ES389293A1 - A procedure for the preparation of a derivative of cefalosporine c. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for the preparation of a derivative of cefalosporine c. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES389293A1 ES389293A1 ES389293A ES389293A ES389293A1 ES 389293 A1 ES389293 A1 ES 389293A1 ES 389293 A ES389293 A ES 389293A ES 389293 A ES389293 A ES 389293A ES 389293 A1 ES389293 A1 ES 389293A1
- Authority
- ES
- Spain
- Prior art keywords
- hydrogen
- formula
- lower alkyl
- mixing
- see formula
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- -1 amine cation Chemical group 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical class 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 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000002184 metal Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
A process for the preparation of a cephalosporin C derivative, called 7-aminocephalosporinic acid, by means of breaking cephalosporin C derivatives, characterized by the fact that it involves the following successive steps; (A) Mixing a compound of formula **(See formula)** in which: each of the M is hydrogen, metal or amine cation, and R is lower alkyl or a group of formula: **(See formula)** where n is an integer from 1 to 6 when B is -OR and 0 to 6 when B is -NHR, and R2 and R3 are the same or different and each can be H, Cl, Br, F, NO2, lower alkyl or lower alkoxy with a silyl compound of the formula **(See formula)** where R5, R6 and R7 are selected from the group consisting of hydrogen, halogen, lower alkyl, haloalkyl (lower) and phenyl, at least one of said groups R5, R6 and R7 being different from halogen or hydrogen; R4 is (lower) alkyl, m is an integer that takes values 1 or 2 and X is selected from the group consisting of halogen and **(See formula)** where R8 is hydrogen or lower alkyl and R9 is hydrogen, lower alkyl or **(See formula)** under anhydrous conditions, in the presence of an acid-deactivating tertiary amine in an inert solvent, to obtain the corresponding silyl ester of compound III; (B) mixing said silyl ester with a halogenating agent in a molar ratio of at least one mole of halogenating agent per mole of silyl ester, in an inert solvent in the presence of an acid-deactivating tertiary amine and at a temperature below 0ºC, to produce the corresponding iminohalide in solution; (C) mixing with said iminohalide solution an alcohol at a temperature below 0ºC, to produce in the solution the corresponding iminoether; and (D) mixing said iminoether solution, under acidic conditions, with water or an alcohol, or a mixture of both, to obtain 7-aminocephalosporanic acid. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74130168A | 1968-07-01 | 1968-07-01 | |
| US74135168A | 1968-07-01 | 1968-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES389293A1 true ES389293A1 (en) | 1973-06-16 |
Family
ID=27113833
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES369029A Expired ES369029A1 (en) | 1968-07-01 | 1969-07-01 | A procedure for preparing a derivative of cefalosporine c. (Machine-translation by Google Translate, not legally binding) |
| ES389293A Expired ES389293A1 (en) | 1968-07-01 | 1971-03-16 | A procedure for the preparation of a derivative of cefalosporine c. (Machine-translation by Google Translate, not legally binding) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES369029A Expired ES369029A1 (en) | 1968-07-01 | 1969-07-01 | A procedure for preparing a derivative of cefalosporine c. (Machine-translation by Google Translate, not legally binding) |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS5432793B1 (en) |
| BE (1) | BE735502A (en) |
| CH (1) | CH534695A (en) |
| DE (1) | DE1933187C3 (en) |
| DK (1) | DK143030C (en) |
| ES (2) | ES369029A1 (en) |
| FR (1) | FR2012122A1 (en) |
| NL (2) | NL145900B (en) |
| SE (1) | SE372274B (en) |
| YU (2) | YU35449B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793037A (en) * | 1971-12-23 | 1973-06-20 | Fujisawa Pharmaceutical Co | PROCESS FOR THE PREPARATION OF 7-ACYLAMINO-3-SUBSTITUE-3-CEPHEM-4-CARBOXYLIC ACID DERIVATIVES AND NEW PRODUCTS THUS OBTAINED |
| GB1425081A (en) * | 1972-06-27 | 1976-02-18 | Fujisawa Pharmaceutical Co | Antibiotics ws-3442a, b,c,d and e and n-acyl derivatives thereof |
| JPS5814923U (en) * | 1981-07-20 | 1983-01-29 | アマノ株式会社 | Filter material for baggage filter |
| JP7197134B2 (en) | 2019-03-12 | 2022-12-27 | 株式会社日立ハイテクサイエンス | Fluorometer and observation method |
-
1969
- 1969-06-30 SE SE924469A patent/SE372274B/xx unknown
- 1969-06-30 DK DK352569A patent/DK143030C/en not_active IP Right Cessation
- 1969-06-30 YU YU166369A patent/YU35449B/en unknown
- 1969-06-30 DE DE19691933187 patent/DE1933187C3/en not_active Expired
- 1969-07-01 JP JP5171369A patent/JPS5432793B1/ja active Pending
- 1969-07-01 ES ES369029A patent/ES369029A1/en not_active Expired
- 1969-07-01 CH CH1006969A patent/CH534695A/en not_active IP Right Cessation
- 1969-07-01 BE BE735502D patent/BE735502A/xx unknown
- 1969-07-01 FR FR6922242A patent/FR2012122A1/en not_active Withdrawn
- 1969-07-01 NL NL6910055A patent/NL145900B/en not_active IP Right Cessation
-
1971
- 1971-03-16 ES ES389293A patent/ES389293A1/en not_active Expired
-
1972
- 1972-06-16 NL NL7208266A patent/NL7208266A/xx unknown
-
1973
- 1973-02-22 JP JP2071973A patent/JPS5235679B1/ja active Pending
-
1977
- 1977-06-18 YU YU149477A patent/YU149477A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU35449B (en) | 1981-02-28 |
| CH534695A (en) | 1973-03-15 |
| DK143030B (en) | 1981-03-16 |
| FR2012122A1 (en) | 1970-03-13 |
| YU149477A (en) | 1983-01-21 |
| ES369029A1 (en) | 1971-10-16 |
| NL7208266A (en) | 1972-08-25 |
| SE372274B (en) | 1974-12-16 |
| BE735502A (en) | 1970-01-02 |
| DE1933187B2 (en) | 1979-10-18 |
| DK143030C (en) | 1981-10-12 |
| NL6910055A (en) | 1970-01-05 |
| DE1933187A1 (en) | 1970-01-08 |
| JPS5432793B1 (en) | 1979-10-16 |
| NL145900B (en) | 1975-05-15 |
| DE1933187C3 (en) | 1980-07-03 |
| JPS5235679B1 (en) | 1977-09-10 |
| YU166369A (en) | 1980-09-25 |
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