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WO2007054974B1 - A green chemistry process for the preparation of pregnadiene esters - Google Patents

A green chemistry process for the preparation of pregnadiene esters

Info

Publication number
WO2007054974B1
WO2007054974B1 PCT/IN2006/000399 IN2006000399W WO2007054974B1 WO 2007054974 B1 WO2007054974 B1 WO 2007054974B1 IN 2006000399 W IN2006000399 W IN 2006000399W WO 2007054974 B1 WO2007054974 B1 WO 2007054974B1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
preparation
esters
pregnadiene
green chemistry
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.)
Ceased
Application number
PCT/IN2006/000399
Other languages
French (fr)
Other versions
WO2007054974A2 (en
WO2007054974A3 (en
Inventor
Ashish Ujagare
D A Kochrekar
Mathew C Uzagare
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arch Pharmalabs Ltd
Original Assignee
Arch Pharmalabs Ltd
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 Arch Pharmalabs Ltd filed Critical Arch Pharmalabs Ltd
Publication of WO2007054974A2 publication Critical patent/WO2007054974A2/en
Publication of WO2007054974A3 publication Critical patent/WO2007054974A3/en
Publication of WO2007054974B1 publication Critical patent/WO2007054974B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals
    • C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Steroid Compounds (AREA)

Abstract

A process for the preparation of Pregna-1, 4-diene - 3,20-dione-16,17-acetal-21 esters of Formula (I) by a green process chemistry using a combination of an ionic liquid, organic solvent optionally in the presence of an inorganic nitrite. Formula I, wherein R and R' represent a) R= H, R'-cyclohexyl or b) R=CO-CH (CH3) 2, R'=cyclohexyl or c) R=H, R'=CH2-CH2-CH3.

Claims

20AMENDED CLAIMS(received by the International Bureau on 11 September 2007 (11.09.07); Claim 1 amended, rest claims remain unchanged (pagei))+Statement
1. A process for the preparation of compounds of Formula (I)
Figure imgf000002_0001
Formula I
Wherein R and R represent a) R= H1 R'-cyclohexyl or b) R=CO-CH(CH3)2, R'=cyclohexyl or c) R=H1 R^GH2-CH2-CH3
in predominantly epimerically pure form comprising the step of: i. reacting the compound of Formula (II)
Figure imgf000002_0002
Formula Il Wherein R, R1 and R2 represent a) (R = H1 R1 = CH3, R2= CH3] or b) (R= CO-CH (CH3) 2, R1 = CH3, R2= CH3)
or reacting the compound of Formula (III)
PCT/IN2006/000399 2005-09-28 2006-09-28 A green chemistry process for the preparation of pregnadiene esters Ceased WO2007054974A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1210MU2005 2005-09-28
IN1210/MUM/2005 2005-09-28

Publications (3)

Publication Number Publication Date
WO2007054974A2 WO2007054974A2 (en) 2007-05-18
WO2007054974A3 WO2007054974A3 (en) 2007-08-30
WO2007054974B1 true WO2007054974B1 (en) 2007-11-22

Family

ID=38023687

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2006/000399 Ceased WO2007054974A2 (en) 2005-09-28 2006-09-28 A green chemistry process for the preparation of pregnadiene esters

Country Status (1)

Country Link
WO (1) WO2007054974A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106290695A (en) * 2015-06-25 2017-01-04 重庆华邦制药有限公司 Desonide and the separation of related impurities and assay method

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070020299A1 (en) 2003-12-31 2007-01-25 Pipkin James D Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid
US12370352B2 (en) 2007-06-28 2025-07-29 Cydex Pharmaceuticals, Inc. Nasal and ophthalmic delivery of aqueous corticosteroid solutions
EA201000436A1 (en) 2007-10-04 2010-10-29 Астразенека Аб STEROID [3,2-С] PYRAZOLIC COMPOUNDS WITH GLUCOCORTICOID ACTIVITY
WO2009108118A1 (en) * 2008-02-27 2009-09-03 Astrazeneca Ab 16 alpha, 17 alpa-acetal glucocorticosteroidal derivatives and their use
UY32520A (en) 2009-04-03 2010-10-29 Astrazeneca Ab COMPOUNDS THAT HAVE AGONIST ACTIVITY OF THE GLUCOCORTICOESTEROID RECEPTOR
CN101875681B (en) * 2010-06-22 2012-08-08 浙江工业大学 Synthetic method of 16alpha-hydroxy prednisonlone
US9109005B2 (en) 2012-02-23 2015-08-18 Boehringer Ingelheim International Gmbh Method for manufacturing of ciclesonide
ES2877548T3 (en) 2016-06-02 2021-11-17 Abbvie Inc Glucocorticoid receptor agonist and immunoconjugates thereof
AU2018374634A1 (en) 2017-12-01 2020-05-28 Abbvie Inc. Glucocorticoid receptor agonist and immunoconjugates thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4124707A (en) * 1976-12-22 1978-11-07 Schering Corporation 7α-Halogeno-3,20-dioxo-1,4-pregnadienes, methods for their manufacture, their use as anti-inflammatory agents, and pharmaceutical formulations useful therefor
IT1196142B (en) * 1984-06-11 1988-11-10 Sicor Spa PROCEDURE FOR THE PREPARATION OF 16.17-ACETALS OF PREGNANIC DERIVATIVES AND NEW COMPOUNDS OBTAINED
DE59407183D1 (en) * 1993-04-02 1998-12-03 Byk Gulden Lomberg Chem Fab NEW PREDNISOLON DERIVATIVES
DE10055820C1 (en) * 2000-11-10 2002-07-25 Byk Gulden Lomberg Chem Fab Preparation of 16,17-cyclohexylmethylene-dioxy-pregnadiene derivative, useful as glucocorticoid, by reacting 16,17-ketal with cyclohexylaldehyde to give high epimeric purity
CN1264855C (en) * 2000-11-10 2006-07-19 奥坦纳医药公司 Production of 16,17-[(cyclohexylmethylene)bis(oxy)]-11,21-dihydroxy-pregna-1,4-diene-3,20-dione or its 21 by transketalization - Isobutyrate method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106290695A (en) * 2015-06-25 2017-01-04 重庆华邦制药有限公司 Desonide and the separation of related impurities and assay method

Also Published As

Publication number Publication date
WO2007054974A2 (en) 2007-05-18
WO2007054974A3 (en) 2007-08-30

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