US4128658A
Expired / Lapsed
US
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Aminoalkyl furan derivatives
Assignee: Allen and Hanburys Ltd
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Filing: 1977-07-25
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Granted: 1978-12-05
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Expires: 1997-07-25
Abstract
Abstract Compounds of the general formula I: ##STR1## and physiologically acceptable salts thereof and N-oxides and hydrates, in which R 1 and R 2 which may be the same or different represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group ##STR2## in which R 4 represents hydrogen or lower alkyl or R 1 and R 2 may, together with the nitrogen atom to which they are attached, form a heterocyclic ring which may contain other heteroatoms selected from O and ##STR3## R 3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH 2 --, O or S; Y represents ═ S, ═ O, ═ NR 5 or ═ CHR 6 ; Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms; R 5 is H, nitro, cyano, lower alkyl, aryl, alkylsulphonyl, or arylsulphonyl; R 6 represents nitro, arylsulphonyl or alkylsulphonyl; M is an integer from 2 to 4; and N is 1 or 2; or when X ═ S, or --CH 2 --, n is zero, 1 or 2. These compounds have H 2 -antagonist activity. Intermediates in the production thereof are also provided.
Inventors
- 👤 Barry J. Price
- 👤 John W. Clitherow
- 👤 John Bradshaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 12:12
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/02; C07D275/03; A; A61; A61K; A61K31/00; A61K31/33; A61K31/335; A61K31/34; A61P; A61P43/00; C07D207/00; C07D207/02; C07D207/04; C07D207/08; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52; C07D307/56; C07D307/64
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
206 words
A compound of the general formula I: ##STR39## or a physiologically acceptable salt, N-oxide or hydrate thereof in which R 1 and R 2 which may be the same or different represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo or lower alkyl interrupted by an oxygen atom or a group ##STR40## in which R 4 represents hydrogen or lower alkyl; R 3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH 2 --, O or S; Y represents ═ S, ═ O, ═ NR 5 or ═ CHR 6 ; Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms; R 5 is H, nitro, cyano, lower alkyl, phenyl, phenyl substituted by alkyl, alkoxy or halo, alkylsulphonyl, or arylsulphonyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo; R 6 represents nitro, arylsulphonyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo or alkylsulphonyl; m is an integer from 2 to 4; and n is 1 or 2; or when X ═ S, or --CH 2 --, n is zero, 1 or 2.
Claim 2
Dependent Claim
206 words
A compound of the general formula I: ##STR39## or a physiologically acceptable salt, N-oxide or hydrate thereof in which R 1 and R 2 which may be the same or different represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo or lower alkyl interrupted by an oxygen atom or a group ##STR40## in which R 4 represents hydrogen or lower alkyl; R 3 is hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X is --CH 2 --, O or S; Y represents ═ S, ═ O, ═ NR 5 or ═ CHR 6 ; Alk denotes a straight or branched alkylene chain of 1 to 6 carbon atoms; R 5 is H, nitro, cyano, lower alkyl, phenyl, phenyl substituted by alkyl, alkoxy or halo, alkylsulphonyl, or arylsulphonyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo; R 6 represents nitro, arylsulphonyl in which the aryl portion is phenyl or phenyl substituted by alkyl, alkoxy or halo or alkylsulphonyl; m is an integer from 2 to 4; and n is 1 or 2; or when X ═ S, or --CH 2 --, n is zero, 1 or 2.
Claim 3
Dependent Claim
72 words
A compound as claimed in claim 1 in which R 1 and R 2 independently represent hydrogen, alkyl, phenylalkyl, or dialkylamino alkyl, Alk represents a straight alkylene chain of 1 to 4 carbon atoms, Y is ═ S, ═ O, ═ CHNO 2 or ═NR 5 where R 5 is hydrogen, nitro, cyano, lower alkyl, alkylsulphonyl or benzenesulphonyl, and X, m, n, and R 3 have the meanings given in claim 1.
Claim 4
Dependent Claim
19 words
A compound as claimed in claim 1 in which the lower alkyl groups have 1 to 8 carbon atoms.
Claim 5
Dependent Claim
18 words
A compound as claimed in claim 1 in which the alkenyl groups have 3 to 6 carbon atoms.
Claim 6
Dependent Claim
16 words
A compound as claimed in claim 1 in which n + m is 3 or 4.
Claim 7
Dependent Claim
14 words
A compound as claimed in claim 1 in which Alk represents a methylene group.
Claim 8
Dependent Claim
24 words
A compound as claimed in claim 1 in which R 1 is H or C 1-4 alkyl and R 2 is C 1-4 alkyl.
Claim 9
Dependent Claim
19 words
A compound as claimed in claim 1 in which R 1 and R 2 are independently methyl or ethyl.
