CA2254120A1 - 1,3-benzodioxoles substitues - Google Patents
1,3-benzodioxoles substitues Download PDFInfo
- Publication number
- CA2254120A1 CA2254120A1 CA002254120A CA2254120A CA2254120A1 CA 2254120 A1 CA2254120 A1 CA 2254120A1 CA 002254120 A CA002254120 A CA 002254120A CA 2254120 A CA2254120 A CA 2254120A CA 2254120 A1 CA2254120 A1 CA 2254120A1
- Authority
- CA
- Canada
- Prior art keywords
- propyl
- phenyl
- chloro
- dioxole
- benzo
- 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.)
- Abandoned
Links
- 150000005529 1,3-benzodioxoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 286
- 150000003839 salts Chemical class 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims abstract description 94
- 239000001257 hydrogen Substances 0.000 claims abstract description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 81
- -1 arylakyl Chemical group 0.000 claims abstract description 64
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims description 106
- JEDJMKTVUPSHFW-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C=1C=C2OC(C(O)=O)(C(O)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JEDJMKTVUPSHFW-UHFFFAOYSA-N 0.000 claims description 35
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- 201000001421 hyperglycemia Diseases 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- JEDJMKTVUPSHFW-ABAIWWIYSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(O)=O)C(O)=O)C)=CC=CC(Cl)=C1 JEDJMKTVUPSHFW-ABAIWWIYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims description 3
- OFMKGUGVTUABKO-BAACLCEWSA-N 2-(1-adamantylmethoxycarbonyl)-5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(O)=O)C(=O)OCC23CC4CC(CC(C4)C2)C3)C)=CC=CC(Cl)=C1 OFMKGUGVTUABKO-BAACLCEWSA-N 0.000 claims description 2
- UUVYRBFKOYZXSV-XTQAFDQHSA-N 2-[1,3-bis(diethylamino)-1,3-dioxopropan-2-yl]oxycarbonyl-5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1([C@@H](O)CN([C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OC(C(=O)N(CC)CC)C(=O)N(CC)CC)C(O)=O)C(=O)OC(C)(C)C)=CC=CC(Cl)=C1 UUVYRBFKOYZXSV-XTQAFDQHSA-N 0.000 claims description 2
- FRPOEAJVJSLVGY-UHFFFAOYSA-N 2-[bis(cyclohexanecarbonyloxy)methoxycarbonyl]-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OC(OC(=O)C1CCCCC1)OC(=O)C1CCCCC1 FRPOEAJVJSLVGY-UHFFFAOYSA-N 0.000 claims description 2
- OZEPVEBYPNGSRR-MXZBBBRTSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(2-ethoxyethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OCCOCC)C(O)=O)=CC=CC(Cl)=C1 OZEPVEBYPNGSRR-MXZBBBRTSA-N 0.000 claims description 2
- DDLJLQQNSYZHDP-UHFFFAOYSA-N 5-[2-[2-(3-chlorophenyl)-1,3-oxazolidin-3-yl]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid Chemical compound C=1C=C2OC(C(O)=O)(C(O)=O)OC2=CC=1CC(C)N1CCOC1C1=CC=CC(Cl)=C1 DDLJLQQNSYZHDP-UHFFFAOYSA-N 0.000 claims description 2
- JFUJQONLBMJKLL-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(1,3-diethoxy-1,3-dioxopropan-2-yl)oxycarbonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(C(=O)OCC)C(=O)OCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JFUJQONLBMJKLL-UHFFFAOYSA-N 0.000 claims description 2
- VWIYFOZWBNCEOX-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)oxycarbonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(C(=O)OC)C(=O)OC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 VWIYFOZWBNCEOX-UHFFFAOYSA-N 0.000 claims description 2
- GEQMRAYOOGDQMN-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(dibenzoyloxymethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OC(OC(=O)C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 GEQMRAYOOGDQMN-UHFFFAOYSA-N 0.000 claims description 2
- DUYAYEGIEPDQRS-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(dibenzylcarbamoyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DUYAYEGIEPDQRS-UHFFFAOYSA-N 0.000 claims description 2
- UCKVEYJXISHXHZ-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[di(butanoyloxy)methoxycarbonyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(OC(=O)CCC)OC(=O)CCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 UCKVEYJXISHXHZ-UHFFFAOYSA-N 0.000 claims description 2
- XBDYSWGWUNRFQE-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[di(heptanoyloxy)methoxycarbonyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(OC(=O)CCCCCC)OC(=O)CCCCCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 XBDYSWGWUNRFQE-UHFFFAOYSA-N 0.000 claims description 2
- HSZLVYNXYJWOHB-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[di(hexanoyloxy)methoxycarbonyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(OC(=O)CCCCC)OC(=O)CCCCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 HSZLVYNXYJWOHB-UHFFFAOYSA-N 0.000 claims description 2
- BSZQYTKJYONFIX-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[di(propan-2-yl)carbamoyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)N(C(C)C)C(C)C)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 BSZQYTKJYONFIX-UHFFFAOYSA-N 0.000 claims description 2
- RFUADYLBKNLOGD-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[di(propanoyloxy)methoxycarbonyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(OC(=O)CC)OC(=O)CC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 RFUADYLBKNLOGD-UHFFFAOYSA-N 0.000 claims description 2
- POPYUQLMDUTTBY-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-propan-2-yloxycarbonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(C)C)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 POPYUQLMDUTTBY-UHFFFAOYSA-N 0.000 claims description 2
- RTLOYJIVIRGUHV-UHFFFAOYSA-N C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCOC(=O)CCC1CCCC1)C(=O)OCOC(=O)CCC1CCCC1 Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCOC(=O)CCC1CCCC1)C(=O)OCOC(=O)CCC1CCCC1 RTLOYJIVIRGUHV-UHFFFAOYSA-N 0.000 claims description 2
- CJSNUAXCJPOSFZ-UHFFFAOYSA-N bis(1-ethoxy-1-oxopropan-2-yl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OC(C)C(=O)OCC)(C(=O)OC(C)C(=O)OCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 CJSNUAXCJPOSFZ-UHFFFAOYSA-N 0.000 claims description 2
- SZBBAKJFGGSINX-UHFFFAOYSA-N bis(1-methoxy-1-oxopropan-2-yl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OC(C)C(=O)OC)(C(=O)OC(C)C(=O)OC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 SZBBAKJFGGSINX-UHFFFAOYSA-N 0.000 claims description 2
- IMJUBJBXKRWNAH-UHFFFAOYSA-N bis(1-propanoyloxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OC(C)OC(=O)CC)(C(=O)OC(C)OC(=O)CC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 IMJUBJBXKRWNAH-UHFFFAOYSA-N 0.000 claims description 2
- YMCPLCLBRCTBNW-XXBNENTESA-N bis(2,2-dimethylpropyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(=O)OCC(C)(C)C)C(=O)OCC(C)(C)C)C)=CC=CC(Cl)=C1 YMCPLCLBRCTBNW-XXBNENTESA-N 0.000 claims description 2
- DHVRZWGUXZXISF-UHFFFAOYSA-N bis(2-ethoxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCOCC)(C(=O)OCCOCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 DHVRZWGUXZXISF-UHFFFAOYSA-N 0.000 claims description 2
- GVWCDKVKGDLHFD-UHFFFAOYSA-N bis(2-propan-2-yloxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCOC(C)C)(C(=O)OCCOC(C)C)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 GVWCDKVKGDLHFD-UHFFFAOYSA-N 0.000 claims description 2
- VQWBFZUXHYOCLP-UHFFFAOYSA-N bis(2-trimethylsilylethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCC[Si](C)(C)C)(C(=O)OCC[Si](C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 VQWBFZUXHYOCLP-UHFFFAOYSA-N 0.000 claims description 2
- ILUBYRXBBOIXLI-UHFFFAOYSA-N bis(3,3-dimethylbutanoyloxymethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCOC(=O)CC(C)(C)C)(C(=O)OCOC(=O)CC(C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 ILUBYRXBBOIXLI-UHFFFAOYSA-N 0.000 claims description 2
- LNLCBPXETCWIHH-UHFFFAOYSA-N bis(3,3-dimethylbutyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCCC(C)(C)C)(C(=O)OCCC(C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 LNLCBPXETCWIHH-UHFFFAOYSA-N 0.000 claims description 2
- BFUSPRCMZMZPNZ-UHFFFAOYSA-N bis(cyclopropylmethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCC1CC1)C(=O)OCC1CC1 BFUSPRCMZMZPNZ-UHFFFAOYSA-N 0.000 claims description 2
- DADCBMMZNZCFEZ-UHFFFAOYSA-N bis[(1-methylcyclopropyl)methyl] 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCC1(C)CC1)C(=O)OCC1(C)CC1 DADCBMMZNZCFEZ-UHFFFAOYSA-N 0.000 claims description 2
- REILEOOPSNTBHF-UHFFFAOYSA-N diheptyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCCCCCC)(C(=O)OCCCCCCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 REILEOOPSNTBHF-UHFFFAOYSA-N 0.000 claims description 2
- HCYJCCHZPFJEFY-UHFFFAOYSA-N dihexyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCCCCC)(C(=O)OCCCCCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 HCYJCCHZPFJEFY-UHFFFAOYSA-N 0.000 claims description 2
- CAXFOOLGTVUCAK-UHFFFAOYSA-N dioctyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCCCCCCC)(C(=O)OCCCCCCCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 CAXFOOLGTVUCAK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- PKFOTSGFOSSTLK-UHFFFAOYSA-N 2-[bis(2-methylpropanoyloxy)methoxycarbonyl]-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)OC(OC(=O)C(C)C)OC(=O)C(C)C)(C(O)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 PKFOTSGFOSSTLK-UHFFFAOYSA-N 0.000 claims 1
- WFTBOKHIBNVBMD-UHFFFAOYSA-N 2-[bis(furan-2-ylmethyl)carbamoyl]-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)N(CC=1OC=CC=1)CC1=CC=CO1 WFTBOKHIBNVBMD-UHFFFAOYSA-N 0.000 claims 1
- YXJCAFDQAQIXOB-UHFFFAOYSA-N 2-[bis(trimethylsilyl)methoxycarbonyl]-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)OC([Si](C)(C)C)[Si](C)(C)C)(C(O)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 YXJCAFDQAQIXOB-UHFFFAOYSA-N 0.000 claims 1
- VVMGEZKQENIOJS-PTGMXARNSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(1-phenylethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OC(C)C1=CC=CC=C1 VVMGEZKQENIOJS-PTGMXARNSA-N 0.000 claims 1
- YTNVHDGHMXNPQC-HKHZIOOCSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(2,2-dimethylpropoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(O)=O)C(=O)OCC(C)(C)C)C)=CC=CC(Cl)=C1 YTNVHDGHMXNPQC-HKHZIOOCSA-N 0.000 claims 1
- UDHMWSQUVHHROZ-MUHMMENPSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(2-phenylethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCCC1=CC=CC=C1 UDHMWSQUVHHROZ-MUHMMENPSA-N 0.000 claims 1
- HZEIFUHFVDGIJZ-NLDMFTSSSA-N 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(3-methylbutoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OCCC(C)C)C(O)=O)=CC=CC(Cl)=C1 HZEIFUHFVDGIJZ-NLDMFTSSSA-N 0.000 claims 1
- RXOVMVOWWJIIFV-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(2-thiophen-3-ylethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCCC=1C=CSC=1 RXOVMVOWWJIIFV-UHFFFAOYSA-N 0.000 claims 1
- MYIPLLCEXHRJFO-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(cyclobutylmethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC1CCC1 MYIPLLCEXHRJFO-UHFFFAOYSA-N 0.000 claims 1
- PXLYFOLEZNQFMQ-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(cyclopropylmethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC1CC1 PXLYFOLEZNQFMQ-UHFFFAOYSA-N 0.000 claims 1
- KHOCFUJMTVASCC-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(dibutylcarbamoyl)-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)N(CCCC)CCCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 KHOCFUJMTVASCC-UHFFFAOYSA-N 0.000 claims 1
- DGGNVOFPQGYNOT-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[1,3-dioxo-1,3-di(propan-2-yloxy)propan-2-yl]oxycarbonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OC(C(=O)OC(C)C)C(=O)OC(C)C)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 DGGNVOFPQGYNOT-UHFFFAOYSA-N 0.000 claims 1
- DUSWVRCIPDUGDK-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[2-[(2-methylpropan-2-yl)oxy]ethoxycarbonyl]-1,3-benzodioxole-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)OCCOC(C)(C)C)(C(O)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 DUSWVRCIPDUGDK-UHFFFAOYSA-N 0.000 claims 1
- YYYUACPGSFCIFC-UHFFFAOYSA-N 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-ethoxycarbonyl-1,3-benzodioxole-2-carboxylic acid Chemical compound C1=C2OC(C(=O)OCC)(C(O)=O)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 YYYUACPGSFCIFC-UHFFFAOYSA-N 0.000 claims 1
- JHYORHSRKUXTSS-UHFFFAOYSA-N C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(O)=O)C(=O)OCC(C=1C=CC=CC=1)C1=CC=CC=C1 JHYORHSRKUXTSS-UHFFFAOYSA-N 0.000 claims 1
- BBYGZUBFEWQBBH-UHFFFAOYSA-N [4-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-[(3-chlorophenyl)methoxycarbonyloxy]phenyl] (3-chlorophenyl)methyl carbonate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1OC(=O)OCC=2C=C(Cl)C=CC=2)=CC=C1OC(=O)OCC1=CC=CC(Cl)=C1 BBYGZUBFEWQBBH-UHFFFAOYSA-N 0.000 claims 1
- OIFIBFSYQIXBEQ-CQSJYNICSA-N bis(1-adamantylmethyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(=O)OCC23CC4CC(CC(C4)C2)C3)C(=O)OCC23CC4CC(CC(C4)C2)C3)C)=CC=CC(Cl)=C1 OIFIBFSYQIXBEQ-CQSJYNICSA-N 0.000 claims 1
- KRVMSMVZLFOBIC-UHFFFAOYSA-N bis(1-phenylethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OC(C)C=1C=CC=CC=1)C(=O)OC(C)C1=CC=CC=C1 KRVMSMVZLFOBIC-UHFFFAOYSA-N 0.000 claims 1
- FZYOUEHWGFCWPY-IRPSRAIASA-N bis(2,2,4-trimethylpentyl) 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound CC(C)CC(C)(C)COC(=O)C1(Oc2ccc(C[C@@H](C)NC[C@H](O)c3cccc(Cl)c3)cc2O1)C(=O)OCC(C)(C)CC(C)C FZYOUEHWGFCWPY-IRPSRAIASA-N 0.000 claims 1
- QXBUMTDMIPSRAQ-UYHPJTEGSA-N bis(2,2-dimethyl-3-phenylpropyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC(C)(C)CC=1C=CC=CC=1)C(=O)OCC(C)(C)CC1=CC=CC=C1 QXBUMTDMIPSRAQ-UYHPJTEGSA-N 0.000 claims 1
- JMJKZFIBIWQREX-UHFFFAOYSA-N bis(2,2-dimethylbutanoyloxymethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCOC(=O)C(C)(C)CC)(C(=O)OCOC(=O)C(C)(C)CC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 JMJKZFIBIWQREX-UHFFFAOYSA-N 0.000 claims 1
- PYDKUVWEDWESJW-KCWPFWIISA-N bis(2,2-dimethylpentyl) 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound CCCC(C)(C)COC(=O)C1(Oc2ccc(C[C@@H](C)NC[C@H](O)c3cccc(Cl)c3)cc2O1)C(=O)OCC(C)(C)CCC PYDKUVWEDWESJW-KCWPFWIISA-N 0.000 claims 1
- BHRFUBDYFWJCEF-UHFFFAOYSA-N bis(2,2-dimethylpropanoyloxymethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCOC(=O)C(C)(C)C)(C(=O)OCOC(=O)C(C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 BHRFUBDYFWJCEF-UHFFFAOYSA-N 0.000 claims 1
- QZSYXEPUIYBYHT-UHFFFAOYSA-N bis(2-benzoyloxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCCOC(=O)C=1C=CC=CC=1)C(=O)OCCOC(=O)C1=CC=CC=C1 QZSYXEPUIYBYHT-UHFFFAOYSA-N 0.000 claims 1
- KJCHKGANNQGNTF-UHFFFAOYSA-N bis(2-butoxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCOCCCC)(C(=O)OCCOCCCC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 KJCHKGANNQGNTF-UHFFFAOYSA-N 0.000 claims 1
- BOHPQLXKYXILDD-UHFFFAOYSA-N bis(2-cyclopentylethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCCC1CCCC1)C(=O)OCCC1CCCC1 BOHPQLXKYXILDD-UHFFFAOYSA-N 0.000 claims 1
- MYVDZUNJHBGGOD-ZBLYBZFDSA-N bis(2-ethylbutyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OCC(CC)CC)C(=O)OCC(CC)CC)=CC=CC(Cl)=C1 MYVDZUNJHBGGOD-ZBLYBZFDSA-N 0.000 claims 1
- RCCRBLQUBNJYCY-UHFFFAOYSA-N bis(2-methoxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCOC)(C(=O)OCCOC)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 RCCRBLQUBNJYCY-UHFFFAOYSA-N 0.000 claims 1
- AHVVUAOMUCDHGJ-UTKZUKDTSA-N bis(2-methyl-2-nitropropyl) 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound CC(COC(=O)C1(OC2=C(O1)C=CC(=C2)C[C@@H](C)NC[C@H](O)C2=CC(=CC=C2)Cl)C(=O)OCC(C)([N+](=O)[O-])C)(C)[N+](=O)[O-] AHVVUAOMUCDHGJ-UTKZUKDTSA-N 0.000 claims 1
- LVPLNRZNJRTIGH-UHFFFAOYSA-N bis(2-phenoxyethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCCOC=1C=CC=CC=1)C(=O)OCCOC1=CC=CC=C1 LVPLNRZNJRTIGH-UHFFFAOYSA-N 0.000 claims 1
- OEQATHUTASMBCW-XXBNENTESA-N bis(3-carbamoylpentan-3-yl) 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OC(CC)(CC)C(N)=O)C(=O)OC(CC)(CC)C(N)=O)=CC=CC(Cl)=C1 OEQATHUTASMBCW-XXBNENTESA-N 0.000 claims 1
- ZIUMGRFSNUHFRY-UHFFFAOYSA-N bis(3-cyclopentylpropyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCCCC1CCCC1)C(=O)OCCCC1CCCC1 ZIUMGRFSNUHFRY-UHFFFAOYSA-N 0.000 claims 1
- DWMQGAYDLFINSV-XXBNENTESA-N bis(3-hydroxy-2,2-dimethylpropyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(=O)OCC(C)(C)CO)C(=O)OCC(C)(C)CO)C)=CC=CC(Cl)=C1 DWMQGAYDLFINSV-XXBNENTESA-N 0.000 claims 1
- FHFZLRVQWNWHKK-BWKNWUBXSA-N bis(3-methylbutyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@H](C)CC2=CC=C3OC(OC3=C2)(C(=O)OCCC(C)C)C(=O)OCCC(C)C)=CC=CC(Cl)=C1 FHFZLRVQWNWHKK-BWKNWUBXSA-N 0.000 claims 1
- WMWHRXNMXHUDHU-UYHPJTEGSA-N bis(3-phenylmethoxypropyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCCCOCC=1C=CC=CC=1)C(=O)OCCCOCC1=CC=CC=C1 WMWHRXNMXHUDHU-UYHPJTEGSA-N 0.000 claims 1
- VFCAKLHJHIBUSE-UHFFFAOYSA-N bis(3-trimethylsilylpropyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCCC[Si](C)(C)C)(C(=O)OCCC[Si](C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 VFCAKLHJHIBUSE-UHFFFAOYSA-N 0.000 claims 1
- HYLIYAIRWFDNMS-UHFFFAOYSA-N bis(4-methylpentanoyloxymethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCOC(=O)CCC(C)C)(C(=O)OCOC(=O)CCC(C)C)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 HYLIYAIRWFDNMS-UHFFFAOYSA-N 0.000 claims 1
- XNHDAXYFERIURL-REBFLZFKSA-N bis(4-phenylmethoxybut-2-enyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC=CCOCC=1C=CC=CC=1)C(=O)OCC=CCOCC1=CC=CC=C1 XNHDAXYFERIURL-REBFLZFKSA-N 0.000 claims 1
- HVCKQHOQLXAGQU-UHFFFAOYSA-N bis(acetyloxymethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCOC(C)=O)(C(=O)OCOC(C)=O)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 HVCKQHOQLXAGQU-UHFFFAOYSA-N 0.000 claims 1
- RMKPONPOKHSDDT-UHFFFAOYSA-N bis(cyclohexylmethyl) 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCC1CCCCC1)C(=O)OCC1CCCCC1 RMKPONPOKHSDDT-UHFFFAOYSA-N 0.000 claims 1
- HOBFKAMPPUNREC-OFVOXUNVSA-N bis(oxan-2-ylmethyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC1OCCCC1)C(=O)OCC1CCCCO1 HOBFKAMPPUNREC-OFVOXUNVSA-N 0.000 claims 1
- FPSHVGKMJDSSCL-ONCCDENISA-N bis(oxolan-2-ylmethyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC1OCCC1)C(=O)OCC1CCCO1 FPSHVGKMJDSSCL-ONCCDENISA-N 0.000 claims 1
- AMOLEAUVLPOKDK-XQKWPDNKSA-N bis(oxolan-3-ylmethyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC1COCC1)C(=O)OCC1CCOC1 AMOLEAUVLPOKDK-XQKWPDNKSA-N 0.000 claims 1
- UYCZLHNZHMVBDJ-UTKZUKDTSA-N bis(prop-2-enyl) 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C(=O)OCC=C)C(=O)OCC=C)C)=CC=CC(Cl)=C1 UYCZLHNZHMVBDJ-UTKZUKDTSA-N 0.000 claims 1
- DJODLMUTKJOZRI-USVBERQTSA-N bis[(1-methylcyclohex-3-en-1-yl)methyl] 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C[C@H](Cc1ccc2OC(Oc2c1)(C(=O)OCC1(C)CCC=CC1)C(=O)OCC1(C)CCC=CC1)NC[C@H](O)c1cccc(Cl)c1 DJODLMUTKJOZRI-USVBERQTSA-N 0.000 claims 1
- IHCBHCYLHOVQST-IRPSRAIASA-N bis[(1-methylcyclohexyl)methyl] 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCC1(C)CCCCC1)C(=O)OCC1(C)CCCCC1 IHCBHCYLHOVQST-IRPSRAIASA-N 0.000 claims 1
- OQEPLQKASGIDPK-BWKNWUBXSA-N bis[(5-methyl-1,3-dioxan-5-yl)methyl] 5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound CC1(COCOC1)COC(=O)C1(OC2=C(O1)C=CC(=C2)C[C@@H](C)NC[C@H](O)C2=CC(=CC=C2)Cl)C(=O)OCC2(COCOC2)C OQEPLQKASGIDPK-BWKNWUBXSA-N 0.000 claims 1
- ZXUYCGHRHVCOMQ-UHFFFAOYSA-N bis[2-(2-methylpropoxy)ethyl] 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C1=C2OC(C(=O)OCCOCC(C)C)(C(=O)OCCOCC(C)C)OC2=CC=C1CC(C)NCC(O)C1=CC=CC(Cl)=C1 ZXUYCGHRHVCOMQ-UHFFFAOYSA-N 0.000 claims 1
- NSZCTMKNYBPTMF-JWBZVWOHSA-N bis[2-(3-bromophenyl)ethyl] 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate;hydrochloride Chemical compound Cl.C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCCC=1C=C(Br)C=CC=1)C(=O)OCCC1=CC=CC(Br)=C1 NSZCTMKNYBPTMF-JWBZVWOHSA-N 0.000 claims 1
- YEUNMODXFISSTQ-XPWJQZKUSA-N bis[2-(3-methylphenyl)ethyl] 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate;hydrochloride Chemical compound Cl.C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OCCC=1C=C(C)C=CC=1)C(=O)OCCC1=CC=CC(C)=C1 YEUNMODXFISSTQ-XPWJQZKUSA-N 0.000 claims 1
- DBTPEBHLKQRHQD-UHFFFAOYSA-N bis[2-[(2-methylpropan-2-yl)oxy]ethyl] 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=C2OC(C(=O)OCCOC(C)(C)C)(C(=O)OCCOC(C)(C)C)OC2=CC=1CC(C)NCC(O)C1=CC=CC(Cl)=C1 DBTPEBHLKQRHQD-UHFFFAOYSA-N 0.000 claims 1
- WMZLOAORDSQZFM-UHFFFAOYSA-N dibenzyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 WMZLOAORDSQZFM-UHFFFAOYSA-N 0.000 claims 1
- HCUYDELGRGZNGA-UHFFFAOYSA-N dicyclohexyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OC1CCCCC1)C(=O)OC1CCCCC1 HCUYDELGRGZNGA-UHFFFAOYSA-N 0.000 claims 1
- MWKAXUPLJSMKBM-NJHZRGNWSA-N dicyclooctyl 5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C(C=C1O2)=CC=C1OC2(C(=O)OC1CCCCCCC1)C(=O)OC1CCCCCCC1 MWKAXUPLJSMKBM-NJHZRGNWSA-N 0.000 claims 1
- SLQRINHXENCPDI-UHFFFAOYSA-N dicyclopentyl 5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC(C)CC(C=C1O2)=CC=C1OC2(C(=O)OC1CCCC1)C(=O)OC1CCCC1 SLQRINHXENCPDI-UHFFFAOYSA-N 0.000 claims 1
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- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- BPRVJFRRXJYYQF-UHFFFAOYSA-N iodomethyl 3,3-dimethylbutanoate Chemical compound CC(C)(C)CC(=O)OCI BPRVJFRRXJYYQF-UHFFFAOYSA-N 0.000 description 1
- NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 1
- AHWAPPBPAIVQBI-UHFFFAOYSA-N iodomethyl heptanoate Chemical compound CCCCCCC(=O)OCI AHWAPPBPAIVQBI-UHFFFAOYSA-N 0.000 description 1
- IFZADQLLMDQVOK-UHFFFAOYSA-N iodomethyl hexanoate Chemical compound CCCCCC(=O)OCI IFZADQLLMDQVOK-UHFFFAOYSA-N 0.000 description 1
- JSPZULPOZBGXGJ-UHFFFAOYSA-N iodomethyl pentanoate Chemical compound CCCCC(=O)OCI JSPZULPOZBGXGJ-UHFFFAOYSA-N 0.000 description 1
- GLQOBGUEBABWDN-UHFFFAOYSA-N iodomethyl propanoate Chemical compound CCC(=O)OCI GLQOBGUEBABWDN-UHFFFAOYSA-N 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PCPUMGYALMOCHF-UHFFFAOYSA-N oxolan-3-ylmethanol Chemical compound OCC1CCOC1 PCPUMGYALMOCHF-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- JCWLEWKPXYZHGQ-UHFFFAOYSA-N propan-2-yl 2-bromoacetate Chemical compound CC(C)OC(=O)CBr JCWLEWKPXYZHGQ-UHFFFAOYSA-N 0.000 description 1
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical compound CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Nouveaux composés présentant une activité antidiurétique et/ou antihyperglycémique et/ou anti-obésité, et compositions pharmaceutiques et méthodes de traitement utilisant les composés et procédés de fabrication de ces composés, qui sont de formule (II), dans laquelle R¿1? et R¿6? sont indépendamment hydrogène, alkyle en C¿1?-C¿6?, trifluorométhyle, cyano, alcoxy en C¿1?-C¿6?, ou halogène; R¿2? est hydrogène ou trialkylsilyle en C¿1?-C¿6?; R¿3? est hydrogène ou alcoxycarbonyle en C¿1?-C¿6?; ou R¿2? et R¿3? ensemble forment un noyau (a) dans lequel R' est hydrogène, alkyle en C¿1?-C¿6? ou aryle; R¿4? et R¿5? sont indépendamment hydrogène ou alkyle en C¿1?-C¿6?; R¿7? et R¿8? sont indépendamment OR¿9? ou NR¿10?R¿11?; R¿9? est hydrogène, alkyle en C¿1?-C¿12?, cycloalkyle en C¿1?-C¿12?, silylalkyle en C¿1?-C¿12?, aryle, arylakyle, alcoxyalkyle, hétéroaryle, -CHR¿12?COOR¿13?, -CHR¿12?C(O)R¿13?, -CHR¿12?CONR¿10?R¿11?, -CHR¿12?OCOOR¿13?, ou -CHR¿12?OC(O)R¿13?, à condition que R¿9? ne soit pas hydrogène à la fois dans R¿7? et R¿8?; R¿10? et R¿11? sont indépendamment hydrogène, alkyle en C¿1?-C¿12?, aralkyle, aryle, furanylalkyle, ou alcoxycarbonylalkyle; R¿12? et R¿13? sont indépendamment hydrogène, alkyle en C¿1?-C¿12?, aryle, ou aralkyle; leurs sels pharmaceutiquement acceptables, leurs énantiomères, les mélanges racémiques correspondants et les mélanges diastéréomériques correspondants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64597096A | 1996-05-14 | 1996-05-14 | |
| US08/645,970 | 1996-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2254120A1 true CA2254120A1 (fr) | 1997-11-20 |
Family
ID=24591209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002254120A Abandoned CA2254120A1 (fr) | 1996-05-14 | 1997-05-09 | 1,3-benzodioxoles substitues |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0901484A1 (fr) |
| JP (1) | JP2000510150A (fr) |
| KR (1) | KR20000011001A (fr) |
| AU (1) | AU730659B2 (fr) |
| BR (1) | BR9708948A (fr) |
| CA (1) | CA2254120A1 (fr) |
| HU (1) | HUP9902088A2 (fr) |
| IL (1) | IL126780A0 (fr) |
| NZ (1) | NZ332713A (fr) |
| WO (1) | WO1997043273A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3100977A1 (fr) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulateurs d'enzymes de modification de methyle, compositions et utilisations de ceux-ci |
| AU2020316072A1 (en) * | 2019-07-24 | 2022-02-24 | Constellation Pharmaceuticals, Inc. | EZH2 inhibition in combination therapies for the treatment of cancers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061727A (en) * | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| US5482971A (en) * | 1993-10-01 | 1996-01-09 | American Cyanamid Company | Beta3 -adrenergic agents and their use in pharmaceutical compositions |
-
1997
- 1997-05-05 EP EP97924720A patent/EP0901484A1/fr not_active Withdrawn
- 1997-05-05 HU HU9902088A patent/HUP9902088A2/hu unknown
- 1997-05-09 BR BR9708948A patent/BR9708948A/pt unknown
- 1997-05-09 WO PCT/US1997/008148 patent/WO1997043273A1/fr not_active Application Discontinuation
- 1997-05-09 JP JP09541097A patent/JP2000510150A/ja active Pending
- 1997-05-09 CA CA002254120A patent/CA2254120A1/fr not_active Abandoned
- 1997-05-09 KR KR1019980709151A patent/KR20000011001A/ko not_active Application Discontinuation
- 1997-05-09 NZ NZ332713A patent/NZ332713A/xx unknown
- 1997-05-09 IL IL12678097A patent/IL126780A0/xx unknown
- 1997-05-09 AU AU30067/97A patent/AU730659B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9902088A2 (hu) | 2001-04-28 |
| KR20000011001A (ko) | 2000-02-25 |
| EP0901484A1 (fr) | 1999-03-17 |
| JP2000510150A (ja) | 2000-08-08 |
| AU730659B2 (en) | 2001-03-08 |
| BR9708948A (pt) | 1999-08-03 |
| NZ332713A (en) | 2000-07-28 |
| IL126780A0 (en) | 1999-08-17 |
| WO1997043273A1 (fr) | 1997-11-20 |
| AU3006797A (en) | 1997-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |