ZA200104410B - Novel bicyclic compounds. - Google Patents
Novel bicyclic compounds. Download PDFInfo
- Publication number
- ZA200104410B ZA200104410B ZA200104410A ZA200104410A ZA200104410B ZA 200104410 B ZA200104410 B ZA 200104410B ZA 200104410 A ZA200104410 A ZA 200104410A ZA 200104410 A ZA200104410 A ZA 200104410A ZA 200104410 B ZA200104410 B ZA 200104410B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzofuran
- methyl
- pyridin
- ylmethyl
- propoxy
- Prior art date
Links
- 125000002619 bicyclic group Chemical group 0.000 title claims description 42
- -1 benzoimidazolyl Chemical group 0.000 claims description 440
- 125000000217 alkyl group Chemical group 0.000 claims description 157
- 150000001875 compounds Chemical class 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 49
- 125000005842 heteroatom Chemical group 0.000 claims description 49
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 125000001931 aliphatic group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000002168 alkylating agent Substances 0.000 claims description 8
- 229940100198 alkylating agent Drugs 0.000 claims description 8
- 230000002152 alkylating effect Effects 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 208000031888 Mycoses Diseases 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- UYQSNRSISGNDIN-UHFFFAOYSA-N ethyl 3-cyclopropyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C3CC3)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 UYQSNRSISGNDIN-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- YUPKKOHDTWNQEB-UHFFFAOYSA-N ethyl 4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=CC2=C1OCCCNCC1=CC=CN=C1 YUPKKOHDTWNQEB-UHFFFAOYSA-N 0.000 claims description 3
- UGQISDYHYKWELL-UHFFFAOYSA-N ethyl 4-[3-(tert-butylamino)propoxy]-3-propyl-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCNC(C)(C)C)=C2C(CCC)=C(C(=O)OCC)OC2=C1 UGQISDYHYKWELL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- CEAYDFRFGXDHEU-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-[5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]methanone Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC(C=C1C=2)=CC=C1OC=2C(=O)N1CCC(O)CC1 CEAYDFRFGXDHEU-UHFFFAOYSA-N 0.000 claims description 2
- YQOBCQPLIRWBGV-UHFFFAOYSA-N (5,6-difluoro-1-methylbenzimidazol-2-yl)-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methanone Chemical compound C=12C(C)=C(C(=O)C=3N(C4=CC(F)=C(F)C=C4N=3)C)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 YQOBCQPLIRWBGV-UHFFFAOYSA-N 0.000 claims description 2
- PHCVBYJSFJLZJA-UHFFFAOYSA-N 2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-n-propan-2-yl-1,3-oxazole-4-carboxamide Chemical compound CC(C)NC(=O)C1=COC(C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=N1 PHCVBYJSFJLZJA-UHFFFAOYSA-N 0.000 claims description 2
- YEUVEKXMDVVJEE-UHFFFAOYSA-N 2-cyclohexylethyl 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound CC=1C=2C(OCC(O)CNC(C)C)=CC=CC=2OC=1C(=O)OCCC1CCCCC1 YEUVEKXMDVVJEE-UHFFFAOYSA-N 0.000 claims description 2
- FXVJAKYFWDZRLZ-UHFFFAOYSA-N 3-[[2-(2-methoxyphenyl)-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound COC1=CC=CC=C1C1=C(C)C2=C(OCCCNCC=3C=NC=CC=3)C=CC=C2O1 FXVJAKYFWDZRLZ-UHFFFAOYSA-N 0.000 claims description 2
- XLCMCWQJVSBPMN-UHFFFAOYSA-N 3-[[2-[(2,4-difluorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-methyl-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound C=1C=CN=CC=1CN(C)CCCOC(C=1C=2C)=CC=CC=1OC=2COC1=CC=C(F)C=C1F XLCMCWQJVSBPMN-UHFFFAOYSA-N 0.000 claims description 2
- YAVPHENICCAKQD-UHFFFAOYSA-N 3-[[2-[(2-fluorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=CC=C1F YAVPHENICCAKQD-UHFFFAOYSA-N 0.000 claims description 2
- KWZSFGQMKYRCJI-UHFFFAOYSA-N 3-[[2-[(3-fluorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=CC(F)=C1 KWZSFGQMKYRCJI-UHFFFAOYSA-N 0.000 claims description 2
- YXBVEDYIACFQGK-UHFFFAOYSA-N 3-[[2-[(4-chlorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=C(Cl)C=C1 YXBVEDYIACFQGK-UHFFFAOYSA-N 0.000 claims description 2
- ULOQWYDKSGDSEL-UHFFFAOYSA-N 3-[[2-[3-[(3-fluorophenyl)methoxy]propyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CCCOCC1=CC=CC(F)=C1 ULOQWYDKSGDSEL-UHFFFAOYSA-N 0.000 claims description 2
- ARJQTHOPXIYNOJ-UHFFFAOYSA-N 3-[[2-[[2-(ethoxymethyl)-1-benzofuran-5-yl]oxymethyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-methyl-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound C=1C=C2OC(COCC)=CC2=CC=1OCC(=C(C1=2)C)OC1=CC=CC=2OCCCN(C)CC1=CC=CN=C1 ARJQTHOPXIYNOJ-UHFFFAOYSA-N 0.000 claims description 2
- IFHSJXHCSOIBLN-UHFFFAOYSA-N 3-[[3-methyl-2-(2-phenylethyl)-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CCC1=CC=CC=C1 IFHSJXHCSOIBLN-UHFFFAOYSA-N 0.000 claims description 2
- UVIRLAKAGZOYAT-UHFFFAOYSA-N 3-[[3-methyl-2-(2-phenylethylsulfanylmethyl)-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CSCCC1=CC=CC=C1 UVIRLAKAGZOYAT-UHFFFAOYSA-N 0.000 claims description 2
- IAXPYHXYWUAXED-UHFFFAOYSA-N 3-[[3-methyl-2-(2-phenylethylsulfanylmethyl)-1-benzofuran-4-yl]oxy]-n-propan-2-ylpropan-1-amine Chemical compound CC=1C=2C(OCCCNC(C)C)=CC=CC=2OC=1CSCCC1=CC=CC=C1 IAXPYHXYWUAXED-UHFFFAOYSA-N 0.000 claims description 2
- LSVOXWPYBBWXTM-UHFFFAOYSA-N 3-[[3-methyl-2-[(2,3,4,5,6-pentafluorophenoxy)methyl]-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=C(F)C(F)=C(F)C(F)=C1F LSVOXWPYBBWXTM-UHFFFAOYSA-N 0.000 claims description 2
- MMFUMYYLCVNBEA-UHFFFAOYSA-N 3-[[4-[[2-[[2-(ethoxymethyl)-1-benzofuran-5-yl]oxymethyl]-3-methyl-1-benzofuran-4-yl]oxy]piperidin-1-yl]methyl]pyridine Chemical compound C=1C=C2OC(COCC)=CC2=CC=1OCC(=C(C1=2)C)OC1=CC=CC=2OC(CC1)CCN1CC1=CC=CN=C1 MMFUMYYLCVNBEA-UHFFFAOYSA-N 0.000 claims description 2
- ZRJWWAGSBIGGBA-UHFFFAOYSA-N 3-methyl-n'-(3-nitrophenyl)-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carbohydrazide Chemical compound C=12C(C)=C(C(=O)NNC=3C=C(C=CC=3)[N+]([O-])=O)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 ZRJWWAGSBIGGBA-UHFFFAOYSA-N 0.000 claims description 2
- STNDLVAMIAXTQH-UHFFFAOYSA-N 3-methyl-n-phenyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NC=3C=CC=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 STNDLVAMIAXTQH-UHFFFAOYSA-N 0.000 claims description 2
- OSAYRUAPWAQEJW-UHFFFAOYSA-N 4-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]benzonitrile Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=C(C#N)C=C1 OSAYRUAPWAQEJW-UHFFFAOYSA-N 0.000 claims description 2
- HOAOEJXPLRRYQX-UHFFFAOYSA-N C=12C(C)=C(C(=S)NC=3C(=CC(F)=CC=3)F)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 Chemical compound C=12C(C)=C(C(=S)NC=3C(=CC(F)=CC=3)F)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 HOAOEJXPLRRYQX-UHFFFAOYSA-N 0.000 claims description 2
- UNOXJCJZOFPZCB-UHFFFAOYSA-N COC1=CC(OC)=CC(NC(=O)C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=C1 Chemical compound COC1=CC(OC)=CC(NC(=O)C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=C1 UNOXJCJZOFPZCB-UHFFFAOYSA-N 0.000 claims description 2
- HLDZSWHYIROVAD-UHFFFAOYSA-N [2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-1,3-oxazol-4-yl]-(1,3-thiazolidin-3-yl)methanone Chemical compound C=12C(C)=C(C=3OC=C(N=3)C(=O)N3CSCC3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 HLDZSWHYIROVAD-UHFFFAOYSA-N 0.000 claims description 2
- AZIHYXDCMXTHEQ-UHFFFAOYSA-N [3-cyclopropyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methanol Chemical compound C=12C(C3CC3)=C(CO)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 AZIHYXDCMXTHEQ-UHFFFAOYSA-N 0.000 claims description 2
- KSMWRTSICDAGPU-UHFFFAOYSA-N [3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-pyridin-2-ylmethanone Chemical compound C=12C(C)=C(C(=O)C=3N=CC=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 KSMWRTSICDAGPU-UHFFFAOYSA-N 0.000 claims description 2
- KDPBHVMEOGYPBM-UHFFFAOYSA-N [3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methanol Chemical compound C=12C(C)=C(CO)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 KDPBHVMEOGYPBM-UHFFFAOYSA-N 0.000 claims description 2
- MFHAETMQYGVXLQ-UHFFFAOYSA-N [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1-benzofuran-2-yl]-piperidin-1-ylmethanone Chemical compound CC=1C=2C(OCC(O)CNC(C)C)=CC=CC=2OC=1C(=O)N1CCCCC1 MFHAETMQYGVXLQ-UHFFFAOYSA-N 0.000 claims description 2
- VHJSXAWXBUOKIG-UHFFFAOYSA-N [5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]-piperazin-1-ylmethanone Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC(C=C1C=2)=CC=C1OC=2C(=O)N1CCNCC1 VHJSXAWXBUOKIG-UHFFFAOYSA-N 0.000 claims description 2
- DWAUSTLVCYCSSV-UHFFFAOYSA-N [5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]methanol Chemical compound C=12C(C)=C(COC=3C=C4C=C(CO)OC4=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 DWAUSTLVCYCSSV-UHFFFAOYSA-N 0.000 claims description 2
- FSIRWECAOGSMTB-UHFFFAOYSA-N [5-[[3-methyl-4-[[1-(pyridin-3-ylmethyl)piperidin-3-yl]methoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]methyl acetate Chemical compound C=1C=C2OC(COC(=O)C)=CC2=CC=1OCC(=C(C1=2)C)OC1=CC=CC=2OCC(C1)CCCN1CC1=CC=CN=C1 FSIRWECAOGSMTB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- QTEMXGYXKDDOOS-UHFFFAOYSA-N ethyl 2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-1,3-oxazole-4-carboxylate Chemical compound CCOC(=O)C1=COC(C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=N1 QTEMXGYXKDDOOS-UHFFFAOYSA-N 0.000 claims description 2
- ZFUMKNOPFNNPKJ-UHFFFAOYSA-N ethyl 2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=N1 ZFUMKNOPFNNPKJ-UHFFFAOYSA-N 0.000 claims description 2
- UYYQVHQCKLDIOO-UHFFFAOYSA-N ethyl 3-(aminomethyl)-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(CN)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 UYYQVHQCKLDIOO-UHFFFAOYSA-N 0.000 claims description 2
- YATWOBGGMKUMHB-UHFFFAOYSA-N ethyl 3-butyl-4-[3-(tert-butylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCNC(C)(C)C)=C2C(CCCC)=C(C(=O)OCC)OC2=C1 YATWOBGGMKUMHB-UHFFFAOYSA-N 0.000 claims description 2
- JMQTXYVAPRXHMV-UHFFFAOYSA-N ethyl 3-ethyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(CC)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 JMQTXYVAPRXHMV-UHFFFAOYSA-N 0.000 claims description 2
- JTRGDVDJOWAPHG-UHFFFAOYSA-N ethyl 3-methyl-4-[1-(pyridin-3-ylmethyl)piperidin-4-yl]oxy-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OC(CC1)CCN1CC1=CC=CN=C1 JTRGDVDJOWAPHG-UHFFFAOYSA-N 0.000 claims description 2
- CSDFPNRSGFWPAY-UHFFFAOYSA-N ethyl 3-methyl-4-[3-(2-pyridin-3-ylethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCCC1=CC=CN=C1 CSDFPNRSGFWPAY-UHFFFAOYSA-N 0.000 claims description 2
- WELXOMGYGDZAMR-UHFFFAOYSA-N ethyl 3-methyl-4-[[1-(pyridin-3-ylmethyl)piperidin-3-yl]methoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCC(C1)CCCN1CC1=CC=CN=C1 WELXOMGYGDZAMR-UHFFFAOYSA-N 0.000 claims description 2
- ALTJVRJYLMTZGU-UHFFFAOYSA-N ethyl 3-propan-2-yl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C(C)C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 ALTJVRJYLMTZGU-UHFFFAOYSA-N 0.000 claims description 2
- DLNSNOYTEZNQIQ-UHFFFAOYSA-N ethyl 4-[2-(tert-butylamino)ethoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCNC(C)(C)C)=C2C(C)=C(C(=O)OCC)OC2=C1 DLNSNOYTEZNQIQ-UHFFFAOYSA-N 0.000 claims description 2
- DGMXISJISSQFBE-UHFFFAOYSA-N ethyl 4-[3-(benzylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CC=C1 DGMXISJISSQFBE-UHFFFAOYSA-N 0.000 claims description 2
- FNFAPPSVXWBZTF-UHFFFAOYSA-N ethyl 4-[3-(diaminomethylideneamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(OCCCNC(N)=N)=C2C(C)=C(C(=O)OCC)OC2=C1 FNFAPPSVXWBZTF-UHFFFAOYSA-N 0.000 claims description 2
- UYHYFQZBGYPYFS-UHFFFAOYSA-N ethyl 4-[3-(tert-butylamino)propoxy]-3-(ethoxymethyl)-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCNC(C)(C)C)=C2C(COCC)=C(C(=O)OCC)OC2=C1 UYHYFQZBGYPYFS-UHFFFAOYSA-N 0.000 claims description 2
- GZVJVKHZBBOTEC-UHFFFAOYSA-N ethyl 4-[3-[[4-(dimethylamino)phenyl]methylamino]propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=C(N(C)C)C=C1 GZVJVKHZBBOTEC-UHFFFAOYSA-N 0.000 claims description 2
- JBAHFSJPHFPFKG-UHFFFAOYSA-N ethyl 4-[4-(tert-butylamino)butoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCCNC(C)(C)C)=C2C(C)=C(C(=O)OCC)OC2=C1 JBAHFSJPHFPFKG-UHFFFAOYSA-N 0.000 claims description 2
- JGZDVTYUYRFWCS-UHFFFAOYSA-N ethyl 4-[5-(tert-butylamino)pentoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCCCNC(C)(C)C)=C2C(C)=C(C(=O)OCC)OC2=C1 JGZDVTYUYRFWCS-UHFFFAOYSA-N 0.000 claims description 2
- OMQIIQWDDJKMDY-UHFFFAOYSA-N ethyl 5-[[3-cyclopropyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-carboxylate Chemical compound C=1C=C2OC(C(=O)OCC)=CC2=CC=1OCC(=C(C1=2)C3CC3)OC1=CC=CC=2OCCCNCC1=CC=CN=C1 OMQIIQWDDJKMDY-UHFFFAOYSA-N 0.000 claims description 2
- RBQKDZAVPGDTKQ-UHFFFAOYSA-N ethyl 5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-carboxylate Chemical compound C=1C=C2OC(C(=O)OCC)=CC2=CC=1OCC(=C(C1=2)C)OC1=CC=CC=2OCCCNCC1=CC=CN=C1 RBQKDZAVPGDTKQ-UHFFFAOYSA-N 0.000 claims description 2
- XAAWPSXSVJDATO-UHFFFAOYSA-N ethyl 5-bromo-4-[3-(tert-butylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C1=C(Br)C(OCCCNC(C)(C)C)=C2C(C)=C(C(=O)OCC)OC2=C1 XAAWPSXSVJDATO-UHFFFAOYSA-N 0.000 claims description 2
- ZWLOSLWWJMNBLW-UHFFFAOYSA-N ethyl 5-fluoro-3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=C(F)C=1OCCCNCC1=CC=CN=C1 ZWLOSLWWJMNBLW-UHFFFAOYSA-N 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- BHJOLAOPQCMCHJ-UHFFFAOYSA-N methyl 4-[3-(tert-butylamino)propoxy]-3-(hydroxymethyl)-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCCCNC(C)(C)C)=C2C(CO)=C(C(=O)OC)OC2=C1 BHJOLAOPQCMCHJ-UHFFFAOYSA-N 0.000 claims description 2
- VOBRMXZSLRWMIM-UHFFFAOYSA-N n'-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carbonyl]pyridine-4-carbohydrazide Chemical compound C=12C(C)=C(C(=O)NNC(=O)C=3C=CN=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 VOBRMXZSLRWMIM-UHFFFAOYSA-N 0.000 claims description 2
- POSJWOCLABVWGQ-UHFFFAOYSA-N n-(2,4-difluorophenyl)-3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NC=3C(=CC(F)=CC=3)F)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 POSJWOCLABVWGQ-UHFFFAOYSA-N 0.000 claims description 2
- JNUJBZFKFWNCIR-UHFFFAOYSA-N n-(2-cyclohexylethyl)-3-methyl-4-(3-pyrrolidin-1-ylpropoxy)-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NCCC3CCCCC3)OC2=CC=CC=1OCCCN1CCCC1 JNUJBZFKFWNCIR-UHFFFAOYSA-N 0.000 claims description 2
- QWLOKDMVHLNIKY-UHFFFAOYSA-N n-(3,5-difluorophenyl)-2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-1,3-oxazole-4-carboxamide Chemical compound C=12C(C)=C(C=3OC=C(N=3)C(=O)NC=3C=C(F)C=C(F)C=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 QWLOKDMVHLNIKY-UHFFFAOYSA-N 0.000 claims description 2
- GIYCMAWDRWJTOY-UHFFFAOYSA-N n-cyclohexyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1-benzofuran-2-carboxamide Chemical compound CC=1C=2C(OCC(O)CNC(C)C)=CC=CC=2OC=1C(=O)NC1CCCCC1 GIYCMAWDRWJTOY-UHFFFAOYSA-N 0.000 claims description 2
- FUBGKMXYXHZZEG-UHFFFAOYSA-N n-cyclopropyl-5-[[3-cyclopropyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC(OCC3=C(C4=C(OCCCNCC=5C=NC=CC=5)C=CC=C4O3)C3CC3)=CC=C2OC=1C(=O)NC1CC1 FUBGKMXYXHZZEG-UHFFFAOYSA-N 0.000 claims description 2
- ISFQOZSJARSCQE-UHFFFAOYSA-N n-ethyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1-benzofuran-2-carboxamide Chemical compound C1=CC(OCC(O)CNC(C)C)=C2C(C)=C(C(=O)NCC)OC2=C1 ISFQOZSJARSCQE-UHFFFAOYSA-N 0.000 claims description 2
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 claims description 2
- ROWWFURUTODPTB-UHFFFAOYSA-N 1-[5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]ethanone Chemical compound C=1C=C2OC(C(=O)C)=CC2=CC=1OCC(=C(C1=2)C)OC1=CC=CC=2OCCCNCC1=CC=CN=C1 ROWWFURUTODPTB-UHFFFAOYSA-N 0.000 claims 1
- OELKWCREEWEJAL-UHFFFAOYSA-N 2-[5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]propan-2-ol Chemical compound C=12C(C)=C(COC=3C=C4C=C(OC4=CC=3)C(C)(C)O)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 OELKWCREEWEJAL-UHFFFAOYSA-N 0.000 claims 1
- LLRYVKRCAUSHQQ-UHFFFAOYSA-N 3-[[2-(ethoxyiminomethyl)-3-methyl-1-benzofuran-4-yl]oxy]-n-methyl-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound C=12C(C)=C(C=NOCC)OC2=CC=CC=1OCCCN(C)CC1=CC=CN=C1 LLRYVKRCAUSHQQ-UHFFFAOYSA-N 0.000 claims 1
- CBKBXWFRVHPWBU-UHFFFAOYSA-N 3-[[2-[(2,4-difluorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=C(F)C=C1F CBKBXWFRVHPWBU-UHFFFAOYSA-N 0.000 claims 1
- RULWTXQIOCZCKK-UHFFFAOYSA-N 3-[[2-[(2,5-difluorophenoxy)methyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC(F)=CC=C1F RULWTXQIOCZCKK-UHFFFAOYSA-N 0.000 claims 1
- HUPUYMDTNBHKCW-UHFFFAOYSA-N 3-[[2-[(4-chlorophenyl)methylsulfanylmethyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CSCC1=CC=C(Cl)C=C1 HUPUYMDTNBHKCW-UHFFFAOYSA-N 0.000 claims 1
- VYAVUXDMHFKDIQ-UHFFFAOYSA-N 3-[[2-[(4-chlorophenyl)sulfanylmethyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CSC1=CC=C(Cl)C=C1 VYAVUXDMHFKDIQ-UHFFFAOYSA-N 0.000 claims 1
- CGZDSAJNHIHBDT-UHFFFAOYSA-N 3-[[2-[(4-fluorophenyl)sulfinylmethyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CS(=O)C1=CC=C(F)C=C1 CGZDSAJNHIHBDT-UHFFFAOYSA-N 0.000 claims 1
- VNVNWIBATQDBRX-UHFFFAOYSA-N 3-[[2-[(4-fluorophenyl)sulfonylmethyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CS(=O)(=O)C1=CC=C(F)C=C1 VNVNWIBATQDBRX-UHFFFAOYSA-N 0.000 claims 1
- ZGVPSECDCSVNNG-UHFFFAOYSA-N 3-[[2-[c-(4,5-dimethyl-1,3-thiazol-2-yl)-n-[(4-nitrophenyl)methoxy]carbonimidoyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound S1C(C)=C(C)N=C1C(C1=C(C2=C(OCCCNCC=3C=NC=CC=3)C=CC=C2O1)C)=NOCC1=CC=C([N+]([O-])=O)C=C1 ZGVPSECDCSVNNG-UHFFFAOYSA-N 0.000 claims 1
- HDNRKHOILMHBEZ-UHFFFAOYSA-N 3-[[2-[c-(4,5-dimethyl-1,3-thiazol-2-yl)-n-phenoxycarbonimidoyl]-3-methyl-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound S1C(C)=C(C)N=C1C(C1=C(C2=C(OCCCNCC=3C=NC=CC=3)C=CC=C2O1)C)=NOC1=CC=CC=C1 HDNRKHOILMHBEZ-UHFFFAOYSA-N 0.000 claims 1
- KSVSTWISXHSZMM-UHFFFAOYSA-N 3-[[3-methyl-2-(2,2,2-trifluoroethoxymethyl)-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound C=12C(C)=C(COCC(F)(F)F)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 KSVSTWISXHSZMM-UHFFFAOYSA-N 0.000 claims 1
- OIPBAHSPXYERSN-UHFFFAOYSA-N 3-[[3-methyl-2-(2-phenylethylsulfinylmethyl)-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CS(=O)CCC1=CC=CC=C1 OIPBAHSPXYERSN-UHFFFAOYSA-N 0.000 claims 1
- XRLSTFAITYINFD-UHFFFAOYSA-N 3-[[3-methyl-2-(phenylsulfanylmethyl)-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1CSC1=CC=CC=C1 XRLSTFAITYINFD-UHFFFAOYSA-N 0.000 claims 1
- KIAXWJBWWBGOIS-UHFFFAOYSA-N 3-[[3-methyl-2-[(2,3,6-trifluorophenoxy)methyl]-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=C(F)C=CC(F)=C1F KIAXWJBWWBGOIS-UHFFFAOYSA-N 0.000 claims 1
- XIISIJINCXIEGE-UHFFFAOYSA-N 3-[[3-methyl-2-[(2,4,6-trifluorophenoxy)methyl]-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=C(F)C=C(F)C=C1F XIISIJINCXIEGE-UHFFFAOYSA-N 0.000 claims 1
- KASPNIPHEABOFQ-UHFFFAOYSA-N 3-[[3-methyl-2-[[3-(trifluoromethyl)phenoxy]methyl]-1-benzofuran-4-yl]oxy]-n-(pyridin-3-ylmethyl)propan-1-amine Chemical compound O1C2=CC=CC(OCCCNCC=3C=NC=CC=3)=C2C(C)=C1COC1=CC=CC(C(F)(F)F)=C1 KASPNIPHEABOFQ-UHFFFAOYSA-N 0.000 claims 1
- WWEMQHMHNDPPMH-UHFFFAOYSA-N 3-methyl-N-(4-morpholin-4-ylphenyl)-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 WWEMQHMHNDPPMH-UHFFFAOYSA-N 0.000 claims 1
- DVWXQGFSMAZXGE-UHFFFAOYSA-N 5-[[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(COC=3C=C4C=C(OC4=CC=3)C(N)=O)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 DVWXQGFSMAZXGE-UHFFFAOYSA-N 0.000 claims 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
- VNUKVBWDYJURQP-UHFFFAOYSA-N 5-methyl-n-[[3-methyl-4-[3-[methyl(pyridin-3-ylmethyl)amino]propoxy]-1-benzofuran-2-yl]methyl]-1,2-oxazol-3-amine Chemical compound C=1C=CN=CC=1CN(C)CCCOC(C=1C=2C)=CC=CC=1OC=2CNC=1C=C(C)ON=1 VNUKVBWDYJURQP-UHFFFAOYSA-N 0.000 claims 1
- UTDBUTWDSMZPMU-UHFFFAOYSA-N [3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-[1-(2-pyridin-2-ylethyl)benzimidazol-2-yl]methanone Chemical compound C=12C(C)=C(C(=O)C=3N(C4=CC=CC=C4N=3)CCC=3N=CC=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 UTDBUTWDSMZPMU-UHFFFAOYSA-N 0.000 claims 1
- PDEGIOJEHUSMII-UHFFFAOYSA-N [5-[[3-methyl-4-[[1-(pyridin-3-ylmethyl)piperidin-3-yl]methoxy]-1-benzofuran-2-yl]methoxy]-1-benzofuran-2-yl]methanol Chemical compound C=12C(C)=C(COC=3C=C4C=C(CO)OC4=CC=3)OC2=CC=CC=1OCC(C1)CCCN1CC1=CC=CN=C1 PDEGIOJEHUSMII-UHFFFAOYSA-N 0.000 claims 1
- WBQJCTIXGOYQAW-UHFFFAOYSA-N ethyl 2-[2-[3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-yl]-1,3-oxazol-4-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C=2N=C(OC=2)C2=C(C3=C(OCCCNCC=4C=NC=CC=4)C=CC=C3O2)C)=N1 WBQJCTIXGOYQAW-UHFFFAOYSA-N 0.000 claims 1
- AISDDYNMUSTOCP-UHFFFAOYSA-N ethyl 2-[[4-[3-(tert-butylamino)propoxy]-3-methyl-1-benzofuran-2-carbonyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC(=O)C1=C(C)C2=C(OCCCNC(C)(C)C)C=CC=C2O1 AISDDYNMUSTOCP-UHFFFAOYSA-N 0.000 claims 1
- WVIFNQSMGQMTKX-UHFFFAOYSA-N ethyl 3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 WVIFNQSMGQMTKX-UHFFFAOYSA-N 0.000 claims 1
- IOLJQBDBXFMIHQ-UHFFFAOYSA-N ethyl 3-methyl-4-[4-(pyridin-3-ylmethylamino)butan-2-yloxy]-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OC(C)CCNCC1=CC=CN=C1 IOLJQBDBXFMIHQ-UHFFFAOYSA-N 0.000 claims 1
- CKLCQECOHDZVDS-UHFFFAOYSA-N ethyl 4-[2-hydroxy-3-(pyridin-3-ylmethylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCC(O)CNCC1=CC=CN=C1 CKLCQECOHDZVDS-UHFFFAOYSA-N 0.000 claims 1
- BUULVZKKSYQFRF-UHFFFAOYSA-N ethyl 4-[3-(2,3-dihydro-1h-inden-1-ylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C1CC2=CC=CC=C2C1NCCCOC1=C(C(=C(C(=O)OCC)O2)C)C2=CC=C1 BUULVZKKSYQFRF-UHFFFAOYSA-N 0.000 claims 1
- AUMMAAIUEGFFOA-UHFFFAOYSA-N ethyl 4-[3-[(1-benzylpiperidin-4-yl)amino]propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNC(CC1)CCN1CC1=CC=CC=C1 AUMMAAIUEGFFOA-UHFFFAOYSA-N 0.000 claims 1
- QXRFKNDYVIEOCR-UHFFFAOYSA-N ethyl 4-[3-[(1-ethylpiperidin-4-yl)amino]propoxy]-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=CC=CC=1OCCCNC1CCN(CC)CC1 QXRFKNDYVIEOCR-UHFFFAOYSA-N 0.000 claims 1
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- BWPXXHDOPIOQTF-UHFFFAOYSA-N n-(2-cyclohexylethyl)-3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NCCC3CCCCC3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 BWPXXHDOPIOQTF-UHFFFAOYSA-N 0.000 claims 1
- NHUDYPDRKZQXJG-UHFFFAOYSA-N n-(4-chlorophenyl)-3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carboxamide Chemical compound C=12C(C)=C(C(=O)NC=3C=CC(Cl)=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 NHUDYPDRKZQXJG-UHFFFAOYSA-N 0.000 claims 1
- IZRKHRSUZAEWJE-UHFFFAOYSA-N n-(4-fluorophenyl)-3-methyl-4-[3-(pyridin-3-ylmethylamino)propoxy]-1-benzofuran-2-carbohydrazide Chemical compound C=12C(C)=C(C(=O)N(N)C=3C=CC(F)=CC=3)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 IZRKHRSUZAEWJE-UHFFFAOYSA-N 0.000 claims 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000006510 trifluorobenzyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98124120 | 1998-12-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200104410B true ZA200104410B (en) | 2002-08-29 |
Family
ID=8233179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200104410A ZA200104410B (en) | 1998-12-18 | 2001-05-29 | Novel bicyclic compounds. |
Country Status (18)
Country | Link |
---|---|
US (1) | US6376491B1 (pt) |
EP (1) | EP1149094B1 (pt) |
JP (1) | JP3435404B2 (pt) |
KR (1) | KR20010081117A (pt) |
CN (1) | CN1333770A (pt) |
AR (1) | AR021714A1 (pt) |
AT (1) | ATE264855T1 (pt) |
AU (1) | AU754233B2 (pt) |
BR (1) | BR9916318A (pt) |
CA (1) | CA2355694A1 (pt) |
DE (1) | DE69916664T2 (pt) |
DK (1) | DK1149094T3 (pt) |
ES (1) | ES2217882T3 (pt) |
MX (1) | MXPA01006218A (pt) |
PE (1) | PE20001324A1 (pt) |
TR (1) | TR200101779T2 (pt) |
WO (1) | WO2000037464A2 (pt) |
ZA (1) | ZA200104410B (pt) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0011542A (pt) | 1999-05-24 | 2002-03-05 | Mitsubishi Pharma Corp | Compostos de fenoxipropilamina |
SE9902987D0 (sv) * | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
AU2002224105A1 (en) * | 2000-11-27 | 2002-06-03 | Mitsubishi Pharma Corporation | Piperidine compounds and medicinal use thereof |
US7078541B2 (en) * | 2002-02-07 | 2006-07-18 | Galileo Pharmaceuticals, Inc. | Benzofuran derivatives |
US6653346B1 (en) * | 2002-02-07 | 2003-11-25 | Galileo Pharmaceuticals, Inc. | Cytoprotective benzofuran derivatives |
WO2006015279A1 (en) * | 2004-07-28 | 2006-02-09 | Neurogen Corporation | Heterocyclic diamine compounds as ligands of the melanin concentrating hormone receptor useful for the treatment of obesity, diabetes, eating and sexual disorders |
WO2007020936A1 (ja) * | 2005-08-17 | 2007-02-22 | Daiichi Sankyo Company, Limited | 抗真菌作用二環性複素環化合物 |
US20090270496A1 (en) * | 2007-05-03 | 2009-10-29 | Courchesne William E | Antifungal compounds |
GB0815947D0 (en) * | 2008-09-02 | 2008-10-08 | Univ Dundee | Compounds |
CN102186845B (zh) | 2008-10-17 | 2016-09-07 | 阿卡制药有限公司 | S1p受体调节剂以及它们的用途 |
WO2010042998A1 (en) | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1p receptors modulators |
GB201120993D0 (en) | 2011-12-06 | 2012-01-18 | Imp Innovations Ltd | Novel compounds and their use in therapy |
GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
CN107540725B (zh) * | 2016-06-29 | 2020-04-07 | 孙青� | 一种水溶性丹参酮ⅱa衍生物及其制备与应用 |
GB201820660D0 (en) | 2018-12-19 | 2019-01-30 | Imperial Innovations Ltd | Cancer treatments |
GB201820659D0 (en) | 2018-12-19 | 2019-01-30 | Imperial Innovations Ltd | Novel compostions and their use in therapy |
GB202014736D0 (en) | 2020-09-18 | 2020-11-04 | Imperial College Innovations Ltd | Novel compounds and their use in therapy |
GB202017367D0 (en) | 2020-11-02 | 2020-12-16 | Imperial College Innovations Ltd | Novel use |
WO2024052684A1 (en) | 2022-09-09 | 2024-03-14 | MyricX Pharma Limited | Antibody drug conjugate comprising nmt inhibitor and its use |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1129072A (en) * | 1966-02-01 | 1968-10-02 | Ici Ltd | Benzofuran and indole derivatives |
GB1256735A (pt) * | 1969-03-06 | 1971-12-15 | ||
US4056626A (en) | 1971-05-13 | 1977-11-01 | Kakenyaku Kako Co., Ltd. | Pharmaceutical composition containing benzofuran derivative |
US3853923A (en) * | 1971-05-13 | 1974-12-10 | Kakenyaku Kako Kk | 2-substituted-(2-hydroxy-3-lower alkaminopropoxy)-benzofurans |
CA1089866A (en) * | 1975-10-20 | 1980-11-18 | Kiyoshi Ito | Benzofuran derivatives, preparation thereof and pharmaceutical compositions thereof |
SU671256A1 (ru) * | 1977-06-08 | 1986-11-23 | Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе | Гидрохлорид 1-(2-карбэтокси-3-метилбензофуран-4-илокси-3-изопропиламино)-2-пропанола,обладающий антиаритмическим и @ -адреноблокирующим действием |
JPS5740479A (en) * | 1980-08-21 | 1982-03-06 | Kaken Pharmaceut Co Ltd | Preparation of benzofuran derivative and its acid addition salt |
EP0146243A1 (en) * | 1983-10-31 | 1985-06-26 | Merck Frosst Canada Inc. | Lipoxygenase inhibitors |
US5082967A (en) * | 1988-06-16 | 1992-01-21 | Washington University | Novel fatty acid analog enzyme substrates |
FR2672598A1 (fr) * | 1991-02-11 | 1992-08-14 | Adir | Nouveaux inhibiteurs de n-myristoyltransferase, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
JPH07215940A (ja) * | 1994-01-27 | 1995-08-15 | Torii Yakuhin Kk | 抗ウイルス活性を有する化合物 |
JPH08198826A (ja) * | 1995-01-23 | 1996-08-06 | Torii Yakuhin Kk | 抗ウイルス活性を有する化合物 |
-
1999
- 1999-12-10 CA CA002355694A patent/CA2355694A1/en not_active Abandoned
- 1999-12-10 CN CN99815722A patent/CN1333770A/zh active Pending
- 1999-12-10 AT AT99968791T patent/ATE264855T1/de not_active IP Right Cessation
- 1999-12-10 EP EP99968791A patent/EP1149094B1/en not_active Expired - Lifetime
- 1999-12-10 ES ES99968791T patent/ES2217882T3/es not_active Expired - Lifetime
- 1999-12-10 JP JP2000589535A patent/JP3435404B2/ja not_active Expired - Fee Related
- 1999-12-10 TR TR2001/01779T patent/TR200101779T2/xx unknown
- 1999-12-10 KR KR1020017007661A patent/KR20010081117A/ko active IP Right Grant
- 1999-12-10 WO PCT/EP1999/009763 patent/WO2000037464A2/en active IP Right Grant
- 1999-12-10 MX MXPA01006218A patent/MXPA01006218A/es unknown
- 1999-12-10 BR BR9916318-7A patent/BR9916318A/pt not_active IP Right Cessation
- 1999-12-10 AU AU26606/00A patent/AU754233B2/en not_active Ceased
- 1999-12-10 DE DE69916664T patent/DE69916664T2/de not_active Expired - Fee Related
- 1999-12-10 DK DK99968791T patent/DK1149094T3/da active
- 1999-12-14 PE PE1999001249A patent/PE20001324A1/es not_active Application Discontinuation
- 1999-12-15 US US09/464,240 patent/US6376491B1/en not_active Expired - Fee Related
- 1999-12-16 AR ARP990106457A patent/AR021714A1/es not_active Application Discontinuation
-
2001
- 2001-05-29 ZA ZA200104410A patent/ZA200104410B/en unknown
Also Published As
Publication number | Publication date |
---|---|
AR021714A1 (es) | 2002-07-31 |
ES2217882T3 (es) | 2004-11-01 |
DE69916664T2 (de) | 2005-03-31 |
US6376491B1 (en) | 2002-04-23 |
TR200101779T2 (tr) | 2001-12-21 |
WO2000037464A2 (en) | 2000-06-29 |
KR20010081117A (ko) | 2001-08-27 |
PE20001324A1 (es) | 2000-12-02 |
AU2660600A (en) | 2000-07-12 |
BR9916318A (pt) | 2001-08-14 |
DK1149094T3 (da) | 2004-08-16 |
DE69916664D1 (de) | 2004-05-27 |
MXPA01006218A (es) | 2002-04-17 |
EP1149094A2 (en) | 2001-10-31 |
WO2000037464A3 (en) | 2000-11-02 |
JP3435404B2 (ja) | 2003-08-11 |
AU754233B2 (en) | 2002-11-07 |
CN1333770A (zh) | 2002-01-30 |
CA2355694A1 (en) | 2000-06-29 |
EP1149094B1 (en) | 2004-04-21 |
ATE264855T1 (de) | 2004-05-15 |
JP2002533340A (ja) | 2002-10-08 |
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