KR920002607A - 테트라히드로티에노[3,2-c] 피리딘의 n- 페닐아세트 유도체 제조방법 및 그의 화학 중간 생성물 - Google Patents
테트라히드로티에노[3,2-c] 피리딘의 n- 페닐아세트 유도체 제조방법 및 그의 화학 중간 생성물 Download PDFInfo
- Publication number
- KR920002607A KR920002607A KR1019910011791A KR910011791A KR920002607A KR 920002607 A KR920002607 A KR 920002607A KR 1019910011791 A KR1019910011791 A KR 1019910011791A KR 910011791 A KR910011791 A KR 910011791A KR 920002607 A KR920002607 A KR 920002607A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- process according
- compound
- group
- formylating agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- OJYDKYKQCVPTFG-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-c]pyridine Chemical class C1N=CC=C2SCCC21 OJYDKYKQCVPTFG-UHFFFAOYSA-N 0.000 title 1
- 239000000126 substance Substances 0.000 title 1
- 239000002253 acid Substances 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000003839 salts Chemical group 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000001351 cycling effect Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical group 0.000 claims 1
- PAOGEKGFTGONII-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-2-(2-thiophen-2-ylethylamino)acetate Chemical compound C=1C=CC=C(Cl)C=1C(C(=O)OC)NCCC1=CC=CS1 PAOGEKGFTGONII-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 하기 일반식(Ⅰ)의 화합물을 제조하기 위해서, 포르밀화제를 하기 일반식(Ⅱ)화합물과 반응시키고 형성된 화합물이 산의 존재하에 사이클화 되는 것을 특징으로 하는 화합물 제조방법.
- 제1항에 있어서, 상기 일반식(Ⅱ) 화합물의 거울상 이성질체들중 하나를 상기 일반식(Ⅰ)화합물 하나의 거울상 이성질체를 얻기위해 반응시키는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 포르밀화제가 포름알데히드, 그의 수화물 또는 그의 중합체 형태, X가 할로겐원자 C1-C4알콕시기, C1-C4알킬티오기 또는 아미노기이고, Y는 C1-C4알콕시기, C1-C4알킬티오기, 아미노기 또는 C2-C5알콕시-카르보닐 또는 페녹시카르보닐기 및 Z가 O,S,NH인 하기 일반식의 헤테로시클릭 화합물들로 부터 선택되는 것을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 포르밀화제가 포름알데히드, 그의 수화물 또는 그의 중합체 형태인것을 특징으로하는 방법.
- 제1항 내지 제4항중 어느 한항에 있어서, 산은 무기산이고 포르밀화후에 첨가되는 것을 특징으로 하는 방법.
- 제5항에 있어서, 사이클화가 강한 무기산 및 디메틸포름아미드 존재하에 수행되는 것을 특징으로 하는 방법.
- 제1항 내지 제4항중 어느 한항에 있어서, 산이 유기산이라는 것을 특징으로하는 방법.
- 제7항에 있어서, 산이 포름산이고 또한 반응에 대한 용매로 채택된다는 것을 특징으로 하는 방법.
- 제1항중 내지 제4항중 어느 한항에 있어서, 산이 상기 화합물 Ⅱ와 함께 그의 염 형태로 도입되는 강산인것을 특징으로 하는 방법.
- 라세믹 메틸 알파-(2-티에닐에틸아미노) (2-클로로페닐) 아세테이트 및 그의 염.
- 우회전성 메틸 알파-(2-티에닐에틸아미노) (2-클로로페닐) 아세테이트 및 그의 염.
