IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0548606
(1975-02-10)
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발명자
/ 주소 |
- Bodor Nicolae S. (Lawrence KS) Yuan Sun-Shine (Lawrence KS)
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출원인 / 주소 |
- Interx Research Corporation (Lawrence KS 02)
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인용정보 |
피인용 횟수 :
5 인용 특허 :
0 |
초록
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Optically and therapeutically active compounds of the formula: WHEREIN R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C1-C5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an OR3
Optically and therapeutically active compounds of the formula: WHEREIN R represents a member selected from the group consisting of a straight or branched alkyl group of from one to twenty carbon atoms (C1-C5 being preferred), an ethoxycarbonyl group, a benzyloxycarbonyl group, a phenyl group, an OR3 �3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion, are prepared using optically active m-hydroxy-aa
대표청구항
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A method for preparing an optically and therapeutically active (m-acyloxy-a3 �3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid add
A method for preparing an optically and therapeutically active (m-acyloxy-a3 �3 is a member selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group, and a 2-, 3-, or 4-pyridyl group, or the HX salts thereof, wherein X represents a pharmaceutically acceptable acid addition salt anion which consists essentially of 1. reacting optically active phenylephrine with an excess of a carbonyl compound of the formula: R1-CO-R2, wherein R1 and R2 which can be the same or different and represent a member selected from the group consisting of a hydrogen atom, a C1-C10 alkyl group, and a di(C1-C2)alkylamino(C1-C10)alkyl group, or wherein R1 and R2 together with the carbonyl group to which they are attached can form a member selected from the group consisting of a C5-C7 cycloalkanone group and a substituted or unsubstituted N- or O-heterocyclic (C5-C7) alkanone group, wherein said substituent is a C1-C2 alkyl group, either in the presence of a dehydrating agent selected from the group consisting of an alkaline earth metal carbide, a molecular sieve of from 4 to 5 A, calcium chloride, magnesium sulfate, and sodium sulfate, or in the presence of a conventional inert aromatic hydrocarbon solvent plus an organic or inorganic acid catalyst to eliminate the water formed as an azeotropic mixture, said step being carried out at a temperature of from 20°to 140°C, standard pressure, and for a period of time ranging from 2°to 2 to 48 hours, whereby the intermediate; wherein R1 and R2 are defined as above is formed; 2. reacting the intermediate of step (1) with a member selected from the group consisting of an M-hydroxide, an M-hydride, and an M-alkoxide, wherein M represents a member selected from the group consisting of an alkali earth metal, an alkaline earth metal and thallium in the presence of an inert organic solvent selected from the group consisting of an aliphatic hydrocarbon solvent or from five to 10 carbon atoms, an aromatic hydrocarbon solvent, and C1-C4 aliphatic alcohol, a conventional ether and dimethylformamide, said step being carried out at room temperature, standard pressure, and for a period of time ranging from 1 to 24 hours, whereby the intermediate: wherein M, R1, and R2 are defined above is formed; 3. reacting the intermediate of step (2) with a stoichiometric amOunt of an acyl halide of the formula: R-CO-Y, wherein R is defined as above and Y represents a halogen atom in the presence of an inert organic solvent selected from the group consisting of an aliphatic hydrocarbon solvent of from five to 10 carbon atoms, an aromatic hydrocarbon solvent, methanol, propanol, butanol, a conventional ether, and dimethylformamide, said step being carried out at room temperature, standard pressure, and for a period of time ranging from 1 to 24 hours, whereby the intermediate: wherein R, R1, and R2 are defined as above is formed; and 4. cleaving the R1-CO-R2 moiety of the intermediate from step (3) in an organic inert solvent selected from the group consisting of an aliphatic hydrocarbon solvent of from five to ten carbon atoms, an aromatic hydrocarbon solvent, a C1-C4 aliphatic alcohol, a conventional ether, and dimethyl formamide and further in the presence of a stoichiometric or excess amount of water and a catalytic amount of an HX acid, wherein X is defined as above, said step being carried out at a temperature of from 20°to 100°C, standard pressure, and for a period of time of from 1 to 24 hours, whereby the free base of formula (I) is obtained.
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