CN1102527A - 末梢血管舒张剂 - Google Patents
末梢血管舒张剂 Download PDFInfo
- Publication number
- CN1102527A CN1102527A CN94190064A CN94190064A CN1102527A CN 1102527 A CN1102527 A CN 1102527A CN 94190064 A CN94190064 A CN 94190064A CN 94190064 A CN94190064 A CN 94190064A CN 1102527 A CN1102527 A CN 1102527A
- Authority
- CN
- China
- Prior art keywords
- alkyl group
- low alkyl
- salt
- hydrogen atom
- carbostyril derivative
- 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
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- 239000000810 peripheral vasodilating agent Substances 0.000 title abstract description 4
- 229960002116 peripheral vasodilator Drugs 0.000 title description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 118
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims description 151
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- -1 nitro, amino Chemical group 0.000 claims description 82
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229940124549 vasodilator Drugs 0.000 claims description 5
- 239000003071 vasodilator agent Substances 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 3
- 229960005222 phenazone Drugs 0.000 claims 3
- 230000002093 peripheral effect Effects 0.000 abstract description 9
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 114
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 81
- 239000002904 solvent Substances 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 235000019441 ethanol Nutrition 0.000 description 48
- 238000005160 1H NMR spectroscopy Methods 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- 150000001412 amines Chemical class 0.000 description 46
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- 239000000243 solution Substances 0.000 description 40
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- 239000002253 acid Substances 0.000 description 30
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
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- 230000002829 reductive effect Effects 0.000 description 27
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 description 26
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 235000011167 hydrochloric acid Nutrition 0.000 description 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 150000002170 ethers Chemical class 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 235000015320 potassium carbonate Nutrition 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 238000010531 catalytic reduction reaction Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 150000008282 halocarbons Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002798 polar solvent Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- 230000017531 blood circulation Effects 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 description 8
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 235000010755 mineral Nutrition 0.000 description 8
- 239000011707 mineral Substances 0.000 description 8
- 239000000825 pharmaceutical preparation Substances 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
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- 150000004678 hydrides Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 235000011118 potassium hydroxide Nutrition 0.000 description 7
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- 238000010898 silica gel chromatography Methods 0.000 description 7
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 3
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
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- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
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- 238000003419 tautomerization reaction Methods 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000037997 venous disease Diseases 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26594/93 | 1993-02-16 | ||
| JP5026594A JPH06239858A (ja) | 1993-02-16 | 1993-02-16 | 末梢血管拡張剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1102527A true CN1102527A (zh) | 1995-05-10 |
Family
ID=12197866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94190064A Pending CN1102527A (zh) | 1993-02-16 | 1994-02-03 | 末梢血管舒张剂 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5591751A (enExample) |
| EP (1) | EP0636128A1 (enExample) |
| JP (1) | JPH06239858A (enExample) |
| KR (1) | KR950700900A (enExample) |
| CN (1) | CN1102527A (enExample) |
| AU (1) | AU666259B2 (enExample) |
| CA (1) | CA2133207A1 (enExample) |
| PH (1) | PH30979A (enExample) |
| TW (1) | TW259789B (enExample) |
| WO (1) | WO1994019339A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143751A (zh) * | 2022-07-15 | 2023-05-23 | 中国人民解放军军事科学院防化研究院 | 一种含苯乙烯吡啶的喹喔啉酮化合物及其制备方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06239858A (ja) * | 1993-02-16 | 1994-08-30 | Otsuka Pharmaceut Co Ltd | 末梢血管拡張剤 |
| BR0114253A (pt) * | 2000-10-02 | 2003-07-01 | Janssen Pharmaceutica Nv | Antagonistas de receptor de glutamato metabotrópico |
| US7612078B2 (en) * | 2003-03-31 | 2009-11-03 | Epix Delaware, Inc. | Piperidinylamino-thieno[2,3-D] pyrimidine compounds |
| US20050222175A1 (en) * | 2004-03-31 | 2005-10-06 | Dhanoa Dale S | New piperidinylamino-thieno[2,3-D] pyrimidine compounds |
| KR101159118B1 (ko) * | 2003-12-05 | 2012-06-22 | 얀센 파마슈티카 엔.브이. | 폴리(ａｄｐ-리보스)폴리머라제 저해제로서의 6-치환된2-퀴놀리논 및 2-퀴녹살리논 |
| US7488736B2 (en) * | 2004-05-17 | 2009-02-10 | Epix Delaware, Inc. | Thienopyridinone compounds and methods of treatment |
| US7598265B2 (en) * | 2004-09-30 | 2009-10-06 | Epix Delaware, Inc. | Compositions and methods for treating CNS disorders |
| US7576211B2 (en) | 2004-09-30 | 2009-08-18 | Epix Delaware, Inc. | Synthesis of thienopyridinone compounds and related intermediates |
| US7407966B2 (en) * | 2004-10-07 | 2008-08-05 | Epix Delaware, Inc. | Thienopyridinone compounds and methods of treatment |
| US7487406B2 (en) * | 2005-11-29 | 2009-02-03 | International Business Machines Corporation | Systems, methods, and media for managing software defects |
| TW200803855A (en) * | 2006-02-24 | 2008-01-16 | Kalypsys Inc | Quinolones useful as inducible nitric oxide synthase inhibitors |
| EP2445877B1 (en) * | 2008-12-03 | 2014-07-23 | Nanotherapeutics, Inc. | Bicyclic compounds and methods of making and using same |
| WO2018132829A1 (en) * | 2017-01-16 | 2018-07-19 | Drexel University | Novel glutamate transporter activators and methods using same |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5165770A (ja) * | 1974-12-04 | 1976-06-07 | Otsuka Pharma Co Ltd | Karubosuchirirujudotaino seizoho |
| JPS5168574A (ja) * | 1974-12-07 | 1976-06-14 | Otsuka Pharma Co Ltd | Karubosuchirirujudotaino seizoho |
| JPS51118771A (en) * | 1975-04-09 | 1976-10-18 | Otsuka Pharmaceut Co Ltd | Method for preparing carbostyryl derivatives |
| JPS597707B2 (ja) * | 1975-06-23 | 1984-02-20 | オオツカセイヤク カブシキガイシヤ | カルボスチリルユウドウタイノ セイゾウホウ |
| JPS52283A (en) * | 1975-06-23 | 1977-01-05 | Otsuka Pharmaceut Co Ltd | Process for preparation of carbostyril derivatives |
| JPS5283380A (en) * | 1975-12-26 | 1977-07-12 | Otsuka Pharmaceut Co Ltd | Synthesis of thiocarbostyril derivatives |
| JPS52118474A (en) * | 1976-03-31 | 1977-10-04 | Otsuka Pharmaceut Co Ltd | Alpha-substituted aminoalkanyol-3,4-dihydrocarbostyril derivatives and method of preparing the same |
| JPS5416478A (en) * | 1977-07-08 | 1979-02-07 | Otsuka Pharmaceut Co Ltd | 3,4-dihydrocarbostyril herivative |
| FI77852C (fi) * | 1981-02-17 | 1989-05-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av nya, saosom hjaertmediciner anvaendbara substituerade amid- och (maettad heterocykel)karbonylkarbostyrilderivat. |
| JPS57171974A (en) * | 1981-04-15 | 1982-10-22 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| JPS57154129A (en) * | 1981-03-16 | 1982-09-22 | Otsuka Pharmaceut Co Ltd | Cardiotonic drug |
| JPS5929668A (ja) * | 1982-08-13 | 1984-02-16 | Otsuka Pharmaceut Co Ltd | カルボスチリル誘導体 |
| US4845100A (en) * | 1985-04-12 | 1989-07-04 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof, processes for preparing the same and cardiotonic composition containing the same |
| US4886809A (en) * | 1986-07-31 | 1989-12-12 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof |
| JPH0696555B2 (ja) * | 1986-07-31 | 1994-11-30 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| US5405602A (en) * | 1989-01-31 | 1995-04-11 | Simmons; Paul L. | Nonaqueous cold sterilant |
| ES2056259T3 (es) * | 1989-02-10 | 1994-10-01 | Otsuka Pharma Co Ltd | Derivados de carboestirilo. |
| JPH06239858A (ja) * | 1993-02-16 | 1994-08-30 | Otsuka Pharmaceut Co Ltd | 末梢血管拡張剤 |
-
1993
- 1993-02-16 JP JP5026594A patent/JPH06239858A/ja active Pending
-
1994
- 1994-02-03 US US08/318,801 patent/US5591751A/en not_active Expired - Fee Related
- 1994-02-03 CA CA002133207A patent/CA2133207A1/en not_active Abandoned
- 1994-02-03 WO PCT/JP1994/000157 patent/WO1994019339A1/en not_active Ceased
- 1994-02-03 CN CN94190064A patent/CN1102527A/zh active Pending
- 1994-02-03 AU AU59788/94A patent/AU666259B2/en not_active Ceased
- 1994-02-03 EP EP94905839A patent/EP0636128A1/en not_active Withdrawn
- 1994-02-04 TW TW083100952A patent/TW259789B/zh active
- 1994-02-16 PH PH47776A patent/PH30979A/en unknown
- 1994-10-15 KR KR1019940703696A patent/KR950700900A/ko not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143751A (zh) * | 2022-07-15 | 2023-05-23 | 中国人民解放军军事科学院防化研究院 | 一种含苯乙烯吡啶的喹喔啉酮化合物及其制备方法 |
| CN116143751B (zh) * | 2022-07-15 | 2025-07-15 | 中国人民解放军军事科学院防化研究院 | 一种含苯乙烯吡啶的喹喔啉酮化合物及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW259789B (enExample) | 1995-10-11 |
| JPH06239858A (ja) | 1994-08-30 |
| AU666259B2 (en) | 1996-02-01 |
| AU5978894A (en) | 1994-09-14 |
| WO1994019339A1 (en) | 1994-09-01 |
| PH30979A (en) | 1997-12-23 |
| US5591751A (en) | 1997-01-07 |
| KR950700900A (ko) | 1995-02-20 |
| CA2133207A1 (en) | 1994-09-01 |
| EP0636128A1 (en) | 1995-02-01 |
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| AD01 | Patent right deemed abandoned | ||
| C20 | Patent right or utility model deemed to be abandoned or is abandoned |