KR840005816A - 세팜로스포틴 화합물의 제조방법 - Google Patents
세팜로스포틴 화합물의 제조방법 Download PDFInfo
- Publication number
- KR840005816A KR840005816A KR1019830003647A KR830003647A KR840005816A KR 840005816 A KR840005816 A KR 840005816A KR 1019830003647 A KR1019830003647 A KR 1019830003647A KR 830003647 A KR830003647 A KR 830003647A KR 840005816 A KR840005816 A KR 840005816A
- Authority
- KR
- South Korea
- Prior art keywords
- salt
- compound
- medicament
- hydrogen
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 6
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 1-methyl-1H-tetrazol-5-yl Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 13
- 239000003814 drug Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 229930186147 Cephalosporin Natural products 0.000 claims 5
- 229940124587 cephalosporin Drugs 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 241001024304 Mino Species 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000000845 anti-microbial effect Effects 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000003536 tetrazoles Chemical class 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (35)
- (ⅰ) 일반식 :
-
- 의 화합물 또는 이것의 반응유도체를 일반식 :
-
- 의 화합물 또는 이것의 염으로 축합시키는 것;
- (ⅱ) 그 보호기 또 기들을 제거하는 것; 및
- (ⅲ) 만일 필요하다면 전술한 생성물을 이것의 약제로 사용할 수 있는 염으로 전환시키는 공정을 포함하는 것으로 된 일반식 :
-
- 의 7β-〔(Z)-2-(2-아마노티아졸-4-일)-2-옥시아마노-아세트아마도〕-3-세펨-4-카르복시산 화합물 또는 이것의 약제로 사용할 수 있는 염의 제조방법.
- (위 식에서, R1은 수소 또는 저급알킬이고; R2는 아세톡시 또는 (1-메틸-1H-테트라졸-5-일)리오이며, R3는 카르복시이거나; 또는 R2는 일반식 :의 기이며, R3는 -COO-이고, Y는 수소, 히드록시메틸 또는 카르바모일이고; 그리고 n은 2 또는 3의 정수이다. 또한 R4는 보호기이고; R5는 R2가 아세톡시 또는(1-메틸-1H-테트라졸-5-일) 티오일 때에는 보호 카르복시이고, R2가 일반식:의 기 일때에는 -CCO-이다.)
- 일반식 :
- (ⅰ)
-
- 의 화합물 또는 이것의 염을 일반식 :
-
- 의 피리딘 화합물, (1-페닐-5-페르캅토) 테트라졸 또는 이것의 염과 반응시키는 것;
- (ⅱ) R7이 보호기인 경우에는 동일 보호기를 제거하는 것; 및
- (ⅲ) 만일 필요하다면 전술한 생성물을 이것의 약제로 사용할 수 있는 염으로 전환시키는 공정으로 된 일반식:
-
- 의 7β-〔(Z)-2-(2-아마노티아졸-4-일)-2-옥시아마노-아세트아마도〕-3-세펨-4-카르복시산 화합물 또는 이것의 약제로 사용할 수 있는 염의 제조방법.
- 위 식에서, R1은 수소 또는 저급알킬이고; R6은 (1-메틸-1H-테트라졸-5-일)티오, 그리고 R3는 카르복시이거나; 또는 R6이 일반식 :의 기, R3이 -COO-이고, 그리고 Y가 수소, 히드록시메틸 또는 카르바모일; 그리고 n이 2 또는 3의 정수이며 R7은 수소 또는 보호기이고, 또 Y와 n은 앞에서 정의한 바와 같다.
- 항마생물 유효량의 일반식 :
-
- 의 7β-〔(Z)-2-(2-아마노티아졸-4-일)-2-옥시아마노-아세트아마도〕-3-세펨-4-카르복시산 화합물 또는 이것의 약제로 사용할 수 있는 염과 약제로 사용할 수 있는 캐리어를 함유하는 약제조성물.
- 위 식에서, R1,R2,R3, Y 및 n은 앞에서 정의한 바와 같다.
- 제3항에서 전술한 세팔로스포틴 화합물이 R1이 수소, R2가 일반식 :의 기, R3가 -COO-Y가 수소, 4-히드록시메틸, 3-히드록시메틸 또는 4-카르바모일 그리고 n이 2의 정수인 일반식(Ⅰ)의 화합물인 약제 조성물.
- 제3항에서 전술한 세팔로스포린 화합물이 7β-{(Z)-2-(2-아미노티아졸-4-일) -2-〔2-피르롤리든-3-일)옥시이미노〕아세트아미}도-3-(1-피리디니오메틸)-3-세펨-4-카르복실레이트 또는 이것의 약제로 사용할 수 있는 염인 약제 조성물.
- 제3항에서 전술한 세팔로스포린 화합물이 7β-{(Z)-2-(2-아미노티아졸-4-일) -2-〔(3S)-2-피르롤리든-3-일)옥시이미노〕-아세트아미도}-3-(1-피리디니오메틸)-3-세펨-4-카르복실레이트 또는 이것의 약제로 사용할 수 있는 염인 약제조성물.
- 온혈동물에 항미생물 유효량의 일반식 :
-
- 의 7β-〔(Z)-2-(2-아마노티아졸-4-일)-2-옥시아마노-아세트아마도〕-3-세펨-4-카르복시산 화합물 또는 이것의 약제로 사용할 수 있는 염을 투약하는 것으로 된 미생물 전염병 치료방법, 위 식에서 R1,R2,R3, Y 및 n은 앞에서 정의한 바와 같다.
- 제7항에서 전술한 세팔로스포린 화합물이, R1이 수소, R2가 일반식 :의 기, R3가 -COO-Y가 수소, 4-히드록시메틸, 3-히드록시메틸 또는 4-카르바모일 그리고 n이 2의 정수인 방법.
- 제7항에서 진술한 세팔로스포린 화합물이 7β-{(Z)-2-(2-아미노티아졸-4-일) -2-〔2-피르롤리든-3-일)옥시이미노〕-아세트아미도}-3-(1-피리디니오메틸)-3-세펨-4-카르복실레이트 또는 이것의 약제로 사용할 수 있는 염인방법.
- 제7항에서 전술한 세팜로스포린 화합물이 7β-{(Z)-2-(2-아미노티아졸-4-일) -2-〔(3S)-2-피르롤리든-3-일)옥시이미노〕-아세트아미도}-3-(1-피리디니오메틸)-3--4-세펨카르복실레이트 또는 이것의 약제로 사용할 수 있는 염인방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019870005206A KR870001441B1 (ko) | 1982-08-07 | 1987-05-26 | 세팔로스포린 화합물의 제조방법 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB82-22823 | 1982-08-07 | ||
GB8222823 | 1982-08-07 | ||
JP22823 | 1982-08-07 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019870005206A Division KR870001441B1 (ko) | 1982-08-07 | 1987-05-26 | 세팔로스포린 화합물의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840005816A true KR840005816A (ko) | 1984-11-19 |
KR870001440B1 KR870001440B1 (ko) | 1987-08-06 |
Family
ID=10532181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830003647A KR870001440B1 (ko) | 1982-08-07 | 1983-08-04 | 세팔로스포린 화합물의 제조방법 |
Country Status (23)
Country | Link |
---|---|
US (4) | US4598075A (ko) |
EP (2) | EP0101265B1 (ko) |
JP (3) | JPS5951292A (ko) |
KR (1) | KR870001440B1 (ko) |
AT (2) | ATE35413T1 (ko) |
AU (1) | AU562248B2 (ko) |
BG (3) | BG40967A3 (ko) |
CA (1) | CA1231940A (ko) |
CS (2) | CS243484B2 (ko) |
DD (1) | DD210053A5 (ko) |
DE (2) | DE3381734D1 (ko) |
DK (2) | DK358983A (ko) |
ES (3) | ES8502121A1 (ko) |
FI (1) | FI74972C (ko) |
GR (1) | GR78864B (ko) |
IE (1) | IE55406B1 (ko) |
IL (1) | IL69246A (ko) |
NO (1) | NO161068C (ko) |
PH (1) | PH18498A (ko) |
PL (2) | PL139932B1 (ko) |
PT (1) | PT77166B (ko) |
SU (2) | SU1227116A3 (ko) |
ZA (1) | ZA835411B (ko) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL69246A (en) * | 1982-08-07 | 1986-07-31 | Tanabe Seiyaku Co | 7-((2-aminothiazolyl-2-pyrrolidonyl or(piperidonyl)-oxyimino)acetamido)cephem carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
JPS60132983A (ja) * | 1983-12-21 | 1985-07-16 | Tanabe Seiyaku Co Ltd | チアゾ−ル酢酸誘導体及びその製法 |
JPS6178792A (ja) * | 1984-09-26 | 1986-04-22 | Yamanouchi Pharmaceut Co Ltd | 7−〔α−(2−アミノ−4−チアゾリル)−α−(4−オキソ−2−アゼチジニル置換イミノ)アセトアミド〕−3−置換メチル−Δ↑3−セフエム−4−カルボン酸およびその製造法 |
