CA2654915C - Tetrazole-substituted arylamides - Google Patents
Tetrazole-substituted arylamides Download PDFInfo
- Publication number
- CA2654915C CA2654915C CA2654915A CA2654915A CA2654915C CA 2654915 C CA2654915 C CA 2654915C CA 2654915 A CA2654915 A CA 2654915A CA 2654915 A CA2654915 A CA 2654915A CA 2654915 C CA2654915 C CA 2654915C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- ethyl
- tetrazol
- amide
- carboxylic acid
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- 150000003839 salts Chemical class 0.000 claims abstract description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 65
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
- 201000010099 disease Diseases 0.000 claims abstract description 32
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 29
- 102100040460 P2X purinoceptor 3 Human genes 0.000 claims abstract description 22
- 101710189970 P2X purinoceptor 3 Proteins 0.000 claims abstract description 20
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 7
- -1 3-oxo-2,3-dihydro-isoxazolyl Chemical group 0.000 claims description 996
- 229910052739 hydrogen Inorganic materials 0.000 claims description 142
- 239000001257 hydrogen Substances 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
- 239000002253 acid Substances 0.000 claims description 90
- 125000001153 fluoro group Chemical group F* 0.000 claims description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- IIGXIHLJMZQHJY-UHFFFAOYSA-N 1-pyrazin-2-ylethanamine Chemical compound CC(N)C1=CN=CC=N1 IIGXIHLJMZQHJY-UHFFFAOYSA-N 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 230000036407 pain Effects 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 18
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims description 16
- 102100040479 P2X purinoceptor 2 Human genes 0.000 claims description 15
- 101710189968 P2X purinoceptor 2 Proteins 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 102000000033 Purinergic Receptors Human genes 0.000 claims description 8
- 108010080192 Purinergic Receptors Proteins 0.000 claims description 8
- 230000002496 gastric effect Effects 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- VKYJXDOIGACUMA-UHFFFAOYSA-N 3-(4-methylphenyl)-5-(tetrazol-1-yl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C(O)=O)=CC(N2N=NN=C2)=C1 VKYJXDOIGACUMA-UHFFFAOYSA-N 0.000 claims description 5
- 208000025609 Urogenital disease Diseases 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 208000023504 respiratory system disease Diseases 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 3
- 208000027753 pain disease Diseases 0.000 claims description 2
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- ZRIGXRVEDXWVRX-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)-3-(4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)NC(CO)C)=CC(C=2C=CC(C)=CC=2)=CC=1N1N=NN=C1C(C)C ZRIGXRVEDXWVRX-UHFFFAOYSA-N 0.000 claims 3
- KTSMCQAWKMISEK-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)-3-(4-methylphenyl)-5-[5-(trifluoromethyl)tetrazol-1-yl]benzamide Chemical compound C=1C(C(=O)NC(CO)C)=CC(C=2C=CC(C)=CC=2)=CC=1N1N=NN=C1C(F)(F)F KTSMCQAWKMISEK-UHFFFAOYSA-N 0.000 claims 3
- NRKLWCKXDGDXDV-LBPRGKRZSA-N 3-(2-fluoro-4-methylphenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-methyltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C NRKLWCKXDGDXDV-LBPRGKRZSA-N 0.000 claims 2
- SQONOOOZKUWFFO-AWEZNQCLSA-N 3-(2-fluoro-4-methylphenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C(C)C SQONOOOZKUWFFO-AWEZNQCLSA-N 0.000 claims 2
- FBUOXIUEHURPJY-UHFFFAOYSA-N 3-(4-methylphenyl)-n-(2-oxo-1h-pyrimidin-6-yl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC2=NC(=O)NC=C2)=CC(C=2C=CC(C)=CC=2)=C1 FBUOXIUEHURPJY-UHFFFAOYSA-N 0.000 claims 2
- QRSNQXVKLYJXQJ-LBPRGKRZSA-N 3-[5-(1,1-difluoroethyl)tetrazol-1-yl]-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-methylpyridin-2-yl)benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2N=CC(C)=CC=2)=CC=1N1N=NN=C1C(C)(F)F QRSNQXVKLYJXQJ-LBPRGKRZSA-N 0.000 claims 2
- JYPLNXGNHJXDCN-UHFFFAOYSA-N 3-[5-(1-methoxyethyl)tetrazol-1-yl]-5-(4-methylphenyl)-n-(1-pyrimidin-5-ylethyl)benzamide Chemical compound COC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 JYPLNXGNHJXDCN-UHFFFAOYSA-N 0.000 claims 2
- PSBNIYZSJFUYRP-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)-3-(4-methylphenyl)-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NC(C)CO)=CC(C=2C=CC(C)=CC=2)=C1 PSBNIYZSJFUYRP-UHFFFAOYSA-N 0.000 claims 2
- SPJBSTXMKNSQOS-UHFFFAOYSA-N n-[(5-methylpyrazin-2-yl)methyl]-3-(5-methylpyridin-2-yl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2N=CC(C)=CC=2)=C1 SPJBSTXMKNSQOS-UHFFFAOYSA-N 0.000 claims 2
- XHEXFBXPMRBWRT-UHFFFAOYSA-N n-[(5-methylpyrazin-2-yl)methyl]-3-(5-methylpyridin-2-yl)-5-[5-(trifluoromethyl)tetrazol-1-yl]benzamide Chemical compound N1=CC(C)=CC=C1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(N2C(=NN=N2)C(F)(F)F)=C1 XHEXFBXPMRBWRT-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- HWZCZRQAMAYGPY-UHFFFAOYSA-N 1-pyridazin-3-ylethanamine Chemical compound CC(N)C1=CC=CN=N1 HWZCZRQAMAYGPY-UHFFFAOYSA-N 0.000 claims 1
- KIEIXWJUWMQIQC-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-(5-ethyltetrazol-1-yl)-n-(1-hydroxypropan-2-yl)benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)CO)=CC(C=2C(=CC(Cl)=CC=2)Cl)=C1 KIEIXWJUWMQIQC-UHFFFAOYSA-N 0.000 claims 1
- OAPJCTMCRMMQOM-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-(5-ethyltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(Cl)=CC=2)Cl)=C1 OAPJCTMCRMMQOM-UHFFFAOYSA-N 0.000 claims 1
- KIEIXWJUWMQIQC-NSHDSACASA-N 3-(2,4-dichlorophenyl)-5-(5-ethyltetrazol-1-yl)-n-[(2s)-1-hydroxypropan-2-yl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(Cl)=CC=2)Cl)=C1 KIEIXWJUWMQIQC-NSHDSACASA-N 0.000 claims 1
- NKUPCUYVLULSQY-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(F)=CC=2)Cl)=C1 NKUPCUYVLULSQY-UHFFFAOYSA-N 0.000 claims 1
- GAXANXHKPOONPD-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-n-(1-hydroxypropan-2-yl)-5-[5-(2-methylpropyl)tetrazol-1-yl]benzamide Chemical compound CC(C)CC1=NN=NN1C1=CC(C(=O)NC(C)CO)=CC(C=2C(=CC(F)=CC=2)Cl)=C1 GAXANXHKPOONPD-UHFFFAOYSA-N 0.000 claims 1
- QQUGIYFBGAWCDZ-LBPRGKRZSA-N 3-(2-chloro-4-fluorophenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(F)=CC=2)Cl)=C1 QQUGIYFBGAWCDZ-LBPRGKRZSA-N 0.000 claims 1
- GAXANXHKPOONPD-ZDUSSCGKSA-N 3-(2-chloro-4-fluorophenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-[5-(2-methylpropyl)tetrazol-1-yl]benzamide Chemical compound CC(C)CC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(F)=CC=2)Cl)=C1 GAXANXHKPOONPD-ZDUSSCGKSA-N 0.000 claims 1
