ZA200500340B - Novel benzodioxoles - Google Patents
Novel benzodioxoles Download PDFInfo
- Publication number
- ZA200500340B ZA200500340B ZA200500340A ZA200500340A ZA200500340B ZA 200500340 B ZA200500340 B ZA 200500340B ZA 200500340 A ZA200500340 A ZA 200500340A ZA 200500340 A ZA200500340 A ZA 200500340A ZA 200500340 B ZA200500340 B ZA 200500340B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- fluoro
- benzo
- dioxol
- methanone
- Prior art date
Links
- 150000005528 benzodioxoles Chemical class 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 274
- 150000001875 compounds Chemical class 0.000 claims description 146
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
- 125000003545 alkoxy group Chemical group 0.000 claims description 85
- 150000002367 halogens Chemical class 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 77
- -1 dioxo Chemical group 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000001589 carboacyl group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 235000002639 sodium chloride Nutrition 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 20
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 19
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 229960005141 piperazine Drugs 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 102000005962 receptors Human genes 0.000 claims description 14
- 108020003175 receptors Proteins 0.000 claims description 14
- 239000012442 inert solvent Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical group C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003725 azepanyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 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 3
- XIZXADDGOCJZAL-UHFFFAOYSA-N 3h-dioxole-5-carboxylic acid Chemical compound OC(=O)C1=CCOO1 XIZXADDGOCJZAL-UHFFFAOYSA-N 0.000 claims description 3
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- MWPRYEVXYYJFFA-UHFFFAOYSA-N n-benzyl-2,2-diphenyl-1,3-benzodioxole-5-sulfonamide Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 MWPRYEVXYYJFFA-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 3
- YGYOXYYVENEFEV-UHFFFAOYSA-N (6-chloro-2,2-diphenyl-1,3-benzodioxol-5-yl)-morpholin-4-ylmethanone Chemical compound ClC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCOCC1 YGYOXYYVENEFEV-UHFFFAOYSA-N 0.000 claims description 2
- XTESHPWNXCEONX-UHFFFAOYSA-N (6-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound FC1=CC=2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC=2C=C1C(=O)N1CCCCC1 XTESHPWNXCEONX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SFZQVTZHYVPOEA-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]piperazine Chemical compound ClC1=CC(Cl)=CC=C1N1CCN(S(=O)(=O)C=2C=C3OC(OC3=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 SFZQVTZHYVPOEA-UHFFFAOYSA-N 0.000 claims description 2
- CKTFIKKUMMHAAM-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1S(=O)(=O)C1=CC=C(OC(O2)(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 CKTFIKKUMMHAAM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- KFCMDPWYCAHJPA-UHFFFAOYSA-N 1-[[2,2-bis(4-chlorophenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(Cl)=CC=2)OC2=CC(S(=O)(=O)N3CCCCC3)=CC=C2O1 KFCMDPWYCAHJPA-UHFFFAOYSA-N 0.000 claims description 2
- MJZJCSNSDCIHGV-UHFFFAOYSA-N 1-[[6-fluoro-2,2-bis(4-methylphenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC(C)=CC=2)OC2=CC(S(=O)(=O)N3CCCCC3)=C(F)C=C2O1 MJZJCSNSDCIHGV-UHFFFAOYSA-N 0.000 claims description 2
- CNWAXQZNUTXKNX-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-ethyl-6-fluoro-2-(4-fluorophenyl)-n-methyl-1,3-benzodioxole-5-carboxamide Chemical compound O1C=2C=C(F)C(C(=O)N(C)CC)=CC=2OC1(C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(F)C=C1 CNWAXQZNUTXKNX-UHFFFAOYSA-N 0.000 claims description 2
- KOHBEDRJXKOYHL-UHFFFAOYSA-N 2-methoxy-n-methylethanamine Chemical compound CNCCOC KOHBEDRJXKOYHL-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- QSTCDGIMYPERQN-UHFFFAOYSA-N [6-fluoro-2,2-bis(4-fluorophenyl)-1,3-benzodioxol-5-yl]-[4-(trifluoromethyl)piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1(C=2C=CC(F)=CC=2)OC2=CC(C(=O)N3CCC(CC3)C(F)(F)F)=C(F)C=C2O1 QSTCDGIMYPERQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims description 2
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- ZMCWJLMTPBAXFX-UHFFFAOYSA-N n-(2,2-diphenyl-1,3-benzodioxol-5-yl)butanamide Chemical compound O1C2=CC(NC(=O)CCC)=CC=C2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 ZMCWJLMTPBAXFX-UHFFFAOYSA-N 0.000 claims description 2
- ZLSCRWNCXFFBKP-UHFFFAOYSA-N n-(2,2-diphenyl-1,3-benzodioxol-5-yl)cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC(C=C1O2)=CC=C1OC2(C=1C=CC=CC=1)C1=CC=CC=C1 ZLSCRWNCXFFBKP-UHFFFAOYSA-N 0.000 claims description 2
- FROVTOWPFHKTOL-UHFFFAOYSA-N n-benzyl-n-methyl-2,2-diphenyl-1,3-benzodioxole-5-sulfonamide Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 FROVTOWPFHKTOL-UHFFFAOYSA-N 0.000 claims description 2
- MMCCUCUPYFHMEM-UHFFFAOYSA-N n-butylsulfonyl-n-(2,2-diphenyl-1,3-benzodioxol-5-yl)butane-1-sulfonamide Chemical compound O1C2=CC(N(S(=O)(=O)CCCC)S(=O)(=O)CCCC)=CC=C2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 MMCCUCUPYFHMEM-UHFFFAOYSA-N 0.000 claims description 2
- KKVUFSINQFSJNK-UHFFFAOYSA-N o-tert-butylhydroxylamine Chemical compound CC(C)(C)ON KKVUFSINQFSJNK-UHFFFAOYSA-N 0.000 claims description 2
- VPBCWHDJJAEBGL-UHFFFAOYSA-N piperidin-1-ium-1-sulfonate Chemical compound OS(=O)(=O)N1CCCCC1 VPBCWHDJJAEBGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 44
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 2
- LTEXPJKPLVJFGS-UHFFFAOYSA-N (2,2-diphenyl-1,3-benzodioxol-5-yl)-[3-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound C1C(CO)CCCN1C(=O)C1=CC=C(OC(O2)(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 LTEXPJKPLVJFGS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WFUDPWLCEJSWBC-UHFFFAOYSA-N (2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1C(=O)N1CCCCC1 WFUDPWLCEJSWBC-UHFFFAOYSA-N 0.000 claims 1
- NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 0.000 claims 1
- ADIXHJHAPRNODN-UHFFFAOYSA-N (7-hydroxy-2,2-diphenyl-1,3-benzodioxol-5-yl)-piperidin-1-ylmethanone Chemical compound O1C=2C(O)=CC(C(=O)N3CCCCC3)=CC=2OC1(C=1C=CC=CC=1)C1=CC=CC=C1 ADIXHJHAPRNODN-UHFFFAOYSA-N 0.000 claims 1
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- GBBVHDGKDQAEOT-UHFFFAOYSA-N 1,7-dioxaspiro[5.5]undecane Chemical compound O1CCCCC11OCCCC1 GBBVHDGKDQAEOT-UHFFFAOYSA-N 0.000 claims 1
- MYOSYXDGCAIQJF-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]-4-(3-methoxyphenyl)piperazine Chemical compound COC1=CC=CC(N2CCN(CC2)S(=O)(=O)C=2C=C3OC(OC3=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MYOSYXDGCAIQJF-UHFFFAOYSA-N 0.000 claims 1
- PCYILJNSFUGXFQ-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(OC(O2)(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=C1 PCYILJNSFUGXFQ-UHFFFAOYSA-N 0.000 claims 1
- XDHZURQXJVJWGQ-UHFFFAOYSA-N 1-[(2,2-diphenyl-1,3-benzodioxol-5-yl)sulfonyl]-4-phenyl-3,6-dihydro-2h-pyridine Chemical compound C=1C=C2OC(C=3C=CC=CC=3)(C=3C=CC=CC=3)OC2=CC=1S(=O)(=O)N(CC=1)CCC=1C1=CC=CC=C1 XDHZURQXJVJWGQ-UHFFFAOYSA-N 0.000 claims 1
- NZAJPBNDRAFVEF-UHFFFAOYSA-N 1-[[2,2-bis(2,4-difluorophenyl)-6-fluoro-1,3-benzodioxol-5-yl]sulfonyl]-4,4-difluoropiperidine Chemical compound FC1=CC(F)=CC=C1C1(C=2C(=CC(F)=CC=2)F)OC2=CC(S(=O)(=O)N3CCC(F)(F)CC3)=C(F)C=C2O1 NZAJPBNDRAFVEF-UHFFFAOYSA-N 0.000 claims 1
- FZFZEXQJKJHYOE-UHFFFAOYSA-N 1-[[2-(2-chlorophenyl)-2-(4-chlorophenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C1(C=2C(=CC=CC=2)Cl)OC2=CC(S(=O)(=O)N3CCCCC3)=CC=C2O1 FZFZEXQJKJHYOE-UHFFFAOYSA-N 0.000 claims 1
- GJMMDWLWLNIEIK-UHFFFAOYSA-N 1-[[2-(3-chlorophenyl)-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1=CC(F)=CC=C1C1(C=2C=C(Cl)C=CC=2)OC2=CC(S(=O)(=O)N3CCCCC3)=CC=C2O1 GJMMDWLWLNIEIK-UHFFFAOYSA-N 0.000 claims 1
- YAGVPCYHXFPPEZ-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]sulfonyl]piperidine Chemical compound C1=CC(F)=CC=C1C1(C=2C=CC(Cl)=CC=2)OC2=CC(S(=O)(=O)N3CCCCC3)=CC=C2O1 YAGVPCYHXFPPEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- MGCLRMPXVCFQMJ-UHFFFAOYSA-N 4-[2-(4-cyanophenyl)-5-fluoro-6-(morpholine-4-carbonyl)-1,3-benzodioxol-2-yl]benzonitrile Chemical compound FC1=CC=2OC(C=3C=CC(=CC=3)C#N)(C=3C=CC(=CC=3)C#N)OC=2C=C1C(=O)N1CCOCC1 MGCLRMPXVCFQMJ-UHFFFAOYSA-N 0.000 claims 1
- BATZBBJXUUQWQD-UHFFFAOYSA-N 4-[[2-(4-methoxyphenyl)-2-(3-nitrophenyl)-1,3-benzodioxol-5-yl]sulfonyl]morpholine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)[N+]([O-])=O)OC2=CC(S(=O)(=O)N3CCOCC3)=CC=C2O1 BATZBBJXUUQWQD-UHFFFAOYSA-N 0.000 claims 1
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- 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
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- 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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