RU2006102664A - Новый способ получения имипенема - Google Patents
Новый способ получения имипенема Download PDFInfo
- Publication number
- RU2006102664A RU2006102664A RU2006102664/04A RU2006102664A RU2006102664A RU 2006102664 A RU2006102664 A RU 2006102664A RU 2006102664/04 A RU2006102664/04 A RU 2006102664/04A RU 2006102664 A RU2006102664 A RU 2006102664A RU 2006102664 A RU2006102664 A RU 2006102664A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- formula
- nitrobenzyl
- ketone
- group
- Prior art date
Links
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
- C07D477/02—Preparation
- C07D477/06—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (9)
1. Соединение формулы II
где R1 представляет п-нитробензильную или п-метоксибензильную группу; и R2 и R3 могут быть одинаковыми или разными, и каждый независимо представляет С1-6 алкильную или арильную группу,
или его производное.
2. Способ получения соединения формулы II
где R1 представляет п-нитробензильную или п-метоксибензильную группу; и R2 и R3 могут быть одинаковыми или разными, и каждый независимо представляет С1-6 алкильную или арильную группу, путем сочетания соединения формулы IV
где R1 представляет п-нитробензильную или п-метоксибензильную группу, или его производного с гидрохлоридом 2-аминоэтантиола в присутствии основания с последующей реакцией с кетоном.
3. Способ по п.2, в котором кетон выбран из группы, состоящей из ацетона, метилэтилкетона, дифенилкетона и их смесей.
4. Способ по п.2 или 3, в котором соединение формулы IV или его производное получают путем конденсации соединения формулы III
где R1 представляет п-нитробензильную или п-метоксибензильную группу, с дифенилхлорфосфатом в присутствии основания.
5. Способ по п.4, в котором растворитель для реакции является смешанным растворителем из ацетонитрила и тетрагидрофурана.
6. Способ по п.4, в котором температура реакции находится в интервале от 0 до -10С.
7. Способ получения соединения формулы I
путем взаимодействия соединения формулы II
где R1 представляет п-нитробензильную или п-метоксибензильную группу; и R2 и R3 могут быть одинаковыми или разными, и каждый независимо представляет С1-6 алкильную или арильную группу, с изопропилформимидатом или бензилформимидатом в присутствии основания с получением соединения формулы V
где R1 представляет п-нитробензильную или п-метоксибензильную группу, гидрирования соединения формулы V в присутствии катализатора-металла, выделения гидрированного соединения и кристаллизации выделенного соединения в присутствии спирта или кетона.
8. Способ по п.7, в котором гидрирование проводят в присутствии палладиевого катализатора, содержащего большое количество воды, при давлении водорода 4-6 кг/см2.
9. Способ по п.7, в котором растворитель для реакции является смешанным растворителем из воды и тетрагидрофурана.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20030088857 | 2003-12-09 | ||
| KR10-2003-0088857 | 2003-12-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006102664A true RU2006102664A (ru) | 2006-08-10 |
| RU2314308C2 RU2314308C2 (ru) | 2008-01-10 |
Family
ID=36642326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006102664/04A RU2314308C2 (ru) | 2003-12-09 | 2004-12-09 | Новый способ получения имипенема |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7507814B2 (ru) |
| EP (1) | EP1692135A4 (ru) |
| JP (1) | JP4500814B2 (ru) |
| KR (1) | KR100667373B1 (ru) |
| CN (1) | CN100383142C (ru) |
| AU (1) | AU2004296261B2 (ru) |
| BR (1) | BRPI0413057B8 (ru) |
| CA (1) | CA2531578C (ru) |
| MX (1) | MXPA06001115A (ru) |
| NO (1) | NO20062602L (ru) |
| NZ (1) | NZ547641A (ru) |
| RU (1) | RU2314308C2 (ru) |
| WO (1) | WO2005056553A1 (ru) |
| ZA (1) | ZA200604446B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1395587B1 (en) * | 2001-05-18 | 2009-07-29 | Ranbaxy Laboratories Limited | Process for the preparation of imipenem |
| KR100667373B1 (ko) * | 2003-12-09 | 2007-01-10 | 주식회사 중외제약 | 이미페넴의 신규 제조방법 |
| CN102690266B (zh) * | 2011-09-02 | 2014-06-18 | 深圳市海滨制药有限公司 | 一种制备厄他培南钠的方法 |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235920A (en) * | 1975-11-21 | 1980-11-25 | Merck & Co., Inc. | N-Alkylated derivatives of thienamycin |
| GB1570988A (en) * | 1975-11-21 | 1980-07-09 | Merck & Co Inc | Antibiotics of the thienamycin class |
| US4172144A (en) * | 1976-10-18 | 1979-10-23 | Merck & Co., Inc. | Schiff's base derivatives of thienamycin |
| US4150145A (en) * | 1977-09-15 | 1979-04-17 | Merck & Co., Inc. | N-alkylated derivatives of thienamycin sulfoxide and sulfone |
| US4292436A (en) | 1980-06-25 | 1981-09-29 | Merck & Co., Inc. | Process for the preparation of N-protected N-formimidoyl 2-aminoethanethiol |
| US4845261A (en) | 1987-05-11 | 1989-07-04 | Merck & Co., Inc. | Process for bis(substituted phenyl) phosphorohalidates |
| US4894450A (en) * | 1987-05-11 | 1990-01-16 | Merck & Co., Inc. | Process for 2-(aminoalkylthio) carbapenems |
| IN191798B (ru) * | 2000-11-03 | 2004-01-03 | Ranbaxy Lab Ltd | |
| ITMI20010077A1 (it) * | 2001-01-17 | 2002-07-18 | Acs Dobfar Spa | Procedimento per la produzione dell'imipenem |
| EP1395587B1 (en) * | 2001-05-18 | 2009-07-29 | Ranbaxy Laboratories Limited | Process for the preparation of imipenem |
| KR100667373B1 (ko) * | 2003-12-09 | 2007-01-10 | 주식회사 중외제약 | 이미페넴의 신규 제조방법 |
-
2004
- 2004-12-09 KR KR1020040103762A patent/KR100667373B1/ko active IP Right Grant
- 2004-12-09 WO PCT/KR2004/003224 patent/WO2005056553A1/en active Application Filing
- 2004-12-09 EP EP04808355A patent/EP1692135A4/en not_active Withdrawn
- 2004-12-09 JP JP2006523142A patent/JP4500814B2/ja active Active
- 2004-12-09 BR BRPI0413057A patent/BRPI0413057B8/pt active IP Right Grant
- 2004-12-09 NZ NZ547641A patent/NZ547641A/en unknown
- 2004-12-09 MX MXPA06001115A patent/MXPA06001115A/es active IP Right Grant
- 2004-12-09 AU AU2004296261A patent/AU2004296261B2/en active Active
- 2004-12-09 US US10/563,250 patent/US7507814B2/en active Active
- 2004-12-09 CA CA002531578A patent/CA2531578C/en active Active
- 2004-12-09 CN CNB2004800217450A patent/CN100383142C/zh active Active
- 2004-12-09 RU RU2006102664/04A patent/RU2314308C2/ru active
-
2006
- 2006-05-31 ZA ZA200604446A patent/ZA200604446B/en unknown
- 2006-06-06 NO NO20062602A patent/NO20062602L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1692135A1 (en) | 2006-08-23 |
| BRPI0413057B1 (pt) | 2018-02-06 |
| AU2004296261A1 (en) | 2005-06-23 |
| KR20050056161A (ko) | 2005-06-14 |
| ZA200604446B (en) | 2007-10-31 |
| MXPA06001115A (es) | 2006-04-11 |
| JP4500814B2 (ja) | 2010-07-14 |
| US20060167243A1 (en) | 2006-07-27 |
| US7507814B2 (en) | 2009-03-24 |
| WO2005056553A1 (en) | 2005-06-23 |
| BRPI0413057A (pt) | 2006-10-17 |
| AU2004296261B2 (en) | 2007-08-23 |
| RU2314308C2 (ru) | 2008-01-10 |
| CA2531578C (en) | 2008-10-07 |
| EP1692135A4 (en) | 2009-02-25 |
| BRPI0413057B8 (pt) | 2021-05-25 |
| KR100667373B1 (ko) | 2007-01-10 |
| CN100383142C (zh) | 2008-04-23 |
| CN1829716A (zh) | 2006-09-06 |
| NZ547641A (en) | 2009-02-28 |
| NO20062602L (no) | 2006-08-31 |
| JP2007501838A (ja) | 2007-02-01 |
| CA2531578A1 (en) | 2005-06-23 |
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