Claims
- 1. A compound of the general formula I: ##STR39## or a physiologically acceptable acid addition salt, N-oxide or hydrate thereof, in which R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated heterocyclic ring selected from the group consisting of morpholino, piperidino, pyrrolidino, and N-alkylpiperazino;
- R.sub.3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH.sub.2 --, --O-- or --S--;
- Y represents .dbd.S, .dbd.O, .dbd.NR.sub.5 or .dbd.CHR.sub.6 ;
- Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms;
- R.sub.5 is H, nitro, cyano, lower alkyl, phenyl, phenyl substituted by alkyl, alkoxy or halogen, alkylsulphonyl, or arylsulphonyl in which the aryl moiety is phenyl or phenyl substituted by alkyl, alkoxy or halogen;
- R.sub.6 represents nitro, arylsulphonyl in which the aryl moiety is phenyl or phenyl substituted by alkyl, alkoxy or halogen, or alkylsulphonyl;
- m is an integer from 2 to 4; and
- n is 1 or 2; or when X is --S-- or --CH.sub.2 --, n is zero, 1 or 2.
- 2. A compound as claimed in claim 1 in which Alk represents a straight alkylene chain of 1 to 4 carbon atoms, Y is .dbd.S, .dbd.O, .dbd.CHNO.sub.2 or .dbd.NR.sub.5 where R.sub.5 is hydrogen, nitro, cyano, lower alkyl, alkylsulphonyl or benzenesulphonyl, and X, m, n, and R.sub.3 having the meanings given in claim 1.
- 3. A compound as claimed in claim 1 in which the lower alkyl groups have 1 to 8 carbon atoms.
- 4. A compound as claimed in claim 1 in which the alkenyl groups have 3 to 6 carbon atoms.
- 5. A compound as claimed in claim 1 in which n+m is 3 or 4.
- 6. A compound as claimed in claim 1 in which Alk represents a methylene group.
- 7. A compound as claimed in claim 1 in which X is a sulphur atom.
- 8. A compound as claimed in claim 1 in which X represents a group --CH.sub.2 --.
- 9. A compound as claimed in claim 1 in which R.sub.1 and R.sub.2 together with the nitrogen atom form a pyrrolidine ring; Alk represents an alkylene chain of 1 to 3 carbon atoms; Y is .dbd.S, .dbd.CHNO.sub.2, or .dbd.NR.sub.5, where R.sub.5 is nitro, cyano, methylsulphonyl or benzenesulphonyl; R.sub.3 represents hydrogen, alkyl of 1 to 3 carbon atoms, propenyl or alkoxyalkyl of 3 carbon atoms; n+m is 3 or 4, and X is as defined in claim 1.
- 10. A compound as claimed in claim 1 in which R.sub.1 and R.sub.2 together with the nitrogen atom form a pyrrolidine ring; Alk represents an alkylene group of 1 to 3 carbon atoms; Y is .dbd.S, .dbd.CHNO.sub.2, or .dbd.NR.sub.5, where R.sub.5 is nitro, cyano, methylsulphonyl or benzenesulphonyl; X is S or --CH.sub.2 --; R.sub.3 is hydrogen, methyl or methoxyethyl; n is 1 and m is 2 or 3.
- 11. A compound as claimed in claim 1 which is a hydrochloride.
- 12. A compound as claimed in claim 1 in which R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached are pyrrolidinyl.
- 13. The compound of claim 1 which is N-methyl-N'-[2-[[[5-(1-pyrrolidinyl)methyl-2-furanyl]methyl]thio]ethyl]thiourea.
- 14. The compound of claim 1 which is N-methyl-N'-[2-[[[5-(1-pyrrolidinyl)methyl-2-furanyl]methyl]thio]ethyl]urea.
- 15. The compound of claim 1 which is N-cyano-N'-[2-[[[5-(1-pyrrolindinyl)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine.
- 16. The compound of claim 1 which is N-methyl-2-nitro-N'-[2-[[[5-[(1-pyrrolidinyl)methyl]-2-furanyl]methyl]thio]ethyl]-1,1-ethenediamine.
- 17. A pharmaceutical composition for treating a condition mediated through histamine H.sub.2 -receptors, comprising a pharmaceutically effective amount of a compound as claimed in claim 1 in association with a pharmaceutically acceptable carrier or diluent.
- 18. A composition as claimed in claim 17 in a form suitable for oral, topical or parenteral administration or administration by suppository.
- 19. A composition as claimed in claim 18 in oral form as tablets.
- 20. A composition as claimed in claim 19 in the form of slow release tablets.
- 21. A composition as claimed in claim 19 containing 20 to 200 mg of active ingredient per tablet.
- 22. A composition as claimed in claim 18 in topical form as a spray, ointment or cream.
- 23. A method of treating a condition mediated through histamine H.sub.2 -receptors which comprises administering to a patient an effective amount of a compound as claimed in claim 1 to relieve said condition.
- 24. A method as claimed in claim 23 in which the condition is peptic ulceration.
- 25. A method as claimed in claim 23 in which the condition is an allergic skin condition.
Priority Claims (3)
Number |
Date |
Country |
Kind |
32465/76 |
Aug 1976 |
GBX |
|
50685/76 |
Dec 1976 |
GBX |
|
20187/77 |
May 1977 |
GBX |
|
Parent Case Info
This is a division of application Ser. No. 818,762, filed July 25, 1977, now U.S. Pat. No. 4,128,658.
US Referenced Citations (4)
Foreign Referenced Citations (4)
Number |
Date |
Country |
1307539 |
Feb 1973 |
GBX |
1338169 |
Nov 1973 |
GBX |
1397436 |
Jun 1975 |
GBX |
1421792 |
Jan 1976 |
GBX |
Divisions (1)
|
Number |
Date |
Country |
Parent |
818762 |
Jul 1977 |
|