CA2239694A1 - Indane dimer compounds and their pharmaceutical use - Google Patents

Indane dimer compounds and their pharmaceutical use

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Publication number
CA2239694A1
CA2239694A1 CA002239694A CA2239694A CA2239694A1 CA 2239694 A1 CA2239694 A1 CA 2239694A1 CA 002239694 A CA002239694 A CA 002239694A CA 2239694 A CA2239694 A CA 2239694A CA 2239694 A1 CA2239694 A1 CA 2239694A1
Authority
CA
Canada
Prior art keywords
pharmaceutical use
dimer compounds
activity
indane
indane dimer
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
CA002239694A
Other languages
French (fr)
Other versions
CA2239694C (en
Inventor
John Walsh
Neil Frankish
Helen Sheridan
Ronan Farrell
William Byrne
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.)
Venantius Ltd
Original Assignee
Venantius Limited
John Walsh
Neil Frankish
Helen Sheridan
Ronan Farrell
William Byrne
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 Venantius Limited, John Walsh, Neil Frankish, Helen Sheridan, Ronan Farrell, William Byrne filed Critical Venantius Limited
Publication of CA2239694A1 publication Critical patent/CA2239694A1/en
Application granted granted Critical
Publication of CA2239694C publication Critical patent/CA2239694C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/20Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P11/00Drugs for disorders of the respiratory system
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C2602/08One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Abstract

Indame dimer compounds and their pharmaceutical use particularly to achieve smooth muscle relaxing activity and/or mast cell stabilising activity and/or anti-inflammatory activity are described.
CA002239694A 1995-12-06 1996-12-06 Indane dimer compounds and their pharmaceutical use Expired - Lifetime CA2239694C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IE950922 1995-12-06
IE950922 1995-12-06
IE960762 1996-10-31
IE960762 1996-10-31
PCT/IE1996/000080 WO1997020802A1 (en) 1995-12-06 1996-12-06 Indane dimer compounds and their pharmaceutical use

Publications (2)

Publication Number Publication Date
CA2239694A1 true CA2239694A1 (en) 1997-06-12
CA2239694C CA2239694C (en) 2008-05-06

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CA002239853A Expired - Fee Related CA2239853C (en) 1995-12-06 1996-12-06 Indane dimer compounds and their pharmaceutical use
CA002239694A Expired - Lifetime CA2239694C (en) 1995-12-06 1996-12-06 Indane dimer compounds and their pharmaceutical use

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CA002239853A Expired - Fee Related CA2239853C (en) 1995-12-06 1996-12-06 Indane dimer compounds and their pharmaceutical use

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US (3) US6300376B1 (en)
EP (3) EP0873301B1 (en)
JP (3) JP2000506497A (en)
KR (2) KR19990072007A (en)
AT (3) ATE260241T1 (en)
AU (3) AU1169397A (en)
CA (2) CA2239853C (en)
DE (3) DE69631688T2 (en)
DK (1) DK0865419T3 (en)
GB (3) GB2322858A (en)
IE (1) IE960865A1 (en)
IL (3) IL124756A0 (en)
WO (3) WO1997020805A1 (en)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2458697A (en) 1996-04-18 1997-11-07 Alcon Laboratories, Inc. Calcium channel blockers as human conjunctival mast cell degranulation inhibitors for treating ocular allergic conditions
WO1998055439A1 (en) * 1997-06-05 1998-12-10 Venantius Limited Indane compounds and their pharmaceutical use
JP2001064202A (en) * 1999-08-25 2001-03-13 Kissei Pharmaceut Co Ltd Prophylactic and therapeutic agent of cardiac failure
DE10142660A1 (en) 2001-08-31 2003-03-20 Aventis Pharma Gmbh Use of derivatives of C2-substituted indan-1-ol systems for the preparation of medicaments for the prophylaxis or treatment of obesity
DE10142663B4 (en) * 2001-08-31 2004-08-19 Aventis Pharma Deutschland Gmbh C2-Disubstituted indan-1-ol systems
DE10142667B4 (en) 2001-08-31 2004-06-09 Aventis Pharma Deutschland Gmbh C2-substituted indan-1-oles and their derivatives and their use as medicines
DE10142666A1 (en) 2001-08-31 2003-03-20 Aventis Pharma Gmbh Use of C2-substituted indan-1-ol systems for the preparation of medicaments for the prophylaxis or treatment of obesity
DE10142668A1 (en) 2001-08-31 2003-03-20 Aventis Pharma Gmbh Use of C2-substituted indan-1-one systems for the preparation of medicaments for the prophylaxis or treatment of obesity
DE10142722A1 (en) * 2001-08-31 2003-03-27 Aventis Pharma Gmbh C2-substituted indan-1-ones and their derivatives, processes for their preparation and their use as medicaments
DE10142661B4 (en) * 2001-08-31 2004-06-09 Aventis Pharma Deutschland Gmbh Poly-substituted indan-1-ol systems and their use as pharmaceuticals
DE10142665B4 (en) 2001-08-31 2004-05-06 Aventis Pharma Deutschland Gmbh C2-Disubstituted indan-1-ones and their derivatives
DE10142659A1 (en) 2001-08-31 2003-03-20 Aventis Pharma Gmbh Use of multiply substituted indan-1-ol. Systems for the preparation of medicaments for the prophylaxis or treatment of obesity
DE10142662B4 (en) 2001-08-31 2004-07-08 Aventis Pharma Deutschland Gmbh Derivatives of C2-substituted indan-1-ol systems and their use as pharmaceuticals
US10517839B2 (en) * 2008-06-09 2019-12-31 Cornell University Mast cell inhibition in diseases of the retina and vitreous
US9260376B2 (en) 2011-07-22 2016-02-16 Venantius Limited Compounds for use in the treatment of immune related inflammatory disease
CN103764608B (en) 2011-07-22 2016-02-03 贝南蒂乌斯有限公司 Be used for the treatment of the indene derivative of inflammatory bowel
WO2013014660A1 (en) * 2011-07-22 2013-01-31 Venantius Limited Indane dimers for use in the treatment of autoimmune inflammatory disease
WO2013174917A1 (en) 2012-05-24 2013-11-28 Venantius Limited Compounds for use in the treatment of autoimmune inflammatory disease
EP2855416A1 (en) * 2012-05-24 2015-04-08 Venantius Limited Indane dimers for use in the treatment of autoimmune inflammatory disease
TWI799691B (en) * 2019-03-29 2023-04-21 景凱生物科技股份有限公司 Peripheral alkyl and alkenyl chains extended benzene derivatives and pharmaceutical composition including the same
CN111533764B (en) * 2020-05-12 2023-06-06 杭州师范大学 Method for preparing siloxyindene derivative by utilizing domino reaction

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1205537B (en) * 1961-08-19 1965-11-25 Thomae Gmbh Dr K Process for making new steroid esters
US3668258A (en) * 1969-03-17 1972-06-06 Uniroyal Inc Sulfur-containing polyaryl polyphenolic compounds and process
SE421305B (en) * 1973-10-12 1981-12-14 Merck & Co Inc PROCEDURE FOR PREPARING 1-HYDROXY-5-INDANYLOXYETIC ACIDS

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