KR860008976A - 2-(4-벤조일-1- 피페리딜)-1- 페닐알칸올 유도체 - Google Patents
2-(4-벤조일-1- 피페리딜)-1- 페닐알칸올 유도체 Download PDFInfo
- Publication number
- KR860008976A KR860008976A KR1019860003714A KR860003714A KR860008976A KR 860008976 A KR860008976 A KR 860008976A KR 1019860003714 A KR1019860003714 A KR 1019860003714A KR 860003714 A KR860003714 A KR 860003714A KR 860008976 A KR860008976 A KR 860008976A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- process according
- salt
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 4-benzoyl-1-piperidyl Chemical group 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- AGAVKPLLEUXKPI-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)piperidine Chemical compound O1CCOC1N1CCCCC1 AGAVKPLLEUXKPI-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D211/36—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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- (a) 일반식(Ⅴ)(여기서 R은 수소 또는 메틸이고 R1은 비치환 페닐, 4-메톡시-3,5-디메틸페닐 또는 2-, 3-또는 4-위치중 하나에서 할로겐, C1-4알킬, C1-4알콕시, 히드록시, 벤질옥시, 트리플루오로메틸, 시아노, 니트로, 아미노, 아세틸아미노, 메틸티오, 메틸술포닐 또는 아미노술포닐에 의해 치환된 페닐이고 R2는 비치환 페닐, 2,4,6-트리메톡시페닐 또는 3-또는 4-위치중 하나에서 불소, 염소, 메틸 또는 메톡시에 의해 치환된페닐이다)의 화합물을 산으로 처리하거나 또는 (b) 일반식 (Ⅵ)의 화합물을 일반식 (Ⅵ)의 화합물과 반응시키고 그리하여 형성된 일반식(I)(상기 Ⅵ,Ⅶ 및 I식에서 R,R1및 R2는 일반식 Ⅴ에서 정의 한 대로이다)의 화합물을 그후 임의적으로 더 어상의 일반식(I)의 화합물로 전환시키거나 또는 일반식(I)의 염기를 해당염으로 전환시이거나 또는 염을 일반식(I)의 해당염기로 전키시키는 것으로 이루어지는 것을 특징으로 하는 일반식(I)의 화합물또는 그의 산부가 염의 제조방법.
- 제1항에 있어서, R1은 할로게노페닐 도는 알킬페닐이고 R2는 플루오로페닐인 것을 특징으로 하는 제조방법.
- 제1항에 있어서, 제약상 허용되는 산과의 산부가 염의 형태인 것을 특징으로 하는 제조방법.
- 제1항 내지 제3항중 어느 하나에 있어서, 순수한 광학이성질체의 형태인 것을 특징으로 하는 제조방법.
- 일반식(Ⅱ)(여기서 R 및 R1은 제1항에서 정의한 바와 같고 X는 염소 또는 브롬이다)의 화합물을 일반식(Ⅲ)(여기서 R2는 제1항에서 정의한 바와 같다)의 화합물과 반응시킴으로써 임의적으로 염의 형태로 일반식 (Ⅳ)의 화합물을 생성시킨 다음 일반식 (Ⅳ)의 화합물을 환원시킴으로써 일반식(Ⅴ)의 화합물을 얻는 것을 특징으로 하는 일반식 (Ⅴ)의 화합물의 제조방법.
- 제5항에 있어서, 할로겐화케톤(Ⅲ)을 염의 형태인 디옥솔라닐피페리딘(Ⅳ)과 용매중에서 염기의 존재하에 반응시키는 것을 특징으로 하는 제조방법.
- 제5항 또는 제6항에 있어서, 화합물(Ⅳ)을 수소 화붕소 알칼리금속에 의해 환원시키는 것을 특징으로 하는 제조방법.
- 제7항에 있어서, 아세트산의 존재하에 환원을 수행하는 것을 특징으로 하는 제조방법.
- 제8항에 있어서, 산의 부재하에 환원을 수행하는 것을 특징으로 하는 제조방법.
- 제1항의 제조방법에 의해 제조되는 모든 일반식(Ⅰ)의 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR85/07270 | 1985-05-14 | ||
| FR8507270A FR2581993B1 (fr) | 1985-05-14 | 1985-05-14 | Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR860008976A true KR860008976A (ko) | 1986-12-19 |
Family
ID=9319247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860003714A Withdrawn KR860008976A (ko) | 1985-05-14 | 1986-05-13 | 2-(4-벤조일-1- 피페리딜)-1- 페닐알칸올 유도체 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4711899A (ko) |
| EP (1) | EP0202164B1 (ko) |
| JP (1) | JPS61260063A (ko) |
| KR (1) | KR860008976A (ko) |
| AT (1) | ATE40684T1 (ko) |
| AU (1) | AU584701B2 (ko) |
| DE (1) | DE3662044D1 (ko) |
| DK (1) | DK220386A (ko) |
| ES (2) | ES8802138A1 (ko) |
| FI (1) | FI861995A7 (ko) |
| FR (1) | FR2581993B1 (ko) |
| GR (1) | GR861253B (ko) |
| HU (1) | HU195640B (ko) |
| IL (1) | IL78773A (ko) |
| NO (1) | NO861897L (ko) |
| NZ (1) | NZ216145A (ko) |
| PT (1) | PT82569B (ko) |
| ZA (1) | ZA863533B (ko) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| JP2573195B2 (ja) * | 1986-09-30 | 1997-01-22 | エーザイ株式会社 | 環状アミン誘導体 |
| US4870083A (en) * | 1987-11-24 | 1989-09-26 | Merrell Dow Pharmaceuticals Inc. | 1,4-Disubstituted-piperidinyl compounds useful as analgesics and muscle relaxants |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5166211A (en) * | 1987-12-17 | 1992-11-24 | Merrell Dow Pharmaceuticals Inc. | Method of using 1,4-disubstituted piperidinyl compounds in the treatment of coronary vasospasons and variant angina |
| US5064838A (en) * | 1988-01-21 | 1991-11-12 | Merrell Dow Pharmaceuticals | 1,4-disubstituted-piperidinyl compounds as pain relievers |
| FR2634206B1 (fr) * | 1988-07-12 | 1992-05-15 | Synthelabo | Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2 et quinoleinones-2, leur preparation et leur application en therapeutique |
| FR2640266B2 (fr) * | 1988-07-12 | 1992-07-10 | Synthelabo | Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2, quinoleinones-2, benzo(b)azepinones-2 et benzimidazolones-2, leur preparation et leur application en therapeutique |
| GB8823775D0 (en) * | 1988-10-11 | 1988-11-16 | Scras | New 2-carbonyl substituted n n'-di-(trimethoxybenzoyl)piperazines |
| GB8823776D0 (en) * | 1988-10-11 | 1988-11-16 | Scras | New 2-methoxycarbonyl sustituted n n'-di-(trimethoxybenzoyl)piperazines |
| US4994460A (en) * | 1989-06-01 | 1991-02-19 | Bristol-Myers Squibb Co. | Agents for treatment of brain ischemia |
| US5055470A (en) * | 1989-06-01 | 1991-10-08 | Bristol-Myers Squibb Co. | Method of treatment of ischemia in brain |
| NZ236501A (en) * | 1989-12-21 | 1992-12-23 | Merrell Dow Pharma | Piperidine derivatives and antithrombotic compositions |
| US5292752A (en) * | 1989-12-21 | 1994-03-08 | Merrell Dow Pharmaceuticals Inc. | Antithrombotic compounds |
| US5306723A (en) * | 1990-05-10 | 1994-04-26 | Pfizer Inc. | Neuroprotective indolone and related derivatives |
| CA2084082C (en) * | 1990-06-07 | 2002-03-19 | Albert A. Carr | 1-pyperidinyl alkanoylarysulfonamide derivatives |
| US5478846A (en) * | 1990-06-07 | 1995-12-26 | Merrell Dow Pharmaceuticals Inc. | 1-piperidinyl alkanoylanyl sulfonamides for treatment of cardiac arrhythmia |
| US5512584A (en) * | 1991-04-16 | 1996-04-30 | Basf Aktiengesellschaft | 1,3,4-trisubstituted piperidine derivatives, the preparation and use thereof |
| FR2678269B1 (fr) * | 1991-06-27 | 1995-01-13 | Synthelabo | Derives de 1-(4-chlorophenyl)-2-[4-(2-phenylethyl)piperidin-1-yl]ethanol, leur application et leur preparation en therapeutique. |
| FR2688504B1 (fr) * | 1992-03-13 | 1995-05-05 | Synthelabo | Derives de 2-(piperidin-1-yl)ethanol, leur preparation et leur application en therapeutique. |
| US5436255A (en) * | 1992-07-23 | 1995-07-25 | Pfizer Inc. | Method of treating diseases susceptable to treatment by blocking NMDA-receptors |
| US5498610A (en) * | 1992-11-06 | 1996-03-12 | Pfizer Inc. | Neuroprotective indolone and related derivatives |
| NZ275151A (en) * | 1994-01-31 | 1998-02-26 | Pfizer | 3r*4s*3-[4-(4-fluorophenyl)-4-hydroxy-piperidin-1-yl]-chroman-4 ,7-diol; isomers and salts |
| FR2737494B1 (fr) * | 1995-08-04 | 1997-08-29 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leur application en therapeutique |
| US6770659B2 (en) * | 2002-08-26 | 2004-08-03 | Sk Corporation | Benzoyl piperidine compounds |
| US20050158270A1 (en) * | 2004-01-15 | 2005-07-21 | Seren Frantz | Pearlizer concentrate and its use in personal care compositions |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH491917A (de) * | 1968-01-11 | 1970-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| US3632767A (en) * | 1968-02-12 | 1972-01-04 | Mallinckrodt Chemical Works | Treatment of depression with 4-substituted piperidines |
| US3576810A (en) * | 1968-06-20 | 1971-04-27 | Robins Co Inc A H | 1-substituted-3-(-4)-aroylpiperidines |
| BE791088A (fr) * | 1971-11-09 | 1973-03-01 | Richardson Merrell Inc | Nouveaux derives d'aryl (piperidyl-4) cetone, utiles notamment comme analgesiques et anticoagulants, et leur procede de preparation |
| US4101662A (en) * | 1973-05-03 | 1978-07-18 | A. H. Robins Company, Incorporated | Method for inhibiting emesis and compositions therefor |
| GB1535791A (en) * | 1975-05-07 | 1978-12-13 | Ferrosan Ab | Derivatives of 4-piperidinol |
| US4035369A (en) * | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| CH602642A5 (ko) * | 1975-11-14 | 1978-07-31 | Orgamol Sa | |
| FR2408602A2 (fr) * | 1977-11-15 | 1979-06-08 | Synthelabo | Nouveaux derives de piperidine et leur methode de preparation |
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| US4198419A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenylthiophenylpiperidines |
| US4443451A (en) * | 1981-07-15 | 1984-04-17 | Janssen Pharmaceutica N.V. | Bicyclic pyrimidin-5-one derivatives |
| FR2534580A1 (fr) * | 1982-10-13 | 1984-04-20 | Synthelabo | Derives de phenyl-1 piperidino-2 propanol, leur preparation, et medicaments qui les contiennent |
| DK159420C (da) * | 1983-03-09 | 1991-03-11 | Ciba Geigy Ag | N-(piperidinyl-alkyl)-carboxamider og salte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelsen af forbindelserne til fremstilling af antipsykotiske farmaceutiske praeparater |
| US4458076A (en) * | 1983-05-31 | 1984-07-03 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
-
1985
- 1985-05-14 FR FR8507270A patent/FR2581993B1/fr not_active Expired
-
1986
- 1986-05-12 DE DE8686401000T patent/DE3662044D1/de not_active Expired
- 1986-05-12 EP EP86401000A patent/EP0202164B1/fr not_active Expired
- 1986-05-12 AT AT86401000T patent/ATE40684T1/de active
- 1986-05-13 JP JP61110463A patent/JPS61260063A/ja active Pending
- 1986-05-13 NO NO861897A patent/NO861897L/no unknown
- 1986-05-13 KR KR1019860003714A patent/KR860008976A/ko not_active Withdrawn
- 1986-05-13 HU HU861975A patent/HU195640B/hu not_active IP Right Cessation
- 1986-05-13 NZ NZ216145A patent/NZ216145A/xx unknown
- 1986-05-13 IL IL78773A patent/IL78773A/xx unknown
- 1986-05-13 US US06/862,715 patent/US4711899A/en not_active Expired - Fee Related
- 1986-05-13 ES ES554895A patent/ES8802138A1/es not_active Expired
- 1986-05-13 DK DK220386A patent/DK220386A/da not_active Application Discontinuation
- 1986-05-13 AU AU57406/86A patent/AU584701B2/en not_active Ceased
- 1986-05-13 GR GR861253A patent/GR861253B/el unknown
- 1986-05-13 ZA ZA863533A patent/ZA863533B/xx unknown
- 1986-05-13 FI FI861995A patent/FI861995A7/fi not_active Application Discontinuation
- 1986-05-13 PT PT82569A patent/PT82569B/pt unknown
-
1987
- 1987-06-08 ES ES557582A patent/ES8801631A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HUT40790A (en) | 1987-02-27 |
| DK220386A (da) | 1986-11-15 |
| ZA863533B (en) | 1986-12-30 |
| FI861995A0 (fi) | 1986-05-13 |
| ATE40684T1 (de) | 1989-02-15 |
| FR2581993A1 (fr) | 1986-11-21 |
| AU5740686A (en) | 1986-11-20 |
| NO861897L (no) | 1986-11-17 |
| AU584701B2 (en) | 1989-06-01 |
| PT82569B (fr) | 1988-04-12 |
| ES557582A0 (es) | 1988-02-16 |
| ES8801631A1 (es) | 1988-02-16 |
| GR861253B (en) | 1986-09-10 |
| US4711899A (en) | 1987-12-08 |
| ES8802138A1 (es) | 1988-04-01 |
| PT82569A (fr) | 1986-06-01 |
| ES554895A0 (es) | 1988-04-01 |
| FI861995A7 (fi) | 1986-11-15 |
| HU195640B (en) | 1988-06-28 |
| JPS61260063A (ja) | 1986-11-18 |
| EP0202164A1 (fr) | 1986-11-20 |
| DE3662044D1 (en) | 1989-03-16 |
| EP0202164B1 (fr) | 1989-02-08 |
| NZ216145A (en) | 1988-10-28 |
| DK220386D0 (da) | 1986-05-13 |
| FR2581993B1 (fr) | 1988-03-18 |
| IL78773A (en) | 1990-09-17 |
| IL78773A0 (en) | 1986-08-31 |
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