KR960010615A - Monocarbamate Compound Derived from 2-phenyl-1,3-propanediol - Google Patents

Monocarbamate Compound Derived from 2-phenyl-1,3-propanediol Download PDF

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KR960010615A
KR960010615A KR1019940023910A KR19940023910A KR960010615A KR 960010615 A KR960010615 A KR 960010615A KR 1019940023910 A KR1019940023910 A KR 1019940023910A KR 19940023910 A KR19940023910 A KR 19940023910A KR 960010615 A KR960010615 A KR 960010615A
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South Korea
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carbamate
acetoxy
phenylpropanol
phenyl
following formula
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KR1019940023910A
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Korean (ko)
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KR0150239B1 (en
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최용문
한동일
김형철
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조규향
주식회사 유공
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Priority to KR1019940023910A priority Critical patent/KR0150239B1/en
Application filed by 조규향, 주식회사 유공 filed Critical 조규향
Priority to EP95931455A priority patent/EP0730576A1/en
Priority to PCT/KR1995/000125 priority patent/WO1996009284A1/en
Priority to ES95931454T priority patent/ES2134491T3/en
Priority to US08/612,903 priority patent/US5849772A/en
Priority to CA002176960A priority patent/CA2176960C/en
Priority to CN95190934A priority patent/CN1071315C/en
Priority to EP95931454A priority patent/EP0730575B1/en
Priority to JP8510764A priority patent/JP2809883B2/en
Priority to DE69509745T priority patent/DE69509745T2/en
Priority to CA002176968A priority patent/CA2176968A1/en
Priority to JP8510765A priority patent/JP2809884B2/en
Priority to CN95190935A priority patent/CN1135751A/en
Priority to PCT/KR1995/000124 priority patent/WO1996009283A1/en
Publication of KR960010615A publication Critical patent/KR960010615A/en
Application granted granted Critical
Publication of KR0150239B1 publication Critical patent/KR0150239B1/en
Priority to CN001374621A priority patent/CN1216858C/en

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Abstract

본 발명은 2-페닐-1,3-프로판디올로 부터 유도되는 단일카바메이트를 화합물들에 관한 것으로서, 좀 더 상세하게는 3-아세톡시-2-페닐-프로판올 카바메이트, (S)-3-아세톡시-2-페닐-프로판올 카바메이트, (R)-3-아세톡시-2-페닐-프로판올 카바메이트, 2-페닐-1,3-프로판디올 단일카바메이트, (S)-2-페닐-1,3-프로판디올 단일카바메이트, (R)-2-페닐-1,3-프로판디올 단일카바메이트 6종에 관한 것이다.The present invention relates to compounds of a single carbamate derived from 2-phenyl-1,3-propanediol, more particularly 3-acetoxy-2-phenyl-propanol carbamate, (S) -3 -Acetoxy-2-phenyl-propanol carbamate, (R) -3-acetoxy-2-phenyl-propanol carbamate, 2-phenyl-1,3-propanediol single carbamate, (S) -2-phenyl It relates to 6 kinds of -1,3-propanediol single carbamate and (R) -2-phenyl-1,3-propanediol single carbamate.

본 발명에 따른 광학이성체는 중추신경계 질병, 예를 들어 신경성 근육통, 간질 및 뇌졸증의 치료 및 예방에 유용하다.The optical isomers according to the invention are useful for the treatment and prevention of central nervous system diseases such as neuromuscular pain, epilepsy and stroke.

Description

2-페닐-1,3-프로판디올로 부터 유도되는 단일 카바메이트 화합물Single carbamate compound derived from 2-phenyl-1,3-propanediol

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (24)

