IE36192B1 - Antibiotics and processes for their production - Google Patents
Antibiotics and processes for their productionInfo
- Publication number
- IE36192B1 IE36192B1 IE8972A IE8972A IE36192B1 IE 36192 B1 IE36192 B1 IE 36192B1 IE 8972 A IE8972 A IE 8972A IE 8972 A IE8972 A IE 8972A IE 36192 B1 IE36192 B1 IE 36192B1
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- group
- benzyl
- compounds
- chloride
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 4
- 229940124587 cephalosporin Drugs 0.000 abstract 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- -1 Cephalosporin compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- QAMQBROWEMDMOK-CQSZACIVSA-N (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](CCCC(=O)OCC1=CC=CC=C1)C(O)=O QAMQBROWEMDMOK-CQSZACIVSA-N 0.000 abstract 1
- UQLRAAASUFVOLL-LLVKDONJSA-N (2R)-2-amino-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound N[C@H](CCCC(=O)OCC1=CC=CC=C1)C(O)=O UQLRAAASUFVOLL-LLVKDONJSA-N 0.000 abstract 1
- FZBNFTSTPLZIOZ-MRVPVSSYSA-N (5R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-(2,2,2-trichloroethoxy)hexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](CCCC(O)=O)C(=O)OCC(Cl)(Cl)Cl FZBNFTSTPLZIOZ-MRVPVSSYSA-N 0.000 abstract 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 abstract 1
- QXAJNNROHSRLNQ-UHFFFAOYSA-N 2-benzhydryl-2-phenylpropanedioyl dichloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)(C(Cl)=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 QXAJNNROHSRLNQ-UHFFFAOYSA-N 0.000 abstract 1
- AVBHHECXXFKOHS-UHFFFAOYSA-N 3-benzhydryloxy-3-oxo-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 AVBHHECXXFKOHS-UHFFFAOYSA-N 0.000 abstract 1
- OYIFNHCXNCRBQI-SCSAIBSYSA-N D-2-aminoadipic acid Chemical compound OC(=O)[C@H](N)CCCC(O)=O OYIFNHCXNCRBQI-SCSAIBSYSA-N 0.000 abstract 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- OPEBOTYCWHBJJL-UHFFFAOYSA-N bromoformonitrile oxide Chemical compound [O-][N+]#CBr OPEBOTYCWHBJJL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 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
- 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
-
- 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
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB329571A GB1350772A (en) | 1971-01-27 | 1971-01-27 | Antibiotics and processes for their production |
| GB2852271 | 1971-06-17 | ||
| GB3965471 | 1971-08-24 | ||
| GB182972 | 1972-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36192L IE36192L (en) | 1972-07-27 |
| IE36192B1 true IE36192B1 (en) | 1976-09-15 |
Family
ID=27447180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE8972A IE36192B1 (en) | 1971-01-27 | 1972-01-24 | Antibiotics and processes for their production |
Country Status (10)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905963A (en) * | 1972-01-25 | 1975-09-16 | Lilly Co Eli | Process for preparing primary 3-carbamoyloxymethyl cephalosporins |
| US3994875A (en) * | 1974-06-24 | 1976-11-30 | Yeda Research & Development Co. Ltd. | Antibiotics |
| CA1128930A (en) | 1978-04-07 | 1982-08-03 | Stuart B. Laing | Cephalosporin compounds |
| AU1672492A (en) * | 1991-05-03 | 1992-12-21 | University Technologies International Inc. | Biofilm reduction method |
| WO2004083217A1 (en) * | 2003-03-20 | 2004-09-30 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of cefoxitin |
| CN101830913B (zh) * | 2010-04-09 | 2012-10-31 | 烟台宝华生物技术有限公司 | 头孢母核衍生化合物、由其制备的头孢烯类鎓盐化合物及采用其制备硫酸头孢吡唑的方法 |
| CN103848851B (zh) * | 2012-11-29 | 2016-03-02 | 上海交通大学 | 一种盐酸头孢卡品酯的合成方法 |
| EP4252794A1 (en) | 2019-01-29 | 2023-10-04 | Nipro Corporation | Artificial lung device |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445633A1 (de) | 1963-10-07 | 1968-12-05 | Ciba Geigy | Verfahren zur Herstellung neuer Amide |
| CH480365A (de) * | 1965-01-18 | 1969-10-31 | Ciba Geigy | Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure |
-
1971
- 1971-01-27 GB GB329571A patent/GB1350772A/en not_active Expired
-
1972
- 1972-01-01 AR AR24020972A patent/AR204899A1/es active
- 1972-01-18 CA CA132,726A patent/CA1003404A/en not_active Expired
- 1972-01-24 IE IE8972A patent/IE36192B1/xx unknown
- 1972-01-26 AU AU38356/72A patent/AU468248B2/en not_active Expired
- 1972-01-26 BE BE778508A patent/BE778508A/xx unknown
- 1972-01-26 DE DE19722203653 patent/DE2203653C3/de not_active Expired
- 1972-01-26 CH CH112472A patent/CH569021A5/xx not_active IP Right Cessation
- 1972-01-27 JP JP7210183A patent/JPS5418274B1/ja active Pending
- 1972-01-27 FR FR7202751A patent/FR2161866B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1350772A (en) | 1974-04-24 |
| BE778508A (fr) | 1972-07-26 |
| JPS5418274B1 (enrdf_load_stackoverflow) | 1979-07-06 |
| AU468248B2 (en) | 1976-01-08 |
| IE36192L (en) | 1972-07-27 |
| AU3835672A (en) | 1973-08-02 |
| DE2203653B2 (de) | 1974-12-19 |
| AR204899A1 (es) | 1976-03-19 |
| FR2161866A1 (enrdf_load_stackoverflow) | 1973-07-13 |
| DE2203653A1 (de) | 1972-08-10 |
| CA1003404A (en) | 1977-01-11 |
| DE2203653C3 (de) | 1975-07-31 |
| FR2161866B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| CH569021A5 (enrdf_load_stackoverflow) | 1975-11-14 |
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