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Last Updated: January 23, 2020

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Claims for Patent: 9,670,202

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Summary for Patent: 9,670,202
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, as well as to intermediate compounds useful in the preparation of said compounds. ##STR00001##
Inventor(s): Schirok; Hartmut (Langenfeld, DE), Schulze; Volker (OT Bergf, DE), Kosemund; Dirk (Berlin, DE), Briem; Hans (Berlin, DE), Bader; Benjamin (Berlin, DE), Bomer; Ulf (Glienicke, DE), Wengner; Antje Margret (Berlin, DE), Siemeister; Gerhard (Berlin, DE), Lienau; Philip (Berlin, DE)
Assignee: BAYER PHARMA AKTIENGESELLSCHAFT (Berlin, DE)
Application Number:14/896,426
Patent Claims:1. A compound of formula (I): ##STR00093## wherein: R.sup.1 is a ##STR00094## group, wherein * indicates the point of attachment of said group to the rest of the molecule; Q is CH or N, with the proviso that Q is CH if R.sup.Q is --N(H)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)N(H)R.sup.6 or --N(H)C(.dbd.O)NR.sup.6R.sup.7; R.sup.Q is a group selected from: --N(H)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)N(H)R.sup.6, --N(H)C(.dbd.O)NR.sup.6R.sup.7, --C(.dbd.O)N(H)R.sup.6, and --C(.dbd.O)NR.sup.6R.sup.7; R.sup.2 is a phenyl- or pyridyl- group which is substituted one or more times, identically or differently, with a substituent selected from R.sup.5a and R.sup.5b; R.sup.3 is a hydrogen atom; R.sup.4 is a hydrogen atom; R.sup.5 is a hydrogen atom; R.sup.5a is a group selected from: halo-, 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-, 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--, --O--(CH.sub.2).sub.n--C(.dbd.O)NR.sup.8R.sup.7, 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, --NR.sup.7R.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, and --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.5b is a group selected from: halo-, 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-, 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--, --O--(CH.sub.2).sub.n--C(.dbd.O)NR.sup.8R.sup.7, 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, --NR.sup.7R.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, and --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.6 is a group selected from: --(CH.sub.2).sub.q-aryl, --(CH.sub.2).sub.q-heteroaryl, --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), and --(CH.sub.2).sub.q-(3- to 10-membered heterocycloalkyl), wherein said group is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, 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-, 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, --NH.sub.2, --N(H)R.sup.8, --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, and --N.dbd.S(.dbd.O)(R.sup.8)R.sup.7; R.sup.7 is a C.sub.1-C.sub.3-alkyl- group or a C.sub.3-C.sub.6-cycloalkyl-group; R.sup.8 is a C.sub.1-C.sub.6-alkyl- or C.sub.3-C.sub.6-cycloalkyl-group, wherein said C.sub.1-C.sub.6-alkyl- or C.sub.3-C.sub.6-cycloalkyl- group is optionally substituted, one or more times, identically or differently, with a substituent selected from: halo-, hydroxy-, --NHR.sup.7, --NR.sup.7R.sup.7, --N(C.sub.1-C.sub.3-alkyl)-C(.dbd.O)R.sup.7, --N(C.sub.1-C.sub.3-alkyl)-C(.dbd.O)OR.sup.7, C.sub.1-C.sub.3-alkyl-, R.sup.7--S(.dbd.O).sub.2--, C.sub.1-C.sub.3-alkoxy-, and halo-C.sub.1-C.sub.3-alkoxy-; or R.sup.7 and R.sup.8 are taken together with the molecular fragment to which they are attached to form a 4- to 6-membered heterocycloalkyl- group, which is optionally substituted, one or more times, identically or differently, with a halogen atom, a C.sub.1-C.sub.3-alkyl-, halo-C.sub.1-C.sub.3-alkyl-or C.sub.1-C.sub.3-alkoxy-group; n, m, and p are, independently from each other, an integer of 0, 1, 2 or 3; q is an integer of 0, 1, 2 or 3; and z is 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 any of the foregoing.

2. The compound according to claim 1, wherein: R.sup.Q is a group selected from: --N(H)C(.dbd.O)R.sup.6, --N(H)C(.dbd.O)N(H)R.sup.6, and --C(.dbd.O)N(H)R.sup.6, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

3. The compound according to claim 1, wherein: R.sup.1 is a group selected from: ##STR00095## or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

4. The compound according to claim 1, wherein: R.sup.2 is selected from: ##STR00096## or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

5. The compound according to claim 1, wherein: R.sup.5a is a group selected from: methoxy-, ethoxy-, and F.sub.3C--CH.sub.2--O--, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

6. The compound according to claim 1, wherein: R.sup.5b is a group selected from: --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--, and --S(.dbd.O)(.dbd.NR.sup.7)R.sup.8, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

7. The compound according to claim 1, wherein: R.sup.6 represents is a group selected from: --(CH.sub.2).sub.q-phenyl, and --(CH.sub.2).sub.q--(C.sub.3-C.sub.6-cycloalkyl), wherein said group is optionally substituted with a halogen atom, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

8. The compound according to claim 1, wherein: R.sup.7 is a C.sub.1-C.sub.3-alkyl-group; R.sup.8 is a C.sub.1-C.sub.6-alkyl- or C.sub.3-C.sub.6-cycloalkyl-group, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

9. The compound according to claim 1, wherein: R.sup.7 and R.sup.8 are taken together with the molecular fragment to which they are attached to form a 4- to 6-membered heterocycloalkyl-group, which is optionally substituted with a C.sub.1-C.sub.3-alkyl-group, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

10. The compound according to claim 1, wherein: q is 1, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

11. The compound according to claim 1, which is selected from the group consisting of: 4-(2-{[2-ethoxy-4-(ethylcarbamoyl)phenyl]amino}[1,2,4]triazolo[1,5-a]pyri- din-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[4-(tert-butylcarbamoyl)-2-(2,2,2-trifluoroethoxy)phenyl]amino}[1,2- ,4]-triazolo[1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamid- e; 4-(2-{[4-(diethylcarbamoyl)-2-methoxyphenyl]amino}[1,2,4]triazolo[1,5-a- ]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1,- 5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[4-(diethylcarbamoyl)-2-propoxyphenyl]amino}[1,2,4]triazolo[1,5-a]p- yridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[4-(diethylcarbamoyl)-2-(2-methylpropoxy)phenyl]amino}[1,2,4]triazo- lo [1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide trifluoroacetate; 4-(2-{[2-(cyclopropylmethoxy)-4-(diethylcarbamoyl)phenyl]amino}[1,2,4]tri- azolo [1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[4-(diethylcarbamoyl)-2-(2-methoxyethoxy)phenyl]amino}[1,2,4]triazo- lo[1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide; 4-(2-{[4-(diethylcarbamoyl)-2-(2,2,2-trifluoroethoxy)phenyl]amino}[1,2,4]- triazolo [1,5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperazine-1-carboxamide trifluoroacetate; N-(4-fluorobenzyl)-4-(2-{[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]amin- o}-[1,2,4]triazolo[1,5-a]pyridin-6-yl)piperazine-1-carboxamide; N-(4-fluorobenzyl)-4-(2-{[3-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]-ami- no}[1,2,4]triazolo[1,5-a]pyridin-6-yl)piperazine-1-carboxamide; N-(4-fluorobenzyl)-4-{2-[(2-methoxypyridin-3-yl)amino][1,2,4]triazolo[1,5- -a]pyridin-6-yl}piperazine-1-carboxamide; 4-{2-[(2-ethoxypyridin-3-yl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-(- 4-fluoro-benzyl)piperazine-1-carboxamide; 4-{2-[(2-cyanophenyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}-N-(4-fluor- o-benzyl)piperazine-1-carboxamide; 1-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo[1,- 5-a]pyridin-6-yl)-N-(4-fluorobenzyl)piperidine-4-carboxamide; N-(cyclopropylmethyl)-1-(2-{[2-ethoxy-4-(ethylcarbamoyl)phenyl]amino}-[1,- 2,4]triazolo[1,5-a]pyridin-6-yl)piperidine-4-carboxamide; N-(cyclopropylmethyl)-1-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]-a- mino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)piperidine-4-carboxamide; N-(cyclopropylmethyl)-1-(2-{[2-(2,2,2-trifluoroethoxy)pyridin-3-yl]amino}- -[1,2,4]triazolo[1,5-a]pyridin-6-yl)piperidine-4-carboxamide; 3-ethoxy-N-ethyl-4-{[6-(4-{[(4-fluorophenyl)acetyl]amino}piperidin-1-yl)-- [1,2,4]triazolo [1,5-a]pyridin-2-yl]amino}benzamide; N-[1-(2-{[2-ethoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}[1,2,4]triazolo [1,5-a]pyridin-6-yl)piperidin-4-yl]-2-(4-fluorophenyl)acetamide; N-(1-{2-[(2-ethoxypyridin-3-yl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}p- iperidin-4-yl)-2-(4-fluorophenyl)acetamide; and 1-(4-fluorobenzyl)-3-[1-(2-{[4-(morpholin-4-ylcarbonyl)-2-(2,2,2-trifluor- oethoxy)phenyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)pyrrolidin-3-yl]ur- ea, or a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of any of the foregoing.

12. A pharmaceutical composition comprising the compound according to claim 1, or a tautomer, an N-oxide, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of any of the foregoing, and a pharmaceutically acceptable diluent or carrier.

13. A pharmaceutical combination comprising: the compound according to claim 1, or a tautomer, an N-oxide, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of any of the foregoing; and an agent 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.

14. A method for treatment of a disease of uncontrolled cell growth, proliferation or survival, an inappropriate cellular immune response, or an inappropriate cellular inflammatory response, comprising administering to a patient in need thereof a therapeutically effective amount of the compound according to claim 1, or a tautomer, an N-oxide, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, or a mixture of any of the foregoing, wherein the uncontrolled cell growth, proliferation or survival, inappropriate cellular immune response, or inappropriate cellular inflammatory response is mediated by Mps-1.

15. The method according to claim 14, wherein the disease of uncontrolled cell growth, proliferation or survival, inappropriate cellular immune response, or inappropriate cellular inflammatory response mediated by Mps-1 is a haemotological tumour, a solid tumour or metastases thereof.

16. The method according to claim 15, wherein the haemotological tumour, solid tumour or metastases thereof is selected from leukemias and myelodysplastic syndrome, malignant lymphomas, head and neck tumours, brain tumours and brain metastases, tumours of the thorax, non-small cell and small cell lung tumours, gastrointestinal tumours, endocrine tumours, mammary and other gynaecological tumours, urological tumours, renal, bladder and prostate tumours, skin tumours, and sarcomas, and metastases thereof.

Summary for Patent:   Start Trial

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
13171039Jun 7, 2013
PCT Information
PCT FiledJune 03, 2014PCT Application Number:PCT/EP2014/061410
PCT Publication Date:December 11, 2014PCT Publication Number:WO2014/195274

Details for Patent 9,670,202

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech RITUXAN rituximab VIAL 103705 001 1997-11-26   Start Trial BAYER PHARMA AKTIENGESELLSCHAFT (Berlin, DE) 2033-06-07 RX Orphan search
Genentech Inc RITUXAN HYCELA rituximab; hyaluronidase (human recombinant) SOLUTION;SUBCUTANEOUS 761064 001 2017-06-22   Start Trial BAYER PHARMA AKTIENGESELLSCHAFT (Berlin, DE) 2033-06-07 RX Orphan search
Genentech Inc RITUXAN HYCELA rituximab; hyaluronidase (human recombinant) SOLUTION;SUBCUTANEOUS 761064 002 2017-06-22   Start Trial BAYER PHARMA AKTIENGESELLSCHAFT (Berlin, DE) 2033-06-07 RX Orphan search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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