KR960700255A - 광학활성 β-아미노알콕시보란 복합체[OPTICALLY ACTIVE β-AMINOALKOXYBORANE CONPLEX] - Google Patents
광학활성 β-아미노알콕시보란 복합체[OPTICALLY ACTIVE β-AMINOALKOXYBORANE CONPLEX]Info
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- KR960700255A KR960700255A KR1019950702983A KR19950702983A KR960700255A KR 960700255 A KR960700255 A KR 960700255A KR 1019950702983 A KR1019950702983 A KR 1019950702983A KR 19950702983 A KR19950702983 A KR 19950702983A KR 960700255 A KR960700255 A KR 960700255A
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- alkyl
- optically active
- formula
- hydrogen
- aralkyl
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
- 239000001257 hydrogen Substances 0.000 claims abstract 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical group 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 229920000642 polymer Polymers 0.000 claims abstract 3
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000001931 aliphatic group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- -1 methoxy , Methoxymethyl Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 239000011575 calcium Chemical group 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052744 lithium Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000011591 potassium Chemical group 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 239000011734 sodium Chemical group 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101150046432 Tril gene Proteins 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910000085 borane Inorganic materials 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C07F5/022—Boron compounds without C-boron linkages
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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Abstract
본 발명은 식(Ⅰ)의 광학활성 β-아미노알콕시보란 복합체에 관한 것이다:
(여기서, R1은 C1-C8알킬, C3-C7시클로아킬, C7-C11아르알킬 혹은 C6-C10아릴이고, R2은수소, C1-C8알킬, C3-C7시클로알킬, C7-C11아르알킬이며, 또는 R1과 R2가 합쳐서 (CH2)n(여기서 n은 3 또는 4임)을 이루며, Ar은 나프틸, 안트릴 혹은 페난트릴인데, 할로겐, 니트로, C1-C6알킬, C3-C7시클로알킬, C2-C6알케닐, C2-C6알키닐, C7-C1아르알킬, C6-C10아릴, C1-C6알콜시 및 스티렌 중합체 치환기들로 이루어지는 군에서 1~3개의 치환기로 치환될 수 있다)
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 식(Ⅰ)의 광학활성 β-아미노알콕시보란 복합체:(Ⅰ)(여기서, R1은 C1-C8알킬, C3-C7시클로아킬, C7-C11아르알킬 혹은 C6-C10아릴이고, R2은수소, C1-C8알킬, C3-C7시클로알킬, C7-C11아르알킬이며, 또는 R1과 R2가 합쳐서 (CH2)n(여기서 n은 3 또는 4임)을 이루며, Ar은 나프틸, 안트릴 혹은 페난트릴인데, 할로겐, 니트로, C1-C6알킬, C3-C7시클로알킬, C2-C6알케닐, C2-C6알키닐, C7-C1아르알킬, C6-C10아릴, C1-C6알콜시 및 스티렌 중합체 치환기들로 이루어지는 군에서 1~3개의 치환기로 치환될 수 있다)
- 식(Ⅲ)의 광학활성 β-아미노알코올 화합물:(Ⅱ)(여기서, R1은 C1-C8알킬, C3-C7시클로아킬, C7-C11아르알킬 혹은 C6-C10아릴이고, R2은수소, C1-C8알킬, 혹은 C7-C11아르알킬이며, 또는 R1과 R2가 합쳐서 (CH2)n(여기서 n은 3 또는 4임)을 이루며, Ar은 나프틸, 안트릴 혹은 페난트릴인데, 할로겐, 니트로, C1-C6알킬, C3-C7시클로알킬, C2-C6알케닐, C2-C6알키닐, C7-C1아르알킬, C6-C10아릴, C1-C6알콜시 및 스티렌 중합체 치환기들로 이루어지는 군에서 1~3개의 치환기로 치환될 수 있다)
- 제2항에서 정의한 바의 식(Ⅱ)의 광학활성 β-아미노알코올 화합물을 보란시약으로 반응시키는것으로 구성되는, 제1항에서 정의한 바의 식(Ⅰ)을 갖는 광학활성 β-아미노알콕시보란 복합체의 제조방법.
- 제1항에서 정의한 바의 광학활성 β-아미노알콕시보란 복합체를 사용하여 식(Ⅲ):(Ⅲ)(여기서 R3과 R4는아래에 정의한 바와 같다)의 카르보닐 화합물을 환원시키는 것으로 구성되는 식(Ⅳ):(Ⅳ)(여기서, R3과 R4는 서로 다르고, C1-C8알킬, C3-C7시클로아킬, C2-C10알키닐, C3-C10시클로알케닐, C7-C10아르알킬킬, 및 C6-C14아릴을 나타내거나, 또는 R3과 R4가 합쳐서 고리모양의 구조를 이루며, *는 광학활성중심을 나타낸다)의 광학활성 화합물의 제조방법.
- 제1항에서 정의한 바의 광학활성 β-아미노알콕시보란 복합체를 사용하여 식(Ⅴ):(Ⅴ)(여기서 R5, R6및 X는 아래에 정의한 바와 같고, 서로 독립적인 Y와 Z의 각각은 Y와 Z가 동시에 -CH(OH)-가 아니라면 -CO- 혹은 -CH(OH)-이다)의 카르보닐 화합물을 환원시키는 것으로 구성되는 식(Ⅵ):(Ⅵ)[여기서 X는 화학결합이고, R5는 CHO, CH(OR9)(OR10)(여기서 서로 독립적인 R9와 R10의 각각은 수소이거나 C1-C3알킬이며, 또는 R9와 R10이 합쳐서 C2-C5알킬렌을 이룸), CH2OR11(여기서 R11은 수소, C1-C5알킬, 메틸이나 메톡시로 치환될 수 있는 벤질, 트리틸, 테트라히드로피라닐, 메톡시메틸, 트리메틸실릴, 디메틸-tert-부틸실릴 혹은 디페닐-tert-부틸실릴임) CH2R12는 플루오로, 클로로, 브로모 혹은 요오도임), CN, CO2R13(여기서, R13은 수소, C1-C3알킬, 혹은 메틸이나 메톡시로 치환돌 수 있는 벤질임), 혹은 CONR14R15(여기서 서로 독립적인 R14와 R15의 각각은 수소, C1-C3알킬, 벤질, 1-메틸벤질, 혹은 메틸이나 메톡시로 치환될 수 있는 페닐)이며, X가 -CH2- -CH2CH2- -CH=CH-, -(CH3)C=CH-, -CH=C(CH3)--C≡C-인 경우, R5는수소, 트리알킬실릴, 탄소고리 지방족 기, 탄소고리 방향족 기, 헤테로고리 방향족 기, 축합 헤테로고리 방향족 기, 사슬 불포화 지방족 기 혹은 고리 불포화지방족 기이며, R6은 히드록실, C1-C10알콕시, OM(여기서 M은 리튬, 나트륨, 칼륨, 칼슘, NHR'3(여기서 R'은 수소, C1-C3알킬, C3-C7시클로알킬, C2-C5알케닐, 페닐 혹은 벤질임)혹은 C6-C7아미노이고, *는 2개의 중심이 서로에 대해 syn입체형태(conformation)를 취하는 것이라면 광학활성 중심이다]의 화합물의 제조방법.
- 제1항에서 정의한 바의 광학활성 β-아미노알콕시보란 복합체를 사용하여 식(Ⅴ-1)(Ⅴ-1)(여기서 R6,R7및 R8은 아래에 정의한 바와 같다)의 1,3-디카르보닐 화합물을 환원시키는 것으로 구성되는, 식(Ⅵ-1)(Ⅵ-1)[여기서, R6는 히드록실, C1-C10알콕시, OM(여기서 M은 리튬, 나트륨, 칼륨, 칼슘, NHR'3(여기서 R'은 수소, C1-C3알킬, C3-C7시클로알킬, C2-C5알케닐, 페닐 혹은 벤질임) 혹은 C6-C7아미노이고, R7은 C1-C7알킬 혹은 브로모로 치환될 수 있음)이며, *는 2개의 중심이 서로에 대해 syn 입체형태를 취하는 것이라면 광학활성 중심이다]의 화합물의 제조방법.
