KR950703517A - 키누레니나제 및/또는 키누레닌-3-하이드록실라제 억제 활성을 갖는 2-아미노-4-페닐-4-옥소-부티르산 유도체(2-Amino-4-phenyl-4-oxo-butyric acid derivatives with kynureninase and/or kynurenine-3-hydroxylase inhibiting activity) - Google Patents
키누레니나제 및/또는 키누레닌-3-하이드록실라제 억제 활성을 갖는 2-아미노-4-페닐-4-옥소-부티르산 유도체(2-Amino-4-phenyl-4-oxo-butyric acid derivatives with kynureninase and/or kynurenine-3-hydroxylase inhibiting activity) Download PDFInfo
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- KR950703517A KR950703517A KR1019950701103A KR19950701103A KR950703517A KR 950703517 A KR950703517 A KR 950703517A KR 1019950701103 A KR1019950701103 A KR 1019950701103A KR 19950701103 A KR19950701103 A KR 19950701103A KR 950703517 A KR950703517 A KR 950703517A
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- 108010031676 Kynureninase Proteins 0.000 title claims abstract 4
- 102000005447 kynureninase Human genes 0.000 title claims abstract 4
- QXRCVKLRAOSZCP-UHFFFAOYSA-N alpha-Amino-beta-benzoylpropionic acid Chemical class OC(=O)C(N)CC(=O)C1=CC=CC=C1 QXRCVKLRAOSZCP-UHFFFAOYSA-N 0.000 title claims 3
- 102100037652 Kynurenine 3-monooxygenase Human genes 0.000 title 2
- 108010033242 Kynurenine 3-monooxygenase Proteins 0.000 title 2
- 230000002401 inhibitory effect Effects 0.000 title 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 6
- 230000004770 neurodegeneration Effects 0.000 claims abstract 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 5
- 229940125532 enzyme inhibitor Drugs 0.000 claims abstract 4
- 239000002532 enzyme inhibitor Substances 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 34
- 239000000203 mixture Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 9
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- -1 2-Amino-4- (3'-chlorophenylphenyl) -4-oxo-butyric acid Chemical compound 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- JLXIAMYZJLYAAJ-UHFFFAOYSA-N 2-amino-4-(2-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1Cl JLXIAMYZJLYAAJ-UHFFFAOYSA-N 0.000 claims 2
- QMSVTRCOYUVRRQ-UHFFFAOYSA-N 2-amino-4-(2-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1F QMSVTRCOYUVRRQ-UHFFFAOYSA-N 0.000 claims 2
- SPJHXRHVIFGFCY-UHFFFAOYSA-N 2-amino-4-(2-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=CC=C1C(=O)CC(N)C(O)=O SPJHXRHVIFGFCY-UHFFFAOYSA-N 0.000 claims 2
- NJPWJCRSWNKWDA-UHFFFAOYSA-N 2-amino-4-(2-methylphenyl)-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)CC(N)C(O)=O NJPWJCRSWNKWDA-UHFFFAOYSA-N 0.000 claims 2
- MXBKZYGNMKXYQE-UHFFFAOYSA-N 2-amino-4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=C(Cl)C(Cl)=C1 MXBKZYGNMKXYQE-UHFFFAOYSA-N 0.000 claims 2
- YFNBEUVUCSHYTF-UHFFFAOYSA-N 2-amino-4-(3-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(Cl)=C1 YFNBEUVUCSHYTF-UHFFFAOYSA-N 0.000 claims 2
- YFSJVMZKNPQZOM-UHFFFAOYSA-N 2-amino-4-(3-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=CC(C(=O)CC(N)C(O)=O)=C1 YFSJVMZKNPQZOM-UHFFFAOYSA-N 0.000 claims 2
