WO2019133445A1 - Aminothiazoles utilisés en tant qu'inhibiteurs de vanin-1 - Google Patents
Aminothiazoles utilisés en tant qu'inhibiteurs de vanin-1 Download PDFInfo
- Publication number
- WO2019133445A1 WO2019133445A1 PCT/US2018/066882 US2018066882W WO2019133445A1 WO 2019133445 A1 WO2019133445 A1 WO 2019133445A1 US 2018066882 W US2018066882 W US 2018066882W WO 2019133445 A1 WO2019133445 A1 WO 2019133445A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- thiazol
- amino
- phenyl
- ketone
- methyl
- Prior art date
Links
- 108010029648 pantetheinase Proteins 0.000 title claims description 14
- 102100020749 Pantetheinase Human genes 0.000 title claims description 10
- 239000003112 inhibitor Substances 0.000 title description 87
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- 150000003839 salts Chemical class 0.000 claims abstract description 98
- 239000012453 solvate Substances 0.000 claims abstract description 68
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 15
- 208000011231 Crohn disease Diseases 0.000 claims abstract description 15
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 15
- -1 3-pyridylmethyl Chemical group 0.000 claims description 160
- 150000002576 ketones Chemical class 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
- 230000000694 effects Effects 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 210000004027 cell Anatomy 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 102100020748 Pantetheine hydrolase VNN2 Human genes 0.000 claims description 8
- 125000005466 alkylenyl group Chemical group 0.000 claims description 8
- DLALITXAVNRDSG-UHFFFAOYSA-N [2-(1-pyridin-3-ylethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC(=CC=C1)C(C)NC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C(F)(F)F DLALITXAVNRDSG-UHFFFAOYSA-N 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 101000854773 Mus musculus Vascular non-inflammatory molecule 3 Proteins 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- IYKJLYNAQBYDHU-UHFFFAOYSA-N (3-bromophenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound BrC=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1 IYKJLYNAQBYDHU-UHFFFAOYSA-N 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 101000854774 Homo sapiens Pantetheine hydrolase VNN2 Proteins 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- POOXOHISLGOAEF-UHFFFAOYSA-N bis[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 POOXOHISLGOAEF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- ZHVLZEMPNWOZPO-UHFFFAOYSA-N (3-chlorophenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)Cl ZHVLZEMPNWOZPO-UHFFFAOYSA-N 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 208000007882 Gastritis Diseases 0.000 claims description 4
- FHVIATDAQJJUFM-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(pyrrolidine-1-carbonyl)phenyl]methanone Chemical compound N1(CCCC1)C(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1 FHVIATDAQJJUFM-UHFFFAOYSA-N 0.000 claims description 4
- DREZZDMYLMLGCC-UHFFFAOYSA-N [2-[(2-methoxycyclopentyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1C(CCC1)OC)(F)F DREZZDMYLMLGCC-UHFFFAOYSA-N 0.000 claims description 4
- FFGCGDBLGQWALO-UHFFFAOYSA-N [3-(1-methylpyrazol-3-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=NN(C=C1)C FFGCGDBLGQWALO-UHFFFAOYSA-N 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- HTJSLCMKAPBACO-UHFFFAOYSA-N bis(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C HTJSLCMKAPBACO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- JXGYASQNGJDYLT-UHFFFAOYSA-N (3-cyclopropylsulfonylphenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C1CC1 JXGYASQNGJDYLT-UHFFFAOYSA-N 0.000 claims description 3
- XEULGZDCQBGAJV-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(1,3-thiazol-2-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound S1C(=NC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C XEULGZDCQBGAJV-UHFFFAOYSA-N 0.000 claims description 3
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 3
- APYSORCILNCREO-UHFFFAOYSA-N 5-[[[5-(3-methylsulfonylbenzoyl)-1,3-thiazol-2-yl]amino]methyl]-1H-pyridin-2-one Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC(=CC=1)O APYSORCILNCREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- KTHKYGNTVLAWLT-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-(3-pyridin-3-ylphenyl)methanone Chemical compound N1=CC(=CC=C1)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1 KTHKYGNTVLAWLT-UHFFFAOYSA-N 0.000 claims description 3
- PATXTCMHNJAEKG-UHFFFAOYSA-N [2-[(2-aminopyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C(=NC=CC=1)N)(F)F PATXTCMHNJAEKG-UHFFFAOYSA-N 0.000 claims description 3
- IUVMOROKOUQCSZ-UHFFFAOYSA-N [2-[(3-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC(=CC=C1)F)(F)F IUVMOROKOUQCSZ-UHFFFAOYSA-N 0.000 claims description 3
- QPGRZRGLOBFJMZ-INIZCTEOSA-N [2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)N[C@@H](CO)C1=CC=CC=C1 QPGRZRGLOBFJMZ-INIZCTEOSA-N 0.000 claims description 3
- RAVAEXPBJMDQBE-UHFFFAOYSA-N [2-[[3-hydroxy-1-(4-methoxyphenyl)propyl]amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC(CCO)C1=CC=C(C=C1)OC RAVAEXPBJMDQBE-UHFFFAOYSA-N 0.000 claims description 3
- GVEYECKSUCMYEW-UHFFFAOYSA-N [3-(1-methylpyrazol-4-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C=1C=NN(C=1)C GVEYECKSUCMYEW-UHFFFAOYSA-N 0.000 claims description 3
- GMPXJPMTBOUPFH-UHFFFAOYSA-N [3-(2-methylpyrazol-3-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC=NN1C GMPXJPMTBOUPFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 210000002919 epithelial cell Anatomy 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- UJNVUGOZLOELEC-UHFFFAOYSA-N (3,4-dichlorophenyl)-[2-(pyridin-3-ylmethyl)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CC=1SC(=CN=1)C(=O)C1=CC(=C(C=C1)Cl)Cl UJNVUGOZLOELEC-UHFFFAOYSA-N 0.000 claims description 2
- JVMXFUVHEWWJQZ-UHFFFAOYSA-N (3,4-dichlorophenyl)-[2-[(4-fluorophenyl)methyl]-1,3-thiazol-5-yl]methanone Chemical compound FC1=CC=C(C=C1)CC=1SC(=CN=1)C(=O)C1=CC(=C(C=C1)Cl)Cl JVMXFUVHEWWJQZ-UHFFFAOYSA-N 0.000 claims description 2
- CRRBPZUKOLIQKX-UHFFFAOYSA-N (3-fluorophenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-4-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC=C(N=1)C(=O)C1=CC(=CC=C1)F CRRBPZUKOLIQKX-UHFFFAOYSA-N 0.000 claims description 2
- KUESJGAAXDRMJZ-UHFFFAOYSA-N (3-fluorophenyl)-[2-[(4-fluorophenyl)methylamino]-1,3-thiazol-4-yl]methanone Chemical compound FC1=CC=C(C=C1)CNC=1SC=C(N=1)C(=O)C1=CC(=CC=C1)F KUESJGAAXDRMJZ-UHFFFAOYSA-N 0.000 claims description 2
- UHRFBDCTCMQALF-UHFFFAOYSA-N (3-methoxyphenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)OC UHRFBDCTCMQALF-UHFFFAOYSA-N 0.000 claims description 2
- DKGVHUUZQQALRT-UHFFFAOYSA-N (3-methylphenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C DKGVHUUZQQALRT-UHFFFAOYSA-N 0.000 claims description 2
- YLYYSEOCEXLMGO-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(1,3-oxazol-2-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound O1C(=NC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C YLYYSEOCEXLMGO-UHFFFAOYSA-N 0.000 claims description 2
- CUSLAEZODWYRST-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(1,3-thiazol-4-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound S1C=NC(=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C CUSLAEZODWYRST-UHFFFAOYSA-N 0.000 claims description 2
- NKYMTNCBUYILGO-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(1,3-thiazol-5-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound S1C=NC=C1CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C NKYMTNCBUYILGO-UHFFFAOYSA-N 0.000 claims description 2
- ZSGVJOVZHOXCPN-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(1H-pyrazol-5-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1N=C(C=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C ZSGVJOVZHOXCPN-UHFFFAOYSA-N 0.000 claims description 2
- CZXDAVCINKLPDE-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C CZXDAVCINKLPDE-UHFFFAOYSA-N 0.000 claims description 2
- ZRXLURJJTVUDRL-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(pyrimidin-5-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CN=CC(=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C ZRXLURJJTVUDRL-UHFFFAOYSA-N 0.000 claims description 2
- BCEYLOWQKXXUPF-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-[(1-phenylcyclobutyl)methylamino]-1,3-thiazol-5-yl]methanone Chemical compound C1(=CC=CC=C1)C1(CCC1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C BCEYLOWQKXXUPF-UHFFFAOYSA-N 0.000 claims description 2
- TXNQVANPPIFBBP-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-[(2-pyrrolidin-1-ylphenyl)methylamino]-1,3-thiazol-5-yl]methanone Chemical compound N1(CCCC1)C1=C(C=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C TXNQVANPPIFBBP-UHFFFAOYSA-N 0.000 claims description 2
- XYKZCGULXBFFBJ-UHFFFAOYSA-N (3-morpholin-4-ylsulfonylphenyl)-(2-pyrrolidin-1-yl-1,3-thiazol-5-yl)methanone Chemical compound N1(CCCC1)C=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)N1CCOCC1 XYKZCGULXBFFBJ-UHFFFAOYSA-N 0.000 claims description 2
- SUUWEYSGLNFEED-UHFFFAOYSA-N (3-phenylphenyl)-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC=CC=C1 SUUWEYSGLNFEED-UHFFFAOYSA-N 0.000 claims description 2
- QHPODIZNDGKZNX-UHFFFAOYSA-N 3-[2-[(4-fluorophenyl)methylamino]-1,3-thiazole-5-carbonyl]-N,N-dimethylbenzenesulfonamide Chemical compound FC1=CC=C(C=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)N(C)C QHPODIZNDGKZNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- GYSSSTCLKZEYPQ-UHFFFAOYSA-N N,N-dimethyl-3-[2-(pyridin-3-ylmethylamino)-1,3-thiazole-5-carbonyl]benzenesulfonamide Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)N(C)C GYSSSTCLKZEYPQ-UHFFFAOYSA-N 0.000 claims description 2
- SAJOQSNKNVECST-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-N-methyl-3-[2-(pyridin-3-ylmethylamino)-1,3-thiazole-5-carbonyl]benzamide Chemical compound FC1=CC=C(C=C1)CN(C(=O)C1=CC(=CC=C1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)C SAJOQSNKNVECST-UHFFFAOYSA-N 0.000 claims description 2
- FZUBRSNBTCYWPL-UHFFFAOYSA-N [2-(1H-pyrazol-4-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NNC=1)(F)F FZUBRSNBTCYWPL-UHFFFAOYSA-N 0.000 claims description 2
- BYKDYFHHTYEOHI-UHFFFAOYSA-N [2-(2-pyridin-3-ylpropan-2-ylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC(C)(C=1C=NC=CC=1)C)(F)F BYKDYFHHTYEOHI-UHFFFAOYSA-N 0.000 claims description 2
- RNBHWVXOUAWGAF-UHFFFAOYSA-N [2-(benzylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC=CC=C1)(F)F RNBHWVXOUAWGAF-UHFFFAOYSA-N 0.000 claims description 2
- KUXQKQBZSRCVMR-UHFFFAOYSA-N [2-(oxolan-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1COCC1)(F)F KUXQKQBZSRCVMR-UHFFFAOYSA-N 0.000 claims description 2
- PVHIYDYHJBOLQE-UHFFFAOYSA-N [2-(pyrazin-2-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=NC=CN=C1)(F)F PVHIYDYHJBOLQE-UHFFFAOYSA-N 0.000 claims description 2
- RVEGRXWHJYDYTJ-UHFFFAOYSA-N [2-(pyridin-2-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=NC=CC=C1)(F)F RVEGRXWHJYDYTJ-UHFFFAOYSA-N 0.000 claims description 2
- MSYLCKCGZCIYMR-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-(3-pyrrolidin-1-ylsulfonylphenyl)methanone Chemical compound N1(CCCC1)S(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1 MSYLCKCGZCIYMR-UHFFFAOYSA-N 0.000 claims description 2
- FDNUQWIQKUQTJF-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethoxy)phenyl]methanone Chemical compound FC(OC=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)(F)F FDNUQWIQKUQTJF-UHFFFAOYSA-N 0.000 claims description 2
- QOFNMBPZQWNZCA-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)(F)F QOFNMBPZQWNZCA-UHFFFAOYSA-N 0.000 claims description 2
- MXWUSRQAGSNPSW-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethylsulfanyl)phenyl]methanone Chemical compound FC(SC=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)(F)F MXWUSRQAGSNPSW-UHFFFAOYSA-N 0.000 claims description 2
- FIEPXJSTXWDING-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethylsulfonyl)phenyl]methanone Chemical compound FC(S(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)(F)F FIEPXJSTXWDING-UHFFFAOYSA-N 0.000 claims description 2
- NHSAIANWBNGPLB-UHFFFAOYSA-N [2-(pyrimidin-2-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=C(N=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C(F)(F)F NHSAIANWBNGPLB-UHFFFAOYSA-N 0.000 claims description 2
- KDLMSDUYXVQWFC-UHFFFAOYSA-N [2-(pyrimidin-4-ylmethylamino)-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=NC=NC=C1)(F)F KDLMSDUYXVQWFC-UHFFFAOYSA-N 0.000 claims description 2
- PTKCEQNPSJYQRP-UHFFFAOYSA-N [2-[(1-hydroxycyclopentyl)methylamino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1(CCCC1)O PTKCEQNPSJYQRP-UHFFFAOYSA-N 0.000 claims description 2
- UDOVVDXJXFFKBL-UHFFFAOYSA-N [2-[(1-hydroxycyclopentyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1(CCCC1)O)(F)F UDOVVDXJXFFKBL-UHFFFAOYSA-N 0.000 claims description 2
- PJOMLXCAQCNNAM-UHFFFAOYSA-N [2-[(1-methylimidazol-2-yl)methylamino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1N(C=CN=1)C PJOMLXCAQCNNAM-UHFFFAOYSA-N 0.000 claims description 2
- GPWFRUSYLXWMRD-UHFFFAOYSA-N [2-[(1-methylsulfonylcyclopentyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1(CCCC1)S(=O)(=O)C)(F)F GPWFRUSYLXWMRD-UHFFFAOYSA-N 0.000 claims description 2
- FSQWCXAOMTYHAU-UHFFFAOYSA-N [2-[(1-pyridin-3-ylcyclopropyl)amino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC1(CC1)C=1C=NC=CC=1)(F)F FSQWCXAOMTYHAU-UHFFFAOYSA-N 0.000 claims description 2
- LXXONRUETOPZOV-UHFFFAOYSA-N [2-[(2,3-difluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C(=CC=C1)F)F)(F)F LXXONRUETOPZOV-UHFFFAOYSA-N 0.000 claims description 2
- QUMHXHFHUZYHOJ-UHFFFAOYSA-N [2-[(2,4-difluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C=C(C=C1)F)F)(F)F QUMHXHFHUZYHOJ-UHFFFAOYSA-N 0.000 claims description 2
- FOULDWITDUOPEU-UHFFFAOYSA-N [2-[(2,5-difluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C=CC(=C1)F)F)(F)F FOULDWITDUOPEU-UHFFFAOYSA-N 0.000 claims description 2
- CARXBUCHZGAMKQ-UHFFFAOYSA-N [2-[(2,6-difluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C=CC=C1F)F)(F)F CARXBUCHZGAMKQ-UHFFFAOYSA-N 0.000 claims description 2
- MCZPQHAIEKGIFL-UHFFFAOYSA-N [2-[(2-bromophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C=CC=C1)Br)(F)F MCZPQHAIEKGIFL-UHFFFAOYSA-N 0.000 claims description 2
- LZPVUZJZPJFKOZ-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=C(C=CC=C1)F)(F)F LZPVUZJZPJFKOZ-UHFFFAOYSA-N 0.000 claims description 2
- KEINYCJVBRRHQZ-UHFFFAOYSA-N [2-[(2-hydroxy-1-pyridin-3-ylethyl)amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC(CO)C=1C=NC=CC=1 KEINYCJVBRRHQZ-UHFFFAOYSA-N 0.000 claims description 2
- UVHVIAHBKLJILH-UHFFFAOYSA-N [2-[(2-methylpyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C(=NC=CC=1)C)(F)F UVHVIAHBKLJILH-UHFFFAOYSA-N 0.000 claims description 2
- QUDOCNSAATWLME-UHFFFAOYSA-N [2-[(3,3-difluorocyclopentyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1CC(CC1)(F)F)(F)F QUDOCNSAATWLME-UHFFFAOYSA-N 0.000 claims description 2
- LWMCKNKJTOLYPF-UHFFFAOYSA-N [2-[(3,4-difluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC(=C(C=C1)F)F)(F)F LWMCKNKJTOLYPF-UHFFFAOYSA-N 0.000 claims description 2
- SRTMWGHYWSTNOC-UHFFFAOYSA-N [2-[(3-methylphenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC(=CC=C1)C)(F)F SRTMWGHYWSTNOC-UHFFFAOYSA-N 0.000 claims description 2
- CNLQKIQKTHVKQE-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound COC=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC=C(C=C1)F CNLQKIQKTHVKQE-UHFFFAOYSA-N 0.000 claims description 2
- UXBLVHYCIPWYMI-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound CC=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC=C(C=C1)F UXBLVHYCIPWYMI-UHFFFAOYSA-N 0.000 claims description 2
- JJPDURBHRSCUFD-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(1,3-thiazol-2-ylmethylsulfonyl)phenyl]methanone Chemical compound S1C(=NC=C1)CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC=C(C=C1)F JJPDURBHRSCUFD-UHFFFAOYSA-N 0.000 claims description 2
- QEOLFANJYWTBBH-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC1=CC=C(C=C1)F)(F)F QEOLFANJYWTBBH-UHFFFAOYSA-N 0.000 claims description 2
- UVWSVYSJCSSWER-UHFFFAOYSA-N [2-[(4-methylpyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1C)(F)F UVWSVYSJCSSWER-UHFFFAOYSA-N 0.000 claims description 2
- NBWBQCOJHXEEKF-UHFFFAOYSA-N [2-[(5-fluoropyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=C(C=1)F)(F)F NBWBQCOJHXEEKF-UHFFFAOYSA-N 0.000 claims description 2
- TVONTTSUJIFNIX-UHFFFAOYSA-N [2-[(5-hydroxypyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=C(C=1)O)(F)F TVONTTSUJIFNIX-UHFFFAOYSA-N 0.000 claims description 2
- YKIUGQSATIOMHC-UHFFFAOYSA-N [2-[(5-methoxypyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=C(C=1)OC)(F)F YKIUGQSATIOMHC-UHFFFAOYSA-N 0.000 claims description 2
- DZPJCNALOUKVOA-UHFFFAOYSA-N [2-[(5-methylpyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=C(C=1)C)(F)F DZPJCNALOUKVOA-UHFFFAOYSA-N 0.000 claims description 2
- SORZEHKXBHNBHC-UHFFFAOYSA-N [2-[(6-methylpyridin-3-yl)methylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC(=CC=1)C)(F)F SORZEHKXBHNBHC-UHFFFAOYSA-N 0.000 claims description 2
- OFZPPFLTURKIDF-UHFFFAOYSA-N [2-[1-(4-fluorophenyl)cyclobutyl]-1,3-thiazol-5-yl]-[3-(trifluoromethylsulfonyl)phenyl]methanone Chemical compound FC(S(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)C1(CCC1)C1=CC=C(C=C1)F)(F)F OFZPPFLTURKIDF-UHFFFAOYSA-N 0.000 claims description 2
- QRDXWZFSROIGOA-UHFFFAOYSA-N [2-[2-(4-fluorophenyl)ethylamino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCCC1=CC=C(C=C1)F)(F)F QRDXWZFSROIGOA-UHFFFAOYSA-N 0.000 claims description 2
- PQISRYTVCXCUIO-GXTWGEPZSA-N [2-[[(1S,2R)-2-hydroxycyclopentyl]methylamino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC[C@H]1[C@@H](CCC1)O PQISRYTVCXCUIO-GXTWGEPZSA-N 0.000 claims description 2
- IOYPSDSDOLAWRU-UHFFFAOYSA-N [2-[[1-(4-fluorophenyl)cyclobutyl]amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC1(CCC1)C1=CC=C(C=C1)F IOYPSDSDOLAWRU-UHFFFAOYSA-N 0.000 claims description 2
- SNZDSAYKWFMEOV-UHFFFAOYSA-N [2-[[1-(4-fluorophenyl)cyclobutyl]amino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC1(CCC1)C1=CC=C(C=C1)F)(F)F SNZDSAYKWFMEOV-UHFFFAOYSA-N 0.000 claims description 2
- ARFXJNXTNIUWOX-UHFFFAOYSA-N [2-[[1-(4-fluorophenyl)cyclopropyl]amino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC1(CC1)C1=CC=C(C=C1)F)(F)F ARFXJNXTNIUWOX-UHFFFAOYSA-N 0.000 claims description 2
- GZVNMIWZFYBSCB-UHFFFAOYSA-N [2-[[3-(4-fluorophenyl)oxetan-3-yl]amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NC1(COC1)C1=CC=C(C=C1)F GZVNMIWZFYBSCB-UHFFFAOYSA-N 0.000 claims description 2
- OISKFWPFACTXGK-UHFFFAOYSA-N [2-[cyclopropyl(2-pyridin-3-ylethyl)amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)N(CCC=1C=NC=CC=1)C1CC1 OISKFWPFACTXGK-UHFFFAOYSA-N 0.000 claims description 2
- XXCLIBYZVIQKNF-UHFFFAOYSA-N [2-[methyl(2-pyridin-3-ylethyl)amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)N(CCC=1C=NC=CC=1)C XXCLIBYZVIQKNF-UHFFFAOYSA-N 0.000 claims description 2
- RZJJXDLRDNEIJI-UHFFFAOYSA-N [2-[methyl(pyridin-3-ylmethyl)amino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)N(CC=1C=NC=CC=1)C)(F)F RZJJXDLRDNEIJI-UHFFFAOYSA-N 0.000 claims description 2
- RVPXPHOFUGVWJP-UHFFFAOYSA-N [2-[methyl-(2-methyl-1-pyridin-3-ylpropyl)amino]-1,3-thiazol-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)N(C(C(C)C)C=1C=NC=CC=1)C RVPXPHOFUGVWJP-UHFFFAOYSA-N 0.000 claims description 2
- POXWZNKLAHVEFQ-UHFFFAOYSA-N [3-(1H-pyrazol-5-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC=NN1 POXWZNKLAHVEFQ-UHFFFAOYSA-N 0.000 claims description 2
- MSFPQUNBXZKBDN-UHFFFAOYSA-N [3-(2,4-dimethylpyrazol-3-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=C(C=NN1C)C MSFPQUNBXZKBDN-UHFFFAOYSA-N 0.000 claims description 2
- NXJHTRPFGHTAGA-UHFFFAOYSA-N [3-(2,5-dimethylpyrazol-3-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC(=NN1C)C NXJHTRPFGHTAGA-UHFFFAOYSA-N 0.000 claims description 2
- JZNGRUVDGOMKDS-UHFFFAOYSA-N [3-(2-phenylpyrazol-3-yl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC=NN1C1=CC=CC=C1 JZNGRUVDGOMKDS-UHFFFAOYSA-N 0.000 claims description 2
- CMPARGONARYDED-UHFFFAOYSA-N [3-(4-fluorophenyl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)C1=CC=C(C=C1)F CMPARGONARYDED-UHFFFAOYSA-N 0.000 claims description 2
- JYWMSGJRALFGKL-UHFFFAOYSA-N [3-(pentafluoro-lambda6-sulfanyl)phenyl]-[2-(pyridin-3-ylmethylamino)-1,3-thiazol-5-yl]methanone Chemical compound FS(C=1C=C(C=CC=1)C(=O)C1=CN=C(S1)NCC=1C=NC=CC=1)(F)(F)(F)F JYWMSGJRALFGKL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 160
- 238000005160 1H NMR spectroscopy Methods 0.000 description 107
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 83
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 77
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 59
- 201000010099 disease Diseases 0.000 description 46
- 239000000203 mixture Substances 0.000 description 42
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 39
- 239000003795 chemical substances by application Substances 0.000 description 36
- OVSMURBVBQUOSF-UHFFFAOYSA-N 3-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=CC(C=O)=C1 OVSMURBVBQUOSF-UHFFFAOYSA-N 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 208000027866 inflammatory disease Diseases 0.000 description 23
- 125000002950 monocyclic group Chemical group 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 239000005557 antagonist Substances 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 208000035475 disorder Diseases 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000556 agonist Substances 0.000 description 11
- 125000002619 bicyclic group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 201000011040 acute kidney failure Diseases 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- RYGOBSYXIIUFOR-UHFFFAOYSA-N (1-methylpyrazol-4-yl)boronic acid Chemical compound CN1C=C(B(O)O)C=N1 RYGOBSYXIIUFOR-UHFFFAOYSA-N 0.000 description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 201000009594 Systemic Scleroderma Diseases 0.000 description 9
- 206010042953 Systemic sclerosis Diseases 0.000 description 9
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 9
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 208000030159 metabolic disease Diseases 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 8
- 208000028622 Immune thrombocytopenia Diseases 0.000 description 8
- 206010061218 Inflammation Diseases 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 208000002193 Pain Diseases 0.000 description 8
- 201000004681 Psoriasis Diseases 0.000 description 8
- 229940125708 antidiabetic agent Drugs 0.000 description 8
- 239000003472 antidiabetic agent Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 230000001684 chronic effect Effects 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 201000003067 thrombocytopenia due to platelet alloimmunization Diseases 0.000 description 8
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 7
- 208000024172 Cardiovascular disease Diseases 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 230000001154 acute effect Effects 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 208000016097 disease of metabolism Diseases 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 6
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 230000001363 autoimmune Effects 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 201000001421 hyperglycemia Diseases 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 230000036542 oxidative stress Effects 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- WWTWOLHPDSNPRP-UHFFFAOYSA-N 3-(2-chloro-1,3-thiazole-5-carbonyl)benzonitrile Chemical compound ClC=1SC(=CN=1)C(=O)C=1C=C(C#N)C=CC=1 WWTWOLHPDSNPRP-UHFFFAOYSA-N 0.000 description 5
- BUXMJMHFPYNLAJ-UHFFFAOYSA-N 3-(trifluoromethylsulfonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)C(F)(F)F)=C1 BUXMJMHFPYNLAJ-UHFFFAOYSA-N 0.000 description 5
- 208000023275 Autoimmune disease Diseases 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010016654 Fibrosis Diseases 0.000 description 5
- 201000005569 Gout Diseases 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 5
- 229940005513 antidepressants Drugs 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 5
- 230000004761 fibrosis Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 206010020718 hyperplasia Diseases 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 description 5
- 230000000155 isotopic effect Effects 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229960003151 mercaptamine Drugs 0.000 description 5
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 description 5
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 4
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 4
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 4
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 description 4
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 4
- 206010012289 Dementia Diseases 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 206010018364 Glomerulonephritis Diseases 0.000 description 4
- 102000004877 Insulin Human genes 0.000 description 4
- 108090001061 Insulin Proteins 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 102000002689 Toll-like receptor Human genes 0.000 description 4
- 108020000411 Toll-like receptor Proteins 0.000 description 4
- 206010047115 Vasculitis Diseases 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229960003180 glutathione Drugs 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 230000004968 inflammatory condition Effects 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 208000017169 kidney disease Diseases 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 201000006417 multiple sclerosis Diseases 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 230000000626 neurodegenerative effect Effects 0.000 description 4
- 230000002314 neuroinflammatory effect Effects 0.000 description 4
- 201000008482 osteoarthritis Diseases 0.000 description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 description 4
- 229940055726 pantothenic acid Drugs 0.000 description 4
- 235000019161 pantothenic acid Nutrition 0.000 description 4
- 239000011713 pantothenic acid Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 3
- LHUUOGVUZRDYBW-UHFFFAOYSA-N 3-[(2-chloro-1,3-thiazol-5-yl)-hydroxymethyl]benzonitrile Chemical compound ClC=1SC(=CN=1)C(C=1C=C(C#N)C=CC=1)O LHUUOGVUZRDYBW-UHFFFAOYSA-N 0.000 description 3
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 3
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 3
- 208000009304 Acute Kidney Injury Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 description 3
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 description 3
- 229940127291 Calcium channel antagonist Drugs 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 3
- 108010011459 Exenatide Proteins 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 102000014150 Interferons Human genes 0.000 description 3
- 108010050904 Interferons Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 3
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- 208000033626 Renal failure acute Diseases 0.000 description 3
- 206010039710 Scleroderma Diseases 0.000 description 3
- 102100036922 Tumor necrosis factor ligand superfamily member 13B Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000002249 anxiolytic agent Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000012131 assay buffer Substances 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000000480 calcium channel blocker Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 208000033679 diabetic kidney disease Diseases 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 235000009200 high fat diet Nutrition 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000007954 hypoxia Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000028709 inflammatory response Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229940125396 insulin Drugs 0.000 description 3
- 102000006495 integrins Human genes 0.000 description 3
- 108010044426 integrins Proteins 0.000 description 3
- 230000037356 lipid metabolism Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229960001078 lithium Drugs 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 3
- 210000004877 mucosa Anatomy 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- USRYWZFLGFQQEB-UHFFFAOYSA-N pyrimidin-5-ylmethanamine Chemical compound NCC1=CN=CN=C1 USRYWZFLGFQQEB-UHFFFAOYSA-N 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 229940044601 receptor agonist Drugs 0.000 description 3
- 239000000018 receptor agonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 230000000306 recurrent effect Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 3
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 3
- 239000007909 solid dosage form Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- UJLAWZDWDVHWOW-YPMHNXCESA-N tofacitinib Chemical compound C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)C1=NC=NC2=C1C=CN2 UJLAWZDWDVHWOW-YPMHNXCESA-N 0.000 description 3
- 229960001722 verapamil Drugs 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 2
- 0 *C(N(*)c1ncc(C(c2c(*)c(*)c(*)c(*)c2*)=O)[s]1)=* Chemical compound *C(N(*)c1ncc(C(c2c(*)c(*)c(*)c(*)c2*)=O)[s]1)=* 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 102100024341 10 kDa heat shock protein, mitochondrial Human genes 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- MCIDWGZGWVSZMK-UHFFFAOYSA-N 2-[6-(1h-indol-4-yl)-1h-indazol-4-yl]-5-[(4-propan-2-ylpiperazin-1-yl)methyl]-1,3-oxazole Chemical compound C1CN(C(C)C)CCN1CC1=CN=C(C=2C=3C=NNC=3C=C(C=2)C=2C=3C=CNC=3C=CC=2)O1 MCIDWGZGWVSZMK-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- KLEYVGWAORGTIT-UHFFFAOYSA-N 2-chlorothiazole Chemical compound ClC1=NC=CS1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 2
- ZYUAOEFMKIYOPZ-UHFFFAOYSA-N 3-(dimethylsulfamoyl)benzoic acid Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C(O)=O)=C1 ZYUAOEFMKIYOPZ-UHFFFAOYSA-N 0.000 description 2
