JPH0433785B2 - - Google Patents
Info
- Publication number
- JPH0433785B2 JPH0433785B2 JP24646489A JP24646489A JPH0433785B2 JP H0433785 B2 JPH0433785 B2 JP H0433785B2 JP 24646489 A JP24646489 A JP 24646489A JP 24646489 A JP24646489 A JP 24646489A JP H0433785 B2 JPH0433785 B2 JP H0433785B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound according
- group
- amino
- tetrazolyl
- 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 122
- 125000004432 carbon atom Chemical group C* 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- -1 methylene, ethylene, trimethylene, tetramethylene, vinylene, propenylene, butenylene Chemical group 0.000 claims description 42
- 159000000000 sodium salts Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- LMTDPKYREUZYAO-UHFFFAOYSA-N 1,4-dioxepane Chemical group C1COCCOC1 LMTDPKYREUZYAO-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical group C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- JTVTWLHBQOLJGZ-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)quinoline Chemical compound C1=CC2=CC=CC=C2N=C1C=1N=NNN=1 JTVTWLHBQOLJGZ-UHFFFAOYSA-N 0.000 claims 1
- AFXYIBLCYKGHHW-UHFFFAOYSA-N 3-(4-pentylphenyl)-n-[2-(2h-tetrazol-5-yl)-1,3-benzodioxol-4-yl]prop-2-enamide Chemical compound C1=CC(CCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)O2 AFXYIBLCYKGHHW-UHFFFAOYSA-N 0.000 claims 1
- QANDNBARFAVZPJ-UHFFFAOYSA-N 3-(4-pentylphenyl)-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]prop-2-enamide Chemical compound C1=CC(CCCCC)=CC=C1C=CC(=O)NC1=CC=CC2=C1OC(C1=NNN=N1)=C2 QANDNBARFAVZPJ-UHFFFAOYSA-N 0.000 claims 1
- XZWYEEDZBHBFAL-UHFFFAOYSA-N 4-(4-phenylbutoxy)-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1O2)=CC=CC=1C=C2C1=NN=NN1 XZWYEEDZBHBFAL-UHFFFAOYSA-N 0.000 claims 1
- XTDWCGRQOXPPNV-UHFFFAOYSA-N 4-(4-phenylbutoxy)-n-[2-(2h-tetrazol-5-yl)quinolin-8-yl]benzamide Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C1=N2)=CC=CC1=CC=C2C1=NN=NN1 XTDWCGRQOXPPNV-UHFFFAOYSA-N 0.000 claims 1
- QOJQXYPNTGJZGD-UHFFFAOYSA-N 4-(4-phenylbutoxy)-n-[7-(2h-tetrazol-5-yl)naphthalen-1-yl]benzamide Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C1=C2)=CC=CC1=CC=C2C=1N=NNN=1 QOJQXYPNTGJZGD-UHFFFAOYSA-N 0.000 claims 1
- LRKGHBLQPYBZRV-UHFFFAOYSA-N 4-(6-chlorohexoxy)-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCCl)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=C2 LRKGHBLQPYBZRV-UHFFFAOYSA-N 0.000 claims 1
- ZOMVCEXHSBTMOL-UHFFFAOYSA-N 4-(6-chlorohexoxy)-n-[2-(2h-tetrazol-5-yl)quinolin-8-yl]benzamide Chemical compound C1=CC(OCCCCCCCl)=CC=C1C(=O)NC1=CC=CC2=CC=C(C=3NN=NN=3)N=C12 ZOMVCEXHSBTMOL-UHFFFAOYSA-N 0.000 claims 1
- PPDPKYFKFDTKAQ-UHFFFAOYSA-N 4-(6-chlorohexoxy)-n-[7-(2h-tetrazol-5-yl)naphthalen-1-yl]benzamide Chemical compound C1=CC(OCCCCCCCl)=CC=C1C(=O)NC1=CC=CC2=CC=C(C3=NNN=N3)C=C12 PPDPKYFKFDTKAQ-UHFFFAOYSA-N 0.000 claims 1
- NSSVDDDMPRVFAJ-UHFFFAOYSA-N 4-heptoxy-n-[2-(2h-tetrazol-5-yl)-1,3-benzodioxol-4-yl]benzamide Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)O2 NSSVDDDMPRVFAJ-UHFFFAOYSA-N 0.000 claims 1
- VFNLCIPDTHLSDN-UHFFFAOYSA-N 4-heptoxy-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=C2 VFNLCIPDTHLSDN-UHFFFAOYSA-N 0.000 claims 1
- GRRXGMNZDIZEDB-UHFFFAOYSA-N 4-heptoxy-n-[2-(2h-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)C2 GRRXGMNZDIZEDB-UHFFFAOYSA-N 0.000 claims 1
- MPEMARICUJLAKA-UHFFFAOYSA-N 4-heptoxy-n-[2-(2h-tetrazol-5-yl)-3,4-dihydro-2h-1,4-benzoxazin-8-yl]benzamide Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)CN2 MPEMARICUJLAKA-UHFFFAOYSA-N 0.000 claims 1
- MSUFRWHNNZNLPG-UHFFFAOYSA-N 4-hexoxy-n-[2-(2h-tetrazol-5-yl)-1,3-benzodioxol-4-yl]benzamide Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)O2 MSUFRWHNNZNLPG-UHFFFAOYSA-N 0.000 claims 1
- DZYBZHDLVYBMBA-UHFFFAOYSA-N 4-hexoxy-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=C2 DZYBZHDLVYBMBA-UHFFFAOYSA-N 0.000 claims 1
- STKAGEXQTCKBAH-UHFFFAOYSA-N 4-hexoxy-n-[2-(2h-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)C2 STKAGEXQTCKBAH-UHFFFAOYSA-N 0.000 claims 1
- YIFARHFOWFXAHP-UHFFFAOYSA-N 4-nonoxy-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=C2 YIFARHFOWFXAHP-UHFFFAOYSA-N 0.000 claims 1
- JEUJRRYNOHNPFS-UHFFFAOYSA-N 4-nonoxy-n-[2-(2h-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)C2 JEUJRRYNOHNPFS-UHFFFAOYSA-N 0.000 claims 1
- PQDBJVRGKMLEFB-UHFFFAOYSA-N 4-octoxy-n-[2-(2h-tetrazol-5-yl)-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)=C2 PQDBJVRGKMLEFB-UHFFFAOYSA-N 0.000 claims 1
- QCWQKQYIZQJIIM-UHFFFAOYSA-N 4-octoxy-n-[2-(2h-tetrazol-5-yl)-2,3-dihydro-1-benzofuran-7-yl]benzamide Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)NC1=CC=CC2=C1OC(C=1NN=NN=1)C2 QCWQKQYIZQJIIM-UHFFFAOYSA-N 0.000 claims 1
- PKGXDYYULRHHTA-UHFFFAOYSA-N 4-oxo-8-[[4-(4-phenylbutoxy)benzoyl]amino]-1h-quinoline-2-carboxylic acid Chemical compound C12=NC(C(=O)O)=CC(O)=C2C=CC=C1NC(=O)C(C=C1)=CC=C1OCCCCC1=CC=CC=C1 PKGXDYYULRHHTA-UHFFFAOYSA-N 0.000 claims 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- FVSFZNLYVLBLPX-UHFFFAOYSA-N n-[4-oxo-2-(2h-tetrazol-5-yl)-1h-quinolin-8-yl]-4-(4-phenylbutoxy)benzamide Chemical compound C1=CC=C2C(O)=CC(C=3NN=NN=3)=NC2=C1NC(=O)C(C=C1)=CC=C1OCCCCC1=CC=CC=C1 FVSFZNLYVLBLPX-UHFFFAOYSA-N 0.000 claims 1
- 125000005447 octyloxy 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])O* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 150000003180 prostaglandins Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 229940114079 arachidonic acid Drugs 0.000 description 13
- 235000021342 arachidonic acid Nutrition 0.000 description 13
- 150000002617 leukotrienes Chemical class 0.000 description 13
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 8
- 230000000144 pharmacologic effect Effects 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 108010064785 Phospholipases Proteins 0.000 description 6
- 102000015439 Phospholipases Human genes 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 208000026935 allergic disease Diseases 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 208000010668 atopic eczema Diseases 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- NNDIXBJHNLFJJP-UHFFFAOYSA-N 20-Hydroxyeicosatetraenoic acid Chemical compound OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O NNDIXBJHNLFJJP-UHFFFAOYSA-N 0.000 description 4
- 102000016912 Aldehyde Reductase Human genes 0.000 description 4
- 108010053754 Aldehyde reductase Proteins 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 102000003820 Lipoxygenases Human genes 0.000 description 4
- 108090000128 Lipoxygenases Proteins 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 125000005133 alkynyloxy group Chemical group 0.000 description 4
- 230000007815 allergy Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 3
- 208000002874 Acne Vulgaris Diseases 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000014181 Bronchial disease Diseases 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 208000019693 Lung disease Diseases 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 206010000496 acne Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000005108 alkenylthio group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 125000005109 alkynylthio group Chemical group 0.000 description 3
- 231100000360 alopecia Toxicity 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000037353 metabolic pathway Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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- Quinoline Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24646489A JPH02138242A (ja) | 1989-09-25 | 1989-09-25 | 新規な縮合アリール（チオ）カルバモイル化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24646489A JPH02138242A (ja) | 1989-09-25 | 1989-09-25 | 新規な縮合アリール（チオ）カルバモイル化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59246363A Division JPS61126061A (ja) | 1984-08-20 | 1984-11-22 | アリールカルバモイル化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02138242A JPH02138242A (ja) | 1990-05-28 |
| JPH0433785B2 true JPH0433785B2 (fr) | 1992-06-04 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24646489A Granted JPH02138242A (ja) | 1989-09-25 | 1989-09-25 | 新規な縮合アリール（チオ）カルバモイル化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02138242A (fr) |
-
1989
- 1989-09-25 JP JP24646489A patent/JPH02138242A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02138242A (ja) | 1990-05-28 |
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