CA2251060A1 - Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action - Google Patents

Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action

Info

Publication number
CA2251060A1
CA2251060A1 CA002251060A CA2251060A CA2251060A1 CA 2251060 A1 CA2251060 A1 CA 2251060A1 CA 002251060 A CA002251060 A CA 002251060A CA 2251060 A CA2251060 A CA 2251060A CA 2251060 A1 CA2251060 A1 CA 2251060A1
Authority
CA
Canada
Prior art keywords
acylated
prodrugs
hydroxy methyl
immunomodulator
action
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.)
Granted
Application number
CA002251060A
Other languages
French (fr)
Other versions
CA2251060C (en
Inventor
Johannes Schneider
Werner Winter
Stephan Wnendt
Kai Zwingenberger
Kurt Eger
Michaela Akermann
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.)
Gruenenthal GmbH
Original Assignee
Grunenthal Gmbh
Johannes Schneider
Werner Winter
Stephan Wnendt
Kai Zwingenberger
Kurt Eger
Michaela Akermann
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
Priority claimed from DE19613976A external-priority patent/DE19613976C1/en
Application filed by Grunenthal Gmbh, Johannes Schneider, Werner Winter, Stephan Wnendt, Kai Zwingenberger, Kurt Eger, Michaela Akermann filed Critical Grunenthal Gmbh
Publication of CA2251060A1 publication Critical patent/CA2251060A1/en
Application granted granted Critical
Publication of CA2251060C publication Critical patent/CA2251060C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention relates to thalidomide prodrugs of the formula (I), in which R is -CHR1-NHR2 or -(CH2)n COOH, R1 is H or C1-4-alkyl, R2 is H, C1-3-alkyl, C(O)-CH2-NHR3 or an amino protective group, R3 is H or an amino protective group, and n is an integer between 2 and 4, in the form of their bases or salts of physiological acids. It also relates to a process for the preparation of said prodrugs and the use thereof as an active drug substance.
CA002251060A 1996-04-09 1997-03-22 Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action Expired - Fee Related CA2251060C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19613976A DE19613976C1 (en) 1996-04-09 1996-04-09 Thalidomide prodrugs with immunomodulatory effects
DE19613976.7 1996-04-09
PCT/EP1997/001475 WO1997037988A1 (en) 1996-04-09 1997-03-22 Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action

Publications (2)

Publication Number Publication Date
CA2251060A1 true CA2251060A1 (en) 1997-10-16
CA2251060C CA2251060C (en) 2006-09-12

Family

ID=36999576

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002251060A Expired - Fee Related CA2251060C (en) 1996-04-09 1997-03-22 Acylated n-hydroxy methyl thalidomide prodrugs with immunomodulator action

Country Status (1)

Country Link
CA (1) CA2251060C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7320991B2 (en) 2001-02-27 2008-01-22 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health Analogs of thalidomide as potential angiogenesis inhibitors
US7973057B2 (en) 2003-09-17 2011-07-05 The United States Of America As Represented By The Department Of Health And Human Services Thalidomide analogs
US8853253B2 (en) 2003-09-17 2014-10-07 P2D, Inc. Thalidomide analogs
US9084783B2 (en) 2011-12-02 2015-07-21 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7320991B2 (en) 2001-02-27 2008-01-22 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health Analogs of thalidomide as potential angiogenesis inhibitors
US8716315B2 (en) 2001-02-27 2014-05-06 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Analogs of thalidomide as potential angiogenesis inhibitors
US7973057B2 (en) 2003-09-17 2011-07-05 The United States Of America As Represented By The Department Of Health And Human Services Thalidomide analogs
US8546430B2 (en) 2003-09-17 2013-10-01 P2D, Inc. Thalidomide analogs
US8853253B2 (en) 2003-09-17 2014-10-07 P2D, Inc. Thalidomide analogs
US9084783B2 (en) 2011-12-02 2015-07-21 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds
US9623020B2 (en) 2011-12-02 2017-04-18 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds
US10220028B2 (en) 2011-12-02 2019-03-05 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds

Also Published As

Publication number Publication date
CA2251060C (en) 2006-09-12

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