


Preference is likewise given to the compounds of the formula I.91, particularly preferably the compounds I.91.1-I.91.3434, in particular the compounds (Z,S)-I.91.1-I.91.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylthiophen-2-yl.


Preference is likewise given to the compounds of the formula I.92, particularly preferably the compounds I.92.1-I.92.3434, in particular the compounds (Z,S)-I.92.1-I.92.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylthiophen-2-yl.


Preference is likewise given to the compounds of the formula I.93, particularly preferably the compounds I.93.1-I.93.3434, in particular the compounds (Z,S)-I.93.1-I.93.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxythiophen-2-yl.


Preference is likewise given to the compounds of the formula I.94, particularly preferably the compounds I.94.1-I.94.3434, in particular the compounds (Z,S)-I.94.1-I.94.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxythiophen-2-yl.


Preference is likewise given to the compounds of the formula I.95, particularly preferably the compounds I.95.1-I.95.3434, in particular the compounds (Z,S)-I.95.1-I.95.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxythiophen-2-yl.


Preference is likewise given to the compounds of the formula I.96, particularly preferably the compounds I.96.1-I.96.3434, in particular the compounds (Z,S)-I.96.1-I.96.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.97, particularly preferably the compounds I.97.1-I.97.3434, in particular the compounds (Z,S)-I.97.1-I.97.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.98, particularly preferably the compounds I.98.1-I.98.3434, in particular the compounds (Z,S)-I.98.1-I.98.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorothiophen-2-yl.


Preference is likewise given to the compounds of the formula I.99, particularly preferably the compounds I.99.1-I.99.3434, in particular the compounds (Z,S)-I.99.1-I.99.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is thiophen-3-yl.


Preference is likewise given to the compounds of the formula I.100, particularly preferably the compounds I.100.1-I.100.3434, in particular the compounds (Z,S)-I.100.1-I.100.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.101, particularly preferably the compounds I.101.1-I.101.3434, in particular the compounds (Z,S)-I.101.1-I.101.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.102, particularly preferably the compounds I.102.1-I.102.3434, in particular the compounds (Z,S)-I.102.1-I.102.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.103, particularly preferably the compounds I.103.1-I.103.3434, in particular the compounds (Z,S)-I.103.1-I.103.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.104, particularly preferably the compounds I.104.1-I.104.3434, in particular the compounds (Z,S)-I.104.1-I.104.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.105, particularly preferably the compounds I.105.1-I.105.3434, in particular the compounds (Z,S)-I.105.1-I.105.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorothiophen-3-yl.


Preference is likewise given to the compounds of the formula I.106, particularly preferably the compounds I.106.1-I.106.3434, in particular the compounds (Z,S)-I.106.1-I.106.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxythiophen-3-yl.


Preference is likewise given to the compounds of the formula I.107, particularly preferably the compounds I.107.1-I.107.3434, in particular the compounds (Z,S)-I.107.1-I.107.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxythiophen-3-yl.


Preference is likewise given to the compounds of the formula I.108, particularly preferably the compounds I.108.1-I.108.3434, in particular the compounds (Z,S)-I.108.1-I.108.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxythiophen-3-yl.


Preference is likewise given to the compounds of the formula I.109, particularly preferably the compounds I.109.1-I.109.3434, in particular the compounds (Z,S)-I.109.1-I.109.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylthiophen-3-yl.


Preference is likewise given to the compounds of the formula I.110, particularly preferably the compounds I.110.1-I.110.3434, in particular the compounds (Z,S)-I.110.1-I.110.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylthiophen-3-yl.


Preference is likewise given to the compounds of the formula I.111, particularly preferably the compounds I.111.1-I.111.3434, in particular the compounds (Z,S)-I.111.1-I.111.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylthiophen-3-yl.


Preference is likewise given to the compounds of the formula I.112, particularly preferably the compounds I.112.1-I.112.3434, in particular the compounds (Z,S)-I.112.1-I.112.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is furan-2-yl.


Preference is likewise given to the compounds of the formula I.113, particularly preferably the compounds I.113.1-I.113.3434, in particular the compounds (Z,S)-I.113.1-I.113.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-1.1.1-I.1.3434 in that A2RdReRf is 3-chlorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.114, particularly preferably the compounds I.114.1-I.114.3434, in particular the compounds (Z,S)-I.114.1-I.114.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.115, particularly preferably the compounds I.115.1-I.115.3434, in particular the compounds (Z,S)-I.115.1-I.115.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.116, particularly preferably the compounds I.116.1-I.116.3434, in particular the compounds (Z,S)-I.116.1-I.116.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.117, particularly preferably the compounds I.117.1-I.117.3434, in particular the compounds (Z,S)-I.117.1-I.117.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.118, particularly preferably the compounds I.118.1-I.118.3434, in particular the compounds (Z,S)-I.118.1-I.118.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorofuran-2-yl.


Preference is likewise given to the compounds of the formula I.119, particularly preferably the compounds I.119.1-I.119.3434, in particular the compounds (Z,S)-I.119.1-I.119.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is furan-3-yl.


Preference is likewise given to the compounds of the formula I.120, particularly preferably the compounds I.120.1-I.120.3434, in particular the compounds (Z,S)-I.120.1-I.120.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.121, particularly preferably the compounds I.121.1-I.121.3434, in particular the compounds (Z,S)-I.121.1-I.121.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.122, particularly preferably the compounds I.122.1-I.122.3434, in particular the compounds (Z,S)-I.122.1-I.122.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.123, particularly preferably the compounds I.123.1-I.123.3434, in particular the compounds (Z,S)-I.123.1-I.123.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.124, particularly preferably the compounds I.124.1-I.124.3434, in particular the compounds (Z,S)-I.24.1-I.124.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.125, particularly preferably the compounds I.125.1-I.125.3434, in particular the compounds (Z,S)-I.125.1-I.125.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.126, particularly preferably the compounds I.126.1-I.126.3434, in particular the compounds (Z,S)-I.126.1-I.126.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorofuran-3-yl.


Preference is likewise given to the compounds of the formula I.127, particularly preferably the compounds I.127.1-I.127.3434, in particular the compounds (Z,S)-I.127.1-I.127.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that R1 is CH3.


