KR840007014A - 세팔로스포린 유도체의 제조방법 - Google Patents
세팔로스포린 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840007014A KR840007014A KR1019830006057A KR830006057A KR840007014A KR 840007014 A KR840007014 A KR 840007014A KR 1019830006057 A KR1019830006057 A KR 1019830006057A KR 830006057 A KR830006057 A KR 830006057A KR 840007014 A KR840007014 A KR 840007014A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- alkyl
- radical
- substituted
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 2
- -1 salt ions Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002537 isoquinolines Chemical group 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 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
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Control Of Electric Motors In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Fats And Perfumes (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 하기 일반식(Ⅱ)의 화합물, 이의 염 또는 이의 반응성 유도체를 피리딘, 또는 이소퀴놀린퀴놀린 유도체와 반응시키고, 존재할 수 있는 보호 그룹을 제거시키고, 필요시, 생성물을 생리학적으로 허용되는 산부가염으로 전환시키거나;
- 아미노 그룹이 반응성 유도체의 형으로 존재할 수도 있는 하기 일반삭(Ⅲ)의 7-아미노세펨 화합물 또는 이의 산부가염을 하기 일반식(Ⅳ)의 2-(5-아미노-1,2,4-티아디아졸-3-일)-2-신-옥시미노 아세트산 또는 이의 활성화 유도체와 반응시키고, 존재할 수 있는 보호 그룹을 제거시키고, 필요시, 생성물을 생리학적으로 호용되는 산부가염으로 전환시킴을 특징으로 하는 하기 일반식(Ⅰ)의 화합물 및 이의 생리학적으로 허용되는 산부가염의 제조방법 :
-
-
- 상기식에서,
- R1은 수소, 임의 치환된 C1-C6-알킬, 임의 치환된 C2-C6-알케닐, C3-C7-시클로알킬, C3-C7-시클로알킬-C1-C6-알킬, C4-C7-시클로알케닐이거나, 하기일반식의 그룹이며;
-
- 〔여기서, n,m은 각각 0 또는 1일 수 있고, R3및 R4는 동일 또는 상이하며, 수소, 아릴 또는 C1-C4-알킬그룹이거나, 이들이 견합하고 있는 탄소원자와 함께 메틸렌 그룹 또는 C3-C7-시클로알킬 리덴그룹을 형성하며, 여기에서 알킬 및 시클로알킬을 더 단일치환 또는 다중치환 시킬 수 있으며 ; R5는 그룹-CO2R6(여기서, R6는 수소, C1-C4-알킬, -CH2O-C1-C4-알킬,-CH2OOC-C1-알킬 또는 1가의 알칼리금속, 알칼리토금속, 암모늄 또는 유기아민염기이다)이거나, 질소상에 단일치환 또는 이중 치환될 수 있는 니트릴 그룹 또는 카바모일그룹-CONH2이다〕, R2는 피리디늄 라디칼(이것은, 결합되어, 한 개의 환 탄소원자가 헤테로 원자로 치환될 수 있고, 1개 또는 2개의 이중 견합이 존재할 수도 있는 임의 치환된 디-내지 데카 메틸렌을 형성하는 2개의 알킬그룹으로 오르토-위치에서 치환된다)이거나, 1-퀴놀리늄 라다칼 또는 2-이소카놀라늄라디칼(이들 각 라디칼은 임의 치환도니 C1-C6-알킬, C1-C6-알콕시, 한로겐, 트리플루오로메틸 또는 히드록실 그룹으로 동일 또는 상이하게 단일 치환 또는 다중 치환될 수 있다)이며, R1O그룹은 선-위치에 위치하며, R7은 아미노 그룹 또는 보호된 아미노그룹이고, R8은 라디칼 R2에 상응하라 피리딘, 퀴놀린 또는 이소퀴놀린 유도체로 치환시킬 수 있는 그룹이다.
- 제 1항에 있어서, 치환기 R8의 친핵 치환을 중성 염 이온, 특히 요오다이드 또는 티오시아네이트 이온의 존재하에 수행하는 방법.
- 제 1항에 있어서, 치환기 R8의 친핵 치환 반응을 라디칼 R2가 유도된 염기 존재하 및 트리메틸 요오도실란의 존재하에 수행하는 방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823247613 DE3247613A1 (de) | 1982-12-23 | 1982-12-23 | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DEP3247613.2 | 1982-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840007014A true KR840007014A (ko) | 1984-12-04 |
Family
ID=6181484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830006057A KR840007014A (ko) | 1982-12-23 | 1983-12-21 | 세팔로스포린 유도체의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0111934B1 (ko) |
| JP (1) | JPS59130295A (ko) |
| KR (1) | KR840007014A (ko) |
| AT (1) | ATE36534T1 (ko) |
| AU (1) | AU2281083A (ko) |
| CA (1) | CA1235689A (ko) |
| CS (1) | CS248714B2 (ko) |
| DE (2) | DE3247613A1 (ko) |
| DK (1) | DK594183A (ko) |
| ES (1) | ES528248A0 (ko) |
| FI (1) | FI834711A (ko) |
| GR (1) | GR79456B (ko) |
| HU (1) | HU189793B (ko) |
| IL (1) | IL70521A0 (ko) |
| MA (1) | MA19984A1 (ko) |
| NO (1) | NO834774L (ko) |
| NZ (1) | NZ206660A (ko) |
| PH (1) | PH21026A (ko) |
| PT (1) | PT77878B (ko) |
| ZA (1) | ZA839537B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ATE114657T1 (de) * | 1985-12-26 | 1994-12-15 | Eisai Co Ltd | Cephalosporin-verbindungen. |
| IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
| US4929612A (en) * | 1987-04-17 | 1990-05-29 | Eisai Co., Ltd. | Thiadiazolylacetamide cephem derivatives |
| DE3910421A1 (de) * | 1989-03-31 | 1990-10-04 | Hoechst Ag | Polare cephalosporinderivate und verfahren zu ihrer herstellung |
| WO2013036783A2 (en) | 2011-09-09 | 2013-03-14 | Cubist Pharmaceuticals, Inc. | Methods for treating intrapulmonary infections |
| 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 |
| US9872906B2 (en) | 2013-03-15 | 2018-01-23 | Merck Sharp & Dohme Corp. | Ceftolozane antibiotic compositions |
| KR102329764B1 (ko) | 2013-03-15 | 2021-11-23 | 머크 샤프 앤드 돔 코포레이션 | 세프톨로잔 항균성 조성물 |
| US20140274991A1 (en) | 2013-03-15 | 2014-09-18 | Cubist Pharmaceuticals, Inc. | Ceftolozane pharmaceutical compositions |
| WO2015035376A2 (en) | 2013-09-09 | 2015-03-12 | Calixa Therapeutics, Inc. | Treating infections with ceftolozane/tazobactam in subjects having impaired renal function |
| US8906898B1 (en) | 2013-09-27 | 2014-12-09 | Calixa Therapeutics, Inc. | Solid forms of ceftolozane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU536842B2 (en) * | 1978-12-29 | 1984-05-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephalosporin antibiotics |
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
-
1982
- 1982-12-23 DE DE19823247613 patent/DE3247613A1/de not_active Withdrawn
-
1983
- 1983-12-19 HU HU834333A patent/HU189793B/hu unknown
- 1983-12-21 DE DE8383112859T patent/DE3377714D1/de not_active Expired
- 1983-12-21 GR GR73321A patent/GR79456B/el unknown
- 1983-12-21 EP EP83112859A patent/EP0111934B1/de not_active Expired
- 1983-12-21 AT AT83112859T patent/ATE36534T1/de not_active IP Right Cessation
- 1983-12-21 PH PH30018A patent/PH21026A/en unknown
- 1983-12-21 IL IL70521A patent/IL70521A0/xx unknown
- 1983-12-21 KR KR1019830006057A patent/KR840007014A/ko not_active Application Discontinuation
- 1983-12-21 ES ES528248A patent/ES528248A0/es active Granted
- 1983-12-21 FI FI834711A patent/FI834711A/fi not_active Application Discontinuation
- 1983-12-21 NZ NZ206660A patent/NZ206660A/en unknown
- 1983-12-22 DK DK594183A patent/DK594183A/da not_active Application Discontinuation
- 1983-12-22 ZA ZA839537A patent/ZA839537B/xx unknown
- 1983-12-22 NO NO834774A patent/NO834774L/no unknown
- 1983-12-22 JP JP58243059A patent/JPS59130295A/ja active Pending
- 1983-12-22 AU AU22810/83A patent/AU2281083A/en not_active Abandoned
- 1983-12-22 CS CS839806A patent/CS248714B2/cs unknown
- 1983-12-22 PT PT77878A patent/PT77878B/pt unknown
- 1983-12-22 CA CA000444077A patent/CA1235689A/en not_active Expired
- 1983-12-23 MA MA20205A patent/MA19984A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI834711A (fi) | 1984-06-24 |
| PT77878A (de) | 1984-01-01 |
| IL70521A0 (en) | 1984-03-30 |
| ES8406493A1 (es) | 1984-08-01 |
| PH21026A (en) | 1987-06-30 |
| HUT34035A (en) | 1985-01-28 |
| CA1235689A (en) | 1988-04-26 |
| FI834711A0 (fi) | 1983-12-21 |
| CS248714B2 (en) | 1987-02-12 |
| EP0111934A3 (en) | 1985-05-15 |
| DE3247613A1 (de) | 1984-07-05 |
| ATE36534T1 (de) | 1988-09-15 |
| EP0111934B1 (de) | 1988-08-17 |
| GR79456B (ko) | 1984-10-30 |
| ZA839537B (en) | 1984-08-29 |
| DK594183D0 (da) | 1983-12-22 |
| AU2281083A (en) | 1984-06-28 |
| NO834774L (no) | 1984-06-25 |
| MA19984A1 (fr) | 1984-07-01 |
| NZ206660A (en) | 1987-07-31 |
| JPS59130295A (ja) | 1984-07-26 |
| DE3377714D1 (en) | 1988-09-22 |
| HU189793B (en) | 1986-07-28 |
| ES528248A0 (es) | 1984-08-01 |
| EP0111934A2 (de) | 1984-06-27 |
| PT77878B (de) | 1986-04-21 |
| DK594183A (da) | 1984-06-24 |
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