- 좌회전성 메틸 알파-(2-티에닐에틸아미노) (2-클로로페닐) 아세테이트 및 그의 염.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9008749 | 1990-07-10 | ||
FR909008749A FR2664596B1 (fr) | 1990-07-10 | 1990-07-10 | Procede de preparation d'un derive n-phenylacetique de tetrahydrothieno [3,2-c] pyridine et son intermediaire de synthese. |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920002607A true KR920002607A (ko) | 1992-02-28 |
KR100198503B1 KR100198503B1 (ko) | 1999-06-15 |
Family
ID=9398542
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910011791A KR100198503B1 (ko) | 1990-07-10 | 1991-07-09 | 테트라히드로티에노 (3,2-c) 피리딘의 n-페닐아세트 유도체 제조방법 및 그의 화학 중간 생성물 |
Country Status (16)
Country | Link |
---|---|
US (1) | US5204469A (ko) |
EP (1) | EP0466569B1 (ko) |
JP (1) | JP2945174B2 (ko) |
KR (1) | KR100198503B1 (ko) |
AT (1) | ATE136899T1 (ko) |
AU (1) | AU645816B2 (ko) |
CA (1) | CA2046482C (ko) |
DE (1) | DE69118765T2 (ko) |
DK (1) | DK0466569T3 (ko) |
ES (1) | ES2086505T3 (ko) |
FR (1) | FR2664596B1 (ko) |
GR (1) | GR3020434T3 (ko) |
HU (1) | HU215957B (ko) |
IE (1) | IE73222B1 (ko) |
PL (1) | PL172216B1 (ko) |
PT (1) | PT98244B (ko) |
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FI101150B (fi) * | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
US5576328A (en) * | 1994-01-31 | 1996-11-19 | Elf Sanofi | Method for the secondary prevention of ischemic events |
FR2760456B1 (fr) * | 1997-03-05 | 2000-05-12 | Sanofi Sa | Procede de preparation de derives de 2-thienyl-ethylamine |
HU225503B1 (en) * | 1997-05-13 | 2007-01-29 | Sanofi Aventis | Novel 2-(2-halophenyl)-2-(2-(2-thienyl)-ethylamino)-acetamides and process for producing them |
HU222283B1 (hu) | 1997-05-13 | 2003-05-28 | Sanofi-Synthelabo | Eljárás tieno[3,2-c]piridin-származékok előállítására |
HU225504B1 (en) * | 1997-05-13 | 2007-01-29 | Sanofi Aventis | Novel halophenyl-(2-(2-thienyl)-ethylamino)-acetonitriles and process for producing them |
FR2769313B1 (fr) * | 1997-10-06 | 2000-04-21 | Sanofi Sa | Derives d'esters hydroxyacetiques, leur procede de preparation et leur utilisation comme intermediaires de synthese |
HU226421B1 (en) | 1998-11-09 | 2008-12-29 | Sanofi Aventis | Process for racemizing optically active 2-(2-chlorophenyl)-2-(2-(2-thienyl)-ethylamino)-acetamides |
WO2002018357A1 (en) * | 2000-08-29 | 2002-03-07 | Rpg Life Sciences Limited | A ONE-POT PROCESS FOR THE PREPARATION OF PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS OF 4, 5, 6, 7 - TETRAHYDROTHIENO (3,2-c) PYRIDINE DERIVATIVES HAVING ANTITHROMBOTIC ACTIVITY |
US6495691B1 (en) | 2001-07-06 | 2002-12-17 | Brantford Chemicals Inc. | Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives |
US6767913B2 (en) | 2001-12-18 | 2004-07-27 | Teva Pharmaceutical Industries Ltd. | Crystal forms iii, iv, v, and novel amorphous form of clopidogrel hydrogensulfate, processes for their preparation, processes for the preparation of form i, compositions containing the new forms and methods of administering the new forms |
US7074928B2 (en) | 2002-01-11 | 2006-07-11 | Teva Pharmaceutical Industries, Ltd. | Polymorphs of clopidogrel hydrogensulfate |
HUP0200438A3 (en) * | 2002-02-06 | 2003-10-28 | Egis Gyogyszergyar Nyilvanosan | Novel clopidogrel hydrochloride polymorphs, process for the preparation thereof, their use and pharmaceutical compositions containing them |
ITMI20020933A1 (it) * | 2002-05-03 | 2003-11-03 | Danimite Dipharma S P A | Procedimento per la sintesi di clopidogrel |
US6800759B2 (en) * | 2002-08-02 | 2004-10-05 | Teva Pharmaceutical Industries Ltd. | Racemization and enantiomer separation of clopidogrel |
IL166593A0 (en) | 2002-08-02 | 2006-01-15 | Racemization and enantiomer separation of clopidogrel | |
US6812363B2 (en) * | 2002-10-15 | 2004-11-02 | Usv Limited | Racemization of optically active 2-substituted phenyl glycine esters |
EP1606231A1 (en) * | 2003-02-03 | 2005-12-21 | Nadkarni, Sunil Sadanand | Process for preparation of clopidogrel, its salts and pharmaceutical compositions |
WO2004081016A1 (en) | 2003-03-12 | 2004-09-23 | Cadila Healthcare Limited | Polymorphs and amorphous form of (s) - (+) -clopidogrel bisulfate |
WO2004108665A2 (en) * | 2003-04-24 | 2004-12-16 | Sun Pharmaceutical Industries Limited | A process for preparation of clopidogrel |
GB0321256D0 (en) | 2003-09-11 | 2003-10-08 | Generics Uk Ltd | Novel crystalline compounds |
CA2676121A1 (en) | 2003-11-03 | 2005-07-14 | Cadila Healthcare Limited | Processes for preparing different forms of (s)-(+)-clopidogrel bisulfate |
CA2457459A1 (en) * | 2004-02-11 | 2005-08-11 | Brantford Chemicals Inc. | Resolution of racemates of methyl alpha-5-(4,5,6,7-tetrahydro(3,2-c)thienopyridyl)-(2-chlorophenyl) acetate |
KR100553398B1 (ko) * | 2004-03-12 | 2006-02-16 | 한미약품 주식회사 | 티에노[3,2-c]피리딘 유도체의 제조 방법 및 이에사용되는 중간체 |
WO2006003671A1 (en) * | 2004-07-02 | 2006-01-12 | Srinivasa Reddy Battula | A process for resolution of methylamino(2-chlorophenyl)acetate |
WO2007032023A2 (en) | 2005-07-12 | 2007-03-22 | Rpg Life Sciences Limited | A process for preparation of methyl-(+)-(s)-alpha-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4h)-acetic acid methyl ester or salts thereof having higher chiral purity and products thereof |
CN101253271A (zh) * | 2005-09-02 | 2008-08-27 | 第一精密化学株式会社 | 光学活性α-羟基羧酸的制造方法 |
WO2007028337A1 (en) * | 2005-09-08 | 2007-03-15 | Zhejiang Huahai Pharmaceutical Co., Ltd. | Preparation of clopidogrel and its analogues methyl tetrahydrothienopyridine acetate compounds |
CN100390180C (zh) * | 2005-12-15 | 2008-05-28 | 上海应用技术学院 | 氯吡格雷及其盐的制备方法 |
KR101235117B1 (ko) * | 2005-12-26 | 2013-02-20 | 에스케이케미칼주식회사 | 광학분리에 의한 (s)-(+)-클로피도그렐의 제조방법 |
US20070191609A1 (en) * | 2006-02-13 | 2007-08-16 | Lee Pharma Limited | Process for preparation of clopidogrel bisulphate form-1 |
US20070225320A1 (en) * | 2006-03-27 | 2007-09-27 | Eswaraiah Sajja | Process for preparing clopidogrel |
WO2007144729A1 (en) * | 2006-06-13 | 2007-12-21 | Orchid Chemicals & Pharmaceuticals Limited | An improved process for the preparation of clopidogrel |
CA2655844A1 (en) * | 2006-08-03 | 2008-02-14 | Teva Pharmaceutical Industries Ltd. | Process for preparing clopidogrel bisulphate |
PT2064217E (pt) * | 2006-09-04 | 2011-04-19 | Ranbaxy Lab Ltd | Processo melhorado para a preparação de clopidogrel e seus sais farmaceuticamente aceitáveis |
EP1980563A1 (en) | 2007-04-09 | 2008-10-15 | BATTULA, Srinivasa Reddy | Procedure for the preparation of methyl (+)-(S)-Alpha-(O-chlorophenyl)-6,7-dihydrothieno-[3,2-C]pyridine-5(4H) acetate |
BRPI0803101A2 (pt) * | 2007-04-18 | 2014-04-22 | Teva Pharma | Processos melhores para preparação de clopidogrel |
KR100990949B1 (ko) * | 2008-06-09 | 2010-10-29 | 엔자이텍 주식회사 | 클로피도그렐 및 그의 유도체의 제조방법 |
EP2346879A1 (en) * | 2008-10-24 | 2011-07-27 | Sandoz AG | A process for the preparation of s-clopidogrel |
CN101434540B (zh) * | 2008-12-23 | 2011-07-20 | 重庆莱美药业股份有限公司 | α-氯(2-氯)苯乙酸甲酯的合成方法 |
CN101775001B (zh) * | 2010-01-28 | 2012-07-04 | 天津市中央药业有限公司 | 采用固体酸催化酯化合成硫酸氢氯吡格雷中间体的方法 |
CN102558138A (zh) * | 2010-12-08 | 2012-07-11 | 湖北成田制药股份有限公司 | 2-卤代苯基-2-(2-噻吩乙氨基)乙酸酯类及其盐的制备方法 |