Preference is likewise given to the compounds of the formula I.128, particularly preferably the compounds I.128.1-I.128.3434, in particular the compounds (Z,S)-I.128.1-I.128.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.129, particularly preferably the compounds I.129.1-I.129.3434, in particular the compounds (Z,S)-I.129.1-I.129.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.130, particularly preferably the compounds I.130.1-I.130.3434, in particular the compounds (Z,S)-I.130.1-I.130.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.131, particularly preferably the compounds I.131.1-I.131.3434, in particular the compounds (Z,S)-I.131.1-I.131.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.132, particularly preferably the compounds I.132.1-I.132.3434, in particular the compounds (Z,S)-I.132.1-I.132.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.133, particularly preferably the compounds I.133.1-I.133.3434, in particular the compounds (Z,S)-I.133.1-I.133.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.134, particularly preferably the compounds I.134.1-I.134.3434, in particular the compounds (Z,S)-I.134.1-I.134.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxyphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.135, particularly preferably the compounds I.135.1-I.135.3434, in particular the compounds (Z,S)-I.135.1-I.135.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxyphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.136, particularly preferably the compounds I.136.1-I.136.3434, in particular the compounds (Z,S)-I.136.1-I.136.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxyphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.137, particularly preferably the compounds I.137.1-I.137.3434, in particular the compounds (Z,S)-I.37.1-I.137.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.138, particularly preferably the compounds I.138.1-I.138.3434, in particular the compounds (Z,S)-I.138.1-I.138.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.139, particularly preferably the compounds I.139.1-I.139.3434, in particular the compounds (Z,S)-I.139.1-I.139.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.140, particularly preferably the compounds I.140.1-I.140.3434, in particular the compounds (Z,S)-I.140.1-I.140.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.141, particularly preferably the compounds I.141.1-I.141.3434, in particular the compounds (Z,S)-I.141.1-I.141.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.142, particularly preferably the compounds I.142.1-I.142.3434, in particular the compounds (Z,S)-I.142.1-I.142.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.143, particularly preferably the compounds I.143.1-I.143.3434, in particular the compounds (Z,S)-I.143.1-I.143.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-3-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.144, particularly preferably the compounds I.144.1-I.144.3434, in particular the compounds (Z,S)-I.144.1-I.144.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-4-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.145, particularly preferably the compounds I.145.1-I.145.3434, in particular the compounds (Z,S)-I.145.1-I.145.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-5-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.146, particularly preferably the compounds I.146.1-I.146.3434, in particular the compounds (Z,S)-I.146.1-I.146.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-6-methylphenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.147, particularly preferably the compounds I.147.1-I.147.3434, in particular the compounds (Z,S)-I.147.1-I.147.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,3-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.148, particularly preferably the compounds I.148.1-I.148.3434, in particular the compounds (Z,S)-I.148.1-I.148.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,4-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.149, particularly preferably the compounds I.149.1-I.149.3434, in particular the compounds (Z,S)-I.149.1-I.149.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,5-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.150, particularly preferably the compounds I.150.1-I.150.3434, in particular the compounds (Z,S)-I.150.1-I.150.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,6-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.151, particularly preferably the compounds I.151.1-I.151.3434, in particular the compounds (Z,S)-I.151.1-I.151.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-3-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.152, particularly preferably the compounds I.152.1-I.152.3434, in particular the compounds (Z,S)-I.152.1-I.152.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-4-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.153, particularly preferably the compounds I.153.1-I.153.3434, in particular the compounds (Z,S)-I.153.1-I.153.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-5-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.154, particularly preferably the compounds I.154.1-I.154.3434, in particular the compounds (Z,S)-I.154.1-I.154.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloro-6-fluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.155, particularly preferably the compounds I.155.1-I.155.3434, in particular the compounds (Z,S)-I.155.1-I.155.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,3-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.156, particularly preferably the compounds I.156.1-I.156.3434, in particular the compounds (Z,S)-I.156.1-I.156.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,4-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.157, particularly preferably the compounds I.157.1-I.157.3434, in particular the compounds (Z,S)-I.157.1-I.157.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,5-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.158, particularly preferably the compounds I.158.1-I.158.3434, in particular the compounds (Z,S)-I.158.1-I.158.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2,6-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.159, particularly preferably the compounds I.159.1-I.159.3434, in particular the compounds (Z,S)-I.159.1-I.159.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-3-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.160, particularly preferably the compounds I.160.1-I.160.3434, in particular the compounds (Z,S)-I.160.1-I.160.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-4-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.161, particularly preferably the compounds I.161.1-I.161.3434, in particular the compounds (Z,S)-I.161.1-I.161.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoro-5-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.162, particularly preferably the compounds I.162.1-I.162.3434, in particular the compounds (Z,S)-I.162.1-I.162.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,4-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.163, particularly preferably the compounds I.163.1-I.163.3434, in particular the compounds (Z,S)-I.163.1-I.163.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,5-difluorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.164, particularly preferably the compounds I.164.1-I.164.3434, in particular the compounds (Z,S)-I.164.1-I.164.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,4-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.165, particularly preferably the compounds I.165.1-I.165.3434, in particular the compounds (Z,S)-I.165.1-I.165.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3,5-dichlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.166, particularly preferably the compounds I.166.1-I.166.3434, in particular the compounds (Z,S)-I.166.1-I.166.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoro-4-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.167, particularly preferably the compounds I.167.1-I.167.3434, in particular the compounds (Z,S)-I.167.1-I.167.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoro-3-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.168, particularly preferably the compounds I.168.1-I.168.3434, in particular the compounds (Z,S)-I.168.1-I.168.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoro-5-chlorophenyl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.169, particularly preferably the compounds I.169.1-I.169.3434, in particular the compounds (Z,S)-I.169.1-I.169.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.170, particularly preferably the compounds I.170.1-I.170.3434, in particular the compounds (Z,S)-I.170.1-I.170.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chloropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.171, particularly preferably the compounds I.171.1-I.171.3434, in particular the compounds (Z,S)-I.171.1-I.171.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chloropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.172, particularly preferably the compounds I.172.1-I.172.3434, in particular the compounds (Z,S)-I.172.1-I.172.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chloropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.173, particularly preferably the compounds I.173.1-I.173.3434, in particular the compounds (Z,S)-I.173.1-I.173.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-chloropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.174, particularly preferably the compounds I.174.1-I.174.3434, in particular the compounds (Z,S)-I.174.1-I.174.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylpyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.175, particularly preferably the compounds I.175.1-I.175.3434, in particular the compounds (Z,S)-I.175.1-I.175.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylpyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.176, particularly preferably the compounds I.176.1-I.176.3434, in particular the compounds (Z,S)-I.176.1-I.176.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylpyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.177, particularly preferably the compounds I.177.1-I.177.3434, in particular the compounds (Z,S)-I.177.1-I.177.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-trifluoromethylpyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.178, particularly preferably the compounds I.178.1-I.178.3434, in particular the compounds (Z,S)-I.178.1-I.178.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxypyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.179, particularly preferably the compounds I.179.1-I.179.3434, in particular the compounds (Z,S)-I.179.1-I.179.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxypyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.180, particularly preferably the compounds I.180.1-I.180.3434, in particular the compounds (Z,S)-I.180.1-I.180.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxypyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.181, particularly preferably the compounds I.181.1-I.181.3434, in particular the compounds (Z,S)-I.181.1-I.181.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-methoxypyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.182, particularly preferably the compounds I.182.1-I.182.3434, in particular the compounds (Z,S)-I.182.1-I.182.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.183, particularly preferably the compounds I.183.1-I.183.3434, in particular the compounds (Z,S)-I.83.1-I.183.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.184, particularly preferably the compounds I.184.1-I.184.3434, in particular the compounds (Z,S)-I.184.1-I.184.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluoropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.185, particularly preferably the compounds I.185.1-I.185.3434, in particular the compounds (Z,S)-I.185.1-I.185.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-fluoropyridin-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.186, particularly preferably the compounds I.186.1-I.186.3434, in particular the compounds (Z,S)-I.186.1-I.186.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.187, particularly preferably the compounds I.187.1-I.187.3434, in particular the compounds (Z,S)-I.187.1-I.187.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.188, particularly preferably the compounds I.188.1-I.188.3434, in particular the compounds (Z,S)-I.188.1-I.188.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chloropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.189, particularly preferably the compounds I.189.1-I.189.3434, in particular the compounds (Z,S)-I.189.1-I.189.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chloropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.190, particularly preferably the compounds I.190.1-I.190.3434, in particular the compounds (Z,S)-I.190.1-I.190.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-chloropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.191, particularly preferably the compounds I.191.1-I.191.3434, in particular the compounds (Z,S)-I.191.1-I.191.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylpyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.192, particularly preferably the compounds I.192.1-I.192.3434, in particular the compounds (Z,S)-I.192.1-I.192.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylpyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.193, particularly preferably the compounds I.193.1-I.193.3434, in particular the compounds (Z,S)-I.193.1-I.193.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylpyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.194, particularly preferably the compounds I.194.1-I.194.3434, in particular the compounds (Z,S)-I.194.1-I.194.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-trifluoromethylpyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.195, particularly preferably the compounds I.195.1-I.195.3434, in particular the compounds (Z,S)-I.195.1-I.195.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxypyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.196, particularly preferably the compounds I.196.1-I.196.3434, in particular the compounds (Z,S)-I.196.1-I.196.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxypyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.197, particularly preferably the compounds I.197.1-I.197.3434, in particular the compounds (Z,S)-I.197.1-I.197.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxypyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.198, particularly preferably the compounds I.198.1-I.198.3434, in particular the compounds (Z,S)-I.198.1-I.198.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-methoxypyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.199, particularly preferably the compounds I.199.1-I.199.3434, in particular the compounds (Z,S)-I.199.1-I.199.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.200, particularly preferably the compounds I.200.1-I.200.3434, in particular the compounds (Z,S)-I.200.1-I.200.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluoropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.201, particularly preferably the compounds I.201.1-I.201.3434, in particular the compounds (Z,S)-I.201.1-I.201.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluoropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.202, particularly preferably the compounds I.202.1-I.202.3434, in particular the compounds (Z,S)-I.202.1-I.202.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 6-fluoropyridin-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.203, particularly preferably the compounds I.203.1-I.203.3434, in particular the compounds (Z,S)-I.203.1-I.203.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is pyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.204, particularly preferably the compounds I.204.1-I.204.3434, in particular the compounds (Z,S)-I.204.1-I.204.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluoropyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.205, particularly preferably the compounds I.205.1-I.205.3434, in particular the compounds (Z,S)-I.205.1-I.205.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluoropyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.206, particularly preferably the compounds I.206.1-I.206.3434, in particular the compounds (Z,S)-I.206.1-I.206.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxypyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.207, particularly preferably the compounds I.207.1-I.207.3434, in particular the compounds (Z,S)-I.207.1-I.207.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxypyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.208, particularly preferably the compounds I.208.1-I.208.3434, in particular the compounds (Z,S)-I.208.1-I.208.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylpyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.209, particularly preferably the compounds I.209.1-I.209.3434, in particular the compounds (Z,S)-I.209.1-I.209.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylpyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.210, particularly preferably the compounds I.210.1-I.210.3434, in particular the compounds (Z,S)-I.210.1-I.210.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chloropyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.211, particularly preferably the compounds I.211.1-I.211.3434, in particular the compounds (Z,S)-I.211.1-I.211.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chloropyridin-4-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.212, particularly preferably the compounds I.212.1-I.212.3434, in particular the compounds (Z,S)-I.212.1-I.212.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is thiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.213, particularly preferably the compounds I.213.1-I.213.3434, in particular the compounds (Z,S)-I.213.1-I.213.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chlorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.214, particularly preferably the compounds I.214.1-I.214.3434, in particular the compounds (Z,S)-I.214.1-I.214.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.215, particularly preferably the compounds I.215.1-I.215.3434, in particular the compounds (Z,S)-I.215.1-I.215.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.216, particularly preferably the compounds I.216.1-I.216.3434, in particular the compounds (Z,S)-I.216.1-I.216.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-trifluoromethylthiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.217, particularly preferably the compounds I.217.1-I.217.3434, in particular the compounds (Z,S)-I.217.1-I.217.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylthiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.218, particularly preferably the compounds I.218.1-I.218.3434, in particular the compounds (Z,S)-I.218.1-I.218.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylthiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.219, particularly preferably the compounds I.219.1-I.219.3434, in particular the compounds (Z,S)-I.219.1-I.219.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-methoxythiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.220, particularly preferably the compounds I.220.1-I.220.3434, in particular the compounds (Z,S)-I.220.1-I.220.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxythiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.221, particularly preferably the compounds I.221.1-I.221.3434, in particular the compounds (Z,S)-I.221.1-I.221.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxythiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.222, particularly preferably the compounds I.222.1-I.222.3434, in particular the compounds (Z,S)-I.222.1-I.222.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.223, particularly preferably the compounds I.223.1-I.223.3434, in particular the compounds (Z,S)-I.223.1-I.223.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.224, particularly preferably the compounds I.224.1-I.224.3434, in particular the compounds (Z,S)-I.224.1-I.224.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorothiophen-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.225, particularly preferably the compounds I.225.1-I.225.3434, in particular the compounds (Z,S)-I.225.1-I.225.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.13434 in that A2RdReRf is thiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.226, particularly preferably the compounds I.226.1-I.226.3434, in particular the compounds (Z,S)-I.226.1-I.226.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.227, particularly preferably the compounds I.227.1-I.227.3434, in particular the compounds (Z,S)-I.227.1-I.227.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.228, particularly preferably the compounds I.228.1-I.228.3434, in particular the compounds (Z,S)-I.228.1-I.228.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.229, particularly preferably the compounds I.229.1-I.229.3434, in particular the compounds (Z,S)-I.229.1-I.229.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.230, particularly preferably the compounds I.230.1-I.230.3434, in particular the compounds (Z,S)-I.230.1-I.230.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.13434 in that A2RdReRf is 4-fluorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.231, particularly preferably the compounds I.231.1-I.231.3434, in particular the compounds (Z,S)-I.231.1-I.231.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorothiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.232, particularly preferably the compounds I.232.1-I.232.3434, in particular the compounds (Z,S)-I.232.1-I.232.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-methoxythiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.233, particularly preferably the compounds I.233.1-I.233.3434, in particular the compounds (Z,S)-I.233.1-I.233.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-methoxythiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.234, particularly preferably the compounds I.234.1-I.234.3434, in particular the compounds (Z,S)-I.234.1-I.234.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-methoxythiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.235, particularly preferably the compounds I.235.1-I.235.3434, in particular the compounds (Z,S)-I.235.1-I.235.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-trifluoromethylthiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.236, particularly preferably the compounds I.236.1-I.236.3434, in particular the compounds (Z,S)-I.236.1-I.236.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-trifluoromethylthiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.237, particularly preferably the compounds I.237.1-I.237.3434, in particular the compounds (Z,S)-I.237.1-I.237.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-trifluoromethylthiophen-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.238, particularly preferably the compounds I.238.1-I.238.3434, in particular the compounds (Z,S)-I.238.1-I.238.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is furan-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.239, particularly preferably the compounds I.239.1-I.239.3434, in particular the compounds (Z,S)-I.239.1-I.239.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-chlorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.240, particularly preferably the compounds I.240.1-I.240.3434, in particular the compounds (Z,S)-I.240.1-I.240.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.241, particularly preferably the compounds I.241.1-I.241.3434, in particular the compounds (Z,S)-I.241.1-I.241.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.242, particularly preferably the compounds I.242.1-I.242.3434, in particular the compounds (Z,S)-I.242.1-I.242.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 3-fluorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.243, particularly preferably the compounds I.243.1-I.243.3434, in particular the compounds (Z,S)-I.243.1-I.243.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.244, particularly preferably the compounds I.244.1-I.244.3434, in particular the compounds (Z,S)-I.244.1-I.244.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorofuran-2-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.245, particularly preferably the compounds I.245.1-I.245.3434, in particular the compounds (Z,S)-I.245.1-I.245.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is furan-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.246, particularly preferably the compounds I.246.1-I.246.3434, in particular the compounds (Z,S)-I.246.1-I.246.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-chlorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.247, particularly preferably the compounds I.247.1-I.247.3434, in particular the compounds (Z,S)-I.247.1-I.247.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-chlorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.248, particularly preferably the compounds I.248.1-I.248.3434, in particular the compounds (Z,S)-I.248.1-I.248.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-chlorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.249, particularly preferably the compounds I.249.1-I.249.3434, in particular the compounds (Z,S)-I.249.1-I.249.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 2-fluorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.250, particularly preferably the compounds I.250.1-I.250.3434, in particular the compounds (Z,S)-I.250.1-I.250.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 4-fluorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.251, particularly preferably the compounds I.251.1-I.251.3434, in particular the compounds (Z,S)-I.251.1-I.251.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2RdReRf is 5-fluorofuran-3-yl and R1 is CH3.


Preference is likewise given to the compounds of the formula I.252, particularly preferably the compounds I.252.1-I.252.3434, in particular the compounds (Z,S)-I.252.1-I.252.3434, which differ from the corresponding compounds I.1.1-I.1.3434 or (Z,S)-I.1.1-I.1.3434 in that A2 is 5-fluorofuran-3-yl and R1 is CH3.


The piperazine compounds of the formula I can be prepared by standard methods for synthesizing organic compounds by various routes, for example by the processes illustrated in more detail below:


Process A

The compounds of the formula I can be prepared, for example, analogously to processes known from the literature by dehydrating the corresponding alcohol precursor of the formula II.







Accordingly, the invention furthermore provides a process for preparing piperazine compounds of the general formula I according to the invention which comprises reacting a compound of the formula II







in which the variables A1, A2, R1, R2, R3, R4, R5, R6, Ra, Rb, Rc, Rd, Re and Rf are as defined above for the compound of the formula I, either

  • (A.1) to give a compound of the formula III







in which LG is a leaving group, and formally eliminating the compound H-LG from the compound III, giving the corresponding compound I;


or

  • (A.2) dehydrating corresponding compound I if LG is OH, wherein the dehydration is, if appropriate, carried out in the presence of a dehydrating agent.


For the preferred meanings of the variables A1, A2, R1, R2, R3, R4, R5, R6, Ra, Rb, Rc, Rd, Re and Rf, reference is made to what was stated above. Preferred embodiments of the process according to the invention are described below.


Variant A.1

In a first variant (variant A.1), the alcohol function of the compound II can initially be converted into a suitable leaving group, and this can then be eliminated formally as the compound H-LG. The elimination reaction is preferably carried out in the presence of a suitable base. This reaction is illustrated in the scheme below.







In formula II, the variables A1, A2, R1-R6, Ra, Rb, Rc, Rd, Re and Rf are as defined for formula I. LG is a leaving group.


The leaving group LG is a customary leaving group which is easy to prepare from a hydroxyl group. Examples of these are 4-toluenesulfonyloxy (LG=—O—SO2C6H4CH3), trifluoromethanesulfonyloxy (LG=—O—SO2CF3) and methanesulfonyloxy (LG=—O—SO2CH3), the latter being particularly suitable. Such a leaving group is introduced in accordance with customary processes, for example by reacting the alcohol II with a base and then with the appropriate sulfonyl chloride, for example using methanesulfonyl chloride or trifluoromethanesulfonyl chloride. Suitable bases are the bases listed below for the elimination. However, preference is given to using bases soluble in organic solvents, for example the amines or nitrogen heterocycles mentioned below. Use is made in particular of pyridine or substituted pyridines, such as dimethylaminopyridine, lutidine or collidine, or mixtures thereof. It is expedient to chose the organic bases such that they can also act as solvent.


Bases suitable for the elimination are, in general, inorganic compounds such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, an aqueous ammonia solution, alkali metal or alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, for example lithium diisopropylamide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate, cesium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, 2-hydroxypyridine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. It is, of course, also possible to use a mixture of different bases.


Particularly suitable, however, are bases which are sufficiently basic but substantially not nucleophilic, for example sterically hindered alkali metal alkoxides, for example alkali metal tert-butoxides, such as potassium tert-butoxide, and in particular cyclic amidines, such as DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[3.4.0]non-5-ene). Preference is given to using the last-mentioned amidines.


The elimination is generally carried out in a solvent, preferably in an inert organic solvent. Suitable inert organic solvents include aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as dichloromethane, dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, water and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, and also morpholine and N-methylmorpholine. It is also possible to use mixtures of the solvents mentioned. Preference is given to using tetrahydrofuran.


The dehydration of alcohols II by converting the alcohol function into a good leaving group and the subsequent elimination can be carried out analogously to known processes of the prior art, for example analogously to the processes described in Helv. Chim. Acta 1947, 30, 1454; Liebigs Ann. Chem. 1992, (7), 687-692, Carbanions. 24. Rearrangements of (E)- and (Z)-2,2-diphenyl-3-pentenylalkali metal compounds; Sch. Chem., Georgia inst. Technol., Atlanta, Ga., USA; J. Org. Chem. 1989, 54(7), 1671-1679; Chemical & Pharmaceutical Bulletin 1986, 34(7), 2786-2798, which are expressly incorporated herein in their entirety.


Variant A.2

In a second variant (variant A.2), the compound I is prepared by dehydrating the compound II in the presence of a suitable dehydrating agent, as illustrated by the scheme below.







Suitable dehydrating agents are, for example, the system triphenylphosphine/DEAD (DEAD=diethyl azodicarboxylate) and the Burgess reagent. The combination of triphenylphosphine and DEAD is generally employed for the targeted inversion at a hydroxyl-substituted center of chirality (Mitsunobu reaction); however, in the absence of nucleophiles it acts as a mild dehydrating agent. Based on the compound II, the system is preferably employed in excess, where the two components triphenylphosphine and DEAD are suitably present in an approximately equimolar ratio.


