WO2011021223A3 - Novel salts of ethyl (3r, 4s, 5r)-4,5-imino-3-(l-ethylpropoxy)-1- cvclohexene-1-carboxylate and its use - Google Patents

Novel salts of ethyl (3r, 4s, 5r)-4,5-imino-3-(l-ethylpropoxy)-1- cvclohexene-1-carboxylate and its use Download PDF

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Publication number
WO2011021223A3
WO2011021223A3 PCT/IN2010/000545 IN2010000545W WO2011021223A3 WO 2011021223 A3 WO2011021223 A3 WO 2011021223A3 IN 2010000545 W IN2010000545 W IN 2010000545W WO 2011021223 A3 WO2011021223 A3 WO 2011021223A3
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WO
WIPO (PCT)
Prior art keywords
ethyl
ethylpropoxy
imino
carboxylate
cvclohexene
Prior art date
Application number
PCT/IN2010/000545
Other languages
French (fr)
Other versions
WO2011021223A2 (en
Inventor
Manne Satyanarayana Reddy
Srinivasan Thirumalai Rajan
Karamala Rama Subba Reddy
Original Assignee
Msn Laboratories Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Msn Laboratories Limited filed Critical Msn Laboratories Limited
Publication of WO2011021223A2 publication Critical patent/WO2011021223A2/en
Publication of WO2011021223A3 publication Critical patent/WO2011021223A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/08—Acetic acid
    • C07C53/10—Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/06—Oxalic acid
    • C07C55/07—Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/08—Malonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/10—Succinic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/145—Maleic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265—Citric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/26—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to novel salts of ethyl (3R,4S,5R)- 4,5-imino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate and its use in the preparation of (3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethyl propoxy)-1-cyclohexene-1-carboxylic acid ethyl ester and its pharmaceutically acceptable salts.
PCT/IN2010/000545 2009-08-19 2010-08-18 Novel salts of ethyl (3r, 4s, 5r)-4,5-imino-3-(l-ethylpropoxy)-1- cvclohexene-1-carboxylate and its use WO2011021223A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1974CH2009 2009-08-19
IN1974/CHE/2009 2009-08-19

Publications (2)

Publication Number Publication Date
WO2011021223A2 WO2011021223A2 (en) 2011-02-24
WO2011021223A3 true WO2011021223A3 (en) 2011-04-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2010/000545 WO2011021223A2 (en) 2009-08-19 2010-08-18 Novel salts of ethyl (3r, 4s, 5r)-4,5-imino-3-(l-ethylpropoxy)-1- cvclohexene-1-carboxylate and its use

Country Status (1)

Country Link
WO (1) WO2011021223A2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103833570B (en) * 2014-03-19 2015-05-27 浙江师范大学 Synthesis method of oseltamivir
CN108047076B (en) * 2017-12-26 2020-05-08 杭州新博思生物医药有限公司 Preparation method of oseltamivir enantiomer
CN110194728B (en) * 2019-06-19 2021-04-30 湖南华腾制药有限公司 Continuous synthesis method of oseltamivir phosphate intermediate
CN110698374A (en) * 2019-07-09 2020-01-17 苏州奥普拓新材料有限公司 Synthesis of continuous oseltamivir phosphate intermediate
CN111153818B (en) * 2020-03-13 2023-03-28 遂成药业股份有限公司 Method for preparing antiviral drug Tamiflu intermediate tert-butylamine derivative I
CN114133364B (en) * 2021-11-05 2023-06-27 中润药业有限公司 Synthesis method of oseltamivir intermediate
CN115266965B (en) * 2022-07-01 2024-04-02 苏州博研医药科技有限公司 High performance liquid chromatography method for detecting oseltamivir phosphate key intermediate specific impurities
CN115745921A (en) * 2022-10-28 2023-03-07 北京格林意锐医药科技有限责任公司 Preparation method and application of oseltamivir intermediate impurity
CN116375595A (en) * 2023-03-31 2023-07-04 重庆医药高等专科学校 Preparation method and refining method of oseltamivir phosphate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996026933A1 (en) * 1995-02-27 1996-09-06 Gilead Sciences, Inc. Novel selective inhibitors of viral or bacterial neuraminidases
WO2001032617A1 (en) * 1999-11-02 2001-05-10 Sagami Chemical Research Center Process for the preparation of 7-azabicyclo[4.1.0]-hept-3-ene-3-carboxylic acid esters

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996026933A1 (en) * 1995-02-27 1996-09-06 Gilead Sciences, Inc. Novel selective inhibitors of viral or bacterial neuraminidases
WO2001032617A1 (en) * 1999-11-02 2001-05-10 Sagami Chemical Research Center Process for the preparation of 7-azabicyclo[4.1.0]-hept-3-ene-3-carboxylic acid esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ROHLOFF J.C. ET AL: "Practical Total Synthesis of the Anti-Influenza Drug GS-4104", J. ORG. CHEM., vol. 63, no. 13, 5 June 1998 (1998-06-05), pages 4545 - 4550 *

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