TWI742067B - 新吡唑並嘧啶衍生物 - Google Patents

Info

Publication number

TWI742067B

TWI742067B TW106112313A TW106112313A TWI742067B TW I742067 B TWI742067 B TW I742067B TW 106112313 A TW106112313 A TW 106112313A TW 106112313 A TW106112313 A TW 106112313A TW I742067 B TWI742067 B TW I742067B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

hydrogen

methyl

haloalkyl

Prior art date

2016-04-15

Links

• Espacenet
• Global Dossier
• Discuss

• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 322
• 238000000034 method Methods 0.000 claims abstract description 174
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 230000006806 disease prevention Effects 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 3
• -1 -OH Chemical group 0.000 claims description 295
• 229910052739 hydrogen Inorganic materials 0.000 claims description 235
• 239000001257 hydrogen Substances 0.000 claims description 235
• 239000000203 mixture Substances 0.000 claims description 126
• 125000005843 halogen group Chemical group 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 104
• 239000000460 chlorine Chemical group 0.000 claims description 94
• 229910052801 chlorine Inorganic materials 0.000 claims description 94
• 229910052731 fluorine Inorganic materials 0.000 claims description 93
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 91
• 239000011737 fluorine Substances 0.000 claims description 91
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 84
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
• 239000012453 solvate Substances 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 150000004677 hydrates Chemical class 0.000 claims description 56
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
• 150000001204 N-oxides Chemical class 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical group 0.000 claims description 45
• 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 claims description 43
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 28
• 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims description 28
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
• 229910052794 bromium Inorganic materials 0.000 claims description 25
• 208000006968 Helminthiasis Diseases 0.000 claims description 23
• 241001465754 Metazoa Species 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
• 229910052727 yttrium Inorganic materials 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000002757 morpholinyl 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 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 238000006243 chemical reaction Methods 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 16
• 125000002950 monocyclic group Chemical group 0.000 claims description 15
• 238000006467 substitution reaction Methods 0.000 claims description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 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
• 150000003053 piperidines Chemical class 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
• IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 6
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 6
• 241001061127 Thione Species 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 150000002460 imidazoles Chemical class 0.000 claims description 4
• 150000002576 ketones Chemical class 0.000 claims description 4
• 150000003217 pyrazoles Chemical class 0.000 claims description 4
• 150000003233 pyrroles Chemical class 0.000 claims description 4
• 150000003235 pyrrolidines Chemical class 0.000 claims description 4
• 150000003852 triazoles Chemical class 0.000 claims description 4
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 3
• NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 3
• 150000002780 morpholines Chemical class 0.000 claims description 3
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 80
• 125000005323 thioketone group Chemical group 0.000 claims 2
• 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 1
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
• 150000001538 azepines Chemical class 0.000 claims 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 abstract description 28
• 244000000013 helminth Species 0.000 abstract description 5
• 108010034145 Helminth Proteins Proteins 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 109
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 64
• 239000000243 solution Substances 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 43
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
• 238000005160 1H NMR spectroscopy Methods 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
• 238000000746 purification Methods 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• 238000001514 detection method Methods 0.000 description 29
• 239000003480 eluent Substances 0.000 description 29
• 239000007787 solid Substances 0.000 description 28
• 230000002496 gastric effect Effects 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 229910052805 deuterium Inorganic materials 0.000 description 24
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• 239000000543 intermediate Chemical class 0.000 description 22
• 241000244206 Nematoda Species 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 239000000463 material Substances 0.000 description 21
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 20
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• 238000003756 stirring Methods 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 238000005516 engineering process Methods 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• 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 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 235000019253 formic acid Nutrition 0.000 description 16
• 208000015181 infectious disease Diseases 0.000 description 16
• 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
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
• 239000003153 chemical reaction reagent Substances 0.000 description 15
• 238000010992 reflux 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
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 13
• 239000001099 ammonium carbonate Substances 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 229920006395 saturated elastomer Polymers 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 12
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 12
• 150000001721 carbon Chemical group 0.000 description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• 239000002585 base Substances 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• 150000001408 amides Chemical class 0.000 description 10
• 238000009833 condensation Methods 0.000 description 10
• 230000005494 condensation Effects 0.000 description 10
• 125000004494 ethyl ester group Chemical group 0.000 description 10
• 150000002430 hydrocarbons Chemical group 0.000 description 10
• PVKOBDBNKFBZQZ-UHFFFAOYSA-N 1h-pyrazolo[1,5-a]pyrimidin-2-one Chemical compound N1=CC=CN2N=C(O)C=C21 PVKOBDBNKFBZQZ-UHFFFAOYSA-N 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 239000003112 inhibitor Substances 0.000 description 9
• 230000000155 isotopic effect Effects 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 230000008878 coupling Effects 0.000 description 8
• 238000010168 coupling process Methods 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 239000007789 gas Substances 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 239000002207 metabolite Substances 0.000 description 8
• 238000007127 saponification reaction Methods 0.000 description 8
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 7
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 7
• 229940050176 methyl chloride Drugs 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• 241000238421 Arthropoda Species 0.000 description 6
• 241000282412 Homo Species 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 238000004458 analytical method Methods 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
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