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US4139619A
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US
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6-Amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, topical compositions and process for hair growth
Assignee: Pharmacia and Upjohn Co
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Filing: 1977-08-19
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Granted: 1979-02-13
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Expires: 1997-08-19
Abstract
Abstract This invention relates to a process for stimulating the growth of mammalian hair comprising the application to mammalian skin of a compound of the formula: <IMAGE> Formula I wherein R1 is a moiety selected from the group consisting of moieties of the formula <IMAGE> wherein R3 and R4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R3 and R4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy wherein R2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof in association with a topical pharmaceutical carrier.
Inventors
- 👤 Charles A. Chidsey, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 19:36
CPC Classifications
A; A61; A61Q; A61Q7/00; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/494; A61K8/4953
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
169 words
A topical composition for application to mammalian skin comprising an effective amount of a compound of the formula: ##STR3## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR4## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralky, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier selected from the group consisting of ointments, lotions, pastes, jellies, sprays, and aerosols.
Claim 2
Dependent Claim
169 words
A topical composition for application to mammalian skin comprising an effective amount of a compound of the formula: ##STR3## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR4## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralky, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier selected from the group consisting of ointments, lotions, pastes, jellies, sprays, and aerosols.
Claim 3
Dependent Claim
21 words
The composition of claim 1 wherein the concentration of the compound is from about 0.1% to about 20% of the composition.
Claim 4
Dependent Claim
22 words
The composition of claim 1 wherein the compound is 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine in the form of the free base or acid addition salts thereof.
Claim 5
Dependent Claim
173 words
A process for increasing the rate of terminal hair growth in mammalian species comprising the application to mammalian skin at the locale of terminal hair of an effective amount of a compound of the formula: ##STR5## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR6## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier.
Claim 6
Dependent Claim
173 words
A process for increasing the rate of terminal hair growth in mammalian species comprising the application to mammalian skin at the locale of terminal hair of an effective amount of a compound of the formula: ##STR5## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR6## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier.
Claim 7
Dependent Claim
22 words
The process of claim 4 wherein the concentration of the compound applied is from about 0.1% to about 20% of the composition.
Claim 8
Dependent Claim
10 words
The process of claim 4 wherein compound applied is 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine.
Claim 9
Dependent Claim
173 words
A process for the conversion of vellus hair to growth as terminal hair comprising the application to mammalian skin at the locale of vellous hair of an effective amount of a compound of the formula: ##STR7## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR8## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier.
Claim 10
Dependent Claim
173 words
A process for the conversion of vellus hair to growth as terminal hair comprising the application to mammalian skin at the locale of vellous hair of an effective amount of a compound of the formula: ##STR7## wherein R 1 is a moiety selected from the group consisting of moieties of the formula ##STR8## wherein R 3 and R 4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R 3 and R 4 may be a heterocyclic moiety selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexahydroazepinyl, heptamethylenimino, octamethylenimino, morpholino, and 4-lower-alkylpiperazinyl, each of said heterocyclic moieties having attached as substituents on the carbon atoms 0-3 lower alkyl groups, hydroxy or alkoxy, and wherein R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower cycloalkyl, lower aryl, lower aralkyl, lower alkaryl, lower alkaralkyl, lower alkoxyaralkyl, and lower haloaralkyl and the pharmacologically acceptable acid addition salts thereof, in association with a topical pharmaceutical carrier.
Claim 11
Dependent Claim
22 words
The process of claim 7 wherein the concentration of the compound applied is from about 0.1% to about 20% of the composition.
Claim 12
Dependent Claim
11 words
The process of claim 7 wherein the compound applied is 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine.
References Cited (Backward Citations)
US3461461A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-12 | 1982-08-14 | 1983-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-12 | 1986-08-14 | 1987-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-12 | 1990-08-14 | 1991-02-13 | $7700.00 | Window Closed / Lapsed |