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1. WO2000039103 - DIHYDRO-BENZO(1,4)OXAZINES AND TETRAHYDROQUINOXALINES

Publication Number WO/2000/039103
Publication Date 06.07.2000
International Application No. PCT/GB1999/004430
International Filing Date 23.12.1999
IPC
C07D 241/38 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
241Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
36condensed with carbocyclic rings or ring systems
38with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
C07D 265/36 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
265Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
281,4-Oxazines; Hydrogenated 1,4-oxazines
34condensed with carbocyclic rings
36condensed with one six-membered ring
CPC
A61P 11/06
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
11Drugs for disorders of the respiratory system
06Antiasthmatics
C07D 241/38
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
241Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
36condensed with carbocyclic rings or ring systems
38with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
C07D 265/36
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
265Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
281,4-Oxazines; Hydrogenated 1,4-oxazines
34condensed with carbocyclic rings
36condensed with one six-membered ring
Applicants
  • AVENTIS PHARMA LIMITED [GB/GB]; Aventis House 50 Kings Hill Avenue Kings Hill West Malling Kent ME19 4AH, GB (AllExceptUS)
  • BOURZAT, Jean-Dominique [FR/FR]; FR (UsOnly)
  • COMMERCON, Alain [FR/FR]; FR (UsOnly)
  • FILOCHE, Bruno, Jacques, Christophe [FR/FR]; FR (UsOnly)
  • HARRIS, Neil, Victor [GB/GB]; GB (UsOnly)
  • PALLIN, Thomas, David [GB/GB]; GB (UsOnly)
  • STUTTLE, Keith, Alfred, James [GB/GB]; GB (UsOnly)
Inventors
  • BOURZAT, Jean-Dominique; FR
  • COMMERCON, Alain; FR
  • FILOCHE, Bruno, Jacques, Christophe; FR
  • HARRIS, Neil, Victor; GB
  • PALLIN, Thomas, David; GB
  • STUTTLE, Keith, Alfred, James; GB
Agents
  • CAFFIN, Lee; Aventis Pharma Limited Rainham Road South Dagenham Essex RM10 7XS, GB
Priority Data
60/126,08425.03.1999US
9828417.723.12.1998GB
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) DIHYDRO-BENZO(1,4)OXAZINES AND TETRAHYDROQUINOXALINES
(FR) DIHYDRO-BENZO(1,4)OXAZINES ET TETRAHYDROQUINOXALINES
Abstract
(EN)
The invention is directed to physiologically active compounds of formula (I) wherein R1 represents R3-Z3, R3-L2-R4-Z3-, R3-L3-Ar1-L4-Z3- or R3-L3-Ar1-L2-R4-Z3-; R2 represents hydrogen, halogen, lower alkyl or lower alkoxy; A1 represents a straight chain C2-3alkylene linkage optionally substituted by one or more groups chosen from alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, imino, oxo, thioxo, or alkyl substituted by -ZR6, -NY1Y2, -CO2R6 or -C(=O)-NY1Y2; L1 represents a direct bond; an alkenylene, alkylene, alkynylene, cycloalkenylene, cycloalkylene, heteroaryldiyl, heterocycloalkylene or arylene linkage each optionally substituted by (a) an acidic functional group, cyano, oxo, -S(O)mR9, R3, -C(=O)-R3, -C(=O)-OR3, -N(R8)-C(=O)-R9, -N(R8)-C(=O)-OR9, -N(R8)-SO2-R9, -NY4Y5 or -[C(=O)-N(R10)-C(R5)(R11)]p-C(=O)-NY4Y5, or by (b) alkyl substituted by an acidic functional group, or by S(O)mR9, -C(=O)-NY4Y5 or -NY4Y5; a -[C(=O)-N(R10)-C(R5)(R11)]p-linkage; a-Z2-R12-linkage; a -C(=O)-CH2-C(=O)-linkage; a -R12-Z2-R12- linkage; a -C(R4)(R13)-[C(=O)-N(R10)-C(R5)(R11)]p- linkage; or a -L5-L6-L7- linkage; Z1 is NR17 or O; Y is carboxy or an acid bioisostere; and the corresponding N-oxides, and their prodrugs; and pharmaceutically acceptable salts and solvates of such compounds and their N-oxides and prodrugs. Such compounds have valuable pharmaceutical properties, in particular the ability to regulate the interaction of VCAM-1 and fibronectin with the integrin VLA-4 ($g(a)4$g(b)1).
(FR)
L'invention concerne des composés, actifs sur le plan physiologique, représentés par la formule (I) dans laquelle R1 représente R3-Z3-, R3-L2-R4-Z3-, R3-L3-Ar1-L4-Z3- ou R3-L3-Ar1-L2-R4-Z3-; R2 représente hydrogène, halogène, alkyle inférieur ou alcoxy inférieur; A1 représente une liaison alkylène C2-3 à chaîne linéaire, éventuellement substituée par un ou plusieurs groupes choisis parmi alkyle, aryle, arylalkyle, hétéroaryle, hétéroarylalkyle, imino, oxo, thioxo, ou alkyle substitué par -ZR6, -NY1Y2, -CO2R6 ou -C(=O)-NY1Y2; L1 représente une liaison directe; une liaison arylène, alcénylène, alkylène, alkynylène, cycloalcénylène, cycloalkylène, hétéroaryldiyle ou hétérocycloalkylène, chacune éventuellement substituée par (a) un groupe fonctionnel acide, cyano, oxo, -S(O)mR9, R3, -C(=O)-R3, -C(=O)-OR3, -N(R8)-C(=O)-R9, -N(R8)-C(=O)-OR9, -N(R8)-SO2-R9, -NY4Y5 ou [C(=O)-N(R10)-C(R5)(R11)]p-C(=O)-NY4Y5, ou par (b) alkyle substitué par un groupe fonctionnel acide, ou par S(O)mR9, -C(=O)-NY4Y5 ou -NY4Y5; une liaison -[C(=O)-N(R10)-C(R5)(R11)]p-; une liaison -Z2-R12-; une liaison -C(=O)-CH2-C(=O)-; une liaison R12-Z2-R12-; une liaison -C(R4)(R13)-[C(=O)-N(R10)-C(R5)(R11)]p-; ou une liaison L5-L6-L7-; Z1 représente NR17 ou O; Y représente carboxy ou un bioisostère d'acide; et les N-oxydes correspondant, ainsi que leurs promédicaments; et des sels et des solvates, pharmaceutiquement acceptables, desdits composés, ainsi que leurs N-oxydes et promédicaments. Lesdits composés possèdent des propriétés pharmaceutiques appréciables, notamment la capacité de réguler l'interaction de VCAM-1 et de la fibronectine avec l'intégrine VLA-4 ($g(a)4$g(b)1).
Also published as
CZPV2000-3431
SK14192000
SK200001419
US09644308
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