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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Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR122021012629B1 (pt) * | 2013-02-01 | 2022-06-07 | Wellstat Therapeutics Corporation | Compostos de amina, composição compreendendo os referidos compostos e usos dos mesmos |
| JP6247992B2 (ja) * | 2014-04-17 | 2017-12-13 | 株式会社ダイセル | ハロゲン化合物の製造方法 |
| US10231958B2 (en) | 2014-10-24 | 2019-03-19 | The Board Of Regents Of The University Of Texas System | Methods and compositions for enhancing chemotherapy |
| SG11201606876RA (en) | 2015-03-04 | 2016-10-28 | Gilead Sciences Inc | Toll like receptor modulator compounds |
| SI3507276T1 (sl) | 2016-09-02 | 2022-01-31 | Gilead Sciences, Inc. | Spojine modulatorja toličnih receptorjev |
| WO2018045150A1 (en) | 2016-09-02 | 2018-03-08 | Gilead Sciences, Inc. | 4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators |
| WO2018122746A1 (en) | 2016-12-28 | 2018-07-05 | Minoryx Therapeutics S.L. | Isoquinoline compounds, methods for their preparation, and therapeutic uses thereof in conditions associated with the alteration of the activity of beta galactosidase |
| US12539297B2 (en) | 2017-02-07 | 2026-02-03 | Oncocross Co., Ltd. | Composition for inhibiting cancer metastasis and treating cancer |
| WO2018147612A1 (ko) * | 2017-02-07 | 2018-08-16 | 주식회사 온코크로스 | 암의 전이 억제 및 치료용 조성물 |
| EP3596043B1 (en) * | 2017-03-15 | 2025-12-03 | Lunella Biotech, Inc. | Mitoriboscins: mitochondrial-based therapeutics targeting cancer cells, bacteria, and pathogenic yeast |
| 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 |
| CN108997172B (zh) * | 2018-08-08 | 2020-12-15 | 中国人民解放军总医院 | 抗肿瘤化合物 |
| CN113286785A (zh) * | 2019-01-04 | 2021-08-20 | 贝尔布鲁克实验室有限责任公司 | 作为治疗剂的cGAS活性的抑制剂 |
| 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 |
| TWI751517B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| KR102286897B1 (ko) | 2019-06-25 | 2021-08-09 | (주)앰틱스바이오 | 신규한 아미노알칸산에 바이페닐기를 도입한 유도체 화합물 및 이를 포함하는 항진균성 약학적 조성물 |
| 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 |
| AU2021347360A1 (en) * | 2020-09-25 | 2023-05-25 | Escient Pharmaceuticals, Inc. | Modulators of mas-related g-protein receptor x2 and related products and methods |
| BR112023011284A2 (pt) | 2020-12-09 | 2024-02-06 | Wellstat Therapeutics Corp | Composto de imidazoquinolina com atividade anti-inflamatória, antifúngica, antiparasítica e antineoplásica |
| TW202320766A (zh) * | 2021-09-29 | 2023-06-01 | 大陸商上海海和藥物研究開發股份有限公司 | 一類具有吡啶并六員環結構的ｓｏｓ１抑制劑 |
| EP4580618A2 (en) * | 2022-08-30 | 2025-07-09 | Pannex Therapeutics Inc. | Pannexin-1 modulators and methods of treating disorders in which pannexin-1 is implicated |
| WO2025069039A1 (en) * | 2023-09-28 | 2025-04-03 | Rajaram Samant | An in situ process for the preparation of primary amine compounds |
| WO2025143877A1 (ko) * | 2023-12-28 | 2025-07-03 | (주)앰틱스바이오 | 아미노 니코틴아마이드 구조를 포함하는 유도체 화합물 및 이를 포함하는 항진균성 약학적 조성물 |
Family Cites Families (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4320294Y1 (enExample) | 1964-10-31 | 1968-08-26 | ||
| CH492395A (de) * | 1966-04-26 | 1970-06-30 | Sandoz Ag | Mittel zur Bekämpfung von Pflanzenschädlingen und Verwendung des Mittels |
| GB1496371A (en) * | 1975-08-18 | 1977-12-30 | Serdex | 4-amino-quinoline derivatives process for their preparation and therapeutic applications thereof |
| GB1582407A (en) * | 1977-06-07 | 1981-01-07 | Worcester Controls Uk Ltd | Annular seals |
| JPS53103484A (en) * | 1977-02-21 | 1978-09-08 | Takeda Chem Ind Ltd | Quinazoline derivatives, process for their preparation and nsecticedes and fungicides |
| JPS542325A (en) | 1977-06-07 | 1979-01-09 | Sankyo Co Ltd | Agricultural and horticultural pesticide |
| JPS5576803A (en) * | 1978-12-06 | 1980-06-10 | Sankyo Co Ltd | Agent for controlling noxious life |
| GB2068732B (en) * | 1980-02-08 | 1983-06-02 | Sandoz Ltd | Ectoparasites compounds |
| US4331667A (en) * | 1980-02-08 | 1982-05-25 | Sandoz Ltd. | Quinazolines for controlling ectoparasites |
| GB2135887A (en) | 1983-03-08 | 1984-09-12 | Sandoz Ltd | 4-Alkylamino-quinazolines used as insecticides |
| GB8306360D0 (en) | 1983-03-08 | 1983-04-13 | Sandoz Ltd | Quinazolines |
| ZA848968B (en) | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| CA1271477A (en) * | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| US5114939A (en) * | 1988-01-29 | 1992-05-19 | Dowelanco | Substituted quinolines and cinnolines as fungicides |
| US5294622A (en) * | 1988-01-29 | 1994-03-15 | Dowelanco | Substituted quinolines and cinnolines |
| IL89026A (en) * | 1988-01-29 | 1993-02-21 | Lilly Co Eli | Substituted quinolines and cinnolines, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them |
| US5278173A (en) * | 1988-06-30 | 1994-01-11 | Davis Michael H | Method of inhibiting the activity of human immunodeficiency virus (HIV) in vivo |
| JPH03505579A (ja) * | 1988-06-30 | 1991-12-05 | デービス，マイクル，エイチ | ヒト免疫不全ウイルス（ｈｉｖ）のインビボにおける活性の阻害方法 |
| US5141941A (en) | 1988-11-21 | 1992-08-25 | Ube Industries, Ltd. | Aralkylamine derivatives, and fungicides containing the same |
| US5389640A (en) | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| DE69229114T2 (de) * | 1991-03-01 | 1999-11-04 | Minnesota Mining And Mfg. Co., Saint Paul | 1,2-substituierte 1h-imidazo[4,5-c]chinolin-4-amine |
| NZ243082A (en) * | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| GB9510757D0 (en) * | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| GB9612829D0 (en) | 1996-06-19 | 1996-08-21 | Univ London | Potassium channel blockers |
| DE19647317A1 (de) | 1996-11-15 | 1998-05-20 | Hoechst Schering Agrevo Gmbh | Substituierte Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| SE0102858D0 (sv) * | 2001-08-27 | 2001-08-27 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
| HUP0105407A3 (en) | 2001-12-21 | 2004-04-28 | Sanofi Aventis | Triazolo[1,5-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| HUP0105406A3 (en) | 2001-12-21 | 2003-12-29 | Sanofi Aventis | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| EP2573079A3 (en) | 2002-08-23 | 2015-03-11 | Novartis AG | Benzimidazole quinolinones and uses thereof |
| HUP0203976A3 (en) | 2002-11-15 | 2004-08-30 | Sanofi Aventis | Adenozine a3 receptors, process for their preparation and pharmaceutical compositions containing them |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| US7932272B2 (en) * | 2003-09-30 | 2011-04-26 | Eisai R&D Management Co., Ltd. | Antifungal agent containing heterocyclic compound |
| JP4823914B2 (ja) | 2003-11-07 | 2011-11-24 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | Ｆｇｆｒ３の阻害および多発性骨髄腫の治療 |
| EP1718306A2 (en) | 2004-02-20 | 2006-11-08 | Chiron Corporation | Modulation of inflammatory and metastatic processes |
| US20060074105A1 (en) * | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| EP1844023A1 (en) | 2004-12-31 | 2007-10-17 | Sk Chemicals Co., Ltd. | Quinazoline derivatives for the treatment and prevention of diabetes and obesity |
| EP1945222B1 (en) * | 2005-11-02 | 2012-12-26 | Bayer Pharma Aktiengesellschaft | Pyrrolo[2,1-f] [1,2,4]-triazin-4-ylamines as igf-1r kinase inhibitors for the treatment of cancer and other hyperproliferative diseases |
| ES2429170T3 (es) | 2005-11-04 | 2013-11-13 | 3M Innovative Properties Company | 1H-Imidazoquinolinas sustituidas con hidroxilo y alcoxilo y métodos |
| US7928111B2 (en) | 2007-06-08 | 2011-04-19 | Senomyx, Inc. | Compounds including substituted thienopyrimidinone derivatives as ligands for modulating chemosensory receptors |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| ES2523169T3 (es) | 2008-01-25 | 2014-11-21 | High Point Pharmaceuticals, Llc | Compuestos tricíclicos como moduladores de la síntesis de TNF y como inhibidores de PDE4 |
| JP5599783B2 (ja) | 2008-05-30 | 2014-10-01 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| JP2012502067A (ja) | 2008-09-10 | 2012-01-26 | カリプシス・インコーポレーテッド | 疾患の治療のためのヒスタミン受容体の複素環阻害剤 |
| WO2010074783A1 (en) | 2008-12-23 | 2010-07-01 | The Trustees Of Columbia University In The City Of New York | Phosphodiesterase inhibitors and uses thereof |
| JP2012513464A (ja) * | 2008-12-23 | 2012-06-14 | ザ トラスティーズ オブ コロンビア ユニヴァーシティ イン ザ シティ オブ ニューヨーク | ホスホジエステラーゼ阻害剤及びその使用 |
| KR101699991B1 (ko) | 2009-02-11 | 2017-01-26 | 메르크 파텐트 게엠베하 | 신규의 아미노 아자헤테로시클릭 카르복사미드 |
| CN102625799A (zh) | 2009-06-25 | 2012-08-01 | 安姆根有限公司 | 杂环化合物及其用途 |
| PH12012500097A1 (en) | 2009-07-21 | 2011-01-27 | Shanghai Inst Organic Chem | Potent small molecule inhibitors of autophagy, and methods of use thereof |
| JP2011026251A (ja) | 2009-07-27 | 2011-02-10 | Kowa Co | ２−アリールアミノキノリン化合物及びこれを有効成分として含有するエリスロポエチン産生促進剤 |
| KR101467996B1 (ko) * | 2010-04-30 | 2014-12-11 | 전북대학교산학협력단 | 에이디피-리보실 사이클라제 활성을 저해하는 퀴나졸린 유도체 |
| WO2012079079A1 (en) * | 2010-12-10 | 2012-06-14 | President And Fellows Of Harvard College | Production of induced pluripotent stem cells |
| US20140050696A1 (en) | 2011-04-29 | 2014-02-20 | Ravi K. Amaravadi | Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use |
| BR122021012629B1 (pt) | 2013-02-01 | 2022-06-07 | Wellstat Therapeutics Corporation | Compostos de amina, composição compreendendo os referidos compostos e usos dos mesmos |
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