CA2691512A1 - Heteroaryl amide analogues - Google Patents
Heteroaryl amide analogues Download PDFInfo
- Publication number
- CA2691512A1 CA2691512A1 CA002691512A CA2691512A CA2691512A1 CA 2691512 A1 CA2691512 A1 CA 2691512A1 CA 002691512 A CA002691512 A CA 002691512A CA 2691512 A CA2691512 A CA 2691512A CA 2691512 A1 CA2691512 A1 CA 2691512A1
- Authority
- CA
- Canada
- Prior art keywords
- indole
- pyrimidin
- carboxamide
- methyl
- chloro
- 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
- -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 133
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 138
- 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 137
- 208000002193 Pain Diseases 0.000 claims abstract description 89
- 230000036407 pain Effects 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 58
- 239000000556 agonist Substances 0.000 claims abstract description 27
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 206010061218 Inflammation Diseases 0.000 claims abstract description 19
- 230000004054 inflammatory process Effects 0.000 claims abstract description 19
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
- 208000022873 Ocular disease Diseases 0.000 claims abstract description 7
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 5
- 208000026278 immune system disease Diseases 0.000 claims abstract description 5
- 230000000926 neurological effect Effects 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims description 91
- 150000003839 salts Chemical class 0.000 claims description 81
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 72
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 70
- 230000000694 effects Effects 0.000 claims description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 66
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 51
- 238000003556 assay Methods 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 210000004027 cell Anatomy 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 32
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 31
- 125000004429 atom Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 208000004296 neuralgia Diseases 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000000338 in vitro Methods 0.000 claims description 14
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 14
- 206010016654 Fibrosis Diseases 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 208000021722 neuropathic pain Diseases 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 206010029240 Neuritis Diseases 0.000 claims description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 230000001154 acute effect Effects 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- 201000008482 osteoarthritis Diseases 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 239000006071 cream Substances 0.000 claims description 6
- 238000000099 in vitro assay Methods 0.000 claims description 6
- 210000005036 nerve Anatomy 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 210000003994 retinal ganglion cell Anatomy 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 230000034994 death Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- 208000008035 Back Pain Diseases 0.000 claims description 4
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 201000005569 Gout Diseases 0.000 claims description 4
- 206010023230 Joint stiffness Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 230000008484 agonism Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- ATWCIOGPHPGOGT-UHFFFAOYSA-N 2-(1-adamantyl)-n-(4-chloro-1-pyrimidin-2-ylindol-3-yl)acetamide Chemical compound C1=C(NC(=O)CC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 ATWCIOGPHPGOGT-UHFFFAOYSA-N 0.000 claims description 3
- VEEYSQAYZKOZIT-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 VEEYSQAYZKOZIT-UHFFFAOYSA-N 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000003106 haloaryl group Chemical group 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 230000008653 root damage Effects 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- FPHOPYWEFQYZLM-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 FPHOPYWEFQYZLM-UHFFFAOYSA-N 0.000 claims description 2
- ANAIABPQJGVDQA-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 ANAIABPQJGVDQA-UHFFFAOYSA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 206010068065 Burning mouth syndrome Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 208000001387 Causalgia Diseases 0.000 claims description 2
- 206010014020 Ear pain Diseases 0.000 claims description 2
- 206010015958 Eye pain Diseases 0.000 claims description 2
- 206010016059 Facial pain Diseases 0.000 claims description 2
- 208000033830 Hot Flashes Diseases 0.000 claims description 2
- 206010060800 Hot flush Diseases 0.000 claims description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 206010049002 Scar pain Diseases 0.000 claims description 2
- 206010072005 Spinal pain Diseases 0.000 claims description 2
- 206010042496 Sunburn Diseases 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 208000004967 femoral neuropathy Diseases 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 208000032184 meralgia paresthetica Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 208000013465 muscle pain Diseases 0.000 claims description 2
- JZYSYXDHRXPHKQ-UHFFFAOYSA-N n-(1-adamantylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 JZYSYXDHRXPHKQ-UHFFFAOYSA-N 0.000 claims description 2
- YJCCGSIXSDHVLI-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YJCCGSIXSDHVLI-UHFFFAOYSA-N 0.000 claims description 2
- 230000008764 nerve damage Effects 0.000 claims description 2
- 201000009985 neuronitis Diseases 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 239000002435 venom Substances 0.000 claims description 2
- 210000001048 venom Anatomy 0.000 claims description 2
- 231100000611 venom Toxicity 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- TZKDHXJYDQGLFK-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 TZKDHXJYDQGLFK-UHFFFAOYSA-N 0.000 claims 2
- LKMRWAUYFFIPLS-UHFFFAOYSA-N 1-(3-cyanopyridin-2-yl)-4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)indole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 LKMRWAUYFFIPLS-UHFFFAOYSA-N 0.000 claims 1
- JCSUYDVTWQJBCI-UHFFFAOYSA-N 1-(3-ethylpyrazin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound CCC1=NC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 JCSUYDVTWQJBCI-UHFFFAOYSA-N 0.000 claims 1
- DVQJAIGHURJMKU-UHFFFAOYSA-N 1-(5-fluoropyrimidin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound N1=CC(F)=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 DVQJAIGHURJMKU-UHFFFAOYSA-N 0.000 claims 1
- FLPKUPFRCHXLDY-UHFFFAOYSA-N 1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FLPKUPFRCHXLDY-UHFFFAOYSA-N 0.000 claims 1
- GGNNKOPRPONVQA-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3,4-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2C(C(=O)O)=CN1C1=NC=CC=N1 GGNNKOPRPONVQA-UHFFFAOYSA-N 0.000 claims 1
- STSVLKXCUGQLSX-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C2=CC=CC=C2C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 STSVLKXCUGQLSX-UHFFFAOYSA-N 0.000 claims 1
- RVHSUIQQODJJDG-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]pentanoic acid Chemical compound C12=CC=CC=C2N(C(C(O)=O)CCC)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 RVHSUIQQODJJDG-UHFFFAOYSA-N 0.000 claims 1
- LCLKNJIWBCOANV-UHFFFAOYSA-N 3-chloro-1-[(1-methylimidazol-2-yl)methyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-2-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C1=C(Cl)C2=CC=CC=C2N1CC1=NC=CN1C LCLKNJIWBCOANV-UHFFFAOYSA-N 0.000 claims 1
- YZFMHZXAUUEHDM-UHFFFAOYSA-N 3-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 YZFMHZXAUUEHDM-UHFFFAOYSA-N 0.000 claims 1
- QYDVTNYUERGOIZ-UHFFFAOYSA-N 3-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCOCC1 QYDVTNYUERGOIZ-UHFFFAOYSA-N 0.000 claims 1
- GHPANTLFSOVSKV-UHFFFAOYSA-N 4-bromo-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Br)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 GHPANTLFSOVSKV-UHFFFAOYSA-N 0.000 claims 1
- SZMUXKSFYOVBLZ-UHFFFAOYSA-N 4-chloro-1-[2-(dimethylamino)ethyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 SZMUXKSFYOVBLZ-UHFFFAOYSA-N 0.000 claims 1
- KCGVNAOUYOFNIB-UHFFFAOYSA-N 4-chloro-1-[3-(dimethylamino)propyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 KCGVNAOUYOFNIB-UHFFFAOYSA-N 0.000 claims 1
- FTKQORPRCLRPNX-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-(3,3,5-trimethylcyclohexyl)indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FTKQORPRCLRPNX-UHFFFAOYSA-N 0.000 claims 1
- XUTHDCGXPKNBGI-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XUTHDCGXPKNBGI-UHFFFAOYSA-N 0.000 claims 1
- GBQVSGPQEXAYLT-VMBOVVBDSA-N 4-chloro-N-[[(1R)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C([C@]1(C2(C)C)[H])C2CCC1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 GBQVSGPQEXAYLT-VMBOVVBDSA-N 0.000 claims 1
- LRSPAPPWXYSXKT-UHFFFAOYSA-N 4-chloro-n-(2,3-diphenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1=CC=CC=C1 LRSPAPPWXYSXKT-UHFFFAOYSA-N 0.000 claims 1
- WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
- YTJSTQCNEZOXLZ-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 YTJSTQCNEZOXLZ-UHFFFAOYSA-N 0.000 claims 1
- WXIVLUUFVMVXNN-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 WXIVLUUFVMVXNN-UHFFFAOYSA-N 0.000 claims 1
- QKSVJBHORLUNPE-UHFFFAOYSA-N 4-chloro-n-(2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 QKSVJBHORLUNPE-UHFFFAOYSA-N 0.000 claims 1
- RGVNVQZTKWHPNU-UHFFFAOYSA-N 4-chloro-n-(3-cyclopentyl-2-phenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1CCCC1 RGVNVQZTKWHPNU-UHFFFAOYSA-N 0.000 claims 1
- NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
- JNXFOEOZSYOZCN-UHFFFAOYSA-N 4-chloro-n-(3-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CCNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JNXFOEOZSYOZCN-UHFFFAOYSA-N 0.000 claims 1
- OYPGSBLIRKBVFP-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OYPGSBLIRKBVFP-UHFFFAOYSA-N 0.000 claims 1
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- 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
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- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95525007P | 2007-08-10 | 2007-08-10 | |
| US60/955,250 | 2007-08-10 | ||
| PCT/US2008/072760 WO2009023623A1 (en) | 2007-08-10 | 2008-08-11 | Heteroaryl amide analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2691512A1 true CA2691512A1 (en) | 2009-02-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002691512A Abandoned CA2691512A1 (en) | 2007-08-10 | 2008-08-11 | Heteroaryl amide analogues |
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| BR (1) | BRPI0812594A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2691512A1 (cg-RX-API-DMAC7.html) |
| CO (1) | CO6251319A2 (cg-RX-API-DMAC7.html) |
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| WO2012163456A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| CN103687860B (zh) | 2011-07-22 | 2016-06-08 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
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| KR102232744B1 (ko) * | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| CA2896790C (en) | 2013-01-22 | 2022-05-10 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| BR112015019276A2 (pt) | 2013-02-19 | 2017-07-18 | Pfizer | compostos de azabenzimidazol como inibidores de isoenzimas de pde4 para o tratamento de distúrbios do snc e outros distúrbios |
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| JO3509B1 (ar) | 2013-03-14 | 2020-07-05 | Janssen Pharmaceutica Nv | معدلات p2x7 |
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| CA2918487C (en) * | 2013-07-17 | 2021-08-03 | Global Alliance For Tb Drug Development | Azaindole compounds, synthesis thereof, and methods of using the same |
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| EP3233841A1 (en) * | 2014-12-15 | 2017-10-25 | Merck Patent GmbH | Indole and azaindoles derivatives and their use in neurodegenerative diseases |
| JP6462493B2 (ja) | 2015-05-29 | 2019-01-30 | 株式会社デンソー | 進入判定装置、進入判定方法 |
| CA3010615C (en) | 2016-01-14 | 2024-02-20 | Beth Israel Deaconess Medical Center, Inc. | Mast-cell modulators and uses thereof |
| TW201819361A (zh) | 2016-09-03 | 2018-06-01 | 印度商托仁特生技有限公司 | 新穎吲唑化合物 |
| MY205440A (en) | 2018-09-28 | 2024-10-21 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| KR20210069079A (ko) | 2018-09-28 | 2021-06-10 | 얀센 파마슈티카 엔.브이. | 모노아실글리세롤 리파아제 조절제 |
| JP7697934B2 (ja) | 2019-09-30 | 2025-06-24 | ヤンセン ファーマシューティカ エヌ．ベー． | 放射線標識されたｍｇｌ ｐｅｔリガンド |
| BR112022019077A2 (pt) | 2020-03-26 | 2022-12-27 | Janssen Pharmaceutica Nv | Moduladores da monoacilglicerol lipase |
| CN116323581B (zh) * | 2020-09-22 | 2025-05-30 | 苏州恩华生物医药科技有限公司 | 吲哚衍生物及其应用 |
| CN119156388A (zh) * | 2022-04-15 | 2024-12-17 | 海南先声再明医药股份有限公司 | 膜缔合酪氨酸和苏氨酸激酶抑制剂 |
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-
2008
- 2008-08-11 CA CA002691512A patent/CA2691512A1/en not_active Abandoned
- 2008-08-11 CN CN200880021498A patent/CN101778850A/zh active Pending
- 2008-08-11 EP EP08797591A patent/EP2185560A4/en not_active Withdrawn
- 2008-08-11 BR BRPI0812594-5A patent/BRPI0812594A2/pt not_active IP Right Cessation
- 2008-08-11 EA EA200971085A patent/EA020332B1/ru not_active IP Right Cessation
- 2008-08-11 JP JP2010520343A patent/JP2010535816A/ja not_active Ceased
- 2008-08-11 AU AU2008286946A patent/AU2008286946B2/en not_active Ceased
- 2008-08-11 SG SG2012058533A patent/SG183699A1/en unknown
- 2008-08-11 UA UAA200913336A patent/UA99729C2/ru unknown
- 2008-08-11 NZ NZ582056A patent/NZ582056A/xx not_active IP Right Cessation
- 2008-08-11 WO PCT/US2008/072760 patent/WO2009023623A1/en not_active Ceased
- 2008-08-11 KR KR1020097026704A patent/KR20100066422A/ko not_active Ceased
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2009
- 2009-12-06 IL IL202550A patent/IL202550A0/en unknown
- 2009-12-22 CO CO09146587A patent/CO6251319A2/es not_active Application Discontinuation
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2014
- 2014-11-25 JP JP2014238138A patent/JP2015110566A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EA020332B1 (ru) | 2014-10-30 |
| JP2015110566A (ja) | 2015-06-18 |
| AU2008286946A1 (en) | 2009-02-19 |
| EA200971085A1 (ru) | 2010-06-30 |
| EP2185560A1 (en) | 2010-05-19 |
| WO2009023623A1 (en) | 2009-02-19 |
| UA99729C2 (en) | 2012-09-25 |
| IL202550A0 (en) | 2010-06-30 |
| NZ582056A (en) | 2012-08-31 |
| CN101778850A (zh) | 2010-07-14 |
| AU2008286946B2 (en) | 2013-11-21 |
| KR20100066422A (ko) | 2010-06-17 |
| CO6251319A2 (es) | 2011-02-21 |
| BRPI0812594A2 (pt) | 2015-06-23 |
| EP2185560A4 (en) | 2011-10-05 |
| JP2010535816A (ja) | 2010-11-25 |
| SG183699A1 (en) | 2012-09-27 |
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