US4318913A
Expired / Lapsed
US
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1,2,4-Triazole-3,5-diamine derivatives
Assignee: Glaxo Group Ltd
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Filing: 1979-04-26
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Granted: 1982-03-09
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Expires: 1999-04-26
Abstract
Abstract The invention relates to compounds of the formula (I) ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in which R 1 and R 2 represent hydrogen, an aliphatic or cycloaliphatic group, or R 1 and R 2 together with the nitrogen atom form a 5 to 10 membered heterocyclic ring: Alk represents a straight or branched alkylene chain; Q represents furan, thiophen or benzene ring which is incorporated into the rest of the molecule; X represents --CH 2 --, ##STR2## --O-- or --S-- where R 6 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, a substituted or unsubstituted aliphatic or aryl group and; R 4 and R 5 , which may be the same or different, each represent hydrogen, a substituted or unsubstituted aliphatic, aryl, or together with the nitrogen atom form a heterocyclic group.
Inventors
- 👤 John W. Clitherow
- 👤 John Bradshaw
- 👤 John W. M. Mackinnon
- 👤 Barry J. Price
- 👤 Michael Martin-Smith
- 👤 Duncan B. Judd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 08:43
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/14; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52; C07D317/00; C07D317/08; C07D317/10; C07D317/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
237 words
A compound of the formula (I) ##STR33## and physiologically acceptable acid addition salts thereof, in which R 1 and R 2 together with the nitrogen atom to which they are attached form a 5 to 8 membered alicyclic heterocyclic ring which may be saturated or may contain at least one double bond, may be unsubstituted or may be substituted by one or more C 1-3 alkyl groups or a hydroxy group and/or may contain another heteroatom which is oxygen; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; X represents --CH 2 --, ##STR34## --O-- or --S-- where R 6 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl C 1-6 alkyl, hydroxyalkyl having from two to six carbon atoms, C 1-6 alkoxy C 1-6 alkyl or phenyl, substituted phenyl wherein the substituent is one or more C 1-3 alkyl, C 1-3 alkoxy or halogen atoms; and R 4 and R 5 , which may be the same or different each represent hydrogen, C 1-6 alkyl, C 1-6 alkyl substituted by hydroxy or C 1-3 alkoxy, C 3-6 alkenyl, phenyl C 1-6 alkyl or pyridyl C 1-6 alkyl.
Claim 2
Dependent Claim
237 words
A compound of the formula (I) ##STR33## and physiologically acceptable acid addition salts thereof, in which R 1 and R 2 together with the nitrogen atom to which they are attached form a 5 to 8 membered alicyclic heterocyclic ring which may be saturated or may contain at least one double bond, may be unsubstituted or may be substituted by one or more C 1-3 alkyl groups or a hydroxy group and/or may contain another heteroatom which is oxygen; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; X represents --CH 2 --, ##STR34## --O-- or --S-- where R 6 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, phenyl C 1-6 alkyl, hydroxyalkyl having from two to six carbon atoms, C 1-6 alkoxy C 1-6 alkyl or phenyl, substituted phenyl wherein the substituent is one or more C 1-3 alkyl, C 1-3 alkoxy or halogen atoms; and R 4 and R 5 , which may be the same or different each represent hydrogen, C 1-6 alkyl, C 1-6 alkyl substituted by hydroxy or C 1-3 alkoxy, C 3-6 alkenyl, phenyl C 1-6 alkyl or pyridyl C 1-6 alkyl.
Claim 3
Dependent Claim
16 words
A compound according to claim 1 in which the total of m+n is 3 or 4.
Claim 4
Dependent Claim
14 words
A compound according to claim 2 in which the total of m+n is 3.
Claim 5
Dependent Claim
18 words
A compound according to claim 1 in which X is sulphur, n is 1 and m is 2.
Claim 6
Dependent Claim
22 words
A compound according to claim 1 in which X is oxygen or ##STR35## n is zero and m is 3 or 4.
Claim 7
Dependent Claim
26 words
A compound of claim 1, wherein R 4 and R 5 , which may be the same or different, each represent hydrogen or C 1-6 alkyl.
Claim 8
Dependent Claim
52 words
A compound of claim 1, wherein Alk represents a methylene, ethylene or propylene group; n is zero; X is oxygen or NH; m is 3 or 4; R 4 represents hydrogen or C 1-3 alkyl optionally substituted by a phenyl or pyridyl group and R 5 represents hydrogen or C 1-3 alkyl.
Claim 9
Dependent Claim
24 words
A compound of claim 7, wherein R 3 represents hydrogen, methyl, ethyl or hydroxyethyl; R 4 and R 5 both represent hydrogen or ethyl.
Claim 10
Dependent Claim
40 words
A compound of claim 1 wherein Q is benzene incorporated into the rest of the molecule through bonds at the 1 and 3 positions and in which Alk represents methylene, n is zero, X is --O--, and m is 3.
Claim 11
Dependent Claim
18 words
A compound of claim 9, wherein R 3 represents methyl and R 4 and R 5 represent hydrogen.
Claim 12
Dependent Claim
16 words
A compound according to claim 1 in which Alk represents a methylene, ethylene or propylene group.
Claim 13
Dependent Claim
18 words
A compound according to claim 1 in which R 3 represents hydrogen or C 1-4 alkyl or hydroxyalkyl.
Claim 14
Dependent Claim
49 words
A compound according to claim 1 in which R 1 and R 2 together with the nitrogen atom to which they are attached form heterocyclic ring which is selected from pyrrolidine, piperidine, piperidine substituted in the 4-position by C 1-3 alkyl or hydroxy, tetrahydropyridine, morpholine, 2,6-dialkylmorpholine, hexamethyleneimine and heptamethyleneimine.
Claim 15
Dependent Claim
119 words
A compound according to claim 1 Alk represents a methylene, ethylene or propylene group; n is zero; X is oxygen or NH; m is 3 or 4; R 1 and R 2 together with the nitrogen atom to which they are attached form a 5 to 8 membered alicyclic heterocyclic ring which may be saturated or contain at least one double bond, or be saturated and substituted by one or more C 1-3 alkyl groups and may contain an additional heteroatom which is oxygen; R 3 is hydrogen or C 1-2 alkyl or hydroxyethyl; R 4 represents hydrogen or C 1-3 alkyl optionally substituted by a phenyl or pyridyl group and R 5 represents hydrogen or C 1-3 alkyl.
Claim 16
Dependent Claim
36 words
A compound according to claim 1 in which R 4 represents hydrogen or C 1-5 alkyl optionally substituted by phenyl, pyridyl, hydroxy or C 1-3 alkoxy group and R 5 represents hydrogen or C 1-3 alkyl.
Claim 17
Dependent Claim
63 words
A compound according to claim 1 and physiologically acceptable salts thereof, in which Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3-positions; X represents --CH 2 --, --O-- or --S--; and R 4 and R 5 which may be the same or different, each represent hydrogen or C 1-6 alkyl.
Claim 18
Dependent Claim
22 words
A compound according to claim 1 which is: 1-methyl-N 5 -[3-[3-[1-pyrrolidinylmethyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine 1-methyl-N 5 -[3-[3-[1-hexamethyleneiminylmethyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine N 3 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine or their physiologically acceptable salts.
Claim 19
Dependent Claim
28 words
A compound according to claim 1 which is: 1-methyl-N 5 -[3-[3-[1-(1,2,3,6-tetrahydropyridinyl)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine 1-ethyl-N 5 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine 1-methyl-N 5 -[4-[3-(1-piperidinylmethyl)phenoxy]butyl]-1H-1,2,4-triazole-3,5-diamine 1-methyl-N 5 -[3-[3-[1-(4-methylpiperidinyl)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine 1-(2-hydroxyethyl)-N 5 -[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine or their physiologically acceptable salts.
Claim 20
Dependent Claim
11 words
The compound 1-methyl-N 5 -[3-[3-[1-piperidinylmethyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine or a physiologically acceptable salt thereof.
Claim 21
Dependent Claim
11 words
The compound 1-methyl-N 5 -[3-[3-[1-piperidinylmethyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine or a physiologically acceptable salt thereof.
Claim 22
Dependent Claim
45 words
A pharmaceutical composition for the treatment of conditions mediated through H 2 -receptors comprising an effective amount of at least one compound as defined in claim 1 together with at least one pharmaceutically acceptable carrier or diluent and optionally at least one other active ingredient.
Claim 23
Dependent Claim
19 words
A pharmaceutical composition according to claim 20 in which the active compound is in the form of a salt.
Claim 24
Dependent Claim
23 words
A pharmaceutical composition as claimed in claim 21 in which the salt is a hydrochloride, hydrobromide, sulphate, acetate, maleate, succinate, citrate or fumarate.
Claim 25
Dependent Claim
17 words
A pharmaceutical composition as claimed in claim 20 in the form of tablets, capsules or a syrup.
Claim 26
Dependent Claim
33 words
A method of treating a condition mediated through histamine H 2 -receptors which comprises administering to a patient an effective amount of a compound as defined in claim 1 to relieve said condition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-03-08 | 1985-09-07 | 1986-03-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-08 | 1989-09-07 | 1990-03-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-08 | 1993-09-07 | 1994-03-09 | $7700.00 | Window Closed / Lapsed |