- MXLOKVAYMWXPQO-UHFFFAOYSA-N 3-(2-chloro-4-methylphenyl)-n-(1-hydroxypropan-2-yl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)NC(CO)C)=CC(C=2C(=CC(C)=CC=2)Cl)=CC=1N1N=NN=C1C(C)C MXLOKVAYMWXPQO-UHFFFAOYSA-N 0.000 claims 1
- BNLRERGWJNSQBI-OAHLLOKOSA-N 3-(2-chloro-4-methylphenyl)-n-[(2r)-1-methoxypropan-2-yl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)N[C@H](C)COC)=CC(C=2C(=CC(C)=CC=2)Cl)=CC=1N1N=NN=C1C(C)C BNLRERGWJNSQBI-OAHLLOKOSA-N 0.000 claims 1
- XETZMGJGEZRRIH-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-methyltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound C=1N=CC=NC=1C(C)NC(=O)C(C=1)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C XETZMGJGEZRRIH-UHFFFAOYSA-N 0.000 claims 1
- KXMMIYLIIVJFGN-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 KXMMIYLIIVJFGN-UHFFFAOYSA-N 0.000 claims 1
- XZCITZGLPLFNNW-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyridin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=CC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 XZCITZGLPLFNNW-UHFFFAOYSA-N 0.000 claims 1
- QJRXVGWKHOTJRF-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyridin-3-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=CC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 QJRXVGWKHOTJRF-UHFFFAOYSA-N 0.000 claims 1
- OOIWVGCAAJQJLV-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyridin-4-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=CN=CC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 OOIWVGCAAJQJLV-UHFFFAOYSA-N 0.000 claims 1
- KXMMIYLIIVJFGN-INIZCTEOSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-[(1s)-1-pyrazin-2-ylethyl]benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)N[C@@H](C)C=2N=CC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 KXMMIYLIIVJFGN-INIZCTEOSA-N 0.000 claims 1
- SMWXCBYAEUPGCM-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propyltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 SMWXCBYAEUPGCM-UHFFFAOYSA-N 0.000 claims 1
- OFNZZAMHRXUDFC-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propyltetrazol-1-yl)-n-(1-pyridin-3-ylethyl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=CC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 OFNZZAMHRXUDFC-UHFFFAOYSA-N 0.000 claims 1
- ROUQDJFVLUBMGH-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-(5-propyltetrazol-1-yl)-n-(1-pyridin-4-ylethyl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NC(C)C=2C=CN=CC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 ROUQDJFVLUBMGH-UHFFFAOYSA-N 0.000 claims 1
- RFABZTRYGVNRGO-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-hydroxyethyl)tetrazol-1-yl]-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(O)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 RFABZTRYGVNRGO-UHFFFAOYSA-N 0.000 claims 1
- PUAPAQQAJDUPPH-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-hydroxyethyl)tetrazol-1-yl]-n-(1-pyrimidin-5-ylethyl)benzamide Chemical compound CC(O)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 PUAPAQQAJDUPPH-UHFFFAOYSA-N 0.000 claims 1
- WCHVWKYYKQGESO-UEWDXFNNSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-hydroxyethyl)tetrazol-1-yl]-n-[(2s)-1-hydroxypropan-2-yl]benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C(C)O WCHVWKYYKQGESO-UEWDXFNNSA-N 0.000 claims 1
- RCGBQZGFRSAJAH-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-hydroxyethyl)tetrazol-1-yl]-n-[(5-methylpyrazin-2-yl)methyl]benzamide Chemical compound CC(O)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 RCGBQZGFRSAJAH-UHFFFAOYSA-N 0.000 claims 1
- HMNUPBVTJKSSSE-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-methoxyethyl)tetrazol-1-yl]-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound COC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 HMNUPBVTJKSSSE-UHFFFAOYSA-N 0.000 claims 1
- YZTUGPHTVCDLNV-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-5-[5-(1-methoxyethyl)tetrazol-1-yl]-n-[(5-methylpyrazin-2-yl)methyl]benzamide Chemical compound COC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 YZTUGPHTVCDLNV-UHFFFAOYSA-N 0.000 claims 1
- KUXYICZEIZKXHC-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-N-(2-oxo-1H-pyrimidin-6-yl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC2=NC(=O)NC=C2)=CC(C=2C(=CC(C)=CC=2)F)=C1 KUXYICZEIZKXHC-UHFFFAOYSA-N 0.000 claims 1
- IYQPAJJYZUJGKJ-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-n-(1-methoxypropan-2-yl)-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)NC(C)COC)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C(C)C IYQPAJJYZUJGKJ-UHFFFAOYSA-N 0.000 claims 1
- IYQPAJJYZUJGKJ-OAHLLOKOSA-N 3-(2-fluoro-4-methylphenyl)-n-[(2r)-1-methoxypropan-2-yl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound C=1C(C(=O)N[C@H](C)COC)=CC(C=2C(=CC(C)=CC=2)F)=CC=1N1N=NN=C1C(C)C IYQPAJJYZUJGKJ-OAHLLOKOSA-N 0.000 claims 1
- LFIPSPXNGOWGII-AWEZNQCLSA-N 3-(2-fluoro-4-methylphenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(C)=CC=2)F)=C1 LFIPSPXNGOWGII-AWEZNQCLSA-N 0.000 claims 1
- PMRNLWNBCFAPDU-LSLKUGRBSA-N 3-(2-fluoro-4-methylphenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-[5-(1-methoxyethyl)tetrazol-1-yl]benzamide Chemical compound COC(C)C1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(C)=CC=2)F)=C1 PMRNLWNBCFAPDU-LSLKUGRBSA-N 0.000 claims 1
- IFSUWEPLLNHNEB-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-n-[(5-methylpyrazin-2-yl)methyl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 IFSUWEPLLNHNEB-UHFFFAOYSA-N 0.000 claims 1
- QJONWAZNSSIIHU-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenyl)-n-[(5-methylpyrazin-2-yl)methyl]-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C(=CC(C)=CC=2)F)=C1 QJONWAZNSSIIHU-UHFFFAOYSA-N 0.000 claims 1
- PUZLNTRYKKNMDY-UHFFFAOYSA-N 3-(4-chloro-2-fluorophenyl)-5-(5-ethyltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C(=CC(Cl)=CC=2)F)=C1 PUZLNTRYKKNMDY-UHFFFAOYSA-N 0.000 claims 1
- IGMABCFEWFEZJM-NSHDSACASA-N 3-(4-chloro-2-fluorophenyl)-5-(5-ethyltetrazol-1-yl)-n-[(2s)-1-hydroxypropan-2-yl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(Cl)=CC=2)F)=C1 IGMABCFEWFEZJM-NSHDSACASA-N 0.000 claims 1
- BBBSQZBCGSMLCX-LBPRGKRZSA-N 3-(4-chloro-2-fluorophenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(Cl)=CC=2)F)=C1 BBBSQZBCGSMLCX-LBPRGKRZSA-N 0.000 claims 1
- KVUOIAJKZMMSCF-LBPRGKRZSA-N 3-(4-chloro-2-fluorophenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C(=CC(Cl)=CC=2)F)=C1 KVUOIAJKZMMSCF-LBPRGKRZSA-N 0.000 claims 1
- VXEMYPAAQDSXKG-LBPRGKRZSA-N 3-(4-chlorophenyl)-5-(5-ethyltetrazol-1-yl)-n-[(2s)-1-hydroxypropan-2-yl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C=CC(Cl)=CC=2)=C1 VXEMYPAAQDSXKG-LBPRGKRZSA-N 0.000 claims 1
