JP2016506965A5 - - Google Patents
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- Publication number
- JP2016506965A5 JP2016506965A5 JP2015556146A JP2015556146A JP2016506965A5 JP 2016506965 A5 JP2016506965 A5 JP 2016506965A5 JP 2015556146 A JP2015556146 A JP 2015556146A JP 2015556146 A JP2015556146 A JP 2015556146A JP 2016506965 A5 JP2016506965 A5 JP 2016506965A5
- Authority
- JP
- Japan
- Prior art keywords
- amine
- quinolin
- carbon atoms
- hexyloxy
- alkyl
- 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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- 125000004432 carbon atom Chemical group C* 0.000 claims 61
- 125000000217 alkyl group Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 37
- 125000003545 alkoxy group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 14
- -1 amino, dimethylamino, hydroxy Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000005059 halophenyl group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 2
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 208000031888 Mycoses Diseases 0.000 claims 2
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 230000001613 neoplastic effect Effects 0.000 claims 2
- 229960002715 nicotine Drugs 0.000 claims 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 230000036281 parasite infection Effects 0.000 claims 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- SRKFOBFEIJDICP-UHFFFAOYSA-N 1-(10-butoxydecyl)imidazo[4,5-c]pyridine Chemical compound N1=CC=C2N(CCCCCCCCCCOCCCC)C=NC2=C1 SRKFOBFEIJDICP-UHFFFAOYSA-N 0.000 claims 1
- GMOINKUVFFTIMG-UHFFFAOYSA-N 1-(10-butoxydecyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCCCOCCCC)C=NC3=CN=C21 GMOINKUVFFTIMG-UHFFFAOYSA-N 0.000 claims 1
- ZXUOIJATQROHIH-UHFFFAOYSA-N 1-(2-dodecoxyethyl)-n,n-dimethylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCOCCCCCCCCCCCC)C=NC3=C(N(C)C)N=C21 ZXUOIJATQROHIH-UHFFFAOYSA-N 0.000 claims 1
- WQLHLGRZOAMQRF-UHFFFAOYSA-N 1-(2-dodecoxyethyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCOCCCCCCCCCCCC)C=NC3=CN=C21 WQLHLGRZOAMQRF-UHFFFAOYSA-N 0.000 claims 1
- YOHBGPBSPBTBHV-UHFFFAOYSA-N 1-(2-methylpropyl)-2-pentadecyl-5h-imidazo[4,5-c]quinolin-4-one Chemical compound C12=CC=CC=C2NC(=O)C2=C1N(CC(C)C)C(CCCCCCCCCCCCCCC)=N2 YOHBGPBSPBTBHV-UHFFFAOYSA-N 0.000 claims 1
- MNVYNVXOTBMLNV-UHFFFAOYSA-N 1-(3-decoxypropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCOCCCCCCCCCC)C=NC3=CN=C21 MNVYNVXOTBMLNV-UHFFFAOYSA-N 0.000 claims 1
- IQLWUSRZZXDYND-UHFFFAOYSA-N 1-(4-decoxybutyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCOCCCCCCCCCC)C=NC3=CN=C21 IQLWUSRZZXDYND-UHFFFAOYSA-N 0.000 claims 1
- FHFRHWWECLHUFT-UHFFFAOYSA-N 1-(6-octoxyhexyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCOCCCCCCCC)C=NC3=CN=C21 FHFRHWWECLHUFT-UHFFFAOYSA-N 0.000 claims 1
- KKANBEKKIZXKBY-UHFFFAOYSA-N 1-(8-butoxyoctyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCOCCCC)C=NC3=CN=C21 KKANBEKKIZXKBY-UHFFFAOYSA-N 0.000 claims 1
- NUTDIBQLDCINFN-UHFFFAOYSA-N 1-(8-ethoxyoctyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCOCC)C=NC3=CN=C21 NUTDIBQLDCINFN-UHFFFAOYSA-N 0.000 claims 1
- PUIXSTZANOAUSB-UHFFFAOYSA-N 1-(8-hexoxyoctyl)-4-phenylimidazole Chemical compound CCCCCCOCCCCCCCCN1C=NC(C=2C=CC=CC=2)=C1 PUIXSTZANOAUSB-UHFFFAOYSA-N 0.000 claims 1
- IJOMQXULPZIBCK-UHFFFAOYSA-N 1-(8-hexoxyoctyl)benzimidazole Chemical compound C1=CC=C2N(CCCCCCCCOCCCCCC)C=NC2=C1 IJOMQXULPZIBCK-UHFFFAOYSA-N 0.000 claims 1
- BKIOFILMQQANLO-UHFFFAOYSA-N 1-(8-hexoxyoctyl)imidazo[4,5-c]pyridine Chemical compound N1=CC=C2N(CCCCCCCCOCCCCCC)C=NC2=C1 BKIOFILMQQANLO-UHFFFAOYSA-N 0.000 claims 1
- DCKDZCFGAGLTJK-UHFFFAOYSA-N 1-(8-hexoxyoctyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCOCCCCCC)C=NC3=CN=C21 DCKDZCFGAGLTJK-UHFFFAOYSA-N 0.000 claims 1
- IZLKYWOOQMZMIV-UHFFFAOYSA-N 1-(8-hexoxyoctyl)indole Chemical compound C1=CC=C2N(CCCCCCCCOCCCCCC)C=CC2=C1 IZLKYWOOQMZMIV-UHFFFAOYSA-N 0.000 claims 1
- OSJGEWBTDRKAOH-UHFFFAOYSA-O 1-(8-hexoxyoctyl)pyridin-1-ium-4-amine Chemical class CCCCCCOCCCCCCCC[N+]1=CC=C(N)C=C1 OSJGEWBTDRKAOH-UHFFFAOYSA-O 0.000 claims 1
- GHCFMJCHQQLACQ-UHFFFAOYSA-N 1-(8-methoxyoctyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCOC)C=NC3=CN=C21 GHCFMJCHQQLACQ-UHFFFAOYSA-N 0.000 claims 1
- CVIRBHYAUQWXQE-UHFFFAOYSA-N 1-(9-hexoxynonyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCCOCCCCCC)C=NC3=CN=C21 CVIRBHYAUQWXQE-UHFFFAOYSA-N 0.000 claims 1
- MYKUTOOCWPZANP-UHFFFAOYSA-N 1-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=CN=C21 MYKUTOOCWPZANP-UHFFFAOYSA-N 0.000 claims 1
- XWBVARVUJUFZRD-UHFFFAOYSA-N 1-[3-(3-hexoxyphenoxy)propyl]imidazo[4,5-c]quinoline Chemical compound CCCCCCOC1=CC=CC(OCCCN2C3=C4C=CC=CC4=NC=C3N=C2)=C1 XWBVARVUJUFZRD-UHFFFAOYSA-N 0.000 claims 1
- JBFFUKCOKQFAKS-UHFFFAOYSA-N 1-[5-(3-hexoxypropoxy)pentyl]imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCOCCCOCCCCCC)C=NC3=CN=C21 JBFFUKCOKQFAKS-UHFFFAOYSA-N 0.000 claims 1
- SGFUBMSPDGPTBO-UHFFFAOYSA-N 1-dodecylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCCCCC)C=NC3=CN=C21 SGFUBMSPDGPTBO-UHFFFAOYSA-N 0.000 claims 1
- DFJUBPJXENJNOT-UHFFFAOYSA-N 1-hexadecylimidazo[4,5-c]pyridine Chemical compound N1=CC=C2N(CCCCCCCCCCCCCCCC)C=NC2=C1 DFJUBPJXENJNOT-UHFFFAOYSA-N 0.000 claims 1
- IQRQKYKEQPMBCG-UHFFFAOYSA-N 1-hexadecylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCCCCCCCCCCCCC)C=NC3=C(N)N=C21 IQRQKYKEQPMBCG-UHFFFAOYSA-N 0.000 claims 1
- TVEUKUZUDMCZMO-UHFFFAOYSA-N 1-hexadecylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCCCCCCCCCC)C=NC3=CN=C21 TVEUKUZUDMCZMO-UHFFFAOYSA-N 0.000 claims 1
- YGYLXGMKGYJPGX-UHFFFAOYSA-N 1-octylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CCCCCCCC)C=NC3=CN=C21 YGYLXGMKGYJPGX-UHFFFAOYSA-N 0.000 claims 1
- ABUODLKBWVMNHS-UHFFFAOYSA-N 2-hexoxy-n-[3-(quinolin-4-ylamino)propyl]benzamide Chemical compound CCCCCCOC1=CC=CC=C1C(=O)NCCCNC1=CC=NC2=CC=CC=C12 ABUODLKBWVMNHS-UHFFFAOYSA-N 0.000 claims 1
- WNMFTRBSOKCJRI-UHFFFAOYSA-N 2-hexoxy-n-[4-(quinolin-4-ylamino)butyl]benzamide Chemical compound CCCCCCOC1=CC=CC=C1C(=O)NCCCCNC1=CC=NC2=CC=CC=C12 WNMFTRBSOKCJRI-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- OLIUAKLWCBPKIB-UHFFFAOYSA-N 3-(8-hexoxyoctyl)imidazo[4,5-b]pyridine Chemical compound C1=CN=C2N(CCCCCCCCOCCCCCC)C=NC2=C1 OLIUAKLWCBPKIB-UHFFFAOYSA-N 0.000 claims 1
- SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 claims 1
- DBQWJFZPVCIJAJ-UHFFFAOYSA-N 3-methoxy-n-[8-(quinolin-4-ylamino)octyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCCCCCCCCNC=2C3=CC=CC=C3N=CC=2)=C1 DBQWJFZPVCIJAJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
- VMYHAUSJRGALHC-UHFFFAOYSA-N 4-methoxy-n-[8-(quinolin-4-ylamino)octyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCCCCCCCNC1=CC=NC2=CC=CC=C12 VMYHAUSJRGALHC-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- VAOXVWMKJCWDGL-UHFFFAOYSA-N 7-chloro-n-(8-hexoxyoctyl)quinolin-4-amine Chemical compound ClC1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=NC2=C1 VAOXVWMKJCWDGL-UHFFFAOYSA-N 0.000 claims 1
- KGJFQADNAKDDFD-UHFFFAOYSA-N 7-chloro-n-decylquinazolin-4-amine Chemical compound ClC1=CC=C2C(NCCCCCCCCCC)=NC=NC2=C1 KGJFQADNAKDDFD-UHFFFAOYSA-N 0.000 claims 1
- NAPHWHLDJWWAFT-UHFFFAOYSA-N 7-chloro-n-decylquinolin-4-amine Chemical compound ClC1=CC=C2C(NCCCCCCCCCC)=CC=NC2=C1 NAPHWHLDJWWAFT-UHFFFAOYSA-N 0.000 claims 1
- BRUUKKPOIHXBIY-UHFFFAOYSA-N 7-chloro-n-dodecylquinazolin-4-amine Chemical compound ClC1=CC=C2C(NCCCCCCCCCCCC)=NC=NC2=C1 BRUUKKPOIHXBIY-UHFFFAOYSA-N 0.000 claims 1
- YLIUKFRPGHKGBP-UHFFFAOYSA-N 7-chloro-n-dodecylquinolin-4-amine Chemical compound ClC1=CC=C2C(NCCCCCCCCCCCC)=CC=NC2=C1 YLIUKFRPGHKGBP-UHFFFAOYSA-N 0.000 claims 1
- ATHMVBCQNFBFPC-UHFFFAOYSA-N 8-chloro-n-(8-hexoxyoctyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=NC2=C1Cl ATHMVBCQNFBFPC-UHFFFAOYSA-N 0.000 claims 1
- VIBMMNMKMMIAQG-UHFFFAOYSA-N C1(=CC=CC=C1)CCC=1C=C(CNC2=CC=NC3=CC=CC=C23)C=CC1 Chemical compound C1(=CC=CC=C1)CCC=1C=C(CNC2=CC=NC3=CC=CC=C23)C=CC1 VIBMMNMKMMIAQG-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WRNDADRVYSIERI-UHFFFAOYSA-N hexyl 4-(quinolin-4-ylamino)benzoate Chemical compound C1=CC(C(=O)OCCCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 WRNDADRVYSIERI-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YDRQHRCWVHTUCP-UHFFFAOYSA-N n,n'-di(quinolin-4-yl)octane-1,8-diamine Chemical compound C1=CC=C2C(NCCCCCCCCNC=3C4=CC=CC=C4N=CC=3)=CC=NC2=C1 YDRQHRCWVHTUCP-UHFFFAOYSA-N 0.000 claims 1
- DOPWOJAVJJJTRS-UHFFFAOYSA-N n-(10-butoxydecyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCCOCCCC)=CC=NC2=C1 DOPWOJAVJJJTRS-UHFFFAOYSA-N 0.000 claims 1
- RMCSNNKMHAZDGC-UHFFFAOYSA-N n-(10-hexoxydecyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCCOCCCCCC)=CC=NC2=C1 RMCSNNKMHAZDGC-UHFFFAOYSA-N 0.000 claims 1
- IRXQHKWBKBJNBA-UHFFFAOYSA-N n-(2-fluoro-4-hexoxyphenyl)quinolin-4-amine Chemical compound FC1=CC(OCCCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 IRXQHKWBKBJNBA-UHFFFAOYSA-N 0.000 claims 1
- NPJZMCMNVXQYKJ-UHFFFAOYSA-N n-(2-hexoxyphenyl)quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1NC1=CC=NC2=CC=CC=C12 NPJZMCMNVXQYKJ-UHFFFAOYSA-N 0.000 claims 1
- QCDAWYHWZGXWSV-UHFFFAOYSA-N n-(2-phenoxyphenyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NC1=CC=CC=C1OC1=CC=CC=C1 QCDAWYHWZGXWSV-UHFFFAOYSA-N 0.000 claims 1
- FGKUOPSGOIHRAV-UHFFFAOYSA-N n-(2-phenylethyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCCC1=CC=CC=C1 FGKUOPSGOIHRAV-UHFFFAOYSA-N 0.000 claims 1
- VQDFCGCTFUQNSZ-UHFFFAOYSA-N n-(2-phenylmethoxyphenyl)quinolin-4-amine Chemical compound C=1C=CC=C(NC=2C3=CC=CC=C3N=CC=2)C=1OCC1=CC=CC=C1 VQDFCGCTFUQNSZ-UHFFFAOYSA-N 0.000 claims 1
- DEHXYOGWICOZRD-UHFFFAOYSA-N n-(3-hexoxyphenyl)quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC(NC=2C3=CC=CC=C3N=CC=2)=C1 DEHXYOGWICOZRD-UHFFFAOYSA-N 0.000 claims 1
- CCTMIADRZHWUER-UHFFFAOYSA-N n-(3-phenoxyphenyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NC(C=1)=CC=CC=1OC1=CC=CC=C1 CCTMIADRZHWUER-UHFFFAOYSA-N 0.000 claims 1
- NCSOMDAZOSDYNR-UHFFFAOYSA-N n-(3-phenylmethoxyphenyl)quinolin-4-amine Chemical compound C=1C=CC(NC=2C3=CC=CC=C3N=CC=2)=CC=1OCC1=CC=CC=C1 NCSOMDAZOSDYNR-UHFFFAOYSA-N 0.000 claims 1
- ZMDTVWKPZUSYRV-UHFFFAOYSA-N n-(4-butoxyphenyl)quinolin-4-amine Chemical compound C1=CC(OCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 ZMDTVWKPZUSYRV-UHFFFAOYSA-N 0.000 claims 1
- LPOAZLOUTYRISZ-UHFFFAOYSA-N n-(4-hexoxyphenyl)quinolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 LPOAZLOUTYRISZ-UHFFFAOYSA-N 0.000 claims 1
- XEXJCSNBUIARJF-UHFFFAOYSA-N n-(4-methoxyphenyl)quinolin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC2=CC=CC=C12 XEXJCSNBUIARJF-UHFFFAOYSA-N 0.000 claims 1
- CHAYZJWZKSNHRQ-UHFFFAOYSA-N n-(4-phenoxyphenyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 CHAYZJWZKSNHRQ-UHFFFAOYSA-N 0.000 claims 1
- SFORYKJJEOODMD-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)quinolin-4-amine Chemical compound C=1C=C(NC=2C3=CC=CC=C3N=CC=2)C=CC=1OCC1=CC=CC=C1 SFORYKJJEOODMD-UHFFFAOYSA-N 0.000 claims 1
- NORLLMDOBFEMHH-UHFFFAOYSA-N n-(4-phenylphenyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NC(C=C1)=CC=C1C1=CC=CC=C1 NORLLMDOBFEMHH-UHFFFAOYSA-N 0.000 claims 1
- IGWWCHGWHQVVFF-UHFFFAOYSA-N n-(5-methoxypentyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCOC)=CC=NC2=C1 IGWWCHGWHQVVFF-UHFFFAOYSA-N 0.000 claims 1
- WQXRUZGVYYYFMA-UHFFFAOYSA-N n-(6-butoxyhexyl)quinazolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCOCCCC)=NC=NC2=C1 WQXRUZGVYYYFMA-UHFFFAOYSA-N 0.000 claims 1
- VKBXGXDOKDVVLQ-UHFFFAOYSA-N n-(6-butoxyhexyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCOCCCC)=CC=NC2=C1 VKBXGXDOKDVVLQ-UHFFFAOYSA-N 0.000 claims 1
- HNQZLYJIQXSZCS-UHFFFAOYSA-N n-(6-hexoxyhexyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCOCCCCCC)=CC=NC2=C1 HNQZLYJIQXSZCS-UHFFFAOYSA-N 0.000 claims 1
- XBHIUJCMACEZCW-UHFFFAOYSA-N n-(6-phenoxyhexyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCOC1=CC=CC=C1 XBHIUJCMACEZCW-UHFFFAOYSA-N 0.000 claims 1
- CECCFVMUWPFZNN-UHFFFAOYSA-N n-(8-butoxyoctyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCC)=CC=NC2=C1 CECCFVMUWPFZNN-UHFFFAOYSA-N 0.000 claims 1
- JMOGHXSIRUXZMY-UHFFFAOYSA-N n-(8-hexoxyoctyl)-2-(trifluoromethyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC(C(F)(F)F)=NC2=C1 JMOGHXSIRUXZMY-UHFFFAOYSA-N 0.000 claims 1
- NKEFAXUWWNGEBM-UHFFFAOYSA-N n-(8-hexoxyoctyl)-2-methylquinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC(C)=NC2=C1 NKEFAXUWWNGEBM-UHFFFAOYSA-N 0.000 claims 1
- DYWRXXWJEQDHNR-UHFFFAOYSA-N n-(8-hexoxyoctyl)-7-(trifluoromethyl)quinolin-4-amine Chemical compound FC(F)(F)C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=NC2=C1 DYWRXXWJEQDHNR-UHFFFAOYSA-N 0.000 claims 1
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| US10231958B2 (en) | 2014-10-24 | 2019-03-19 | The Board Of Regents Of The University Of Texas System | Methods and compositions for enhancing chemotherapy |
| WO2016141092A1 (en) | 2015-03-04 | 2016-09-09 | Gilead Sciences, Inc. | Toll-like receptor modulating 4,6-diamino-pyrido[3,2-d]pyrimidine compounds |
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| CN109923106B (zh) | 2016-09-02 | 2022-09-13 | 吉利德科学公司 | toll样受体调节剂化合物 |
| CN110494432B (zh) | 2016-12-28 | 2022-08-12 | 米尼奥尔克斯治疗有限公司 | 异喹啉化合物，其制备方法及其在与β-半乳糖苷酶活性改变相关的病症中的治疗用途 |
| US12539297B2 (en) | 2017-02-07 | 2026-02-03 | Oncocross Co., Ltd. | Composition for inhibiting cancer metastasis and treating cancer |
| US11364237B2 (en) * | 2017-02-07 | 2022-06-21 | Oncocross Co., Ltd. | Composition for inhibiting cancer metastasis and treating cancer |
| BR112019019109B1 (pt) * | 2017-03-15 | 2023-11-07 | Lunella Biotech, Inc | Compostos mitorriboscina, composição farmacêutica compreendendo os mesmos, e seus usos direcionados para células cancerosas, bactérias e levedura patogênica |
| JP6635999B2 (ja) * | 2017-10-13 | 2020-01-29 | 株式会社ダイセル | カリウム塩の製造方法、及びカリウム塩 |
| CN108084089B (zh) * | 2017-12-08 | 2020-10-23 | 华南农业大学 | 一种防治白色念珠菌的2-烷基胺喹啉类化合物及其制备方法与应用 |
| CN108892634B (zh) * | 2018-06-19 | 2021-04-23 | 浙江工业大学 | 一种吲哚甲基苯胺类化合物及其应用 |
| CN111960970B (zh) * | 2018-08-08 | 2021-08-20 | 中国人民解放军总医院 | 抗肿瘤化合物 |
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| TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
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| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
| GB201909659D0 (en) * | 2019-07-04 | 2019-08-21 | Aberystwyth Univ | Anti-infective compounds |
| CN110804013B (zh) * | 2019-10-09 | 2024-04-05 | 南京工业大学 | 一种邻位二胺类化合物的合成方法 |
| JP2023542541A (ja) * | 2020-09-25 | 2023-10-10 | エサイエント ファーマシューティカルズ，インコーポレイティド | Ｍａｓ関連ｇタンパク質受容体ｘ２のモジュレーター、並びに関連製品及び方法 |
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