DE1795178A1 - Verfahren zur Herstellung von Verbindungen der Cephalosporinreihe - Google Patents
Verfahren zur Herstellung von Verbindungen der CephalosporinreiheInfo
- Publication number
- DE1795178A1 DE1795178A1 DE19681795178 DE1795178A DE1795178A1 DE 1795178 A1 DE1795178 A1 DE 1795178A1 DE 19681795178 DE19681795178 DE 19681795178 DE 1795178 A DE1795178 A DE 1795178A DE 1795178 A1 DE1795178 A1 DE 1795178A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- acid
- formula
- compound
- hydrogen
- 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
- 238000000034 method Methods 0.000 title claims 85
- 150000001875 compounds Chemical class 0.000 title claims 15
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- -1 imide halide Chemical class 0.000 claims 29
- 239000002253 acid Substances 0.000 claims 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 150000003512 tertiary amines Chemical class 0.000 claims 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 229910052783 alkali metal Inorganic materials 0.000 claims 7
- 150000003949 imides Chemical class 0.000 claims 7
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- 230000002378 acidificating effect Effects 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 5
- 230000032050 esterification Effects 0.000 claims 5
- 238000005886 esterification reaction Methods 0.000 claims 5
- 150000007529 inorganic bases Chemical class 0.000 claims 5
- 150000007530 organic bases Chemical class 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 238000006884 silylation reaction Methods 0.000 claims 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000002879 Lewis base Substances 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000007527 lewis bases Chemical class 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
- 229910021529 ammonia Inorganic materials 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 3
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 3
- 239000011707 mineral Substances 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 150000001718 carbodiimides Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 claims 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 241000776450 PVC group Species 0.000 claims 1
- 241000282320 Panthera leo Species 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 238000006136 alcoholysis reaction Methods 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000002440 hydroxy compounds Chemical group 0.000 claims 1
- RFGNMWINQUUNKG-UHFFFAOYSA-N iron phosphoric acid Chemical compound [Fe].OP(O)(O)=O RFGNMWINQUUNKG-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000006000 trichloroethyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only starting from compounds containing carbon-to-metal bonds and followed by conversion of the -O- metal to -OH groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mycology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3849267A GB1241655A (en) | 1967-08-21 | 1967-08-21 | Improvements in or relating to cephalosporin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795178A1 true DE1795178A1 (de) | 1972-08-10 |
Family
ID=10403818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681795178 Pending DE1795178A1 (de) | 1967-08-21 | 1968-08-20 | Verfahren zur Herstellung von Verbindungen der Cephalosporinreihe |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5437157B1 (cg-RX-API-DMAC7.html) |
| AT (1) | AT303956B (cg-RX-API-DMAC7.html) |
| BE (1) | BE719712A (cg-RX-API-DMAC7.html) |
| CA (1) | CA924302A (cg-RX-API-DMAC7.html) |
| CH (1) | CH553816A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1795178A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR1585971A (cg-RX-API-DMAC7.html) |
| GB (2) | GB1241655A (cg-RX-API-DMAC7.html) |
| IL (1) | IL30581A (cg-RX-API-DMAC7.html) |
| NL (1) | NL6811828A (cg-RX-API-DMAC7.html) |
| PH (1) | PH9433A (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1385683A (en) * | 1971-03-01 | 1975-02-26 | Glaxo Lab Ltd | Antibiotics |
| GB1385685A (en) * | 1971-04-21 | 1975-02-26 | Glaxo Lab Ltd | Cephalosporin derivatives |
| GB1391271A (en) * | 1971-04-30 | 1975-04-16 | Glaxo Lab Ltd | Preparation of antibiotic compounds |
| AT378774B (de) * | 1982-08-06 | 1985-09-25 | Biochemie Gmbh | Verfahren zur deacylierung von penicillinen und cephalosporinen |
| US5750682A (en) * | 1994-07-22 | 1998-05-12 | Antibioticos S.P.A. | Glutaryl 7-ACA derivatives and processes for obtaining them |
-
1967
- 1967-08-21 GB GB3849267A patent/GB1241655A/en not_active Expired
-
1968
- 1968-08-12 GB GB3849268D patent/GB1208515A/en not_active Expired
- 1968-08-20 CH CH1251268A patent/CH553816A/xx not_active IP Right Cessation
- 1968-08-20 DE DE19681795178 patent/DE1795178A1/de active Pending
- 1968-08-20 FR FR1585971D patent/FR1585971A/fr not_active Expired
- 1968-08-20 JP JP5910668A patent/JPS5437157B1/ja active Pending
- 1968-08-20 AT AT811568A patent/AT303956B/de not_active IP Right Cessation
- 1968-08-20 IL IL3058168A patent/IL30581A/xx unknown
- 1968-08-20 NL NL6811828A patent/NL6811828A/xx unknown
- 1968-08-20 CA CA027932A patent/CA924302A/en not_active Expired
- 1968-08-20 BE BE719712A patent/BE719712A/xx unknown
- 1968-08-21 PH PH9489*UA patent/PH9433A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1585971A (cg-RX-API-DMAC7.html) | 1970-02-06 |
| BE719712A (cg-RX-API-DMAC7.html) | 1969-02-20 |
| GB1241655A (en) | 1971-08-04 |
| AT303956B (de) | 1972-12-27 |
| JPS5437157B1 (cg-RX-API-DMAC7.html) | 1979-11-13 |
| GB1208515A (en) | 1970-10-14 |
| PH9433A (en) | 1975-11-26 |
| IL30581A (en) | 1975-05-22 |
| CA924302A (en) | 1973-04-10 |
| NL6811828A (cg-RX-API-DMAC7.html) | 1969-02-25 |
| CH553816A (de) | 1974-09-13 |
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