BR112012017441B1 - compostos e métodos - Google Patents

Info

Publication number

BR112012017441B1

BR112012017441B1 BR112012017441-0A BR112012017441A BR112012017441B1 BR 112012017441 B1 BR112012017441 B1 BR 112012017441B1 BR 112012017441 A BR112012017441 A BR 112012017441A BR 112012017441 B1 BR112012017441 B1 BR 112012017441B1

Authority

BR

Brazil

Prior art keywords

alkyl

methyl

optionally substituted

compound

phenyl

Prior art date

2010-01-13

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 407
• 238000000034 method Methods 0.000 title abstract description 26
• -1 aryl (C1-C4) alkyl Chemical group 0.000 claims description 440
• 125000000217 alkyl group Chemical group 0.000 claims description 159
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 95
• 150000003839 salts Chemical class 0.000 claims description 82
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 81
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 36
• 125000004429 atom Chemical group 0.000 claims description 35
• 125000001188 haloalkyl group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 31
• 239000000460 chlorine Substances 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229910052731 fluorine Inorganic materials 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 239000011737 fluorine Substances 0.000 claims description 26
• 125000001544 thienyl group Chemical group 0.000 claims description 26
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
• 125000002971 oxazolyl group Chemical group 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• NLUHMENALNPHJA-UHFFFAOYSA-N 3-[7-methyl-1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]-2,3-dihydroindol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2CC1 NLUHMENALNPHJA-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
• WVXPYMGHPGVJKO-UHFFFAOYSA-N n-benzyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine Chemical compound O1C(C(F)(F)F)=NC(C=2C(=NON=2)NCC=2C=CC=CC=2)=N1 WVXPYMGHPGVJKO-UHFFFAOYSA-N 0.000 claims description 3
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
• SWCAWZMNVIXNKH-UHFFFAOYSA-N 3-[1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=CC=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 SWCAWZMNVIXNKH-UHFFFAOYSA-N 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• MFGOBRZBIXOVQL-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-n-[3-(trifluoromethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]propanamide Chemical compound O1C(C(F)(F)F)=NC(C=2C(=CC(NC(=O)CCC=3C=CC(=CC=3)C(F)(F)F)=CC=2)C(F)(F)F)=N1 MFGOBRZBIXOVQL-UHFFFAOYSA-N 0.000 claims 1
• NVCUFLNOWZTXPQ-UHFFFAOYSA-N 3-[7-methyl-2-[4-(3-methyl-1,2-oxazol-5-yl)butyl]-1-benzofuran-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCC1=CC2=CC(C=3N=C(ON=3)C(F)(F)F)=CC(C)=C2O1 NVCUFLNOWZTXPQ-UHFFFAOYSA-N 0.000 claims 1
• BRMIYYWPBPHSQY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CC(C=2SC(=CC=2)C(=O)C(F)(F)F)=C1 BRMIYYWPBPHSQY-UHFFFAOYSA-N 0.000 claims 1
• JQYWWORDYVNBGY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(C=2SC(=CC=2)C(=O)C(F)(F)F)C=C1 JQYWWORDYVNBGY-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 333
• 238000005481 NMR spectroscopy Methods 0.000 description 299
• 239000011541 reaction mixture Substances 0.000 description 187
• 235000019439 ethyl acetate Nutrition 0.000 description 163
• 239000000243 solution Substances 0.000 description 157
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 149
• 238000010992 reflux Methods 0.000 description 140
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 124
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 104
• 238000000746 purification Methods 0.000 description 99
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
• 239000007787 solid Substances 0.000 description 87
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
• 239000012267 brine Substances 0.000 description 71
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 71
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 68
• 239000012043 crude product Substances 0.000 description 68
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 65
• 239000003480 eluent Substances 0.000 description 63
• 239000012044 organic layer Substances 0.000 description 62
• 239000003208 petroleum Substances 0.000 description 61
• 238000004440 column chromatography Methods 0.000 description 60
• 239000000203 mixture Substances 0.000 description 60
• 239000002253 acid Substances 0.000 description 59
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 59
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
• 239000000047 product Substances 0.000 description 56
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 54
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 52
• 239000011734 sodium Substances 0.000 description 50
• 239000002904 solvent Substances 0.000 description 45
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 41
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 39
• 239000005725 8-Hydroxyquinoline Substances 0.000 description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
• 229960003540 oxyquinoline Drugs 0.000 description 34
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 33
• MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 33
• 229910002027 silica gel Inorganic materials 0.000 description 33
• 239000000377 silicon dioxide Substances 0.000 description 32
• 239000000284 extract Substances 0.000 description 31
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 29
• 102000003964 Histone deacetylase Human genes 0.000 description 28
• 108090000353 Histone deacetylase Proteins 0.000 description 28
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 27
• 239000010410 layer Substances 0.000 description 23
• ZTOAUVQUTVRHBJ-UHFFFAOYSA-N 3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C(F)(F)F)=C1 ZTOAUVQUTVRHBJ-UHFFFAOYSA-N 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
• 239000007788 liquid Substances 0.000 description 22
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
• 201000010099 disease Diseases 0.000 description 17
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
• 238000011282 treatment Methods 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 14
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 12
• NCCMJENTBCOPQF-UHFFFAOYSA-N [4-(4-phenyl-1,3-thiazol-2-yl)oxan-4-yl]methanamine Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1C1(CN)CCOCC1 NCCMJENTBCOPQF-UHFFFAOYSA-N 0.000 description 12
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 12
• 239000005457 ice water Substances 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• XDOXQQBUPUADQB-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=NC=NO1 XDOXQQBUPUADQB-UHFFFAOYSA-N 0.000 description 10
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 10
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 125000003884 phenylalkyl group Chemical group 0.000 description 10
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• 206010028980 Neoplasm Diseases 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 239000012453 solvate Substances 0.000 description 9
• SOFCSIBVJROWGI-UHFFFAOYSA-N 2-(4-phenyl-1,3-thiazol-2-yl)acetonitrile Chemical compound S1C(CC#N)=NC(C=2C=CC=CC=2)=C1 SOFCSIBVJROWGI-UHFFFAOYSA-N 0.000 description 8
• ADGBGWQDEPPMIR-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-methylpropan-1-amine Chemical compound NCC(C)(C)C1=COC(C=2C=CC(F)=CC=2)=N1 ADGBGWQDEPPMIR-UHFFFAOYSA-N 0.000 description 8
• ICPJQQSFDRMJCR-UHFFFAOYSA-N 5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(C=2N=C(ON=2)C(F)(F)F)=C1 ICPJQQSFDRMJCR-UHFFFAOYSA-N 0.000 description 8
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• WAUSXDAVLUXHPM-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]acetonitrile Chemical compound C1=CC(F)=CC=C1C1=NC(CC#N)=CO1 WAUSXDAVLUXHPM-UHFFFAOYSA-N 0.000 description 7
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
• 239000005711 Benzoic acid Substances 0.000 description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 235000010233 benzoic acid Nutrition 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 150000004677 hydrates Chemical class 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 208000023275 Autoimmune disease Diseases 0.000 description 6
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