EP0329168A2
Expired / Lapsed
EP
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Psychotropic heterobicycloalkylpiperazine derivatives
Assignee: Bristol Myers Squibb Co
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Filing: 1989-02-17
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Granted: —
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Expires: 2009-02-17
Abstract
Abstract A series of psychotropic heterobicycloalkylpiperazine derivatives having the structure wherein V is a 3- or 4-membered unsaturated chain, containing all carbon atoms when 4-membered, or when a 3-membered chain, V contains an oxygen or sulfur atom as one of the members; R is H or C₁₋₄ alkyl; W is CH, N, CH₂, or a chemical bond; X is CH, N, SO₂, or CO, with the proviso that both W and X cannot simultaneously be N; and Z is a heteroaromatic ring system. These compounds are useful antipsychotic and/or anxiolytic agents.
Inventors
- 👤 James Stewart New
- 👤 William Lynn Christopher
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 16:27
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; C07D275/06; A; A61; A61P; A61P25/00; C07D401/00; C07D401/02; C07D401/12; C07D491/00; C07D491/02; C07D491/04; C07D495/00; C07D495/02; C07D495/04
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
129 words
A compound of Formula I and its pharmaceutically acceptable acid addition salts thereof wherein V is either (A) or (B) in which one of Q¹, Q² or Q³ is an oxygen or sulfur atom and the other two Qs are carbon atoms bearing either a hydrogen atom or R which is a C₁₋₄ alkyl group; W is CH, N, CH₂, or a chemical bond; X is CH, N, SO₂, or CO with the proviso that both W and X cannot be N at the same time; The dotted line accompanying the full line can be either a single or double bond; and Z is a heteroaromatic ring system selected from pyrimidine,1,2-benzisothiazole, thieno[3,2- c ]pyridine, and furo[3,2- c pyridine , or a pharmaceutically acceptable acid addition salt or solvate thereof.
Claim 2
Dependent Claim
129 words
A compound of Formula I and its pharmaceutically acceptable acid addition salts thereof wherein V is either (A) or (B) in which one of Q¹, Q² or Q³ is an oxygen or sulfur atom and the other two Qs are carbon atoms bearing either a hydrogen atom or R which is a C₁₋₄ alkyl group; W is CH, N, CH₂, or a chemical bond; X is CH, N, SO₂, or CO with the proviso that both W and X cannot be N at the same time; The dotted line accompanying the full line can be either a single or double bond; and Z is a heteroaromatic ring system selected from pyrimidine,1,2-benzisothiazole, thieno[3,2- c ]pyridine, and furo[3,2- c pyridine , or a pharmaceutically acceptable acid addition salt or solvate thereof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 where V is (A).
Claim 4
Dependent Claim
9 words
The compound of claim 1 wherein Z is pyrimidine.
Claim 5
Dependent Claim
18 words
The compound of claim 1 wherein Z is selected from 1,2-benzisothiazole, thieno[3,2- c ]pyridine and furo[3,2- c ]pyridine.
Claim 6
Dependent Claim
45 words
The compounds of claim 3: 2-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-1,3(2 H ,4 H )-isoquinolinedione , 5-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]thieno[3,2- c ]pyridin-4(5 H )-one, 5-[3-[4-(2-Pyrimidinyl)-1-piperazinyl]propyl]thieno[3,2- c ]pyridin-4(5 H )-one , 6-Methyl-3-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]thieno[2,3- d ]pyrimidin-4(3 H )-one , 6-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]thieno[2,3- d ]pyridazin-7(6 H )-one , 5-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]]butyl]furo[3,2- c ]pyridin-4(5 H )-one and 6-[2-[4-(2-Pyrimidinyl)-1-piperazinyl]ethyl]thieno[2,3- d ]pyridazin-7(6 H )-one.
Claim 7
Dependent Claim
49 words
The compounds of claim 4: 2-[4-[4-(Thieno[3,2- c ]pyridin-4-yl)-1-piperazinyl]butyl]-1 H -1,3(2 H )-dione, 2-[4-[4-(Thieno[3,2- c ]pyridin-4-yl)-1-piperazinyl]butyl]1,2-benzisothiazol-3(2 H )-one 1,1-dioxide, 5-[4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]butyl]thieno[2,3- c ]pyridin-4(5 H )-one , 6-Methyl-3-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]thieno[3,2- d ] pyrimidin-4(3 H )-one , 2-[4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]butyl]-1,2-benzisothiazol-3(2 H )-one 1,1-dioxide , 2-[4-[4-(Furo[3,2- c ]pyridin-4-yl)-1-piperazinyl]butyl]-1 H -isoindole-1,3(2 H )-dione and 6-[4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]butyl]thieno[2,3- d ]pyridazin-7(6 H )-one.
Claim 8
Dependent Claim
113 words
A process for preparing the compounds of claims 1 to 6 characterized in that a compound of the general formula: wherein V, W, X and R are as defined in claim 1, is reacted with a base and then with 1,4-dihalobutane, wherein halo is chloro, bromo or iodo, to obtain a compound of the general formula III: a compound of the general formula III is reacted with a compound of the general formula II: wherein Z is as defined in claim 1 to obtain a compound of the general formula I and optionally converting a compound of formula I in free base form into a pharmaceutically acceptable acid addition salt or solvate thereof.
Claim 9
Dependent Claim
24 words
A pharmaceutical composition comprising at least one compound of anyone of claims 1 to 6, optionally together with a pharmaceutically acceptable carrier and/or diluent.
Claim 10
Dependent Claim
35 words
A process for preparing the pharmaceutical composition of claim 8 which comprises providing at least one compound of claims 1 to 6 in a suitable dosage form, optionally incorporated to a suitable carrier and/or diluent.
Claim 11
Dependent Claim
22 words
The use of at least one compound of claims 1 to 6 for preparing a pharmaceutical composition for treating anxiety or psychosis.
References Cited (Backward Citations)
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