JPH0430955B2 - - Google Patents
Info
- Publication number
- JPH0430955B2 JPH0430955B2 JP17257084A JP17257084A JPH0430955B2 JP H0430955 B2 JPH0430955 B2 JP H0430955B2 JP 17257084 A JP17257084 A JP 17257084A JP 17257084 A JP17257084 A JP 17257084A JP H0430955 B2 JPH0430955 B2 JP H0430955B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- compound according
- tetrazolyl
- benzodioxane
- group
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 365
- 125000004432 carbon atom Chemical group C* 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 71
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 71
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 44
- -1 2-tetrazolylmethyl group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 29
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 150000002617 leukotrienes Chemical class 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000004494 ethyl ester group Chemical group 0.000 claims description 9
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- VAOABFFKRMVKOB-UHFFFAOYSA-N 6-[4-[[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]carbamoyl]phenoxy]hexyl acetate Chemical compound C1=CC(OCCCCCCOC(=O)C)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 VAOABFFKRMVKOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005569 butenylene group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- LITCMHPQYJGSFC-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-2h-1,4-benzodioxin-3-amine Chemical compound C1OC2=CC=CC=C2OC1(N)C1=NN=NN1 LITCMHPQYJGSFC-UHFFFAOYSA-N 0.000 claims 20
- JCIDEANDDNSHQC-UHFFFAOYSA-N 4H-chromene Chemical compound C1=CC=C2CC=COC2=C1 JCIDEANDDNSHQC-UHFFFAOYSA-N 0.000 claims 8
- GGRBXOWLFXBECG-UHFFFAOYSA-N 5-(2,3-dihydro-1,4-benzodioxin-3-yl)-2h-tetrazole Chemical compound C1OC2=CC=CC=C2OC1C=1N=NNN=1 GGRBXOWLFXBECG-UHFFFAOYSA-N 0.000 claims 7
- 150000004702 methyl esters Chemical class 0.000 claims 4
- HTXQVFXXVXOLCF-UHFFFAOYSA-N 6-methylchromen-4-one Chemical compound O1C=CC(=O)C2=CC(C)=CC=C21 HTXQVFXXVXOLCF-UHFFFAOYSA-N 0.000 claims 3
- PXPNSQMWVPLERM-UHFFFAOYSA-N 2-methylchromen-4-one Chemical compound C1=CC=C2OC(C)=CC(=O)C2=C1 PXPNSQMWVPLERM-UHFFFAOYSA-N 0.000 claims 2
- HGBUQTOGNIRVHU-UHFFFAOYSA-N 3-(4-pentylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 HGBUQTOGNIRVHU-UHFFFAOYSA-N 0.000 claims 2
- ROHMBASLHILJFK-UHFFFAOYSA-N 2-pentoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound CCCCCOC1=CC=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 ROHMBASLHILJFK-UHFFFAOYSA-N 0.000 claims 1
- DWULGIQYOMUEAN-UHFFFAOYSA-N 3-(2-pentylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound CCCCCC1=CC=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 DWULGIQYOMUEAN-UHFFFAOYSA-N 0.000 claims 1
- YBABDDMQWBJFPH-UHFFFAOYSA-N 3-(3-methoxy-4-pentoxyphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=C(OC)C(OCCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 YBABDDMQWBJFPH-UHFFFAOYSA-N 0.000 claims 1
- TWHHLJSHRKLRCH-UHFFFAOYSA-N 3-(3-octylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound CCCCCCCCC1=CC=CC(C=CC(=O)NC=2C=3OC(COC=3C=CC=2)C2=NNN=N2)=C1 TWHHLJSHRKLRCH-UHFFFAOYSA-N 0.000 claims 1
- MGYZMMFPQHHKTJ-UHFFFAOYSA-N 3-(4-butoxyphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(OCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 MGYZMMFPQHHKTJ-UHFFFAOYSA-N 0.000 claims 1
- QSEWBONWOPSITJ-UHFFFAOYSA-N 3-(4-butylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 QSEWBONWOPSITJ-UHFFFAOYSA-N 0.000 claims 1
- GCYSHIKPUSQCCV-UHFFFAOYSA-N 3-(4-decylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCCCCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 GCYSHIKPUSQCCV-UHFFFAOYSA-N 0.000 claims 1
- FMGLFXCMBZGPDL-UHFFFAOYSA-N 3-(4-ethylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 FMGLFXCMBZGPDL-UHFFFAOYSA-N 0.000 claims 1
- PWEJTHONIDHCLI-UHFFFAOYSA-N 3-(4-hexylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 PWEJTHONIDHCLI-UHFFFAOYSA-N 0.000 claims 1
- FOXMBBUVVFEBAX-UHFFFAOYSA-N 3-(4-nonylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCCCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 FOXMBBUVVFEBAX-UHFFFAOYSA-N 0.000 claims 1
- WZLAUXKXTLNMDW-UHFFFAOYSA-N 3-(4-octylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 WZLAUXKXTLNMDW-UHFFFAOYSA-N 0.000 claims 1
- UGASCOSKCDZWOP-UHFFFAOYSA-N 3-(4-pentylphenyl)-n-[2-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodithiin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1SCC(C1=NNN=N1)S2 UGASCOSKCDZWOP-UHFFFAOYSA-N 0.000 claims 1
- BPOYJKOITPOGHN-UHFFFAOYSA-N 3-(4-pentylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodithiin-5-yl]prop-2-enamide Chemical compound C1=CC(CCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1SC(C1=NNN=N1)CS2 BPOYJKOITPOGHN-UHFFFAOYSA-N 0.000 claims 1
- GHYJLDJJOTYUQB-UHFFFAOYSA-N 3-(4-propoxyphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(OCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 GHYJLDJJOTYUQB-UHFFFAOYSA-N 0.000 claims 1
- KAIRIRDEGZVHEP-UHFFFAOYSA-N 3-(4-propylphenyl)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 KAIRIRDEGZVHEP-UHFFFAOYSA-N 0.000 claims 1
- AZCNARPKKPXNPR-UHFFFAOYSA-N 3-[2-methyl-4-(4-methylpentoxy)phenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound CC1=CC(OCCCC(C)C)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 AZCNARPKKPXNPR-UHFFFAOYSA-N 0.000 claims 1
- DGGSULIRXWPFKZ-UHFFFAOYSA-N 3-[4-(2-cyclohexylethoxy)phenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C=1C=C(OCCC2CCCCC2)C=CC=1C=CC(=O)NC(C=1O2)=CC=CC=1OCC2C=1N=NNN=1 DGGSULIRXWPFKZ-UHFFFAOYSA-N 0.000 claims 1
- FYYXJYAQHSQJBS-UHFFFAOYSA-N 3-[4-(2-methylpropyl)phenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C1=CC(CC(C)C)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 FYYXJYAQHSQJBS-UHFFFAOYSA-N 0.000 claims 1
- OMJKILYNTWEMKY-UHFFFAOYSA-N 3-[4-(4-cyclohexylbutoxy)phenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C=1C=C(OCCCCC2CCCCC2)C=CC=1C=CC(=O)NC(C=1O2)=CC=CC=1OCC2C=1N=NNN=1 OMJKILYNTWEMKY-UHFFFAOYSA-N 0.000 claims 1
- IQDPAKOIAQDBLX-UHFFFAOYSA-N 3-[4-(4-methylpentoxy)-2-phenylphenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C=1C=CC=CC=1C1=CC(OCCCC(C)C)=CC=C1C=CC(=O)NC(C=1O2)=CC=CC=1OCC2C=1N=NNN=1 IQDPAKOIAQDBLX-UHFFFAOYSA-N 0.000 claims 1
- KHNCBHCSSMKOGE-UHFFFAOYSA-N 3-[4-(4-methylpentoxy)phenyl]-n-[4-oxo-2-(2h-tetrazol-5-yl)chromen-8-yl]prop-2-enamide Chemical compound C1=CC(OCCCC(C)C)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)=CC2=O KHNCBHCSSMKOGE-UHFFFAOYSA-N 0.000 claims 1
- LCRGOVPUUUWMOL-UHFFFAOYSA-N 3-[4-(5-phenylpentoxy)phenyl]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]prop-2-enamide Chemical compound C=1C=C(OCCCCCC=2C=CC=CC=2)C=CC=1C=CC(=O)NC(C=1O2)=CC=CC=1OCC2C=1N=NNN=1 LCRGOVPUUUWMOL-UHFFFAOYSA-N 0.000 claims 1
- MVUYWVDQCAWJIM-UHFFFAOYSA-N 3-amino-6-fluoro-2-(2H-tetrazol-5-yl)chromen-4-one Chemical compound NC1=C(OC2=C(C1=O)C=C(C=C2)F)C1=NN=NN1 MVUYWVDQCAWJIM-UHFFFAOYSA-N 0.000 claims 1
- JSBVWPNRYNKYFI-NTUHNPAUSA-N 3-chloro-4-[(e)-oct-1-enoxy]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=C(Cl)C(O/C=C/CCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 JSBVWPNRYNKYFI-NTUHNPAUSA-N 0.000 claims 1
- NKRNGXYZEZTQOE-UHFFFAOYSA-N 3-pentoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound CCCCCOC1=CC=CC(C(=O)NC=2C=3OC(COC=3C=CC=2)C=2NN=NN=2)=C1 NKRNGXYZEZTQOE-UHFFFAOYSA-N 0.000 claims 1
- ICEMINZYWCXWCT-UHFFFAOYSA-N 3-pentyl-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzenecarbothioamide Chemical compound CCCCCC1=CC=CC(C(=S)NC=2C=3OC(COC=3C=CC=2)C=2NN=NN=2)=C1 ICEMINZYWCXWCT-UHFFFAOYSA-N 0.000 claims 1
- SXEZKGXFQBSILK-UHFFFAOYSA-N 4-(3,7-dimethyloctoxy)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCC(C)CCCC(C)C)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 SXEZKGXFQBSILK-UHFFFAOYSA-N 0.000 claims 1
- SIKGFXVWCAHOND-UHFFFAOYSA-N 4-(3-phenylprop-2-enoxy)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C=1C=C(OCC=CC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1O2)=CC=CC=1OCC2C=1N=NNN=1 SIKGFXVWCAHOND-UHFFFAOYSA-N 0.000 claims 1
- XEOHUSDYIHFREO-UHFFFAOYSA-N 4-(3-phenylsulfanylpropoxy)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C=1C=C(OCCCSC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1O2)=CC=CC=1OCC2C1=NN=NN1 XEOHUSDYIHFREO-UHFFFAOYSA-N 0.000 claims 1
- ONSIRBRNAGFNKF-UHFFFAOYSA-N 4-(4-chlorobutoxy)-n-[4-oxo-2-(2h-tetrazol-5-yl)chromen-8-yl]benzamide Chemical compound C1=CC(OCCCCCl)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=CC2=O ONSIRBRNAGFNKF-UHFFFAOYSA-N 0.000 claims 1
- YNKGMCPQHSVJBM-UHFFFAOYSA-N 4-(6-hydroxyhexoxy)-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCCO)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 YNKGMCPQHSVJBM-UHFFFAOYSA-N 0.000 claims 1
- DFVKZBJIWBRFMN-CSNJMMPQSA-N 4-[(1e,3e)-octa-1,3-dienoxy]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(O/C=C/C=C/CCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 DFVKZBJIWBRFMN-CSNJMMPQSA-N 0.000 claims 1
- QLGKJENFCAUWEO-NBVRZTHBSA-N 4-[(2e)-3,7-dimethylocta-2,6-dienoxy]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OC/C=C(C)/CCC=C(C)C)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 QLGKJENFCAUWEO-NBVRZTHBSA-N 0.000 claims 1
- QZGPHIPRWAQPCF-UHFFFAOYSA-N 4-[5-(dimethylamino)pentoxy]-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCN(C)C)=CC=C1C(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)CO2 QZGPHIPRWAQPCF-UHFFFAOYSA-N 0.000 claims 1
- OKPACELMVBBRER-UHFFFAOYSA-N 4-butoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 OKPACELMVBBRER-UHFFFAOYSA-N 0.000 claims 1
- PULYGNHSSUPCKL-UHFFFAOYSA-N 4-decoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 PULYGNHSSUPCKL-UHFFFAOYSA-N 0.000 claims 1
- AIANCPCQGZTGKM-UHFFFAOYSA-N 4-heptoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 AIANCPCQGZTGKM-UHFFFAOYSA-N 0.000 claims 1
- KEAPEQBCDVILQF-UHFFFAOYSA-N 4-hexoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 KEAPEQBCDVILQF-UHFFFAOYSA-N 0.000 claims 1
- YBNVSQIAVPPCOR-UHFFFAOYSA-N 4-nonoxy-n-[3-(2h-tetrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-5-yl]benzamide Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CO2 YBNVSQIAVPPCOR-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59172570A JPS6150977A (ja) | 1984-08-20 | 1984-08-20 | 新規な縮合ベンズ（チオ）アミド、それらの製造方法およびそれらを有効成分として含有する薬剤 |
| ZA856009A ZA856009B (en) | 1984-08-20 | 1985-08-08 | (fused)benz(thio)amides |
| CA000488741A CA1261835A (en) | 1984-08-20 | 1985-08-14 | (fused) benz(thio)amides |
| EP85305802A EP0173516B1 (en) | 1984-08-20 | 1985-08-15 | (Fused)benz(thio)amides |
| DE3588025T DE3588025T2 (de) | 1984-08-20 | 1985-08-15 | Aminophenylderivate. |
| EP91114142A EP0463638B1 (en) | 1984-08-20 | 1985-08-15 | Aminophenyl derivatives |
| AT85305802T ATE97897T1 (de) | 1984-08-20 | 1985-08-15 | (kondensierte) benz(thio)amide. |
| DE85305802T DE3587671T2 (de) | 1984-08-20 | 1985-08-15 | (Kondensierte) Benz(thio)amide. |
| AT91114142T ATE123019T1 (de) | 1984-08-20 | 1985-08-15 | Aminophenylderivate. |
| HU853184A HU208133B (en) | 1984-08-20 | 1985-08-17 | Process for producing condensed benzamide and benzthiamide derivatives and pharmaceutical compositions comprising same |
| IE203585A IE64552B1 (en) | 1984-08-20 | 1985-08-19 | (Fused)benz(thio)amides |
| PT80986A PT80986B (pt) | 1984-08-20 | 1985-08-19 | Processo para a preparacao de benzo(tio)amidas (condensadas) e de composicoes farmaceuticas que as contem |
| YU1321/85A YU45002B (en) | 1984-08-20 | 1985-08-19 | Process for preparing (condensed) benz(thio)amides |
| IE940268A IE74959B1 (en) | 1984-08-20 | 1985-08-19 | Aminophenyl derivatives |
| KR1019850005970A KR920006237B1 (ko) | 1984-08-20 | 1985-08-19 | 융합된 벤즈(티오)아미드의 제조방법 |
| ES546269A ES8609217A1 (es) | 1984-08-20 | 1985-08-19 | Benzo(tio)amidas (fusionadas) nuevas |
| DK198503753A DK174022B1 (da) | 1984-08-20 | 1985-08-19 | Kondenserede benz(thio)amider, fremgangsmåde til deres fremstilling samt deres anvendelse til fremstilling af lægemidler |
| FI853178A FI87782C (fi) | 1984-08-20 | 1985-08-19 | Foerfarande foer framstaellning av terapeutiskt anvaendbara kondenserade bens(tio)amider |
| NO853261A NO159447C (no) | 1984-08-20 | 1985-08-19 | Analogifremgangsmaate for fremstilling av terapeutisk aktive (kondenserte)benz(tio)-amider. |
| SI8511321A SI8511321A8 (sl) | 1984-08-20 | 1985-08-19 | Postopek za pripravo (kondenziranih) benz(tio)amidov |
| US06/767,538 US4780469A (en) | 1984-08-20 | 1985-08-20 | (Fused) benz(thio)amides and pharmaceutical use |
| GR852014A GR852014B (nl) | 1984-08-20 | 1985-08-20 | |
| AU46462/85A AU579398B2 (en) | 1984-08-20 | 1985-08-20 | (Fused) Benz (Thio) Amides |
| ES552747A ES8704455A1 (es) | 1984-08-20 | 1986-03-06 | Un procedimiento para la preparacion de nuevas benzo(tio)amidas (fusionadas) |
| ES552745A ES8800211A1 (es) | 1984-08-20 | 1986-03-06 | Un procedimiento para la preparacion de nuevas benzo(tio)amidas (fusionadas) |
| ES552746A ES8704476A1 (es) | 1984-08-20 | 1986-03-06 | Un procedimiento para la preparacion de nuevas benzo(tio)amidas (fusionadas) |
| YU1447/87A YU44955B (en) | 1984-08-20 | 1987-07-31 | Process for preparing (condensed) benzamides |
| YU01446/87A YU144687A (en) | 1984-08-20 | 1987-07-31 | Process for preparing benz(thio)amides |
| SI8711447A SI8711447A8 (sl) | 1984-08-20 | 1987-07-31 | Postopek za pripravo (kondenziranih) benzamidov |
| YU01448/87A YU144887A (en) | 1984-08-20 | 1987-08-31 | Process for preparing benz(thio)amides |
| US07/207,994 US4847275A (en) | 1984-08-20 | 1988-06-17 | (Fused) benz (thio) amides |
| US07/332,930 US4939141A (en) | 1984-08-20 | 1989-04-04 | (Fused) benz (thio) amides and pharmaceutical compositions, thereof |
| US07/800,253 US5446058A (en) | 1984-08-20 | 1991-11-29 | (Fused) benz(thio)amides |
| US08/327,825 US5459134A (en) | 1984-08-20 | 1994-10-21 | (Fused) benz (thio) amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59172570A JPS6150977A (ja) | 1984-08-20 | 1984-08-20 | 新規な縮合ベンズ（チオ）アミド、それらの製造方法およびそれらを有効成分として含有する薬剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6150977A JPS6150977A (ja) | 1986-03-13 |
| JPH0430955B2 true JPH0430955B2 (nl) | 1992-05-25 |
Family
ID=15944283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59172570A Granted JPS6150977A (ja) | 1984-08-20 | 1984-08-20 | 新規な縮合ベンズ（チオ）アミド、それらの製造方法およびそれらを有効成分として含有する薬剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6150977A (nl) |
| ZA (1) | ZA856009B (nl) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0623608B1 (en) * | 1992-01-24 | 2001-05-30 | Teijin Limited | Benzopyran derivative, production thereof, and pharmaceutical preparation containing the same as active ingredient |
| JP2668483B2 (ja) * | 1992-05-29 | 1997-10-27 | キャシー・カザンジアン | ゴルフボール回収装置 |
| AU9002798A (en) * | 1997-09-19 | 1999-04-12 | Ono Pharmaceutical Co. Ltd. | Fused or nonfused benzene compounds |
| JP4752121B2 (ja) * | 2001-03-12 | 2011-08-17 | 住友化学株式会社 | ニトリル誘導体の製造方法、その中間体および中間体の製造方法 |
| CN100509751C (zh) | 2002-02-28 | 2009-07-08 | 住友化学株式会社 | 苯并吡喃酮化合物的制备方法 |
| KR20060123329A (ko) * | 2003-12-16 | 2006-12-01 | 오노 야꾸힝 고교 가부시키가이샤 | 월경 곤란증의 예방 및/또는 치료제 |
| JPWO2005058879A1 (ja) * | 2003-12-17 | 2007-07-12 | 学校法人関西医科大学 | 滲出性中耳炎の予防および／または治療剤 |
| JP4544856B2 (ja) * | 2003-12-25 | 2010-09-15 | 日医工株式会社 | プランルカスト水和物含有製剤 |
| JPWO2006003910A1 (ja) * | 2004-06-30 | 2008-04-17 | 小野薬品工業株式会社 | メニエール病の予防および／または治療剤 |
| KR100739439B1 (ko) | 2006-03-02 | 2007-07-13 | 주식회사 에스텍파마 | 8-아미노-4-옥소-2-(테트라졸-5-일)-4에이치-1-벤조피란 또는 그의 염의 제조방법 및 그의 제조용 중간체 |
| WO2010002075A1 (en) * | 2008-07-02 | 2010-01-07 | Pharmacostech Co., Ltd. | Methods for preparing amide derivatives |
-
1984
- 1984-08-20 JP JP59172570A patent/JPS6150977A/ja active Granted
-
1985
- 1985-08-08 ZA ZA856009A patent/ZA856009B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA856009B (en) | 1986-04-30 |
| JPS6150977A (ja) | 1986-03-13 |
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