- JLGMRLRHRYCBPT-HNNXBMFYSA-N 3-(4-chlorophenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-[(1s)-1-pyrazin-2-ylethyl]benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)N[C@@H](C)C=2N=CC=NC=2)=CC(C=2C=CC(Cl)=CC=2)=C1 JLGMRLRHRYCBPT-HNNXBMFYSA-N 0.000 claims 1
- NXKOFMZNRCEEPN-ZDUSSCGKSA-N 3-(4-chlorophenyl)-n-[(2s)-1-hydroxypropan-2-yl]-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)CO)=CC(C=2C=CC(Cl)=CC=2)=C1 NXKOFMZNRCEEPN-ZDUSSCGKSA-N 0.000 claims 1
- ULYIWDCHKDLZNQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(5-methylpyrazin-2-yl)methyl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C=CC(Cl)=CC=2)=C1 ULYIWDCHKDLZNQ-UHFFFAOYSA-N 0.000 claims 1
- NSMISNZZWRHXCZ-UHFFFAOYSA-N 3-(4-methyl-2-oxopyridin-1-yl)-n-(1-morpholin-4-ylpropan-2-yl)-5-(tetrazol-1-yl)benzamide Chemical compound C=1C(N2N=NN=C2)=CC(N2C(C=C(C)C=C2)=O)=CC=1C(=O)NC(C)CN1CCOCC1 NSMISNZZWRHXCZ-UHFFFAOYSA-N 0.000 claims 1
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- NREBHLJBTQYWEB-UHFFFAOYSA-N 3-(4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 NREBHLJBTQYWEB-UHFFFAOYSA-N 0.000 claims 1
- VGVPYZBSSIBTQC-UHFFFAOYSA-N 3-(4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-(pyrazin-2-ylmethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 VGVPYZBSSIBTQC-UHFFFAOYSA-N 0.000 claims 1
- NREBHLJBTQYWEB-QGZVFWFLSA-N 3-(4-methylphenyl)-5-(5-propan-2-yltetrazol-1-yl)-n-[(1r)-1-pyrazin-2-ylethyl]benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)N[C@H](C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 NREBHLJBTQYWEB-QGZVFWFLSA-N 0.000 claims 1
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- HJKWQDHZKDUSPP-UHFFFAOYSA-N 3-(4-methylphenyl)-5-[5-(2-methylpropyl)tetrazol-1-yl]-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)CC1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 HJKWQDHZKDUSPP-UHFFFAOYSA-N 0.000 claims 1
- BPEGZINEJBBUTD-UHFFFAOYSA-N 3-(4-methylphenyl)-n-(4-phenylbutan-2-yl)-5-(tetrazol-1-yl)benzamide Chemical compound C=1C(C=2C=CC(C)=CC=2)=CC(N2N=NN=C2)=CC=1C(=O)NC(C)CCC1=CC=CC=C1 BPEGZINEJBBUTD-UHFFFAOYSA-N 0.000 claims 1
- VFCKHMUPIQQVSI-UHFFFAOYSA-N 3-(4-methylphenyl)-n-[(3-oxo-1,2-oxazol-5-yl)methyl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2ONC(=O)C=2)=CC(C=2C=CC(C)=CC=2)=C1 VFCKHMUPIQQVSI-UHFFFAOYSA-N 0.000 claims 1
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- SRMHRWIFJAHECS-UHFFFAOYSA-N 3-(5-bromopyridin-2-yl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2N=CC(Br)=CC=2)=C1 SRMHRWIFJAHECS-UHFFFAOYSA-N 0.000 claims 1
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- PNZJPEUGEBBRAJ-UHFFFAOYSA-N 3-(5-chloropyridin-2-yl)-5-[5-(2-methylpropyl)tetrazol-1-yl]-n-[(5-methylpyrazin-2-yl)methyl]benzamide Chemical compound CC(C)CC1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2N=CC(Cl)=CC=2)=C1 PNZJPEUGEBBRAJ-UHFFFAOYSA-N 0.000 claims 1
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- IPYYWXRGBBYBNO-UHFFFAOYSA-N 3-(5-chloropyridin-2-yl)-n-[(5-methylpyrazin-2-yl)methyl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2N=CC(Cl)=CC=2)=C1 IPYYWXRGBBYBNO-UHFFFAOYSA-N 0.000 claims 1
- PQGSBUVZLTTXGP-UHFFFAOYSA-N 3-(5-chloropyridin-2-yl)-n-[(5-methylpyrazin-2-yl)methyl]-5-(5-propyltetrazol-1-yl)benzamide Chemical compound CCCC1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2N=CC(Cl)=CC=2)=C1 PQGSBUVZLTTXGP-UHFFFAOYSA-N 0.000 claims 1
- CGEOPJKMHAEUPW-UHFFFAOYSA-N 3-(5-chloropyridin-2-yl)-n-[(5-methylpyrazin-2-yl)methyl]-5-[5-(trifluoromethyl)tetrazol-1-yl]benzamide Chemical compound C1=NC(C)=CN=C1CNC(=O)C1=CC(C=2N=CC(Cl)=CC=2)=CC(N2C(=NN=N2)C(F)(F)F)=C1 CGEOPJKMHAEUPW-UHFFFAOYSA-N 0.000 claims 1
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- CIFXASDFCMECMA-MRXNPFEDSA-N 3-(5-ethyltetrazol-1-yl)-5-(4-methylphenyl)-n-[(1r)-1-pyrazin-2-ylethyl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)N[C@H](C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 CIFXASDFCMECMA-MRXNPFEDSA-N 0.000 claims 1
- CIFXASDFCMECMA-INIZCTEOSA-N 3-(5-ethyltetrazol-1-yl)-5-(4-methylphenyl)-n-[(1s)-1-pyrazin-2-ylethyl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)N[C@@H](C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 CIFXASDFCMECMA-INIZCTEOSA-N 0.000 claims 1
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- WNKWZFPYKWIDRK-UHFFFAOYSA-N 3-(5-ethyltetrazol-1-yl)-5-(4-methylphenyl)-n-[1-(1,3-thiazol-2-yl)ethyl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)C=2SC=CN=2)=CC(C=2C=CC(C)=CC=2)=C1 WNKWZFPYKWIDRK-UHFFFAOYSA-N 0.000 claims 1
- WSFAQVCDRDTZTK-UHFFFAOYSA-N 3-(5-ethyltetrazol-1-yl)-5-(4-methylphenyl)-n-[1-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)ethyl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)C=2ON=C(N=2)C=2C=NC=CC=2)=CC(C=2C=CC(C)=CC=2)=C1 WSFAQVCDRDTZTK-UHFFFAOYSA-N 0.000 claims 1
- UTRGXYRWTPDNBT-UHFFFAOYSA-N 3-(5-ethyltetrazol-1-yl)-5-(4-methylphenyl)-n-[1-(3-pyridin-4-yl-1,2,4-oxadiazol-5-yl)ethyl]benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)C=2ON=C(N=2)C=2C=CN=CC=2)=CC(C=2C=CC(C)=CC=2)=C1 UTRGXYRWTPDNBT-UHFFFAOYSA-N 0.000 claims 1
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- KPWVWEONOIAHMY-UHFFFAOYSA-N 3-(5-ethyltetrazol-1-yl)-n-(1-hydroxypropan-2-yl)-5-(4-methylphenyl)benzamide Chemical compound CCC1=NN=NN1C1=CC(C(=O)NC(C)CO)=CC(C=2C=CC(C)=CC=2)=C1 KPWVWEONOIAHMY-UHFFFAOYSA-N 0.000 claims 1
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- OHZJYEXBHCXRFK-UHFFFAOYSA-N 3-(5-methylpyridin-2-yl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2N=CC(C)=CC=2)=C1 OHZJYEXBHCXRFK-UHFFFAOYSA-N 0.000 claims 1
- ZKKRRXGSWATVCU-UHFFFAOYSA-N 3-(5-methylpyridin-2-yl)-5-(5-propan-2-yltetrazol-1-yl)-n-(1-pyrimidin-5-ylethyl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=NC=2)=CC(C=2N=CC(C)=CC=2)=C1 ZKKRRXGSWATVCU-UHFFFAOYSA-N 0.000 claims 1
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- XJIXFWPXTRWNHI-UHFFFAOYSA-N 3-(5-methylpyridin-2-yl)-5-(5-propan-2-yltetrazol-1-yl)-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NCC=2C=NC(=CC=2)C(F)(F)F)=CC(C=2N=CC(C)=CC=2)=C1 XJIXFWPXTRWNHI-UHFFFAOYSA-N 0.000 claims 1
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- AYVYULUOQQFXCJ-UHFFFAOYSA-N 3-(5-methylpyridin-2-yl)-n-(1-pyrazin-2-ylethyl)-5-[5-(trifluoromethyl)tetrazol-1-yl]benzamide Chemical compound C=1N=CC=NC=1C(C)NC(=O)C(C=1)=CC(C=2N=CC(C)=CC=2)=CC=1N1N=NN=C1C(F)(F)F AYVYULUOQQFXCJ-UHFFFAOYSA-N 0.000 claims 1
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- ZDEDLNKQISPFHU-UHFFFAOYSA-N 3-(5-methylpyridin-2-yl)-n-[1-(6-methylpyridin-2-yl)ethyl]-5-(5-propan-2-yltetrazol-1-yl)benzamide Chemical compound CC(C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=C(C)C=CC=2)=CC(C=2N=CC(C)=CC=2)=C1 ZDEDLNKQISPFHU-UHFFFAOYSA-N 0.000 claims 1
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- BBZMGIBUJWSKJV-LYKKTTPLSA-N 3-[5-[(1s)-1-hydroxyethyl]tetrazol-1-yl]-5-(4-methylphenyl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound C[C@H](O)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 BBZMGIBUJWSKJV-LYKKTTPLSA-N 0.000 claims 1
- FXANCCNEMVKOTH-INIZCTEOSA-N 3-[5-[(1s)-1-hydroxyethyl]tetrazol-1-yl]-5-(4-methylphenyl)-n-[(5-methylpyrazin-2-yl)methyl]benzamide Chemical compound C[C@H](O)C1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 FXANCCNEMVKOTH-INIZCTEOSA-N 0.000 claims 1
- GTSHRJFLOMKJSP-KBPBESRZSA-N 3-[5-[(1s)-1-hydroxyethyl]tetrazol-1-yl]-n-[(2s)-1-hydroxypropan-2-yl]-5-(4-methylphenyl)benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2C=CC(C)=CC=2)=CC=1N1N=NN=C1[C@H](C)O GTSHRJFLOMKJSP-KBPBESRZSA-N 0.000 claims 1
- JYPLNXGNHJXDCN-DJNXLDHESA-N 3-[5-[(1s)-1-methoxyethyl]tetrazol-1-yl]-5-(4-methylphenyl)-n-(1-pyrimidin-5-ylethyl)benzamide Chemical compound CO[C@@H](C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2C=NC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 JYPLNXGNHJXDCN-DJNXLDHESA-N 0.000 claims 1
- OXRFKESEGZDELK-ZENAZSQFSA-N 3-[5-[(2r)-1-methoxypropan-2-yl]tetrazol-1-yl]-5-(4-methylphenyl)-n-(1-pyrazin-2-ylethyl)benzamide Chemical compound COC[C@H](C)C1=NN=NN1C1=CC(C(=O)NC(C)C=2N=CC=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 OXRFKESEGZDELK-ZENAZSQFSA-N 0.000 claims 1
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- CPBSDZJTJYNMET-UHFFFAOYSA-N 3-[5-[(dimethylamino)methyl]tetrazol-1-yl]-5-(4-methylphenyl)-n-[(5-methylpyrazin-2-yl)methyl]benzamide Chemical compound CN(C)CC1=NN=NN1C1=CC(C(=O)NCC=2N=CC(C)=NC=2)=CC(C=2C=CC(C)=CC=2)=C1 CPBSDZJTJYNMET-UHFFFAOYSA-N 0.000 claims 1
- OSZAWMKQOHPLHV-HNNXBMFYSA-N 3-[5-[(dimethylamino)methyl]tetrazol-1-yl]-n-[(2s)-1-hydroxypropan-2-yl]-5-(4-methylphenyl)benzamide Chemical compound C=1C(C(=O)N[C@H](CO)C)=CC(C=2C=CC(C)=CC=2)=CC=1N1N=NN=C1CN(C)C OSZAWMKQOHPLHV-HNNXBMFYSA-N 0.000 claims 1
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| JP5539235B2 (ja) | 2008-02-29 | 2014-07-02 | エボテック・アーゲー | アミド化合物、組成物およびそれらの使用 |
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| EP2246259B1 (en) | 2009-04-29 | 2012-12-12 | Eurocopter Deutschland GmbH | Rotor wing with integrated tension-torque-transmission element and method for its production |
| JP5685203B2 (ja) * | 2009-05-29 | 2015-03-18 | ラクオリア創薬株式会社 | カルシウムチャネル遮断薬またはナトリウムチャネル遮断薬としてのアリール置換カルボキサミド誘導体 |
| AR077033A1 (es) * | 2009-06-11 | 2011-07-27 | Hoffmann La Roche | Compuestos inhibidores de las quinasas de janus y su uso en el tratamiento de enfermedades inmunologicas |
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| PT3381917T (pt) * | 2013-01-31 | 2021-10-27 | Bellus Health Cough Inc | Compostos imidazopiridina e suas utilizações |
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| US10183937B2 (en) | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| CN107207449B (zh) * | 2015-04-23 | 2020-11-10 | 豪夫迈·罗氏有限公司 | 用于治疗精神障碍的四唑衍生物 |
| JP6877359B2 (ja) * | 2015-06-04 | 2021-05-26 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | イミダゾール誘導体 |
| JP6831376B2 (ja) * | 2015-10-06 | 2021-02-17 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | トリアゾール誘導体 |
