Claims
- 1. A method of treating acne and/or hirsutism comprising the step of delivering to a mammal in need thereof a composition comprising a compound of formula I, or a tautomer thereof, and a physiologically compatible carrier, wherein formula I is:
- 2. The method according to claim 1, wherein:
R1 and R2 are joined to form a —CH2(CH2)nCH2— ring; n is 3; R3 and R4 are H; R5 is the substituted benzene ring having the structure: 38X is selected from the group consisting of halogen, CN, CONH2, CSNH2, CORB, CSRB, C1 to C3 alkoxy, C1 to C3 alkyl, NO2, C1 to C3 perfluoroalkyl, 5 membered heterocyclic ring comprising 1 to 3 heteroatoms, and C1 to C3 thioalkyl; RB is C1 to C3 aminoalkyl or substituted C, to C3 aminoalkyl, wherein said aminoalkyl is NH(alkyl) or N(alkyl)2; Y is selected from the group consisting of H, halogen, CN, NO2, C1 to C3 alkoxy, C1 to C4 alkyl, and C1 to C3 thioalkyl.
- 3. The method according to claim 1, wherein:
R1 and R2 are joined to form the —CH2(CH2)nCH2-ring; n is 3; R3 and R4 are H; R5 is the five membered ring having the structure: 39U is O, S, or NR6; X′ is selected from the group consisting of halogen, CN, NO2, CONH2, CSNH2, CORB, CSRB, C1 to C3 alkyl, and C1 to C3 alkoxy; RB is C1 to C3 aminoalkyl or substituted C1 to C3 aminoalkyl, wherein said aminoalkyl is NH(alkyl) or N(alkyl)2; Y′ is selected from the group consisting of H, halogen, and C1 to C4 alkyl, wherein said halogen is F.
- 4. The method according to claim 1, wherein:
R1 and R2 are joined to form a —CH2(CH2)nCH2— ring; n is 3; R3 and R4 are H; R5 is the six membered ring having the structure: 40X1 is N or CX2; X2 is halogen, CN, CONH2, CSNH2, COR , CSR B, or NO2; RB is C1 to C3 aminoalkyl or substituted C1 to C3 aminoalkyl, wherein said aminoalkyl is NH(alkyl) or N(alkyl)2.
- 5. The method according to claim 1, wherein:
R1 and R2 are alkyl or substituted alkyl; R3 is H.
- 6. The method according to claim 1, wherein:
R1 and R2 are joined to form a ring selected from the group consisting of —CH2(CH2)nCH2—, —CH2CH2C(CH3)2CH2CH2—, —O(CH2)mCH2—, —O(CH2)pO—, —CH2CH2OCH2CH2—, —CH2CH2N(H)CH2CH2—, and —CH2CH2N(alkyl)CH2CH2—; R3 is H.
- 7. The method according to claim 1, wherein:
R3 is H; Q1 is S or NR7.
- 8. The method according to claim 1, wherein the compound is delivered orally.
- 9. The method according to claims 1, wherein said compound of formula I is selected from the group consisting of 5′-(3-Chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-thione, 3-(1′,2′-Dihydro-2′-thioxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)benzonitrile, 4-1′,2′-Dihydro-2′-thioxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-2-thiophenecarbonitrile, 3-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-5-fluorobenzonitrile, 4-Methyl-5-(1,2-dihydro-2-thioxospiro [cyclohexane-1,3-[3H]-indol]-5-yl)-2-thiophenethioamide, 5-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5′-yl)-1H-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-1-(tert-butoxycarbonyl)-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-1-H-pyrrole-2-carbonitrile, 5-(2′-thioxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5-yl)-3-thiophenecarbonitrile, 5-(1,2-Dihydro-thioxospiro [cyclopentane-1,3-[3H]indol]-5-yl)-2-thiophenecarbonitrile, 5-(3-Fluoro-4-methoxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(2-Amino-5-pyrimidinyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 3-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5-yl)-5-fluorobenzonitrile, 5-(3-chlorophenyl)-3,3-dimethyl-1,3-dihydro-2H-indole-2-thione, 3-Benzyl-5-(3-chlorophenyl)-3-methyl-1,3-dihydro-2H-indole-2-thione, 4-(3,3-dimethyl-2-thioxo-2,3-dihydro-1H-indol-5-yl)-2-furonitrile, 5-(3-methoxyphenyl)-3,3-dimethyl-1,3-dihydro-2H-indole-2-thione, 3-(1,2-Dihydro-2-thioxospiro [cyclohexane-1,3-[3H]indol]-5-yl)-4-fluorobenzonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-3-pyridinecarbonitrile, 5-(3,4-Difluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(5-Chloro-2-thienyl)spiro [cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(1,2-Dihydro-2-thioxospiro [cyclohexane-1,3-[3H] indol]-5-yl)-3-furancarbonitrile, 5-(3-Chloro-4-fluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-Chloro-5-fluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3,5-Difluorophenyl)spiro [cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-4-propyl-2-thiophenecarbonitrile, 5-(3-Fluoro-4-nitrophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 4-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-2-furancarbonitrile, 5″-(3-Chlorophenyl)spiro [cyclobutane-1,3″-[3H]indol]-2″(1″H)-thione, 5″-(2-Chlorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5″-(4-Chlorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5-(1″,2″-Dihydro-2″-thioxospiro[cyclohexane-1,3″-[3H]indol]-5″-yl)-4-methyl-2-thiophenecarbonitrile, 5-(1″,2″-Dihydro-2″-thioxospiro[cyclohexane-1,3″-[3H]indol]-5″-yl)-2-thiophenecarbonitrile, 5″-(3-Fluorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5-(3-Hydroxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-chlorophenyl)-3,3-diethyl-1,3-dihydro-2H-indole-2-thione, 5-(4-Fluoro-3-(trifluoromethyl)phenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 4-(1,2-Dihydro-2-thioxospiro [cyclohexane-1,3-[3H]indol]-5-yl)-2-fluorobenzonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-4-n-butyl-2-thiophenecarbonitrile, 5-(3-Fluoro-5-methoxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-Chlorophenyl)-N-hydroxyspiro[cyclohexane-1,3′-[3H]indol]-2-amine, N-(Acetyloxy)-5′-(3-chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2″amine, 5′-(3-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 5′-(2-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(4-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(3,4-difluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(3-methoxyphenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(3-nitrophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(3-cyanophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 3-(1′,2′-Dihydro-2′-(hydroxyimino)spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluorobenzonitrile, 5-(Spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-4-methyl-2-thiophenecarbonitrile, 5-(Spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarbonitrile, 4-(Spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarbonitrile, 5-(Spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-1H-pyrrole-1-methyl-2-carbonitrile, 5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-1H-pyrrole-2-carbonitrile, 4-(Spiro[cyclohexane-1,3′-[3H]indol]-2′(acetoxyimino)-5′-yl)-2-thiophenecarbonitrile, 3-Fluoro-N′-hydroxy-5-(2′-(hydroxyamino)spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)benzenecarboximidamide, N′-Hydroxy-5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-4-methyl-2-thiophenecarboximidamide, N′-Hydroxy-4-(spiro[cyclohexane-1,3′-[3H]indol]-2′-hydroxyimino)-5′-yl-2-thiophenecarboximidamide, N′-Hydroxy-5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarboxidamide, 5′-(3-Chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(3-Cyano-5-fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2-ylidenecyanamide, 5′-(5-Cyano-thiophen-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-3-methyl-thiophen-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-thiophen-3-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 3-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluoro-benzonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1H-pyrrole-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-1H-pyrrole-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-thiophene-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-4-methyl-thiophene-2-carbonitrile, and 4-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-thiophene-2-carbonitrile, or a pharmaceutically acceptable salt, tautomer, metabolite, or prodrug thereof.
- 10. The method according to claims 1, wherein said compound is 5′-(5-Cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, or a pharmaceutically acceptable salt, tautomer, metabolite, or prodrug thereof.
- 11. A method of treating acne and/or hirsutism comprising the step of delivering to a mammal in need thereof a composition comprising a compound of formula II, or a tautomer thereof, and a physiologically compatible carrier, wherein formula II is:
- 12. The method according to claim 11, wherein R5 is said five membered ring and U is O or S.
- 13. A method of treating acne and/or hirsutism comprising the step of delivering to a mammal in need thereof a composition comprising a compound of formula III, or a tautomer thereof, and a physiologically compatible carrier, wherein formula III is:
- 14. The method according to claim 13, wherein R5 is the five membered ring (ii) and U is O or S.
- 15. A method of treating acne and/or hirsutism comprising the step of delivering to a mammal in need thereof a composition comprising a compound of formula IV, or a tautomer thereof, and a physiologically compatible carrier, wherein formula IV is:
- 16. The method according to claim 15, wherein R5 is the five-membered ring (ii) and U is O or S.
- 17. A method of treating acne and hirsutism comprising the step of delivering to a mammal in need thereof a composition comprising a compound of formula V, or a tautomer thereof, and a physiologically compatible carrier, wherein formula V is:
- 18. The method according to claim 17, wherein R5 is the five membered ring (ii) and U is O or S.
- 19. A composition for conditioning the skin of a mammal in need thereof comprising:
(i) a skin conditioning component; and (ii) a compound of formula I, or a tautomer thereof: 57wherein: R1 and R2 are selected from the group consisting of H, alkyl, substituted alkyl, OH, O(alkyl), O(substituted alkyl), O(Acetyl), aryl, substituted aryl, heterocyclic ring, substituted heterocyclic ring, alkylaryl, substituted alkylaryl, alkylheteroaryl, substituted alkylheteroaryl, 1-propynyl, substituted 1-propynyl, 3-propynyl, and substituted 3-propynyl; or R1 and R2 are joined to form a ring selected from the group consisting of —CH2(CH2)nCH2—, —CH2CH2C(CH3)2CH2CH2—, —O(CH2)mCH2—, —O(CH2)pO—, —CH2CH2OCH2CH2—, —CH2CH2N(H)CH2CH2—, and —CH2CH2N(alkyl)CH2CH2—; m is an integer from 1 to 4; n is an integer from 1 to 5; p is an integer from 1 to 4; or R1 and R2 form a double bond to C(CH3)2, C(cycloalkyl), O, or C(cycloether); R3 is selected from the group consisting of H, OH, NH2, C1 to C6 alkyl, substituted C, to C6 alkyl, C3 to C6 alkenyl, substituted C3 to C6 alkenyl, alkynyl, substituted alkynyl, and CORA; RA is selected from the group consisting of H, C1 to C3 alkyl, substituted C1 to C3 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, and substituted C1 to C3 aminoalkyl; R4 is selected from the group consisting of H, halogen, CN, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C1 to C6 alkoxy, substituted C1 to C6 alkoxy, C1 to C6 aminoalkyl, and substituted C, to C6 aminoalkyl; R5 is selected from the group consisting of a), b) and c):
a) a substituted benzene ring having the structure: 58X is selected from the group consisting of halogen, OH, CN, C1 to C3 alkyl, substituted C1 to C3 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 thioalkyl, substituted C1 to C3 thioalkyl, S(O)alkyl, S(O)2alkyl, C1 to C3 aminoalkyl, substituted C1 to C3 aminoalkyl, NO2, C1 to C3 perfluoroalkyl, substituted C1 to C3 perfluoroalkyl, 5 or 6 membered heterocyclic ring comprising 1 to 3 heteroatoms, CONH2, CSNH2, CNHNHOH, CNH2NOH, CNHNOH, CORB, CSRB, OCORB, and NRCCORB; RB is selected from the group consisting of H, C, to C3 alkyl, substituted C1 to C3 alkyl, aryl, substituted aryl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, and substituted C1 to C3 aminoalkyl; RC is H, C1 to C3 alkyl, or substituted C to C3 alkyl; Y and Z are independently selected from the group consisting of H, halogen, CN, NO2, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C4 alkyl, substituted C1 to C4 alkyl, C1 to C3 thioalkyl, and substituted C1 to C3 thioalkyl; b) a five or six membered heterocyclic ring comprising 1, 2, or 3 heteroatoms selected from the group consisting of O, S, SO, SO2 and NR6 and having one or two independent substituents from the group consisting of H, halogen, CN, NO2, C1 to C4 alkyl, substituted C1 to C4 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, substituted C1 to C3 aminoalkyl, CORD, CSRD, and NRECORD; RD is H, NH2, C1 to C3 alkyl, substituted C1 to C3 alkyl, aryl, substituted aryl, C1 to C3 alkoxy, substituted C, to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; RE is H, C1 to C3 alkyl, or substituted C1 to C3 alkyl; R6 is H, C1 to C3 alkyl, substituted C1 to C3 alkyl, or C1 to C4CO2alkyl; or