The Burgess reagent is the zwitterion methyl N-(triethylammoniumsulfonylcarbamate ((C2H5)3N+—SO2—N−—COOCH3), a mild dehydrating agent. This can be employed in an equimolar amount or in a molar excess, based on the alcohol II. The reaction with the Burgess reagent is generally carried out in an inert organic solvent. Suitable inert organic solvents include aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as dichloromethane, dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, and ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone. Preference is given to using aromatic hydrocarbons or mixtures thereof and especially toluene.


The dehydration of alcohols II using dehydrating agents can be carried out analogously to known processes of the prior art, for example analogously to the processes described in Synthesis 2003, 201 and J. Indian Sci. 2001, 81, 461, which are expressly incorporated herein in their entirety.


Process B

The alcohols of the formula II used in the two variants (A.1 and A.2) of process A can be prepared, for example, analogously to processes known from the literature by cyclizing corresponding dipeptide precursors of the formula IV, for example analogously to the method described by T. Kawasaki et al., Org. Lett. 2(19) (2000), 3027-3029, Igor L. Rodionov et al., Tetrahedron 58(42) (2002), 8515-8523 or A. L. Johnson et al., Tetrahedron 60 (2004), 961-965. Hereinbelow, the cyclization of dipeptides of the formula IV to the alcohols II is also referred to below as process B and is illustrated in the scheme below.







In formula IV, the variables A1, A2, R1-R6, Ra, Rb, Rc, Rd, Re and Rf are as defined for formula I. The group ORx is a suitable leaving group attached via oxygen. Here, Rx is, for example, C1-C6-alkyl, in particular methyl or ethyl, or phenyl-C1-C6-alkyl, for example benzyl.


The cyclization can be carried out, for example, by reacting a dipeptide of the formula IV either in the presence of acid or base (acidic or basic cyclization) or by heating of the reaction mixture (thermal cyclization).


The bases or acids are added to the dipeptide IV either in equimolar amounts or in excess. In a particular embodiment of the process according to the invention, the bases or acids are employed in excess, based on the dipeptide.


The reaction of the dipeptide IV in the presence of a base is generally carried out at temperatures in the range from 0° C. to the boiling point of the reaction mixture, preferably from 10° C. to 50° C., particularly preferably from 15° C. to 35° C. In general, the reaction is carried out in a solvent, preferably in an inert organic solvent.


Suitable inert organic solvents include aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C5-C8-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as dichloromethane, dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, water and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide and also morpholine and N-methylmorpholine. It is also possible to use mixtures of the solvents mentioned.


In a preferred embodiment of the invention, the reaction is carried out in a tetrahydrofuran-water mixture using, for example, a mixing ratio of 1:10 to 10:1 (parts by volume).


Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, an aqueous solution of ammonia, alkali metal or alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, for example lithium diisopropylamide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate, cesium carbonate and calcium carbonate and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, 2-hydroxypyridine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. It is, of course, also possible to use a mixture of different bases.


In one embodiment of the process according to the invention, the reaction of IV is carried out in the presence of bases, preferably in the presence of the bases potassium tert-butoxide, 2-hydroxypyridine or an aqueous solution of ammonia or a mixture of these bases. Preference is given to using only one of these bases. In a particularly preferred embodiment, the reaction is carried out in the presence of an aqueous solution of ammonia which, for example, may be from 10 to 50% strength (w/v).


The reaction of IV in the presence of an acid is usually carried out at temperatures in the range from 10° C. to the boiling point of the reaction mixture, preferably from 50° C. to the boiling point, particularly preferably at the boiling point under reflux. In general, the reaction is carried out in a solvent, preferably in an inert organic solvent.


In principle, suitable solvents are those solvents which can also be used for the basic cyclization, in particular alcohols. In a preferred embodiment, the reaction is carried out in n-butanol.


In principle, suitable acids for the cyclization of IV are both Brönstedt and Lewis acids. In particular, it is possible to employ inorganic acids, for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, inorganic oxo acids, such as sulfuric acid and perchloric acid, furthermore inorganic Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and also organic acids, for example carboxylic acids and hydroxycarboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid, and also organic sulfonic acids, such as toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid and the like. It is, of course, also possible to use a mixture of different acids.


In one embodiment of the process according to the invention, the reaction is carried out in the presence of organic acids, for example in the presence of carboxylic acids, such as formic acid, acetic acid or trifluoroacetic acid or a mixture of these acids. Preferably, only one of these acids is used. In a preferred embodiment, the reaction is carried out in acetic acid.


A particularly preferred embodiment of the acidic cyclization is carried out in the presence of n-butanol, N-methylmorpholine and acetic acid under reflux conditions.


In a further embodiment of the invention, the reaction is carried out just by heating the reaction mixture (thermal cyclization). Here, the reaction is usually carried out at temperatures in the range from 10° C. to the boiling point of the reaction mixture, preferably from 50° C. to the boiling point of the reaction mixture, particularly preferably at the boiling point of the reaction mixture under reflux. In general, the reaction is carried out in a solvent, preferably in an inert organic solvent.


In principle, suitable solvents are those solvents which can be used for the basic cyclization. Preference is given to polar aprotic solvents, for example dimethyl sulfoxide or dimethylformamide or mixtures thereof. In a preferred embodiment, the reaction is carried out in dimethyl sulfoxide.


The reaction mixtures obtained in process B, but also the reaction mixtures obtained in processes A1 and A2 and the reaction mixtures of the processes described hereinbelow, can be worked-up in a customary manner. This may take place, for example, by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of viscous oils which can generally be purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products can be obtained as solids, the purification can also be carried out by recrystallisation or digestion.


Some of the precursors and intermediates required for preparing the compounds of the formula II are commercially available, known from the literature or can be prepared by processes known from the literature.


The dipeptide compounds of the formula IV can be prepared, for example, from N-protected dipeptides of the general formula V analogously to processes known from the literature, for example according to Glenn L. Stahl et al., J. Org. Chem. 43(11), (1978), 2285-6 or A. K. Ghosh et al., Org. Lett. 3(4), (2001), 635-638.







In the formulae IV and V, the variables A1, A2, R1-R6, Ra, Rb, Rc, Rd, Re and Rf are as defined for formula I, SG is a nitrogen protective group, such as Boc (=tert-butoxycarbonyl), and ORx is a leaving group attached via an oxygen atom. Of course, in each case the preferred meanings for the compounds of the formula II apply correspondingly to the compounds of the formula IV or V. With respect to the leaving group ORx, what was stated above for the dipeptides of the formula IV applies.


Thus, for example, a dipeptide of the formula V in which SG is Boc and ORx is a suitable leaving group, where Rx is, for example, C1-C6-alkyl, in particular methyl, ethyl or benzyl, can be converted in the presence of an acid into a compound of the formula IV.


The reaction is usually carried out at temperatures in the range from −30° C. to the boiling point of the reaction mixture, preferably from 0° C. to 50° C., particularly preferably from 20° C. to 35° C.


The reaction can take place in a solvent, in particular in an inert organic solvent. Suitable solvents are, in principle, the compounds cited for the basic cyclization, in particular tetrahydrofuran or dichloromethane or mixtures thereof. In a preferred embodiment, the reaction is carried out in dichloromethane.


The acids used are the acids cited for the cyclization of dipeptide IV to piperazine II.


In one embodiment of the process according to the invention, the reaction is carried out in the presence of organic acids, for example in the presence of strong organic acids, such as formic acid, acetic acid or trifluoroacetic acid or mixtures thereof. In a preferred embodiment, the reaction is carried out in the presence of trifluoroacetic acid.


The work-up can be carried out analogously to the procedure described for the cyclization of dipeptide IV to piperazine II.


The protected dipeptides of the formula V can be prepared analogously to processes known from the literature, for example according to Wilford L. Mendelson et al., Int. J. Peptide & Protein Research 35(3), (1990), 249-57. A typical route is the amidation of a Boc-protected amino acid VI with an amino acid ester of the formula VII, as shown in the scheme below:







In this scheme, the variables are as defined above. Instead of Boc, it is also possible to use other amino protective groups.


In general, the reaction of VII with VI is carried out at temperatures in a range from −30° C. to the boiling point of the reaction mixture, preferably from 0° C. to 50° C., particularly preferably from 20° C. to 35° C. The reaction can be carried out in a solvent, preferable in an inert organic solvent. Suitable solvents are the solvents mentioned in the context of the basic cyclization of IV to II.


In general, the reaction requires the presence of an activating agent. Suitable activating agents are condensing agents, such as, for example, polystyrene- or non-polystyrene-supported dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide, 1-ethyl-3-(dimethylaminopropyl)carbodiimide (EDAC), carbonyldiimidazole, chlorocarbonic esters, such as methyl chloroformate, ethyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis(2-oxo-3-oxazolidinyl)-phosphoryl chloride (BOPCl) or sulfonyl chlorides, such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride. According to one embodiment, a preferred activating agent is EDAC or DCC.


The reaction of VII with VI is preferably carried out in the presence of a base. Suitable bases are the compounds cited for the cyclization of dipeptide IV to piperazine II. In one embodiment, the base used is triethylamine or N-ethyldiisopropylamine or mixtures thereof, particularly preferably N-ethyldiisopropylamine.


The work-up can be carried out analogously to the procedure described for the cyclization of dipeptide IV to piperazine II.


For their part, the compounds of the formula VII can be prepared by deprotecting corresponding protected amino acid compounds VIII analogously to processes known from the literature, for example according to Glenn L. Stahl et al., J. Org. Chem. 43(11), (1978), 2285-6 or A. K. Ghosh et al., Org. Lett. 3(4), (2001), 635-638. The preparation of VII from a Boc-protected amino acid compound VIII is shown in the scheme below.







In this scheme, the variables are as defined above. Instead of Boc, it is also possible to use other amino protective groups.


The conversion of a compound of the formula VIII into the compound VII is typically carried out in the presence of an acid at temperatures in a range from −30° C. to the boiling point of the reaction mixture, preferably from 0° C. to 50° C., particularly preferably from 20° C. to 35° C. The reaction can be carried out in a solvent, preferably in an inert organic solvent.


Suitable solvents are, in principle, the compounds mentioned under the basic cyclization, in particular tetrahydrofuran or dichloromethane or mixtures thereof. In a preferred embodiment, the reaction is carried out in dichloromethane.


The acids and acidic catalysts used are the substances cited for the cyclization of dipeptide IV to piperazine II.


In one embodiment of the process according to the invention, the reaction is carried out in the presence of organic acids, for example in the presence of strong organic acids, such as formic acid, acetic acid or trifluoroacetic acid or mixtures thereof. In a preferred embodiment, the reaction is carried out in the presence of trifluoroacetic acid.


The work-up can be carried out analogously to the procedure described for the cyclization of dipeptide IV to piperazine II.


The compounds of the formula VIII can be prepared according to the reaction shown in the scheme below. The reaction of compound XI with the protected amino acid compound X can be carried out analogously to processes known from the literature, for example according to I. Ojima et al., J. Am. Chem. Soc., 109(21), (1987), 6537-6538 or J. M. McIntosh et al., Tetrahedron 48(30), (1992), 6219-6224.







In this scheme, the variables are as defined above. L is a leaving group. Instead of Boc, it is also possible to use other amino protective groups.


The reaction of XI with X is generally carried out in the presence of base. Suitable bases are the compounds cited for the cyclization of dipeptide IV to piperazine II. In a further preferred embodiment, the base used is lithium diisopropylamide, particularly preferably in a substantially equimolar amount, in particular in an equimolar amount. Usually, the reaction is carried out at temperatures in the range from −78° C. to the boiling point of the reaction mixture, preferably from −78° C. to the boiling point, particularly preferably from 78° C. to 30° C.


The reaction can be carried out in a solvent, preferably in an inert organic solvent. Suitable solvents are, in principle, the solvents mentioned under the basic cyclization, in particular dichloromethane or tetrahydrofuran or mixtures thereof. In a preferred embodiment, the reaction is carried out in tetrahydrofuran.


The work-up can be carried out analogously to the procedure described for the cyclization of dipeptide IV to piperazine II.


Some of the compounds of the formula XI are commercially available or can be prepared by transformations, described in the literature, of the corresponding commercially available precursors.


Process C

Compounds of the formula II.1 in which R3 is H can also be prepared by coupling, in an aldol reaction, the aldehyde XII with the piperazine XIII, as illustrated in the scheme below:







In the formulae II.1, XII and XIII, the variables A1, A2, R1-R6, Ra, Rb, Rc, Rd, Re and Rf are as defined for formula I.


The reaction is generally carried out in the presence of suitable bases. Suitable bases are bases usually employed for aldol reactions. Examples of these are the compounds mentioned for the cyclization of IV to II. Preference is given to using alkali metal amides, such as lithium diisopropylamide. Suitable reaction conditions are known from the prior art and are described, for example, in J. Org. Chem. 2000, 65 (24), 8402-8405, which are expressly incorporated herein in their entirety.


The aldol reaction may also yield directly the corresponding aldol condensation product, i.e. compounds of the formula I.1 in which R3 is H. This is the case in particular when the reaction proceeds at elevated temperatures and with relatively long reaction times.







The aldehyde XII is either commercially available or can be synthesized according to known processes for the preparation of aldehydes. Such aldol condensations can be carried out analogously to the processes described in J. Org. Chem. 2000, 65 (24), 8402-8405, which is expressly incorporated herein in its entirety.


In principle, the aldol reaction or condensation can also be employed for preparing compounds I in which R3 is not necessarily hydrogen but can also be C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C8-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl and especially C1-C6-alkyl. In this case, instead of the aldehyde XII, the ketone IX is used







in which R3 is C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl and especially C1-C6-alkyl.


However, it is possible here that complex reaction mixtures are formed, in particular when R3 is a group in which the carbon atom attached in the α-position to the point of attachment carries a hydrogen atom. Moreover, in most cases more drastic reaction conditions are required, so that the aldolization is preferably only used for preparing compounds I.1.


The compounds of the formula XIII can be prepared by intramolecular cyclization of compounds of the general formula XIV analogously to further processes known from the literature, for example according to T. Kawasaki et al., Org. Lett. 2(19) (2000), 3027-3029, Igor L. Rodionov et al., Tetrahedron 58(42) (2002), 8515-8523 or A. L. Johnson et al., Tetrahedron 60 (2004), 961-965.







