IL30392A - תהליך להכנת חומצה 7 - אמינו צפאלוספוראנית ותולדותיה - Google Patents
תהליך להכנת חומצה 7 - אמינו צפאלוספוראנית ותולדותיהInfo
- Publication number
- IL30392A IL30392A IL30392A IL3039268A IL30392A IL 30392 A IL30392 A IL 30392A IL 30392 A IL30392 A IL 30392A IL 3039268 A IL3039268 A IL 3039268A IL 30392 A IL30392 A IL 30392A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- formula
- compound
- agent
- halide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 64
- 238000002360 preparation method Methods 0.000 title claims description 14
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 150000004820 halides Chemical class 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- -1 imino halide Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical group ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 8
- 229930195733 hydrocarbon Natural products 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- NCLIGEZQAPUUQU-UHFFFAOYSA-N 2-silylacetamide Chemical compound NC(=O)C[SiH3] NCLIGEZQAPUUQU-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000005051 trimethylchlorosilane Substances 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229940124587 cephalosporin Drugs 0.000 description 9
- 150000001780 cephalosporins Chemical class 0.000 description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 230000020176 deacylation Effects 0.000 description 4
- 238000005947 deacylation reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 3
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229960000603 cefalotin Drugs 0.000 description 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL676710835A NL150798B (nl) | 1967-08-07 | 1967-08-07 | Werkwijze voor de bereiding van 7-aminocefalosoranzuur en derivaten daarvan. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30392A0 IL30392A0 (en) | 1968-09-26 |
| IL30392A true IL30392A (he) | 1971-12-29 |
Family
ID=19800883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30392A IL30392A (he) | 1967-08-07 | 1968-07-18 | תהליך להכנת חומצה 7 - אמינו צפאלוספוראנית ותולדותיה |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT280475B (he) |
| BE (1) | BE718824A (he) |
| CH (1) | CH513920A (he) |
| DK (1) | DK142912B (he) |
| ES (1) | ES356543A1 (he) |
| FR (1) | FR1583480A (he) |
| GB (1) | GB1239814A (he) |
| IE (1) | IE32230B1 (he) |
| IL (1) | IL30392A (he) |
| IT (1) | IT1035011B (he) |
| NL (1) | NL150798B (he) |
| SE (1) | SE373591B (he) |
| YU (1) | YU34589B (he) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758587A (fr) * | 1969-11-17 | 1971-05-06 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 7-aminocephalosporanique et nouveaux produits ainsi obtenus |
| JPS4948760B1 (he) * | 1970-12-25 | 1974-12-23 | ||
| GB1388267A (en) * | 1971-06-17 | 1975-03-26 | Glaxo Lab Ltd | Preparation of antibiotic compounds |
| GR70261B (he) * | 1977-12-12 | 1982-09-02 | Takeda Chemical Industries Ltd | |
| US4242509A (en) * | 1979-04-13 | 1980-12-30 | Eli Lilly And Company | Process for producing 7-amino-7-alkoxycephalosporins |
| AT378774B (de) * | 1982-08-06 | 1985-09-25 | Biochemie Gmbh | Verfahren zur deacylierung von penicillinen und cephalosporinen |
| EP1379531A2 (en) | 2001-04-19 | 2004-01-14 | Bioferma Murcia, S.A. | Enzymatic process for preparing cephalosporanic acid derivatives using alpha-ketoacid derivatives |
-
1967
- 1967-08-07 NL NL676710835A patent/NL150798B/xx not_active IP Right Cessation
-
1968
- 1968-07-18 IL IL30392A patent/IL30392A/he unknown
- 1968-07-26 ES ES356543A patent/ES356543A1/es not_active Expired
- 1968-07-26 GB GB35757/68A patent/GB1239814A/en not_active Expired
- 1968-07-30 CH CH1141768A patent/CH513920A/de not_active IP Right Cessation
- 1968-07-30 IE IE920/68A patent/IE32230B1/xx unknown
- 1968-07-31 BE BE718824D patent/BE718824A/xx not_active IP Right Cessation
- 1968-08-01 DK DK372068AA patent/DK142912B/da not_active IP Right Cessation
- 1968-08-01 YU YU1833/68A patent/YU34589B/xx unknown
- 1968-08-05 SE SE6810565A patent/SE373591B/xx unknown
- 1968-08-05 IT IT38917/68A patent/IT1035011B/it active
- 1968-08-06 AT AT766168A patent/AT280475B/de not_active IP Right Cessation
- 1968-08-06 FR FR1583480D patent/FR1583480A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770980B2 (de) | 1977-04-07 |
| AT280475B (de) | 1970-04-10 |
| YU183368A (en) | 1979-04-30 |
| DK142912C (he) | 1981-10-05 |
| ES356543A1 (es) | 1970-01-16 |
| CH513920A (de) | 1971-10-15 |
| IE32230B1 (en) | 1973-05-16 |
| FR1583480A (he) | 1969-10-31 |
| NL150798B (nl) | 1976-09-15 |
| SE373591B (sv) | 1975-02-10 |
| DK142912B (da) | 1981-02-23 |
| YU34589B (en) | 1979-10-31 |
| NL6710835A (he) | 1969-02-11 |
| GB1239814A (en) | 1971-07-21 |
| IT1035011B (it) | 1979-10-20 |
| IL30392A0 (en) | 1968-09-26 |
| IE32230L (en) | 1969-02-07 |
| BE718824A (he) | 1969-01-31 |
| DE1770980A1 (de) | 1972-03-02 |
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