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Claims for Patent: 4,139,619

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Claims for Patent: 4,139,619

Title: 6-Amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, topical compositions and process for hair growth
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: ##STR1## wherein R.sub.1 is a moiety selected from the group consisting of moieties of the formula ##STR2## wherein R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R.sub.3 and R.sub.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 wherein R.sub.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.
Inventor(s): Chidsey, III; Charles A. (Denver, CO)
Assignee: The Upjohn Company (Kalmazoo, MI)
Application Number:05/826,180
Patent Claims: 1. A topical composition for application to mammalian skin comprising an effective amount of a compound of the formula: ##STR3## wherein R.sub.1 is a moiety selected from the group consisting of moieties of the formula ##STR4## wherein R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralky, and lower cycloalkyl, and taken together R.sub.3 and R.sub.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.sub.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.

2. The composition of claim 1 wherein the concentration of the compound is from about 0.1% to about 20% of the composition.

3. 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.

4. 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.sub.1 is a moiety selected from the group consisting of moieties of the formula ##STR6## wherein R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R.sub.3 and R.sub.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.sub.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.

5. The process of claim 4 wherein the concentration of the compound applied is from about 0.1% to about 20% of the composition.

6. The process of claim 4 wherein compound applied is 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine.

7. 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.sub.1 is a moiety selected from the group consisting of moieties of the formula ##STR8## wherein R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower aralkyl, and lower cycloalkyl, and taken together R.sub.3 and R.sub.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.sub.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.

8. The process of claim 7 wherein the concentration of the compound applied is from about 0.1% to about 20% of the composition.

9. The process of claim 7 wherein the compound applied is 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine.
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