c) an indol-4-yl, indol-7-yl or benzo-2-thiophene moiety, wherein said moiety is optionally substituted by from 1 to 3 substituents selected from the group consisting of halogen, alkyl, substituted alkyl, CN, NO2, alkoxy, substituted alkoxy, and CF3; Q1 is S, NR7, or CR8R9; R7 is selected from the group consisting of CN, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, substituted aryl, heterocyclic ring, substituted heterocyclic ring, acyl, substituted acyl, aroyl, substituted aroyl, SO2CF3, OR11 and NR11R12; R8 and R9 are independent substituents selected from the group consisting of H, C1 to C6 alkyl, substituted C, to C6 alkyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, substituted aryl, heterocyclic ring, substituted heterocyclic ring, NO2, CN, and CO2R10; R10 is C1 to C3 alkyl or substituted C, to C3 alkyl; or CR8R9 comprise a six membered ring having the structure: 59R11 and R12 are independently selected from the group consisting of H, alkyl, substituted alkyl, aryl, substituted aryl, heterocyclic ring, substituted heterocyclic ring, acyl, substituted acyl, aroyl, substituted aroyl, sulfonyl, and substituted sulfonyl; or a pharmaceutically acceptable salt, tautomer, metabolite, or prodrug thereof.
- 20. The composition according to claim 19, wherein:
R1 and R2 are alkyl or substituted alkyl; R3 is H.
- 21. The composition according to claim 19, wherein:
R1 and R2 are joined to form a ring selected from the group consisting of —CH2(CH2)nCH2—, —CH2CH2C(CH3)2CH2CH2—, —O(CH2)mCH2—, —O(CH2)pO—, —CH2CH2OCH2CH2—, —CH2CH2N(H)CH2CH2—, and —CH2CH2N(alkyl)CH2CH2—; R3 is H.
- 22. The composition according to claim 19, wherein:
R3 is H; Q1 is S or NR7.
- 23. A method of conditioning the skin comprising the step of delivering to a mammal in need thereof a composition according to claim 19.
- 24. The method according to claims 23 wherein said compound of formula I is selected from the group consisting of 5′-(3-Chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-thione, 3-(1′,2′-Dihydro-2′-thioxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)benzonitrile, 4-1′,2′-Dihydro-2′-thioxospiro[cyclohekane-1,3′-[3H]indol]-5′-yl)-2-thiophenecarbonitrile, 3-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-5-fluorobenzonitrile, 4-Methyl-5-(1,2-dihydro-2-thioxospiro[cyclohexane-1,3-[3H]-indol]-5′-yl)-2-thiophenethioamide, 5-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5′-yl)-1H-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-1-(tert-butoxycarbonyl)-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-1-H-pyrrole-2-carbonitrile, 5-(2′-thioxospiro [cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5-yl)-3thiophenecarbonitrile, 5-(1,2-Dihydro-thioxospiro[cyclopentane-1,3-[3H]indol]-5-yl)-2thiophenecarbonitrile, 5-(3-Fluoro-4-methoxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(2-Amino-5-pyrimidinyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 3-(1,2-Dihydro-2-thioxospiro[cyclopentane-1,3-[3H]indol]-5-yl)-5-fluorobenzonitrile, 5-(3-chlorophenyl)-3,3-dimethyl-1,3-dihydro-2H-indole-2-thione, 3-Benzyl-5-(3-chlorophenyl)-3-methyl-1,3-dihydro-2H-indole-2-thione, 4-(3,3-dimethyl-2-thioxo-2,3-dihydro-1H-indol-5-yl)-2-furonitrile, 5-(3-methoxyphenyl)-3,3-dimethyl-1,3-dihydro-2H-indole-2-thione, 3-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-4-fluorobenzonitrile, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-3-pyridinecarbonitrile, 5-(3,4-Difluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(5-Chloro-2-thienyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-3-furancarbonitrile, 5-(3-Chloro-4-fluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-Chloro-5-fluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3,5-Difluorophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(1,2-Dihydro-2-thioxospiro [cyclohexane-1,3-[3H]indol]-5-yl)-4-propyl-2-thiophenecarbonitrile, 5-(3-Fluoro-4-nitrophenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 4-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H]indol]-5-yl)-2-furancarbonitrile, 5″-(3-Chlorophenyl)spiro[cyclobutane-1,3″-[3H]indol]-2″(1″H)-thione, 5″-(2-Chlorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5″-(4-Chlorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5-(1″,2″-Dihydro-2″-thioxospiro[cyclohexane-1,3″-[3H]indol]-5″-yl)-4-methyl-2-thiophenecarbonitrile, 5-(1″,2″-Dihydro-2″-thioxospiro[cyclohexane-1,3″-[3H]indol]-5″-yl)-2-thiophenecarbonitrile, 5″-(3-Fluorophenyl)spiro[cyclohexane-1,3″-[3H]indol]-2″(1″H)-thione, 5-(3-Hydroxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-chlorophenyl)-3,3-diethyl-1,3-dihydro-2H-indole-2-thione, 5-(4-Fluoro-3-(trifluoromethyl)phenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 4-(1,2-Dihydro-2-thioxospiro[cyclohexane-1,3-[3H] indol]-5-yl)-2-fluorobenzonitrile, 5-(1,2-Dihydro-2-thioxospiro [cyclohexane-1,3-[3H]indol]-5-yl)-4-n-butyl-2-thiophenecarbonitrile, 5-(3-Fluoro-5-methoxyphenyl)spiro[cyclohexane-1,3-[3H]indol]-2(1H)-thione, 5-(3-Chlorophenyl)-N-hydroxyspiro[cyclohexane-1,3′-[3H]indol]-2-amine, N-(Acetyloxy)-5′-(3-chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2″amine, 5′-(3-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(2-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 5′-(4-Fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 5′-(3,4-difluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 5′-(3-methoxyphenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′ (1′H)-one oxime, 5′-(3-nitrophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 5′-(3-cyanophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one oxime, 3-(1′,2′-Dihydro-2′-(hydroxyimino)spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluorobenzonitrile, 5-(Spiro [cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-4-methyl-2-thiophenecarbonitrile, 5-(Spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarbonitrile, 4-(Spiro [cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarbonitrile, 5-(Spiro [cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-1H-pyrrole-1-methyl-2-carbonitrile, 5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-1H-pyrrole-2-carbonitrile, 4-(Spiro[cyclohexane-1,3′-[3H]indol]-2′(acetoxyimino)-5′-yl)-2-thiophenecarbonitrile, 3-Fluoro-N′-hydroxy-5-(2′-(hydroxyamino)spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)benzenecarboximidamide, N′-Hydroxy-5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-4-methyl-2-thiophenecarboximidamide, N′-Hydroxy-4-(spiro[cyclohexane-1,3′-[3H]indol]-2′-hydroxyimino)-5′-yl-2-thiophenecarboximidamide, N′-Hydroxy-5-(spiro[cyclohexane-1,3′-[3H]indol]-2′-(hydroxyimino)-5′-yl)-2-thiophenecarboxidamide, 5′-(3-Chlorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(3-Cyano-5-fluorophenyl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2-ylidenecyanamide, 5′-(5-Cyano-thiophen-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-3-methyl-thiophen-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 5′-(5-Cyano-thiophen-3-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, 3-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-fluoro-benzonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1H-pyrrole-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-1H-pyrrole-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-thiophene-2-carbonitrile, 5-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-4-methyl-thiophene-2-carbonitrile, and 4-(2′-Cyanomethylene-spiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-thiophene-2-carbonitrile, or a pharmaceutically acceptable salt, tautomer, metabolite, or prodrug thereof.
- 25. The method according to claim 23, wherein said compound is 5′-(5-Cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide, or a pharmaceutically acceptable salt, tautomer, metabolite, or prodrug thereof.
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This is a non-provisional of U.S. Patent Application No. 60/391,913, filed Jun. 25, 2002.
Provisional Applications (1)
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Number |
Date |
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60391913 |
Jun 2002 |
US |