WO2012160576A3 - A process for preparation of meropenem - Google Patents
A process for preparation of meropenem Download PDFInfo
- Publication number
- WO2012160576A3 WO2012160576A3 PCT/IN2012/000369 IN2012000369W WO2012160576A3 WO 2012160576 A3 WO2012160576 A3 WO 2012160576A3 IN 2012000369 W IN2012000369 W IN 2012000369W WO 2012160576 A3 WO2012160576 A3 WO 2012160576A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meropenem
- sterile
- trihydrate
- diprotected
- preparation
- Prior art date
Links
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 title abstract 7
- 229960002260 meropenem Drugs 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 238000010926 purge Methods 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention relates to a novel, cost-effective process for the preparation of Sterile Meropenem Trihydrate, which is prepared by a) condensation of l-Azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid, 3- [(diphenoxyphosphinyl)oxy]-6-(l-hydroxyethyl)-4-methyl-7-oxo-(4-nitrobenzyl) methyl ester,[4R-[4a,5b,6b(R*)]] with (2S,4S)-2-(Dimethylaminqcarbonyl)-4- mercapto-l -(p-nitrobenzyloxycarbonyl)-l -pyrrolidine to obtain diprotected Meropenem; b) deprotection and hydrogenation of diprotected Meropenem to obtain non-sterile Meropenem Trihydrate; c) conversion of NS Meropenem Trihydrate into Sterile Meropenem Trihydrate by using water, methanolic ammonia solution and purging carbon dioxide gas.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1780/CHE/2011 | 2011-05-26 | ||
| IN1780CH2011 | 2011-05-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2012160576A2 WO2012160576A2 (en) | 2012-11-29 |
| WO2012160576A3 true WO2012160576A3 (en) | 2013-03-28 |
Family
ID=47217832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2012/000369 WO2012160576A2 (en) | 2011-05-26 | 2012-05-25 | A process for preparation of meropenem |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2012160576A2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102977102A (en) * | 2012-12-21 | 2013-03-20 | 卫宏远 | Preparation method of meropenem trihydrate crystal |
| KR101331762B1 (en) * | 2012-12-28 | 2013-11-20 | 주식회사 대웅제약 | Process for preparing meropenem.trihydrate |
| CN118806701B (en) * | 2024-09-19 | 2024-12-10 | 青松(天津)制药有限公司 | Meropenem-containing injection and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036120A (en) * | 1958-11-10 | 1962-05-22 | Pfizer & Co C | Dicarboxylic acid derivatives of tetracycline and its analogs |
| US4962103A (en) * | 1984-11-08 | 1990-10-09 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and production thereof |
| WO2009047604A1 (en) * | 2007-10-08 | 2009-04-16 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of carbapenem antibiotic |
| US20090264643A1 (en) * | 2005-09-15 | 2009-10-22 | Orchid Chemicals & Pharmaceuticals Ltd. | Process for The Preparation of Beta-Lactam Antibiotic |
-
2012
- 2012-05-25 WO PCT/IN2012/000369 patent/WO2012160576A2/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036120A (en) * | 1958-11-10 | 1962-05-22 | Pfizer & Co C | Dicarboxylic acid derivatives of tetracycline and its analogs |
| US4962103A (en) * | 1984-11-08 | 1990-10-09 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and production thereof |
| US20090264643A1 (en) * | 2005-09-15 | 2009-10-22 | Orchid Chemicals & Pharmaceuticals Ltd. | Process for The Preparation of Beta-Lactam Antibiotic |
| WO2009047604A1 (en) * | 2007-10-08 | 2009-04-16 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of carbapenem antibiotic |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012160576A2 (en) | 2012-11-29 |
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