EP0159889A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
4-Substituted piperazine-2-carboxylic acids process and pharmaceutical compositions
Assignee: BTG International Ltd
•
Filing: 1985-04-15
•
Granted: —
•
Expires: 2005-04-15
Abstract
Abstract Compounds of the general formula wherein X is C 1 -C 6 , straight chain saturated or unsaturated hydrocarbyl group, the group R 4 and the group Y are situated in any position in this chain and wherein at least one of the hydrogen atoms in X can be a heavy isotope of hydrogen; R 4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R 4 , together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms; Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R 4 -X-Y represents a carboxylic acyl group; R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl; R 1 is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R2, R 3 and R 5 which may be the same or different is each hydrogen or an alkyl, hydroxy, alkoxy, carboxy, alkyloxycarbonyl, halo, aryl, haloaryl or aryloxycarbonyl group; or R 2 and R 3 together with the carbon atoms to which they are attached form a ring system or R 3 and R 4 together and/or R 3 and X together form one or more than one ring system, and physiologically acceptable salts thereof have activity in the central nervous system.
Inventors
- 👤 Jeffery Clifton Watkins
- 👤 Arwel Wyn Jones
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 21:02
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/06; A; A61; A61P; A61P25/00; A61P25/08; C07D241/00; C07D241/02; C07D241/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/650952
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
252 words
A compound of the general formula wherein X is a C 1 -C 6 , straight chain saturated or unsaturated hydrocarbyl group, the group R 4 and the group Y are situated in any position in this chain and wherein one or more of the hydrogen atoms in X can be a heavy isotope of hydrogen; R 4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R 4 , together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms; Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R 4 -X-Y represents a carboxylic acyl group; R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R 1 is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R 2 , R 3 and R which may be the same or different is each hydrogen or an alkyl, hydroxy, alkoxy, carboxy, alkyloxycarbonyl, halo, aryl, haloaryl or aryloxycarbonyl group; or R 2 and R 3 together with the carbon atoms to which they are attached form a ring system or R 3 and R 4 together and/or R 3 and X together form one or more than one ring systems; or a physiologically acceptable salt thereof.
Claim 2
Dependent Claim
252 words
A compound of the general formula wherein X is a C 1 -C 6 , straight chain saturated or unsaturated hydrocarbyl group, the group R 4 and the group Y are situated in any position in this chain and wherein one or more of the hydrogen atoms in X can be a heavy isotope of hydrogen; R 4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R 4 , together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms; Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R 4 -X-Y represents a carboxylic acyl group; R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R 1 is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R 2 , R 3 and R which may be the same or different is each hydrogen or an alkyl, hydroxy, alkoxy, carboxy, alkyloxycarbonyl, halo, aryl, haloaryl or aryloxycarbonyl group; or R 2 and R 3 together with the carbon atoms to which they are attached form a ring system or R 3 and R 4 together and/or R 3 and X together form one or more than one ring systems; or a physiologically acceptable salt thereof.
Claim 3
Dependent Claim
16 words
A compound as claimed in claim 1 wherein X is C 1 -C 4 hydrocarbyl group.
Claim 4
Dependent Claim
20 words
A compound as claimed in claim 2 wherein X is a C 3 straight chain saturated or unsaturated hydrocarbyl group.
Claim 5
Dependent Claim
11 words
A compound as claimed in claim 3 wherein X is mono-unsaturated.
Claim 6
Dependent Claim
48 words
A compound as claimed in any one of claims 1 to 4 wherein Y is selected from: or or or or where R 6 and R 7 , which may be the same or different, each is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group;
Claim 7
Dependent Claim
16 words
A compound as claimed in claim 5 wherein Y is a phosphonic acid or ester thereof.
Claim 8
Dependent Claim
2 words
3-((±)-2-carboxypiperazin-4-yl)propyl-1-phosphonic acid.
Claim 9
Dependent Claim
2 words
3-((±)-2-carboxypiperazin-4-yl)propyl-1-phosphonic acid.
Claim 10
Dependent Claim
66 words
A process for producing a compound according to any one of claims 1 to 7 comprising reacting a piperazine-2-carboxylic acid or ester of the formula III: with a compound of formula IV in which formulae R , R 1 , R 2 , R 3 , R 4 , R 5 , and Y are as defined in claim 1 and Z represents a reactive group.
Claim 11
Dependent Claim
84 words
A process for producing a compound according to claim 1 wherein X is a saturated hydrocarbyl group comprising (a) reacting a piperazine-2-carboxylic acid or ester of the formula III: with a compound of formula IV in which formulae R, R 1 , R 2 , R 3 , R 4 , R 5 , and Y are as defined above and wherein X is an unsaturated hydrocarbyl group and Z represents a reactive group and (b) subsequently catalytically hydrogenating the product of step (a).
Claim 12
Dependent Claim
18 words
A process according to claim 8 or claim 9 wherein Z is a reactive halogeno or p-tosyl group.
Claim 13
Dependent Claim
23 words
A pharmaceutical composition comprising a compound according to any one of claims 1 to 7 and a pharmaceutically acceptable diluent or carrier therefor.
Claim 14
Dependent Claim
25 words
A compound according to any one of claims 1 to 7 for use in a method of therapy practised on the human or animal body.
Claim 15
Dependent Claim
307 words
A process for producing a compound of the general formula wherein X is a C 1 -C 6 , straight chain saturated or unsaturated hydrocarbyl group, the group R 4 and the group Y are situated in any position in this chain and wherein one or more of the hydrogen atoms in X can be a heavy isotope of hydrogen; R 4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R 4 , together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms; Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R4-X-Y represents a carboxylic acyl group; R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group; R 2 , R 3 and R 5 which may be the same or different is each hydrogen or an alkyl, hydroxy, alkoxy, carboxy, alkyloxycarbonyl, halo, aryl, haloaryl or aryloxycarbonyl group; or R 2 and R 3 together with the carbon atoms to which they are attached form a ring system or R 3 and R 4 together and/or R 3 and X together form one or more than one ring systems or a physiologically acceptable salt thereof, which process comprises reacting a piperazine-2-carboxylic acid or ester of the formula III: with a compound of formula IV in which formulae R , R 1 , R 2 , R 3 , R 4 , R 5 , and Y are as defined in claim 1 and Z represents a reactive group.
Claim 16
Dependent Claim
84 words
A process according to claim 1 for producing a compound wherein X is a saturated hydrocarbyl group which process comprises (a) reacting a piperazine-2-carboxylic acid or ester of the formula III: with a compound of formula IV in which formulae R, R1, R 2 , R 3 , R 4 , R 5 , and Y are as defined above and wherein X is an unsaturated hydrocarbyl group and Z represents a reactive group and (b) subsequently catalytically hydrogenating the product of step (a).
Claim 17
Dependent Claim
18 words
A process according to claim 1 or claim 2 wherein Z is a reactive halogeno or p-tosyl group.
Claim 18
Dependent Claim
25 words
A process as claimed in any one of claims 1 to 3 wherein X, in the compound produced is C 1 -C 4 hydrocarbyl group.
Claim 19
Dependent Claim
20 words
A process as claimed in claim 4 wherein X is a C 3 straight chain saturated or unsaturated hydrocarbyl group.
Claim 20
Dependent Claim
11 words
A process as claimed in claim 5 wherein X is mono-unsaturated.
Claim 21
Dependent Claim
52 words
A process as claimed in any one of claims 1 to 6 wherein Y, in the compound produced, is selected from: or or or or where R 6 and R 7 , which may be the same or different, each is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group;
Claim 22
Dependent Claim
16 words
A process as claimed in claim 7 wherein Y is a phosphonic acid or ester thereof.
Claim 23
Dependent Claim
16 words
A process as claimed in any one of claims 1 to 3 for producing 3-((+)-2-carboxypiperazin-4-yl)propyl-1-phosphonic acid.
Claim 24
Dependent Claim
24 words
A pharmaceutical composition comprising a compound produced according to any one of claims 1 to 9 and a pharmaceutically acceptable diluent or carrier therefor.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.