- NDBGGSKCXFIQPQ-UHFFFAOYSA-N 2-amino-4-(5-fluoro-2-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(F)C=C1C(=O)CC(N)C(O)=O NDBGGSKCXFIQPQ-UHFFFAOYSA-N 0.000 claims 2
- DAYCFBKZOWZXAM-UHFFFAOYSA-N 2-amino-4-oxo-4-[2-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1C(F)(F)F DAYCFBKZOWZXAM-UHFFFAOYSA-N 0.000 claims 2
- VQOCYLCCBIFNGD-UHFFFAOYSA-N 2-amino-4-oxo-4-[3-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(C(F)(F)F)=C1 VQOCYLCCBIFNGD-UHFFFAOYSA-N 0.000 claims 2
- CQLSOTAGCGJASP-UHFFFAOYSA-N 2-amino-4-oxo-4-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=C(C(F)(F)F)C=C1 CQLSOTAGCGJASP-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- AARUKZVPSZZDPQ-UHFFFAOYSA-N 1,1-dihydroxyhydrazine Chemical group NN(O)O AARUKZVPSZZDPQ-UHFFFAOYSA-N 0.000 claims 1
- VQEMEQQNXUSENW-UHFFFAOYSA-N 2-amino-4-(3-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(F)=C1 VQEMEQQNXUSENW-UHFFFAOYSA-N 0.000 claims 1
- CKLOTMANRVIPIE-UHFFFAOYSA-N 2-amino-4-(4-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)C(N)CC(=O)C1=CC=C(Cl)C=C1 CKLOTMANRVIPIE-UHFFFAOYSA-N 0.000 claims 1
- TZKBKUJPNKOKHZ-UHFFFAOYSA-N 2-amino-4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CC(N)C(O)=O)C=C1 TZKBKUJPNKOKHZ-UHFFFAOYSA-N 0.000 claims 1
- XLNGZTMLVRIMNS-UHFFFAOYSA-N 2-amino-4-(5-bromo-2-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(Br)C=C1C(=O)CC(N)C(O)=O XLNGZTMLVRIMNS-UHFFFAOYSA-N 0.000 claims 1
- NCVFYWJEQCKNIW-UHFFFAOYSA-N 2-amino-4-(5-chloro-2-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)CC(N)C(O)=O NCVFYWJEQCKNIW-UHFFFAOYSA-N 0.000 claims 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000002381 Brain Hypoxia Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000004007 neuromodulation Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical class OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
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- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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Abstract
본 발명은 신경변성 질환을 예방 및/또는 치료하기 위한, 키누레니나제 효소 억제제 및/또는 키누레닌-3-하이드록실라제 효소 억제제로서 작용하는 일반식(Ⅰ)의 2-아미노-4-페닐-4-옥소-부티르산 유도체의 용도에 관한 것이다.
상기식에서, X 및 Y는 각각 독립적으로 수소, 할로겐, 트리플루오로메틸, 하이드록시, C1-C6알킬, 벤질, C6-C10아릴, -OR′, -SR′,또는(여기서, R′는 C1-C6알킬 또는 벤질이다)
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 신경변경 질환을 예방 및/또는 치료하기 위한, 키누레니나제 효소 억제제 및/또는 키누레닌-3-하이드록실라제 효소 억제제로서 작용하는, 단일 이성질체 또는 이성질체의 혼합물로서 존재하는 일반식(Ⅰ)의 2-아미노-4-페닐-4-옥소-부티르산 유도체 및 약제학적으로 허용되는 이의 염.상기식에서, X 및 Y는 각각 독립적으로 수소, 할로겐, 트리플루오로메틸, 하이드록시, C1-C6알킬, 벤질, C6-C10아릴, -OR′, -SR′,또는(여기서, R′는 C1-C6알킬 또는 벤질이다)이고, R은 하이드록시, 아미노, 하이드록실아민, -OR′, -NHR′,또는 -NHOR′(여기서, R′는 위에서 정의한 바와 같다)이다.
- 신경변성 질환의 예방 및/또는 치료에 유용한 약제의 제조에 있어서, 제1항에 따르는 일반식(Ⅰ)으 화합물 및 약제학적으로 허용되는 염의 용도.
- 제1항 또는 제2항에 있어서, 신경변성 질환이 헌팅톤 무도병, 알쯔하이며 질환, 파킨슨 질환, 후천성 면역결핍증(AIDS)에 의해 야기된 치매, 다경색 치매, 뇌 빈혈 뇌 저산소증 또는 간질인, 단일 이성질체 또는 이성질체의 혼합물로서 존재하는 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 이의 염의 용도.
- 신경변성 질환의 예방 및/또는 치료에 사용하기 위한, 단일 이성질체 또는 이성질체의 혼합물로서 존재하는, 2-아미노-4-페닐-4-옥소-부티르산; 2-아미노-4-(2′-메록시페닐)-4-옥소-부티르산; 2-아미노-4-(2′-플루오로페닐)-4-옥소-부티르산; 2-아미노-4-(4′-메톡시페닐)-4-옥소-부티르산; 2-아미노-4-(2′-메틸페닐)-4-옥소-부티르산; 2-아미노-4-(3′-메록시페닐)-4-옥소-부티르산; 2-아미노-4-(2′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(3′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(4′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(4′-클로로페닐)-4-옥소-부티르산; 2-아미노-4-(3′-클로로페닐페닐)-4-옥소-부티르산; 2-아미노-4-(.2′-클로로페닐)-4-옥소-부티르산; 2-아미노-4-(3′-클로로페닐)-4-옥소-부티르산; 2-아미노-4-(2′-메톡시-5′-플루오로페닐)-4-옥소-부티르산; 2-아미노-4-(3′,4′-디클로로페닐)-4-옥소-부티르산; 2-아미노-4-(2′-메톡시-5′-클로로페닐)-4-옥소-부티르산 및 2-아미노-4-(2′-메톡시--5′-브로모페닐)-4-옥소-부티르산으로 이루어진 그룹 중에서 선택된 화합물 또는 약제학적으로 허용되는 이의 염.
- 단일 이성질체 또는 이성질체의 혼합물로서 존재하는 일반식(ⅠA)의 화합물 또는 약제학적으로 허용되는 이의 염.상기식에서, X 및 Y는 각각 독립적으로 수소, 할로겐, 트리플루오로메틸, 하이드록시, C1-C6알킬, 벤질, C6-C10아릴, -OR′, -SR′,또는(여기서, R′는 C1-C6알킬 또는 벤질이다)이고, R은 하이드록시, -OR, 아미노, -NHR′,, 하이드록실 아민 또는 -NHOR′(여기서, R′는 위에서 정의한 바와 같다)인데, 단 R은, (ⅰ) X 및 Y가 동시에 수소이거나, (ⅱ) X 및 Y가 페닐 환의 3위치 및 4위치에 존재하고 동시에 하이드록시 그룹 또는 -OR′그룹(여기서, R′은 메틸이다)이거나, (ⅲ) X 및 Y 중의 하나가 수소이고 다른 하나가 페닐 환의 4위치에 존재하며 하이드록시, 염소, 불소, 메틸, n-프로필 또는 메톡시인 경우에는 하이드록시가 아니다.
- 제5항에 있어서, 하이드록시이고 (a) X 및 Y중의 하나가 수소이고 다른 하나가 페닐 환의 2위치, 3위치 또는 4위치에 존재하는 C1-C6알킬 또는 트리플루오로메틸이며, 단 C1-C6알킬이 페닐 환의 4위치에 존재하는 경우, 이는 메틸도 n-프로필도 아니거나, (b) X 및 Y중의 하나가 수소이고 다른 하나가 페닐 환의 2위치, 3위치 또는 4위치에 존재하는 경우, 이는 염소 또는 불소도 아니거나, (c) X 및 Y중의 하나가 수소이고 다른 하나가 페닐 환의 2위치, 3위치 도는 4위치에 존재하는 -OR′(여기서, R′은 C1-C6알킬이다)이며, 단 -OR′이 페닐 환의 4위치에 존재하는 경우, C1-C6알킬은 메틸이 아니거나, (d) X 및 Y 중의 하나가 OR′(여기서, R′은 C1-C6알킬이다)이고 다른 하나가 할로겐인, 단일 이성질체로서 또는 이성질체의 혼합물로서 존재하는 일반식(ⅠA)의 화합물 또는 약제학적으로 허용되는 이의 염.
- 단일 이성질체 또는 이성질체의 혼합물 형태로 존재하는, 2-아미노-4-(2′-메톡시페닐)-4-옥소-부티르산; 2-아미노-4-(3′-메톡시페닐)-4-옥소-부티르산; 2-아미노-4-(2′-플루오로페닐)-4-옥소-부티르산; 2-아미노-4-(3′-플루오로페닐)-4-옥소-부티르산; 2-아미노-4-(2′-클로로페닐)-4-옥소-부티르산; 2-아미노-4-(3′-클로로페닐)-4-옥소-부티르산; 2-아미노-4-(3′,4′-디클로로페닐)-4-옥소-부티르산; 2-아미노-4-(2′-메틸페닐)-4-옥소-부티르산; 2-아미노-4-(2′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(3′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(4′-트리플루오로메틸페닐)-4-옥소-부티르산; 2-아미노-4-(2′-메톡시-5′-브로모페닐)-4-옥소-부티르산; 2-아미노-4-(2′-클로로페닐)-4-옥소-부티르산 및 2-아미노-4-(2′-메톡시-5′-플루오로페닐)-4-옥소-부티르산으로 이루어진 그룹 중에서 선택된 화합물 또는 약제학적으로 허용되는 이의 염.
- 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물의 알칼리 금속 또는 알칼리 토금속 염과 반응시켜 일반식(Ⅳ)의 화합물을 수득하는 단계(A), 일반식(Ⅳ)의 화합물을 진한 할로겐산으로 처리하여 일반식(Ⅰ) 도는 (ⅠA)의 화합물(여기서, X 및 Y는 상기 정의한 바와 같고 R은 하이드록시는 아니다)로 전환시키는 단계(C), 임의로 일반식(Ⅰ) 또는 (ⅠA)의 화합물을 염화시키는 단계(D) 및 임의로 일반식(Ⅰ) 또는 (ⅠA)의 화합물의 이성질체 혼합물을 단일 이성질체로 분리하는 단계(E)를 포함함을 특징으로 하여, 제1항에 따르는 일반식(Ⅰ)의 화합물 또는 제5항에 따르는 일반식(ⅠA)의 화합물을 제조하는 방법.상기식에서, X 및 Y는 제1항에 따르는 일반식(Ⅰ) 또는 제5항에 따르는 일반식(IA)에서 정의한 바와 같고, R″는 수소 또는 메틸이다.
- 일반식(Ⅴ)의 일반식(Ⅵ)의 화합물의 단일(R) 또는 (S) 에난티오머와 반응시켜 일반식(Ⅶ)의 화합물의 단일 (R) 또는 (S) 에난티오머를 수득하는 단계(a), 일반식(Ⅶ)의 화합물을 탈보호시켜 일반식(Ⅶ)의 화합물의 단일(R) 또는 (S) 에난티오머를 수득하는 단계(b) 및 추가로 일반식(Ⅶ)의 화합물을 탈보호시켜, 반응 조건에 따라 유리 아미노산 또는 이의 염인 일반식(Ⅰ) 또는 (ⅠA)의 화합물의 단일 (R) 또는 (S) 에난티오머를 수득하는 단계(c)[이때, 일반식(Ⅵ)의 화합물은 일반식(Ⅰ) 또는 (ⅠA)의 화합물을 유도하는 전체 공정을 통해 존재한다]를 포함함을 특징으로 하여, 제1항에 따르는 일반식(Ⅰ)의 화합물 또는 제5항에 따르는 일반식(ⅠA)의 화합물의 단일(R) 또는 (S) 에난티오머를 제조하는 방법.상기식에서, X 및 Y는 제1항에 따르는 일반식(Ⅰ) 또는 제5항에 따르는 일반식(ⅠA)에서 정의한 바와 같고, Z는 적합한 아미노 보호 그룹이다.
- 일반식(Ⅸ)의 화합물을 단일(R) 또는 (S) 에난티오머로서 또는 라세미체 혼합물로서 존재하는 일반식(Ⅶ)의 화합물을 수득하는 단계(a′) 및 단일(R) 또는 (S) 에난티오머로서 또는 라세미체 혼합물로서 존재하는 일반식(Ⅸ)의 화합물을(Ⅰ) 또는 (ⅠA)의 화합물(여기서, X 및 Y는 위에서 정의한 바와 같고, R은 하이드록시 이다)의 단일(R) 또는 (S) 에난티오머 또는 라세미체 혼합물로 전환시키고, 필요한 경우, 일반식(Ⅰ) 또는 (ⅠA)의 화합물(여기서, R은 하이드록시이다)을 일반식(Ⅰ) 또는 (ⅠA)의 화합물(여기서, R은 하이드록시는 아니다)로 전환시키는 단계(b′)를 포함함을 특징으로 하여, 단일(R) 또는 (S) 에난티오머로서 또는 라세미체 혼합물로서 존재하는, 제1항에 따르는 일반식(Ⅰ)의 화합물 또는 제5항에 따르는 일반식(ⅠA)의 화합물을 제조하는 방법.상기식에서, X 및 Y는 제1항에 따르는 일반식(Ⅰ) 또는 제5항에 따르는 일반식(ⅠA)에서 정의한 바와 같고, R은 수소, 메틸, 트리플루오로메틸, C1-C6알콕시 또는 벤질옥시이다.
- 단일 이성질체 또는 이성질체의 혼합물로서 존재하는, 활성성분으로서의 제1항에 따르는 일반식(Ⅰ)의 화합물 또는 제5항에 따르는 일반식(ⅠA)의 화합물 또는 약제학적으로 허용되는 이의 염과 담체 및/또는 약제학적으로 허용되는 희석제를 포함하는 약제학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
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| IT93MI001649A IT1265101B1 (it) | 1993-07-23 | 1993-07-23 | Derivati dell'acido 2-ammino-4-fenil-4-osso butirrico |
| ITMI93A001649 | 1993-07-23 | ||
| PCT/EP1994/002280 WO1995003271A1 (en) | 1993-07-23 | 1994-07-12 | 2-amino-4-phenyl-4-oxo-butyric acid derivatives with kynureninase and/or kynurenine-3-hydroxylase inhibiting activity |
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| KR950703517A true KR950703517A (ko) | 1995-09-20 |
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| KR1019950701103A KR950703517A (ko) | 1993-07-23 | 1994-07-12 | 키누레니나제 및/또는 키누레닌-3-하이드록실라제 억제 활성을 갖는 2-아미노-4-페닐-4-옥소-부티르산 유도체(2-Amino-4-phenyl-4-oxo-butyric acid derivatives with kynureninase and/or kynurenine-3-hydroxylase inhibiting activity) |
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| EP (1) | EP0662948B1 (ko) |
| JP (1) | JPH08501805A (ko) |
| KR (1) | KR950703517A (ko) |
| CN (1) | CN1112786A (ko) |
| AT (1) | ATE171935T1 (ko) |
| AU (1) | AU678273B2 (ko) |
| CA (1) | CA2144521A1 (ko) |
| DE (1) | DE69413789T2 (ko) |
| DK (1) | DK0662948T3 (ko) |
| ES (1) | ES2123801T3 (ko) |
| FI (1) | FI951298A0 (ko) |
| HU (1) | HUT70478A (ko) |
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| US5519055A (en) * | 1993-08-06 | 1996-05-21 | University Of Maryland At Baltimore | Substituted kynurenines and process for their preparation |
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| GB9521486D0 (en) * | 1995-10-20 | 1995-12-20 | Pharmacia Spa | Fluoro-substituted benzoylpropionic acid derivatives |
| GB9615441D0 (en) * | 1996-07-23 | 1996-09-04 | Pharmacia Spa | Benzoylpropionic acid ester derivatives |
| ES2231879T3 (es) * | 1996-08-16 | 2005-05-16 | Warner-Lambert Company Llc | Inhibidores de metaloproteinasas de la matriz de acido butirico. |
| GB9618349D0 (en) * | 1996-09-03 | 1996-10-16 | Pharmacia Spa | N-substituted 2-amino-4-phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibitory activity |
| GB9716103D0 (en) * | 1997-07-30 | 1997-10-01 | Pharmacia & Upjohn Spa | Condensed heterocyclic compounds |
| GB9725055D0 (en) * | 1997-11-26 | 1998-01-28 | Pharmacia & Upjohn Spa | 1,3,4-thiadiazoles compounds |
| GB9725141D0 (en) * | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Benzenesulfonamide compounds |
| EP1056452B1 (en) * | 1998-02-23 | 2006-07-19 | South Alabama Medical Science Foundation | Indole-3-propionic acids, salts and esters thereof used as medicaments |
| US6783965B1 (en) * | 2000-02-10 | 2004-08-31 | Mountain View Pharmaceuticals, Inc. | Aggregate-free urate oxidase for preparation of non-immunogenic polymer conjugates |
| ATE288414T1 (de) * | 1998-11-11 | 2005-02-15 | Novartis Pharma Gmbh | Herstellung von 2-amino-2(2-(4- alkylphenyl)äthyl)propan-1,3-diolen |
| CN1144779C (zh) * | 1999-03-11 | 2004-04-07 | 杭州中美华东制药有限公司 | 制备2-[2-(4-烷基苯基)-乙基]-2-氨基-丙二醇的方法以及其中制得的中间产物 |
| NZ530051A (en) * | 2001-06-12 | 2006-12-22 | Wellstat Therapeutics Corp | Polycyclic oxy-aromatic acid derivatives for the treatment of metabolic disorders |
| FR2827045B1 (fr) * | 2001-07-05 | 2007-08-10 | Univ Pasteur | Methodes et compositions pour la selection et le developpement de nouveaux agents pharmacologiques ou de nouveaux medicaments |
| FR2827859B1 (fr) | 2001-07-30 | 2005-09-23 | Lipha | Derives 4-(arylthio) - ou 4-(heteroarylthio) -butyrique dans la preparation de medicaments destines au traitement du diabete |
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| ITMI20041626A1 (it) * | 2004-08-06 | 2004-11-06 | Roberto Pellicciari | Inibitori della chinurenina-ammino-trasferasi |
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-
1993
- 1993-07-23 IT IT93MI001649A patent/IT1265101B1/it active IP Right Grant
-
1994
- 1994-07-12 DE DE69413789T patent/DE69413789T2/de not_active Expired - Fee Related
- 1994-07-12 ES ES94921642T patent/ES2123801T3/es not_active Expired - Lifetime
- 1994-07-12 PL PL94308142A patent/PL179857B1/pl unknown
- 1994-07-12 NZ NZ268896A patent/NZ268896A/en unknown
- 1994-07-12 AU AU72285/94A patent/AU678273B2/en not_active Ceased
- 1994-07-12 KR KR1019950701103A patent/KR950703517A/ko active IP Right Grant
- 1994-07-12 HU HU9501146A patent/HUT70478A/hu unknown
- 1994-07-12 AT AT94921642T patent/ATE171935T1/de not_active IP Right Cessation
- 1994-07-12 DK DK94921642T patent/DK0662948T3/da active
- 1994-07-12 RU RU95111308A patent/RU2139850C1/ru active
- 1994-07-12 EP EP94921642A patent/EP0662948B1/en not_active Expired - Lifetime
- 1994-07-12 CA CA002144521A patent/CA2144521A1/en not_active Abandoned
- 1994-07-12 JP JP7503289A patent/JPH08501805A/ja active Pending
- 1994-07-12 WO PCT/EP1994/002280 patent/WO1995003271A1/en active IP Right Grant
- 1994-07-12 CN CN94190531A patent/CN1112786A/zh active Pending
- 1994-07-19 IL IL110365A patent/IL110365A/en not_active IP Right Cessation
- 1994-07-21 TW TW083106674A patent/TW268937B/zh active
- 1994-07-22 ZA ZA945425A patent/ZA945425B/xx unknown
-
1995
- 1995-03-20 FI FI951298A patent/FI951298A0/fi unknown
-
1997
- 1997-10-14 US US08/949,392 patent/US20010008947A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ZA945425B (en) | 1995-03-01 |
| CN1112786A (zh) | 1995-11-29 |
| AU7228594A (en) | 1995-02-20 |
| DE69413789D1 (de) | 1998-11-12 |
| EP0662948B1 (en) | 1998-10-07 |
| ES2123801T3 (es) | 1999-01-16 |
| AU678273B2 (en) | 1997-05-22 |
| PL179857B1 (pl) | 2000-11-30 |
| ATE171935T1 (de) | 1998-10-15 |
| TW268937B (ko) | 1996-01-21 |
| ITMI931649A1 (it) | 1995-01-23 |
| HU9501146D0 (en) | 1995-06-28 |
| RU2139850C1 (ru) | 1999-10-20 |
| CA2144521A1 (en) | 1995-02-02 |
| ITMI931649A0 (it) | 1993-07-23 |
| FI951298A (fi) | 1995-03-20 |
| IT1265101B1 (it) | 1996-10-30 |
| DK0662948T3 (da) | 1999-06-21 |
| NZ268896A (en) | 1997-01-29 |
| JPH08501805A (ja) | 1996-02-27 |
| DE69413789T2 (de) | 1999-05-06 |
| EP0662948A1 (en) | 1995-07-19 |
| IL110365A0 (en) | 1994-10-21 |
| HUT70478A (en) | 1995-10-30 |
| PL308142A1 (en) | 1995-07-24 |
| IL110365A (en) | 1998-06-15 |
| FI951298A0 (fi) | 1995-03-20 |
| WO1995003271A1 (en) | 1995-02-02 |
| RU95111308A (ru) | 1996-12-27 |
| US20010008947A1 (en) | 2001-07-19 |
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