IE35110B1 - Antibiotics and their preparation - Google Patents
Antibiotics and their preparationInfo
- Publication number
- IE35110B1 IE35110B1 IE303/71A IE30371A IE35110B1 IE 35110 B1 IE35110 B1 IE 35110B1 IE 303/71 A IE303/71 A IE 303/71A IE 30371 A IE30371 A IE 30371A IE 35110 B1 IE35110 B1 IE 35110B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- lower alkyl
- compound
- radical
- compounds
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract 4
- 229940088710 antibiotic agent Drugs 0.000 title abstract 4
- -1 α-methoxy-p-sulphooxycinnamoyloxy Chemical group 0.000 abstract 21
- 150000001875 compounds Chemical class 0.000 abstract 19
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical class S1C(=NN=C1)* 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 241000187747 Streptomyces Species 0.000 abstract 2
- 241000187392 Streptomyces griseus Species 0.000 abstract 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000003957 anion exchange resin Substances 0.000 abstract 2
- LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RGEARSFHQFORKA-OZFKEBCOSA-M sodium;(6r,7s)-7-[(5-amino-5-carboxypentanoyl)amino]-7-methoxy-3-[[(z)-2-methoxy-3-(4-sulfooxyphenyl)prop-2-enoyl]oxymethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].S([C@H]1N(C([C@@]1(OC)NC(=O)CCCC(N)C(O)=O)=O)C=1C([O-])=O)CC=1COC(=O)C(/OC)=C/C1=CC=C(OS(O)(=O)=O)C=C1 RGEARSFHQFORKA-OZFKEBCOSA-M 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- 241000187390 Amycolatopsis lactamdurans Species 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 241000187130 Streptomyces chartreusis Species 0.000 abstract 1
- 241000970227 Streptomyces fimbriatus Species 0.000 abstract 1
- 241000187216 Streptomyces halstedii Species 0.000 abstract 1
- 241000187418 Streptomyces rochei Species 0.000 abstract 1
- 241000187191 Streptomyces viridochromogenes Species 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012990 dithiocarbamate Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 241000894007 species Species 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000335 thiazolyl group Chemical class 0.000 abstract 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/08—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin disubstituted in the 7 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1949670A | 1970-03-13 | 1970-03-13 | |
| US5131970A | 1970-06-30 | 1970-06-30 | |
| US9659470A | 1970-12-09 | 1970-12-09 | |
| US05/115,779 US4302578A (en) | 1970-12-09 | 1971-02-16 | Cephalosporin antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35110L IE35110L (en) | 1971-09-13 |
| IE35110B1 true IE35110B1 (en) | 1975-11-12 |
Family
ID=27486855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE303/71A IE35110B1 (en) | 1970-03-13 | 1971-03-10 | Antibiotics and their preparation |
Country Status (19)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1040620A (en) * | 1972-11-14 | 1978-10-17 | Frank J. Urban | 6-alkoxy-6-acylamidopenicillins 7-alkoxy-7-acylamido acetoxycephalosporins and process |
| US4065356A (en) | 1976-02-12 | 1977-12-27 | Merck & Co., Inc. | Production of antibiotic FR-02A (efrotomycin) by streptomyces lactamdurans |
| US4327093A (en) | 1978-10-24 | 1982-04-27 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-2 or 3-cephem-4-carboxylic acid compounds |
| JPS5931517B2 (ja) * | 1978-12-12 | 1984-08-02 | 山之内製薬株式会社 | 新規７↓−メトキシセファロスポリン誘導体 |
| US4379920A (en) * | 1979-10-31 | 1983-04-12 | Glaxo Group Limited | Cephalosporins |
| EP0137365A3 (en) * | 1983-09-06 | 1986-01-15 | Takeda Chemical Industries, Ltd. | Cephalosporins and their production |
| EP0160745A3 (en) * | 1984-05-07 | 1986-11-05 | Takeda Chemical Industries, Ltd. | Cephem compounds and their production |
| KR20060061295A (ko) | 2003-05-28 | 2006-06-07 | 디에스엠 아이피 어셋츠 비.브이. | 세펨 화합물 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4945594A (enrdf_load_html_response) * | 1972-09-08 | 1974-05-01 |
-
1971
- 1971-02-24 IL IL36281A patent/IL36281A/en unknown
- 1971-03-02 DE DE2109854A patent/DE2109854C3/de not_active Expired
- 1971-03-02 DE DE19712166462 patent/DE2166462B2/de active Granted
- 1971-03-02 DE DE19712166463 patent/DE2166463A1/de active Pending
- 1971-03-08 CH CH1294175A patent/CH587856A5/de not_active IP Right Cessation
- 1971-03-08 CH CH1294275A patent/CH589655A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH1273075A patent/CH587911A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH333371A patent/CH579576A5/xx not_active IP Right Cessation
- 1971-03-08 PH PH12269A patent/PH12292A/en unknown
- 1971-03-08 CH CH1273175A patent/CH586226A5/xx not_active IP Right Cessation
- 1971-03-08 AR AR234333A patent/AR200370A1/es active
- 1971-03-10 IE IE303/71A patent/IE35110B1/xx unknown
- 1971-03-11 SE SE7103119A patent/SE385713B/xx unknown
- 1971-03-11 FI FI710711A patent/FI51484C/fi active
- 1971-03-12 DD DD153734A patent/DD96254A5/xx unknown
- 1971-03-12 YU YU626/71A patent/YU35164B/xx unknown
- 1971-03-12 DK DK118171A patent/DK131639C/da not_active IP Right Cessation
- 1971-03-12 NO NO932/71A patent/NO134219C/no unknown
- 1971-03-12 CA CA107,642A patent/CA960169A/en not_active Expired
- 1971-03-12 FR FR7108668A patent/FR2085702B1/fr not_active Expired
- 1971-03-12 NL NLAANVRAGE7103360,A patent/NL171285C/xx not_active IP Right Cessation
- 1971-03-12 DD DD164638A patent/DD100002A5/xx unknown
- 1971-03-12 BE BE764160A patent/BE764160A/xx not_active IP Right Cessation
- 1971-03-12 DD DD164639A patent/DD99166A5/xx unknown
- 1971-03-12 IT IT49017/71A patent/IT1045524B/it active
- 1971-03-13 JP JP46013630A patent/JPS581919B1/ja active Granted
- 1971-04-19 GB GB2340771*A patent/GB1321412A/en not_active Expired
-
1972
- 1972-05-31 AR AR242279A patent/AR212149A1/es active
-
1974
- 1974-04-29 AR AR253505A patent/AR201142A1/es active
Also Published As
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