KR970042525A - 아미노 알콜 유도체 및 이의 제조방법 - Google Patents
아미노 알콜 유도체 및 이의 제조방법 Download PDFInfo
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- KR970042525A KR970042525A KR1019960064982A KR19960064982A KR970042525A KR 970042525 A KR970042525 A KR 970042525A KR 1019960064982 A KR1019960064982 A KR 1019960064982A KR 19960064982 A KR19960064982 A KR 19960064982A KR 970042525 A KR970042525 A KR 970042525A
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- 150000001414 amino alcohols Chemical class 0.000 title claims abstract 19
- 238000002360 preparation method Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract 5
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000001412 amines Chemical class 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 230000002194 synthesizing effect Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- -1 piperazino group Chemical group 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000003277 amino group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical class [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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- 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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- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- 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
- C07C215/04—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 saturated
- C07C215/06—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 saturated and acyclic
- C07C215/18—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 saturated and acyclic with hydroxy groups and at least two amino groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- 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
- C07D207/10—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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Abstract
본 발명은 (A) 화학식 1의 아미노프로판올 유도체를 화학식 5의 아민과 반응시켜 화학식 2의 아미노 알콜 유도체를 합성하는 단계; (B) 상기 단계 (A)의 화학식 2의 아미노 알콜 유도체로부터 P1을 제거하여 화학식 3의 아미노 알콜 유도체를 합성하는 단계; (C) 상기 단계 (B)의 화학식 3의 아미노 알콜 유도체를 화학식 6 또는 이의 반응성 유도체와 반응시켜 화학식 4의 2-아실아미노 알콜 유도체를 제조하는 단계를 포함하는, 2-아실아미노 알콜 유도체의 제조 방법에 관한 것이다. 화학식 1 : Y-CH2-C*H(NHP1)-C*H(OH)-R1, 화학식 2 : R2-CH2-C*H(NHP1)-C*H(OH)-R1, 화학식 3 : R2-CH2-C*H(NH2)-C*H(OH)-R1, 화학식 4 : R2-CH2-C*H(NHCOR11)-C*H(OH)-R1, 화학식 5 : R2H, 화학식 6 : R11COOH ; 상기식에서, *는 비대칭 탄소 원자이고, P1, R1, R2및 R11은 명세서에서 정의한 바와 같다. 또한 본 발명은 아미노 그룹-보호된 2-아미노프로판을 유도체로부터 여러 단계를 통하여 아실아미노 그룹에 있는 알콜 유도체를 제조하는 방법, 빛 알콜 유도체를 제조하기 위한 방법에서 중간체로써 유용한 신규의 아미노 알콜에 관한 것이다.