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- LAMQVIQMVKWXOC-UHFFFAOYSA-N 4-methyl-n-[2-[3-(morpholin-4-ylmethyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2C=NC=CC=2)SC=1C(=O)NC1=CC=CC=C1C(N=C1SC=2)=CN1C=2CN1CCOCC1 LAMQVIQMVKWXOC-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- KHOITXIGCFIULA-UHFFFAOYSA-N Alophen Chemical compound C1=CC(OC(=O)C)=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OC(C)=O)C=C1 KHOITXIGCFIULA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 108010058207 Anistreplase Proteins 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 108010087765 Antipain Proteins 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 208000020084 Bone disease Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 description 2
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 2
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 2
- 102100031168 CCN family member 2 Human genes 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 108010059013 Chaperonin 10 Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 229920001268 Cholestyramine Polymers 0.000 description 2
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 description 2
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 2
- 208000015943 Coeliac disease Diseases 0.000 description 2
- 108010039419 Connective Tissue Growth Factor Proteins 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010012434 Dermatitis allergic Diseases 0.000 description 2
- 102100035762 Diacylglycerol O-acyltransferase 2 Human genes 0.000 description 2
- 101710167503 Diacylglycerol O-acyltransferase 2 Proteins 0.000 description 2
- 206010052337 Diastolic dysfunction Diseases 0.000 description 2
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 description 2
- HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 102100040133 Free fatty acid receptor 2 Human genes 0.000 description 2
- 102100025353 G-protein coupled bile acid receptor 1 Human genes 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000890668 Homo sapiens Free fatty acid receptor 2 Proteins 0.000 description 2
- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 description 2
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 2
- 102100030643 Hydroxycarboxylic acid receptor 2 Human genes 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 201000001431 Hyperuricemia Diseases 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 description 2
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 description 2
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 2
- 208000012659 Joint disease Diseases 0.000 description 2
- 208000005777 Lupus Nephritis Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010026749 Mania Diseases 0.000 description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 208000029578 Muscle disease Diseases 0.000 description 2
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
- 206010029164 Nephrotic syndrome Diseases 0.000 description 2
- 108090000028 Neprilysin Proteins 0.000 description 2
- 102000003729 Neprilysin Human genes 0.000 description 2
- PETUGLVTOGGZJT-UHFFFAOYSA-N OC(c1cc(C(c2cnc(NCc3cnccc3)[s]2)=O)ccc1)=O Chemical compound OC(c1cc(C(c2cnc(NCc3cnccc3)[s]2)=O)ccc1)=O PETUGLVTOGGZJT-UHFFFAOYSA-N 0.000 description 2
- 208000025157 Oral disease Diseases 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- ZNXZGRMVNNHPCA-UHFFFAOYSA-N Pantetheine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- 102000003923 Protein Kinase C Human genes 0.000 description 2
- 108090000315 Protein Kinase C Proteins 0.000 description 2
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 108091006277 SLC5A1 Proteins 0.000 description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 2
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 2
- 102100021495 Solute carrier family 22 member 12 Human genes 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 102000000551 Syk Kinase Human genes 0.000 description 2
- 108010016672 Syk Kinase Proteins 0.000 description 2
- 102000003623 TRPC6 Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 2
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 2
- 239000004012 Tofacitinib Substances 0.000 description 2
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 description 2
- 102100039390 Toll-like receptor 7 Human genes 0.000 description 2
- 102100033117 Toll-like receptor 9 Human genes 0.000 description 2
- 102000004357 Transferases Human genes 0.000 description 2
- 108090000992 Transferases Proteins 0.000 description 2
- 108050001421 Transient receptor potential channel, canonical 6 Proteins 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- 206010047249 Venous thrombosis Diseases 0.000 description 2
- 229930003571 Vitamin B5 Natural products 0.000 description 2
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 206010000891 acute myocardial infarction Diseases 0.000 description 2
- 239000000048 adrenergic agonist Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- OGWAVGNOAMXIIM-UHFFFAOYSA-N albiglutide Chemical compound O=C(O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)CNC(=O)C(N)CC=1(N=CNC=1))CCC(=O)O)C(O)C)CC2(=CC=CC=C2))C(O)C)CO)CC(=O)O)C(C)C)CO)CO)CC3(=CC=C(O)C=C3))CC(C)C)CCC(=O)O)CCC(=O)N)C)C)CCCCN)CCC(=O)O)CC4(=CC=CC=C4))C(CC)C)C)CC=6(C5(=C(C=CC=C5)NC=6)))CC(C)C)C(C)C)CCCCN)CCCNC(=N)N OGWAVGNOAMXIIM-UHFFFAOYSA-N 0.000 description 2
- 229960004733 albiglutide Drugs 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 229940083712 aldosterone antagonist Drugs 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- JSWZEAMFRNKZNL-UHFFFAOYSA-N alosetron Chemical compound N1C=NC(CN2C(C3=C(N(C4=CC=CC=C43)C)CC2)=O)=C1C JSWZEAMFRNKZNL-UHFFFAOYSA-N 0.000 description 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 2
- 229960000528 amlodipine Drugs 0.000 description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000007131 anti Alzheimer effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000003529 anticholesteremic agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 2
- 229960004676 antithrombotic agent Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- XUZMWHLSFXCVMG-UHFFFAOYSA-N baricitinib Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 XUZMWHLSFXCVMG-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- PQPLTRKVISEBJL-UHFFFAOYSA-N bis(2-methylsulfonylphenyl)methanone Chemical compound CS(=O)(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1S(C)(=O)=O PQPLTRKVISEBJL-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 2
- 229960002079 calcium pantothenate Drugs 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940097217 cardiac glycoside Drugs 0.000 description 2
- 239000002368 cardiac glycoside Substances 0.000 description 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- LPAUOXUZGSBGDU-STDDISTJSA-N chembl1096146 Chemical compound O=C1N(C=2C(=CC=CC=2)C)C(=N/CCC)/S\C1=C/C1=CC=C(OC[C@H](O)CO)C(Cl)=C1 LPAUOXUZGSBGDU-STDDISTJSA-N 0.000 description 2
- DREIJXJRTLTGJC-ZLBJMMTISA-N chembl3137308 Chemical compound C([C@H]1C[C@@](O)(C2)C3)C2C[C@H]3[C@H]1NC1=C2C=CNC2=NC=C1C(=O)N DREIJXJRTLTGJC-ZLBJMMTISA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229960003728 ciclesonide Drugs 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 2
- 239000005516 coenzyme A Substances 0.000 description 2
- 229940093530 coenzyme a Drugs 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 2
- 229940099500 cystamine Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 2
- 201000001981 dermatomyositis Diseases 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 125000004212 difluorophenyl group Chemical group 0.000 description 2
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 2
- 229960004166 diltiazem Drugs 0.000 description 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 2
- HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229960001519 exenatide Drugs 0.000 description 2
- 239000003527 fibrinolytic agent Substances 0.000 description 2
- 230000003176 fibrotic effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 208000007565 gingivitis Diseases 0.000 description 2
- 229960004580 glibenclamide Drugs 0.000 description 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003862 health status Effects 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 208000018706 hematopoietic system disease Diseases 0.000 description 2
- 208000007475 hemolytic anemia Diseases 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- RDOIQAHITMMDAJ-UHFFFAOYSA-N loperamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 RDOIQAHITMMDAJ-UHFFFAOYSA-N 0.000 description 2
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 208000024714 major depressive disease Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 2
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 2
- 229960004963 mesalazine Drugs 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000006384 methylpyridyl group Chemical group 0.000 description 2
- 239000002394 mineralocorticoid antagonist Substances 0.000 description 2
- 208000030194 mouth disease Diseases 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960002009 naproxen Drugs 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-M naproxen(1-) Chemical compound C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-M 0.000 description 2
- 230000009826 neoplastic cell growth Effects 0.000 description 2
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
- 229960001597 nifedipine Drugs 0.000 description 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 229960002657 orciprenaline Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- CINJIXGRSTYIHP-UHFFFAOYSA-N oxolan-3-ylmethanamine Chemical compound NCC1CCOC1 CINJIXGRSTYIHP-UHFFFAOYSA-N 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 2
- 229960002702 piroxicam Drugs 0.000 description 2
- 229960002797 pitavastatin Drugs 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 102000054765 polymorphisms of proteins Human genes 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 108700027806 rGLP-1 Proteins 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 238000007634 remodeling Methods 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- YOZBGTLTNGAVFU-UHFFFAOYSA-N roxadustat Chemical compound C1=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 YOZBGTLTNGAVFU-UHFFFAOYSA-N 0.000 description 2
- 229960002052 salbutamol Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229960003310 sildenafil Drugs 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- OAVGBZOFDPFGPJ-UHFFFAOYSA-N sotrastaurin Chemical compound C1CN(C)CCN1C1=NC(C=2C(NC(=O)C=2C=2C3=CC=CC=C3NC=2)=O)=C(C=CC=C2)C2=N1 OAVGBZOFDPFGPJ-UHFFFAOYSA-N 0.000 description 2
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 2
- 229960002256 spironolactone Drugs 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229930002534 steroid glycoside Natural products 0.000 description 2
- 150000008143 steroidal glycosides Chemical class 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229960001940 sulfasalazine Drugs 0.000 description 2
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 2
- 229960000894 sulindac Drugs 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- RRNKBPDIEQLQEW-UHFFFAOYSA-N tert-butyl 3-[2-(pyridin-3-ylmethylamino)-1,3-thiazole-5-carbonyl]benzoate Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C=1C=C(C(=O)OC(C)(C)C)C=CC=1 RRNKBPDIEQLQEW-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- 208000037816 tissue injury Diseases 0.000 description 2
- 229960000187 tissue plasminogen activator Drugs 0.000 description 2
- 229960001350 tofacitinib Drugs 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 235000009492 vitamin B5 Nutrition 0.000 description 2
- 239000011675 vitamin B5 Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- PZSMLGOAJXSDMK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methanamine Chemical compound CN1C=CN=C1CN PZSMLGOAJXSDMK-UHFFFAOYSA-N 0.000 description 1
- YIHCDJHLBGVHNU-UHFFFAOYSA-N (1-methylsulfonylcyclopentyl)methanamine Chemical compound CS(=O)(=O)C1(CN)CCCC1 YIHCDJHLBGVHNU-UHFFFAOYSA-N 0.000 description 1
- AUOZFCSMXYBIQW-UHFFFAOYSA-N (1-phenylcyclobutyl)methanamine Chemical compound C=1C=CC=CC=1C1(CN)CCC1 AUOZFCSMXYBIQW-UHFFFAOYSA-N 0.000 description 1
- VORALDSQPSWPRK-NTSWFWBYSA-N (1r,2s)-2-(aminomethyl)cyclopentan-1-ol Chemical compound NC[C@@H]1CCC[C@H]1O VORALDSQPSWPRK-NTSWFWBYSA-N 0.000 description 1
- CNXNMLQATFFYLX-ICTDYHGOSA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5s)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol;[2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-fluoro-11-hydroxy-10,13,16-trime Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CNXNMLQATFFYLX-ICTDYHGOSA-N 0.000 description 1
- VORALDSQPSWPRK-RITPCOANSA-N (1s,2r)-2-(aminomethyl)cyclopentan-1-ol Chemical compound NC[C@H]1CCC[C@@H]1O VORALDSQPSWPRK-RITPCOANSA-N 0.000 description 1
- OHZUCDHZOHSBPZ-UHFFFAOYSA-N (2,3-difluorophenyl)methanamine Chemical compound NCC1=CC=CC(F)=C1F OHZUCDHZOHSBPZ-UHFFFAOYSA-N 0.000 description 1
- QDZZDVQGBKTLHV-UHFFFAOYSA-N (2,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1F QDZZDVQGBKTLHV-UHFFFAOYSA-N 0.000 description 1
- GDFBHCMFIUBEQT-UHFFFAOYSA-N (2,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC=C1F GDFBHCMFIUBEQT-UHFFFAOYSA-N 0.000 description 1
- PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 description 1
- NOYASZMZIBFFNZ-UHFFFAOYSA-N (2-bromophenyl)methanamine Chemical compound NCC1=CC=CC=C1Br NOYASZMZIBFFNZ-UHFFFAOYSA-N 0.000 description 1
- CSZDQVCUINDZJP-UHFFFAOYSA-N (2-chloro-1,3-thiazol-5-yl)-[3-(1,3-thiazol-2-ylmethylsulfonyl)phenyl]methanol Chemical compound ClC=1SC(=CN=1)C(O)C1=CC(=CC=C1)S(=O)(=O)CC=1SC=CN=1 CSZDQVCUINDZJP-UHFFFAOYSA-N 0.000 description 1
- QWSVMRONVPFFDA-UHFFFAOYSA-N (2-chloro-1,3-thiazol-5-yl)-[3-(trifluoromethylsulfanyl)phenyl]methanol Chemical compound ClC=1SC(=CN=1)C(O)C1=CC(=CC=C1)SC(F)(F)F QWSVMRONVPFFDA-UHFFFAOYSA-N 0.000 description 1
- LDHIJHYWTWVSMX-UHFFFAOYSA-N (2-chloro-1,3-thiazol-5-yl)-[3-(trifluoromethylsulfonyl)phenyl]methanone Chemical compound ClC=1SC(=CN=1)C(=O)C1=CC(=CC=C1)S(=O)(=O)C(F)(F)F LDHIJHYWTWVSMX-UHFFFAOYSA-N 0.000 description 1
- LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 1
- UYYOZFLVQQRFBD-UHFFFAOYSA-N (2-methoxycyclopentyl)methanamine Chemical compound COC1CCCC1CN UYYOZFLVQQRFBD-UHFFFAOYSA-N 0.000 description 1
- YMROUWDKBBTAPS-UHFFFAOYSA-N (2-methylpyridin-3-yl)methanamine Chemical compound CC1=NC=CC=C1CN YMROUWDKBBTAPS-UHFFFAOYSA-N 0.000 description 1
- PLXNYYYHSZRVJH-UHFFFAOYSA-N (2-pyrrolidin-1-ylphenyl)methanamine Chemical compound NCC1=CC=CC=C1N1CCCC1 PLXNYYYHSZRVJH-UHFFFAOYSA-N 0.000 description 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- YWPHCCPCQOJSGZ-LLVKDONJSA-N (2r)-2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OC[C@@H]1OCCNC1 YWPHCCPCQOJSGZ-LLVKDONJSA-N 0.000 description 1
- ZEYYDOLCHFETHQ-JOCHJYFZSA-N (2r)-2-cyclopentyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic acid Chemical compound C1([C@@H](C(=O)O)C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)CCCC1 ZEYYDOLCHFETHQ-JOCHJYFZSA-N 0.000 description 1
- FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 description 1
- NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 description 1
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- DXRXYJYFADHAPA-AUTRQRHGSA-N (2s)-2-[[2-[[(2s)-5-amino-2-[[(2s)-2-aminopropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)N DXRXYJYFADHAPA-AUTRQRHGSA-N 0.000 description 1
- YOKBGCTZYPOSQM-HPSWDUTRSA-N (2s)-2-acetamido-n-[(3s,9s,12s,15r,18s)-15-(cyclohexylmethyl)-9-[3-(diaminomethylideneamino)propyl]-12-(1h-indol-3-ylmethyl)-2,8,11,14,17-pentaoxo-1,7,10,13,16-pentazabicyclo[16.3.0]henicosan-3-yl]-3-phenylpropanamide Chemical compound C([C@H](NC(=O)C)C(=O)N[C@@H]1C(N2CCC[C@H]2C(=O)N[C@H](CC2CCCCC2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCCC1)=O)C1=CC=CC=C1 YOKBGCTZYPOSQM-HPSWDUTRSA-N 0.000 description 1
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical compound OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 description 1
- SFVLTCAESLKEHH-WKAQUBQDSA-N (2s)-6-amino-2-[[(2s)-2-[[(2r)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-n-[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]hexanamide Chemical compound CC1=CC(O)=CC(C)=C1C[C@H](NC(=O)[C@H](N)CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N)=O)CC1=CC=CC=C1 SFVLTCAESLKEHH-WKAQUBQDSA-N 0.000 description 1
- ISOCDPQFIXDIMS-QHCPKHFHSA-N (2s)-n-[4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1NCCC1)NC(C=C1)=CC=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1N1CCOCC1 ISOCDPQFIXDIMS-QHCPKHFHSA-N 0.000 description 1
- PUTJFIQGLGDLIT-RNDOZLNUSA-N (2s,3s,3ar,5as,9as,9br)-3-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-3,4,5,5a,7,8,9,9b-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde Chemical compound C=1([C@@H](O)C[C@H]2[C@@]3(C)[C@@H]([C@]4(CCCC(C)(C)[C@@H]4CC3)C)C[C@]2(C)C=O)C=COC=1 PUTJFIQGLGDLIT-RNDOZLNUSA-N 0.000 description 1
- NPBCMXATLRCCLF-IRRLEISYSA-N (2s,4r)-4-[(3r,5s,6r,7r,8r,9s,10s,12s,13r,14s,17r)-6-ethyl-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2C[C@H](O)[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 NPBCMXATLRCCLF-IRRLEISYSA-N 0.000 description 1
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
- MBNJAGKPJGONBM-UHFFFAOYSA-N (3,3-difluorocyclopentyl)methanamine Chemical compound NCC1CCC(F)(F)C1 MBNJAGKPJGONBM-UHFFFAOYSA-N 0.000 description 1
- PHLZUDXEBCQHKM-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1 PHLZUDXEBCQHKM-UHFFFAOYSA-N 0.000 description 1
- QVSVMNXRLWSNGS-UHFFFAOYSA-N (3-fluorophenyl)methanamine Chemical compound NCC1=CC=CC(F)=C1 QVSVMNXRLWSNGS-UHFFFAOYSA-N 0.000 description 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
- IIFVWLUQBAIPMJ-ZFJHNFROSA-N (4-fluorophenyl)methanamine Chemical group NC[13C]1=[13CH][13CH]=[13C](F)[13CH]=[13CH]1 IIFVWLUQBAIPMJ-ZFJHNFROSA-N 0.000 description 1
- VLIQJGACTLGWCQ-UHFFFAOYSA-N (4-methylpyridin-3-yl)methanamine Chemical compound CC1=CC=NC=C1CN VLIQJGACTLGWCQ-UHFFFAOYSA-N 0.000 description 1
- XTAUIEMSNCLHEG-GGVFYUGVSA-N (4S)-4-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phosphonooxypropanoyl]amino]acetyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-3-methylpentanoyl]amino]-5-[[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-5-oxopentanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CCCNC(N)=N)[C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](COP(O)(O)=O)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C1=CN=CN1 XTAUIEMSNCLHEG-GGVFYUGVSA-N 0.000 description 1
- MQXRTCVZPIHBLD-TUAOUCFPSA-N (4s)-5-[[(1s)-1-carboxyethyl]amino]-4-[5-[(3r)-dithiolan-3-yl]pentanoylamino]-5-oxopentanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)CCCC[C@@H]1CCSS1 MQXRTCVZPIHBLD-TUAOUCFPSA-N 0.000 description 1
- RYICOVXDBBDCNT-UHFFFAOYSA-N (5-fluoropyridin-3-yl)methanamine Chemical compound NCC1=CN=CC(F)=C1 RYICOVXDBBDCNT-UHFFFAOYSA-N 0.000 description 1
- HODRJLWIXVIVOC-UHFFFAOYSA-N (5-methoxypyridin-3-yl)methanamine Chemical compound COC1=CN=CC(CN)=C1 HODRJLWIXVIVOC-UHFFFAOYSA-N 0.000 description 1
- NXTVBKWLOZSCQE-UHFFFAOYSA-N (5-methylpyridin-2-yl)methanamine Chemical compound CC1=CC=C(CN)N=C1 NXTVBKWLOZSCQE-UHFFFAOYSA-N 0.000 description 1
- ZKAUZQFUIATOQP-UHFFFAOYSA-N (5-methylpyridin-3-yl)methanamine Chemical compound CC1=CN=CC(CN)=C1 ZKAUZQFUIATOQP-UHFFFAOYSA-N 0.000 description 1
- SHWPFRVVBIKGAT-LYWBODIJSA-N (5R,15'S,18'R)-3-(2-methoxyethyl)-15'-methylspiro[1,3-oxazolidine-5,16'-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8,10,12,20,22,24,26-nonaene]-2,3',4-trione Chemical compound COCCN1C(=O)O[C@@]2(C[C@H]3O[C@]2(C)n2c4ccccc4c4c5CNC(=O)c5c5c6ccccc6n3c5c24)C1=O SHWPFRVVBIKGAT-LYWBODIJSA-N 0.000 description 1
- QJLPWVUZFKETMK-LLVKDONJSA-N (5r)-1,5,7,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1C[C@@H](O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-LLVKDONJSA-N 0.000 description 1
- IJXJGQCXFSSHNL-QMMMGPOBSA-N (R)-(-)-2-Phenylglycinol Chemical compound OC[C@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-QMMMGPOBSA-N 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- NNYBQONXHNTVIJ-QGZVFWFLSA-N (R)-etodolac Chemical compound C1CO[C@](CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-QGZVFWFLSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 description 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- ZLKZGKDNYHEPFV-UHFFFAOYSA-N 1,3-oxazol-2-ylmethanamine Chemical compound NCC1=NC=CO1 ZLKZGKDNYHEPFV-UHFFFAOYSA-N 0.000 description 1
- JOZSYOPADROCMP-UHFFFAOYSA-N 1,3-thiazol-2-ylmethanamine Chemical compound NCC1=NC=CS1 JOZSYOPADROCMP-UHFFFAOYSA-N 0.000 description 1
- YFEQTUUFQKDATK-UHFFFAOYSA-N 1,3-thiazol-4-ylmethanamine Chemical compound NCC1=CSC=N1 YFEQTUUFQKDATK-UHFFFAOYSA-N 0.000 description 1
- XDNQVUAKCAPBIG-UHFFFAOYSA-N 1,3-thiazol-5-ylmethanamine Chemical compound NCC1=CN=CS1 XDNQVUAKCAPBIG-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- ZUHZNKJIJDAJFD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 ZUHZNKJIJDAJFD-UHFFFAOYSA-N 0.000 description 1
- FVJCUZCRPIMVLB-UHFFFAOYSA-N 1-(2-propan-2-yloxyethyl)-2-sulfanylidene-5h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound O=C1NC(=S)N(CCOC(C)C)C2=C1NC=C2 FVJCUZCRPIMVLB-UHFFFAOYSA-N 0.000 description 1
- MMSNEKOTSJRTRI-LLVKDONJSA-N 1-[(2r)-4-[5-[(4-fluorophenyl)methyl]thiophen-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound S1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1CC1=CC=C(F)C=C1 MMSNEKOTSJRTRI-LLVKDONJSA-N 0.000 description 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
- NGYNBSHYFOFVLS-LBPRGKRZSA-N 1-[4-chloro-2-hydroxy-3-[(3s)-piperidin-3-yl]sulfonylphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)[C@@H]2CNCCC2)=C1O NGYNBSHYFOFVLS-LBPRGKRZSA-N 0.000 description 1
- VGEXRDWWPSGZDH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]-3-[[2-[[3-[2-(2-hydroxyethylsulfanyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl]sulfanyl]phenyl]methyl]urea Chemical compound C=1C=C(O)C(Cl)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NCC1=CC=CC=C1SC(=CN12)C=CC1=NN=C2C1=CC=CC=C1SCCO VGEXRDWWPSGZDH-UHFFFAOYSA-N 0.000 description 1
- LNMRSSIMGCDUTP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[[5-fluoro-2-[1-(2-hydroxyethyl)indazol-5-yl]oxyphenyl]methyl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NCC=2C(=CC=C(F)C=2)OC=2C=C3C=NN(CCO)C3=CC=2)=CC(C(C)(C)C)=N1 LNMRSSIMGCDUTP-UHFFFAOYSA-N 0.000 description 1
- LLJFMFZYVVLQKT-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea Chemical compound C=1C(OC)=CC=C(C(C2=O)(C)C)C=1C(=O)N2CCC(C=C1)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 LLJFMFZYVVLQKT-UHFFFAOYSA-N 0.000 description 1
- VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LIDZELUIEIAIDJ-UHFFFAOYSA-N 1h-pyrazol-4-ylmethanamine Chemical compound NCC=1C=NNC=1 LIDZELUIEIAIDJ-UHFFFAOYSA-N 0.000 description 1
- IYSPNYLFKSTATA-UHFFFAOYSA-N 1h-pyrazol-5-ylmethanamine Chemical compound NCC=1C=CNN=1 IYSPNYLFKSTATA-UHFFFAOYSA-N 0.000 description 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 1
- HRCMXYXVAWHBTH-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazole Chemical compound C1=CC=C2OCNC2=C1 HRCMXYXVAWHBTH-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- LATZVDXOTDYECD-UFTFXDLESA-N 2,3-dihydroxybutanedioic acid (3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide tetrahydrate Chemical compound O.O.O.O.OC(C(O)C(O)=O)C(O)=O.CC[C@@H]1CN(C[C@@H]1c1cnc2cnc3[nH]ccc3n12)C(=O)NCC(F)(F)F LATZVDXOTDYECD-UFTFXDLESA-N 0.000 description 1
- NHJVRSWLHSJWIN-UHFFFAOYSA-N 2,4,6-trinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O NHJVRSWLHSJWIN-UHFFFAOYSA-N 0.000 description 1
- OHMPXDCOVKOOAN-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-n-[3-(4-fluorophenyl)-4-pyrimidin-4-yl-1,2-oxazol-5-yl]acetamide Chemical compound C1=CC(F)=CC=C1C1=NOC(NC(=O)CC=2C(=CC=CC=2F)Cl)=C1C1=CC=NC=N1 OHMPXDCOVKOOAN-UHFFFAOYSA-N 0.000 description 1
- IJMBOKOTALXLKS-UHFFFAOYSA-N 2-(6-morpholin-4-ylpyrimidin-4-yl)-4-(triazol-1-yl)-1h-pyrazol-3-one Chemical compound O=C1C(N2N=NC=C2)=CNN1C(N=CN=1)=CC=1N1CCOCC1 IJMBOKOTALXLKS-UHFFFAOYSA-N 0.000 description 1
- JHFUMBOPCRFCOT-UHFFFAOYSA-N 2-(trifluoromethylsulfonyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1S(=O)(=O)C(F)(F)F JHFUMBOPCRFCOT-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- RUEYEZADQJCKGV-UHFFFAOYSA-N 2-[(1,3-dicyclohexyl-2,4,6-trioxo-1,3-diazinane-5-carbonyl)amino]acetic acid Chemical compound O=C1N(C2CCCCC2)C(=O)C(C(=O)NCC(=O)O)C(=O)N1C1CCCCC1 RUEYEZADQJCKGV-UHFFFAOYSA-N 0.000 description 1
- FOFXXEHXOCAJIW-GNAFDRTKSA-N 2-[(3s)-6-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid;hydrate Chemical compound O.CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C1=CC=CC(COC=2C=C3OC[C@@H](CC(O)=O)C3=CC=2)=C1 FOFXXEHXOCAJIW-GNAFDRTKSA-N 0.000 description 1
- YGWFCQYETHJKNX-UHFFFAOYSA-N 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCC[NH2+]1 YGWFCQYETHJKNX-UHFFFAOYSA-N 0.000 description 1
- NFGVHWUWINDVLR-UHFFFAOYSA-N 2-[(5-hydroxy-3-oxo-8-thia-2,6-diazatricyclo[7.5.0.02,7]tetradeca-1(9),4,6-triene-4-carbonyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)c1c(O)nc2sc3CCCCCc3n2c1=O NFGVHWUWINDVLR-UHFFFAOYSA-N 0.000 description 1
- NFTMKHWBOINJGM-UHFFFAOYSA-N 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-4-[[4-(tetrazol-1-yl)phenoxy]methyl]-1,3-thiazole Chemical compound N1=CC(CC)=CN=C1N1CCC(C=2SC=C(COC=3C=CC(=CC=3)N3N=NN=C3)N=2)CC1 NFTMKHWBOINJGM-UHFFFAOYSA-N 0.000 description 1
- WRFHGDPIDHPWIQ-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(ethoxymethyl)phenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(COCC)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 WRFHGDPIDHPWIQ-UHFFFAOYSA-N 0.000 description 1
- YMWJDWJXIXITMD-UHFFFAOYSA-N 2-[4-[3-[2-(2-chloro-6-fluorophenyl)ethyl-[(2,3-dichlorophenyl)carbamoyl]amino]propyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCCN(C(=O)NC=1C(=C(Cl)C=CC=1)Cl)CCC1=C(F)C=CC=C1Cl YMWJDWJXIXITMD-UHFFFAOYSA-N 0.000 description 1
- YXFNPRHZMOGREC-UHFFFAOYSA-N 2-[4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl]acetic acid Chemical compound N1=C(C(N)=O)C(C)=NC(C)=C1C1=CC=C(C2CCC(CC(O)=O)CC2)C=C1 YXFNPRHZMOGREC-UHFFFAOYSA-N 0.000 description 1
- GXALXAKNHIROPE-UHFFFAOYSA-N 2-[4-[4-[5-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyridin-2-yl]phenyl]cyclohexyl]acetic acid Chemical compound C1CC(CC(=O)O)CCC1C1=CC=C(C=2N=CC(NC=3C=NC(=CC=3)C(F)(F)F)=CC=2)C=C1 GXALXAKNHIROPE-UHFFFAOYSA-N 0.000 description 1
- JWYIGNODXSRKGP-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JWYIGNODXSRKGP-UHFFFAOYSA-N 0.000 description 1
- AYKLXGCULGWUJX-UHFFFAOYSA-N 2-[5-chloro-2-[[1-[(3,4-difluorophenyl)methyl]-4-[(4-methylsulfonylphenyl)methyl]pyrrole-2-carbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC1=CN(CC=2C=C(F)C(F)=CC=2)C(C(=O)NC=2SC(Cl)=C(CC(O)=O)N=2)=C1 AYKLXGCULGWUJX-UHFFFAOYSA-N 0.000 description 1
- HPGJSAAUJGAMLV-UHFFFAOYSA-N 2-[[2-[[cyclohexyl-(4-propoxycyclohexyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound C1CC(OCCC)CCC1N(C(=O)NC=1SC(SCC(O)=O)=CN=1)C1CCCCC1 HPGJSAAUJGAMLV-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- POPPVIRYGJQIOF-UHFFFAOYSA-N 2-acetyloxyethyl(trimethyl)azanium;3-(1-methylpyrrolidin-2-yl)pyridine Chemical compound CC(=O)OCC[N+](C)(C)C.CN1CCCC1C1=CC=CN=C1 POPPVIRYGJQIOF-UHFFFAOYSA-N 0.000 description 1
- RTBSTLCUXKGLPI-UHFFFAOYSA-N 2-amino-2-pyridin-3-ylethanol Chemical compound OCC(N)C1=CC=CN=C1 RTBSTLCUXKGLPI-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QINPEPAQOBZPOF-UHFFFAOYSA-N 2-amino-n-[3-[[3-(2-chloro-5-methoxyanilino)quinoxalin-2-yl]sulfamoyl]phenyl]-2-methylpropanamide Chemical compound COC1=CC=C(Cl)C(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=C(NC(=O)C(C)(C)N)C=CC=2)=C1 QINPEPAQOBZPOF-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 description 1
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- HPJALMWOZYIZGE-UHFFFAOYSA-N 2-oxa-6-azaspiro[3.3]heptane Chemical compound C1NCC11COC1 HPJALMWOZYIZGE-UHFFFAOYSA-N 0.000 description 1
- MXNGYQJJYRVGGJ-QFIPXVFZSA-N 2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 MXNGYQJJYRVGGJ-QFIPXVFZSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- FXIBFBGQYAPGLP-UHFFFAOYSA-N 2-pyridin-3-ylpropan-2-amine Chemical compound CC(C)(N)C1=CC=CN=C1 FXIBFBGQYAPGLP-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 1
- ZFYBRHUYNCEPPR-UHFFFAOYSA-N 3-(4-fluorophenyl)oxetan-3-amine Chemical compound C=1C=C(F)C=CC=1C1(N)COC1 ZFYBRHUYNCEPPR-UHFFFAOYSA-N 0.000 description 1
- VKHVAUKFLBBZFJ-SFHVURJKSA-N 3-(4-methoxy-2-methylphenyl)-2,5-dimethyl-n-[(1s)-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N([C@@H](CC)C=1ON=C(C)N=1)C(N1N=C2C)=CC(C)=NC1=C2C1=CC=C(OC)C=C1C VKHVAUKFLBBZFJ-SFHVURJKSA-N 0.000 description 1
- MSEQBCDSEVCGDC-UHFFFAOYSA-N 3-(aminomethyl)pyridin-2-amine Chemical compound NCC1=CC=CN=C1N MSEQBCDSEVCGDC-UHFFFAOYSA-N 0.000 description 1
- FQEVHRCPXFKJHF-UHFFFAOYSA-N 3-(trifluoromethoxy)benzaldehyde Chemical compound FC(F)(F)OC1=CC=CC(C=O)=C1 FQEVHRCPXFKJHF-UHFFFAOYSA-N 0.000 description 1
- MMDFTYGZZLJQER-UHFFFAOYSA-N 3-(trifluoromethylsulfanyl)benzaldehyde Chemical compound FC(F)(F)SC1=CC=CC(C=O)=C1 MMDFTYGZZLJQER-UHFFFAOYSA-N 0.000 description 1
- KZGLTOBKIREXJB-UHFFFAOYSA-N 3-[2-(pyridin-3-ylmethylamino)-1,3-thiazole-5-carbonyl]benzonitrile Chemical compound N1=CC(=CC=C1)CNC=1SC(=CN=1)C(=O)C=1C=C(C#N)C=CC=1 KZGLTOBKIREXJB-UHFFFAOYSA-N 0.000 description 1
- FJEJHJINOKKDCW-INIZCTEOSA-N 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(5-methylpyrazin-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2N=CC(C)=NC=2)=CC(O[C@@H](C)COC)=CC=1OC(N=C1)=CN=C1C(=O)N1CCC1 FJEJHJINOKKDCW-INIZCTEOSA-N 0.000 description 1
- VGUSQKZDZHAAEE-UHFFFAOYSA-N 3-[5-amino-4-(3-cyanobenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(C#N)=C1 VGUSQKZDZHAAEE-UHFFFAOYSA-N 0.000 description 1
- WHWMCHUIUINGOD-UHFFFAOYSA-N 3-amino-3-(4-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(C(N)CCO)C=C1 WHWMCHUIUINGOD-UHFFFAOYSA-N 0.000 description 1
- NEOIOGUWEUTYIH-UHFFFAOYSA-N 3-azabicyclo[3.2.0]heptane Chemical compound C1NCC2CCC21 NEOIOGUWEUTYIH-UHFFFAOYSA-N 0.000 description 1
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- LYGWBPDKDLWHHB-UHFFFAOYSA-N 3-morpholin-4-ylsulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)N2CCOCC2)=C1 LYGWBPDKDLWHHB-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UZMCSTKSVWZMJA-UHFFFAOYSA-N 3-pyrrolidin-1-ylsulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)N2CCCC2)=C1 UZMCSTKSVWZMJA-UHFFFAOYSA-N 0.000 description 1
- PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 1
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 1
- BGLPECHZZQDNCD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-ethylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BGLPECHZZQDNCD-UHFFFAOYSA-N 0.000 description 1
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 1
- GDTQLZHHDRRBEB-UHFFFAOYSA-N 4-[5-(cyclopropylcarbamoyl)-2-methylanilino]-5-methyl-n-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C12=C(C)C(C(=O)NCCC)=CN2N=CN=C1NC(C(=CC=1)C)=CC=1C(=O)NC1CC1 GDTQLZHHDRRBEB-UHFFFAOYSA-N 0.000 description 1
- UBVZQGOVTLIHLH-UHFFFAOYSA-N 4-[5-pyridin-4-yl-1h-[1,2,4]triazol-3-yl]-pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC(C=2N=C(NN=2)C=2C=CN=CC=2)=C1 UBVZQGOVTLIHLH-UHFFFAOYSA-N 0.000 description 1
- LUUMLYXKTPBTQR-UHFFFAOYSA-N 4-chloro-n-[5-methyl-2-(7h-pyrrolo[2,3-d]pyrimidine-4-carbonyl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C=1C(C)=CN=C(C(=O)C=2C=3C=CNC=3N=CN=2)C=1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 LUUMLYXKTPBTQR-UHFFFAOYSA-N 0.000 description 1
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- JRWROCIMSDXGOZ-UHFFFAOYSA-N 4-tert-butyl-n-[4-chloro-2-(1-oxidopyridin-1-ium-4-carbonyl)phenyl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=[N+]([O-])C=C1 JRWROCIMSDXGOZ-UHFFFAOYSA-N 0.000 description 1
- IFGWYHGYNVGVRB-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-n-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)indazole-6-carboxamide Chemical compound CN(C)CCNC(=O)C=1C=C2N(CC(C)C)N=CC2=CC=1OC1=CC=C(F)C=C1F IFGWYHGYNVGVRB-UHFFFAOYSA-N 0.000 description 1
- CSVYITCBZGOVBG-UHFFFAOYSA-N 5-(aminomethyl)-1h-pyridin-2-one Chemical compound NCC=1C=CC(=O)NC=1 CSVYITCBZGOVBG-UHFFFAOYSA-N 0.000 description 1
- LXMHSJKKDQCDKN-UHFFFAOYSA-N 5-(aminomethyl)pyridin-3-ol Chemical compound NCC1=CN=CC(O)=C1 LXMHSJKKDQCDKN-UHFFFAOYSA-N 0.000 description 1
- NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
- ZISJNXNHJRQYJO-CMDGGOBGSA-N 5-[(e)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=C(O)C=C1\C=C\C1=CC=CC=C1 ZISJNXNHJRQYJO-CMDGGOBGSA-N 0.000 description 1
- XPPBBJCBDOEXDN-UHFFFAOYSA-N 5-[2-tert-butyl-4-(4-fluorophenyl)-1h-imidazol-5-yl]-3-(2,2-dimethylpropyl)imidazo[4,5-b]pyridin-2-amine Chemical compound N1=C2N(CC(C)(C)C)C(N)=NC2=CC=C1C=1N=C(C(C)(C)C)NC=1C1=CC=C(F)C=C1 XPPBBJCBDOEXDN-UHFFFAOYSA-N 0.000 description 1
- MPLLLQUZNJSVTK-UHFFFAOYSA-N 5-[3-[4-[2-(4-fluorophenyl)ethoxy]phenyl]propyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CCCC(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 MPLLLQUZNJSVTK-UHFFFAOYSA-N 0.000 description 1
- AYJRTVVIBJSSKN-UHFFFAOYSA-N 5-[4-[[6-(4-methylsulfonylphenyl)pyridin-3-yl]oxymethyl]piperidin-1-yl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(N2CCC(COC=3C=NC(=CC=3)C=3C=CC(=CC=3)S(C)(=O)=O)CC2)=N1 AYJRTVVIBJSSKN-UHFFFAOYSA-N 0.000 description 1
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
- IETKPTYAGKZLKY-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IETKPTYAGKZLKY-UHFFFAOYSA-N 0.000 description 1
- XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 description 1
- MJZJYWCQPMNPRM-UHFFFAOYSA-N 6,6-dimethyl-1-[3-(2,4,5-trichlorophenoxy)propoxy]-1,6-dihydro-1,3,5-triazine-2,4-diamine Chemical compound CC1(C)N=C(N)N=C(N)N1OCCCOC1=CC(Cl)=C(Cl)C=C1Cl MJZJYWCQPMNPRM-UHFFFAOYSA-N 0.000 description 1
- LFMPVTVPXHNXOT-HNNXBMFYSA-N 6-amino-2-[(2s)-pentan-2-yl]oxy-9-(5-piperidin-1-ylpentyl)-7h-purin-8-one Chemical compound C12=NC(O[C@@H](C)CCC)=NC(N)=C2NC(=O)N1CCCCCN1CCCCC1 LFMPVTVPXHNXOT-HNNXBMFYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ORVNHOYNEHYKJG-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(NC(CO)CO)=NC2=C1C=CC(=O)N2C1=C(F)C=CC=C1F ORVNHOYNEHYKJG-UHFFFAOYSA-N 0.000 description 1
- SJVQHLPISAIATJ-ZDUSSCGKSA-N 8-chloro-2-phenyl-3-[(1S)-1-(7H-purin-6-ylamino)ethyl]-1-isoquinolinone Chemical compound C1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)=CC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC=C1 SJVQHLPISAIATJ-ZDUSSCGKSA-N 0.000 description 1
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
- 208000007122 AIDS-Associated Nephropathy Diseases 0.000 description 1
- 108010009522 AMG623 peptibody Proteins 0.000 description 1
- 229940127110 AZD1656 Drugs 0.000 description 1
- 108010048280 AcPhe(ornithine-Pro-cyclohexylamine-Trp-Arg) Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- 201000004625 Acrodermatitis Diseases 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 206010000748 Acute febrile neutrophilic dermatosis Diseases 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 108010053754 Aldehyde reductase Proteins 0.000 description 1
- 102100027265 Aldo-keto reductase family 1 member B1 Human genes 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010001767 Alopecia universalis Diseases 0.000 description 1
- 208000024985 Alport syndrome Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 description 1
- 229940122816 Amylase inhibitor Drugs 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 description 1
- 208000001839 Antisynthetase syndrome Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- QNZCBYKSOIHPEH-UHFFFAOYSA-N Apixaban Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(CC2)C=3C=CC(=CC=3)N3C(CCCC3)=O)=C2C(C(N)=O)=N1 QNZCBYKSOIHPEH-UHFFFAOYSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 1
- 200000000007 Arterial disease Diseases 0.000 description 1
- 206010003162 Arterial injury Diseases 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 206010058029 Arthrofibrosis Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 208000004300 Atrophic Gastritis Diseases 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 1
- 102100022716 Atypical chemokine receptor 3 Human genes 0.000 description 1
- 208000035913 Atypical hemolytic uremic syndrome Diseases 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 description 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 description 1
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 1
- MREBEPTUUMTTIA-PCLIKHOPSA-N Azimilide Chemical compound C1CN(C)CCN1CCCCN1C(=O)N(\N=C\C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1=O MREBEPTUUMTTIA-PCLIKHOPSA-N 0.000 description 1
- 108010028006 B-Cell Activating Factor Proteins 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 208000032568 B-cell prolymphocytic leukaemia Diseases 0.000 description 1
- 102100038080 B-cell receptor CD22 Human genes 0.000 description 1
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
- 239000005465 B01AC22 - Prasugrel Substances 0.000 description 1
- 108091005625 BRD4 Proteins 0.000 description 1
- 229940124291 BTK inhibitor Drugs 0.000 description 1
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WPTTVJLTNAWYAO-KPOXMGGZSA-N Bardoxolone methyl Chemical group C([C@@]12C)=C(C#N)C(=O)C(C)(C)[C@@H]1CC[C@]1(C)C2=CC(=O)[C@@H]2[C@@H]3CC(C)(C)CC[C@]3(C(=O)OC)CC[C@]21C WPTTVJLTNAWYAO-KPOXMGGZSA-N 0.000 description 1
- 208000023328 Basedow disease Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
- 206010004663 Biliary colic Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102100029895 Bromodomain-containing protein 4 Human genes 0.000 description 1
- 102000001805 Bromodomains Human genes 0.000 description 1
- 108050009021 Bromodomains Proteins 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 208000023611 Burkitt leukaemia Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 1
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 1
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 1
- 102100025074 C-C chemokine receptor-like 2 Human genes 0.000 description 1
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 1
- 102100025618 C-X-C chemokine receptor type 6 Human genes 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 208000029574 C3 glomerulopathy Diseases 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 102100032957 C5a anaphylatoxin chemotactic receptor 1 Human genes 0.000 description 1
- 101710098483 C5a anaphylatoxin chemotactic receptor 1 Proteins 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- 102100032976 CCR4-NOT transcription complex subunit 6 Human genes 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- WDLFVWVYIPPTMI-UHFFFAOYSA-N COc1cc(C(c2cnc(NCc(cc3)ccc3F)[s]2)=O)c2cc1C2 Chemical compound COc1cc(C(c2cnc(NCc(cc3)ccc3F)[s]2)=O)c2cc1C2 WDLFVWVYIPPTMI-UHFFFAOYSA-N 0.000 description 1
- OSYSNDKNRZKHNI-UHFFFAOYSA-N CS(c1cc(C(c2cnc(N(Cc3cccnc3)C3CC3)[s]2)=O)ccc1)(=O)=O Chemical compound CS(c1cc(C(c2cnc(N(Cc3cccnc3)C3CC3)[s]2)=O)ccc1)(=O)=O OSYSNDKNRZKHNI-UHFFFAOYSA-N 0.000 description 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 1
- 229910014455 Ca-Cb Inorganic materials 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000003952 Caspase 3 Human genes 0.000 description 1
- 108090000397 Caspase 3 Proteins 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 102000003902 Cathepsin C Human genes 0.000 description 1
- 108090000267 Cathepsin C Proteins 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 206010008088 Cerebral artery embolism Diseases 0.000 description 1
- 206010008092 Cerebral artery thrombosis Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
- 208000024699 Chagas disease Diseases 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- 208000022497 Cocaine-Related disease Diseases 0.000 description 1
- 208000010007 Cogan syndrome Diseases 0.000 description 1
- 208000027691 Conduct disease Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010071503 Crystal nephropathy Diseases 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- JVHXJTBJCFBINQ-ADAARDCZSA-N Dapagliflozin Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl JVHXJTBJCFBINQ-ADAARDCZSA-N 0.000 description 1
- 206010051055 Deep vein thrombosis Diseases 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 102000002148 Diacylglycerol O-acyltransferase Human genes 0.000 description 1
- 108010001348 Diacylglycerol O-acyltransferase Proteins 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 1
- 208000035762 Disorder of lipid metabolism Diseases 0.000 description 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
- 102000004073 Dopamine D3 Receptors Human genes 0.000 description 1
- 108090000525 Dopamine D3 Receptors Proteins 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 206010013754 Drug withdrawal syndrome Diseases 0.000 description 1
- DVJAMEIQRSHVKC-BDAKNGLRSA-N Dutogliptin Chemical compound OB(O)[C@@H]1CCCN1C(=O)CN[C@H]1CNCC1 DVJAMEIQRSHVKC-BDAKNGLRSA-N 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 206010014513 Embolism arterial Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 229940118365 Endothelin receptor antagonist Drugs 0.000 description 1
- 102400001329 Epiregulin Human genes 0.000 description 1
- 101800000155 Epiregulin Proteins 0.000 description 1
- 108020002908 Epoxide hydrolase Proteins 0.000 description 1
- 108010056764 Eptifibatide Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- 208000026097 Factitious disease Diseases 0.000 description 1
- 208000026019 Fanconi renotubular syndrome Diseases 0.000 description 1
- 201000006328 Fanconi syndrome Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 102000003973 Fibroblast growth factor 21 Human genes 0.000 description 1
- 108090000376 Fibroblast growth factor 21 Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 1
- 208000001914 Fragile X syndrome Diseases 0.000 description 1
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 description 1
- 102100040136 Free fatty acid receptor 3 Human genes 0.000 description 1
- 102100040134 Free fatty acid receptor 4 Human genes 0.000 description 1
- 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
- 108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
- 102100030280 G-protein coupled receptor 39 Human genes 0.000 description 1
- 108010007934 GSK-2793660 Proteins 0.000 description 1
- QTQMRBZOBKYXCG-MHZLTWQESA-N GW 1929 Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCN(C)C=1N=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 QTQMRBZOBKYXCG-MHZLTWQESA-N 0.000 description 1
- 108010001517 Galectin 3 Proteins 0.000 description 1
- 102100039558 Galectin-3 Human genes 0.000 description 1
- 206010061968 Gastric neoplasm Diseases 0.000 description 1
- 208000036495 Gastritis atrophic Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 208000007465 Giant cell arteritis Diseases 0.000 description 1
- 108010072051 Glatiramer Acetate Proteins 0.000 description 1
- 108010063919 Glucagon Receptors Proteins 0.000 description 1
- 102100040890 Glucagon receptor Human genes 0.000 description 1
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 1
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 1
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
- 102100033417 Glucocorticoid receptor Human genes 0.000 description 1
- 229940117965 Glucocorticoid receptor modulator Drugs 0.000 description 1
- 102000030595 Glucokinase Human genes 0.000 description 1
- 108010021582 Glucokinase Proteins 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 102100033305 Glutathione S-transferase A3 Human genes 0.000 description 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- 208000024869 Goodpasture syndrome Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 206010070737 HIV associated nephropathy Diseases 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 208000001204 Hashimoto Disease Diseases 0.000 description 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 description 1
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 102000007625 Hirudins Human genes 0.000 description 1
- 108010007267 Hirudins Proteins 0.000 description 1
- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 1
- 101000678890 Homo sapiens Atypical chemokine receptor 3 Proteins 0.000 description 1
- 101000884305 Homo sapiens B-cell receptor CD22 Proteins 0.000 description 1
- 101000716068 Homo sapiens C-C chemokine receptor type 6 Proteins 0.000 description 1
- 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 description 1
- 101000856683 Homo sapiens C-X-C chemokine receptor type 6 Proteins 0.000 description 1
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 description 1
- 101000890662 Homo sapiens Free fatty acid receptor 3 Proteins 0.000 description 1
- 101000890672 Homo sapiens Free fatty acid receptor 4 Proteins 0.000 description 1
- 101001009541 Homo sapiens G-protein coupled receptor 39 Proteins 0.000 description 1
- 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 description 1
- 101000870590 Homo sapiens Glutathione S-transferase A3 Proteins 0.000 description 1
- 101000843810 Homo sapiens Hydroxycarboxylic acid receptor 1 Proteins 0.000 description 1
- 101000843809 Homo sapiens Hydroxycarboxylic acid receptor 2 Proteins 0.000 description 1
- 101001019598 Homo sapiens Interleukin-17 receptor A Proteins 0.000 description 1
- 101000998146 Homo sapiens Interleukin-17A Proteins 0.000 description 1
- 101001043352 Homo sapiens Lysyl oxidase homolog 2 Proteins 0.000 description 1
- 101001056015 Homo sapiens Mannan-binding lectin serine protease 2 Proteins 0.000 description 1
- 101001018196 Homo sapiens Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 description 1
- 101001059984 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 4 Proteins 0.000 description 1
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 description 1
- 101000588302 Homo sapiens Nuclear factor erythroid 2-related factor 2 Proteins 0.000 description 1
- 101001121539 Homo sapiens P2Y purinoceptor 14 Proteins 0.000 description 1
- 101100463125 Homo sapiens PDK4 gene Proteins 0.000 description 1
- 101000684208 Homo sapiens Prolyl endopeptidase FAP Proteins 0.000 description 1
- 101001098868 Homo sapiens Proprotein convertase subtilisin/kexin type 9 Proteins 0.000 description 1
- 101001093899 Homo sapiens Retinoic acid receptor RXR-alpha Proteins 0.000 description 1
- 101000821903 Homo sapiens Solute carrier family 22 member 12 Proteins 0.000 description 1
- 101000829127 Homo sapiens Somatostatin receptor type 2 Proteins 0.000 description 1
- 101000829138 Homo sapiens Somatostatin receptor type 3 Proteins 0.000 description 1
- 101000829153 Homo sapiens Somatostatin receptor type 5 Proteins 0.000 description 1
- 101100537522 Homo sapiens TNFSF13B gene Proteins 0.000 description 1
- 101000831567 Homo sapiens Toll-like receptor 2 Proteins 0.000 description 1
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 1
- 101000764872 Homo sapiens Transient receptor potential cation channel subfamily A member 1 Proteins 0.000 description 1
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 1
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 1
- 101001117143 Homo sapiens [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229940124036 Hydrolase inhibitor Drugs 0.000 description 1
- 102100030642 Hydroxycarboxylic acid receptor 1 Human genes 0.000 description 1
- 101710125793 Hydroxycarboxylic acid receptor 2 Proteins 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- 102100034980 ICOS ligand Human genes 0.000 description 1
- 101710093458 ICOS ligand Proteins 0.000 description 1
- ALOBUEHUHMBRLE-UHFFFAOYSA-N Ibutilide Chemical compound CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ALOBUEHUHMBRLE-UHFFFAOYSA-N 0.000 description 1
- 208000010159 IgA glomerulonephritis Diseases 0.000 description 1
- 206010021263 IgA nephropathy Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 208000030990 Impulse-control disease Diseases 0.000 description 1
- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- 108010034143 Inflammasomes Proteins 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 208000031773 Insulin resistance syndrome Diseases 0.000 description 1
- 201000006347 Intellectual Disability Diseases 0.000 description 1
- 102000007438 Interferon alpha-beta Receptor Human genes 0.000 description 1
- 108010086140 Interferon alpha-beta Receptor Proteins 0.000 description 1
- 102000013462 Interleukin-12 Human genes 0.000 description 1
- 108010065805 Interleukin-12 Proteins 0.000 description 1
- 102000003816 Interleukin-13 Human genes 0.000 description 1
- 108090000176 Interleukin-13 Proteins 0.000 description 1
- 102100035018 Interleukin-17 receptor A Human genes 0.000 description 1
- 102100033461 Interleukin-17A Human genes 0.000 description 1
- 102000013264 Interleukin-23 Human genes 0.000 description 1
- 108010065637 Interleukin-23 Proteins 0.000 description 1
- 102000017761 Interleukin-33 Human genes 0.000 description 1
- 108010067003 Interleukin-33 Proteins 0.000 description 1
- 102000004388 Interleukin-4 Human genes 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 102100020941 Interleukin-4 Human genes 0.000 description 1
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 229940125772 JTE-052 Drugs 0.000 description 1
- 108010024121 Janus Kinases Proteins 0.000 description 1
- 102000015617 Janus Kinases Human genes 0.000 description 1
- 206010060820 Joint injury Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010023347 Keratoacanthoma Diseases 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 208000016593 Knee injury Diseases 0.000 description 1
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- RITKHVBHSGLULN-WHFBIAKZSA-N L-gamma-glutamyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(O)=O RITKHVBHSGLULN-WHFBIAKZSA-N 0.000 description 1
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 239000002144 L01XE18 - Ruxolitinib Substances 0.000 description 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 102100024102 Leucine-rich repeat and immunoglobulin-like domain-containing nogo receptor-interacting protein 1 Human genes 0.000 description 1
- 101710174924 Leucine-rich repeat and immunoglobulin-like domain-containing nogo receptor-interacting protein 1 Proteins 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 206010065433 Ligament rupture Diseases 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 102100025357 Lipid-phosphate phosphatase Human genes 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- YSDQQAXHVYUZIW-QCIJIYAXSA-N Liraglutide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)CC[C@H](NC(=O)CCCCCCCCCCCCCCC)C(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 YSDQQAXHVYUZIW-QCIJIYAXSA-N 0.000 description 1
- 108010019598 Liraglutide Proteins 0.000 description 1
- 108010007859 Lisinopril Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XVVOERDUTLJJHN-UHFFFAOYSA-N Lixisenatide Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(CC(N)=O)C(=O)NCC(=O)NCC(=O)N1C(CCC1)C(=O)NC(CO)C(=O)NC(CO)C(=O)NCC(=O)NC(C)C(=O)N1C(CCC1)C(=O)N1C(CCC1)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)CC)NC(=O)C(NC(=O)C(CC(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(CCC(O)=O)NC(=O)C(CCC(O)=O)NC(=O)C(CCSC)NC(=O)C(CCC(N)=O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)NC(=O)C(CO)NC(=O)C(NC(=O)C(CC=1C=CC=CC=1)NC(=O)C(NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)CNC(=O)C(N)CC=1NC=NC=1)C(C)O)C(C)O)C(C)C)CC1=CC=CC=C1 XVVOERDUTLJJHN-UHFFFAOYSA-N 0.000 description 1
- 208000000185 Localized scleroderma Diseases 0.000 description 1
- 229940110339 Long-acting muscarinic antagonist Drugs 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- WHSOLWOTCHFFBK-ZQGJOIPISA-N Luseogliflozin Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)S2)O)=C(OC)C=C1C WHSOLWOTCHFFBK-ZQGJOIPISA-N 0.000 description 1
- 208000016604 Lyme disease Diseases 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- 206010052178 Lymphocytic lymphoma Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102100021948 Lysyl oxidase homolog 2 Human genes 0.000 description 1
- 102000019149 MAP kinase activity proteins Human genes 0.000 description 1
- 108040008097 MAP kinase activity proteins Proteins 0.000 description 1
- 239000012820 MEK1 Inhibitor Substances 0.000 description 1
- 206010054805 Macroangiopathy Diseases 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 208000009777 Majeed syndrome Diseases 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 102100026046 Mannan-binding lectin serine protease 2 Human genes 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 description 1
- 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 description 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 1
- 208000004451 Membranoproliferative Glomerulonephritis Diseases 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
- 206010027603 Migraine headaches Diseases 0.000 description 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
- 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 description 1
- 102100033127 Mitogen-activated protein kinase kinase kinase 5 Human genes 0.000 description 1
- 102100028194 Mitogen-activated protein kinase kinase kinase kinase 4 Human genes 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 206010027982 Morphoea Diseases 0.000 description 1
- 101100091494 Mus musculus Rorc gene Proteins 0.000 description 1
- 101100115705 Mus musculus Stfa1 gene Proteins 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 102100038610 Myeloperoxidase Human genes 0.000 description 1
- 229940122159 Myeloperoxidase inhibitor Drugs 0.000 description 1
- 108090000235 Myeloperoxidases Proteins 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- FJHHZXWJVIEFGJ-UHFFFAOYSA-N N-(3-methoxy-5-methyl-2-pyrazinyl)-2-[4-(1,3,4-oxadiazol-2-yl)phenyl]-3-pyridinesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CN=C1C1=CC=C(C=2OC=NN=2)C=C1 FJHHZXWJVIEFGJ-UHFFFAOYSA-N 0.000 description 1
- PJTGSIKANITYOO-RCOXNQKVSA-N N-[(1R,2S,5R)-5-[methyl(propan-2-yl)amino]-2-[(3S)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]methanesulfonamide Chemical compound CC(C)N(C)[C@@H]1CC[C@@H]([C@@H](C1)NS(C)(=O)=O)N1CC[C@H](Nc2ncnc3ccc(cc23)C(F)(F)F)C1=O PJTGSIKANITYOO-RCOXNQKVSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical class 0.000 description 1
- AJRGAVKWPOTBCA-UHFFFAOYSA-N N-methoxy-N-methyl-3-(trifluoromethylsulfonyl)benzamide Chemical compound CON(C(C1=CC(=CC=C1)S(=O)(=O)C(F)(F)F)=O)C AJRGAVKWPOTBCA-UHFFFAOYSA-N 0.000 description 1
- NALAUGMPMIVAOW-UHFFFAOYSA-N N12N=CN=C2C(C(=O)NCC(=O)O)=C(O)C=C1CCC1=CC=CC=C1 Chemical compound N12N=CN=C2C(C(=O)NCC(=O)O)=C(O)C=C1CCC1=CC=CC=C1 NALAUGMPMIVAOW-UHFFFAOYSA-N 0.000 description 1
- 102100031455 NAD-dependent protein deacetylase sirtuin-1 Human genes 0.000 description 1
- 108010082699 NADPH Oxidase 4 Proteins 0.000 description 1
- 102100021872 NADPH oxidase 4 Human genes 0.000 description 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910003827 NRaRb Inorganic materials 0.000 description 1
- 101150111783 NTRK1 gene Proteins 0.000 description 1
- DJDFFEBSKJCGHC-UHFFFAOYSA-N Naphazoline Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 DJDFFEBSKJCGHC-UHFFFAOYSA-N 0.000 description 1
- 208000018526 Narcotic-Related disease Diseases 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 208000028389 Nerve injury Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 101100426589 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) trp-3 gene Proteins 0.000 description 1
- 206010058105 Neutrophilic dermatosis Diseases 0.000 description 1
- 206010067115 Neutrophilic panniculitis Diseases 0.000 description 1
- 206010057852 Nicotine dependence Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 description 1
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- 102100031701 Nuclear factor erythroid 2-related factor 2 Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 206010031009 Oral pain Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 102100025808 P2Y purinoceptor 14 Human genes 0.000 description 1
- KCAJXIDMCNPGHZ-UHFFFAOYSA-N PH 797804 Chemical compound CNC(=O)C1=CC=C(C)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KCAJXIDMCNPGHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012828 PI3K inhibitor Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150014691 PPARA gene Proteins 0.000 description 1
- 101150020891 PRKCA gene Proteins 0.000 description 1
- 206010033554 Palmoplantar keratoderma Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 208000006199 Parasomnias Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 206010034158 Pathological gambling Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 206010034277 Pemphigoid Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 208000031845 Pernicious anaemia Diseases 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
- 229940123263 Phosphodiesterase 3 inhibitor Drugs 0.000 description 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 description 1
- 208000007452 Plasmacytoma Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 206010065159 Polychondritis Diseases 0.000 description 1
- CYLWJCABXYDINA-UHFFFAOYSA-N Polythiazide Polymers ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CSCC(F)(F)F)NC2=C1 CYLWJCABXYDINA-UHFFFAOYSA-N 0.000 description 1
- 201000009916 Postpartum depression Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- QJLPWVUZFKETMK-UHFFFAOYSA-N Pradimicin Q Natural products O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CC(O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-UHFFFAOYSA-N 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- MWQCHHACWWAQLJ-UHFFFAOYSA-N Prazepam Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MWQCHHACWWAQLJ-UHFFFAOYSA-N 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 206010065347 Premenstrual pain Diseases 0.000 description 1
- 206010065857 Primary Effusion Lymphoma Diseases 0.000 description 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
- 102100040918 Pro-glucagon Human genes 0.000 description 1
- 206010036774 Proctitis Diseases 0.000 description 1
- 102000004079 Prolyl Hydroxylases Human genes 0.000 description 1
- 108010043005 Prolyl Hydroxylases Proteins 0.000 description 1
- 208000035416 Prolymphocytic B-Cell Leukemia Diseases 0.000 description 1
- 102100038955 Proprotein convertase subtilisin/kexin type 9 Human genes 0.000 description 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 description 1
- 102100024218 Prostaglandin D2 receptor 2 Human genes 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 208000029808 Psychomotor disease Diseases 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010037437 Pulmonary thrombosis Diseases 0.000 description 1
- 206010037575 Pustular psoriasis Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 108010001946 Pyrin Domain-Containing 3 Protein NLR Family Proteins 0.000 description 1
- 108091008680 RAR-related orphan receptors Proteins 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 206010038419 Renal colic Diseases 0.000 description 1
- 206010038563 Reocclusion Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 description 1
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 1
- 102100035178 Retinoic acid receptor RXR-alpha Human genes 0.000 description 1
- 102100038246 Retinol-binding protein 4 Human genes 0.000 description 1
- 101710137011 Retinol-binding protein 4 Proteins 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 108091006745 SLC22A12 Proteins 0.000 description 1
- 208000006117 ST-elevation myocardial infarction Diseases 0.000 description 1
- OCTNNXHKAOLDJL-BMGYQPLYSA-N Salbostatin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 OCTNNXHKAOLDJL-BMGYQPLYSA-N 0.000 description 1
- OCTNNXHKAOLDJL-UHFFFAOYSA-N Salbostatin Natural products OC1C(O)C(CO)OCC1NC1C(O)C(O)C(O)C(CO)=C1 OCTNNXHKAOLDJL-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 208000020186 Schizophreniform disease Diseases 0.000 description 1
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 description 1
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 description 1
- DLSWIYLPEUIQAV-UHFFFAOYSA-N Semaglutide Chemical compound CCC(C)C(NC(=O)C(Cc1ccccc1)NC(=O)C(CCC(O)=O)NC(=O)C(CCCCNC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CCC(NC(=O)CCCCCCCCCCCCCCCCC(O)=O)C(O)=O)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(N)=O)NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(CO)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)C(NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(C)(C)NC(=O)C(N)Cc1cnc[nH]1)C(C)O)C(C)O)C(C)C)C(=O)NC(C)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CCCNC(N)=N)C(=O)NCC(O)=O DLSWIYLPEUIQAV-UHFFFAOYSA-N 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 108010041191 Sirtuin 1 Proteins 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000010340 Sleep Deprivation Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 description 1
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 1
- 102100029329 Somatostatin receptor type 1 Human genes 0.000 description 1
