EA023258B1 - 1,4-пиперазиновые производные в качестве средства от вирусного гриппа - Google Patents

Info

Publication number

EA023258B1

EA023258B1 EA201390362A EA201390362A EA023258B1 EA 023258 B1 EA023258 B1 EA 023258B1 EA 201390362 A EA201390362 A EA 201390362A EA 201390362 A EA201390362 A EA 201390362A EA 023258 B1 EA023258 B1 EA 023258B1

Authority

EA

Eurasian Patent Office

Prior art keywords

mmol

formula

methyl

phenyl

compound according

Prior art date

2010-09-08

Links

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• Global Dossier
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• 206010022000 influenza Diseases 0.000 title description 19
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
• 239000003443 antiviral agent Substances 0.000 title 1
• 229940121357 antivirals Drugs 0.000 title 1
• -1 isoxazole-4-yl Chemical group 0.000 claims abstract description 167
• 150000001875 compounds Chemical class 0.000 claims abstract description 149
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
• 125000001424 substituent group Chemical group 0.000 claims abstract description 20
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
• 150000002367 halogens Chemical class 0.000 claims abstract description 18
• 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
• 241000712461 unidentified influenza virus Species 0.000 claims abstract description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 3
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 239000002904 solvent Substances 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003368 amide group Chemical group 0.000 claims description 12
• 230000000840 anti-viral effect Effects 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 2
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
• 239000000203 mixture Substances 0.000 abstract description 55
• 230000002265 prevention Effects 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• 238000002360 preparation method Methods 0.000 description 104
• 238000005481 NMR spectroscopy Methods 0.000 description 59
• 238000004128 high performance liquid chromatography Methods 0.000 description 51
• 229940079593 drug Drugs 0.000 description 43
• 239000003814 drug Substances 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• 239000000047 product Substances 0.000 description 39
• 239000000543 intermediate Substances 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 37
• 239000000243 solution Substances 0.000 description 37
• 229910052739 hydrogen Inorganic materials 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 238000005160 1H NMR spectroscopy Methods 0.000 description 23
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 19
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 238000000746 purification Methods 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000002953 preparative HPLC Methods 0.000 description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 125000000623 heterocyclic group Chemical group 0.000 description 12
• KOQSJBSGCNLIJY-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound COC1=CC=CC=C1C1=NOC(C)=C1C(O)=O KOQSJBSGCNLIJY-UHFFFAOYSA-N 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 10
• 125000000753 cycloalkyl group Chemical group 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 229910052700 potassium Inorganic materials 0.000 description 8
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
• VSCBATMPTLKTOV-UHFFFAOYSA-N 2-tert-butylimino-n,n-diethyl-1,3-dimethyl-1,3,2$l^{5}-diazaphosphinan-2-amine Chemical compound CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C VSCBATMPTLKTOV-UHFFFAOYSA-N 0.000 description 7
• 241000700605 Viruses Species 0.000 description 7
• MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 125000004104 aryloxy group Chemical group 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 125000005404 thioheteroaryloxy group Chemical group 0.000 description 6
• 125000005190 thiohydroxy group Chemical group 0.000 description 6
• YDKWTEYRNMUJKC-UHFFFAOYSA-N 4-(2-oxopyrrolidin-1-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(=O)CCC1 YDKWTEYRNMUJKC-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 5
• 125000005309 thioalkoxy group Chemical group 0.000 description 5
• 125000005296 thioaryloxy group Chemical group 0.000 description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
• HHSYXYRGTNBGGU-UHFFFAOYSA-N 4-chloro-2-nitro-5-piperazin-1-ylaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(N2CCNCC2)=C1Cl HHSYXYRGTNBGGU-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 230000037396 body weight Effects 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 150000001805 chlorine compounds Chemical class 0.000 description 4
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
• 208000015181 infectious disease Diseases 0.000 description 4
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• KZZHPWMVEVZEFG-UHFFFAOYSA-N tert-butyl n-phenylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1 KZZHPWMVEVZEFG-UHFFFAOYSA-N 0.000 description 4
• 125000005152 trihalomethanesulfonyl group Chemical group 0.000 description 4
• 125000004953 trihalomethyl group Chemical group 0.000 description 4
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 3
• BGHXUMZQYBZECU-SNAWJCMRSA-N (e)-1,1,1-trichloro-4-ethoxy-3-methylbut-3-en-2-one Chemical compound CCO\C=C(/C)C(=O)C(Cl)(Cl)Cl BGHXUMZQYBZECU-SNAWJCMRSA-N 0.000 description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
• FVZODFVCIDBDGS-UHFFFAOYSA-N 3-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C(Br)=C1 FVZODFVCIDBDGS-UHFFFAOYSA-N 0.000 description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• UUHCWPKPPBWCPI-UHFFFAOYSA-N 5-chloro-3-nitro-6-piperazin-1-ylpyridin-2-amine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(N2CCNCC2)=C1Cl UUHCWPKPPBWCPI-UHFFFAOYSA-N 0.000 description 3
• PXRRJXZFSMXIEX-UHFFFAOYSA-N 5-methyl-3-naphthalen-1-yl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C1=CC=CC2=CC=CC=C12 PXRRJXZFSMXIEX-UHFFFAOYSA-N 0.000 description 3
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 206010011224 Cough Diseases 0.000 description 3
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• XNKMCXBVBVGTEY-UHFFFAOYSA-N [4-(5-amino-2-chloro-4-nitrophenyl)piperazin-1-yl]-[3-(2-methoxyphenyl)-5-methyl-1,2-oxazol-4-yl]methanone Chemical compound COC1=CC=CC=C1C1=NOC(C)=C1C(=O)N1CCN(C=2C(=CC(=C(N)C=2)[N+]([O-])=O)Cl)CC1 XNKMCXBVBVGTEY-UHFFFAOYSA-N 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 239000000443 aerosol Substances 0.000 description 3
• 150000001299 aldehydes Chemical class 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
• 229910000024 caesium carbonate Inorganic materials 0.000 description 3
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 150000001735 carboxylic acids Chemical class 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 210000003918 fraction a Anatomy 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
• 150000002431 hydrogen Chemical class 0.000 description 3
• 150000002545 isoxazoles Chemical class 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
• 230000003000 nontoxic effect Effects 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 125000005499 phosphonyl group Chemical group 0.000 description 3
• 150000003217 pyrazoles Chemical class 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• RDDJGGDBEXQEQZ-UHFFFAOYSA-N tert-butyl 4-(5-amino-2-chloro-4-nitrophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC(N)=C([N+]([O-])=O)C=C1Cl RDDJGGDBEXQEQZ-UHFFFAOYSA-N 0.000 description 3
• 125000005423 trihalomethanesulfonamido group Chemical group 0.000 description 3
• 229910052727 yttrium Inorganic materials 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
• HKZCFGQSWLWNQA-UHFFFAOYSA-N 1,3-thiazole-2-carbonyl chloride Chemical compound ClC(=O)C1=NC=CS1 HKZCFGQSWLWNQA-UHFFFAOYSA-N 0.000 description 2
• MREZSSGRNNMUKZ-UHFFFAOYSA-N 2,4-difluoro-5-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=C(F)C=C1F MREZSSGRNNMUKZ-UHFFFAOYSA-N 0.000 description 2
• NXRWYPPOQTVDLE-UHFFFAOYSA-N 3,5-dichloro-6-piperazin-1-ylpyridin-2-amine Chemical compound C1=C(Cl)C(N)=NC(N2CCNCC2)=C1Cl NXRWYPPOQTVDLE-UHFFFAOYSA-N 0.000 description 2
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
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