| Heteroaryl derivatives and their use as medicaments -> Monitor Keywords |
|
|
 
Heteroaryl derivatives and their use as medicamentsRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai, Hetero Ring Is Six-membered Consisting Of Three Nitrogens And Three Carbon AtomsHeteroaryl derivatives and their use as medicaments description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20050245523, Heteroaryl derivatives and their use as medicaments. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS REFERENCE TO RELATED APPLICATION [0001] This application is a division of application Ser. No. 10/741,310 filed Dec. 19, 2003, which is a continuation of application Ser. No. 09/910,141 filed Jul. 20, 2001, now U.S. Pat. No. 6,890,926. Both applications are incorporated herein by reference in their entirety. FIELD OF THE INVENTION [0002] The invention relates to novel heteroaryl derivatives of the formula 1, to their preparation and to their use as medicaments, in particular for treating tumors. DESCRIPTION OF THE INVENTION [0003] According to one aspect of the invention, novel quinoline derivatives of the formula 1 in which 2 [0004] in which [0005] R, R.sub.1, R.sub.2, R.sub.3; can be attached to any of the quinoline carbon atoms C.sub.2 to C.sub.8, are the same or different and independently of one another denote hydrogen, straight-chain or branched (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.1)-cycloalkyl, straight-chain or branched (C.sub.1-C.sub.8)-alkylcarbonyl, preferably acetyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxy, halogen, aryl-(C.sub.1-C.sub.8)-alkoxy, preferably benzyloxy or phenylethyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)alkylamino, di-(C.sub.1-C.sub.4)-alky- l amino, (C.sub.1-C.sub.8) alkoxycarbonylamino, (C.sub.1-C.sub.6)-alkoxyca- rbonylamino-(C.sub.1-C.sub.8)alkyl, cyano, straight-chain or branched cyano-(C.sub.1-C.sub.6)-alkyl, carboxyl, (C.sub.1-C.sub.8)-alkoxycarbonyl- , (C.sub.1-C.sub.4)-alkyl which is substituted by one or more fluorine atoms, preferably the trifluoromethyl group, carboxy-(C.sub.1-C.sub.8)-al- kyl or (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, preferably allyl, (C.sub.2-C.sub.6)-alkynyl, preferably ethynyl or propargyl, straight-chain or branched cyano-(C.sub.1-C.sub.6)-alkyl, preferably cyanomethyl, aryl, where the aryl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of halogen, straight-chain or branched (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, carboxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxycarbonyl, preferably tertbutoxycarbonyl, by trifluoromethyl, hydroxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxy, preferably methoxy or ethoxy, benzyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, cyano, straight-chain or branched cyano-(C.sub.1-C.sub.6)-alkyl, where additionally R and R.sub.1 or R.sub.2 and R.sub.3 may form a fused aromatic 6-membered ring with the quinoline ring forming an acridine ring which for its part can be substituted at any C atom ring position by the radicals R, R.sub.1, R.sub.2 and R; having the meanings mentioned above; [0006] Z is oxygen or sulfur, where the radical 3 [0007] substituted on the quinoline heterocycle can be attached to C atoms C.sub.2-C.sub.8 of the quinoline ring skeleton; [0008] P, Q independently of one another represent oxygen or in each case two hydrogen atoms (i.e. --CH.sub.2--); [0009] X is nitrogen or C--R.sub.5, where R.sub.5 represents hydrogen or (C.sub.1-C.sub.6)-alkyl; [0010] n,m independently of one another denotes an integer between 0-3, with the proviso that in the case n=0, X denotes a CR.sub.5R.sub.6 group where R.sub.5 and R.sub.6 independently of one another represent hydrogen or (C.sub.1-C.sub.6)-alkyl and that the nitrogen atom adjacent to the C=Z group is substituted by a hydrogen atom or a (C.sub.1-C.sub.6)-alkyl group; [0011] R.sub.4 or a straight-chain or branched (C.sub.1-C.sub.20)-alkyl radical which can be saturated or unsaturated, with one to three double and/or triple bonds, and which can be unsubstituted or may optionally be substituted at the same or different C atoms by one, two or more aryl, heteroaryl, halogen, cyano, (C.sub.1-C.sub.6)-alkoxycarbonylamino, (C.sub.1-C.sub.6)-alkoxy, amino, mono-(C.sub.1-C.sub.4)-alkylamino or di-(C.sub.1-C.sub.4)alkylamino; a (C.sub.6-C.sub.14)-aryl radical, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.4)-alkyl radical, or a a (C.sub.2-C.sub.10)-heteroaryl or (C.sub.2-C.sub.10)-heteroaryl-(C.sub.1-C- .sub.4)-alkyl radical which contains one or more heteroatoms selected from the group of N, O and S, where the (C.sub.1-C.sub.4)-alkyl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of (C.sub.1-C.sub.6)-alkyl, halogen or oxo (.dbd.O), and where the (C.sub.6-C.sub.14)-aryl or (C.sub.2-C.sub.10)-heteroaryl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of straight-chain or branched (C.sub.1-C.sub.8)alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halogen, cyano, (C.sub.1-C.sub.6)alkoxycarb- onylamino, (C.sub.1-C.sub.6)-alkoxy, carboxyl, (C.sub.1-C.sub.8)-alkoxycar- bonyl, straight-chain or branched (C.sub.1-C.sub.6)-alkyl which is substituted by one or more fluorine atoms, preferably trifluoromethyl, hydroxyl, straight-chain or branched (C.sub.1-C.sub.8)alkoxy, preferably methoxy or ethoxy, where adjacent oxygen atoms may also be linked by (C.sub.1-C.sub.2)-alkylene groups, preferably by a methylene group, benzyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aryl, which for its part can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of straight-chain or branched (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, carboxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxycarbonyl, by trifluoromethyl, hydroxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxy, preferably methoxy or ethoxy, benzyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino- , cyano, straight-chain or branched cyano-(C.sub.1-C.sub.6)-alkyl; [0012] and their structural isomers and stereoisomers, in particular tautomers, diastereomers and enantiomers, and their pharmaceutically acceptable salts, in particular acid addition salts, are provided. [0013] Thus, for example, the compounds of the formula (1) according to the invention which have one or more centers of chirality and which are present as racemates can be separated by methods known per se into their optical isomers, i.e. enantiomers or diastereomers. The separation can be carried out by column separation on chiral phases or by recrystallization from an optically active solvent or using an optically active acid or base or by derivatization with an optically active reagent, such as, for example, an optically active alcohol, and subsequent removal of the radical. [0014] Furthermore, the quinoline derivatives of the formula (1) according to the invention can be converted into their salts with inorganic or organic acids, in particular, for pharmaceutical use, into their physiologically acceptable salts. Acids which are suitable for this purpose are, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, fumaric acid, succinic acid, lactic acid, citric acid, acetic acid, tartaric acid, malic acid, embonic acid, malonic acid, trifluoroacetic acid or maleic acid. [0015] Moreover, the compounds of the formula (1) according to the invention can, if they contain a sufficiently acidic group, such as a carboxyl group, be converted, if desired, into their salts with inorganic or organic bases, in particular, for pharmaceutical use, into their physiologically acceptable salts. Bases which are suitable for this purpose are, for example, sodium hydroxide, potassium hydroxide, calcium hydroxide, lysine, cyclohexylamine, ethanolamine, diethanolamine and triethanolamine. [0016] According to a preferred embodiment, quinoline derivatives of the formula 1 are provided in which R, R.sub.1, R.sub.2, R.sub.3, X, Z, P, Q, n and m have the meanings given above and R.sub.4 denotes a straight-chain or branched (C.sub.1-C.sub.20)-alkyl radical which can be saturated or unsaturated, with one to three double and/or triple bonds, and which can be unsubstituted or optionally substituted on the same or different C atoms by one, two or more aryl, heteroaryl, halogen, (C.sub.1-C.sub.6)-alkoxy, amino, mono-(C.sub.1-C.sub.4)-alkylamino or di(C.sub.1-C.sub.4)-alkylamino; [0017] a phenyl ring or a naphthyl ring, each of which can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of straight-chain or branched (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, halogen, carboxyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, straight-chain or branched (C.sub.1-C.sub.6)-alkyl which is substituted by one or more fluorine atoms, preferably trifluoromethyl, hydroxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxy, preferably methoxy or ethoxy, where adjacent oxygen atoms may also be linked by (C.sub.1-C.sub.2)-alkylene groups, preferably a methylene group, benzyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aryl, which for its part can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of straight-chain or branched (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, carboxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxycarbonyl, by trifluoromethyl, hydroxyl, straight-chain or branched (C.sub.1-C.sub.8)-alkoxy, preferably methoxy or ethoxy, benzyloxy, nitro, amino, mono-(C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino- , cyano, straight-chain or branched cyano-(C.sub.1-C.sub.6)alkyl; [0018] a 2-, 4-, 5- or 6-pyrimidinyl radical, or a 2-, 4-, 5- or 6-pyrimidinyl(C.sub.1-C.sub.4)-alkyl radical, where the (C.sub.1-C.sub.4)-alkyl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of (C.sub.1-C.sub.6)-alkyl, halogen or oxo (.dbd.O), and the 2-, 4-, 5- or 6-pyrimidinyl radical can be unsubstituted or mono- to trisubstituted by the same or different substituents from the group of hydrogen, (C.sub.1-C.sub.6)-alkyl, halogen, nitro, amino, mono-(C.sub.1-C.sub.6)-al- kylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxyl, (C.sub.1-C.sub.6)-alkoxy, benzyloxy, carboxyl, (C.sub.1-C.sub.6)-alkoxyca- rbonyl, (C.sub.1-C.sub.6)-alkoxycarbonylamino or (C.sub.1-C.sub.6)-alkyl which is mono- or polysubstituted by fluorine, preferably trifluoromethyl, (C.sub.6-C.sub.10)-aryl and (C.sub.6-C.sub.10)-aryl-(C.s- ub.1-C.sub.6)-alkyl; [0019] a 3-, 4-, 5- or 6-pyridazinyl radical, or a 3-, 4-, 5- or 6-pyridazinyl(C.sub.1-C.sub.4)-alkyl radical, where the (C.sub.1-C.sub.4)-alkyl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of (C.sub.1-C.sub.6)-alkyl, halogen or oxo (.dbd.O), and the 3-, 4-, 5- or 6-pyridazinyl radical can be unsubstituted or mono- to trisubstituted by the same or different substituents from the group of hydrogen, (C.sub.1-C.sub.6)-alkyl, halogen, nitro, amino, mono-(C.sub.1-C.sub.6)-al- kylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxyl, (C.sub.1-C.sub.6)-alkoxy, benzyloxy, carboxyl, (C.sub.1-C.sub.6)-alkoxyca- rbonyl, (C.sub.1-C.sub.6)-alkoxycarbonylamino or (C.sub.1-C.sub.6)-alkyl which is mono- or polysubstituted by fluorine, preferably trifluoromethyl, (C.sub.6-C.sub.10)-aryl and (C.sub.6-C.sub.10)-aryl-(C.s- ub.1-C.sub.6)-alkyl; [0020] a 2-, 3-, 5- or 6-pyrazinyl radical, or a 2-, 3-, 5- or 6-pyrazinyl-(C.sub.1-C.sub.4)-alkyl radical, where the (C.sub.1-C.sub.4)-alkyl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of (C.sub.1-C.sub.6)-alkyl, halogen or oxo (.dbd.O), and the 2-, 3-, 5- or 6-pyrazinyl radical can be unsubstituted or mono- to trisubstituted by the same or different substituents from the group of hydrogen, (C.sub.1-C.sub.6)-alkyl, halogen, nitro, amino, mono-(C.sub.1-C.sub.6)-al- kylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxyl, (C.sub.1-C.sub.6)-alkoxy, benzyloxy, carboxyl, (C.sub.1-C.sub.6)-alkoxyca- rbonyl, (C.sub.1-C.sub.6)alkoxycarbonylamino or (C.sub.1-C.sub.6)-alkyl which is mono- or polysubstituted by fluorine, preferably trifluoromethyl, (C.sub.6-C.sub.10)-aryl and (C.sub.6-C.sub.10)-aryl-(C.s- ub.1-C.sub.6)-alkyl; [0021] a 3-, 4-, 5-, 6-, 7-, or 8-cinnolinyl radical, or a 3-, 4-, 5-, 6-, 7-, or 8cinnolinyl-(C.sub.1-C.sub.4)-alkyl radical, where the (C.sub.1-C.sub.4)-alkyl radical can be unsubstituted or mono- or polysubstituted by the same or different substituents from the group of (C.sub.1-C.sub.6)-alkyl, halogen or oxo (.dbd.O), and the 3-, 4-, 5-, 6-, 7-, or 8-cinnolinyl radical can be unsubstituted or mono- to pentasubstituted by the same or different substituents from the group of hydrogen, (C.sub.1-C.sub.6)-alkyl, halogen, nitro, amino, mono-(C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxyl, (C.sub.1-C.sub.6)-alkoxy, benzyloxy, carboxyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-alkoxycarbonylamino or (C.sub.1-C.sub.6)-, alkyl which is mono- or polysubstituted by fluorine, preferably trifluoromethyl, (C.sub.6-C.sub.10)-aryl and (C.sub.6-C.sub.10)-aryl-(C.sub.1-C.sub.6)-alkyl; Continue reading about Heteroaryl derivatives and their use as medicaments... Full patent description for Heteroaryl derivatives and their use as medicaments Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Heteroaryl derivatives and their use as medicaments patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. Start now! - Receive info on patent apps like Heteroaryl derivatives and their use as medicaments or other areas of interest. ### Previous Patent Application: Novel compounds Next Patent Application: Benzotriazine inhibitors of kinases Industry Class: Drug, bio-affecting and body treating compositions ### FreshPatents.com Support Thank you for viewing the Heteroaryl derivatives and their use as medicaments patent info. IP-related news and info Results in 0.64444 seconds Other interesting Feshpatents.com categories: Tyco , Unilever , Warner-lambert , 3m pbckp |
 * Protect your Inventions * US Patent Office filing 
PATENT INFO |
|