- 102100023802 Somatostatin receptor type 2 Human genes 0.000 description 1
- 102100023803 Somatostatin receptor type 3 Human genes 0.000 description 1
- 102100023806 Somatostatin receptor type 5 Human genes 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- 229940127530 Sphingosine 1-Phosphate Receptor Modulators Drugs 0.000 description 1
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 244000166550 Strophanthus gratus Species 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 206010049418 Sudden Cardiac Death Diseases 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 208000010265 Sweet syndrome Diseases 0.000 description 1
- 208000008253 Systolic Heart Failure Diseases 0.000 description 1
- 206010071436 Systolic dysfunction Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 108700002718 TACI receptor-IgG Fc fragment fusion Proteins 0.000 description 1
- 101150109894 TGFA gene Proteins 0.000 description 1
- 108091000182 THR-184 Proteins 0.000 description 1
- 102000003629 TRPC3 Human genes 0.000 description 1
- 102000003621 TRPC5 Human genes 0.000 description 1
- 101150042815 TRPC5 gene Proteins 0.000 description 1
- 108010014401 TWEAK Receptor Proteins 0.000 description 1
- 102000016946 TWEAK Receptor Human genes 0.000 description 1
- 108010039185 Tenecteplase Proteins 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 229940123712 Thyroid hormone receptor antagonist Drugs 0.000 description 1
- 208000031737 Tissue Adhesions Diseases 0.000 description 1
- 229940127428 Tissue Plasminogen Activator Inhibitors Drugs 0.000 description 1
- 208000025569 Tobacco Use disease Diseases 0.000 description 1
- ZXOCGDDVNPDRIW-NHFZGCSJSA-N Tofogliflozin Chemical compound O.C1=CC(CC)=CC=C1CC1=CC=C(CO[C@@]23[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C2=C1 ZXOCGDDVNPDRIW-NHFZGCSJSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 102100024333 Toll-like receptor 2 Human genes 0.000 description 1
- 102100033110 Toll-like receptor 8 Human genes 0.000 description 1
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 1
- 108060008539 Transglutaminase Proteins 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 102100026186 Transient receptor potential cation channel subfamily A member 1 Human genes 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 229930186167 Trestatin Natural products 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 101150037542 Trpc3 gene Proteins 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- 102100033081 Tumor necrosis factor receptor type 1-associated DEATH domain protein Human genes 0.000 description 1
- 101710117293 Tumor necrosis factor receptor type 1-associated DEATH domain protein Proteins 0.000 description 1
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 1
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 1
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 1
- 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 101150008519 VNN1 gene Proteins 0.000 description 1
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 206010072810 Vascular wall hypertrophy Diseases 0.000 description 1
- 102100038286 Vasoactive intestinal polypeptide receptor 2 Human genes 0.000 description 1
- 101710137651 Vasoactive intestinal polypeptide receptor 2 Proteins 0.000 description 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
- 208000003728 Vulvodynia Diseases 0.000 description 1
- 206010069055 Vulvovaginal pain Diseases 0.000 description 1
- 208000027207 Whipple disease Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- JGGNOCUEWOGWPL-MUUNZHRXSA-N [(2R)-2-(4-carboxybutoxy)-3-hexadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OCCCCC(O)=O)COP([O-])(=O)OCC[N+](C)(C)C JGGNOCUEWOGWPL-MUUNZHRXSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- BVXLAHSJXXSWFF-KEKPKEOLSA-N [(2r,4as,10ar)-4a-benzyl-7-[(2-methylpyridin-3-yl)carbamoyl]-2-(trifluoromethyl)-1,3,4,9,10,10a-hexahydrophenanthren-2-yl] dihydrogen phosphate Chemical compound CC1=NC=CC=C1NC(=O)C1=CC=C2[C@]3(CC=4C=CC=CC=4)CC[C@@](C(F)(F)F)(OP(O)(O)=O)C[C@H]3CCC2=C1 BVXLAHSJXXSWFF-KEKPKEOLSA-N 0.000 description 1
- NZDMRJGAFPUTMZ-UHFFFAOYSA-N [1-(3,4-dihydroxyphenyl)-1-hydroxybutan-2-yl]azanium;chloride Chemical compound [Cl-].CCC([NH3+])C(O)C1=CC=C(O)C(O)=C1 NZDMRJGAFPUTMZ-UHFFFAOYSA-N 0.000 description 1
- XDJGNPSZQSWJCV-UHFFFAOYSA-N [2-[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-indazol-3-yl]-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]-(5-piperidin-1-ylpyrazin-2-yl)methanone Chemical compound CCC1=CC(O)=C(F)C=C1C1=CC=C(C(=NN2)C=3NC=4CCN(CC=4N=3)C(=O)C=3N=CC(=NC=3)N3CCCCC3)C2=C1 XDJGNPSZQSWJCV-UHFFFAOYSA-N 0.000 description 1
- RYVJQEZJUFRANT-UHFFFAOYSA-N [3-[4-(3-ethoxy-2-hydroxypropoxy)anilino]-3-oxopropyl]-dimethylsulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCOCC(O)COC1=CC=C(NC(=O)CC[S+](C)C)C=C1 RYVJQEZJUFRANT-UHFFFAOYSA-N 0.000 description 1
- 102100024150 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Human genes 0.000 description 1
- 102100034825 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial Human genes 0.000 description 1
- 229960003697 abatacept Drugs 0.000 description 1
- 229960000446 abciximab Drugs 0.000 description 1
- 229950008347 abrilumab Drugs 0.000 description 1
- IUEWXNHSKRWHDY-PHIMTYICSA-N abrocitinib Chemical compound C1[C@@H](NS(=O)(=O)CCC)C[C@H]1N(C)C1=NC=NC2=C1C=CN2 IUEWXNHSKRWHDY-PHIMTYICSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- FHEAIOHRHQGZPC-KIWGSFCNSA-N acetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FHEAIOHRHQGZPC-KIWGSFCNSA-N 0.000 description 1
- 229960001466 acetohexamide Drugs 0.000 description 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 208000033017 acquired idiopathic inflammatory myopathy Diseases 0.000 description 1
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 description 1
- 206010069351 acute lung injury Diseases 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 239000002404 acyltransferase inhibitor Substances 0.000 description 1
- 229960002964 adalimumab Drugs 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000010085 airway hyperresponsiveness Effects 0.000 description 1
- 108010047506 alanyl-glutaminyl-glycyl-valine Proteins 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229960001445 alitretinoin Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010435 allergic urticaria Diseases 0.000 description 1
- 229960003459 allopurinol Drugs 0.000 description 1
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
- ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 description 1
- 229960001667 alogliptin Drugs 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 208000032775 alopecia universalis congenita Diseases 0.000 description 1
- 229960003550 alosetron Drugs 0.000 description 1
- 239000002160 alpha blocker Substances 0.000 description 1
- 102000003801 alpha-2-Antiplasmin Human genes 0.000 description 1
- 108090000183 alpha-2-Antiplasmin Proteins 0.000 description 1
- 108010065387 alpha-N-(1,2-dithiolane-3-pentanoyl)glutamylalanine Proteins 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229960004538 alprazolam Drugs 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960002414 ambrisentan Drugs 0.000 description 1
- OUJTZYPIHDYQMC-LJQANCHMSA-N ambrisentan Chemical compound O([C@@H](C(OC)(C=1C=CC=CC=1)C=1C=CC=CC=1)C(O)=O)C1=NC(C)=CC(C)=N1 OUJTZYPIHDYQMC-LJQANCHMSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- 229960002576 amiloride Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 description 1
- 229960005260 amiodarone Drugs 0.000 description 1
- 229940040386 amitiza Drugs 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 229960002519 amoxapine Drugs 0.000 description 1
- QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 description 1
- 239000003392 amylase inhibitor Substances 0.000 description 1
- 206010002022 amyloidosis Diseases 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229960000983 anistreplase Drugs 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 229950005794 anrukinzumab Drugs 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 230000003510 anti-fibrotic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 230000003262 anti-osteoporosis Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229940125714 antidiarrheal agent Drugs 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 229960003886 apixaban Drugs 0.000 description 1
- 230000005735 apoptotic response Effects 0.000 description 1
- 229960001164 apremilast Drugs 0.000 description 1
- IMOZEMNVLZVGJZ-QGZVFWFLSA-N apremilast Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CS(C)(=O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 IMOZEMNVLZVGJZ-QGZVFWFLSA-N 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 108010033284 arginyl-2,'6'-dimethyltyrosyl-lysyl-phenylalaninamide Proteins 0.000 description 1
- 229960004372 aripiprazole Drugs 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 1
- 229950009925 atacicept Drugs 0.000 description 1
- 229960002274 atenolol Drugs 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- MOTJMGVDPWRKOC-QPVYNBJUSA-N atrasentan Chemical compound C1([C@H]2[C@@H]([C@H](CN2CC(=O)N(CCCC)CCCC)C=2C=C3OCOC3=CC=2)C(O)=O)=CC=C(OC)C=C1 MOTJMGVDPWRKOC-QPVYNBJUSA-N 0.000 description 1
- 229950010993 atrasentan Drugs 0.000 description 1
- 229950010288 atreleuton Drugs 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- PUKBOVABABRILL-YZNIXAGQSA-N avacopan Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC(=O)[C@@H]1[C@H](C=2C=CC(NC3CCCC3)=CC=2)N(C(=O)C=2C(=CC=CC=2C)F)CCC1 PUKBOVABABRILL-YZNIXAGQSA-N 0.000 description 1
- 229950001740 avacopan Drugs 0.000 description 1
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 1
- 229960001671 azapropazone Drugs 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960004574 azelastine Drugs 0.000 description 1
- 229950001786 azimilide Drugs 0.000 description 1
- 229960000794 baclofen Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229950010663 balaglitazone Drugs 0.000 description 1
- 229950000971 baricitinib Drugs 0.000 description 1
- HDRGJRSISASRAJ-WKPMUQCKSA-N bazlitoran Chemical compound CO[C@@H]1[C@H](O)[C@@H](COP(=O)(S)O[C@@H]2[C@@H](COP(=O)(S)O[C@H]3C[C@@H](O[C@@H]3COP(=O)(S)O[C@H]4C[C@@H](O[C@@H]4COP(=O)(S)O[C@H]5C[C@@H](O[C@@H]5COP(=O)(S)O[C@H]6C[C@@H](O[C@@H]6COP(=O)(S)O[C@H]7C[C@@H](O[C@@H]7COP(=O)(S)O[C@H]8C[C@@H](O[C@@H]8COP(=O)(S)O[C@H]9C[C@@H](O[C@@H]9COP(=O)(S)O[C@H]%10C[C@@H](O[C@@H]%10COP(=O)(S)O[C@@H]%11[C@@H](COP(=O)(S)O[C@@H]%12[C@@H](COP(=O)(S)O[C@H]%13C[C@@H](O[C@@H]%13COP(=O)(S)O[C@H]%14C[C@@H](O[C@@H]%14COP(=O)(S)O[C@H]%15C[C@@H](O[C@@H]%15COP(=O)(S)O[C@H]%16C[C@@H](O[C@@H]%16COP(=O)(S)O[C@H]%17C[C@@H](O[C@@H]%17COP(=O)(S)O[C@H]%18C[C@@H](O[C@@H]%18CO)N%19C=CC(=NC%19=O)N)N%20C=C(C)C(=O)NC%20=O)n%21cnc%22c(N)ncnc%21%22)N%23C=C(C)C(=O)NC%23=O)N%24C=CC(=NC%24=O)N)N%25C=C(C)C(=O)NC%25=O)O[C@H]([C@@H]%12OC)n%26cnc%27C(=O)NC(=Nc%26%27)N)O[C@H]([C@@H]%11OC)N%28C=CC(=O)NC%28=O)N%29C=C(C)C(=NC%29=O)N)n%30ccc%31C(=O)NC(=Nc%30%31)N)N%32C=C(C)C(=O)NC%32=O)N%33C=C(C)C(=O)NC%33=O)N%34C=CC(=NC%34=O)N)N%35C=C(C)C(=O)NC%35=O)N%36C=CC(=NC%36=O)N)N%37C=C(C)C(=O)NC%37=O)O[C@H]([C@@H]2OC)n%38cnc%39C(=O)NC(=Nc%38%39)N)O[C@H]1N%40C=CC(=O)NC%40=O HDRGJRSISASRAJ-WKPMUQCKSA-N 0.000 description 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
- 229940092705 beclomethasone Drugs 0.000 description 1
- 229960003270 belimumab Drugs 0.000 description 1
- 229960003515 bendroflumethiazide Drugs 0.000 description 1
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 description 1
- 229950000321 benralizumab Drugs 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 229960002529 benzbromarone Drugs 0.000 description 1
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229960001541 benzthiazide Drugs 0.000 description 1
- NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229950011103 betrixaban Drugs 0.000 description 1
- XHOLNRLADUSQLD-UHFFFAOYSA-N betrixaban Chemical compound C=1C=C(Cl)C=NC=1NC(=O)C1=CC(OC)=CC=C1NC(=O)C1=CC=C(C(=N)N(C)C)C=C1 XHOLNRLADUSQLD-UHFFFAOYSA-N 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 229920000080 bile acid sequestrant Polymers 0.000 description 1
- 229940096699 bile acid sequestrants Drugs 0.000 description 1
- 208000014679 binge eating disease Diseases 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- CRMSZGRTWXOBKL-UHFFFAOYSA-N bis(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=C(OC)C=CC=2)=C1 CRMSZGRTWXOBKL-UHFFFAOYSA-N 0.000 description 1
- CGXDIDXEMHMPIX-UHFFFAOYSA-N bis(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=C(C)C=CC=2)=C1 CGXDIDXEMHMPIX-UHFFFAOYSA-N 0.000 description 1
- IIFGXTNXSVLMSF-UHFFFAOYSA-N bis[3-(trifluoromethoxy)phenyl]methanone Chemical compound FC(F)(F)OC1=CC=CC(C(=O)C=2C=C(OC(F)(F)F)C=CC=2)=C1 IIFGXTNXSVLMSF-UHFFFAOYSA-N 0.000 description 1
- SAJDLEQJHPTZPY-UHFFFAOYSA-N bis[3-(trifluoromethylsulfanyl)phenyl]methanone Chemical compound FC(SC=1C=C(C=CC=1)C(=O)C1=CC(=CC=C1)SC(F)(F)F)(F)F SAJDLEQJHPTZPY-UHFFFAOYSA-N 0.000 description 1
- 229950004201 blisibimod Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- JCINBYQJBYJGDM-UHFFFAOYSA-N bms-911543 Chemical compound CCN1C(C(=O)N(C2CC2)C2CC2)=CC(C=2N(C)C=NC=22)=C1N=C2NC=1C=C(C)N(C)N=1 JCINBYQJBYJGDM-UHFFFAOYSA-N 0.000 description 1
- 229950011350 bococizumab Drugs 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229960003065 bosentan Drugs 0.000 description 1
- SXTRWVVIEPWAKM-UHFFFAOYSA-N bosentan hydrate Chemical compound O.COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SXTRWVVIEPWAKM-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 208000009973 brain hypoxia - ischemia Diseases 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 229960003735 brodalumab Drugs 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229960004436 budesonide Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 208000000594 bullous pemphigoid Diseases 0.000 description 1
- MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 1
- 229960004064 bumetanide Drugs 0.000 description 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
- 229960002495 buspirone Drugs 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229960004301 butriptyline Drugs 0.000 description 1
- ALELTFCQZDXAMQ-UHFFFAOYSA-N butriptyline Chemical compound C1CC2=CC=CC=C2C(CC(C)CN(C)C)C2=CC=CC=C21 ALELTFCQZDXAMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940084891 byetta Drugs 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 description 1
- 229960002882 calcipotriol Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 229950001261 camiglibose Drugs 0.000 description 1
- 229960001713 canagliflozin Drugs 0.000 description 1
- VHOFTEAWFCUTOS-TUGBYPPCSA-N canagliflozin hydrate Chemical compound O.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1.CC1=CC=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C=C1CC(S1)=CC=C1C1=CC=C(F)C=C1 VHOFTEAWFCUTOS-TUGBYPPCSA-N 0.000 description 1
- 229960001838 canakinumab Drugs 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 231100001012 cardiac lesion Toxicity 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
- 230000020411 cell activation Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 229950006295 cerdulatinib Drugs 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229960003115 certolizumab pegol Drugs 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 229960002155 chlorothiazide Drugs 0.000 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
- 239000000064 cholinergic agonist Substances 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 208000002849 chondrocalcinosis Diseases 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 description 1
- 208000013116 chronic cough Diseases 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- 208000013507 chronic prostatitis Diseases 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
- 229950009226 ciglitazone Drugs 0.000 description 1
- 229960004588 cilostazol Drugs 0.000 description 1
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
- 229940090100 cimzia Drugs 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 229960003120 clonazepam Drugs 0.000 description 1
- DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 229960003009 clopidogrel Drugs 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- 229960004362 clorazepate Drugs 0.000 description 1
- XDDJGVMJFWAHJX-UHFFFAOYSA-N clorazepic acid Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(C(=O)O)N=C1C1=CC=CC=C1 XDDJGVMJFWAHJX-UHFFFAOYSA-N 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 201000006145 cocaine dependence Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 210000004953 colonic tissue Anatomy 0.000 description 1
- 201000002758 colorectal adenoma Diseases 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000024203 complement activation Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 238000007887 coronary angioplasty Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 101150031809 cox1/2 gene Proteins 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- USZAGAREISWJDP-UHFFFAOYSA-N crisaborole Chemical compound C=1C=C2B(O)OCC2=CC=1OC1=CC=C(C#N)C=C1 USZAGAREISWJDP-UHFFFAOYSA-N 0.000 description 1
- 229950008199 crisaborole Drugs 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 229960003850 dabigatran Drugs 0.000 description 1
- YBSJFWOBGCMAKL-UHFFFAOYSA-N dabigatran Chemical compound N=1C2=CC(C(=O)N(CCC(O)=O)C=3N=CC=CC=3)=CC=C2N(C)C=1CNC1=CC=C(C(N)=N)C=C1 YBSJFWOBGCMAKL-UHFFFAOYSA-N 0.000 description 1
- 229960002806 daclizumab Drugs 0.000 description 1
- 229960004969 dalteparin Drugs 0.000 description 1
- 229950003518 danirixin Drugs 0.000 description 1
- 229960003834 dapagliflozin Drugs 0.000 description 1
- 229950004456 darapladib Drugs 0.000 description 1
- QQKNSPHAFATFNQ-UHFFFAOYSA-N darglitazone Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)NC1=O QQKNSPHAFATFNQ-UHFFFAOYSA-N 0.000 description 1
- 229950006689 darglitazone Drugs 0.000 description 1
- DBOBAIHRZONIPT-GHCHSQRSSA-N decanedioic acid;2,2-dimethyl-3-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]propylamino]propanamide Chemical compound OC(=O)CCCCCCCCC(O)=O.C=1C=C(OCCCNCC(C)(C)C(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.C=1C=C(OCCCNCC(C)(C)C(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DBOBAIHRZONIPT-GHCHSQRSSA-N 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
- 229960005227 delapril Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- LOWWYYZBZNSPDT-ZBEGNZNMSA-N delgocitinib Chemical compound C[C@H]1CN(C(=O)CC#N)[C@@]11CN(C=2C=3C=CNC=3N=CN=2)CC1 LOWWYYZBZNSPDT-ZBEGNZNMSA-N 0.000 description 1
- 208000022401 dense deposit disease Diseases 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 229960001271 desloratadine Drugs 0.000 description 1
- 229960002593 desoximetasone Drugs 0.000 description 1
- VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960002777 dicycloverine Drugs 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 229950009763 dilmapimod Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- WQAWEUZTDVWTDB-UHFFFAOYSA-N dimethyl(oxo)phosphanium Chemical compound C[P+](C)=O WQAWEUZTDVWTDB-UHFFFAOYSA-N 0.000 description 1
- 229960004192 diphenoxylate Drugs 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- VXIHRIQNJCRFQX-UHFFFAOYSA-K disodium aurothiomalate Chemical compound [Na+].[Na+].[O-]C(=O)CC(S[Au])C([O-])=O VXIHRIQNJCRFQX-UHFFFAOYSA-K 0.000 description 1
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
- 229960002994 dofetilide Drugs 0.000 description 1
- 229960003530 donepezil Drugs 0.000 description 1
- 229960001393 dosulepin Drugs 0.000 description 1
- 229960005426 doxepin Drugs 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 229960000413 doxercalciferol Drugs 0.000 description 1
- HKXBNHCUPKIYDM-CGMHZMFXSA-N doxercalciferol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C HKXBNHCUPKIYDM-CGMHZMFXSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229960001850 droxicam Drugs 0.000 description 1
- OEHFRZLKGRKFAS-UHFFFAOYSA-N droxicam Chemical compound C12=CC=CC=C2S(=O)(=O)N(C)C(C2=O)=C1OC(=O)N2C1=CC=CC=N1 OEHFRZLKGRKFAS-UHFFFAOYSA-N 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229960005175 dulaglutide Drugs 0.000 description 1
- 108010005794 dulaglutide Proteins 0.000 description 1
- 229940099198 dulcolax Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229950003693 dutogliptin Drugs 0.000 description 1
- 229950004949 duvelisib Drugs 0.000 description 1
- 229960002224 eculizumab Drugs 0.000 description 1
- 229960000622 edoxaban Drugs 0.000 description 1
- PSMMNJNZVZZNOI-SJILXJHISA-N edoxaban tosylate hydrate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1.N([C@H]1CC[C@@H](C[C@H]1NC(=O)C=1SC=2CN(C)CCC=2N=1)C(=O)N(C)C)C(=O)C(=O)NC1=CC=C(Cl)C=N1 PSMMNJNZVZZNOI-SJILXJHISA-N 0.000 description 1
- 229950000269 emiglitate Drugs 0.000 description 1
- 229960003345 empagliflozin Drugs 0.000 description 1
- OBWASQILIWPZMG-QZMOQZSNSA-N empagliflozin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(Cl)C(CC=2C=CC(O[C@@H]3COCC3)=CC=2)=C1 OBWASQILIWPZMG-QZMOQZSNSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 229960000873 enalapril Drugs 0.000 description 1
- 108091016497 enarodustat Proteins 0.000 description 1
- 229950003048 enavatuzumab Drugs 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 239000002308 endothelin receptor antagonist Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229950002375 englitazone Drugs 0.000 description 1
- 229960000610 enoxaparin Drugs 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 229960001208 eplerenone Drugs 0.000 description 1
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 1
- 229960001123 epoprostenol Drugs 0.000 description 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
- 229950009760 epratuzumab Drugs 0.000 description 1
- GLGOPUHVAZCPRB-LROMGURASA-N eptifibatide Chemical compound N1C(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCCNC(=N)N)NC(=O)CCSSC[C@@H](C(N)=O)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]1CC1=CN=C2[C]1C=CC=C2 GLGOPUHVAZCPRB-LROMGURASA-N 0.000 description 1
- 229960004468 eptifibatide Drugs 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 229960003199 etacrynic acid Drugs 0.000 description 1
- AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 description 1
- 229960000403 etanercept Drugs 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- NWWORXYTJRPSMC-QKPAOTATSA-N ethyl 4-[2-[(2r,3r,4r,5s)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 NWWORXYTJRPSMC-QKPAOTATSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 229960000745 ethylnorepinephrine hydrochloride Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229960004945 etoricoxib Drugs 0.000 description 1
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 108010015174 exendin 3 Proteins 0.000 description 1
- LMHMJYMCGJNXRS-IOPUOMRJSA-N exendin-3 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@H](C)O)[C@H](C)O)C(C)C)C1=CC=CC=C1 LMHMJYMCGJNXRS-IOPUOMRJSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 description 1
- 229960005101 febuxostat Drugs 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 229960003592 fexofenadine Drugs 0.000 description 1
- DFQGDHBGRSTTHX-UHFFFAOYSA-N fiboflapon Chemical compound C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C(O)=O DFQGDHBGRSTTHX-UHFFFAOYSA-N 0.000 description 1
- 229950002834 fiboflapon Drugs 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- RGUQWGXAYZNLMI-UHFFFAOYSA-N flumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O RGUQWGXAYZNLMI-UHFFFAOYSA-N 0.000 description 1
- 229960003028 flumethiazide Drugs 0.000 description 1
- 229960000676 flunisolide Drugs 0.000 description 1
- 229960000785 fluocinonide Drugs 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 229960000289 fluticasone propionate Drugs 0.000 description 1
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 201000005206 focal segmental glomerulosclerosis Diseases 0.000 description 1
- 231100000854 focal segmental glomerulosclerosis Toxicity 0.000 description 1
- 229960001318 fondaparinux Drugs 0.000 description 1
- KANJSNBRCNMZMV-ABRZTLGGSA-N fondaparinux Chemical compound O[C@@H]1[C@@H](NS(O)(=O)=O)[C@@H](OC)O[C@H](COS(O)(=O)=O)[C@H]1O[C@H]1[C@H](OS(O)(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O4)NS(O)(=O)=O)[C@H](O3)C(O)=O)O)[C@@H](COS(O)(=O)=O)O2)NS(O)(=O)=O)[C@H](C(O)=O)O1 KANJSNBRCNMZMV-ABRZTLGGSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229960002848 formoterol Drugs 0.000 description 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960002490 fosinopril Drugs 0.000 description 1
- 229950004003 fresolimumab Drugs 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 229960003980 galantamine Drugs 0.000 description 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- YRSVDSQRGBYVIY-GJZGRUSLSA-N gemopatrilat Chemical compound O=C1N(CC(O)=O)C(C)(C)CCC[C@@H]1NC(=O)[C@@H](S)CC1=CC=CC=C1 YRSVDSQRGBYVIY-GJZGRUSLSA-N 0.000 description 1
- 229950006480 gemopatrilat Drugs 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 208000016361 genetic disease Diseases 0.000 description 1
- 229960003776 glatiramer acetate Drugs 0.000 description 1
- 229960000346 gliclazide Drugs 0.000 description 1
- 229960004346 glimepiride Drugs 0.000 description 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960003468 gliquidone Drugs 0.000 description 1
- 229950008402 glisentide Drugs 0.000 description 1
- NSJYMFYVNWVGON-UHFFFAOYSA-N glisentide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCC2)C=C1 NSJYMFYVNWVGON-UHFFFAOYSA-N 0.000 description 1
- GZKDXUIWCNCNBJ-UHFFFAOYSA-N glisolamide Chemical compound O1C(C)=CC(C(=O)NCCC=2C=CC(=CC=2)S(=O)(=O)NC(=O)NC2CCCCC2)=N1 GZKDXUIWCNCNBJ-UHFFFAOYSA-N 0.000 description 1
- 229950005319 glisolamide Drugs 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 230000001890 gluconeogenic effect Effects 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000035780 glucosuria Effects 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229940015042 glycopyrrolate Drugs 0.000 description 1
- 229960001743 golimumab Drugs 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 239000003119 guanylate cyclase activator Substances 0.000 description 1
- 229950010864 guselkumab Drugs 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 230000003400 hallucinatory effect Effects 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 208000003215 hereditary nephritis Diseases 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
- 229940006607 hirudin Drugs 0.000 description 1
- 238000002657 hormone replacement therapy Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229960003313 hydroflumethiazide Drugs 0.000 description 1
- DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000004093 hydrolase inhibitor Substances 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 229960004171 hydroxychloroquine Drugs 0.000 description 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 206010020765 hypersomnia Diseases 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 206010020871 hypertrophic cardiomyopathy Diseases 0.000 description 1
- PUTJFIQGLGDLIT-UHFFFAOYSA-N hyrtiosal Natural products O=CC1(C)CC(C2(CCCC(C)(C)C2CC2)C)C2(C)C1CC(O)C=1C=COC=1 PUTJFIQGLGDLIT-UHFFFAOYSA-N 0.000 description 1
- 229960004053 ibutilide Drugs 0.000 description 1
- 229960003445 idelalisib Drugs 0.000 description 1
- YKLIKGKUANLGSB-HNNXBMFYSA-N idelalisib Chemical compound C1([C@@H](NC=2[C]3N=CN=C3N=CN=2)CC)=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1 YKLIKGKUANLGSB-HNNXBMFYSA-N 0.000 description 1
- BBPRUNPUJIUXSE-DXKRWKNPSA-N ifetroban Chemical compound CCCCCNC(=O)C1=COC([C@H]2[C@H]([C@@H]3CC[C@H]2O3)CC=2C(=CC=CC=2)CCC(O)=O)=N1 BBPRUNPUJIUXSE-DXKRWKNPSA-N 0.000 description 1
- 229950004274 ifetroban Drugs 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000005232 imidazopyridines Chemical class 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229940095970 imodium Drugs 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000937 inactivator Effects 0.000 description 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 208000015266 indolent plasma cell myeloma Diseases 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229940050282 inebilizumab-cdon Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000008798 inflammatory stress Effects 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004001 inositols Chemical class 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000004026 insulin derivative Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 208000015046 intermittent explosive disease Diseases 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 201000010849 intracranial embolism Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 208000026876 intravascular large B-cell lymphoma Diseases 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- AHFWIQIYAXSLBA-RQXATKFSSA-N ipragliflozin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(F)C(CC=2SC3=CC=CC=C3C=2)=C1 AHFWIQIYAXSLBA-RQXATKFSSA-N 0.000 description 1
- 229960001361 ipratropium bromide Drugs 0.000 description 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
- 229950003599 ipsapirone Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960002672 isocarboxazid Drugs 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- ACRHBAYQBXXRTO-OAQYLSRUSA-N ivabradine Chemical group C1CC2=CC(OC)=C(OC)C=C2CC(=O)N1CCCN(C)C[C@H]1CC2=C1C=C(OC)C(OC)=C2 ACRHBAYQBXXRTO-OAQYLSRUSA-N 0.000 description 1
- 229960003825 ivabradine Drugs 0.000 description 1
- 229960005435 ixekizumab Drugs 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 230000008463 key metabolic pathway Effects 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229950010645 lanoteplase Drugs 0.000 description 1
- 108010051044 lanoteplase Proteins 0.000 description 1
- GKWPCEFFIHSJOE-UHFFFAOYSA-N laquinimod Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 GKWPCEFFIHSJOE-UHFFFAOYSA-N 0.000 description 1
- 229960004577 laquinimod Drugs 0.000 description 1
- 208000003849 large cell carcinoma Diseases 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 229950002183 lebrikizumab Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960000681 leflunomide Drugs 0.000 description 1
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 1
- FGQFOYHRJSUHMR-UHFFFAOYSA-N lesinurad Chemical compound OC(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 FGQFOYHRJSUHMR-UHFFFAOYSA-N 0.000 description 1
- 229960003838 lesinurad Drugs 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 229960002397 linagliptin Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229960002701 liraglutide Drugs 0.000 description 1
- 229960002394 lisinopril Drugs 0.000 description 1
- CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229960001093 lixisenatide Drugs 0.000 description 1
- 108010004367 lixisenatide Proteins 0.000 description 1
- 229940087973 lomotil Drugs 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229940125389 long-acting beta agonist Drugs 0.000 description 1
- 229960001571 loperamide Drugs 0.000 description 1
- 229960003088 loratadine Drugs 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 229960004391 lorazepam Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- 229940060963 lotronex Drugs 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 229940127215 low-molecular weight heparin Drugs 0.000 description 1
- WGFOBBZOWHGYQH-MXHNKVEKSA-N lubiprostone Chemical compound O1[C@](C(F)(F)CCCC)(O)CC[C@@H]2[C@@H](CCCCCCC(O)=O)C(=O)C[C@H]21 WGFOBBZOWHGYQH-MXHNKVEKSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 229950004397 luseogliflozin Drugs 0.000 description 1
- 201000007919 lymphoplasmacytic lymphoma Diseases 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- JGCMEBMXRHSZKX-UHFFFAOYSA-N macitentan Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 JGCMEBMXRHSZKX-UHFFFAOYSA-N 0.000 description 1
- 229960001039 macitentan Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960004090 maprotiline Drugs 0.000 description 1
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 208000008585 mastocytosis Diseases 0.000 description 1
- 229950007254 mavrilimumab Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229940103185 mefenamate Drugs 0.000 description 1
- 229950004994 meglitinide Drugs 0.000 description 1
- 229960002137 melagatran Drugs 0.000 description 1
- DKWNMCUOEDMMIN-PKOBYXMFSA-N melagatran Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)[C@H]1N(C(=O)[C@H](NCC(O)=O)C2CCCCC2)CC1 DKWNMCUOEDMMIN-PKOBYXMFSA-N 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229960001929 meloxicam Drugs 0.000 description 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- 201000008350 membranous glomerulonephritis Diseases 0.000 description 1
- 229960005108 mepolizumab Drugs 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- FEFIBEHSXLKJGI-UHFFFAOYSA-N methyl 2-[3-[[3-(6-amino-2-butoxy-8-oxo-7h-purin-9-yl)propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCOCC1 FEFIBEHSXLKJGI-UHFFFAOYSA-N 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 1
- 229960003793 midazolam Drugs 0.000 description 1
- 229960001110 miglitol Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940060946 miralax Drugs 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 description 1
- 229960004644 moclobemide Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229960002744 mometasone furoate Drugs 0.000 description 1
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 1
- 229960004866 mycophenolate mofetil Drugs 0.000 description 1
- 210000000066 myeloid cell Anatomy 0.000 description 1
- 210000003098 myoblast Anatomy 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000001016 myotrophic effect Effects 0.000 description 1
- DNGNRXXCOAVIDS-UHFFFAOYSA-N n,2-dimethyl-1-pyridin-3-ylpropan-1-amine Chemical compound CNC(C(C)C)C1=CC=CN=C1 DNGNRXXCOAVIDS-UHFFFAOYSA-N 0.000 description 1
- PWDYHMBTPGXCSN-VCBMUGGBSA-N n,n'-bis[3,5-bis[(e)-n-(diaminomethylideneamino)-c-methylcarbonimidoyl]phenyl]decanediamide Chemical compound NC(N)=N/N=C(\C)C1=CC(C(=N/N=C(N)N)/C)=CC(NC(=O)CCCCCCCCC(=O)NC=2C=C(C=C(C=2)C(\C)=N\N=C(N)N)C(\C)=N\N=C(N)N)=C1 PWDYHMBTPGXCSN-VCBMUGGBSA-N 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- OUQVKRKGTAUJQA-UHFFFAOYSA-N n-[(1-chloro-4-hydroxyisoquinolin-3-yl)carbonyl]glycine Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 OUQVKRKGTAUJQA-UHFFFAOYSA-N 0.000 description 1
- WDPFJWLDPVQCAJ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[2-[(4-fluorophenyl)methylsulfanyl]-4-oxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-1-yl]-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide Chemical compound C1=2CCCC=2C(=O)N=C(SCC=2C=CC(F)=CC=2)N1CC(=O)N(CCN(CC)CC)CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 WDPFJWLDPVQCAJ-UHFFFAOYSA-N 0.000 description 1
- QZECRCLSIGFCIO-RISCZKNCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[(2r,3s)-3,4-dihydroxybutan-2-yl]oxypyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(O[C@H](C)[C@@H](O)CO)=CC=1NS(=O)(=O)N1CCC1 QZECRCLSIGFCIO-RISCZKNCSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- RTDCVLCTBQDLBW-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 RTDCVLCTBQDLBW-UHFFFAOYSA-N 0.000 description 1
- MPYACSQFXVMWNO-UHFFFAOYSA-N n-[5-[4-(3,3-dimethylazetidine-1-carbonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide Chemical compound C1C(C)(C)CN1C(=O)C1=CC=C(C=2N3N=C(NC(=O)C4CC4)N=C3C=CC=2)C=C1 MPYACSQFXVMWNO-UHFFFAOYSA-N 0.000 description 1
- VLVWKOPMGYYNKV-UHFFFAOYSA-N n-[5-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide;trihydrate;hydrochloride Chemical compound O.O.O.Cl.C1CC1C(=O)NC(=NN12)N=C1C=CC=C2C(C=C1)=CC=C1CN1CCS(=O)(=O)CC1 VLVWKOPMGYYNKV-UHFFFAOYSA-N 0.000 description 1
- IGLNXKVGKIFNBQ-UHFFFAOYSA-N n-[5-[[5-fluoro-4-(4-prop-2-ynoxyanilino)pyrimidin-2-yl]amino]-2-methylphenyl]sulfonylpropanamide Chemical compound C1=C(C)C(S(=O)(=O)NC(=O)CC)=CC(NC=2N=C(NC=3C=CC(OCC#C)=CC=3)C(F)=CN=2)=C1 IGLNXKVGKIFNBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RYLMQQMCVLCCOT-UHFFFAOYSA-N n-methyl-1-pyridin-3-ylethanamine Chemical compound CNC(C)C1=CC=CN=C1 RYLMQQMCVLCCOT-UHFFFAOYSA-N 0.000 description 1
- MCSAQVGDZLPTBS-UHFFFAOYSA-N n-methyl-1-pyridin-3-ylmethanamine Chemical compound CNCC1=CC=CN=C1 MCSAQVGDZLPTBS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004760 naphazoline hydrochloride Drugs 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 229960005027 natalizumab Drugs 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 208000013435 necrotic lesion Diseases 0.000 description 1
- 208000025440 neoplasm of neck Diseases 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- 201000009925 nephrosclerosis Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 208000027134 non-immunoglobulin-mediated membranoproliferative glomerulonephritis Diseases 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 102000006255 nuclear receptors Human genes 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 238000013116 obese mouse model Methods 0.000 description 1
- 229950005751 ocrelizumab Drugs 0.000 description 1
- 229960002450 ofatumumab Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229950010006 olokizumab Drugs 0.000 description 1
- CGBJSGAELGCMKE-UHFFFAOYSA-N omipalisib Chemical compound COC1=NC=C(C=2C=C3C(C=4C=NN=CC=4)=CC=NC3=CC=2)C=C1NS(=O)(=O)C1=CC=C(F)C=C1F CGBJSGAELGCMKE-UHFFFAOYSA-N 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- ZTCHEOLGUZDPAN-UHFFFAOYSA-N oxan-3-ylmethanamine Chemical compound NCC1CCCOC1 ZTCHEOLGUZDPAN-UHFFFAOYSA-N 0.000 description 1
- IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 description 1
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 1
- 229960004535 oxazepam Drugs 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229960001609 oxitropium bromide Drugs 0.000 description 1
- LCELQERNWLBPSY-KHSTUMNDSA-M oxitropium bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CC)=CC=CC=C1 LCELQERNWLBPSY-KHSTUMNDSA-M 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001528 oxymetazoline Drugs 0.000 description 1
- WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 1
- 229960001057 paliperidone Drugs 0.000 description 1
- 201000008743 palmoplantar keratosis Diseases 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 201000010198 papillary carcinoma Diseases 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 208000021237 paraquat poisoning Diseases 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229960000987 paricalcitol Drugs 0.000 description 1
- BPKAHTKRCLCHEA-UBFJEZKGSA-N paricalcitol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1C[C@@H](O)C[C@H](O)C1 BPKAHTKRCLCHEA-UBFJEZKGSA-N 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950011485 pascolizumab Drugs 0.000 description 1
- SVCSMAZYWOQCBW-NVJMFHFGSA-N pefcalcitol Chemical compound C1(/[C@@H]2CC=C([C@]2(CCC1)C)[C@@H](OCC(=O)NCC(F)(F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C SVCSMAZYWOQCBW-NVJMFHFGSA-N 0.000 description 1
- 229950005157 peficitinib Drugs 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 229950008492 pentopril Drugs 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229950002913 pexmetinib Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960000964 phenelzine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960003733 phenylephrine hydrochloride Drugs 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960002305 phenylpropanolamine hydrochloride Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229950005769 pilaralisib Drugs 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 1
- 229960005414 pirbuterol Drugs 0.000 description 1
- 229960003073 pirfenidone Drugs 0.000 description 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 description 1
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
- RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 description 1
- 108010010907 pitrakinra Proteins 0.000 description 1
- 229950008185 pitrakinra Drugs 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229960005483 polythiazide Drugs 0.000 description 1
- 229920000046 polythiazide Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229950009275 ponesimod Drugs 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 229960004197 prasugrel Drugs 0.000 description 1
- DTGLZDAWLRGWQN-UHFFFAOYSA-N prasugrel Chemical compound C1CC=2SC(OC(=O)C)=CC=2CN1C(C=1C(=CC=CC=1)F)C(=O)C1CC1 DTGLZDAWLRGWQN-UHFFFAOYSA-N 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 229960004856 prazepam Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- 229960001233 pregabalin Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Chemical class 0.000 description 1
- 230000008741 proinflammatory signaling process Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
- 229960000203 propafenone Drugs 0.000 description 1
- WPDCHTSXOPUOII-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)N=C1C WPDCHTSXOPUOII-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229960002601 protriptyline Drugs 0.000 description 1
- BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003447 pseudoephedrine hydrochloride Drugs 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- HQIBSDCOMQYSPF-UHFFFAOYSA-N pyrazin-2-ylmethanamine Chemical compound NCC1=CN=CC=N1 HQIBSDCOMQYSPF-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ROSKZJGILXBSFM-UHFFFAOYSA-N pyrimidin-2-ylmethanamine Chemical compound NCC1=NC=CC=N1 ROSKZJGILXBSFM-UHFFFAOYSA-N 0.000 description 1
- AUHXBTKGPUVFCB-UHFFFAOYSA-N pyrimidin-4-ylmethanamine Chemical compound NCC1=CC=NC=N1 AUHXBTKGPUVFCB-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229940073095 questran Drugs 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
- 229960001455 quinapril Drugs 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229950010994 ralimetinib Drugs 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 229940075993 receptor modulator Drugs 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000009169 relapsing polychondritis Diseases 0.000 description 1
- 201000002793 renal fibrosis Diseases 0.000 description 1
- 239000002461 renin inhibitor Substances 0.000 description 1
- 229940086526 renin-inhibitors Drugs 0.000 description 1
- 229960003254 reslizumab Drugs 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 235000021283 resveratrol Nutrition 0.000 description 1
- 229940016667 resveratrol Drugs 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 230000000250 revascularization Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960000529 riociguat Drugs 0.000 description 1
- WXXSNCNJFUAIDG-UHFFFAOYSA-N riociguat Chemical compound N1=C(N)C(N(C)C(=O)OC)=C(N)N=C1C(C1=CC=CN=C11)=NN1CC1=CC=CC=C1F WXXSNCNJFUAIDG-UHFFFAOYSA-N 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229960004641 rituximab Drugs 0.000 description 1
- 229960001148 rivaroxaban Drugs 0.000 description 1
- KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 1
- 229960002586 roflumilast Drugs 0.000 description 1
- 229950010316 rontalizumab Drugs 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
- 229960000215 ruxolitinib Drugs 0.000 description 1
- HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical compound C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 description 1
- 229960004937 saxagliptin Drugs 0.000 description 1
- 108010033693 saxagliptin Proteins 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 208000022610 schizoaffective disease Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 229960004540 secukinumab Drugs 0.000 description 1
- 229950011186 semaglutide Drugs 0.000 description 1
- 108010060325 semaglutide Proteins 0.000 description 1
- 229950011005 semapimod Drugs 0.000 description 1
- IPQVTOJGNYVQEO-KGFNBKMBSA-N sennoside A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1[C@@H]2[C@H]1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-KGFNBKMBSA-N 0.000 description 1
- 229940063651 senokot Drugs 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RGYQPQARIQKJKH-UHFFFAOYSA-N setanaxib Chemical compound CN(C)C1=CC=CC(C2=C3C(=O)N(C=4C(=CC=CC=4)Cl)NC3=CC(=O)N2C)=C1 RGYQPQARIQKJKH-UHFFFAOYSA-N 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 229950010077 sifalimumab Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960003323 siltuximab Drugs 0.000 description 1
- 229950009513 simtuzumab Drugs 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 229950006094 sirukumab Drugs 0.000 description 1
- MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 description 1
- 229960004034 sitagliptin Drugs 0.000 description 1
- 229960002578 sitaxentan Drugs 0.000 description 1
- PHWXUGHIIBDVKD-UHFFFAOYSA-N sitaxentan Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC=3OCOC=3C=2)C)=C1Cl PHWXUGHIIBDVKD-UHFFFAOYSA-N 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229960001315 sodium aurothiomalate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 108010082379 somatostatin receptor type 1 Proteins 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 229950005814 sotrastaurin Drugs 0.000 description 1
- 229950002009 sparsentan Drugs 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 206010062113 splenic marginal zone lymphoma Diseases 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229960003329 sulfinpyrazone Drugs 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229950011082 suplatast tosilate Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229950010265 tabalumab Drugs 0.000 description 1
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 description 1
- 229960000835 tadalafil Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229950004351 telenzepine Drugs 0.000 description 1
- 206010043207 temporal arteritis Diseases 0.000 description 1
- CBPNZQVSJQDFBE-HGVVHKDOSA-N temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CCC2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-HGVVHKDOSA-N 0.000 description 1
- 229950001790 tendamistat Drugs 0.000 description 1
- 108010037401 tendamistate Proteins 0.000 description 1
- 229960000216 tenecteplase Drugs 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- FOHWAQGURRYJFK-ONEGZZNKSA-N terevalefim Chemical compound C=1C=NNC=1/C=C/C1=CC=CS1 FOHWAQGURRYJFK-ONEGZZNKSA-N 0.000 description 1
- 229960000331 teriflunomide Drugs 0.000 description 1
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 description 1
- UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 description 1
- GGPVOXVKIVXELX-UHFFFAOYSA-N tert-butyl 3-formylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(C=O)=C1 GGPVOXVKIVXELX-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
- BJORNXNYWNIWEY-UHFFFAOYSA-N tetrahydrozoline hydrochloride Chemical compound Cl.N1CCN=C1C1C2=CC=CC=C2CCC1 BJORNXNYWNIWEY-UHFFFAOYSA-N 0.000 description 1
- 229940021790 tetrahydrozoline hydrochloride Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- CJIAPFQLVZPUQJ-UHFFFAOYSA-N thiadiazol-4-ylmethanamine Chemical compound NCC1=CSN=N1 CJIAPFQLVZPUQJ-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000005403 thiohaloalkoxy group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- OEKWJQXRCDYSHL-FNOIDJSQSA-N ticagrelor Chemical compound C1([C@@H]2C[C@H]2NC=2N=C(N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](OCCO)C4)O)N=NC3=2)SCCC)=CC=C(F)C(F)=C1 OEKWJQXRCDYSHL-FNOIDJSQSA-N 0.000 description 1
- 229960002528 ticagrelor Drugs 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229950005515 tildrakizumab Drugs 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 description 1
- 229960003425 tirofiban Drugs 0.000 description 1
- 229960001787 tisopurine Drugs 0.000 description 1
- PYAOPMWCFSVFOT-UHFFFAOYSA-N tisopurine Chemical compound SC1=NC=NC2=C1C=NN2 PYAOPMWCFSVFOT-UHFFFAOYSA-N 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 229960003989 tocilizumab Drugs 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 229950004176 topiroxostat Drugs 0.000 description 1
- 229960005461 torasemide Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229950000835 tralokinumab Drugs 0.000 description 1
- PHTUQLWOUWZIMZ-GZTJUZNOSA-N trans-dothiepin Chemical compound C1SC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 PHTUQLWOUWZIMZ-GZTJUZNOSA-N 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 102000042565 transient receptor (TC 1.A.4) family Human genes 0.000 description 1
- 108091053409 transient receptor (TC 1.A.4) family Proteins 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
- 229960003991 trazodone Drugs 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229950010086 tregalizumab Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960002431 trimipramine Drugs 0.000 description 1
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-O tritert-butylphosphanium Chemical compound CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-O 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- WUJVPODXELZABP-FWJXURDUSA-N trodusquemine Chemical compound C([C@@H]1C[C@H]2O)[C@@H](NCCCNCCCCNCCCN)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C(C)C)OS(O)(=O)=O)[C@@]2(C)CC1 WUJVPODXELZABP-FWJXURDUSA-N 0.000 description 1
- 229950004499 trodusquemine Drugs 0.000 description 1
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 1
- 229930004006 tropane Natural products 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 208000010576 undifferentiated carcinoma Diseases 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229960003824 ustekinumab Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- 229960002381 vardenafil Drugs 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- 229960004751 varenicline Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 229960004914 vedolizumab Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229950008314 veliflapon Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- 229950007805 vercirnon Drugs 0.000 description 1
- 229950005117 verucerfont Drugs 0.000 description 1
- RNOBTWYQAWEZHH-JGVFFNPUSA-N vi5lr1eu47 Chemical compound C12=CC(C(F)(F)F)=CC=C2[C@]2([H])CNC[C@@]1([H])C2 RNOBTWYQAWEZHH-JGVFFNPUSA-N 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- 229960001255 viloxazine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 102000009310 vitamin D receptors Human genes 0.000 description 1
- 108050000156 vitamin D receptors Proteins 0.000 description 1
- 229960005289 voclosporin Drugs 0.000 description 1
- BICRTLVBTLFLRD-PTWUADNWSA-N voclosporin Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C=C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O BICRTLVBTLFLRD-PTWUADNWSA-N 0.000 description 1
- 108010057559 voclosporin Proteins 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 229960001095 xylometazoline hydrochloride Drugs 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- 229950003684 zibotentan Drugs 0.000 description 1
- BPKIMPVREBSLAJ-QTBYCLKRSA-N ziconotide Chemical compound C([C@H]1C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]2C(=O)N[C@@H]3C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@H](C(N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC2)C(N)=O)=O)CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CSSC3)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N1)=O)CCSC)[C@@H](C)O)C1=CC=C(O)C=C1 BPKIMPVREBSLAJ-QTBYCLKRSA-N 0.000 description 1
- 229960002811 ziconotide Drugs 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Definitions
- Vanin- 1 is a pantetheinase that hydrolyses pantetheine to form pantothenic acid (vitamin B5) and the low-molecular-weight thiol cysteamine. Vanin- 1 expression is up- regulated in multiple cells types exposed to various stimuli including inflammatory and oxidative stress conditions.
- the vanin family includes secreted and membrane- associated enzymes. Specifically, three family members have been described in humans (vanin- 1, vanin-2 and vanin-3) and two in mice (vanin-l and vanin-3) all of which have pantetheinase activity.
- vanin-l The only known substrate of the vanin enzymes is pantetheine and vanin-l is believed to be the major pantetheinase in vivo (Pitari et al ., FEBS Lett 483, 149-154 (2000)).
- Pantothenic acid is an essential factor in the synthesis of coenzyme A (CoA) which is involved in multiple cellular processes, for example, the metabolism of short- and long-chain fatty acids (Leonardi et al., Prog. Lipid. Res., 44, 125-153 (2005)).
- Cysteamine is thought to be a key regulator of essential metabolic pathways, putatively inhibiting enzymes such as transglutaminases (Jeitner et al. , Biochem. Pharmacol. 69, 961-970 (2005) and Elli et al. , Lab. Invest.
- caspase 3 (Lesort et al. , J. Biol. Chem., 278, 3825-3830 (2003)), GSTA3 (Di Leandro et al. , Free Radic. Biol. Med., 44, 1088-1096 (2008)), protein kinase Ce (Chu et al, Cancer Res., 65, 10478-10485 (2005)), and g-glutamylcysteine synthase (g-GCS) which catalyzes a key step in the synthesis of glutathione (GSH), the major cellular antioxidant molecule (Martin et al, J. Clin. Invest., 113, 591-597 (2004)).
- GSH glutathione
- vanin-l expression and activity have been shown to be inversely correlated with levels of PPARy, a nuclear receptor involved in the dampening of pro- inflammatory signaling.
- vanin-l may upregulate oxidative stress and inflammation and contribute to disease pathogenesis (F. Martin et al, supra, and C. Berruyer et al, J. Exp. Med., 203, 2817-2827 (2006), particularly in tissues where vanin-l is highly expressed, such as the mucosa of patients with inflammatory bowel diseases (IBD) (Gensollen et al. , Inflamm. Bowel. Dis., 19, 2315-2325 (2013)).
- IBD inflammatory bowel diseases
- vanin-l -deficient mice are more resistant to paraquat poisoning and to exposure to lethal doses of g-irradiation. These mice have reduced levels of pro-inflammatory cytokines as well as a reduced apoptotic response in the small intestine following exposure to oxidative stress (Berruyer et al ., Mol. Cell. Biol. 24, 7214-7224 (2004)). In addition to the reported reduced inflammation, vanin-l KO mice have increased GSH levels and absence of cysteamine in tissues where vanin-l expression is predominant (liver and kidney) (Pitari et al, supra).
- cystamine Intraperitoneal administration of cystamine abrogates the resistant phenotype of the mutant mice demonstrating that cysteamine/cystamine participate in the tissue response following exposure to stress (Berruyer et al, 2004, supra). Vanin-l deficiency also reduces inflammation and injury in the gut in animals exposed acutely to indomethacin or infected chronically with Schistosoma mansoni (Martin et al, supra).
- vanin-l -deficient mice are protected in DSS- and TNBS-induced mouse models of colitis, by showing reduced levels of multiple pro-inflammatory cytokines, attenuated recruitment of myeloid cells to the mucosa, and reduced colonic tissue damage (Berruyer et al, 2006, supra and Pouyet et al, Inflamm. Bowel Dis., 16, 96-104 (2010)).
- Vanin-l may also be implicated in other diseases beyond IBD.
- vanin-l has been associated with the regulation of multiple key metabolic pathways. Expression of vanin-l is high in liver and strongly induced by fasting via PPARa induction, and leads to an increase the expression of gluconeogenic genes and hepatic glucose output, resulting in hyperglycemia (van Diepen et al, Sci. Rep., 6, 21906 (2016) and Chen et al, Diabetes, 63, 2073-2085 (2014)). Recently, increased vanin-l activity was observed in plasma and liver of high fat diet (HFD)-induced obese mice, as well as ZDF-diabetic rats.
- HFD high fat diet
- VNN1 KO mice have mildly improved glucose tolerance and insulin sensitivity in HFD-fed animals (van Diepen et al. , supra). Vanin-l expression is high in human psoriatic skin leading to the proposal that vanin-l plays a role in Thl 7/Th 1 -driven inflammatory skin conditions (Jansen et al. , J. Invest. Dermatol., 129, 2167-2174 (2009)). In addition, expression of vanin-l in whole blood is higher in patients suffering from chronic pediatric immune thrombocytopenia (ITP) (Zhang et al. , Blood, 117, 4569-4579 (2011)).
- ITP chronic pediatric immune thrombocytopenia
- Vanin-l mRNA expression levels have been shown to correlate with HDL-C levels supporting a potential role of vanin-l in cardiovascular disease (Kaskow et al. , Eur. J. Hum. Genet., 22, 688-695 (2014)).
- polymorphisms in VNN1 gene are associated with blood pressure and HDL levels further supporting a role for vanin in cardiovascular diseases (Wang et al. , PLoS Genet., 10, el00464l (2014)).
- Vanin-l may also be a potential therapeutic target for neointimal hyperplasia following revascularization as it plays a role in driving smooth muscle cell activation in post-arterial injury (Dammanahalli et al.
- compositions comprising compounds of Formula (I), or pharmaceutically acceptable salts thereof and methods of making and using compounds of Formula (I), or pharmaceutically acceptable salts thereof.
- Certain compounds of Formula (I), or pharmaceutically acceptable salts thereof are inhibitors of vanin proteins, such as vanin- 1, and may be used for treating certain diseases, disorders, and conditions, either as mono-therapies or as components of combination therapies.
- X 1 is N or CR al ;
- X 2 is N or CR 32 ;
- X 3 is N or CR a3 ; and
- X 4 is N or CR a4 ; provided that not more than two of X 1 - X 4 are N.
- X 1 is CR al ;
- X 2 is CR a2 ;
- X 3 is CR a3 ;
- X 4 is CR a4 .
- R al , R a2 , R a3 , and R a4 are each independently selected from hydrogen and halogen.
- R 1 is selected from: (a) Ci-C6alkyl, (b) Ci-C6haloalkyl, (c) Ci-C6alkoxy, (d) Ci-C6haloalkoxy, (e) C3-C6cycloalkyl, (f) halogen, (g) C 6 -C1 0 aryl, optionally substituted with halogen; (h) 5- to lO-membered heteroaryl optionally substituted with Ci-C 4 alkyl or phenyl; (i) C0 2 R b , G) CONR c R d , (k) S(0)nR e , (1) S0 2 NR c R d , (m) P(0)(Ci- C 4 alkyl) 2 , (n) SFs, and (o) CN. In some embodiments, R 1 is selected from: (a) C1-C3 fluoroalkyl,
- R 1 is selected from: (a) C1-C 3 fluoroalkyl, (b) pyrazolyl, optionally substituted with one or two groups independently selected from Ci-C 4 alkyl,
- R 2 is selected from: (a) H, (b) C1-C 6 alkyl, (c) C 3 -C 6 cycloalkyl, (d) phenyl, and (e) 5- or 6-membered heteroaryl; wherein choices (b) - (e) are each optionally substituted with one or two groups independently selected from R f .
- R 2 is selected from: (a) H, (b) C1-C 3 alkyl, and (c) C 3 -C 6 cycloalkyl.
- R 3 and R 4 are each independently selected from the goup consisting of: (a) H, and (b) C1-C 6 alkyl optionally substituted with one or two groups independently selected from R f .
- R 3 and R 4 together with the carbon atom to which they are attached form a 3-6 membered ring optionally containing a heteroatom selected from O, S and NR C .
- R 3 and R 4 are each independently selected from: (a) H, and (b) C1-C 3 alkyl; or R 3 and R 4 , together with the carbon atom to which they are attached form a 3 - or 4-membered ring.
- R 5 is selected from: (a) C 3 -C 6 cycloalkyl, optionally substituted with phenyl; (b) C 6 -C1 0 aryl, (c) 5 to lO-membered heteroaryl, and (d) 3- to 10- membered heterocyclyl; wherein choices (a) - (d) are each optionally substituted with one or two groups independently selected from R f .
- R 5 is selected from: (a) C 3 -C 6 cycloalkyl, (b) phenyl, (c) monocyclic 5 or 6-membered heteroaryl, and (d) heterocyclyl selected from tetrahydropyranyl and tetrahydrofuranyl, wherein choices (a) - (d) are each optionally substituted with one or two groups independently selected from R f .
- R 5 is selected from: (a) phenyl, optionally substituted with one or two halogen atoms, and (b) monocyclic 5 or 6-membered heteroaryl, optionally substituted with one or two groups independently selected from R f .
- R b is selected from: (a) H, and (b) C1-C6 alkyl.
- R c and R d are independently selected from: (a) H, (b) Ci-Ce alkyl, (c) C3-C6 cycloalkyl, (d) benzyl optionally substituted with halogen.
- R c and R d together with the nitrogen atom to which they are attached form a 4- to 6-membered ring optionally containing a second heteroatom selected from O, S and N-R g ;
- R e is selected from: (a) Ci-C 6 alkyl, (b) Ci-C6haloalkyl, (c) C3-C6 cycloalkyl, (d) (CH 2 )n-5- to lO-membered heteroaryl, (e) (CH 2 ) n -aryl, wherein the 5- to lO-membered heteroaryl and the C6-C10 aryl are each optionally substituted with 1 or 2 halogen atoms.
- R f is selected from: (a) halogen, (b) CN, (c) C1-C6 alkyl, (d) OR b , (e) NR c R d , (f) S0 2 R e , and (g) Cs-Cecycloalkyl.
- R g is selected from: (a) H, (b) C1-C6 alkyl, (c)
- n 0, 1 or 2.
- the compound of formula (I) is a compound of formula (la):
- Some embodiments provide a pharmaceutical composition comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. [0023] Some embodiments provide a method for the treatment of inflammatory bowel disease which comprises administering to a patient in need thereof a therapeutically effective amount of a compound of formula (I).
