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WO2007054974A3 - A green chemistry process for the preparation of pregnadiene esters - Google Patents

A green chemistry process for the preparation of pregnadiene esters Download PDF

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Publication number
WO2007054974A3
WO2007054974A3 PCT/IN2006/000399 IN2006000399W WO2007054974A3 WO 2007054974 A3 WO2007054974 A3 WO 2007054974A3 IN 2006000399 W IN2006000399 W IN 2006000399W WO 2007054974 A3 WO2007054974 A3 WO 2007054974A3
Authority
WO
WIPO (PCT)
Prior art keywords
esters
preparation
pregnadiene
green chemistry
chemistry process
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
WO2007054974B1 (en
WO2007054974A2 (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)
  • Steroid Compounds (AREA)
  • Macromonomer-Based Addition Polymer (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.
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
IN1210/MUM/2005 2005-09-28
IN1210MU2005 2005-09-28

Publications (3)

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

Families Citing this family (10)

* 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
EP2207788A1 (en) 2007-10-04 2010-07-21 AstraZeneca AB Steroidal [3, 2-c]pyrazole compounds, with glucocorticoid activity
CA2716476A1 (en) * 2008-02-27 2009-09-03 Astrazeneca Ab 16 alpha, 17 alpha-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
CN106290695B (en) * 2015-06-25 2020-02-18 重庆华邦胜凯制药有限公司 Method for separating and measuring desonide and related impurities
BR112018074922B1 (en) 2016-06-02 2022-10-25 Abbvie Inc GLUCOCORTICOID RECEPTOR AGONIST COMPOUNDS, PHARMACEUTICAL COMPOSITION COMPRISING SUCH COMPOUNDS AND THERAPEUTIC USE THEREOF
KR20200095477A (en) 2017-12-01 2020-08-10 애브비 인코포레이티드 Glucocorticoid receptor agonists and immunoconjugates thereof

Citations (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
EP0164636A2 (en) * 1984-06-11 1985-12-18 SICOR Società Italiana Corticosteroidi S.p.A. A process for the preparation of 16,17 acetals of pregnane derivatives and compounds obtained therefrom
WO1994022899A1 (en) * 1993-04-02 1994-10-13 Byk Gulden Lomberg Chemische Fabrik Gmbh New prednisolone derivates
WO2002038584A1 (en) * 2000-11-10 2002-05-16 Altana Pharma Ag Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-dihydroxy-pregna-1,4-dien-3,20-dion or its 21-isobutyrat by transketalisation
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

Patent Citations (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
EP0164636A2 (en) * 1984-06-11 1985-12-18 SICOR Società Italiana Corticosteroidi S.p.A. A process for the preparation of 16,17 acetals of pregnane derivatives and compounds obtained therefrom
WO1994022899A1 (en) * 1993-04-02 1994-10-13 Byk Gulden Lomberg Chemische Fabrik Gmbh New prednisolone derivates
WO2002038584A1 (en) * 2000-11-10 2002-05-16 Altana Pharma Ag Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-dihydroxy-pregna-1,4-dien-3,20-dion or its 21-isobutyrat by transketalisation
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

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CUIHUA XUEBAO , 26(9), 815-818 CODEN: THHPD3; ISSN: 0253-9837, 1 September 2005 (2005-09-01) *
DATABASE CA1 [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 31 October 2005 (2005-10-31), ZHANG, FAN ET AL: "Acetalization of aldehydes (ketones) with diols catalyzed by Bronsted acidic ionic liquids", XP002439980, retrieved from STN Database accession no. 2005:1160197 *
WU H-H ET AL: "An efficient procedure for protection of carbonyls in Bronsted acidic ionic liquid [Hmim]BF4", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 25, 14 June 2004 (2004-06-14), pages 4963 - 4965, XP004510985, ISSN: 0040-4039 *

Also Published As

Publication number Publication date
WO2007054974B1 (en) 2007-11-22
WO2007054974A2 (en) 2007-05-18

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