| CN108473462B (zh) | 2016-02-02 | 2021-06-22 | 豪夫迈·罗氏有限公司 | 作为eaat3抑制剂的吡唑-吡啶衍生物 |
| TWI696615B (zh) * | 2016-05-05 | 2020-06-21 | 瑞士商伊蘭科動物健康公司 | 雜芳基-1,2,4-三唑及雜芳基-三唑化合物 |
| EP3464246B1 (en) | 2016-05-27 | 2020-07-08 | H. Hoffnabb-La Roche Ag | Pyrazol compounds as eaat3 inhibitors |
| CN109563049B (zh) | 2016-10-14 | 2022-11-29 | 豪夫迈·罗氏有限公司 | 作为eaat3抑制剂的咪唑化合物 |
| TWI741040B (zh) * | 2016-10-20 | 2021-10-01 | 德商拜耳作物科學公司 | 製備3-烷基硫基-2-氯-n-(1-烷基-1h-四唑-5-基)-4-三氟甲基苯甲醯胺之方法 |
| RU2650780C1 (ru) | 2016-12-06 | 2018-04-17 | Общество с ограниченной ответственностью "Анальгетики будущего" | Пептидный модулятор пуринергических рецепторов |
| KR20220016074A (ko) | 2019-05-31 | 2022-02-08 | 키에시 파르마슈티시 엣스. 피. 에이. | P2x3 억제제로서 피리도피리미딘 유도체 |
| BR112021022099A2 (pt) | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
| CA3196335A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Phthalazine derivatives as p2x3 inhibitors |
| AU2021386684A1 (en) | 2020-11-27 | 2023-05-25 | Chiesi Farmaceutici S.P.A. | (aza)quinoline 4-amines derivatives as p2x3 inhibitors |
| CN116601149A (zh) | 2020-11-27 | 2023-08-15 | 奇斯药制品公司 | 作为p2x3抑制剂的氨基喹唑啉衍生物 |
| AR131715A1 (es) * | 2023-01-30 | 2025-04-23 | Eurofarma Laboratorios S A | AMIDAS BLOQUEADORAS DE Nav 1.7 Y/O Nav 1.8, SUS PROCESOS DE OBTENCIÓN, COMPOSICIONES, USOS, MÉTODOS DE TRATAMIENTO DE LOS MISMOS Y KITS |
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| IL109570A0 (en) * | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| JPH10501122A (ja) * | 1994-05-27 | 1998-02-03 | グラクソ、グループ、リミテッド | P▲下2x▼レセプター(プリノセプターファミリー) |
| US6133434A (en) * | 1997-04-28 | 2000-10-17 | Glaxo Group Limited | Purinergic receptor |
| JP2000281664A (ja) * | 1999-03-30 | 2000-10-10 | Otsuka Pharmaceut Co Ltd | チアゾール誘導体 |
| AU773892B2 (en) | 1999-06-30 | 2004-06-10 | H. Lundbeck A/S | Selective NPY (Y5) antagonists |
| US6599926B2 (en) | 2000-06-23 | 2003-07-29 | Bristol-Myers Squibb Company | Heteroaryl-phenyl substituted factor Xa inhibitors |
| DE10055713A1 (de) | 2000-11-10 | 2002-05-23 | Dingwei Tim Yu | Neue Klasse von Antifungimitteln |
| PA8557501A1 (es) * | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| TW200304374A (en) * | 2001-11-30 | 2003-10-01 | Smithkline Beecham Plc | Novel compounds |
| US20030236439A1 (en) | 2002-01-30 | 2003-12-25 | Gregory Agoston | Non-steroidal analogs of 2-methoxyestradiol |
| CA2480856A1 (en) * | 2002-04-05 | 2003-10-23 | Merck & Co., Inc. | Substituted aryl amides |
| WO2004009816A1 (en) | 2002-07-18 | 2004-01-29 | Ceretek Llc | Methods of treating conditions associated with an edg-1 receptor |
| US7078423B2 (en) * | 2002-07-18 | 2006-07-18 | Inotek Pharmaceuticals Corporation | 5-Aryltetrazole compounds, compositions thereof, and uses therefor |
| DE10312963A1 (de) * | 2003-03-24 | 2004-10-07 | Aventis Pharma Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| JP2006523701A (ja) | 2003-04-18 | 2006-10-19 | メルク エンド カムパニー インコーポレーテッド | ナトリウムチャネルブロッカーとしてのビアリール置換チアゾール、オキサゾール、およびイミダゾール |
| NZ551974A (en) * | 2004-07-02 | 2010-01-29 | Inst Medical W & E Hall | Alpha-helical minetics |
| EP1917262B1 (en) * | 2005-08-15 | 2011-12-14 | F. Hoffmann-La Roche AG | Piperidine and piperazine derivatives as p2x3 antagonists |
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