CA2917050A1 - Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof - Google Patents

Info

Publication number

CA2917050A1

CA2917050A1 CA2917050A CA2917050A CA2917050A1 CA 2917050 A1 CA2917050 A1 CA 2917050A1 CA 2917050 A CA2917050 A CA 2917050A CA 2917050 A CA2917050 A CA 2917050A CA 2917050 A1 CA2917050 A1 CA 2917050A1

Authority

CA

Canada

Prior art keywords

pyrrole

carboxylate

methyl

octahydropyrrolo

hexafluoropropan

Prior art date

2013-07-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000008194 pharmaceutical composition Substances 0.000 title claims description 51
• LVQORWACYOGJPF-UHFFFAOYSA-N C(N)(O)=O.N1=CC=C2C1=CC=N2 Chemical compound C(N)(O)=O.N1=CC=C2C1=CC=N2 LVQORWACYOGJPF-UHFFFAOYSA-N 0.000 title abstract description 34
• 150000002894 organic compounds Chemical class 0.000 title abstract description 33
• 150000001875 compounds Chemical class 0.000 claims abstract description 475
• 238000000034 method Methods 0.000 claims abstract description 132
• 239000000203 mixture Substances 0.000 claims abstract description 100
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
• 208000035475 disorder Diseases 0.000 claims abstract description 37
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 35
• 208000002193 Pain Diseases 0.000 claims abstract description 24
• 230000036407 pain Effects 0.000 claims abstract description 20
• 201000010374 Down Syndrome Diseases 0.000 claims abstract description 17
• 206010044688 Trisomy 21 Diseases 0.000 claims abstract description 17
• 201000011510 cancer Diseases 0.000 claims abstract description 16
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 15
• 208000008589 Obesity Diseases 0.000 claims abstract description 12
• 235000020824 obesity Nutrition 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 334
• -1 cyano, phenyl Chemical group 0.000 claims description 237
• 229910052736 halogen Inorganic materials 0.000 claims description 221
• 150000002367 halogens Chemical group 0.000 claims description 221
• WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 206
• 125000001424 substituent group Chemical group 0.000 claims description 195
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 167
• 125000001188 haloalkyl group Chemical group 0.000 claims description 137
• 239000001257 hydrogen Substances 0.000 claims description 135
• 229910052739 hydrogen Inorganic materials 0.000 claims description 135
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 124
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 123
• 125000003545 alkoxy group Chemical group 0.000 claims description 121
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 109
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 88
• 150000003839 salts Chemical class 0.000 claims description 79
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 75
• 125000001072 heteroaryl group Chemical group 0.000 claims description 71
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 71
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 239000012453 solvate Substances 0.000 claims description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 125000004043 oxo group Chemical group O=* 0.000 claims description 49
• 239000003937 drug carrier Substances 0.000 claims description 42
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 42
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 208000015181 infectious disease Diseases 0.000 claims description 33
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 150000001204 N-oxides Chemical class 0.000 claims description 16
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 14
• 125000002393 azetidinyl group Chemical group 0.000 claims description 14
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 125000003386 piperidinyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000005549 heteroarylene group Chemical group 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 241000894006 Bacteria Species 0.000 claims description 8
• 210000000577 adipose tissue Anatomy 0.000 claims description 8
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• BQTIZWACTUVAGT-UHFFFAOYSA-N 2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1NCC2CN(C(=O)O)CC21 BQTIZWACTUVAGT-UHFFFAOYSA-N 0.000 claims description 6
• 241000233866 Fungi Species 0.000 claims description 6
• 125000000732 arylene group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 244000045947 parasite Species 0.000 claims description 5
• 241000700605 Viruses Species 0.000 claims description 4
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000005551 pyridylene group Chemical group 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• LRRIXSXTOMALTQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-methyl-3-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1=CC=C(N2CCCCC2)C(C)=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O LRRIXSXTOMALTQ-UHFFFAOYSA-N 0.000 claims description 2
• GUDNOEUDNIYXST-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(CC=3C(=CC=CC=3)C=3C=CC=CC=3)CC2CN1C(=O)ON1C(=O)CCC1=O GUDNOEUDNIYXST-UHFFFAOYSA-N 0.000 claims description 2
• XWPGBPOVTZVBBS-UHFFFAOYSA-N CNC(=O)C(OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1)C(F)(F)F Chemical compound CNC(=O)C(OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1)C(F)(F)F XWPGBPOVTZVBBS-UHFFFAOYSA-N 0.000 claims description 2
• MXDQCWQQNUWIND-UHFFFAOYSA-N CS(=O)(=O)N1CCN(CC1)c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound CS(=O)(=O)N1CCN(CC1)c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F MXDQCWQQNUWIND-UHFFFAOYSA-N 0.000 claims description 2
• KECJUFQKEMLDBE-UHFFFAOYSA-N CS(=O)(=O)N1CCN(CC1)c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CS(=O)(=O)N1CCN(CC1)c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O KECJUFQKEMLDBE-UHFFFAOYSA-N 0.000 claims description 2
• VJLUFGHHTCAAMS-UHFFFAOYSA-N Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC(CC1)C(=O)N1CCCC1 Chemical compound Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC(CC1)C(=O)N1CCCC1 VJLUFGHHTCAAMS-UHFFFAOYSA-N 0.000 claims description 2
• ZALUANUKBRAJFU-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(N4CCC5(CCOC5)C4)c3C(F)(F)F)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(N4CCC5(CCOC5)C4)c3C(F)(F)F)CC2C1)C(F)(F)F ZALUANUKBRAJFU-UHFFFAOYSA-N 0.000 claims description 2
• QWTJUCPZCOIYSO-UHFFFAOYSA-N FC1CCN(CC1)c1c(Cl)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound FC1CCN(CC1)c1c(Cl)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O QWTJUCPZCOIYSO-UHFFFAOYSA-N 0.000 claims description 2
• IYBRDNIYDIMXHU-UHFFFAOYSA-N O=C(ON1C(=O)CCC1=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1 Chemical compound O=C(ON1C(=O)CCC1=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1 IYBRDNIYDIMXHU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• GUPMECCZRLCQFP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(1-methyl-3-phenylpyrazol-4-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1 GUPMECCZRLCQFP-UHFFFAOYSA-N 0.000 claims 2
• AZPAHQURTGHFLI-UHFFFAOYSA-N FC(F)(F)Oc1cc(CN2CCCC2)cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1 Chemical compound FC(F)(F)Oc1cc(CN2CCCC2)cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1 AZPAHQURTGHFLI-UHFFFAOYSA-N 0.000 claims 2
• SKKMNDJFMBCHFI-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound FC1=CC(N2CCOCC2)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O SKKMNDJFMBCHFI-UHFFFAOYSA-N 0.000 claims 1
• WFKVNPVZRPKAPP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-morpholin-4-yl-4-propan-2-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1COCCN1C1=CC(C(C)C)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O WFKVNPVZRPKAPP-UHFFFAOYSA-N 0.000 claims 1
• JVWFRPDSSLUJAL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1COCCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O JVWFRPDSSLUJAL-UHFFFAOYSA-N 0.000 claims 1
• RBLUADGCZMXOAX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-chloro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O RBLUADGCZMXOAX-UHFFFAOYSA-N 0.000 claims 1
• WGCTUGFXQLBHFW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1COCCN1C1=CC(F)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O WGCTUGFXQLBHFW-UHFFFAOYSA-N 0.000 claims 1
• XTJHVWYAYOMXNW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-fluoro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(F)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O XTJHVWYAYOMXNW-UHFFFAOYSA-N 0.000 claims 1
• QKKJXUOPLBNLKW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(CC=3C=CC(=CC=3)C=3C=CC=CC=3)CC2CN1C(=O)ON1C(=O)CCC1=O QKKJXUOPLBNLKW-UHFFFAOYSA-N 0.000 claims 1
• FLEDTRIQUOHVGQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-propan-2-yl-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(C(C)C)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O FLEDTRIQUOHVGQ-UHFFFAOYSA-N 0.000 claims 1
• OVTWKLNUMXQFBT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-(4-acetylpiperazin-1-yl)-4-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 OVTWKLNUMXQFBT-UHFFFAOYSA-N 0.000 claims 1
• BIUAVTIMQQXYJE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-(4-acetylpiperazin-1-yl)-4-fluorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 BIUAVTIMQQXYJE-UHFFFAOYSA-N 0.000 claims 1
• KQCMGWLWNGILNW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-(4-acetylpiperazin-1-yl)-4-propan-2-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(C)=O)CCN1C1=CC(C(C)C)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O KQCMGWLWNGILNW-UHFFFAOYSA-N 0.000 claims 1
• SGECPJNVXUYEGP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-chloro-4-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C(C=C1Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 SGECPJNVXUYEGP-UHFFFAOYSA-N 0.000 claims 1
• DUOMKACOVQCHJX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-fluoro-4-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C(C=C1F)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 DUOMKACOVQCHJX-UHFFFAOYSA-N 0.000 claims 1
• BYILKVNTBJWPED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-(4-acetylpiperazin-1-yl)-2-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(C=C1Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 BYILKVNTBJWPED-UHFFFAOYSA-N 0.000 claims 1
• RMFWBQDASIAUGU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-chloro-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CC2(C(NCC2)=O)CCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O RMFWBQDASIAUGU-UHFFFAOYSA-N 0.000 claims 1
• QLSDIEJHGPBKOU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-chloro-2-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 QLSDIEJHGPBKOU-UHFFFAOYSA-N 0.000 claims 1
• YQJQFUVBLIJOOX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-fluoro-2-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 YQJQFUVBLIJOOX-UHFFFAOYSA-N 0.000 claims 1
• GNEAFYKODSFJMK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound FC(F)(F)OC1=CC(N2CCOCC2)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O GNEAFYKODSFJMK-UHFFFAOYSA-N 0.000 claims 1
• CKADIUGXWLYCHR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-morpholin-4-yl-2-(trifluoromethyl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O CKADIUGXWLYCHR-UHFFFAOYSA-N 0.000 claims 1
• MSKRXEICVNFEMQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[bis(4-chlorophenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 MSKRXEICVNFEMQ-UHFFFAOYSA-N 0.000 claims 1
• YRAQCEMCMKWYJP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(1-ethyl-3-pyridin-2-ylpyrazol-4-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=N1 YRAQCEMCMKWYJP-UHFFFAOYSA-N 0.000 claims 1
• NNJQVPNEFKFUDG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-chloro-3-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C=1Cl)=CC=CC=1N1CCOCC1 NNJQVPNEFKFUDG-UHFFFAOYSA-N 0.000 claims 1
• WBWXAVSISKFMNU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-chloro-4-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C(=C1)Cl)=CC=C1N1CCOCC1 WBWXAVSISKFMNU-UHFFFAOYSA-N 0.000 claims 1
• ZQIRVRDHXCQWEF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-cyclohexyl-5-methylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCCCC1 ZQIRVRDHXCQWEF-UHFFFAOYSA-N 0.000 claims 1
• OOYPIHJULVUGEB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-cyclohexyl-5-propan-2-ylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCCCC1 OOYPIHJULVUGEB-UHFFFAOYSA-N 0.000 claims 1
• DRJAHSSTXNPHMS-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C(F)=CC=1N1CCOCC1 DRJAHSSTXNPHMS-UHFFFAOYSA-N 0.000 claims 1
• VSPCXZZEUGFDAL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-methyl-3-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1N1CCOCC1 VSPCXZZEUGFDAL-UHFFFAOYSA-N 0.000 claims 1
• MEVQYEWUCLPVNX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-methyl-3-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1N1CCCCC1 MEVQYEWUCLPVNX-UHFFFAOYSA-N 0.000 claims 1
• TWPNMNBRTMYDCV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-morpholin-4-yl-4-propan-2-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(C(C)C)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCOCC1 TWPNMNBRTMYDCV-UHFFFAOYSA-N 0.000 claims 1
• HPKSIINLLINMFO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=CC=C1C1=CC=CC=C1 HPKSIINLLINMFO-UHFFFAOYSA-N 0.000 claims 1
• XEHGFXMSMHRUJX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=CC(Cl)=C1N1CCOCC1 XEHGFXMSMHRUJX-UHFFFAOYSA-N 0.000 claims 1
• QFRXYUHUZYXDIR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-methyl-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=CC=CC(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=C1N1CCOCC1 QFRXYUHUZYXDIR-UHFFFAOYSA-N 0.000 claims 1
• FRRIOGDSAYLQBH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-methyl-2-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=CC=CC(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=C1N1CCCCC1 FRRIOGDSAYLQBH-UHFFFAOYSA-N 0.000 claims 1
• HHSUBEJPQGJXKP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-phenyl-1-propan-2-ylpyrazol-4-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1 HHSUBEJPQGJXKP-UHFFFAOYSA-N 0.000 claims 1
• UMYQNJQIJWKSRH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N1CCOCC1 UMYQNJQIJWKSRH-UHFFFAOYSA-N 0.000 claims 1
• ANUGAKABTTXCID-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-chloro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N1CCCC1 ANUGAKABTTXCID-UHFFFAOYSA-N 0.000 claims 1
• BYLBIZIQXNAYTJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(F)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCOCC1 BYLBIZIQXNAYTJ-UHFFFAOYSA-N 0.000 claims 1
• XHFXZXOHRAWDIN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-fluoro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(F)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCCC1 XHFXZXOHRAWDIN-UHFFFAOYSA-N 0.000 claims 1
• YPFURSFOBNHDRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C=C1)=CC=C1C1=CC=CC=C1 YPFURSFOBNHDRO-UHFFFAOYSA-N 0.000 claims 1
• GROSUVLLDKTZMY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(5-methyl-2-propan-2-ylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC(C)N1N=C(C)C=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 GROSUVLLDKTZMY-UHFFFAOYSA-N 0.000 claims 1
• OZTNLWMHWOXZQO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(3-morpholin-4-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=1)=CC=CC=1N1CCOCC1 OZTNLWMHWOXZQO-UHFFFAOYSA-N 0.000 claims 1
• ZRWRFCSMVPWYKY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(3-pyrrolidin-1-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=1)=CC=CC=1N1CCCC1 ZRWRFCSMVPWYKY-UHFFFAOYSA-N 0.000 claims 1
• PFSDNZSZQQDAHC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(4-morpholin-4-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=C1)=CC=C1N1CCOCC1 PFSDNZSZQQDAHC-UHFFFAOYSA-N 0.000 claims 1
• VIEZONNMUIGMMQ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(4-pyrrolidin-1-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=C1)=CC=C1N1CCCC1 VIEZONNMUIGMMQ-UHFFFAOYSA-N 0.000 claims 1
• YOXCLRDXZTYJPZ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(morpholine-4-carbonyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(=O)N1CCOCC1 YOXCLRDXZTYJPZ-UHFFFAOYSA-N 0.000 claims 1
• ZYSXWYSHUIAXLB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-methyl-3-(1-methylsulfonylpiperidin-4-yl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1CCN(S(C)(=O)=O)CC1 ZYSXWYSHUIAXLB-UHFFFAOYSA-N 0.000 claims 1
• GETJHMNSCNZETI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(1-acetylpiperidin-4-yl)-5-methylpyrazol-3-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCC1N1C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=CC(C)=N1 GETJHMNSCNZETI-UHFFFAOYSA-N 0.000 claims 1
• INXUQCMRQHCANI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetamidopiperidin-1-yl)-5-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CC(NC(=O)C)CCN1C1=CC=C(Cl)C=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 INXUQCMRQHCANI-UHFFFAOYSA-N 0.000 claims 1
• RVRCFUYVXYANTH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetylpiperazin-1-yl)-4-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 RVRCFUYVXYANTH-UHFFFAOYSA-N 0.000 claims 1
• CERGHDKYTLVEHR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetylpiperazin-1-yl)-4-fluorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 CERGHDKYTLVEHR-UHFFFAOYSA-N 0.000 claims 1
• SYZQUCNTJQZBBD-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetylpiperazin-1-yl)-4-propan-2-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(C(C)C)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCN(C(C)=O)CC1 SYZQUCNTJQZBBD-UHFFFAOYSA-N 0.000 claims 1
• WAUWECBQOJNYOG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(azetidin-1-yl)-4-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N1CCC1 WAUWECBQOJNYOG-UHFFFAOYSA-N 0.000 claims 1
• CZPMRGQOYYDTSW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(oxan-4-yl)-5-propan-2-ylpyrazol-3-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCOCC1 CZPMRGQOYYDTSW-UHFFFAOYSA-N 0.000 claims 1
• UOAWPMBZAUBMSP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-chloro-3-(2-oxa-7-azaspiro[4.4]nonan-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C=1Cl)=CC=CC=1N(C1)CCC21CCOC2 UOAWPMBZAUBMSP-UHFFFAOYSA-N 0.000 claims 1
• OZHJHXZHOURUFG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-fluoro-4-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C(C=C1F)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 OZHJHXZHOURUFG-UHFFFAOYSA-N 0.000 claims 1
• RUKBGCOYTZBMOW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-methyl-3-(2-oxa-7-azaspiro[4.4]nonan-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1N(C1)CCC21CCOC2 RUKBGCOYTZBMOW-UHFFFAOYSA-N 0.000 claims 1
• XULMSYLPGIXWJY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-morpholin-4-yl-3-(trifluoromethyl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=CC(C(F)(F)F)=C1N1CCOCC1 XULMSYLPGIXWJY-UHFFFAOYSA-N 0.000 claims 1
• VVILSJCMQZTXBQ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(1-acetylpiperidin-4-yl)-1-methylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCC1C1=NN(C)C=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 VVILSJCMQZTXBQ-UHFFFAOYSA-N 0.000 claims 1
• XCZZHWMKUIEVPV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(1-acetylpiperidin-4-yl)-1-propan-2-ylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1CCN(C(C)=O)CC1 XCZZHWMKUIEVPV-UHFFFAOYSA-N 0.000 claims 1
• FRMDPQCIVILBFU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(1-methylsulfonylpiperidin-4-yl)-1-propan-2-ylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1CCN(S(C)(=O)=O)CC1 FRMDPQCIVILBFU-UHFFFAOYSA-N 0.000 claims 1
• WZLWEMBYBYKOGV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(2-chlorophenyl)-1-methylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1Cl WZLWEMBYBYKOGV-UHFFFAOYSA-N 0.000 claims 1
• MLXDDZWTTYHFTP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(2-chlorophenyl)-1-propan-2-ylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1Cl MLXDDZWTTYHFTP-UHFFFAOYSA-N 0.000 claims 1
• TWPJHBLVMSNEDV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(benzylcarbamoyl)-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(=O)NCC1=CC=CC=C1 TWPJHBLVMSNEDV-UHFFFAOYSA-N 0.000 claims 1
• MVOQZBQHCUQEHU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-(cyclopropylcarbamoyl)-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(=O)NC1CC1 MVOQZBQHCUQEHU-UHFFFAOYSA-N 0.000 claims 1
• KTIOKMSYNNIURV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-[2-(azetidin-1-yl)phenyl]-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1N1CCC1 KTIOKMSYNNIURV-UHFFFAOYSA-N 0.000 claims 1
• TTXFQHHMQSORNW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-[3-(azetidin-1-yl)phenyl]-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=1)=CC=CC=1N1CCC1 TTXFQHHMQSORNW-UHFFFAOYSA-N 0.000 claims 1
• IDQHUDZWTOQSTH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-[4-(azetidin-1-yl)phenyl]-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=C1)=CC=C1N1CCC1 IDQHUDZWTOQSTH-UHFFFAOYSA-N 0.000 claims 1
• TXGOQHZATMPXAT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[3-chloro-2-(2-oxa-7-azaspiro[4.4]nonan-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=CC(Cl)=C1N(C1)CCC21CCOC2 TXGOQHZATMPXAT-UHFFFAOYSA-N 0.000 claims 1
• QXBPVSHFQOIZBX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-(4-acetylpiperazin-1-yl)-2-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(C=C1Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 QXBPVSHFQOIZBX-UHFFFAOYSA-N 0.000 claims 1
• XLAJUEQUINWTSX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-(4-acetylpiperazin-1-yl)-2-fluorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(C=C1F)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 XLAJUEQUINWTSX-UHFFFAOYSA-N 0.000 claims 1
• DVHNNGNBGHJJLC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N(CC1)CCC21CCNC2=O DVHNNGNBGHJJLC-UHFFFAOYSA-N 0.000 claims 1
• CGRZGYSARCILPB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 CGRZGYSARCILPB-UHFFFAOYSA-N 0.000 claims 1
• YMLZKWDXFHQGPF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2=CC=CN=C2CN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 YMLZKWDXFHQGPF-UHFFFAOYSA-N 0.000 claims 1
• FZFPMYOMIZBFKT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(6,8-dihydro-5h-[1,2,4]triazolo[1,5-a]pyrazin-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN2N=CN=C2CN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 FZFPMYOMIZBFKT-UHFFFAOYSA-N 0.000 claims 1
• WXBKCSHBUSCAAU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN2C=CN=C2CN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 WXBKCSHBUSCAAU-UHFFFAOYSA-N 0.000 claims 1
• WSGBZTHCIIIMLS-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(8-oxa-2-azaspiro[4.5]decan-2-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N(C1)CCC21CCOCC2 WSGBZTHCIIIMLS-UHFFFAOYSA-N 0.000 claims 1
• AQDDUCJYJACKJZ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C(O2)CCC2CN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 AQDDUCJYJACKJZ-UHFFFAOYSA-N 0.000 claims 1
• CDTHCWZHNLVFLW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-chloro-2-[4-(pyrrolidine-1-carbonyl)piperidin-1-yl]phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=C(Cl)C=C1N(CC1)CCC1C(=O)N1CCCC1 CDTHCWZHNLVFLW-UHFFFAOYSA-N 0.000 claims 1
• GHYNBRUXJXQIEV-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-fluoro-2-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 GHYNBRUXJXQIEV-UHFFFAOYSA-N 0.000 claims 1
• MJQYGNICPKCZQI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C(OC(F)(F)F)=CC=1N1CCOCC1 MJQYGNICPKCZQI-UHFFFAOYSA-N 0.000 claims 1
• KPXASHXWTZABCI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[5-(benzylcarbamoyl)-1-ethylpyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CCN1N=CC(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=C1C(=O)NCC1=CC=CC=C1 KPXASHXWTZABCI-UHFFFAOYSA-N 0.000 claims 1
• VFOLXVWWFUZJMT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[5-chloro-2-[4-(methanesulfonamido)piperidin-1-yl]phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CC(NS(=O)(=O)C)CCN1C1=CC=C(Cl)C=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 VFOLXVWWFUZJMT-UHFFFAOYSA-N 0.000 claims 1
• XMADNOAXJXHINM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[bis(4-chlorophenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XMADNOAXJXHINM-UHFFFAOYSA-N 0.000 claims 1
• BYLUWBFKAHNFLU-UHFFFAOYSA-N 2-[[1-ethyl-3-(prop-2-ynylcarbamoyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CCN1C=C(C(=N1)C(=O)NCC#C)CN2CC3CN(CC3C2)C(=O)O BYLUWBFKAHNFLU-UHFFFAOYSA-N 0.000 claims 1
• GCVJGMIVXOTPMT-UHFFFAOYSA-N 2-[[4-(difluoromethyl)-2-pyrrolidin-1-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1CCN(C1)C2=C(C=CC(=C2)C(F)F)CN3CC4CN(CC4C3)C(=O)O GCVJGMIVXOTPMT-UHFFFAOYSA-N 0.000 claims 1
• HVHCPIMSHYDTAO-UHFFFAOYSA-N 4-(2,5-dioxopyrrolidin-1-yl)-2-[[2-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3F)C(=O)N3CCCC3)CC2C1N1C(=O)CCC1=O HVHCPIMSHYDTAO-UHFFFAOYSA-N 0.000 claims 1
• DXONQFAIAFRRJF-UHFFFAOYSA-N C(C)(=O)NC1CN(C1)C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C=C1)Cl Chemical compound C(C)(=O)NC1CN(C1)C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C=C1)Cl DXONQFAIAFRRJF-UHFFFAOYSA-N 0.000 claims 1
• RZSYJHORVDWSJF-UHFFFAOYSA-N C(C)(C)(C)C1=NN(C(=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1=C(C=CC=C1)Cl Chemical compound C(C)(C)(C)C1=NN(C(=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1=C(C=CC=C1)Cl RZSYJHORVDWSJF-UHFFFAOYSA-N 0.000 claims 1
• YRPQXZPRGGKPGC-UHFFFAOYSA-N C(C)N1N=CC(=C1C(=O)N1CCOCC1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound C(C)N1N=CC(=C1C(=O)N1CCOCC1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F YRPQXZPRGGKPGC-UHFFFAOYSA-N 0.000 claims 1
• RDDTVGVPXBDYFQ-UHFFFAOYSA-N C(C)N1N=CC(=C1C(NC1CCOCC1)=O)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound C(C)N1N=CC(=C1C(NC1CCOCC1)=O)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F RDDTVGVPXBDYFQ-UHFFFAOYSA-N 0.000 claims 1
• DEJXUBLPXFOMAV-UHFFFAOYSA-N C(C)N1N=CC(=C1C(NCC1CCOCC1)=O)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound C(C)N1N=CC(=C1C(NCC1CCOCC1)=O)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F DEJXUBLPXFOMAV-UHFFFAOYSA-N 0.000 claims 1
• UBJRGUVLQUMIDM-UHFFFAOYSA-N C1(CC1)NC(=O)C1=C(C=NN1CC)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound C1(CC1)NC(=O)C1=C(C=NN1CC)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F UBJRGUVLQUMIDM-UHFFFAOYSA-N 0.000 claims 1
• SYLUENBACIBLHA-UHFFFAOYSA-N C1OCC2C1CN(C2)C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)C(F)(F)F Chemical compound C1OCC2C1CN(C2)C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)C(F)(F)F SYLUENBACIBLHA-UHFFFAOYSA-N 0.000 claims 1
• MNSKIBSAXCOHEX-UHFFFAOYSA-N CC(=O)N1CC2(C1)CCN(C2)c1ccccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound CC(=O)N1CC2(C1)CCN(C2)c1ccccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F MNSKIBSAXCOHEX-UHFFFAOYSA-N 0.000 claims 1
• CHXXOVYXYKOTMK-UHFFFAOYSA-N CC(=O)N1CCC(CC1)c1nn(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CC(=O)N1CCC(CC1)c1nn(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O CHXXOVYXYKOTMK-UHFFFAOYSA-N 0.000 claims 1
• DFVNPJQZDBKXTG-UHFFFAOYSA-N CC(=O)N1CCC(CC1)n1nc(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CC(=O)N1CCC(CC1)n1nc(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O DFVNPJQZDBKXTG-UHFFFAOYSA-N 0.000 claims 1
• BPUBFNFQPDMMCM-UHFFFAOYSA-N CC(=O)N1CCC2(CCN(C2)c2ccccc2CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1 Chemical compound CC(=O)N1CCC2(CCN(C2)c2ccccc2CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1 BPUBFNFQPDMMCM-UHFFFAOYSA-N 0.000 claims 1
• BVNHJLIJPARIQL-UHFFFAOYSA-N CC(=O)N1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C Chemical compound CC(=O)N1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C BVNHJLIJPARIQL-UHFFFAOYSA-N 0.000 claims 1
• NWKRATJSTAZGHG-UHFFFAOYSA-N CC(=O)N1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1C Chemical compound CC(=O)N1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1C NWKRATJSTAZGHG-UHFFFAOYSA-N 0.000 claims 1
• JASJSPDQSZJWQE-UHFFFAOYSA-N CC(=O)NC1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1C Chemical compound CC(=O)NC1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1C JASJSPDQSZJWQE-UHFFFAOYSA-N 0.000 claims 1
• QBKYONMHOLMPKO-UHFFFAOYSA-N CC(C)(C)c1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)C1CCOCC1 Chemical compound CC(C)(C)c1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)C1CCOCC1 QBKYONMHOLMPKO-UHFFFAOYSA-N 0.000 claims 1
• XIVFGCVYCUATLZ-UHFFFAOYSA-N CC(C)c1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)n(n1)C1CCCCC1 Chemical compound CC(C)c1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)n(n1)C1CCCCC1 XIVFGCVYCUATLZ-UHFFFAOYSA-N 0.000 claims 1
• YQCIKTQPDAVDSS-UHFFFAOYSA-N CC(C)c1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)n(n1)C1CCOCC1 Chemical compound CC(C)c1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)n(n1)C1CCOCC1 YQCIKTQPDAVDSS-UHFFFAOYSA-N 0.000 claims 1
• UHGKMCPHDBUXCP-UHFFFAOYSA-N CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1cccc(Cl)c1 Chemical compound CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1cccc(Cl)c1 UHGKMCPHDBUXCP-UHFFFAOYSA-N 0.000 claims 1
• DXTYTNQVHMMDKU-UHFFFAOYSA-N CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1 Chemical compound CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1 DXTYTNQVHMMDKU-UHFFFAOYSA-N 0.000 claims 1
• RRZNUXWSZAVPNE-UHFFFAOYSA-N CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1Cl Chemical compound CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1Cl RRZNUXWSZAVPNE-UHFFFAOYSA-N 0.000 claims 1
• NMZNVNVEUDQUHS-UHFFFAOYSA-N CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)C1CCN(CC1)C(C)=O Chemical compound CC(C)n1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)C1CCN(CC1)C(C)=O NMZNVNVEUDQUHS-UHFFFAOYSA-N 0.000 claims 1
• FTKMBTWHXULSOK-UHFFFAOYSA-N CC(C)n1nc(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CC(C)n1nc(C)cc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O FTKMBTWHXULSOK-UHFFFAOYSA-N 0.000 claims 1
• MNMHXVLOIKWQRV-UHFFFAOYSA-N CC1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1C(=O)N1CCCCC1 Chemical compound CC1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1C(=O)N1CCCCC1 MNMHXVLOIKWQRV-UHFFFAOYSA-N 0.000 claims 1
• DMHWPJXLNJDWKW-UHFFFAOYSA-N CC1=CC=C(C=C1C1=CC=CC=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound CC1=CC=C(C=C1C1=CC=CC=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F DMHWPJXLNJDWKW-UHFFFAOYSA-N 0.000 claims 1
• OVOMQSJIMDAZFW-UHFFFAOYSA-N CCN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound CCN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F OVOMQSJIMDAZFW-UHFFFAOYSA-N 0.000 claims 1
• WMYXZOHGCQVJEK-UHFFFAOYSA-N CCN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CCN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O WMYXZOHGCQVJEK-UHFFFAOYSA-N 0.000 claims 1
• FCPJKRSNDRBVQG-UHFFFAOYSA-N CCN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C Chemical compound CCN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C FCPJKRSNDRBVQG-UHFFFAOYSA-N 0.000 claims 1
• FHTFKUFBHRUVFW-UHFFFAOYSA-N CCN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC2C(=O)CCC2=O)c1C Chemical compound CCN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC2C(=O)CCC2=O)c1C FHTFKUFBHRUVFW-UHFFFAOYSA-N 0.000 claims 1
• ODKWUTKJIDYQRF-UHFFFAOYSA-N CCc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)-c1ccccc1Cl Chemical compound CCc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)-c1ccccc1Cl ODKWUTKJIDYQRF-UHFFFAOYSA-N 0.000 claims 1
• JATDGBDAMOBKAW-UHFFFAOYSA-N CCc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)C1CCOCC1 Chemical compound CCc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)n(n1)C1CCOCC1 JATDGBDAMOBKAW-UHFFFAOYSA-N 0.000 claims 1
• MNMLODISMNINDA-UHFFFAOYSA-N CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccc(cc1)N1CCCCC1 Chemical compound CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccc(cc1)N1CCCCC1 MNMLODISMNINDA-UHFFFAOYSA-N 0.000 claims 1
• KMONKCHJSASZDA-UHFFFAOYSA-N CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1cccc(c1)N1CCCCC1 Chemical compound CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1cccc(c1)N1CCCCC1 KMONKCHJSASZDA-UHFFFAOYSA-N 0.000 claims 1
• BLAJADABSUKRBX-UHFFFAOYSA-N CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccccc1N1CCCCC1 Chemical compound CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccccc1N1CCCCC1 BLAJADABSUKRBX-UHFFFAOYSA-N 0.000 claims 1
• JXBTWPULJMGWPM-UHFFFAOYSA-N CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccccc1N1CCOCC1 Chemical compound CCn1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c(n1)-c1ccccc1N1CCOCC1 JXBTWPULJMGWPM-UHFFFAOYSA-N 0.000 claims 1
• QAVKFYVVYPDOER-UHFFFAOYSA-N CN1CCN(CC1)C(=O)c1ccc(CN2CC3CN(C(C3C2)N2C(=O)CCC2=O)C(O)=O)c(Cl)c1 Chemical compound CN1CCN(CC1)C(=O)c1ccc(CN2CC3CN(C(C3C2)N2C(=O)CCC2=O)C(O)=O)c(Cl)c1 QAVKFYVVYPDOER-UHFFFAOYSA-N 0.000 claims 1
• ZAYNYZHBQOSGFI-UHFFFAOYSA-N CN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F Chemical compound CN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F ZAYNYZHBQOSGFI-UHFFFAOYSA-N 0.000 claims 1
• RTPZFBRQWOMQPX-UHFFFAOYSA-N CN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound CN1CCN(CC1)c1c(C)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O RTPZFBRQWOMQPX-UHFFFAOYSA-N 0.000 claims 1
• VUIXREFOAFEAPS-UHFFFAOYSA-N CN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C Chemical compound CN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1C VUIXREFOAFEAPS-UHFFFAOYSA-N 0.000 claims 1
• QABYOPQMCCTNLZ-UHFFFAOYSA-N CN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC2C(=O)CCC2=O)c1C Chemical compound CN1CCN(CC1)c1cccc(CN2CC3CN(CC3C2)C(=O)OC2C(=O)CCC2=O)c1C QABYOPQMCCTNLZ-UHFFFAOYSA-N 0.000 claims 1
• SHGDQUDFFVUGST-UHFFFAOYSA-N CN1N=C(C(=C1)CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C2=CC=CC=C2 Chemical compound CN1N=C(C(=C1)CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C2=CC=CC=C2 SHGDQUDFFVUGST-UHFFFAOYSA-N 0.000 claims 1
• QDPZCGJGXAQCOI-UHFFFAOYSA-N CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=2C=C(C=CC2)C Chemical compound CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=2C=C(C=CC2)C QDPZCGJGXAQCOI-UHFFFAOYSA-N 0.000 claims 1
• ILSPQYWWMKBXRY-UHFFFAOYSA-N CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C2=CC=CC=C2 Chemical compound CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C2=CC=CC=C2 ILSPQYWWMKBXRY-UHFFFAOYSA-N 0.000 claims 1
• WAADFNZUJOUIFD-UHFFFAOYSA-N CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C=2C=C(C=CC2)C Chemical compound CN1N=C(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C=2C=C(C=CC2)C WAADFNZUJOUIFD-UHFFFAOYSA-N 0.000 claims 1
• BMGLXXVIMSSRDY-UHFFFAOYSA-N CNC(=O)C(OC(=O)N1CC2CN(CC2C1)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1)C(F)(F)F Chemical compound CNC(=O)C(OC(=O)N1CC2CN(CC2C1)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1)C(F)(F)F BMGLXXVIMSSRDY-UHFFFAOYSA-N 0.000 claims 1
• XBGAAYBVCYKSEY-UHFFFAOYSA-N CS(=O)(=O)N1CCC(CC1)C1=NN(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C(C)C Chemical compound CS(=O)(=O)N1CCC(CC1)C1=NN(C=C1CN1CC2C(C1)CN(C2)C(=O)ON2C(CCC2=O)=O)C(C)C XBGAAYBVCYKSEY-UHFFFAOYSA-N 0.000 claims 1
• CFTHYTUAJKTPIO-UHFFFAOYSA-N CS(=O)(=O)N1CCC2(CCN(C2)c2ccccc2CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1 Chemical compound CS(=O)(=O)N1CCC2(CCN(C2)c2ccccc2CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C1 CFTHYTUAJKTPIO-UHFFFAOYSA-N 0.000 claims 1
• VEOXHCYMTQEWJR-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)cccc1N1CCC(CC1)NS(C)(=O)=O Chemical compound Cc1c(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)cccc1N1CCC(CC1)NS(C)(=O)=O VEOXHCYMTQEWJR-UHFFFAOYSA-N 0.000 claims 1
• ZDJWWCWZWDNPNM-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)cccc1N1CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)cccc1N1CCN(CC1)S(C)(=O)=O ZDJWWCWZWDNPNM-UHFFFAOYSA-N 0.000 claims 1
• WEKWGUXFNWPRAM-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCC(CC1)NS(C)(=O)=O Chemical compound Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCC(CC1)NS(C)(=O)=O WEKWGUXFNWPRAM-UHFFFAOYSA-N 0.000 claims 1
• BKUGHAIWCRPYRD-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCC(F)(F)CC1 Chemical compound Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCC(F)(F)CC1 BKUGHAIWCRPYRD-UHFFFAOYSA-N 0.000 claims 1
• URMGXBVWRAZWMU-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCN(CC1)S(C)(=O)=O Chemical compound Cc1c(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)cccc1N1CCN(CC1)S(C)(=O)=O URMGXBVWRAZWMU-UHFFFAOYSA-N 0.000 claims 1
• JUUYLYGPPBZVFT-UHFFFAOYSA-N Cc1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1N1CCC2(CCOC2)C1 Chemical compound Cc1cccc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)c1N1CCC2(CCOC2)C1 JUUYLYGPPBZVFT-UHFFFAOYSA-N 0.000 claims 1
• AVLPKHNDVNDYOC-UHFFFAOYSA-N Cc1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1N1CCCCC1 Chemical compound Cc1cccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c1N1CCCCC1 AVLPKHNDVNDYOC-UHFFFAOYSA-N 0.000 claims 1
• MULUKBVAKQBQKU-UHFFFAOYSA-N ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CC3C(C1)COC3 Chemical compound ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CC3C(C1)COC3 MULUKBVAKQBQKU-UHFFFAOYSA-N 0.000 claims 1
• MGEXBXBZWKQDFN-FAFZWHIHSA-N ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1C[C@@H]2N(CC1)CCC2 Chemical compound ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1C[C@@H]2N(CC1)CCC2 MGEXBXBZWKQDFN-FAFZWHIHSA-N 0.000 claims 1
• UBDKPWCQXXXCFY-UHFFFAOYSA-N ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=C1)N1CC=2N(CC1)N=CN=2 Chemical compound ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=C1)N1CC=2N(CC1)N=CN=2 UBDKPWCQXXXCFY-UHFFFAOYSA-N 0.000 claims 1
• YWCWVVHYULMLAP-GZNCHQMQSA-N ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)ON3C(CCC3=O)=O)C=C1)N1C[C@@H]3N(CC1)CCC3 Chemical compound ClC1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)ON3C(CCC3=O)=O)C=C1)N1C[C@@H]3N(CC1)CCC3 YWCWVVHYULMLAP-GZNCHQMQSA-N 0.000 claims 1
• IBTAYNCNUDKUCS-UHFFFAOYSA-N ClC=1C(=C(C=CC1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N2CC1(CC2)CCOCC1 Chemical compound ClC=1C(=C(C=CC1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N2CC1(CC2)CCOCC1 IBTAYNCNUDKUCS-UHFFFAOYSA-N 0.000 claims 1
• CQQXADPTIFZTKE-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCC(CC1)F Chemical compound ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCC(CC1)F CQQXADPTIFZTKE-UHFFFAOYSA-N 0.000 claims 1
• KUDDJSVWSVAISZ-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCN(CC1)C Chemical compound ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCN(CC1)C KUDDJSVWSVAISZ-UHFFFAOYSA-N 0.000 claims 1
• RDOPZPZOSOHXKO-IUDNXUCKSA-N ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C[C@H](CC1)CF Chemical compound ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C[C@H](CC1)CF RDOPZPZOSOHXKO-IUDNXUCKSA-N 0.000 claims 1
• XFGVTIDYZIGQSJ-UHFFFAOYSA-N Clc1cc(ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O)C(=O)N1CCCCC1 Chemical compound Clc1cc(ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O)C(=O)N1CCCCC1 XFGVTIDYZIGQSJ-UHFFFAOYSA-N 0.000 claims 1
• KVUAMUFSOPPQQK-UHFFFAOYSA-N Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC1 Chemical compound Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC1 KVUAMUFSOPPQQK-UHFFFAOYSA-N 0.000 claims 1
• SABPILITLNIOKZ-UHFFFAOYSA-N Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC2(C1)CCOCC2 Chemical compound Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1CCC2(C1)CCOCC2 SABPILITLNIOKZ-UHFFFAOYSA-N 0.000 claims 1
• SPAZHRICOJJUBI-UHFFFAOYSA-N Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1Cc2cccnc2C1 Chemical compound Clc1ccc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(c1)N1Cc2cccnc2C1 SPAZHRICOJJUBI-UHFFFAOYSA-N 0.000 claims 1
• GMCLQTMGVKLSNU-UHFFFAOYSA-N Cn1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1Cl Chemical compound Cn1cc(CN2CC3CN(CC3C2)C(=O)ON2C(=O)CCC2=O)c(n1)-c1ccccc1Cl GMCLQTMGVKLSNU-UHFFFAOYSA-N 0.000 claims 1
• BLZJYKJIETXILH-UHFFFAOYSA-N Cn1nc(cc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F)-c1ccccc1 Chemical compound Cn1nc(cc1CN1CC2CN(CC2C1)C(=O)OC(C(F)(F)F)C(F)(F)F)-c1ccccc1 BLZJYKJIETXILH-UHFFFAOYSA-N 0.000 claims 1
• DKVAJIOKVGRXGR-UHFFFAOYSA-N FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCCC1)F Chemical compound FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCCC1)F DKVAJIOKVGRXGR-UHFFFAOYSA-N 0.000 claims 1
• XXTZPSBHSIVPGC-UHFFFAOYSA-N FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCCCC1)F Chemical compound FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCCCC1)F XXTZPSBHSIVPGC-UHFFFAOYSA-N 0.000 claims 1
• XZTFFRRCFBBPGP-UHFFFAOYSA-N FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCOCC1)F Chemical compound FC(C1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC(=C1)N1CCOCC1)F XZTFFRRCFBBPGP-UHFFFAOYSA-N 0.000 claims 1
• UNTXNMZSKCBWAU-UHFFFAOYSA-N FC(C1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CCCCC1)F Chemical compound FC(C1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CCCCC1)F UNTXNMZSKCBWAU-UHFFFAOYSA-N 0.000 claims 1
• GSGDERHQXRVCGD-UHFFFAOYSA-N FC(C1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CCOCC1)F Chemical compound FC(C1=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)N1CCOCC1)F GSGDERHQXRVCGD-UHFFFAOYSA-N 0.000 claims 1
• KFHPRWOJMOMPCA-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3ccc(Cl)cc3)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3ccc(Cl)cc3)CC2C1)C(F)(F)F KFHPRWOJMOMPCA-UHFFFAOYSA-N 0.000 claims 1
• CMJNRHVBKMGVHP-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3)CC2C1)C(F)(F)F CMJNRHVBKMGVHP-UHFFFAOYSA-N 0.000 claims 1
• BLXNDUBEHGJFHF-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3C4CCC3COC4)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3C4CCC3COC4)CC2C1)C(F)(F)F BLXNDUBEHGJFHF-UHFFFAOYSA-N 0.000 claims 1
• QINSDTSAJNBMAB-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)(F)CC3)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)(F)CC3)CC2C1)C(F)(F)F QINSDTSAJNBMAB-UHFFFAOYSA-N 0.000 claims 1
• GITJBFIWRVWUSS-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(N4CCOCC4)c3C(F)(F)F)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(N4CCOCC4)c3C(F)(F)F)CC2C1)C(F)(F)F GITJBFIWRVWUSS-UHFFFAOYSA-N 0.000 claims 1
• XGIPKPKBHNEYIE-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1)C(F)(F)F XGIPKPKBHNEYIE-UHFFFAOYSA-N 0.000 claims 1
• ATEFTWVRPBIKII-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3ccccc3Cl)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3ccccc3Cl)CC2C1)C(F)(F)F ATEFTWVRPBIKII-UHFFFAOYSA-N 0.000 claims 1
• KRWCEPGUUDJMFD-UHFFFAOYSA-N FC(F)(F)Oc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)ccc1C(=O)N1CCCCC1 Chemical compound FC(F)(F)Oc1cc(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)ccc1C(=O)N1CCCCC1 KRWCEPGUUDJMFD-UHFFFAOYSA-N 0.000 claims 1
• DXABLJQFTDCLDF-UHFFFAOYSA-N FC1(CCN(CC1)C=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C)F Chemical compound FC1(CCN(CC1)C=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C)F DXABLJQFTDCLDF-UHFFFAOYSA-N 0.000 claims 1
• WGJAUVPQVDTBJO-UHFFFAOYSA-N FC=1C=C(C=CC1)C1=NN(C(=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C Chemical compound FC=1C=C(C=CC1)C1=NN(C(=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C WGJAUVPQVDTBJO-UHFFFAOYSA-N 0.000 claims 1
• CZKCZTYYHVLRCY-UHFFFAOYSA-N N1(CCCC1)C(=O)C1=C(C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)OC(F)(F)F Chemical compound N1(CCCC1)C(=O)C1=C(C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C1)OC(F)(F)F CZKCZTYYHVLRCY-UHFFFAOYSA-N 0.000 claims 1
• FJWFZJSNXRFJOS-UHFFFAOYSA-N N1(CCCC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1)OC(F)(F)F Chemical compound N1(CCCC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1)OC(F)(F)F FJWFZJSNXRFJOS-UHFFFAOYSA-N 0.000 claims 1
• IZTFQIPJSXBPRU-UHFFFAOYSA-N N1(CCCCC1)CC=1C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C=1)OC(F)(F)F Chemical compound N1(CCCCC1)CC=1C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C=1)OC(F)(F)F IZTFQIPJSXBPRU-UHFFFAOYSA-N 0.000 claims 1
• LSKSXDABALWWIV-UHFFFAOYSA-N N1(CCCCC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C1)OC(F)(F)F Chemical compound N1(CCCCC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C1)OC(F)(F)F LSKSXDABALWWIV-UHFFFAOYSA-N 0.000 claims 1
• WZQCEOGJHUGEHM-UHFFFAOYSA-N N1(CCOCC1)C1=CC(=C(C=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C(F)(F)F Chemical compound N1(CCOCC1)C1=CC(=C(C=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C(F)(F)F WZQCEOGJHUGEHM-UHFFFAOYSA-N 0.000 claims 1
• GJUOKDLHGFEBEZ-UHFFFAOYSA-N O1CCN(CC1)CC=1C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C1)OC(F)(F)F Chemical compound O1CCN(CC1)CC=1C=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=C(C1)OC(F)(F)F GJUOKDLHGFEBEZ-UHFFFAOYSA-N 0.000 claims 1
• BIWMECIYASRQLE-UHFFFAOYSA-N O1CCN(CC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1)OC(F)(F)F Chemical compound O1CCN(CC1)CC=1C=CC(=C(CN2CC3C(C2)CN(C3)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1)OC(F)(F)F BIWMECIYASRQLE-UHFFFAOYSA-N 0.000 claims 1
• FEVSSZNCGPNGMC-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCC3)CC2C1N1C(=O)CCC1=O Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCC3)CC2C1N1C(=O)CCC1=O FEVSSZNCGPNGMC-UHFFFAOYSA-N 0.000 claims 1
• BSNVGDZCZDPSGR-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCOCC3)CC2C1N1C(=O)CCC1=O Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCOCC3)CC2C1N1C(=O)CCC1=O BSNVGDZCZDPSGR-UHFFFAOYSA-N 0.000 claims 1
• YENLEPUEEKNXEW-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3F)C(=O)N3CCC3)CC2C1N1C(=O)CCC1=O Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3F)C(=O)N3CCC3)CC2C1N1C(=O)CCC1=O YENLEPUEEKNXEW-UHFFFAOYSA-N 0.000 claims 1
• LJHSHKCEWYIMTM-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3F)C(=O)N3CCCCC3)CC2C1N1C(=O)CCC1=O Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3F)C(=O)N3CCCCC3)CC2C1N1C(=O)CCC1=O LJHSHKCEWYIMTM-UHFFFAOYSA-N 0.000 claims 1
• BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 abstract description 10
• 101000929834 Homo sapiens Monoacylglycerol lipase ABHD6 Proteins 0.000 abstract description 9
• 102100035912 Monoacylglycerol lipase ABHD6 Human genes 0.000 abstract description 9
• 230000000694 effects Effects 0.000 abstract description 9
• 102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 abstract description 6
• 150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 6
• 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 abstract 1
• 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 abstract 1
• 102100029814 Monoglyceride lipase Human genes 0.000 abstract 1
• 101710116393 Monoglyceride lipase Proteins 0.000 abstract 1
• 238000003556 assay Methods 0.000 abstract 1
• DDLIQEWTNHONBH-UHFFFAOYSA-N carbamic acid;1h-pyrrole Chemical class NC(O)=O.C=1C=CNC=1 DDLIQEWTNHONBH-UHFFFAOYSA-N 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 149
• 235000002639 sodium chloride Nutrition 0.000 description 76
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 72
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
• 238000005160 1H NMR spectroscopy Methods 0.000 description 54
• 125000002947 alkylene group Chemical group 0.000 description 49
• 239000002904 solvent Substances 0.000 description 46
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 44
• 239000003921 oil Substances 0.000 description 43
• 235000019198 oils Nutrition 0.000 description 43
• 238000002360 preparation method Methods 0.000 description 40
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 125000004432 carbon atom Chemical group C* 0.000 description 34
• 239000000243 solution Substances 0.000 description 34
• 150000002431 hydrogen Chemical class 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• 239000003814 drug Substances 0.000 description 28
• 239000007787 solid Substances 0.000 description 28
• 239000000126 substance Substances 0.000 description 27
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
• FYUVLZRRIRGSTE-UHFFFAOYSA-N tert-butyl 2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1NCC2CN(C(=O)OC(C)(C)C)CC21 FYUVLZRRIRGSTE-UHFFFAOYSA-N 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 239000002585 base Substances 0.000 description 24
• 150000003254 radicals Chemical group 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• 125000004452 carbocyclyl group Chemical group 0.000 description 19
• 229940124597 therapeutic agent Drugs 0.000 description 19
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 18
• 208000035473 Communicable disease Diseases 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• 150000001299 aldehydes Chemical class 0.000 description 17
• 125000003709 fluoroalkyl group Chemical group 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 16
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
• 239000003795 chemical substances by application Substances 0.000 description 15
• 235000019441 ethanol Nutrition 0.000 description 15
• UVGYSEIWAOOIJR-UHFFFAOYSA-N 4-chloro-2-fluorobenzaldehyde Chemical compound FC1=CC(Cl)=CC=C1C=O UVGYSEIWAOOIJR-UHFFFAOYSA-N 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 102000005398 Monoacylglycerol Lipase Human genes 0.000 description 14
• 108020002334 Monoacylglycerol lipase Proteins 0.000 description 14
• 238000011282 treatment Methods 0.000 description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• 125000005884 carbocyclylalkyl group Chemical group 0.000 description 13
• 125000004122 cyclic group Chemical group 0.000 description 13
• 239000000543 intermediate Substances 0.000 description 13
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 12
• 201000010099 disease Diseases 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• 230000001225 therapeutic effect Effects 0.000 description 12
• 125000004450 alkenylene group Chemical group 0.000 description 11
• 230000008901 benefit Effects 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• RCRCTBLIHCHWDZ-UHFFFAOYSA-N 2-Arachidonoyl Glycerol Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 229910052799 carbon Inorganic materials 0.000 description 10
• 125000005843 halogen group Chemical group 0.000 description 10
• 229910052701 rubidium Inorganic materials 0.000 description 10
• 238000006467 substitution reaction Methods 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 10
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 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 8
• 239000002253 acid Substances 0.000 description 8
• 239000004480 active ingredient Substances 0.000 description 8
• 125000002619 bicyclic group Chemical group 0.000 description 8
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• 150000002429 hydrazines Chemical class 0.000 description 8
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 244000201986 Cassia tora Species 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 150000002430 hydrocarbons Chemical class 0.000 description 7
• NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 229910052705 radium Inorganic materials 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 125000003107 substituted aryl group Chemical group 0.000 description 7
• WCGPCBACLBHDCI-UHFFFAOYSA-N 2,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(F)=C1 WCGPCBACLBHDCI-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 208000035143 Bacterial infection Diseases 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 150000001502 aryl halides Chemical class 0.000 description 6
• 230000001580 bacterial effect Effects 0.000 description 6
• 208000022362 bacterial infectious disease Diseases 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 229930195733 hydrocarbon Natural products 0.000 description 6
• 239000002808 molecular sieve Substances 0.000 description 6
• 239000002674 ointment Substances 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 239000003208 petroleum Substances 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 235000011181 potassium carbonates Nutrition 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 238000006722 reduction reaction Methods 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
• PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 5
• 239000000443 aerosol Substances 0.000 description 5
• 230000001476 alcoholic effect Effects 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 230000009286 beneficial effect Effects 0.000 description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 238000002648 combination therapy Methods 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 108010046094 fatty-acid amide hydrolase Proteins 0.000 description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 230000004770 neurodegeneration Effects 0.000 description 5
• 239000001301 oxygen Chemical group 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000000377 silicon dioxide Substances 0.000 description 5
• 239000012279 sodium borohydride Substances 0.000 description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 description 5
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 238000007920 subcutaneous administration Methods 0.000 description 5
• 239000000829 suppository Substances 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
• UGQAXUDFJWQPHM-UHFFFAOYSA-N 2-oxa-7-azaspiro[4.4]nonane Chemical compound C1NCCC11COCC1 UGQAXUDFJWQPHM-UHFFFAOYSA-N 0.000 description 4
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 208000019901 Anxiety disease Diseases 0.000 description 4
• 239000004215 Carbon black (E152) Substances 0.000 description 4
• 241000282414 Homo sapiens Species 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 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
• 241001465754 Metazoa Species 0.000 description 4
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
• 150000001200 N-acyl ethanolamides Chemical class 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 150000001499 aryl bromides Chemical class 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 229920002301 cellulose acetate Polymers 0.000 description 4
• 208000010877 cognitive disease Diseases 0.000 description 4
• 229920001577 copolymer Polymers 0.000 description 4
• 239000006071 cream Substances 0.000 description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 239000002621 endocannabinoid Substances 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 238000007918 intramuscular administration Methods 0.000 description 4
• 238000001990 intravenous administration Methods 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 239000002207 metabolite Substances 0.000 description 4
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
• 201000001119 neuropathy Diseases 0.000 description 4
• 230000007823 neuropathy Effects 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 208000033808 peripheral neuropathy Diseases 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 150000003217 pyrazoles Chemical class 0.000 description 4
• 239000000376 reactant Substances 0.000 description 4
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 230000000707 stereoselective effect Effects 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• 239000006188 syrup Substances 0.000 description 4
• 235000020357 syrup Nutrition 0.000 description 4
• 239000000454 talc Substances 0.000 description 4
• 235000012222 talc Nutrition 0.000 description 4
• 229910052623 talc Inorganic materials 0.000 description 4
• 238000010626 work up procedure Methods 0.000 description 4
• 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 3
• 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 3
• QKZVBSSZYNPGCZ-UHFFFAOYSA-N 2-[(4-chloro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1CCN(C1)C2=C(C=CC(=C2)Cl)CN3CC4CN(CC4C3)C(=O)O QKZVBSSZYNPGCZ-UHFFFAOYSA-N 0.000 description 3
• YAOZCMANASAVFN-UHFFFAOYSA-N 3-chloro-2-fluorobenzaldehyde Chemical compound FC1=C(Cl)C=CC=C1C=O YAOZCMANASAVFN-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• VVYOBIMAYCZOOE-UHFFFAOYSA-N C(C)(C)(C)OC(NC1CCN(CC1)C1=C(C=C(C=C1)Cl)C=O)=O Chemical compound C(C)(C)(C)OC(NC1CCN(CC1)C1=C(C=C(C=C1)Cl)C=O)=O VVYOBIMAYCZOOE-UHFFFAOYSA-N 0.000 description 3
• 241000242722 Cestoda Species 0.000 description 3
• 208000000094 Chronic Pain Diseases 0.000 description 3
• 208000028698 Cognitive impairment Diseases 0.000 description 3
• 206010009944 Colon cancer Diseases 0.000 description 3
• 239000007821 HATU Substances 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• 102000004157 Hydrolases Human genes 0.000 description 3
• 108090000604 Hydrolases Proteins 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• 235000019502 Orange oil Nutrition 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• 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 3
• 229930006000 Sucrose Natural products 0.000 description 3
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 3
• 241000242541 Trematoda Species 0.000 description 3
• 238000010521 absorption reaction Methods 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 235000010443 alginic acid Nutrition 0.000 description 3
• 229920000615 alginic acid Polymers 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• 125000004419 alkynylene group Chemical group 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 3
• 150000005840 aryl radicals Chemical class 0.000 description 3
• 235000012216 bentonite Nutrition 0.000 description 3
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
• PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
• 229910000024 caesium carbonate Inorganic materials 0.000 description 3
• 125000002837 carbocyclic group Chemical group 0.000 description 3
• 150000001718 carbodiimides Chemical class 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 3
• 238000000576 coating method Methods 0.000 description 3
• 239000012230 colorless oil Substances 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 238000010511 deprotection reaction Methods 0.000 description 3
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 150000004677 hydrates Chemical class 0.000 description 3
• 238000011065 in-situ storage Methods 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 230000002401 inhibitory effect Effects 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• 230000000670 limiting effect Effects 0.000 description 3
• 239000006210 lotion Substances 0.000 description 3
• 201000001441 melanoma Diseases 0.000 description 3
• 230000015654 memory Effects 0.000 description 3
• 239000010502 orange oil Substances 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 239000006072 paste Substances 0.000 description 3
• 235000015320 potassium carbonate Nutrition 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000003380 propellant Substances 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• 125000003373 pyrazinyl group Chemical group 0.000 description 3
• BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 3
• 229910052702 rhenium Inorganic materials 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 230000007781 signaling event Effects 0.000 description 3
• 235000012239 silicon dioxide Nutrition 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 208000011580 syndromic disease Diseases 0.000 description 3
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 238000004809 thin layer chromatography Methods 0.000 description 3
• 125000000464 thioxo group Chemical group S=* 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
• 230000009466 transformation Effects 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• NMFQPFSIPWZZMR-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropan-2-ol Chemical compound FC(F)C(F)(O)C(F)(F)F NMFQPFSIPWZZMR-UHFFFAOYSA-N 0.000 description 2
• LKBJQRZQDCMBBJ-UHFFFAOYSA-N 1-chloro-4-[chloro-(4-chlorophenyl)methyl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(Cl)C1=CC=C(Cl)C=C1 LKBJQRZQDCMBBJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• HDJKUPICCDVIEB-UHFFFAOYSA-N 2-[(2-chloro-4-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=CC(=C(C=C2)CN3CC4CN(CC4C3)C(=O)O)Cl HDJKUPICCDVIEB-UHFFFAOYSA-N 0.000 description 2
• UWICRDKMDROWON-UHFFFAOYSA-N 2-[(3-methyl-2-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CC1=C(C(=CC=C1)CN2CC3CN(CC3C2)C(=O)O)N4CCCCC4 UWICRDKMDROWON-UHFFFAOYSA-N 0.000 description 2
• LZDLJDUHSYJHOX-UHFFFAOYSA-N 2-[(4-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=C(C=CC(=C2)Cl)CN3CC4CN(CC4C3)C(=O)O LZDLJDUHSYJHOX-UHFFFAOYSA-N 0.000 description 2
• SKUARWYQCHAPCH-UHFFFAOYSA-N 2-[(4-fluoro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1CCN(C1)C2=C(C=CC(=C2)F)CN3CC4CN(CC4C3)C(=O)O SKUARWYQCHAPCH-UHFFFAOYSA-N 0.000 description 2
• JGAPWTQYJBKINM-UHFFFAOYSA-N 2-[[2-fluoro-4-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CC1COCCN1C2=CC(=C(C=C2)CN3CC4CN(CC4C3)C(=O)O)F JGAPWTQYJBKINM-UHFFFAOYSA-N 0.000 description 2
• LOEUFGNGEIEILM-UHFFFAOYSA-N 2-[[5-chloro-2-[4-(methanesulfonamido)piperidin-1-yl]phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CS(=O)(=O)NC1CCN(CC1)C2=C(C=C(C=C2)Cl)CN3CC4CN(CC4C3)C(=O)O LOEUFGNGEIEILM-UHFFFAOYSA-N 0.000 description 2
• VTYCJXMPNYVBSZ-UHFFFAOYSA-N 2-bromo-4-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=C(C=O)C(Br)=C1 VTYCJXMPNYVBSZ-UHFFFAOYSA-N 0.000 description 2
• PIZVRLVKXWEMGO-UHFFFAOYSA-N 2-chloro-3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1Cl PIZVRLVKXWEMGO-UHFFFAOYSA-N 0.000 description 2
• KMQWNQKESAHDKD-UHFFFAOYSA-N 2-chloro-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(Cl)=C1 KMQWNQKESAHDKD-UHFFFAOYSA-N 0.000 description 2
• CERGYJCALDGESV-UHFFFAOYSA-N 2-fluoro-3-methylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1F CERGYJCALDGESV-UHFFFAOYSA-N 0.000 description 2
• LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 2
• HSUCYMJBFHBMTB-UHFFFAOYSA-N 3-fluoro-2-methylbenzaldehyde Chemical compound CC1=C(F)C=CC=C1C=O HSUCYMJBFHBMTB-UHFFFAOYSA-N 0.000 description 2
• MSOCQCWIEBVSLF-UHFFFAOYSA-N 3-methylmorpholin-4-ium;chloride Chemical compound Cl.CC1COCCN1 MSOCQCWIEBVSLF-UHFFFAOYSA-N 0.000 description 2
• SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 2
• ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• 241000505629 Amoebozoa Species 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• 241000223836 Babesia Species 0.000 description 2
• 208000008035 Back Pain Diseases 0.000 description 2
• 241001284802 Bertiella <tapeworm> Species 0.000 description 2
• VKSUMQQYQGUABN-UHFFFAOYSA-N CC1COCCN1c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(O)=O Chemical compound CC1COCCN1c1cc(Cl)ccc1CN1CC2CN(CC2C1)C(O)=O VKSUMQQYQGUABN-UHFFFAOYSA-N 0.000 description 2
• DFQJXVHOYURMOT-UHFFFAOYSA-N CC1COCCN1c1cc(F)ccc1CN1CC2CN(CC2C1)C(O)=O Chemical compound CC1COCCN1c1cc(F)ccc1CN1CC2CN(CC2C1)C(O)=O DFQJXVHOYURMOT-UHFFFAOYSA-N 0.000 description 2
• MNGUDLBKKVNSPW-UHFFFAOYSA-N CC1COCCN1c1ccc(CN2CC3CN(CC3C2)C(O)=O)c(Cl)c1 Chemical compound CC1COCCN1c1ccc(CN2CC3CN(CC3C2)C(O)=O)c(Cl)c1 MNGUDLBKKVNSPW-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 102000018208 Cannabinoid Receptor Human genes 0.000 description 2
• 108050007331 Cannabinoid receptor Proteins 0.000 description 2
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
• 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
• 241000606161 Chlamydia Species 0.000 description 2
• 241001327942 Clonorchis Species 0.000 description 2
• 241001327965 Clonorchis sinensis Species 0.000 description 2
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 2
• 206010010904 Convulsion Diseases 0.000 description 2
• 241000186216 Corynebacterium Species 0.000 description 2
• 229920000858 Cyclodextrin Polymers 0.000 description 2
• 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 2
• 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 2
• 208000020401 Depressive disease Diseases 0.000 description 2
• 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
• 241000224432 Entamoeba histolytica Species 0.000 description 2
• 241000498256 Enterobius Species 0.000 description 2
• SHUXOXNWKQUOHB-UHFFFAOYSA-N FC1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C)(C)C)C=CC(=C1)N1CCOCC1 Chemical compound FC1=C(CN2CC3C(C2)CN(C3)C(=O)OC(C)(C)C)C=CC(=C1)N1CCOCC1 SHUXOXNWKQUOHB-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 239000007818 Grignard reagent Substances 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 206010065390 Inflammatory pain Diseases 0.000 description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 description 2
• 208000008930 Low Back Pain Diseases 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• 201000009906 Meningitis Diseases 0.000 description 2
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 241000186359 Mycobacterium Species 0.000 description 2
• 241000204031 Mycoplasma Species 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• 241000588653 Neisseria Species 0.000 description 2
• 241000244206 Nematoda Species 0.000 description 2
• KIIIHUBVKVPYFH-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(F)cc3N3CCOCC3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3ccc(F)cc3N3CCOCC3)CC2C1 KIIIHUBVKVPYFH-UHFFFAOYSA-N 0.000 description 2
• DZVOJFPNKWVRSH-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1 DZVOJFPNKWVRSH-UHFFFAOYSA-N 0.000 description 2
• ZGSRZTWPGZPATA-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3F)N3CCOCC3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3F)N3CCOCC3)CC2C1 ZGSRZTWPGZPATA-UHFFFAOYSA-N 0.000 description 2
• 208000021155 Paediatric autoimmune neuropsychiatric disorders associated with streptococcal infection Diseases 0.000 description 2
• 241001480233 Paragonimus Species 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
• 206010060862 Prostate cancer Diseases 0.000 description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
• 241000606701 Rickettsia Species 0.000 description 2
• 241000224003 Sarcocystis Species 0.000 description 2
• 206010040070 Septic Shock Diseases 0.000 description 2
• 208000004078 Snake Bites Diseases 0.000 description 2
• 241000244031 Toxocara Species 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 2
• 206010047700 Vomiting Diseases 0.000 description 2
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
• 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 229940024606 amino acid Drugs 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 230000036506 anxiety Effects 0.000 description 2
• 239000003125 aqueous solvent Substances 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• 201000008680 babesiosis Diseases 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 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
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
• 239000011230 binding agent Substances 0.000 description 2
• 239000003124 biologic agent Substances 0.000 description 2
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
• 210000004556 brain Anatomy 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 229930003827 cannabinoid Natural products 0.000 description 2
• 239000003557 cannabinoid Substances 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 230000001149 cognitive effect Effects 0.000 description 2
• 208000029742 colonic neoplasm Diseases 0.000 description 2
• 208000010247 contact dermatitis Diseases 0.000 description 2
• 238000006880 cross-coupling reaction Methods 0.000 description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 description 2
• 125000002993 cycloalkylene group Chemical group 0.000 description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 229940097362 cyclodextrins Drugs 0.000 description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 230000001419 dependent effect Effects 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
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
• 229940038472 dicalcium phosphate Drugs 0.000 description 2
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
• 235000014113 dietary fatty acids Nutrition 0.000 description 2
• 239000008298 dragée Substances 0.000 description 2
• 210000001198 duodenum Anatomy 0.000 description 2
• 229940007078 entamoeba histolytica Drugs 0.000 description 2
• 206010015037 epilepsy Diseases 0.000 description 2
• 230000008029 eradication Effects 0.000 description 2
• 239000000194 fatty acid Substances 0.000 description 2
• 229930195729 fatty acid Natural products 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• 239000000499 gel Substances 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
• 150000004795 grignard reagents Chemical class 0.000 description 2
• 244000000013 helminth Species 0.000 description 2
• OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 230000003301 hydrolyzing effect Effects 0.000 description 2
• 150000004679 hydroxides Chemical class 0.000 description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
• 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 2
• 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 2
• 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 description 2
• 210000003405 ileum Anatomy 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
• 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 2
• 239000003701 inert diluent Substances 0.000 description 2
• 238000001802 infusion Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 238000010253 intravenous injection Methods 0.000 description 2
• 210000001630 jejunum Anatomy 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• 229940067606 lecithin Drugs 0.000 description 2
• 150000002632 lipids Chemical class 0.000 description 2
• 238000004811 liquid chromatography Methods 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 208000030159 metabolic disease Diseases 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 238000006241 metabolic reaction Methods 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
• 238000000465 moulding Methods 0.000 description 2
• 210000000653 nervous system Anatomy 0.000 description 2
• 239000012457 nonaqueous media Substances 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 201000008482 osteoarthritis Diseases 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 150000002923 oximes Chemical class 0.000 description 2
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
• 230000008058 pain sensation Effects 0.000 description 2
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 230000001717 pathogenic effect Effects 0.000 description 2
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
• 230000000704 physical effect Effects 0.000 description 2
• 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 230000000069 prophylactic effect Effects 0.000 description 2
• 229960004063 propylene glycol Drugs 0.000 description 2
• 150000003180 prostaglandins Chemical class 0.000 description 2
• 208000020016 psychiatric disease Diseases 0.000 description 2
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 239000007909 solid dosage form Substances 0.000 description 2
• 239000008247 solid mixture Substances 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 235000010356 sorbitol Nutrition 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 229940032147 starch Drugs 0.000 description 2
• 210000002784 stomach Anatomy 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 150000008163 sugars Chemical class 0.000 description 2
• 229940124530 sulfonamide Drugs 0.000 description 2
• 150000003456 sulfonamides Chemical class 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000004094 surface-active agent Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 235000010487 tragacanth Nutrition 0.000 description 2
• 239000000196 tragacanth Substances 0.000 description 2
• 229940116362 tragacanth Drugs 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-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
• WRRSFOZOETZUPG-FFHNEAJVSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC WRRSFOZOETZUPG-FFHNEAJVSA-N 0.000 description 1
• FTTATHOUSOIFOQ-SSDOTTSWSA-N (8ar)-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCC[C@@H]21 FTTATHOUSOIFOQ-SSDOTTSWSA-N 0.000 description 1
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 1
• 125000006313 (C5-C8) alkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 1
• JZKWRGMHEXSNDT-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl carbonochloridate Chemical class FC(F)(F)C(C(F)(F)F)OC(Cl)=O JZKWRGMHEXSNDT-UHFFFAOYSA-N 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
• ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 description 1
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
• ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 description 1
• WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
• HHIOFHJYOIVJJK-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCNCC1 HHIOFHJYOIVJJK-UHFFFAOYSA-N 0.000 description 1
• QVYUOZBXTACBNA-UHFFFAOYSA-N 2-[(2-chloro-3-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=CC=CC(=C2Cl)CN3CC4CN(CC4C3)C(=O)O QVYUOZBXTACBNA-UHFFFAOYSA-N 0.000 description 1
• ILBZNFOLVMDKEF-UHFFFAOYSA-N 2-[(2-methyl-3-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CC1=C(C=CC=C1N2CCCCC2)CN3CC4CN(CC4C3)C(=O)O ILBZNFOLVMDKEF-UHFFFAOYSA-N 0.000 description 1
• QIPNFSOPLGRYPV-UHFFFAOYSA-N 2-[(2-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1C2CN(CC2CN1CC3=CC=CC=C3C4=CC=CC=C4)C(=O)O QIPNFSOPLGRYPV-UHFFFAOYSA-N 0.000 description 1
• KVTLRECSXKRHFZ-UHFFFAOYSA-N 2-[(3-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=C(C=CC=C2Cl)CN3CC4CN(CC4C3)C(=O)O KVTLRECSXKRHFZ-UHFFFAOYSA-N 0.000 description 1
• UETNTEQEEIQLSB-UHFFFAOYSA-N 2-[(3-methyl-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CC1=C(C(=CC=C1)CN2CC3CN(CC3C2)C(=O)O)N4CCOCC4 UETNTEQEEIQLSB-UHFFFAOYSA-N 0.000 description 1
• IYWSMPAQJXJILQ-UHFFFAOYSA-N 2-[[1-ethyl-3-(2-piperidin-1-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CCN1C=C(C(=N1)C2=CC=CC=C2N3CCCCC3)CN4CC5CN(CC5C4)C(=O)O IYWSMPAQJXJILQ-UHFFFAOYSA-N 0.000 description 1
• VPHDTTADJXXHGI-UHFFFAOYSA-N 2-[[2-(difluoromethyl)-4-morpholin-4-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=CC(=C(C=C2)CN3CC4CN(CC4C3)C(=O)O)C(F)F VPHDTTADJXXHGI-UHFFFAOYSA-N 0.000 description 1
• MGRGKGZSPSBCOR-UHFFFAOYSA-N 2-[[2-methyl-3-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CC1=C(C=CC=C1N2C3CCC2COC3)CN4CC5CN(CC5C4)C(=O)O MGRGKGZSPSBCOR-UHFFFAOYSA-N 0.000 description 1
• ZKPAPMSLXSBQDD-UHFFFAOYSA-N 2-[[3-(morpholin-4-ylmethyl)-5-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1CC2=CC(=CC(=C2)OC(F)(F)F)CN3CC4CN(CC4C3)C(=O)O ZKPAPMSLXSBQDD-UHFFFAOYSA-N 0.000 description 1
• PXPRDDPEZRJHHZ-UHFFFAOYSA-N 2-[[3-(piperidin-1-ylmethyl)-5-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1CCN(CC1)CC2=CC(=CC(=C2)OC(F)(F)F)CN3CC4CN(CC4C3)C(=O)O PXPRDDPEZRJHHZ-UHFFFAOYSA-N 0.000 description 1
• JKDVYSWMRGOHCW-UHFFFAOYSA-N 2-[[3-chloro-2-(4-methylpiperazin-1-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound CN1CCN(CC1)C2=C(C=CC=C2Cl)CN3CC4CN(CC4C3)C(=O)O JKDVYSWMRGOHCW-UHFFFAOYSA-N 0.000 description 1
• ZSNGNCUQXRYKQR-UHFFFAOYSA-N 2-[[4-(difluoromethyl)-2-morpholin-4-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1COCCN1C2=C(C=CC(=C2)C(F)F)CN3CC4CN(CC4C3)C(=O)O ZSNGNCUQXRYKQR-UHFFFAOYSA-N 0.000 description 1
• VYERBIOYUARZQB-UHFFFAOYSA-N 2-[[5-(piperidin-1-ylmethyl)-2-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1CCN(CC1)CC2=CC(=C(C=C2)OC(F)(F)F)CN3CC4CN(CC4C3)C(=O)O VYERBIOYUARZQB-UHFFFAOYSA-N 0.000 description 1
• CYQUDJGXCABLPN-UHFFFAOYSA-N 2-bromo-3-methylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1Br CYQUDJGXCABLPN-UHFFFAOYSA-N 0.000 description 1
• NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical class BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
• ANDFLRNDOCVCFM-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylbenzaldehyde Chemical compound C1=C(C=O)C(Cl)=CC(N2CCOCC2)=C1 ANDFLRNDOCVCFM-UHFFFAOYSA-N 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• XDMZVNQKVMTCSP-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzaldehyde Chemical compound FC1=C(C=O)C=CC=C1C(F)(F)F XDMZVNQKVMTCSP-UHFFFAOYSA-N 0.000 description 1
• UEKCASSBRLOEDR-UHFFFAOYSA-N 2-fluoro-4-morpholin-4-ylbenzaldehyde Chemical compound C1=C(C=O)C(F)=CC(N2CCOCC2)=C1 UEKCASSBRLOEDR-UHFFFAOYSA-N 0.000 description 1
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
• JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
• 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• 125000006088 2-oxoazepinyl group Chemical group 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
• LGCYVLDNGBSOOW-UHFFFAOYSA-N 2H-benzotriazol-4-ol 1-hydroxybenzotriazole Chemical compound OC1=CC=CC2=C1N=NN2.C1=CC=C2N(O)N=NC2=C1 LGCYVLDNGBSOOW-UHFFFAOYSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• HHVUFPUWPWOWOA-UHFFFAOYSA-N 3-bromo-2-methylbenzaldehyde Chemical compound CC1=C(Br)C=CC=C1C=O HHVUFPUWPWOWOA-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
• ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
• MNILDQSRDHCFJG-UHFFFAOYSA-N 3-oxa-8-azabicyclo[3.2.1]octane Chemical compound C1OCC2CCC1N2 MNILDQSRDHCFJG-UHFFFAOYSA-N 0.000 description 1
• KFKSIUOALVIACE-UHFFFAOYSA-N 3-phenylbenzaldehyde Chemical compound O=CC1=CC=CC(C=2C=CC=CC=2)=C1 KFKSIUOALVIACE-UHFFFAOYSA-N 0.000 description 1
• PHUYGURFBULKPA-UHFFFAOYSA-N 4,4'-dichlorobenzhydrol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1=CC=C(Cl)C=C1 PHUYGURFBULKPA-UHFFFAOYSA-N 0.000 description 1
• AXZVKHIUQLEMPJ-UHFFFAOYSA-N 4-bromo-2-(trifluoromethoxy)benzaldehyde Chemical compound FC(F)(F)OC1=CC(Br)=CC=C1C=O AXZVKHIUQLEMPJ-UHFFFAOYSA-N 0.000 description 1
• MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
• NONOHEMDNFTKCZ-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC=C(C=O)C(C(F)(F)F)=C1 NONOHEMDNFTKCZ-UHFFFAOYSA-N 0.000 description 1
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
• DXJKRLHHCGXHMB-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound C1NCCN2N=CN=C21 DXJKRLHHCGXHMB-UHFFFAOYSA-N 0.000 description 1
• SWBUHQQTIPEPMK-UHFFFAOYSA-N 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Chemical compound C1NCCN2C=CN=C21 SWBUHQQTIPEPMK-UHFFFAOYSA-N 0.000 description 1
• WDTUCEMLUHTMCB-UHFFFAOYSA-N 5-chloro-2-fluorobenzaldehyde Chemical compound FC1=CC=C(Cl)C=C1C=O WDTUCEMLUHTMCB-UHFFFAOYSA-N 0.000 description 1
• SJMNQXLXIIXDDS-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-b]pyridine Chemical compound C1=CC=C2CNCC2=N1 SJMNQXLXIIXDDS-UHFFFAOYSA-N 0.000 description 1
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
• JVBOTGLQUHBBCV-UHFFFAOYSA-N 8-oxa-2-azaspiro[4.5]decane Chemical compound C1NCCC21CCOCC2 JVBOTGLQUHBBCV-UHFFFAOYSA-N 0.000 description 1
• POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 208000037415 AIDS wasting syndrome Diseases 0.000 description 1
• 208000004998 Abdominal Pain Diseases 0.000 description 1
• 241000224422 Acanthamoeba Species 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 241000589291 Acinetobacter Species 0.000 description 1
• 241000588626 Acinetobacter baumannii Species 0.000 description 1
• 208000009304 Acute Kidney Injury Diseases 0.000 description 1
• 208000008811 Agoraphobia Diseases 0.000 description 1
• 241001036151 Aichi virus 1 Species 0.000 description 1
• 208000003130 Alcoholic Neuropathy Diseases 0.000 description 1
• 241000388165 Alphapapillomavirus 4 Species 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
• 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
• 241000498253 Ancylostoma duodenale Species 0.000 description 1
• UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
• 241000359199 Angiostrongylus costaricensis Species 0.000 description 1
• 241000244023 Anisakis Species 0.000 description 1
• 235000003276 Apios tuberosa Nutrition 0.000 description 1
• YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 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
• 241000700607 Archiacanthocephala Species 0.000 description 1
• 208000006820 Arthralgia Diseases 0.000 description 1
• 206010003399 Arthropod bite Diseases 0.000 description 1
• 241000244186 Ascaris Species 0.000 description 1
• 241000244185 Ascaris lumbricoides Species 0.000 description 1
• 241000228212 Aspergillus Species 0.000 description 1
• 241000228193 Aspergillus clavatus Species 0.000 description 1
• 241000228197 Aspergillus flavus Species 0.000 description 1
• 241001225321 Aspergillus fumigatus Species 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 241000295638 Australian bat lyssavirus Species 0.000 description 1
• 241000223840 Babesia bigemina Species 0.000 description 1
• 241001455947 Babesia divergens Species 0.000 description 1
• 241001648338 Babesia duncani Species 0.000 description 1
• 241000193830 Bacillus <bacterium> Species 0.000 description 1
• 241000193738 Bacillus anthracis Species 0.000 description 1
• 241000606125 Bacteroides Species 0.000 description 1
• 241000606124 Bacteroides fragilis Species 0.000 description 1
• 241000934146 Balamuthia mandrillaris Species 0.000 description 1
• 241001235572 Balantioides coli Species 0.000 description 1
• 241001302512 Banna virus Species 0.000 description 1
• 241000710946 Barmah Forest virus Species 0.000 description 1
• 241000244183 Baylisascaris procyonis Species 0.000 description 1
• 241001284800 Bertiella studeri Species 0.000 description 1
• 206010005003 Bladder cancer Diseases 0.000 description 1
• 241000726108 Blastocystis Species 0.000 description 1
• 241000588807 Bordetella Species 0.000 description 1
• 241000588832 Bordetella pertussis Species 0.000 description 1
• 241000589968 Borrelia Species 0.000 description 1
• 241000589969 Borreliella burgdorferi Species 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 241000589562 Brucella Species 0.000 description 1
• 241000589567 Brucella abortus Species 0.000 description 1
• 241001509299 Brucella canis Species 0.000 description 1
• 241001148106 Brucella melitensis Species 0.000 description 1
• 241001148111 Brucella suis Species 0.000 description 1
• 241000244036 Brugia Species 0.000 description 1
• 241000244038 Brugia malayi Species 0.000 description 1
• 241000143302 Brugia timori Species 0.000 description 1
• 208000032841 Bulimia Diseases 0.000 description 1
• 206010006550 Bulimia nervosa Diseases 0.000 description 1
• 241001493154 Bunyamwera virus Species 0.000 description 1
• 206010070237 Burning feet syndrome 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
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• SCQRNGOXZFNDJG-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C(C=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C)(C)C Chemical compound C1(=CC=CC=C1)C1=CC=C(C=C1)CN1CC2C(C1)CN(C2)C(=O)OC(C)(C)C SCQRNGOXZFNDJG-UHFFFAOYSA-N 0.000 description 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
• WSBTYIKTJFFJLR-ONEGZZNKSA-N CON(C)C(=O)\C=C\[N+]([O-])=O Chemical compound CON(C)C(=O)\C=C\[N+]([O-])=O WSBTYIKTJFFJLR-ONEGZZNKSA-N 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 241000589876 Campylobacter Species 0.000 description 1
• 241000589875 Campylobacter jejuni Species 0.000 description 1
• 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
• 241000222122 Candida albicans Species 0.000 description 1
• 241000282465 Canis Species 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• 241001156781 Carpediemonas Species 0.000 description 1
• 208000001387 Causalgia Diseases 0.000 description 1
• 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
• DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• 241000711969 Chandipura virus Species 0.000 description 1
• 206010008479 Chest Pain Diseases 0.000 description 1
• 241001502567 Chikungunya virus Species 0.000 description 1
• 201000005019 Chlamydia pneumonia Diseases 0.000 description 1
• 241001647378 Chlamydia psittaci Species 0.000 description 1
• 241000606153 Chlamydia trachomatis Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
• 241000193163 Clostridioides difficile Species 0.000 description 1
• 241000193403 Clostridium Species 0.000 description 1
• 241000193155 Clostridium botulinum Species 0.000 description 1
• 241000193468 Clostridium perfringens Species 0.000 description 1
• 241000193449 Clostridium tetani Species 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
• 239000004859 Copal Substances 0.000 description 1
• OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 241000700626 Cowpox virus Species 0.000 description 1
• 241000709687 Coxsackievirus Species 0.000 description 1
• 241000150230 Crimean-Congo hemorrhagic fever orthonairovirus Species 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• 201000007336 Cryptococcosis Diseases 0.000 description 1
• 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
• 241001522864 Cryptococcus gattii VGI Species 0.000 description 1
• 241000221204 Cryptococcus neoformans Species 0.000 description 1
• 201000003808 Cystic echinococcosis Diseases 0.000 description 1
• 206010063057 Cystitis noninfective Diseases 0.000 description 1
• 241000205707 Cystoisospora belli Species 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
• 206010012289 Dementia Diseases 0.000 description 1
• 241000725619 Dengue virus Species 0.000 description 1
• 241000702421 Dependoparvovirus Species 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• 241000202828 Dermatobia hominis Species 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 241000712471 Dhori virus Species 0.000 description 1
• 241000577456 Dicrocoelium dendriticum Species 0.000 description 1
• 241000157306 Dientamoeba fragilis Species 0.000 description 1
• 241000690786 Dioctophyme renale Species 0.000 description 1
• 241000866683 Diphyllobothrium latum Species 0.000 description 1
• 241000243988 Dirofilaria immitis Species 0.000 description 1
• 241001319090 Dracunculus medinensis Species 0.000 description 1
• 241000149824 Dugbe orthonairovirus Species 0.000 description 1
• 241001520695 Duvenhage lyssavirus Species 0.000 description 1
• 208000032928 Dyslipidaemia Diseases 0.000 description 1
• 208000005171 Dysmenorrhea Diseases 0.000 description 1
• 208000030814 Eating disease Diseases 0.000 description 1
• 241001115402 Ebolavirus Species 0.000 description 1
• 241000244160 Echinococcus Species 0.000 description 1
• 241000244170 Echinococcus granulosus Species 0.000 description 1
• 241000244163 Echinococcus multilocularis Species 0.000 description 1
• 241000244162 Echinococcus oligarthrus Species 0.000 description 1
• 241000244165 Echinococcus vogeli Species 0.000 description 1
• 241001126301 Echinostoma Species 0.000 description 1
• 241001466953 Echovirus Species 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 241000710188 Encephalomyocarditis virus Species 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• 208000037487 Endotoxemia Diseases 0.000 description 1
• 208000004232 Enteritis Diseases 0.000 description 1
• 241000588914 Enterobacter Species 0.000 description 1
• 241000588697 Enterobacter cloacae Species 0.000 description 1
• 241000498255 Enterobius vermicularis Species 0.000 description 1
• 241000194033 Enterococcus Species 0.000 description 1
• 241000194032 Enterococcus faecalis Species 0.000 description 1
• 241000194031 Enterococcus faecium Species 0.000 description 1
• 241000991587 Enterovirus C Species 0.000 description 1
• 241000146324 Enterovirus D68 Species 0.000 description 1
• 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• 241000588722 Escherichia Species 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
• 229920003143 Eudragit® FS 30 D Polymers 0.000 description 1
• 229920003139 Eudragit® L 100 Polymers 0.000 description 1
• 229920003138 Eudragit® L 30 D-55 Polymers 0.000 description 1
• 229920003141 Eudragit® S 100 Polymers 0.000 description 1
• 241001520680 European bat lyssavirus Species 0.000 description 1
• TZGFGABNIIASMV-UHFFFAOYSA-N FC=1C=C(C=CC1CN1CC2CNCC2C1)N1CCOCC1 Chemical compound FC=1C=C(C=CC1CN1CC2CNCC2C1)N1CCOCC1 TZGFGABNIIASMV-UHFFFAOYSA-N 0.000 description 1
• 241000204939 Fasciola gigantica Species 0.000 description 1
• 241000242711 Fasciola hepatica Species 0.000 description 1
• 241001126302 Fasciolopsis buski Species 0.000 description 1
• 208000019454 Feeding and Eating disease Diseases 0.000 description 1
• 241000282324 Felis Species 0.000 description 1
• 241000239183 Filaria Species 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
• 241000589601 Francisella Species 0.000 description 1
• 241000589602 Francisella tularensis Species 0.000 description 1
• 241000531123 GB virus C Species 0.000 description 1
• 241000207202 Gardnerella Species 0.000 description 1
• 241000207201 Gardnerella vaginalis Species 0.000 description 1
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• 241000224466 Giardia Species 0.000 description 1
• 241000224467 Giardia intestinalis Species 0.000 description 1
• 208000010412 Glaucoma Diseases 0.000 description 1
• 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 1
• 239000004471 Glycine Substances 0.000 description 1
• 241000880292 Gnathostoma Species 0.000 description 1
• 241000497087 Gnathostoma hispidum Species 0.000 description 1
• 241001276383 Gnathostoma spinigerum Species 0.000 description 1
• 241000782205 Guibourtia conjugata Species 0.000 description 1
• 208000003577 HIV wasting syndrome Diseases 0.000 description 1
• 241000243974 Haemonchus contortus Species 0.000 description 1
• 241000606790 Haemophilus Species 0.000 description 1
• 241000606768 Haemophilus influenzae Species 0.000 description 1
• 241000196812 Halicephalobus gingivalis Species 0.000 description 1
• 241000150562 Hantaan orthohantavirus Species 0.000 description 1
• 206010019233 Headaches Diseases 0.000 description 1
• 241000589989 Helicobacter Species 0.000 description 1
• 241000590002 Helicobacter pylori Species 0.000 description 1
• 241000893570 Hendra henipavirus Species 0.000 description 1
• 241000711549 Hepacivirus C Species 0.000 description 1
• 241000700721 Hepatitis B virus Species 0.000 description 1
• 241000724675 Hepatitis E virus Species 0.000 description 1
• 241000724709 Hepatitis delta virus Species 0.000 description 1
• 241000709721 Hepatovirus A Species 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 241000228402 Histoplasma Species 0.000 description 1
• 241000228404 Histoplasma capsulatum Species 0.000 description 1
• 101000989653 Homo sapiens Membrane frizzled-related protein Proteins 0.000 description 1
• 101100151951 Homo sapiens SARS1 gene Proteins 0.000 description 1
• 241000928771 Horsepox virus Species 0.000 description 1
• 244000309467 Human Coronavirus Species 0.000 description 1
• 241000598436 Human T-cell lymphotropic virus Species 0.000 description 1
• 241000598171 Human adenovirus sp. Species 0.000 description 1
• 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
• 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
• 241000701085 Human alphaherpesvirus 3 Species 0.000 description 1
• 241001479210 Human astrovirus Species 0.000 description 1
• 241000701024 Human betaherpesvirus 5 Species 0.000 description 1
• 241000701041 Human betaherpesvirus 7 Species 0.000 description 1
• 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
• 241001502974 Human gammaherpesvirus 8 Species 0.000 description 1
• 241000701027 Human herpesvirus 6 Species 0.000 description 1
• 241000725303 Human immunodeficiency virus Species 0.000 description 1
• 241000711920 Human orthopneumovirus Species 0.000 description 1
• 241000701806 Human papillomavirus Species 0.000 description 1
• 241000702617 Human parvovirus B19 Species 0.000 description 1
• 241000829111 Human polyomavirus 1 Species 0.000 description 1
• 241000829106 Human polyomavirus 3 Species 0.000 description 1
• 241000430519 Human rhinovirus sp. Species 0.000 description 1
• 241000714192 Human spumaretrovirus Species 0.000 description 1
• 241000947839 Human torovirus Species 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 241000404582 Hymenolepis <angiosperm> Species 0.000 description 1
• 241000244166 Hymenolepis diminuta Species 0.000 description 1
• 241001464384 Hymenolepis nana Species 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 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
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
• 241000712431 Influenza A virus Species 0.000 description 1
• 241000713196 Influenza B virus Species 0.000 description 1
• 241000713297 Influenza C virus Species 0.000 description 1
• 208000006877 Insect Bites and Stings Diseases 0.000 description 1
• 208000005615 Interstitial Cystitis Diseases 0.000 description 1
• 241001109688 Isfahan virus Species 0.000 description 1
• 206010023076 Isosporiasis Diseases 0.000 description 1
• 241000701460 JC polyomavirus Species 0.000 description 1
• 241000710842 Japanese encephalitis virus Species 0.000 description 1
• 241000712890 Junin mammarenavirus Species 0.000 description 1
• 241000588748 Klebsiella Species 0.000 description 1
• 241000588915 Klebsiella aerogenes Species 0.000 description 1
• 201000008225 Klebsiella pneumonia Diseases 0.000 description 1
• 241000588747 Klebsiella pneumoniae Species 0.000 description 1
• 241000710912 Kunjin virus Species 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
• 241000713102 La Crosse virus Species 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 241001520693 Lagos bat lyssavirus Species 0.000 description 1
• 241000710770 Langat virus Species 0.000 description 1
• 241000712902 Lassa mammarenavirus Species 0.000 description 1
• 241000589248 Legionella Species 0.000 description 1
• 241000589242 Legionella pneumophila Species 0.000 description 1
• 208000007764 Legionnaires' Disease Diseases 0.000 description 1
• 241000222722 Leishmania <genus> Species 0.000 description 1
• 241000222727 Leishmania donovani Species 0.000 description 1
• 241000589902 Leptospira Species 0.000 description 1
• 241000589929 Leptospira interrogans Species 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 description 1
• 241001541121 Linguatula Species 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• 241000186781 Listeria Species 0.000 description 1
• 241000186779 Listeria monocytogenes Species 0.000 description 1
• 239000012448 Lithium borohydride Substances 0.000 description 1
• 241000255640 Loa loa Species 0.000 description 1
• 241001635205 Lordsdale virus Species 0.000 description 1
• 241000710769 Louping ill virus Species 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 208000016604 Lyme disease Diseases 0.000 description 1
• 241000712899 Lymphocytic choriomeningitis mammarenavirus Species 0.000 description 1
• 241000712898 Machupo mammarenavirus Species 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241001559185 Mammalian rubulavirus 5 Species 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 241000022705 Mansonella streptocerca Species 0.000 description 1
• 241000711937 Marburg marburgvirus Species 0.000 description 1
• 241000608292 Mayaro virus Species 0.000 description 1
• 241000712079 Measles morbillivirus Species 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
• 102100029357 Membrane frizzled-related protein Human genes 0.000 description 1
• 241000710185 Mengo virus Species 0.000 description 1
• 241000579048 Merkel cell polyomavirus Species 0.000 description 1
• 241001660194 Metagonimus yokogawai Species 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 208000019695 Migraine disease Diseases 0.000 description 1
• 241000725171 Mokola lyssavirus Species 0.000 description 1
• 241000700560 Molluscum contagiosum virus Species 0.000 description 1
• 241000700602 Moniliformis moniliformis Species 0.000 description 1
• 241000700627 Monkeypox virus Species 0.000 description 1
• 206010028116 Mucosal inflammation Diseases 0.000 description 1
• 201000010927 Mucositis Diseases 0.000 description 1
• 241000711386 Mumps virus Species 0.000 description 1
• 241000358374 Mupapillomavirus 1 Species 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 241000710908 Murray Valley encephalitis virus Species 0.000 description 1
• 208000023178 Musculoskeletal disease Diseases 0.000 description 1
• 241000186362 Mycobacterium leprae Species 0.000 description 1
• 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
• 241000187917 Mycobacterium ulcerans Species 0.000 description 1
• 208000001572 Mycoplasma Pneumonia Diseases 0.000 description 1
• 241000204048 Mycoplasma hominis Species 0.000 description 1
• 201000008235 Mycoplasma pneumoniae pneumonia Diseases 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
• 239000007832 Na2SO4 Substances 0.000 description 1
• 241000224438 Naegleria fowleri Species 0.000 description 1
• 241001443590 Naganishia albida Species 0.000 description 1
• 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 1
• 206010028813 Nausea Diseases 0.000 description 1
• 241000498270 Necator americanus Species 0.000 description 1
• 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
• 208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 1
• 206010029279 Neurogenic bladder Diseases 0.000 description 1
• 208000036110 Neuroinflammatory disease Diseases 0.000 description 1
• 241000168432 New York hantavirus Species 0.000 description 1
• 229910005883 NiSi Inorganic materials 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• 241000526636 Nipah henipavirus Species 0.000 description 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
• 241000714209 Norwalk virus Species 0.000 description 1
• 241000710944 O'nyong-nyong virus Species 0.000 description 1
• ADKXPELRORWUPE-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3cc(CN4CCOCC4)ccc3OC(F)(F)F)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3cc(CN4CCOCC4)ccc3OC(F)(F)F)CC2C1 ADKXPELRORWUPE-UHFFFAOYSA-N 0.000 description 1
• ZOORWKMUSFZLHE-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCCCC3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3Cl)C(=O)N3CCCCC3)CC2C1 ZOORWKMUSFZLHE-UHFFFAOYSA-N 0.000 description 1
• OKYIRGBNBYXQGN-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)(F)CC3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)(F)CC3)CC2C1 OKYIRGBNBYXQGN-UHFFFAOYSA-N 0.000 description 1
• XZKUOPGHYLMYOJ-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)CC3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CCC(F)CC3)CC2C1 XZKUOPGHYLMYOJ-UHFFFAOYSA-N 0.000 description 1
• HYVDGUASZWCTID-IUDNXUCKSA-N OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CC[C@H](CF)C3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3cccc(Cl)c3N3CC[C@H](CF)C3)CC2C1 HYVDGUASZWCTID-IUDNXUCKSA-N 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 102100027069 Odontogenic ameloblast-associated protein Human genes 0.000 description 1
• 101710091533 Odontogenic ameloblast-associated protein Proteins 0.000 description 1
• 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
• 241000158589 Oestroidea Species 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 241000243985 Onchocerca volvulus Species 0.000 description 1
• 241000242716 Opisthorchis Species 0.000 description 1
• 241001324821 Opisthorchis felineus Species 0.000 description 1
• 241000242726 Opisthorchis viverrini Species 0.000 description 1
• 241000700635 Orf virus Species 0.000 description 1
• 241000250439 Oropouche virus Species 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 206010061535 Ovarian neoplasm Diseases 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 241000222051 Papiliotrema laurentii Species 0.000 description 1
• 241000057252 Paragonimus africanus Species 0.000 description 1
• 241000551217 Paragonimus caliensis Species 0.000 description 1
• 241001446258 Paragonimus kellicotti Species 0.000 description 1
• 241000610664 Paragonimus skrjabini Species 0.000 description 1
• 241001480234 Paragonimus westermani Species 0.000 description 1
• 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
• 208000030852 Parasitic disease Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 244000025272 Persea americana Species 0.000 description 1
• 235000008673 Persea americana Nutrition 0.000 description 1
• 201000007100 Pharyngitis Diseases 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
• 206010034912 Phobia Diseases 0.000 description 1
• 241000712910 Pichinde mammarenavirus Species 0.000 description 1
• 241000224016 Plasmodium Species 0.000 description 1
• 241000223960 Plasmodium falciparum Species 0.000 description 1
• 241000223801 Plasmodium knowlesi Species 0.000 description 1
• 241000223821 Plasmodium malariae Species 0.000 description 1
• 241001505293 Plasmodium ovale Species 0.000 description 1
• 241000223810 Plasmodium vivax Species 0.000 description 1
• 241000233870 Pneumocystis Species 0.000 description 1
• 241000233872 Pneumocystis carinii Species 0.000 description 1
• 241000142787 Pneumocystis jirovecii Species 0.000 description 1
• 206010035717 Pneumonia klebsiella Diseases 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 239000004952 Polyamide Substances 0.000 description 1
• 208000004550 Postoperative Pain Diseases 0.000 description 1
• 241000710884 Powassan virus Species 0.000 description 1
• 241000588769 Proteus <enterobacteria> Species 0.000 description 1
• 241000588770 Proteus mirabilis Species 0.000 description 1
• 241000588767 Proteus vulgaris Species 0.000 description 1
• 241000588768 Providencia Species 0.000 description 1
• 241000588777 Providencia rettgeri Species 0.000 description 1
• 241000588778 Providencia stuartii Species 0.000 description 1
• 208000003251 Pruritus Diseases 0.000 description 1
• 241000589516 Pseudomonas Species 0.000 description 1
• 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
• 206010037249 Psychotic behaviour Diseases 0.000 description 1
• 241000014360 Punta Toro phlebovirus Species 0.000 description 1
• 241000150264 Puumala orthohantavirus Species 0.000 description 1
• 241000711798 Rabies lyssavirus Species 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 208000033626 Renal failure acute Diseases 0.000 description 1
• 206010063897 Renal ischaemia Diseases 0.000 description 1
• 241000293824 Rhinosporidium seeberi Species 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 241000713124 Rift Valley fever virus Species 0.000 description 1
• 241000710942 Ross River virus Species 0.000 description 1
• 241001137860 Rotavirus A Species 0.000 description 1
• 241001137861 Rotavirus B Species 0.000 description 1
• 241001506005 Rotavirus C Species 0.000 description 1
• 241000710799 Rubella virus Species 0.000 description 1
• 241000315672 SARS coronavirus Species 0.000 description 1
• 229910006124 SOCl2 Inorganic materials 0.000 description 1
• 241000608282 Sagiyama virus Species 0.000 description 1
• 241000607142 Salmonella Species 0.000 description 1
• 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
• 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
• 241001135555 Sandfly fever Sicilian virus Species 0.000 description 1
• 241000369753 Sapporo virus Species 0.000 description 1
• 241001473628 Sarcocystis suihominis Species 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 241000257185 Sarcophagidae Species 0.000 description 1
• 241000242678 Schistosoma Species 0.000 description 1
• 241000242683 Schistosoma haematobium Species 0.000 description 1
• 241000242677 Schistosoma japonicum Species 0.000 description 1
• 241000242680 Schistosoma mansoni Species 0.000 description 1
• 241001520868 Schistosoma mekongi Species 0.000 description 1
• 241001442514 Schistosomatidae Species 0.000 description 1
• 241000710961 Semliki Forest virus Species 0.000 description 1
• 241000150278 Seoul orthohantavirus Species 0.000 description 1
• 206010040047 Sepsis Diseases 0.000 description 1
• 206010053879 Sepsis syndrome Diseases 0.000 description 1
• 102100035712 Serrate RNA effector molecule homolog Human genes 0.000 description 1
• 108010036039 Serrate-Jagged Proteins Proteins 0.000 description 1
• 102000007562 Serum Albumin Human genes 0.000 description 1
• 108010071390 Serum Albumin Proteins 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 241000607768 Shigella Species 0.000 description 1
• 241000607760 Shigella sonnei Species 0.000 description 1
• 241000713656 Simian foamy virus Species 0.000 description 1
• 241000710960 Sindbis virus Species 0.000 description 1
• 206010040744 Sinus headache Diseases 0.000 description 1
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
• 241000713134 Snowshoe hare virus Species 0.000 description 1
• 206010041250 Social phobia Diseases 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 241000714208 Southampton virus Species 0.000 description 1
• 208000003589 Spider Bites Diseases 0.000 description 1
• 241000422838 Spirometra erinaceieuropaei Species 0.000 description 1
• 241000710888 St. Louis encephalitis virus Species 0.000 description 1
• 241001279361 Stachybotrys Species 0.000 description 1
• 206010041925 Staphylococcal infections Diseases 0.000 description 1
• 241000191940 Staphylococcus Species 0.000 description 1
• 241000191967 Staphylococcus aureus Species 0.000 description 1
• 241000191963 Staphylococcus epidermidis Species 0.000 description 1
• 241000191984 Staphylococcus haemolyticus Species 0.000 description 1
• 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000005718 Stomach Neoplasms Diseases 0.000 description 1
• 241000194017 Streptococcus Species 0.000 description 1
• 241000193985 Streptococcus agalactiae Species 0.000 description 1
• 201000005010 Streptococcus pneumonia Diseases 0.000 description 1
• 241000193998 Streptococcus pneumoniae Species 0.000 description 1
• 241000193996 Streptococcus pyogenes Species 0.000 description 1
• 241001312524 Streptococcus viridans Species 0.000 description 1
• 241000244177 Strongyloides stercoralis Species 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• 206010042496 Sunburn Diseases 0.000 description 1
• 241000244155 Taenia Species 0.000 description 1
• 241000356560 Taenia multiceps Species 0.000 description 1
• 241000244159 Taenia saginata Species 0.000 description 1
• 241000244157 Taenia solium Species 0.000 description 1
• 206010043269 Tension headache Diseases 0.000 description 1
• 208000008548 Tension-Type Headache Diseases 0.000 description 1
• 208000024313 Testicular Neoplasms Diseases 0.000 description 1
• 206010057644 Testis cancer Diseases 0.000 description 1
• 241000223776 Theileria equi Species 0.000 description 1
• 241001477954 Thelazia Species 0.000 description 1
• 244000309734 Thelazia californiensis Species 0.000 description 1
• 241001477955 Thelazia callipaeda Species 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
• 241000960387 Torque teno virus Species 0.000 description 1
• 241000713154 Toscana virus Species 0.000 description 1
• 206010067722 Toxic neuropathy Diseases 0.000 description 1
• 231100000126 Toxic neuropathy Toxicity 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• 241000244020 Toxocara cati Species 0.000 description 1
• 241000223997 Toxoplasma gondii Species 0.000 description 1
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
• 208000030886 Traumatic Brain injury Diseases 0.000 description 1
• 241000589886 Treponema Species 0.000 description 1
• 241000589884 Treponema pallidum Species 0.000 description 1
• 241000243774 Trichinella Species 0.000 description 1
• 241000194297 Trichinella britovi Species 0.000 description 1
• 241000243776 Trichinella nativa Species 0.000 description 1
• 241000243779 Trichinella nelsoni Species 0.000 description 1
• 241000243777 Trichinella spiralis Species 0.000 description 1
• 241000031115 Trichobilharzia regenti Species 0.000 description 1
• 241000224526 Trichomonas Species 0.000 description 1
• 241000224527 Trichomonas vaginalis Species 0.000 description 1
• 241001489151 Trichuris Species 0.000 description 1
• 241001489145 Trichuris trichiura Species 0.000 description 1
• 241001638368 Trichuris vulpis Species 0.000 description 1
• 241000223104 Trypanosoma Species 0.000 description 1
• 241000223105 Trypanosoma brucei Species 0.000 description 1
• 241000224557 Trypanosoma brucei brucei Species 0.000 description 1
• 241000223109 Trypanosoma cruzi Species 0.000 description 1
• 241001584775 Tunga penetrans Species 0.000 description 1
• 241000202898 Ureaplasma Species 0.000 description 1
• 241000202921 Ureaplasma urealyticum Species 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 208000002495 Uterine Neoplasms Diseases 0.000 description 1
• 241000713152 Uukuniemi virus Species 0.000 description 1
• 241000700618 Vaccinia virus Species 0.000 description 1
• 241000700647 Variola virus Species 0.000 description 1
• 241000710959 Venezuelan equine encephalitis virus Species 0.000 description 1
• 241000711975 Vesicular stomatitis virus Species 0.000 description 1
• 241000607598 Vibrio Species 0.000 description 1
• 241000607626 Vibrio cholerae Species 0.000 description 1
• 241000607265 Vibrio vulnificus Species 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• 206010047601 Vitamin B1 deficiency Diseases 0.000 description 1
• 241000379754 WU Polyomavirus Species 0.000 description 1
• 241000710886 West Nile virus Species 0.000 description 1
• 241000710951 Western equine encephalitis virus Species 0.000 description 1
• 241000244005 Wuchereria bancrofti Species 0.000 description 1
• 241001536558 Yaba monkey tumor virus Species 0.000 description 1
• 241000913725 Yaba-like disease virus Species 0.000 description 1
• 241000710772 Yellow fever virus Species 0.000 description 1
• 241000607734 Yersinia <bacteria> Species 0.000 description 1
• 241000607479 Yersinia pestis Species 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• 229920002494 Zein Polymers 0.000 description 1
• COERJHDMQUPDCV-UHFFFAOYSA-N [K].FB(F)F Chemical class [K].FB(F)F COERJHDMQUPDCV-UHFFFAOYSA-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
• 238000009825 accumulation Methods 0.000 description 1
• UTKBLLDLHPDWDU-ODZAUARKSA-N acetic acid;(z)-but-2-enedioic acid Chemical compound CC(O)=O.OC(=O)\C=C/C(O)=O UTKBLLDLHPDWDU-ODZAUARKSA-N 0.000 description 1
• IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 description 1
• ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 1
• AEMQUICCWRPKDB-UHFFFAOYSA-N acetic acid;cyclohexane-1,2-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1CCCCC1C(O)=O AEMQUICCWRPKDB-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical class CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 201000011040 acute kidney failure Diseases 0.000 description 1
• 206010069351 acute lung injury Diseases 0.000 description 1
• 208000005298 acute pain Diseases 0.000 description 1
• 208000012998 acute renal failure Diseases 0.000 description 1
• 208000026345 acute stress disease Diseases 0.000 description 1
• 150000001263 acyl chlorides Chemical class 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 230000003044 adaptive effect Effects 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 208000020701 alcoholic polyneuropathy Diseases 0.000 description 1
• 229940072056 alginate Drugs 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
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 150000001347 alkyl bromides Chemical class 0.000 description 1
• 150000001351 alkyl iodides Chemical class 0.000 description 1
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 239000002519 antifouling agent Substances 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 230000036528 appetite Effects 0.000 description 1
• 235000019789 appetite Nutrition 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 229940114078 arachidonate Drugs 0.000 description 1
• 229940114079 arachidonic acid Drugs 0.000 description 1
• 235000021342 arachidonic acid Nutrition 0.000 description 1
• LGEQQWMQCRIYKG-UHFFFAOYSA-N arachidonic acid ethanolamide Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO LGEQQWMQCRIYKG-UHFFFAOYSA-N 0.000 description 1
• 206010003074 arachnoiditis Diseases 0.000 description 1
• 150000001543 aryl boronic acids Chemical class 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 229940091771 aspergillus fumigatus Drugs 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 150000001540 azides Chemical class 0.000 description 1
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
• 229940065181 bacillus anthracis Drugs 0.000 description 1
• 230000003385 bacteriostatic effect Effects 0.000 description 1
• 208000007456 balantidiasis Diseases 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 239000011324 bead Substances 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 230000003542 behavioural effect Effects 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005870 benzindolyl group Chemical group 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000005875 benzo[b][1,4]dioxepinyl group Chemical group 0.000 description 1
• 125000005876 benzo[b][1,4]oxazinyl group Chemical group 0.000 description 1
• 125000005873 benzo[d]thiazolyl group Chemical group 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• 208000002894 beriberi Diseases 0.000 description 1
• 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 1
• BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 239000003139 biocide Substances 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 229940056450 brucella abortus Drugs 0.000 description 1
• 229940038698 brucella melitensis Drugs 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 239000001273 butane Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 235000012241 calcium silicate Nutrition 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
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 229940095731 candida albicans Drugs 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 150000001768 cations Chemical class 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
• 229960000590 celecoxib Drugs 0.000 description 1
• 230000012292 cell migration Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
• 229920006218 cellulose propionate Polymers 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
• 229940038705 chlamydia trachomatis Drugs 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
• 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
• 201000001352 cholecystitis Diseases 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 238000011260 co-administration Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 229960004126 codeine Drugs 0.000 description 1
• OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Natural products C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
• 230000006999 cognitive decline Effects 0.000 description 1
• 230000003920 cognitive function Effects 0.000 description 1
• 230000007370 cognitive improvement Effects 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
• 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 150000001924 cycloalkanes Chemical class 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 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
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 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
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
• WUAVKVSBOPMONC-UHFFFAOYSA-N cyclopenta[b][1,4]oxazine Chemical compound O1C=CN=C2C1=CC=C2 WUAVKVSBOPMONC-UHFFFAOYSA-N 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 229960003428 dexibuprofen Drugs 0.000 description 1
• HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• 229960000616 diflunisal Drugs 0.000 description 1
• HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 206010013023 diphtheria Diseases 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 229940099686 dirofilaria immitis Drugs 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 235000014632 disordered eating Nutrition 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 239000006196 drop Substances 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
• 229960001850 droxicam Drugs 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 244000078703 ectoparasite Species 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 229940092559 enterobacter aerogenes Drugs 0.000 description 1
• 229940032049 enterococcus faecalis Drugs 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 238000006911 enzymatic reaction Methods 0.000 description 1
• 201000004101 esophageal cancer Diseases 0.000 description 1
• LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 229940093499 ethyl acetate Drugs 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
• GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 229960005293 etodolac Drugs 0.000 description 1
• XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 1
• 239000004060 excitotoxin Substances 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 229960001419 fenoprofen Drugs 0.000 description 1
• 229960002428 fentanyl Drugs 0.000 description 1
• IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 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
• 239000012530 fluid Substances 0.000 description 1
• 239000011737 fluorine Chemical group 0.000 description 1
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 229940118764 francisella tularensis Drugs 0.000 description 1
• 235000021588 free fatty acids Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
• 125000003844 furanonyl group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
• 206010017758 gastric cancer Diseases 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 229940085435 giardia lamblia Drugs 0.000 description 1
• 239000008103 glucose Substances 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
• 125000000262 haloalkenyl group Chemical group 0.000 description 1
• 125000000232 haloalkynyl group Chemical group 0.000 description 1
• 210000003128 head Anatomy 0.000 description 1
• 231100000869 headache Toxicity 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 229940037467 helicobacter pylori Drugs 0.000 description 1
• 201000005787 hematologic cancer Diseases 0.000 description 1
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
• 125000005553 heteroaryloxy group Chemical group 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
• LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
• 229960000240 hydrocodone Drugs 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• KJDJPXUIZYHXEZ-UHFFFAOYSA-N hydrogen sulfate;methylaminoazanium Chemical compound CN[NH3+].OS([O-])(=O)=O KJDJPXUIZYHXEZ-UHFFFAOYSA-N 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 description 1
• 229960001410 hydromorphone Drugs 0.000 description 1
• RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 230000009610 hypersensitivity Effects 0.000 description 1
• 229960001680 ibuprofen Drugs 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 229960000905 indomethacin Drugs 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 206010022437 insomnia Diseases 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 208000002551 irritable bowel syndrome Diseases 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000000644 isotonic solution Substances 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 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
• 150000002576 ketones Chemical class 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
• OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
• 229960004752 ketorolac Drugs 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 229940115932 legionella pneumophila Drugs 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 229960003406 levorphanol Drugs 0.000 description 1
• 229940115931 listeria monocytogenes Drugs 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 208000014018 liver neoplasm Diseases 0.000 description 1
• OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 description 1
• 229960002202 lornoxicam Drugs 0.000 description 1
• 229960002373 loxoprofen Drugs 0.000 description 1
• BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229960001929 meloxicam Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000037353 metabolic pathway Effects 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 1
• CFQWORRYXRDOLU-UHFFFAOYSA-N methyl 2-carbonochloridoyloxy-3,3,3-trifluoropropanoate Chemical class COC(=O)C(C(F)(F)F)OC(Cl)=O CFQWORRYXRDOLU-UHFFFAOYSA-N 0.000 description 1
• ORNQCBRCAKLZDO-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-hydroxypropanoate Chemical compound COC(=O)C(O)C(F)(F)F ORNQCBRCAKLZDO-UHFFFAOYSA-N 0.000 description 1
• XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 206010027599 migraine Diseases 0.000 description 1
• 235000013336 milk Nutrition 0.000 description 1
• 239000008267 milk Substances 0.000 description 1
• 210000004080 milk Anatomy 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000007932 molded tablet Substances 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 229960005181 morphine Drugs 0.000 description 1
• 210000004400 mucous membrane Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 208000017445 musculoskeletal system disease Diseases 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• SXGRRNXWWIQUOO-UHFFFAOYSA-N n-(azetidin-3-yl)acetamide Chemical compound CC(=O)NC1CNC1 SXGRRNXWWIQUOO-UHFFFAOYSA-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
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229960002009 naproxen Drugs 0.000 description 1
• 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 1
• 239000000025 natural resin Substances 0.000 description 1
• 230000008693 nausea Effects 0.000 description 1
• 210000003739 neck Anatomy 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 208000004296 neuralgia Diseases 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 230000003959 neuroinflammation Effects 0.000 description 1
• 230000002981 neuropathic effect Effects 0.000 description 1
• 208000021722 neuropathic pain Diseases 0.000 description 1
• 230000000324 neuroprotective effect Effects 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• PSACHCMMPFMFAJ-UHFFFAOYSA-N nmm n-methylmorpholine Chemical compound CN1CCOCC1.CN1CCOCC1 PSACHCMMPFMFAJ-UHFFFAOYSA-N 0.000 description 1
• 238000013546 non-drug therapy Methods 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
• 239000002736 nonionic surfactant 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
• 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229960002969 oleic acid Drugs 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 230000002611 ovarian Effects 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 229960002739 oxaprozin Drugs 0.000 description 1
• OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 229960005118 oxymorphone Drugs 0.000 description 1
• 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• 208000019906 panic disease Diseases 0.000 description 1
• 229960005489 paracetamol Drugs 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 1
• 229960004662 parecoxib Drugs 0.000 description 1
• 244000052769 pathogen Species 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
• JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
• 239000008024 pharmaceutical diluent Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 230000003285 pharmacodynamic effect Effects 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 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
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• JVBSYPAMUFSLLZ-UHFFFAOYSA-N piperidin-4-yl(pyrrolidin-1-yl)methanone;hydrochloride Chemical compound Cl.C1CCCN1C(=O)C1CCNCC1 JVBSYPAMUFSLLZ-UHFFFAOYSA-N 0.000 description 1
• 229960002702 piroxicam Drugs 0.000 description 1
• 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 1
• IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• 229940118768 plasmodium malariae Drugs 0.000 description 1
• 201000000317 pneumocystosis Diseases 0.000 description 1
• 208000030773 pneumonia caused by chlamydia Diseases 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• 229920002647 polyamide Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 229920000136 polysorbate Polymers 0.000 description 1
• 229920002744 polyvinyl acetate phthalate 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
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000000770 proinflammatory effect Effects 0.000 description 1
• 239000001294 propane Substances 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 229940007042 proteus vulgaris Drugs 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000006340 racemization Effects 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 238000009790 rate-determining step (RDS) Methods 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 238000011946 reduction process Methods 0.000 description 1
• 238000006268 reductive amination reaction Methods 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 239000003340 retarding agent Substances 0.000 description 1
• 238000004007 reversed phase HPLC Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 1
• 229960003015 rimonabant Drugs 0.000 description 1
• 239000012487 rinsing solution Substances 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 229960000953 salsalate Drugs 0.000 description 1
• 201000000980 schizophrenia Diseases 0.000 description 1
• 230000036303 septic shock Effects 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 229940115939 shigella sonnei Drugs 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 208000019116 sleep disease Diseases 0.000 description 1
• 230000004617 sleep duration Effects 0.000 description 1
• 230000003860 sleep quality Effects 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 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
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 201000001716 specific phobia Diseases 0.000 description 1
• 238000004611 spectroscopical analysis Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 208000020431 spinal cord injury Diseases 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 201000011549 stomach cancer Diseases 0.000 description 1
• 229940076156 streptococcus pyogenes Drugs 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 150000005846 sugar alcohols Chemical class 0.000 description 1
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
• 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 1
• 229960000894 sulindac Drugs 0.000 description 1
• 235000011149 sulphuric acid Nutrition 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 238000007910 systemic administration Methods 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• WZWYJBNHTWCXIM-UHFFFAOYSA-N tenoxicam Chemical compound O=C1C=2SC=CC=2S(=O)(=O)N(C)C1=C(O)NC1=CC=CC=N1 WZWYJBNHTWCXIM-UHFFFAOYSA-N 0.000 description 1
• 229960002871 tenoxicam Drugs 0.000 description 1
• GXRWQSIBOSHOGI-UHFFFAOYSA-N tert-butyl 4-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(N2CCOCC2)C=C1F GXRWQSIBOSHOGI-UHFFFAOYSA-N 0.000 description 1
• 201000003120 testicular cancer Diseases 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
• 229960001017 tolmetin Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 208000004371 toothache Diseases 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 229960004380 tramadol Drugs 0.000 description 1
• TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
• LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 230000009529 traumatic brain injury Effects 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 229940116861 trichinella britovi Drugs 0.000 description 1
• 229940096911 trichinella spiralis Drugs 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 206010044652 trigeminal neuralgia Diseases 0.000 description 1
• 125000005591 trimellitate group Chemical group 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• 241001529453 unidentified herpesvirus Species 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 208000019206 urinary tract infection Diseases 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 235000019871 vegetable fat Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 231100000611 venom Toxicity 0.000 description 1
• 229940118696 vibrio cholerae Drugs 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 208000009935 visceral pain Diseases 0.000 description 1
• 230000008673 vomiting Effects 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 229940051021 yellow-fever virus Drugs 0.000 description 1
• 229940093612 zein Drugs 0.000 description 1
• 239000005019 zein Substances 0.000 description 1
• 239000011787 zinc oxide Substances 0.000 description 1
• 235000014692 zinc oxide Nutrition 0.000 description 1