- 제1항에서 정의한 바의 광학활성 β-아미노알콕시보란 복합체를 사용하여 식(Ⅴ-2)(Ⅴ-2)(여기서 R5,R6은 아래에 정의한 바와 같다)의 1,3-디카르보닐 화합물을 환원시키는 것으로 구성되는, 식(Ⅵ-2)(Ⅵ-2)[여기서, R5는 수소, 트리알킬실릴, 탄소고리 지방족 기, 탄소고리 방향족 기, 헤테로고리 방향족 기, 축합 헤테로고리 방향족 기, 사슬불포화 지방족 기 혹은 고리 불포화 지방족 기이고,R6은 히드록실, C1-C10알콕시, OM(여기서 M은 리튬, 나트륨, 칼륨, 칼슘, NHR'3(여기서 R'은 수소, C1-C3알킬, C3-C7시클로알킬, C2-C5알케닐, 페닐 혹은 벤질임) 혹은 C0-C7아미노이고, *는 2개의 중심이 서로에 대해 syn 입체형태를 취하는 것이라면 광학활성 중심을 나타낸다]의 광학활성 1,3-syn-디올 화합물의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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JP782793 | 1993-01-20 | ||
JP93-7827 | 1993-01-20 | ||
JP93-66825 | 1993-03-25 | ||
JP6682593 | 1993-03-25 | ||
PCT/JP1994/000056 WO1994017079A1 (en) | 1993-01-20 | 1994-01-17 | OPTICALLY ACTIVE β-AMINOALKOXYBORANE COMPLEX |
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KR960700255A true KR960700255A (ko) | 1996-01-19 |
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US (6) | US5663348A (ko) |
EP (1) | EP0680484B1 (ko) |
JP (1) | JPH06329679A (ko) |
KR (1) | KR960700255A (ko) |
CN (2) | CN1047173C (ko) |
AT (1) | ATE169921T1 (ko) |
AU (1) | AU678427B2 (ko) |
CA (1) | CA2153695A1 (ko) |
CZ (1) | CZ185295A3 (ko) |
DE (1) | DE69412588T2 (ko) |
HU (1) | HU217182B (ko) |
IL (2) | IL108387A (ko) |
MX (1) | MX9400566A (ko) |
NO (2) | NO305602B1 (ko) |
NZ (1) | NZ259585A (ko) |
RU (1) | RU2126412C1 (ko) |
TW (1) | TW383309B (ko) |
WO (1) | WO1994017079A1 (ko) |
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NZ249302A (en) * | 1992-05-14 | 1996-11-26 | Pfizer | 4,5-diphenyl-1,3,2-oxazaborolidine derivatives and their use as catalysts in reduction of ketones to chiral alcohols |
JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
EP0713848B1 (en) * | 1994-10-28 | 1999-09-08 | SUMIKA FINE CHEMICALS Company, Limited | Process for producing optically active carbinols |
US6262283B1 (en) * | 1996-12-06 | 2001-07-17 | Magainin Pharmaceuticals Inc. | Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds |
EP1274718B1 (en) | 2000-04-12 | 2006-10-18 | Genaera Corporation | A process for the preparation of 7.alpha.-hydroxy 3-aminosubstituted sterols using intermediates with an unprotected 7.alpha.-hydroxy group |
US6509472B2 (en) * | 2000-09-11 | 2003-01-21 | Schering Corporation | 4-Cyclohexyl-1,3,2-oxazaborolidine chiral accessories |
US7173073B2 (en) * | 2002-01-14 | 2007-02-06 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices containing heterocyclic compounds and methods for their production |
US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
TWI504394B (zh) | 2011-04-29 | 2015-10-21 | Ind Tech Res Inst | 安托芬之製備方法 |
CA2837774A1 (en) | 2013-12-20 | 2015-06-20 | Heiner Ophardt | Piston pump with vacuum relief |
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CA772624A (en) * | 1967-11-28 | F. Crowther Albert | Substituted oxazolidines | |
US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
JPS57146786A (en) * | 1981-03-09 | 1982-09-10 | Kyowa Hakko Kogyo Co Ltd | Optically active borane compound and preparation of optically active compound using the same |
GB8313571D0 (en) * | 1983-05-17 | 1983-06-22 | Wellcome Found | Chemical compounds |
US4719055A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Phenanthrene derivatives |
JPS6118790A (ja) * | 1984-07-05 | 1986-01-27 | Sumitomo Chem Co Ltd | 光学活性ボラン錯体およびその製造法 |
JPH0778052B2 (ja) * | 1986-11-28 | 1995-08-23 | 富士薬品工業株式会社 | Dl−パントラクトンの光学分割法 |
US4897490A (en) * | 1987-02-25 | 1990-01-30 | Bristol-Meyers Company | Antihypercholesterolemic tetrazole compounds |
US5254692A (en) * | 1990-04-06 | 1993-10-19 | Bayer Aktiengesellschaft | 2,6-dialkyl-4-(benzothiazol- or benzoxazol-7-yl)-1,4-dihydropyridines |
US5157129A (en) * | 1990-04-18 | 1992-10-20 | Merck & Co., Inc. | Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide |
NZ249302A (en) * | 1992-05-14 | 1996-11-26 | Pfizer | 4,5-diphenyl-1,3,2-oxazaborolidine derivatives and their use as catalysts in reduction of ketones to chiral alcohols |
JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
ES2108484T3 (es) * | 1993-11-30 | 1997-12-16 | Pfizer | Procedimiento para la preparacion de una tetralona asimetrica. |
US5763688A (en) * | 1994-12-07 | 1998-06-09 | Research Development Corporation Of Japan | Method for producing an alcohol |
-
1993
- 1993-12-27 JP JP5332498A patent/JPH06329679A/ja active Pending
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1994
- 1994-01-14 TW TW083100279A patent/TW383309B/zh not_active IP Right Cessation
- 1994-01-17 WO PCT/JP1994/000056 patent/WO1994017079A1/en not_active Application Discontinuation
- 1994-01-17 NZ NZ259585A patent/NZ259585A/en unknown
- 1994-01-17 DE DE69412588T patent/DE69412588T2/de not_active Expired - Fee Related
- 1994-01-17 EP EP94904332A patent/EP0680484B1/en not_active Expired - Lifetime
- 1994-01-17 US US08/481,505 patent/US5663348A/en not_active Expired - Fee Related
- 1994-01-17 CZ CZ951852A patent/CZ185295A3/cs unknown
- 1994-01-17 AT AT94904332T patent/ATE169921T1/de not_active IP Right Cessation
- 1994-01-17 CA CA002153695A patent/CA2153695A1/en not_active Abandoned
- 1994-01-17 HU HU9502184A patent/HU217182B/hu not_active IP Right Cessation
- 1994-01-17 CN CN94190966A patent/CN1047173C/zh not_active Expired - Fee Related
- 1994-01-17 RU RU95115845A patent/RU2126412C1/ru active
- 1994-01-17 KR KR1019950702983A patent/KR960700255A/ko not_active Application Discontinuation
- 1994-01-17 AU AU58431/94A patent/AU678427B2/en not_active Ceased
- 1994-01-20 IL IL10838794A patent/IL108387A/xx not_active IP Right Cessation
- 1994-01-20 MX MX9400566A patent/MX9400566A/es not_active Application Discontinuation
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1995
- 1995-07-19 NO NO952870A patent/NO305602B1/no unknown
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1996
- 1996-11-26 IL IL11969696A patent/IL119696A0/xx unknown
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1997
- 1997-01-07 US US08/779,621 patent/US5767277A/en not_active Expired - Fee Related
- 1997-04-29 US US08/848,172 patent/US5786485A/en not_active Expired - Fee Related
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- 1997-04-29 US US08/848,173 patent/US5739347A/en not_active Expired - Fee Related
- 1997-04-29 US US08/848,174 patent/US5852221A/en not_active Expired - Fee Related
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1998
- 1998-10-28 NO NO985016A patent/NO985016D0/no not_active Application Discontinuation
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1999
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