ES2182330T3 - Procedimiento para la preparacion selectiva de isomeros z de 3-(2-vinil-sustituido) cefalosporina. - Google Patents
Procedimiento para la preparacion selectiva de isomeros z de 3-(2-vinil-sustituido) cefalosporina.Info
- Publication number
- ES2182330T3 ES2182330T3 ES98929666T ES98929666T ES2182330T3 ES 2182330 T3 ES2182330 T3 ES 2182330T3 ES 98929666 T ES98929666 T ES 98929666T ES 98929666 T ES98929666 T ES 98929666T ES 2182330 T3 ES2182330 T3 ES 2182330T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- hydrogen atom
- indicates
- amino protecting
- vinyl
- 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.)
- Expired - Lifetime
Links
- HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical compound 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 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- MAUHLWUADQYTDD-XCGJVMPOSA-N (6r)-4-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C=C)S[C@@H]2CC(=O)N12 MAUHLWUADQYTDD-XCGJVMPOSA-N 0.000 abstract 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 abstract 1
- 229950003476 aminothiazole Drugs 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- -1 pivaloyloxymethyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un procedimiento para la producción selectiva del isómero Z de un ácido 7-N-amino(sustituido o no sustituido)-3-[2-(4-tiazol(sustituido o no sustituido)-5-il)]vinil-3-cefemo-4-carboxílico o un éster suyo representado por la siguiente fórmula general (IV) **(Ver fórmula)** en la que R1 indica un átomo de hidrógeno o un grupo protector monovalente del amino, o R1 indica un grupo 2-(2-N-aminotiazol(protegido o no protegido)-4-il)-2-alcoxiiminoacetilo que tiene la siguiente fórmula (II) **(Ver fórmula)** donde R5 es un átomo de hidrógeno o un grupo monovalente protector del amino y R6 es un átomo de hidrógeno, o R5 y R6, tomados conjuntamente, significan un grupo divalente protector del amino, y R7 es un grupo alquilo de 1-4 átomos de carbono y en la que R2 indica un átomo de hidrógeno, o R1 y R2, tomados conjuntamente, significan un grupo divalente protector del amino y R3 indica un átomo de hidrógeno, un grupo pivaloiloximetilo o un grupo formador de éster, como un grupo protector del carboxilo, y R8 indica un átomo de hidrógeno, un grupo alquilo de 1-4 átomos de carbono, un grupo trifluorometilo o un grupo cloro.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16694897 | 1997-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2182330T3 true ES2182330T3 (es) | 2003-03-01 |
Family
ID=15840609
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES98929666T Expired - Lifetime ES2182330T3 (es) | 1997-06-24 | 1998-06-24 | Procedimiento para la preparacion selectiva de isomeros z de 3-(2-vinil-sustituido) cefalosporina. |
Country Status (24)
Country | Link |
---|---|
US (1) | US6288223B1 (es) |
EP (1) | EP1016665B1 (es) |
JP (1) | JP3713282B2 (es) |
KR (1) | KR100515273B1 (es) |
CN (1) | CN1107679C (es) |
AT (1) | ATE221890T1 (es) |
AU (1) | AU731265B2 (es) |
BR (1) | BR9810313B1 (es) |
CA (1) | CA2294178C (es) |
CZ (1) | CZ295599B6 (es) |
DE (1) | DE69807093T2 (es) |
EA (1) | EA002449B1 (es) |
ES (1) | ES2182330T3 (es) |
HU (1) | HU228767B1 (es) |
ID (1) | ID24210A (es) |
IL (1) | IL133681A (es) |
NZ (1) | NZ502234A (es) |
PL (1) | PL193367B1 (es) |
PT (1) | PT1016665E (es) |
RO (1) | RO120261B1 (es) |
SK (1) | SK283525B6 (es) |
TR (1) | TR200000310T2 (es) |
UA (1) | UA55463C2 (es) |
WO (1) | WO1998058932A1 (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4157177B2 (ja) * | 1997-06-04 | 2008-09-24 | 大塚化学ホールディングス株式会社 | 3−アルケニルセフェム化合物の製造法 |
WO2005003141A2 (en) * | 2003-07-04 | 2005-01-13 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of cefditoren |
EP1660505A2 (en) * | 2003-08-14 | 2006-05-31 | Ranbaxy Laboratories Limited | Process for selective preparation of z-isomer of cefditoren and pharmaceutically acceptable salts and esters thereof |
WO2005100369A1 (en) * | 2004-04-13 | 2005-10-27 | Ranbaxy Laboratories Limited | Depletion of e-isomers in preparation of z-enriched 3-(2-substituted vinyl) cephalosporins |
WO2005100367A1 (en) * | 2004-04-13 | 2005-10-27 | Ranbaxy Laboratories Limited | Intermediates useful in the synthesis of 3-(2-substituted vinyl) cephalosporins |
JP4064948B2 (ja) * | 2004-06-04 | 2008-03-19 | 明治製菓株式会社 | 3−アルケニルセフェム化合物及び製造方法 |
JP4046708B2 (ja) * | 2004-06-04 | 2008-02-13 | 明治製菓株式会社 | 3−アルケニルセフェム化合物の製造方法 |
TW200619222A (en) * | 2004-09-02 | 2006-06-16 | Rohm & Haas Elect Mat | Method for making organometallic compounds |
JP2006096679A (ja) * | 2004-09-28 | 2006-04-13 | Meiji Seika Kaisha Ltd | セファロスポリン化合物の製造方法 |
CN101665499A (zh) * | 2008-09-01 | 2010-03-10 | 日本化学工业株式会社 | 头孢烯化合物的制造方法 |
EP2520578A1 (en) | 2011-05-06 | 2012-11-07 | Lupin Limited | Process for purification of cephalosporins |
CN105622636B (zh) * | 2016-02-05 | 2017-08-25 | 河南理工大学 | 一种头孢妥仑匹酯中间体的制备方法 |
CN113480491B (zh) * | 2021-09-08 | 2022-05-06 | 山东昌邑四方医药化工有限公司 | 一种从头孢托仑母核生产废液中回收4-甲基噻唑-5-甲醛和三苯基氧膦的方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6219593A (ja) | 1985-07-18 | 1987-01-28 | Meiji Seika Kaisha Ltd | 新規セフエム化合物 |
IE58487B1 (en) * | 1984-09-07 | 1993-09-22 | Kaisha Maiji Seika | New cephalosporin compounds and the production thereof |
JPH03128382A (ja) | 1989-07-18 | 1991-05-31 | Eisai Co Ltd | チアゾリルアセトアミドセフェム系化合物 |
JPH06219593A (ja) * | 1993-01-21 | 1994-08-09 | Oki Electric Ind Co Ltd | 電子写真記録装置 |
JP3128382B2 (ja) | 1993-03-11 | 2001-01-29 | 旭 中野 | 鉄道車両運行支援表示装置 |
ATE198892T1 (de) * | 1993-11-17 | 2001-02-15 | Biochemie Gmbh | Trennung von cephalosporinisomeren |
JPH0867684A (ja) | 1994-08-31 | 1996-03-12 | Kyorin Pharmaceut Co Ltd | 新規セフェム化合物、その製造法及び抗菌剤 |
-
1998
- 1998-06-24 UA UA2000010366A patent/UA55463C2/uk unknown
- 1998-06-24 EP EP98929666A patent/EP1016665B1/en not_active Expired - Lifetime
- 1998-06-24 NZ NZ502234A patent/NZ502234A/en not_active IP Right Cessation
- 1998-06-24 AT AT98929666T patent/ATE221890T1/de not_active IP Right Cessation
- 1998-06-24 US US09/446,380 patent/US6288223B1/en not_active Expired - Lifetime
- 1998-06-24 KR KR10-1999-7012110A patent/KR100515273B1/ko not_active IP Right Cessation
- 1998-06-24 RO RO99-01373A patent/RO120261B1/ro unknown
- 1998-06-24 WO PCT/JP1998/002820 patent/WO1998058932A1/ja active IP Right Grant
- 1998-06-24 SK SK1857-99A patent/SK283525B6/sk not_active IP Right Cessation
- 1998-06-24 IL IL13368198A patent/IL133681A/xx not_active IP Right Cessation
- 1998-06-24 PL PL339361A patent/PL193367B1/pl not_active IP Right Cessation
- 1998-06-24 EA EA200000065A patent/EA002449B1/ru not_active IP Right Cessation
- 1998-06-24 CA CA002294178A patent/CA2294178C/en not_active Expired - Lifetime
- 1998-06-24 BR BRPI9810313-0A patent/BR9810313B1/pt not_active IP Right Cessation
- 1998-06-24 TR TR2000/00310T patent/TR200000310T2/xx unknown
- 1998-06-24 AU AU79331/98A patent/AU731265B2/en not_active Ceased
- 1998-06-24 HU HU0002458A patent/HU228767B1/hu unknown
- 1998-06-24 PT PT98929666T patent/PT1016665E/pt unknown
- 1998-06-24 DE DE69807093T patent/DE69807093T2/de not_active Expired - Fee Related
- 1998-06-24 CN CN98807781A patent/CN1107679C/zh not_active Expired - Lifetime
- 1998-06-24 JP JP50417799A patent/JP3713282B2/ja not_active Expired - Lifetime
- 1998-06-24 ES ES98929666T patent/ES2182330T3/es not_active Expired - Lifetime
- 1998-06-24 ID IDW991680A patent/ID24210A/id unknown
- 1998-06-24 CZ CZ19994718A patent/CZ295599B6/cs not_active IP Right Cessation
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