CA2724715A1 - Heterocycles as protein kinase inhibitors - Google Patents
Heterocycles as protein kinase inhibitors Download PDFInfo
- Publication number
- CA2724715A1 CA2724715A1 CA2724715A CA2724715A CA2724715A1 CA 2724715 A1 CA2724715 A1 CA 2724715A1 CA 2724715 A CA2724715 A CA 2724715A CA 2724715 A CA2724715 A CA 2724715A CA 2724715 A1 CA2724715 A1 CA 2724715A1
- Authority
- CA
- Canada
- Prior art keywords
- alkylene
- nr5r5a
- triazolo
- pyridin
- quinolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000000623 heterocyclic group Chemical group 0.000 title description 10
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 33
- 201000011510 cancer Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- -1 diastereomers Chemical class 0.000 claims description 330
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 38
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000003981 vehicle Substances 0.000 claims description 11
- 206010027476 Metastases Diseases 0.000 claims description 10
- 230000009401 metastasis Effects 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- MOPSJMVERRFXAX-HNNXBMFYSA-N 5-(3,4-difluorophenyl)-3-[(1s)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC=C(F)C(F)=C1 MOPSJMVERRFXAX-HNNXBMFYSA-N 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- NKKSQKKEWMSMOE-HNNXBMFYSA-N 5-(3,5-difluorophenyl)-3-[(1s)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC(F)=CC(F)=C1 NKKSQKKEWMSMOE-HNNXBMFYSA-N 0.000 claims description 5
- JNNIYZXJZPEHOP-AWEZNQCLSA-N 5-(4-methylthiophen-2-yl)-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC(C)=CS1 JNNIYZXJZPEHOP-AWEZNQCLSA-N 0.000 claims description 5
- KQXCXQZMDWFXKY-AWEZNQCLSA-N 5-(5-methylthiophen-2-yl)-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC=C(C)S1 KQXCXQZMDWFXKY-AWEZNQCLSA-N 0.000 claims description 5
- OKGVVWPGTZEYQS-ZDUSSCGKSA-N 5-[4-chloro-3-(trifluoromethyl)phenyl]-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC=C(Cl)C(C(F)(F)F)=C1 OKGVVWPGTZEYQS-ZDUSSCGKSA-N 0.000 claims description 5
- UEAMRYLTQQUNJM-INIZCTEOSA-N 5-benzyl-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1CC1=CC=CC=C1 UEAMRYLTQQUNJM-INIZCTEOSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- JVDYRYXVFKFESW-CYBMUJFWSA-N 3-[(1r)-1-(3-methoxyquinolin-6-yl)ethyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C)C=3C=CC4=NC=C(C=C4C=3)OC)N=NC=2C=CN1C1=CC(C)=NS1 JVDYRYXVFKFESW-CYBMUJFWSA-N 0.000 claims description 4
- ACDVIHRBYWUYPZ-OAHLLOKOSA-N 3-[(1r)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC(C)=NS1 ACDVIHRBYWUYPZ-OAHLLOKOSA-N 0.000 claims description 4
- SMJCNDZHMUKNNK-OAHLLOKOSA-N 3-[(1r)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]-5-thiophen-2-yltriazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC=CS1 SMJCNDZHMUKNNK-OAHLLOKOSA-N 0.000 claims description 4
- JVDYRYXVFKFESW-ZDUSSCGKSA-N 3-[(1s)-1-(3-methoxyquinolin-6-yl)ethyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C)C=3C=CC4=NC=C(C=C4C=3)OC)N=NC=2C=CN1C1=CC(C)=NS1 JVDYRYXVFKFESW-ZDUSSCGKSA-N 0.000 claims description 4
