JPH0156069B2 - - Google Patents
Info
- Publication number
- JPH0156069B2 JPH0156069B2 JP14005180A JP14005180A JPH0156069B2 JP H0156069 B2 JPH0156069 B2 JP H0156069B2 JP 14005180 A JP14005180 A JP 14005180A JP 14005180 A JP14005180 A JP 14005180A JP H0156069 B2 JPH0156069 B2 JP H0156069B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrazole
- thio
- methyl
- propyl
- melting point
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003536 tetrazoles Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 160
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 158
- 238000002844 melting Methods 0.000 description 156
- 230000008018 melting Effects 0.000 description 156
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 137
- 150000001875 compounds Chemical class 0.000 description 121
- 238000006243 chemical reaction Methods 0.000 description 113
- -1 β-phenethyl Chemical group 0.000 description 96
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 88
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 58
- 235000019441 ethanol Nutrition 0.000 description 55
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- 238000003756 stirring Methods 0.000 description 50
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 239000007788 liquid Substances 0.000 description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
- 235000019341 magnesium sulphate Nutrition 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 150000002576 ketones Chemical class 0.000 description 17
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- OTJJUPGWWNIPGH-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)CCCSC1=NN=NN1C OTJJUPGWWNIPGH-UHFFFAOYSA-N 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- YUHMQKUKKNCTCR-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-naphthalen-2-ylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=C(C=CC=C2)C2=C1 YUHMQKUKKNCTCR-UHFFFAOYSA-N 0.000 description 12
- OMWWJHVYRYUDQO-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-thiophen-2-ylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=CS1 OMWWJHVYRYUDQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- RTKZYJQPALPQIV-UHFFFAOYSA-N 1-(2,5-dimethylfuran-3-yl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound O1C(C)=CC(C(=O)CCCSC=2N(N=NN=2)C)=C1C RTKZYJQPALPQIV-UHFFFAOYSA-N 0.000 description 11
- TVNGQTONLIDKQA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)CCCSC1=NN=NN1C TVNGQTONLIDKQA-UHFFFAOYSA-N 0.000 description 11
- XQNCKBPYZHGBQB-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-(1h-pyrrol-2-yl)butan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=CN1 XQNCKBPYZHGBQB-UHFFFAOYSA-N 0.000 description 11
- NCCDWULUGXRBRN-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-(5-methylthiophen-2-yl)butan-1-one Chemical compound S1C(C)=CC=C1C(=O)CCCSC1=NN=NN1C NCCDWULUGXRBRN-UHFFFAOYSA-N 0.000 description 11
- RKYXTELYNYVQNB-UHFFFAOYSA-N 5-(1-methyltetrazol-5-yl)sulfanyl-1-phenylpentan-2-one Chemical compound CN1N=NN=C1SCCCC(=O)CC1=CC=CC=C1 RKYXTELYNYVQNB-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- NNLAFJVYHCDCAT-UHFFFAOYSA-N 1-(furan-2-yl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=CO1 NNLAFJVYHCDCAT-UHFFFAOYSA-N 0.000 description 10
- DCPHPQXKGRBJDZ-UHFFFAOYSA-N 6-(1-methyltetrazol-5-yl)sulfanyl-1-phenylhexan-3-one Chemical compound CN1N=NN=C1SCCCC(=O)CCC1=CC=CC=C1 DCPHPQXKGRBJDZ-UHFFFAOYSA-N 0.000 description 10
- 150000004795 grignard reagents Chemical class 0.000 description 10
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- CUFPKUDWGVXRMI-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=C(Cl)C=C1 CUFPKUDWGVXRMI-UHFFFAOYSA-N 0.000 description 7
- ILAFEFPRSFLMDW-UHFFFAOYSA-N 1-(5-chlorothiophen-2-yl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=C(Cl)S1 ILAFEFPRSFLMDW-UHFFFAOYSA-N 0.000 description 7
- 239000007818 Grignard reagent Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000003699 antiulcer agent Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- IFPPNCFWTWTZFA-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=C(O)C=C1 IFPPNCFWTWTZFA-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- ZJDLUYHJKKYKQL-UHFFFAOYSA-N 1-(4-ethylphenyl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound C1=CC(CC)=CC=C1C(=O)CCCSC1=NN=NN1C ZJDLUYHJKKYKQL-UHFFFAOYSA-N 0.000 description 5
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- OUWNKPUPTFFRNS-UHFFFAOYSA-N n-[4-[4-(1-methyltetrazol-5-yl)sulfanylbutanoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)CCCSC1=NN=NN1C OUWNKPUPTFFRNS-UHFFFAOYSA-N 0.000 description 5
- IQCMXYFCVORCEJ-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-pyridin-2-ylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)C1=CC=CC=N1 IQCMXYFCVORCEJ-UHFFFAOYSA-N 0.000 description 4
- PABFAYDRJSWBIU-UHFFFAOYSA-N 4-chloro-1-pyridin-2-ylbutan-1-one Chemical compound ClCCCC(=O)C1=CC=CC=N1 PABFAYDRJSWBIU-UHFFFAOYSA-N 0.000 description 4
- DZHZPUBHGIUESP-UHFFFAOYSA-N 5-chloro-1-methyltetrazole Chemical compound CN1N=NN=C1Cl DZHZPUBHGIUESP-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 229940099112 cornstarch Drugs 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14005180A JPS5764682A (en) | 1980-10-06 | 1980-10-06 | Tetrazole derivative |
| FI810571A FI73423C (fi) | 1980-02-29 | 1981-02-24 | Foerfarande foer framstaellning av farmakologiskt verksamma tetrazolderivat. |
| EP81101352A EP0035228B1 (en) | 1980-02-29 | 1981-02-25 | Tetrazole derivatives, process for the preparation thereof, and anti-ulcer composition containing the same |
| AU67638/81A AU537266B2 (en) | 1980-02-29 | 1981-02-25 | Tetrazole derivatives |
| DE8181101352T DE3167997D1 (en) | 1980-02-29 | 1981-02-25 | Tetrazole derivatives, process for the preparation thereof, and anti-ulcer composition containing the same |
| PT72569A PT72569B (en) | 1980-02-29 | 1981-02-25 | Tetrazole derivatives process for the preparation thereof and anti-ulcer composition |
| DK088081A DK162524C (da) | 1980-02-29 | 1981-02-26 | Analogifremgangsmaade til fremstilling af 5-alkylthio-tetrazolderivater |
| CA000372021A CA1162196A (en) | 1980-02-29 | 1981-02-27 | Tetrazole derivatives having prophylactic and therapeutic activities against peptic and duodenal ulcers |
| US06/239,044 US4372953A (en) | 1980-02-29 | 1981-02-27 | Tetrazole derivatives, and anti-ulcer composition containing the same |
| NO810675A NO166320C (no) | 1980-02-29 | 1981-02-27 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive tetrazolderivater. |
| PH25282A PH17406A (en) | 1980-02-29 | 1981-02-27 | Tetrazole derivatives and anti-ulcer composition containing the same |
| SU813252652A SU1212324A3 (ru) | 1980-03-01 | 1981-02-27 | Способ получени производных тетразола или их фармакологически приемлемых кислотно-аддитивных солей |
| MX815964A MX157430A (es) | 1980-02-29 | 1981-02-27 | Procedimiento para la preparacion de derivados de tetrazol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14005180A JPS5764682A (en) | 1980-10-06 | 1980-10-06 | Tetrazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5764682A JPS5764682A (en) | 1982-04-19 |
| JPH0156069B2 true JPH0156069B2 (ko) | 1989-11-28 |
Family
ID=15259836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14005180A Granted JPS5764682A (en) | 1980-02-29 | 1980-10-06 | Tetrazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5764682A (ko) |
-
1980
- 1980-10-06 JP JP14005180A patent/JPS5764682A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5764682A (en) | 1982-04-19 |
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