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Last Updated: March 29, 2024

Claims for Patent: 9,199,999


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Summary for Patent: 9,199,999
Title:Substituted imidazopyrazines
Abstract: The present invention relates to substituted imidazopyrazine compounds of general formula (I) in which A, R.sup.1, R.sup.3 and R.sup.5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds. ##STR00001##
Inventor(s): Klar; Ulrich (Berlin, DE), Koppitz; Marcus (Berlin, DE), Jautelat; Rolf (Haan, DE), Kosemund; Dirk (Berlin, DE), Bohlmann; Rolf (Berlin, DE), Bader; Benjamin (Berlin, DE), Lienau; Philip (Berlin, DE), Siemeister; Gerhard (Berlin, DE), Scott; William (Guilford, CT)
Assignee: Bayer Intellectual Property GmbH (Monheim, DE)
Application Number:13/700,956
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent 9,199,999
Patent Claims:1. A compound of general formula (I): ##STR00149## in which: A represents a ##STR00150## group; Z represents a --C(.dbd.O)N(H)R.sup.2 group, or a group selected from: ##STR00151## R.sup.1 represents a hydrogen atom; R.sup.2 represents a hydrogen atom, or a C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.6-alkyl-, HO--C.sub.1-C.sub.6-alkyl-, --C.sub.1-C.sub.6-alkyl-CN, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, C.sub.2-C.sub.6-alkenyl-, C.sub.2-C.sub.6-alkynyl- or C.sub.3-C.sub.6-cycloalkyl- group; wherein said C.sub.3-C.sub.6-cycloalkyl- group is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, C.sub.1-C.sub.3-alkyl-, cyano-, C.sub.1-C.sub.3-alkoxy-; R.sup.3 represents a hydrogen atom, or a --CN, C.sub.1-C.sub.6-alkyl-, --(CH.sub.2).sub.m--C.sub.3-C.sub.6-cycloalkyl, --(CH.sub.2).sub.m-(3- to 6-membered heterocycloalkyl), aryl-C.sub.1-C.sub.6-alkyl-, heteroaryl-C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, C.sub.3-C.sub.6-cycloalkyl-, 3- to 6-membered heterocycloalkyl-, aryl-, C.sub.1-C.sub.6-alkyl-aryl- or heteroaryl- group; said C.sub.1-C.sub.6-alkyl-, --(CH.sub.2).sub.m--C.sub.3-C.sub.6-cycloalkyl, --(CH.sub.2).sub.m-(3- to 6-membered heterocycloalkyl), aryl-C.sub.1-C.sub.6-alkyl-, heteroaryl-C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, C.sub.3-C.sub.6-cycloalkyl-, 3- to 6-membered heterocycloalkyl-, aryl-, C.sub.1-C.sub.6-alkyl-aryl- or heteroaryl- group being optionally substituted, identically or differently, with 1 or 2 R.sup.7 groups; R.sup.4a and R.sup.4c represent a hydrogen atom; R.sup.4b represents a hydrogen atom or C.sub.1-C.sub.6-alkyl-; R.sup.4d represents a hydrogen atom or C.sub.1-C.sub.6-alkoxy-; R.sup.5 represents a hydrogen atom, or a C.sub.1-C.sub.6-alkyl-, C.sub.2-C.sub.6-alkenyl-, --(CH.sub.2).sub.n--C.sub.2-C.sub.6-alkenyl, --(CH.sub.2).sub.n--C.sub.2-C.sub.3-alkynyl, --(CH.sub.2).sub.m--C.sub.3-C.sub.6-cycloalkyl, --(CH.sub.2).sub.m-(3- to 6-membered heterocycloalkyl), aryl-C.sub.1-C.sub.3-alkyl-, heteroaryl-C.sub.1-C.sub.3-alkyl-, halo-C.sub.1-C.sub.3-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.3-alkyl-, HO--C.sub.1-C.sub.3-alkyl-, --C.sub.1-C.sub.3-alkyl-CN, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, halo-C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.3-C.sub.6-cycloalkyl-, 3- to 6-membered heterocycloalkyl-, C.sub.3-C.sub.6-cycloalkenyl-, C.sub.2-C.sub.6-alkynyl-, aryl- or heteroaryl- group; said C.sub.1-C.sub.6-alkyl-, C.sub.2-C.sub.6-alkenyl-, --(CH.sub.2).sub.n--C.sub.2-C.sub.6-alkenyl, --(CH.sub.2).sub.n--C.sub.2-C.sub.3-alkynyl, --(CH.sub.2).sub.m--C.sub.3-C.sub.6-cycloalkyl, --(CH.sub.2).sub.m-(3- to 6-membered heterocycloalkyl), aryl-C.sub.1-C.sub.3-alkyl-, heteroaryl-C.sub.1-C.sub.3-alkyl-, halo-C.sub.1-C.sub.3-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.3-alkyl-, HO--C.sub.1-C.sub.3-alkyl-, --C.sub.1-C.sub.3-alkyl-CN, C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, halo-C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl-, C.sub.3-C.sub.6-cycloalkyl-, 3- to 6-membered heterocycloalkyl-, C.sub.3-C.sub.6-cycloalkenyl-, C.sub.2-C.sub.6-alkynyl-, aryl- or heteroaryl- group being optionally substituted, identically or differently, with 1 or 2 R.sup.8 groups; R.sup.6, R.sup.6a, R.sup.6b, R.sup.6c, represent, independently from each other, a hydrogen atom, or a C.sub.1-C.sub.6-alkyl-, HO--C.sub.1-C.sub.6-alkyl-, C.sub.3-C.sub.6-cycloalkyl-, C.sub.2-C.sub.6-alkenyl-, 3- to 7-membered heterocycloalkyl-, aryl-, heteroaryl-, aryl-C.sub.1-C.sub.6-alkyl-, or heteroaryl-C.sub.1-C.sub.6-alkyl- group; R.sup.7 represents a hydrogen or halogen atom, or a HO--, --CN, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.6-alkyl-, HO--C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, C.sub.2-C.sub.6-alkenyl-, 3- to 7-membered heterocycloalkyl-, --C(.dbd.O)R.sup.6, --C(.dbd.O)N(H)R.sup.6a, --C(.dbd.O)N(R.sup.6a)R.sup.6b, --C(.dbd.O)O--R.sup.6, --N(R.sup.6a)R.sup.6b, --NO.sub.2, --N(H)C(.dbd.O)R.sup.6, --N(R.sup.6c)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)N(R.sup.6a)R.sup.6b, --N(R.sup.6c)C(.dbd.O)N(R.sup.6a)R.sup.6b, --N(H)C(.dbd.O) OR.sup.6, --N(R.sup.6c)C(.dbd.O)OR.sup.6, --N(H)S(.dbd.O)R.sup.6, --N(R.sup.6c)S(.dbd.O)R.sup.6, --N(H)S(.dbd.O).sub.2R.sup.6, --N(R.sup.6c)S(.dbd.O).sub.2R.sup.6, --N.dbd.S(.dbd.O)(R.sup.6a)R.sup.6b, --O(C.dbd.O)R.sup.6, --O(C.dbd.O)N(R.sup.6a)R.sup.6b, --O(C.dbd.O)OR.sup.6, --SR.sup.6, --S(.dbd.O)R.sup.6, --S(.dbd.O)N(H)R.sup.6, --S(.dbd.O)N(R.sup.6a)R.sup.6b, --S(.dbd.O).sub.2R.sup.6, --S(.dbd.O).sub.2N(H)R.sup.6, --S(.dbd.O).sub.2N(R.sup.6a)R.sup.6b or --S(.dbd.O)(.dbd.NR.sup.6c)R.sup.6 group; R.sup.8 represents a hydrogen or halogen atom, or a --CN, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkyl-, R.sup.6a(R.sup.6b)N--C.sub.1-C.sub.6-alkyl-, HO--C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl-, C.sub.2-C.sub.6-alkenyl-, 3- to 7-membered heterocycloalkyl-, --C(.dbd.O)R.sup.6, --C(.dbd.O)N(H)R.sup.6a, --C(.dbd.O)N(R.sup.6a)R.sup.6b, --C(.dbd.O)O--R.sup.6, --N(R.sup.6a)R.sup.6b, --NO.sub.2, --N(H)C(.dbd.O)R.sup.6, --N(R.sup.6c)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)N(R.sup.6a)R.sup.6b, --N(R.sup.6c)C(.dbd.O)N(R.sup.6a)R.sup.6b, --N(H)C(.dbd.O) OR.sup.6, --N(R.sup.6c)C(.dbd.O)OR.sup.6, --N(H)S(.dbd.O)R.sup.6, --N(R.sup.6c)S(.dbd.O)R.sup.6, --N(H)S(.dbd.O).sub.2R.sup.6, --N(R.sup.6c)S(.dbd.O).sub.2R.sup.6, --N.dbd.S(.dbd.O)(R.sup.6a)R.sup.6b, --OR.sup.6, --O(C.dbd.O)R.sup.6, --O(C.dbd.O)N(R.sup.6a)R.sup.6b, --O(C.dbd.O)OR.sup.6, --SR.sup.6, --S(.dbd.O)R.sup.6, --S(.dbd.O)N(H)R.sup.6, --S(.dbd.O)N(R.sup.6a)R.sup.6b, --S(.dbd.O).sub.2R.sup.6, --S(.dbd.O).sub.2N(H)R.sup.6, --S(.dbd.O).sub.2N(R.sup.6a)R.sup.6b or --S(.dbd.O)(.dbd.NR.sup.6c)R.sup.6 group; m is an integer of 0, 1, 2, 3 or 4; and n is an integer of 1, 2, 3 or 4; or a stereoisomer, a tautomer, a hydrate, a solvate, or a salt thereof, or a mixture of same.

2. The compound according to claim 1, which is selected from the group consisting of: N-cyclopropyl-4-{8-[(3-hydroxypropyl)amino]-6-(3-hydroxyprop-1-yn-1-yl)im- idazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-[6-(3-hydroxyprop-1-yn-1-yl)-8-(isobutylamino)imidazo[1,2- -a]pyrazin-3-yl]benzamide, N-cyclopropyl-4-[8-(isobutylamino)-6-(phenylethynyl)imidazo[1,2-a]pyrazin- -3-yl]benzamide, N-cyclopropyl-4-{6-[(2-fluorophenyl)ethynyl]-8-(isobutylamino)imidazo[1,2- -a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(4-hydroxybutyl)amino]-6-(3-hydroxy-3-methylbut-1-yn-- 1-yl)imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(4-hydroxybutyl)amino]-6-[(1-hydroxycyclopentyl)ethyn- yl]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-hydroxyprop-1-y- n-1-yl)imidazo[1,2-a]pyrazin-3-yl}benzamide, 4-{8-[(3-aminopropyl)amino]-6-(3-hydroxyprop-1-yn-1-yl)imidazo[1,2-a]pyra- zin-3-yl}-N-cyclopropyl-3-methoxybenzamide, 4-{6-(cyclohexylethynyl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3- -yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{6-(3-hydroxy-3-methylbut-1-yn-1-yl)-8-[(2-methylpropyl)a- mino]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-(4-hydroxybut-1-yn-1-yl)-8-[(2-methylpropyl)amino]imid- azo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-[(1-hydroxycyclopentyl)ethynyl]-8-[(2-methylpropyl)ami- no]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-[3-(dimethylamino)prop-1-yn-1-yl]-8-[(2-methylpropyl)a- mino]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-(3-methoxyprop-1-yn-1-yl)-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-(3,3-dimethylbut-1-yn-1-yl)-8-[(2-methylpropyl)amino]i- midazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-(3-hydroxybut-1-yn-1-yl)-8-[(2-methylpropyl)amino]imid- azo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-(4-hydroxypent-1-yn-1-yl)-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl}benzamide, 4-{6-(5-cyanopent-1-yn-1-yl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyraz- in-3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{6-(3-hydroxypent-1-yn-1-yl)-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl}benzamide, 4-(6-{3-[benzyl(methyl)amino]prop-1-yn-1-yl}-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl)-N-cyclopropylbenzamide, 4-{6-(3-aminoprop-1-yn-1-yl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyraz- in-3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{6-(3-hydroxyhex-1-yn-1-yl)-8-[(2-methylpropyl)amino]imid- azo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(2-methylpropyl)amino]-6-(5-phenylpent-1-yn-1-yl)imid- azo[1,2-a]pyrazin-3-yl}benzamide, 6-{3-[4-(cyclopropylcarbamoyl)phenyl]-8-[(2-methylpropyl)amino]imidazo[1,- 2-a]pyrazin-6-yl}hex-5-ynoic acid, N-cyclopropyl-4-{8-[(2-methylpropyl)amino]-6-(pyridin-2-ylethynyl)imidazo- [1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(2-methylpropyl)amino]-6-(4-phenylbut-1-yn-1-yl)imida- zo[1,2-a]pyrazin-3-yl}benzamide, 4-{6-(5-cyclohexylpent-1-yn-1-yl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]- pyrazin-3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{6-(4-methylpent-1-yn-1-yl)-8-[(2-methylpropyl)amino]imid- azo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-[(3- hydroxyphenyl)ethynyl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-y- l}benzamide, 4-{6-[3-(carbamoylamino)prop-1-yn-1-yl]-8-[(2-methylpropyl)amino]imidazo[- 1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{8-[(2-methylpropyl)amino]-6-(3-phenylprop-1-yn-1-yl)imid- azo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-[(4-fluorophenyl)ethynyl]-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{6-[(3S)-3-hydroxyoct-1-yn-1-yl]-8-[(2-methylpropyl)amino- ]imidazo[1,2-a]pyrazin-3-yl}benzamide, methyl 6-{3-[4-(cyclopropylcarbamoyl)phenyl]-8-[(2-methylpropyl)amino]imidazo[1,- 2-a]pyrazin-6-yl}hex-5-ynoate, 9-{3-[4-(cyclopropylcarbamoyl)phenyl]-8-[(2-methylpropyl)amino]imidazo[1,- 2-a]pyrazin-6-yl}non-8-ynoic acid, N-cyclopropyl-4-(6-{3-[(methylcarbamoyl)amino]prop-1-yn-1-yl}-8-[(2-methy- lpropyl)amino]imidazo[1,2-a]pyrazin-3-yl)benzamide, N-cyclopropyl-4-(6-{4-[methyl(methylcarbamoyl)amino]but-1-yn-1-yl}-8-[(2-- methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl)benzamide, N-cyclopropyl-4-{6-[6-(methylamino)-6-oxohex-1-yn-1-yl]-8-[(2-methylpropy- l)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-(6-{3-[methyl(methylcarbamoyl)amino]prop-1-yn-1-yl}-8-[(2- -methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl)benzamide, 4-{6-[(4-carbamoylphenyl)ethynyl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]- pyrazin-3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-(6-{4-[(methylcarbamoyl)amino]but-1-yn-1-yl}-8-[(2-methyl- propyl)amino]imidazo[1,2-a]pyrazin-3-yl)benzamide, N-cyclopropyl-4-{6-[5-(methylamino)-5-oxopent-1-yn-1-yl]-8-[(2-methylprop- yl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide, N-cyclopropyl-4-{8-[(2-methylpropyl)amino]-6-[(4-sulfamoylphenyl)ethynyl]- imidazo[1,2-a]pyrazin-3-yl}benzamide, 4-{6-(cyclopentylethynyl)-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-- 3-yl}-N-cyclopropylbenzamide, N-cyclopropyl-4-{6-ethynyl-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin- -3-yl}benzamide, N-cyclopropyl-4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(2-methylpropyl)amino]imi- dazo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, (2S)-3-({3-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]-6-(3-hydroxyprop-1-- yn-1-yl)imidazo[1,2-a]pyrazin-8-yl}amino)propane-1,2-diol, 3-{3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-[(4,4,4-trifluorobutyl)- amino]imidazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-[(2-methylprop-2-en-1-y- l)amino]imidazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{8-(Allylamino)-3-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]imidazo[1,2- -a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-(isobutylamino)imidazo[- 1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{3-[3-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-(isobutylamino)imidazo[- 1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 4-({3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-6-(3-hydroxyprop-1-yn-1-- yl)imidazo[1,2-a]pyrazin-8-yl}amino)butan-1-ol, 3-{3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-[(3,3,3-trifluoropropyl- )amino]imidazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{8-[(Cyclobutylmethyl)amino]-3-[4-(2-cyclopropyl-1H-imidazol-5-yl)pheny- l]imidazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{3-[4-(2-Cyclopropyl-1H-imidazol-5-yl)phenyl]-8-[(3-hydroxypropyl)amino- ]imidazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-{8-[(3-Aminopropyl)amino]-3-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]i- midazo[1,2-a]pyrazin-6-yl}prop-2-yn-1-ol, 3-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]-6-[3-(1,1-dioxidothiomorphol- in-4-yl)prop-1-yn-1-yl]-N-(3,3,3-trifluoropropyl)imidazo[1,2-a]pyrazin-8-a- mine, N-cyclopropyl-4-{6-[3-(1,1-dioxidothiomorpholin-4-yl)prop-1-yn-1-yl]- -8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-2-methylbenza- mide), 4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-- 3-yl}-N,2-dimethylbenzamide, N-ethyl-4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazi- n-3-yl}-2-methylbenzamide, N-(2,2-difluoroethyl)-4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidaz- o[1,2-a]pyrazin-3-yl}-2-methylbenzamide, 4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-- 2-methyl-N-(1-methylcyclopropyl)benzamide, N-(1-cyanocyclopropyl)-4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imida- zo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, 4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-- N-(1-methoxycyclopropyl)-2-methylbenzamide, 4-{6-ethynyl-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-- N-[rel(1S,2S)-2-fluorocyclopropyl]-2-methylbenzamide, 4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,- 2-a]pyrazin-3-yl}-N,2-dimethylbenzamide, N-ethyl-4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluoropropyl)amino]im- idazo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, N-(2,2-difluoroethyl)-4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluorop- ropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, 4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,- 2-a]pyrazin-3-yl}-2-methyl-N-(1-methylcyclopropyl)benzamide, N-(1-cyanocyclopropyl)-4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluoro- propyl)amino]imidazo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, 4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,- 2-a]pyrazin-3-yl}-N-(1-methoxycyclopropyl)-2-methylbenzamide, N-[rel(1S,2S)-2-fluorocyclopropyl]-4-{6-(3-hydroxyprop-1-yn-1-yl)-8-[(3,3- ,3-trifluoropropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-2-methylbenzamide, or a stereoisomer, a tautomer, a hydrate, a solvate, or a salt thereof, or a mixture of same.

3. A pharmaceutical composition comprising a compound of general formula (I), or a stereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of same, according to claim 1, and a pharmaceutically acceptable diluent or carrier.

4. A pharmaceutical combination comprising: a compound of general formula (I), or a stereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of same, according to claim 1; and one or more agents selected from: a taxane, Docetaxel, Paclitaxel, or Taxol; an epothilone, Ixabepilone, Patupilone, or Sagopilone; Mitoxantrone; Predinisolone; Dexamethasone; Estramustin; Vinblastin; Vincristin; Doxorubicin; Adriamycin; Idarubicin; Daunorubicin; Bleomycin; Etoposide; Cyclophosphamide; Ifosfamide; Procarbazine; Melphalan; 5-Fluorouracil; Capecitabine; Fludarabine; Cytarabine; Ara-C; 2-Chloro-2''-deoxyadenosine; Thioguanine; an anti-androgen, Flutamide, Cyproterone acetate, or Bicalutamide; Bortezomib; a platinum derivative, Cisplatin, or Carboplatin; Chlorambucil; Methotrexate; and Rituximab.

5. A method of preparing a compound of general formula (I): ##STR00152## in which A, R.sup.1, R.sup.3 and R.sup.5 are as defined in claim 1, comprising reacting an intermediate compound of general formula (II): ##STR00153## in which A, R.sup.1 and R.sup.5 are as defined in claim 1, with an alkyne of general formula (IIa): R.sup.3-.ident.-M (IIa) in which R.sup.3 is as defined in claim 1, and -M represents a hydrogen atom or a functional group suitable to be coupled to the Br-bearing carbon atom of the compound of general formula (II).

Details for Patent 9,199,999

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Genentech, Inc. RITUXAN rituximab Injection 103705 11/26/1997 ⤷  Try a Trial 2030-06-01
Idec Pharmaceuticals Corp. RITUXAN rituximab Injection 103737 02/19/2002 ⤷  Try a Trial 2030-06-01
Genentech, Inc. RITUXAN HYCELA rituximab and hyaluronidase human Injection 761064 06/22/2017 ⤷  Try a Trial 2030-06-01
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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