Claims
- 1. A compound of the formula I wherein R.sub.1 and R.sub.2 are the same or different and are
- a) H,
- b) fluoro,
- c) chloro,
- d) bromo,
- e) iodo,
- f) C.sub.1 -C.sub.4 alkyl,
- g) C.sub.3 -C.sub.7 cycloalkyl,
- h) CN,
- i) CONR.sub.11 R.sub.12,
- j) SO.sub.2 NR.sub.11 R.sub.12,
- k) NR.sub.11 R.sub.12,
- l) N(R.sub.11)SO.sub.2 R.sub.12,
- m) N(R.sub.11)CO(R.sub.12),
- n) NO.sub.2,
- o) OH,
- p) O(C.sub.1 -C.sub.3 alkyl),
- q) O-phenyl,
- r) O--CF.sub.3,
- s) O--SO.sub.2 CF.sub.3,
- t) SH,
- u) S(C.sub.1 -C.sub.3 alkyl),
- v) thiazolyl,
- w) imidazolyl,
- x) oxadiazolyl,
- y) aryl optionally substituted with R.sub.13, or
- z) CF.sub.3 ;
- wherein R.sub.3 is
- a) H,
- b) halo,
- c) CN,
- d) OH,
- e) OR.sub.4,
- f) (CH.sub.2).sub.n OH,
- g) (CH.sub.2).sub.n OR.sub.4,
- h) (CH.sub.2).sub.n OCOR.sub.4,
- i) (CH.sub.2).sub.n OCOOR.sub.4,
- j) (CH.sub.2).sub.n OCONR.sub.11 R.sub.12,
- k) (CH.sub.2).sub.n N(R.sub.11)CONR.sub.11 R.sub.12,
- l) C.sub.1 -C.sub.4 alkyl,
- m) (CH.sub.2).sub.p COOR.sub.4,
- n) (CH.sub.2).sub.n CONR.sub.11 R.sub.12,
- o) CHO, or
- p) (CH.sub.2).sub.n --A--(CH.sub.2).sub.m --Ar(R.sub.8)(R.sub.9)(R.sub.10);
- wherein A is
- a) CH.sub.2,
- b) O,
- c) S, or
- d) N(R.sub.11);
- wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and are
- a) H,
- b) C.sub.1 -C.sub.4 alkyl,
- c) C.sub.3 -C.sub.7 cycloalkyl,
- d) C.sub.1 -C.sub.3 -alkyl-C.sub.3 -C.sub.7 cycloalkyl, or
- e) aryl optionally substituted with R.sub.13 ;
- wherein W is
- a) CH,
- wherein X is
- a) absent, or
- b) N(R.sub.4);
- wherein Y is
- a) phenyl,
- b) 2-, 3- or 4-pyridinyl,
- c) 2-, 4- or 5-pyrimidinyl,
- d) 3- or 4-pyridazinyl,
- e) 2-pyrazinyl,
- f) 2-, 3-, 6- or 7-imidazo[1,2-a]pyridinyl,
- g) 2-benzoxazolyl,
- h) 2-thiobenzoxazolyl,
- i) 2-thiazolyl,
- j) 1,3-dihydro-2H-benzimidazol-2-onyl, or
- k) 1,3-dihydro-3-methyl-2H-benzimidazol-2-onyl;
- wherein R.sub.8, R.sub.9 and R.sub.10 are the same or different and are
- a) hydrogen,
- b) fluoro,
- c) chloro,
- d) bromo,
- e) iodo,
- f) C.sub.1 -C.sub.4 alkyl,
- g) C.sub.3 -C.sub.7 cycloalkyl,
- h) CN,
- i) CONR.sub.11 R.sub.12
- j) SO.sub.2 NR.sub.11 R.sub.12,
- k) NR.sub.11 R.sub.12,
- l) N(R.sub.11)SO.sub.2 R.sub.12,
- m) N(R.sub.11)COR.sub.12,
- n) NO.sub.2,
- o) OH,
- p) O(C.sub.1 -C.sub.3 alkyl),
- q) O-aryl optionally substituted with R.sub.13,
- r) O--CF.sub.3,
- s) O--SO.sub.2 CF.sub.3,
- t) SH,
- u) S(C.sub.1 -C.sub.3 alkyl),
- v) thiazolyl,
- w) imidazolyl,
- x) oxadiazolyl,
- y) phenyl,
- z) 2-, 3- or 4-pyridinyl;
- a1) CF.sub.3,
- b1) --C(O)C.sub.1 -C.sub.4 alkyl,
- c1) C(O)OR.sub.4, or
- d1) SO.sub.2 -phenyl optionally substituted with R.sub.13 ;
- wherein R.sub.11 and R.sub.12 are the same or different and are
- a) H,
- b) C.sub.1 -C.sub.4 alkyl,
- c) C.sub.3 -C.sub.7 cycloalkyl,
- d) C.sub.1 -C.sub.3 alkyl-C.sub.3 -C.sub.7 cycloalkyl, or
- e) aryl optionally substituted with R.sub.13 ;
- when R.sub.11 and R.sub.12 occur in NR.sub.11 R.sub.12, R.sub.11 and R.sub.12 may be taken together with a methylene group or a heteroatom to form piperazine, morpholine, thiomorpholine, piperidine, or pyrrolidine;
- wherein aryl in each of the above occurrence is
- a) phenyl,
- b) naphthyl,
- c) 2-, 3- or 4-pyridinyl, or
- d) 2-, 4- or 5-pyrimidinyl;
- wherein R.sub.13 is
- a) H,
- b) fluoro,
- c) chloro,
- d) bromo,
- e) iodo,
- f) CH.sub.3,
- g) CF.sub.3,
- h) CN,
- i) OH, or
- j) OCH.sub.3 ;
- wherein n is one (1) to four (4) inclusive;
- wherein m is zero (0) to four (4) inclusive;
- wherein p is two (2) to four (4) inclusive;
- or pharmaceutically acceptable salts or enantiomers or diastereomers thereof;
- with the following provisos:
- 1) when R.sub.1 or R.sub.2 is --CONR.sub.11 R.sub.12, then R.sub.11 and R.sub.12 are not both H; and
- 2) when R.sub.8, R.sub.9 or R.sub.10 is --CONR.sub.11 R.sub.12 wherein R.sub.11 and R.sub.12 are both H, then X is absent.
- 2. The compound of claim 1 of the formula II ##STR3## wherein R.sub.1 and R.sub.2 are the same or different and are a) H,
- b) chloro,
- c) bromo,
- d) CH.sub.3
- e) O(C.sub.1 -C.sub.2 alkyl),
- f) phenyl, or
- g) CF.sub.3 ;
- wherein R.sub.3 is
- a) H,
- b) (CH.sub.2)OH, or
- c) CH.sub.2 --O--CH.sub.2 -phenyl;
- wherein R.sub.6 is
- a) H, or
- b) CH.sub.3 ;
- wherein W is
- a) CH;
- wherein Y is
- a) phenyl,
- b) 2-pyridinyl,
- c) 2-pyrimidinyl,
- d) 1,3-dihydro-2H-benzimidazol-2-one, or
- e) 1,3-dihydro-3-methyl-2H-benzimidazol-2-one;
- wherein R.sub.8 and R.sub.9 are the same or different and are
- a) hydrogen,
- b) fluoro,
- c) chloro,
- d) CN,
- e) CONH.sub.2
- f) OCH.sub.3,
- g) CF.sub.3,
- h) C(O)CH.sub.3, or
- i) SO.sub.2 NH.sub.2 ;
- or pharmaceutically acceptable salts.
- 3. The compound of claim 2 of the formula IV ##STR4## wherein R.sub.2 is chloro; wherein Y is
- a) phenyl,
- b) 1,3-dihydro-2H-benzimidazol-2-one, or
- c) 1,3-dihydro-3-methyl-2H-benzimidazol-2-one.
- 4. The compound of claim 2 selected from the group consisting of:
- (a) 1-[1-[(6-Chloroimidazo[1,2-a]pyridin-2-yl)methyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;
- (b) 1-[1-[(6-Chloroimidazo[1,2-a]pyridin-2-yl)methyl]-4-piperidinyl]-1,3-dihydro-3-methyl-2H-benzimidazol-2-one; and
- (c) 6-Chloro-2-[(4-Phenyl-1-piperidinyl)methyl]imidazo[1,2-a]pyridine.
- 5. A method for treating a patient having schizophrenia or psychosis which comprises administering an effective amount of a compound of formula I of claim 1.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional application of U.S. Ser. No. 08/894,179, filed Aug. 14, 1997, now pending issuance; which is the continuation (National Phase) patent application of PCT application PCt/US96/01114, filed Feb. 12, 1996, which was a continuation-in-part application of U.S. Ser. No. 08/388,682, filed Feb. 15, 1995, now abandoned.
US Referenced Citations (9)
Foreign Referenced Citations (8)
Number |
Date |
Country |
0 050 563 A1 |
Apr 1982 |
EPX |
306408 |
Sep 1988 |
EPX |
54039093 |
Aug 1977 |
JPX |
57206685 |
Jun 1981 |
JPX |
92-17475-A1 |
Oct 1992 |
WOX |
9420497 |
Sep 1994 |
WOX |
WO 9424105 |
Oct 1994 |
WOX |
9422839 |
Oct 1994 |
WOX |
Non-Patent Literature Citations (3)
Entry |
VanTol et al., Nature, vol.350, p. 610-614, 1991. |
Derwent Abstracts 10911 K/05, for JP 57-20685 (Dec. 18, 1982). |
Derwent Abstracts 34368B/18, for JP 54-39093 (Mar. 24, 1979). |
Divisions (1)
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Number |
Date |
Country |
Parent |
894179 |
Aug 1997 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
PCTUS9601114 |
Feb 1996 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
388682 |
Feb 1995 |
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