JP6090801B2 - キナーゼ阻害剤としてのアミノキナゾリン - Google Patents

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Publication number

JP6090801B2

JP6090801B2 JP2014526237A JP2014526237A JP6090801B2 JP 6090801 B2 JP6090801 B2 JP 6090801B2 JP 2014526237 A JP2014526237 A JP 2014526237A JP 2014526237 A JP2014526237 A JP 2014526237A JP 6090801 B2 JP6090801 B2 JP 6090801B2

Authority

JP

Japan

Prior art keywords

alkyl

alkoxy

tert

thiazol

benzo

Prior art date

2011-08-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical class C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 218
• -1 cyano, hydroxyl Chemical group 0.000 claims description 186
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 160
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 123
• 150000003839 salts Chemical class 0.000 claims description 113
• 229910052736 halogen Inorganic materials 0.000 claims description 101
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 92
• 125000003545 alkoxy group Chemical group 0.000 claims description 90
• 150000002367 halogens Chemical class 0.000 claims description 89
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 125000001072 heteroaryl group Chemical group 0.000 claims description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000004429 atom Chemical group 0.000 claims description 28
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 21
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 239000001301 oxygen Chemical group 0.000 claims description 19
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 201000000306 sarcoidosis Diseases 0.000 claims description 13
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
• 239000011593 sulfur Chemical group 0.000 claims description 10
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 9
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 9
• BQIIWCWVXUAUOJ-UHFFFAOYSA-N 4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-ol Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)O)S(=O)(=O)C(C)(C)C)=C1 BQIIWCWVXUAUOJ-UHFFFAOYSA-N 0.000 claims description 9
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
• 208000011231 Crohn disease Diseases 0.000 claims description 7
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
• 208000009766 Blau syndrome Diseases 0.000 claims description 6
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• DEMKOIXJPXTNIA-UHFFFAOYSA-N n-(6-tert-butylsulfanyl-7-methoxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)SC(C)(C)C)OC)=C1 DEMKOIXJPXTNIA-UHFFFAOYSA-N 0.000 claims description 6
• GHBWUMFAKHRCHP-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-ethenylquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)C=C)S(=O)(=O)C(C)(C)C)=C1 GHBWUMFAKHRCHP-UHFFFAOYSA-N 0.000 claims description 6
• PZRBSRCAICQLLT-UHFFFAOYSA-N 3-[4-(1,3-benzothiazol-5-ylamino)quinazolin-6-yl]sulfonyl-3-methylbutan-1-ol Chemical compound C1=C2SC=NC2=CC(NC2=NC=NC3=CC=C(C=C32)S(=O)(=O)C(C)(CCO)C)=C1 PZRBSRCAICQLLT-UHFFFAOYSA-N 0.000 claims description 5
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 206010046851 Uveitis Diseases 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• NBVNURWDQZEWFF-UHFFFAOYSA-N ethyl 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxy-2-methylpropanoate Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC(C)(C)C(=O)OCC)=C1 NBVNURWDQZEWFF-UHFFFAOYSA-N 0.000 claims description 5
• XNUUHYUGXNCBIN-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-methoxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC)=C1 XNUUHYUGXNCBIN-UHFFFAOYSA-N 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• WXXFAHPFWATROX-UHFFFAOYSA-N 4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfanylquinazolin-7-ol Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)O)SC(C)(C)C)=C1 WXXFAHPFWATROX-UHFFFAOYSA-N 0.000 claims description 4
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
• KLKPOUXGYGHSRC-UHFFFAOYSA-N n-(6-tert-butylsulfanyl-7-propan-2-yloxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)SC(C)(C)C)OC(C)C)=C1 KLKPOUXGYGHSRC-UHFFFAOYSA-N 0.000 claims description 4
• OEHMGZBZOPNPKA-UHFFFAOYSA-N n-(6-tert-butylsulfanylquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=NC=NC3=CC=C(C=C32)SC(C)(C)C)=C1 OEHMGZBZOPNPKA-UHFFFAOYSA-N 0.000 claims description 4
• SXKVPBAVQVMTMP-UHFFFAOYSA-N n-(6-tert-butylsulfinyl-7-methoxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)C(C)(C)C)OC)=C1 SXKVPBAVQVMTMP-UHFFFAOYSA-N 0.000 claims description 4
• XOGMEWSQTVYLLA-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-ethenoxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)OC=C)S(=O)(=O)C(C)(C)C)=C1 XOGMEWSQTVYLLA-UHFFFAOYSA-N 0.000 claims description 4
• AKZMMJSAMCQMEN-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-ethoxyquinazolin-4-yl)-n-ethyl-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(N(CC)C=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OCC)=C1 AKZMMJSAMCQMEN-UHFFFAOYSA-N 0.000 claims description 4
• HKYLKSMCVOFYTL-UHFFFAOYSA-N n-(6-tert-butylsulfonylquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=NC=NC3=CC=C(C=C32)S(=O)(=O)C(C)(C)C)=C1 HKYLKSMCVOFYTL-UHFFFAOYSA-N 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• WFFNANOPOVMPSU-CYBMUJFWSA-N (2r)-2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropan-1-ol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)O[C@@H](CO)C)=C1 WFFNANOPOVMPSU-CYBMUJFWSA-N 0.000 claims description 3
• WFFNANOPOVMPSU-ZDUSSCGKSA-N (2s)-2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropan-1-ol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)O[C@H](CO)C)=C1 WFFNANOPOVMPSU-ZDUSSCGKSA-N 0.000 claims description 3
• MZEDHTHAYKNCDA-SNAWJCMRSA-N (e)-3-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]prop-2-en-1-ol Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)\C=C\CO)S(=O)(=O)C(C)(C)C)=C1 MZEDHTHAYKNCDA-SNAWJCMRSA-N 0.000 claims description 3
• RTEHDLUIOYJIND-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxy-2-methylpropan-1-ol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC(C)(CO)C)=C1 RTEHDLUIOYJIND-UHFFFAOYSA-N 0.000 claims description 3
• WFFNANOPOVMPSU-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropan-1-ol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC(CO)C)=C1 WFFNANOPOVMPSU-UHFFFAOYSA-N 0.000 claims description 3
• MZLFZLVSRDZFFJ-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-5-ylamino)-7-methoxyquinazolin-6-yl]sulfonylethanol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)CCO)OC)=C1 MZLFZLVSRDZFFJ-UHFFFAOYSA-N 0.000 claims description 3
• LLJFMVIGBWDCOB-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxyquinazolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OC)=CC2=NC=NC=1NC1=NNC(C)=C1C LLJFMVIGBWDCOB-UHFFFAOYSA-N 0.000 claims description 3
• RGOCFAMCSZFRKJ-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(5-fluoro-2h-pyrazolo[3,4-b]pyridin-3-yl)-7-methoxyquinazolin-4-amine Chemical compound C1=C(F)C=C2C(NC=3N=CN=C4C=C(C(=CC4=3)S(=O)(=O)C(C)(C)C)OC)=NNC2=N1 RGOCFAMCSZFRKJ-UHFFFAOYSA-N 0.000 claims description 3
• 201000004624 Dermatitis Diseases 0.000 claims description 3
• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• LRROFHLIWGYSEZ-UHFFFAOYSA-N methyl 2-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropanoate Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC(C)C(=O)OC)=C1 LRROFHLIWGYSEZ-UHFFFAOYSA-N 0.000 claims description 3
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 3
• UZXZRLICOHKBTM-UHFFFAOYSA-N n-(5-fluoro-1h-indazol-3-yl)-6-propan-2-ylsulfonylquinazolin-4-amine Chemical compound C1=C(F)C=C2C(NC3=NC=NC4=CC=C(C=C43)S(=O)(=O)C(C)C)=NNC2=C1 UZXZRLICOHKBTM-UHFFFAOYSA-N 0.000 claims description 3
• TVCQPRRPKVXBKS-UHFFFAOYSA-N n-(6-propan-2-ylsulfonylquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=NC=NC3=CC=C(C=C32)S(=O)(=O)C(C)C)=C1 TVCQPRRPKVXBKS-UHFFFAOYSA-N 0.000 claims description 3
• APEAYCSQUUWKDW-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-chloroquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)Cl)S(=O)(=O)C(C)(C)C)=C1 APEAYCSQUUWKDW-UHFFFAOYSA-N 0.000 claims description 3
• MRPRDTAQVGQYOF-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-ethoxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OCC)=C1 MRPRDTAQVGQYOF-UHFFFAOYSA-N 0.000 claims description 3
• XXAZQMDKRUYZBC-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-ethylquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)CC)=C1 XXAZQMDKRUYZBC-UHFFFAOYSA-N 0.000 claims description 3
• UAFOPMYEBLDYTM-UHFFFAOYSA-N n-(6-tert-butylsulfonyl-7-propan-2-yloxyquinazolin-4-yl)-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC(C)C)=C1 UAFOPMYEBLDYTM-UHFFFAOYSA-N 0.000 claims description 3
• MZKXQFPUSVGNNS-UHFFFAOYSA-N n-[6-tert-butylsulfonyl-7-(2-methylsulfanylethoxy)quinazolin-4-yl]-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OCCSC)=C1 MZKXQFPUSVGNNS-UHFFFAOYSA-N 0.000 claims description 3
• OQAUBIIENWLAFJ-UHFFFAOYSA-N n-[7-(2-bromoethoxy)-6-tert-butylsulfonylquinazolin-4-yl]-1,3-benzothiazol-5-amine Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)OCCBr)S(=O)(=O)C(C)(C)C)=C1 OQAUBIIENWLAFJ-UHFFFAOYSA-N 0.000 claims description 3
• OKMDLZFAWISLNG-CYBMUJFWSA-N (2r)-1-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropan-2-ol Chemical compound C1=C2SC=NC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC[C@H](O)C)=C1 OKMDLZFAWISLNG-CYBMUJFWSA-N 0.000 claims description 2
• IYZUIOQTKXSNLZ-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-5-ylamino)quinazolin-6-yl]sulfonylethanol Chemical compound C1=C2SC=NC2=CC(NC2=NC=NC3=CC=C(C=C32)S(=O)(=O)CCO)=C1 IYZUIOQTKXSNLZ-UHFFFAOYSA-N 0.000 claims description 2
• QFXIIWGIPTWHOU-UHFFFAOYSA-N 2-[4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]-7-methoxyquinazolin-6-yl]sulfonylethanol Chemical compound C=12C=C(S(=O)(=O)CCO)C(OC)=CC2=NC=NC=1NC1=NNC(C)=C1C QFXIIWGIPTWHOU-UHFFFAOYSA-N 0.000 claims description 2
• SCHSCCTXBBGLTD-UHFFFAOYSA-N 3-[4-(1,3-benzothiazol-5-ylamino)-6-tert-butylsulfonylquinazolin-7-yl]oxypropan-1-ol Chemical compound C1=C2SC=NC2=CC(NC2=C3C=C(C(=CC3=NC=N2)OCCCO)S(=O)(=O)C(C)(C)C)=C1 SCHSCCTXBBGLTD-UHFFFAOYSA-N 0.000 claims description 2
• BQTHLISEPIXVRZ-UHFFFAOYSA-N 6-tert-butylsulfonyl-7-chloro-n-(4,5-dimethyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=NC=NC2=CC(Cl)=C(S(=O)(=O)C(C)(C)C)C=C12 BQTHLISEPIXVRZ-UHFFFAOYSA-N 0.000 claims description 2
• WEAMADQORMMOAF-UHFFFAOYSA-N 6-tert-butylsulfonyl-7-methoxy-n-(3-methyl-2h-indazol-6-yl)quinazolin-4-amine Chemical compound C1=C2C(C)=NNC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC)=C1 WEAMADQORMMOAF-UHFFFAOYSA-N 0.000 claims description 2
• JRAQIAOKZOOVOF-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(1h-indazol-6-yl)-7-methoxyquinazolin-4-amine Chemical compound C1=C2C=NNC2=CC(NC=2N=CN=C3C=C(C(=CC3=2)S(=O)(=O)C(C)(C)C)OC)=C1 JRAQIAOKZOOVOF-UHFFFAOYSA-N 0.000 claims description 2
• YYCQIMDXTOTJBU-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(2,4,5-trimethylpyrazol-3-yl)quinazolin-4-amine Chemical compound CC1=NN(C)C(NC=2C3=CC(=CC=C3N=CN=2)S(=O)(=O)C(C)(C)C)=C1C YYCQIMDXTOTJBU-UHFFFAOYSA-N 0.000 claims description 2
• NGZONKIWOMPQFA-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(5-fluoro-1h-indazol-3-yl)quinazolin-4-amine Chemical compound C1=C(F)C=C2C(NC3=NC=NC4=CC=C(C=C43)S(=O)(=O)C(C)(C)C)=NNC2=C1 NGZONKIWOMPQFA-UHFFFAOYSA-N 0.000 claims description 2
• KZWFOONWYSBZKF-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-[5-(trifluoromethyl)-1h-pyrazol-3-yl]quinazolin-4-amine Chemical compound C12=CC(S(=O)(=O)C(C)(C)C)=CC=C2N=CN=C1NC=1C=C(C(F)(F)F)NN=1 KZWFOONWYSBZKF-UHFFFAOYSA-N 0.000 claims description 2
• 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
• 206010063837 Reperfusion injury Diseases 0.000 claims description 2
• 206010069351 acute lung injury Diseases 0.000 claims description 2
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 2
• 230000000366 juvenile effect Effects 0.000 claims description 2
• 201000006417 multiple sclerosis Diseases 0.000 claims description 2
• DJUHCRXMBJTHCF-UHFFFAOYSA-N n-(4,5-dimethyl-1h-pyrazol-3-yl)-6-propan-2-ylsulfonylquinazolin-4-amine Chemical compound C12=CC(S(=O)(=O)C(C)C)=CC=C2N=CN=C1NC1=NNC(C)=C1C DJUHCRXMBJTHCF-UHFFFAOYSA-N 0.000 claims description 2
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