JP2019521193A5 - - Google Patents
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- Publication number
- JP2019521193A5 JP2019521193A5 JP2019521185A JP2019521185A JP2019521193A5 JP 2019521193 A5 JP2019521193 A5 JP 2019521193A5 JP 2019521185 A JP2019521185 A JP 2019521185A JP 2019521185 A JP2019521185 A JP 2019521185A JP 2019521193 A5 JP2019521193 A5 JP 2019521193A5
- Authority
- JP
- Japan
- Prior art keywords
- amine
- methoxyphenyl
- chloro
- quinoline
- diamine
- Prior art date
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 3- (trifluoromethyl) phenyl Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 4
- HVVUEQUGVFPGLX-UHFFFAOYSA-N COC=1C=C(C=CC=1OC)NC1=CC(=NC2=CC(=CC=C12)Cl)N1CCN(CC1)C Chemical compound COC=1C=C(C=CC=1OC)NC1=CC(=NC2=CC(=CC=C12)Cl)N1CCN(CC1)C HVVUEQUGVFPGLX-UHFFFAOYSA-N 0.000 claims description 4
- MCNYRRAYOXEGGT-UHFFFAOYSA-N COC=1C=C(C=CC=1OC)NC1=CC(=NC2=CC(=CC=C12)Cl)OCCN1CCOCC1 Chemical compound COC=1C=C(C=CC=1OC)NC1=CC(=NC2=CC(=CC=C12)Cl)OCCN1CCOCC1 MCNYRRAYOXEGGT-UHFFFAOYSA-N 0.000 claims description 4
- BZPJICMAKFOAPD-UHFFFAOYSA-N 4-[[4-amino-4-(3,5-difluorophenyl)-3H-quinolin-7-yl]amino]-2-chlorophenol Chemical compound FC=1C=C(C=C(C=1)F)C1(CC=NC2=CC(=CC=C12)NC1=CC(=C(C=C1)O)Cl)N BZPJICMAKFOAPD-UHFFFAOYSA-N 0.000 claims description 3
- QBEOYDZBNHLGHG-UHFFFAOYSA-N 7-morpholin-4-yl-N-[3-(trifluoromethyl)phenyl]quinolin-4-amine Chemical compound FC(C=1C=C(C=CC=1)NC1=CC=NC2=CC(=CC=C12)N1CCOCC1)(F)F QBEOYDZBNHLGHG-UHFFFAOYSA-N 0.000 claims description 3
- MJIVOGFXOAKNRX-UHFFFAOYSA-N CC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N Chemical compound CC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N MJIVOGFXOAKNRX-UHFFFAOYSA-N 0.000 claims description 3
- JWQMCGDPGDMOJO-UHFFFAOYSA-N CC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC=C(C=C4)OC)N Chemical compound CC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC=C(C=C4)OC)N JWQMCGDPGDMOJO-UHFFFAOYSA-N 0.000 claims description 3
- IVOFBCBKJFLXTA-UHFFFAOYSA-N CC1=CC=CC=C1C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N Chemical compound CC1=CC=CC=C1C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N IVOFBCBKJFLXTA-UHFFFAOYSA-N 0.000 claims description 3
- LFWPXDTYXUGXEH-UHFFFAOYSA-N COC1=C(C=C(C=C1)NC1=CC=NC2=CC(=CC=C12)Cl)OCCOC Chemical compound COC1=C(C=C(C=C1)NC1=CC=NC2=CC(=CC=C12)Cl)OCCOC LFWPXDTYXUGXEH-UHFFFAOYSA-N 0.000 claims description 3
- CAMVNZQCTHSNTM-UHFFFAOYSA-N COC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N Chemical compound COC1=CC=C(C=C1)C2(CC=NC3=C2C=CC(=C3)NC4=CC(=CC=C4)OC)N CAMVNZQCTHSNTM-UHFFFAOYSA-N 0.000 claims description 3
- ASIQDNAPCDYSHV-UHFFFAOYSA-N COC1=CC=C(C=C1)NC2=CC3=C(C=C2)C(CC=N3)(C4=CC(=CC=C4)C(F)(F)F)N Chemical compound COC1=CC=C(C=C1)NC2=CC3=C(C=C2)C(CC=N3)(C4=CC(=CC=C4)C(F)(F)F)N ASIQDNAPCDYSHV-UHFFFAOYSA-N 0.000 claims description 3
- FGDIZKPDAQWKHL-UHFFFAOYSA-N 4-(3,5-difluorophenyl)-7-N-(3-methoxyphenyl)-3H-quinoline-4,7-diamine Chemical compound FC=1C=C(C=C(C=1)F)C1(CC=NC2=CC(=CC=C12)NC1=CC(=CC=C1)OC)N FGDIZKPDAQWKHL-UHFFFAOYSA-N 0.000 claims description 2
- UWSPBYIZLDIQHB-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-7-chloroquinolin-4-amine Chemical compound C1=C2OCOC2=CC(NC=2C3=CC=C(C=C3N=CC=2)Cl)=C1 UWSPBYIZLDIQHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 24
- 230000000155 isotopic effect Effects 0.000 claims 10
- 230000003287 optical effect Effects 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 4
- BVIMHVCLAZHYPT-UHFFFAOYSA-N 7-(3-methoxyphenyl)-6H-quinoline-4,7-diamine Chemical compound COC=1C=C(C=CC=1)C1(CC=C2C(=CC=NC2=C1)N)N BVIMHVCLAZHYPT-UHFFFAOYSA-N 0.000 claims 4
- FSQNPLIPCMZTCS-UHFFFAOYSA-N 7-(4-methoxyphenyl)-6H-quinoline-4,7-diamine Chemical compound COC1=CC=C(C=C1)C1(CC=C2C(=CC=NC2=C1)N)N FSQNPLIPCMZTCS-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 206010038389 Renal cancer Diseases 0.000 claims 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000029742 colonic neoplasm Diseases 0.000 claims 3
- 201000005787 hematologic cancer Diseases 0.000 claims 3
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 3
- 201000010982 kidney cancer Diseases 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- TWLGPWZTMALXOR-UHFFFAOYSA-N quinoline-4,7-diamine Chemical compound NC1=CC=NC2=CC(N)=CC=C21 TWLGPWZTMALXOR-UHFFFAOYSA-N 0.000 claims 2
- VPNIVEOOPXFGHG-UHFFFAOYSA-N 2-chloro-4-(4,7-diamino-6H-quinolin-7-yl)phenol Chemical compound ClC=1C=C(C=CC=1O)C1(CC=C2C(=CC=NC2=C1)N)N VPNIVEOOPXFGHG-UHFFFAOYSA-N 0.000 claims 1
- SHKUVWUJGUOGPO-UHFFFAOYSA-N 7-chloro-N-(2,3-dihydro-1,4-benzodioxin-6-yl)quinolin-4-amine Chemical compound ClC1=CC=C2C(NC3=CC=C4OCCOC4=C3)=CC=NC2=C1 SHKUVWUJGUOGPO-UHFFFAOYSA-N 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 238000011260 co-administration Methods 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- JUGMSTLDVOSLLN-UHFFFAOYSA-N COC1=CC=C(C=C1)NC1=CC(=NC2=CC(=CC=C12)Cl)N1CCN(CC1)C Chemical compound COC1=CC=C(C=C1)NC1=CC(=NC2=CC(=CC=C12)Cl)N1CCN(CC1)C JUGMSTLDVOSLLN-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- FZXNMLPPOQRQBN-UHFFFAOYSA-N FC(OC1=CC=C(C=C1)NC1=CC=NC2=CC(=CC=C12)Cl)F Chemical compound FC(OC1=CC=C(C=C1)NC1=CC=NC2=CC(=CC=C12)Cl)F FZXNMLPPOQRQBN-UHFFFAOYSA-N 0.000 description 1
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| PCT/EP2017/067306 WO2018007648A1 (en) | 2016-07-08 | 2017-07-10 | 4-anilino-quinoline compounds as anti-cancer agents |
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| WO2019134975A1 (en) | 2018-01-05 | 2019-07-11 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Substituted halo-quinoline derivatives, method of preparation and applications thereof |
| CN113549018B (zh) * | 2020-04-24 | 2024-02-27 | 中国药科大学 | 蛋白激酶抑制剂及其衍生物，制备方法、药物组合物和应用 |
| EP4169904A1 (en) | 2021-10-25 | 2023-04-26 | Yukin Therapeutics | Substituted quinolines as improved nf-kb-inducing kinase (nik) inhibitors |
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| US3075981A (en) * | 1958-04-03 | 1963-01-29 | Sterling Drug Inc | 1-[aromatic-(lower-alkyl)]-4-(aromaticimino)-1, 4-dihydroquinolines and their preparation |
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| US3492397A (en) | 1967-04-07 | 1970-01-27 | Warner Lambert Pharmaceutical | Sustained release dosage in the pellet form and process thereof |
| US4060598A (en) | 1967-06-28 | 1977-11-29 | Boehringer Mannheim G.M.B.H. | Tablets coated with aqueous resin dispersions |
| US3538214A (en) | 1969-04-22 | 1970-11-03 | Merck & Co Inc | Controlled release medicinal tablets |
| US4173626A (en) | 1978-12-11 | 1979-11-06 | Merck & Co., Inc. | Sustained release indomethacin |
| WO2008089307A2 (en) * | 2007-01-18 | 2008-07-24 | Lexicon Pharmaceuticals, Inc. | Delta 5 desaturase inhibitors for the treatment of pain, inflammation and cancer |
| CN102249997A (zh) | 2011-05-25 | 2011-11-23 | 沈阳化工大学 | 一组具有抗肿瘤活性的4-取代苯氨基喹啉化合物 |
| US10322125B2 (en) | 2013-02-22 | 2019-06-18 | Emory University | TGF-beta enhancing compositions for cartilage repair and methods related thereto |
| CN103232444B (zh) | 2013-04-18 | 2015-07-22 | 中国人民解放军军事医学科学院微生物流行病研究所 | 萘酚喹衍生物及其制备和其应用 |
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