JP2010535816A5 - - Google Patents
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- 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
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- 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
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| JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| CN104812749B (zh) | 2012-12-12 | 2016-12-14 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的吲哚羧酰胺衍生物 |
| KR102232744B1 (ko) * | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
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| KR102220847B1 (ko) * | 2013-01-22 | 2021-02-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
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| US9163020B2 (en) * | 2013-07-17 | 2015-10-20 | Global Alliance For Tb Drug Development | Azaindole compounds, synthesis thereof, and methods of using the same |
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| 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 |
| EA031201B1 (ru) | 2014-08-06 | 2018-11-30 | Пфайзер Инк. | Соединения имидазопиридазина |
| WO2016039983A1 (en) | 2014-09-12 | 2016-03-17 | Janssen Pharmaceutica Nv | P2x7 modulating n-acyl-triazolopyrazines |
| CA2960968A1 (en) | 2014-09-12 | 2016-03-17 | Janssen Pharmaceutica Nv | P2x7 modulators |
| PT3201203T (pt) | 2014-09-29 | 2021-08-09 | Takeda Pharmaceuticals Co | Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1hindol-3-carboxamida |
| AU2015362700B2 (en) * | 2014-12-15 | 2020-04-16 | 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 |
| 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 |
| CA3111380A1 (en) | 2018-09-28 | 2020-04-02 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| BR112021005936A2 (pt) | 2018-09-28 | 2021-06-29 | Janssen Pharmaceutica Nv | moduladores de monoacilglicerol lipase |
| KR20220075386A (ko) | 2019-09-30 | 2022-06-08 | 얀센 파마슈티카 엔.브이. | 방사성 표지된 mgl pet 리간드 |
| BR112022019077A2 (pt) | 2020-03-26 | 2022-12-27 | Janssen Pharmaceutica Nv | Moduladores da monoacilglicerol lipase |
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| TW229140B (en:Method) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
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| AU2001277731A1 (en) * | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
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| DE10253426B4 (de) * | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| US20060183753A1 (en) * | 2002-12-20 | 2006-08-17 | Bayer Healthcare Ag | Use of substituted 2,5-diamidoindoles for the treatment of urological diseases |
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| 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 |
| US20070213359A1 (en) * | 2005-12-30 | 2007-09-13 | Acadia Pharmaceuticals Inc. | Bicyclic-nitrogen compounds as modulators of ghrelin receptor and uses thereof |
| US20070265270A1 (en) * | 2006-02-21 | 2007-11-15 | Hitchcock Stephen A | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
-
2008
- 2008-08-11 EA EA200971085A patent/EA020332B1/ru not_active IP Right Cessation
- 2008-08-11 UA UAA200913336A patent/UA99729C2/ru unknown
- 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 KR KR1020097026704A patent/KR20100066422A/ko not_active Ceased
- 2008-08-11 NZ NZ582056A patent/NZ582056A/xx not_active IP Right Cessation
- 2008-08-11 AU AU2008286946A patent/AU2008286946B2/en not_active Ceased
- 2008-08-11 WO PCT/US2008/072760 patent/WO2009023623A1/en not_active Ceased
- 2008-08-11 SG SG2012058533A patent/SG183699A1/en unknown
- 2008-08-11 JP JP2010520343A patent/JP2010535816A/ja not_active Ceased
- 2008-08-11 CN CN200880021498A patent/CN101778850A/zh active Pending
- 2008-08-11 CA CA002691512A patent/CA2691512A1/en not_active Abandoned
-
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
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