DE4010097A1 - Ungesaettigte n-benzoxodiazolopyranyllactame, ihre herstellung und verwendung - Google Patents
Ungesaettigte n-benzoxodiazolopyranyllactame, ihre herstellung und verwendungInfo
- Publication number
- DE4010097A1 DE4010097A1 DE4010097A DE4010097A DE4010097A1 DE 4010097 A1 DE4010097 A1 DE 4010097A1 DE 4010097 A DE4010097 A DE 4010097A DE 4010097 A DE4010097 A DE 4010097A DE 4010097 A1 DE4010097 A1 DE 4010097A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- oxadiazole
- pyrano
- benzo
- dimethyl
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000003814 drug Substances 0.000 claims abstract description 4
- -1 N-benzoxadiazolopyranyl lactams Chemical class 0.000 claims description 29
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- ASOVLPIXFLYHLT-UHFFFAOYSA-N 1-(6,6-dimethylpyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)pyridin-2-one Chemical compound C=1C(C)(C)OC2=CC3=NON=C3C=C2C=1N1C=CC=CC1=O ASOVLPIXFLYHLT-UHFFFAOYSA-N 0.000 claims description 3
- QCTPMZMVKAVILP-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)pyridin-2-one Chemical compound OC1C(C)(C)OC2=CC3=NON=C3C=C2C1N1C=CC=CC1=O QCTPMZMVKAVILP-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- ALPRCGZQJGIWBV-UHFFFAOYSA-N 1-(6,6-diethylpyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)pyridin-2-one Chemical compound C=1C(CC)(CC)OC2=CC3=NON=C3C=C2C=1N1C=CC=CC1=O ALPRCGZQJGIWBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- GRLGYCIRUHXOMO-UHFFFAOYSA-N 1-(6,6-dimethylpyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)-4-ethoxypyridin-2-one Chemical compound O=C1C=C(OCC)C=CN1C1=CC(C)(C)OC2=CC3=NON=C3C=C12 GRLGYCIRUHXOMO-UHFFFAOYSA-N 0.000 claims 1
- WJGINLQFZKRZAQ-UHFFFAOYSA-N 1-(6,6-dimethylpyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)-4-methoxypyridin-2-one Chemical compound O=C1C=C(OC)C=CN1C1=CC(C)(C)OC2=CC3=NON=C3C=C12 WJGINLQFZKRZAQ-UHFFFAOYSA-N 0.000 claims 1
- QIOZSQFOQXYHOV-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)-4-methoxypyridin-2-one Chemical compound O=C1C=C(OC)C=CN1C1C2=CC3=NON=C3C=C2OC(C)(C)C1O QIOZSQFOQXYHOV-UHFFFAOYSA-N 0.000 claims 1
- FLQQZRPRIQZJHW-UHFFFAOYSA-N 4-ethoxy-1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)pyridin-2-one Chemical compound O=C1C=C(OCC)C=CN1C1C2=CC3=NON=C3C=C2OC(C)(C)C1O FLQQZRPRIQZJHW-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PEQKKMDUWQAZHN-UHFFFAOYSA-N 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6h-pyrano [2,3-f] benzo-2,1,3-oxadiazole Chemical compound CC1(C)OC2=CC3=NON=C3C=C2C2C1O2 PEQKKMDUWQAZHN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- FZKWXWQVJUGUBH-UHFFFAOYSA-N trimethyl(pyridin-2-yloxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=N1 FZKWXWQVJUGUBH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- LLUYKLZRJOSZIQ-UHFFFAOYSA-N 6,6-diethyl-3-oxidopyrano[3,2-f][2,1,3]benzoxadiazol-3-ium Chemical compound C1=C2C=CC(CC)(CC)OC2=CC2=[N+]([O-])ON=C21 LLUYKLZRJOSZIQ-UHFFFAOYSA-N 0.000 description 2
- BJYBIXLJGNDGCA-UHFFFAOYSA-N 6,6-diethylpyrano[3,2-f][2,1,3]benzoxadiazole Chemical compound C1=C2C=CC(CC)(CC)OC2=CC2=NON=C21 BJYBIXLJGNDGCA-UHFFFAOYSA-N 0.000 description 2
- LBDJDSQBVCDKRN-UHFFFAOYSA-N 6h-pyrano[2,3-f][2,1,3]benzoxadiazole Chemical compound C1=C2C=CCOC2=CC2=NON=C21 LBDJDSQBVCDKRN-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- MRUBLFLEOOBCOE-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1C2=CC3=NON=C3C=C2OC(C)(C)C1O MRUBLFLEOOBCOE-UHFFFAOYSA-N 0.000 description 1
- LKQMHAIMVYQYMD-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)-5-nitropyridin-2-one Chemical compound CC1(C(C(C=2C(=CC=3C(=NON=3)C=2)O1)N1C(C=CC(=C1)[N+](=O)[O-])=O)O)C LKQMHAIMVYQYMD-UHFFFAOYSA-N 0.000 description 1
- IIVQRVOPTNREBN-UHFFFAOYSA-N 13,13-diethyl-5,11,14-trioxa-4,6-diazatetracyclo[7.5.0.03,7.010,12]tetradeca-1,3,6,8-tetraene Chemical compound CCC1(CC)OC2=CC3=NON=C3C=C2C2C1O2 IIVQRVOPTNREBN-UHFFFAOYSA-N 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 210000001989 nasopharynx Anatomy 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4010097A DE4010097A1 (de) | 1990-03-29 | 1990-03-29 | Ungesaettigte n-benzoxodiazolopyranyllactame, ihre herstellung und verwendung |
| CA002078139A CA2078139A1 (fr) | 1990-03-29 | 1991-03-20 | N-benzoxadioazolopyranyllactames insatures, leur obtention et leur emploi |
| HU9230V HU9203092D0 (en) | 1990-03-29 | 1991-03-20 | Method for producing n-benzoxa-diazolo-pyranyl-lactames and pharmaceutical preparatives containing them |
| PCT/EP1991/000537 WO1991014690A1 (fr) | 1990-03-29 | 1991-03-20 | Lactames de n-benzoxodiazolopyranyl insatures, leur fabrication et utilisation |
| EP91906395A EP0521936A1 (fr) | 1990-03-29 | 1991-03-20 | Lactames de n-benzoxodiazolopyranyl insatures, leur fabrication et utilisation |
| JP91506303A JPH05505801A (ja) | 1990-03-29 | 1991-03-20 | 不飽和ｎ―ベンズオキサジアゾロピラニルラクタム、その製造及び使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4010097A DE4010097A1 (de) | 1990-03-29 | 1990-03-29 | Ungesaettigte n-benzoxodiazolopyranyllactame, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4010097A1 true DE4010097A1 (de) | 1991-10-02 |
Family
ID=6403333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4010097A Withdrawn DE4010097A1 (de) | 1990-03-29 | 1990-03-29 | Ungesaettigte n-benzoxodiazolopyranyllactame, ihre herstellung und verwendung |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0521936A1 (fr) |
| JP (1) | JPH05505801A (fr) |
| CA (1) | CA2078139A1 (fr) |
| DE (1) | DE4010097A1 (fr) |
| HU (1) | HU9203092D0 (fr) |
| WO (1) | WO1991014690A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0693283A4 (fr) * | 1993-04-02 | 1997-07-23 | Nissan Chemical Ind Ltd | Remede contre l'insuffisance cardiaque |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164509A (en) * | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| WO1996034871A1 (fr) * | 1995-05-01 | 1996-11-07 | Nissan Chemical Industries, Ltd. | Derives de benzopyrane |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3163018D1 (en) * | 1980-02-02 | 1984-05-17 | Beecham Group Plc | Pyrano derivatives, a process for their preparation and antihypertensive compositions containing them |
| DE3726261A1 (de) * | 1986-12-23 | 1988-07-07 | Merck Patent Gmbh | Chromanderivate |
| JPH0699439B2 (ja) * | 1988-02-03 | 1994-12-07 | 日産化学工業株式会社 | ピラノベンゾオキサジアゾール誘導体 |
-
1990
- 1990-03-29 DE DE4010097A patent/DE4010097A1/de not_active Withdrawn
-
1991
- 1991-03-20 WO PCT/EP1991/000537 patent/WO1991014690A1/fr not_active Ceased
- 1991-03-20 JP JP91506303A patent/JPH05505801A/ja active Pending
- 1991-03-20 HU HU9230V patent/HU9203092D0/hu unknown
- 1991-03-20 CA CA002078139A patent/CA2078139A1/fr not_active Abandoned
- 1991-03-20 EP EP91906395A patent/EP0521936A1/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0693283A4 (fr) * | 1993-04-02 | 1997-07-23 | Nissan Chemical Ind Ltd | Remede contre l'insuffisance cardiaque |
| US5919806A (en) * | 1993-04-02 | 1999-07-06 | Nissan Chemical Industries, Ltd. | Medicines for cardiac insufficiency |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0521936A1 (fr) | 1993-01-13 |
| HU9203092D0 (en) | 1992-12-28 |
| WO1991014690A1 (fr) | 1991-10-03 |
| CA2078139A1 (fr) | 1991-09-30 |
| JPH05505801A (ja) | 1993-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |