US4022962A
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Carbamylguanidine antimicrobial compounds
Assignee: Gillette Co LLC
•
Filing: 1975-02-03
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Granted: 1977-05-10
•
Expires: 1995-02-03
Abstract
Abstract Antimicrobial compounds are disclosed having the formula:
Inventors
- 👤 Julius Diamond
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 00:26
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/13; A61K31/135; A61K31/16; A61K31/165; A61K31/17; A61K31/21; A61K31/27; A61K31/33; A61K31/335; A61K31/35; C; C07; C07C; C07C279/00; C07C279/04; C07C279/14
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
259 words
A compound having the formula Z--B--Y--B--Z .sup.. nHA wherein Y is a C 2 -C 12 alkylene, [C 5 -C 12 cycloalkylene, C 5 -C 12 cycloalkylenebis(loweralkyl), C 6 -C 12 arylene and loweralkylarylene, C 7 -C 12 aryleneloweralkyl, and C 8 -C 12 arylenebis(loweralkyl)]; B is a [substituted guandino] carbamylguanidino group [selected from the group consisting of carbamylguanidino and thiocarbamylguanidino]; [or biguanidino provided that B' is biguanidino only when B is carbamylguanidino bonded to Y through the guanidino portion of the group]; and Z is selected from the group consisting of [C 1 -C 12 alkyl; C 4 C 12 dialkylaminoalkyl; C 3 -C 12 alkenyl; C 3 -C 12 alkynyl; C 3 -C 12 cycloalkyl, C 4 -C 12 cycloalkylalkyl; C 1 -C 10 alkoxy C 10 -C 2 alkyl having a total carbon content of C 3 -C 14 ; C 1 -C 10 alkylthio C 10 -C 2 alkyl having a total carbon content of C 3 -c 14 ; phenoxy C 2 -C 6 alkyl; phenylthio C 2 -C 6 alkyl]; C 6 -C 14 aryl; [C 7 -C 14 aralkyl and arylcycloalkyl]; and C 6 -C 14 aryl [and aralkyl]]substituted with one or more radicals selected from the group consisting of lower alkyl, trifluoromethyl, loweralkoxy, trifluoromethyoxy, [phenoxy,] loweralkylthio, halo, [nitro, cyano, C 2 -C 6 acyl, benzoyl, alkoxycarbonyl, diloweralkylamino,] and loweralkylsulfonyl, [fluorosulfonyl and alkylsulfinyl]; and pharmacologically acceptable addition salts of these compounds with acids represented by nHA wherein n=0, 1/3, 1/2, 2/3, 1, and 2 and HA is an inorganic or organic acid.
Claim 2
Dependent Claim
259 words
A compound having the formula Z--B--Y--B--Z .sup.. nHA wherein Y is a C 2 -C 12 alkylene, [C 5 -C 12 cycloalkylene, C 5 -C 12 cycloalkylenebis(loweralkyl), C 6 -C 12 arylene and loweralkylarylene, C 7 -C 12 aryleneloweralkyl, and C 8 -C 12 arylenebis(loweralkyl)]; B is a [substituted guandino] carbamylguanidino group [selected from the group consisting of carbamylguanidino and thiocarbamylguanidino]; [or biguanidino provided that B' is biguanidino only when B is carbamylguanidino bonded to Y through the guanidino portion of the group]; and Z is selected from the group consisting of [C 1 -C 12 alkyl; C 4 C 12 dialkylaminoalkyl; C 3 -C 12 alkenyl; C 3 -C 12 alkynyl; C 3 -C 12 cycloalkyl, C 4 -C 12 cycloalkylalkyl; C 1 -C 10 alkoxy C 10 -C 2 alkyl having a total carbon content of C 3 -C 14 ; C 1 -C 10 alkylthio C 10 -C 2 alkyl having a total carbon content of C 3 -c 14 ; phenoxy C 2 -C 6 alkyl; phenylthio C 2 -C 6 alkyl]; C 6 -C 14 aryl; [C 7 -C 14 aralkyl and arylcycloalkyl]; and C 6 -C 14 aryl [and aralkyl]]substituted with one or more radicals selected from the group consisting of lower alkyl, trifluoromethyl, loweralkoxy, trifluoromethyoxy, [phenoxy,] loweralkylthio, halo, [nitro, cyano, C 2 -C 6 acyl, benzoyl, alkoxycarbonyl, diloweralkylamino,] and loweralkylsulfonyl, [fluorosulfonyl and alkylsulfinyl]; and pharmacologically acceptable addition salts of these compounds with acids represented by nHA wherein n=0, 1/3, 1/2, 2/3, 1, and 2 and HA is an inorganic or organic acid.
Claim 3
Dependent Claim
42 words
A compound according to claim 1 wherein Y is a C 4 -C 8 alkylene[, C 5 -C 8 cycloalkylene, C 5 -C 8 cycloalkylenebis(loweralkyl), C 6 -C 8 arylene and loweralkylarylene, C 7 -C 8 aryleneloweralkyl, and C 8 arylenebis(loweralkyl)] radical.
Claim 4
Dependent Claim
88 words
A compound according to claim 1 wherein Z is selected from the group consisting of [C 4 -C 10 alkyl, C 5 -C 9 cycloalkyl, C 6 -C 9 cycloalkylalkyl,] phenyl, naphthyl, [phenyl C 1 -C 4 alkyl, phenyl C 3 cycloalkyl,] C 1 -C 4 alkylphenyl, [C 1 -C 3 alkylbenzyl,] trifluoromethylphenyl, [trifluoromethylbenzyl,] C 1 -C 4 alkoxyphenyl, trifluoromethoxyphenyl, [phenoxyphenyl,] C 1 -C 4 alkylthiophenyl, halophenyl, [halobenzyl, C 2 -C 4 acylphenyl, C 1 -C 4 alkoxycarbonylphenyl,] and C 1 -C 4 alkylsulfonylphenyl [, and fluorosulfonylphenyl] radicals.
Claim 5
Dependent Claim
21 words
A compound according to claim 1 having the formula: wherein Z and Y have the meaning defined in claim 1. ##STR22##
Claim 6
Dependent Claim
52 words
A compound according to claim 1 wherein said acid, HA, is selected from the group consisting of hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, acetic acid, glycolic acid, 2,3-dihydroxypropionic acid, saccharic acid, gluconic acid, lactobionic acid, maleic acid, fumaric acid, lactic acid, citric acid, malic acid, methanesulfonic acid, and ethanesulfonic acid.
Claim 7
Dependent Claim
21 words
A compound according to claim 1 having the formula: ##STR23## wherein Z and Y have the meaning defined in claim 1.
Claim 8
Dependent Claim
16 words
A compound according to claim 6 wherein Y is a C 4 -C 8 alkylene radical.
Claim 9
Dependent Claim
42 words
A compound according to claim 6 wherein Z is selected from the group consisting of phenyl, naphthyl, C 1 -C 4 alkylphenyl, trifluoromethylphenyl, C 1 -C 4 alkoxyphenyl, trifluoromethoxyphenyl, C 1 -C 4 alkylthiophenyl, halophenyl, and C 1 -C 4 alkylsulfonylphenyl radicals.
Claim 10
Dependent Claim
52 words
A compound according to claim 6 wherein Y is a C 4 -C 8 alkylene radical, and Z is selected from the group consisting of phenyl, naphthyl, C 1 -C 4 alkylphenyl, trifluoromethylphenyl, C 1 -C 4 alkoxyphenyl, trifluoromethoxyphenyl, C 1 -C 4 alkylthiophenyl, halophenyl, and C 1 -C 4 alkylsulfonylphenyl radicals.
Claim 11
Dependent Claim
49 words
A compound according to claim 9 wherein Y is selected from the group consisting of pentamethylene, hexamethylene, and heptamethylene radicals and Z is selected from the group consisting of phenyl, 4-tolyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 4-ethoxyphenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, and 4-methylthio-3-chlorophenyl radicals.
Claim 12
Dependent Claim
18 words
A compound according to claim 9 wherein Y is C 5 -C 7 polymethylene and Z is halophenyl.
Claim 13
Dependent Claim
18 words
A compound according to claim 9 wherein Y is C 5 -C 7 polymethylene and Z is trifluormethylphenyl.
Claim 14
Dependent Claim
18 words
A compound according to claim 8 wherein Y is C 5 -C 7 polymethylene and Z is phenyl.
Claim 15
Dependent Claim
7 words
1,5-bis(4-chlorophenylcarbamylguanidino)pentane and pharmacologically acceptable acid addition salts.
Claim 16
Dependent Claim
7 words
1,5-bis(4-chlorophenylcarbamylguanidino)pentane and pharmacologically acceptable acid addition salts.
Claim 17
Dependent Claim
7 words
1,6-bis(4-chlorophenylcarbamylguanidino(hexane and pharmacologically acceptable acid addition salts.
Claim 18
Dependent Claim
7 words
1,6-bis(4-chlorophenylcarbamylguanidino(hexane and pharmacologically acceptable acid addition salts.
Claim 19
Dependent Claim
7 words
1,7-bis(4-chlorophenylcarbamylguanidino)heptane and pharmacologically acceptable acid addition salts.
Claim 20
Dependent Claim
7 words
1,7-bis(4-chlorophenylcarbamylguanidino)heptane and pharmacologically acceptable acid addition salts.
Claim 21
Dependent Claim
7 words
1,6-bis(2-chlorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 22
Dependent Claim
7 words
1,6-bis(2-chlorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 23
Dependent Claim
7 words
1,6-bis(3-chlorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 24
Dependent Claim
7 words
1,6-bis(3-chlorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 25
Dependent Claim
7 words
1,6-bis(4-fluorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 26
Dependent Claim
7 words
1,6-bis(4-fluorophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 27
Dependent Claim
7 words
1,6-bis(4-bromophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 28
Dependent Claim
7 words
1,6-bis(4-bromophenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 29
Dependent Claim
7 words
1.6-bis(3-trifluoromethylphenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 30
Dependent Claim
7 words
1.6-bis(3-trifluoromethylphenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 31
Dependent Claim
7 words
1,6-bis(phenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
Claim 32
Dependent Claim
7 words
1,6-bis(phenylcarbamylguanidino)hexane and pharmacologically acceptable acid addition salts.
References Cited (Backward Citations)
US2684924A
Cited
US3183230A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-09 | 1980-11-08 | 1981-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-09 | 1984-11-08 | 1985-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-09 | 1988-11-08 | 1989-05-10 | $7700.00 | Window Closed / Lapsed |