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Last Updated: April 19, 2024

Claims for Patent: 9,555,022


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Summary for Patent: 9,555,022
Title:Substituted triazolopyridines
Abstract: The present invention relates to substituted triazolopyridine compounds of general formula (I): in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, 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 of uncontrolled cell growth, proliferation and/or survival as well as to the use of intermediate compounds for the preparation of said compounds. ##STR00001##
Inventor(s): Schulze; Volker (OT Bergfelde, DE), Kosemund; Dirk (Berlin, DE), Schirok; Hartmut (Langenfeld, DE), Bader; Benjamin (Berlin, DE), Lienau; Philip (Berlin, DE), Wengner; Antje Margret (Berlin, DE), Briem; Hans (Berlin, DE), Holton; Simon (Berlin, DE), Siemeister; Gerhard (Berlin, DE), Prechtl; Stefan (Berlin, DE), Koppitz; Marcus (Berlin, DE), Stockigt; Detlef (Potsdam, DE), Prien; Olaf (Berlin, DE)
Assignee: Bayer Intellectual Property GmbH (Monheim, DE)
Application Number:13/704,859
Patent Claims:1. A compound of general formula (I): ##STR00229## in which: R.sup.1 represents an aryl or heteroaryl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.6--(C.sub.1-C.sub.6-alkyl)-, R.sup.6--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.6--(C.sub.1-C.sub.6-alkoxy)-, R.sup.6--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.6--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.6--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, R.sup.6--O--, --C(.dbd.O)R.sup.6, --C(.dbd.O)O--R.sup.6, --OC(.dbd.O)--R.sup.6, --N(H)C(.dbd.O)R.sup.6, --N(R.sup.7)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)NR.sup.6R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.6R.sup.7, --NR.sup.6R.sup.7, --C(.dbd.O)N(H)R.sup.6, --C(.dbd.O)NR.sup.6R.sup.7, R.sup.6--S--, R.sup.6--S(.dbd.O)--, R.sup.6--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.6, --N(R.sup.7)S(.dbd.O)R.sup.6, --S(.dbd.O)N(H)R.sup.6, --S(.dbd.O)NR.sup.6R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.6, --N(R.sup.7)S(.dbd.O).sub.2R.sup.6, --S(.dbd.O).sub.2N(H)R.sup.6, --S(.dbd.O).sub.2NR.sup.6R.sup.7, --S(.dbd.O)(.dbd.NR.sup.6)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.6, --N.dbd.S(.dbd.O)(R.sup.6)R.sup.7; and which is optionally substituted, one or more times, identically or differently, with a substituent R.sup.xy selected from: halo-, hydroxyl-, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, R.sup.8--(C.sub.1-C.sub.6-alkyl)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.8--(C.sub.1-C.sub.6-alkoxy)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, R.sup.8--O--, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S--, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.8, --N(R.sup.7)S(.dbd.O)R.sup.8, --S(.dbd.O)N(H)R.sup.8, --S(.dbd.O)NR.sup.8R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.8, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8, --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.2 represents an aryl group or heteroaryl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.9--, R.sup.9--(C.sub.1-C.sub.6-alkyl)-, R.sup.9--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.9--(C.sub.1-C.sub.6-alkoxy)-, R.sup.9--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.9--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.9--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, --O--(CH.sub.2).sub.n--C(.dbd.O)NR.sup.9R.sup.7, R.sup.9--O--, --C(.dbd.O)R.sup.9, --C(.dbd.O)O--R.sup.9, --OC(.dbd.O)--R.sup.9, --N(H)C(.dbd.O)R.sup.9, --N(R.sup.7)C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)NR.sup.9R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.9R.sup.7, --NR.sup.9R.sup.7, --C(.dbd.O)N(H)R.sup.9, --C(.dbd.O)NR.sup.9R.sup.7, R.sup.9--S--, R.sup.9--S(.dbd.O)--, R.sup.9--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.9, --N(R.sup.7)S(.dbd.O)R.sup.9, --S(.dbd.O)N(H)R.sup.9, --S(.dbd.O)NR.sup.9R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.9, --N(R.sup.7)S(.dbd.O).sub.2R.sup.9, --S(.dbd.O).sub.2N(H)R.sup.9, --S(.dbd.O).sub.2NR.sup.9R.sup.7, --S(.dbd.O)(.dbd.NR.sup.9)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.9, --N.dbd.S(.dbd.O)(R.sup.9)R.sup.7; and which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, R.sup.8--(C.sub.1-C.sub.6-alkyl)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sup.m--, R.sup.8--(C.sub.1-C.sub.6-alkoxy)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, --O--(CH.sub.2).sub.n--C(.dbd.O)NR.sup.8R, R.sup.8--O--, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S--, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.8, --N(R.sup.7)S(.dbd.O)R.sup.8, --S(.dbd.O)N(H)R.sup.8, --S(.dbd.O)NR.sup.8R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.8, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8, --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.3 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, nitro-, C.sub.1-C.sub.4-alkyl-, halo-C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.4-alkoxy-, halo-C.sub.1-C.sub.4-alkoxy-, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl-, halo-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl-, C.sub.2-C.sub.6-alkenyl-, C.sub.2-C.sub.6-alkynyl-, halo-C.sub.2-C.sub.6-alkenyl-, halo-C.sub.2-C.sub.6-alkynyl-, C.sub.3-C.sub.6-cycloalkyl-, or halo-C.sub.3-C.sub.6-cycloalkyl-group; R.sup.4 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, nitro-, C.sub.1-C.sub.4-alkyl-, halo-C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.4-alkoxy-, halo-C.sub.1-C.sub.4-alkoxy-, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl-, halo-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl-, C.sub.2-C.sub.6-alkenyl-, C.sub.2-C.sub.6-alkynyl-, halo-C.sub.2-C.sub.6-alkenyl-, halo-C.sub.2-C.sub.6-alkynyl-, C.sub.3-C.sub.6-cycloalkyl-, or halo-C.sub.3-C.sub.6-cycloalkyl-group; R.sup.5 represents a hydrogen atom; R.sup.6 represents a group selected from: C.sub.3-C.sub.6-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-, heteroaryl-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), --(CH.sub.2).sub.q-(3- to 10-membered heterocycloalkyl), --(CH.sub.2).sub.q-aryl, or --(CH.sub.2).sub.q-heteroaryl; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, R.sup.8--(C.sub.1-C.sub.6-alkyl)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.8--(C.sub.1-C.sub.6-alkoxy)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, aryl-, R.sup.8--O--, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S--, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.8, --N(R.sup.7)S(.dbd.O)R.sup.8, --S(.dbd.O)N(H)R.sup.8, --S(.dbd.O)NR8R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.8, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8, --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.7 represents a hydrogen atom, a C.sub.1-C.sub.6-alkyl-, or C.sub.3-C.sub.6-cycloalkyl-group; or R.sup.6 and R.sup.7, together with the nitrogen atom to which they are attached, represent a 3- to 10-membered heterocycloalkyl-group, which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, C.sub.2-C.sub.6-alkynyl- or C.sub.3-C.sub.6-cycloalkyl-; R.sup.8 represents a hydrogen atom or a C.sub.1-C.sub.6-alkyl-group; R.sup.9 represents a group selected from: C.sub.7-C.sub.10-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, aryl-, heteroaryl-; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.8--(C.sub.1-C.sub.6-alkoxy)-, R.sup.8--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.8--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, aryl-, R.sup.8--O--, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S--, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.8, --N(R.sup.7)S(.dbd.O)R.sup.8, --S(.dbd.O)N(H)R.sup.8, --S(.dbd.O)NR.sup.8R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.8, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8, --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; or R.sup.9 and R.sup.7, together with the nitrogen atom to which they are attached, represent a 3- to 10-memberered heterocycloalkyl-group, which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, cyano-, nitro-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-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-, C.sub.2-C.sub.6-alkynyl-, --C(.dbd.O)O--R.sup.8 or C.sub.3-C.sub.6-cycloalkyl-; n, m, p represent, independently from each other, an integer of 0, 1, 2, 3, 4, or 5; q represents an integer of 0, 1, 2 or 3; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

2. The compound according to claim 1, wherein: R.sup.1 represents an aryl or heteroaryl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.6--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.m--, R.sup.6--(C.sub.1-C.sub.6-alkoxy)-, R.sup.6--(CH.sub.2).sub.n(CHOH)(CH.sub.2).sub.p--O--, R.sup.6--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-, R.sup.6--(C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl)-O--, R.sup.6--O--, --C(.dbd.O)R.sup.6, --C(.dbd.O)O--R.sup.6, --OC(.dbd.O)--R.sup.6, --N(H)C(.dbd.O)R.sup.6, --N(R.sup.7)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)NR.sup.6R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.6R.sup.7, --NR.sup.6R.sup.7, --C(.dbd.O)N(H)R.sup.6, --C(.dbd.O)NR.sup.6R.sup.7, R.sup.6--S--, R.sup.6--S(.dbd.O)--, R.sup.6--S(.dbd.O).sub.2--, --N(H)S(.dbd.O)R.sup.6, --N(R.sup.7)S(.dbd.O)R.sup.6, --S(.dbd.O)N(H)R.sup.6, --S(.dbd.O)NR.sup.6R.sup.7, --N(H)S(.dbd.O).sub.2R.sup.6, --N(R.sup.7)S(.dbd.O).sub.2R.sup.6, --S(.dbd.O).sub.2N(H)R.sup.6, --S(.dbd.O).sub.2NR.sup.6R.sup.7, --S(.dbd.O)(.dbd.NR.sup.6)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.6, --N.dbd.S(.dbd.O)(R.sup.6)R.sup.7; and which is optionally substituted, one or more times, identically or differently, with a substituent R.sup.xy selected from: halo-, hydroxyl-, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-C.sub.1-C.sub.6-alkyl-, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

3. The compound according to claim 1, wherein: R.sup.2 represents an aryl group or heteroaryl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.9--, R.sup.9--(C.sub.1-C.sub.6-alkyl)-, R.sup.9--(C.sub.1-C.sub.6-alkoxy)-, R.sup.9--O--, --C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)R.sup.9, --N(R.sup.7)C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)NR.sup.9R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.9R.sup.7, --NR.sup.9R.sup.7, C(.dbd.O)N(H)R.sup.9, --C(.dbd.O)NR.sup.9R.sup.7, R.sup.9--S(.dbd.O)--, R.sup.9--S(.dbd.O).sub.2--, --N(H)S(.dbd.O).sub.2R.sup.9, N(R.sup.7)S(.dbd.O).sub.2R.sup.9, --S(.dbd.O).sub.2N(H)R.sup.9, --S(.dbd.O).sub.2NR.sup.9R.sup.7, --S(.dbd.O)(.dbd.NR.sup.9)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.9; and which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S--, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

4. The compound according to claim 1, wherein: R.sup.3 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, C.sub.1-C.sub.4-alkyl-, hydroxy-C.sub.1-C.sub.4-alkyl or C.sub.2-C.sub.6-alkynyl-group; R.sup.4 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, C.sub.1-C.sub.4-alkyl-, hydroxy-C.sub.1-C.sub.4-alkyl or C.sub.2-C.sub.6-alkynyl-group; R.sup.6 represents a group selected from: --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), --(CH.sub.2).sub.q-(3- to 10-membered heterocycloalkyl), --(CH.sub.2).sub.q-aryl, or --(CH.sub.2).sub.q-heteroaryl; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy- or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