JPS6185392A (ja) * | 1984-10-03 | 1986-04-30 | Tanabe Seiyaku Co Ltd | セフアロスポリン化合物の新規製法 |
JPS61143381A (ja) * | 1984-12-14 | 1986-07-01 | Tanabe Seiyaku Co Ltd | 光学活性チアゾ−ル酢酸誘導体の製法 |
JPS61143380A (ja) * | 1984-12-14 | 1986-07-01 | Tanabe Seiyaku Co Ltd | チアゾ−ル酢酸誘導体の製法 |
JPS61143379A (ja) * | 1984-12-14 | 1986-07-01 | Tanabe Seiyaku Co Ltd | チアゾ−ル酢酸誘導体の製法 |
CA1263399A (en) * | 1984-12-19 | 1989-11-28 | Hoffmann-La Roche Limited | Process for the manufacture of aminothiazole acetic acid derivatives |
JPS61171464A (ja) * | 1985-01-23 | 1986-08-02 | Dai Ichi Seiyaku Co Ltd | オキシイミノ酪酸誘導体の製法 |
JPS63107989A (ja) * | 1986-06-04 | 1988-05-12 | Tanabe Seiyaku Co Ltd | セファロスポリン化合物 |
IL82738A0 (en) * | 1986-06-16 | 1987-12-20 | Tanabe Seiyaku Co | Cephalosporin compounds,their preparation and pharmaceutical compositions containing them |
AT389701B (de) * | 1987-10-08 | 1990-01-25 | Tanabe Seiyaku Co | Neue cephalosporinverbindungen und diese enthaltende pharmazeutische zusammensetzungen |
JP4773154B2 (ja) * | 2005-07-29 | 2011-09-14 | 小澤物産株式会社 | レバー式カップリング |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
IE44888B1 (en) * | 1976-03-09 | 1982-05-05 | Fujisawa Pharmaceutical Co | 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation theroef |
GR63088B (en) * | 1976-04-14 | 1979-08-09 | Takeda Chemical Industries Ltd | Preparation process of novel cephalosporins |
FR2384782A1 (fr) * | 1977-03-25 | 1978-10-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-acetoxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
SE448379B (sv) * | 1978-03-31 | 1987-02-16 | Roussel Uclaf | O-substituerade oximderivat av 7-amino-tiazolyl-acetamidocefalosporansyra |
AR229883A1 (es) * | 1978-05-26 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato |
US4288435A (en) * | 1978-07-17 | 1981-09-08 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutical antibacterial compositions containing them |
US4284631A (en) * | 1978-07-31 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them |
GB2028305A (en) * | 1978-08-03 | 1980-03-05 | Hoechst Ag | Cephem derivatives and processes for their manufacture |
GB2061276B (en) * | 1979-10-25 | 1983-05-25 | Squibb & Sons Inc | Imidazole and tetrazole derivatives of 7-((2-amino-4-thiazolyl)-oximino)cephalosporins |
US4271157A (en) * | 1980-02-28 | 1981-06-02 | E. R. Squibb & Sons, Inc. | Imidazole derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
US4416879A (en) * | 1980-09-08 | 1983-11-22 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
IL69246A (en) * | 1982-08-07 | 1986-07-31 | Tanabe Seiyaku Co | 7-((2-aminothiazolyl-2-pyrrolidonyl or(piperidonyl)-oxyimino)acetamido)cephem carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
JPS59155391A (ja) * | 1983-02-22 | 1984-09-04 | Tanabe Seiyaku Co Ltd | 新規セファロスポリン誘導体 |
-
1983
- 1983-07-15 IL IL69246A patent/IL69246A/xx unknown
- 1983-07-15 IE IE1648/83A patent/IE55406B1/en unknown
- 1983-07-20 AU AU17104/83A patent/AU562248B2/en not_active Ceased
- 1983-07-21 US US06/516,053 patent/US4598075A/en not_active Expired - Fee Related
- 1983-07-25 ZA ZA835411A patent/ZA835411B/xx unknown
- 1983-07-27 JP JP58138674A patent/JPS5951292A/ja active Granted
- 1983-08-01 GR GR72100A patent/GR78864B/el unknown
- 1983-08-02 FI FI832770A patent/FI74972C/fi not_active IP Right Cessation
- 1983-08-03 BG BG8467044A patent/BG40967A3/xx unknown
- 1983-08-03 BG BG8465072A patent/BG42835A3/xx unknown
- 1983-08-03 BG BG8361975A patent/BG37838A3/xx unknown
- 1983-08-03 CA CA000433824A patent/CA1231940A/en not_active Expired
- 1983-08-04 KR KR1019830003647A patent/KR870001440B1/ko not_active IP Right Cessation
- 1983-08-04 CS CS831964A patent/CS243484B2/cs unknown
- 1983-08-04 CS CS835791A patent/CS236798B2/cs unknown
- 1983-08-05 NO NO832828A patent/NO161068C/no unknown
- 1983-08-05 ES ES524775A patent/ES8502121A1/es not_active Expired
- 1983-08-05 PL PL1983243329A patent/PL139932B1/pl unknown
- 1983-08-05 DK DK358983A patent/DK358983A/da not_active Application Discontinuation
- 1983-08-05 DE DE8787103997T patent/DE3381734D1/de not_active Expired - Fee Related
- 1983-08-05 PT PT77166A patent/PT77166B/pt unknown
- 1983-08-05 PH PH29359A patent/PH18498A/en unknown
- 1983-08-05 SU SU833631901A patent/SU1227116A3/ru active
- 1983-08-05 DE DE8383304527T patent/DE3377213D1/de not_active Expired
- 1983-08-05 EP EP83304527A patent/EP0101265B1/en not_active Expired
- 1983-08-05 AT AT83304527T patent/ATE35413T1/de not_active IP Right Cessation
- 1983-08-05 DD DD83253755A patent/DD210053A5/de not_active IP Right Cessation
- 1983-08-05 PL PL1983249964A patent/PL140023B1/pl unknown
- 1983-08-05 EP EP87103997A patent/EP0245619B1/en not_active Expired - Lifetime
- 1983-08-05 AT AT87103997T patent/ATE54450T1/de not_active IP Right Cessation
-
1984
- 1984-01-27 SU SU843697655A patent/SU1324586A3/ru active
- 1984-04-04 ES ES531296A patent/ES8506707A1/es not_active Expired
- 1984-08-17 ES ES535281A patent/ES535281A0/es active Granted
-
1985
- 1985-01-18 US US06/692,497 patent/US4598154A/en not_active Expired - Fee Related
-
1986
- 1986-03-04 US US06/835,886 patent/US4727071A/en not_active Expired - Fee Related
- 1986-10-17 US US06/920,180 patent/US4742174A/en not_active Expired - Fee Related
-
1987
- 1987-05-29 JP JP62137563A patent/JPS62294681A/ja active Granted
- 1987-05-29 JP JP62137562A patent/JPS62294615A/ja active Granted
- 1987-07-10 DK DK361587A patent/DK361587A/da not_active Application Discontinuation
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