GB1494452A - Process for preparing 7-aminocephalosporanic acid derivatives - Google Patents
Process for preparing 7-aminocephalosporanic acid derivativesInfo
- Publication number
- GB1494452A GB1494452A GB2162/76A GB216276A GB1494452A GB 1494452 A GB1494452 A GB 1494452A GB 2162/76 A GB2162/76 A GB 2162/76A GB 216276 A GB216276 A GB 216276A GB 1494452 A GB1494452 A GB 1494452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- keto
- formula
- acid
- derivative
- acid derivatives
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 abstract 1
- 229920006310 Asahi-Kasei Polymers 0.000 abstract 1
- 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 abstract 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 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
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 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 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP863675A JPS5186490A (ja) | 1975-01-22 | 1975-01-22 | Sefuarosuhorinkagobutsuno seiho |
| JP8357575A JPS5929599B2 (ja) | 1975-07-09 | 1975-07-09 | ７−アミノセフアロスポラン酸誘導体の製造法 |
| JP8357475A JPS527986A (en) | 1975-07-09 | 1975-07-09 | Process for preparing 7-aminocephalosporanic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1494452A true GB1494452A (en) | 1977-12-07 |
Family
ID=27278114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2162/76A Expired GB1494452A (en) | 1975-01-22 | 1976-01-20 | Process for preparing 7-aminocephalosporanic acid derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4079180A (https=) |
| BE (1) | BE837766A (https=) |
| CA (1) | CA1069120A (https=) |
| CH (1) | CH621124A5 (https=) |
| DE (2) | DE2602099C3 (https=) |
| DK (1) | DK153554C (https=) |
| FR (1) | FR2298552A1 (https=) |
| GB (1) | GB1494452A (https=) |
| HU (1) | HU171208B (https=) |
| IT (1) | IT1053405B (https=) |
| NL (1) | NL163789C (https=) |
| SE (1) | SE427184B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4175185A (en) * | 1976-05-19 | 1979-11-20 | Meiji Seika Kaisha Ltd. | Process for preparing cephalosporanic acid derivatives |
| EP0409521B1 (en) * | 1989-07-19 | 1995-10-11 | Eli Lilly And Company | Improved enzymatic oxidation of ceph C to glutaryl-7-amino-cephalosporanic acid |
| CN1130908A (zh) * | 1994-07-22 | 1996-09-11 | 安蒂比奥蒂科斯公司 | 戊二酸单酰基7-氨基头孢烷酸衍生物及其制备方法 |
| KR0174117B1 (ko) * | 1995-12-28 | 1999-02-01 | 윤원영 | 새로운 세팔로스포린 유도체 및 그 제조방법 |
| CN107868812A (zh) * | 2017-12-20 | 2018-04-03 | 焦作健康元生物制品有限公司 | 一种7‑氨基头孢烷酸的改进生产工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK142367B (da) * | 1968-08-02 | 1980-10-20 | Glaxo Lab Ltd | 7-Acylamidocephalosporanderivater til anvendelse som mellemprodukter ved fremstilling af 7-aminocephalosporansyre eller derivater deraf, samt fremgangsmåde til fremstilling deraf. |
| BE793448A (fr) * | 1971-12-31 | 1973-06-28 | Roussel Uclaf | Procede de preparation de nouveaux derives des cephalosporines et produits obtenus |
| US3928324A (en) * | 1973-02-08 | 1975-12-23 | Pfizer | Malonyl derivatives of 6-({60 -aminoacylamido)penicillanic acids |
| US3932392A (en) * | 1974-01-14 | 1976-01-13 | Bristol-Myers Company | Process for the preparation of 7-aminocephalosporanic acids |
-
1976
- 1976-01-20 US US05/650,701 patent/US4079180A/en not_active Expired - Lifetime
- 1976-01-20 GB GB2162/76A patent/GB1494452A/en not_active Expired
- 1976-01-21 NL NL7600602.A patent/NL163789C/xx not_active IP Right Cessation
- 1976-01-21 SE SE7600585A patent/SE427184B/xx not_active IP Right Cessation
- 1976-01-21 HU HU76AA00000842A patent/HU171208B/hu unknown
- 1976-01-21 BE BE163675A patent/BE837766A/xx not_active IP Right Cessation
- 1976-01-21 DK DK022576A patent/DK153554C/da not_active IP Right Cessation
- 1976-01-21 DE DE2602099A patent/DE2602099C3/de not_active Expired
- 1976-01-21 CA CA243,992A patent/CA1069120A/en not_active Expired
- 1976-01-21 CH CH74376A patent/CH621124A5/de not_active IP Right Cessation
- 1976-01-21 DE DE19762659857 patent/DE2659857A1/de not_active Ceased
- 1976-01-21 IT IT47732/76A patent/IT1053405B/it active
- 1976-01-21 FR FR7601588A patent/FR2298552A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH621124A5 (https=) | 1981-01-15 |
| SE7600585L (sv) | 1976-07-23 |
| HU171208B (hu) | 1977-12-28 |
| SE427184B (sv) | 1983-03-14 |
| NL163789B (nl) | 1980-05-16 |
| NL7600602A (nl) | 1976-07-26 |
| DE2659857A1 (de) | 1977-10-27 |
| DK153554B (da) | 1988-07-25 |
| DE2602099C3 (de) | 1979-05-23 |
| US4079180A (en) | 1978-03-14 |
| FR2298552B1 (https=) | 1978-07-21 |
| DK22576A (da) | 1976-07-23 |
| CA1069120A (en) | 1980-01-01 |
| FR2298552A1 (fr) | 1976-08-20 |
| IT1053405B (it) | 1981-08-31 |
| NL163789C (nl) | 1980-10-15 |
| DK153554C (da) | 1988-12-05 |
| DE2602099B2 (de) | 1978-10-05 |
| DE2602099A1 (de) | 1976-07-29 |
| BE837766A (fr) | 1976-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960119 |