Claim 10
Dependent Claim
14 words
A compound as claimed in claim 1 in which X is a sulphur atom.
Claim 11
Dependent Claim
16 words
A compound as claimed in claim 1 in which X represents a group --CH 2 --.
Claim 12
Dependent Claim
92 words
A compound as claimed in claim 1 in which R 1 and R 2 independently represent hydrogen, alkyl of 1 to 3 carbon atoms or phenethyl; Alk represents an alkylene chain of 1 to 3 carbon atoms; Y is ═ S, ═ CHNO 2 , or ═ NR 5 , where R 5 is nitro, cyano, methylsulphonyl or benzenesulphonyl; R 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.
Claim 13
Dependent Claim
81 words
A compound as claimed in claim 1 in which R 1 and R 2 independently represent H, alkyl of 1 to 3 carbon atoms, phenethyl; Alk represents an alkylene group of 1 to 3 carbon atoms; Y is ═ S, ═ CHNO 2 , or ═ NR 5 , where R 5 is nitro, cyano, methylsulphonyl or benzenesulphonyl; X is S or --CH 2 --; R 3 is hydrogen, methyl or methoxyethyl; n is 1 and m is 2 or 3.
Claim 14
Dependent Claim
61 words
A compound as claimed in claim 1 in which R 1 is hydrogen, methyl or ethyl; R 2 is methyl or ethyl; Alk represents a methylene group; Y is ═ NCN, ═ NNO 2 , or ═ CHNO 2 ; R 3 is hydrogen or methyl; X is S or --CH 2 --; and n is 1 and m is 2.
Claim 15
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylthiourea.
Claim 16
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-cyano-N'-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine.
Claim 17
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 18
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-cyano-N'-[2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine.
Claim 19
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(diethylamino)methyl-2furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 20
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(2-methoxyethyl)-2-nitro-1,1-ethenediamine.
Claim 21
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(2-methoxyethyl)thiourea.
Claim 22
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 23
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[3-[[5-(dimethylamino)methyl-2-furanyl]thio]propyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 24
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[-2-[[[5-(ethylmethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 25
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-nitroguanidine.
Claim 26
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methanesulphonyl-N"-methylguanidine.
Claim 27
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[4-[5-(dimethylamino)methyl-2-furanyl]butyl]-N'-methylthiourea.
Claim 28
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-benzene-sulphonyl-N'-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N"-methylguanidine.
Claim 29
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[5-[5-(dimethylamino)methyl-2-furanyl]pentyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 30
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-cyano-N'-[5-[5-(dimethylamino)methyl2-furanyl]pentyl]-N'-methylguanidine
Claim 31
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[4-[5-(dimethylamino)methyl-2-furanyl]butyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 32
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-cyano-N'-[4-[5-(dimethylamino)methyl-2-furanyl]butyl]-N"-methylguanidine.
Claim 33
Dependent Claim
11 words
A compound as claimed in claim 1 which is N-[2-[[[5-[3 [dimethylamino]propyl]-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 34
Dependent Claim
10 words
A compound as claimed in claim 1 which is N-[2-[[[5-[[2-(dimethylamino)ethyl]amino]methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 35
Dependent Claim
15 words
A compound as claimed in claim 1 which is a physiologically acceptable acid addition salt.
Claim 36
Dependent Claim
11 words
A compound as claimed in claim 34 which is a hydrochloride.
Claim 37
Dependent Claim
25 words
A pharmaceutical composition comprising a pharmaceutically effective amount of a compound as claimed in claim 1 in association with a pharmaceutically acceptable carrier or diluent.
Claim 38
Dependent Claim
21 words
A composition as claimed in claim 36 in a form suitable for oral, topical or parenteral administration or administration by suppository.
Claim 39
Dependent Claim
12 words
A composition as claimed in claim 37 in oral form as tablets.
Claim 40
Dependent Claim
14 words
A composition as claimed in claim 38 in the form of slow release tablets.
Claim 41
Dependent Claim
17 words
A composition as claimed in claim 39 containing 20 to 200 mg of active ingredient per tablet.
Claim 42
Dependent Claim
16 words
A composition as claimed in claim 37 in topical form as a spray, ointment or cream.
Claim 43
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 claimed in claim 1 to relieve said condition.
Claim 44
Dependent Claim
14 words
A method as claimed in claim 42 in which the condition is peptic ulceration.
Claim 45
Dependent Claim
16 words
A method as claimed in claim 42 in which the condition is an allergic skin condition.
Claim 46
Dependent Claim
4 words
The hydrochloride of N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
Claim 47
Dependent Claim
4 words
The hydrochloride of N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine.
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) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |