DE2105191A1 - 2 Tetrazolylchromondenvate, Ver fahren zu ihrer Herstellung und Arznei praparate - Google Patents
2 Tetrazolylchromondenvate, Ver fahren zu ihrer Herstellung und Arznei praparateInfo
- Publication number
- DE2105191A1 DE2105191A1 DE19712105191 DE2105191A DE2105191A1 DE 2105191 A1 DE2105191 A1 DE 2105191A1 DE 19712105191 DE19712105191 DE 19712105191 DE 2105191 A DE2105191 A DE 2105191A DE 2105191 A1 DE2105191 A1 DE 2105191A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrazol
- ethanol
- yield
- radicals
- dimethylformamide
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 229940126601 medicinal product Drugs 0.000 title description 2
- -1 hydroxy, carboxyl Chemical class 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- ZZLXVXGOFGHKHP-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C=C1C=1N=NNN=1 ZZLXVXGOFGHKHP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- BEOKBEMARSHQIW-UHFFFAOYSA-N 6-methyl-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C2=CC(C)=CC=C2OC=1C=1N=NNN=1 BEOKBEMARSHQIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- FHPXSLWCBTUXQN-UHFFFAOYSA-N 6-bromo-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C2=CC(Br)=CC=C2OC=1C=1N=NNN=1 FHPXSLWCBTUXQN-UHFFFAOYSA-N 0.000 claims description 2
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 2
- 229950009263 methylchromone Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- OXVXNMWLJXQXFC-UHFFFAOYSA-N 6-chloro-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C2=CC(Cl)=CC=C2OC=1C=1N=NNN=1 OXVXNMWLJXQXFC-UHFFFAOYSA-N 0.000 claims 1
- RTOLKYBAJMRTMR-UHFFFAOYSA-N 7-phenylmethoxy-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C=C2C(=O)C=C(C3=NNN=N3)OC2=CC=1OCC1=CC=CC=C1 RTOLKYBAJMRTMR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 33
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 32
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 235000019270 ammonium chloride Nutrition 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 4
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LYKDOWJROLHYOT-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1O LYKDOWJROLHYOT-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- PGSHBYARXCSZMV-UHFFFAOYSA-N 2,6-bis(2H-tetrazol-5-yl)chromen-4-one Chemical compound O=C1C=C(OC2=CC=C(C=C12)C1=NN=NN1)C1=NN=NN1 PGSHBYARXCSZMV-UHFFFAOYSA-N 0.000 description 2
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 2
- LPKGQHBYVFYNTI-UHFFFAOYSA-N 3-chloro-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(Cl)=C1C=1N=NNN=1 LPKGQHBYVFYNTI-UHFFFAOYSA-N 0.000 description 2
- AKVXTSKRPXOFBK-UHFFFAOYSA-N 3-chloro-4-oxochromene-2-carbonitrile Chemical compound C1=CC=C2C(=O)C(Cl)=C(C#N)OC2=C1 AKVXTSKRPXOFBK-UHFFFAOYSA-N 0.000 description 2
- KXWDRZJUSGYAEZ-UHFFFAOYSA-N 4-oxo-7-phenylmethoxychromene-2-carbonitrile Chemical compound C=1C=C2C(=O)C=C(C#N)OC2=CC=1OCC1=CC=CC=C1 KXWDRZJUSGYAEZ-UHFFFAOYSA-N 0.000 description 2
- MQAQREONYKDKJC-UHFFFAOYSA-N 4-oxo-7-phenylmethoxychromene-2-carboxamide Chemical compound C1=C2OC(C(=O)N)=CC(=O)C2=CC=C1OCC1=CC=CC=C1 MQAQREONYKDKJC-UHFFFAOYSA-N 0.000 description 2
- HMQHYYZVLDWEPT-UHFFFAOYSA-N 4-oxochromene-2,6-dicarbonitrile Chemical compound C(#N)C=1OC2=CC=C(C=C2C(C1)=O)C#N HMQHYYZVLDWEPT-UHFFFAOYSA-N 0.000 description 2
- BMVQNVITYXDTLC-UHFFFAOYSA-N 5-methoxy-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=C1C=CC=C2OC BMVQNVITYXDTLC-UHFFFAOYSA-N 0.000 description 2
- DYWHBTJZSVUMDI-UHFFFAOYSA-N 6-methyl-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=CC(C)=CC=C21 DYWHBTJZSVUMDI-UHFFFAOYSA-N 0.000 description 2
- IEZXNXOBTJVBJV-UHFFFAOYSA-N 6-nitro-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C2=CC([N+](=O)[O-])=CC=C2OC=1C=1N=NNN=1 IEZXNXOBTJVBJV-UHFFFAOYSA-N 0.000 description 2
- YAQLDRTTWWSTKJ-UHFFFAOYSA-N 6-nitro-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=CC([N+](=O)[O-])=CC=C21 YAQLDRTTWWSTKJ-UHFFFAOYSA-N 0.000 description 2
- ORWADBVBOPTYQT-UHFFFAOYSA-N 6-nitrochromen-4-one Chemical compound O1C=CC(=O)C2=CC([N+](=O)[O-])=CC=C21 ORWADBVBOPTYQT-UHFFFAOYSA-N 0.000 description 2
- MOOMZGUMQRVUTP-UHFFFAOYSA-N 8-methyl-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=C1C(C)=CC=C2 MOOMZGUMQRVUTP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QFRFXLVXDJOQBB-UHFFFAOYSA-N C(C)OC(=O)COC1=CC=C2C(C=C(OC2=C1)C(=O)OCC)=O Chemical compound C(C)OC(=O)COC1=CC=C2C(C=C(OC2=C1)C(=O)OCC)=O QFRFXLVXDJOQBB-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KDUWXMIHHIVXER-UHFFFAOYSA-N 2'-hydroxypropiophenone Chemical compound CCC(=O)C1=CC=CC=C1O KDUWXMIHHIVXER-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- ZUHXADCMYFAQEY-UHFFFAOYSA-N 2-hydroxy-1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(=O)CO ZUHXADCMYFAQEY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ZKNBEVSECMLVAN-UHFFFAOYSA-N 3-methyl-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C)=C1C=1N=NNN=1 ZKNBEVSECMLVAN-UHFFFAOYSA-N 0.000 description 1
- VEQYFJSASLNUPK-UHFFFAOYSA-N 3-methyl-4-oxochromene-2-carbonitrile Chemical compound C1=CC=C2C(=O)C(C)=C(C#N)OC2=C1 VEQYFJSASLNUPK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XJYIEJXFIORQEU-UHFFFAOYSA-N 4-oxo-2-(2H-tetrazol-5-yl)chromene-6-carboxylic acid Chemical compound N1N=NN=C1C=1OC2=CC=C(C=C2C(C1)=O)C(=O)O XJYIEJXFIORQEU-UHFFFAOYSA-N 0.000 description 1
- CJEWQOCXIZVERD-UHFFFAOYSA-N 4-oxochromene-2-carbonitrile Chemical compound C1=CC=C2C(=O)C=C(C#N)OC2=C1 CJEWQOCXIZVERD-UHFFFAOYSA-N 0.000 description 1
- FBHJCKIOSMTRGB-UHFFFAOYSA-N 5,7-dimethyl-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(C)=CC(C)=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 FBHJCKIOSMTRGB-UHFFFAOYSA-N 0.000 description 1
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- FWVRNMAQCWSFML-UHFFFAOYSA-N 5,7-dimethylchromen-4-one Chemical compound O1C=CC(=O)C=2C1=CC(C)=CC=2C FWVRNMAQCWSFML-UHFFFAOYSA-N 0.000 description 1
- QYVSSPVOVMLAEU-UHFFFAOYSA-N 5-(2-hydroxyethoxy)-2-(2H-tetrazol-5-yl)chromen-4-one hydrate Chemical compound O.N1N=NN=C1C=1OC2=CC=CC(=C2C(C1)=O)OCCO QYVSSPVOVMLAEU-UHFFFAOYSA-N 0.000 description 1
- FUTRGIVXNVZCQY-UHFFFAOYSA-N 5-methoxy-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C=2C(OC)=CC=CC=2OC=1C=1N=NNN=1 FUTRGIVXNVZCQY-UHFFFAOYSA-N 0.000 description 1
- TYBAUWDPHYNKFQ-UHFFFAOYSA-N 5-methoxy-4-oxochromene-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C2=C1C=CC=C2OC TYBAUWDPHYNKFQ-UHFFFAOYSA-N 0.000 description 1
- YXMJERSBVSUMCI-UHFFFAOYSA-N 6,8-dibromo-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(=O)C2=CC(Br)=CC(Br)=C2OC=1C=1N=NNN=1 YXMJERSBVSUMCI-UHFFFAOYSA-N 0.000 description 1
- LSUDRONULLAHLF-UHFFFAOYSA-N 6-bromo-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=CC(Br)=CC=C21 LSUDRONULLAHLF-UHFFFAOYSA-N 0.000 description 1
- KPKDODIBNVVHBG-UHFFFAOYSA-N 6-bromo-4-oxochromene-2-carboxamide Chemical compound BrC1=CC=C2OC(C(=O)N)=CC(=O)C2=C1 KPKDODIBNVVHBG-UHFFFAOYSA-N 0.000 description 1
- VFZQATFTQAZCMO-UHFFFAOYSA-N 6-chlorochromen-4-one Chemical compound O1C=CC(=O)C2=CC(Cl)=CC=C21 VFZQATFTQAZCMO-UHFFFAOYSA-N 0.000 description 1
- UMTVSAMWMQVVMN-UHFFFAOYSA-N 7-methoxy-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(OC)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UMTVSAMWMQVVMN-UHFFFAOYSA-N 0.000 description 1
- GIFSFCBCSKZISN-UHFFFAOYSA-N 7-methoxy-4-oxochromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C=2C1=CC(OC)=CC=2 GIFSFCBCSKZISN-UHFFFAOYSA-N 0.000 description 1
- VDPPPVMTEAHVLI-UHFFFAOYSA-N 7-methoxy-4-oxochromene-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C=2C1=CC(OC)=CC=2 VDPPPVMTEAHVLI-UHFFFAOYSA-N 0.000 description 1
- SKMRAKVMLHQHQT-UHFFFAOYSA-N 7-methyl-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C=1C(C)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 SKMRAKVMLHQHQT-UHFFFAOYSA-N 0.000 description 1
- BPJQHSNHLHNXRM-UHFFFAOYSA-N 7-methyl-4-oxochromene-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C=2C1=CC(C)=CC=2 BPJQHSNHLHNXRM-UHFFFAOYSA-N 0.000 description 1
- JJYZKDKAKOHVRX-UHFFFAOYSA-N 8-methyl-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound CC1=CC=CC(C(C=2)=O)=C1OC=2C=1N=NNN=1 JJYZKDKAKOHVRX-UHFFFAOYSA-N 0.000 description 1
- YAHVDMFRYJHLEN-UHFFFAOYSA-N 8-methyl-4-oxochromene-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C2=C1C(C)=CC=C2 YAHVDMFRYJHLEN-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CKJQMBIBUNFWER-UHFFFAOYSA-N N#CC(OC(C1=C2)=CC=C2C(O)=O)=CC1=O Chemical compound N#CC(OC(C1=C2)=CC=C2C(O)=O)=CC1=O CKJQMBIBUNFWER-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 241001114003 Seira Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RKAHVFLCAKJDDP-UHFFFAOYSA-N ethyl 2-cyano-4-oxochromene-6-carboxylate Chemical compound C(#N)C=1OC2=CC=C(C=C2C(C1)=O)C(=O)OCC RKAHVFLCAKJDDP-UHFFFAOYSA-N 0.000 description 1
- ZGEGDOHAFHDXAU-UHFFFAOYSA-N ethyl 3-acetyl-4-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(C(C)=O)=C1 ZGEGDOHAFHDXAU-UHFFFAOYSA-N 0.000 description 1
- OQATUSWUYAWKPX-UHFFFAOYSA-N ethyl 3-methyl-4-oxochromene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C(=O)OCC)OC2=C1 OQATUSWUYAWKPX-UHFFFAOYSA-N 0.000 description 1
- CJVFJZNWXDFXHF-UHFFFAOYSA-N ethyl 4-oxochromene-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 CJVFJZNWXDFXHF-UHFFFAOYSA-N 0.000 description 1
- IQFLHTXYKJGSBM-UHFFFAOYSA-N ethyl 5-(2-hydroxyethoxy)-4-oxochromene-2-carboxylate Chemical compound OCCOC1=C2C(C=C(OC2=CC=C1)C(=O)OCC)=O IQFLHTXYKJGSBM-UHFFFAOYSA-N 0.000 description 1
- OJRFUZPONYSMKF-UHFFFAOYSA-N ethyl 5-methoxy-4-oxochromene-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1OC OJRFUZPONYSMKF-UHFFFAOYSA-N 0.000 description 1
- VFGSPHMOFHZRGB-UHFFFAOYSA-N ethyl 6,8-dibromo-4-oxochromene-2-carboxylate Chemical compound BrC1=CC(Br)=C2OC(C(=O)OCC)=CC(=O)C2=C1 VFGSPHMOFHZRGB-UHFFFAOYSA-N 0.000 description 1
- BDESGNKGTJQLCI-UHFFFAOYSA-N ethyl 6-bromo-4-oxochromene-2-carboxylate Chemical compound BrC1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 BDESGNKGTJQLCI-UHFFFAOYSA-N 0.000 description 1
- JKMIKRDROJBJMP-UHFFFAOYSA-N ethyl 6-chloro-4-oxochromene-2-carboxylate Chemical compound ClC1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 JKMIKRDROJBJMP-UHFFFAOYSA-N 0.000 description 1
- OUPTVBRQLKDPCJ-UHFFFAOYSA-N ethyl 6-methyl-4-oxochromene-2-carboxylate Chemical compound CC1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 OUPTVBRQLKDPCJ-UHFFFAOYSA-N 0.000 description 1
- RWGUGNHDBXRLSD-UHFFFAOYSA-N ethyl 6-nitro-4-oxochromene-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 RWGUGNHDBXRLSD-UHFFFAOYSA-N 0.000 description 1
- RKIMFICEWCXBCE-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxochromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OCC)=CC(=O)C2=C1 RKIMFICEWCXBCE-UHFFFAOYSA-N 0.000 description 1
- DTYYWXDWSQOSNT-UHFFFAOYSA-N ethyl 7-methyl-4-oxochromene-2-carboxylate Chemical compound C1=C(C)C=C2OC(C(=O)OCC)=CC(=O)C2=C1 DTYYWXDWSQOSNT-UHFFFAOYSA-N 0.000 description 1
