IE33571L - Preparation of cephalosporins - Google Patents
Preparation of cephalosporinsInfo
- Publication number
- IE33571L IE33571L IE691159A IE115969A IE33571L IE 33571 L IE33571 L IE 33571L IE 691159 A IE691159 A IE 691159A IE 115969 A IE115969 A IE 115969A IE 33571 L IE33571 L IE 33571L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- nitrogen
- aliphatic unsaturation
- ring
- bonded
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 6
- 229940124587 cephalosporin Drugs 0.000 title abstract 6
- 150000001780 cephalosporins Chemical class 0.000 title abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 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 abstract 1
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 abstract 1
- -1 N-acylated silyl ester Chemical class 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 abstract 1
- 229950004030 cefaloglycin Drugs 0.000 abstract 1
- 229960000603 cefalotin Drugs 0.000 abstract 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 abstract 1
- 229940106164 cephalexin Drugs 0.000 abstract 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 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1,269,697. Silylated cephalosporin derivatives. ELI LILLY & CO. 22 Aug., 1969 [23 Aug., 1968], No. 42066/69. Heading C2A. [Also in Division C3] Novel silylated cephalosporin derivatives of Formula VI wherein R<SP>11</SP> is hydrogen or acetoxy, and R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are each hydrogen or a C 1 to C 8 hydrocarbon radical free from aliphatic unsaturation, with not more than two of R<SP>1</SP> , R<SP>2</SP> and R<SP>3</SP> bonded to the same silicon atom being hydrogen, and R<SP>10</SP> is hydrogen or the group: are prepared by reacting 7-aminocephalosporanic acid or 7-amino-desacetoxycephalosporanic acid or a salt thereof, with a mono- or bissilylamide of one of the Formulµ I to V wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as defined above; R<SP>5</SP> and R<SP>9</SP> are each hydrogen or C 1 to C 8 hydrocarbon free from aliphatic unsaturation, R<SP>8</SP> is C 1 to C 8 hydrocarbon free from aliphatic unsaturation; each of R<SP>4</SP>, R<SP>6</SP> and R<SP>7</SP> is hydrogen or C 1 to C 8 hydrocarbon free from aliphatic unsaturation, or R<SP>6</SP> and R<SP>7</SP> together with the common nitrogen complete a heterocyclic ring containing 5 to 6 ring-forming atoms, one of which can be oxygen para to the nitrogen, or 4 to 6 ring-forming carbons provided that R<SP>6</SP> and R<SP>7</SP> together contain not more than 18 carbons and that if R<SP>6</SP> is alkyl with tert. carbon bonded to the nitrogen then R<SP>7</SP> is hydrogen; or R<SP>4</SP> and R<SP>6</SP> together with the attached nitrogens and the carbonyl group form a heterocyclic ring containing 5 to 6 ring-forming atoms and 2 to 3 methylene ring-forming carbon atoms; and Y is a C 3 to C 18 alkylene group with a 3 to 5 carbon chain between the nitrogen and the carbonyl group to which Y is bonded, the reaction being effected in an anhydrous aprotic solvent at - 25 to +50 C. The invention includes a composition comprising (a) a compound of Formula VI above, (b) a silylamide of one of Formulµ I to V above and (c) an anhydrous solvent for (a) and (b) of which the molecules do not contain Zerewitinoff hydrogen. The silylated cephalosporins may be converted to known antibiotically active cephalosporins by reacting with an appropriate acylating agent to give the corresponding N-acylated silyl ester which is treated with a C 1 to C 6 alkanol to give the required cephalosporin which is recovered from the solution preferably as the Na or K salt. Cephalothin, cephaloglycin and cephalexin are prepared in this way.
[GB1269697A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75499268A | 1968-08-23 | 1968-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33571L true IE33571L (en) | 1970-02-23 |
| IE33571B1 IE33571B1 (en) | 1974-08-21 |
Family
ID=25037254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1159/69A IE33571B1 (en) | 1968-08-23 | 1969-08-15 | Preparation of cephalosporin compounds |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5127676B1 (en) |
| AT (1) | AT313472B (en) |
| BE (1) | BE737761A (en) |
| CH (1) | CH531005A (en) |
| CY (1) | CY795A (en) |
| DE (1) | DE1942454A1 (en) |
| FR (1) | FR2016284B1 (en) |
| GB (1) | GB1269697A (en) |
| HK (1) | HK17276A (en) |
| IE (1) | IE33571B1 (en) |
| IL (1) | IL32815A (en) |
| MY (1) | MY7500103A (en) |
| NL (1) | NL168840C (en) |
| SE (1) | SE385898B (en) |
| ZA (1) | ZA695612B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
| IT1053313B (en) * | 1976-01-15 | 1981-08-31 | Ankerfarm Spa | PROCEDURE FOR PRODUCING SEMI-SYNTHETIC ANTIBIOTICS |
| IT1063088B (en) * | 1976-06-01 | 1985-02-11 | Dobfar Spa | AZETIDINONIC DERIVATIVES AND PROCEDURE FOR THE PREPARATION OF CEPHALOSPORINE |
| CN103193799B (en) * | 2013-03-29 | 2015-08-12 | 武汉回盛生物科技有限公司 | A kind of chemical synthesis process of Cefquinome sulfate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE311519B (en) * | 1962-12-14 | 1969-06-16 | Astra Ab |
-
1969
- 1969-08-05 ZA ZA695612A patent/ZA695612B/en unknown
- 1969-08-12 IL IL32815A patent/IL32815A/en unknown
- 1969-08-15 IE IE1159/69A patent/IE33571B1/en unknown
- 1969-08-20 DE DE19691942454 patent/DE1942454A1/en not_active Ceased
- 1969-08-21 SE SE6911604A patent/SE385898B/en unknown
- 1969-08-21 BE BE737761D patent/BE737761A/xx not_active IP Right Cessation
- 1969-08-22 CH CH1281569A patent/CH531005A/en not_active IP Right Cessation
- 1969-08-22 AT AT1070971A patent/AT313472B/en active
- 1969-08-22 FR FR6928829A patent/FR2016284B1/fr not_active Expired
- 1969-08-22 GB GB42066/69A patent/GB1269697A/en not_active Expired
- 1969-08-22 JP JP44066045A patent/JPS5127676B1/ja active Pending
- 1969-08-22 CY CY795A patent/CY795A/en unknown
- 1969-08-22 NL NLAANVRAGE6912811,A patent/NL168840C/en not_active IP Right Cessation
-
1974
- 1974-03-25 HK HK172/76*UA patent/HK17276A/en unknown
-
1975
- 1975-12-30 MY MY103/75A patent/MY7500103A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE385898B (en) | 1976-07-26 |
| FR2016284B1 (en) | 1974-02-01 |
| IE33571B1 (en) | 1974-08-21 |
| FR2016284A1 (en) | 1970-05-08 |
| IL32815A0 (en) | 1969-11-12 |
| DE1942454A1 (en) | 1970-08-27 |
| IL32815A (en) | 1974-06-30 |
| JPS5127676B1 (en) | 1976-08-13 |
| CY795A (en) | 1976-12-01 |
| NL168840C (en) | 1982-05-17 |
| AT313472B (en) | 1974-02-25 |
| NL6912811A (en) | 1970-02-25 |
| MY7500103A (en) | 1975-12-31 |
| BE737761A (en) | 1970-02-23 |
| GB1269697A (en) | 1972-04-06 |
| NL168840B (en) | 1981-12-16 |
| CH531005A (en) | 1972-11-30 |
| ZA695612B (en) | 1971-03-31 |
| HK17276A (en) | 1976-04-02 |
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