Claims
- 1. A compound of the formula ##STR98## wherein: a is 1 or 2;
- b is 0 or 1;
- c is 2, 3 or 4;
- X is oxygen, sulfur, ##STR99## Z is --NHR.sub.7 ; R.sub.1 is --NR.sub.5 R.sub.6 ;
- R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen, lower alkyl, allyl, arylloweralkyl wherein aryl is phenyl or substituted phenyl, loweralkoxycarbonyl or lower alkyl substituted by hydroxy, loweralkoxycarbonyl or NR.sub.5 R.sub.6 ;
- R.sub.5 and R.sub.6 are each independently H or alkyl, or both together with the nitrogen to which they are attached form a 5, 6 or 7-membered ring which may include one to three additional hetero atoms of N, O or S;
- R.sub.7 is selected from the group consisting of ##STR100## R.sub.8 is H or lower alkyl; or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1 wherein a is 1.
- 3. A compound according to claim 2 wherein:
- B is 0;
- C is oxygen;
- Z is NHR.sub.7 ;
- R.sub.1 is NR.sub.5 R.sub.6 ; and
- R.sub.3 and R.sub.4 are hydrogen.
- 4. A compound of the formula ##STR101## wherein: b is 0 or 1;
- c is 2, 3 or 4;
- X is oxygen or sulfur;
- Z is --NHR.sub.7 ;
- R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen lower alkyl, allyl, arylloweralkyl wherein aryl is phenyl or substituted phenyl, loweralkoxycarbonyl or lower alkyl substituted by hydroxy, loweralkoxycarbonyl or NR.sub.5 R.sub.6 ;
- R.sub.5 and R.sub.6 are each independently H or alkyl, or both together with the nitrogen to which they are attached form a 5, 6 or 7-membered ring which may include one to three additional hetero atoms of N, O or S;
- R.sub.7 is selected from the group consisting of ##STR102## R.sub.8 is H or lower alkyl; or a pharmaceutically acceptable salt thereof.
- 5. A compound according to claim 4 wherein:
- b is 0;
- X is oxygen;
- R.sub.1 is NR.sub.5 R.sub.6 ; and
- R.sub.3 is hydrogen.
- 6. A compound of the formula: ##STR103## wherein: b is 0 or 1;
- c is 2, 3 or 4;
- X is oxygen or sulfur;
- Z is --NHR.sub.7 ;
- R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen, lower alkyl, allyl, arylloweralkyl wherein aryl is phenyl or substituted phenyl, loweralkoxycarbonyl or lower alkyl substituted by hydroxy, loweralkoxycarbonyl or NR.sub.5 R.sub.6 ;
- R.sub.5 and R.sub.6 are each independently H or alkyl, or both together with the nitrogen to which they are attached form a 5, 6 or 7-membered ring which may include one to three additional hetero atoms of N, O or S;
- R.sub.7 is selected from the group consisting of ##STR104## R.sub.8 is H or lower alkyl; or a pharmaceutically acceptable salt thereof.
- 7. A compound according to claim 6 wherein:
- b is 0;
- X is oxygen;
- R.sub.1 is NR.sub.5 R.sub.6 ; and
- R.sub.3 is hydrogen.
- 8. A compound of the formula: ##STR105## wherein: c is 2, 3 or 4;
- n is 4, 5 or 6;
- R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen, lower alkyl, allyl, arylloweralkyl wherein aryl is phenyl or substituted phenyl, loweralkoxycarbonyl or lower alkyl substituted by hydroxy, loweralkoxycarbonyl or NR.sub.5 R.sub.6 ;
- R.sub.5 and R.sub.6 are each independently H or alkyl, or both together with the nitrogen to which they are attached form a 5, 6 or 7-membered ring which may include one to three additional hetero atoms of N, O or S;
- R.sub.7 is selected form the group consisting of ##STR106## R.sub.8 is H or lower alkyl; or a pharmaceutically acceptable salt thereof.
- 9. A compound according to claim 8 wherein:
- c is 3; and
- R.sub.2, R.sub.3 and R.sub.4 are hydrogen.
- 10. A compound according to claim 8 wherein:
- c is 3; and
- R.sub.3 and R.sub.4 are hydrogen.
- 11. A compound according to claim 8 wherein:
- c is 3; and
- R.sub.2 is hydrogen.
- 12. A compound according to claim 8 wherein:
- c is 3; and
- R.sub.2 and R.sub.3 are hydrogen.
- 13. A compound according to claim 12 wherein the R.sub.4 substituent is cis relative to the (CH.sub.2)n N--CH.sub.2 --substituent.
- 14. A compound according to claim 13 wherein the R.sub.4 substituent is trans relative to the (CH.sub.2)n N--CH.sub.2 --substituent.
- 15. A compound according to claim 1 which is 3-amino-4-[3-[5-[1-(1-piperidinylmethyl)benzocyclobutenyloxy]propylamino]]-1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 16. A compound according to claim 1 which is 3-amino-4-[3-[5-[1-methyl-1-(piperidinylmethyl)benzocyclobutenyloxy]propylamino]]-1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 17. A compound according to claim 1 which is 3-amino-4-[3-[5-[trans-2-methyl-1-(piperidinylmethyl)benzocyclobutenyloxy]propylamino]]-1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 18. A compound according to claim 1 which is 3-amino-4-[3-[5-[cis-2-methyl-1-(1-piperidinylmethyl)benzocyclobutenyloxy]propylamino]]1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 19. A compound according to claim 1 which is 3-amino-4-[3-[5-[1-allyl-1-(1-piperidinylmethyl)benzocyclobutenyloxy]propylamino]]-1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 20. A compound according to claim 1 which is 3-amino-4-[3-[5-[1-dimethylaminomethyl-1-(1-piperidinylmethyl)benzocyclobutenyloxy]propylamino]]-1,2,5-thiadiazole-1-oxide, or a pharmaceutically acceptable salt thereof.
- 21. A pharmaceutical composition wherein the active ingredient is a compound according to claim 1 in admixture with a pharmaceutical carrier.
- 22. A method for decreasing acid secretion in the gastrointestinal tract of mammals by administering thereto an anti-secretory effective amount of a compound according to claim 1.
- 23. A method for the treatment of gastrointestinal hyperacidity and ulceration in a mammal comprising administering thereto an effective amount of a compound according to claim 1.
- 24. A method for enhancing the gastrointestinal resistance to gastrointestinal irritants in humans and mammals comprising administering thereto an effective cytoprotective amount of a compound of the formula according to claim 1.
Parent Case Info
This is a divisional of co-pending application Ser. No. 798,697 filed on Nov. 1, 1985 now U.S. Pat. No. 4,639,442, which is a continuation-in-part of application Ser. No. 664,222 filed on Oct. 23, 1984, now U.S. Pat. No. 4,558,719 issued on May 13, 1986, which is a continuation-in-part of copending application Ser. No. 604,813 filed on Apr. 27, 1984 now U.S. Pat. No. 4,638,001, which is a continuation-in-part of application Ser. No. 489,702 filed on Apr. 29, 1983, now U.S. Pat. No. 4,529,723 issued on July 16, 1985.
Foreign Referenced Citations (1)
Number |
Date |
Country |
167588 |
Sep 1984 |
JPX |
Divisions (1)
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Number |
Date |
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Parent |
798697 |
Nov 1985 |
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Continuation in Parts (3)
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Number |
Date |
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Parent |
664222 |
Oct 1984 |
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Parent |
604813 |
Apr 1984 |
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Parent |
489702 |
Apr 1983 |
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