Description
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Claims (12)
- (A) 화학식 1의 아미노프로판올 유도체를 화학식 5의 아민과 반응시켜 화학식 2의 아미노 알콜 유도체를 합성하는 단계; (B) 상기 단계 (A)의 화학식 2의 아미노 알콜 유도체로부터 P1을 제거하여 화학식 3의 아미노 알콜 유도체를 합성하는 단계; (C) 상기 단계 (B)의 화학식 3의 아미노 알콜 유도체를 화학식 6 또는 이의 반응성 유도체와 반응시켜 화학식 4의 2-아실아미노 알콜 유도체를 제조하는 단계를 포함하는, 2-아실아미노 알콜 유도체의 제조 방법. 화학식 1 : Y-CH2-C*H(NHP1)-C*H(OH)-R1, 화학식 2 : R2-CH2-C*H(NHP1)-C|*H(OH)-R1, 화학식 3 : R2-CH2-C*H(NH2)-C*H(OH)-R1, 화학식 4 : R2-CH2-C*H(NHCOR11)-C*H(OH)-R1, 화학식 5 : R2H, 화학식 6 : R11COOH ; 상기식에서, *는 비대칭 탄소 원자이고, P1은 알킬그룹 또는 아미노-보호 그룹이며, Y는 이탈 그룹이고, R1은 알킬 그룹, 사이클로알킬 그룹 또는 아릴 그룹이며, R2는 화학식으로 나타내고, R3및 R4는 동일하거나 상이하며 각각 수소원자, 저급 알킬 그룹, 저급 알케닐 그룹, 하이드록시-저급-알킬 그룹, 저급 알콕시알킬 그룹, 아미노-저급 -알킬 그룹, 사이클로알킬 그룹, 하이드록시사이클로알킬 그룹, 아르알킬 그룹, 또는 저급 알킬 그룹으로 치환될 수 있는 피페라지노 그룹이며; R5는 수소 원자, 또는 동일하거나 상이하며 하디드록실 그룹, 저급 알킬 그룹, 저급 알콕실 그룹, 하이드록시-저급-알킬 그룹, 카복실 그룹, (저급 알콕실)카보닐 그룹, 아르알킬 그룹, 피페리디노 그룹, 아실옥시 그룹, 아니노 그룹 및 아미노-저급 알킬 그룹으로부터 선택된 하나이상의 치환체이고; R6은 수소 원자, 또는 동일하거나 상이하며 상기 R5에서 정의한 바와 같은 치환체로부터 선택된 하나 이상의 전환체이고; R7은 산소 원자에 의해 불연속될 수 있는 저급 알킬렌 그룹이며; R8및 R9는 동일하거나 상이하며, 각각 수소 원자, 저급 알킬 그룹 또는 하이드록실-저급-알킬 그룹이거나, R8및 R9가 이들이 결합되어 있는 질소 원자와 함께, 저급 알킬 그룹으로 치환될 수 있는 모르폴리노 그룹 또는 피페리디노 그룹이고; m은 2 내지 6의 정수이며; p는 2 또는 3의 정수이고; X는 화학식R10은 수소원자, 저급 알킬 그룹, 아실 그룹, (저급 알콕실)카보닐 그룹 또는 피리딜 그룹이고, R11은 하이드록실 그룹으로 치환될 수 있는, 탄소수 3 내지 18의 알킬 또는 알케닐 그룹이다.
- 제 1 항에 있어서, 화학식 1 중 R1이 알킬 그룹; 사이클로알킬 그룹; 또는 동일하거나 상이하여 저급 알킬 그룹, 저급 알콕실 그룹, 하이드록실 그룹, 하이드록실-저급-알킬 그룹 및 니트로 그룹으로부터 선택된 1 내지 3 개의 치환체에 의해 치환될 수 있는 페닐 그룹이고; 화학식 1중 P1이 탄소수 2 내지 18의 알킬 그룹, 또는 (i) 니트로 그룹, 할로겐 원자, 저급 알콕실 그룹, (저급 알콕실)페닐아조 그룹 또는 페닐아조 그룹으로 치환될 수 있는 벤질옥시카보닐 그룹 및 (ii) 플루오레닐 그룹 또는 메틸설포닐 그룹으로 치환될 수 있는, 직쇄, 측쇄 또는 사이클릭 알킬 그룹을 함유하는 알콕시카보닐 그룹으로부터 선택된 아미노-보호 그룹인 방법.
- 제 1 항에 있어서, 화학식 1중 R1이 페닐 그룹, 디메톡시페닐 그룹 또는 디하이드록시페닐 그룹이고, R2가 모르폴리노 그룹인 방법.
- 제 1 항에 있어서, 화학식 1중 R1이 탄소수 6 내지 15의 알킬 그룹, 사이클로 헥실 그룹 또는 페닐 그룹이고, R2가 (저급 알킬) 아미노 그룹, (모르폴리노-저급알킬)아미노 그룹, 하이드록실 그룹으로 치환될 수 있는 사이클로알킬아미노 그룹, 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피롤리디노그룹, 저급 알킬 그룹으로 치환될 수 있는 피페라지노 그룹, 비스(하이드록실-저급-알킬)아미노 그룹, 또는 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피페리디노 그룹인 방법.
- 화학식 2의 아미노 알콜 유도체. 화학식 2 : R2-CH2-C*H(NHP1)-C|*H(OH)-R1, 상기식에서, *는 비대칭 탄소 원자이고, P1, R1및 R2는 각각 제 1항에서 정의한 바와 같다.
