EP0429984A2
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Indole derivatives
Assignee: Nisshin Seifun Group Inc
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Filing: 1990-11-16
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Granted: —
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Expires: 2010-11-16
Abstract
Abstract Disclosed are compounds of formula I wherein R₁ is a hydrogen atom, a C₁-C₆ alkyl group, benzyl or an indolyl carbonyl group, R₂ is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C₁-C₆ alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain -(CH₂) n - are optionally substituted by a C₁-C₆ alkyl, phenyl and/or hydroxyl group, physiologically acceptable salts and quaternary ammonium salts thereof. The compounds are selective antagonists of 5-HT₃ receptors and are useful in the treatment of psychotic disorders, neurotic diseases, gastric stasis symptoms, gastrointestinal disorders, nausea and vomiting.
Inventors
- 👤 Haruhiko Kikuchi
- 👤 Hiroaki Satoh
- 👤 Makoto C/O Nisshin Flour Milling Co. Ltd. Yanai
- 👤 Toshio Suguro
- 👤 Koichiro Hagihara
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 13:04
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; C07D403/00; C07D403/02; C07D403/12; C07D403/14
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
120 words
A compound of formula I wherein R₁ is a hydrogen atom, a C₁-C₆ alkyl group, benzyl or an indolyl carbonyl group, R₂ is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C₁-C₆ alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain -(CH₂) n - are optionally substituted by a C₁-C₆ alkyl, phenyl and/or hydroxyl group, with the proviso of excluding a compound wherein n is 1 and R₂ is 1-methyl-2-pyrrolidinyl or 1-benzyl-2-pyrrolidinyl, or a physiologically acceptable salt or quaternary ammonium salt thereof.
Claim 2
Dependent Claim
120 words
A compound of formula I wherein R₁ is a hydrogen atom, a C₁-C₆ alkyl group, benzyl or an indolyl carbonyl group, R₂ is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C₁-C₆ alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain -(CH₂) n - are optionally substituted by a C₁-C₆ alkyl, phenyl and/or hydroxyl group, with the proviso of excluding a compound wherein n is 1 and R₂ is 1-methyl-2-pyrrolidinyl or 1-benzyl-2-pyrrolidinyl, or a physiologically acceptable salt or quaternary ammonium salt thereof.
Claim 3
Dependent Claim
15 words
A compound of claim 1 wherein R₁ is hydrogen, C₁-C₅ alkyl, benzyl or indole-3-yl carbonyl.
Claim 4
Dependent Claim
43 words
A compound of claim 1 or 2 wherein R₂ is a saturated 5- to 7-membered heterocyclic group containing one or two nitrogen atoms as a hetero atom, which is optionally substituted at an N or C atom by C₁-C₅ alkyl, benzyl or phenethyl.
Claim 5
Dependent Claim
29 words
A compound of claim 3 wherein R₂ is pyrrolidinyl, piperidyl, piperazinyl or hexahydroazepinyl, which is optionally substituted at an N or C atom by C₁-C₅ alkyl, benzyl or phenethyl.
Claim 6
Dependent Claim
43 words
A compound of claim 1 or 2 wherein R₂ is an unsaturated 5- to 7-membered heterocyclic group containing one or two nitrogen atoms as a hetero atom, which is optionally substituted at an N or C atom by C₁-C₅ alkyl, benzyl or phenethyl.
Claim 7
Dependent Claim
30 words
A compound of claim 5 wherein R₂ is pyrrolyl, imidazolyl, pyrazolyl, pyridyl or pyridazinyl, which is optionally substituted at an N or C atom by C₁-C₅ alkyl, benzyl or phenethyl.
Claim 8
Dependent Claim
15 words
A compound of claims 1 or 2 to 6 wherein n is 1 to 3.
Claim 9
Dependent Claim
20 words
A compound of claim 1 or 7 wherein the alkylene chain -(CH₂)₁₋₃- is substituted by C₁-C₆ alkyl, phenyl or hydroxyl.
Claim 10
Dependent Claim
44 words
A pharmaceutical composition comprising as an active ingredient at least one compound of formula I as defined in claims 1 or 2 to 8 or a physiologically acceptable salt or quaternary ammonium salt thereof together with at least one physiologically acceptable carrier or excipient.
Claim 11
Dependent Claim
184 words
A process for the preparation of a compound of formula I wherein R₁ is a hydrogen atom, a C₁ -C₆ alkyl group, benzyl or an indolyl carbonyl group, R₂ is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C₁-C₆ alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain -(CH₂) n - are optionally substituted by a C₁-C₆ alkyl, phenyl and/or hydroxyl group, with the proviso of excluding a compound wherein n is 1 and R₂ is 1-methyl-2-pyrrolidinyl or 1-benzyl-2-pyrrolidinyl, or a physiologically acceptable salt or quaternary ammonium salt thereof, which comprises reacting a compound of formula II or its reactive derivatives wherein R₁ is as defined above, with a compound of formula III HO-(CH₂) n -R₂ (III) wherein R₂ and n are as defined above and if necessary converting the resulting compound in a free base into the physiologically acceptable salt or quaternary ammonium salt thereof.
Claim 12
Dependent Claim
184 words
A process for the preparation of a compound of formula I wherein R₁ is a hydrogen atom, a C₁ -C₆ alkyl group, benzyl or an indolyl carbonyl group, R₂ is a saturated or unsaturated 5- or 8-membered heterocyclic group containing as a hetero atom one or more nitrogen atoms, the heterocyclic group is optionally substituted at an N or C atom by a C₁-C₆ alkyl or aralkyl group, n is an integer of 1 to 5 and one or more hydrogen atoms, in an alkylene chain -(CH₂) n - are optionally substituted by a C₁-C₆ alkyl, phenyl and/or hydroxyl group, with the proviso of excluding a compound wherein n is 1 and R₂ is 1-methyl-2-pyrrolidinyl or 1-benzyl-2-pyrrolidinyl, or a physiologically acceptable salt or quaternary ammonium salt thereof, which comprises reacting a compound of formula II or its reactive derivatives wherein R₁ is as defined above, with a compound of formula III HO-(CH₂) n -R₂ (III) wherein R₂ and n are as defined above and if necessary converting the resulting compound in a free base into the physiologically acceptable salt or quaternary ammonium salt thereof.
References Cited (Backward Citations)
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