KR840004117A - 세팔로스포린 유도체의 제조방법 - Google Patents
세팔로스포린 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840004117A KR840004117A KR1019830000834A KR830000834A KR840004117A KR 840004117 A KR840004117 A KR 840004117A KR 1019830000834 A KR1019830000834 A KR 1019830000834A KR 830000834 A KR830000834 A KR 830000834A KR 840004117 A KR840004117 A KR 840004117A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- alkyl
- substituted
- optionally substituted
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- -1 pyridinium radicals Chemical class 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 2
- 150000003222 pyridines Chemical class 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 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
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon 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, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
-
- 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
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)
- Rigid Pipes And Flexible Pipes (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (2)
- 일반식(Ⅱ)의 화합물을 일반식(Ⅰ)에서의 피리디늄 라디칼 B중의 하나에 상응하게 하는 그러한 피리딘 또는 피리딘 유도체와 반응시키고, R3및 R6라디칼이 후술할 바와 같은 용이하게 제거될 수 있는 그룹을 나타낼 경우 산가수분해제로 또는 가수소분해제로 처리하거나 티오우레아로 처리하여 용이하게 제거 될 수 있는 그룹을 제거하고 일반식(Ⅰ)의 화합물을 제조하거나, 일반식(Ⅲ)의 7-아미노세펨 화합물 또는 그의 산부가염(여기에서 아미노그룹은 반응성 유도체의 형태로 또한 존재할 수 있다)을 일반식(Ⅳ)의 2-(2-아미노티아졸-4-일)-2-신-옥스이미노아세트산과 반응시키거나 R2가 COOR3(여기에서 R3는 후술할 바와 같거나 산가수분해 또는 가수소분해로 용이하게 제거될 수 있는 에스테르 그룹을 나타낸다)를 나타낼 경우 일반식(Ⅳ) 화합물의 활성화된 유도체와 반응시키고, 보호그룹이 존재하면 보호그룹을 제거하고 필요시 수득된 생성물을 생리적으로 허용될 수 있는 산부가염으로 전환시킴을 특징으로 하여 일반식(Ⅰ)의 세펨화합물 및 그의 생리적으로 허용될 수 있는 산부가염을 제조하는 방법.상기 식에서,R1은 수소 또는 할로겐이며,R2는 -CO2R3그룹이거나(여기에서 R3는 소수, C1-C4-알킬, -CH2O-C1-C4알킬, -CH2OOC-C1-C4알킬 또는 1당량의 알카리금속, 알카리토금속, 암모늄 또는 1당량의 유기아민염기이다) 니트릴 그룹 또는 질소상에서 단일치환 또는 이치환될 수 있는 카바모일 그룹 -CONH2이며,ℓ, m 및 n은 각 경우 0 또는 1이고,A는 아릴라디칼 또는 그룹(여기에서 R4및 R5는 동일하거나 상이하고 수소, 아릴, C1-C4-알킬 그룹이거나 이들이 결합된 탄소원자와 함께 메틸렌 또는 C3-C7-시클로알킬리덴 그룹이며, 알킬과 시클로알킬은 또한 단일치환되거나 다중치환될 수 있다)이고,B는 동일하거나 상이한 치환체로 단일치환되거나 다중치환될 수 있는 피리디늄 라디칼이고, 여기에서 치환될 수 있는 치환체로는 치환된 C1-C6-알킬(그중의 2알킬 그룹은 또한 연결되어 1개 또는 2개의 이중결합을 추가로 함유할 수 있으면서 환중의 C원자는 헤테로원자로 대치될 수 있는 가능한 치환된 디-내지 데카-메틸렌환을 형성할 수 있다); 시아노-C1-C3-알킬, 에폭시-C2-C6-알킬, 트리플루오로메틸 또는 펜타플루오로에틸; 히드록시이미노메틸 또는 C1-C4-알콕시이미노메틸; 임의 치환된 C2-C2-알케닐, C6-C6-알키닐, C3-C7-시클로알킬 또는 C3-C7-시클로알킬메틸(여기에서 두 치환체환은 또한 치환될 수 있고 C원자는 헤테로원자로 대치될 수 있다); C4-C7-시클로알케닐; 임의 치환된 C4-C7-시클로알케닐; 임의 치환된 C1-C6-알콕시; 에폭시-C2-C6-알콕시; C2-C6-알케닐옥시 또는 C2-C6-알키닐옥시; 할로겐, 시아노, 히드록실 또는 멀캅토; 각각 알킬부위에서 임의 치환된 C1-C6-알킬설포닐, C1-C6-알킬설피닐 또는 C1-C6-알킬티오; 각각 메틸라디칼에서 치환된 메틸설포닐, 메틸실피닐 또는 메틸티오; C2-C6-알케닐티오, C2-C6-알케닐설피닐 또는 C2-C6-알케닐설포닐; 임의 치환된 펜닐, 벤질 또는 헤테로아릴; 포르밀 또는 케탈화된 포르밀; 케탈화된 형태로 또한 존재할 수있는 임의 치환된 C1-C6-알킬카보닐; 아릴카보닐; C1-C6-알킬카보닐아미노; 카복실 또는 C1-C6-알콕시카보닐; 질소상에서 단일 치환되거나 이치환될 수 있는 카바모일; 임의 치환된 카바조일; 질소상에서 단일 치환될 수 있는 설파모일; 또는 피리딜 또는 4-피리돈-1-일이며, 그룹 -C-(CH2)n(A)mR2는 신(syn)위치에 있으며,R6는 수소 또는 아미노보호그룹이고,R7은 일반식(Ⅰ)의 피리디늄 라디칼 B에 상응하는 피리딘 또는 치환된 피리딘으로 치환될 수 있는 그룹이며.R8은 수소원자 또는 1당량의 알카리금속, 알카리토금속, 암모늄 또는 1당량의 유기아민 염기이고, 일반식(Ⅱ)에서, R2는 전술된 바와 같으며, 그중 -CO2R3그룹에서 R3는 전술된 바와 같거나 산가수분해 또는 가수분해에 의해 용이하게 제거될 수 있는 에스테르 그룹을 나타낸다.
