DE2166463A1 - Derivate der 7-beta-(d-5-amino-5carboxyvaleramido)-7-methoxy-3-cephem-4carbonsaeure - Google Patents
Derivate der 7-beta-(d-5-amino-5carboxyvaleramido)-7-methoxy-3-cephem-4carbonsaeureInfo
- Publication number
- DE2166463A1 DE2166463A1 DE19712166463 DE2166463A DE2166463A1 DE 2166463 A1 DE2166463 A1 DE 2166463A1 DE 19712166463 DE19712166463 DE 19712166463 DE 2166463 A DE2166463 A DE 2166463A DE 2166463 A1 DE2166463 A1 DE 2166463A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- cephem
- carboxylic acid
- carboxyvaleramido
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 D-5-AMINO-5CARBOXYVALERAMIDO Chemical class 0.000 title claims description 240
- 239000002253 acid Substances 0.000 title description 15
- 150000002148 esters Chemical class 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005141 piperazine Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- OMKVZYFAGQKILB-UHFFFAOYSA-M potassium;butoxymethanedithioate Chemical compound [K+].CCCCOC([S-])=S OMKVZYFAGQKILB-UHFFFAOYSA-M 0.000 description 1
- GZFUTXWXSUUNAK-UHFFFAOYSA-M potassium;cyclohexyloxymethanedithioate Chemical compound [K+].[S-]C(=S)OC1CCCCC1 GZFUTXWXSUUNAK-UHFFFAOYSA-M 0.000 description 1
- TVLAOGVTDQGZIV-UHFFFAOYSA-M potassium;cyclopentyloxymethanedithioate Chemical compound [K+].[S-]C(=S)OC1CCCC1 TVLAOGVTDQGZIV-UHFFFAOYSA-M 0.000 description 1
- ZTHBGWDIOJXYNC-UHFFFAOYSA-M potassium;hexoxymethanedithioate Chemical compound [K+].CCCCCCOC([S-])=S ZTHBGWDIOJXYNC-UHFFFAOYSA-M 0.000 description 1
- ZMWBGRXFDPJFGC-UHFFFAOYSA-M potassium;propan-2-yloxymethanedithioate Chemical compound [K+].CC(C)OC([S-])=S ZMWBGRXFDPJFGC-UHFFFAOYSA-M 0.000 description 1
- NZUFLKMNMAHESJ-UHFFFAOYSA-M potassium;propoxymethanedithioate Chemical compound [K+].CCCOC([S-])=S NZUFLKMNMAHESJ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- FFWJHVGUAKWTKW-UHFFFAOYSA-N pyridine-3-thiol Chemical compound SC1=CC=CN=C1 FFWJHVGUAKWTKW-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- ILNWEIMZWZNAKF-UHFFFAOYSA-M sodium;n,n-dipropylcarbamodithioate Chemical compound [Na+].CCCN(C([S-])=S)CCC ILNWEIMZWZNAKF-UHFFFAOYSA-M 0.000 description 1
- AAHBHQAOQQKTLD-UHFFFAOYSA-M sodium;n-[2-(diethylamino)ethyl]-n-ethylcarbamodithioate Chemical compound [Na+].CCN(CC)CCN(CC)C([S-])=S AAHBHQAOQQKTLD-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 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 (1)
| Publication Number | Publication Date |
|---|---|
| DE2166463A1 true DE2166463A1 (de) | 1974-05-02 |
Family
ID=27486855
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166463 Pending DE2166463A1 (de) | 1970-03-13 | 1971-03-02 | Derivate der 7-beta-(d-5-amino-5carboxyvaleramido)-7-methoxy-3-cephem-4carbonsaeure |
| DE19712166462 Granted DE2166462B2 (de) | 1970-03-13 | 1971-03-02 | 7 beta -(d-5-amino-5-carboxyvaleramido)-3-(alpha-methoxy-cinnamoyloxymethyl)-7-methoxy-3-cephem-4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und solche verbindungen enthaltende arzneimittel |
| DE2109854A Expired DE2109854C3 (de) | 1970-03-13 | 1971-03-02 | 7beta-(D-5- Amino- 5-carboxyvaleramido) -3- (carbamoyloxymethyl) -7-methoxy-3-cephem-4-carbonsäure und deren Salze, Verfahren zu Ihrer Herstellung und solche Verbindungen enthaltende Arzneimittel |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166462 Granted DE2166462B2 (de) | 1970-03-13 | 1971-03-02 | 7 beta -(d-5-amino-5-carboxyvaleramido)-3-(alpha-methoxy-cinnamoyloxymethyl)-7-methoxy-3-cephem-4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und solche verbindungen enthaltende arzneimittel |
| DE2109854A Expired DE2109854C3 (de) | 1970-03-13 | 1971-03-02 | 7beta-(D-5- Amino- 5-carboxyvaleramido) -3- (carbamoyloxymethyl) -7-methoxy-3-cephem-4-carbonsäure und deren Salze, Verfahren zu Ihrer Herstellung und solche Verbindungen enthaltende Arzneimittel |
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 |
| EP1658296B1 (en) | 2003-05-28 | 2012-12-19 | DSM Sinochem Pharmaceuticals Netherlands B.V. | Cephem compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4945594A (enrdf_load_stackoverflow) * | 1972-09-08 | 1974-05-01 |
-
1971
- 1971-02-24 IL IL36281A patent/IL36281A/en unknown
- 1971-03-02 DE DE19712166463 patent/DE2166463A1/de active Pending
- 1971-03-02 DE DE19712166462 patent/DE2166462B2/de active Granted
- 1971-03-02 DE DE2109854A patent/DE2109854C3/de not_active Expired
- 1971-03-08 CH CH1273175A patent/CH586226A5/xx not_active IP Right Cessation
- 1971-03-08 PH PH12269A patent/PH12292A/en unknown
- 1971-03-08 CH CH1273075A patent/CH587911A5/xx not_active IP Right Cessation
- 1971-03-08 AR AR234333A patent/AR200370A1/es active
- 1971-03-08 CH CH333371A patent/CH579576A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH1294275A patent/CH589655A5/xx not_active IP Right Cessation
- 1971-03-08 CH CH1294175A patent/CH587856A5/de not_active IP Right Cessation
- 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 BE BE764160A patent/BE764160A/xx not_active IP Right Cessation
- 1971-03-12 DD DD164639A patent/DD99166A5/xx unknown
- 1971-03-12 DD DD153734A patent/DD96254A5/xx 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 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 NL NLAANVRAGE7103360,A patent/NL171285C/xx not_active IP Right Cessation
- 1971-03-12 DD DD164638A patent/DD100002A5/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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |