RU2769448C2 - Новые пиразолпиримидиновые производные - Google Patents
Новые пиразолпиримидиновые производные Download PDFInfo
- Publication number
- RU2769448C2 RU2769448C2 RU2018140092A RU2018140092A RU2769448C2 RU 2769448 C2 RU2769448 C2 RU 2769448C2 RU 2018140092 A RU2018140092 A RU 2018140092A RU 2018140092 A RU2018140092 A RU 2018140092A RU 2769448 C2 RU2769448 C2 RU 2769448C2
- Authority
- RU
- Russia
- Prior art keywords
- hydrogen
- group
- alkyl
- methyl
- cyclopropyl
- Prior art date
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- KEUDMLLLHGLIGH-UHFFFAOYSA-N 1h-pyrazole;pyrimidine Chemical class C=1C=NNC=1.C1=CN=CN=C1 KEUDMLLLHGLIGH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 337
- -1 pyrazole pyrimidine compound Chemical class 0.000 claims abstract description 273
- 238000000034 method Methods 0.000 claims abstract description 251
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 204
- 239000001257 hydrogen Substances 0.000 claims abstract description 204
- 239000000203 mixture Substances 0.000 claims abstract description 151
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 132
- 150000003839 salts Chemical class 0.000 claims abstract description 97
- 239000000460 chlorine Substances 0.000 claims abstract description 92
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 91
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 88
- 125000005843 halogen group Chemical group 0.000 claims abstract description 73
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 68
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 67
- 239000011737 fluorine Substances 0.000 claims abstract description 65
- 239000012453 solvate Substances 0.000 claims abstract description 57
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 52
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 41
- 208000006968 Helminthiasis Diseases 0.000 claims abstract description 30
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 241001465754 Metazoa Species 0.000 claims abstract description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 101100421668 Caenorhabditis elegans slo-1 gene Proteins 0.000 claims abstract description 5
- 102000004310 Ion Channels Human genes 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims description 41
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 40
- 238000011282 treatment Methods 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 13
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- AAFATJBXUGMOMP-UHFFFAOYSA-N N-[diethylamino-[1-(dimethylamino)-1-(ethylamino)ethyl]sulfonylamino]-2-(difluoromethoxy)-N-(methylamino)-2-(2,2,2-trifluoroethoxy)-2-(trifluoromethoxy)acetamide Chemical compound FC(OC(C(=O)N(N(S(=O)(=O)C(NCC)(C)N(C)C)N(CC)CC)NC)(OCC(F)(F)F)OC(F)F)(F)F AAFATJBXUGMOMP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
- 230000000507 anthelmentic effect Effects 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 8
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 261
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 90
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 86
- 239000011541 reaction mixture Substances 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 76
- 239000000243 solution Substances 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- 238000000746 purification Methods 0.000 description 57
- 238000005160 1H NMR spectroscopy Methods 0.000 description 54
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
- 238000003818 flash chromatography Methods 0.000 description 43
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 42
- 229910052938 sodium sulfate Inorganic materials 0.000 description 42
- 235000011152 sodium sulphate Nutrition 0.000 description 42
- 239000002904 solvent Substances 0.000 description 42
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 150000001204 N-oxides Chemical class 0.000 description 39
- 125000001424 substituent group Chemical group 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000003480 eluent Substances 0.000 description 33
- 239000012267 brine Substances 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- 239000007787 solid Substances 0.000 description 31
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- 238000001514 detection method Methods 0.000 description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 29
- 239000012044 organic layer Substances 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 28
- 229910052805 deuterium Inorganic materials 0.000 description 27
- 125000004093 cyano group Chemical group *C#N 0.000 description 26
- 230000002496 gastric effect Effects 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 25
- 239000000543 intermediate Substances 0.000 description 25
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 19
- 241000244206 Nematoda Species 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 208000015181 infectious disease Diseases 0.000 description 17
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 150000001735 carboxylic acids Chemical class 0.000 description 16
- 238000005516 engineering process Methods 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- 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 15
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 14
- 244000000013 helminth Species 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000001099 ammonium carbonate Substances 0.000 description 13
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 13
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 13
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 13
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 125000004043 oxo group Chemical group O=* 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 239000003643 water by type Substances 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 239000002480 mineral oil Substances 0.000 description 11
- 235000010446 mineral oil Nutrition 0.000 description 11
- 235000011056 potassium acetate Nutrition 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 description 10
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 230000000155 isotopic effect Effects 0.000 description 10
- 239000000921 anthelmintic agent Substances 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000002207 metabolite Substances 0.000 description 9
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 8
- TVOJIBGZFYMWDT-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CNN=C1 TVOJIBGZFYMWDT-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000005909 Kieselgur Substances 0.000 description 8
- 229940124339 anthelmintic agent Drugs 0.000 description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000006356 dehydrogenation reaction Methods 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- BCJQJAVVUTUJPF-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical class N1=CC=CN2N=C(C(=O)N)C=C21 BCJQJAVVUTUJPF-UHFFFAOYSA-N 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000006806 disease prevention Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- BVMKYKMJUZEGBU-QRPNPIFTSA-N (4s)-3,4-dihydro-2h-chromen-4-amine;hydrochloride Chemical compound Cl.C1=CC=C2[C@@H](N)CCOC2=C1 BVMKYKMJUZEGBU-QRPNPIFTSA-N 0.000 description 6
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 6
- WUIYGXGXVOHAFW-UHFFFAOYSA-N 2-[3-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(CBr)=C1 WUIYGXGXVOHAFW-UHFFFAOYSA-N 0.000 description 6
- ZQARVLMZLATKQJ-UHFFFAOYSA-N 5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2C=C(C=CC=2)C(F)(F)F)=C1C ZQARVLMZLATKQJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241000238421 Arthropoda Species 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QBQOFGAGRMJUSR-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-4-methyl-3-oxopentanoate Chemical compound CCOC=C(C(=O)C(C)C)C(=O)OCC QBQOFGAGRMJUSR-UHFFFAOYSA-N 0.000 description 6
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 6
- 238000000105 evaporative light scattering detection Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
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- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
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- 150000003626 triacylglycerols Chemical class 0.000 description 1
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- XOIOGKHKNQYULW-HTNNXBMUSA-N tribendimidine Chemical compound C1=CC(/N=C(\C)N(C)C)=CC=C1\N=C\C(C=C1)=CC=C1\C=N\C1=CC=C(\N=C(/C)N(C)C)C=C1 XOIOGKHKNQYULW-HTNNXBMUSA-N 0.000 description 1
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- 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
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- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- 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
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
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| EP16165572 | 2016-04-15 | ||
| EP16165572.5 | 2016-04-15 | ||
| PCT/EP2017/058519 WO2017178416A1 (en) | 2016-04-15 | 2017-04-10 | Pyrazolopyrimidine derivatives |
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| RU2018140092A RU2018140092A (ru) | 2020-05-15 |
| RU2018140092A3 RU2018140092A3 (enExample) | 2020-06-25 |
| RU2769448C2 true RU2769448C2 (ru) | 2022-03-31 |
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| SG (1) | SG11201808214TA (enExample) |
| TW (1) | TWI742067B (enExample) |
| UY (1) | UY37201A (enExample) |
| WO (1) | WO2017178416A1 (enExample) |
| ZA (1) | ZA201807656B (enExample) |
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| WO2016022066A1 (en) | 2014-08-04 | 2016-02-11 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| CA3018802A1 (en) | 2016-04-15 | 2017-10-19 | Abbvie Inc. | Bromodomain inhibitors |
| ES2953467T3 (es) | 2016-04-15 | 2023-11-13 | Elanco Animal Health Gmbh | Derivados de pirazolopirimidina |
| US11672800B2 (en) | 2017-04-21 | 2023-06-13 | Epizyme, Inc. | Combination therapies with EHMT2 inhibitors |
| WO2018197401A1 (en) | 2017-04-27 | 2018-11-01 | Bayer Animal Health Gmbh | New bicyclic pyrazole derivatives |
| JP2020533376A (ja) | 2017-09-15 | 2020-11-19 | アドゥロ バイオテック，インク． | ピラゾロピリミジノン化合物およびその使用 |
| KR20250065422A (ko) | 2017-12-15 | 2025-05-12 | 타르서스 파마수티칼스, 아이엔씨. | 안검염을 치료하기 위한 이속사졸린 구충제 제제 및 방법 |
| SG11202010024UA (en) * | 2018-05-09 | 2020-11-27 | Bayer Animal Health Gmbh | New quinoline derivatives |
| WO2020014068A1 (en) | 2018-07-09 | 2020-01-16 | Boehringer Ingelheim Animal Health USA Inc. | Anthelminthic heterocyclic compounds |
| EP3643711A1 (en) * | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
| NZ777370A (en) * | 2018-12-18 | 2024-11-29 | Elanco Tiergesundheit Ag | Bicyclic derivatives |
| PL3897842T3 (pl) * | 2018-12-18 | 2025-05-19 | Elanco Tiergesundheit Ag | Pochodne bicykliczne |
| CA3133100A1 (en) * | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| US12448391B2 (en) | 2019-06-07 | 2025-10-21 | Elanco Tiergesundheit Ag | Bicyclic derivatives for treating endoparasites |
| TWI865563B (zh) * | 2019-07-30 | 2024-12-11 | 德商拜耳動物保健有限公司 | 新穎異喹啉衍生物 |
| CA3164098A1 (en) * | 2019-12-18 | 2021-06-24 | Intervet International B.V. | Anthelmintic compounds comprising a quinoline structure |
| WO2021122906A1 (en) | 2019-12-18 | 2021-06-24 | Intervet International B.V. | Anthelmintic compounds comprising azaindoles structure |
| AU2021278889A1 (en) * | 2020-05-29 | 2023-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelmintic heterocyclic compounds |
| CN116685584A (zh) * | 2020-11-18 | 2023-09-01 | 礼蓝动物保健有限公司 | 用于治疗心丝虫感染的n-(2,3-二氢-1,4-苯并噁嗪-4-基)-3-异丙基-7-(2,3,5-三氟苯基)苯并噻吩-2-甲酰胺衍生物和类似化合物 |
| JP2023553269A (ja) | 2020-11-18 | 2023-12-21 | エランコ・ティアゲゾンタイト・アーゲー | イヌ糸状虫感染症を治療するためのｎ－（２，３－ジヒドロ－１，４－ベンゾオキサジン－４－イル）－３－イソプロピル－７－（２，３，５－トリフルオロフェニル）ベンゾ－チオフェン－２－カルボキサミド誘導体及び類似化合物 |
| TW202237600A (zh) | 2020-12-04 | 2022-10-01 | 瑞士商禮藍動物保健股份有限公司 | 雙環衍生物 |
| US20240043446A1 (en) * | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a thienopyridine structure |
| CN113252824B (zh) * | 2021-06-17 | 2022-04-19 | 湖南农业大学 | 测定水体中三氟苯嘧啶含量的气相色谱-电子捕获检测器法 |
| KR102660894B1 (ko) * | 2021-09-17 | 2024-04-26 | 기초과학연구원 | 피리미딘-2-아민 화합물의 제조방법 |
| UY39995A (es) | 2021-11-01 | 2023-05-15 | Boehringer Ingelheim Vetmedica GmbH | Compuestos de pirrolopiridazina como antihelmínticos |
| WO2024213752A1 (en) | 2023-04-14 | 2024-10-17 | Elanco Animal Health Gmbh | Long-term prevention and/or treatment of a disease by slo-1 inhibitors |
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