KR840009302A - 인돌화합물의 제조방법 - Google Patents
인돌화합물의 제조방법 Download PDFInfo
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- KR840009302A KR840009302A KR1019840002658A KR840002658A KR840009302A KR 840009302 A KR840009302 A KR 840009302A KR 1019840002658 A KR1019840002658 A KR 1019840002658A KR 840002658 A KR840002658 A KR 840002658A KR 840009302 A KR840009302 A KR 840009302A
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- hydrogen
- pyridyl
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- -1 indole compound Chemical class 0.000 title claims 9
- 238000004519 manufacturing process Methods 0.000 title claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 238000000034 method Methods 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- GUXQOVBGUZZBPJ-MKMNVTDBSA-N (e)-2-methyl-5-(1-pyridin-3-ylindol-3-yl)pent-2-enoic acid Chemical compound C12=CC=CC=C2C(CC\C=C(/C)C(O)=O)=CN1C1=CC=CN=C1 GUXQOVBGUZZBPJ-MKMNVTDBSA-N 0.000 claims 1
- GUXQOVBGUZZBPJ-NSIKDUERSA-N (z)-2-methyl-5-(1-pyridin-3-ylindol-3-yl)pent-2-enoic acid Chemical compound C12=CC=CC=C2C(CC/C=C(/C)C(O)=O)=CN1C1=CC=CN=C1 GUXQOVBGUZZBPJ-NSIKDUERSA-N 0.000 claims 1
- VSKZGHVPGOMFAV-UHFFFAOYSA-N 1-pyridin-2-ylindole Chemical class C1=CC2=CC=CC=C2N1C1=CC=CC=N1 VSKZGHVPGOMFAV-UHFFFAOYSA-N 0.000 claims 1
- ZEHHUSHFHPIFOA-UHFFFAOYSA-N 2-methyl-3-(1-pyridin-3-ylindol-3-yl)prop-2-enoic acid Chemical compound C12=CC=CC=C2C(C=C(C)C(O)=O)=CN1C1=CC=CN=C1 ZEHHUSHFHPIFOA-UHFFFAOYSA-N 0.000 claims 1
- VMYNZSGRXMWFQI-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2C(CCC(=O)O)=CN1C1=CC=CN=C1 VMYNZSGRXMWFQI-UHFFFAOYSA-N 0.000 claims 1
- MCAPFZFMMUIMEH-UHFFFAOYSA-N 5-(2-methyl-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound CC1=C(CCCCC(O)=O)C2=CC=CC=C2N1C1=CC=CN=C1 MCAPFZFMMUIMEH-UHFFFAOYSA-N 0.000 claims 1
- NOSDTQKCYJKFBL-UHFFFAOYSA-N 5-(5-bromo-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C12=CC=C(Br)C=C2C(CCCCC(=O)O)=CN1C1=CC=CN=C1 NOSDTQKCYJKFBL-UHFFFAOYSA-N 0.000 claims 1