하기 식(I)로 표시되는 3-아세톡시-2-페닐프로판올 카바메이트.3-acetoxy-2-phenylpropanol carbamate represented by the following formula (I). 하기 식(II)로 표시되는 (S)-3-아세톡시-2-페닐프로판올 카바메이트.(S) -3-acetoxy-2-phenylpropanol carbamate represented by the following formula (II). 하기 식(III)로 표시되는 (R)-3-아세톡시-2-페닐프로판올 카바메이트.(R) -3-acetoxy-2-phenylpropanol carbamate represented by the following formula (III). 하기 식(IV)로 표시되는 2-페닐-1,3-프로판디올 단일 티오카바메이트.2-phenyl-1,3-propanediol single thiocarbamate represented by the following formula (IV). 하기 식(V)로 표시되는 (S)-2-페닐-1,3-프로판디올 단일 카바메이트.(S) -2-phenyl-1,3-propanediol single carbamate represented by the following formula (V). 하기 식(VI)로 표시되는 (R)-2-페닐-1,3-프로판디올 단일 카바메이트.(R) -2-phenyl-1,3-propanediol single carbamate represented by the following formula (VI). 하기 식(VII)의 (R)-3-아세톡시-2-페닐프로판올을 방향족 탄화수소와 할로겐화 탄화수소의 혼합용매를 사용하여, 아민계 염기의 존재하에서 포스겐으로 처리한 후 암모니아로 처리하여 하기 식(II)로 표시되는 (S)-3-아세톡시-2-페닐프로판올 카바메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 (S)-3-아세톡시-2-페닐프로판올 카바메이트 제조방법.(R) -3-acetoxy-2-phenylpropanol of the formula (VII) was treated with phosgene in the presence of an amine base using a mixed solvent of an aromatic hydrocarbon and a halogenated hydrocarbon, followed by treatment with ammonia. (S) -3-acetoxy-2-phenylpropanol carba characterized by preparing (S) -3-acetoxy-2-phenylpropanol carbamate represented by II) with high yield and high optical purity in a short time. Mate manufacturing method. 제7항에 있어서 상기 포스겐을 반응시킬 때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method according to claim 7, wherein the temperature at which the phosgene is reacted is maintained at -10 ° C to 10 ° C. 제7항에 있어서 상기 암모니아를 반응시킬때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method according to claim 7, wherein the temperature when reacting the ammonia is maintained at -10 ° C to 10 ° C. 하기 식(VIII)의 (S)-3-아세톡시-2-페닐프로판올을 방향족 탄화수소와 할로겐화 탄화수소의 혼합용매를 사용하여, 아민계 염기의 존재하에서 포스겐으로 처리한 후 암모니아로 처리하여 하기 식(III)로 표시되는 (R)-3-아세톡시-2-페닐프로판올 카바메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 (R)-3-아세톡시-2-페닐프로판올 카바메이트 제조방법.(S) -3-acetoxy-2-phenylpropanol of the following formula (VIII) was treated with phosgene in the presence of an amine base using a mixed solvent of an aromatic hydrocarbon and a halogenated hydrocarbon, followed by treatment with ammonia. (R) -3-acetoxy-2-phenylpropanol carba characterized by preparing (R) -3-acetoxy-2-phenylpropanol carbamate represented by III) in high yield and high optical purity in a short time. Mate manufacturing method. 제10항에 있어서 상기 포스겐을 반응시킬 때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method according to claim 10, wherein the temperature at which the phosgene is reacted is maintained at -10 ° C to 10 ° C. 제10항에 있어서 상기 암모니아를 반응시킬때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method of claim 10, wherein the temperature when reacting the ammonia is maintained at -10 ° C to 10 ° C. 하기 식(IX)의 3-아세톡시-2-페닐프로판올을 방향족 탄화수소와 할로겐화 탄화수소의 혼합용매를 사용하여, 아민계 염기의 존재하에서 포스겐으로 처리한 후 암모니아로 처리하여 하기 식(I)로 표시되는 3-아세톡시-2-페닐프로판올 카바메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 3-아세톡시-2-페닐프로판올 카바메이트 제조방법.3-acetoxy-2-phenylpropanol of the formula (IX) was treated with phosgene in the presence of an amine base using a mixed solvent of an aromatic hydrocarbon and a halogenated hydrocarbon, and then treated with ammonia to represent the following formula (I): The 3-acetoxy-2-phenylpropanol carbamate is prepared in a short time in high yield and high optical purity, characterized in that 3-acetoxy-2-phenylpropanol carbamate production method. 제13항에 있어서 상기 포스겐을 반응시킬 때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method according to claim 13, wherein the temperature at which the phosgene is reacted is maintained at -10 ° C to 10 ° C. 제13항에 있어서 상기 암모니아를 반응시킬때의 온도는 -10℃∼10℃가 유지됨을 특징으로 하는 방법.The method according to claim 13, wherein the temperature at which the ammonia is reacted is maintained at -10 ° C to 10 ° C. 하기 식(II)의 (S)-3-아세톡시-2-페닐프로판올 카바메이트를 완충용액하에서 효소로 가수분해 시켜서 하기 식(V)로 표시되는 (S)-2-페닐-1,3-프로판디올 단일카바메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 (S)-2-페닐-1,3-프로판디올 단일카바메이트의 제조방법.(S) -2-phenyl-1,3- represented by the following formula (V) by hydrolyzing (S) -3-acetoxy-2-phenylpropanol carbamate of formula (II) with an enzyme in a buffer solution A process for producing (S) -2-phenyl-1,3-propanediol single carbamate, comprising producing propanediol single carbamate in a short time with high yield and high optical purity. 제16항에 있어서 상기 효소가 돼지의 췌장에서 추출한 리파제(PPL), 칸디다 리파제(CCL), 아스파질러스 리파제(ANL), 슈도모나스 리파제(PSL) 또는 돼지의 간에서 추출 한 에스테라제(PLE)인 것을 특징으로 하는 방법.17. The enzyme according to claim 16, wherein the enzyme is lipase (PPL), Candida lipase (CCL), Asparagus lipase (ANL), Pseudomonas lipase (PSL), or esterase (PLE) extracted from pig liver. Method characterized in that. 제16항에 있어서 상기 반응온도는 0℃∼30℃가 유지됨을 특징으로 하는 방법.The method of claim 16, wherein the reaction temperature is maintained at 0 ℃ to 30 ℃. 제16항에 있어서 상기 사용된 완충용액의 pH가 7로 유지됨을 특징으로 하는 방법The method of claim 16, wherein the pH of the used buffer solution is maintained at 7. 하기 식(III)의 (R)-3-아세톡시-2-페닐프로판올 카바메이트를 완충용액하에서 효소로 가수분해 시켜서 하기 식(VI)로 표시되는 (R)-2-페닐-1,3-프로판디올 단일카바메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 (R)-2-페닐-1,3-프로판디올 단일카바메이트의 제조방법(R) -2-phenyl-1,3- represented by the following formula (VI) by hydrolyzing (R) -3-acetoxy-2-phenylpropanol carbamate of formula (III) with an enzyme in a buffer solution Method for preparing (R) -2-phenyl-1,3-propanediol single carbamate, characterized in that the propanediol single carbamate is prepared in a short time with high yield and high optical purity 제20항에 있어서 상기 효소가 돼지의 췌장에서 추출한 리파제(PPL), 칸디다 리파제(CCL), 아스파질러스 리파제(ANL), 슈도모나스 리파제(PSL) 또는 돼지의 간에서 추출 한 에스테라제(PLE)인 것을 특징으로 하는 방법The enzyme according to claim 20, wherein the enzyme is lipase (PPL), Candida lipase (CCL), Asparagus lipase (ANL), Pseudomonas lipase (PSL), or esterase (PLE) extracted from pig liver. Method characterized by 제20항에 있어서 상기 반응온도는 0℃∼30℃가 유지됨을 특징으로 하는 방법.The method of claim 20, wherein the reaction temperature is maintained at 0 ℃ to 30 ℃. 제20항에 있어서 상기 사용된 완충용액의 pH가 7로 유지됨을 특징으로 하는 방법.21. The method of claim 20, wherein the pH of the used buffer is maintained at 7. 하기 식(I)의 3-아세톡시-2-페닐프로판올 카바메이트를 가성소다 수용액과 에탄올의 혼합용액하에서 가수분해 시켜서 하기 식(IV)로 표시되는 2-페닐-1,3-프로판디올 단일카바메이트 라세메이트를 단시간내에 고수율과 높은 광학적 순도로 제조하는 것을 특징으로 하는 2-페닐-1,3-프로판디올 단일카바메이트의 제조방법.2-phenyl-1,3-propanediol monocarbamide represented by the following formula (IV) by hydrolyzing 3-acetoxy-2-phenylpropanol carbamate of formula (I) in a mixed solution of caustic soda solution and ethanol A method for producing 2-phenyl-1,3-propanediol single carbamate, characterized in that mate racemate is prepared in a short time with high yield and high optical purity. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940023910A 1994-09-22 1994-09-22 Monocarbamate Compound Derived from 2-phenyl-1,3-propanediol KR0150239B1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
KR1019940023910A KR0150239B1 (en) 1994-09-22 1994-09-22 Monocarbamate Compound Derived from 2-phenyl-1,3-propanediol
CA002176968A CA2176968A1 (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
ES95931454T ES2134491T3 (en) 1994-09-22 1995-09-21 NEW CARBAMATE COMPOUNDS AND PROCEDURES FOR ITS PREPARATION.
US08/612,903 US5849772A (en) 1994-09-22 1995-09-21 Carbamate compounds and processes for preparing the same
CA002176960A CA2176960C (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
CN95190934A CN1071315C (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
EP95931455A EP0730576A1 (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
JP8510764A JP2809883B2 (en) 1994-09-22 1995-09-21 Novel carbamate compound and method for producing the same
DE69509745T DE69509745T2 (en) 1994-09-22 1995-09-21 NEW CARBAMATE COMPOUNDS AND METHOD FOR THEIR PRODUCTION
PCT/KR1995/000125 WO1996009284A1 (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
JP8510765A JP2809884B2 (en) 1994-09-22 1995-09-21 Novel carbamate compound and method for producing the same
CN95190935A CN1135751A (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
PCT/KR1995/000124 WO1996009283A1 (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
EP95931454A EP0730575B1 (en) 1994-09-22 1995-09-21 Novel carbamate compounds and processes for preparing the same
CN001374621A CN1216858C (en) 1994-09-22 2000-12-20 Carbamate compound and its prep.

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Application Number Priority Date Filing Date Title
KR1019940023910A KR0150239B1 (en) 1994-09-22 1994-09-22 Monocarbamate Compound Derived from 2-phenyl-1,3-propanediol

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KR0150239B1 KR0150239B1 (en) 1998-10-15

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