HRP20050044A2 - Novel benzodioxoles - Google Patents
Novel benzodioxoles Download PDFInfo
- Publication number
- HRP20050044A2 HRP20050044A2 HR20050044A HRP20050044A HRP20050044A2 HR P20050044 A2 HRP20050044 A2 HR P20050044A2 HR 20050044 A HR20050044 A HR 20050044A HR P20050044 A HRP20050044 A HR P20050044A HR P20050044 A2 HRP20050044 A2 HR P20050044A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- fluoro
- benzo
- dioxol
- methanone
- Prior art date
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- 150000005528 benzodioxoles Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 488
- 238000002360 preparation method Methods 0.000 claims description 464
- 238000000034 method Methods 0.000 claims description 286
- 125000000217 alkyl group Chemical group 0.000 claims description 275
- -1 dioxo Chemical group 0.000 claims description 149
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
- PRBIGHBSZUXNPL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxole-5-carboxylic acid Chemical compound O1C=2C=C(F)C(C(=O)O)=CC=2OC1(C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(F)C=C1 PRBIGHBSZUXNPL-UHFFFAOYSA-N 0.000 claims description 87
- 125000003545 alkoxy group Chemical group 0.000 claims description 87
- 150000002367 halogens Chemical class 0.000 claims description 83
- 229910052736 halogen Inorganic materials 0.000 claims description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 74
- 229910001868 water Inorganic materials 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 59
- 125000001589 carboacyl group Chemical group 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 39
- 150000001412 amines Chemical class 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- VUCKSZWMRCSPME-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCOCC3)=C(F)C=C2O1 VUCKSZWMRCSPME-UHFFFAOYSA-N 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 239000012442 inert solvent Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- HTDWPDKJCFFSEL-UHFFFAOYSA-N 2,2-diphenyl-1,3-benzodioxol-5-amine Chemical compound O1C2=CC(N)=CC=C2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 HTDWPDKJCFFSEL-UHFFFAOYSA-N 0.000 claims description 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- GKBAASGRLHNBPI-UHFFFAOYSA-N [2,2-bis(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C(=CC(Br)=CC=3)F)(C=3C(=CC(Br)=CC=3)F)OC=2C=C1C(=O)N1CCOCC1 GKBAASGRLHNBPI-UHFFFAOYSA-N 0.000 claims description 7
- ZAQILESACFCOBN-UHFFFAOYSA-N (6-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCOCC1 ZAQILESACFCOBN-UHFFFAOYSA-N 0.000 claims description 6
- REGQBPFXVQQNAU-UHFFFAOYSA-N [2,2-bis(4-chlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound FC1=CC=2OC(C=3C=CC(Cl)=CC=3)(C=3C=CC(Cl)=CC=3)OC=2C=C1C(=O)N1CCCCC1 REGQBPFXVQQNAU-UHFFFAOYSA-N 0.000 claims description 6
- XYDVBMQRONWAHV-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-thiomorpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCSCC3)=C(F)C=C2O1 XYDVBMQRONWAHV-UHFFFAOYSA-N 0.000 claims description 6
- DQAAJRWQFIWYBX-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-methoxyphenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCCCC3)=C(F)C=C2O1 DQAAJRWQFIWYBX-UHFFFAOYSA-N 0.000 claims description 6
- ABIINTHUMZUGCG-UHFFFAOYSA-N [2-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C(=CC(Cl)=CC=3)Cl)(C=3C=CC(Cl)=CC=3)OC=2C=C1C(=O)N1CCOCC1 ABIINTHUMZUGCG-UHFFFAOYSA-N 0.000 claims description 6
- PZFRHXUJWPTAGV-UHFFFAOYSA-N [6-fluoro-2,2-bis(2-fluorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound FC1=CC=CC=C1C1(C=2C(=CC=CC=2)F)OC2=CC(C(=O)N3CCCCC3)=C(F)C=C2O1 PZFRHXUJWPTAGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003725 azepanyl group Chemical group 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- YTGUIZSEZJBJRX-UHFFFAOYSA-N (2,2-diphenyl-1,3-benzodioxol-5-yl)-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1C(=O)N1CCOCC1 YTGUIZSEZJBJRX-UHFFFAOYSA-N 0.000 claims description 5
- OUONCAGZTUTCGU-UHFFFAOYSA-N 4-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]morpholine Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1S(=O)(=O)N1CCOCC1 OUONCAGZTUTCGU-UHFFFAOYSA-N 0.000 claims description 5
- SERJCABUYZJOGM-UHFFFAOYSA-N [2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C1CC(O)CCN1C(=O)C(C(=C1)F)=CC2=C1OC(C=1C(=CC(F)=CC=1)F)(C=1C(=CC(F)=CC=1)F)O2 SERJCABUYZJOGM-UHFFFAOYSA-N 0.000 claims description 5
- IPGGXACUBFSSHA-UHFFFAOYSA-N [2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(C(=O)N3CCOCC3)=C(F)C=C2O1 IPGGXACUBFSSHA-UHFFFAOYSA-N 0.000 claims description 5
- SJMBODNIXZRCSX-UHFFFAOYSA-N [2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(C(=O)N3CCCCC3)=C(F)C=C2O1 SJMBODNIXZRCSX-UHFFFAOYSA-N 0.000 claims description 5
- CYHVPHOGXLICFE-UHFFFAOYSA-N [2,2-bis(4-bromophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C=CC(Br)=CC=3)(C=3C=CC(Br)=CC=3)OC=2C=C1C(=O)N1CCOCC1 CYHVPHOGXLICFE-UHFFFAOYSA-N 0.000 claims description 5
- HNHOAJREYUMMOB-UHFFFAOYSA-N [2,2-bis(4-chlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-pyrrolidin-1-ylmethanone Chemical compound FC1=CC=2OC(C=3C=CC(Cl)=CC=3)(C=3C=CC(Cl)=CC=3)OC=2C=C1C(=O)N1CCCC1 HNHOAJREYUMMOB-UHFFFAOYSA-N 0.000 claims description 5
- ZYJFHTSOOUFNFJ-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCCCC3)=C(F)C=C2O1 ZYJFHTSOOUFNFJ-UHFFFAOYSA-N 0.000 claims description 5
- GFSKZAXITVNQLK-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-methoxyphenyl)-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCOCC3)=C(F)C=C2O1 GFSKZAXITVNQLK-UHFFFAOYSA-N 0.000 claims description 5
- NECZGXNGANIBNO-UHFFFAOYSA-N [2-(2-chlorophenyl)-6-fluoro-2-(4-methoxyphenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1(C=2C(=CC=CC=2)Cl)OC2=CC(C(=O)N3CCCCC3)=C(F)C=C2O1 NECZGXNGANIBNO-UHFFFAOYSA-N 0.000 claims description 5
- BLVMJAMKFLXJPH-UHFFFAOYSA-N [2-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound FC1=CC=2OC(C=3C(=CC(Cl)=CC=3)Cl)(C=3C=CC(Cl)=CC=3)OC=2C=C1C(=O)N1CCCCC1 BLVMJAMKFLXJPH-UHFFFAOYSA-N 0.000 claims description 5
- NSEMFPPPPJYRQT-UHFFFAOYSA-N [2-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-pyrrolidin-1-ylmethanone Chemical compound FC1=CC=2OC(C=3C(=CC(Cl)=CC=3)Cl)(C=3C=CC(Cl)=CC=3)OC=2C=C1C(=O)N1CCCC1 NSEMFPPPPJYRQT-UHFFFAOYSA-N 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 5
- DNEXYKQLITTWLZ-UHFFFAOYSA-N (2,2-diphenyl-1,3-benzodioxol-5-yl)-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=CCN(C(=O)C=2C=C3OC(OC3=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 DNEXYKQLITTWLZ-UHFFFAOYSA-N 0.000 claims description 4
- VLWTYITXDDMXHO-UHFFFAOYSA-N (6-bromo-2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound BrC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCCCC1 VLWTYITXDDMXHO-UHFFFAOYSA-N 0.000 claims description 4
- LRKYMAKUKFGSSF-UHFFFAOYSA-N (6-chloro-2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound ClC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCCCC1 LRKYMAKUKFGSSF-UHFFFAOYSA-N 0.000 claims description 4
- XROVBJDGBSGDIS-UHFFFAOYSA-N (6-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)C=2C(=CC=3OC(OC=3C=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)F)CC1 XROVBJDGBSGDIS-UHFFFAOYSA-N 0.000 claims description 4
- ZSSJHHFAPWKTTC-UHFFFAOYSA-N (6-methyl-2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound CC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCCCC1 ZSSJHHFAPWKTTC-UHFFFAOYSA-N 0.000 claims description 4
- HAQRKBMHJXTTRZ-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]-4-(4-fluorophenyl)-3,6-dihydro-2h-pyridine Chemical compound C1=CC(F)=CC=C1C1=CCN(S(=O)(=O)C=2C=C3OC(OC3=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 HAQRKBMHJXTTRZ-UHFFFAOYSA-N 0.000 claims description 4
- PRJGXZKLMDRCRI-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]piperidine Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1S(=O)(=O)N1CCCCC1 PRJGXZKLMDRCRI-UHFFFAOYSA-N 0.000 claims description 4
- ISASPHHGOOZIEE-UHFFFAOYSA-N 1-[[2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]sulfonyl]pyrrolidine Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(S(=O)(=O)N3CCCC3)=C(F)C=C2O1 ISASPHHGOOZIEE-UHFFFAOYSA-N 0.000 claims description 4
- AGYWPAPJPZRILB-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)-2-(2-fluoro-4-methoxyphenyl)-1,3-benzodioxol-5-yl]sulfonyl]morpholine Chemical compound FC1=CC(OC)=CC=C1C1(C=2C=CC(Cl)=CC=2)OC2=CC(S(=O)(=O)N3CCOCC3)=CC=C2O1 AGYWPAPJPZRILB-UHFFFAOYSA-N 0.000 claims description 4
- YQMBJYDCUARSPU-UHFFFAOYSA-N 4-fluoro-1-[[6-fluoro-2,2-bis(4-fluorophenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1CC(F)CCN1S(=O)(=O)C(C(=C1)F)=CC2=C1OC(C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)O2 YQMBJYDCUARSPU-UHFFFAOYSA-N 0.000 claims description 4
- NOFFBSSIYMWRMO-UHFFFAOYSA-N [2,2-bis(2,3-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=CC(C2(OC3=CC(=C(F)C=C3O2)C(=O)N2CCOCC2)C=2C(=C(F)C=CC=2)F)=C1F NOFFBSSIYMWRMO-UHFFFAOYSA-N 0.000 claims description 4
- HULLXBIOTMMJOU-UHFFFAOYSA-N [2,2-bis(2,4-dichlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound C1C(O)CCN1C(=O)C(C(=C1)F)=CC2=C1OC(C=1C(=CC(Cl)=CC=1)Cl)(C=1C(=CC(Cl)=CC=1)Cl)O2 HULLXBIOTMMJOU-UHFFFAOYSA-N 0.000 claims description 4
- CSHYFNSQQACJIU-UHFFFAOYSA-N [2,2-bis(2,4-dichlorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C(=CC(Cl)=CC=3)Cl)(C=3C(=CC(Cl)=CC=3)Cl)OC=2C=C1C(=O)N1CCOCC1 CSHYFNSQQACJIU-UHFFFAOYSA-N 0.000 claims description 4
- DFZYXLNHGGVKJO-UHFFFAOYSA-N [2,2-bis(2,4-difluorophenyl)-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(C(=O)N3CCOCC3)=CC=C2O1 DFZYXLNHGGVKJO-UHFFFAOYSA-N 0.000 claims description 4
- YTHMRYNWHQGSRZ-UHFFFAOYSA-N [2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(C(=O)N3CCC(F)(F)CC3)=C(F)C=C2O1 YTHMRYNWHQGSRZ-UHFFFAOYSA-N 0.000 claims description 4
- PKSUZKLELJHAEG-UHFFFAOYSA-N [2,2-bis(2,5-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=C(F)C(C2(OC3=CC(=C(F)C=C3O2)C(=O)N2CCOCC2)C=2C(=CC=C(F)C=2)F)=C1 PKSUZKLELJHAEG-UHFFFAOYSA-N 0.000 claims description 4
- YQKPPXZFPFSGMC-UHFFFAOYSA-N [2,2-bis(3,5-dichlorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound ClC1=CC(Cl)=CC(C2(OC3=CC(=CC=C3O2)C(=O)N2CCCCC2)C=2C=C(Cl)C=C(Cl)C=2)=C1 YQKPPXZFPFSGMC-UHFFFAOYSA-N 0.000 claims description 4
- GUWKSVJTJRIOBL-UHFFFAOYSA-N [2,2-bis(3,5-difluorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound FC1=CC(F)=CC(C2(OC3=CC(=CC=C3O2)C(=O)N2CCCCC2)C=2C=C(F)C=C(F)C=2)=C1 GUWKSVJTJRIOBL-UHFFFAOYSA-N 0.000 claims description 4
- COHHGOAJXJKXAC-UHFFFAOYSA-N [2,2-bis(3-bromophenyl)-6-fluoro-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC=2OC(C=3C=C(Br)C=CC=3)(C=3C=C(Br)C=CC=3)OC=2C=C1C(=O)N1CCOCC1 COHHGOAJXJKXAC-UHFFFAOYSA-N 0.000 claims description 4
- TVLRNVYYUGRZTF-UHFFFAOYSA-N [2,2-bis(3-chlorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound ClC1=CC=CC(C2(OC3=CC(=CC=C3O2)C(=O)N2CCCCC2)C=2C=C(Cl)C=CC=2)=C1 TVLRNVYYUGRZTF-UHFFFAOYSA-N 0.000 claims description 4
- SCQXFMZXRHXQKM-UHFFFAOYSA-N [2,2-bis(3-methoxyphenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound COC1=CC=CC(C2(OC3=CC(=CC=C3O2)C(=O)N2CCCCC2)C=2C=C(OC)C=CC=2)=C1 SCQXFMZXRHXQKM-UHFFFAOYSA-N 0.000 claims description 4
- NOLHOVGVUWMYJV-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-(4,4-difluoropiperidin-1-yl)methanone Chemical compound C1=CC(F)=CC=C1C1(C=2C(=CC(Cl)=CC=2)Cl)OC2=CC(C(=O)N3CCC(F)(F)CC3)=C(F)C=C2O1 NOLHOVGVUWMYJV-UHFFFAOYSA-N 0.000 claims description 4
- YUILXPOHIGOSDW-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-(4-fluoropiperidin-1-yl)methanone Chemical compound C1CC(F)CCN1C(=O)C(C(=C1)F)=CC2=C1OC(C=1C(=CC(Cl)=CC=1)Cl)(C=1C=CC(F)=CC=1)O2 YUILXPOHIGOSDW-UHFFFAOYSA-N 0.000 claims description 4
- VYTATJCDUJNQSK-UHFFFAOYSA-N [2-(2-chloro-4-fluorophenyl)-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)Cl)OC2=CC(C(=O)N3CCCCC3)=CC=C2O1 VYTATJCDUJNQSK-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- 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
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- 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
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
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