KR102767739B1 - T 세포 활성화제로서 유용한 치환된 나프티리디논 화합물 - Google Patents

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Publication number

KR102767739B1

KR102767739B1 KR1020217002231A KR20217002231A KR102767739B1 KR 102767739 B1 KR102767739 B1 KR 102767739B1 KR 1020217002231 A KR1020217002231 A KR 1020217002231A KR 20217002231 A KR20217002231 A KR 20217002231A KR 102767739 B1 KR102767739 B1 KR 102767739B1

Authority

KR

South Korea

Prior art keywords

methyl

dehydro

oxo

naphthyridine

carbonitrile

Prior art date

2018-06-27

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.)

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• VHSIAYLBCLUAFT-UHFFFAOYSA-N n-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,8-naphthyridin-4-yl]acetamide Chemical class C=1C=C(Cl)C=CC=1C=1C=C2C(NC(=O)C)=C(C(C)=O)C(=O)N(C)C2=NC=1C1=CC=C(Cl)C=C1Cl VHSIAYLBCLUAFT-UHFFFAOYSA-N 0.000 title description 4
• 229940126530 T cell activator Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 286
• 150000003839 salts Chemical class 0.000 claims abstract description 105
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 30
• 201000011510 cancer Diseases 0.000 claims abstract description 22
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 208000036142 Viral infection Diseases 0.000 claims abstract description 13
• 230000009385 viral infection Effects 0.000 claims abstract description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 712
• -1 cyanocyclopropyl Chemical group 0.000 claims description 560
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 324
• 125000000217 alkyl group Chemical group 0.000 claims description 249
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 243
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 228
• 229910052731 fluorine Inorganic materials 0.000 claims description 186
• 229910052801 chlorine Inorganic materials 0.000 claims description 185
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 137
• 125000001424 substituent group Chemical group 0.000 claims description 127
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 124
• 229910052794 bromium Inorganic materials 0.000 claims description 113
• 229910052799 carbon Inorganic materials 0.000 claims description 113
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 89
• 125000003545 alkoxy group Chemical group 0.000 claims description 83
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 82
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 75
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 72
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 67
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 65
• 125000004122 cyclic group Chemical group 0.000 claims description 57
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 54
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 52
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 44
• 125000004076 pyridyl group Chemical group 0.000 claims description 41
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 125000002757 morpholinyl group Chemical group 0.000 claims description 35
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 125000001425 triazolyl group Chemical group 0.000 claims description 24
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 21
• 125000001544 thienyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 239000003937 drug carrier Substances 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 19
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 19
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 17
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 16
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 16
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 15
• 125000001041 indolyl group Chemical group 0.000 claims description 15
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 15
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
• JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000000597 dioxinyl group Chemical group 0.000 claims description 11
• BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 claims description 11
• XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 claims description 10
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 201000001441 melanoma Diseases 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 8
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005348 fluorocycloalkyl group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 4
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 239000005711 Benzoic acid Substances 0.000 claims description 4
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 4
• 235000010233 benzoic acid Nutrition 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
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• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 2
• XRRDFIPYLFCYLU-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical group [CH2]C1=CC(C)=CC(C)=C1 XRRDFIPYLFCYLU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
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• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
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• WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 claims description 2
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
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