JP2013529179A5 - - Google Patents
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- Publication number
- JP2013529179A5 JP2013529179A5 JP2012557516A JP2012557516A JP2013529179A5 JP 2013529179 A5 JP2013529179 A5 JP 2013529179A5 JP 2012557516 A JP2012557516 A JP 2012557516A JP 2012557516 A JP2012557516 A JP 2012557516A JP 2013529179 A5 JP2013529179 A5 JP 2013529179A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrrolo
- amino
- pyridin
- chlorophenyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 14
- -1 cyano, amino, hydroxyl Chemical group 0.000 claims description 12
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- FZFSUNWMWPGDQM-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[2,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C=2CCNCC=2)=C1 FZFSUNWMWPGDQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical group C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000000968 intestinal effect Effects 0.000 claims 2
- 208000023589 ischemic disease Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- AZIUJAOZSXAHOD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(oxan-4-yl)pyrrolo[2,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCOCC2)=C1 AZIUJAOZSXAHOD-UHFFFAOYSA-N 0.000 claims 1
- FUESDKXSKZBKIW-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(piperazin-1-ylmethyl)pyrrolo[2,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(CN2CCNCC2)=C1 FUESDKXSKZBKIW-UHFFFAOYSA-N 0.000 claims 1
- AHTLZZSSNIMDDX-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[(4-methylpiperazin-1-yl)methyl]pyrrolo[2,3-c]pyridine Chemical compound C1CN(C)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 AHTLZZSSNIMDDX-UHFFFAOYSA-N 0.000 claims 1
- UXBOPANQZQDGFP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(1h-pyrazol-5-ylmethyl)piperidin-4-yl]pyrrolo[2,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CC3=NNC=C3)CC2)=C1 UXBOPANQZQDGFP-UHFFFAOYSA-N 0.000 claims 1
- ICTHLQAYBCVJAA-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-[(1-methylpyrazol-4-yl)methyl]piperidin-4-yl]pyrrolo[2,3-c]pyridine Chemical compound C1=NN(C)C=C1CN1CCC(C=2C3=CC=NC=C3N(C=3C=CC(Cl)=CC=3)C=2)CC1 ICTHLQAYBCVJAA-UHFFFAOYSA-N 0.000 claims 1
- SWWYQXOTEUNCHM-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-piperidin-4-ylpyrrolo[2,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCNCC2)=C1 SWWYQXOTEUNCHM-UHFFFAOYSA-N 0.000 claims 1
- SNTSYBHIFUFMNR-UHFFFAOYSA-N 1-(4-methylphenyl)-3-(oxan-4-yl)pyrrolo[2,3-c]pyridine Chemical compound C1=CC(C)=CC=C1N1C2=CN=CC=C2C(C2CCOCC2)=C1 SNTSYBHIFUFMNR-UHFFFAOYSA-N 0.000 claims 1
- KUKHQQQVBFTSPF-UHFFFAOYSA-N 1-(5-chloropyridin-2-yl)-3-(oxan-4-yl)pyrrolo[2,3-c]pyridine Chemical compound N1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCOCC2)=C1 KUKHQQQVBFTSPF-UHFFFAOYSA-N 0.000 claims 1
- BCTZJRGISGITFZ-UHFFFAOYSA-N 1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 BCTZJRGISGITFZ-UHFFFAOYSA-N 0.000 claims 1
- VIUQFKJKEZNIOV-UHFFFAOYSA-N 1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 VIUQFKJKEZNIOV-UHFFFAOYSA-N 0.000 claims 1
- PVKFTMXILNTSOY-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 PVKFTMXILNTSOY-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- AGOLRJPOKXWUNE-UHFFFAOYSA-N 2-[1-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 AGOLRJPOKXWUNE-UHFFFAOYSA-N 0.000 claims 1
- SNUPNVCHYSJETG-UHFFFAOYSA-N 2-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 SNUPNVCHYSJETG-UHFFFAOYSA-N 0.000 claims 1
- ZZPKYLOQWXZCBX-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methylamino]ethanol Chemical compound C12=CN=CC=C2C(CNCCO)=CN1C1=CC=C(Cl)C=C1 ZZPKYLOQWXZCBX-UHFFFAOYSA-N 0.000 claims 1
- WDTBPWKPLTZJPQ-UHFFFAOYSA-N 2-amino-1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 WDTBPWKPLTZJPQ-UHFFFAOYSA-N 0.000 claims 1
- GIYVZZSXUQYABS-UHFFFAOYSA-N 3-(3,6-dihydro-2h-pyran-4-yl)-2-methyl-1-(4-methylphenyl)pyrrolo[2,3-c]pyridine Chemical compound C12=CC=NC=C2N(C=2C=CC(C)=CC=2)C(C)=C1C1=CCOCC1 GIYVZZSXUQYABS-UHFFFAOYSA-N 0.000 claims 1
- PAIVUCFYABFSFP-UHFFFAOYSA-N 3-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]propanenitrile Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CCC#N)CC2)=C1 PAIVUCFYABFSFP-UHFFFAOYSA-N 0.000 claims 1
- SXONDVGUWVLMQZ-UHFFFAOYSA-N 3-amino-1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 SXONDVGUWVLMQZ-UHFFFAOYSA-N 0.000 claims 1
- ZSMAHLWYKQUKJJ-UHFFFAOYSA-N 4-[1-(4-chloro-2-methylphenyl)pyrrolo[2,3-c]pyridin-3-yl]cyclohexan-1-amine Chemical compound CC1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCC(N)CC2)=C1 ZSMAHLWYKQUKJJ-UHFFFAOYSA-N 0.000 claims 1
- AOHGNGRSRMZXLI-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 AOHGNGRSRMZXLI-UHFFFAOYSA-N 0.000 claims 1
- VPNRBAOCCZTCJQ-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]morpholine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(N2CCOCC2)=C1 VPNRBAOCCZTCJQ-UHFFFAOYSA-N 0.000 claims 1
- SFUCPNXUZHQVCG-UHFFFAOYSA-N 4-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]butanenitrile Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(C2CCN(CCCC#N)CC2)=C1 SFUCPNXUZHQVCG-UHFFFAOYSA-N 0.000 claims 1
- FGYKHVGONVOUOE-UHFFFAOYSA-N 4-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]morpholine Chemical compound C1=CC(Cl)=CC=C1N1C2=CN=CC=C2C(CN2CCOCC2)=C1 FGYKHVGONVOUOE-UHFFFAOYSA-N 0.000 claims 1
- GWESHTVIEYBLRM-UHFFFAOYSA-N 4-amino-1-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]butan-1-one Chemical compound C1CN(C(=O)CCCN)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 GWESHTVIEYBLRM-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- QKXXUOISKVZSIE-UHFFFAOYSA-N [1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methanol Chemical compound C12=CN=CC=C2C(CO)=CN1C1=CC=C(Cl)C=C1 QKXXUOISKVZSIE-UHFFFAOYSA-N 0.000 claims 1
- ACDAWIRIJKZIBF-UHFFFAOYSA-N [1-[[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]methyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CC(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 ACDAWIRIJKZIBF-UHFFFAOYSA-N 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000018093 autoimmune cholangitis Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 208000019069 chronic childhood arthritis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- GXVYGQANNRMYKO-UHFFFAOYSA-N tert-butyl n-[4-[1-(4-chlorophenyl)pyrrolo[2,3-c]pyridin-3-yl]cyclohexyl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCC1C(C1=CC=NC=C11)=CN1C1=CC=C(Cl)C=C1 GXVYGQANNRMYKO-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 102100027159 Membrane primary amine oxidase Human genes 0.000 description 2
- 101710132836 Membrane primary amine oxidase Proteins 0.000 description 2
- PQAQMVCBXVPTNZ-UHFFFAOYSA-N CC1=CC=C(C=C1)N1C=C(C=2C1=CN=CC2)C2CCOCC2.ClC2=CC=C(C=C2)N2C=C(C=1C2=CN=CC1)C1CCOCC1 Chemical compound CC1=CC=C(C=C1)N1C=C(C=2C1=CN=CC2)C2CCOCC2.ClC2=CC=C(C=C2)N2C=C(C=1C2=CN=CC1)C1CCOCC1 PQAQMVCBXVPTNZ-UHFFFAOYSA-N 0.000 description 1
- NJJPRPZCWLKRRT-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1C=C(C=2C1=CN=CC2)C2CCN(CC2)C(=O)O.NCCCC(=O)N2CCC(CC2)C2=CN(C1=CN=CC=C12)C1=CC=C(C=C1)Cl.N1CCOCC1 Chemical compound ClC1=CC=C(C=C1)N1C=C(C=2C1=CN=CC2)C2CCN(CC2)C(=O)O.NCCCC(=O)N2CCC(CC2)C2=CN(C1=CN=CC=C12)C1=CC=C(C=C1)Cl.N1CCOCC1 NJJPRPZCWLKRRT-UHFFFAOYSA-N 0.000 description 1
- BFFHVBOJWTWDJR-UHFFFAOYSA-N NCCC1=C2C(=CN=C1)N(C(=C2C=2CCOCC2)C)C2=CC=C(C=C2)C Chemical compound NCCC1=C2C(=CN=C1)N(C(=C2C=2CCOCC2)C)C2=CC=C(C=C2)C BFFHVBOJWTWDJR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1004311.5A GB201004311D0 (en) | 2010-03-15 | 2010-03-15 | New enzyme inhibitor compounds |
| GB1004311.5 | 2010-03-15 | ||
| PCT/EP2011/053818 WO2011113798A2 (en) | 2010-03-15 | 2011-03-14 | New enzyme inhibitor compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014221061A Division JP2015017141A (ja) | 2010-03-15 | 2014-10-30 | 新規酵素阻害化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013529179A JP2013529179A (ja) | 2013-07-18 |
| JP2013529179A5 true JP2013529179A5 (https=) | 2014-09-25 |
| JP5643347B2 JP5643347B2 (ja) | 2014-12-17 |
Family
ID=42261625
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012557516A Expired - Fee Related JP5643347B2 (ja) | 2010-03-15 | 2011-03-14 | 新規酵素阻害化合物 |
| JP2014221061A Pending JP2015017141A (ja) | 2010-03-15 | 2014-10-30 | 新規酵素阻害化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014221061A Pending JP2015017141A (ja) | 2010-03-15 | 2014-10-30 | 新規酵素阻害化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9227967B2 (https=) |
| EP (2) | EP2927233A1 (https=) |
| JP (2) | JP5643347B2 (https=) |
| KR (1) | KR20130057971A (https=) |
| CN (1) | CN103180319A (https=) |
| AU (1) | AU2011229267B2 (https=) |
| BR (1) | BR112012023315A2 (https=) |
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| US9290499B2 (en) | 2010-05-19 | 2016-03-22 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| GB201115853D0 (en) * | 2011-09-14 | 2011-10-26 | Proximagen Ltd | New enzyme inhibitor compounds |
| IN2014DN01883A (https=) * | 2011-09-14 | 2015-05-15 | Proximagen Ltd | |
| MX2014004086A (es) | 2011-10-03 | 2014-09-22 | Univ North Carolina | Compuestos de pirrolopirimidina para el tratamiento del cancer. |
| AU2013255103B2 (en) | 2012-05-02 | 2016-09-29 | Syntara Limited | Substituted 3-haloallylamine inhibitors of SSAO and uses thereof |
| AU2013266438B2 (en) | 2012-05-22 | 2017-09-07 | The University Of North Carolina At Chapel Hill | Pyrimidine compounds for the treatment of cancer |
| WO2014026330A1 (en) * | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| EP2909211A4 (en) | 2012-10-17 | 2016-06-22 | Univ North Carolina | PYRAZOLOPYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| EP2925752A4 (en) | 2012-11-27 | 2016-06-01 | Univ North Carolina | PYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| GB201304527D0 (en) * | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304526D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| US20160113893A1 (en) | 2013-06-12 | 2016-04-28 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| US9555031B2 (en) | 2014-04-11 | 2017-01-31 | The University Of North Carolina At Chapel Hill | Therapeutic uses of selected pyrrolopyrimidine compounds with anti-mer tyrosine kinase activity |
| WO2015188368A1 (en) * | 2014-06-13 | 2015-12-17 | Merck Sharp & Dohme Corp. | Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles |
| GB201416444D0 (en) | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| GB201416446D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| KR102412146B1 (ko) | 2015-02-11 | 2022-06-22 | 주식회사 아이엔테라퓨틱스 | 소디움 채널 차단제 |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| WO2017098236A1 (en) | 2015-12-07 | 2017-06-15 | Proximagen Limited | Vap-1 inhibitors for treating pain |
| US10709708B2 (en) | 2016-03-17 | 2020-07-14 | The University Of North Carolina At Chapel Hill | Method of treating cancer with a combination of MER tyrosine kinase inhibitor and an epidermal growth factor receptor (EGFR) inhibitor |
| CN106045876B (zh) * | 2016-06-07 | 2018-02-09 | 四川福思达生物技术开发有限责任公司 | 一种对氯苯肼盐酸盐的合成方法 |
| AU2017326006B2 (en) * | 2016-09-16 | 2021-10-28 | Vitae Pharmaceuticals, LLC. | Inhibitors of the menin-MLL interaction |
| AR117398A1 (es) | 2018-03-12 | 2021-08-04 | Abbvie Inc | Inhibidores de la señalización mediada por tirosina cinasa 2 |
| IL308862A (en) | 2021-06-01 | 2024-01-01 | Janssen Pharmaceutica Nv | Altered phenyl-1H-pyrrolo[3,2-c]pyridine histories |
| US20250066308A1 (en) * | 2021-10-01 | 2025-02-27 | Yuhan Corporation | Bicyclic fused ring derivative or salt thereof and pharmaceutical composition comprising same |
| US12110276B2 (en) | 2021-11-24 | 2024-10-08 | Genentech, Inc. | Pyrazolo compounds and methods of use thereof |
| US12275745B2 (en) | 2021-11-24 | 2025-04-15 | Genentech, Inc. | Therapeutic compounds and methods of use |
| US20250197392A1 (en) * | 2022-04-08 | 2025-06-19 | Janssen Pharmaceutica Nv | Crystalline forms of an inhibitor of the menin/mll interaction |
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| WO1992006979A1 (de) * | 1990-10-15 | 1992-04-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Neue diazine |
| US6143749A (en) | 1995-06-07 | 2000-11-07 | Abbott Laboratories | Heterocyclic substituted cyclopentane compounds |
| DE19649460A1 (de) | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
| PL354514A1 (en) | 1999-09-14 | 2004-01-26 | Aventis Pharmaceuticals Inc. | Benzisoxazolyl-, pyridoisoxazolyl- and benzthienyl-phenoxy derivatives useful as d4 |
| AU2002214505A1 (en) | 2000-11-09 | 2002-05-21 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-(4,5-c)pyridine derivatives |
| US6982286B2 (en) | 2001-07-12 | 2006-01-03 | Biotie Therapies Corp. | Carbocyclic hydrazino inhibitors of copper-containing amine oxidases |
| WO2003029209A2 (en) | 2001-10-02 | 2003-04-10 | Smithkline Beecham Corporation | Chemical compounds |
| MY126268A (en) | 2001-11-07 | 2006-09-29 | Schering Corp | Heteroaryl derivatives as superior ligands for nociceptin receptor orl-1 |
| US7456169B2 (en) | 2003-02-27 | 2008-11-25 | Abbott Laboratories Inc. | Heterocyclic kinase inhibitors |
| WO2005014530A2 (en) | 2003-08-08 | 2005-02-17 | La Jolla Pharmaceutical Co. | Inhibitors of semicarbazide-sensitive amine oxidase (ssao) and vap-1 mediated adhesion useful for treatment of diseases |
| ES2319539T3 (es) | 2003-09-17 | 2009-05-08 | Janssen Pharmaceutica Nv | Compuestos heterociclicos condensados como moduladores del receptor de serotonina. |
| JP2007520559A (ja) * | 2004-02-03 | 2007-07-26 | アボット・ラボラトリーズ | 治療薬としてのアミノベンゾオキサゾール類 |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| WO2006114180A1 (de) * | 2005-04-25 | 2006-11-02 | Merck Patent Gmbh | Neuartige aza-heterozyklen als kinase-inhibitoren |
| PT1906965E (pt) | 2005-06-22 | 2015-09-03 | Chemocentryx Inc | Compostos de azaindazol e métodos de utilização |
| US20070293548A1 (en) | 2006-03-31 | 2007-12-20 | Wang Eric Y | Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment and prevention of diseases |
| BRPI0710527B8 (pt) | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
| GB0610242D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| EP2078004B1 (en) | 2006-10-31 | 2015-02-25 | Merck Sharp & Dohme Corp. | 2-aminothiazole-4-carboxylic amides as protein kinase inhibitors |
| AU2007329548A1 (en) | 2006-12-06 | 2008-06-12 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| WO2008088744A1 (en) | 2007-01-17 | 2008-07-24 | Merck & Co., Inc. | Decahydroquinoline analogs as cb2 receptor modulators |
| EP2152716A1 (en) | 2007-05-02 | 2010-02-17 | Novartis Ag | Heterocyclic compounds and their use as pesticides |
| GB0725103D0 (en) | 2007-12-21 | 2008-01-30 | Glaxo Group Ltd | Novel compounds |
| CA2712701A1 (en) | 2008-01-31 | 2009-08-06 | Henning Steinhagen | Cyclic azaindole-3-carboxamides, their preparation and their use as pharmaceuticals |
| WO2009108551A2 (en) * | 2008-02-25 | 2009-09-03 | H. Lundbeck A/S | Heteroaryl amide analogues |
| DK2334672T3 (da) | 2008-09-16 | 2013-12-02 | Proximagen Ltd | 4,5,6,7-tetrahydroimidazo[4,5-c]pyridinforbindelser som inhibitorer af SSAO |
| US8633318B2 (en) * | 2008-09-16 | 2014-01-21 | Proximagen Ltd | Compounds for treatment or prevention of inflammation, an inflammatory disease, or an immune or an autoimmune disorder |
| EP2376490B1 (en) | 2008-12-04 | 2013-01-23 | Proximagen Limited | Imidazopyridine compounds |
| JP2012211085A (ja) | 2009-08-12 | 2012-11-01 | Kyowa Hakko Kirin Co Ltd | ヘッジホッグシグナル阻害剤 |
-
2010
- 2010-03-15 GB GBGB1004311.5A patent/GB201004311D0/en not_active Ceased
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2011
- 2011-03-14 NZ NZ602141A patent/NZ602141A/en not_active IP Right Cessation
- 2011-03-14 JP JP2012557516A patent/JP5643347B2/ja not_active Expired - Fee Related
- 2011-03-14 CA CA2793125A patent/CA2793125A1/en not_active Abandoned
- 2011-03-14 MX MX2012010292A patent/MX2012010292A/es not_active Application Discontinuation
- 2011-03-14 ES ES11707689.3T patent/ES2538526T3/es active Active
- 2011-03-14 SG SG2012066023A patent/SG183936A1/en unknown
- 2011-03-14 CN CN2011800140213A patent/CN103180319A/zh active Pending
- 2011-03-14 DK DK11707689.3T patent/DK2547677T3/en active
- 2011-03-14 BR BR112012023315A patent/BR112012023315A2/pt not_active IP Right Cessation
- 2011-03-14 AU AU2011229267A patent/AU2011229267B2/en not_active Ceased
- 2011-03-14 EP EP15158284.8A patent/EP2927233A1/en not_active Withdrawn
- 2011-03-14 WO PCT/EP2011/053818 patent/WO2011113798A2/en not_active Ceased
- 2011-03-14 KR KR1020127025301A patent/KR20130057971A/ko not_active Withdrawn
- 2011-03-14 EA EA201290880A patent/EA023038B1/ru not_active IP Right Cessation
- 2011-03-14 US US13/634,732 patent/US9227967B2/en not_active Expired - Fee Related
- 2011-03-14 EP EP20110707689 patent/EP2547677B1/en not_active Not-in-force
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2012
- 2012-08-27 ZA ZA2012/06424A patent/ZA201206424B/en unknown
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2014
- 2014-10-30 JP JP2014221061A patent/JP2015017141A/ja active Pending
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