AU2008286946B2 - Heteroaryl amide analogues - Google Patents
Heteroaryl amide analogues Download PDFInfo
- Publication number
- AU2008286946B2 AU2008286946B2 AU2008286946A AU2008286946A AU2008286946B2 AU 2008286946 B2 AU2008286946 B2 AU 2008286946B2 AU 2008286946 A AU2008286946 A AU 2008286946A AU 2008286946 A AU2008286946 A AU 2008286946A AU 2008286946 B2 AU2008286946 B2 AU 2008286946B2
- Authority
- AU
- Australia
- 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.)
- Ceased
Links
- -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 128
- 150000001875 compounds Chemical class 0.000 claims abstract description 218
- 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 124
- 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 123
- 208000002193 Pain Diseases 0.000 claims abstract description 105
- 230000036407 pain Effects 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 206010061218 Inflammation Diseases 0.000 claims abstract description 18
- 230000004054 inflammatory process Effects 0.000 claims abstract description 18
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 208000022873 Ocular disease Diseases 0.000 claims abstract description 6
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
- 208000026278 immune system disease Diseases 0.000 claims abstract description 4
- 230000000926 neurological effect Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims description 65
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical group 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 208000004296 neuralgia Diseases 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 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 description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 150000005215 alkyl ethers Chemical class 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 17
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 206010016654 Fibrosis Diseases 0.000 claims description 13
- 208000006673 asthma Diseases 0.000 claims description 13
- 208000021722 neuropathic pain Diseases 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 13
- 206010029240 Neuritis Diseases 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 230000001154 acute effect Effects 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 210000005036 nerve Anatomy 0.000 claims description 8
- 201000008482 osteoarthritis Diseases 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- VVFCLFKBZYOEQN-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N)=CN1C1=NC=CC=N1 VVFCLFKBZYOEQN-UHFFFAOYSA-N 0.000 claims description 6
- 208000008035 Back Pain Diseases 0.000 claims description 6
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 206010025135 lupus erythematosus Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 230000009529 traumatic brain injury Effects 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 5
- 201000005569 Gout Diseases 0.000 claims description 5
- 206010023230 Joint stiffness Diseases 0.000 claims description 5
- 206010039710 Scleroderma Diseases 0.000 claims description 5
- 206010003246 arthritis Diseases 0.000 claims description 5
- 230000007882 cirrhosis Effects 0.000 claims description 5
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 206010019233 Headaches Diseases 0.000 claims description 4
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 230000008653 root damage Effects 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- CQZYCDBHEULOFD-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=N1 CQZYCDBHEULOFD-UHFFFAOYSA-N 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
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 206010068065 Burning mouth syndrome Diseases 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
- 208000001387 Causalgia Diseases 0.000 claims description 3
- 206010014020 Ear pain Diseases 0.000 claims description 3
- 206010015958 Eye pain Diseases 0.000 claims description 3
- 206010016059 Facial pain Diseases 0.000 claims description 3
- 208000033830 Hot Flashes Diseases 0.000 claims description 3
- 206010060800 Hot flush Diseases 0.000 claims description 3
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
- 208000000112 Myalgia Diseases 0.000 claims description 3
- 206010049002 Scar pain Diseases 0.000 claims description 3
- 206010042496 Sunburn Diseases 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 3
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 3
- 208000004967 femoral neuropathy Diseases 0.000 claims description 3
- 208000032184 meralgia paresthetica Diseases 0.000 claims description 3
- 208000013465 muscle pain Diseases 0.000 claims description 3
- 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 3
- 230000008764 nerve damage Effects 0.000 claims description 3
- 201000009985 neuronitis Diseases 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000002435 venom Substances 0.000 claims description 3
- 210000001048 venom Anatomy 0.000 claims description 3
- 231100000611 venom Toxicity 0.000 claims description 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 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 description 2
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- 206010072005 Spinal pain Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 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
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 2
- STWNGMSGPBZFMX-UHFFFAOYSA-N pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC(=O)C1=CC=CN=C1 STWNGMSGPBZFMX-UHFFFAOYSA-N 0.000 claims description 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
- 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
- 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
- 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
- KQVGATDURWAKBQ-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 KQVGATDURWAKBQ-UHFFFAOYSA-N 0.000 claims 1
- YPHBXMYPYMXXKK-UHFFFAOYSA-N 4-chloro-n-(4-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCCCC1=CC=CC=C1 YPHBXMYPYMXXKK-UHFFFAOYSA-N 0.000 claims 1
- QNCAVWZEJVXGSL-UHFFFAOYSA-N 4-chloro-n-(cycloheptylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1CCCCCC1 QNCAVWZEJVXGSL-UHFFFAOYSA-N 0.000 claims 1
- IXEUUUTXRDEESS-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycycloheptyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCCC1 IXEUUUTXRDEESS-UHFFFAOYSA-N 0.000 claims 1
- QHXNCWYVURIMHA-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 QHXNCWYVURIMHA-UHFFFAOYSA-N 0.000 claims 1
- MJSYWSCNWAHYJT-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclopentyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCC1 MJSYWSCNWAHYJT-UHFFFAOYSA-N 0.000 claims 1
- NDLYAXIBRQFGQO-UHFFFAOYSA-N 4-chloro-n-[(4-hydroxythian-4-yl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCSCC1 NDLYAXIBRQFGQO-UHFFFAOYSA-N 0.000 claims 1
- HUMJOZFHUVTLGE-UHFFFAOYSA-N 4-chloro-n-[2-(2,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound FC1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 HUMJOZFHUVTLGE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WSZARDIHNUIOKO-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 WSZARDIHNUIOKO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- 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
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- 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
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- 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
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- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| 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 (2)
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| AU2008286946A1 AU2008286946A1 (en) | 2009-02-19 |
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| KR (1) | KR20100066422A (OSRAM) |
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| UA (1) | UA99729C2 (OSRAM) |
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| ATE541832T1 (de) * | 2009-04-14 | 2012-02-15 | Affectis Pharmaceuticals Ag | Neuartige p2x7r-antagonisten und ihre verwendung |
| WO2012110190A1 (en) * | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| US9556166B2 (en) | 2011-05-12 | 2017-01-31 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| 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 |
| MX2014000894A (es) | 2011-07-22 | 2014-02-27 | Actelion Pharmaceuticals Ltd | Derivados de amidas heterociclicas como antagonistas de receptores p2x7. |
| BR112014017735B1 (pt) * | 2012-01-20 | 2022-06-28 | Idorsia Pharmaceuticals Ltd | Compostos derivados de amida heterocíclicos como antagonistas do receptor de p2x7, composição farmacêutica, e, uso de um composto |
| JOP20130213B1 (ar) * | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| EP2931717B1 (en) | 2012-12-12 | 2016-12-07 | Actelion Pharmaceuticals Ltd. | Indole carboxamide derivatives as p2x7 receptor antagonists |
| CA2891499C (en) * | 2012-12-18 | 2021-07-06 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| CN104918617B (zh) | 2013-01-22 | 2017-05-10 | 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 |
| JP6282017B2 (ja) * | 2013-01-22 | 2018-02-21 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｐ２ｘ７受容体アンタゴニストとしての複素環アミド誘導体 |
| EA201591360A1 (ru) | 2013-02-19 | 2016-03-31 | Пфайзер Инк. | Азабензимидазолы в качестве ингибиторов изозимов фдэ4 для лечения цнс и других расстройств |
| TWI627174B (zh) | 2013-03-14 | 2018-06-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調控劑 |
| ES2689526T3 (es) | 2013-03-14 | 2018-11-14 | Janssen Pharmaceutica Nv | Moduladores de P2X7 |
| JP6294953B2 (ja) | 2013-03-14 | 2018-03-14 | ヤンセン ファーマシューティカ エヌ．ベー． | Ｐ２ｘ７調節物質 |
| TWI599567B (zh) | 2013-03-14 | 2017-09-21 | 健生藥品公司 | Ｐ２ｘ７調節劑 |
| CN105636646B (zh) * | 2013-07-17 | 2017-12-19 | 全球结核病药物研发联盟 | 氮杂吲哚化合物、其合成及其使用方法 |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| EP3172210B1 (en) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Pyrazolopyrimidine compounds |
| PT3177624T (pt) | 2014-08-06 | 2019-07-11 | Pfizer | Compostos de imidazopiridazina |
| EP3191492B1 (en) | 2014-09-12 | 2019-01-09 | Janssen Pharmaceutica NV | P2x7 modulators |
| WO2016039983A1 (en) | 2014-09-12 | 2016-03-17 | Janssen Pharmaceutica Nv | P2x7 modulating n-acyl-triazolopyrazines |
| HUE055175T2 (hu) | 2014-09-29 | 2021-11-29 | Takeda Pharmaceuticals Co | Az 1-(1-metil-1H-pirazol-4-il)-N-((1R,5S,7S)-9-metil-3-oxa-9-azabiciklo[3.3.1] nonan-7-il)-1H-indol-3-karboxamid kristályos formája |
| CN107207476B (zh) * | 2014-12-15 | 2021-03-19 | 默克专利有限公司 | 吲哚和氮杂吲哚衍生物及其用于神经退化性疾病中的用途 |
| 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 |
| US20190016680A1 (en) | 2016-01-14 | 2019-01-17 | 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 |
| CN113164459B (zh) | 2018-09-28 | 2024-09-03 | 詹森药业有限公司 | 单酰基甘油脂肪酶调节剂 |
| CA3111309A1 (en) | 2018-09-28 | 2020-04-02 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| CA3156100A1 (en) | 2019-09-30 | 2021-04-08 | Janssen Pharmaceutica Nv | Radiolabelled mgl pet ligands |
| CA3176946A1 (en) | 2020-03-26 | 2021-09-30 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| 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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- 2008-08-11 UA UAA200913336A patent/UA99729C2/ru unknown
- 2008-08-11 EP EP08797591A patent/EP2185560A4/en not_active Withdrawn
- 2008-08-11 SG SG2012058533A patent/SG183699A1/en unknown
- 2008-08-11 NZ NZ582056A patent/NZ582056A/xx not_active IP Right Cessation
- 2008-08-11 EA EA200971085A patent/EA020332B1/ru not_active IP Right Cessation
- 2008-08-11 AU AU2008286946A patent/AU2008286946B2/en not_active Ceased
- 2008-08-11 BR BRPI0812594-5A patent/BRPI0812594A2/pt not_active IP Right Cessation
- 2008-08-11 CN CN200880021498A patent/CN101778850A/zh active Pending
- 2008-08-11 JP JP2010520343A patent/JP2010535816A/ja not_active Ceased
- 2008-08-11 CA CA002691512A patent/CA2691512A1/en not_active Abandoned
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- 2009-12-22 CO CO09146587A patent/CO6251319A2/es not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| EA200971085A1 (ru) | 2010-06-30 |
| CA2691512A1 (en) | 2009-02-19 |
| JP2010535816A (ja) | 2010-11-25 |
| EP2185560A4 (en) | 2011-10-05 |
| NZ582056A (en) | 2012-08-31 |
| UA99729C2 (en) | 2012-09-25 |
| IL202550A0 (en) | 2010-06-30 |
| CO6251319A2 (es) | 2011-02-21 |
| BRPI0812594A2 (pt) | 2015-06-23 |
| KR20100066422A (ko) | 2010-06-17 |
| SG183699A1 (en) | 2012-09-27 |
| WO2009023623A1 (en) | 2009-02-19 |
| CN101778850A (zh) | 2010-07-14 |
| EP2185560A1 (en) | 2010-05-19 |
| JP2015110566A (ja) | 2015-06-18 |
| AU2008286946A1 (en) | 2009-02-19 |
| EA020332B1 (ru) | 2014-10-30 |
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