CA2121230A1 - 1,3-dihydro-2h-imidazo(4,5-b) quinolin-2-one derivatives - Google Patents

1,3-dihydro-2h-imidazo(4,5-b) quinolin-2-one derivatives

Info

Publication number
CA2121230A1
CA2121230A1 CA002121230A CA2121230A CA2121230A1 CA 2121230 A1 CA2121230 A1 CA 2121230A1 CA 002121230 A CA002121230 A CA 002121230A CA 2121230 A CA2121230 A CA 2121230A CA 2121230 A1 CA2121230 A1 CA 2121230A1
Authority
CA
Canada
Prior art keywords
6alkyl
compounds
quinolin
imidazo
dihydro
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
CA002121230A
Other languages
French (fr)
Other versions
CA2121230C (en
Inventor
Eddy J. E. Freyne
Alfons H. M. Raeymaekers
Didier R. G. G. De Chaffoy De Courcelles
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.)
Janssen Pharmaceutica NV
Original Assignee
Eddy J. E. Freyne
Alfons H. M. Raeymaekers
Didier R. G. G. De Chaffoy De Courcelles
Janssen Pharmaceutica, Naamloze Vennootschap
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 Eddy J. E. Freyne, Alfons H. M. Raeymaekers, Didier R. G. G. De Chaffoy De Courcelles, Janssen Pharmaceutica, Naamloze Vennootschap filed Critical Eddy J. E. Freyne
Publication of CA2121230A1 publication Critical patent/CA2121230A1/en
Application granted granted Critical
Publication of CA2121230C publication Critical patent/CA2121230C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07D215/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

Novel 1,3-dihydro-2H-imidazo(4,5-b)quinolin-2-one derivatives of formu-la (I) wherein R is hydrogen, C1-6alkyl, C3-6cycloalkyl, phenyl optionally sub-stituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C1-6alkyloxy, C5-6cycloalkyloxy, C1-6alkyl or trifluoromethyl; pyr-idinyl; thienyl optionally substituted with halo or C1-6alkyl; and (.alpha.) is a radi-cal of formula (a), (b), or (c); the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, said compounds being potent inhibitors of both phosphodiesterase III and IV, which are useful in the treatment of aller-gic disorders, atopic diseases and related afflictions. Intermediates in the prepar-ation thereof. Pharmaceutical compositions containing said compounds as an active ingredient. Methods of preparing said compounds and pharmaceutical compositions.
CA002121230A 1991-10-30 1992-10-27 1,3-dihydro-2h-imidazo(4,5-b) quinolin-2-one derivatives Expired - Lifetime CA2121230C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US78495591A 1991-10-30 1991-10-30
US07/784,955 1991-10-30
PCT/EP1992/002496 WO1993009118A1 (en) 1991-10-30 1992-10-27 1,3-dihydro-2h-imidazo(4,5-b)quinolin-2-one derivatives as phosphodiesterase inhibitors

Publications (2)

Publication Number Publication Date
CA2121230A1 true CA2121230A1 (en) 1993-05-13
CA2121230C CA2121230C (en) 2003-03-11

Family

ID=25134048

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002121230A Expired - Lifetime CA2121230C (en) 1991-10-30 1992-10-27 1,3-dihydro-2h-imidazo(4,5-b) quinolin-2-one derivatives

Country Status (24)

Country Link
US (3) US5521187A (en)
EP (2) EP0610372B1 (en)
JP (1) JP3488922B2 (en)
KR (1) KR100251895B1 (en)
CN (1) CN1041726C (en)
AT (1) ATE131479T1 (en)
AU (1) AU660337B2 (en)
CA (1) CA2121230C (en)
DE (1) DE69206820T2 (en)
DK (1) DK0610372T3 (en)
ES (1) ES2083773T3 (en)
FI (1) FI105548B (en)
GR (1) GR3018909T3 (en)
HU (1) HU220608B1 (en)
IL (1) IL103570A (en)
MX (1) MX9206258A (en)
NO (1) NO300976B1 (en)
NZ (1) NZ244779A (en)
PH (1) PH31245A (en)
PL (1) PL170749B1 (en)
RU (1) RU2127273C1 (en)
TW (1) TW249234B (en)
WO (1) WO1993009118A1 (en)
ZA (1) ZA928373B (en)

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Also Published As

Publication number Publication date
JPH07500599A (en) 1995-01-19
FI942010A (en) 1994-04-29
EP0610372B1 (en) 1995-12-13
NO300976B1 (en) 1997-08-25
CN1041726C (en) 1999-01-20
ATE131479T1 (en) 1995-12-15
HUT66453A (en) 1994-11-28
HU9401245D0 (en) 1994-08-29
US5516908A (en) 1996-05-14
GR3018909T3 (en) 1996-05-31
PH31245A (en) 1998-06-18
IL103570A (en) 1996-03-31
US5541325A (en) 1996-07-30
PL170749B1 (en) 1997-01-31
WO1993009118A1 (en) 1993-05-13
RU2127273C1 (en) 1999-03-10
US5521187A (en) 1996-05-28
NO941497D0 (en) 1994-04-25
AU2908392A (en) 1993-06-07
FI942010A0 (en) 1994-04-29
NO941497L (en) 1994-04-25
CN1072681A (en) 1993-06-02
DE69206820T2 (en) 1996-05-15
ZA928373B (en) 1994-04-29
NZ244779A (en) 1994-10-26
AU660337B2 (en) 1995-06-22
HU220608B1 (en) 2002-03-28
EP0541153A1 (en) 1993-05-12
KR100251895B1 (en) 2000-09-01
CA2121230C (en) 2003-03-11
IL103570A0 (en) 1993-03-15
EP0610372A1 (en) 1994-08-17
MX9206258A (en) 1993-04-01
DE69206820D1 (en) 1996-01-25
TW249234B (en) 1995-06-11
FI105548B (en) 2000-09-15
ES2083773T3 (en) 1996-04-16
DK0610372T3 (en) 1996-01-29
JP3488922B2 (en) 2004-01-19

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