- HUHTZTFOSRDAPC-UHFFFAOYSA-N 5-(7-methyl-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C1=2C(C)=CC=CC=2C(CCCCC(O)=O)=CN1C1=CC=CN=C1 HUHTZTFOSRDAPC-UHFFFAOYSA-N 0.000 claims 1
- UABNOBPFYCXKEW-UHFFFAOYSA-N 6-(1-pyridin-3-ylindol-3-yl)hexanoic acid Chemical compound C12=CC=CC=C2C(CCCCCC(=O)O)=CN1C1=CC=CN=C1 UABNOBPFYCXKEW-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 일반식 (Ⅳ)화합물을 일반식 ArX의 화합물과 축합시키거나;일반식(Ⅴ)화합물 또는 이의 3-할로유도체를 일반식(Ⅵ)화합물의 반응성 작용유도체와 축합시키거나;하나의 R2및 하나의 R4를 함유하는 일반식(Ⅶ)화합물을 폐환시키거나;하나의 R2및 하나의 R4를 함유하는 일반식(Ⅷ)화합물을 폐환시키거나;하나의 R2및 하나의 R4를 함유하는 일반식(Ⅸ)화합물을 폐환시키거나;일반식(Ia)화합물을, 임의로 체인A길이를 그정의 내에서 연장하에 일반식 (Ⅰ)화합물로 전환시키거나;일반식(Ⅹ)화합물을 일반식(Ⅸ)화합물과 축합시키고, 필요한 경우 생성된 일반식(Ⅰ)화합물의 인돌환에 직접 결합되어 있는 이중결합을 환원시키거나;일반식(XII)화합물을 일반식(XIII)화합물과 축합시키고, 필요한 경우 생성된 일반식(Ⅰ)화합물의 인돌환에 직접 결합되어 있는 이중결합을 환원시키거나;일반식(XVII)화합물을, 임의로 간섭 반응성 그룹의 일시적보호하에, 일반식(Ⅵ′)화합물의 반응성 작용 유도체와 축합시키고/시키거나;필요한 경우 생성된 일반식(Ⅰ)화합물을 일반식(Ⅰ)의 다른 화합물로 전환시키고/시키거나, 필요한 경우 생성된 일반식(Ⅰ)화합물을 그 염으로 전환시키거나 생성된 염을 유리화합물 또는 다른 염으로 전환시키거나 생성된 염을 유리화합물 또는 다른염으로 전환시키고, 필요한 경우 수득한 이성체 또는 라세미체혼합물을 단일 이성체 또는 라세미체로 분할하고, 필요한 경우 수득한 라세미체를 광학적 광학대칭체로 분할시킴을 특징으로 하여, 다음 일반식(Ⅰ)의 N-피리딜인돌 및 이의 피리딜-N-옥사이드 및 이의 염을 제조하는 방법.상기식에서Ar은 3-또는 4-피리딜, 또는 저급알킬로 치환된 3-또는 4-피리딜이고R1은 각기 독립적으로, 수소, 할로겐, 트리플루오로메틸, 저급알킬, 하이드록시, 아실화 또는 에테르화된 하이드록시, 저급알킬-(티오,설피닐 또는 설포닐)이거나, 인접 탄소원자상의 R1두개가 알킬렌디옥시를 형성하고P는 1또는 2이고R2는 수소 또는 저급알킬이고R3및 R4중 하나는 수소이고 R3및 R4중 다른 하나는 그룹 A-B[여기에서 A는 탄소수 1내지 12의 알킬렌, 탄소수 2내지 12의알키닐렌, 탄소수 2내지 12의 알케닐렌, 저급알킬렌-페닐렌, 저급알킬렌-(티오 또는 옥시)-저급알킬렌,저급알킬렌-(티오 또는 옥시)-페닐렌, 저급알킬렌페닐렌-저급(알킬렌 또는 알케닐렌), 또는 탄소수 4내지12의 알카디에닐렌이고, B는 카복시, 에스테르화 카복시, 카바모일, 모노-또는 디-저급 알킬 카바모일, 시아노, 하이드록시카바모일, 5-테트라졸릴,4,5-디하이드로-2 옥사졸릴, 또는 저급알킬로 치환된 4,5-디하이드로 -2-옥사졸릴이다]이고, 단, 일반식(Ⅴ)에서 R3는 수소이며,X는 반응성 에스테르화 하이드록시이고R3′및 R'4중 하나는 수소이고 다른하나는 그룹 A-B(여기에서 C는 B와 다른 그룹으로서 B로 전환가능한 그룹이다)이고R3 a및 R4 a중 하나는 수소이고 다른 하나는 포르밀 또는 저급알카노일이고A″는 상기 A정의와 같으나 그 체인길이가 1개의 탄소원자만큼 짧아진 것이고R5는 디알킬포스포노 또는 트리아릴포스포늄라디칼이고R3 b및 R4 b중 하나는 수소이고 다른 하나는 반응성에스테르화 하이드록시이고A는 상기 A정의와 같으나, 그 체인길이가 2개의 탄소원자만큼 짧아진 것이나, 직접결합을 나타낸다.
- 제1항에 있어서, Ar이 3-피리딜이고, R1이 수소, 할로겐, 트리플루오로메틸, 저급알킬, 저급알콕시,저급알킬티오, 하이드록시 또는 저급알카노일옥시이고 P가 1이고 R2가 수소 또는 저급알킬이고 R3가 수소이며 R4가 그룹 A-B(메기에서 A는 제1항의 정의와 같고 B는 카복시, 저급알콕시카보닐,카바모일, 시아노, 하이드록시카바모일 또는 5-테트라졸릴이다), 일반식(Ⅰ)화합물 및 그 염을 제조함을 특징으로하는 방법.
- 제1항에 있어서, 다음 일반식(Ⅱ)화합물 및 약학적으로 허용되는 그 염을 제조함을 특징으로하는 방법.상기식에서,R1′는 수소, 저급알킬, 할로겐, 트리플루오로메틸, 하이드록시, 저급알킬티오 또는 저급알콕시이고,R2′는 수소 또는 저급알킬이고,m은 1 내지 10의 정수이고,R6는 하이드록시, 저급알콕시 또는 아미노이다.
- 제3항에 있어서, R1′가 수소 또는 클로로이고, R2′가 수소이고, m이 4또는 5이며, R6가 하이드록시인 일반식(Ⅱ)화합물 및 약학적으로 허용되는 그 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 다음 일반식(Ⅲ)화합물 및 약학적으로 허용되는 그 염을 제조함을 특징으로 하는 방법.상기식에서,R1′는 수소, 저급알킬, 할로겐, 트리플루오로메틸, 하이드록시, 저급알킬티오 또는 저급알콕시이고R2′는 수소 또는 저급알킬이고R6는 하이드드록시, 저급알콕시 또는 아미노이고n은 1내지 4의 정수이고A′는 탄소수 1내지4의 (디오 또는 옥시)알킬렌, (티오 또는 옥시)-1,4-페닐렌, 에테닐렌 또는 저급알킬-치환된 에테닐렌이다.
- 제1항에 있어서, 3-(2-카복시부틸)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(2-카복시에틸)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, (E)-3-(4-카복시펜트-3-에닐)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, (Z)-3-(4-카복시펜트-3-에닐)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(2-카복시프로프-1-에닐)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 5-브로모-3-(4-카복시부틸)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(4-카복시부틸)-2-메틸-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(4-카복시부틸)-7-메틸-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(5-카복시부틸)-5-클로로-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(4-카복시부틸)-5-메틸-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.
- 제1항에 있어서, 3-(5-카복시펜틸)-N-(3-피리딜)인돌 또는 약학적으로 허용되는 이의 염을 제조함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US495370 | 1983-05-17 | ||
| US06/495,370 US4536505A (en) | 1983-05-17 | 1983-05-17 | Certain N-(pyridyl) indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840009302A true KR840009302A (ko) | 1984-12-26 |
Family
ID=23968377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840002658A KR840009302A (ko) | 1983-05-17 | 1984-05-16 | 인돌화합물의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4536505A (ko) |
| EP (1) | EP0126401A1 (ko) |
| JP (1) | JPS59212489A (ko) |
| KR (1) | KR840009302A (ko) |
| AU (1) | AU2809484A (ko) |
| DD (1) | DD224588A5 (ko) |
| DK (1) | DK242484A (ko) |
| ES (5) | ES8602652A1 (ko) |
| FI (1) | FI841925A (ko) |
| GR (1) | GR79934B (ko) |
| HU (1) | HUT34182A (ko) |
| IL (1) | IL71832A0 (ko) |
| NO (1) | NO841958L (ko) |
| PT (1) | PT78582A (ko) |
| ZA (1) | ZA843677B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100807718B1 (ko) * | 2006-10-17 | 2008-02-28 | 한국생명공학연구원 | 인돌 유도체를 유효성분으로 함유하는 대사성 질환 예방 및치료용 약학적 조성물 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| US4609733A (en) * | 1984-12-27 | 1986-09-02 | Ciba-Geigy Corporation | 3-keto-substituted-N-pyridylindoles |
| US4758586A (en) * | 1985-02-01 | 1988-07-19 | Usv Pharmaceutical Corp. | Indolyl compounds and hyposensitivity use thereof |
| US4880822A (en) * | 1987-04-24 | 1989-11-14 | Hoechst-Roussel Pharmaceuticals, Inc. | N-(pyridinyl)-1H-indol-1-amines |
| US4970218A (en) * | 1987-04-24 | 1990-11-13 | Hoechst-Roussel Pharmaceuticals Inc. | N-(pyridinyl)-1H-indol-1-amines |
| US5039811A (en) * | 1987-04-24 | 1991-08-13 | Hoechst-Roussel Pharmaceuticals Inc. | Preparation of N-(pyridinyl)-1H-indol-1-amines |
| US5550118A (en) * | 1994-01-31 | 1996-08-27 | Eli Lilly And Company | Polyhydronorharman synthase inhibitors |
| US5977125A (en) * | 1994-10-31 | 1999-11-02 | Eisai Co., Ltd. | Mono-or polyenic carboxylic acid derivatives |
| GB2295151B (en) * | 1994-11-18 | 1998-12-09 | Nmc | Polymerization of substituted heterocyclic monomers |
| BR9908165A (pt) * | 1998-02-23 | 2000-10-31 | Univ South Alabama | Processos de prevenção de um citotóxico de proteìna beta amilóide em células, de tratamento de uma fibrilogênica em um sujeito humano, de diminuição da oxidação em uma amostra biológica e de tratamento de doenças ou outros quadros em que radicais livres e/ou tensão oxidativa desempenham um papel, e, uso de ácido indol-3-propiÈnico ou um seu sal ou éster. |
| WO2003027107A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl oxazoles as c17,20 lyase inhibitors |
| BRPI0617271A2 (pt) * | 2005-10-11 | 2011-07-19 | Intermune Inc | inibidores de replicação viral |
| US20090047246A1 (en) * | 2007-02-12 | 2009-02-19 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| US8293781B2 (en) * | 2007-03-29 | 2012-10-23 | Daiichi Sankyo Company, Limited | Indole derivatives having cPLA2 inhibiting activity and applications and production methods of the same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449348A (en) * | 1968-01-08 | 1969-06-10 | Merck & Co Inc | Alpha-halomethyl-1-pyridine or quinoline carbonyl-3-indolylacetic acids |
| AT299938B (de) * | 1971-02-03 | 1972-07-10 | Italiana Sint Spa | Verfahren zur Herstellung des neuen Natriumsalzes der (1-Nicotinoyl-2-methyl-5-methoxy-3-indolyl)-essigsäure, gegebenenfalls im Gemisch mit der freien Säure |
| FR2171936B1 (ko) * | 1972-02-16 | 1975-04-25 | Clin Midy | |
| FR2171937A1 (en) * | 1972-02-16 | 1973-09-28 | Clin Midy | Aminoketo indoles - analgesics and antidepressants |
| AT323154B (de) * | 1973-02-02 | 1975-06-25 | Hurka Wilhelm | Verfahren zur herstellung von neuen 5-methoxy-2-methylindol-3-essigsäurederivaten sowie von deren salzen |
| DE2862340D1 (en) * | 1978-02-01 | 1983-11-24 | Wellcome Found | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
| US4322533A (en) * | 1980-03-17 | 1982-03-30 | Lesher George Y | 1H-Indole-2,3-dione derivatives |
| US4363912A (en) * | 1980-12-15 | 1982-12-14 | Pfizer Inc. | Indole thromboxane synthetase inhibitors |
| CS229934B2 (en) * | 1981-07-07 | 1984-07-16 | Pfizer | Production method subst.indolylacryte acid derivative |
| GB2102795A (en) * | 1981-07-31 | 1983-02-09 | Pfizer Ltd | Indole derivatives |
| US4478842A (en) * | 1981-11-19 | 1984-10-23 | Ciba-Geigy Corporation | N-Substituted-2-pyridylindoles |
| US4460777A (en) * | 1981-11-19 | 1984-07-17 | Ciba-Geigy Corporation | N-Substituted-2-pyridylindoles |
| US4511573A (en) * | 1983-05-17 | 1985-04-16 | Ciba-Geigy Corporation | 3-Substituted-2-(heteroaryl) indoles |
-
1983
- 1983-05-17 US US06/495,370 patent/US4536505A/en not_active Expired - Fee Related
-
1984
- 1984-05-14 FI FI841925A patent/FI841925A/fi not_active Application Discontinuation
- 1984-05-14 EP EP84105449A patent/EP0126401A1/de not_active Ceased
- 1984-05-15 IL IL71832A patent/IL71832A0/xx unknown
- 1984-05-15 GR GR74706A patent/GR79934B/el unknown
- 1984-05-15 PT PT78582A patent/PT78582A/pt unknown
- 1984-05-15 JP JP59095771A patent/JPS59212489A/ja active Pending
- 1984-05-16 AU AU28094/84A patent/AU2809484A/en not_active Abandoned
- 1984-05-16 KR KR1019840002658A patent/KR840009302A/ko not_active Application Discontinuation
- 1984-05-16 DK DK242484A patent/DK242484A/da not_active Application Discontinuation
- 1984-05-16 NO NO841958A patent/NO841958L/no unknown
- 1984-05-16 ZA ZA843677A patent/ZA843677B/xx unknown
- 1984-05-16 DD DD84263081A patent/DD224588A5/de unknown
- 1984-05-16 HU HU841893A patent/HUT34182A/hu unknown
- 1984-05-17 ES ES532572A patent/ES8602652A1/es not_active Expired
-
1985
- 1985-07-12 ES ES545151A patent/ES8604195A1/es not_active Expired
- 1985-07-12 ES ES545153A patent/ES8604197A1/es not_active Expired
- 1985-07-12 ES ES545154A patent/ES8604922A1/es not_active Expired
- 1985-07-12 ES ES545152A patent/ES8604196A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100807718B1 (ko) * | 2006-10-17 | 2008-02-28 | 한국생명공학연구원 | 인돌 유도체를 유효성분으로 함유하는 대사성 질환 예방 및치료용 약학적 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL71832A0 (en) | 1984-09-30 |
| US4536505A (en) | 1985-08-20 |
| ES532572A0 (es) | 1985-12-01 |
| JPS59212489A (ja) | 1984-12-01 |
| FI841925A0 (fi) | 1984-05-14 |
| ES8604196A1 (es) | 1986-01-16 |
| PT78582A (en) | 1984-06-01 |
| NO841958L (no) | 1984-11-19 |
| DK242484D0 (da) | 1984-05-16 |
| ES8604922A1 (es) | 1986-02-16 |
| ES545153A0 (es) | 1986-01-16 |
| ZA843677B (en) | 1985-02-27 |
| DK242484A (da) | 1984-11-18 |
| ES545154A0 (es) | 1986-02-16 |
| AU2809484A (en) | 1984-11-22 |
| ES8604195A1 (es) | 1986-01-16 |
| ES8602652A1 (es) | 1985-12-01 |
| EP0126401A1 (de) | 1984-11-28 |
| ES545151A0 (es) | 1986-01-16 |
| ES8604197A1 (es) | 1986-01-16 |
| DD224588A5 (de) | 1985-07-10 |
| ES545152A0 (es) | 1986-01-16 |
| HUT34182A (en) | 1985-02-28 |
| FI841925A (fi) | 1984-11-18 |
| GR79934B (ko) | 1984-10-31 |
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