OA12608A - Process for the isolation of crystalline imiponem. - Google Patents
Process for the isolation of crystalline imiponem. Download PDFInfo
- Publication number
- OA12608A OA12608A OA1200300302A OA1200300302A OA12608A OA 12608 A OA12608 A OA 12608A OA 1200300302 A OA1200300302 A OA 1200300302A OA 1200300302 A OA1200300302 A OA 1200300302A OA 12608 A OA12608 A OA 12608A
- Authority
- OA
- OAPI
- Prior art keywords
- water
- organic solvent
- imipenem
- daim
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000002955 isolation Methods 0.000 title claims description 7
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229960002182 imipenem Drugs 0.000 claims abstract description 24
- GSOSVVULSKVSLQ-JJVRHELESA-N imipenem hydrate Chemical compound O.C1C(SCCNC=N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 GSOSVVULSKVSLQ-JJVRHELESA-N 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- -1 éthanol Chemical compound 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 206010053317 Hydrophobia Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 1
- LSNKBVFMXFAUOF-UHFFFAOYSA-N benzyl methanimidate;hydrochloride Chemical compound Cl.N=COCC1=CC=CC=C1 LSNKBVFMXFAUOF-UHFFFAOYSA-N 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical group C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN595DE2001 | 2001-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12608A true OA12608A (en) | 2006-06-08 |
Family
ID=11097062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200300302A OA12608A (en) | 2001-05-18 | 2002-05-20 | Process for the isolation of crystalline imiponem. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7241885B2 (pl) |
| EP (1) | EP1395588A4 (pl) |
| JP (1) | JP2005514323A (pl) |
| KR (1) | KR20040010649A (pl) |
| CN (1) | CN1522255A (pl) |
| AR (1) | AR036018A1 (pl) |
| BR (1) | BR0209844A (pl) |
| CA (1) | CA2447673A1 (pl) |
| CZ (1) | CZ20033351A3 (pl) |
| HU (1) | HUP0501093A2 (pl) |
| MX (1) | MXPA03010548A (pl) |
| NO (1) | NO20035137D0 (pl) |
| OA (1) | OA12608A (pl) |
| PL (1) | PL373527A1 (pl) |
| SK (1) | SK15092003A3 (pl) |
| WO (1) | WO2002094773A2 (pl) |
| ZA (1) | ZA200309288B (pl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1395587E (pt) * | 2001-05-18 | 2009-09-03 | Ranbaxy Lab Ltd | Processo para a preparação de imipenem |
| EP1426376A4 (en) * | 2001-08-13 | 2004-12-22 | Eisai Co Ltd | PROCESS FOR THE PREPARATION OF CARBAPENEM-BASED ANTIBIOTICS |
| BR0214209A (pt) * | 2001-11-16 | 2004-10-26 | Ranbaxy Lab Ltd | Processo para a preparação de imipenem cristalino e composto preparado pelo dito processo |
| EP2209787A4 (en) * | 2007-10-08 | 2011-08-03 | Orchid Chemicals & Pharm Ltd | METHOD FOR PRODUCING A CARBAPENEM ANTIBIOTICS |
| CN103524508B (zh) * | 2013-09-02 | 2016-03-30 | 上海龙翔生物医药开发有限公司 | 一种亚胺培南一水合物的结晶方法 |
| CN108623598A (zh) * | 2018-05-21 | 2018-10-09 | 重庆天地药业有限责任公司 | 一种亚胺培南中间体及亚胺培南的制备方法 |
| CN113135916A (zh) * | 2020-01-20 | 2021-07-20 | 鲁南制药集团股份有限公司 | 一种亚胺培南制备工艺的除钯方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138433A (en) * | 1975-06-26 | 1979-02-06 | Hoechst Aktiengesellschaft | Process for preparing 1,2-oxa-phospholanes |
| US4194047A (en) | 1975-11-21 | 1980-03-18 | Merck & Co., Inc. | Substituted N-methylene derivatives of thienamycin |
| US4081455A (en) * | 1976-06-02 | 1978-03-28 | Pfizer Inc. | 6-Amino-2,2-dimethyl-3-cyanopenams |
| US4260543A (en) | 1978-07-03 | 1981-04-07 | Merck & Co., Inc. | Crystalline N-formimidoyl thienamycin |
| US4292436A (en) * | 1980-06-25 | 1981-09-29 | Merck & Co., Inc. | Process for the preparation of N-protected N-formimidoyl 2-aminoethanethiol |
| US4374772A (en) | 1981-03-19 | 1983-02-22 | Merck & Co., Inc. | Process for the preparation of N-formimidoyl thienamycin and reagents therefor |
| US4894450A (en) | 1987-05-11 | 1990-01-16 | Merck & Co., Inc. | Process for 2-(aminoalkylthio) carbapenems |
| US5245069A (en) * | 1992-10-27 | 1993-09-14 | Merck & Co., Inc. | Process for the preparation of bis(aryl)-phosphorohalidates |
| IN191798B (pl) | 2000-11-03 | 2004-01-03 | Ranbaxy Lab Ltd | |
| BR0214209A (pt) * | 2001-11-16 | 2004-10-26 | Ranbaxy Lab Ltd | Processo para a preparação de imipenem cristalino e composto preparado pelo dito processo |
-
2002
- 2002-05-20 AR ARP020101854A patent/AR036018A1/es not_active Application Discontinuation
- 2002-05-20 CZ CZ20033351A patent/CZ20033351A3/cs unknown
- 2002-05-20 EP EP02730574A patent/EP1395588A4/en not_active Withdrawn
- 2002-05-20 JP JP2002591446A patent/JP2005514323A/ja not_active Withdrawn
- 2002-05-20 MX MXPA03010548A patent/MXPA03010548A/es unknown
- 2002-05-20 OA OA1200300302A patent/OA12608A/en unknown
- 2002-05-20 HU HU0501093A patent/HUP0501093A2/hu unknown
- 2002-05-20 CN CNA028131207A patent/CN1522255A/zh active Pending
- 2002-05-20 PL PL02373527A patent/PL373527A1/pl not_active Application Discontinuation
- 2002-05-20 KR KR10-2003-7015043A patent/KR20040010649A/ko not_active Withdrawn
- 2002-05-20 SK SK1509-2003A patent/SK15092003A3/sk not_active Application Discontinuation
- 2002-05-20 CA CA002447673A patent/CA2447673A1/en not_active Abandoned
- 2002-05-20 US US10/478,624 patent/US7241885B2/en not_active Expired - Fee Related
- 2002-05-20 WO PCT/IB2002/001718 patent/WO2002094773A2/en not_active Ceased
- 2002-05-20 BR BR0209844-0A patent/BR0209844A/pt not_active IP Right Cessation
-
2003
- 2003-11-18 NO NO20035137A patent/NO20035137D0/no not_active Application Discontinuation
- 2003-11-28 ZA ZA200309288A patent/ZA200309288B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0209844A (pt) | 2005-04-05 |
| CA2447673A1 (en) | 2002-11-28 |
| EP1395588A4 (en) | 2004-09-15 |
| US20040242865A1 (en) | 2004-12-02 |
| WO2002094773A3 (en) | 2003-10-16 |
| US7241885B2 (en) | 2007-07-10 |
| JP2005514323A (ja) | 2005-05-19 |
| HUP0501093A2 (en) | 2006-03-28 |
| SK15092003A3 (sk) | 2004-09-08 |
| WO2002094773A2 (en) | 2002-11-28 |
| CN1522255A (zh) | 2004-08-18 |
| EP1395588A2 (en) | 2004-03-10 |
| KR20040010649A (ko) | 2004-01-31 |
| MXPA03010548A (es) | 2004-05-27 |
| AR036018A1 (es) | 2004-08-04 |
| CZ20033351A3 (cs) | 2007-12-27 |
| PL373527A1 (pl) | 2005-09-05 |
| ZA200309288B (en) | 2005-02-28 |
| NO20035137D0 (no) | 2003-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7332600B2 (en) | Process for the preparation of crystalline imipenem | |
| MX2011009532A (es) | Metodo mejorado para preparar meropenem usando polvo de zinc. | |
| KR100364339B1 (ko) | 안정화된 카바페넴 중간체 및 합성적 용도 | |
| CA2461565C (en) | Process for making carbapenem compounds | |
| US7241885B2 (en) | Process for the isolation of crystalline imipenem | |
| US7078534B2 (en) | Process for the preparation of crystalline N-formimidoyl thienamycin monohydrate (imipenem monohydrate) | |
| ES2328117T3 (es) | Proceso para la preparacion de imipenem. | |
| CN100383142C (zh) | 一种制备亚胺培南的方法 | |
| AU2002302887A1 (en) | Process for the isolation of crystalline imipenem | |
| WO2012081033A2 (en) | A process for preparation of imipenem | |
| KR20130028203A (ko) | 무정형 도리페넴·일수화물의 제조방법 | |
| AU2002347451A1 (en) | Process for the preparation of crystalline imipenem | |
| WO1997031922A1 (en) | Process for the preparation of 2-halomethyl-penems and their use for the preparation of antibacterial penems | |
| AU2002302882A1 (en) | Process for the preparation of imipenem |