DE2501219C2 - Verfahren zur Herstellung von 7-Aminocephalosporansäuren - Google Patents
Verfahren zur Herstellung von 7-AminocephalosporansäurenInfo
- Publication number
- DE2501219C2 DE2501219C2 DE2501219A DE2501219A DE2501219C2 DE 2501219 C2 DE2501219 C2 DE 2501219C2 DE 2501219 A DE2501219 A DE 2501219A DE 2501219 A DE2501219 A DE 2501219A DE 2501219 C2 DE2501219 C2 DE 2501219C2
- Authority
- DE
- Germany
- Prior art keywords
- dicyclohexylamine
- added
- ester
- compound
- slurry
- 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
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- 238000000034 method Methods 0.000 title claims description 20
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- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000007513 acids Chemical class 0.000 title claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 12
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- -1 phenylacetyl Chemical group 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 33
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- 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 description 28
- 239000002002 slurry Substances 0.000 description 28
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound 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 25
- 239000000460 chlorine Substances 0.000 description 21
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 13
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- 238000003776 cleavage reaction Methods 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
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- 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 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
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- 229910052794 bromium Inorganic materials 0.000 description 5
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- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 5
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- 238000011835 investigation Methods 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- 229930186147 Cephalosporin Natural products 0.000 description 4
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- 229910004013 NO 2 Inorganic materials 0.000 description 4
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- 238000013146 percutaneous coronary intervention Methods 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
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- FJSYPCRVAYJCEX-AWKYBWMHSA-N N-[(6R)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]-2-phenylacetamide Chemical compound C1(=CC=CC=C1)CC(=O)NC1[C@@H]2N(C=C(CS2)C)C1=O FJSYPCRVAYJCEX-AWKYBWMHSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
- 229950004616 tribromoethanol Drugs 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/433,336 US3932392A (en) | 1974-01-14 | 1974-01-14 | Process for the preparation of 7-aminocephalosporanic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2501219A1 DE2501219A1 (de) | 1975-07-17 |
| DE2501219C2 true DE2501219C2 (de) | 1982-11-04 |
Family
ID=23719798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2501219A Expired DE2501219C2 (de) | 1974-01-14 | 1975-01-14 | Verfahren zur Herstellung von 7-Aminocephalosporansäuren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3932392A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS604190B2 (cg-RX-API-DMAC7.html) |
| CH (1) | CH594688A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2501219C2 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1484231A (cg-RX-API-DMAC7.html) |
| IE (1) | IE41406B1 (cg-RX-API-DMAC7.html) |
| LU (1) | LU71636A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL180750C (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1494452A (en) * | 1975-01-22 | 1977-12-07 | Asahi Chemical Ind | Process for preparing 7-aminocephalosporanic acid derivatives |
| DE2619243C2 (de) * | 1975-05-06 | 1985-07-04 | Takeda Chemical Industries, Ltd., Osaka | Verfahren zur Herstellung von 3-Acyloxymethyl-cephem-Verbindungen |
| US4097670A (en) * | 1976-04-05 | 1978-06-27 | E. R. Squibb & Sons, Inc. | Carboxyalkylureido cephalosporins |
| US4086422A (en) * | 1976-08-16 | 1978-04-25 | E. R. Squibb & Sons, Inc. | Carbamoylalkylureido cephalosporins |
| JPS5811955B2 (ja) * | 1977-08-08 | 1983-03-05 | 山之内製薬株式会社 | ７ａ−メトキシセフアロスポラン酸誘導体の新規合成法 |
| GR70261B (cg-RX-API-DMAC7.html) * | 1977-12-12 | 1982-09-02 | Takeda Chemical Industries Ltd | |
| US4252973A (en) * | 1979-07-06 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Process for chemically removing the acyl sidechain from cephalosporins and penicillins |
| US4520101A (en) * | 1983-03-07 | 1985-05-28 | Bristol-Myers Company | Production of cephalosporin C |
| JPS6433893U (cg-RX-API-DMAC7.html) * | 1987-08-25 | 1989-03-02 | ||
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| WO1998054194A1 (en) * | 1997-05-30 | 1998-12-03 | Nof Corporation | Process for producing (meth)acrylate derivatives |
| JP2002316991A (ja) * | 2001-04-18 | 2002-10-31 | Otsuka Chem Co Ltd | ペニシリン及びセファロスポリン化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO138629C (no) * | 1969-03-11 | 1978-10-11 | Glaxo Lab Ltd | Fremgangsmaate for fremstilling av 7beta-acylamidometyl-ceph-3-em-4-karboksylsyre-estere. |
| GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1974
- 1974-01-14 US US05/433,336 patent/US3932392A/en not_active Expired - Lifetime
-
1975
- 1975-01-10 NL NLAANVRAGE7500321,A patent/NL180750C/xx not_active IP Right Cessation
- 1975-01-13 IE IE53/75A patent/IE41406B1/en unknown
- 1975-01-13 GB GB1320/75A patent/GB1484231A/en not_active Expired
- 1975-01-13 LU LU71636A patent/LU71636A1/xx unknown
- 1975-01-14 DE DE2501219A patent/DE2501219C2/de not_active Expired
- 1975-01-14 JP JP50006005A patent/JPS604190B2/ja not_active Expired
- 1975-01-14 CH CH37475A patent/CH594688A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7500321A (nl) | 1975-07-16 |
| DE2501219A1 (de) | 1975-07-17 |
| IE41406L (en) | 1975-07-14 |
| IE41406B1 (en) | 1980-01-02 |
| GB1484231A (en) | 1977-09-01 |
| NL180750C (nl) | 1987-04-16 |
| US3932392A (en) | 1976-01-13 |
| JPS50116487A (cg-RX-API-DMAC7.html) | 1975-09-11 |
| JPS604190B2 (ja) | 1985-02-01 |
| LU71636A1 (cg-RX-API-DMAC7.html) | 1975-12-09 |
| CH594688A5 (cg-RX-API-DMAC7.html) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |