JP2016506965A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- MHIDLPOVGSZHGV-UHFFFAOYSA-N n-(8-hexoxyoctyl)-8-(trifluoromethyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=NC2=C1C(F)(F)F MHIDLPOVGSZHGV-UHFFFAOYSA-N 0.000 claims 1
- XKBFWRFVUXNZGO-UHFFFAOYSA-N n-(8-hexoxyoctyl)isoquinolin-1-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=NC=CC2=C1 XKBFWRFVUXNZGO-UHFFFAOYSA-N 0.000 claims 1
- OVIKDWHPRZJULL-UHFFFAOYSA-N n-(8-hexoxyoctyl)isoquinolin-5-amine Chemical compound N1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=CC2=C1 OVIKDWHPRZJULL-UHFFFAOYSA-N 0.000 claims 1
- KNKDNUXUKHKMJO-UHFFFAOYSA-N n-(8-hexoxyoctyl)pyrazin-2-amine Chemical compound CCCCCCOCCCCCCCCNC1=CN=CC=N1 KNKDNUXUKHKMJO-UHFFFAOYSA-N 0.000 claims 1
- AQTLHFFJNOKLNK-UHFFFAOYSA-N n-(8-hexoxyoctyl)pyridin-2-amine Chemical compound CCCCCCOCCCCCCCCNC1=CC=CC=N1 AQTLHFFJNOKLNK-UHFFFAOYSA-N 0.000 claims 1
- MQNGLVCJTDLLII-UHFFFAOYSA-N n-(8-hexoxyoctyl)pyridin-3-amine Chemical compound CCCCCCOCCCCCCCCNC1=CC=CN=C1 MQNGLVCJTDLLII-UHFFFAOYSA-N 0.000 claims 1
- HTUQJKPLVGFFGH-UHFFFAOYSA-N n-(8-hexoxyoctyl)pyrimidin-2-amine Chemical compound CCCCCCOCCCCCCCCNC1=NC=CC=N1 HTUQJKPLVGFFGH-UHFFFAOYSA-N 0.000 claims 1
- BMIJOUGFLKUCTQ-UHFFFAOYSA-N n-(8-hexoxyoctyl)quinazolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=NC=NC2=C1 BMIJOUGFLKUCTQ-UHFFFAOYSA-N 0.000 claims 1
- YPUYMIHIBMAESN-UHFFFAOYSA-N n-(8-hexoxyoctyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCCCC)=CC=NC2=C1 YPUYMIHIBMAESN-UHFFFAOYSA-N 0.000 claims 1
- PHXZBQGDNAJUKS-UHFFFAOYSA-N n-(8-hexoxyoctyl)quinolin-6-amine Chemical compound N1=CC=CC2=CC(NCCCCCCCCOCCCCCC)=CC=C21 PHXZBQGDNAJUKS-UHFFFAOYSA-N 0.000 claims 1
- SILHWOFYQMPFIX-UHFFFAOYSA-N n-(8-hexoxyoctyl)quinolin-8-amine Chemical compound C1=CN=C2C(NCCCCCCCCOCCCCCC)=CC=CC2=C1 SILHWOFYQMPFIX-UHFFFAOYSA-N 0.000 claims 1
- XSNWIRSJIKYJEX-UHFFFAOYSA-N n-(8-hexoxyoctyl)quinoxalin-2-amine Chemical compound C1=CC=CC2=NC(NCCCCCCCCOCCCCCC)=CN=C21 XSNWIRSJIKYJEX-UHFFFAOYSA-N 0.000 claims 1
- BYNPJVKSEHCXTF-UHFFFAOYSA-N n-(8-methoxyoctyl)-1-methylpyridin-1-ium-4-amine;iodide Chemical compound [I-].COCCCCCCCCNC1=CC=[N+](C)C=C1 BYNPJVKSEHCXTF-UHFFFAOYSA-N 0.000 claims 1
- GJRJIIJIIOHCJI-UHFFFAOYSA-N n-(8-methoxyoctyl)pyridin-4-amine Chemical compound COCCCCCCCCNC1=CC=NC=C1 GJRJIIJIIOHCJI-UHFFFAOYSA-N 0.000 claims 1
- MDXHVPBEKHCVMO-UHFFFAOYSA-N n-(8-methoxyoctyl)quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOC)=CC=NC2=C1 MDXHVPBEKHCVMO-UHFFFAOYSA-N 0.000 claims 1
- OMKCNMPZLHCNHR-UHFFFAOYSA-N n-(8-phenylmethoxyoctyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCCCOCC1=CC=CC=C1 OMKCNMPZLHCNHR-UHFFFAOYSA-N 0.000 claims 1
- JTRUPXOYKJDGTJ-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC1=CC=CC=N1 JTRUPXOYKJDGTJ-UHFFFAOYSA-N 0.000 claims 1
- AZDDXJLIOJOKAG-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC1=CC=CN=C1 AZDDXJLIOJOKAG-UHFFFAOYSA-N 0.000 claims 1
- BOIOFONSCYXBGQ-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC1=CC=NC=C1 BOIOFONSCYXBGQ-UHFFFAOYSA-N 0.000 claims 1
- RGRCMSYBYURECJ-UHFFFAOYSA-N n-[(2-hexoxyphenyl)methyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1CNC1=CC=NC2=CC=CC=C12 RGRCMSYBYURECJ-UHFFFAOYSA-N 0.000 claims 1
- MMVOCRBGNBNJLZ-UHFFFAOYSA-N n-[(3-decoxyphenyl)methyl]quinazolin-4-amine Chemical compound CCCCCCCCCCOC1=CC=CC(CNC=2C3=CC=CC=C3N=CN=2)=C1 MMVOCRBGNBNJLZ-UHFFFAOYSA-N 0.000 claims 1
- CLPMSJZNPHTHFV-UHFFFAOYSA-N n-[(3-decoxyphenyl)methyl]quinolin-4-amine Chemical compound CCCCCCCCCCOC1=CC=CC(CNC=2C3=CC=CC=C3N=CC=2)=C1 CLPMSJZNPHTHFV-UHFFFAOYSA-N 0.000 claims 1
- DBIKBEYDSGYFHZ-UHFFFAOYSA-N n-[(3-fluoro-4-hexoxyphenyl)methyl]quinolin-4-amine Chemical compound C1=C(F)C(OCCCCCC)=CC=C1CNC1=CC=NC2=CC=CC=C12 DBIKBEYDSGYFHZ-UHFFFAOYSA-N 0.000 claims 1
- INNLQSWTKFNYHD-UHFFFAOYSA-N n-[(3-hexoxyphenyl)methyl]quinazolin-4-amine Chemical compound CCCCCCOC1=CC=CC(CNC=2C3=CC=CC=C3N=CN=2)=C1 INNLQSWTKFNYHD-UHFFFAOYSA-N 0.000 claims 1
- KRIWNALJSJOFLM-UHFFFAOYSA-N n-[(3-hexoxyphenyl)methyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC(CNC=2C3=CC=CC=C3N=CC=2)=C1 KRIWNALJSJOFLM-UHFFFAOYSA-N 0.000 claims 1
- JPHNTMMAHGKCIN-UHFFFAOYSA-N n-[(3-phenoxyphenyl)methyl]quinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NCC(C=1)=CC=CC=1OC1=CC=CC=C1 JPHNTMMAHGKCIN-UHFFFAOYSA-N 0.000 claims 1
- LXEHXASEWHONIH-UHFFFAOYSA-N n-[(3-phenoxyphenyl)methyl]quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC(C=1)=CC=CC=1OC1=CC=CC=C1 LXEHXASEWHONIH-UHFFFAOYSA-N 0.000 claims 1
- FDEZRSUFFATXGG-UHFFFAOYSA-N n-[(3-phenylmethoxyphenyl)methyl]quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC(C=1)=CC=CC=1OCC1=CC=CC=C1 FDEZRSUFFATXGG-UHFFFAOYSA-N 0.000 claims 1
- CVTZIIQCJOLALT-UHFFFAOYSA-N n-[(4-decoxyphenyl)methyl]quinazolin-4-amine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1CNC1=NC=NC2=CC=CC=C12 CVTZIIQCJOLALT-UHFFFAOYSA-N 0.000 claims 1
- FLJSDQPOZUWDIW-UHFFFAOYSA-N n-[(4-decoxyphenyl)methyl]quinolin-4-amine Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1CNC1=CC=NC2=CC=CC=C12 FLJSDQPOZUWDIW-UHFFFAOYSA-N 0.000 claims 1
- GRUDSNALKVAVSN-UHFFFAOYSA-N n-[(4-hexoxyphenyl)methyl]quinazolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1CNC1=NC=NC2=CC=CC=C12 GRUDSNALKVAVSN-UHFFFAOYSA-N 0.000 claims 1
- XTCDJVKGNVGQCW-UHFFFAOYSA-N n-[(4-hexoxyphenyl)methyl]quinolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1CNC1=CC=NC2=CC=CC=C12 XTCDJVKGNVGQCW-UHFFFAOYSA-N 0.000 claims 1
- SBWKIVPGRQIPOI-UHFFFAOYSA-N n-[2-(2-hexoxyphenoxy)ethyl]quinazolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1OCCNC1=NC=NC2=CC=CC=C12 SBWKIVPGRQIPOI-UHFFFAOYSA-N 0.000 claims 1
- QBAFCWRJPQEVKS-UHFFFAOYSA-N n-[2-(3-hexoxyphenoxy)ethyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC(OCCNC=2C3=CC=CC=C3N=CC=2)=C1 QBAFCWRJPQEVKS-UHFFFAOYSA-N 0.000 claims 1
- JKEXWLDHMIFAJZ-UHFFFAOYSA-N n-[2-(4-hexoxyphenoxy)ethyl]quinolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1OCCNC1=CC=NC2=CC=CC=C12 JKEXWLDHMIFAJZ-UHFFFAOYSA-N 0.000 claims 1
- DLPDWVQZSBKKCP-UHFFFAOYSA-N n-[3-(2-ethoxyphenoxy)propyl]quinolin-4-amine Chemical compound CCOC1=CC=CC=C1OCCCNC1=CC=NC2=CC=CC=C12 DLPDWVQZSBKKCP-UHFFFAOYSA-N 0.000 claims 1
- BRZOMJORIJNFLX-UHFFFAOYSA-N n-[3-(2-hexoxyphenoxy)propyl]quinazolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1OCCCNC1=NC=NC2=CC=CC=C12 BRZOMJORIJNFLX-UHFFFAOYSA-N 0.000 claims 1
- LISPMEIINAEAII-UHFFFAOYSA-N n-[3-(2-hexoxyphenoxy)propyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1OCCCNC1=CC=NC2=CC=CC=C12 LISPMEIINAEAII-UHFFFAOYSA-N 0.000 claims 1
- ASRJKQIOWZDICR-UHFFFAOYSA-N n-[3-(2-methoxyphenoxy)propyl]quinolin-4-amine Chemical compound COC1=CC=CC=C1OCCCNC1=CC=NC2=CC=CC=C12 ASRJKQIOWZDICR-UHFFFAOYSA-N 0.000 claims 1
- CUFKXIZLXBFZJX-UHFFFAOYSA-N n-[3-(2-phenylmethoxyphenoxy)propyl]quinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCOC1=CC=CC=C1OCC1=CC=CC=C1 CUFKXIZLXBFZJX-UHFFFAOYSA-N 0.000 claims 1
- BBTMXAFCZDHKSC-UHFFFAOYSA-N n-[3-(3-hexoxyphenoxy)propyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC(OCCCNC=2C3=CC=CC=C3N=CC=2)=C1 BBTMXAFCZDHKSC-UHFFFAOYSA-N 0.000 claims 1
- LLLTZMGSDNZJDT-UHFFFAOYSA-N n-[3-(4-hexoxyphenoxy)propyl]quinolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1OCCCNC1=CC=NC2=CC=CC=C12 LLLTZMGSDNZJDT-UHFFFAOYSA-N 0.000 claims 1
- ILUFWRVSHJZCLJ-UHFFFAOYSA-N n-[3-(5-hexoxypentoxy)propyl]quinolin-4-amine Chemical compound C1=CC=C2C(NCCCOCCCCCOCCCCCC)=CC=NC2=C1 ILUFWRVSHJZCLJ-UHFFFAOYSA-N 0.000 claims 1
- JMXHPCIKPLFEBD-UHFFFAOYSA-N n-[3-(quinolin-4-ylamino)phenyl]hexanamide Chemical compound CCCCCC(=O)NC1=CC=CC(NC=2C3=CC=CC=C3N=CC=2)=C1 JMXHPCIKPLFEBD-UHFFFAOYSA-N 0.000 claims 1
- NCZOAUATNYGHTI-UHFFFAOYSA-N n-[4-(2-hexoxyphenoxy)butyl]quinazolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1OCCCCNC1=NC=NC2=CC=CC=C12 NCZOAUATNYGHTI-UHFFFAOYSA-N 0.000 claims 1
- PEKAINBKSUNCGW-UHFFFAOYSA-N n-[4-(2-hexoxyphenoxy)butyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC=C1OCCCCNC1=CC=NC2=CC=CC=C12 PEKAINBKSUNCGW-UHFFFAOYSA-N 0.000 claims 1
- JFWBQUMHNIMRLH-UHFFFAOYSA-N n-[4-(3-hexoxyphenoxy)butyl]quinolin-4-amine Chemical compound CCCCCCOC1=CC=CC(OCCCCNC=2C3=CC=CC=C3N=CC=2)=C1 JFWBQUMHNIMRLH-UHFFFAOYSA-N 0.000 claims 1
- ASYOOHKZRGPJOU-UHFFFAOYSA-N n-[4-(4-hexoxyphenoxy)butyl]quinolin-4-amine Chemical compound C1=CC(OCCCCCC)=CC=C1OCCCCNC1=CC=NC2=CC=CC=C12 ASYOOHKZRGPJOU-UHFFFAOYSA-N 0.000 claims 1
- PFPPCHOWFQUUSQ-UHFFFAOYSA-N n-[4-(quinolin-4-ylamino)butyl]benzamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCNC(=O)C1=CC=CC=C1 PFPPCHOWFQUUSQ-UHFFFAOYSA-N 0.000 claims 1
- YAWRQXQOCOYPRS-UHFFFAOYSA-N n-[4-(quinolin-4-ylamino)phenyl]hexanamide Chemical compound C1=CC(NC(=O)CCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 YAWRQXQOCOYPRS-UHFFFAOYSA-N 0.000 claims 1
- GXTFNRLQTBXIHQ-UHFFFAOYSA-N n-[5-(3-hexoxypropoxy)pentyl]quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCOCCCOCCCCCC)=CC=NC2=C1 GXTFNRLQTBXIHQ-UHFFFAOYSA-N 0.000 claims 1
- JTYYJPKQSIIVIR-UHFFFAOYSA-N n-[6-(4-methoxyphenoxy)hexyl]quinolin-4-amine Chemical compound C1=CC(OC)=CC=C1OCCCCCCNC1=CC=NC2=CC=CC=C12 JTYYJPKQSIIVIR-UHFFFAOYSA-N 0.000 claims 1
- OXFNTCHLAHXWDD-UHFFFAOYSA-N n-[6-(quinolin-4-ylamino)hexyl]benzamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCNC(=O)C1=CC=CC=C1 OXFNTCHLAHXWDD-UHFFFAOYSA-N 0.000 claims 1
- ZSOQANVPPATGJN-UHFFFAOYSA-N n-[8-(2-fluorophenoxy)octyl]quinolin-4-amine Chemical compound FC1=CC=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 ZSOQANVPPATGJN-UHFFFAOYSA-N 0.000 claims 1
- ZSVJAUVNPFNOIF-UHFFFAOYSA-N n-[8-(2-methylphenoxy)octyl]quinolin-4-amine Chemical compound CC1=CC=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 ZSVJAUVNPFNOIF-UHFFFAOYSA-N 0.000 claims 1
- ALSZOFKYCSSHBX-UHFFFAOYSA-N n-[8-(2-propoxyethoxy)octyl]quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCOCCC)=CC=NC2=C1 ALSZOFKYCSSHBX-UHFFFAOYSA-N 0.000 claims 1
- AEDRGUFWOIFSDY-UHFFFAOYSA-N n-[8-(3-ethoxypropoxy)octyl]quinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCOCCCOCC)=CC=NC2=C1 AEDRGUFWOIFSDY-UHFFFAOYSA-N 0.000 claims 1
- MCIIQJRHQFRUQA-UHFFFAOYSA-N n-[8-(3-fluorophenoxy)octyl]quinolin-4-amine Chemical compound FC1=CC=CC(OCCCCCCCCNC=2C3=CC=CC=C3N=CC=2)=C1 MCIIQJRHQFRUQA-UHFFFAOYSA-N 0.000 claims 1
- NDXSCLDAMDNKIR-UHFFFAOYSA-N n-[8-(3-methoxyphenoxy)octyl]quinolin-4-amine Chemical compound COC1=CC=CC(OCCCCCCCCNC=2C3=CC=CC=C3N=CC=2)=C1 NDXSCLDAMDNKIR-UHFFFAOYSA-N 0.000 claims 1
- TWVWIYRRMUADQY-UHFFFAOYSA-N n-[8-(3-methylphenoxy)octyl]quinolin-4-amine Chemical compound CC1=CC=CC(OCCCCCCCCNC=2C3=CC=CC=C3N=CC=2)=C1 TWVWIYRRMUADQY-UHFFFAOYSA-N 0.000 claims 1
- ZDKUVEBZJMFTNR-UHFFFAOYSA-N n-[8-(4-fluorophenoxy)octyl]quinolin-4-amine Chemical compound C1=CC(F)=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 ZDKUVEBZJMFTNR-UHFFFAOYSA-N 0.000 claims 1
- NBSKKRXCESZVCC-UHFFFAOYSA-N n-[8-(4-methoxyphenoxy)octyl]quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1OCCCCCCCCNC1=NC=NC2=CC=CC=C12 NBSKKRXCESZVCC-UHFFFAOYSA-N 0.000 claims 1
- FFIRVIAAQLSSBM-UHFFFAOYSA-N n-[8-(4-methoxyphenoxy)octyl]quinolin-4-amine Chemical compound C1=CC(OC)=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 FFIRVIAAQLSSBM-UHFFFAOYSA-N 0.000 claims 1
- NZQPOWIUUTUXNO-UHFFFAOYSA-N n-[8-(4-methylphenoxy)octyl]quinolin-4-amine Chemical compound C1=CC(C)=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 NZQPOWIUUTUXNO-UHFFFAOYSA-N 0.000 claims 1
- CEBINMSREOMHMS-UHFFFAOYSA-N n-[8-(4-tert-butylphenoxy)octyl]quinolin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCCCCCCCNC1=CC=NC2=CC=CC=C12 CEBINMSREOMHMS-UHFFFAOYSA-N 0.000 claims 1
- ADZZHESKAHSNJJ-UHFFFAOYSA-N n-[8-(quinazolin-4-ylamino)octyl]pyridine-3-carboxamide Chemical compound N=1C=NC2=CC=CC=C2C=1NCCCCCCCCNC(=O)C1=CC=CN=C1 ADZZHESKAHSNJJ-UHFFFAOYSA-N 0.000 claims 1
- CPCMNJFWTYTGOB-UHFFFAOYSA-N n-[8-(quinolin-4-ylamino)octyl]benzamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCCCNC(=O)C1=CC=CC=C1 CPCMNJFWTYTGOB-UHFFFAOYSA-N 0.000 claims 1
- KMMRBCVOLKAHFZ-UHFFFAOYSA-N n-[8-(quinolin-4-ylamino)octyl]pyridine-2-carboxamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCCCNC(=O)C1=CC=CC=N1 KMMRBCVOLKAHFZ-UHFFFAOYSA-N 0.000 claims 1
- YOITYJKYIGUEDL-UHFFFAOYSA-N n-[8-(quinolin-4-ylamino)octyl]pyridine-3-carboxamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCCCNC(=O)C1=CC=CN=C1 YOITYJKYIGUEDL-UHFFFAOYSA-N 0.000 claims 1
- VLPLMYKQHDFAFM-UHFFFAOYSA-N n-[8-(quinolin-4-ylamino)octyl]pyridine-4-carboxamide Chemical compound C=1C=NC2=CC=CC=C2C=1NCCCCCCCCNC(=O)C1=CC=NC=C1 VLPLMYKQHDFAFM-UHFFFAOYSA-N 0.000 claims 1
- IEIBZPOWNOCCAT-UHFFFAOYSA-N n-benzylquinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1NCC1=CC=CC=C1 IEIBZPOWNOCCAT-UHFFFAOYSA-N 0.000 claims 1
- LMYAWBRBBUTZQH-UHFFFAOYSA-N n-decyl-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(NCCCCCCCCCC)=NC=NC2=C1 LMYAWBRBBUTZQH-UHFFFAOYSA-N 0.000 claims 1
- VZOBKPIQCJYTLQ-UHFFFAOYSA-N n-decylquinazolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCC)=NC=NC2=C1 VZOBKPIQCJYTLQ-UHFFFAOYSA-N 0.000 claims 1
- JCWMRNNEBVWIFS-UHFFFAOYSA-N n-decylquinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCC)=CC=NC2=C1 JCWMRNNEBVWIFS-UHFFFAOYSA-N 0.000 claims 1
- CDSJGRBQZLUJHI-UHFFFAOYSA-N n-dodecyl-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(NCCCCCCCCCCCC)=NC=NC2=C1 CDSJGRBQZLUJHI-UHFFFAOYSA-N 0.000 claims 1
- FXPAFSNOEVASDH-UHFFFAOYSA-N n-dodecylquinazolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCCCC)=NC=NC2=C1 FXPAFSNOEVASDH-UHFFFAOYSA-N 0.000 claims 1
- BSNZXYWUNSHLHG-UHFFFAOYSA-N n-dodecylquinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCCCCCCCC)=CC=NC2=C1 BSNZXYWUNSHLHG-UHFFFAOYSA-N 0.000 claims 1
- NMARBHKBIZWEEW-UHFFFAOYSA-N n-hexyl-3-(quinolin-4-ylamino)benzamide Chemical compound CCCCCCNC(=O)C1=CC=CC(NC=2C3=CC=CC=C3N=CC=2)=C1 NMARBHKBIZWEEW-UHFFFAOYSA-N 0.000 claims 1
- PGXOALWNBBIAKO-UHFFFAOYSA-N n-hexyl-4-(quinolin-4-ylamino)benzamide Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1NC1=CC=NC2=CC=CC=C12 PGXOALWNBBIAKO-UHFFFAOYSA-N 0.000 claims 1
- LTFYUVAOGATXQX-UHFFFAOYSA-N n-hexylquinolin-4-amine Chemical compound C1=CC=C2C(NCCCCCC)=CC=NC2=C1 LTFYUVAOGATXQX-UHFFFAOYSA-N 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361759512P | 2013-02-01 | 2013-02-01 | |
| US61/759,512 | 2013-02-01 | ||
| PCT/US2014/013992 WO2014120995A2 (en) | 2013-02-01 | 2014-01-31 | Amine compounds having anti-inflammatory, antifungal, antiparasitic and anticancer activity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018247914A Division JP6724128B2 (ja) | 2013-02-01 | 2018-12-28 | 抗炎症、抗真菌、抗寄生生物及び抗癌活性を有するアミン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016506965A JP2016506965A (ja) | 2016-03-07 |
| JP2016506965A5 true JP2016506965A5 (enExample) | 2017-02-09 |
| JP6463276B2 JP6463276B2 (ja) | 2019-01-30 |
Family
ID=51263115
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015556146A Expired - Fee Related JP6463276B2 (ja) | 2013-02-01 | 2014-01-31 | 抗炎症、抗真菌、抗寄生生物及び抗癌活性を有するアミン化合物 |
| JP2018247914A Active JP6724128B2 (ja) | 2013-02-01 | 2018-12-28 | 抗炎症、抗真菌、抗寄生生物及び抗癌活性を有するアミン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018247914A Active JP6724128B2 (ja) | 2013-02-01 | 2018-12-28 | 抗炎症、抗真菌、抗寄生生物及び抗癌活性を有するアミン化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US10030015B2 (enExample) |
| EP (2) | EP2950649B1 (enExample) |
| JP (2) | JP6463276B2 (enExample) |
| KR (2) | KR102205202B1 (enExample) |
| CN (2) | CN108250142B (enExample) |
| AU (2) | AU2014212242B2 (enExample) |
| BR (2) | BR122021012629B1 (enExample) |
| CA (3) | CA3217159A1 (enExample) |
| DK (1) | DK2950649T3 (enExample) |
| ES (1) | ES2790675T3 (enExample) |
| IL (2) | IL240205B (enExample) |
| MX (5) | MX369611B (enExample) |
| NZ (1) | NZ709885A (enExample) |
| PL (1) | PL2950649T3 (enExample) |
| RU (2) | RU2721418C2 (enExample) |
| WO (1) | WO2014120995A2 (enExample) |
| ZA (1) | ZA201504954B (enExample) |
Families Citing this family (25)
| 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 |
| MY188211A (en) | 2015-03-04 | 2021-11-24 | Gilead Sciences Inc | Toll-like receptor modulating 4,6-diamino-pyrido[3,2-d]pyrimidine compounds |
| MA46093A (fr) | 2016-09-02 | 2021-05-19 | Gilead Sciences Inc | Composés modulateurs du recepteur de type toll |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| 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 |
| US11364237B2 (en) * | 2017-02-07 | 2022-06-21 | Oncocross Co., Ltd. | Composition for inhibiting cancer metastasis and treating cancer |
| RU2019132396A (ru) * | 2017-03-15 | 2021-04-15 | Лунелла Байотек, Инк. | Миторибосцины: терапевтические средства на основе митохондрий, направленные на раковые клетки, бактерии и патогенные дрожжи |
| 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 |
| CN111960985A (zh) * | 2018-08-08 | 2020-11-20 | 中国人民解放军总医院 | 抗肿瘤化合物 |
| AU2020204991A1 (en) | 2019-01-04 | 2021-07-22 | Bellbrook Labs, Llc | Inhibitors of cGAS activity as therapeutic agents |
| 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 |
| PL3992177T3 (pl) | 2019-06-25 | 2024-08-26 | Amtixbio Co., Ltd. | Nowatorska pochodna kwasu aminoalkanowego, zawierająca w swojej strukturze ugrupowanie bifenylowe, oraz kompozycja farmaceutyczna o działaniu przeciwgrzybiczym, w skład której wchodzi ta pochodna |
| 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 |
| CA3193207A1 (en) * | 2020-09-25 | 2022-03-31 | Marion Lanier | Modulators of mas-related g-protein receptor x2 and related products and methods |
| WO2023051628A1 (zh) * | 2021-09-29 | 2023-04-06 | 上海海和药物研究开发股份有限公司 | 一类具有吡啶并六元环结构的sos1抑制剂 |
| 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 |
| GB8306360D0 (en) * | 1983-03-08 | 1983-04-13 | Sandoz Ltd | Quinazolines |
| GB2135887A (en) | 1983-03-08 | 1984-09-12 | Sandoz Ltd | 4-Alkylamino-quinazolines used as insecticides |
| CA1271477A (en) | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| 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 |
| US5114939A (en) * | 1988-01-29 | 1992-05-19 | Dowelanco | Substituted quinolines and cinnolines as fungicides |
| 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 |
| US5294622A (en) * | 1988-01-29 | 1994-03-15 | Dowelanco | Substituted quinolines and cinnolines |
| WO1990000055A1 (en) | 1988-06-30 | 1990-01-11 | Davis Michael H | Method of inhibiting the activity of human immunodeficiency virus (hiv) in vivo |
| US5278173A (en) * | 1988-06-30 | 1994-01-11 | Davis Michael H | Method of inhibiting the activity of human immunodeficiency virus (HIV) in vivo |
| US5141941A (en) * | 1988-11-21 | 1992-08-25 | Ube Industries, Ltd. | Aralkylamine derivatives, and fungicides containing the same |
| HU222250B1 (hu) * | 1991-03-01 | 2003-05-28 | Minnesota Mining And Manufacturing Company | 1- és 2-helyzetben szubsztituált 1H-imidazo[4,5-c]kinolin-4-amin-származékok előállításában alkalmazható intermedierek |
| 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 |
| 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 |
| JP4613130B2 (ja) | 2002-08-23 | 2011-01-12 | 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 | ベンゾイミダゾールキノリノンおよびそれらの使用 |
| 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 |
| EP1669348A4 (en) * | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| MXPA06004194A (es) | 2003-11-07 | 2006-06-28 | Chiron Corp | Inhibicion de fgfr3 y tratamiento de mieloma multiple. |
| US7875624B2 (en) | 2004-02-20 | 2011-01-25 | Novartis Vaccines And Diagnostics, Inc. | Modulating and measuring cellular adhesion |
| US20060074105A1 (en) | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| JP2008526734A (ja) | 2004-12-31 | 2008-07-24 | エスケー ケミカルズ カンパニー リミテッド | 糖尿及び肥満治療予防に有効なキナゾリン誘導体 |
| US8431695B2 (en) * | 2005-11-02 | 2013-04-30 | Bayer Intellectual Property Gmbh | Pyrrolo[2,1-f][1,2,4]triazin-4-ylamines IGF-1R kinase inhibitors for the treatment of cancer and other hyperproliferative diseases |
| EP1948173B1 (en) | 2005-11-04 | 2013-07-17 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| US7928111B2 (en) | 2007-06-08 | 2011-04-19 | Senomyx, Inc. | Compounds including substituted thienopyrimidinone derivatives as ligands for modulating chemosensory receptors |
| EP2219646A4 (en) | 2007-12-21 | 2010-12-22 | Univ Rochester | PROCESS FOR EXTENDING THE LIFE OF EUKARYOTIC ORGANISMS |
| EA018462B1 (ru) | 2008-01-25 | 2013-08-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | ТРИЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ КАК МОДУЛЯТОРЫ СИНТЕЗА TNF-α И КАК ИНГИБИТОРЫ PDE4 |
| EP2307400B1 (en) | 2008-05-30 | 2014-04-23 | Amgen, Inc | Inhibitors of pi3 kinase |
| 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 |
| EP2379076B1 (en) * | 2008-12-23 | 2014-11-12 | The Trustees of Columbia University in the City of New York | Phosphodiesterase inhibitors and uses thereof |
| WO2010074783A1 (en) | 2008-12-23 | 2010-07-01 | The Trustees Of Columbia University In The City Of New York | Phosphodiesterase inhibitors and uses thereof |
| KR101699991B1 (ko) | 2009-02-11 | 2017-01-26 | 메르크 파텐트 게엠베하 | 신규의 아미노 아자헤테로시클릭 카르복사미드 |
| JP2012531438A (ja) | 2009-06-25 | 2012-12-10 | アムジエン・インコーポレーテツド | 複素環式化合物およびその使用 |
| 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 |
| JP6162687B2 (ja) | 2011-04-29 | 2017-07-12 | ザ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・ペンシルベニア | 新規のビスアミノキノリン化合物、それから調製した医薬組成物、及びそれらの使用 |
| BR122021012629B1 (pt) | 2013-02-01 | 2022-06-07 | Wellstat Therapeutics Corporation | Compostos de amina, composição compreendendo os referidos compostos e usos dos mesmos |
-
2014
- 2014-01-31 BR BR122021012629-1A patent/BR122021012629B1/pt not_active IP Right Cessation
- 2014-01-31 WO PCT/US2014/013992 patent/WO2014120995A2/en not_active Ceased
- 2014-01-31 ES ES14746786T patent/ES2790675T3/es active Active
- 2014-01-31 AU AU2014212242A patent/AU2014212242B2/en active Active
- 2014-01-31 RU RU2019100054A patent/RU2721418C2/ru active
- 2014-01-31 NZ NZ709885A patent/NZ709885A/en active IP Right Revival
- 2014-01-31 CN CN201810151916.5A patent/CN108250142B/zh active Active
- 2014-01-31 EP EP14746786.4A patent/EP2950649B1/en active Active
- 2014-01-31 BR BR112015018282-8A patent/BR112015018282B1/pt not_active IP Right Cessation
- 2014-01-31 CA CA3217159A patent/CA3217159A1/en active Pending
- 2014-01-31 PL PL14746786T patent/PL2950649T3/pl unknown
- 2014-01-31 CA CA3102531A patent/CA3102531A1/en active Pending
- 2014-01-31 KR KR1020157023305A patent/KR102205202B1/ko active Active
- 2014-01-31 EP EP19201890.1A patent/EP3632426A1/en active Pending
- 2014-01-31 DK DK14746786.4T patent/DK2950649T3/da active
- 2014-01-31 US US14/764,207 patent/US10030015B2/en active Active
- 2014-01-31 KR KR1020217000847A patent/KR20210007046A/ko not_active Ceased
- 2014-01-31 MX MX2015009864A patent/MX369611B/es active IP Right Grant
- 2014-01-31 CN CN201480007029.0A patent/CN104968200B/zh not_active Expired - Fee Related
- 2014-01-31 JP JP2015556146A patent/JP6463276B2/ja not_active Expired - Fee Related
- 2014-01-31 RU RU2015137094A patent/RU2677229C2/ru active
- 2014-01-31 CA CA2898018A patent/CA2898018C/en active Active
-
2015
- 2015-07-09 ZA ZA2015/04954A patent/ZA201504954B/en unknown
- 2015-07-28 IL IL24020515A patent/IL240205B/en active IP Right Grant
- 2015-07-30 MX MX2024007304A patent/MX2024007304A/es unknown
- 2015-07-30 MX MX2024007308A patent/MX2024007308A/es unknown
- 2015-07-30 MX MX2019004884A patent/MX2019004884A/es unknown
- 2015-07-30 MX MX2024007306A patent/MX2024007306A/es unknown
-
2018
- 2018-02-21 AU AU2018201239A patent/AU2018201239A1/en not_active Abandoned
- 2018-06-22 US US16/015,264 patent/US20180298000A1/en not_active Abandoned
- 2018-12-28 JP JP2018247914A patent/JP6724128B2/ja active Active
-
2019
- 2019-02-26 US US16/285,460 patent/US10934284B2/en active Active
- 2019-09-24 IL IL269583A patent/IL269583B/en unknown
-
2021
- 2021-02-16 US US17/176,923 patent/US12139483B2/en active Active
-
2024
- 2024-10-04 US US18/906,289 patent/US20250034139A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016506965A5 (enExample) | ||
| RU2015137094A (ru) | Соединения амина, имеющие противовоспалительную, противогрибковую, противопаразитарную и противораковую активность | |
| Vandekerckhove et al. | Quinoline-based antimalarial hybrid compounds | |
| JP2016525076A5 (enExample) | ||
| JP2010531313A5 (enExample) | ||
| JP2016516791A5 (enExample) | ||
| JP2017504652A5 (enExample) | ||
| EA004939B1 (ru) | Ингибиторы репликации респираторно-синцитиального вируса | |
| NZ607060A (en) | Substituted imidazoquinoline derivatives as kinase inhibitors | |
| EP3898654A2 (en) | Inhibitors of fibroblast activation protein | |
| JP2013510125A5 (enExample) | ||
| RU2018131775A (ru) | 6-арил-4-морфолин-1-илпиридоны, пригодные для лечения рака или диабета | |
| JP2011503230A5 (enExample) | ||
| JP2016504290A5 (enExample) | ||
| NZ630124A (en) | Estrogen receptor modulators and uses thereof | |
| PH12013500773A1 (en) | Crystalline and other forms of 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-1h-quinolin-2-one lactic acid salts | |
| NZ547615A (en) | Quinoline derivatives and use thereof as mycobacterial inhibitors | |
| JP2013542261A5 (enExample) | ||
| SK8582003A3 (en) | Substituted alkylamine derivatives and methods of use | |
| SK17932001A3 (sk) | Imidazochinolíny substituované amidom | |
| JP2019505594A5 (enExample) | ||
| CA2579087A1 (en) | Pyrrolo[2,3-c]pyridine derivatives and processes for the preparation thereof | |
| JP2017517512A5 (enExample) | ||
| NZ590954A (en) | Compounds as kinase inhibitors | |
| RU2016111659A (ru) | Соединение с агонистической активностью в отношении рецепторов соматостатина и его фармацевтическое применение |