KR850001178A - 류코트리엔 길항제의 제조방법 - Google Patents
류코트리엔 길항제의 제조방법 Download PDFInfo
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- KR850001178A KR850001178A KR1019840004213A KR840004213A KR850001178A KR 850001178 A KR850001178 A KR 850001178A KR 1019840004213 A KR1019840004213 A KR 1019840004213A KR 840004213 A KR840004213 A KR 840004213A KR 850001178 A KR850001178 A KR 850001178A
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- South Korea
- Prior art keywords
- compound
- formula
- propyl
- alkyl
- pharmaceutically nontoxic
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- 238000000034 method Methods 0.000 title claims 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- 231100000252 nontoxic Toxicity 0.000 claims 10
- 230000003000 nontoxic effect Effects 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- -1 alkali metal azide Chemical class 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- FDBJFCYJEZHEDJ-UHFFFAOYSA-N 4-[(3,4-dichloro-2-propylphenyl)methoxy]butanoic acid Chemical compound CCCC1=C(Cl)C(Cl)=CC=C1COCCCC(O)=O FDBJFCYJEZHEDJ-UHFFFAOYSA-N 0.000 claims 1
- QQNDRADNZAEJDE-UHFFFAOYSA-N 5-(3,4-dichloro-2-propylphenoxy)pentanoic acid Chemical compound CCCC1=C(Cl)C(Cl)=CC=C1OCCCCC(O)=O QQNDRADNZAEJDE-UHFFFAOYSA-N 0.000 claims 1
- DGFYQWSHQSVNLY-UHFFFAOYSA-N 5-[2-[(3,4-dichloro-2-propylphenyl)methoxy]ethylsulfanyl]-2h-tetrazole Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1COCCSC1=NN=NN1 DGFYQWSHQSVNLY-UHFFFAOYSA-N 0.000 claims 1
- LQCSJTSLGVAGCA-UHFFFAOYSA-N 5-[3-(3,4-dichloro-2-propylphenoxy)propylsulfanyl]-2h-tetrazole Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1OCCCSC1=NN=NN1 LQCSJTSLGVAGCA-UHFFFAOYSA-N 0.000 claims 1
- HFAMIADRMRGPIU-UHFFFAOYSA-N 5-[3-[(3,4-dichloro-2-propylphenyl)methoxy]propyl]-2h-tetrazole Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1COCCCC1=NN=NN1 HFAMIADRMRGPIU-UHFFFAOYSA-N 0.000 claims 1
- QXNMEKNZLUTDKZ-UHFFFAOYSA-N 5-[4-(3,4-dichloro-2-propylphenoxy)butyl]-2h-tetrazole Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1OCCCCC1=NNN=N1 QXNMEKNZLUTDKZ-UHFFFAOYSA-N 0.000 claims 1
- GRMMUEYETVGCCQ-UHFFFAOYSA-N 5-[4-(3,4-dichloro-2-propylphenyl)butylsulfanyl]-2h-tetrazole Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1CCCCSC1=NN=NN1 GRMMUEYETVGCCQ-UHFFFAOYSA-N 0.000 claims 1
- HWJROAIGJYKEHW-UHFFFAOYSA-N 6-(3,4-dichloro-2-propylphenyl)hexanoic acid Chemical compound CCCC1=C(Cl)C(Cl)=CC=C1CCCCCC(O)=O HWJROAIGJYKEHW-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1786—Unsaturated ethers containing hydroxy or O-metal groups containing halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 일반식(II)의 화합물을 일반식(III)의 화합물과 반응시켜 Y가 S 또는 O인 일반식(I)의 화합물을 수득하거나, 일반식(VIII)의 화합물을 일반식(IX)의 화합물과 반응시켜 Z가 O 또는 S인 일반식(I)의 화합물을 수득하거나, 일반식(XIII)의 화합물을 일반식(XIV)의 화합물과 반응시켜 Y-Z가 -CH=CH-인 일반식(I)의 화합물을 수득하거나, 일반식(XVI)의 화합물을 일반식(XVII)의 화합물과 반응시켜 Y-Z가 -CH=CH-인 일반식(I)의 화합물과 수득하거나, D가 CN인 일반식(I)의 화합물을 알칼리금속아지드 및 염화암모늄과 반응시키거나 테트라메틸구아니디늄아지드와 반응시켜 D가 5-테트라졸릴인 일반식(I)의 화합물을 수득하거나, 일반식(IV)의 화합물을 알칼리금속시아나이드 또는 알칼리금속티오시아네이트와 반응시켜 D가 CN 또는 SCN인 일반식(I)의 화합물을 수득하거나, D'가 할로인 일반식(IV)의 화합물을 5-머캅토테트라졸과 반응시켜 D가 티오테트라졸인 일반식(I)의 화합물을 수득하거나, Y 또는 Z가 S 또는 SO인 일반식(I)의 화합물을 산화시켜, Y 또는 Z가 SO 또는 SO2인 상응하는 일반식(I)의 화합물을 수득한후, 임의로 수득된 일반식(I)의 화합물을 염화시킴을 특징으로 하여, 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 염을 제조하는 방법.상기 식에서, R1은(R는 수소, C1-C6알킬, C3-C8시클로알킬이거나, 할로, C1-C4알킬 또는 C1-C4알콕시로 임의 치환된 페닐기이다) 또는 할로이고, R2는 할로 또는 히드록시이고, R3는 C1-C12알킬, 히드록시-치환된 C1-C12알킬 또는 C2-C6알케닐이고, Y는 -0-,(P는 0,1 또는 2이다) 또는 -CR6R7-(R6및 R7은 각각 수소, C1-C10알킬, 페닐 또는 벤질이다)이고, 단, 일반식(II) 및 (IV)에서, Y는 S 또는 O이고, Z는 -0-,또는 -CR8R9-(R8및 R9은 각각 수소, C1-C10알킬, 페닐 또는 벤질이다)이거나, 함께일 경우, -Y-Z 는 -CH=CH-이고, n은 1 내지 10이고, D는 CN, SCN 또는 QR4[여기에서, Q는 -0-, -NR-(R은 수소 또는 C1-C3알킬이다),또는 하나의 결합이고, R4는 -COR10<R10은 히드록시, C1-C4알콕시, -NHOH 또는 -NR11R12(R11및 R12는 각각 수소 또는 C1-C3알킬이거나, R11및 R12는 질소원자와 함께 몰폴린 또는 N-메틸피페라진환을 형성한다)이다>, 히드록시, NR11R12, -SC(=NH)NH2또는이다]이며, 단, a) R1이일 경우, R2가 히드록시일 수 없고, b) Y 및 Z중의 하나가 -0- 또는일 경우, 다른 하나가 -0- 또는일 수 없고, c) R4가 COR10, 히드록시, -NR11R12또는 -SC(=NH)NH2일 경우, Q는 하나의 결합일 수만 있으며, X는 이탈그룹이고, V 및 W중의 하나는 이탈그룹이고, 다른 하나는 -ZH(Z는 O 또는 S이다)이고, X' 및 D'는 할로이다.
- 제1항에 있어서, D가 QR4인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 5-(2-프로필-3,4-디클로로페녹시)펜타노산 또는 이의 약제학적으로 무독한 염, 4-(2-프로필-3,4-디클로로벤질옥시)부타노산 또는 이의 약제학적으로 무독한 염, 6-(2-프로필-3,4-디클로로페닐)헥사노산 또는 이의 약제학적으로 무독한 염, 5-[4-(2-프로필-3,4-디클로로페녹시)부틸]-테트라졸 또는 이의 약제학적으로 무독한 염, 5-[3-(2-프로필-3,4-디클로로벤질옥시)프로필]-테트라졸 또는 이의 약제학적으로 무독한 염, 5-[5-(2-프로필)-3,4-디클로로페닐)펜틸]-테트라졸 또는 이의 약제학적으로 무독한 염, 5-[3-(2-프로필-3,4-디클로로페녹시)프로필티오]-테트라졸 또는 이의 약제학적으로 무독한 염, 5-[2-(2-프로필-3,4-디클로로벤질옥시)에틸티오]-테트라졸 또는 이의 약제학적으로 무독한 염, 또는 5-[4-(2-프로필-3,4-디클로로페닐)부틸티오]-테트라졸 또는 이의 약제학적으로 무독한 염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51439483A | 1983-07-18 | 1983-07-18 | |
| US514394 | 1983-07-18 | ||
| US514,394 | 1983-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850001178A true KR850001178A (ko) | 1985-03-16 |
| KR860001980B1 KR860001980B1 (ko) | 1986-11-07 |
Family
ID=24046947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004213A KR860001980B1 (ko) | 1983-07-18 | 1984-07-18 | 류코트리엔 길항제의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0132367B1 (ko) |
| JP (1) | JPS6051138A (ko) |
| KR (1) | KR860001980B1 (ko) |
| AT (1) | ATE34972T1 (ko) |
| AU (1) | AU571244B2 (ko) |
| CA (1) | CA1242195A (ko) |
| DE (1) | DE3471924D1 (ko) |
| DK (1) | DK349084A (ko) |
| ES (1) | ES534267A0 (ko) |
| FI (1) | FI842843A (ko) |
| GB (1) | GB2144123B (ko) |
| GR (1) | GR81524B (ko) |
| HU (1) | HU198192B (ko) |
| IL (1) | IL72385A (ko) |
| NZ (1) | NZ208879A (ko) |
| PH (1) | PH21019A (ko) |
| PT (1) | PT78920B (ko) |
| ZA (1) | ZA845407B (ko) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143931A (en) * | 1982-06-24 | 1992-09-01 | Smithkline Beecham Corporation | Leukotriene antagonists containing tetrazolyl groups |
| US5105017A (en) * | 1983-07-18 | 1992-04-14 | Eli Lilly And Company | Leukotriene antagonist intermediates |
| US4939279A (en) * | 1985-04-19 | 1990-07-03 | Smithkline Beecham Corporation | Leukotriene antagonists |
| US4874792A (en) * | 1985-04-19 | 1989-10-17 | Smithkline Beckman Corporation | Thiophenyl Alkanoic acids useful as leukotriene antagonists |
| US4937253A (en) * | 1985-04-19 | 1990-06-26 | Smithkline Beecham Corporation | Ester prodrugs |
| DE3518655A1 (de) * | 1985-05-24 | 1986-11-27 | Grünenthal GmbH, 5190 Stolberg | Neue phenolderivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel |
| US4737493A (en) | 1985-07-01 | 1988-04-12 | Warner-Lambert Company | 7-((substituted)amino)-8-((substituted)carbonyl)-methylamino)-1-oxaspiro(4,5)decanes as analgesic agents |
| PT81492B (pt) * | 1985-09-17 | 1988-03-03 | Ciba Geigy Ag | Processo para a preparacao de novos eteres de resorcina fluorados |
| US4808604A (en) * | 1985-10-03 | 1989-02-28 | Ciba-Geigy Corporation | N-(substituted phenyl) tetrazol-5-yl carboxamides and anti-allergic use thereof |
| PT81374B (pt) * | 1985-10-25 | 1988-02-17 | Ciba Geigy Ag | Processo para a preparacao de novos eteres da resorcina |
| US4801616A (en) * | 1986-03-25 | 1989-01-31 | Eli Lilly And Company | Diphenylmethanone compounds and anti-inflammatory use thereof |
| US5171882A (en) * | 1987-01-12 | 1992-12-15 | Eli Lilly And Company | Leukotriene antagonists |
| US4992576A (en) * | 1987-01-12 | 1991-02-12 | Eli Lilly And Company | Intermediates for leukotriene antagonists |
| US5235064A (en) * | 1987-01-12 | 1993-08-10 | Eli Lilly And Company | Leukotriene antagonists |
| US5294613A (en) * | 1987-01-12 | 1994-03-15 | Eli Lilly And Company | Method of treating endotoxic shock in mammals |
| US4973731A (en) * | 1987-04-23 | 1990-11-27 | Riker Laboratories, Inc. | Di-t-butylphenyl alkyl and benzyl ether nitriles |
| US5314918A (en) * | 1987-06-24 | 1994-05-24 | Smithkline Beecham Corporation | Leukotriene antagonists |
| PT87616B (pt) * | 1987-06-24 | 1992-09-30 | Smithkline Beecham Corp | Processo de preparacao de antagonistas do leucotrieno e de composicoes farmaceuticas |
| US5066822A (en) * | 1987-11-13 | 1991-11-19 | Riker Laboratories, Inc | Di-t-butylphenols substituted by an alkoxy or benzyloxy group or a benzylthio group |
| US4968710A (en) * | 1987-11-13 | 1990-11-06 | Riker Laboratories, Inc. | Substituted di-t-butylphenols and anti-allergic use thereof |
| US4954513A (en) * | 1988-12-23 | 1990-09-04 | Smithkline Beecham Corporation | Leukotriene antagonists |
| DE4028866A1 (de) * | 1990-09-07 | 1992-03-12 | Schering Ag | Neue leukotrien-b(pfeil abwaerts)4(pfeil abwaerts)-antagonisten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB743513A (en) * | 1952-10-08 | 1956-01-18 | Ca Nat Research Council | Method for introducing water into vulcanizable compositions |
| NL95401C (ko) * | 1954-07-06 | |||
| NL90237C (ko) * | 1955-01-10 | |||
| GB804565A (en) * | 1956-08-31 | 1958-11-19 | George Whiteley Kitchingman | Manufacture of ª†-(4-chloro-2-methylphenoxy)-n-butyric acid and ª†-(2:4-dichlorophenoxy)-n-butyric acid |
| GB810154A (en) * | 1956-11-28 | 1959-03-11 | Monsanto Chemicals | Preparation of chlorinated aryloxybutyric acids |
| GB793230A (en) * | 1956-12-31 | 1958-04-09 | Shell Res Ltd | Improvements in or relating to the preparation of gamma-phenoxybutyric acids and salts thereof |
| DE1124296B (de) * | 1958-03-28 | 1962-02-22 | Amchem Prod | Herbicide Mittel und Verfahren zur Herstellung der Wirkstoffe in ihren Loesungen in OElen |
| GB883255A (en) * | 1958-04-03 | 1961-11-29 | Ici Australia Ltd | Preparation of chloro-substituted gamma-phenoxy butyric acids |
| US3379752A (en) * | 1964-05-20 | 1968-04-23 | Merck & Co Inc | Phenoxy substituted 3-hydroxyalkanoic acids and a method for their preparation |
| BR6679625D0 (pt) * | 1965-05-27 | 1973-10-23 | Merck & Co Inc | Processo para preparar acidos carboxilicos |
| GB1591063A (en) * | 1977-07-11 | 1981-06-10 | Ici Ltd | Monoalkylation of dihydroxybenzenes |
| FR2509725A1 (fr) * | 1981-07-15 | 1983-01-21 | Choay Sa | (hydroxyalkyl)phenylsulfures, leurs procedes de preparation et compositions pharmaceutiques les contenant |
| US5105017A (en) * | 1983-07-18 | 1992-04-14 | Eli Lilly And Company | Leukotriene antagonist intermediates |
-
1984
- 1984-07-11 IL IL72385A patent/IL72385A/xx unknown
- 1984-07-11 GR GR75277A patent/GR81524B/el unknown
- 1984-07-11 CA CA000458595A patent/CA1242195A/en not_active Expired
- 1984-07-12 ZA ZA845407A patent/ZA845407B/xx unknown
- 1984-07-12 NZ NZ208879A patent/NZ208879A/en unknown
- 1984-07-12 ES ES534267A patent/ES534267A0/es active Granted
- 1984-07-13 PH PH30978A patent/PH21019A/en unknown
- 1984-07-16 PT PT78920A patent/PT78920B/pt unknown
- 1984-07-16 FI FI842843A patent/FI842843A/fi not_active Application Discontinuation
- 1984-07-17 DE DE8484304858T patent/DE3471924D1/de not_active Expired
- 1984-07-17 HU HU842783A patent/HU198192B/hu unknown
- 1984-07-17 DK DK349084A patent/DK349084A/da not_active Application Discontinuation
- 1984-07-17 EP EP84304858A patent/EP0132367B1/en not_active Expired
- 1984-07-17 AT AT84304858T patent/ATE34972T1/de not_active IP Right Cessation
- 1984-07-17 AU AU30752/84A patent/AU571244B2/en not_active Ceased
- 1984-07-17 GB GB08418173A patent/GB2144123B/en not_active Expired
- 1984-07-18 KR KR1019840004213A patent/KR860001980B1/ko active IP Right Grant
- 1984-07-18 JP JP59151109A patent/JPS6051138A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR860001980B1 (ko) | 1986-11-07 |
| FI842843A (fi) | 1985-01-19 |
| PH21019A (en) | 1987-06-30 |
| ES8600259A1 (es) | 1985-10-01 |
| FI842843A0 (fi) | 1984-07-16 |
| ZA845407B (en) | 1986-02-26 |
| AU571244B2 (en) | 1988-04-14 |
| DE3471924D1 (en) | 1988-07-14 |
| CA1242195A (en) | 1988-09-20 |
| IL72385A (en) | 1988-03-31 |
| NZ208879A (en) | 1987-03-31 |
| PT78920B (en) | 1986-10-23 |
| PT78920A (en) | 1984-08-01 |
| GB2144123A (en) | 1985-02-27 |
| DK349084A (da) | 1985-01-19 |
| ES534267A0 (es) | 1985-10-01 |
| HU198192B (en) | 1989-08-28 |
| ATE34972T1 (de) | 1988-06-15 |
| EP0132367A2 (en) | 1985-01-30 |
| AU3075284A (en) | 1985-01-24 |
| DK349084D0 (da) | 1984-07-17 |
| GB2144123B (en) | 1987-06-10 |
| EP0132367B1 (en) | 1988-06-08 |
| JPS6051138A (ja) | 1985-03-22 |
| GR81524B (ko) | 1984-12-11 |
| HUT45961A (en) | 1988-09-28 |
| EP0132367A3 (en) | 1985-05-15 |
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