- HTBQNHVXXPOWAT-UHFFFAOYSA-N ethyl 8-methyl-4-oxochromene-2-carboxylate Chemical compound C1=CC(C)=C2OC(C(=O)OCC)=CC(=O)C2=C1 HTBQNHVXXPOWAT-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 101150085091 lat-2 gene Proteins 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ABJKIHHNDMEBNA-UHFFFAOYSA-N methylchromone Chemical compound C1=CC=C2C(=O)C(C)=COC2=C1 ABJKIHHNDMEBNA-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB553370 | 1970-02-05 | ||
| GB680470 | 1970-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2105191A1 true DE2105191A1 (de) | 1971-08-26 |
Family
ID=26239955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712105191 Pending DE2105191A1 (de) | 1970-02-05 | 1971-02-04 | 2 Tetrazolylchromondenvate, Ver fahren zu ihrer Herstellung und Arznei praparate |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5511674B1 (enrdf_load_stackoverflow) |
| BE (1) | BE762468A (enrdf_load_stackoverflow) |
| CA (1) | CA960223A (enrdf_load_stackoverflow) |
| DE (1) | DE2105191A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2081490A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7101597A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2154518A1 (enrdf_load_stackoverflow) * | 1971-09-16 | 1973-05-11 | Fisons Ltd | |
| US3896114A (en) * | 1972-04-12 | 1975-07-22 | Akira Nohara | Chromone derivatives |
| EP0115142A1 (en) * | 1982-12-23 | 1984-08-08 | Ici Americas Inc. | Chroman compounds |
| EP0634409A1 (en) * | 1993-07-13 | 1995-01-18 | Sumitomo Chemical Company, Limited | Process of producing 2-cyano-4-oxo-4H-benzopyran compounds |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1362782A (en) * | 1970-08-26 | 1974-08-07 | Fisons Ltd | Tetrazole derivatives |
| GB1356379A (en) * | 1970-08-27 | 1974-06-12 | Fisons Ltd | Tetrazole derivatives |
| GB1447479A (en) * | 1972-12-15 | 1976-08-25 | Fisons Ltd | Chromone carboxamido tetrazoles |
| KR100683274B1 (ko) * | 2004-02-12 | 2007-02-15 | 에스케이케미칼주식회사 | 치환된 벤조피란 화합물의 제조방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL70267C (enrdf_load_stackoverflow) * | ||||
| CH305038A (de) * | 1951-10-12 | 1955-01-31 | Ag Dr A Wander | Verfahren zur Herstellung eines basisch substituierten Chromons. |
-
1971
- 1971-01-20 CA CA103,461A patent/CA960223A/en not_active Expired
- 1971-02-03 BE BE762468A patent/BE762468A/xx unknown
- 1971-02-04 JP JP468971A patent/JPS5511674B1/ja active Pending
- 1971-02-04 FR FR7103715A patent/FR2081490A1/fr active Granted
- 1971-02-04 DE DE19712105191 patent/DE2105191A1/de active Pending
- 1971-02-05 NL NL7101597A patent/NL7101597A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2154518A1 (enrdf_load_stackoverflow) * | 1971-09-16 | 1973-05-11 | Fisons Ltd | |
| US3896114A (en) * | 1972-04-12 | 1975-07-22 | Akira Nohara | Chromone derivatives |
| EP0115142A1 (en) * | 1982-12-23 | 1984-08-08 | Ici Americas Inc. | Chroman compounds |
| EP0634409A1 (en) * | 1993-07-13 | 1995-01-18 | Sumitomo Chemical Company, Limited | Process of producing 2-cyano-4-oxo-4H-benzopyran compounds |
| US5659051A (en) * | 1993-07-13 | 1997-08-19 | Sumitomo Chemical Company, Limited | Process of producing 2-cyano-4-oxo-4H-benzopyran compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2081490A1 (en) | 1971-12-03 |
| CA960223A (en) | 1974-12-31 |
| BE762468A (fr) | 1971-08-03 |
| NL7101597A (enrdf_load_stackoverflow) | 1971-08-09 |
| JPS5511674B1 (enrdf_load_stackoverflow) | 1980-03-26 |
| FR2081490B1 (enrdf_load_stackoverflow) | 1975-04-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |