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US 8,895,581 B2Granted
1H-imidazo[4,5-c]quinolines
AssigneeBoehringer Ingelheim International GmbH
InventorsDarryl McConnell, Harald Engelhardt, Christiane Kofink
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Abstract
The present invention encompasses compounds of general formula (1), wherein the groups R1 to R7, Qa, Qb, L, n and m are defined as in claim 1, which are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation, pharmaceutical preparations containing such compounds and their use as medicaments.
Claims18
A compound of the formula (1)
- wherein
- Qa is a ring system optionally substituted by one or more, identical or different Ra and/or Rb, selected from among C3-10cycloalkyl, C6-10aryl, 5-12 membered heteroaryl and 3-14 membered heterocyclyl;
- R1 and R2 are selected independently of one another from among hydrogen, halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4haloalkyl, —NH2, —CN, —NHC1-4alkyl, —N(C1-4alkyl)2, —OH, —OC1-4alkyl, HO—C1-4alkylene-, C1-4alkyl-O—C1-4alkylene-, H2N—C1-4alkylene-, —O—C1-4haloalkyl, (C1-4alkyl)NH—C1-4alkylene- and (C1-4alkyl)2N—C1-4alkylene-, wherein the alkyl, alkenyl, alkynyl and alkylene mentioned in the above groups may optionally be substituted by one or more identical or different halogen atoms;
- the ring system Qb is
- each R3 is independently selected from among halogen, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4haloalkyl, —NH2, —CN, —N(C1-4alkyl, —N(C1-4alkyl)2, —OH, —O—C1-4alkyl, HO—C1-4alkylene-, HO—C2-4alkylene-O—, C1-4alkyl-O—C1-4alkylene-, C1-4haloalkyl-O—C1-4alkylene-, H2N—C1-4alkylene-, C1-4alkyl-O—C2-4alkylene-O—, (C1-4alkyl)NH—C1-4alkylene-, (C1-4alkyl)2N—C1-4alkylene-, —OC1-4haloalkyl, H2N—C2-4alkylene-O—, —NH(C2-4alkylene-NH2), —NH[C2-4alkylene-NH(C1-4alkyl)], NH[C2-4alkylene-N(C1-4alkyl)2], (C1-4alkyl)2N—C2-4alkylene-O—, (C1-4haloalkyl)2N—C2-4alkylene-O—, (C1-4haloalkyl)NH—C2-4alkylene-O— and (C1-4alkyl)NH—C2-4alkylene-O—;
- n denotes the number 0, 1, 2 or 3;
- wherein a group R3 in the ring system Qb-4 replaces a hydrogen in each case;
- R4 denotes hydrogen or C1-4alkyl;
- L denotes the group
- wherein
- the group —CR8R9— binds to the group —NR4—, in case (ii) both a cis and a trans configuration may be present with respect to the double bond and
- R8 and R9 are independently selected from among hydrogen, halogen, C1-4alkyl and C1-4haloalkyl;
- R5 is selected from among Ra and Rb;
- R6 is selected from among Ra and Rb;
- each R7 is independently selected from among Ra and Rb;
- m denotes the number 0, 1 or 2;
- each Ra independently denotes hydrogen or a group optionally substituted by one or more, identical or different Rb and/or Rc, selected from among C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C6-10aryl, 5-12 membered heteroaryl and 3-14 membered heterocyclyl;
- each Rb is independently selected from among —ORc, —NRcRc, halogen, —CN, —NO2, —C(O)Rc, —C(O)ORc, —C(O)NRcRc, —S(O)2Rc, —S(O)2NRcRc, —NHC(O)Rc and —N(C1-4alkyl)C(O)Rc as well as the bivalent substituent ═O, wherein the latter may only be a substituent in non-aromatic ring systems;
- each Rc independently denotes hydrogen or a group optionally substituted by one or more, identical or different Rd and/or Re, selected from among C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C6-10aryl, 5-12 membered heteroaryl and 3-14 membered heterocyclyl;
- each Rd is independently selected from among —ORe, —NReRe, halogen, —CN, —NO2, —C(O)Re, —C(O)ORe, —C(O)NReRe, —S(O)2Re, —S(O)2NReRe, —NHC(O)Re and —N(C1-4alkyl)C(O)Re, as well as the bivalent substituent ═0, wherein the latter may only be a substituent in non-aromatic ring systems;
- each Re independently denotes hydrogen or a group optionally substituted by one or more, identical or different Rf and/or Rg, selected from among C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C6-10aryl, 5-12 membered heteroaryl and 3-14 membered heterocyclyl;
- each Rf is independently selected from among —ORg, —NRgRg, halogen, —CN, —NO2, —C(O)Rg, —C(O)ORg, —C(O)NRgRg, —S(O)2Rg, —S(O)2NRgRg, —NHC(O)Rg and —N(C1-4alkyl)C(O)Rg, as well as the bivalent substituent ═O, wherein the latter may only be a substituent in non-aromatic ring systems and
- each Rg is independently selected from among hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C6-10aryl, 5-12 membered heteroaryl and 3-14 membered heterocyclyl;
- wherein the compounds (1) may optionally also be present in the form of their tautomers, racemates, enantiomers, diastereomers or mixtures thereof or as the respective salts of all the above-mentioned forms.
21 more elements
Dependencies are inferred from the claim text.