- ACDVIHRBYWUYPZ-HNNXBMFYSA-N 3-[(1s)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC(C)=NS1 ACDVIHRBYWUYPZ-HNNXBMFYSA-N 0.000 claims description 4
- SMJCNDZHMUKNNK-HNNXBMFYSA-N 3-[(1s)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]-5-thiophen-2-yltriazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC=CS1 SMJCNDZHMUKNNK-HNNXBMFYSA-N 0.000 claims description 4
- NKKSQKKEWMSMOE-OAHLLOKOSA-N 5-(3,5-difluorophenyl)-3-[(1r)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC(F)=CC(F)=C1 NKKSQKKEWMSMOE-OAHLLOKOSA-N 0.000 claims description 4
- DIENJHWZNHLZFW-UHFFFAOYSA-N 5-(3-methyl-1,2-thiazol-5-yl)-3-(quinolin-6-ylmethyl)-6,7-dihydrotriazolo[4,5-c]pyridin-4-one Chemical compound S1N=C(C)C=C1N1C(=O)C(N(CC=2C=C3C=CC=NC3=CC=2)N=N2)=C2CC1 DIENJHWZNHLZFW-UHFFFAOYSA-N 0.000 claims description 4
- JNNIYZXJZPEHOP-CQSZACIVSA-N 5-(4-methylthiophen-2-yl)-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC(C)=CS1 JNNIYZXJZPEHOP-CQSZACIVSA-N 0.000 claims description 4
- KQXCXQZMDWFXKY-CQSZACIVSA-N 5-(5-methylthiophen-2-yl)-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC=C(C)S1 KQXCXQZMDWFXKY-CQSZACIVSA-N 0.000 claims description 4
- OKGVVWPGTZEYQS-CYBMUJFWSA-N 5-[4-chloro-3-(trifluoromethyl)phenyl]-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC=C(Cl)C(C(F)(F)F)=C1 OKGVVWPGTZEYQS-CYBMUJFWSA-N 0.000 claims description 4
- UEAMRYLTQQUNJM-MRXNPFEDSA-N 5-benzyl-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1CC1=CC=CC=C1 UEAMRYLTQQUNJM-MRXNPFEDSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 230000002062 proliferating effect Effects 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- OESNLUUWYQGKDB-UHFFFAOYSA-N 3-[(3-methoxyquinolin-6-yl)methyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound C=1C2=CC(OC)=CN=C2C=CC=1CN(C=1C2=O)N=NC=1C=CN2C1=CC(C)=NS1 OESNLUUWYQGKDB-UHFFFAOYSA-N 0.000 claims description 3
- YHLFNYJSVQHEJN-UHFFFAOYSA-N 3-[[3-(2-methoxyethoxy)quinolin-6-yl]methyl]-5-(3-methyl-1,2-thiazol-5-yl)triazolo[4,5-c]pyridin-4-one Chemical compound C=1C2=CC(OCCOC)=CN=C2C=CC=1CN(C=1C2=O)N=NC=1C=CN2C1=CC(C)=NS1 YHLFNYJSVQHEJN-UHFFFAOYSA-N 0.000 claims description 3
- FDSDLKQVKLJTNN-UHFFFAOYSA-N 3-[[3-(2-methoxyethoxy)quinolin-6-yl]methyl]-5-thiophen-2-yltriazolo[4,5-c]pyridin-4-one Chemical compound C=1C2=CC(OCCOC)=CN=C2C=CC=1CN(C=1C2=O)N=NC=1C=CN2C1=CC=CS1 FDSDLKQVKLJTNN-UHFFFAOYSA-N 0.000 claims description 3
- KOTCZGOJAHNTGC-NSHDSACASA-N 5-(1-methylpyrazol-4-yl)-3-[(1S)-1-quinolin-6-ylethyl]-6H-triazolo[4,5-d]pyrimidin-7-one Chemical compound N1([C@H](C=2C=C3C=CC=NC3=CC=2)C)N=NC(C(N2)=O)=C1N=C2C=1C=NN(C)C=1 KOTCZGOJAHNTGC-NSHDSACASA-N 0.000 claims description 3
- PEUAHYDTRUVITP-CYBMUJFWSA-N 5-(1-methylpyrazol-4-yl)-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C=1C=NN(C)C=1 PEUAHYDTRUVITP-CYBMUJFWSA-N 0.000 claims description 3
- PEUAHYDTRUVITP-ZDUSSCGKSA-N 5-(1-methylpyrazol-4-yl)-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C=1C=NN(C)C=1 PEUAHYDTRUVITP-ZDUSSCGKSA-N 0.000 claims description 3