- 제 5 항에 있어서, R1이 알킬 그룹; 사이클로알킬 그룹; 또는 동일하거나 상이하여 저급 알킬 그룹, 저급 알콕실 그룹, 하이드록실 그룹, 하이드록실-저급-알킬 그룹 및 니트로 그룹으로부터 선택된 1 내지 3 개의 치환체에 의해 치환될 수 있는 페닐 그룹이고; P1이 탄소수 3 내지 18의 알킬 그룹, 또는 (i) 니트로 그룹, 할로겐 원자, 저급 알콕실 그룹, (저급 알콕실)페닐아조 그룹 또는 페닐아조 그룹으로 치환될 수 있는 벤질옥시카보닐 그룹 및 (ii) 플루오레닐 그룹 또는 메틸설포닐 그룹으로 치환될 수 있는, 직쇄, 측쇄 또는 사이클릭 알킬 그룹을 함유하는 알콕시카보닐 그룹으로부터 선택된 아미노-보호 그룹인 아미노 알콜 유도체.
- 제 5 항에 있어서, R1이 탄소수 6 내지 15의 알킬 그룹, 사이클로 헥실 그룹 또는 페닐 그룹이고, P1이 데실 그룹이거나, 벤질옥시카보닐 그룹, t-부톡시카보닐 그룹 및 옥틸옥시카보닐 그룹으로부터 선택된 아미노-보호 그룹이며, R2가 모르폴리노 그룹, (저급 알킬) 아미노 그룹, (모르폴리노-저급알킬)아미노 그룹, 하이드록실 그룹으로 치환될 수 있는 사이클로알킬아미노 그룹, 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피롤리디노그룹, 저급 알킬 그룹으로 치환될 수 있는 피페라지노 그룹, 비스(하이드록실-저급-알킬)아미노 그룹, 또는 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피페리디노 그룹인 아미노 알콜 유도체.
- 제 5 항에 있어서, R1이 페닐 그룹이고, P1이 벤질옥시카보닐 그룹이며, R2가 모르폴리노 그룹, 피롤리디노그룹, 하이드록시피롤리디노 그룹, 하이드록시피페리디노 그룹, N-메틸피페라지노 그룹, 디에탄올아미노 그룹 또는 하이드록시사이클로헥실아미노 그룹이며, 이의 배위가 (1S,2S)인 아미노 알콜 유도체.
- 제 5 항에 있어서, R1이 페닐 그룹이고, P1이 벤질옥시카보닐 그룹이며, R2가 모르폴리노 그룹, 피롤리디노그룹, 피페리디노 그룹, 사이클로헥실아미노 그룹 또는 사이클로펜틸아미노 그룹이고, 이의 배위가 (1R,2R)인 아미노 알콜 유도체.
- (A) 화학식 1의 아미노프로판올 유도체를 화학식 5의 아민과 반응시켜 화학식 2의 아미노 알콜 유도체를 수득하는 단계를 포함하는, 제 5항 내지 제 9항중 어느 한 항에 따른 아미노 알콜 유도체의 제조방법. 화학식 1 : Y-CH2-C*H(NHP1)-C*H(OH)-R1, 화학식 2 : R2-CH2-C*H(NHP1)-C|*H(OH)-R1, 화학식 5 : R2H 상기식에서, *는 비대칭 탄소 원자이고, P1은 알킬그룹 또는 아미노-보호 그룹이며, Y는 이탈 그룹이고, R1은 알킬 그룹, 사이클로알킬 그룹 또는 아릴 그룹이며, R2는 제 1항에서 정의한 바와 같다.
- 화학식 3의 아미노 알콜 유도체. 화학식 3 : R2-CH2-C*H(NH2)-C|*H(OH)-R1상기식에서, *는 비대칭 탄소 원자이고, R1및 R2는 제 1항에서 정의한 바와 같다.