- 제1항에 있어서, 중성염 이온 특히 요다이드 이온 또는 티오시아네이트 이온의 존재하에서 치환체 R3의 친핵적 치환반응을 수행함이 특징인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3207840.4 | 1982-03-04 | ||
| DE19823207840 DE3207840A1 (de) | 1982-03-04 | 1982-03-04 | "cephalosporinderivate und verfahren zu ihrer herstellung" |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840004117A true KR840004117A (ko) | 1984-10-06 |
Family
ID=6157330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830000834A KR840004117A (ko) | 1982-03-04 | 1983-03-02 | 세팔로스포린 유도체의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4647556A (ko) |
| EP (1) | EP0088320B1 (ko) |
| JP (1) | JPS58162592A (ko) |
| KR (1) | KR840004117A (ko) |
| AT (1) | ATE39696T1 (ko) |
| AU (1) | AU565927B2 (ko) |
| CA (1) | CA1219857A (ko) |
| DE (2) | DE3207840A1 (ko) |
| DK (1) | DK108183A (ko) |
| ES (1) | ES520226A0 (ko) |
| FI (1) | FI830704L (ko) |
| GR (1) | GR77915B (ko) |
| HU (1) | HU190442B (ko) |
| IL (1) | IL68026A0 (ko) |
| MA (1) | MA19736A1 (ko) |
| MT (1) | MTP925B (ko) |
| NO (1) | NO830729L (ko) |
| NZ (1) | NZ203436A (ko) |
| OA (1) | OA07335A (ko) |
| PT (1) | PT76336B (ko) |
| ZA (1) | ZA831452B (ko) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL66726A0 (en) * | 1981-09-08 | 1982-12-31 | Lilly Co Eli | Improvements in or relating to thieno and furopyridinium-substituted cephalosporin derivatives |
| US4690921A (en) * | 1983-10-11 | 1987-09-01 | Yamanouchi Pharmaceutical Co., Ltd. | Cephalosporin compounds and salts thereof |
| GB2148289B (en) * | 1983-10-17 | 1987-09-23 | Lilly Co Eli | 3-bicyclicpyridinium-methyl cephalosporins |
| JPS6094984A (ja) * | 1983-10-28 | 1985-05-28 | Dai Ichi Seiyaku Co Ltd | セフエム誘導体 |
| DE150507T1 (de) * | 1983-12-29 | 1987-02-26 | Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp | Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate. |
| JPS60142987A (ja) * | 1983-12-29 | 1985-07-29 | Mochida Pharmaceut Co Ltd | セフアロスポリン誘導体 |
| EP0148004A3 (en) * | 1983-12-30 | 1986-04-23 | Glaxo Group Limited | Cephalosporin antibiotics |
| EP0150609A3 (en) * | 1983-12-30 | 1986-04-23 | Glaxo Group Limited | Cephalosporin antibiotics |
| JPS60169486A (ja) * | 1984-02-10 | 1985-09-02 | Yamanouchi Pharmaceut Co Ltd | ７−アミノ−３−置換メチル−３−セフエム−４−カルボン酸およびその低級アルキルシリル誘導体の製造法 |
| DE3404906A1 (de) * | 1984-02-11 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | 1-oxadethiacephalosporinderivate sowie verfahren zu ihrer herstellung |
| JPS60222490A (ja) * | 1984-04-17 | 1985-11-07 | Dai Ichi Seiyaku Co Ltd | セフアロスポリン誘導体およびその塩 |
| EP0160546A3 (en) * | 1984-04-26 | 1986-12-17 | Yamanouchi Pharmaceutical Co. Ltd. | Cephalosporin compounds, and their production, and medicaments containing them |
| EP0182633A3 (en) * | 1984-11-20 | 1987-09-02 | Ici Pharma | Cephalosporin derivatives |
| US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| GB8626245D0 (en) * | 1985-11-27 | 1986-12-03 | Ici Pharma | Cephalosporin compounds |
| US5147871A (en) * | 1986-07-03 | 1992-09-15 | Hoffmann La-Roche, Inc. | Anti-bacterial cephalosporin compounds |
| US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| JPS63132893A (ja) * | 1986-11-25 | 1988-06-04 | Mochida Pharmaceut Co Ltd | 新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤 |
| US5162523A (en) * | 1989-07-21 | 1992-11-10 | Hoffmann-La Roche Inc. | Cephalosporin antibacterial compounds |
| US5159077A (en) * | 1989-07-21 | 1992-10-27 | Hoffmann-La Roche Inc. | Penam antibacterial compounds |
| DE69736775T2 (de) * | 1996-04-04 | 2007-08-23 | Shionogi & Co., Ltd. | Cephemverbindungen und medikamente die diese verbindungen enthalten |
| TWI335332B (en) | 2001-10-12 | 2011-01-01 | Theravance Inc | Cross-linked vancomycin-cephalosporin antibiotics |
| PT2960244T (pt) * | 2008-10-31 | 2016-11-02 | Shionogi & Co | Cefalosporina contendo grupo catecol |
| KR20130018845A (ko) | 2010-04-05 | 2013-02-25 | 시오노기세야쿠 가부시키가이샤 | 카테콜기를 갖는 세펨 화합물 |
| WO2011136268A1 (ja) | 2010-04-28 | 2011-11-03 | 塩野義製薬株式会社 | 新規なセフェム誘導体 |
| JP6151257B2 (ja) | 2011-09-09 | 2017-06-21 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 肺内感染症の治療方法 |
| WO2013051597A1 (ja) * | 2011-10-04 | 2013-04-11 | 塩野義製薬株式会社 | カテコール基を有するセフェム誘導体 |
| TWI547496B (zh) * | 2011-10-04 | 2016-09-01 | 葛蘭素集團公司 | 抗菌化合物 |
| US8809314B1 (en) | 2012-09-07 | 2014-08-19 | Cubist Pharmacueticals, Inc. | Cephalosporin compound |
| US8476425B1 (en) | 2012-09-27 | 2013-07-02 | Cubist Pharmaceuticals, Inc. | Tazobactam arginine compositions |
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| UA121298C2 (uk) | 2013-03-15 | 2020-05-12 | Мерк Шарп І Доум Корп. | Антибіотична композиція на основі цефтолозану і тазобактаму |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4970990A (ko) * | 1973-09-29 | 1974-07-09 | ||
| US4298606A (en) * | 1974-12-19 | 1981-11-03 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| JPS5919553B2 (ja) * | 1976-01-01 | 1984-05-07 | 武田薬品工業株式会社 | セフアロスポリン |
| US4440766A (en) * | 1976-03-09 | 1984-04-03 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-3-cephem-4-carboxylic acid compounds |
| GB1591439A (en) * | 1976-10-01 | 1981-06-24 | Glaxo Operations Ltd | 7-syn (oxyimino -acylamido) cephalosporins |
| BE876538A (fr) * | 1978-05-26 | 1979-11-26 | Glaxo Group Ltd | Procede de preparation de cephalosporines |
| AR228726A1 (es) * | 1978-05-26 | 1983-04-15 | Glaxo Group Ltd | Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato |
| US4237168A (en) * | 1979-06-11 | 1980-12-02 | The Dow Chemical Company | N-(4-Chloro-2-methylphenyl)-N-hydroxy methanimidamide and its pesticidal use |
| DE3006888A1 (de) * | 1980-02-23 | 1981-09-10 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| JPS56131592A (en) * | 1980-03-18 | 1981-10-15 | Bristol Mayers Kenkyusho Kk | Antimicrobial agent |
| ZA813787B (en) * | 1980-06-18 | 1982-07-28 | Fujisawa Pharmaceutical Co | New cephem compounds and processes for preparation thereof |
| FR2485540A1 (fr) * | 1980-06-30 | 1981-12-31 | Sanofi Sa | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant |
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| ZA826538B (en) * | 1981-09-08 | 1984-04-25 | Lilly Co Eli | Thieno and furopyridinium-substituted cephalosporin derivatives |
| US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
| US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
| JPS5859991A (ja) * | 1981-09-14 | 1983-04-09 | Fujisawa Pharmaceut Co Ltd | 新規セフェム化合物 |
| US4501739A (en) * | 1982-01-19 | 1985-02-26 | Eli Lilly And Company | Thieno and furopyridinium-substituted cephalosporins |
-
1982
- 1982-03-04 DE DE19823207840 patent/DE3207840A1/de not_active Withdrawn
-
1983
- 1983-02-25 JP JP58030679A patent/JPS58162592A/ja active Pending
- 1983-02-26 DE DE8383101915T patent/DE3378827D1/de not_active Expired
- 1983-02-26 EP EP83101915A patent/EP0088320B1/de not_active Expired
- 1983-02-26 AT AT83101915T patent/ATE39696T1/de not_active IP Right Cessation
- 1983-03-02 MA MA19954A patent/MA19736A1/fr unknown
- 1983-03-02 FI FI830704A patent/FI830704L/fi not_active Application Discontinuation
- 1983-03-02 GR GR70647A patent/GR77915B/el unknown
- 1983-03-02 ES ES520226A patent/ES520226A0/es active Granted
- 1983-03-02 MT MT925A patent/MTP925B/xx unknown
- 1983-03-02 NZ NZ203436A patent/NZ203436A/xx unknown
- 1983-03-02 KR KR1019830000834A patent/KR840004117A/ko not_active Application Discontinuation
- 1983-03-03 HU HU83735A patent/HU190442B/hu unknown
- 1983-03-03 AU AU12039/83A patent/AU565927B2/en not_active Ceased
- 1983-03-03 IL IL8368026A patent/IL68026A0/xx unknown
- 1983-03-03 ZA ZA831452A patent/ZA831452B/xx unknown
- 1983-03-03 NO NO830729A patent/NO830729L/no unknown
- 1983-03-03 CA CA000422765A patent/CA1219857A/en not_active Expired
- 1983-03-03 DK DK108183A patent/DK108183A/da not_active Application Discontinuation
- 1983-03-03 PT PT76336A patent/PT76336B/pt unknown
- 1983-03-03 US US06/471,649 patent/US4647556A/en not_active Expired - Lifetime
- 1983-03-04 OA OA57929A patent/OA07335A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT76336A (de) | 1983-04-01 |
| CA1219857A (en) | 1987-03-31 |
| EP0088320B1 (de) | 1989-01-04 |
| AU1203983A (en) | 1983-09-08 |
| GR77915B (ko) | 1984-09-25 |
| DK108183A (da) | 1983-09-05 |
| IL68026A0 (en) | 1983-06-15 |
| JPS58162592A (ja) | 1983-09-27 |
| ES8401492A1 (es) | 1983-12-01 |
| EP0088320A3 (en) | 1986-03-19 |
| DE3207840A1 (de) | 1983-09-15 |
| ES520226A0 (es) | 1983-12-01 |
| US4647556A (en) | 1987-03-03 |
| ZA831452B (en) | 1983-11-30 |
| FI830704L (fi) | 1983-09-05 |
| PT76336B (de) | 1985-12-13 |
| FI830704A0 (fi) | 1983-03-02 |
| DK108183D0 (da) | 1983-03-03 |
| OA07335A (fr) | 1984-08-31 |
| MA19736A1 (fr) | 1983-10-01 |
| ATE39696T1 (de) | 1989-01-15 |
| NZ203436A (en) | 1986-06-11 |
| NO830729L (no) | 1983-09-05 |
| EP0088320A2 (de) | 1983-09-14 |
| MTP925B (en) | 1984-02-13 |
| HU190442B (en) | 1986-09-29 |
| AU565927B2 (en) | 1987-10-01 |
| DE3378827D1 (en) | 1989-02-09 |
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Legal Events
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| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |