RU2769448C2 - Новые пиразолпиримидиновые производные - Google Patents

Info

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

2016-04-15

Links

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• Global Dossier
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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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