EP0191562A2
Expired / Lapsed
EP
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Tetrahydrocarbazolone derivatives
Assignee: Glaxo Group Ltd
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Filing: 1986-01-22
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Granted: —
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Expires: 2006-01-22
Abstract
Abstract The invention relates to compounds of formula (I), wherein R 1 represents a C 3-7 cycloalkyl-(C 1-4 ) alkyl group or a C 3-10 alkynyl group; and one of the groups represented by R 2 , R 3 and R 4 is a hydrogen atom or a C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl or phenyl-(C 1-3 ) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C 1-6 alkyl group; and physiologically acceptable salts and solvates, e.g. hydrates, thereof. The compounds are potent selective antagonists at 5-hydroxytryptamine receptors and are useful in the treatment of psychotic disorders such as schizophrenia or mania and in the treatment of anxiety, pain, gastric stasis, symptoms of gastrointestinal dysfunction, migraine and nausea.
Inventors
- 👤 Ian Harold Coates
- 👤 James Angus Bell
- 👤 David Cedric Humber
- 👤 George Blanch Ewan
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 15:13
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D403/00; C07D403/02; C07D403/06
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
413 words
A process for the preparation of compounds of the general formula (I) wherein R 1 represents a C 3- y cycloalkyl-(C 1-4 )alkyl group or a C 3-10 alkynyl group; and one of the groups represented 2 4 by R2 , R 3 and R is a hydrogen atom or a C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl or phenyl-(C 1-3 ) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C 1-6 alkyl group; and physiologically acceptable salts and solvates thereof, which process comprises: (A) reacting a compound of general formula (II) (in which R 1 is as defined in claim 1 and Y represents a reactive substituent) or a protected derivative thereof with an imidazole of general formula (III) (in which R 2 , R 3 and R 4 are as defined in claim 1) or a salt thereof with subsequent removal of any protecting group which is present; or (B) oxidizing a compound of formula (IV) (in which A represents a hydrogen atom or a hydroxyl group and R 1 , R 2 , R3 and R 4 are as defined in claim 1) or a salt or a protected derivative thereof with subsequent removal of any protecting group which is present; or (C) alkylating a compound of general formula (V) 4 (in which R 2 , R and R are as defined in claim 1) or a salt or protected derivative thereof with subsequent removal of any protecting group which is present; or (D) for the production of a compound of general formula (I) in which R 1 represents a C 3-7 cycloalkyl-(C 1-4 ) alkyl group, hydrogenating a compound of general formula (I) in which R 1 represents a C 3-7 cycloalkenyl-(C 1-4 ) alkyl group and/or one of R 2 , R and R represents an alkenyl group and each of the other groups are as defined in claim 1, or a salt or a protected derivative thereof with subsequent removal of any protecting group which is present; or (E) removing a protecting group or groups from a protected form of a compound of formula (I); and when a compound of formula (I) is obtained as a mixture of enantiomers, optionally resolving the mixture to obtain the desired enantiomer; and/or where the compound of formula (I) is in the form of a free base, optionally converting the free base into a salt.
Claim 2
Dependent Claim
33 words
A process as claimed in claim 1(A) in which Y represents an alkenyl group =CH 2 or a group of formula CH 2 Z where Z represents a readily displaceable atom or group.
Claim 3
Dependent Claim
61 words
A process as claimed in claim 1 or 2 for the preparation of compounds in which one of the groups 4 represented R , R and R represents a C l-3 alkyl or C 3-6 alkenyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C 1-3 alkyl group.
Claim 4
Dependent Claim
52 words
A process as claimed in claim 1 or 2 for the preparation of compounds in which either R 2 represents a hydrogen atom and R 3 and/or R 4 represents a C 1-3 alkyl group or R represents a C 1-3 alkyl group and R 3 and R both represent hydrogen atoms.
Claim 5
Dependent Claim
35 words
A process as claimed in claim 1 or 2 for the preparation of a compound selected from 9-[(cyclopropyl) methyl]-1,2,3,9-tetrahydro-3-[(2-methyl-lH-imidazol-1-yl) methyl]-4H-carbazol-4-one; 1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yI)methyl] -9-(2-propynyl)-4H-carbazol-4-one; 9-(cyclobutylmethyl)-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one; 9-cyclocentylmethcl)-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one; 1,2,3,9-tetrahcdro-3-[(2-methyl-1H-imidazol-1-yl)methyl] -9-(2-octynyl)-4H-carbazol-4-one; 9-(3-cyclopentylpropyl)-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one; 9-(cycloheptylmethyl)-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)meZhyl]-4H-carbazol-4-one; and physiologically acceptable salts and solvates thereof.
References Cited (Backward Citations)
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