WO2007126840A3 - Production of gossypol co-crystals - Google Patents

Production of gossypol co-crystals Download PDF

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Publication number
WO2007126840A3
WO2007126840A3 PCT/US2007/007604 US2007007604W WO2007126840A3 WO 2007126840 A3 WO2007126840 A3 WO 2007126840A3 US 2007007604 W US2007007604 W US 2007007604W WO 2007126840 A3 WO2007126840 A3 WO 2007126840A3
Authority
WO
WIPO (PCT)
Prior art keywords
crystals
acetic acid
gossypol
gossypol acetic
relates
Prior art date
Application number
PCT/US2007/007604
Other languages
French (fr)
Other versions
WO2007126840A2 (en
Inventor
Shaomeng Wang
Jianyong Chen
John F W Keana
Ming Guo
Original Assignee
Univ Michigan
Shaomeng Wang
Jianyong Chen
John F W Keana
Ming Guo
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 Univ Michigan, Shaomeng Wang, Jianyong Chen, John F W Keana, Ming Guo filed Critical Univ Michigan
Priority to JP2009502959A priority Critical patent/JP2009532354A/en
Priority to EP07754167A priority patent/EP2007706A2/en
Publication of WO2007126840A2 publication Critical patent/WO2007126840A2/en
Publication of WO2007126840A3 publication Critical patent/WO2007126840A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K31/74—Synthetic polymeric materials
    • A61K31/765—Polymers containing oxygen
    • A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
    • 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
    • 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
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Abstract

This invention relates to relates to methods for producing gossypol acetic acid co- crystals and (-)-gossypol acetic acid co-crystals. The invention also relates to pharmaceutical compositions comprising gossypol acetic acid co-crystals and (-)-gossypol acetic acid co-crystals and the use of gossypol acetic acid co-crystals and (-)-gossypol acetic acid co-crystals for inducing apoptosis in cells and for sensitizing cells to the induction of apoptotic cell death.
PCT/US2007/007604 2006-03-30 2007-03-29 Production of gossypol co-crystals WO2007126840A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2009502959A JP2009532354A (en) 2006-03-30 2007-03-29 Production method of gossypol co-crystal
EP07754167A EP2007706A2 (en) 2006-03-30 2007-03-29 Production of gossypol co-crystals

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US78802506P 2006-03-30 2006-03-30
US60/788,025 2006-03-30

Publications (2)

Publication Number Publication Date
WO2007126840A2 WO2007126840A2 (en) 2007-11-08
WO2007126840A3 true WO2007126840A3 (en) 2008-10-02

Family

ID=38656028

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/007604 WO2007126840A2 (en) 2006-03-30 2007-03-29 Production of gossypol co-crystals

Country Status (5)

Country Link
US (1) US7557251B2 (en)
EP (1) EP2007706A2 (en)
JP (1) JP2009532354A (en)
CN (1) CN101454269A (en)
WO (1) WO2007126840A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7696372B2 (en) * 2007-10-01 2010-04-13 Ascenta Therapeutics, Inc. Process for preparing R-gossypol L-phenylalaninol dienamine
US20090285865A1 (en) * 2008-05-14 2009-11-19 Shalaby Shalaby W Palatable, solid oral formulations for male chemical sterilization
WO2011031441A1 (en) * 2009-08-28 2011-03-17 The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Therapy with a chimeric molecule and a pro-apoptotic agent
CN105125536B (en) * 2015-07-29 2018-05-04 无锡宏瑞生物医药科技有限公司 Treat bacterium, fungi, virus or dermopathic composition caused by parasite
CN109942455A (en) * 2019-03-10 2019-06-28 陕西科技大学 Gossypol with anti-tumor activity-Eflornithine schiff base compounds and its synthetic method
KR102259892B1 (en) * 2019-08-05 2021-06-04 주식회사 하임바이오 Method for mass-refining of plant-derived polyphenols
CN113214066A (en) * 2020-02-04 2021-08-06 中国医学科学院药物研究所 Gossypol crystal II substance, preparation method, composition and application thereof
JP2023528090A (en) * 2020-06-01 2023-07-03 コロナ フィード アディティブス エル．エル．シー． Porcine contraceptive compositions, systems and methods

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040214902A1 (en) * 2001-05-30 2004-10-28 The Regents Of The University Of Michigan Small molecule antagonists of BCL-2 family proteins
CN1557799A (en) * 2004-02-02 2004-12-29 陕西盘龙制药集团有限公司 Production process for gossypol acetic acid materials
CN1887838A (en) * 2006-07-14 2007-01-03 中国科学院上海有机化学研究所 One-step prepn process of acid gossypol derivative with acid and acetone aqua

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1017705B (en) 1987-12-26 1992-08-05 中国医学科学院药物研究所 Preparation method of optically-active cotton phenol
CA2449245A1 (en) 2001-05-30 2002-12-05 The Regents Of The University Of Michigan Small molecule antagonists of bcl2 family proteins

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040214902A1 (en) * 2001-05-30 2004-10-28 The Regents Of The University Of Michigan Small molecule antagonists of BCL-2 family proteins
CN1557799A (en) * 2004-02-02 2004-12-29 陕西盘龙制药集团有限公司 Production process for gossypol acetic acid materials
CN1887838A (en) * 2006-07-14 2007-01-03 中国科学院上海有机化学研究所 One-step prepn process of acid gossypol derivative with acid and acetone aqua

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHIRALITY, vol. 15, no. 6, 2003, pages 486 - 493 *
DATABASE CA [online] DOWD ET AL., XP008135059, accession no. STN Database accession no. (132:93495) *
DATABASE CA [online] DOWD ET AL., XP008135060, accession no. STN Database accession no. (140:164037) *
JOURNAL OF THE AMERICAN OIL CHEMIST'S SOCIETY, vol. 76, no. 11, 1999, pages 1343 - 1350 *

Also Published As

Publication number Publication date
CN101454269A (en) 2009-06-10
US20080021110A1 (en) 2008-01-24
US7557251B2 (en) 2009-07-07
EP2007706A2 (en) 2008-12-31
JP2009532354A (en) 2009-09-10
WO2007126840A2 (en) 2007-11-08

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