5. The compound according to claim 1, wherein: R.sup.1 represents an aryl group which is substituted, one or more times, identically or differently, with a substituent selected from: --C(.dbd.O)R.sup.6, --C(.dbd.O)O--R.sup.6, --OC(.dbd.O)--R.sup.6, --N(H)C(.dbd.O)R.sup.6, --C(.dbd.O)N(H)R.sup.6, --C(.dbd.O)NR.sup.6R.sup.7, R.sup.6--S(.dbd.O)--, R.sup.6--S(.dbd.O).sub.2--, --N(H)S(.dbd.O).sub.2R.sup.6, --S(.dbd.O).sub.2N(H)R.sup.6, --S(.dbd.O)(.dbd.NR.sup.6)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.6; and which is optionally substituted, one or more times, identically or differently, with a substituent R.sup.xy selected from: halo-, hydroxyl-, cyano-, C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, hydroxy-C.sub.1-C.sub.6-alkyl-, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7; R.sup.2 represents an aryl group or heteroaryl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.9--, R.sup.9--(C.sub.1-C.sub.6-alkyl)-, R.sup.9--(C.sub.1-C.sub.6-alkoxy)-, --C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)R.sup.9, --N(R.sup.7)C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)NR.sup.9R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.9R.sup.7, --NR.sup.9R.sup.7, --C(.dbd.O)N(H)R.sup.9, --C(.dbd.O)NR.sup.9R.sup.7, R.sup.9--S(.dbd.O)--, R.sup.9--S(.dbd.O).sub.2--, --N(H)S(.dbd.O).sub.2R.sup.9, --N(R.sup.7)S(.dbd.O).sub.2R.sup.9, --S(.dbd.O).sub.2N(H)R.sup.9, --S(.dbd.O).sub.2NR.sup.9R.sup.7, --S(.dbd.O)(.dbd.NR.sup.9)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.9; and which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --OC(.dbd.O)--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(R.sup.7)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S(.dbd.O)--, R.sup.8--S(.dbd.O).sub.2--, --N(R.sup.7)S(.dbd.O).sub.2R.sup.8, --S(.dbd.O).sub.2N(H)R.sup.8, --S(.dbd.O).sub.2NR.sup.8R.sup.7, --S(.dbd.O)(.dbd.NR.sup.8)R.sup.7, --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8; R.sup.3 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, C.sub.1-C.sub.4-alkyl-, hydroxy-C.sub.1-C.sub.4-alkyl or C.sub.2-C.sub.6-alkynyl-group; R.sup.4 represents a hydrogen atom, a halogen atom, a hydroxy-, amino, cyano-, C.sub.1-C.sub.4-alkyl-, hydroxy-C.sub.1-C.sub.4-alkyl or C.sub.2-C.sub.6-alkynyl-group; R.sup.5 represents a hydrogen atom; R.sup.6 represents a group selected from: C.sub.3-C.sub.6-cycloalkyl-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), --(CH.sub.2).sub.q-(3- to 10-membered heterocycloalkyl), --(CH.sub.2).sub.q-aryl, or --(CH.sub.2).sub.q-heteroaryl; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-; R.sup.7 represents a hydrogen atom or a C.sub.1-C.sub.6-alkyl-group; or R.sup.6 and R.sup.7, together with the nitrogen atom to which they are attached, represent a 3- to 10-membered heterocycloalkyl-group, which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy- or C.sub.3-C.sub.6-cycloalkyl-; R.sup.8 represents a hydrogen atom or a C.sub.1-C.sub.6-alkyl-group; R.sup.9 represents a group selected from: C.sub.7-C.sub.10-cycloalkyl-, 3- to 10-membered heterocycloalkyl-, heteroaryl-; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-C.sub.1-C.sub.6-alkyl-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8, --N(H)C(.dbd.O)R.sup.8, --N(H)C(.dbd.O)NR.sup.8R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.8R.sup.7, --NR.sup.8R.sup.7, --C(.dbd.O)N(H)R.sup.8, --C(.dbd.O)NR.sup.8R.sup.7, R.sup.8--S(.dbd.O)-- or R.sup.8--S(.dbd.O).sub.2--; or R.sup.9 and R.sup.7, together with the nitrogen atom to which they are attached, represent a 3- to 10-membered heterocycloalkyl-group, which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, cyano-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, --C(.dbd.O)O--R.sup.8 or C.sub.3-C.sub.6-cycloalkyl; q represents an integer of 0, 1, 2 or 3; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

6. The compound according to claim 1, wherein: R.sup.1 represents a phenyl group which is substituted, one or more times, identically or differently, with a substituent selected from: --N(H)C(.dbd.O)R.sup.6 or --C(.dbd.O)N(H)R.sup.6; and which is optionally substituted, one time with a substituent R.sup.xy selected from: halo-, cyano-, C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-; R.sup.2 represents a phenyl or pyridyl group which is substituted, one or more times, identically or differently, with a substituent selected from: R.sup.9--, --C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)R.sup.9, --N(R.sup.7)C(.dbd.O)R.sup.9, --N(H)C(.dbd.O)NR.sup.9R.sup.7, --N(R.sup.7)C(.dbd.O)NR.sup.9R.sup.7, --NR.sup.9R.sup.7, --C(.dbd.O)N(H)R.sup.9 or --C(.dbd.O)NR.sup.9R.sup.7; and which is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-; R.sup.3 represents a hydrogen atom; R.sup.4 represents a hydrogen atom; R.sup.5 represents a hydrogen atom; R.sup.6 represents a group selected from: C.sub.3-C.sub.6-cycloalkyl-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl) or --(CH.sub.2).sub.q-aryl; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-; R.sup.7 represents a hydrogen atom; R.sup.8 represents a hydrogen atom or a C.sub.1-C.sub.6-alkyl-group; R.sup.9 represents a group selected from: C.sub.7-C.sub.10-cycloalkyl-, 3- to 10-membered heterocycloalkyl-; said group being optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxyl-, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, hydroxy-C.sub.1-C.sub.6-alkyl-, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), --C(.dbd.O)R.sup.8, --C(.dbd.O)O--R.sup.8; or R.sup.9 and R.sup.7, together with the nitrogen atom to which they are attached, represent a 3- to 10-membered heterocycloalkyl-group, which is optionally substituted, one or more times, identically or differently, with halogen, hydroxy, C.sub.1-C.sub.6-alkyl-, halo-C.sub.1-C.sub.6-alkyl-, C.sub.1-C.sub.6-alkoxy-, halo-C.sub.1-C.sub.6-alkoxy-, --C(.dbd.O)O--R.sup.8 or C.sub.3-C.sub.6-cycloalkyl-; q represents an integer of 1 or 2; or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

7. The compound according to claim 1, which is selected from the group consisting of: 2-cyclopropyl-N-[4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}- [1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, 2-cyclopropyl-N-[4-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[- 1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, 2-cyclopropyl-N-[4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]amino}- [1, 2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide trifluoroacetate, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]a- mino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, N-[4-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo- [1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-[4-(2-{[4-(4,4-dimethyl-4,5-dihydro-1, 3-oxazol-2-yl)-2-methoxyphenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)p- henyl]-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-{4-[2-({2-methoxy-4-[(4-methylpiperazin-1-yl)carbony- l] phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl}acetamide, tert-butyl 4-(3-ethoxy-4-{[6-(4-{[(4-fluorophenyl)acetyl]amino}phenyl)[1,2,4]triazol- o[1,5-a]pyridin-2-yl]amino}benzoyl)piperazine-1-carboxylate, N-[4-(2-{[2-ethoxy-4-(piperazin-1-ylcarbonyl)phenyl]amino}[1,2,4]triazolo- [1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-(4-{2-[(4-{[4-(cyclopropylmethyl)piperazin-1-yl]carbonyl}-2-ethoxypheny- l)amino] [1,2,4]triazolo[1,5-a]pyridin-6-yl}phenyl)-2-(4-fluorophenyl)acet- amide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)ph- enyl]amino}[1, 2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide trifluoroacetate, 2-(4-fluorophenyl)-N-[4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(2,2,2-trifluor- oethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, N-(cyclopropylmethyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]a- mino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)benzamide, N-(cyclopropylmethyl)-4-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]am- ino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)benzamide, N-(cyclopropylmethyl)-4-(2-{[4-(4,4-dimethyl-4, 5-dihydro-1, 3-oxazol-2-yl)-2-methoxyphenyl]amino}[1, 2,4]triazolo[1, 5-a]pyridin-6-yl)benzamide, 4-[(6-{4-[(cyclopropylmethyl)carbamoyl]phenyl}[1,2,4]triazolo[1,5-a]pyrid- in-2-yl)amino]-3-ethoxy-N-(1-methylpiperidin-4-yl)benzamide, N-(cyclopropylmethyl)-4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]a- mino}[1, 2,4]triazolo[1,5-a] pyridin-6-yl)benzamide trifluoroacetate, N-(cyclopropylmethyl)-4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(2,2,2-trifluor- oethoxy)phenyl]amino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)benzamide, N-(4-Fluorbenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino- }[1,2,4]triazolo[1, 5-a]pyridin-6-yl)benzamid, 4-(2-{[2-Ethoxy-4-(morpholin-4-ylcarbonyl)phenyl}amino[1,2,4]triazolo[1,5- -a]pyridin-6-yl)-N-(4-fluorbenzyl)benzamid, 2-(4-fluorophenyl)-N-[4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(trifluorometho- xy)phenyl]amino}[1,2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)pheny- l]amino}[1, 2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide, N-[4-(2-{[2-ethoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]amino}[1,2,4]triaz- olo[1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[4-methyl-6-(2-oxo-1, 3-oxazolidin-3-yl)pyridin-3-yl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)p- henyl]acetamide, N-[4-(2-{[4-(4,5-dihydro-1,3-oxazol-2-yl)-2-methoxyphenyl]amino}[1,2,4]tr- iazolo[1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-[4-(2-{[4-(4,5-dihydro-1,3-oxazol-2-yl)-2-methylphenyl]amino}[1,2,4]tri- azolo[1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-{4-[2-({2-methoxy-4-[(1 S,4S)-2-oxa-5-azabicyclo[2.2.1] hept-5-ylcarbonyl] phenyl}amino)[1,2,4]triazolo[1, 5-a]pyridin-6-yl]phenyl}acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(2-oxa-6-azaspiro[3.3]hept-6-ylc- arbonyl)phenyl]amino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, N-{4-[2-({4-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-2-methoxyphenyl}ami- no)[1,2,4]triazolo[1, 5-a]pyridin-6-yl]phenyl}-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-{4-[2-({4-[(3-hydroxyazetidin-1-yl)carbonyl]-2-metho- xyphenyl}amino)[1,2,4]triazolo[1, 5-a]pyridin-6-yl]phenyl}acetamide, 2-(4-fluorophenyl)-N-{4-[2-({4-[(4-hydroxypiperidin-1-yl)carbonyl]-2-meth- oxyphenyl}amino)[1, 2,4]triazolo[1, 5-a]pyridin-6-yl]phenyl}acetamide, 4-{[6-(4-{[(4-fluorophenyl)acetyl]amino}phenyl)[1,2,4]triazolo[1,5-a]pyri- din-2-yl]amino}-3-methoxy-N-(oxetan-3-yl)benzamide, N-[4-(2-{[4-(azetidin-1-ylcarbonyl)-2-methoxyphenyl]amino}[1,2,4]triazolo- [1,5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-[4-(2-{[2-ethoxy-4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)phenyl]amino- }[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-{4-[2-({2-ethoxy-4-[(3-hydroxyazetidin-1-yl)carbonyl] phenyl}amino)[1, 2,4]triazolo[1,5-a]pyridin-6-yl]phenyl}-2-(4-fluorophenyl)acetamide, 3-ethoxy-4-{[6-(4-{[(4-fluorophenyl)acetyl]amino}phenyl)[1,2,4]triazolo[1- ,5-a] pyridin-2-yl]amino}-N-(1-methylpiperidin-4-yl)benzamide, 2-(4-fluorophenyl)-N-[4-(2-{[4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)-2- -(2,2,2-trifluoroethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)ph- enyl]acetamide, 2-(4-fluorophenyl)-N-4-[2-({4-[(3-hydroxyazetidin-1-yl)carbonyl]-2-(2,2,2- -trifluoroethoxy)phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl}ac- etamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)- phenyl]amino}[1, 2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,- 4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, N-[4-(2-{[2-(2-fluoroethoxy)-4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)ph- enyl]amino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, N-[4-(2-{[2-(2,2-difluoroethoxy)-4-(morpholin-4-ylcarbonyl)phenyl]amino}[- 1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(trifluoromethy- l)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(morpholin-4-ylmethyl)phenyl] amino}[1, 2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide, N-{4-[2-({2-ethoxy-4-[(1-methylpiperidin-4-yl)oxy]phenyl}amino)[1,2,4]tri- azolo[1,5-a]pyridin-6-yl] phenyl}-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-{4-[2-({2-methoxy-4-[(1-methylpiperidin-4-yl)oxy]phe- nyl}amino)[1,2,4]triazolo[1, 5-a]pyridin-6-yl] phenyl}acetamide, 2-(4-fluorophenyl)-N-{4-[2-({4-[(1-methylpiperidin-4-yl)oxy]-2-(methylsul- fanyl)phenyl}amino) [1, 2,4] triazolo[1, 5-a] pyridin-6-yl] phenyl}acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-4-(morpholin-4-ylsulfonyl)phenyl]a- mino}[1, 2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methyl-4-(2-oxa-6-azaspiro[3.3]hept-6-ylca- rbonyl)phenyl]amino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methyl-4-(morpholin-4-ylcarbonyl)phenyl]am- ino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)-2- -(trifluoromethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a] pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methoxy-5-(morpholin-4-ylcarbonyl)phenyl]a- mino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methyl-6-(morpholin-4-yl)pyridin-3-yl]amin- o}[1, 2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, 2-(4-fluorophenyl)-N-[4-(2-{[2-methyl-6-(pyrrolidin-1-yl)pyridin-3-yl]ami- no}[1, 2,4]triazolo[1, 5-a]pyridin-6-yl)phenyl]acetamide, N-{4-[2-({4-[(3-fluoroazetidin-1-yl)carbonyl]-2-methoxyphenyl}amino)[1,2,- 4]triazolo[1, 5-a]pyridin-6-yl]phenyl}-2-(4-fluorophenyl)acetamide, N-(cyclopropylmethyl)-4-(2-{[2-methoxy-4-(2-oxa-6-azaspiro[3.3] hept-6-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzami- de, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)pheny- l]amino}[1, 2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 4-(2-{[2-ethoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]amino}[1,2,4]triazolo- [1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)benzamide, 4-(2-{[4-(4,5-dihydro-1,3-oxazol-2-yl)-2-methoxyphenyl]amino}[1,2,4]triaz- olo[1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)benzamide, N-(4-fluorobenzyl)-4-[2-({2-methoxy-4-[(1 S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-ylcarbonyl] phenyl}amino)[1,2,4]triazolo[1, 5-a]pyridin-6-yl]benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarb- onyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-[2-({4-[(3-hydroxyazetidin-1-yl)carbonyl]-2-methoxyp- henyl}amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide, 4-[2-({4-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-2-methoxyphenyl}amino)- [1,2,4]triazolo[1,5-a]pyridin-6-yl]-N-(4-fluorobenzyl)benzamide, N-(4-fluorobenzyl)-4-[2-({4-[(4-hydroxypiperidin-1-yl)carbonyl]-2-methoxy- phenyl}amino)[1,2,4]triazolo[1, 5-a]pyridin-6-yl]benzamide, 4-[(6-{4-[(4-fluorobenzyl)carbamoyl]phenyl}[1,2,4]triazolo[1,5-a]pyridin-- 2-yl)amino]-3-methoxy-N-(oxetan-3-yl)benzamide, 4-(2-{[2-ethoxy-4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)phenyl]amino}[1- ,2,4]triazolo[1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)benzamide, 4-[2-({4-[(4-acetylpiperazin-1-yl)carbonyl]-2-ethoxyphenyl}amino)[1,2,4]t- riazolo[1,5-a] pyridin-6-yl]-N-(4-fluorobenzyl)benzamide, 4-[2-({2-ethoxy-4-[(3-hydroxyazetidin-1-yl)carbonyl] phenyl}amino)[1,2,4]triazolo[1, 5-a] pyridin-6-yl]-N-(4-fluorobenzyl)benzamide, N-(4-fluorobenzyl)-4-(2-{[4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)-2-(2- ,2,2-trifluoroethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benza- mide, N-(4-fluorobenzyl)-4-[2-({4-[(3-hydroxyazetidin-1-yl)carbonyl]-2-(2,- 2,2-trifluoroethoxy)phenyl}amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzam- ide, N-(4-fluorobenzyl)-4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(2, 2, 2-trifluoroethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzami- de, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]a- mino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 4-(2-{[4-(4-tert-butylpiperazin-1-yl)-2-methoxyphenyl]amino}[1,2,4]triazo- lo[1,5-a] pyridin-6-yl)-N-(4-fluorobenzyl)benzamide, N-(4-fluorobenzyl)-4-(2-{[2-fluoro-4-(2-oxa-6-azaspiro[3.3] hept-6-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzami- de, N-(4-fluorobenzyl)-4-(2-{[2-fluoro-4-(morpholin-4-ylcarbonyl)phenyl]am- ino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 4-(2-{[2-(2, 2-difluoroethoxy)-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[- 1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)benzamide, N-(4-fluorobenzyl)-4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(trifluoromethyl)p- henyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-[2-({2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phe- nyl}amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl] benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylmethyl) phenyl] amino}[1, 2,4]triazolo[1, 5-a] pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-[2-({2-methoxy-4-[(1-methylpiperidin-4-yl)oxy]phenyl- }amino)[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide, N-(4-fluorobenzyl)-4-[2-({4-[(1-methylpiperidin-4-yl)oxy]-2-(methylsulfan- yl)phenyl}amino) [1, 2, 4] triazolo[1,5-a] pyridin-6-yl] benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methyl-4-(2-oxa-6-azaspiro[3.3] hept-6-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzami- de, N-(4-fluorobenzyl)-4-(2-{[2-methyl-4-(morpholin-4-ylcarbonyl)phenyl]am- ino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarbonyl)-2-(t- rifluoromethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a] pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[4-(morpholin-4-ylcarbonyl)-2-(trifluoromethoxy)- phenyl]amino}[1,2,4]triazolo[1,5-a] pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-5-(morpholin-4-ylcarbonyl)phenyl]amin- o}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methyl-6-(morpholin-4-yl)pyridin-3-yl]amino}l- [1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methyl-6-(pyrrolidin-1-yl)pyridin-3-yl]amino}- l[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 4-[2-({4-[(3-fluoroazetidin-1-yl)carbonyl]-2-methoxyphenyl}amino)[1,2,4]t- riazolo[1,5-a]pyridin-6-yl]-N-(4-fluorobenzyl)benzamide, N-(4-chlorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amin- o}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1- ,5-a]pyridin-6-yl)-N-(4-methylbenzyl)benzamide, 2-fluoro-N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)ph- enyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, 2-fluoro-N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylmethyl)phen- yl]amino}[1, 2,4]triazolo[1, 5-a] pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amin- o}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)-2-methylbenzamide, N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]a- mino}[1, 2,4]triazolo[1,5-a]pyridin-6-yl)-2-methylbenzamide, 2-chloro-N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)ph- enyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-(4-fluorobenzyl)-2-methoxy-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)p- henyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide, N-[2-fluoro-4-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,- 4]triazolo[1, 5-a]pyridin-6-yl)phenyl]-2-(4-fluorophenyl)acetamide, 2-(4-fluorophenyl)-N-[5-(2-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]a- mino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)pyridin-2-yl]acetamide, N-[5-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo- [1,5-a]pyridin-6-yl)pyridin-2-yl]-2-(4-fluorophenyl)acetamide, N-(2,4-difluorobenzyl)-4-(2-{[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phen- yl]amino}[1, 2,4]triazolo[1,5-a]pyridin-6-yl)-2-methylbenzamide, N-(4-fluorobenzyl)-5-(2-{[2-methoxy-4-(2-oxa-6-azaspiro[3.3]hept-6-ylcarb- onyl)phenyl]amino}[1,2,4]triazolo[1, 5-a]pyridin-6-yl)pyridine-2-carboxamide, or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.

8. A method of preparing a compound of general formula (I) according to claim 1, in which method an intermediate compound of general formula (5): ##STR00230## in which R.sup.1, R.sup.3, R.sup.4, and R.sup.5 are as defined for the compound of general formula (I) in claim 1, is allowed to react with a compound of general formula (5a): R.sup.2--Y (5a) in which R.sup.2 is as defined for the compound of general formula (I) in claim 1 and Y represents a leaving group, thus providing a compound of general formula (I): ##STR00231## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are as defined for the compound of general formula (I) in claim 1.

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

10. A pharmaceutical combination comprising: one or more compounds of general formula (I) according to claim 1, or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of same; and one or more agents selected from: a taxane; an epothilone; 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; Bortezomib; a platinum derivative; Chlorambucil; Methotrexate; and Rituximab.

11. A method for the treatment of breast cancer, non-small cell lung cancer, prostate cancer, cervical cancer, or melanoma, comprising administering to a patient in need thereof an effective amount of a compound of general formula (I) according to claim 1, or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of same.

12. The pharmaceutical combination according to claim 10, in which the taxane is selected from Docetaxel and Paclitaxel.

13. The pharmaceutical combination according to claim 10, in which the epothilone is selected from Ixabepilone, Patupilone, and Sagopilone.

14. The pharmaceutical combination according to claim 10, in which the anti-androgen is selected from Flutamide, Cyproterone acetate, and Bicalutamide.

15. The pharmaceutical combination according to claim 10, in which the a platinum derivative is selected from Cisplatin and Carboplatin.

Details for Patent 9,555,022

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Genentech, Inc. RITUXAN rituximab Injection 103705 11/26/1997 ⤷  Try a Trial 2030-06-16
Idec Pharmaceuticals Corp. RITUXAN rituximab Injection 103737 02/19/2002 ⤷  Try a Trial 2030-06-16
Genentech, Inc. RITUXAN HYCELA rituximab and hyaluronidase human Injection 761064 06/22/2017 ⤷  Try a Trial 2030-06-16
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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