WO2004016596A1 - Composes condenses heterocycliques utilises comme inhibiteurs de pde-iv dans le traitement de troubles inflammatoires et allergiques - Google Patents

Composes condenses heterocycliques utilises comme inhibiteurs de pde-iv dans le traitement de troubles inflammatoires et allergiques Download PDF

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Publication number
WO2004016596A1
WO2004016596A1 PCT/IB2003/003364 IB0303364W WO2004016596A1 WO 2004016596 A1 WO2004016596 A1 WO 2004016596A1 IB 0303364 W IB0303364 W IB 0303364W WO 2004016596 A1 WO2004016596 A1 WO 2004016596A1
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WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
cyclopentyloxy
methoxyphenyl
Prior art date
Application number
PCT/IB2003/003364
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English (en)
Inventor
Abraham Thomas
Gopalan Balasubramanian
Laxmikant Atmaram Gharat
Jitendra Raghunath Mohite
V. S. Prasada Rao Lingam
Aftab Dawoodbhai Lakdawala
Usha Karunakaran
Ruchi Verma
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Glenmark Pharmaceuticals Limited
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Application filed by Glenmark Pharmaceuticals Limited filed Critical Glenmark Pharmaceuticals Limited
Priority to AU2003253130A priority Critical patent/AU2003253130A1/en
Publication of WO2004016596A1 publication Critical patent/WO2004016596A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C07D239/76—N-oxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/84—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • Ri is OH or an ether or ester thereof, X is YR 2 , halogen, nitro, NR R 5 or formyl amine;
  • R 11 , R 12 , and R 13 are independently selected from the group consisting of hydrogen, hydroxy, halogen, cyano, nitro, formyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclylalkyl ring, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substitute
  • alkenyl refers to aliphatic hydrocarbon group containing a carbon- carbon double bond and which may be a straight or branched chain radical having 2 to 10 carbon atoms which is attached to the rest of the molecule by a single bond. Examples include but are not limited to ethenyl, 1-propenyl, 2-propenyl (allyl), iso- propenyl, 2 -methyl- 1-propenyl, 1-butenyl, and 2-butenyl and the like.
  • Examples include but are not limited to phenyl, naphthyl, tetrahydronapthyl, indanyl and biphenyl.
  • Another object of the invention is a method of treating insulin resistant diabetes in a subject in need thereof which comprises administering to said subject a therapeutically effective amount of a compound according to Formula 1.
  • compositions of the present invention may also contain or be co-administered with one or more known drugs selected from other clinically useful therapeutic agents.
  • Step 1 3-Cyclopentyloxy-4-difluoromethoxbenzaldehyde Alkylation of 4-Difluoromethoxy-3-hydroxybenzaldehyde (20 g, 0.1 mol) with cyclopentyl bromide (24 g, 0.16 mol) in the presence of anhydrous potassium carbonate (37 g, 0.268 mol) as described in intermediate 1, step 1 gave 27 g of the product as colourless oil.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux composés hétérocycliques de la formule (I) lesquels inhibent la phosphodiextérase de type 4 (PDE4). Les composés sont utiles pour traiter des états inflammatoires, des maladies du système nerveux central ainsi que le diabète insulino résistant. Dans ladite formule P est choisi dans le groupe constitué d'une liaison directe, d'oxygène, de soufre et de NR1 ; P1 est choisi dans le groupe comprenant hydrogène, un atome d'halogène, -OR1, -S(O)mR1, -C(O)R1, formyle amine, nitro et -NRxRy ; R2 est choisi dans le groupe comprenant hydrogène, halogène, alkyle substitué ou non substitué, cycloalkyle substitué ou non substitué, CN, -CH=CR3R3 ; le cycle 'A' est choisi dans le groupe contenant un cycle aryle substitué ou non substitué, un cycle hétérocyclique de cinq à sept éléments facultativement substitué, saturé ou instauré, contenant un ou plusieurs hétéroatomes sélectionnés dans le groupe contenant O, S, et NR1; et R1, Rx, Ry ainsi que R3 on la notation définie dans la description.
PCT/IB2003/003364 2002-08-19 2003-08-19 Composes condenses heterocycliques utilises comme inhibiteurs de pde-iv dans le traitement de troubles inflammatoires et allergiques WO2004016596A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003253130A AU2003253130A1 (en) 2002-08-19 2003-08-19 Condensed heterocyclic compounds as pde-iv inhibitors for the treatment of inflammatory and allergic disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN754/MUM/2002 2002-08-19
IN754MU2002 2002-08-19

Publications (1)

Publication Number Publication Date
WO2004016596A1 true WO2004016596A1 (fr) 2004-02-26

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AU (1) AU2003253130A1 (fr)
WO (1) WO2004016596A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005105759A1 (fr) * 2004-04-28 2005-11-10 Grünenthal GmbH Composes de 5, 6, 7, 8-tetrahydro-pyrido[4, 3-d]pyrimidine-2-yl et de 5, 6, 7, 8-tetrahydro-quinazoline-2-yl substituees
US7223789B2 (en) 2003-04-11 2007-05-29 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7238725B2 (en) 2002-10-23 2007-07-03 Glenmark Pharmaceuticals Ltd. Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
EP1874308A1 (fr) * 2005-03-08 2008-01-09 Nycomed GmbH Roflumilast pour le traitement de diabetes mellitus
US7563900B2 (en) 2004-10-13 2009-07-21 Glenmark Pharmaceuticals S.A. Process for the preparation N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methane sulfonamido-dibenzo[b,d]furan-1-carboxamide
US7776893B2 (en) 2003-09-05 2010-08-17 Nycomed Gmbh Use of PDE4 inhibitors for the treatment of diabetes mellitus
US7943634B2 (en) 2004-12-17 2011-05-17 Glenmark Pharmaceuticals S.A. Substituted benzo[4,5]furo[3,2-c]pyridine derivatives as PDE 4 inhibitors
US8129401B2 (en) 2004-12-17 2012-03-06 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
WO2014117947A1 (fr) * 2013-02-04 2014-08-07 Grünenthal GmbH Composés pyrimidines condensés 4-amino substitués en tant qu'inhibiteurs de pde4
US8846656B2 (en) 2011-07-22 2014-09-30 Novartis Ag Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators
EP2907806A1 (fr) 2014-02-14 2015-08-19 Universita Degli Studi Di Genova Nouveux composés comme inhibiteurs sélectifs de PDE4D

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993019747A1 (fr) * 1992-04-02 1993-10-14 Smithkline Beecham Corporation Composes destines a traiter les maladies allergiques et inflammatoires
WO1995009837A1 (fr) * 1993-10-01 1995-04-13 Smithkline Beecham Corporation Composes cyano
WO1995024381A1 (fr) * 1994-03-11 1995-09-14 Smithkline Beecham Corporation Composes de cyano et leur preparations
US5814651A (en) * 1992-12-02 1998-09-29 Pfizer Inc. Catechol diethers as selective PDEIV inhibitors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993019747A1 (fr) * 1992-04-02 1993-10-14 Smithkline Beecham Corporation Composes destines a traiter les maladies allergiques et inflammatoires
US5814651A (en) * 1992-12-02 1998-09-29 Pfizer Inc. Catechol diethers as selective PDEIV inhibitors
WO1995009837A1 (fr) * 1993-10-01 1995-04-13 Smithkline Beecham Corporation Composes cyano
WO1995024381A1 (fr) * 1994-03-11 1995-09-14 Smithkline Beecham Corporation Composes de cyano et leur preparations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HULME C ET AL: "Quaternary substituted PDE4 inhibitors I: the synthesis and in vitro evaluation of a novel series of oxindoles", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 8, no. 2, 20 January 1998 (1998-01-20), pages 175 - 178, XP004136840, ISSN: 0960-894X *
J. KOYAMA, T. SUGITA, Y. SUZUTA: "synthesis of alkaloids", HETEROCYCLES, vol. 16, no. 6, 1981, pages 969 - 972, XP009019704 *
SILVESTRE, J. ET AL: "SB-207499. antiasthmatic/antiinflammatory, phosphodiesterase IV inhibitor", DRUGS OF THE FUTURE (1998), 23(6), 607-615, XP000981875 *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7238725B2 (en) 2002-10-23 2007-07-03 Glenmark Pharmaceuticals Ltd. Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7223789B2 (en) 2003-04-11 2007-05-29 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7384962B2 (en) 2003-04-11 2008-06-10 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7393846B2 (en) 2003-04-11 2008-07-01 Glenmark Pharmaceuticals, S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders
US7776893B2 (en) 2003-09-05 2010-08-17 Nycomed Gmbh Use of PDE4 inhibitors for the treatment of diabetes mellitus
DE102004020908A1 (de) * 2004-04-28 2005-11-17 Grünenthal GmbH Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen
WO2005105759A1 (fr) * 2004-04-28 2005-11-10 Grünenthal GmbH Composes de 5, 6, 7, 8-tetrahydro-pyrido[4, 3-d]pyrimidine-2-yl et de 5, 6, 7, 8-tetrahydro-quinazoline-2-yl substituees
US7662828B2 (en) 2004-04-28 2010-02-16 Gruenenthal Gmbh Substituted 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2-yl compounds and 5,6,7,8-tetrahydroquinazoline-2-yl compounds
US7563900B2 (en) 2004-10-13 2009-07-21 Glenmark Pharmaceuticals S.A. Process for the preparation N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methane sulfonamido-dibenzo[b,d]furan-1-carboxamide
US7943634B2 (en) 2004-12-17 2011-05-17 Glenmark Pharmaceuticals S.A. Substituted benzo[4,5]furo[3,2-c]pyridine derivatives as PDE 4 inhibitors
US8129401B2 (en) 2004-12-17 2012-03-06 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
EP1874308A1 (fr) * 2005-03-08 2008-01-09 Nycomed GmbH Roflumilast pour le traitement de diabetes mellitus
US8017633B2 (en) 2005-03-08 2011-09-13 Nycomed Gmbh Roflumilast for the treatment of diabetes mellitus
CN101137368B (zh) * 2005-03-08 2012-05-16 奈科明有限责任公司 治疗糖尿病的罗氟司特
US8541456B2 (en) 2005-03-08 2013-09-24 Takeda Gmbh Roflumilast for the treatment of diabetes mellitus type 2
US8846656B2 (en) 2011-07-22 2014-09-30 Novartis Ag Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators
US9505755B2 (en) 2011-07-22 2016-11-29 Novartis Ag Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5A receptor modulators
WO2014117947A1 (fr) * 2013-02-04 2014-08-07 Grünenthal GmbH Composés pyrimidines condensés 4-amino substitués en tant qu'inhibiteurs de pde4
JP2016506940A (ja) * 2013-02-04 2016-03-07 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Ｐｄｅ４阻害薬としての、４−アミノ置換縮合ピリミジン化合物
US9505724B2 (en) 2013-02-04 2016-11-29 Grünenthal GmbH 4-amino substituted condensed pyrimidine compounds as PDE4 inhibitors
EP2907806A1 (fr) 2014-02-14 2015-08-19 Universita Degli Studi Di Genova Nouveux composés comme inhibiteurs sélectifs de PDE4D
WO2015121212A1 (fr) 2014-02-14 2015-08-20 Università Degli Studi Di Genova Nouveaux composés présentant une activité d'inhibition sélective vis-à-vis de pde4d

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