In formula XIV, the variables Rx, A2, R1, R2, R4, R5, R6, Rd, Re and Rf are as defined for formula IV. The group ORx is a suitable leaving group attached via oxygen. Here, Rx is for example C1-C6-alkyl, in particular methyl or ethyl, or phenyl-C1-C8-alkyl, for example benzyl.


The cyclization of the compounds of the formula XIV can be carried out in the presence of a base. In this case, the reaction is generally carried out at temperatures in the range from 0° C. to the boiling point of the reaction mixture, preferably from 10° C. to 50° C., particularly preferably from 15° C. to 35° C. The reaction can be carried out in a solvent, preferably in an inert organic solvent.


Suitable solvents are, in principle, the compounds cited under the thermal cyclization, in particular a tetrahydrofuran-water mixture having a mixing ratio of from 1:10 to 10:1.


Suitable bases are the bases mentioned for the basic cyclization of IV to II (process B), in particular potassium tert-butoxide, 2-hydroxypyridine or an aqueous solution of ammonia or a mixture of these bases. Preferably, only one of these bases is used. In a particularly preferred embodiment, the reaction is carried out in the presence of an aqueous solution of ammonia which, for example, may be from 10 to 50% strength (w/v).


For their part, the compounds of the formula XIV can be prepared by the synthesis illustrated in the scheme below, analogously to processes known from the literature, for example according to Wilford L. Mendelson et al., Int. J. Peptide & Protein Research 35(3), (1990), 249-57, Glenn L. Stahl et al., J. Org. Chem. 43(11), (1978), 2285-6 or A. K. Ghosh et al., Org. Lett. 3(4), (2001), 635-638.







In the scheme, the variables Rx, A2, R1, R2, R4, R5, Re, Rd, Re and Rf are as defined for formula IV or XIV. In a first step, the synthesis comprises the coupling of amino acid compounds XV with Boc-protected amino acids VI in the presence of an activating agent. Instead of Boc, it is also possible to use another amino protective group.


The reaction of a compound of the formula XV with a compound of the formula VI is usually carried out at temperatures in the range from −30° C. to the boiling point of the reaction mixture, preferably from 0° C. to 50° C., particularly preferably from 20° C. to 35° C. The reaction can be carried out in a solvent, preferably in an inert organic solvent. For further details, reference is made to the preparation of compound V by amidation of the amino acid compound VI with the compound VII.


In general, the reaction requires the presence of an activating agent. Suitable activating agents are condensing agents, such as, for example, polystyrene- or non-polystyrene-supported dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide, 1-ethyl-3-(dimethylaminopropyl)carbodiimide (EDAC), carbonyldiimidazole, chlorocarbonic esters, such as methyl chloroformate, ethyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate, pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis(2-oxo-3-oxazolidinyl)-phosphoryl chloride (BOPCl) or sulfonyl chlorides, such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride. According to one embodiment, a preferred activating agent is EDAC or DCC.


The reaction of XV with VI is preferably carried out in the presence of a base. Suitable bases are the compounds cited under process B (cyclization of dipeptide IV to piperazine II). In one embodiment, the base used is triethylamine or N-ethyldiisopropylamine or mixtures thereof, particularly preferably N-ethyldiisopropylamine.


The work-up can be carried out analogously to the procedure described for process B (cyclization of dipeptide IV to piperazine II).


The deprotection of the compound XVI to give the compound XIV is typically carried out by treatment with an acid. The reaction is usually carried out at temperatures in the range from −30° C. to the boiling point of the reaction mixture, preferably from 0° C. to 50° C., particularly preferably from 20° C. to 35° C. The reaction can be carried out in a solvent, preferably in an inert organic solvent.


Suitable solvents are, in principle, the solvents mentioned under process B in connection with the basic cyclization, in particular tetrahydrofuran or dichloromethane or mixtures thereof. In a preferred embodiment, the reaction is carried out in dichloromethane.


The acids used are the acids mentioned for process B (cyclization of dipeptide IV to piperazine II). For further details, reference is also made to the deprotection of V to compound IV. The reaction conditions mentioned there are also suitable for deprotecting compound XVI. In one embodiment of the process according to the invention, the reaction is carried out in the presence of organic acids, in particular strong organic acids, for example in the presence of formic acid, acetic acid or trifluoroacetic acid or mixtures thereof. In a preferred embodiment, the reaction is carried out in the presence of trifluoroacetic acid.


If, instead of Boc, a different protective group is used, the deprotection process employed is of course suitable for the protective group in question.


The work-up can be carried out analogously to the procedure described for process B (cyclization of dipeptide IV to piperazine II).


Process D

The invention furthermore provides a process for preparing piperazine compounds of the general formula I which comprises reacting, in the presence of a base, a compound of the formula IX







in which the variables A1, Ra, Rb and Rc are as defined above and R3 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl, with a phosphonic ester of the formula XVII







in which the variables A2, R1, R2, R4, R5, R6, Rd, Re and Rf are as defined above and Ry is C1-C4-alkyl, for example methyl, ethyl, propyl, isopropyl, butyl or isobutyl, aryl, for example phenyl, or aryl-C1-C4-alkyl, for example benzyl.


The reaction mentioned above is also referred to as Wittig-Horner-Emmons reaction.


Ry is preferably C1-C4-alkyl and in particular methyl or ethyl.


This process is preferably employed to prepare compounds of the formula I.1 in which R3 is H. To this end, the procedure described above is adopted, the compound IX used being the aldehyde XII (corresponds to the compound IX in which R3 is H), which is reacted with the phosphonic ester XVII. This is illustrated in the scheme below:







In the scheme, the variables A1, A2, R1, R2, R4, R5, R6, Ra, Rb, Rc, Rd, Re and Rf are as defined above. Ry is C1-C4-alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl, aryl, for example phenyl, or aryl-C1-C4-alkyl, for example benzyl. Ry is preferably C1-C4-alkyl and in particular methyl or ethyl.


Suitable reaction conditions are known from the prior art and described, for example, in J. Org. Chem. 2001, 66(11), 3984-3997 and in Tetrahedron Lett. 1987, 28, 4275, which are expressly incorporated herein in their entirety.


Thus, suitable bases are all bases customary for Wittig-Horner-Emmons reactions, for example alkali metal hydrides, such as sodium hydride, and alkali metal amides, such as lithium diisopropylamide. However, preference is given to relatively weak bases, such as, for example, the non-nucleophilic bases mentioned above, for example the amidines DBU and DBN or sterically hindered alkali metal alkoxides, such as potassium tert-butoxide. Suitable solvents are, of course, aprotic and are selected, for example, from halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, and aromatic hydrocarbons, such as benzene and toluene.


In principle, the Wittig-Horner-Emmons reaction can also be employed for preparing compounds I in which R3 is not necessarily hydrogen but may also be C1-C6-alkyl, C1-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl and especially C1-C6-alkyl. In this case, instead of the aldehyde XII, the ketone IX.1 (corresponds to compound IX in which R3 is not hydrogen) is used







in which R3 is C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6 alkenyl, C3-C6-cycloalkenyl, C2-C8 alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl and especially C1-C6-alkyl.


Here, what was said above with respect to the preparation of the piperazine compound of the formula I.1 applies correspondingly. However, here more drastic reaction conditions are required in most cases, for example stronger bases, higher temperatures, longer reaction times, etc., so that the above-described reaction according to Wittig, Horner and Emmons is preferably employed for the preparation of compounds I.1.


The phosphonic ester XVII can be obtained, for example, by cyclization of the phosphonate XVIII:







In the scheme, the variables Ry, A2, R1, R2, R4, R5, R6, Rd, Re and Rf are as defined above. ORx is a leaving group attached via oxygen, where Rx is preferably C1-C6-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, pentyl or hexyl, or phenyl-C1-C6-alkyl, such as benzyl.


The cyclization can be carried out analogously to the cyclization, described above, of compound IV to compound II.


The phosphonate XVIII can be prepared by coupling of the previously N-deprotected phosphonate XIX with the N-protected amino acid XX and subsequent removal of the protective group:







In the scheme, the variables Rx, Ry, A2, R1, R2, R4, R5, R6, Rd, Re and Rf are as defined above. Cbz is the benzyloxycarbonyl protective group. Instead of Cbz and Boc, it is also possible to use other amino protective groups.


The Cbz protective group is generally removed reductively using hydrogen in the presence of palladium-on-carbon. Other customary processes for removing Cbz groups may also be employed. If other protective groups are used, the removal is generally carried out according to the processes suitable for the group in question.


The above reaction can be carried out according to the process described in Tetrahedron 2004, 60, 961-965. Thus, the coupling in Step 2 with the amino acid XX can be carried out analogously to the preparation of compound V from compounds VI and VII. Deprotection of compound XXI to compound XVIII can be carried out analogously to the deprotection of compound V to compound IV.


The phosphonates XIX are either commercially available or they can be prepared according to the processes described in Synthesis 1986, 53-60.


Process E

The invention furthermore provides a process for preparing piperazine compounds of the general formula I which comprises reacting, in the presence of a base, a compound of the formula IX







in which the variables A1, Ra, Rb and Rc are as defined above and R3 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl,


with a phosphonic ester of the formula XXI







in which the variables A2, R1, R2, R4, R5, R6, Rd, Re and Rf are as defined above, ORx is a leaving group attached via oxygen, where Rx is preferably C1-C6-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, pentyl or hexyl, or phenyl-C1-C6-alkyl, such as benzyl, Ry is C1-C4-alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl, aryl, for example phenyl, or aryl-C1-C4-alkyl, for example benzyl, and SG is an amino protective group, for example Boc,


to give the compound of the formula XXII







removing the amino protective group giving the compound of the formula XXIII







and cyclizing the compound of the formula XXIII to the compound of the formula I.


The first step of the process according to the invention is also referred to as Wittig-Horner-Emmons reaction.


Ry is preferably C1-C4-alkyl, in particular methyl or ethyl.


The process according to the invention is preferably used to prepare compounds of the formula I.1 in which R3 is H. To this end, the procedure described above is adopted, where the aldehyde XII (corresponds to the compound IX in which R3 is H) is used for the Wittig-Horner-Emmons reaction. Using the open-chain phosphonic ester XXI.1, the latter is converted into the olefin of the formula XXII.1 which, after removal of the protective group, is cyclized to piperazine I.1, as illustrated in the scheme below:







In the formulae I.1, XII, XXI, XXII.1 and XXIII.1, the variables A1, A2, R1-R6, Ra, Rb, Rc, Rd, Re and Rf are as defined for formula I. ORx is a leaving group attached via oxygen, where Rx is preferably C1-C6-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, pentyl or hexyl, or phenyl-C1-C6-alkyl, such as benzyl. Ry is C1-C4-alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, or isobutyl, aryl, for example phenyl, or aryl-C1-C4-alkyl, for example benzyl. Ry is preferably C1-C4-alkyl, in particular methyl or ethyl. SG is a suitable amino protective group, in particular Boc.


The reaction of the phosphonate XXI with the aldehyde XII can take place analogously to the reaction, described above, of the phosphonate XVII with the aldehyde XII. The reaction can also be carried out analogously to the process described in Synthesis 1992, 487-490, Synthesis 1992, 482-486 and Synthesis 1984, 53-60, which are expressly incorporated herein in their entirety.


The removal of the protective group is generally carried out by processes known form the literature. If, for example, SG is Boc, the protective group can be removed as described above for compound V, for example by reacting the compound XXII.1 with an acid. The deprotection reaction can also be carried out analogously to the process described in Tetrahedron 2004, 60, 961-965, which is expressly incorporated herein in its entirety.


The cyclization of dipeptide XXIII.1 to piperazine I.1 can be carried out analogously to the conversion of compound IV into compound II. In this case, however, only the cyclization in the presence of an acid is suitable, owing to the presence of the double bond. Here, what was stated for the cyclization of the compound IV with respect to suitable and preferred acids and solvents applies correspondingly. The acidic cyclization can also be carried out according to the process described in Tetrahedron 2004, 60, 961-965, which is expressly incorporated herein in its entirety.


Instead of the N-protected, for example the Boc-protected, compound XXI.1 it is also possible to use the corresponding deprotected compound for the Wittig-Horner-Emmons reaction, so that compound XXIII.1 is formed directly. The protective group is generally removed by processes known from the literature. If, for example, SG is Boc, the Boc protective group can be removed from compound XXI as described above for compound V, for example by reacting the compound XXI with an acid. The deprotection reaction may also be carried out analogously to the process described in Tetrahedron 2004, 60, 961-965, which is expressly incorporated herein in its entirety.


In principle, the process according to the invention can also be employed for preparing compounds I in which R3 is not necessarily hydrogen but can also be C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C8-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl and especially C1-C6-alkyl. In this case, instead of the aldehyde XII, the ketone IX.1 is used







in which R3 is C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkynyl, phenyl, phenyl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C8)-alkyl and especially C1-C6-alkyl.


Here, what was said above with respect to the preparation of the piperazine compound of the formula I.1 applies correspondingly. However, here more drastic reaction conditions are required in most cases, for example stronger bases, higher temperatures, longer reaction times, etc., so that the above-described preparation of the compound I via phosphonate XXI is preferably employed for the preparation of compounds I.1.


Process F

The compounds of the formula I where R1≠hydrogen can also be prepared by reacting a piperazine compound of the formula I in which R1 is hydrogen with an alkylating agent or acylating agent which contains the radical R1 different from hydrogen. Such reactions can be carried out analogously to processes known from the literature, for example according to the methods described by I. O. Donkor et al., Bioorg. Med. Chem. Lett. 11 (19) (2001), 2647-2649, B. B. Snider et al., Tetrahedron 57 (16) (2001), 3301-3307, I. Yasuhiro et al., J. Am. Chem. Soc. 124(47) (2002), 14017-14019, or M. Falorni et al., Europ. J. Org. Chem. (8) (2000), 1669-1675.







To this end, the piperazine compound of the formula I where R1=hydrogen is reacted with a suitable alkylating agent, hereinbelow compound X1—R1, or acylating agent, hereinbelow compound X2—R1, which gives a piperazine compound of the formula I where R1≠hydrogen.


