NO318628B1 - Pyrano-, piperidino- og tiopyranoforbindelser, farmasoytiske sammensetninger inneholdende det samme og anvendelse av forbindelsene - Google Patents

Info

Publication number

NO318628B1

NO318628B1 NO20012100A NO20012100A NO318628B1 NO 318628 B1 NO318628 B1 NO 318628B1 NO 20012100 A NO20012100 A NO 20012100A NO 20012100 A NO20012100 A NO 20012100A NO 318628 B1 NO318628 B1 NO 318628B1

Authority

NO

Norway

Prior art keywords

hydrogen

compound according

dione

fluorophenyl

bromo

Prior art date

1998-10-28

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 335
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 title description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 151
• 239000001257 hydrogen Substances 0.000 claims description 151
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 113
• -1 benzoxadiazolyl Chemical group 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 30
• 150000001408 amides Chemical class 0.000 claims description 28
• 150000002148 esters Chemical class 0.000 claims description 28
• 238000002360 preparation method Methods 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 206010046543 Urinary incontinence Diseases 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• SVGVJFUHAFQBJW-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-2,3,5,9-tetrahydro-4h-pyrano[3,4-b]thieno[2,3-e]pyridin-8(7h)-one 1,1-dioxide Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1S(=O)(=O)CC2 SVGVJFUHAFQBJW-UHFFFAOYSA-N 0.000 claims description 7
• GHKXQLMOLJUEMH-UHFFFAOYSA-N O=C1COCC(NC2=C3S(CC2)(=O)=O)=C1C3C1=CC=CC(C#N)=C1 Chemical compound O=C1COCC(NC2=C3S(CC2)(=O)=O)=C1C3C1=CC=CC(C#N)=C1 GHKXQLMOLJUEMH-UHFFFAOYSA-N 0.000 claims description 7
• SSPWAVCEXCHHOU-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-3,4,5,6,7,9-hexahydrofuro[3,4-b][1,7]naphthyridine-1,8-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CNC2)=C2NC2=C1C(=O)OC2 SSPWAVCEXCHHOU-UHFFFAOYSA-N 0.000 claims description 6
• RTACIKQKDIPFHG-UHFFFAOYSA-N 9-(4-fluoro-3-iodophenyl)-2,3,5,9-tetrahydro-4h-pyrano[3,4-b]thieno[2,3-e]pyridin-8(7h)-one 1,1-dioxide Chemical compound C1=C(I)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1S(=O)(=O)CC2 RTACIKQKDIPFHG-UHFFFAOYSA-N 0.000 claims description 6
• 208000030814 Eating disease Diseases 0.000 claims description 6
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 208000019695 Migraine disease Diseases 0.000 claims description 6
• 208000002193 Pain Diseases 0.000 claims description 6
• 208000003782 Raynaud disease Diseases 0.000 claims description 6
• 208000012322 Raynaud phenomenon Diseases 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 235000014632 disordered eating Nutrition 0.000 claims description 6
• 206010015037 epilepsy Diseases 0.000 claims description 6
• 206010027599 migraine Diseases 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• CJEUGZOJCKQPGZ-UHFFFAOYSA-N C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(COCC3=O)NC3=C2S(CC3)(=O)=O)=C1 Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2C3=C(COCC3=O)NC3=C2S(CC3)(=O)=O)=C1 CJEUGZOJCKQPGZ-UHFFFAOYSA-N 0.000 claims description 5
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 4
• HPVZXULMHGKKFN-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-1,2,3,5,7,8,9,10-octahydrobenzo[b][1,7]naphthyridine-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CNC2)=C2NC2=C1C(=O)CCC2 HPVZXULMHGKKFN-UHFFFAOYSA-N 0.000 claims description 4
• MVGIBFCDGKIFDX-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1h-cyclopenta[b][1,7]naphthyridine-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CNC2)=C2NC2=C1C(=O)CC2 MVGIBFCDGKIFDX-UHFFFAOYSA-N 0.000 claims description 4
• KPWZXKCOAZKFCF-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1h-cyclopenta[b][1,7]naphthyridine-4,6-dione Chemical compound C1=C(Cl)C(F)=CC=C1C1C(C(=O)CNC2)=C2NC2=C1C(=O)CC2 KPWZXKCOAZKFCF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• OWPSAEKUUIXVDU-UHFFFAOYSA-N 10-(3,4-dibromophenyl)-2,3,4,5,6,10-hexahydropyrano[3,4-b][1,6]naphthyridine-1,9-dione Chemical compound C1=C(Br)C(Br)=CC=C1C1C(C(=O)NCC2)=C2NC2=C1C(=O)COC2 OWPSAEKUUIXVDU-UHFFFAOYSA-N 0.000 claims description 3
• JNXJTZDHXINUSE-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-1,5,7,8,9,10-hexahydropyrano[3,4-b]quinoline-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)CCC2 JNXJTZDHXINUSE-UHFFFAOYSA-N 0.000 claims description 3
• IXIBEPWVIZVMMC-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-1,5,7,8,9,10-hexahydrothiopyrano[3,4-b]quinoline-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CSC2)=C2NC2=C1C(=O)CCC2 IXIBEPWVIZVMMC-UHFFFAOYSA-N 0.000 claims description 3
• BFVJEPANUDHFNL-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-7,7-dimethyl-5,8,9,10-tetrahydro-1h-pyrano[3,4-b]quinoline-4,6-dione Chemical compound O=C1C(C)(C)CCC(NC2=C3C(COC2)=O)=C1C3C1=CC=C(F)C(Br)=C1 BFVJEPANUDHFNL-UHFFFAOYSA-N 0.000 claims description 3
• ICYHUFIOOVJJSS-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3h-furo [3,4-b]pyrano[4,3-e]pyridine-1,8(4h,7h)-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)OC2 ICYHUFIOOVJJSS-UHFFFAOYSA-N 0.000 claims description 3
• TWKAHLRRKZIIJE-UHFFFAOYSA-N C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)CC2 Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)CC2 TWKAHLRRKZIIJE-UHFFFAOYSA-N 0.000 claims description 3
• IIJWKLFYJXSXKV-UHFFFAOYSA-N C1=C(Br)C(F)=CC=C1C1C(C(=O)CSC2)=C2NC2=C1C(=O)CC2 Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CSC2)=C2NC2=C1C(=O)CC2 IIJWKLFYJXSXKV-UHFFFAOYSA-N 0.000 claims description 3
• ZGLWJIUBWJNBLH-UHFFFAOYSA-N chembl3138579 Chemical compound C1=C(Br)C(F)=CC=C1C1C(S(=O)(=O)CCC2)=C2NC2=C1C(=O)COC2 ZGLWJIUBWJNBLH-UHFFFAOYSA-N 0.000 claims description 3
• 201000001881 impotence Diseases 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• XAXYWABWFVKQOX-UHFFFAOYSA-N 10-(3,4-dichlorophenyl)-2,3,4,5,6,10-hexahydropyrano[3,4-b][1,6]naphthyridine-1,9-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(C(=O)NCC2)=C2NC2=C1C(=O)COC2 XAXYWABWFVKQOX-UHFFFAOYSA-N 0.000 claims description 2
• SBSVMRKHPXQJIF-UHFFFAOYSA-N 10-(3-bromo-4-fluorophenyl)-2,3,4,5,6,10-hexahydropyrano[3,4-b][1,6]naphthyridine-1,9-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)NCC2)=C2NC2=C1C(=O)COC2 SBSVMRKHPXQJIF-UHFFFAOYSA-N 0.000 claims description 2
• PCVWZRUEHPBTRD-UHFFFAOYSA-N 10-(5-nitrothiophen-3-yl)-2,3,4,5,6,10-hexahydropyrano[3,4-b][1,6]naphthyridine-1,9-dione Chemical compound S1C([N+](=O)[O-])=CC(C2C3=C(CCNC3=O)NC3=C2C(COC3)=O)=C1 PCVWZRUEHPBTRD-UHFFFAOYSA-N 0.000 claims description 2
• GNSUWSGMBWMSPA-UHFFFAOYSA-N 10-[4-chloro-3-(trifluoromethyl)phenyl]-2,3,4,5,6,10-hexahydropyrano[3,4-b][1,6]naphthyridine-1,9-dione Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C2C3=C(CCNC3=O)NC3=C2C(COC3)=O)=C1 GNSUWSGMBWMSPA-UHFFFAOYSA-N 0.000 claims description 2
• GEIQGSRESAVZFB-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-1,2,3,5,7,8,9,10-octahydropyrido[3,4-b][1,7]naphthyridine-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)CNC2)=C2NC2=C1C(=O)CNC2 GEIQGSRESAVZFB-UHFFFAOYSA-N 0.000 claims description 2
• CZNFHVVNAROKCU-UHFFFAOYSA-N 5-(3-bromo-4-fluorophenyl)-1,5,7,8,9,10-hexahydropyrano[3,4-b][1,7]naphthyridine-4,6-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)CNC2 CZNFHVVNAROKCU-UHFFFAOYSA-N 0.000 claims description 2
• RPPWFSAXVVNIKV-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-2,3,5,9-tetrahydropyrano[3,4-b]pyrrolo[3,4-e]pyridine-1,8(4h,7h)-dione Chemical compound C1=C(Br)C(F)=CC=C1C1C(C(=O)COC2)=C2NC2=C1C(=O)NC2 RPPWFSAXVVNIKV-UHFFFAOYSA-N 0.000 claims description 2
• QDTMVJADNZUMQR-UHFFFAOYSA-N 9-(3-bromo-4-fluorophenyl)-2-methyl-2,3,5,9-tetrahydropyrano[3,4-b]pyrrolo[3,4-e]pyridine-1,8(4h,7h)-dione Chemical compound O=C1N(C)CC(NC2=C3C(COC2)=O)=C1C3C1=CC=C(F)C(Br)=C1 QDTMVJADNZUMQR-UHFFFAOYSA-N 0.000 claims description 2
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• 208000004483 Dyspareunia Diseases 0.000 claims description 2
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 2
• ICYHUFIOOVJJSS-ZDUSSCGKSA-N chembl2111694 Chemical compound C1=C(Br)C(F)=CC=C1[C@H]1C(C(=O)COC2)=C2NC2=C1C(=O)OC2 ICYHUFIOOVJJSS-ZDUSSCGKSA-N 0.000 claims description 2
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• FEAGUALNKLIJCJ-UHFFFAOYSA-N 10-(3-bromo-4-fluorophenyl)-1,1-dioxo-2,3,4,5,6,7,8,10-octahydrothiopyrano[3,2-b][1,7]naphthyridin-9-one Chemical compound C1=C(Br)C(F)=CC=C1C1C(S(=O)(=O)CCC2)=C2NC2=C1C(=O)CNC2 FEAGUALNKLIJCJ-UHFFFAOYSA-N 0.000 claims 1
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