KR20230092972A - 연충 감염 및 질병의 치료를 위한 헤테로환식 화합물 및 이들의 용도 - Google Patents
연충 감염 및 질병의 치료를 위한 헤테로환식 화합물 및 이들의 용도 Download PDFInfo
- Publication number
- KR20230092972A KR20230092972A KR1020237016754A KR20237016754A KR20230092972A KR 20230092972 A KR20230092972 A KR 20230092972A KR 1020237016754 A KR1020237016754 A KR 1020237016754A KR 20237016754 A KR20237016754 A KR 20237016754A KR 20230092972 A KR20230092972 A KR 20230092972A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- compound
- alkyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 67
- 201000010099 disease Diseases 0.000 title claims abstract description 56
- 208000006968 Helminthiasis Diseases 0.000 title claims description 12
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 title claims description 12
- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 140
- 238000011282 treatment Methods 0.000 title description 31
- 238000000034 method Methods 0.000 claims abstract description 134
- 150000003839 salts Chemical class 0.000 claims abstract description 76
- 241000002163 Mesapamea fractilinea Species 0.000 claims abstract description 62
- 208000015181 infectious disease Diseases 0.000 claims abstract description 46
- -1 2-pyrimidyl Chemical group 0.000 claims description 522
- 150000001875 compounds Chemical class 0.000 claims description 336
- 125000000217 alkyl group Chemical group 0.000 claims description 155
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 125000001424 substituent group Chemical group 0.000 claims description 129
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 125
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 105
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 94
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 72
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 57
- 125000005936 piperidyl group Chemical group 0.000 claims description 57
- 244000000013 helminth Species 0.000 claims description 56
- 125000004193 piperazinyl group Chemical group 0.000 claims description 55
- 206010061217 Infestation Diseases 0.000 claims description 54
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 52
- 108010034145 Helminth Proteins Proteins 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 125000002757 morpholinyl group Chemical group 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 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 27
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 27
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 14
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 229960002418 ivermectin Drugs 0.000 claims description 14
- 230000004899 motility Effects 0.000 claims description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000000921 anthelmintic agent Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004069 aziridinyl group Chemical group 0.000 claims description 11
- RCKMWOKWVGPNJF-UHFFFAOYSA-N diethylcarbamazine Chemical compound CCN(CC)C(=O)N1CCN(C)CC1 RCKMWOKWVGPNJF-UHFFFAOYSA-N 0.000 claims description 11
- 229960003974 diethylcarbamazine Drugs 0.000 claims description 11
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000005412 pyrazyl group Chemical group 0.000 claims description 8
- 201000006353 Filariasis Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000003981 vehicle Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- JEIZLWNUBXHADF-UHFFFAOYSA-N Pelletierine Chemical compound CC(=O)CC1CCCCN1 JEIZLWNUBXHADF-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000002147 killing effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 6
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical compound ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 claims description 5
- AQXXZDYPVDOQEE-MXDQRGINSA-N Pyrantel pamoate Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 AQXXZDYPVDOQEE-MXDQRGINSA-N 0.000 claims description 5
- CPEUVMUXAHMANV-UHFFFAOYSA-N flubendazole Chemical group C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=C(F)C=C1 CPEUVMUXAHMANV-UHFFFAOYSA-N 0.000 claims description 5
- 229960004500 flubendazole Drugs 0.000 claims description 5
- 229960000996 pyrantel pamoate Drugs 0.000 claims description 5
- 229960000323 triclabendazole Drugs 0.000 claims description 5
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 4
- 239000005660 Abamectin Substances 0.000 claims description 4
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims description 4
- 241000604961 Wolbachia Species 0.000 claims description 4
- 229950008167 abamectin Drugs 0.000 claims description 4
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 claims description 4
- IRHZVMHXVHSMKB-UHFFFAOYSA-N fenbendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 IRHZVMHXVHSMKB-UHFFFAOYSA-N 0.000 claims description 4
- 229960005473 fenbendazole Drugs 0.000 claims description 4
- 229960001614 levamisole Drugs 0.000 claims description 4
- 229960003439 mebendazole Drugs 0.000 claims description 4
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 claims description 4
- 229950003439 monepantel Drugs 0.000 claims description 4
- WTERNLDOAPYGJD-SFHVURJKSA-N monepantel Chemical compound C([C@@](C)(NC(=O)C=1C=CC(SC(F)(F)F)=CC=1)C#N)OC1=CC(C#N)=CC=C1C(F)(F)F WTERNLDOAPYGJD-SFHVURJKSA-N 0.000 claims description 4
- 229960001920 niclosamide Drugs 0.000 claims description 4
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960002480 nitazoxanide Drugs 0.000 claims description 4
- 229950003126 oxyclozanide Drugs 0.000 claims description 4
- JYWIYHUXVMAGLG-UHFFFAOYSA-N oxyclozanide Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)C1=C(O)C(Cl)=CC(Cl)=C1Cl JYWIYHUXVMAGLG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229960005314 suramin Drugs 0.000 claims description 4
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims description 4
- 230000008685 targeting Effects 0.000 claims description 4
- 239000004308 thiabendazole Substances 0.000 claims description 4
- 235000010296 thiabendazole Nutrition 0.000 claims description 4
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 4
- 229960004546 thiabendazole Drugs 0.000 claims description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 3
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims description 3
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 claims description 3
- 229960002669 albendazole Drugs 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- DYQFPHHPIWNYFO-UHFFFAOYSA-N n,4-bis(4-methylpyridin-2-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC(NC=2SC=C(N=2)C=2N=CC=C(C)C=2)=C1 DYQFPHHPIWNYFO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- 229960002957 praziquantel Drugs 0.000 claims description 3
- DYVLXWPZFQQUIU-WGNDVSEMSA-N derquantel Chemical compound O1C(C)(C)C=COC2=C1C=CC1=C2NC[C@]11C(C)(C)[C@@H]2C[C@]3(N(C4)CC[C@@]3(C)O)C(=O)N(C)[C@]42C1 DYVLXWPZFQQUIU-WGNDVSEMSA-N 0.000 claims description 2
- 229950004278 derquantel Drugs 0.000 claims description 2
- 229960003722 doxycycline Drugs 0.000 claims description 2
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 229960001575 emodepside Drugs 0.000 claims 1
- ZMQMTKVVAMWKNY-YSXLEBCMSA-N emodepside Chemical compound C([C@@H]1C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@H](C(O[C@H](CC=2C=CC(=CC=2)N2CCOCC2)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O1)=O)CC(C)C)C(C=C1)=CC=C1N1CCOCC1 ZMQMTKVVAMWKNY-YSXLEBCMSA-N 0.000 claims 1
- 108010056417 emodepside Proteins 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 213
- 241001465754 Metazoa Species 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 225
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 164
- 239000011541 reaction mixture Substances 0.000 description 141
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 106
- 239000011734 sodium Substances 0.000 description 95
- 230000002829 reductive effect Effects 0.000 description 83
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 73
- 239000002904 solvent Substances 0.000 description 69
- 239000012267 brine Substances 0.000 description 68
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 68
- 238000004440 column chromatography Methods 0.000 description 66
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000000047 product Substances 0.000 description 60
- 239000012044 organic layer Substances 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
- 229920006395 saturated elastomer Polymers 0.000 description 40
- 239000002585 base Substances 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 36
- 239000002552 dosage form Substances 0.000 description 36
- 241000244206 Nematoda Species 0.000 description 34
- 241000243985 Onchocerca volvulus Species 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 33
- 125000004093 cyano group Chemical group *C#N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000005457 ice water Substances 0.000 description 28
- 208000002042 onchocerciasis Diseases 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
- 238000010561 standard procedure Methods 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 208000030852 Parasitic disease Diseases 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 230000037396 body weight Effects 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 150000003254 radicals Chemical group 0.000 description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 241000282472 Canis lupus familiaris Species 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
- 239000012300 argon atmosphere Substances 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 241000894007 species Species 0.000 description 14
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 14
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 13
- GHHXGWZMJBHPOM-UHFFFAOYSA-N (3-methylpyridin-2-yl)thiourea Chemical compound CC1=CC=CN=C1NC(N)=S GHHXGWZMJBHPOM-UHFFFAOYSA-N 0.000 description 12
- ALLBLAKJCNRLLS-UHFFFAOYSA-N (4-methylpyridin-2-yl)thiourea Chemical compound CC1=CC=NC(NC(N)=S)=C1 ALLBLAKJCNRLLS-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000002953 preparative HPLC Methods 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 241000243988 Dirofilaria immitis Species 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 230000001418 larval effect Effects 0.000 description 11
- 238000013160 medical therapy Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000013058 crude material Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 125000003373 pyrazinyl group Chemical group 0.000 description 9
- 125000002098 pyridazinyl group Chemical group 0.000 description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 241000244036 Brugia Species 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 244000045947 parasite Species 0.000 description 8
- 230000003071 parasitic effect Effects 0.000 description 8
- 239000007821 HATU Substances 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000002441 reversible effect Effects 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- WYFMWHODDPRPHV-UHFFFAOYSA-N CC(C)OC(C=C1)=CN=C1C(CBr)=O Chemical compound CC(C)OC(C=C1)=CN=C1C(CBr)=O WYFMWHODDPRPHV-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- 206010016675 Filariasis lymphatic Diseases 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 208000037263 Lymphatic filariasis Diseases 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 206010047697 Volvulus Diseases 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 208000005239 filarial elephantiasis Diseases 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 201000007647 intestinal volvulus Diseases 0.000 description 6
- 230000000155 isotopic effect Effects 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- RPIWCILWIFNVCU-UHFFFAOYSA-N n-[(3-methylpyridin-2-yl)carbamothioyl]benzamide Chemical compound CC1=CC=CN=C1NC(=S)NC(=O)C1=CC=CC=C1 RPIWCILWIFNVCU-UHFFFAOYSA-N 0.000 description 6
- 201000004409 schistosomiasis Diseases 0.000 description 6
- 238000011894 semi-preparative HPLC Methods 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 5
- 208000003917 Dirofilariasis Diseases 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 241000142892 Mansonella Species 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 229940099686 dirofilaria immitis Drugs 0.000 description 5
- 238000004108 freeze drying Methods 0.000 description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 5
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- GSEZHCLWHDZJAB-UHFFFAOYSA-N oxan-4-yl methanesulfonate Chemical compound CS(=O)(=O)OC1CCOCC1 GSEZHCLWHDZJAB-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
- TUBDSHFXNOJDGI-UHFFFAOYSA-N 2-bromo-1-(5-methoxypyridin-2-yl)ethanone Chemical compound COc1ccc(nc1)C(=O)CBr TUBDSHFXNOJDGI-UHFFFAOYSA-N 0.000 description 4
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 4
- LWMDPZVQAMQFOC-UHFFFAOYSA-N 4-butylpyridine Chemical compound CCCCC1=CC=NC=C1 LWMDPZVQAMQFOC-UHFFFAOYSA-N 0.000 description 4
- DSHKMXFMZNUEHE-UHFFFAOYSA-N 4-propan-2-yloxypyridin-2-amine Chemical compound CC(C)OC1=CC=NC(N)=C1 DSHKMXFMZNUEHE-UHFFFAOYSA-N 0.000 description 4
- DYFGITWCYYDSEZ-UHFFFAOYSA-N C(C)(C)C=1C(=CC(=NC=1)NC(=S)N)C(F)(F)F Chemical compound C(C)(C)C=1C(=CC(=NC=1)NC(=S)N)C(F)(F)F DYFGITWCYYDSEZ-UHFFFAOYSA-N 0.000 description 4
- NCBYXEQVPWEKJJ-UHFFFAOYSA-N CC(C)(CC1=C2)OC1=CN=C2C(CBr)=O Chemical compound CC(C)(CC1=C2)OC1=CN=C2C(CBr)=O NCBYXEQVPWEKJJ-UHFFFAOYSA-N 0.000 description 4
- DBZGENFXOLTDET-UHFFFAOYSA-N CC(C)OC1=CC(C(CBr)=O)=NC=C1 Chemical compound CC(C)OC1=CC(C(CBr)=O)=NC=C1 DBZGENFXOLTDET-UHFFFAOYSA-N 0.000 description 4
- XPJMDXGVUOKFES-UHFFFAOYSA-N CC(C)OC1=CC(NC2=NC(C(C=C3)=NC=C3OC)=CS2)=NC=C1 Chemical compound CC(C)OC1=CC(NC2=NC(C(C=C3)=NC=C3OC)=CS2)=NC=C1 XPJMDXGVUOKFES-UHFFFAOYSA-N 0.000 description 4
- OHMGSTMMIHBSSV-UHFFFAOYSA-N CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OC)=CS1 Chemical compound CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OC)=CS1 OHMGSTMMIHBSSV-UHFFFAOYSA-N 0.000 description 4
- RTANASMFCJNBEM-UHFFFAOYSA-N CN(C(OC(C)(C)C)=O)C=1C=NC(=C(C=1)C(F)(F)F)NC(=S)N Chemical compound CN(C(OC(C)(C)C)=O)C=1C=NC(=C(C=1)C(F)(F)F)NC(=S)N RTANASMFCJNBEM-UHFFFAOYSA-N 0.000 description 4
- 241000242722 Cestoda Species 0.000 description 4
- 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 4
- 241000243990 Dirofilaria Species 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- YOLCAUPKEREGCU-UHFFFAOYSA-N OCC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 Chemical compound OCC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 YOLCAUPKEREGCU-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 241000242541 Trematoda Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- VQXINLNPICQTLR-UHFFFAOYSA-N carbonyl diazide Chemical class [N-]=[N+]=NC(=O)N=[N+]=[N-] VQXINLNPICQTLR-UHFFFAOYSA-N 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 description 4
- 150000002540 isothiocyanates Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 244000144977 poultry Species 0.000 description 4
- 235000013594 poultry meat Nutrition 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- IHRLABACBKPYLT-UHFFFAOYSA-N prop-2-enethioamide Chemical class NC(=S)C=C IHRLABACBKPYLT-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- UUIKPAVVDPUTNH-DAXSKMNVSA-N (z)-3-amino-3-pyridin-2-ylprop-2-enenitrile Chemical compound N#C\C=C(/N)C1=CC=CC=N1 UUIKPAVVDPUTNH-DAXSKMNVSA-N 0.000 description 3
- STDNWDJKSJVMLI-UHFFFAOYSA-N 1-(3-phenylpyridin-2-yl)ethanone Chemical compound CC(=O)C1=NC=CC=C1C1=CC=CC=C1 STDNWDJKSJVMLI-UHFFFAOYSA-N 0.000 description 3
- NBNSGPOXCMVTJL-UHFFFAOYSA-N 1-(5-propan-2-yloxypyridin-2-yl)ethanol Chemical compound CC(C)OC1=CC=C(C(C)O)N=C1 NBNSGPOXCMVTJL-UHFFFAOYSA-N 0.000 description 3
- OBBDMQLHKNVZOV-UHFFFAOYSA-N 1-(5-propan-2-yloxypyridin-2-yl)ethanone Chemical compound CC(C)OC1=CC=C(C(C)=O)N=C1 OBBDMQLHKNVZOV-UHFFFAOYSA-N 0.000 description 3
- IXECYNPZHXXTAN-UHFFFAOYSA-N 1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone Chemical compound CC(=O)C1=CC=C(OCC(F)(F)F)C=N1 IXECYNPZHXXTAN-UHFFFAOYSA-N 0.000 description 3
- IWVHZRXWFIWOMH-UHFFFAOYSA-N 1-pyridin-2-ylbutan-1-one Chemical compound CCCC(=O)C1=CC=CC=N1 IWVHZRXWFIWOMH-UHFFFAOYSA-N 0.000 description 3
- FWDCVEBBTNSXKG-UHFFFAOYSA-N 2-[(5-methoxypyridine-2-carbonyl)amino]acetic acid Chemical compound COC1=CC=C(C(=O)NCC(O)=O)N=C1 FWDCVEBBTNSXKG-UHFFFAOYSA-N 0.000 description 3
- PMAMKVXETFDLHM-UHFFFAOYSA-N 2-bromo-1-pyridin-2-ylbutan-1-one Chemical compound CCC(Br)C(=O)C1=CC=CC=N1 PMAMKVXETFDLHM-UHFFFAOYSA-N 0.000 description 3
- DNPMOGQMEOPVNT-UHFFFAOYSA-N 2-bromo-1-pyridin-2-ylethanone Chemical compound BrCC(=O)C1=CC=CC=N1 DNPMOGQMEOPVNT-UHFFFAOYSA-N 0.000 description 3
- CUYHLTYVNBUNMW-UHFFFAOYSA-N 2-bromo-5-propan-2-yloxypyridine Chemical compound CC(C)OC1=CC=C(Br)N=C1 CUYHLTYVNBUNMW-UHFFFAOYSA-N 0.000 description 3
- SCOJKGRNQDKFRP-UHFFFAOYSA-N 2-chloro-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CCl SCOJKGRNQDKFRP-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- OJXNUAWQULNUCP-UHFFFAOYSA-N 3-phenylpyridin-2-amine Chemical compound NC1=NC=CC=C1C1=CC=CC=C1 OJXNUAWQULNUCP-UHFFFAOYSA-N 0.000 description 3
- TXPVAHIXJWBDFC-UHFFFAOYSA-N 4-butylpyridin-2-amine Chemical compound CCCCC1=CC=NC(N)=C1 TXPVAHIXJWBDFC-UHFFFAOYSA-N 0.000 description 3
- BAOIJCGWLQNKOE-UHFFFAOYSA-N 4-phenylpyridin-2-amine Chemical compound C1=NC(N)=CC(C=2C=CC=CC=2)=C1 BAOIJCGWLQNKOE-UHFFFAOYSA-N 0.000 description 3
- VOEPDUWIDULCAF-UHFFFAOYSA-N 4-pyrazin-2-ylpyridin-2-amine Chemical compound Nc1cc(ccn1)-c1cnccn1 VOEPDUWIDULCAF-UHFFFAOYSA-N 0.000 description 3
- QAINFPRHEISSOY-UHFFFAOYSA-N 4-pyridin-2-yl-n-pyrimidin-2-yl-1,3-thiazol-2-amine Chemical compound N=1C=CC=NC=1NC(SC=1)=NC=1C1=CC=CC=N1 QAINFPRHEISSOY-UHFFFAOYSA-N 0.000 description 3
- NHEZOCSLOBKVOY-UHFFFAOYSA-N 5-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile Chemical compound FC(F)(F)COC1=CC=C(C#N)N=C1 NHEZOCSLOBKVOY-UHFFFAOYSA-N 0.000 description 3
- AEWYLVDLWQPJGW-UHFFFAOYSA-N 5-bromo-4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=C(Br)C=N1 AEWYLVDLWQPJGW-UHFFFAOYSA-N 0.000 description 3
- SXIRUXLEHGHHSJ-UHFFFAOYSA-N 5-propan-2-yloxypyridine-2-carbaldehyde Chemical compound CC(C)OC1=CC=C(C=O)N=C1 SXIRUXLEHGHHSJ-UHFFFAOYSA-N 0.000 description 3
- UUMFIOSLMPIDKB-UHFFFAOYSA-N 6-bromo-n,n-dimethylpyridine-3-carboxamide Chemical compound CN(C)C(=O)C1=CC=C(Br)N=C1 UUMFIOSLMPIDKB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 240000000662 Anethum graveolens Species 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- MZZFBHOSWDCNMM-UHFFFAOYSA-N BrC=1N=C(SC=1)C1=NC=CC=C1C Chemical compound BrC=1N=C(SC=1)C1=NC=CC=C1C MZZFBHOSWDCNMM-UHFFFAOYSA-N 0.000 description 3
- 241000143302 Brugia timori Species 0.000 description 3
- PSKRFZXKVUJOMR-UHFFFAOYSA-N C(N)(=S)NC1=NC=C(C=C1N(C(OC(C)(C)C)=O)C)C(F)(F)F Chemical compound C(N)(=S)NC1=NC=C(C=C1N(C(OC(C)(C)C)=O)C)C(F)(F)F PSKRFZXKVUJOMR-UHFFFAOYSA-N 0.000 description 3
- MYRUQAWHXQGXFU-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC(=NC=C1)NC(=S)N Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1)NC(=S)N MYRUQAWHXQGXFU-UHFFFAOYSA-N 0.000 description 3
- ZMMCESLBWUGKTL-UHFFFAOYSA-N C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C3=NC=CN=C3)=C2)S1 Chemical compound C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C3=NC=CN=C3)=C2)S1 ZMMCESLBWUGKTL-UHFFFAOYSA-N 0.000 description 3
- BTEXJJDVUFPSIY-UHFFFAOYSA-N C1=CNC2=CC=C(NC3=NC(C4=NC=CC=C4)=CS3)N=C12 Chemical compound C1=CNC2=CC=C(NC3=NC(C4=NC=CC=C4)=CS3)N=C12 BTEXJJDVUFPSIY-UHFFFAOYSA-N 0.000 description 3
- HASQXJRPMVBPQT-UHFFFAOYSA-N C=C(C)C=1C(=CC(=NC=1)N)C(F)(F)F Chemical compound C=C(C)C=1C(=CC(=NC=1)N)C(F)(F)F HASQXJRPMVBPQT-UHFFFAOYSA-N 0.000 description 3
- PKIQWGAVRLQPRV-UHFFFAOYSA-N CC(C)(C)C(C(C1=NC=CC=C1)=O)Br Chemical compound CC(C)(C)C(C(C1=NC=CC=C1)=O)Br PKIQWGAVRLQPRV-UHFFFAOYSA-N 0.000 description 3
- RKDVFISDSHYVOE-UHFFFAOYSA-N CC(C)(C)OC(NC1=NC=CC(C2=NC=CN=C2)=C1)=O Chemical compound CC(C)(C)OC(NC1=NC=CC(C2=NC=CN=C2)=C1)=O RKDVFISDSHYVOE-UHFFFAOYSA-N 0.000 description 3
- UPIWACABLWFSHH-UHFFFAOYSA-N CC(C)(C1=CC(C2=CSC(NC3=NC=C(C(F)(F)F)C=C3N(C)C(C)=O)=N2)=NC=C1N1C)C1=O Chemical compound CC(C)(C1=CC(C2=CSC(NC3=NC=C(C(F)(F)F)C=C3N(C)C(C)=O)=N2)=NC=C1N1C)C1=O UPIWACABLWFSHH-UHFFFAOYSA-N 0.000 description 3
- JOORGRXKKOHJDH-UHFFFAOYSA-N CC(C)(CC1=C2)N(C)C1=CN=C2C(CBr)=O Chemical compound CC(C)(CC1=C2)N(C)C1=CN=C2C(CBr)=O JOORGRXKKOHJDH-UHFFFAOYSA-N 0.000 description 3
- QIWIZUSEXGLQGJ-UHFFFAOYSA-N CC(C)(CC1=C2)OC1=CN=C2C1=CSC(NC2=NC=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 Chemical compound CC(C)(CC1=C2)OC1=CN=C2C1=CSC(NC2=NC=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 QIWIZUSEXGLQGJ-UHFFFAOYSA-N 0.000 description 3
- QTCQEIMKHXZRHF-UHFFFAOYSA-N CC(C)(CC1=C2)OC1=CN=C2Cl Chemical compound CC(C)(CC1=C2)OC1=CN=C2Cl QTCQEIMKHXZRHF-UHFFFAOYSA-N 0.000 description 3
- FAOUPLILROOEQG-UHFFFAOYSA-N CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 Chemical compound CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 FAOUPLILROOEQG-UHFFFAOYSA-N 0.000 description 3
- IRUNQEGHXHZIPV-UHFFFAOYSA-N CC(C)NC(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)=O Chemical compound CC(C)NC(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)=O IRUNQEGHXHZIPV-UHFFFAOYSA-N 0.000 description 3
- FHBPWGOHEVRFDK-UHFFFAOYSA-N CC(C)OC(C=C1)=CN=C1C1=CSC(NC(N=C2)=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 Chemical compound CC(C)OC(C=C1)=CN=C1C1=CSC(NC(N=C2)=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 FHBPWGOHEVRFDK-UHFFFAOYSA-N 0.000 description 3
- FBYSYNQQJOCYBI-UHFFFAOYSA-N CC(C)OC1=CC(C2=CSC(NC(N=C3)=C(C(F)(F)F)C=C3N(C)C(C)=O)=N2)=NC=C1 Chemical compound CC(C)OC1=CC(C2=CSC(NC(N=C3)=C(C(F)(F)F)C=C3N(C)C(C)=O)=N2)=NC=C1 FBYSYNQQJOCYBI-UHFFFAOYSA-N 0.000 description 3
- AVMMZIBLCJYEHN-UHFFFAOYSA-N CC(C)OC1=CC(NC(NC(C2=CC=CC=C2)=O)=S)=NC=C1 Chemical compound CC(C)OC1=CC(NC(NC(C2=CC=CC=C2)=O)=S)=NC=C1 AVMMZIBLCJYEHN-UHFFFAOYSA-N 0.000 description 3
- JNKIIJYPNGOUMF-UHFFFAOYSA-N CC(C)OC1=CC=NC(Br)=C1 Chemical compound CC(C)OC1=CC=NC(Br)=C1 JNKIIJYPNGOUMF-UHFFFAOYSA-N 0.000 description 3
- XBQUBEGGXMETJA-UHFFFAOYSA-N CC(C=C1C)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 Chemical compound CC(C=C1C)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 XBQUBEGGXMETJA-UHFFFAOYSA-N 0.000 description 3
- QRZAEOCSYNNEJM-UHFFFAOYSA-N CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C)=C2)S1 Chemical compound CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C)=C2)S1 QRZAEOCSYNNEJM-UHFFFAOYSA-N 0.000 description 3
- JCVVEIKCYVLRIO-UHFFFAOYSA-N CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(OC3CCOCC3)=C2)S1 Chemical compound CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(OC3CCOCC3)=C2)S1 JCVVEIKCYVLRIO-UHFFFAOYSA-N 0.000 description 3
- IXLSSRBCERAAKN-UHFFFAOYSA-N CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2C(N(C)C)=O)=CS1 Chemical compound CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2C(N(C)C)=O)=CS1 IXLSSRBCERAAKN-UHFFFAOYSA-N 0.000 description 3
- YUNYAKVPDXKTTC-UHFFFAOYSA-N CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2C(N)=O)=CS1 Chemical compound CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2C(N)=O)=CS1 YUNYAKVPDXKTTC-UHFFFAOYSA-N 0.000 description 3
- MIFBFMXOIXUFDK-UHFFFAOYSA-N CCC1=C(C2=NC=CC=C2)N=C(NC2=NC(C(F)(F)F)=CC=C2)S1 Chemical compound CCC1=C(C2=NC=CC=C2)N=C(NC2=NC(C(F)(F)F)=CC=C2)S1 MIFBFMXOIXUFDK-UHFFFAOYSA-N 0.000 description 3
- WLIWROAMJAVFIV-UHFFFAOYSA-N CCCCC1=CC(NC(C)(C)C)=NC=C1 Chemical compound CCCCC1=CC(NC(C)(C)C)=NC=C1 WLIWROAMJAVFIV-UHFFFAOYSA-N 0.000 description 3
- GNSVDHXRWDNZEQ-UHFFFAOYSA-N CCCCC1=CC(NC(N)=S)=NC=C1 Chemical compound CCCCC1=CC(NC(N)=S)=NC=C1 GNSVDHXRWDNZEQ-UHFFFAOYSA-N 0.000 description 3
- TWFUVGXBWYXUCT-UHFFFAOYSA-N CCOC(C(C=C1)=NC=C1C(N(C)C)=O)=C Chemical compound CCOC(C(C=C1)=NC=C1C(N(C)C)=O)=C TWFUVGXBWYXUCT-UHFFFAOYSA-N 0.000 description 3
- ZTNFAAUJAGYQMI-UHFFFAOYSA-N CCOC(C(C=C1)=NC=C1OC(C)C)=C Chemical compound CCOC(C(C=C1)=NC=C1OC(C)C)=C ZTNFAAUJAGYQMI-UHFFFAOYSA-N 0.000 description 3
- UHLFSHVZYBQZMF-UHFFFAOYSA-N CCOC(C1=NC=C2OC(C)(C)CC2=C1)=C Chemical compound CCOC(C1=NC=C2OC(C)(C)CC2=C1)=C UHLFSHVZYBQZMF-UHFFFAOYSA-N 0.000 description 3
- JVSLWGDXPXQRLF-UHFFFAOYSA-N CCOC(C1=NC=CC(OC(C)C)=C1)=C Chemical compound CCOC(C1=NC=CC(OC(C)C)=C1)=C JVSLWGDXPXQRLF-UHFFFAOYSA-N 0.000 description 3
- WJYIEXFCAGQCRK-UHFFFAOYSA-N CCOC(C=C1)=CN=C1C1=CSC(N)=N1 Chemical compound CCOC(C=C1)=CN=C1C1=CSC(N)=N1 WJYIEXFCAGQCRK-UHFFFAOYSA-N 0.000 description 3
- XBRRPCXUADDSMD-UHFFFAOYSA-N CCOC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2C#N)=N1 Chemical compound CCOC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2C#N)=N1 XBRRPCXUADDSMD-UHFFFAOYSA-N 0.000 description 3
- CEKFPLLZVOPVTF-UHFFFAOYSA-N CCOC(CNC(C(C=C1)=NC=C1OC)=O)=O Chemical compound CCOC(CNC(C(C=C1)=NC=C1OC)=O)=O CEKFPLLZVOPVTF-UHFFFAOYSA-N 0.000 description 3
- NGDQNVOBVNDEMB-UHFFFAOYSA-N CCOC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O Chemical compound CCOC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O NGDQNVOBVNDEMB-UHFFFAOYSA-N 0.000 description 3
- KGMSZXOFVQZHLP-UHFFFAOYSA-N CN(C(C1=NC=CC=C1C1=CC=CC=C1)=O)OC Chemical compound CN(C(C1=NC=CC=C1C1=CC=CC=C1)=O)OC KGMSZXOFVQZHLP-UHFFFAOYSA-N 0.000 description 3
- PDFXEINAHNSKFW-UHFFFAOYSA-N CN(C)C(C(C=C1)=CN=C1C(CBr)=O)=O Chemical compound CN(C)C(C(C=C1)=CN=C1C(CBr)=O)=O PDFXEINAHNSKFW-UHFFFAOYSA-N 0.000 description 3
- RSKRBZQGBGZXKC-UHFFFAOYSA-N CN(C)CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 Chemical compound CN(C)CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 RSKRBZQGBGZXKC-UHFFFAOYSA-N 0.000 description 3
- VLAUWWLOMOYYTQ-UHFFFAOYSA-N COC(C=C1)=CN=C1C(CCl)=O Chemical compound COC(C=C1)=CN=C1C(CCl)=O VLAUWWLOMOYYTQ-UHFFFAOYSA-N 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- RNOKQVXWKKHQBR-UHFFFAOYSA-N ClC=1C=C2C(=CN=1)N(C(C2(C)C)=O)C Chemical compound ClC=1C=C2C(=CN=1)N(C(C2(C)C)=O)C RNOKQVXWKKHQBR-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000263692 Dirofilaria ursi Species 0.000 description 3
- 241000155708 Dolichocentrus tenuis Species 0.000 description 3
- 241001069183 Elaeophora Species 0.000 description 3
- 241000092921 Elaeophora schneideri Species 0.000 description 3
- 241000530560 Etheostoma sagitta Species 0.000 description 3
- PJVSAOIAUQGOAA-UHFFFAOYSA-N FC(C1=CC(NC2=NC(C(C=C3)=NC=C3F)=CS2)=NC=C1)(F)F Chemical compound FC(C1=CC(NC2=NC(C(C=C3)=NC=C3F)=CS2)=NC=C1)(F)F PJVSAOIAUQGOAA-UHFFFAOYSA-N 0.000 description 3
- YIZLSXDCFQIAFQ-UHFFFAOYSA-N FC(C1=CC(NC2=NC(C3=NC=CC=C3)=C(CN3CCCCC3)S2)=NC=C1)(F)F Chemical compound FC(C1=CC(NC2=NC(C3=NC=CC=C3)=C(CN3CCCCC3)S2)=NC=C1)(F)F YIZLSXDCFQIAFQ-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000255640 Loa loa Species 0.000 description 3
- PWPIIEIGLQYWCE-UHFFFAOYSA-N N#CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 Chemical compound N#CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 PWPIIEIGLQYWCE-UHFFFAOYSA-N 0.000 description 3
- MQONXGLXLZKVCA-UHFFFAOYSA-N N(=C=S)C1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F Chemical compound N(=C=S)C1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F MQONXGLXLZKVCA-UHFFFAOYSA-N 0.000 description 3
- WFTKALJXKPRMKX-UHFFFAOYSA-N NC(C(C=C1)=CN=C1C(CBr)=O)=O Chemical compound NC(C(C=C1)=CN=C1C(CBr)=O)=O WFTKALJXKPRMKX-UHFFFAOYSA-N 0.000 description 3
- ZZVDQZOXHYTKEC-UHFFFAOYSA-N NC(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)=O Chemical compound NC(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)=O ZZVDQZOXHYTKEC-UHFFFAOYSA-N 0.000 description 3
- YKSWNRUPGBYBLQ-UHFFFAOYSA-N NC(NC1=NC=C(C(F)(F)F)C=C1N(CCC1)C1=O)=S Chemical compound NC(NC1=NC=C(C(F)(F)F)C=C1N(CCC1)C1=O)=S YKSWNRUPGBYBLQ-UHFFFAOYSA-N 0.000 description 3
- LUBKZEYYMBPHPO-UHFFFAOYSA-N NC(NC1=NC=CC(C2=NC=CN=C2)=C1)=S Chemical compound NC(NC1=NC=CC(C2=NC=CN=C2)=C1)=S LUBKZEYYMBPHPO-UHFFFAOYSA-N 0.000 description 3
- GMFGDOAYPWJCRT-UHFFFAOYSA-N NC(NC1=NC=CC=C1C1=CC=CC=C1)=S Chemical compound NC(NC1=NC=CC=C1C1=CC=CC=C1)=S GMFGDOAYPWJCRT-UHFFFAOYSA-N 0.000 description 3
- IXHMUMUYBBBRNQ-UHFFFAOYSA-N O=C(C1(CC1)C(F)(F)F)N(CC1)CCN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1 Chemical compound O=C(C1(CC1)C(F)(F)F)N(CC1)CCN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1 IXHMUMUYBBBRNQ-UHFFFAOYSA-N 0.000 description 3
- ZBLMHSFFGHHXRT-UHFFFAOYSA-N O=C(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)N1CCCC1 Chemical compound O=C(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)N1CCCC1 ZBLMHSFFGHHXRT-UHFFFAOYSA-N 0.000 description 3
- COQRWHSAONSFJT-UHFFFAOYSA-N O=C(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)NCC(F)(F)F Chemical compound O=C(C1=CC(NC2=NC(C3=NC=CC=C3)=CS2)=NC=C1)NCC(F)(F)F COQRWHSAONSFJT-UHFFFAOYSA-N 0.000 description 3
- XQDSWDRSWXMRHD-UHFFFAOYSA-N OC(C(CCC1)CN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1)=O Chemical compound OC(C(CCC1)CN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1)=O XQDSWDRSWXMRHD-UHFFFAOYSA-N 0.000 description 3
- KMOCGDUKGCXXTB-UHFFFAOYSA-N OC(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)=O Chemical compound OC(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)=O KMOCGDUKGCXXTB-UHFFFAOYSA-N 0.000 description 3
- 241000243987 Onchocerca gibsoni Species 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 229930006000 Sucrose Natural products 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
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 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
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 3
- BLEBFDYUDVZRFG-UHFFFAOYSA-N dichloromethane;propan-2-ol Chemical compound ClCCl.CC(C)O BLEBFDYUDVZRFG-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- APAROCSWYXDWLU-UHFFFAOYSA-N ethyl 2-bromo-3-(3-methylpyridin-2-yl)-3-oxopropanoate Chemical compound BrC(C(=O)OCC)C(=O)C1=NC=CC=C1C APAROCSWYXDWLU-UHFFFAOYSA-N 0.000 description 3
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229960002449 glycine Drugs 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 3
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
- 230000001926 lymphatic effect Effects 0.000 description 3
- JDRKBLOKFWKWKA-UHFFFAOYSA-N n-methoxy-n-methylpyridine-2-carboxamide Chemical compound CON(C)C(=O)C1=CC=CC=N1 JDRKBLOKFWKWKA-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 3
- MCCLFFQZNBEOAV-UHFFFAOYSA-N pyrimidin-2-ylthiourea Chemical compound NC(=S)NC1=NC=CC=N1 MCCLFFQZNBEOAV-UHFFFAOYSA-N 0.000 description 3
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IYCKMNAVTMOAKD-UHFFFAOYSA-N 1,2-thiazol-3-amine Chemical compound NC=1C=CSN=1 IYCKMNAVTMOAKD-UHFFFAOYSA-N 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical group OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 2
- WRYBFZYPELHYHY-UHFFFAOYSA-N 2-bromo-1-(4-methylpyridin-2-yl)ethanone Chemical compound CC1=CC=NC(C(=O)CBr)=C1 WRYBFZYPELHYHY-UHFFFAOYSA-N 0.000 description 2
- BYKVUGZUYJUSKD-UHFFFAOYSA-N 2-bromo-1-pyridin-2-ylethanone;hydron;bromide Chemical compound [Br-].BrCC(=O)C1=CC=CC=[NH+]1 BYKVUGZUYJUSKD-UHFFFAOYSA-N 0.000 description 2
- YLGIMHONOXNWSQ-UHFFFAOYSA-N 2-bromo-1-pyrimidin-2-ylethanone;hydrobromide Chemical compound Br.BrCC(=O)C1=NC=CC=N1 YLGIMHONOXNWSQ-UHFFFAOYSA-N 0.000 description 2
- CUNUNPUTVNVYRH-UHFFFAOYSA-N 2-bromo-5-(oxan-4-yloxy)pyridine Chemical compound C1=NC(Br)=CC=C1OC1CCOCC1 CUNUNPUTVNVYRH-UHFFFAOYSA-N 0.000 description 2
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- PSRLFNWTVAVWJM-UHFFFAOYSA-N 5-(oxan-4-yloxy)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1OC1CCOCC1 PSRLFNWTVAVWJM-UHFFFAOYSA-N 0.000 description 2
- VEVBKOCTESXAOK-UHFFFAOYSA-N 5-(oxan-4-yloxy)pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1OC1CCOCC1 VEVBKOCTESXAOK-UHFFFAOYSA-N 0.000 description 2
- DIRQZKGUOSKZQX-UHFFFAOYSA-N 5-propan-2-yl-4-(trifluoromethyl)pyridin-2-amine Chemical compound CC(C)C1=CN=C(N)C=C1C(F)(F)F DIRQZKGUOSKZQX-UHFFFAOYSA-N 0.000 description 2
- PTEFNEALEPSHLC-UHFFFAOYSA-N 6-bromopyridin-3-ol Chemical compound OC1=CC=C(Br)N=C1 PTEFNEALEPSHLC-UHFFFAOYSA-N 0.000 description 2
- 241000189162 Acanthocheilonema reconditum Species 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- ASDHHERMDPOODK-UHFFFAOYSA-N C(C1)NCCN1C(C=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 Chemical compound C(C1)NCCN1C(C=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=CS1 ASDHHERMDPOODK-UHFFFAOYSA-N 0.000 description 2
- JWBGCZUDUCGJND-UHFFFAOYSA-N CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=C(NC2=NC(C3=NC=C4OC(C)(C)CC4=C3)=CS2)N=C1)=O Chemical compound CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=C(NC2=NC(C3=NC=C4OC(C)(C)CC4=C3)=CS2)N=C1)=O JWBGCZUDUCGJND-UHFFFAOYSA-N 0.000 description 2
- FJRXQYUWKMOTEX-UHFFFAOYSA-N CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C(C=C2C3(C)C)=NC=C2N(C)C3=O)=CS1)=O Chemical compound CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C(C=C2C3(C)C)=NC=C2N(C)C3=O)=CS1)=O FJRXQYUWKMOTEX-UHFFFAOYSA-N 0.000 description 2
- CQKRTQYDRXYBNF-UHFFFAOYSA-N CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C2=NC=C3N(C)C(C)(C)CC3=C2)=CS1)=O Chemical compound CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C2=NC=C3N(C)C(C)(C)CC3=C2)=CS1)=O CQKRTQYDRXYBNF-UHFFFAOYSA-N 0.000 description 2
- HDHCMWBPHTXYKI-UHFFFAOYSA-N CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C2=NC=C3OC(C)(C)CC3=C2)=CS1)=O Chemical compound CC(C)(C)OC(N(C)C1=CC(C(F)(F)F)=CN=C1NC1=NC(C2=NC=C3OC(C)(C)CC3=C2)=CS1)=O HDHCMWBPHTXYKI-UHFFFAOYSA-N 0.000 description 2
- SRMRCPPDESQQLK-UHFFFAOYSA-N CC(C)(CC1=C2)OC1=CN=C2C1=CSC(NC(N=C2)=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 Chemical compound CC(C)(CC1=C2)OC1=CN=C2C1=CSC(NC(N=C2)=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 SRMRCPPDESQQLK-UHFFFAOYSA-N 0.000 description 2
- QJUUMZGMXKCGPL-UHFFFAOYSA-N CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=C(C)S1 Chemical compound CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC1=NC(C2=NC=CC=C2)=C(C)S1 QJUUMZGMXKCGPL-UHFFFAOYSA-N 0.000 description 2
- BGXMISBINFYBTN-UHFFFAOYSA-N CC(C)OC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2S(N2CCC2)(=O)=O)=N1 Chemical compound CC(C)OC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2S(N2CCC2)(=O)=O)=N1 BGXMISBINFYBTN-UHFFFAOYSA-N 0.000 description 2
- IOFPPXKYZVSSNA-UHFFFAOYSA-N CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(NCC(F)(F)F)=O)=C2)S1 Chemical compound CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(NCC(F)(F)F)=O)=C2)S1 IOFPPXKYZVSSNA-UHFFFAOYSA-N 0.000 description 2
- SMMABDMPCVYRCM-UHFFFAOYSA-N CC1=CC(=NC=C1)NC=1SC(=C(N=1)C1=NC=CC=C1)C(=O)OCC Chemical compound CC1=CC(=NC=C1)NC=1SC(=C(N=1)C1=NC=CC=C1)C(=O)OCC SMMABDMPCVYRCM-UHFFFAOYSA-N 0.000 description 2
- HKSNJEKTVPSLEA-UHFFFAOYSA-N CC1=CC(NC2=NC(C(C=C3)=NC=C3OC)=CS2)=NC=C1 Chemical compound CC1=CC(NC2=NC(C(C=C3)=NC=C3OC)=CS2)=NC=C1 HKSNJEKTVPSLEA-UHFFFAOYSA-N 0.000 description 2
- HJLLQRCJOMJNMD-UHFFFAOYSA-N CC1=CC(NC2=NC(C3=NC=C(C)C=C3)=CS2)=NC=C1 Chemical compound CC1=CC(NC2=NC(C3=NC=C(C)C=C3)=CS2)=NC=C1 HJLLQRCJOMJNMD-UHFFFAOYSA-N 0.000 description 2
- BTVQOLZASAIUOC-UHFFFAOYSA-N CC1=CC(NC2=NC(C3=NC=CC(OC)=C3)=CS2)=NC=C1 Chemical compound CC1=CC(NC2=NC(C3=NC=CC(OC)=C3)=CS2)=NC=C1 BTVQOLZASAIUOC-UHFFFAOYSA-N 0.000 description 2
- ZUSHDQAMPDBPIA-UHFFFAOYSA-N CC1=CC(NC2=NC(C3=NC=CC=N3)=CS2)=NC=C1 Chemical compound CC1=CC(NC2=NC(C3=NC=CC=N3)=CS2)=NC=C1 ZUSHDQAMPDBPIA-UHFFFAOYSA-N 0.000 description 2
- UBEQJVNSFBHUAC-UHFFFAOYSA-N CC1=CC=CN=C1NC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O Chemical compound CC1=CC=CN=C1NC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O UBEQJVNSFBHUAC-UHFFFAOYSA-N 0.000 description 2
- VGSYAIAKRSPZIG-UHFFFAOYSA-N CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OC2CCOCC2)=CS1 Chemical compound CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OC2CCOCC2)=CS1 VGSYAIAKRSPZIG-UHFFFAOYSA-N 0.000 description 2
- XJKPCGFNJNSMTR-UHFFFAOYSA-N CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OCC(F)(F)F)=CS1 Chemical compound CC1=CC=CN=C1NC1=NC(C(C=C2)=NC=C2OCC(F)(F)F)=CS1 XJKPCGFNJNSMTR-UHFFFAOYSA-N 0.000 description 2
- MFIWRWNSYSFWFL-UHFFFAOYSA-N CCOC(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)=O Chemical compound CCOC(C1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1)=O MFIWRWNSYSFWFL-UHFFFAOYSA-N 0.000 description 2
- PWBNYAVIJCJNNJ-UHFFFAOYSA-N COC(C(C=C1)=NC=C1OC1CCOCC1)=O Chemical compound COC(C(C=C1)=NC=C1OC1CCOCC1)=O PWBNYAVIJCJNNJ-UHFFFAOYSA-N 0.000 description 2
- HLIMHNZXSUEEPZ-UHFFFAOYSA-N COC(C=C1)=CN=C1C1=CSC(NC(C=C2)=NC=C2OC2CCOCC2)=N1 Chemical compound COC(C=C1)=CN=C1C1=CSC(NC(C=C2)=NC=C2OC2CCOCC2)=N1 HLIMHNZXSUEEPZ-UHFFFAOYSA-N 0.000 description 2
- DEMZHMRJPJTAPQ-OKILXGFUSA-N C[C@H]1N[C@@H](C)CN(CC2=C(C3=NC=CC=C3)N=C(NC3=NC=CC(C(F)(F)F)=C3)S2)C1 Chemical compound C[C@H]1N[C@@H](C)CN(CC2=C(C3=NC=CC=C3)N=C(NC3=NC=CC(C(F)(F)F)=C3)S2)C1 DEMZHMRJPJTAPQ-OKILXGFUSA-N 0.000 description 2
- AYXQDDPCBKRLAI-GASCZTMLSA-N C[C@H]1O[C@@H](C)CN(CC2=C(C3=NC=CC=C3)N=C(NC3=NC=CC(C(NCC(F)(F)F)=O)=C3)S2)C1 Chemical compound C[C@H]1O[C@@H](C)CN(CC2=C(C3=NC=CC=C3)N=C(NC3=NC=CC(C(NCC(F)(F)F)=O)=C3)S2)C1 AYXQDDPCBKRLAI-GASCZTMLSA-N 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000189163 Dipetalonema Species 0.000 description 2
- 241001023203 Dracunculus lutrae Species 0.000 description 2
- BBXOYOQROKWAIC-UHFFFAOYSA-N FC(C1=CC(NC2=NC(C3=NC=CC=C3)=C(COCC3CC3)S2)=NC=C1)(F)F Chemical compound FC(C1=CC(NC2=NC(C3=NC=CC=C3)=C(COCC3CC3)S2)=NC=C1)(F)F BBXOYOQROKWAIC-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- 239000004471 Glycine Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000243251 Hydra Species 0.000 description 2
- 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 2
- 206010025282 Lymphoedema Diseases 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000530522 Mansonella ozzardi Species 0.000 description 2
- 241000142895 Mansonella perstans Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- OGNCIVHGIQSZEX-WAYWQWQTSA-N NC(/C=C(/C1=NC=CC=C1)\N)=S Chemical compound NC(/C=C(/C1=NC=CC=C1)\N)=S OGNCIVHGIQSZEX-WAYWQWQTSA-N 0.000 description 2
- USTRMRBPUMIQKC-UHFFFAOYSA-N NC1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F Chemical compound NC1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F USTRMRBPUMIQKC-UHFFFAOYSA-N 0.000 description 2
- LQBMLEWRCBANMM-UHFFFAOYSA-N O=C(C1=CC=CC=C1)NC(NC(C=C1)=NC=C1OC1CCOCC1)=S Chemical compound O=C(C1=CC=CC=C1)NC(NC(C=C1)=NC=C1OC1CCOCC1)=S LQBMLEWRCBANMM-UHFFFAOYSA-N 0.000 description 2
- RJVZHOUWPHKQLI-UHFFFAOYSA-N O=C(CBr)C(C=C1)=NC=C1OCC(F)(F)F Chemical compound O=C(CBr)C(C=C1)=NC=C1OCC(F)(F)F RJVZHOUWPHKQLI-UHFFFAOYSA-N 0.000 description 2
- ZOCTTYKRKCJCBM-UHFFFAOYSA-N O=C(CCl)C(C=C1)=NC=C1OC1CCOCC1 Chemical compound O=C(CCl)C(C=C1)=NC=C1OC1CCOCC1 ZOCTTYKRKCJCBM-UHFFFAOYSA-N 0.000 description 2
- HWPJVBYBABFHMR-UHFFFAOYSA-N O=CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 Chemical compound O=CC1=C(C2=NC=CC=C2)N=C(NC2=NC=CC(C(F)(F)F)=C2)S1 HWPJVBYBABFHMR-UHFFFAOYSA-N 0.000 description 2
- LOHVSQKWVQKZMN-UHFFFAOYSA-N OC1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1 Chemical compound OC1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1 LOHVSQKWVQKZMN-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000242594 Platyhelminthes Species 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 208000002848 Schistosomiasis mansoni Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000006626 Weinreb Ketone synthesis reaction Methods 0.000 description 2
- 241000244005 Wuchereria bancrofti Species 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 159000000021 acetate salts Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000033 alkoxyamino group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005602 azabenzimidazolyl group Chemical group 0.000 description 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 2
- 125000003725 azepanyl group Chemical group 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 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 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007910 chewable tablet Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 238000002592 echocardiography Methods 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- NJQLMEKGVBIVIL-UHFFFAOYSA-N ethyl 2-bromo-3-oxo-3-pyridin-2-ylpropanoate Chemical compound CCOC(=O)C(Br)C(=O)C1=CC=CC=N1 NJQLMEKGVBIVIL-UHFFFAOYSA-N 0.000 description 2
- OXBRTZCSNVTDJQ-UHFFFAOYSA-N ethyl 3-(3-methylpyridin-2-yl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=NC=CC=C1C OXBRTZCSNVTDJQ-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002541 furyl group Chemical group 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
- 239000008103 glucose Substances 0.000 description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 125000005638 hydrazono group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000007943 implant Substances 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
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000001524 infective effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 201000006675 intestinal schistosomiasis Diseases 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 208000002502 lymphedema Diseases 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- QMEBVRXZLKAAIG-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)-4-pyridin-2-yl-1,3-thiazol-2-amine Chemical compound CC1=CC=NC(NC=2SC=C(N=2)C=2N=CC=CC=2)=C1 QMEBVRXZLKAAIG-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- QJGQUHMNIGDVPM-OUBTZVSYSA-N nitrogen-15 Chemical compound [15N] QJGQUHMNIGDVPM-OUBTZVSYSA-N 0.000 description 2
- 208000003177 ocular onchocerciasis Diseases 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 210000004681 ovum Anatomy 0.000 description 2
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 210000001147 pulmonary artery Anatomy 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 description 1
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- JCFAFZULKPYMQV-UHFFFAOYSA-N 1-(5-methoxypyridin-2-yl)ethanone Chemical compound COC1=CC=C(C(C)=O)N=C1 JCFAFZULKPYMQV-UHFFFAOYSA-N 0.000 description 1
- SKCBKBCACWDALV-UHFFFAOYSA-N 1-(trifluoromethyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C(F)(F)F)CC1 SKCBKBCACWDALV-UHFFFAOYSA-N 0.000 description 1
- XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- DCALJVULAGICIX-UHFFFAOYSA-N 1-propylpyrrolidin-2-one Chemical compound CCCN1CCCC1=O DCALJVULAGICIX-UHFFFAOYSA-N 0.000 description 1
- SPZUXKZZYDALEY-UHFFFAOYSA-N 1-pyrimidin-2-ylethanone Chemical compound CC(=O)C1=NC=CC=N1 SPZUXKZZYDALEY-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- MKEJZKKVVUZXIS-UHFFFAOYSA-N 2,4-dibromo-1,3-thiazole Chemical compound BrC1=CSC(Br)=N1 MKEJZKKVVUZXIS-UHFFFAOYSA-N 0.000 description 1
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 description 1
- HRVQMQWVGKYDCF-UHFFFAOYSA-N 2-Acetyl-4-methylpyridine Chemical compound CC(=O)C1=CC(C)=CC=N1 HRVQMQWVGKYDCF-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- MFKZMURKFNOBQN-UHFFFAOYSA-N 2-bromo-1-(3-methylpyridin-2-yl)ethanone Chemical compound CC1=CC=CN=C1C(=O)CBr MFKZMURKFNOBQN-UHFFFAOYSA-N 0.000 description 1
- KQTAXBSJYNKNEO-UHFFFAOYSA-N 2-bromo-1-(4-methylpyridin-2-yl)ethanone;hydrobromide Chemical compound Br.CC1=CC=NC(C(=O)CBr)=C1 KQTAXBSJYNKNEO-UHFFFAOYSA-N 0.000 description 1
- SMWOAPIFSJVHPD-UHFFFAOYSA-N 2-bromo-1-(5-fluoropyridin-2-yl)ethanone;hydrobromide Chemical compound Br.FC1=CC=C(C(=O)CBr)N=C1 SMWOAPIFSJVHPD-UHFFFAOYSA-N 0.000 description 1
- UQDYFGWJLXKGAY-UHFFFAOYSA-N 2-bromo-1-(5-methylpyridin-2-yl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)N=C1 UQDYFGWJLXKGAY-UHFFFAOYSA-N 0.000 description 1
- WMHOYHBWJCJLLR-UHFFFAOYSA-N 2-bromo-1-pyrimidin-2-ylethanone Chemical compound BrCC(=O)C1=NC=CC=N1 WMHOYHBWJCJLLR-UHFFFAOYSA-N 0.000 description 1
- GGXSDQDNOMWAFV-UHFFFAOYSA-N 2-bromo-1h-pyridin-4-one Chemical compound BrC1=CC(=O)C=CN1 GGXSDQDNOMWAFV-UHFFFAOYSA-N 0.000 description 1
- IDWYAFGBVHVALW-UHFFFAOYSA-N 2-bromo-3-oxo-3-pyridin-2-ylpropanenitrile Chemical compound N#CC(Br)C(=O)C1=CC=CC=N1 IDWYAFGBVHVALW-UHFFFAOYSA-N 0.000 description 1
- KRIILKQTJUOQCJ-UHFFFAOYSA-N 2-bromo-4-phenylpyridine Chemical compound C1=NC(Br)=CC(C=2C=CC=CC=2)=C1 KRIILKQTJUOQCJ-UHFFFAOYSA-N 0.000 description 1
- WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 description 1
- QIPXEPRGYVAQFI-UHFFFAOYSA-N 2-bromopyridine-3-carbonitrile Chemical compound BrC1=NC=CC=C1C#N QIPXEPRGYVAQFI-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LBFOHFUYEDMEQC-UHFFFAOYSA-N 3,3-dimethyl-1-pyridin-2-ylbutan-1-one Chemical compound CC(C)(C)CC(=O)C1=CC=CC=N1 LBFOHFUYEDMEQC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RBCARPJOEUEZLS-UHFFFAOYSA-N 3-bromopyridin-2-amine Chemical compound NC1=NC=CC=C1Br RBCARPJOEUEZLS-UHFFFAOYSA-N 0.000 description 1
- QWBZMCXMVOZHMO-UHFFFAOYSA-N 3-methyl-5-(trifluoromethyl)pyridine Chemical compound CC1=CN=CC(C(F)(F)F)=C1 QWBZMCXMVOZHMO-UHFFFAOYSA-N 0.000 description 1
- WBXZCDIZXWDPBL-UHFFFAOYSA-N 3-methylpyridine-2-carbonitrile Chemical compound CC1=CC=CN=C1C#N WBXZCDIZXWDPBL-UHFFFAOYSA-N 0.000 description 1
- SJLPJJGKJSOUOR-UHFFFAOYSA-N 3-phenylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1C1=CC=CC=C1 SJLPJJGKJSOUOR-UHFFFAOYSA-N 0.000 description 1
- SVSUYEJKNSMKKW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-prop-1-en-2-yl-1,3,2-dioxaborolane Chemical compound CC(=C)B1OC(C)(C)C(C)(C)O1 SVSUYEJKNSMKKW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-UHFFFAOYSA-N 0.000 description 1
- BAQKUNMKVAPWGU-UHFFFAOYSA-N 4-bromopyridin-2-amine Chemical compound NC1=CC(Br)=CC=N1 BAQKUNMKVAPWGU-UHFFFAOYSA-N 0.000 description 1
- YDPVETCVRMPPOP-UHFFFAOYSA-N 4-butyl-1-oxidopyridin-1-ium Chemical compound CCCCC1=CC=[N+]([O-])C=C1 YDPVETCVRMPPOP-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
- ISESOOISZHSENQ-UHFFFAOYSA-N 5-bromo-2-chloro-4-methylpyridine Chemical compound CC1=CC(Cl)=NC=C1Br ISESOOISZHSENQ-UHFFFAOYSA-N 0.000 description 1
- QKPUTMUWAOGQJD-UHFFFAOYSA-N 5-chloro-1,3-dihydropyrrolo[2,3-c]pyridin-2-one Chemical compound C1=NC(Cl)=CC2=C1NC(=O)C2 QKPUTMUWAOGQJD-UHFFFAOYSA-N 0.000 description 1
- BHXHRMVSUUPOLX-UHFFFAOYSA-N 5-fluoropyridine-2-carbonitrile Chemical compound FC1=CC=C(C#N)N=C1 BHXHRMVSUUPOLX-UHFFFAOYSA-N 0.000 description 1
- YPKUGKJFOOZLHN-UHFFFAOYSA-N 5-methoxypyridine-2-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)N=C1 YPKUGKJFOOZLHN-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- HLPONRCXYZPNFJ-UHFFFAOYSA-N 6-acetylpyridine-3-carbonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=N1 HLPONRCXYZPNFJ-UHFFFAOYSA-N 0.000 description 1
- ZTWYBFHLUJUUDX-UHFFFAOYSA-N 6-aminopyridin-3-ol Chemical compound NC1=CC=C(O)C=N1 ZTWYBFHLUJUUDX-UHFFFAOYSA-N 0.000 description 1
- JDJBRMNTXORYEN-UHFFFAOYSA-N 6-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)N=C1 JDJBRMNTXORYEN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 241000244038 Brugia malayi Species 0.000 description 1
- HXDMYLVVXHUMNN-UHFFFAOYSA-N C1=CC=NC=C1.[Br+].[Br+].[Br+] Chemical compound C1=CC=NC=C1.[Br+].[Br+].[Br+] HXDMYLVVXHUMNN-UHFFFAOYSA-N 0.000 description 1
- IFVGPZJWVVCBRP-UHFFFAOYSA-N CC(C)(C(N(CC1)CCN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1)=O)O Chemical compound CC(C)(C(N(CC1)CCN1C1=CC=C(NC2=NC(C3=NC=CC=C3)=CS2)N=C1)=O)O IFVGPZJWVVCBRP-UHFFFAOYSA-N 0.000 description 1
- OHVFYWGQHUCLIK-UHFFFAOYSA-N CC(C)(CC1=C2)N(C)C1=CN=C2C1=CSC(NC2=NC=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 Chemical compound CC(C)(CC1=C2)N(C)C1=CN=C2C1=CSC(NC2=NC=C(C(F)(F)F)C=C2N(C)C(C)=O)=N1 OHVFYWGQHUCLIK-UHFFFAOYSA-N 0.000 description 1
- VAYYOABBFMLKSM-UHFFFAOYSA-N CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC(NC(C1=CC=CC=C1)=O)=S Chemical compound CC(C)C(C(C(F)(F)F)=C1)=CN=C1NC(NC(C1=CC=CC=C1)=O)=S VAYYOABBFMLKSM-UHFFFAOYSA-N 0.000 description 1
- YGNSAWFWPNORTJ-UHFFFAOYSA-N CC(C)OC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2C)=N1 Chemical compound CC(C)OC(C=C1)=CN=C1C1=CSC(NC2=NC=CC=C2C)=N1 YGNSAWFWPNORTJ-UHFFFAOYSA-N 0.000 description 1
- WQQVISHRBZZOOG-UHFFFAOYSA-N CC(C)OC1=CC(NC(CNC(C(C=C2)=NC=C2OC)=O)=O)=NC=C1 Chemical compound CC(C)OC1=CC(NC(CNC(C(C=C2)=NC=C2OC)=O)=O)=NC=C1 WQQVISHRBZZOOG-UHFFFAOYSA-N 0.000 description 1
- UYOUAPBUWTWIIM-UHFFFAOYSA-N CC1=CC=CN=C1C(C(C1=CC=CC=C1)Br)=O Chemical compound CC1=CC=CN=C1C(C(C1=CC=CC=C1)Br)=O UYOUAPBUWTWIIM-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- GNKNKCJXVVNIDB-UHFFFAOYSA-N ClC1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F Chemical compound ClC1=NC=C(C=C1N1C(CCC1)=O)C(F)(F)F GNKNKCJXVVNIDB-UHFFFAOYSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001442499 Dirofilaria repens Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241001069182 Elaeophora elaphi Species 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 206010061201 Helminthic infection Diseases 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241000143317 Litomosoides sigmodontis Species 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- LOZKSIOYCXZHBR-UHFFFAOYSA-N N(=C=S)C1=C(C=C(C=N1)N(C(OC(C)(C)C)=O)C)C(F)(F)F Chemical compound N(=C=S)C1=C(C=C(C=N1)N(C(OC(C)(C)C)=O)C)C(F)(F)F LOZKSIOYCXZHBR-UHFFFAOYSA-N 0.000 description 1
- UYPBHECWVMHJQR-UHFFFAOYSA-N N-(5-chloropyridin-2-yl)-4-pyrimidin-2-yl-1,3-thiazol-2-amine Chemical compound Clc1ccc(Nc2nc(cs2)-c2ncccn2)nc1 UYPBHECWVMHJQR-UHFFFAOYSA-N 0.000 description 1
- BLGNCMOMLHLNPO-UHFFFAOYSA-N N-(5-methoxypyridin-2-yl)-4-pyridin-2-yl-1,3-thiazol-2-amine Chemical compound COc1ccc(Nc2nc(cs2)-c2ccccn2)nc1 BLGNCMOMLHLNPO-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- MXPOUCQKKMOMNF-UHFFFAOYSA-N NC(C(C=CN=C1)=C1NC(N)=S)=O Chemical compound NC(C(C=CN=C1)=C1NC(N)=S)=O MXPOUCQKKMOMNF-UHFFFAOYSA-N 0.000 description 1
- 240000002778 Neonotonia wightii Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PSXVOBFEKBSQKS-UHFFFAOYSA-N O=C(CBr)C1=NC=CC=C1C1=CC=CC=C1 Chemical compound O=C(CBr)C1=NC=CC=C1C1=CC=CC=C1 PSXVOBFEKBSQKS-UHFFFAOYSA-N 0.000 description 1
- BQCOXSUYBSPGNJ-UHFFFAOYSA-N OC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O Chemical compound OC(CNC(C(C=C1)=NC=C1OC1CCOCC1)=O)=O BQCOXSUYBSPGNJ-UHFFFAOYSA-N 0.000 description 1
- 241000243983 Onchocerca gutturosa Species 0.000 description 1
- 241000244007 Onchocercidae Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000000127 Oxyuriasis Diseases 0.000 description 1
- 241000935974 Paralichthys dentatus Species 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 208000004318 Schistosomiasis haematobia Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-AKLPVKDBSA-N Sulfur-35 Chemical compound [35S] NINIDFKCEFEMDL-AKLPVKDBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000002140 Testicular Hydrocele Diseases 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 208000011312 Vector Borne disease Diseases 0.000 description 1
- 206010047571 Visual impairment Diseases 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-XXSWNUTMSA-N [125I][125I] Chemical compound [125I][125I] PNDPGZBMCMUPRI-XXSWNUTMSA-N 0.000 description 1
- ICVRVNZKPKJZOK-UHFFFAOYSA-N [6-(trifluoromethyl)pyridin-2-yl]thiourea Chemical compound FC(C1=CC=CC(=N1)NC(=S)N)(F)F ICVRVNZKPKJZOK-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005426 adeninyl group Chemical group N1=C(N=C2N=CNC2=C1N)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- LKDRXBCSQODPBY-ZXXMMSQZSA-N alpha-D-fructopyranose Chemical compound OC[C@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-ZXXMMSQZSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 235000015197 apple juice Nutrition 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 201000009361 ascariasis Diseases 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 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
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000005796 circulatory shock Effects 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
- WPOPOPFNZYPKAV-UHFFFAOYSA-N cyclobutylmethanol Chemical compound OCC1CCC1 WPOPOPFNZYPKAV-UHFFFAOYSA-N 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 description 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 125000000597 dioxinyl group Chemical group 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 208000008576 dracunculiasis Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 208000006036 elephantiasis Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- FQHXWZMJALFSJJ-UHFFFAOYSA-N ethyl 3-oxo-3-pyridin-2-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=N1 FQHXWZMJALFSJJ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- ZTUJDPKOHPKRMO-UHFFFAOYSA-N hydron;2,2,2-trifluoroethanamine;chloride Chemical compound Cl.NCC(F)(F)F ZTUJDPKOHPKRMO-UHFFFAOYSA-N 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- OPLZTPRSJUNYJI-UHFFFAOYSA-N isocyanatosulfanylmethylbenzene Chemical compound O=C=NSCC1=CC=CC=C1 OPLZTPRSJUNYJI-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000001638 macrofilaricidal effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- YYAYXDDHGPXWTA-UHFFFAOYSA-N methyl 5-hydroxypyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(O)C=N1 YYAYXDDHGPXWTA-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- GRFNBEZIAWKNCO-UHFFFAOYSA-N mhp Natural products OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 230000002574 microfilaricid Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 description 1
- 229960004816 moxidectin Drugs 0.000 description 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
- OYVXVLSZQHSNDK-UHFFFAOYSA-N n-methoxy-n-methylacetamide Chemical compound CON(C)C(C)=O OYVXVLSZQHSNDK-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- AQIDWPCFDNAMQW-UHFFFAOYSA-N pyridin-3-ol Chemical compound OC1=C=NC=C[CH]1 AQIDWPCFDNAMQW-UHFFFAOYSA-N 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 229960002245 selamectin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 229940001607 sodium bisulfite Drugs 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
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010268 sodium methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- RBOGBIZGALIITO-DTORHVGOSA-N tert-butyl (2s,6r)-2,6-dimethylpiperazine-1-carboxylate Chemical compound C[C@H]1CNC[C@@H](C)N1C(=O)OC(C)(C)C RBOGBIZGALIITO-DTORHVGOSA-N 0.000 description 1
- SAAGMIHGVLKZBC-UHFFFAOYSA-N tert-butyl n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]carbamate Chemical compound C1=NC(NC(=O)OC(C)(C)C)=CC(B2OC(C)(C)C(C)(C)O2)=C1 SAAGMIHGVLKZBC-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QWDWZQDTTVYOBK-UHFFFAOYSA-N tributyl-(3-methylpyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CC=C1C QWDWZQDTTVYOBK-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 208000009920 trichuriasis Diseases 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 201000004410 urinary schistosomiasis Diseases 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 208000029257 vision disease Diseases 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063105013P | 2020-10-23 | 2020-10-23 | |
| US63/105,013 | 2020-10-23 | ||
| PCT/US2021/056127 WO2022087326A1 (en) | 2020-10-23 | 2021-10-22 | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20230092972A true KR20230092972A (ko) | 2023-06-26 |
Family
ID=78676658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020237016754A Pending KR20230092972A (ko) | 2020-10-23 | 2021-10-22 | 연충 감염 및 질병의 치료를 위한 헤테로환식 화합물 및 이들의 용도 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20240025891A1 (https=) |
| EP (1) | EP4232449A1 (https=) |
| JP (1) | JP2023547396A (https=) |
| KR (1) | KR20230092972A (https=) |
| CN (1) | CN116547282A (https=) |
| WO (1) | WO2022087326A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| CN116744917A (zh) | 2020-09-04 | 2023-09-12 | 礼蓝美国公司 | 适口调配物 |
| CA3219348A1 (en) | 2021-05-27 | 2022-12-01 | Anthony B. Pinkerton | Checkpoint kinase 1 (chk1) inhibitors and uses thereof |
| KR20250025634A (ko) * | 2022-05-24 | 2025-02-24 | 바운드리스 바이오, 인크. | 피리딘 관문 키나제 1(chk1) 억제제 및 그의 용도 |
| EP4626433A1 (en) * | 2022-11-29 | 2025-10-08 | Boundless Bio, Inc. | Checkpoint kinase 1 (chk1) inhibitors combinations and uses thereof |
| CN115819429A (zh) * | 2022-12-13 | 2023-03-21 | 成都睿智化学研究有限公司 | 一种5-氯-2,3-二氢呋喃[2,3-c]吡啶的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2140543T3 (es) * | 1993-08-13 | 2000-03-01 | Zeneca Ltd | Derivados de tia- y oxadiazol y su uso como fungicidas o insecticidas. |
| US5614470A (en) * | 1994-04-01 | 1997-03-25 | Sankyo Company, Limited | 13-substituted milbemycin derivatives, their preparation and their use |
| US20050227989A1 (en) * | 2004-04-13 | 2005-10-13 | Icagen, Inc. | Polycyclic thiazoles as potassium ion channel modulators |
| KR20140071472A (ko) * | 2011-10-04 | 2014-06-11 | 인스티튜트 포 헤퍼타이티스 앤드 바이러스 리서치 | 간세포 암종을 포함하는 암의 저해제로서 그리고 간염 바이러스 복제의 저해제로서의 치환된 아미노티아졸 |
| US9695193B2 (en) * | 2013-06-26 | 2017-07-04 | The Trustees Of Columbia University In The City Of New York | Inhibitors of Plasmodium falciparum equilibrative nucleoside transporter type I as anti-parasitic compounds |
| WO2016144678A1 (en) * | 2015-03-12 | 2016-09-15 | E I Du Pont De Nemours And Company | Heterocycle-substituted bicyclic azole pesticides |
| US10913734B2 (en) * | 2016-07-11 | 2021-02-09 | Baruch S. Blumberg Institute | Substituted aminothiazoles |
| US11505548B2 (en) * | 2019-04-26 | 2022-11-22 | Celgene Corporation | Heterocyclic compounds and their use for treatment of helminthic infections and diseases |
-
2021
- 2021-10-22 US US18/032,998 patent/US20240025891A1/en active Pending
- 2021-10-22 EP EP21810484.2A patent/EP4232449A1/en active Pending
- 2021-10-22 JP JP2023524715A patent/JP2023547396A/ja active Pending
- 2021-10-22 WO PCT/US2021/056127 patent/WO2022087326A1/en not_active Ceased
- 2021-10-22 CN CN202180071227.3A patent/CN116547282A/zh active Pending
- 2021-10-22 KR KR1020237016754A patent/KR20230092972A/ko active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN116547282A (zh) | 2023-08-04 |
| US20240025891A1 (en) | 2024-01-25 |
| WO2022087326A1 (en) | 2022-04-28 |
| JP2023547396A (ja) | 2023-11-10 |
| EP4232449A1 (en) | 2023-08-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7546596B2 (ja) | ヘテロ環式化合物ならびに蠕虫感染および疾患におけるその使用 | |
| KR20230092972A (ko) | 연충 감염 및 질병의 치료를 위한 헤테로환식 화합물 및 이들의 용도 | |
| EP4139286B1 (en) | Substituted aminothiazoles as dgkzeta inhibitors for immune activation | |
| ES2935173T3 (es) | Composiciones farmacéuticas que comprenden derivados de imidazotiadiazol e imidazopiridazina como inhibidores del receptor activado por proteasa 4 (PAR4) para tratar la agregación plaquetaria | |
| DK2507245T3 (en) | MULTICYCLIC RELATIONS AND PROCEDURES FOR USE THEREOF | |
| JP6251275B2 (ja) | ナトリウムチャンネル阻害剤、その製造方法およびその用途 | |
| JP7451569B2 (ja) | ヒストン脱アセチル化酵素6阻害剤としての1,3,4-オキサジアゾールホモフタルイミド誘導体化合物、およびそれを含む薬剤学的組成物 | |
| KR20230146012A (ko) | 연충 감염 및 질병의 치료를 위한 설폰아미드 및 이들의용도 | |
| CA3072989A1 (en) | Inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan 2,3-dioxygenase | |
| HK40068974A (en) | Heterocyclic compounds and their use for treatment of helminthic infections and diseases | |
| CA3189672A1 (en) | Copper complexes for treatment of neurodegenerative disorders | |
| BR112022019057B1 (pt) | Aminotiazóis substituídos como inibidores de dgkzeta para ativação imune, seus usos, composição e combinação farmacêuticas, e kit |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20230517 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20241022 Comment text: Request for Examination of Application |