- MOPSJMVERRFXAX-OAHLLOKOSA-N 5-(3,4-difluorophenyl)-3-[(1r)-1-[3-(2-methoxyethoxy)quinolin-6-yl]ethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C)C=3C=CC4=NC=C(C=C4C=3)OCCOC)N=NC=2C=CN1C1=CC=C(F)C(F)=C1 MOPSJMVERRFXAX-OAHLLOKOSA-N 0.000 claims description 3
- JMZOGNSTUZDDRE-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-3-[(3-methoxyquinolin-6-yl)methyl]triazolo[4,5-c]pyridin-4-one Chemical compound C=1C2=CC(OC)=CN=C2C=CC=1CN(C=1C2=O)N=NC=1C=CN2C1=CC(F)=CC(F)=C1 JMZOGNSTUZDDRE-UHFFFAOYSA-N 0.000 claims description 3
- XWYFHGITNSOOBZ-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-3-[[3-(2-methoxyethoxy)quinolin-6-yl]methyl]triazolo[4,5-c]pyridin-4-one Chemical compound C=1C2=CC(OCCOC)=CN=C2C=CC=1CN(C=1C2=O)N=NC=1C=CN2C1=CC(F)=CC(F)=C1 XWYFHGITNSOOBZ-UHFFFAOYSA-N 0.000 claims description 3
- UZMQRFBXIGTUIV-CYBMUJFWSA-N 5-(3-methyl-1,2-thiazol-5-yl)-3-[(1r)-1-quinolin-6-ylethyl]-6,7-dihydrotriazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2CCN1C1=CC(C)=NS1 UZMQRFBXIGTUIV-CYBMUJFWSA-N 0.000 claims description 3
- OQHITEJUTZFJMP-CYBMUJFWSA-N 5-(3-methyl-1,2-thiazol-5-yl)-3-[(1r)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC(C)=NS1 OQHITEJUTZFJMP-CYBMUJFWSA-N 0.000 claims description 3
- UZMQRFBXIGTUIV-ZDUSSCGKSA-N 5-(3-methyl-1,2-thiazol-5-yl)-3-[(1s)-1-quinolin-6-ylethyl]-6,7-dihydrotriazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2CCN1C1=CC(C)=NS1 UZMQRFBXIGTUIV-ZDUSSCGKSA-N 0.000 claims description 3
- ZSFSLLGRLMODAE-UHFFFAOYSA-N 5-phenyl-3-(quinolin-6-ylmethyl)-6,7-dihydrotriazolo[4,5-c]pyridin-4-one Chemical compound C1CC=2N=NN(CC=3C=C4C=CC=NC4=CC=3)C=2C(=O)N1C1=CC=CC=C1 ZSFSLLGRLMODAE-UHFFFAOYSA-N 0.000 claims description 3
- DFWVKPQEDPHBKV-UHFFFAOYSA-N 6-(1-methylpyrazol-4-yl)-1-(1-quinolin-6-ylethyl)-5H-triazolo[4,5-c]pyridin-4-one Chemical compound C=1C=C2N=CC=CC2=CC=1C(C)N1N=NC(C(N2)=O)=C1C=C2C=1C=NN(C)C=1 DFWVKPQEDPHBKV-UHFFFAOYSA-N 0.000 claims description 3
- SMBPKPQUDMDKAG-LBPRGKRZSA-N 6-(3-methyl-1,2-thiazol-5-yl)-1-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-d]pyrimidin-7-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2N=CN1C1=CC(C)=NS1 SMBPKPQUDMDKAG-LBPRGKRZSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- DFJJXOLYKDELAT-UHFFFAOYSA-N 1-(1-quinolin-6-ylethyl)-5H-triazolo[4,5-c]pyridin-4-one Chemical compound N1=NC(C(NC=C2)=O)=C2N1C(C)C1=CC=C(N=CC=C2)C2=C1 DFJJXOLYKDELAT-UHFFFAOYSA-N 0.000 claims description 2
- OQHITEJUTZFJMP-ZDUSSCGKSA-N 5-(3-methyl-1,2-thiazol-5-yl)-3-[(1s)-1-quinolin-6-ylethyl]triazolo[4,5-c]pyridin-4-one Chemical compound O=C1C=2N([C@H](C=3C=C4C=CC=NC4=CC=3)C)N=NC=2C=CN1C1=CC(C)=NS1 OQHITEJUTZFJMP-ZDUSSCGKSA-N 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 101000898034 Homo sapiens Hepatocyte growth factor Proteins 0.000 abstract description 49
- 102100021866 Hepatocyte growth factor Human genes 0.000 abstract description 48
- 101001076408 Homo sapiens Interleukin-6 Proteins 0.000 abstract description 48
- 101000868152 Homo sapiens Son of sevenless homolog 1 Proteins 0.000 abstract description 48
- 201000010099 disease Diseases 0.000 abstract description 26
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 150000003254 radicals Chemical class 0.000 description 60
- 239000000203 mixture Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 102000003745 Hepatocyte Growth Factor Human genes 0.000 description 38
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 38
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
- 235000002639 sodium chloride Nutrition 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12855508P | 2008-05-22 | 2008-05-22 | |
| US61/128,555 | 2008-05-22 | ||
| PCT/US2009/045058 WO2009143477A1 (en) | 2008-05-22 | 2009-05-22 | Heterocycles as protein kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2724715A1 true CA2724715A1 (en) | 2009-11-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2724715A Abandoned CA2724715A1 (en) | 2008-05-22 | 2009-05-22 | Heterocycles as protein kinase inhibitors |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8691838B2 (https=) |
| EP (1) | EP2310389B1 (https=) |
| JP (1) | JP2011520986A (https=) |
| AT (1) | ATE540038T1 (https=) |
| AU (1) | AU2009248839B2 (https=) |
| CA (1) | CA2724715A1 (https=) |
| ES (1) | ES2376404T3 (https=) |
| MX (1) | MX2010012528A (https=) |
| WO (1) | WO2009143477A1 (https=) |
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| EP3795573B1 (en) | 2009-12-31 | 2022-07-06 | Hutchison Medipharma Limited | Certain triazolopyrazines, compositions thereof and methods of use therefor |
| US20140107151A1 (en) * | 2011-05-17 | 2014-04-17 | Principia Biophama Inc. | Tyrosine kinase inhibitors |
| ME03455B (me) | 2012-09-10 | 2020-01-20 | Principia Biopharma Inc | Jedinjenja pirazolopirimidina kao inhibitori kinaze |
| PT3107544T (pt) | 2014-02-21 | 2021-01-05 | Principia Biopharma Inc | Sais e forma sólida de um inibidor de btk |
| US10485797B2 (en) | 2014-12-18 | 2019-11-26 | Principia Biopharma Inc. | Treatment of pemphigus |
| TW201718572A (zh) | 2015-06-24 | 2017-06-01 | 普林斯匹亞生物製藥公司 | 酪胺酸激酶抑制劑 |
| CA2994027C (en) | 2015-07-31 | 2023-10-10 | Merck Patent Gmbh | Bicyclic heterocyclic derivatives |
| MA45547A (fr) | 2016-06-29 | 2019-05-08 | Principia Biopharma Inc | Formulations à libération modifiée à base de 2-[3-[4-amino-3-(2-fluoro-4-phénoxy-phényl)pyrazolo[3,4-d]pyrimidine-1-yl]pipéridine-1-carbonyl]-4-méthyl-4-[4-(oxétane-3-yl)pipérazine-1-yl]pent-2-ènenitrile |
| TWI877239B (zh) | 2019-10-14 | 2025-03-21 | 美商普林斯匹亞生物製藥公司 | 藉由投予(R)-2-[3-[4-胺基-3-(2-氟-4-苯氧基-苯基)吡唑并[3,4-d]嘧啶-1-基]哌啶-1-羰基]-4-甲基-4-[4-(氧呾-3-基)哌-1-基]戊-2-烯腈來治療免疫血小板減少症之方法 |
| JP2023511105A (ja) | 2020-01-22 | 2023-03-16 | プリンシピア バイオファーマ インコーポレイテッド | ２－［３－［４－アミノ－３－（２－フルオロ－４－フェノキシ－フェニル）－１ｈ－ピラゾロ［３，４－ｄ］ピリミジン－１－イル］ピペリジン－１－カルボニル］－４－メチル－４－［４－（オキセタン－３－イル）ピペラジン－１－イル］ペンタ－２－エンニトリルの結晶形態 |
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| US4405619A (en) | 1981-09-02 | 1983-09-20 | Diamond Shamrock Corporation | Antiinflammatory substituted-1,2,4-triazolo[4,3-b]-1,2,4-triazines |
| ZA857647B (en) | 1984-10-12 | 1986-05-28 | Warner Lambert Co | Purine derivatives |
| US4772606A (en) * | 1985-08-22 | 1988-09-20 | Warner-Lambert Company | Purine derivatives |
| DE4110019C2 (de) | 1991-03-27 | 2000-04-13 | Merck Patent Gmbh | Imidazopyridine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| US5798364A (en) | 1992-03-26 | 1998-08-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Imidazopyridines |
| US20050096322A1 (en) | 2002-03-01 | 2005-05-05 | Susumu Igarashi | Nitrogen-containing heterocyclic compound |
| DE10238477A1 (de) | 2002-08-22 | 2004-03-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Purinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| AU2003271064B2 (en) * | 2002-09-27 | 2010-06-17 | Dainippon Sumitomo Pharma Co., Ltd. | Novel adenine compound and use thereof |
| UY28103A1 (es) | 2002-12-03 | 2004-06-30 | Boehringer Ingelheim Pharma | Nuevas imidazo-piridinonas sustituidas, su preparación y su empleo como medicacmentos |
| US7109192B2 (en) * | 2002-12-03 | 2006-09-19 | Boehringer Ingelheim Pharma Gmbh & Co Kg | Substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions |
| US7250212B2 (en) | 2003-05-29 | 2007-07-31 | Nichias Corporation | Porous body-coated fiber, porous body-coated particle, and formed article using the same |
| BRPI0412003A (pt) | 2003-07-02 | 2006-08-15 | Sugen Inc | arilmetil triazol e imidazopirazinas como inibidores de c-met |
| US7122548B2 (en) | 2003-07-02 | 2006-10-17 | Sugen, Inc. | Triazolotriazine compounds and uses thereof |
| PE20080403A1 (es) * | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
-
2009
- 2009-05-22 EP EP09751705A patent/EP2310389B1/en active Active
- 2009-05-22 AT AT09751705T patent/ATE540038T1/de active
- 2009-05-22 JP JP2011510736A patent/JP2011520986A/ja not_active Ceased
- 2009-05-22 MX MX2010012528A patent/MX2010012528A/es active IP Right Grant
- 2009-05-22 AU AU2009248839A patent/AU2009248839B2/en not_active Ceased
- 2009-05-22 CA CA2724715A patent/CA2724715A1/en not_active Abandoned
- 2009-05-22 ES ES09751705T patent/ES2376404T3/es active Active
- 2009-05-22 WO PCT/US2009/045058 patent/WO2009143477A1/en not_active Ceased
- 2009-05-22 US US12/994,068 patent/US8691838B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| MX2010012528A (es) | 2010-12-02 |
| AU2009248839B2 (en) | 2014-04-17 |
| ES2376404T3 (es) | 2012-03-13 |
| US20110118285A1 (en) | 2011-05-19 |
| EP2310389A1 (en) | 2011-04-20 |
| ATE540038T1 (de) | 2012-01-15 |
| US8691838B2 (en) | 2014-04-08 |
| EP2310389B1 (en) | 2012-01-04 |
| JP2011520986A (ja) | 2011-07-21 |
| WO2009143477A1 (en) | 2009-11-26 |
| AU2009248839A1 (en) | 2009-11-26 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20140203 |
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| FZDE | Discontinued |
Effective date: 20160524 |