- 제 11 항에 있어서, R1이 탄소수 6 내지 15의 알킬 그룹, 사이클로 헥실 그룹 또는 페닐 그룹이고, R2가 모르폴리노 그룹, (저급 알킬) 아미노 그룹, (모르폴리노-저급알킬)아미노 그룹, 하이드록실 그룹으로 치환될 수 있는 사이클로알킬아미노 그룹, 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피롤리디노그룹, 저급 알킬 그룹으로 치환될 수 있는 피페라지노 그룹, 비스(하이드록실-저급-알킬)아미노 그룹, 또는 하이드록실 그룹 또는 하이드록실-저급-알킬 그룹으로 치환될 수 있는 피페리디노 그룹인 아미노 알콜 유도체.
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|---|---|---|---|
| JP95-345080 | 1995-12-08 | ||
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| KR970042525A true KR970042525A (ko) | 1997-07-24 |
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| AT (1) | ATE248828T1 (ko) |
| CA (1) | CA2192268C (ko) |
| DE (1) | DE69629789T2 (ko) |
| HU (1) | HUP9603389A3 (ko) |
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| US6916802B2 (en) * | 2002-04-29 | 2005-07-12 | Genzyme Corporation | Amino ceramide-like compounds and therapeutic methods of use |
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| US9314466B2 (en) | 2007-03-06 | 2016-04-19 | Allergan, Inc. | Methods for treating cognitive disorders using 1-benzyl-1-hydroxy-2,3-diamino-propyl amines, 3-benzyl-3-hydroxy-2-amino-propionic acid amides and related compounds |
| US8173683B2 (en) | 2007-03-06 | 2012-05-08 | Allergan, Inc. | Methods for treating cognitive disorders |
| US20100190792A1 (en) * | 2007-03-06 | 2010-07-29 | Allergan, Inc | Methods for treating cognitive disorders using 1-benzyl-1-hydroxy-2,3-diamino-propyl amines, 3-benzyl-3-hydroxy-2-amino-propionic acid amides and related compounds |
| WO2008109286A1 (en) * | 2007-03-06 | 2008-09-12 | Allergan, Inc. | Methods for treating cognitive disorders using 1-aryl-1-hydroxy-2,3-diamino-propyl amines, 1-heteroaryl-1-hydroxy-2,3-diamino-propyl amines and related compounds |
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1996
- 1996-12-05 NO NO965193A patent/NO965193L/no unknown
- 1996-12-06 HU HU9603389A patent/HUP9603389A3/hu unknown
- 1996-12-06 DE DE69629789T patent/DE69629789T2/de not_active Expired - Lifetime
- 1996-12-06 EP EP96119621A patent/EP0782992B1/en not_active Expired - Lifetime
- 1996-12-06 AT AT96119621T patent/ATE248828T1/de not_active IP Right Cessation
- 1996-12-06 CA CA002192268A patent/CA2192268C/en not_active Expired - Fee Related
- 1996-12-07 KR KR1019960064982A patent/KR970042525A/ko not_active Application Discontinuation
- 1996-12-08 CN CN96123806A patent/CN1164530A/zh active Pending
- 1996-12-09 US US08/761,934 patent/US5907039A/en not_active Expired - Lifetime
-
1999
- 1999-02-23 US US09/255,869 patent/US6335444B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HU9603389D0 (en) | 1997-01-28 |
| CA2192268A1 (en) | 1997-06-09 |
| HUP9603389A3 (en) | 2000-03-28 |
| EP0782992A1 (en) | 1997-07-09 |
| DE69629789D1 (de) | 2003-10-09 |
| US5907039A (en) | 1999-05-25 |
| DE69629789T2 (de) | 2004-07-15 |
| HUP9603389A2 (hu) | 1998-08-28 |
| CA2192268C (en) | 2009-05-19 |
| CN1164530A (zh) | 1997-11-12 |
| NO965193L (no) | 1997-06-09 |
| US6335444B1 (en) | 2002-01-01 |
| EP0782992B1 (en) | 2003-09-03 |
| ATE248828T1 (de) | 2003-09-15 |
| NO965193D0 (no) | 1996-12-05 |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |