JP2010535816A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010535816A5 JP2010535816A5 JP2010520343A JP2010520343A JP2010535816A5 JP 2010535816 A5 JP2010535816 A5 JP 2010535816A5 JP 2010520343 A JP2010520343 A JP 2010520343A JP 2010520343 A JP2010520343 A JP 2010520343A JP 2010535816 A5 JP2010535816 A5 JP 2010535816A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- pyrimidin
- carboxamide
- methyl
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 102
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 44
- -1 each of which is Chemical group 0.000 claims description 34
- 208000002193 Pain Diseases 0.000 claims description 33
- 230000036407 pain Effects 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 102000005962 receptors Human genes 0.000 claims description 25
- 108020003175 receptors Proteins 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 150000005215 alkyl ethers Chemical class 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 208000004296 neuralgia Diseases 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 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 description 4
- 208000008035 Back Pain Diseases 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010029240 Neuritis Diseases 0.000 claims description 4
- 208000022873 Ocular disease Diseases 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 210000005036 nerve Anatomy 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 208000021722 neuropathic pain Diseases 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 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 description 2
- 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 description 2
- 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 description 2
- 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
- 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 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
- 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 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- NCQCHKXQFNBEPU-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycycloheptyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=NC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCCC1 NCQCHKXQFNBEPU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JAXLKCRYONSHKK-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=NC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 JAXLKCRYONSHKK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- PTDLAPWZPSAZJT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chloro-3-fluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)N2CCCCC2)=C1 PTDLAPWZPSAZJT-UHFFFAOYSA-N 0.000 claims description 2
- ZHQIUAHDKPUOKT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 ZHQIUAHDKPUOKT-UHFFFAOYSA-N 0.000 claims description 2
- XKBDSAHQQPZOGB-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCOCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 XKBDSAHQQPZOGB-UHFFFAOYSA-N 0.000 claims description 2
- JFUGGKDZPSAIOY-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JFUGGKDZPSAIOY-UHFFFAOYSA-N 0.000 claims description 2
- HFOVPPMTYJOFMT-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CN=C11)=CN1C1=NC=CC=N1 HFOVPPMTYJOFMT-UHFFFAOYSA-N 0.000 claims description 2
- MWHKATVDYBPMRL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(Cl)C=C1 MWHKATVDYBPMRL-UHFFFAOYSA-N 0.000 claims description 2
- LYJDGLXLBJVRCJ-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 LYJDGLXLBJVRCJ-UHFFFAOYSA-N 0.000 claims description 2
- FSSJSUBFNKMDTL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FSSJSUBFNKMDTL-UHFFFAOYSA-N 0.000 claims description 2
- OTOKCOMTTJYKQA-UHFFFAOYSA-N 4-chloro-n-[2-(4-fluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OTOKCOMTTJYKQA-UHFFFAOYSA-N 0.000 claims description 2
- YCOBLIXIJZXBLR-UHFFFAOYSA-N 4-chloro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 YCOBLIXIJZXBLR-UHFFFAOYSA-N 0.000 claims description 2
- IUCVSEOIXFTRMF-UHFFFAOYSA-N 4-chloro-n-[2-piperidin-1-yl-2-[4-(trifluoromethyl)phenyl]ethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 IUCVSEOIXFTRMF-UHFFFAOYSA-N 0.000 claims description 2
- APXFQTNXUQJHBO-UHFFFAOYSA-N 4-chloro-n-[2-piperidin-1-yl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 APXFQTNXUQJHBO-UHFFFAOYSA-N 0.000 claims description 2
- FKCPUVYYGVELQN-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FKCPUVYYGVELQN-UHFFFAOYSA-N 0.000 claims description 2
- FAURIVHGMPPVLE-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FAURIVHGMPPVLE-UHFFFAOYSA-N 0.000 claims description 2
- RUEJAIZHINZZDH-SUMWQHHRSA-N 4-chloro-n-[[(1s,2r)-2-hydroxycyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound O[C@@H]1CCCC[C@H]1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 RUEJAIZHINZZDH-SUMWQHHRSA-N 0.000 claims description 2
- KAENIFYSTKFXFA-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclobutyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCC1 KAENIFYSTKFXFA-UHFFFAOYSA-N 0.000 claims description 2
- OXHUCARSSRATMO-UHFFFAOYSA-N 4-chloro-n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 OXHUCARSSRATMO-UHFFFAOYSA-N 0.000 claims description 2
- DERUNCJUFQBRRW-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 DERUNCJUFQBRRW-UHFFFAOYSA-N 0.000 claims description 2
- GDLABCVOIPYOGZ-UHFFFAOYSA-N 4-chloro-n-[[1-(4-methylpiperazin-1-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1CN(C)CCN1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GDLABCVOIPYOGZ-UHFFFAOYSA-N 0.000 claims description 2
- PIODEHXTCAOMMR-UHFFFAOYSA-N 4-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CC=C3N(C=3N=CC=CN=3)C=2)CCOCC1 PIODEHXTCAOMMR-UHFFFAOYSA-N 0.000 claims description 2
- RRTLCYYRRUBNTG-UHFFFAOYSA-N 4-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=C(Cl)C=CN=C3N(C=3N=CC=CN=3)C=2)CCOCC1 RRTLCYYRRUBNTG-UHFFFAOYSA-N 0.000 claims description 2
- PDAPGQZQFOLEID-UHFFFAOYSA-N 4-cyano-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(C#N)=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 PDAPGQZQFOLEID-UHFFFAOYSA-N 0.000 claims description 2
- SPIDLTVGBQEWBZ-UHFFFAOYSA-N 4-fluoro-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(F)C=CC=C11)=CN1C1=NC=CC=N1 SPIDLTVGBQEWBZ-UHFFFAOYSA-N 0.000 claims description 2
- AHBGYVPATHFLKO-UHFFFAOYSA-N 4-fluoro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 AHBGYVPATHFLKO-UHFFFAOYSA-N 0.000 claims description 2
- QBYJBBMCFSHBTP-UHFFFAOYSA-N 4-fluoro-n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 QBYJBBMCFSHBTP-UHFFFAOYSA-N 0.000 claims description 2
- MYTXBBJPZVAHBU-UHFFFAOYSA-N 4-fluoro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 MYTXBBJPZVAHBU-UHFFFAOYSA-N 0.000 claims description 2
- GEJZOVZEMUQBQK-UHFFFAOYSA-N 4-fluoro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 GEJZOVZEMUQBQK-UHFFFAOYSA-N 0.000 claims description 2
- QJKMIQZBXGSLAK-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 QJKMIQZBXGSLAK-UHFFFAOYSA-N 0.000 claims description 2
- GUCURJGUSGPXIC-UHFFFAOYSA-N 4-fluoro-n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=C(F)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 GUCURJGUSGPXIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- SCBJKZLZBBFRSW-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 SCBJKZLZBBFRSW-UHFFFAOYSA-N 0.000 claims description 2
- FGRZUIMQKHWIGY-UHFFFAOYSA-N 4-methyl-n-(4-methyl-2-morpholin-4-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1COCCN1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 FGRZUIMQKHWIGY-UHFFFAOYSA-N 0.000 claims description 2
- JVYOELCASNKUKK-UHFFFAOYSA-N 4-methyl-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(C)C=CC=C11)=CN1C1=NC=CC=N1 JVYOELCASNKUKK-UHFFFAOYSA-N 0.000 claims description 2
- OIKQYDBRBPIGDB-UHFFFAOYSA-N 4-methyl-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 OIKQYDBRBPIGDB-UHFFFAOYSA-N 0.000 claims description 2
- GPRICYCQYFLCSD-UHFFFAOYSA-N 7-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=CN1C1=NC=CC=N1 GPRICYCQYFLCSD-UHFFFAOYSA-N 0.000 claims description 2
- 208000004998 Abdominal Pain Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 208000001387 Causalgia Diseases 0.000 claims description 2
- 208000002881 Colic Diseases 0.000 claims description 2
- 208000023890 Complex Regional Pain Syndromes 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
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 208000033830 Hot Flashes Diseases 0.000 claims description 2
- 206010060800 Hot flush Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010023230 Joint stiffness Diseases 0.000 claims description 2
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 2
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- XZTSWCQCBWGMSJ-UHFFFAOYSA-N O=C(C(C(C1=CC=C2)=C2Cl)=CN1C1=NC=CC=N1)NCC(CCCCCCl)C1=CC=C(C(F)(F)F)C=C1 Chemical compound O=C(C(C(C1=CC=C2)=C2Cl)=CN1C1=NC=CC=N1)NCC(CCCCCCl)C1=CC=C(C(F)(F)F)C=C1 XZTSWCQCBWGMSJ-UHFFFAOYSA-N 0.000 claims description 2
- 206010031009 Oral pain Diseases 0.000 claims description 2
- 206010049002 Scar pain Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010072005 Spinal pain Diseases 0.000 claims description 2
- 206010042496 Sunburn Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 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 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 201000006549 dyspepsia Diseases 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
- 238000000099 in vitro assay Methods 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus 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
- UUCNBNVIKYMGID-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[2-(dimethylamino)ethyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 UUCNBNVIKYMGID-UHFFFAOYSA-N 0.000 claims description 2
- PFXSYZMQBXGURF-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-[3-(dimethylamino)propyl]indole-3-carboxamide Chemical compound C12=C(Cl)C=CC=C2N(CCCN(C)C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 PFXSYZMQBXGURF-UHFFFAOYSA-N 0.000 claims description 2
- AFWMMWSWXVYLDZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 AFWMMWSWXVYLDZ-UHFFFAOYSA-N 0.000 claims description 2
- NCRXZRNQZWAQQE-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(C)=CC=CC=2N1C1=NC=CC=N1 NCRXZRNQZWAQQE-UHFFFAOYSA-N 0.000 claims description 2
- GXQNBGUOACJYPR-UHFFFAOYSA-N n-(2-adamantyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NC2C3CC4CC(C3)CC2C4)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 GXQNBGUOACJYPR-UHFFFAOYSA-N 0.000 claims description 2
- TZMRUUUUXCOCJO-UHFFFAOYSA-N 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=CC=CC=C11)=CN1C1=NC=CC=N1 TZMRUUUUXCOCJO-UHFFFAOYSA-N 0.000 claims description 2
- VHQQVRXPSSCPOI-UHFFFAOYSA-N 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=CC=CC=C11)=CN1C1=NC=CC=N1 VHQQVRXPSSCPOI-UHFFFAOYSA-N 0.000 claims description 2
- KAKVGAOZPOYJDQ-UHFFFAOYSA-N n-[(1-morpholin-4-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(N2CCOCC2)CCCCC1 KAKVGAOZPOYJDQ-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
- YYRCJXPQPPOVIB-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YYRCJXPQPPOVIB-UHFFFAOYSA-N 0.000 claims description 2
- HCSZLWUZTCBTMA-UHFFFAOYSA-N n-[2-(1-adamantyl)-2-hydroxyethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(O)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 HCSZLWUZTCBTMA-UHFFFAOYSA-N 0.000 claims description 2
- MUCNGXXFDVORKK-UHFFFAOYSA-N n-[2-(1-adamantyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 MUCNGXXFDVORKK-UHFFFAOYSA-N 0.000 claims description 2
- CSLSUGNOOSSJQR-UHFFFAOYSA-N n-[2-(2-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=CC=C1Br CSLSUGNOOSSJQR-UHFFFAOYSA-N 0.000 claims description 2
- QCWQBVHZWNBJBZ-UHFFFAOYSA-N n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=C(F)C(F)=CC=1)N1CCCCC1 QCWQBVHZWNBJBZ-UHFFFAOYSA-N 0.000 claims description 2
- PSJGDAHXFKXRLX-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=C(Br)C=C1 PSJGDAHXFKXRLX-UHFFFAOYSA-N 0.000 claims description 2
- BMBBNQBENWAQSL-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-(3-cyanopyridin-2-yl)-4-methylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 BMBBNQBENWAQSL-UHFFFAOYSA-N 0.000 claims description 2
- JUPFTIKYNNMMRM-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-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)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 JUPFTIKYNNMMRM-UHFFFAOYSA-N 0.000 claims description 2
- XABGESGCAUJZCE-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 XABGESGCAUJZCE-UHFFFAOYSA-N 0.000 claims description 2
- MSFLUMKJDNRDIJ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-4-methyl-1-pyrazin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=NC=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 MSFLUMKJDNRDIJ-UHFFFAOYSA-N 0.000 claims description 2
- XDOZISHMSFCTLB-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-(3-cyanopyridin-2-yl)-4-methylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 XDOZISHMSFCTLB-UHFFFAOYSA-N 0.000 claims description 2
- GKRJPCWGZVYJTR-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-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)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 GKRJPCWGZVYJTR-UHFFFAOYSA-N 0.000 claims description 2
- XVBJHQNEIHWFGJ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 XVBJHQNEIHWFGJ-UHFFFAOYSA-N 0.000 claims description 2
- NMZOKSLIMKWCSU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 NMZOKSLIMKWCSU-UHFFFAOYSA-N 0.000 claims description 2
- VPWBKIPGUKDQEG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrazin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=NC=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 VPWBKIPGUKDQEG-UHFFFAOYSA-N 0.000 claims description 2
- GCXBEEBQOLYVLA-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 GCXBEEBQOLYVLA-UHFFFAOYSA-N 0.000 claims description 2
- QPMCJYOLEYBWBR-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-methylpentyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(F)C=CC=C11)=CN1C1=NC=CC=N1 QPMCJYOLEYBWBR-UHFFFAOYSA-N 0.000 claims description 2
- SUYBFJWMWRJOCU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-methylpentyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 SUYBFJWMWRJOCU-UHFFFAOYSA-N 0.000 claims description 2
- MNQGSJTUNWNUSP-UHFFFAOYSA-N n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 MNQGSJTUNWNUSP-UHFFFAOYSA-N 0.000 claims description 2
- OGULYLDMHWGPIK-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(F)=CC=1)N1CCCCC1 OGULYLDMHWGPIK-UHFFFAOYSA-N 0.000 claims description 2
- UYOZVFBAAGNPAH-UHFFFAOYSA-N n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 UYOZVFBAAGNPAH-UHFFFAOYSA-N 0.000 claims description 2
- BSKWQGRALUGAQK-UHFFFAOYSA-N n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 BSKWQGRALUGAQK-UHFFFAOYSA-N 0.000 claims description 2
- NYPBTJPAMLSQOQ-UHFFFAOYSA-N n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 NYPBTJPAMLSQOQ-UHFFFAOYSA-N 0.000 claims description 2
- KKGOARLCUKPGGM-UHFFFAOYSA-N n-[[1-(4-chloro-3-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C2(CNC(=O)C=3C4=CC=CC=C4N(C=4N=CC=CN=4)C=3)CCCCC2)=C1 KKGOARLCUKPGGM-UHFFFAOYSA-N 0.000 claims description 2
- NJMXJFYCSGXEFJ-UHFFFAOYSA-N n-[[1-(4-chloro-3-fluorophenyl)cyclohexyl]methyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C2(CNC(=O)C=3C4=C(F)C=CC=C4N(C=4N=CC=CN=4)C=3)CCCCC2)=C1 NJMXJFYCSGXEFJ-UHFFFAOYSA-N 0.000 claims description 2
- RFBYRXHGAHIWMU-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 RFBYRXHGAHIWMU-UHFFFAOYSA-N 0.000 claims description 2
- OXYXAQHHQONHMX-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 OXYXAQHHQONHMX-UHFFFAOYSA-N 0.000 claims description 2
- KYMISPJLBMCXEX-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 KYMISPJLBMCXEX-UHFFFAOYSA-N 0.000 claims description 2
- PPTCMFMVYXESNA-UHFFFAOYSA-N n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=C(C=CC=C3N(C=3N=CC=CN=3)C=2)C(F)(F)F)CCCCC1 PPTCMFMVYXESNA-UHFFFAOYSA-N 0.000 claims description 2
- FTRLLIYBIMGYRE-UHFFFAOYSA-N n-[[1-(4-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FTRLLIYBIMGYRE-UHFFFAOYSA-N 0.000 claims description 2
- YQMBEIHSLXMESW-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(C=CC=C3N(C=3N=CC=CN=3)C=2)C(F)(F)F)CCCCC1 YQMBEIHSLXMESW-UHFFFAOYSA-N 0.000 claims description 2
- JZVQKMGKZYXCCJ-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 JZVQKMGKZYXCCJ-UHFFFAOYSA-N 0.000 claims description 2
- ITLQNYHTRGSTRM-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(C)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 ITLQNYHTRGSTRM-UHFFFAOYSA-N 0.000 claims description 2
- RVVOKOYZHSYRLP-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclopentyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCC1 RVVOKOYZHSYRLP-UHFFFAOYSA-N 0.000 claims description 2
- JBBHYKYPYOHBHL-UHFFFAOYSA-N n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 JBBHYKYPYOHBHL-UHFFFAOYSA-N 0.000 claims description 2
- FOZCCIXBLOUDJL-UHFFFAOYSA-N n-[[1-(6-methylpyridin-3-yl)cyclohexyl]methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1(CNC(=O)C=2C3=C(C=CC=C3N(C=3N=CC=CN=3)C=2)C(F)(F)F)CCCCC1 FOZCCIXBLOUDJL-UHFFFAOYSA-N 0.000 claims description 2
- XTFXNXJNPJKQNQ-UHFFFAOYSA-N n-[[1-(6-methylpyridin-3-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XTFXNXJNPJKQNQ-UHFFFAOYSA-N 0.000 claims description 2
- FPGKCDOPNVMSFC-UHFFFAOYSA-N n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCOCC1 FPGKCDOPNVMSFC-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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000008653 root damage Effects 0.000 claims description 2
- 230000001953 sensory effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 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
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- AINBWHVBVYQQAZ-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindole-3-carboxylic acid Chemical compound C12=CC=CC(Cl)=C2C(C(=O)O)=CN1C1=NC=CC=N1 AINBWHVBVYQQAZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 230000008484 agonism Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 208000013287 immunodeficiency 48 Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 13
- 125000001188 haloalkyl group Chemical group 0.000 description 13
- 125000004438 haloalkoxy group Chemical group 0.000 description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 9
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 8
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 4
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000003994 retinal ganglion cell Anatomy 0.000 description 2
- 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 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 208000018629 immunodeficiency 56 Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95525007P | 2007-08-10 | 2007-08-10 | |
| PCT/US2008/072760 WO2009023623A1 (en) | 2007-08-10 | 2008-08-11 | Heteroaryl amide analogues |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014238138A Division JP2015110566A (ja) | 2007-08-10 | 2014-11-25 | ヘテロアリールアミド類似体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010535816A JP2010535816A (ja) | 2010-11-25 |
| JP2010535816A5 true JP2010535816A5 (enExample) | 2011-09-29 |
Family
ID=40351102
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010520343A Ceased JP2010535816A (ja) | 2007-08-10 | 2008-08-11 | ヘテロアリールアミド類似体 |
| JP2014238138A Pending JP2015110566A (ja) | 2007-08-10 | 2014-11-25 | ヘテロアリールアミド類似体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014238138A Pending JP2015110566A (ja) | 2007-08-10 | 2014-11-25 | ヘテロアリールアミド類似体 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP2185560A4 (enExample) |
| JP (2) | JP2010535816A (enExample) |
| KR (1) | KR20100066422A (enExample) |
| CN (1) | CN101778850A (enExample) |
| AU (1) | AU2008286946B2 (enExample) |
| BR (1) | BRPI0812594A2 (enExample) |
| CA (1) | CA2691512A1 (enExample) |
| CO (1) | CO6251319A2 (enExample) |
| EA (1) | EA020332B1 (enExample) |
| IL (1) | IL202550A0 (enExample) |
| NZ (1) | NZ582056A (enExample) |
| SG (1) | SG183699A1 (enExample) |
| UA (1) | UA99729C2 (enExample) |
| WO (1) | WO2009023623A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010118921A1 (en) * | 2009-04-14 | 2010-10-21 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012110190A1 (en) * | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| DK2707101T3 (da) * | 2011-05-12 | 2019-05-13 | Proteostasis Therapeutics Inc | Proteostaseregulatorer |
| WO2012163792A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) * | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| EP2734526B1 (en) | 2011-07-22 | 2016-04-06 | Actelion Pharmaceuticals Ltd. | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| SG11201403933UA (en) * | 2012-01-20 | 2014-08-28 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| JOP20130213B1 (ar) * | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| TWI612034B (zh) * | 2012-12-12 | 2018-01-21 | 愛杜西亞製藥有限公司 | 作爲ｐ２ｘ７受體拮抗劑之吲哚羧醯胺衍生物 |
| ES2614495T3 (es) * | 2012-12-18 | 2017-05-31 | Actelion Pharmaceuticals Ltd. | Derivados de indol carboxamida como antagonistas del receptor P2X7 |
| 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 |
| CA2896790C (en) | 2013-01-22 | 2022-05-10 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| JP6505023B2 (ja) | 2013-02-19 | 2019-04-24 | ファイザー・インク | Ｃｎｓおよび他の障害を治療するための、ｐｄｅ４アイソザイムの阻害薬としてのアザベンゾイミダゾール化合物 |
| EP2970304B1 (en) | 2013-03-14 | 2018-08-15 | Janssen Pharmaceutica NV | P2x7 modulators |
| TWI627174B (zh) | 2013-03-14 | 2018-06-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調控劑 |
| EP3112366B1 (en) | 2013-03-14 | 2018-02-28 | Janssen Pharmaceutica NV | P2x7 modulators |
| TWI644671B (zh) | 2013-03-14 | 2018-12-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調節劑 |
| AU2014290598B2 (en) * | 2013-07-17 | 2018-11-08 | Foundation For Neglected Disease Research | Azaindole compounds, synthesis thereof, and methods of using the same |
| 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 |
| US10131669B2 (en) | 2014-07-24 | 2018-11-20 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| HUE044040T2 (hu) | 2014-08-06 | 2019-09-30 | Pfizer | Imidazopiridazin vegyületek |
| EP3191492B1 (en) | 2014-09-12 | 2019-01-09 | Janssen Pharmaceutica NV | P2x7 modulators |
| AU2015315693B2 (en) | 2014-09-12 | 2020-01-16 | Janssen Pharmaceutica Nv | P2X7 modulating n-acyl-triazolopyrazines |
| WO2016053947A1 (en) | 2014-09-29 | 2016-04-07 | Takeda Pharmaceutical Company Limited | Crystalline form of 1-(1-methyl-1h-pyrazol-4-yl)-n-((1r,5s,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-1h-indole-3-carboxamide |
| JP6673932B2 (ja) * | 2014-12-15 | 2020-03-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | インドール及びアザインドール誘導体、並びに神経変性疾患におけるそれらの使用 |
| 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 |
| EP3402780A1 (en) | 2016-01-14 | 2018-11-21 | 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 |
| MA53721A (fr) | 2018-09-28 | 2021-09-15 | Janssen Pharmaceutica Nv | Modulateurs de la monoacylglycérol lipase |
| US20200102311A1 (en) | 2018-09-28 | 2020-04-02 | Janssen Pharmaceutica Nv | Monoacylglycerol Lipase Modulators |
| 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 |
| WO2021191359A1 (en) | 2020-03-26 | 2021-09-30 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| WO2022062991A1 (zh) * | 2020-09-22 | 2022-03-31 | 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 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557342A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
| DE2931323A1 (de) * | 1979-08-02 | 1981-02-26 | Kali Chemie Pharma Gmbh | Neue n-aminoalkylindol-derivate und ihre salze |
| DE3131527A1 (de) * | 1981-08-08 | 1983-02-24 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5023265A (en) * | 1990-06-01 | 1991-06-11 | Schering Corporation | Substituted 1-H-pyrrolopyridine-3-carboxamides |
| TW229140B (enExample) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
| US5424329A (en) * | 1993-08-18 | 1995-06-13 | Warner-Lambert Company | Indole-2-carboxamides as inhibitors of cell adhesion |
| AU743881B2 (en) * | 1997-12-24 | 2002-02-07 | Sanofi-Aventis Deutschland Gmbh | Indole derivatives as inhibitors or factor Xa |
| CN1147483C (zh) * | 1999-04-09 | 2004-04-28 | 阿斯特拉曾尼卡有限公司 | 金刚烷衍生物 |
| ATE396978T1 (de) * | 1999-10-07 | 2008-06-15 | Amgen Inc | Triazin-kinase-hemmer |
| WO2001058869A2 (en) * | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases |
| US7112594B2 (en) * | 2000-08-09 | 2006-09-26 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| PL368129A1 (en) * | 2001-08-09 | 2005-03-21 | Ono Pharmaceutical Co, Ltd. | Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| ES2293005T3 (es) * | 2002-10-03 | 2008-03-16 | F. Hoffmann-La Roche Ag | Indol-3-carboxamidas como activadores de la glucocinasa. |
| DE10253426B4 (de) * | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| JP2006511562A (ja) * | 2002-12-20 | 2006-04-06 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 泌尿器系疾患の処置のための置換２，５−ジアミドインドール類の使用 |
| FR2857966A1 (fr) * | 2003-07-24 | 2005-01-28 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| FR2874015B1 (fr) * | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| FR2880625B1 (fr) * | 2005-01-07 | 2007-03-09 | Sanofi Aventis Sa | Derives de n-(heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| TW200700387A (en) * | 2005-03-21 | 2007-01-01 | Akzo Nobel Nv | 1-benzylindole-2-carboxamide derivatives |
| FR2888847B1 (fr) * | 2005-07-22 | 2007-08-31 | Sanofi Aventis Sa | Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique |
| WO2007079239A2 (en) * | 2005-12-30 | 2007-07-12 | Acadia Pharmaceuticals Inc. | Bicyclic nitrogen compounds as modulators of ghrelin receptor and uses thereof |
| WO2007098214A1 (en) * | 2006-02-21 | 2007-08-30 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
-
2008
- 2008-08-11 CN CN200880021498A patent/CN101778850A/zh active Pending
- 2008-08-11 KR KR1020097026704A patent/KR20100066422A/ko not_active Ceased
- 2008-08-11 UA UAA200913336A patent/UA99729C2/ru unknown
- 2008-08-11 JP JP2010520343A patent/JP2010535816A/ja not_active Ceased
- 2008-08-11 CA CA002691512A patent/CA2691512A1/en not_active Abandoned
- 2008-08-11 WO PCT/US2008/072760 patent/WO2009023623A1/en not_active Ceased
- 2008-08-11 EP EP08797591A patent/EP2185560A4/en not_active Withdrawn
- 2008-08-11 NZ NZ582056A patent/NZ582056A/xx not_active IP Right Cessation
- 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 AU AU2008286946A patent/AU2008286946B2/en not_active Ceased
- 2008-08-11 SG SG2012058533A patent/SG183699A1/en unknown
-
2009
- 2009-12-06 IL IL202550A patent/IL202550A0/en unknown
- 2009-12-22 CO CO09146587A patent/CO6251319A2/es not_active Application Discontinuation
-
2014
- 2014-11-25 JP JP2014238138A patent/JP2015110566A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010535816A5 (enExample) | ||
| JP7623275B2 (ja) | ＮａＶ１．８を阻害するピリダジン化合物 | |
| JP2010533736A5 (enExample) | ||
| CA2915561C (en) | Novel substituted bicyclic compounds as bromodomain inhibitors | |
| JP6254730B2 (ja) | ベンズアミド類 | |
| CA2664335C (en) | Rho kinase inhibitors | |
| CA2774647C (en) | Substituted amide compound | |
| US8637510B2 (en) | Morpholinothiazoles as alpha 7 positive allosteric modulators | |
| CN105153028B (zh) | 作为c-Met激酶抑制剂的化合物 | |
| JP2010510987A5 (enExample) | ||
| TWI409062B (zh) | 作為５-ｈｔ２ａ５-羥色胺受體之調節子而有用於與該受體有關的疾病之治療之３-苯基吡唑衍生物 | |
| IL271149B1 (en) | Compounds for modulating s1p1 activity and methods of using the same | |
| HUE032169T2 (en) | Quinoline and quinoxaline amides as modulators of sodium channels | |
| JP2019108333A (ja) | 置換キノキサリン誘導体およびｍＧｌｕＲ４の正のアロステリックモジュレーターとしてのそれらの使用 | |
| WO2004046139A1 (en) | Benzofuran derivates, process for their preparation and intermediates thereof | |
| JPWO2020014246A5 (enExample) | ||
| MXPA06007715A (es) | Derivados de (3-oxo-3,4-dihidro-quinoxalin-2-il-amino)-benzamida y compuesto relacionado, como inhibidores de glucogeno fosforilasa para el tratamiento de la diabetes y obesidad. | |
| CN101537001A (zh) | 作为jak-stat3信号通路抑制剂的化合物的应用 | |
| CN104955826B (zh) | 可用于治疗神经学疾病和病症的螺-喹唑酮衍生物 | |
| JP5822079B2 (ja) | 疼痛治療剤 | |
| JP2011500629A (ja) | 神経ペプチドｙ２受容体のモジュレーターとしての置換ピペラジンおよびピペリジン | |
| JP2006117568A (ja) | チオフェン環を有する新規アミド誘導体及びその医薬としての用途 | |
| RU2009136331A (ru) | Индоловые и бензотиофеновые соединения в качестве модуляторов гистаминового н3-рецептора | |
| JP6401265B2 (ja) | Ｎ−（４−クロロ−２−ヒドロキシ−３−（（３ｓ）−３−ピペリジニルスルホニル）フェニル−ｎ’−（３−フルオロ−２−メチルフェニル）尿素の臭化水素酸塩 | |
| WO2008124524A2 (en) | Aryl sulfonamide compounds as modulators of the cck2 receptor |