WO2012123958A1 (en) | 2011-02-14 | 2012-09-20 | Cadila Healthcare Limited | Highly pure salts of clopidogrel free of genotoxic impurities |
CN103172527A (zh) * | 2011-12-26 | 2013-06-26 | 湖北德洲科技发展有限公司 | 一种制备氯吡格雷合成中间体-邻氯苯甘氨酸甲酯的方法 |
CN103435631B (zh) * | 2013-08-29 | 2015-08-26 | 四川峨嵋山药业股份有限公司 | I型硫酸氢氯吡格雷的制备方法 |
CN103483356B (zh) * | 2013-09-30 | 2016-01-13 | 浙江美诺华药物化学有限公司 | 一种(s)-氯吡格雷的硫酸盐或盐酸盐的制备方法 |
CN108707156A (zh) * | 2018-08-03 | 2018-10-26 | 安徽省金楠医疗科技有限公司 | 硫酸氢氯吡格雷合成方法 |
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US4127580A (en) * | 1975-02-07 | 1978-11-28 | Parcor | Process for the preparation of thieno-pyridine derivatives |
FR2397417A1 (fr) * | 1977-07-12 | 1979-02-09 | Parcor | Procede de preparation de derives de la thienopyridine |
FR2530247B1 (fr) * | 1982-07-13 | 1986-05-16 | Sanofi Sa | Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique |
FR2623810B2 (fr) * | 1987-02-17 | 1992-01-24 | Sanofi Sa | Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant |
FR2624860B1 (fr) * | 1987-12-18 | 1990-06-01 | Sanofi Sa | Procede de preparation de la n-(chloro-2 benzyl) (thienyl-2)-2 ethylamine |
US4906756A (en) * | 1988-05-10 | 1990-03-06 | Syntex (U.S.A.) Inc. | 2-(2-nitrovinyl)thiophene reduction and synthesis of thieno[3,2-c]pyridine derivatives |
FR2652575B1 (fr) * | 1989-09-29 | 1992-01-24 | Sanofi Sa | Procede de preparation d'acides alpha-bromo phenylacetiques. |
-
1990
- 1990-07-10 FR FR909008749A patent/FR2664596B1/fr not_active Expired - Lifetime
-
1991
- 1991-06-27 IE IE225091A patent/IE73222B1/en not_active IP Right Cessation
- 1991-07-02 AU AU79492/91A patent/AU645816B2/en not_active Expired
- 1991-07-03 US US07/725,650 patent/US5204469A/en not_active Expired - Lifetime
- 1991-07-08 AT AT91401891T patent/ATE136899T1/de not_active IP Right Cessation
- 1991-07-08 ES ES91401891T patent/ES2086505T3/es not_active Expired - Lifetime
- 1991-07-08 EP EP91401891A patent/EP0466569B1/fr not_active Expired - Lifetime
- 1991-07-08 DE DE69118765T patent/DE69118765T2/de not_active Expired - Lifetime
- 1991-07-08 CA CA002046482A patent/CA2046482C/en not_active Expired - Lifetime
- 1991-07-08 PT PT98244A patent/PT98244B/pt not_active IP Right Cessation
- 1991-07-08 PL PL91290980A patent/PL172216B1/pl unknown
- 1991-07-08 DK DK91401891.6T patent/DK0466569T3/da active
- 1991-07-09 JP JP3168086A patent/JP2945174B2/ja not_active Expired - Lifetime
- 1991-07-09 KR KR1019910011791A patent/KR100198503B1/ko not_active IP Right Cessation
- 1991-07-09 HU HU912311A patent/HU215957B/hu unknown
-
1996
- 1996-07-02 GR GR960401807T patent/GR3020434T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
HU912311D0 (en) | 1991-12-30 |
EP0466569A1 (fr) | 1992-01-15 |
CA2046482A1 (en) | 1992-01-11 |
PL290980A1 (en) | 1992-06-26 |
IE912250A1 (en) | 1992-01-15 |
EP0466569B1 (fr) | 1996-04-17 |
HUT61556A (en) | 1993-01-28 |
CA2046482C (en) | 2001-10-30 |
DE69118765T2 (de) | 1996-10-24 |
FR2664596B1 (fr) | 1994-06-10 |
IE73222B1 (en) | 1997-05-07 |
US5204469A (en) | 1993-04-20 |
AU7949291A (en) | 1992-01-16 |
JP2945174B2 (ja) | 1999-09-06 |
HU215957B (hu) | 1999-03-29 |
JPH04230387A (ja) | 1992-08-19 |
DE69118765D1 (de) | 1996-05-23 |
GR3020434T3 (en) | 1996-10-31 |
PT98244A (pt) | 1992-05-29 |
DK0466569T3 (da) | 1996-08-12 |
KR100198503B1 (ko) | 1999-06-15 |
AU645816B2 (en) | 1994-01-27 |
ATE136899T1 (de) | 1996-05-15 |
FR2664596A1 (fr) | 1992-01-17 |
ES2086505T3 (es) | 1996-07-01 |
PL172216B1 (en) | 1997-08-29 |
PT98244B (pt) | 1998-12-31 |
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