In the alkylating agents X1—R1, X1 can be halogen or O—SO2—Rm, where Rm is C1-C4-alkyl or aryl, which are optionally substituted by halogen, C1-C4-alkyl or halo-C1-C4-alkyl. In the acylating agents X2—R1, X2 can be halogen, in particular Cl. Here, R1≠hydrogen and is as defined above and is in particular C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-cycloalkenyl, C3-C6-alkynyl, C3-C6-cycloalkynyl, phenyl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl; phenyl-[C1-C6-alkoxycarbonyl]-(C1-C6)-alkyl or phenylheterocyclyl-(C1-C6)-alkyl; or COR21 or SO2R25, where the abovementioned aliphatic, cyclic or aromatic moieties of R1 may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, [di-(C1-C4)-alkyl]amino, C1-C4-alkylcarbonyl, hydroxycarbonyl, C1-C4-alkoxycarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, [di-(C1-C4)-alkyl]aminocarbonyl or C1-C4-alkylcarbonyloxy.


The reaction is usually carried out at temperatures in the range from −78° C. to the boiling point of the reaction mixture, preferably from −50° C. bis 65° C., in particular preferably from −30° C. to 65° C. In general, the reaction is carried out in a solvent, preferably in an inert organic solvent.


Suitable solvents are the compounds cited under process B (cyclization of dipeptide IV to piperazine II), inter alia toluene, dichloromethane, tetrahydrofuran or dimethyl formamide or mixtures thereof.


In a preferred embodiment of the invention, the reaction is carried out in tetrahydrofuran.


In a preferred embodiment, the compound I where R1═H is reacted with the alkylating or acylating agent in the presence of a base. Suitable bases are the compounds cited under process B (cyclization of dipeptide IV to piperazine II). The bases are generally employed in equimolar amounts. They can also be used in excess or even as solvent. In a preferred embodiment, the base is added in an equimolar amount or in a substantially equimolar amount. In a further preferred embodiment, the base used is sodium hydride.


Work-up is generally carried out analogously to the procedure described under process B (cyclization of dipeptide IV to piperazine II).


Alternatively, the alkylation or acylation of the group NR1 in which R1 is H, can also be carried out in the precursors. Thus, for example, compounds II, IV, V, XIII, XIV, XVI, XXII or XXIII in which R1 is H can be N-alkylated or N-acylated as described above.


Process G

Analogously to the manner described above, compounds I or precursors thereof in which R2 is hydrogen can be reacted with alkylating agents R2—X1 or acylating agents R2—X2, which gives compounds of the formula I or precursors thereof where R2≠hydrogen. The reaction conditions correspond to the conditions described above.


Process H

Moreover, the compounds of the formula I can be modified on group A1. Thus, they can be prepared, for example, according to the process illustrated in the scheme below by converting the substituent Ra, for example analogously to the methods described by J. Tsuji, Top. Organomet. Chem. (14) (2005), 332 pp., or J. Tsuji, Organic Synthesis with Palladium Compounds, (1980), 207 pp.







To this end, a piperazine compound of the formula Ia which, instead of the substituent Ra, has a suitable leaving group L is converted by reaction with a coupling reagent which contains a group Ra (compound Ra—X3) into another piperazine derivative of the formula I.


The reaction is usually carried out in the presence of a catalyst, preferably in the presence of a transition metal catalyst. In general, the reaction is carried out in the presence of a base.


This reaction sequence is illustrated below using the example of the substituent Ra and can of course be employed in an analogous manner for converting the substituents Rb and Rc.


Suitable leaving groups L are, for example, halogen or S(O)nRk, where n=0, 1, 2 and Rk is C1-C6-alkyl, halo-(C1-C6)-alkyl or optionally halogenated or C1-C4-alkyl-substituted aryl.


Suitable coupling reagents X3—Ra are in particular those compounds in which X3, if Ra is C1-C6-alkyl, C2-C6-alkenyl, aryl or heteroaryl, denotes one of the following groups:

    • Zn—RI where RI is halogen, C1-C6-alkyl, C2-C6-alkenyl, aryl or heteroaryl;
    • B(ORm)2 where Rm is H or C1-C6-alkyl, where two alkyl substituents together may form a C2-C4-alkylene chain; or
    • SnRn3 where Rn is C1-C6-alkyl or aryl.


If Ra is C2-C6-alkynyl, X3 may also be hydrogen.


To prepare the compound I in which Ra is CN, the compound Ia in which L is bromine or iodine can also be reacted with copper cyanide analogously to known processes (see, for example, Organikum, 21st Edition, 2001, Wiley, p. 404 and literature cited therein).


Here, according to a preferred embodiment, L or Ra in the compounds of the formula I are attached in the ortho-position to the point of attachment of A1 to a carbon atom of A1.


This reaction is usually carried out at temperatures in the range from −78° C. to the boiling point of the reaction mixture, preferably from −30° C. to 65° C., particularly preferably at temperatures from 30° C. to 65° C. In general, the reaction is carried out in an inert organic solvent in the presence of a base.


Suitable solvents are the compounds cited under process B (cyclization of dipeptide IV to piperazine II). In one embodiment of the process according to the invention, use is made of tetrahydrofuran with a catalytic amount of water; in another embodiment, only tetrahydrofuran is used.


Suitable bases are the compounds cited under process B (cyclization of dipeptide IV to piperazine II).


The bases are generally employed in equimolar amounts. They can also be employed in excess or even as solvent.


In a preferred embodiment of the process according to the invention, the base is added in an equimolar amount. In a further preferred embodiment, the base used is triethylamine or cesium carbonate, particularly preferably cesium carbonate.


Suitable catalysts for the process according to the invention are, in principle, compounds of the transition metals Ni, Fe, Pd, or Cu. It is possible to use organic or inorganic compounds. Pd(PPh3)2Cl2, Pd(OAc)2, PdCl2 or Na2PdCl4 may be mentioned by way of example. Here, Ph is phenyl.


The different catalysts can be employed either individually or else as mixtures. In a preferred embodiment of the invention, Pd(PPh3)2Cl2 is used.


The work-up can be carried out analogously to the procedure described for process B (cyclization of dipeptide IV to piperazine II).


Alternatively, the conversion of group A1 can also be carried out with the precursors of the compound Ia. Thus, for example, compounds II, IV, V, VII, VIII, IX, XI and XII in which, instead of the radical Ra, there is a group L attached to A1, can be subjected to the reaction described above.


Process I

piperazine compounds of the formula I in which one of the groups Ra, Rb or Rc is COOH can furthermore be prepared from piperazine compounds of the formula I in which Ra, Rb or Rc is COORz, where Rz is alkyl, for example CH3, by hydrolysis of the ester group. The hydrolysis can be performed, for example, by reaction with (H3C)3SnOH, for example according to K. C. Nicolaou et al., Angew. Chem. Int. Ed. Engl. (44) (2005), 1378. The carboxylic acid obtained in this manner can then be converted by standard methods of organic synthesis, if appropriate after conversion into the acid chloride, by reaction with an amine HNRuRv or an alcohol HORw, into the corresponding ester or the amide (cf. e.g. Organikum, Autorenkollektiv, Leipzig 1993, 19. edition, pp. 424, 429). This reaction sequence is illustrated hereinbelow using the example of the substituent Ra, but it is, of course, also possible to employ this sequence in an analogous manner for converting the substituents Rb and Rc.







In this scheme, the variables A1, A2, R1-R6, Rb, Rc, Rd, Re and Rf have the meanings given above. Ru and Rv independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylsulfonyl, C1-C6-alkylaminosulfonyl, [di-(C1-C6)-alkylamino]sulfonyl or optionally substituted phenyl. Rw is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl. Rz is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, benzyl, in particular C1-C4-alkyl.


In a first step, the ester group in the piperazine compound I {Ra═COORz} is hydrolyzed. The hydrolysis can be performed, for example, by reaction with (H3C)3SnOH, which gives the free acid of I {Ra═COOH}. The conversion into the free acid is usually carried out using an excess of (H3C)3SnOH. In general, the reaction is carried out in an inert organic solvent. Suitable solvents include in particular dichloroethane. In general, the reaction is carried out at elevated temperature, for example at about 80° C.


In a second step, the acid I {Ra═COOH} is converted into its acid chloride (Ra═COCl). The conversion into the acid chloride is usually carried out at temperatures of from 10° C. to 50° C., preferably at room temperature, for example 25° C. In general, the reaction is carried out in an inert organic solvent. The suitable solvents include in particular dichloromethane. In a preferred embodiment, the reaction is carried out in dichloromethane and catalytic amounts of dimethylformamide. A large number of reagents are suitable for the chlorination, for example oxalyl chloride or thionyl chloride. Preference is given to using substantially equimolar amounts of the chlorinating reagent, in particular oxalyl chloride.


The reaction with an amine NHRuRv in the subsequent reaction is usually carried out by adding an excess of the amine in question. The reaction can be carried out in a temperature range of from 0° C. to 40° C., preferably at room temperature, for example 25° C.


The reaction with an alcohol HORw in the subsequent reaction is usually carried out by adding an excess both of the alcohol in question and of triethylamine.


The reaction can be carried out in a temperature range of from 0° C. to 40° C., preferably at room temperature, for example at 25° C.


The work-up can be carried out analogously to the procedure described for process B (cyclization of dipeptide IV to piperazine II).


The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. They are suitable as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I or Ia control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.


Depending on the application method in question, the compounds I or Ia, or herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:



Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Clycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.


In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.


In addition, the compounds I can also be used in crops which tolerate insects or fungal attack as the result of breeding, including genetic engineering methods.


Furthermore, it has been found that the compounds of the formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of the formula I.


As desiccants, the compounds of the formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.


Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.


Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.


The compounds I, or the herbicidal compositions comprising them, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading or watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.


The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.


Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and, for seed formulations, adhesives.


Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides, such as xanthan gum (Keizan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).


Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.


Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on dichlorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).


Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.


Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.


Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.


Suitable inert additives are, for example, the following:


mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone, or water.


Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.


Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF AG), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denaturated proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF AG, Sokalan types), polyalkoxylates, polyvinylamine (BASF AG, Lupamine types), polyethyleneimine (BASF AG, Lupasol types), polyvinylpyrrolidone and copolymers thereof.


Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.


Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.


Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of the formulae I or Ia, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.


The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).


The compounds I according to the invention can, for example, be formulated as follows:


1. Products for Dilution with Water


A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.


B Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight


C Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (eg. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.


D Emulsions

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (eg. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.


E Suspensions

In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.


F Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight.


G Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.


H Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.


2. Products to be Applied Undiluted
I Dusts

5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a tracking powder with an active compound content of 5% by weight.


J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.


K ULV Solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.


Specific formulations are given below:

  • I 20 parts by weight of the compound of the formula I are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100 000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
  • II 20 parts by weight of the compound of the formula I are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100 000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
  • III 20 parts by weight of the compound of the formula I are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100 000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
  • IV 20 parts by weight of the compound of the formula I are mixed thoroughly with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20 000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.
  • V 3 parts by weight of the compound of the formula I are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.
  • VI 20 parts by weight of the compound of the formula I are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.
  • VII 1 part by weight of the compound of the formula I is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.
  • VIII 1 part by weight of the compound of the formula I is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.


The compounds I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).


In a further embodiment, the compounds of the formula I or the herbicidal compositions can be applied by treating seed.


The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.


The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds.


The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.


The rates of application of the active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.


To widen the spectrum of action and to achieve synergistic effects, the compounds of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly. Suitable components for mixture partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, 2-hetaroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils, phenylpyrazolines, isoxazolines and derivatives thereof.


It may furthermore be beneficial to apply the compounds I alone or in combination with other herbicides, or in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Further additives such as non-phytotoxic oils and oil concentrates may also be added.


The examples below serve to illustrate the invention.







A PREPARATION EXAMPLES

The products were characterized by their retention time RT (in min) in an HPLC/MS (High Performance Liquid Chromatography combined with Mass Spectrometry), by NMR or by their melting point (m.p.).


HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany)


Eluent: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA in a gradient from 5:95 to 95:5 in 5 minutes at 40° C.


MS: Quadrupol electrospray ionization, 80 V (positive mode)


Example 1
3-Benzyl-1,4-dimethyl-6-(2-nitrobenzylidene)piperazine-2,5-dione






1.1 Ethyl 2-(tert-butoxycarbonylmethylamino)-3-(2-nitrophenyl)-3-trimethylsilanyloxy-propionate








    • At −78° C., lithium diisopropylamide solution (2 M in tetrahydrofuran/n-heptane, 46 ml, 92 mmol) was slowly added dropwise to ethyl (tert-butoxycarbonylmethylamino)acetate (20 g, 92 mmol) in THF (abs., 50 ml). The mixture was stirred at this temperature for 3 h. 2-Nitrobenzaldehyde (13.6 g, 90 mmol) in THF (tetrahydrofuran, absolute, 30 ml) was then slowly added dropwise. The mixture was stirred at −78° C. for 1.5 h, and trimethylsilyl chloride (10 g, 92 mmol) was then added dropwise. The reaction solution was slowly (12 h) warmed to room temperature and then concentrated on a rotary evaporator. The residue was taken up in ethyl acetate, washed, dried and concentrated. The residue obtained in this manner was then purified by column chromatography (SiO2, hexane/ethyl acetate). This gave 7.1 g (18%) of a non-polar isomer which were reacted further in the next step.





M+Na (m/z): 463.


1.2 Ethyl 3-hydroxy-2-methylamino-3-(2-nitrophenyl)propionate








    • Trifluoroacetic acid (20 ml) was added to ethyl 2-(tert-butoxycarbonylmethylamino)-3-(2-nitrophenyl)-3-trimethylsilanyloxypropionate (8.6 g, 19.5 mmol) in CH2Cl2 (100 ml), and the mixture was stirred at room temperature for 12 h. The mixture was then neutralized with NaHCO3 solution (saturated), the phases were separated and concentrated. The residue obtained in this manner was then purified by column chromatography (SiO2, hexane/ethyl acetate). This gave 1.7 g (32%) of the target compound as a light-yellow solid.





M+1 (m/z): 269.


1.3 Ethyl 2-{[2-(tert-butoxycarbonylmethylamino)-3-phenylpropionyl]methylamino}-3-hydroxy-3-(2-nitrophenyl)propionate








    • Ethyl 3-hydroxy-2-methylamino-3-(2-nitrophenyl)propionate (1.7 g, 6.3 mmol), 2-(tert-butoxycarbonylmethylamino)-3-phenylpropionic acid (2 g, 7 mmol), N-ethyldiisopropylamine (4.5 g, 35 mmol) and EDAC (3 g, 15.6 mmol) were stirred in THF (abs., 50 ml) for 3 days. The reaction solution was concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and the resulting solution was washed, dried and concentrated. This gave 2.1 g (63%) of the target compound as a light-yellow oil.





M+1 (m/z): 530.


1.4 Ethyl 3-hydroxy-2-[methyl-(2-methylamino-3-phenylpropionyl)amino]-3-(2-nitro-phenyl)propionate








    • Trifluoroacetic acid (10 ml) was added to ethyl 2-{[2-(tert-butylcarbonylmethylamino)-3-phenylpropionyl]methylamino}-3-hydroxy-3-(2-nitrophenyl)propionate (2.1 g, 3.9 mmol) in CH2Cl2 (20 ml), and the mixture was stirred at room temperature for 2 h and then concentrated on a rotary evaporator. The residue obtained in this manner was reacted as crude product in the next step.





1.5 3-Benzyl-6-[hydroxy-(2-nitrophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione








    • The residue obtained in 1.4 is taken up in THF (50 ml), and NH4OH (25% in H2O, 10 ml) is added. The mixture is stirred at room temperature for 12 h. After addition of H2O (100 ml), the mixture is extracted with methyl tert-butyl ether and the organic phase is dried and concentrated. The residue obtained in this manner is purified by column chromatography (SiO2, hexane/ethyl acetate). This gives 0.57 g (38%) of a polar isomer which is reacted further in the next step





M+1 (m/z): 384.


1.6 (5-Benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-yl)-(2-nitrophenyl)methyl methanesulfonate








    • DMAP (1.8 g, 14.7 mmol) and methanesulfonyl chloride (30 ml) were added to 3-benzyl-6-[hydroxy-(2-nitrophenyl)methyl]-1,4-dimethylpiperazine-2,5-dione (5.5 g, 14.3 mmol) in pyridine (100 ml), and the mixture was stirred at room temperature for 12 h and then concentrated on a rotary evaporator. After addition of H2O and CH2Cl2, the insoluble black resins were filtered off using a nutsch filter, the phases were separated and the organic phase was concentrated. The residue obtained in this manner was purified by column chromatography (SiO2, hexane/ethyl acetate). This gave 5.1 g (77%) of the target compound as a light-yellow foam.





M+1 (m/z): 462.


1.7 3-Benzyl-1,4-dimethyl-6-(2-nitrobenzylidene)piperazine-2,5-dione

At 0° C., DBU (1.4 g, 9 mmol) was slowly added dropwise to (5-benzyl-1,4-dimethyl-3,6-dioxopiperazin-2-yl)-(2-nitrophenyl)methyl methanesulfonate (4.25 g, 9 mmol) in THF (100 ml), and the mixture was stirred at 0° C. for 4 h. At this temperature, the pH was then adjusted to 7 using citric acid (10%) and the mixture was then allowed to warm slowly to room temperature. After addition of H2O and ethyl acetate, then phases were separated and the organic phase was concentrated. The residue obtained in this manner was purified by column chromatography (SiO2, methyl tert-butyl ether/ethyl acetate). This gave 2.5 g (76%) of the target compound as a yellow foam.


The Z:E isomer mixture obtained in this manner was separated by preparative MPLC (silica gel: Merck Lichroprep RP-18 (40-63 μm), MeOH:H2O=60:40). 1H-NMR (CDCl3) of the separated isomers:


a) δ=2.62 (s, 3H), 3.09 (s, 3H), 3.23 (m, 2H), 4.39 (m, 1H), 6.39 (d, 1H), 7.13 (s, 1H), 7.17 (m, 1H), 7.24 (m, 1H), 7.32 (m, 2H), 7.44 (m, 1H), 7.49 (m, 1H), 8.05 (d, 2H).


b) δ=2.91 (s, 3H), 3.15 (dm 1H), 3.33 (s, 3H), 3.29 (dm, 1H), 4.32 (m, 1H), 6.28 (s, 1H), 6.75 (m, 1H), 7.08 (m, 2H), 7.32 (m, 3H), 7.39 (m, 1H), 7.47 (m, 1H), 8.04 (d, 1H).


Example 105/106
3-Benzyl-1,4-dimethyl-6-(2-thiazol-2-ylbenzylidene)piperazine-2,5-dione

In a reaction vessel, 600 mg of 3-benzyl-1,4-dimethyl-6-(2-iodobenzylidene)piperazine-2,5-dione (Example 4, prepared analogously to Example 1), 250 mg of bis(dibenzylideneacetone)palladium and 500 mg of triphenylarsan were initially charged in 30 ml of dioxane under an atmosphere of argon. 1 g of 2-(tributylstannyl)thiazole was added, and the mixture was heated at 60° C. for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel using hexane/methyl tert-butyl ether (2:1 v/v).


In this manner, a total of 404 mg of the title compound were obtained as a wax-like solid.


Example 115
3-Benzyl-1,4-dimethyl-6-(2-cyano-5,6-difluorobenzylidene)piperazine-2,5-dione

In a reaction vessel, 2.0 g of 3-benzyl-1,4-dimethyl-6-(2-bromo-5,6-difluorobenzylidene)piperazine-2,5-dione (Example 119, prepared analogously to Example 1) were reacted with 1.7 g of copper(1) cyanide in 50 ml of N-methylpyrrolidone under an atmosphere of argon at 155° C. for 18 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate, and the resulting solution was washed 3 times with water, dried and again concentrated under reduced pressure. The residue was chromatographed on silica gel using hexane/ethyl acetate (1:1 v/v). This gave 331 mg of the Z isomer as a light-yellow solid of melting point 175° C. and 310 mg of the E isomer as a beige solid of melting point 205° C.


The compounds listed in Tables 2, 3 and 4 below and the compounds listed in Table 5 below were prepared in an analogous manner (Examples 2 to 214).










TABLE 2








I























Example




RT HPLC/MS



No.
Ra
Rb
Rc
R1
or m.p.
Isomer
















1
2-NO2
H
H
CH3
2.831 min








m/z = 366.0







[M + H]+


2
2-NO2
H
H
H
2.724 min
isomer







m/z = 352.4
1







[M + H]+


3
2-NO2
H
H
H
2.773 min
isomer







m/z = 352.4
2







[M + H]+


4
2-I
H
H
CH3
3.286 min







m/z = 446.9







[M + H]+


5
2-(CH3)3Si—C≡C—
H
H
CH3
4.039 min
isomer







m/z = 417.5
1







[M + H]+


6
2-(CH3)3Si—C≡C—
H
H
CH3
4.064 min
isomer







m/z = 417.5
2







[M + H]+


7
2-HC≡C—
H
H
CH3
3.053 min







m/z = 345.0







[M + H]+


8
2-NO2
5-Cl
H
CH3
3.128 min
isomer







m/z = 399.9
1







[M + H]+


9
2-NO2
5-Cl
H
CH3
3.215 min
isomer







m/z = 399.9
2







[M + H]+


10
2-NO2
4-OCH3
5-OCH3
CH3
2.801 min
isomer







m/z = 426.0
1







[M + H]+


11
2-NO2
4-OCH3
5-OCH3
CH3
2.828 min
isomer







m/z = 426.0
2







[M + H]+


12
2-NO2
6-CH3
H
CH3
3.088 min
isomer







m/z = 380.0
1







[M + H]+


13
2-NO2
6-CH3
H
CH3
3.091 min
isomer







m/z = 380.0
2







[M + H]+


14
2-CN
H
H
CH3
2.721 min







m/z = 346.1







[M + H]+







143° C.


15
2-NO2
4-N(CH3)2
H
CH3
3.038 min







m/z = 409.0







[M + H]+












16
2-NO2
4,5-(—O—CH2—O—)
CH3
2.778 min
isomer






m/z = 410.0
1






[M + H]+


17
2-NO2
4,5-(—O—CH2—O—)
CH3
2.856 min
isomer






m/z = 410.0
2






[M + H]+













18
2-NO2
6-Cl
H
CH3
3.105 min








m/z = 400.1







[M + H]+


19
2-NO2
5-F
H
CH3
2.973 min
isomer







m/z = 384.4
1







[M + H]+


20
2-NO2
5-F
H
CH3
3.037 min
isomer







m/z = 384.4
2







[M + H]+


21
2-NO2
3-OCH3
H
CH3
2.926 min







m/z = 396.1







[M + H]+


22
2-NO2
5-OCH3
6-
CH3
3.327 min





O—SO2-

m/z = 552.1





Ph

[M + H]+


23
2-NH2
H
H
CH3
2.249 min
isomer







m/z = 336.4
1







[M + H]+


24
2-NH2
H
H
CH3
2.079 min
isomer







m/z = 336.1
2







[M + H]+


25
2-NH—C(O)—CH3
H
H
CH3
2.372 min







m/z = 378.1







[M + H]+


26
2-NH—C(O)-Ph
H
H
CH3
2.837 min







m/z = 440.2







[M + H]+


27
2-NH—C(O)—NH—SO2-Ph
H
H
CH3
3.095 min







m/z = 533.2







[M + H]+


28
2-NH—SO2—NHCH3
H
H
CH3
2.505 min







m/z = 429.1







[M + H]+


29
2-NH—C(O)—NH-Ph
H
H
CH3
3.140 min







m/z = 455.2







[M + H]+


30
2-NH—C(O)—OCH3
H
H
CH3
2.667 min
isomer







m/z = 394.4
1







[M + H]+


31
2-NH—C(O)—OCH3
H
H
CH3
2.590 min
isomer







m/z = 394.2
2







[M + H]+


32
2-NH—SO2—NHCH2CH3
H
H
CH3
2.642 min







m/z = 443.1







[M + H]+


33
2-NH—SO2—NHCH(CH3)2
H
H
CH3
2.848 min







m/z = 457.1







[M + H]+


34
2-NH—CN
H
H
CH3
2.579 min
isomer







m/z = 361.1
1







[M + H]+


35
2-NH—CN
H
H
CH3
2.637 min
isomer







m/z = 361.2
2







[M + H]+


36
2-F
H
H
CH3
3.009 min
isomer







m/z = 339.4
1







[M + H]+


37
2-F
H
H
CH3
2.762 min
isomer







m/z = 339.4
2







[M + H]+


38
2-I
6-F
H
CH3
3.259 min







m/z = 465.0







[M + H]+


39
2-CN
6-F
H
CH3
3.033 min







m/z = 364.1







[M + H]+







138° C.


40
2-I
6-Cl
H
CH3
3.625 min







m/z = 481.0







[M + H]+


41
2-Br
6-Cl
H
CH3
3.437 min







m/z = 434.9







[M + H]+


42
2-CN
H
H
H
2.656 min







m/z = 332.1







[M + H]+







158° C.





43





H
H
CH3
2.936 min m/z = 404.1 [M + H]+
isomer 1





44





H
H
CH3
2.806 min m/z = 404.1 [M + H]+
isomer 2





45





H
H
CH3
2.878 min m/z = 388.1 [M + H]+
isomer 1





46





H
H
CH3
2.867 min m/z = 388.1 [M + H]+ 153° C.
isomer 2





47
2-(furan-2-yl)
H
H
CH3
3.173 min
isomer







m/z = 387.1
1







[M + H]+


48
2-(furan-2-yl)
H
H
CH3
3.284 min
isomer







m/z = 387.1
2







[M + H]+


49
2-(thiophen-2-yl)
H
H
CH3
3.378 min







m/z = 403.1







[M + H]+


50
2-(pyridin-2-yl)
H
H
CH3
2.131 min







m/z = 398.2







[M + H]+


51
2-(pyridin-3-yl)
H
H
CH3
2.214 min







m/z = 398.2







[M + H]+





52





H
H
CH3
2.963 min m/z = 402.2 [M + H]+
isomer 1





53





H
H
CH3
2.989 min m/z = 402.2 [M + H]+ 128° C.
isomer 2





54
2-CF3
H
H
CH3
3.164 min m/z = 389.1 [M + H]+





55





H
H
CH3
2.601 min m/z = 387.4 [M + Na]+





56





H
H
CH3
2.985 min m/z = 378.2 [M + H]+





57





H
H
CH3
2.803 min m/z = 415.5 [M + H]+





58
2-Br
5-CF3
H
CH3
3.435 min
isomer







m/z = 469.0
1







[M + H]+


59
2-Br
5-CF3
H
CH3
3.490 min
isomer







m/z = 469.0
2







[M + H]+







113° C.


60
2-Br
4-OCH3
5-OCH3
CH3
3.074 min
isomer







m/z = 461.0
1







[M + H]+







121° C.


61
2-Br
4-OCH3
5-OCH3
CH3
3.131 min
isomer







m/z = 461.1
2







[M + H]+


62
2-Br
5-F
H
CH3
3.380 min







m/z = 417.0







[M + H]+







106° C.


63
2-CN
5-CF3
H
CH3
3.338 min
isomer







m/z = 414.1
1







[M + H]+


64
2-CN
5-CF3
H
CH3
3.376 min
isomer







m/z = 414.1
2







[M + H]+


65
2-CN
4-OCH3
5-OCH3
CH3
2.805 min
isomer







m/z = 406.1
1







[M + H]+







163° C.


66
2-CN
4-OCH3
5-OCH3
CH3
2.764 min
isomer







m/z = 406.1
2







[M + H]+


67
2-CN
5-F
H
CH3
2.939 min
isomer







m/z = 364.4
1







[M + H]+


68
2-CN
5-F
H
CH3
2.950 min
isomer







m/z = 364.1
2







[M + H]+







128° C.


69
2-COOH
H
H
CH3
2.539 min







m/z = 365.1







[M + H]+


70
2-
H
H
CH3
2.599 min



C(O)NHCH2CH2CH3



m/z = 406.2







[M + H]+


71
2-C(O)OCH(CH3)2
H
H
CH3
3.271 min







m/z = 407.2







[M + H]+


72
2-C(O)NH—CH2CH═CH2
H
H
CH3
2.537 min








m/z = 404.1







[M + H]+


73
2-C(O)OCH3
H
H
CH3
2.878 min







m/z = 379.1







[M + H]+


74
2-COOCH2CF3
H
H
CH3
3.291 min







m/z = 447.1







[M + H]+


75
2-C(O)N(CH2CH3)2
H
H
CH3
2.752 min







m/z = 420.2







[M + H]+


76
2-C(O)OCH2-(o-F-
H
H
CH3
3.516 min



Ph)



m/z = 473.2







[M + H]+


77
2-C(O)NHCH2-(o,
H
H
CH3
2.937 min



o′-difluoro-Ph)



m/z = 490.2







[M + H]+


78
2-C(O)NHOCH3
H
H
CH3
2.305 min







m/z = 394.1







[M + H]+


79
2-C(O)NH—SO2—N(CH3)(i-Pr)
H
H
CH3
2.796 min







m/z = 499.2







[M + H]+


80
2-C(O)O-(o-NO2-
H
H
CH3
3.335 min



Ph)



m/z = 486.2







[M + H]+


81
2-C(O)NH—SO2—N(CH3)(i-Pr)
H
H
CH3
2.796 min







m/z = 499.2







[M + H]+


82
2-C(O)NH-(m-Br-
H
H
CH3
3.286 min



Ph)



m/z = 520.0







[M + H]+


83
2-C(O)NH2
H
H
CH3
2.220 min







m/z = 364.1







[M + H]+


84
2-C(O)NH—CH(CH3)(CH2—O—CH3)
H
H
CH3
2.520 min







m/z = 436.2







[M + H]+





85





H
H
CH3
2.416 min m/z = 434.2 [M + H]+





86
2-C(O)O—CH2C≡CH
H
H
CH3
3.003 min







m/z = 403.1







[M + H]+





87





H
H
CH3
3.084 min m/z = 432.1 [M + H]+















88
2-Br
4,5-(—O—CH2—O—)
CH3
3.115 min







m/z =






445.0






[M + H]+













89
2-Br
4-F
H
CH3
3.189 min
isomer







m/z =
1







417.0







[M + H]+


90
2-Br
4-F
H
CH3
3.197 min
isomer







m/z =
2







417.0







[M + H]+












91
2-CN
4,5-(—O—CH2—O—)
CH3
2.711 min







m/z =






412.1






[M + Na]+













92
2-CN
4-F
H
CH3
2.848 min








m/z =







386.1







[M + Na]+


93
2-Br
H
H
CH3
3.086 min







m/z =







399.0







[M + H]+


94
2-CN
4-CH3
H
CH3
2.940 min







m/z =







360.1







[M + H]+


95
2-C(S)NH2
H
H
CH3
2.634 min







m/z = 380.1







[M + H]+


96
2-CN
H
H
CH3
2.816 min







m/z =







346.4







[M + H]+







209° C.


97
2-OH
5-NO2
H
CH3
2.709 min







m/z =







382.1







[M + H]+


98
2-CN
5-NO2
H
CH3
3.029 min
isomer







m/z =
1







391.1







[M + H]+


99
2-CN
5-NO2
H
CH3
2.982 min
isomer







m/z =
2







391.1







[M + H]+





100





H
H
CH3
2.660 min m/z = 399.5 [M + H]+
isomer 1





101





H
H
CH3
2.736 min m/z = 399.5 [M + H]+
isomer 2





102





H
H
CH3
2.089 min m/z = 401.4 [M + H]+ 105° C.





103





H
H
CH3
2.780 min m/z = 457.5 [M + H]+ 115° C.
isomer 1





104





H
H
CH3
2.845 min m/z = 457.5 [M + H]+
isomer 2





105





H
H
CH3
3.074 min m/z = 404.1 [M + H]+
isomer 1





106





H
H
CH3
2.886 min m/z = 404.1 [M + H]+
isomer 2





107





H
H
CH3
2.563 min m/z = 387.5 [M + H]+
isomer 1





108





H
H
CH3
2.700 min m/z = 387.5 [M + H]+
isomer 2





109





H
H
CH3
2.680 min m/z = 399.1 [M + H]+
isomer 1





110





H
H
CH3
2.785 min m/z = 399.1 [M + H]+
isomer 2





111
2-NO2
6-Br
H
CH3
3.289 min
isomer







m/z = 444.0
1







[M + H]+







115° C.


112
2-NO2
6-Br
H
CH3
3.333 min
isomer







m/z = 444.0
2







[M + H]+







130° C.


113
2-CN
6-NH2
H
CH3
2.839 min







m/z =







361.1







[M + H]+







193° C.


114
2-CN
5-F
6-OH
CH3
2.716 min







m/z =







380.1







[M + H]+







205° C.


115
2-CN
5-F
6-F
CH3
3.153 min







m/z =







382.1







[M + H]+







175° C.


116
2-CN
6-CN
H
CH3
2.903 min
isomer







m/z =
1







371.4







[M + H]+







225° C.


117
2-CN
6-CN
H
CH3
2.790 min
isomer







m/z =
2







371.4







[M + H]+







235° C.


118
2-CN
6-Br
H
CH3
3.122 min







m/z =







424.4







[M]+







175-180° C.


119
2-Br
5-F
6-F
CH3
3.488 min







m/z =







435.0







[M]+


120
2-CN
6-CH═CH2
H
CH3
3.143 min
isomer







m/z =
1







372.1







[M + H]+


121
2-CN
6-CH═CH2
H
CH3
3.261 min
isomer







m/z =
2







372.0







[M + H]+





122





H
H
CH3
3.343 min m/z = 392.5 [M + H]+





123
2-NHC(O)CH3
6-Br
H
CH3
3.035 min







m/z = 456.2







[M + H]+





124





H
H
CH3
2.654 min m/z = 399.1 [M + H]+





125
2-CN
6-NHC(O)CH3
H
CH3
2.676 min







m/z = 403.5







[M + H]+


126
2-CN
6-NHC(O)NH(Ph)
H
CH3
3.514 min







m/z = 480.5







[M + H]+


127
2-CN
6-N(CH3)2
H
CH3
3.171 min







m/z = 389.5







[M + H]+







58° C.


128
2-NH—SO2—NHCH(CH3)2
H
H
CH3
3.129 min







m/z = 482.0







[M + H]+







103° C.


129
2-CH═CH2
H
H
CH3
3.259 min
isomer







m/z = 347.1
1







[M + H]+


130
2-CH═CH2
H
H
CH3
3.262 min
isomer







m/z = 347.1
2







[M + H]+


131
2-CN
4-Cl
5-Cl
CH3
3.421 min







m/z = 413.0







[M]+


132
2-Br
5-Cl
6-Cl
CH3
3.744 min







m/z = 468.8







[M]+


133
2-CN
5-Cl
6-Cl
CH3
3.430 min
isomer







m/z = 413.9
1







[M]+


134
2-CN
5-Cl
6-Cl
CH3
3.408 min
isomer







m/z = 414.0
2







[M]+


135
2-Phenyl
H
H
CH3
3.534 min







m/z = 397.5







[M + H]+


136
2-CN
H
H
CH2—CH═CH2
3.198







m/z = 372.5







[M + H]+


137
2-CN
H
H
C(O)—(C6H5)
3.648







m/z = 436.5







[M + H]+


138
2-CN
H
H
CH2—OH
2.524







m/z = 362.4







[M + H]+


139
2-CN
H
H
CH2—C(O)—OCH3
3.233







m/z = 403.7







[M + H]+


140
2-CN
H
H
C(O)—CH3
3.322







m/z = 374.0







[M + H]+


141
2-SO2CH3
H
H
CH3
m/z = 399.4
isomer







[M + H]+
1


142
2-SO2CH3
H
H
CH3
m/z = 399.2
isomer







[M + H]+
2


143
2-NO2
6-CH═CH2
H
CH3
m/z = 392.3
isomer







[M + H]+
1


144
2-NO2
6-CH═CH2
H
CH3
m/z = 392.3
isomer







[M + H]+
2





145





H
H
CH3
m/z = 404.4 [M + H]+





146





H
H
CH3
m/z = 404.4 [M + H]+





147





H
H
CH3
m/z = 402.4 [M + H]+ 98° C.
isomer 1





148





H
H
CH3
m/z = 402.4 [M + H]+ 112° C.
isomer 2





149





H
H
CH3
m/z = 389.4 [M + H]+
isomer 1





150





H
H
CH3
m/z = 389.4 [M + H]+
isomer 2





151
2-CN
6-CF3
H
CH3
3.212
isomer







m/z = 414.5
1







[M]+


152
2-CN
6-CF3
H
CH3
3.243
isomer







m/z = 414.5
2







[M]+


153
2-Br
6-CF3
H
CH3
3.522







m/z = 469.4







[M + H]+


154
2-CN
5-Cl
6-Cl
H
3.131 min







m/z = 422.0







[M + Na]+


155
2-Br
5-Cl
6-Cl
C(O)—CH3
4.146 min







m/z = 518.8







[M + Na]+


156
2-Br
5-Cl
6-Cl
H
3.484 min







m/z = 454.8







[M + H]+


157
2-CN
6-Cl
H
CH3
3.070
isomer







m/z = 380.4
1







[M + H]+


158
2-CN
6-Cl
H
CH3
3.117
isomer







m/z = 380.4
2







[M + H]+





Example No. Example Number


m.p. melting point


Ph phenyl


i-Pr isopropyl














TABLE 3








(I)
























Ex-









ample





RT HPLC/MS



No.
Ra
Rb
Rc
R3
R1
or m.p.
Isomer





159
2-NO2
H
H
Br
CH3
3.306 min









m/z = 446.0








[M + H]+


160
2-CN
H
H
Br
CH3
3.113 min








m/z = 424.4








[M]+


161
2-NO2
H
H
CH═CH2
CH3
3.172 min








m/z = 392.1








[M + H]+


162
2-NO2
H
H
CH(CH3)2
CH3
3.369 min
isomer








m/z = 408.2
1








[M + H]+


163
2-NO2
H
H
CH(CH3)2
CH3
3.096 min
isomer








m/z = 408.1
2








[M + H]+


164
2-Br
H
H
CN
CH3
3.180 min








m/z = 424.4








[M]+


165
2-Br
H
H
Br
CH3
3.578 min
isomer








m/z = 478.9
1








[M + H]+


166
2-Br
H
H
Br
CH3
3.643 min
isomer








m/z = 478.9
2








[M + H]+





Example No. Example Number


m.p. melting point














TABLE 4








(I)























Ex-








ample





RT HPLC/MS


No.
Ra
Rb
Rc
R2
R1
or m.p.





167
2-NO2
H
H
CH2CH3
C(O)CH3
3.578 min








m/z = 408.1








[M + H]+


168
2-Br
H
H
C(O)CH3
C(O)CH3
3.812 min








m/z = 456.9








[M + H]+


169
2-Br
H
H
CH2—(C6H5)
CH2—(C6H5)
4.385 min








m/z = 552.9








[M + H]+


170
2-Br
H
H
CH2—CH3
CH2—CH3
3.637 min








m/z = 428.9








[M + H]+


171
2-Br
H
H
CH2—CH═CH2
CH2—CH═CH2
3.879 min








m/z = 453.0








[M + H]+


172
2-CN
H
H
CH2—(C6H5)
CH2—(C6H5)
3.995 min








m/z = 498.1








[M + H]+


173
2-CN
H
H
CH2—CH3
CH2—CH3
3.223 min








m/z = 374.1








[M + H]+


174
2-CN
H
H
CH2—CH═CH2
CH2—CH═CH2
3.469 min








m/z = 398.1








[M + H]+


175
2-Br
H
H
CH2—(C6H5)
C(O)CH3
4.235 min








m/z = 504.9








[M + H]+








98° C.


176
2-Br
H
H
CH2—CH═CH2
C(O)CH3
4.010 min








m/z = 454.9








[M + H]+


177
2-Br
H
H
CH2—CH3
C(O)CH3
3.921 min








m/z = 441.4








[M + H]+


178
2-Br
H
H
CH2—(C6H5)
H
3.620 min








m/z = 463.4








[M + H]+


179
2-Br
H
H
CH2—CH═CH2
H
3.322 min








m/z = 410.9








[M + H]+








78° C.


180
2-Br
H
H
CH2—CH3
H
3.216 min








m/z = 401.0








[M + H]+


181
2-CN
H
H
CH2—(C6H5)
H
3.218 min








m/z = 408.0








[M + H]+


182
2-CN
H
H
CH2—CH═CH2
H
2.929 min








m/z = 358.4








[M + H]+


183
2-CN
H
H
CH2—CH3
H
2.830 min








m/z = 346.4








[M + H]+





Example No. Example Number


m.p. melting point
















TABLE 5





Example

RT HPLC/MS



No.
Name
or m.p.
Isomer







184
3-benzyl-1,4-dimethyl-6-(4-nitro-1H-
2.743 min, m/z = 405.2 [M + H]+
isomer 1



indol-3-ylmethylene)piperazine-2,5-dione
159° C.


185
3-benzyl-1,4-dimethyl-6-(4-nitro-1H-
2.608 min, m/z = 405.1 [M + H]+
isomer 2



indol-3-ylmethylene)piperazine-2,5-dione
238° C.


186
tert-butyl 3-(5-benzyl-1,4-dimethyl-3,6-
3.776 min, m/z = 505.0 [M + H]+
isomer 1



dioxopiperazin-2-ylidenemethyl)-4-nitro-



indole-1-carboxylate


187
tert-butyl 3-(5-benzyl-1,4-dimethyl-3,6-
4.243 min, m/z = 505.5 [M + H]+
isomer 2



dioxopiperazin-2-ylidenemethyl)-4-nitro-



indole-1-carboxylate


188
1-methyl-6-(2-nitrobenzylidene)-3-
2.579 min, m/z = 357.9 [M + H]+
isomer 1



thiophen-2-ylmethylpiperazine-2,5-dione


188
1-methyl-6-(2-nitrobenzylidene)-3-
2.579 min,
isomer 1



thiophen-2-ylmethylpiperazine-2,5-dione
m/z = 357.9 [M + H]+


189
1-methyl-6-(2-nitrobenzylidene)-3-
2.622 min,
isomer 2



thiophen-2-ylmethylpiperazine-2,5-dione
m/z = 358.0 [M + H]+


190
3-benzyl-6-(5-chloro-1-methyl-3-
3.108 min,



trifluoromethyl-1H-pyrazol-4-yl-
m/z = 427.1 [M + H]+



methylene)-1,4-dimethylpiperazine-2,5-



dione


191
3-benzyl-1,4-dimethyl-6-(2-nitro-
2.730 min,
isomer 1



thiophen-3-ylmethylene)piperazine-2,5-
m/z = 372.1 [M + H]+



dione


192
3-benzyl-1,4-dimethyl-6-(2-nitro-
2.784 min,
isomer 2



thiophen-3-ylmethylene)piperazine-2,5-
m/z = 372.1 [M + H]+



dione


193
3-benzyl-1,4-dimethyl-6-(3-nitro-
2.756 min,
isomer 1



thiophen-2-ylmethylene)piperazine-2,5-
m/z = 372.0 [M + H]+



dione


194
3-benzyl-1,4-dimethyl-6-(3-nitro-
2.899 min,
isomer 2



thiophen-2-ylmethylene)piperazine-2,5-
m/z = 372.1 [M + H]+



dione


195
1,4-dimethyl-3-(2-nitrobenzylidene)-6-
2.884 min,



thiophen-2-ylmethylpiperazine-2,5-dione
m/z = 372.1 [M + H]+


196
3-benzyl-1,4-dimethyl-6-(3-nitropyridin-4-
2.425 min,
isomer 1



ylmethylene)piperazine-2,5-dione
m/z = 367.1 [M + H]+




180° C.


197
3-benzyl-1,4-dimethyl-6-(3-nitropyridin-4-
2.418 min,
isomer 2



ylmethylene)piperazine-2,5-dione
m/z = 367.1 [M + H]+




175° C.


198
3-benzyl-1,4-dimethyl-6-(3-nitropyridin-2-
2.606 min,



ylmethylene)piperazine-2,5-dione
m/z = 367.1 [M + H]+




165° C.


199
3-benzyl-1,4-dimethyl-6-(4-bromo-1H-
2.845 min,



indol-3-ylmethylene)piperazine-2,5-dione
m/z = 440.0 [M + H]+




236° C.


200
3-benzyl-1,4-dimethyl-6-(4-cyano-1H-
2.553 min,
isomer 1



indol-3-ylmethylene)piperazine-2,5-dione
m/z = 385.2 [M + H]+


201
3-benzyl-1,4-dimethyl-6-(4-cyano-1H-
2.553 min,
isomer 2



indol-3-ylmethylene)piperazine-2,5-dione
m/z = 385.2 [M + H]+


202
3-benzyl-1,4-dimethyl-6-(4-
3.887 min,



trimethylsilanylethynyl-1H-indol-3-
m/z = 456.1 [M + H]+



ylmethylene)piperazine-2,5-dione


203
2-(1,4-dimethyl-3,6-dioxo-5-thiophen-2-
2.743 min,



ylmethylpiperazin-2-ylidene-
m/z = 352.1 [M + H]+



methyl)benzonitrile


204
3-benzyl-6-(2-bromopyridin-3-
2.615 min,



ylmethylene)-1,4-dimethylpiperazine-2,5-
m/z = 400.0 [M]+



dione


205
3-benzyl-6-(2-cyanopyridin-3-
2.485 min,



ylmethylene)-1,4-dimethylpiperazine-2,5-
m/z = 347.4 [M]+



dione
218° C.


206
3-benzyl-6-(4-iodopyridin-3-yl-
3.029 min,



methylene)-1,4-dimethylpiperazine-2,5-
m/z = 445.9 [M + H]+



dione


207
2-[5-(4-fluorobenzyl)-1,4-dimethyl-3,6-
2.843 min,



dioxopiperazin-2-ylidene-
m/z = 364.0 [M + H]+



methyl]benzonitrile


208
3-benzyl-6-(5-bromo-3H-imidazol-4-
200° C.
isomer 1



ylmethylene)-1,4-dimethylpiperazine-2,5-



dione


209
3-benzyl-6-(5-bromo-3H-imidazol-4-
m/z = 389.1 [M]+
isomer 2



ylmethylene)-1,4-dimethylpiperazine-2,5-



dione


210
3-benzyl-6-(5-cyano-3H-imidazol-4-
170° C.



ylmethylene)-1,4-dimethylpiperazine-2,5-



dione


211
3-benzyl-6-(5-cyano-3H-imidazol-4-
m/z = 336.2 [M + H]+
isomer 2



ylmethylene)-1,4-dimethylpiperazin-2,5-



dione


212
3-benzyl-6-(5-brom-3H-[1,2,3]triazol-4-
m/z = 390.0 [M]+
isomer 1



ylmethylene)-1,4-dimethylpiperazin-2,5-



dione


213
3-benzyl-6-(5-brom-3H-[1,2,3]triazol-4-
m/z = 392.0 [M ]+
isomer 2



ylmethylene)-1,4-dimethylpiperazin-2,5-



dione


214
3-(2-Iodobenzylidene)-1,4-dimethyl-6-
3.303 min



(thiophen-2-ylmethyl)piperazin-2,5-dione
m/z = 453.0 [M + H]+





Ex. No. Example Number


m.p. melting point






Part B
USE EXAMPLES

The herbicidal activity of the compounds of the formula I was demonstrated by greenhouse experiments:


The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.


For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this has been impaired by the active ingredients.


For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.


Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.


Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. Good herbicidal activity is given for values of at least 70 and very good herbicidal activity is given for values of at least 85.


The plants used in the greenhouse experiments belonged to the following species:
















Scientific name
Common name










Lulium perenne (LOLMU)
annual ryegrass




Amaranthus retroflexus

pig weed



(AMARE)




Abutilon theophrasti (ABUTH)
velvet leaf




Apera spica-venti (APESV)
windgrass




Avena fatua (AVEFA)
wild oat




Echinochloa crus galli

barnyard grass



(ECHCG)




Setaria faberi (SETFA)
giant foxtail




Setaria viridis (SETVI)
green foxtail










The compounds of Examples 1, 13, 16, 44, 47, 48, 49, 51, 52, 129, 132, 160 and 170 exhibit good to very good herbicidal activity when applied by the post-emergence method.


The compounds of Examples 44 and 160, applied by the post-emergence method at an application rate of 3 kg/ha, exhibit good herbicidal activity against ABUTH.


The compounds of Examples 1, 16 and 129, applied by the post-emergence method at an application rate of 1 kg/ha, exhibit very good herbicidal activity against AMARE. The compound of Example 13, applied by the post-emergence method at an application rate of 0.5 kg/ha, exhibits very good herbicidal activity against AMARE.


The compound of Example 132, applied by the post-emergence method at an application rate of 3 kg/ha, exhibits very good herbicidal activity against AVEFA.


The compound of Example 1, applied by the post-emergence method at an application rate of 1 kg/ha, exhibits very good herbicidal activity against LOLMU.


The compounds of Examples 44, 47/48 (mixture), 49, 51 and 160, applied by the post-emergence method at an application rate of 3 kg/ha, exhibit very good herbicidal activity, and the compounds of Examples 52 and 132 exhibit good herbicidal activity against SETFA. The compound of Example 170, applied by the post-emergence method at an application rate of 1 kg/ha, exhibits good herbicidal activity against SETFA.


The compounds of Examples 38, 40, 45, 54, 62, 73, 100, 101, 109, 110, 119, 124, 137, 140, 147, 148, 191, 198, 204, 206, 214 exhibit good to very good herbicidal activity when applied by the pre-emergence method.


The compound of Example 73, applied by the pre-emergence method at an application rate of 3 kg/ha, exhibits good herbicidal activity against ABUTH.


The compound of Example 137, applied by the pre-emergence method at an application rate of 1 kg/ha, exhibits good herbicidal activity against AMARE.


The compound of Example 206, applied by the pre-emergence method at an application rate of 1 kg/ha, exhibits good herbicidal activity against AVEFA.


The compounds of Examples 38, 45, 54, 124, 140, 147 and 198, applied by the pre-emergence method at an application rate of 1 kg/ha, exhibit very good herbicidal activity against APSEV. The compounds of Examples 119 and 191, applied by the pre-emergence method at an application rate of 0.5 kg/ha, exhibit good herbicidal activity against APSEV.


The compounds of Examples 38, 45, 100/101 (mixture) and 109/110 (mixture), applied by the pre-emergence method at an application rate of 1 kg/ha, exhibit very good herbicidal activity, and the compound 147 exhibits good herbicidal activity against ECHCG. The compounds of Examples 40 and 204, applied by the pre-emergence method at an application rate of 3 kg/ha, exhibit very good herbicidal activity, and the compound of Example 214 exhibits good herbicidal activity against ECHCG.


The compounds of Examples 109/110 (mixture) and 140, applied by the pre-emergence method at an application rate of 1 kg/ha, exhibit very good herbicidal activity against SETFA. The compound of Example 62, at an application rate of 3 kg/ha, and the compound of Example 206, at an application rate of 2 kg/ha, each exhibit good herbicidal activity against SETFA.


The compounds of Examples 100/101 (mixture), applied by the pre-emergence method at an application rate of 1 kg/ha, exhibit very good herbicidal activity against SETIT. The compounds of Examples 40 and 204, applied by the pre-emergence method at an application rate of 3 kg/ha, exhibit very good herbicidal activity against SETIT. The compound of Example 214, applied by the pre-emergence method at an application rate of 3 kg/ha, exhibits good herbicidal activity against SETIT.

Claims
  • 1-20. (canceled)
  • 21. A method for controlling unwanted vegetation comprising treating a plant, a plant seed, and/or a plant habitat with a herbicidally effective amount of at least one piperazine compound of formula (I)
  • 22. The method of claim 21, wherein Ra is attached in the ortho-position to the point of attachment of A1.
  • 23. The method of claim 21, wherein A1 is bicyclic aryl or hetaryl.
  • 24. The method of claim 21, wherein A1 and A2 are, independently of one another, selected from the group consisting of phenyl, naphthyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl.
  • 25. The method of claim 21, wherein A1 and A2 are, independently of one another, selected from the group consisting of phenyl, furyl, thienyl, triazolyl, tetrazolyl, and pyridinyl.
  • 26. The method of claim 21, wherein A1 is phenyl or pyridinyl.
  • 27. The method of claim 21, wherein A2 is phenyl or thienyl.
  • 28. The method of claim 21, wherein Ra is selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, [tri-(C1-C6)-alkylsilyl]-C2-C6-alkynyl, Z1P(O)(OR1)2, Z1COR11, Z4NR12R13, Z5CH═N—O—R14, Z6OR15, Z7SO2R16, C1-C6-alkylthio, C1-C6-alkylsulfinyl, aryl, and heterocyclyl, wherein Z1 is a bond or CH2 and each R9 is, independently of another, hydrogen or C1-C6-alkyl;Z3 is a bond and R11 is hydrogen, C1-C6-alkyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, [di-(C1-C6)-alkyl]amino, C1-C6-alkoxyamino, (C1-C6)-alkoxy-(C1-C6)-alkylamino, C1-C6-alkylsulfonylamino, C1-C6-alkylaminosulfonylamino, [di-(C1-C6)-alkylamino]sulfonylamino, phenyl, phenoxy, phenylamino, naphthyl, or heterocyclyl;Z4 is a bond or CH2 and R12 and R13 are, independently of one another, hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, [di-(C1-C6)-alkylamino]carbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, phenylcarbonyl, phenylsulfonyl, or heterocyclylcarbonyl;Z5 is a bond and R14 is hydrogen or C1-C6-alkyl;Z6 is a bond or CH2 and R15 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl-(C1-C6)-alkyl, phenyl, or phenyl-(C1-C6)-alkyl; andZ7 is a bond and R16 is C1-C6-alkyl or phenyl;and whereinRb, Rc, Rd, Re, and Rf are, independently of one another, hydrogen or are as defined in Ra, andwherein, when Ra, Rb, Rc, Rd, Re, and Rf are aliphatic, cyclic, or aromatic substituents, said aliphatic, cyclic, or aromatic substituents are optionally partially or fully halogenated.
  • 29. The method of claim 21, wherein R1 is hydrogen or C1-C6-alkyl and R2 is C1-C6-alkyl; wherein C1-C6-alkyl in R1 and R2 is optionally partially or fully halogenated.
  • 30. The method of claim 21, wherein R3 is hydrogen, halogen, C1-C6-alkyl, or halo-C1-C6-alkyl.
  • 31. The method of claim 21, wherein R4, R5, and R6 are hydrogen.
  • 32. The method of claim 21, wherein the center of chirality in the piperazine ring has the (S)-configuration.
  • 33. The method of claim 21, wherein the exo double bond at the piperazine ring has the (Z)-conformation.
  • 34. A composition comprising a herbicidally effective amount of at least one piperazine compound of formula (I)
  • 35. A process for preparing the composition of claim 34 comprising mixing a herbicidally effective amount of at least one piperazine compound of the formula (I) or an agriculturally useful salt thereof and auxiliaries customary for formulating crop protection agents.
  • 36. A piperazine compound of general formula (I)
  • 37. A process for preparing the piperazine compound of claim 36 comprising reacting a compound of formula (II)
  • 38. The process of claim 37, wherein LG is selected from the group consisting of 4-toluenesulfonyloxy, trifluoromethanesulfonyloxy, and methanesulfonyloxy.
  • 39. The process of claim 37, where said dehydrating agent is selected from group consisting of (1) the system triphenylphosphine/diethyl azodicarboxylate and (2) the Burgess reagent.
Priority Claims (1)
Number Date Country Kind
06000185.6 Jan 2006 EP regional
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP07/50067 1/4/2007 WO 00 6/30/2008