- Some embodiments provide a method of inhibiting vanin activity, comprising contacting a cell with a compound of Formula (I), or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof, or a compound of Formula (la), or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof.
- the cell is an epithelial cell.
- the cell is in a subject in need of vanin inhibition.
- the vanin activity is selected from vanin-l activity, vanin-2 activity, vanin-3 activity, or a combination of any of the foregoing.
- X 1 is N or CR al ;
- X 2 is N or CR a2 ;
- X 3 is N or CR a3 ;
- X 4 is N or CR a4 ;
- R 1 is selected of:
- R 2 is selected from:
- choices (b) - (e) are each optionally substituted with one or two groups independently selected from R f ;
- R 3 and R 4 are each independently H or C1-C6 alkyl optionally substituted with one or two groups independently selected from R g ; or
- R 3 and R 4 are joined together to form a 3-6 membered ring optionally containing a heteroatom selected from O, S and NR h ;
- R 5 is selected from:
- choices (a) - (d) are each optionally substituted with one or two groups independently selected from R 1 ;
- R al , R a2 , R a3 , and R a4 are each independently H or halogen;
- R b is H or C1-C6 alkyl
- R c , R d , and R h are each independently selected from:
- R c and R d together with the nitrogen atom to which they are attached form a 3- to 6- membered heterocyclyl optionally containing a second heteroatom selected from O, S and N-R 1 ;
- R e is selected from:
- R f , R g , and R 1 are each independently selected from:
- R 1 is selected from the group consisting of:
- n and m are independently 0, 1 or 2.
- X 1 is N or CR al ;
- X 2 is N or CR a2 ;
- X 3 is N or CR a3 ; and
- X 4 is N or CR a4 ; provided that not more than two of X 1 - X 4 are N.
- one of X 1 - X 4 is N, and the others are CR al , CR a2 , CR a3 , or CR a4 .
- two of X 1 - X 4 are N, and the others are CR al , CR a2 , CR a3 , or CR a4 .
- one, two, three or four of X 1 - X 4 is CH.
- one, two, three or four of X 1 - X 4 is C-halogen such as C-F or C-Cl.
- R 1 is Ci-C6alkyl, including, but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl; in one subset, R 1 is Ci- C3alkyl. In some embodiments, R 1 is methyl.
- R 1 is Ci-C6haloalkyl, including, but not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, l,2-difluoroethyl, 2-chloroethyl, 3-bromopropyl; in one subset R 1 is C1-C3 fluoroalkyl. In some embodiments, R 1 is trifluoromethyl.
- R 1 is Ci-C6alkoxy, including, but not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, t-butoxy, n-pentoxy, n-hexoxy; in one subset, R 1 is Ci-C3alkoxy.
- R 1 is Ci-C6haloalkoxy, including, but not limited to, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, l,2-difluoroethoxy, 2-chloroethoxy, 3-bromopropoxy; in one subset R 1 is C1-C3 fluoroalkoxy.
- R 1 is C3-C6cycloalkyl, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.
- R 1 is halogen, including, but not limited to, fluoro, chloro, bromo, iodo. In some embodiments, R 1 is fluoro or chloro. In some embodiments, R 1 is C6-C10 aryl, optionally substituted with halogen, including, but not limited to, phenyl, naphthyl, 4-fluorophenyl, 3,5-dichlorophenyl, 4-bromophenyl.
- R 1 is monocyclic or bicyclic 5- to lO-membered heteroaryl optionally substituted with Ci-C 4 alkyl or phenyl, including, but not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, pyrrolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, 1 -methyl-3 -pyrazolyl, 1- methyl-5-pyrazolyl, l-methyl-4-pyrazolyl, 1 -isopropyl 5 -pyrazolyl, 1 -phenyl-5 -pyrazolyl, 1,3- dimethyl-5-pyrazolyl, l,4-dimethyl-5-pyrazolyl.
- R 1 is a monocyclic 6- membered heteroaryl, optionally substituted with one or two Ci-C 4 alkyl. In some embodiments, R 1 is a monocyclic 5-membered heteroaryl, optionally substituted with one or two Ci-C 4 alkyl. In some embodiments, R 1 is C02R b , including, but not limited to, CO2H, CO2CH3, CO2CH2CH3, C0 2 CH(CH3)2.
- R 1 is CONR c R d , including, but not limited to CONH2, CONHCft, CON(CH 3 )2, CONHCffcPh, CON(CH 3 )CH 2 -(4-F-Ph), CON(CH 2 )3, CON(CH 2 ) 4 , CO-(4-morpholinyl), CO-(4-CH3-l-piperazinyl), CO-(4-Boc-l-piperazinyl).
- R 1 is S(0)nR e ; in some subsets R 1 is SR e , including, but not limited to, methylthio, trifluoromethylthio, cyclopropylthio, phenylthio, benzylthio, 4-fluorobenzylthio, thiazolylmethylthio, pyridylthio; in some subsets R 1 is SOR e , including, but not limited to, methyl sulfmyl, trifluoromethylsulfmyl, cyclopropylsulfmyl, phenyl sulfmyl, benzylsulfmyl, 4- fluorobenzylsulfmyl,thiazolylmethylsulfmyl, pyridylsulfmyl; in some subsets R 1 is SChR 6 , including, but not limited to, methylsulfonyl, trifluoromethylsulfonyl, cycl
- R 1 is SCkNR ⁇ , including, but not limited to, SO2NH2, SO2NHCH3, S02N(CH 3 )2, S02NH-cyclopropyl, S02-(l-azetinyl), SCk-Q-pyrrolidinyl), S02-(4-morpholinyl).
- R 1 is P(0)(Ci-C 4 alkyl)2, including, but not limited to, P(0)(CH 3 )2.
- R 1 is SFs.
- R 1 is CN.
- R 2 is H. In some embodiments, R 2 is C1-C6 alkyl, as described herein; in one subset, R 2 is Ci-C 3 alkyl. In some embodiments, R 2 is C 3 -C 6 cylcoalkylcycloalkyl, as described herein. In some embodiments, R 2 is phenyl. In some embodiments, R 2 is 5- or 6-membered monocyclic heteroaryl, including, but not limited to, pyridyl, pyrrolyl, imidazolyl, oxazolyl. In some embodiments, C1-C6 alkyl, C 3 -C 6 cycloalkyl, phenyl, and 5- or 6-membered heteroaryl are each substituted with one or two groups independently selected from R f .
- R 3 and R 4 are H.
- one or both of R 3 and R 4 are C1-C6 alkyl optionally substituted with one or two groups independently selected from R f , including, but not limited to, unsubstituted C1-C6 alkyl groups as described herein, 2-hydroxyethyl, hydroxymethyl, methoxymethyl, chloroethyl, trifluoromethyl, cyclopropylmethyl, aminoethyl, methylsulfonylethyl; in some subsets R 3 is Ci-C 3 alkyl.
- R 3 and R 4 together with the carbon atom to which they are attached form a 3-6 membered monocyclic ring optionally containing a heteroatom selected from O, S and NR C , including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, pyrrolidine, piperidine, piperazine, N-methylpiperazine, morpholine; in some subsets R 3 and R 4 , together with the carbon atom to which they are attached form a monocyclic 3- or 4-membered ring.
- a heteroatom selected from O, S and NR C including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, pyrrolidine, piperidine, piperazine, N-methylpiperazine, morpholine; in some subsets R 3 and R 4 , together with the carbon atom to
- R 5 is C 3 -C 6 cycloalkyl, optionally substituted with phenyl or with one or two groups independently selected from R f , including, but not limited to, unsubstituted C 3 -C 6 cycloalkyl groups as describd herein, hydroxycyclopentyl, methoxycyclopentyl, chlorocyclohexyl, cyanocyclobutyl, methylcyclohexyl, dimethoxy cyclopentyl, difluorocyclopentyl, 3 -fluoro-4-m ethoxy cyclohexyl, dimethylaminocyclopentyl, methysulfonylcyclopentyl.
- Rs is monocyclic or bicyclic C6-C10 aryl, optionally substituted with one or two groups independently selected from R f , including, but not limited to, phenyl, naphthyl, fluorophenyl, difluorophenyl, hydroxyphenyl, bromophenyl, chlorophenyl, methoxy phenyl, methylphenyl, dimethylaminophenyl, methylsulfonylphenyl, aminophenyl, cyclopropylphenyl, cyanophenyl.
- R 5 is monocyclic or bicyclic 5- to lO-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f , including, but not limited to, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isoxazolyl, oxadiazolyl, benzothiadiazolyl, hydroxypyridyl, methoxypyridyl, methylpyridyl, aminopyridyl, methylsulfonylpyridyl.
- R 5 is a monocyclic 6-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is a monocyclic 5-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is a monocyclic or bicyclic 3- to lO-membered heterocyclyl, optionally substituted with one or two groups independently selected from R f , including, but not limited to, tetrahydropyranyl, tetrahydrofuranyl, pyrrolidinyl, piperidinyl, piperazinyl.
- the compound of formula (I) is selected from:
- R 1 is Ci-C 6 alkyl, such as those described herein; in one subset, R 1 is Ci-C3alkyl.
- R 1 is Ci-C6haloalkyl, including, but not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, l,2-difluoroethyl, 2-chloroethyl, 3-bromopropyl; in one subset R 1 is C1-C3 fluoroalkyl.
- R 1 is Ci-C 6 alkoxy, such as those described herein; in one subset, R 1 is Ci-C 3 alkoxy.
- R 1 is Ci-C6haloalkoxy, including, but not limited to, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, l,2-difluoroethoxy, 2-chloroethoxy, 3-bromopropoxy; in one subset R 1 is C1-C3 fluoroalkoxy.
- R 1 is C 3 -C 6 cycloalkyl, such as those described herein.
- R 1 is halogen. In some embodiments, R 1 is monocyclic or bicyclic C6-C10 aryl, optionally substituted with halogen, including, but not limited to, phenyl, 4-fluorophenyl, 3,5-dichlorophenyl, 4-bromophenyl.
- R 1 is monocyclic or bicyclic 5- to lO-membered heteroaryl optionally substituted with Ci-C 4 alkyl or phenyl, including, but not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, pyrrolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, 1 -methyl-3 -pyrazolyl, l-methyl-5- pyrazolyl, l-methyl-4-pyrazolyl, l-isopropyl5-pyrazolyl, l-phenyl-5-pyrazolyl, l,3-dimethyl-5- pyrazolyl, l,4-dimethyl-5-pyrazolyl.
- R 1 is C02R b , including, but not limited to, CO2H, CO2CH3, CO2CH2CH3, C02CH(CH 3 )2.
- R 1 is CONR c R d , including, but not limited to CONH2, CONHCH3, CON(CH 3 )2, CONHCH 2 Ph, CON(CH 3 )CH 2 -(4-F-Ph), CON(CH 2 ) 3 , CON(CH 2 ) 4 , CO-(4-morpholinyl), CO-(4-CH 3 -l- piperazinyl), CO-(4-Boc-l-piperazinyl).
- R 1 is S(0)nR e ; in some subsets R 1 is SR e , including, but not limited to, methylthio, trifluoromethylthio, cyclopropylthio, phenylthio, benzylthio, 4-fluorobenzylthio, thiazolylmethylthio, pyridylthio; in some subsets R 1 is SOR e , including, but not limited to, methylsulfmyl, trifluoromethylsulfmyl, cyclopropylsulfmyl, phenylsulfmyl, benzylsulfmyl, 4-fluorobenzyl- sulfmyl,thiazolylmethylsulfmyl, pyridyl sulfmyl; in some subsets R 1 is SCkR 6 , including, but not limited to, methylsulfonyl, trifluoromethylsulfonyl,
- R 1 is S02NR c R d , including, but not limited to, SO2NH2, SO2NHCH3, S0 2 N(CH 3 ) 2 , S02NH-cyclopropyl, S02-(l-azetinyl), S02-(l-pyrrolidinyl), S02-(4-morpholinyl).
- R 1 is P(0)(Ci-C 4 alkyl)2, including, but not limited to, P(0)(CH 3 )2.
- R 1 is SFs.
- R 1 is CN.
- one or both of R 3 and R 4 are H.
- R 3 and R 4 are C1-C6 alkyl optionally substituted with one or two groups independently selected from R f , including, but not limited to, unsubstituted C1-C6 alkyl groups as described herein, 2-hydroxyethyl, hydroxymethyl, methoxymethyl, chloroethyl, trifluoromethyl, cyclopropylmethyl, aminoethyl, methylsulfonylethyl; in some subsets R 3 is C1-C3 alkyl.
- R 3 and R 4 together with the carbon atom to which they are attached form a monocyclic 3-6 membered ring optionally containing a heteroatom selected from O, S and NR C , including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, pyrrolidine, piperidine, piperazine, N-methylpiperazine, morpholine; in some subsets R 3 and R 4 , together with the carbon atom to which they are attached form a monocyclic 3- or 4-membered ring.
- a heteroatom selected from O, S and NR C including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidine, pyrrolidine, piperidine, piperazine, N-methylpiperazine, morpholine; in some subsets R 3 and R 4 , together with the carbon atom to
- R 5 is C3-C6 cycloalkyl, optionally substituted with phenyl or with one or two groups independently selected from R f , including, but not limited to, unsubstituted C3-C6 cycloalkyl groups as described herein, hydroxycyclopentyl, methoxycyclopentyl, chlorocyclohexyl, cyanocyclobutyl, methylcyclohexyl, dimethoxy cyclopentyl, difluorocyclopentyl, 3 -fluoro-4-m ethoxy cyclohexyl, dimethylaminocyclopentyl, methysulfonylcyclopentyl.
- Rs is C6-C 10 aryl, optionally substituted with one or two groups independently selected from R f , including, but not limited to, phenyl, naphthyl, fluorophenyl, difluorophenyl, hydroxyphenyl, bromophenyl, chlorophenyl, methoxy phenyl, methylphenyl, dimethylaminophenyl, methylsulfonylphenyl, aminophenyl, cyclopropylphenyl, cyanophenyl.
- R 5 is 5- to lO-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f , including, but not limited to, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, isoxazolyl, oxadiazolyl, benzothiadiazolyl, hydroxypyridyl, methoxypyridyl, methylpyridyl, aminopyridyl, methylsulfonylpyridyl.
- R 5 is a monocyclic 6-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is a monocyclic 5-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is 3- to lO-membered monocycylic or bicyclic heterocyclyl, optionally substituted with one or two groups independently selected from R f , including, but not limited to, tetrahydropyranyl, tetrahydrofuranyl, pyrrolidinyl, piperidinyl, piperazinyl.
- the compound of formula (I) or (la) is selected from:
- R 1 is Ci-C 6 alkyl, such as those described herein; in one subset, R 1 is Ci-C3alkyl. In some embodiments of this paragraph, R 1 is Ci-C6haloalkyl, such as those described herein; in one subset R 1 is C1-C3 fluoroalkyl. In some embodiments of this paragraph, R 1 is Ci-C 6 alkoxy, such as those described herein; in one subset, R 1 is Ci-C 3 alkoxy. In some embodiments of this paragraph, R 1 is Ci-C6haloalkoxy, such as those described herein; in one subset R 1 is C1-C3 fluoroalkoxy.
- R 1 is C3-C6cycloalkyl, such as those described herein. In some embodiments of this paragraph, R 1 is halogen. In some embodiments of this paragraph, R 1 is C 6 -C1 0 aryl, optionally substituted with halogen, such as those described herein. In some embodiments of this paragraph, R 1 is 5- to 10- membered heteroaryl optionally substituted with Ci-C 4 alkyl or phenyl, such as those described herein. In some embodiments of this paragraph, R 1 is C02R b , such as those described herein. In some embodiments of this paragraph, R 1 is CONR c R d , such as those described herein.
- R 1 is S(0)nR e , such as those described herein; in some subsets R 1 is SR e , such as those described herein; in some subsets R 1 is SOR e , such as those described herein; in some subsets R 1 is SCkR 6 , such as those described herein.
- R 1 is S02NR c R d , such as those described herein.
- R 1 is P(0)(Ci-C 4 alkyl)2, including, but not limited to, R(0)(O3 ⁇ 4)2.
- R 1 is SFs
- R 1 is CN.
- R 3 and R 4 are H. In some embodiments of this paragraph, one or both of R 3 and R 4 are C1-C 6 alkyl optionally substituted with one or two groups independently selected from R f , such as those described herein; in some subsets R 3 is Ci- C 3 alkyl. In some embodiments of this paragraph, R 3 and R 4 are joined together to form a monocyclic 3-6 membered ring optionally containing a heteroatom selected from O, S and NR C , such as those described herein; in some subsets R 3 and R 4 are are joined together to form a monocyclic 3- or 4-membered ring.
- R al , R a2 , R a3 , and R a4 are each hydrogen. In some embodiments of this paragraph, R al , R a2 , R a3 , and R a4 , are each halogen. In some embodiments two of R al , R a2 , R a3 , and R a4 , are hydrogen and two of R al , R 32 , R a3 , and R a4 , are halogen. In some embodiments of this paragraph, R al , R a2 , and R a3 , are each hydrogen; and and R a4 is halogen.
- R al , R a2 , and R a4 are each hydrogen; and and R a3 is halogen. In some embodiments of this paragraph, R al , R a3 , and R a4 , are each hydrogen; and and R a2 is halogen. In some embodiments of this paragraph, R a2 , R a3 , and R a4 , are each hydrogen; and and R al is halogen. In some embodiments of this paragraph, one or both R f are hydrogen. In some embodiments of this paragraph, one or both R f are halogen. In some embodiments of this paragraph, one or both R f are C1-C 6 alkyl, such as those described herein.
- one or both R f are OR b , such as those described herein.
- one or both R f are NR c R d , including, but not limited to, amino, methylamino, dimethylamino, ethylamino, l-pyrrolidinyl, 4-morpholinyl.
- one or both R f are SCkR 6 , such as those described herein.
- one or both R f are C3-C 6 cycloalkyl, such as those described herein.
- the compound of formula (I) or (la) is selected from:
- R 3 and R 4 are H. In some embodiments of this paragraph, one or both of R 3 and R 4 are C1-C6 alkyl optionally substituted with one or two groups independently selected from R f , such as those described herein; in some subsets R 3 is Ci- C3 alkyl. In some embodiments of this paragraph, R 3 and R 4 are joined together to form a monocylic 3-6 membered ring optionally containing a heteroatom selected from O, S and NR C , such as those described herein; in some subsets R 3 and R 4 are are joined together to form a monocyclic 3- or 4-membered ring.
- R 5 is C3-C6 cycloalkyl, optionally substituted with phenyl or with one or two groups independently selected from R f , such as those described herein.
- Rs is C6-C10 aryl, optionally substituted with one or two groups independently selected from R f , such as those described herein.
- R 5 is 5- to lO-membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f , such as those described herein.
- R 5 is a monocyclic 6- membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is a monocyclic 5- membered heteroaryl, optionally substituted with phenyl or with one or two groups independently selected from R f .
- R 5 is 3- to 10- membered heterocyclyl, optionally substituted with one or two groups independently selected from R f , such as those described herein.
- R al , R 32 , R a3 , and R a4 are each hydrogen.
- R al , R 32 , R a3 , and R a4 are each halogen.
- two of R al , R a2 , R a3 , and R a4 are hydrogen and two of R al , R a2 , R a3 , and R a4 , are halogen.
- R al , R a2 , and R a3 are each hydrogen; and and R a4 is halogen.
- R al , R a2 , and R a4 are each hydrogen; and and R a3 is halogen.
- R al , R a3 , and R a4 are each hydrogen; and and R a2 is halogen. In some embodiments of this paragraph, R a2 , R a3 , and R a4 , are each hydrogen; and and R al is halogen.
- the compound of formula (I) is selected from:
- Some embodiments provide a pharmaceutical composition comprising a compound of Formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
- Other embodiments provide a pharmaceutical composition comprising a compound of Formula (la), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
- Some embodiments provide a method for the treatment of inflammatory bowel disease comprising administering to a patient in need thereof a compound of Formula (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
- Other embodiments provide a method for the treatment of inflammatory bowel disease comprising administering to a patient in need thereof a compound of Formula (la), or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising a compound of Formula (la), or a pharmaceutically acceptable salt thereof.
- the inflammatory bowel disease is Crohn’s disease. In some embodiments, the inflammatory bowel disease is ulcerative colitis.
- Some embodiments provide a method of inhibiting vanin activity, comprising contacting a cell with a compound of Formula (I), or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof.
- Other embodiments provide a method of inhibiting vanin activity, comprising contacting a cell with a compound of Formula (la), or a pharmaceutically acceptable salt, solvate or solvate of the salt thereof.
- the cell is an epithelial cell.
- the cell is in a subject in need of vanin inhibition.
- the vanin activity is selected from vanin-l activity, vanin-2 activity, vanin-3 activity, or a combination of any of the foregoing.
- the vanin activity is vanin-l activity.
- the vanin activity is vanin-l activity, vanin-2 activity, and vanin-3 activity.
- any of the features of an embodiment is applicable to all embodiments identified herein. Moreover, any of the features of an embodiment is independently combinable, partly or wholly with other embodiments described herein in any way, e.g., one, two, or three or more embodiments may be combinable in whole or in part. Further, any of the features of an embodiment may be made optional to other embodiments. Any embodiment of a method can comprise another embodiment of a compound, and any embodiment of a compound can be configured to perform a method of another embodiment.
- the terms are to be interpreted synonymously with the phrases“having at least” or “including at least.”
- the term“comprising” means that the process includes at least the recited steps, but may include additional steps.
- the term “comprising” means that the compound, composition, or device includes at least the recited features or components, but may also include additional features or components.
- the term“patient” includes mammals such as mice, rats, cows, sheep, pigs, rabbits, goats, horses, monkeys, dogs, cats, and humans. In some embodiments, the patient is a human.
- a group may be unsubstituted or substituted with the indicated number of the indicated substituents.
- an aryl group optionally substituted with 1 or 2 halogens.
- the indicated group is optionally substituted with one or more of the indicated substituents.
- an aryl group optionally substituted with halogen.
- substituents are indicated, it is meant that the indicated “optionally substituted” or “substituted” group may be substituted with one or more group(s) individually and independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, hydroxy, alkoxy, cyano, halogen, nitro, haloalkyl, haloalkoxy, and amino.
- “C a -Cb” in which“a” and“b” are integers refer to the number of carbon atoms in a group.
- the indicated group can contain from“a” to“b”, inclusive, carbon atoms.
- a“Ci-C 4 alkyl” group refers to all alkyl groups having from 1 to 4 carbons, that is, CFb-, CH3CH2-, CH3CH2CH2-, (Cft ⁇ CH-, CH3CH2CH2CH2-, CFFCFhCFliCFb)- and (CFb ⁇ C-. If no“a” and“b” are designated, the broadest range described in these definitions is to be assumed.
- R groups and the atom(s) they are attached to can form a cycloalkyl, cycloalkenyl, aryl, heteroaryl or heterocyclyl ring.
- R a and R b of an NR a R b group are indicated to be“joined together,” it means that they are covalently bonded to one another to form a ring:
- halo or“halogen” refers to any radical of fluorine, chlorine, bromine or iodine.
- alkyl refers to a saturated hydrocarbon chain that may be a straight chain or branched chain, containing the indicated number of carbon atoms.
- C1-C6 alkyl indicates that the group may have from 1 to 6 (inclusive) carbon atoms in it.
- an alkyl is a C1-C6 alkyl which represents a straight-chain or branched saturated hydrocarbon radical having 1 to 6 carbon atoms.
- alkyl include without limitation methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.
- Alkyl groups may be substituted or unsubstituted.
- cycloalkyl refers to a fully saturated monocyclic, bicyclic, tricyclic or other polycyclic hydrocarbon group having the indicated number of ring carbon atoms between 3 and 12 carbon atoms. Multicyclic cycloalkyls (such as bicyclic) may be fused, bridged or spiro ring systems. Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and norbornyl. Cycloalkyl groups may be substituted or unsubstituted.
- cycloalkenyl refers to partially unsaturated monocyclic, bicyclic, tricyclic, or other polycyclic hydrocarbon groups having the indicated number of ring carbon atoms between 5 and 12 carbon atoms.
- a ring carbon e.g., saturated or unsaturated
- Any atom can be optionally substituted e.g., by one or more substituents.
- Cycloalkenyl moieties can include without limitation, e.g., cyclopentenyl, cyclohexenyl, cyclohexadienyl, or norbornenyl. Cycloalkenyl groups may be substituted or unsubstituted.
- haloalkyl refers to an alkyl group in which at least one hydrogen atom is replaced by halo. In some embodiments, more than one hydrogen atom (e.g., 2, 3, 4, 5 or 6) are replaced by halo. In these embodiments, the hydrogen atoms can each be replaced by the same halogen (e.g., fluoro) or the hydrogen atoms can be replaced by a combination of different halogens (e.g., fluoro and chloro).
- Haloalkyl also includes alkyl moieties in which all hydrogens have been replaced by halo (sometimes referred to herein as perhaloalkyl, e.g., perfluoroalkyl, such as trifluoromethyl). Haloalkyl groups may be substituted or unsubstituted.
- alkoxy refers to a group of formula -O-(alkyl). Alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, butoxy, iso-butoxy, sec-butoxy, pentoxy, 2-pentoxy, 3-pentoxy, or hexyloxy.
- thioalkoxy refers to a group of formula -S-(alkyl).
- haloalkoxy and“thiohaloalkoxy” refer to -O-(haloalkyl) and -S-(haloalkyl), respectively.
- one or more hydrogen atoms in the alkyl portion of the group may be replaced with deuterium, for example, a deutero methoxy group (-OCD3).
- deuterium for example, a deutero methoxy group (-OCD3).
- Alkoxy, deuteroalkoxy, and haloalkoxy groups may be substituted or unsubstituted.
- aralkyl refers to an alkyl moiety in which an alkyl hydrogen atom is replaced by an aryl group. One of the carbons of the alkyl moiety serves as the point of attachment of the aralkyl group to another moiety.
- Non-limiting examples of“aralkyl” include benzyl, 2-phenylethyl, and 3-phenylpropyl groups.
- Aralkyl groups may be substituted or unsubstituted.
- alkenyl refers to a straight or branched hydrocarbon chain containing the indicated number of carbon atoms and having one or more carbon-carbon double bonds.
- Alkenyl groups can include, e.g., vinyl, allyl, l-butenyl, and 2-hexenyl. Alkenyl groups may be substituted or unsubstituted.
- alkynyl refers to a straight or branched hydrocarbon chain containing the indicated number of carbon atoms and having one or more carbon-carbon triple bonds.
- Alkynyl groups include, but are not limited to, ethynyl, propargyl, l-butynyl, and 2- hexynyl. Alkynyl groups may be substituted or unsubstituted.
- heterocycle represents a stable 4-, 5-, 6- or 7-membered monocyclic- or a stable 6-, 7-, 8-, 9-, 10-, 11-, or l2-membered bicyclic heterocyclic ring system which comprises at least one non-aromatic (i.e.
- a heterocycle can be bonded via a ring carbon atom or, if available, via a ring nitrogen atom.
- Bicyclic heterocyclic ring systems may be fused, bridged, or spiro bicyclic heterocyclic ring system(s).
- heterocyclyl is monocyclic having 4 to 7, preferably 4 to 6, ring atoms, of which 1 or 2 are heteroatoms independently selected from N, O and S.
- a heterocyclyl group is bicyclic, and in which case, the second ring may be an aromatic or a non-aromatic ring which consists of carbon atoms and from one to four, preferably up to three, heteroatoms independently selected from N, O and S, or the second ring may be a benzene ring, or a “cycloalkyl”, or a“cycloalkenyl”, as defined herein.
- heterocyclic groups include, but are not limited to azetidine, chroman, dihydrofuran, dihydropyran, dioxane, dioxolane, hexahydroazepine, imidazolidine, imidazoline, indoline, isochroman, isoindoline, isothiazoline, isothiazolidine, isoxazoline, isoxazolidine, morpholine, oxazoline, oxazolidine, oxetane, piperazine, piperidine, dihydropyridine, tetrahydropyridine, dihydropyridazine, pyran, pyrazolidine, pyrazoline, pyrrolidine, pyrroline, tetrahydrofuran, tetrahydropyran, thiamorpholine, tetrahydrothiophene, thiazoline, thiazolidine, thiomorpholine, thiet,
- Heterocyclyl groups may be substituted or unsubstituted.
- aryl as used herein, is intended to mean any stable monocyclic or bicyclic carbon ring of up to 6 members in each ring (i.e., 6 to 10 total ring atoms) wherein at least one ring is aromatic.
- Aryl groups include, but are not limited to phenyl, naphthyl, tetrahydronaphthyl, indanyl, or lH-indenyl. Aryl groups may be substituted or unsubstituted.
- heteroaryl represents a stable 5-, 6- or 7-membered monocyclic- or stable 9- or lO-membered fused bicyclic ring system which comprises at least one aromatic ring, which consists of carbon atoms and from one to four, preferably up to three, heteroatoms selected from N, O and S wherein the nitrogen and sulfur heteroatoms may optionally be oxidized, and the nitrogen heteroatom may optionally be quaternized.
- the second ring need not be aromatic and need not comprise a heteroatom.
- bicyclic“heteroaryl” includes, for example, a stable 5- or 6-membered monocyclic aromatic ring consisting of carbon atoms and from one to four, preferably up to three, heteroatoms, as defined immediately above, fused to a benzene ring, or a second monocyclic“heteroaryl”, or a“heterocyclyl”, a“cycloalkyl”, or a “cycloalkenyl”, as defined above.
- heteroaryl groups include, but are not limited to, benzimidazole, benzopyrazole, benzisothiazole, benzisoxazole, benzofuran, isobenzofuran, benzothiazole, benzothiophene, benzotriazole, benzoxazole, cinnoline, furan, furazan, imidazole, indazole, indole, indolizine, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, phthalazine, pteridine, purine, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, quinazoline, quinoline, quinoxaline, tetrazole, thiadiazole, thiazole, thiophene, triazine, triazole, benzimidazole, benzo
- the term“treating”,“treat”, or“treatment” refers generally to controlling, alleviating, ameliorating, slowing the progress of or eliminating a named condition once the condition has been established.
- the term“preventing”, “prevent”, or“prevention” also refers to delaying the onset of, or reducing the risk of developing a named condition or of a process that can lead to the condition, or the recurrence of symptoms of a condition.
- the term“therapeutically effective amount” or“effective amount” is an amount sufficient to effect beneficial or desired clinical results.
- An effective amount can be administered in one or more administrations.
- An effective amount is typically sufficient to palliate, ameliorate, stabilize, reverse, slow or delay the progression of the disease state.
- the compounds of this disclosure may contain one or more asymmetric centers and thus occur as racemates and racemic mixtures, enantiomerically enriched mixtures, single enantiomers, individual diastereomers and diastereomeric mixtures.
- the compounds of the present disclosure may, either by nature of asymmetric centers or by restricted rotation, be present in the form of isomers (e.g., enantiomers, diastereomers).
- the compounds of the present disclosure include all cis, trans, syn, anti,
- Z) isomers as well as mixtures thereof.
- the compounds of the present disclosure may also be represented in multiple tautomeric forms, in such instances, the present disclosure expressly includes all tautomeric forms of the compounds described herein, even though only a single tautomeric form may be represented.
- a term used in the present disclosure encompasses a group that may tautomerize, all tautomeric forms are expressly included thereunder.
- hydroxy substituted heteroaryl groups include, but are not limited to, 2-hydroxypyridine as well as 2-pyridone, l-hydroxyisoquinoline as well as 1- oxo-l,2-dihyroisoquinoline, 2-hydroxypyrimidine as well as 2-pyrimidone, 2-hydroxy quinoline as well as 2-quinolinone, 5-hydroxy-l,2,4-oxadiazole as well as l,2,4-oxadiazole-5(4H)one, and the like. All such isomeric forms of such compounds are expressly included in the present disclosure.
- the compounds of the present disclosure include the compounds themselves, as well as their salts, solvate, and solvate of the salt, if applicable.
- Salts for the purposes of the present disclosure are preferably pharmaceutically acceptable salts of the compounds according to the present disclosure. Salts which are not themselves suitable for pharmaceutical uses but can be used, for example, for isolation or purification of the compounds according to the disclosure are also included.
- a salt for example, can be formed between an anion and a positively charged substituent (e.g., amino) on a compound described herein. Suitable anions include chloride, bromide, iodide, sulfate, nitrate, phosphate, citrate, methanesulfonate, trifluoroacetate, and acetate.
- a salt can also be formed between a cation and a negatively charged substituent (e.g., carboxylate) on a compound described herein.
- Suitable cations include sodium ion, potassium ion, magnesium ion, calcium ion, and an ammonium cation such as tetramethylammonium ion.
- pharmaceutically acceptable salts refer to derivatives wherein the parent compound is modified by making acid or base salts thereof.
- pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines; alkali or organic salts of acidic residues such as carboxylic acids; and the like.
- pharmaceutically acceptable salts include the conventional non-toxic salts or the quaternary ammonium salts of the parent compound formed, for example, from non-toxic inorganic or organic acids.
- such conventional non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfonic, sulfuric, sulfamic, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, malic, tartaric, citric, ascorbic, pamoic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, salicylic, sulfanilic, 2-acetoxybenzoic, fumaric, benzenesulfonic, toluenesulfonic, naphthalenedisulfonic, methanesulfonic, ethanesulfonic, ethanedi sulfonic, camphorsulfonic, gluconic, mandelic, mucic, pantothenic, oxalic, isethionic, and the like.
- inorganic acids
- salts may be prepared from pharmaceutically acceptable non-toxic bases, including inorganic and organic bases.
- Such salts that may be prepared include lithium salt, sodium salt, potassium salt, magnesium salt, calcium salt, dicyclohexylamine salt, A-methyl -D-gl ucami ne salt, tris(hydroxymethyl)methyl- amine salt, arginine salt, lysine salt, and the like.
- Solvates in the context of the present disclosure are designated as those forms of the compounds according to the present disclosure which form a complex in the solid or liquid state by stoichiometric coordination with solvent molecules. Hydrates are a specific form of solvates, in which the coordination takes place with water. Hydrates are preferred solvates in the context of the present disclosure. The formation of solvates is described in greater detail in “Solvents and Solvent Effects in Organic Chemistry”; Reichardt, C. and Welton T.; John Wiley & Sons, 2011 [ISBN: 978-3-527-32473-6], the contents of which is incorporated herein by reference in its entirety. A person of ordinary skill in the art would recognize the solvates of the present disclosure.
- the present disclosure also encompasses all suitable isotopic variants of the compounds according to the present disclosure, whether radioactive or not.
- An isotopic variant of a compound according to the present disclosure is understood to mean a compound in which at least one atom within the compound according to the present disclosure has been exchanged for another atom of the same atomic number, but with a different atomic mass than the atomic mass which usually or predominantly occurs in nature.
- isotopes which can be incorporated into a compound according to the present disclosure are those of hydrogen, carbon, nitrogen, oxygen, sulfur, fluorine, chlorine, bromine and iodine, such as 2 H (deuterium), 3 H (tritium), 13 C, 14 C, 15 N, 17 0, 18 0, 32 S, 33 S, 34 S, 36 S, 18 F, 36 Cl, 82 Br, 123 I, 124 I, 125 I, 129 I and 131 I.
- Particular isotopic variants of a compound according to the present disclosure may be beneficial, for example, for the examination of the mechanism of action or of the active compound distribution in the body, especially compounds labeled with 3 H, 14 C and/or 18 F isotopes are suitable for this purpose.
- the incorporation of isotopes for example of deuterium, can lead to particular therapeutic benefits for the compounds described herein.
- deuteration may impart greater metabolic stability of the compound and for example, extend the half-life in the body or reduce the active dose required.
- Such modifications of the compounds described herein may therefore in some cases also constitute a preferred embodiment of the present disclosure.
- hydrogen atoms of the compounds described herein may be replaced with deuterium atoms.
- Isotopic variants of the compounds described herein can be prepared by processes known to those skilled in the art, for example by the methods described below and the methods described in the examples, by using corresponding isotopic modifications of the particular reagents and/or starting compounds therein.
- compositions of the present disclosure encompass any composition made by admixing a compound of the present disclosure, or a pharmaceutically acceptable salt, or solvate or solvate of the salt thereof, and a pharmaceutically acceptable carrier.
- pharmaceutically acceptable carrier refers to a carrier or an adjuvant that may be administered to a patient, together with a compound of the present disclosure, or a pharmaceutically acceptable salt, solvate, or salt of the solvate thereof, and which does not destroy the pharmacological activity thereof and is nontoxic when administered in doses sufficient to deliver a therapeutic amount of the compound.
- the quantity of a compound of the present disclosure in a unit dose of preparation is at 1 mg to 1,000 mg, 2 mg to 900 mg, 3 mg to 800 mg, 4 mg to 700 mg, 5 mg to 600 mg, 10 mg to 500 mg, 50 mg to 400 mg, 100 mg to 300 mg, 150 mg to 250 mg, or any value in between.
- the total daily dosage may be divided and administered in portions during the day, for example, once per day, twice per day, three times per day or four times per day. In some embodiments, the total dosage may be administered once per week, twice per week, three times per week, four times per week, five times per week or six times per week.
- the pharmaceutical compositions of the present disclosure for injection comprise pharmaceutically acceptable sterile aqueous or non-aqueous solutions, dispersions, suspensions or emulsions as well as sterile powders for reconstitution into sterile injectable solutions or dispersions just prior to use.
- suitable aqueous and non- aqueous carriers, diluents, solvents or vehicles include water, ethanol, polyols (such as glycerol, propylene glycol, polyethylene glycol, and the like), and suitable mixtures thereof, vegetable oils (such as olive oil), and injectable organic esters such as ethyl oleate.
- Proper fluidity can be maintained, for example, by the use of coating materials such as lecithin, by the maintenance of the required particle size in the case of dispersions, and by the use of surfactants.
- the pharmaceutical compositions may also contain adjuvants such as preservative, wetting agents, emulsifying agents, and dispersing agents. Prevention of the action of micro-organisms may be ensured by the inclusion of various antibacterial and antifungal agents, for example, paraben, chlorobutanol, phenol sorbic acid, and the like. It may also be desirable to include isotonic agents such as sugars, sodium chloride, and the like. Prolonged absorption of the injectable pharmaceutical form may be brought about by the inclusion of agents that delay absorption such as aluminium monostearate and gelatin. If desired, and for more effective distribution, the compounds can be incorporated into slow release or targeted delivery systems such as polymer matrices, liposomes, and microspheres.
- adjuvants such as preservative, wetting agents, emulsifying agents, and dispersing agents.
- the pharmaceutical compositions that are injectable formulations can be sterilized, for example, by filtration through a bacterial -retaining filter, or by incorporating sterilizing agents in the form of sterile solid pharmaceutical compositions that can be dissolved or dispersed in sterile water or other sterile injectable medium just prior to use.
- solid dosage forms of the instant pharmaceutical compositions for oral administration include capsules, tablets, pills, powders, and granules.
- the active compound is mixed with at least one inert, pharmaceutically acceptable excipient or carrier such as sodium citrate or dicalcium phosphate and/or a) fillers or extenders such as starches, lactose, sucrose, glucose, mannitol, and silicic acid, b) binders such as, for example, carboxymethylcellulose, alginates, gelatin, polyvinylpyrrolidone, sucrose, and acacia, c) humectants such as glycerol, d) disintegrating agents such as agar-agar, calcium carbonate, potato or tapioca starch, alginic acid, certain silicates, and sodium carbonate, e) solution retarding agents such as paraffin, f) absorption accelerators such as quaternary
- the dosage form may also comprise buffering agents.
- Solid pharmaceutical compositions of a similar type may also be employed as fillers in soft and hard-filled gelatin capsules using such excipients as lactose or milk sugar as well as high molecular weight polyethylene glycols and the like.
- the solid dosage forms of the instant pharmaceutical compositions of tablets, dragees, capsules, pills, and granules can be prepared with coatings and shells such as enteric coatings and other coatings well known in the pharmaceutical formulating art. They may optionally contain opacifying agents and can also be of a formulation that they release the active ingredient(s) only, or preferentially, in a certain part of the intestinal tract, optionally, in a delayed manner.
- coatings and shells such as enteric coatings and other coatings well known in the pharmaceutical formulating art. They may optionally contain opacifying agents and can also be of a formulation that they release the active ingredient(s) only, or preferentially, in a certain part of the intestinal tract, optionally, in a delayed manner.
- embedding pharmaceutical compositions which can be used include polymeric substances and waxes.
- the active compounds can also be in microencapsulated form, if appropriate, with one or more of the above-mentioned excipients.
- liquid dosage forms of the instant pharmaceutical compositions for oral administration include pharmaceutically acceptable emulsions, solutions, suspensions, syrups and elixirs.
- the liquid dosage forms may contain inert diluents commonly used in the art such as, for example, water or other solvents, solubilizing agents and emulsifiers such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, EtOAc, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butylene glycol, dimethyl formamide, oils (in particular, cottonseed, groundnut, com, germ, olive, castor, and sesame oils), glycerol, tetrahydrofurfuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof.
- inert diluents commonly used in the art such as, for example, water or other solvents, solubilizing agents and emulsifiers such as
- the oral pharmaceutical compositions can also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, and perfuming agents.
- adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, and perfuming agents.
- Suspensions of the instant compounds may contain suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminium metahydroxide, bentonite, agar-agar, and tragacanth, and mixtures thereof.
- suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminium metahydroxide, bentonite, agar-agar, and tragacanth, and mixtures thereof.
- compositions for rectal or vaginal administration are preferably suppositories which can be prepared by mixing the compounds with suitable non irritating excipients or carriers such as cocoa butter, polyethylene glycol or a suppository wax which are solid at RT but liquid at body temperature and therefore melt in the rectum or vaginal cavity and release the active compound.
- suitable non irritating excipients or carriers such as cocoa butter, polyethylene glycol or a suppository wax which are solid at RT but liquid at body temperature and therefore melt in the rectum or vaginal cavity and release the active compound.
- Dosage forms for topical administration of a compound or pharmaceutical composition of the present disclosure include powders, patches, sprays, ointments and inhalants.
- the active compound is mixed under sterile conditions with a pharmaceutically acceptable carrier and any needed preservatives, buffers, or propellants which may be required.
- Some embodiments provide methods of treating diseases or disorders related to systemic or tissue inflammation, inflammatory responses to infection or hypoxia, cellular activation and proliferation, lipid metabolism, fibrosis, or viral infections comprising administering to a patient in need thereof a therapeutically effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof.
- Other embodiments provide the use of an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for the manufacture of a medicament for the treatment of diseases or disorders related to systemic or tissue inflammation, inflammatory responses to infection or hypoxia, cellular activation and proliferation, lipid metabolism, fibrosis, or viral infections.
- Still other embodiments provide an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for treating diseases or disorders related to systemic or tissue inflammation, inflammatory responses to infection or hypoxia, cellular activation and proliferation, lipid metabolism, fibrosis, or viral infections.
- Some embodiments provide methods of treating an inflammatory disease or disorder, autoimmune disease, metabolic disease or cancer, comprising administering a therapeutically effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof.
- inventions provide the use of an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for the manufacture of a medicament for the treatment of an inflammatory disease or disorder, autoimmune disease, metabolic disease or cancer. Still other embodiments provide an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for treating an inflammatory disease or disorder, metabolic disease, autoimmune disease or cancer.
- the disease may be, but not limited to, one of the following classes: autoimmune diseases, inflammatory diseases, allergic diseases, metabolic diseases, infection- based diseases, trauma or tissue-injury based diseases, fibrotic diseases, genetic diseases, cardiovascular diseases, neurological diseases, neurodegenerative diseases, respiratory diseases, pulmonary diseases, airways diseases, renal diseases, skin and/ or dermatological diseases, liver diseases, gastrointestinal diseases, oral diseases, pain and sensory diseases, hematopoietic diseases, joint diseases, muscle diseases, and bone diseases.
- autoimmune diseases inflammatory diseases, allergic diseases, metabolic diseases, infection- based diseases, trauma or tissue-injury based diseases, fibrotic diseases, genetic diseases, cardiovascular diseases, neurological diseases, neurodegenerative diseases, respiratory diseases, pulmonary diseases, airways diseases, renal diseases, skin and/ or dermatological diseases, liver diseases, gastrointestinal diseases, oral diseases, pain and sensory diseases, hematopoietic diseases, joint diseases, muscle diseases, and bone diseases.
- autoimmune diseases include, but are not limited to: rheumatoid arthritis, osteoarthritis, psoriasis, allergic dermatitis, systemic lupus erythematosus (and resulting complications), Sjogren's syndrome, multiple sclerosis, asthma, glomerular nephritis, irritable bowel syndrome, inflammatory bowel disease, Crohn's disease, ankylosing spondylitis, Behcet's disease, lupus nephritis, scleroderma, systemic scleroderma, type 1 or juvenile on-set diabetes, alopecia universalis, acute disseminated encephalomyelitis, Addison's disease, antiphospholipid antibody syndrome, atrophic gastritis of pernicious anemia, autoimmune alopecia, autoimmune hemolytic anemia, autoimmune hepatitis, autoimmune encephalomyelitis, autoimmune thrombocytopenia, Bullous pe
- Inflammatory diseases include, but are not limited to: chronic obstructive pulmonary diseases, airway hyper-responsiveness, cystic fibrosis, acute respiratory distress syndrome, sinusitis, rhinitis, gingivitis, atherosclerosis, chronic prostatitis, glomerular nephritis, ulcerative colitis, uveitis, periodontal disease, or an indication listed in a separate category herein.
- Pain conditions include, but are not limited to: inflammatory pain, surgical pain, visceral pain, dental pain, premenstrual pain, central pain, pain due to burns, migraine or cluster headaches, nerve injury, interstitial cystitis, cancer pain, viral, parasitic or bacterial infection, post-traumatic injury, pain associated with irritable bowel syndrome, gout, pain associated with any of the other indications listed within this specification, or an indication listed in a separate category herein.
- Respiratory, airway and pulmonary conditions include, but are not limited to: asthma (which may encompass chronic, late, bronchial, allergic, intrinsic, extrinsic or dust), chronic obstructive pulmonary disease, idiopathic pulmonary fibrosis, pulmonary arterial hypertension, cystic fibrosis, interstitial lung disease, acute lung injury, sarcoidosis, allergic rhinitis, chronic cough, bronchitis, recurrent airway obstruction, emphysema, or bronchospasm, or an indication listed in a separate disease category herein.
- asthma which may encompass chronic, late, bronchial, allergic, intrinsic, extrinsic or dust
- chronic obstructive pulmonary disease idiopathic pulmonary fibrosis
- pulmonary arterial hypertension cystic fibrosis
- cystic fibrosis interstitial lung disease
- acute lung injury sarcoidosis
- allergic rhinitis allergic rhinitis
- chronic cough bron
- Gastrointestinal (GI) disorders include, but are not limited to: irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), biliary colic and other biliary disorders, renal colic, diarrhea-dominant IBS, pain associated with Gl distension, ulcerative colitis, Crohn's disease, celiac disease, proctitis, eosinophilic gastroenteritis, mastocytosis, or an indication listed in a separate disease category herein.
- IBS irritable bowel syndrome
- IBD inflammatory bowel disease
- biliary colic and other biliary disorders include, but are not limited to: irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), biliary colic and other biliary disorders, renal colic, diarrhea-dominant IBS, pain associated with Gl distension, ulcerative colitis, Crohn's disease, celiac disease, proctitis, eosinophilic gastroenteritis, mastocyto
- Allergic diseases include, but are not limited to: anaphylaxis, allergic rhinitis, allergic dermatitis, allergic urticaria, angioedema, allergic asthma, allergic reactions to: food, drugs, insect bites, pollen; or an indication listed in a separate disease category herein.
- Infection-based diseases include, but are not limited to: sepsis, septic shock, viral diseases, malaria, Lyme disease, ocular infections, conjunctivitis, Whipple Disease, or an indication listed in a separate disease category herein.
- Trauma and tissue injury-based conditions include, but are not limited to: renal glomerular damage, reperfusion injury (for example to heart, kidney, lung), spinal cord injury, tissue scarring, tissue adhesion, tissue repair, transplant rejection (for examples to heart, lung, bone marrow, cartilage, cornea, kidney, limb, liver, muscle, myoblast, pancreas, pancreatic islet, skin, nerve, small intestine, trachea), hypersensitivities, or an indication listed in a separate disease category herein.
- Fibrotic diseases include, but are not limited tobdiopathic pulmonary fibrosis, liver fibrosis, renal fibrosis, or an indication listed in a separate disease category herein.
- Joint, muscle and bone disorders include, but are not limited to: osteoarthritis, osteoporosis, rheumatoid arthritis, juvenile arthritis, psoriatic arthritis, erosive osteoarthritis of the hand, arthrofibrosi s/traumatic knee injury, anterior cruciate knee ligament tear, relapsing polychondritis, recurrent multifocal osteomyelitis, Majeed syndrome, ankylosing spondylitis, gout of the lumbar spine, antisynthetase syndrome, idiopathic inflammatory myopathies, articular chondrocalcinosis, systemic-onset juvenile idiopathic arthritis (SJIA), gout and pyrophosphate crystal arthritis, or an indication listed in a separate disease category herein.
- osteoarthritis osteoporosis
- rheumatoid arthritis juvenile arthritis
- psoriatic arthritis erosive osteoarthritis of the hand
- Skin/ dermatological diseases include, but are not limited to: psoriasis, atopic dermatitis, cutaneous lupus, acne, dermatomyositis, eczema, pruritus, scleroderma, Sweet Syndrome/neutrophilic dermatosis, neutrophilic panniculitis, acrodermatitis (form of pustular psoriasis), or an indication listed in a separate disease category herein.
- Renal diseases include, but are not limited to: acute kidney injury (AKI) (sepsis-AKI, coronary artery bypass graft-AKI, cardiac surgery-AKI, non-cardiac surgery-AKI, transplant surgery-AKI cisplatin-AKI, contrast/imaging agent induced-AKI), glomerulonephritis, IgA nephropathy, crescentic GN, lupus nephritis, HIV associated nephropathy, membraneous nephropathy, C3 glomerulopathy, Dense deposit disease, ANCA vasculitis, diabetic nephropathy, hemolytic-uremic syndrome, atypical Hemolytic-uremic syndrome, nephrotic syndrome, nephritic syndrome, hypertensive nephrosclerosis, ApoLl nephropathy, focal segmental glomerulosclerosis, Alport syndrome, Fanconi syndrome, crystal nephropathy, nephrolithia
- Hematopoietic diseases include, but are not limited to: hemolytic anemia, or an indication listed in a separate disease category herein.
- Liver diseases include, but are not limited to: liver fibrosis, liver cirrhosis, nonalcoholic steatohepatitis (NASH), or an indication listed in a separate disease category herein.
- liver fibrosis liver cirrhosis
- NASH nonalcoholic steatohepatitis
- Oral diseases include, but are not limited to: gingivitis, periodontal disease or an indication listed in a separate disease category herein.
- Metabolic diseases include, but are not limited to: Type 2 diabetes (and resulting complications), gout and hyperuricemia, metabolic syndrome, insulin resistance, obesity, obesity-related hyperglycemia or an indication listed in a separate disease category herein.
- Compounds of the present disclosure are also useful in the treatment of a proliferative disease selected from a benign or malignant tumor, solid tumor, carcinoma of the brain, kidney, liver, adrenal gland, bladder, breast, stomach, gastric tumors, ovaries, colon, rectum, prostate, pancreas, lung, vagina, cervix, testis, genitourinary tract, esophagus, larynx, skin, bone or thyroid, sarcoma, glioblastomas, neuroblastomas, multiple myeloma, gastrointestinal cancer, especially colon carcinoma or colorectal adenoma, a tumor of the neck and head, an epidermal hyperproliferation, psoriasis, prostate hyperplasia
- Cardiovascular diseases include, but are not limited to coronary heart disease, acute coronary syndrome, ischaemic heart disease, first or recurrent myocardial infarction, secondary myocardial infarction, non-ST segment elevation myocardial infarction, or ST segment elevation myocardial infarction, ischemic sudden death, transient ischemic attack, peripheral occlusive arterial disease, angina, atherosclerosis, hypertension, heart failure (such as congestive heart failure), diastolic dysfunction (such as left ventricular diastolic dysfunction, diastolic heart failure, and impaired diastolic filling), systolic dysfunction (such as systolic heart failure with reduced ejection fraction), vasculitis, ANCA vasculitis, post-myocardial infarction cardiac remodeling atrial fibrillation, arrhythmia (ventricular), ischemia, hypertrophic cardiomyopathy, sudden cardiac death, myocardial and vascular fibrosis, impaired arterial compliance, myocardial
- venous thrombosis deep vein thrombosis, thrombophlebitis, arterial embolism, coronary arterial thrombosis, cerebral arterial thrombosis, cerebral embolism, kidney embolism, pulmonary embolism, and thrombosis resulting from (a) prosthetic valves or other implants, (b) indwelling catheters, (c) stents, (d) cardiopulmonary bypass, (e) hemodialysis, or (f) other procedures in which blood is exposed to an artificial surface that promotes thrombosis.
- thrombosis includes occlusion (e.g., after a bypass) and reocclusion (e.g., during or after percutaneous transluminal coronary angioplasty).
- Cardiovascular complications of type 2 diabetes are associated with inflammation, and include conditions such as macrovascular disease, hyperglycemia, metabolic syndrome, impaired glucose tolerance, hyperuricemia, glucosuria, cataracts, diabetic neuropathy, diabetic nephropathy, diabetic retinopathy, obesity, dyslipidemia, hypertension, hyperinsulinemia, and insulin resistance syndrome, or an indication listed in a separate disease category herein.
- Neuroinflammatory and neurodegenerative conditions include diseases or diorders such as multiple sclerosis, migraine; epilepsy; Alzheimer's disease; Parkinson's disease; brain injury; stroke; cerebrovascular diseases (including cerebral arteriosclerosis, cerebral amyloid angiopathy, hereditary cerebral hemorrhage, and brain hypoxia-ischemia); cognitive disorders (including amnesia, senile dementia, HIV associated dementia, Alzheimer's associated dementia, Huntington's associated dementia, Lewy body dementia, vascular dementia, drug related dementia, delirium, and mild cognitive impairment); mental deficiency (including Down syndrome and fragile X syndrome); sleep disorders (including hypersomnia, circadian rhythm sleep disorder, insomnia, parasomnia, and sleep deprivation) and psychiatric disorders (such as anxiety (including acute stress disorder, generalized anxiety disorder, social anxiety disorder, panic disorder, post-traumatic stress disorder and obsessive-compulsive
- the acute or chronic autoimmune and/or inflammatory condition is a disorder of lipid metabolism via the regulation of APO-A1 such as hypercholesterolemia, atherosclerosis and Alzheimer's disease.
- the acute or chronic autoimmune and/or inflammatory condition are respiratory disorders such as asthma, chronic obstructive pulmonary disease, pulmonary arterial hypertension or idiopathic pulmonary fibrosis.
- the acute or chronic autoimmune and/or inflammatory condition is a systemic inflammatory disorder such as rheumatoid arthritis, osteoarthritis, acute gout, psoriasis, systemic lupus erythematosus, multiple sclerosis, scleroderma or inflammatory bowel disease (Crohn's disease and ulcerative colitis).
- a systemic inflammatory disorder such as rheumatoid arthritis, osteoarthritis, acute gout, psoriasis, systemic lupus erythematosus, multiple sclerosis, scleroderma or inflammatory bowel disease (Crohn's disease and ulcerative colitis).
- the acute or chronic autoimmune and/or inflammatory condition is multiple sclerosis.
- Some embodiments provide methods of treating a metabolic disease by administering a therapeutically effective amount of the compound of Formula (I) wherein the metabolic disease is diabetes or hyperglycemia.
- Other embodiments provide the use of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for the manufacture of a medicament for the treatment of a metabolic disease wherein the metabolic disease is diabetes or hyperglycemia.
- Still other embodiments provide an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for treating diabetes or hyperglycemia.
- Some embodiments provide methods of treating an inflammatory disease or disorder, by administering a therapeutically effective amount of the compound of Formula (I) wherein the inflammatory disease or disorder is inflammatory bowel disease (including Crohn’s disease and ulcerative colitis), psoriasis, immune thrombocytopenia (ITP), systemic sclerosis, neointimal hyperplasia, cardiovascular disease or hypertension.
- inflammatory disease or disorder is inflammatory bowel disease (including Crohn’s disease and ulcerative colitis), psoriasis, immune thrombocytopenia (ITP), systemic sclerosis, neointimal hyperplasia, cardiovascular disease or hypertension.
- inflammatory disease or disorder is inflammatory bowel disease (including Crohn’s disease and ulcerative colitis), psoriasis, immune thrombocytopenia (ITP), systemic sclerosis, neointimal hyperplasia, cardiovascular disease or hypertension.
- Still other embodiments provide an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for treating an inflammatory disease or disorder, wherein the inflammatory disease or disorder is inflammatory bowel disease (including Crohn’s disease and ulcerative colitis), psoriasis, immune thrombocytopenia (ITP), systemic sclerosis, neointimal hyperplasia, cardiovascular disease or hypertension.
- inflammatory disease or disorder is inflammatory bowel disease (including Crohn’s disease and ulcerative colitis), psoriasis, immune thrombocytopenia (ITP), systemic sclerosis, neointimal hyperplasia, cardiovascular disease or hypertension.
- the present disclosure relates to methods for the treatment of disease or disorder selected from inflammatory bowel disease (including ulcerative colitis and Crohn's disease), colorectal cancer, and gastritis, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate or salt of a solvate thereof.
- Some embodiments provide the use of a compound of Formula (I), or a pharmaceutically acceptable salt, solvate, or solvate of a salt thereof, for the manufacture of a medicament for the treatment of disease or disorder selected from inflammatory bowel disease (including ulcerative colitis and Crohn's disease), colorectal cancer, and gastritis.
- a disease or disorder selected from inflammatory bowel disease (including ulcerative colitis and Crohn's disease), colorectal cancer, and gastritis.
- said disease or disorder is inflammatory bowel disease.
- said disease or disorder is ulcerative colitis.
- said disease or disorder is Crohn’s disease.
- the compounds and compositions described herein can, for example, be administered orally, parenterally (e.g., subcutaneously, intracutaneously, intravenously, intramuscularly, intraarticularly, intraarterially, intrasynovially, intrasternally, intrathecally, intralesionally and by intracranial injection or infusion techniques), by inhalation spray, topically, rectally, nasally, buccally, vaginally, via an implanted reservoir, by injection, subdermally, intraperitoneally, transmucosally, or in an ophthalmic preparation, with a dosage ranging from about 0.01 mg/kg to about 1000 mg/kg, or any value in between (e.g., from about 0.01 to about 100 mg/kg, from about 0.1 to about 100 mg/kg, from about 1 to about 100 mg/kg, from about 1 to about 10 mg/kg, or any value in between) every 4 to 120 hours, or any value in between.
- parenterally e.g., subcutaneously, intracutaneously
- compositions are administered by oral administration or by injection.
- the methods herein contemplate administration of an effective amount of compound or compound composition to achieve the desired or stated effect.
- the pharmaceutical compositions of the present disclosure will be administered from about 1 to about 6 times per day or alternatively, as a continuous infusion. Such administration can be used as a chronic or acute therapy.
- dosage forms include from 0.001 milligrams to 2,000 milligrams, or any value in between (including, from 0.001 milligrams to 1,000 milligrams, from 0.001 milligrams to 500 milligrams, from 0.01 milligrams to 250 milligrams, from 0.01 milligrams to 100 milligrams, from 0.05 milligrams to 50 milligrams, and from 0.1 milligrams to 25 milligrams, or any value in between) of a compound of Formula (I) (and/or a compound of any of the other formulae described herein) or a salt (e.g., a pharmaceutically acceptable salt) thereof as defined anywhere herein.
- the dosage forms can further include a pharmaceutically acceptable carrier and/or an additional therapeutic agent.
- Appropriate dosage levels may be determined by any suitable method known to one skilled in the art of treating inflammatory diseases.
- the active substance is administered at a frequency of 1 to 4 times per day for topical administration, or less often if a drug delivery system is used.
- Non-steroidal anti-inflammatory drugs including but not limited to, nonselective COX1/2 inhibitors such as piroxicam, naproxen, flubiprofen, fenoprofen, ketoprofen, ibuprofen, etodolac (Lodine), mefanamic acid, sulindac, apazone, pyrazolones (such as phenylbutazone), salicylates (such as aspirin); selective COX2 inhibitors such as: celecoxib, rofecoxib, etoricoxib, valdecoxib, meloxicam; Immunomodulatory and/ or anti-inflammatory agents, including but not limited to, methotrexate, leflunomide, ciclesonide, chloroquine, hydroxychloroquine, d-penicillamine, auranofm, sulfas
- NSAIDs Non-steroidal anti-inflammatory drugs
- Leukotriene pathway modulators including but not limited to, 5-LO inhibitors (such as zileuton), FLAP antagonists (such as veliflapon, fiboflapon), LTD4 antagonists (such as montelukast, zafirlukast or pranlukast); HI receptor antagonists, including but not limited to, cetirizine, loratadine, desloratadine, fexofenadine, astemizole, azelastine or chlorpheniramine; PDE4 inhibitors, including but not limited to, apremilast, roflumilast or AN2728; Vitamin D receptor modulators, including but not limited to, paricalcitol; Nrf2 pathway activators, including but not limited to, fumarates, sulfurophane and bardoxolone methyl; Modulators of the RAR-related orphan receptor (ROR)
- 5-LO inhibitors such as zileuton
- FLAP antagonists such as veliflap
- Additional therapeutic agents include antithrombotic agents (anti-coagulant or coagulation inhibitory agents, anti-platelet or platelet inhibitory agents, thrombin inhibitors, thrombolytic or fibrinolytic agents), anti-arrhythmic agents, anti-hypertensive agents, calcium channel blockers (L-type and T-type), cardiac glycosides, diuretics, mineralocorticoid receptor antagonists, NO donating agents such as organonitrates, NO promoting agents such as phosphodiesterase inhibitors, cholesterol/lipid lowering agents and lipid profile therapies, anti diabetic agents, anti-depressants, anti-inflammatory agents (steroidal and non-steroidal), anti osteoporosis agents, hormone replacement therapies, oral contraceptives, anti-obesity agents, anti-anxiety agents, anti-proliferative agents, anti-tumor agents, anti-ulcer and gastroesophageal reflux disease agents, growth hormone and/or growth hormone secretagogues, thyroid mimetics (including thyroid hormone receptor antagonist), anti-infect
- antithrombotic agents include fondaparinux, edoxaban, betrixaban, apixaban and rivaroxaban, warfarin, heparins (e.g., unfractioned and low molecular weight heparins such as enoxaparin and dalteparin), hirudin, argatrobanas, aspirin, ibuprofen, naproxen, sulindac, indomethacin, mefenamate, droxicam, diclofenac, sulfinpyrazone, piroxicam, ticlopidine, clopidogrel, ticagrelor, prasugrel, tirofiban, ifetroban, eptifibatide, abciximab, dabigatran, melagatran, disulfatohirudin, tissue plasminogen activator, modified tissue plasminogen activator, anistreplase, urokina
- Suitable anti-arrythmic agents include: Class I agents (such as propafenone); Class II agents (such as metoprolol, atenolol, carvadiol and propranolol); Class III agents (such as sotalol, dofetilide, amiodarone, azimilide and ibutilide); Class IV agents (such as ditiazem and verapamil); K + channel openers such as lAch inhibitors, and iKur inhibitors (e.g., compounds such as those disclosed in W001/40231).
- Class I agents such as propafenone
- Class II agents such as metoprolol, atenolol, carvadiol and propranolol
- Class III agents such as sotalol, dofetilide, amiodarone, azimilide and ibutilide
- Class IV agents such as ditiazem and verapamil
- K + channel openers such as lAch inhibitor
- Suitable anti-hypertensive agents include: alpha adrenergic blockers; beta adrenergic blockers; calcium channel blockers (e.g., diltiazem, verapamil, nifedipine and amlodipine); vasodilators (e.g., hydralazine), diruetics (e.g., chlorothiazide, hydrochlorothiazide, flumethi azide, hydroflumethiazide, bendroflumethi azide, methylchlorothiazide, trichloromethiazide, polythiazide, benzthiazide, ethacrynic acid tricrynafen, chlorthalidone, torsemide, furosemide, musolimine, bumetanide, triamtrenene, amiloride, spironolactone); renin inhibitors; ACE inhibitors (e.g., capto
- Dual ET/AII antagonist e.g., compounds disclosed in WO 00/01389
- neutral endopeptidase (NEP) inhibitors neutral endopeptidase (NEP) inhibitors
- vasopepsidase inhibitors dual NEP-ACE inhibitors
- gemopatrilat and nitrates an exemplary antianginal agent is ivabradine.
- Suitable calcium channel blockers include diltiazem, verapamil, nifedipine and amlodipine and mybefradil.
- suitable cardiac glycosides include digitalis and ouabain.
- Examples of suitable combination mineralocorticoid receptor antagonists include spironolactone and eplerenone.
- suitable combination phosphodiesterase inhibitors include: PDE3 inhibitors (such as cilostazol); and PDE5 inhibitors (such as sildenafil).
- Examples of suitable cholesterol/lipid lowering agents and lipid profile therapies include: HMG- CoA reductase inhibitors (e.g., pravastatin, lovastatin, atorvastatin, simvastatin, fluvastatin, NK- 104 (a.k.a. itavastatin, or nisvastatin or nisbastatin) and ZD-4522 (a.k.a.
- Atherosclerotic agents include agents that modulate the action of PCSK9, for example, bococizumab.
- Anti-inflammatory agents also include sPLA2 and lpPLA2 inhibitors (such as darapladib), 5 LO inhibitors (such as atreleuton) and IL-l and IL-l r antagonists (such as canakinumab).
- sPLA2 and lpPLA2 inhibitors such as darapladib
- 5 LO inhibitors such as atreleuton
- IL-l and IL-l r antagonists such as canakinumab
- anti-diabetic agents particularly type 2 anti-diabetic agents.
- suitable anti-diabetic agents include (e.g. insulins, metfomin, DPPIV inhibitors, GLP-l agonists, analogues and mimetics, SGLT1 and SGLT2 inhibitors).
- Suitable anti-diabetic agents include an acetyl-CoA carboxylase- (ACC) inhibitor such as those described in WO2009144554, W02003072197, WO2009144555 and W02008065508, a diacylglycerol O- acyltransferase 1 (DGAT-l) inhibitor, such as those described in W009016462 or W02010086820, AZD7687 or LCQ908, diacylglycerol O-acyltransferase 2 (DGAT-2) inhibitor, monoacylglycerol O-acyltransferase inhibitors, a PDE10 inhibitor, an AMPK activator, a sulfonylurea (e.g., acetohexamide, chlorpropamide, diabinese, glibenclamide, glipizide, glyburide, glimepiride, gliclazide, glipentide, gliquidone, glisolamide, to
- SIRT-l inhibitor e.g., resveratrol, GSK2245840 or GSK184072
- DPP -IV dipeptidyl peptidease IV
- an insulin secreatagogue e.g., those in W02005116014, sitagliptin, vildagliptin, alogliptin, dutogliptin, linagliptin and saxagliptin
- an insulin secreatagogue e.g., those described in W02020116014, sitagliptin, vildagliptin, alogliptin, dutogliptin, linagliptin and saxagliptin
- an insulin secreatagogue e.g., those in W02005116014, sitagliptin, vildagliptin, alogliptin, dutogliptin, linagliptin and saxagliptin
- an insulin secreatagogue
- GSK1362885 a VPAC2 receptor agonist
- SGLT2 inhibitors such as those described in Chao et al ., Nat. Rev. Drug Disc. 9, 551-559 (2010) including dapagliflozin, canagliflozin, empagliflozin, tofogliflozin (CSG452), ASP-1941 , THR1474, TS-071 , ISIS388626 and LX421 1 as well as those in W02010023594, a glucagon receptor modulator such as those described in Demong, et al, Ann. Rep. Med. Chem.
- GPR119 modulators particularly agonists, such as those described in W02010140092, WO2010128425, W02010128414, W02010106457, Jones, et al, Med. Chem. 2009, 44, 149-170 (e.g., MBX-2982, GSK1292263, APD597 and PSN821), FGF21 derivatives or analogs such as those described in Kharitonenkov et al. , Curr. Op. Investig.
- TGR5 also termed GPBAR1 receptor modulators, particularly agonists, such as those described in Zhong, M., Current Topics in Medicinal Chemistry, 2010, 10(4), 386-396 and INT777, GPR40 agonists, such as those described in Medina, J.C., Annual Reports in Medicinal Chemistry, 2008, 43, 75-85, including but not limited to TAK-875, GPR120 modulators, particularly agonists, high affinity nicotinic acid receptor (HM74A) activators, and SGLT1 inhibitors, such as GSK1614235.
- HM74A high affinity nicotinic acid receptor
- anti-diabetic agents that can be combined with the compounds of the present disclosure can be found, for example, at page 28, line 35 through page 30, line 19 of WO201 1005611.
- Other anti diabetic agents could include inhibitors or modulators of carnitine palmitoyi transferase enzymes, inhibitors of fructose 1 ,6-diphosphatase, inhibitors of aldose reductase, inhibitors of TORC2, inhibitors of CCR2 and/or CCR5, inhibitors of PKC isoforms (e.g.
- PKCa, RKOb, PKOy inhibitors of fatty acid synthetase, inhibitors of serine palmitoyi transferase, modulators of GPR81 , GPR39, GPR43, GPR41 , GPR105, Kvl.3, retinol binding protein 4, glucocorticoid receptor, somatostain receptors (e.g. SSTR1 , SSTR2, SSTR3 and SSTR5), inhibitors or modulators of PDHK2 or PDHK4, inhibitors of MAP4K4, modulators of IL1 family including ILI beta, modulators of RXRalpha.
- suitable anti-diabetic agents include mechanisms listed by Carpino, P. A., Goodwin, B.
- the compounds of the present disclosure may be used in combination with neuroinflammatory and neurodegenerative agents in mammals.
- additional neuroinflammatory and neurodegenerative agents include antidepressants, antipsychotics, anti pain agents, anti-Alzheimer's agents, and anti-anxiety agents.
- Examples of particular classes of antidepressants that can be used in combination with the compounds of the present disclosure include norepinephrine reuptake inhibitors, selective serotonin reuptake inhibitors (SSRIs), NK-l receptor antagonists, monoamine oxidase inhibitors (MAOIs), reversible inhibitors of monoamine oxidase (RIMAs), serotonin and noradrenaline reuptake inhibitors (SNRIs), corticotropin releasing factor (CRF) antagonists, and atypical antidepressants.
- Suitable norepinephrine reuptake inhibitors include tertiary amine tricyclics and secondary amine tricyclics.
- Suitable tertiary amine tricyclics and secondary amine tricyclics include amitriptyline, clomipramine, doxepin, imipramine, trimipramine, dothiepin, butriptyline, nortriptyline, protriptyline, amoxapine, desipramine and maprotiline.
- suitable SSRIs include fluoxetine, fluvoxamine, paroxetine, and sertraline.
- monoamine oxidase inhibitors include isocarboxazid, phenelzine, and tranylcyclopramine.
- suitable reversible inhibitors of monoamine oxidase include moclobemide.
- SNRIs of use in the present disclosure include venlafaxine.
- suitable atypical anti depressants include bupropion, lithium, trazodone and viloxazine.
- anti-Alzheimer's agents include NMDA receptor antagonists such as memantine; and cholinesterase inhibitors such as donepezil and galantamine.
- suitable classes of anti-anxiety agents that can be used in combination with the compounds of the present disclosure include benzodiazepines and serotonin 1A receptor (5-HT1A) agonists, and CRF antagonists.
- Suitable benzodiazepines include alprazolam, chlordiazepoxide, clonazepam, chlorazepate, diazepam, lorazepam, oxazepam, and prazepam.
- Suitable 5-HT1A receptor agonists include buspirone and ipsapirone.
- Suitable CRF antagonists include verucerfont.
- Suitable atypical antipsychotics include paliperidone, ziprasidone, risperidone, aripiprazole, olanzapine, and quetiapine.
- Suitable nicotine acetylcholine agonists include CP-601927 and vareni cline.
- Anti -pain agents include pregabalin, gabapentin, clonidine, neostigmine, baclofen, midazolam, ketamine and ziconotide.
- co-administration refers to a combination of a compound of the present disclosure and one or more other pharmaceutically active ingredient, or a pharmaceutically acceptable salt thereof, includes the following:
- hVNN-l IC50 range: A ⁇ 100 niV ; 100 nM ⁇ B ⁇ 500 nM; 500 nM ⁇ C ⁇ 2500 nM; 2500 nM ⁇ D ⁇ 25 mM.
- Example 8 3-((2-r(pyrimidin-5-ylmethvnamino1-E3-thiazol-5- yllcarbonvDbenzenecarbonitrile [0146] The title compound was prepared analogously to Ex. 1, replacing 3- pyridylmethanamine in Step 3 with pyrimidin-5-ylmethanamine.
- MS: m/z 32l.8l (M+H).
- Example 62 2- 4-fluoiOphenvDoxetan-3-yl1aminol( ' l.3-thiazol-5-vD 3-
- Example 66 (2-((l-(pyridin-3-yl)ethyl)amino)thiazol-5-yl)(3-(trifluoromethyl)phenyl)- methanone (faster eluting enantiomer)
- Example 27 The product of Example 27 was separated by chiral SFC chromatography into its constituent enantiomers. The faster eluting enantiomer was assigned as Example 66.
- Example 27 was separated by chiral SFC chromatography into its constituent enantiomers. The slower eluting enantiomer was assigned as Example 67.
- Example 70 3-r(dimethylamino)sulfonyl1phenyl 2-r(3-pyridylmethvOamino1(E3-thiazol-5- vD ketone [0208]
- the title compound was prepared analogously to Example 4, replacing 3- (trifluoromethylsulfonyl)benzoic acid in Step 1 with 3-(N,N-dimethylsulfamoyl)benzoic acid.
- Example 80 2-r(3-pyridylmethvDamino1(E3-thiazol-5-vD 3-(trifluoromethoxy)phenyl ketone
- Example 85 2-( r(2-amino(3-pyridylV)methvnamino
- the THP-protected title compound was prepared analogously to Example 91, replacing 1 -methyl- lH-pyrazole-4-boronic acid with l-tetrahydropyran-2-yl-5-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole.
- the THP-protected product was stirred in methanolic HC1 at 60 °C for 2 hours, followed by in vacuo concentration to provide the title compound.
- Ex. 112 3 -(methyl sulfonvDphenyl 2-r(oxolan-2-ylmethvDamino1(E3-thiazol-5-vD ketone [0253]
- the title compound was prepared analogously to Ex. 1, replacing 3- formylbenzonitrile in Step 1 with 3-(methylsulfonyl)benzaldehyde and replacing 3- pyridylmethanamine in Step 3 with (tetrahydrofuran-2-yl)methanamine.
- the term‘including’ should be read to mean‘including, without limitation,’‘including but not limited to,’ or the like;
- the term‘comprising’ as used herein is synonymous with‘including,’‘containing,’ or‘characterized by,’ and is inclusive or open-ended and does not exclude additional, unrecited elements or method steps;
- the term ‘having’ should be interpreted as‘having at least;’ the term‘includes’ should be interpreted as‘includes but is not limited to;’ the term‘example’ is used to provide exemplary instances of the item in discussion, not an exhaustive or limiting list thereof; adjectives such as ‘known’,‘normal’,‘standard’, and terms of similar meaning should not be construed as limiting the item described to a given time period or to an item available as of a given time, but instead should be read to encompass known, normal, or standard technologies that may be available or known now or at any time in the future; and use of terms like‘preferably,’ ‘preferred,’‘desi
- a group of items linked with the conjunction‘and’ should not be read as requiring that each and every one of those items be present in the grouping, but rather should be read as‘and/or’ unless expressly stated otherwise.
- a group of items linked with the conjunction‘or’ should not be read as requiring mutual exclusivity among that group, but rather should be read as‘and/or’ unless expressly stated otherwise.
- any of the features of an embodiment of any of the aspects is independently combinable, partly or wholly with other embodiments described herein in any way, e.g., one, two, or three or more embodiments may be combinable in whole or in part. Further, any of the features of an embodiment may be made optional to other aspects or embodiments.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La présente invention concerne des composés de formule (I) et des sels, solvates et sels de solvates pharmaceutiquement acceptables de ceux-ci, des compositions pharmaceutiques contenant les composés de formule (I), ainsi que l'utilisation des composés de formule (I) pour le traitement de maladies intestinales inflammatoires, telles que la maladie de Crohn et la colite ulcéreuse.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762611455P | 2017-12-28 | 2017-12-28 | |
US62/611,455 | 2017-12-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2019133445A1 true WO2019133445A1 (fr) | 2019-07-04 |
Family
ID=65024113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2018/066882 WO2019133445A1 (fr) | 2017-12-28 | 2018-12-20 | Aminothiazoles utilisés en tant qu'inhibiteurs de vanin-1 |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2019133445A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020102575A1 (fr) * | 2018-11-16 | 2020-05-22 | Inception Ibd, Inc. | Aminothiazoles hétérocycliques et leurs utilisations |
WO2021214019A1 (fr) | 2020-04-24 | 2021-10-28 | Bayer Aktiengesellschaft | Aminothiazoles substitués utilisés comme inhibiteurs de la dgk zêta pour l'activation immunitaire |
CN115089590A (zh) * | 2022-06-13 | 2022-09-23 | 同济大学 | 环戊基三唑嘧啶类药物作为药物成分在肝炎药物中的应用 |
Citations (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
WO2000001389A1 (fr) | 1998-07-06 | 2000-01-13 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides en tant que doubles antagonistes de recepteurs d'angiotensine et d'endotheline |
US6043265A (en) | 1997-01-30 | 2000-03-28 | Bristol-Myers Squibb Co. | Isoxazolyl endothelin antagonists |
WO2001040231A1 (fr) | 1999-12-06 | 2001-06-07 | Bristol-Myers Squibb Company | Dihydropyrimidines heterocycliques utiles en tant qu'inhibiteurs des canaux potassium |
WO2003072197A1 (fr) | 2002-02-27 | 2003-09-04 | Pfizer Products Inc. | Inhibiteurs de l'acetyl-coa-carboxylase |
WO2005116014A1 (fr) | 2004-05-12 | 2005-12-08 | Pfizer Products Inc. | Derives de proline et leur utilisation en tant qu'inhibiteurs de la dipeptidyl-peptidase iv |
WO2007122482A1 (fr) | 2006-04-20 | 2007-11-01 | Pfizer Products Inc. | Composés phényle amido-hétérocycliques fusionnés pour la prévention et le traitement de maladies à médiation par glucokinase |
WO2008065508A1 (fr) | 2006-11-29 | 2008-06-05 | Pfizer Products Inc. | Inhibiteurs de la spirocétoneacétyl-coa carboxylase |
WO2009016462A2 (fr) | 2007-08-02 | 2009-02-05 | Pfizer Products Inc. | Bicyclolactames substitués |
WO2009144555A1 (fr) | 2008-05-28 | 2009-12-03 | Pfizer Inc. | Inhibiteurs de la pyrazolospirocétone acétyl-coa carboxylase |
WO2009144554A1 (fr) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Inhibiteurs de la pyrazolospirocétone acétl-coa carboxylase |
WO2010013161A1 (fr) | 2008-07-29 | 2010-02-04 | Pfizer Inc. | Hétéroaryles fluorés |
WO2010023594A1 (fr) | 2008-08-28 | 2010-03-04 | Pfizer Inc. | Dérivés de dioxa-bicyclo[3.2.1.]octane-2,3,4-triol |
WO2010086820A1 (fr) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | Dérivés de 4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazépin-6(5h)-yl)phényle |
WO2010103438A1 (fr) | 2009-03-11 | 2010-09-16 | Pfizer Inc. | Indazole amides substitués |
WO2010103437A1 (fr) | 2009-03-11 | 2010-09-16 | Pfizer Inc. | Dérivés de benzofuranyle utilisés comme inhibiteurs de la glucokinase |
WO2010106457A2 (fr) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3,3.1]nonanes |
WO2010128425A1 (fr) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Modulateurs de gpr119 |
WO2010128414A1 (fr) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Modulateurs du gpr119 |
WO2010140092A1 (fr) | 2009-06-05 | 2010-12-09 | Pfizer Inc. | Derives de l-(piperidin-4-yl)-pyrazole utilises en tant que modulateurs du gpr 119 |
WO2011005611A1 (fr) | 2009-07-09 | 2011-01-13 | Merck Sharp & Dohme Corp. | Agonistes du récepteur de la neuromédine u et leurs utilisations |
WO2016193844A1 (fr) * | 2015-05-29 | 2016-12-08 | Pfizer Inc. | Nouveaux composés hétérocycliques utilisés en tant qu'inhibiteurs de l'enzyme vanine-1 |
WO2018011681A1 (fr) * | 2016-07-14 | 2018-01-18 | Pfizer Inc. | Nouveaux pyrimidine carboxamides utilisées comme inhibiteurs de l'enzyme vanin-1 |
-
2018
- 2018-12-20 WO PCT/US2018/066882 patent/WO2019133445A1/fr active Application Filing
Patent Citations (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
US6043265A (en) | 1997-01-30 | 2000-03-28 | Bristol-Myers Squibb Co. | Isoxazolyl endothelin antagonists |
WO2000001389A1 (fr) | 1998-07-06 | 2000-01-13 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides en tant que doubles antagonistes de recepteurs d'angiotensine et d'endotheline |
WO2001040231A1 (fr) | 1999-12-06 | 2001-06-07 | Bristol-Myers Squibb Company | Dihydropyrimidines heterocycliques utiles en tant qu'inhibiteurs des canaux potassium |
WO2003072197A1 (fr) | 2002-02-27 | 2003-09-04 | Pfizer Products Inc. | Inhibiteurs de l'acetyl-coa-carboxylase |
WO2005116014A1 (fr) | 2004-05-12 | 2005-12-08 | Pfizer Products Inc. | Derives de proline et leur utilisation en tant qu'inhibiteurs de la dipeptidyl-peptidase iv |
WO2007122482A1 (fr) | 2006-04-20 | 2007-11-01 | Pfizer Products Inc. | Composés phényle amido-hétérocycliques fusionnés pour la prévention et le traitement de maladies à médiation par glucokinase |
WO2008065508A1 (fr) | 2006-11-29 | 2008-06-05 | Pfizer Products Inc. | Inhibiteurs de la spirocétoneacétyl-coa carboxylase |
WO2009016462A2 (fr) | 2007-08-02 | 2009-02-05 | Pfizer Products Inc. | Bicyclolactames substitués |
WO2009144554A1 (fr) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Inhibiteurs de la pyrazolospirocétone acétl-coa carboxylase |
WO2009144555A1 (fr) | 2008-05-28 | 2009-12-03 | Pfizer Inc. | Inhibiteurs de la pyrazolospirocétone acétyl-coa carboxylase |
WO2010013161A1 (fr) | 2008-07-29 | 2010-02-04 | Pfizer Inc. | Hétéroaryles fluorés |
WO2010023594A1 (fr) | 2008-08-28 | 2010-03-04 | Pfizer Inc. | Dérivés de dioxa-bicyclo[3.2.1.]octane-2,3,4-triol |
WO2010086820A1 (fr) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | Dérivés de 4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazépin-6(5h)-yl)phényle |
WO2010103438A1 (fr) | 2009-03-11 | 2010-09-16 | Pfizer Inc. | Indazole amides substitués |
WO2010103437A1 (fr) | 2009-03-11 | 2010-09-16 | Pfizer Inc. | Dérivés de benzofuranyle utilisés comme inhibiteurs de la glucokinase |
WO2010106457A2 (fr) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3,3.1]nonanes |
WO2010128425A1 (fr) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Modulateurs de gpr119 |
WO2010128414A1 (fr) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Modulateurs du gpr119 |
WO2010140092A1 (fr) | 2009-06-05 | 2010-12-09 | Pfizer Inc. | Derives de l-(piperidin-4-yl)-pyrazole utilises en tant que modulateurs du gpr 119 |
WO2011005611A1 (fr) | 2009-07-09 | 2011-01-13 | Merck Sharp & Dohme Corp. | Agonistes du récepteur de la neuromédine u et leurs utilisations |
WO2016193844A1 (fr) * | 2015-05-29 | 2016-12-08 | Pfizer Inc. | Nouveaux composés hétérocycliques utilisés en tant qu'inhibiteurs de l'enzyme vanine-1 |
WO2018011681A1 (fr) * | 2016-07-14 | 2018-01-18 | Pfizer Inc. | Nouveaux pyrimidine carboxamides utilisées comme inhibiteurs de l'enzyme vanin-1 |
Non-Patent Citations (35)
Title |
---|
"Pharmaceutical Salts: Properties, Selection, and Use. A Handbook", 2002, VERLAG HELVETICA CHIMICA ACTA |
"Remington's Pharmaceutical Sciences", 1985, MACK PUBLISHING COMPANY, pages: 1418 |
BERGE ET AL.: "Pharmaceutical Salts", J. PHARM. SCI., vol. 66, 1977, pages 1 - 19, XP002675560, DOI: doi:10.1002/jps.2600660104 |
BERRUYER ET AL., MOL. CELL. BIOL., vol. 24, 2004, pages 7214 - 7224 |
BIOCHEM., vol. 11, 1972, pages 942 - 944 |
C. BERRUYER ET AL., J. EXP. MED., vol. 203, 2006, pages 2817 - 2827 |
CARPINO, P. A.; GOODWIN, B., EXPERT OPIN. THER. PAT, vol. 20, no. 12, 2010, pages 1627 - 51 |
CHAO ET AL., NAT. REV. DRUG DISC., vol. 9, 2010, pages 551 - 559 |
CHEN ET AL., DIABETES, vol. 63, 2014, pages 2073 - 2085 |
CHU ET AL., CANCER RES., vol. 65, 2005, pages 10478 - 10485 |
DAMMANAHALLI ET AL., PLOS ONE, vol. 7, 2012, pages e39106 |
DEMONG ET AL., ANN. REP. MED. CHEM., vol. 43, no. 1, 2008, pages 19 - 137 |
DI LEANDRO ET AL., FREE RADIC. BIOL. MED., vol. 44, 2008, pages 1088 - 1096 |
ELLI ET AL., LAB. INVEST., vol. 91, 2011, pages 452 - 461 |
GENSOLLEN ET AL., INFLAMM. BOWEL. DIS., vol. 19, 2013, pages 2315 - 2325 |
JANSEN ET AL., J. INVEST. DERMATOL., vol. 129, 2009, pages 2167 - 2174 |
JEITNER ET AL., BIOCHEM. PHARMACOL., vol. 69, 2005, pages 961 - 970 |
JONES ET AL., MED. CHEM., vol. 44, 2009, pages 149 - 170 |
KASKOW ET AL., EUR. J. HUM. GENET., vol. 22, 2014, pages 688 - 695 |
KAVIAN ET AL., J. IMMUNOL., vol. 197, 2016, pages 3326 - 3335 |
KHARITONENKOV ET AL., CURR. OP. INVESTIG. DRUGS, vol. 10, no. 4, 2009, pages 359 - 364 |
LEONARDI ET AL., PROG. LIPID. RES., vol. 44, 2005, pages 125 - 153 |
LESORT ET AL., J. BIOL. CHEM., vol. 278, 2003, pages 3825 - 3830 |
MARTIN ET AL., J. CLIN. INVEST., vol. 113, 2004, pages 591 - 597 |
MEDINA, J.C., ANNUAL REPORTS IN MEDICINAL CHEMISTRY, vol. 43, 2008, pages 75 - 85 |
PITARI ET AL., FEBS LETT, vol. 483, 2000, pages 149 - 154 |
POUYET ET AL., INFLAMM. BOWEL DIS., vol. 16, 2010, pages 96 - 104 |
REICHARDT, C.; WELTON T.: "Solvents and Solvent Effects in Organic Chemistry", 2011, JOHN WILEY & SONS |
RUAN BH ET AL., ANAL. BIOCHEM., vol. 399, no. 2, 2010, pages 284 - 92 |
VAN DIEPEN ET AL., SCI. REP., vol. 6, 2016, pages 21906 |
WANG ET AL., PLOS GENET., vol. 10, 2014, pages el004641 |
Y. MUSHTAQ, NAT. REV. DRUG DISC., vol. 13, no. 4, 2014, pages 253 - 254 |
ZHANG ET AL., BLOOD, vol. 117, 2011, pages 4569 - 4579 |
ZHANG ET AL., DRUG DISC. TODAY, vol. 12, no. 9/10, 2007, pages 373 - 381 |
ZHONG, M., CURRENT TOPICS IN MEDICINAL CHEMISTRY, vol. 10, no. 4, 2010, pages 386 - 396 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020102575A1 (fr) * | 2018-11-16 | 2020-05-22 | Inception Ibd, Inc. | Aminothiazoles hétérocycliques et leurs utilisations |
WO2021214019A1 (fr) | 2020-04-24 | 2021-10-28 | Bayer Aktiengesellschaft | Aminothiazoles substitués utilisés comme inhibiteurs de la dgk zêta pour l'activation immunitaire |
WO2021214020A1 (fr) | 2020-04-24 | 2021-10-28 | Bayer Aktiengesellschaft | Aminothiazoles substitués utilisés comme inhibiteurs de la dgk zêta pour l'activation immunitaire |
CN115697980A (zh) * | 2020-04-24 | 2023-02-03 | 拜耳公司 | 作为dgkzeta抑制剂用于免疫活化的取代的氨基噻唑 |
CN115697979A (zh) * | 2020-04-24 | 2023-02-03 | 拜耳公司 | 作为用于免疫激活的dgkzeta抑制剂的取代的氨基噻唑类 |
US11964953B2 (en) | 2020-04-24 | 2024-04-23 | Bayer Aktiengesellschaft | Substituted aminothiazoles as DGKzeta inhibitors for immune activation |
CN115089590A (zh) * | 2022-06-13 | 2022-09-23 | 同济大学 | 环戊基三唑嘧啶类药物作为药物成分在肝炎药物中的应用 |
CN115089590B (zh) * | 2022-06-13 | 2023-05-12 | 同济大学 | 环戊基三唑嘧啶类药物作为药物成分在肝炎药物中的应用 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7443495B2 (ja) | ヘテロ環式rip1キナーゼ阻害剤 | |
JP6482629B2 (ja) | Trkaキナーゼ阻害剤としてのn−ピロリジニル、n’−ピラゾリル尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 | |
AU2016311376B2 (en) | Bicyclic-fused heteroaryl or aryl compounds as IRAK4 modulators | |
US20230165846A1 (en) | Heterocyclic glp-1 agonists | |
US10308615B2 (en) | Heterocyclic compounds as inhibitors of Vanin-1 enzyme | |
US8637510B2 (en) | Morpholinothiazoles as alpha 7 positive allosteric modulators | |
US11492365B2 (en) | Heterocyclic GLP-1 agonists | |
CN103998042B (zh) | Pi3k的活性或功能的抑制剂的应用 | |
CN111527084A (zh) | 可用作hpk1抑制剂的异呋喃酮化合物 | |
CN116323599A (zh) | 杂环glp-1激动剂 | |
JP2023524493A (ja) | ヘテロ環glp-1アゴニスト | |
CN116554152A (zh) | 用于治疗癌症的2-杂芳基-3-氧代-2,3-二氢哒嗪-4-甲酰胺 | |
WO2020102575A1 (fr) | Aminothiazoles hétérocycliques et leurs utilisations | |
JP2018527337A (ja) | 二環式縮合ヘテロアリールまたはアリール化合物 | |
JP2019518796A (ja) | 2,4−ジアミノ−ピリミジン化合物ならびに該化合物の作製法および使用法 | |
TW201444821A (zh) | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 | |
WO2019133445A1 (fr) | Aminothiazoles utilisés en tant qu'inhibiteurs de vanin-1 | |
KR101374412B1 (ko) | 케모카인 수용체 조절제로서의 3-아미노시클로펜탄카르복스아미드 | |
US20230391769A1 (en) | Substituted heterocyclic compounds and therapeutic uses thereof | |
US20160368919A1 (en) | Novel pyridine pyrazinones as bet-family bromodomain inhibitors | |
US20230339939A1 (en) | Substituted 1h-pyrrolo[3,2-b]pyridine compounds and methods of use thereof | |
WO2022037694A1 (fr) | Classe de composés hétérocycliques à cinq et six chaînons et leur utilisation en tant qu'inhibiteurs de protéine kinase du récepteur | |
CN108069938A (zh) | 2,4-二取代吡啶类化合物及其制备方法和应用 | |
EP4097099B1 (fr) | Agonistes hétérocycliques de glp-1 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 18834233 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 18834233 Country of ref document: EP Kind code of ref document: A1 |