Patent US4254142A successfully refreshed from Google Patents.
US4254142A
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Dithiocarbanilic acids and use thereof as immunosuppressive agent
Assignee: Pharmacia and Upjohn Co
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Filing: 1979-08-08
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Granted: 1981-03-03
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Expires: 1999-08-08
Abstract
Abstract Norbornyl thio- and dithiocarbanilic acid are described. The compounds possess immunoregulatory activity. Also provided are compositions containing and methods of using them.
Inventors
- 👤 David J. Anderson
- 👤 Barbara E. Loughman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:33
CPC Classifications
C; C07; C07C; C07C333/00; C07C333/02
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
201 words
A compound having the formula ##STR18## wherein R 1 through R 4 are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 3 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 ) n A wherein A is selected from the group consisting of carboxyl, carboxylic lower alkylester, carboxylic amide group having the formula ##STR19## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR20## wherein R" and R'" are the same are different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is a cyano or a carboxylic amide group; R 3 or R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amine or carboxyl group.
Claim 2
Dependent Claim
201 words
A compound having the formula ##STR18## wherein R 1 through R 4 are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 3 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 ) n A wherein A is selected from the group consisting of carboxyl, carboxylic lower alkylester, carboxylic amide group having the formula ##STR19## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR20## wherein R" and R'" are the same are different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is a cyano or a carboxylic amide group; R 3 or R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amine or carboxyl group.
Claim 3
Dependent Claim
27 words
A compound according to claim 1 having the formula ##STR21## wherein R 1 thru R 5 , R', and Z are the same as in claim 1.
Claim 4
Dependent Claim
15 words
A compound according to claim 2 wherein R 5 is carboxyl and Z is sulfur.
Claim 5
Dependent Claim
8 words
A compound according to claim 3, Exo-(±)-3-[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
Claim 6
Dependent Claim
27 words
A compound according to claim 1, having the formula ##STR22## wherein R 1 thru R 5 , R', and Z are the same as in claim 1.
Claim 7
Dependent Claim
15 words
A compound according to claim 5 wherein R 5 is carboxyl, and Z is sulfur.
Claim 8
Dependent Claim
8 words
A compound according to claim 6, Endo-(±)-3-[[(bicyclo)[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
Claim 9
Dependent Claim
231 words
A composition useful as an immunoregulatory agent comprising an effective amount of a compound having the formula ##STR23## wherein R 1 through R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein A is selected from the group consisting of carboxyl, carboxylic lower alkylester carboxylic amide group having the formula ##STR24## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR25## wherein R" and R'" are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group, R 3 or R 4 must always be hydrogen; or a pharmaceutically acceptable salt of a compound wherein R 5 is an amine or a carboxyl group in combination with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
231 words
A composition useful as an immunoregulatory agent comprising an effective amount of a compound having the formula ##STR23## wherein R 1 through R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein A is selected from the group consisting of carboxyl, carboxylic lower alkylester carboxylic amide group having the formula ##STR24## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR25## wherein R" and R'" are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group, R 3 or R 4 must always be hydrogen; or a pharmaceutically acceptable salt of a compound wherein R 5 is an amine or a carboxyl group in combination with a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
30 words
A composition according to claim 8 wherein the compound has the formula ##STR26## wherein R 1 thru R 5 , R', and Z are the same as in claim 8.
Claim 12
Dependent Claim
15 words
A composition according to claim 9 wherein R 5 is carboxyl and Z is sulfur.
Claim 13
Dependent Claim
8 words
A composition according to claim 10, Exo-(±)-3-[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
Claim 14
Dependent Claim
27 words
A composition according to claim 8 having the formula ##STR27## wherein R 1 thru R 5 , R', and Z are the same as in claim 8.
Claim 15
Dependent Claim
15 words
A composition according to claim 12 wherein R 5 is carboxyl, and Z is sulfur.
Claim 16
Dependent Claim
8 words
A composition according to claim 13, Endo-(±)-3-[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
Claim 17
Independent Claim
242 words
A method of producing immunosuppression in a mammal exhibiting a hyperimmunity disease which comprises systematically administering in a pharmaceutically acceptable dosage form a compound having the formula ##STR28## wherein R 1 thru R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein Z is selected from the group consisting of carboxyl, carboxylic lower alkylester carboxylic amide group having the formula ##STR29## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR30## wherein R" and R"' are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group R 3 and R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amide or carboxyl group, in an amount effective to ameliorate or cure said hyperimmunity disease.
Claim 18
Independent Claim
242 words
A method of producing immunosuppression in a mammal exhibiting a hyperimmunity disease which comprises systematically administering in a pharmaceutically acceptable dosage form a compound having the formula ##STR28## wherein R 1 thru R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein Z is selected from the group consisting of carboxyl, carboxylic lower alkylester carboxylic amide group having the formula ##STR29## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR30## wherein R" and R"' are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group R 3 and R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amide or carboxyl group, in an amount effective to ameliorate or cure said hyperimmunity disease.
Claim 19
Dependent Claim
21 words
A method according to claim 15 wherein the compound is selected from the group consisting of Exo-(±)-3-[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid, and endo-(±)-3-[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
Claim 20
Independent Claim
232 words
A method of producing selective immunosuppression in a mammal exhibiting a hyperimmunity disease which comprises systematically administering in a pharmaceutically acceptable dosage form a compound having the formula ##STR31## wherein R 1 thru R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; and Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein Z is selected from the group consisting of carboxyl, carboxylic alkylester, carboxylic amide group having the formula ##STR32## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR33## wherein R" and R'" are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group, R 3 or R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amine or carboxyl group.
Claim 21
Independent Claim
232 words
A method of producing selective immunosuppression in a mammal exhibiting a hyperimmunity disease which comprises systematically administering in a pharmaceutically acceptable dosage form a compound having the formula ##STR31## wherein R 1 thru R 4 are the same or different and are selected from the group consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive; and aralkyl of from 7 to 20 carbon atoms, inclusive; R' is selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; and Z is selected from the group consisting of oxygen and sulfur; R 5 is --(CH 2 )n A , wherein Z is selected from the group consisting of carboxyl, carboxylic alkylester, carboxylic amide group having the formula ##STR32## wherein R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen and lower alkyl of from 1 to 8 carbon atoms, inclusive; cyano and an amine group having the formula ##STR33## wherein R" and R'" are the same or different and are selected from the group consisting of hydrogen and alkyl of from 1 to 8 carbon atoms, inclusive; with the proviso that when R 5 is cyano or a carboxylic amide group, R 3 or R 4 must always be hydrogen; and pharmaceutically acceptable salts of compounds wherein R 5 is an amine or carboxyl group.
Claim 22
Dependent Claim
21 words
A method according to claim 17 wherein the compound is selected from the group consisting of Exo-(±)[[(bicyclo[2,2,1]hept-2-ylamino)thioxomethyl]thio]propanoic acid and endo-(±)-3-[[(bicyclo[2,2]hept-2-ylamino)thioxomethyl]thio]propanoic acid.
References Cited (Backward Citations)
US3075875A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-03-02 | 1984-09-01 | 1985-03-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-02 | 1988-09-01 | 1989-03-03 | $3760.00 | Window Closed / Lapsed |
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