RU2054004C1 - Производные 3(2н)-пиридазинона или их фармацевтически приемлемые соли и фармацевтическая композиция на их основе - Google Patents
Производные 3(2н)-пиридазинона или их фармацевтически приемлемые соли и фармацевтическая композиция на их основе Download PDFInfo
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- RU2054004C1 RU2054004C1 SU915010505A SU5010505A RU2054004C1 RU 2054004 C1 RU2054004 C1 RU 2054004C1 SU 915010505 A SU915010505 A SU 915010505A SU 5010505 A SU5010505 A SU 5010505A RU 2054004 C1 RU2054004 C1 RU 2054004C1
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- hydrogen
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- general formula
- alkyl
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- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 230000000694 effects Effects 0.000 claims abstract description 31
- 239000003146 anticoagulant agent Substances 0.000 claims abstract description 5
- 230000002785 anti-thrombosis Effects 0.000 claims abstract description 3
- -1 cyano, phenoxy, thienyl Chemical group 0.000 claims description 147
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229940124549 vasodilator Drugs 0.000 claims description 7
- 239000003071 vasodilator agent Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000297 inotrophic effect Effects 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 32
- 239000000203 mixture Substances 0.000 abstract description 32
- 238000004519 manufacturing process Methods 0.000 abstract description 22
- 230000003177 cardiotonic effect Effects 0.000 abstract description 7
- 208000007536 Thrombosis Diseases 0.000 abstract description 6
- 239000004480 active ingredient Substances 0.000 abstract description 6
- 208000026935 allergic disease Diseases 0.000 abstract description 5
- 208000006673 asthma Diseases 0.000 abstract description 4
- 206010020751 Hypersensitivity Diseases 0.000 abstract description 3
- 206010020772 Hypertension Diseases 0.000 abstract description 3
- 230000007815 allergy Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 230000000304 vasodilatating effect Effects 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 58
- 239000002904 solvent Substances 0.000 description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000003814 drug Substances 0.000 description 34
- 238000012360 testing method Methods 0.000 description 32
- 229940079593 drug Drugs 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 239000000523 sample Substances 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 210000004369 blood Anatomy 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 210000001367 artery Anatomy 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 229910052987 metal hydride Inorganic materials 0.000 description 5
- 150000004681 metal hydrides Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 230000000069 prophylactic effect Effects 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- 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 4
- 229920000084 Gum arabic Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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- 239000008103 glucose Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
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- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
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Images
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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10991490 | 1990-04-25 | ||
| JP109914/90 | 1990-04-25 | ||
| PCT/JP1991/000517 WO1991016314A1 (en) | 1990-04-25 | 1991-04-19 | Pyridazinone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2054004C1 true RU2054004C1 (ru) | 1996-02-10 |
Family
ID=14522343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU915010505A RU2054004C1 (ru) | 1990-04-25 | 1991-04-19 | Производные 3(2н)-пиридазинона или их фармацевтически приемлемые соли и фармацевтическая композиция на их основе |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US5202323A (https=) |
| EP (1) | EP0482208B1 (https=) |
| JP (1) | JPH07107055B2 (https=) |
| KR (1) | KR970002876B1 (https=) |
| AT (1) | ATE194835T1 (https=) |
| AU (1) | AU634655B2 (https=) |
| CA (1) | CA2053863C (https=) |
| DE (1) | DE69132329T2 (https=) |
| DK (1) | DK0482208T3 (https=) |
| ES (1) | ES2149761T3 (https=) |
| GR (1) | GR3034331T3 (https=) |
| HU (1) | HU208124B (https=) |
| RU (1) | RU2054004C1 (https=) |
| TW (1) | TW204348B (https=) |
| UA (1) | UA27031A1 (https=) |
| WO (1) | WO1991016314A1 (https=) |
| ZA (1) | ZA913134B (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2211217C2 (ru) * | 1998-06-05 | 2003-08-27 | Эгиш Дьёдьсердьяр Рт. | Способ получения 5-хлор-4-аминозамещенного производного 3(2н)-пиридазинона |
| RU2237468C2 (ru) * | 2000-05-31 | 2004-10-10 | Фит-Иммун Гмбх | Назальная мазь на основе вазелина |
| RU2291154C2 (ru) * | 2001-04-05 | 2007-01-10 | Торрент Фармасьютикалз Лтд | Гетероциклические соединения для возрастных и диабетических сосудистых осложнений |
| RU2339381C2 (ru) * | 2004-02-09 | 2008-11-27 | Ниссан Кемикал Индастриз, Лтд. | Ингибитор гиперплазии интимы сосудов |
| RU2855516C1 (ru) * | 2020-06-26 | 2026-02-02 | Нихон Нохияку Ко., Лтд. | Производное арилтетрагидропиридазина или его соль, инсектидный агент, содержащий соединение, и способ его применения |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2149761T3 (es) * | 1990-04-25 | 2000-11-16 | Nissan Chemical Ind Ltd | Derivado de piridazinona. |
| US5403590A (en) * | 1992-12-21 | 1995-04-04 | New England Deaconess Hospital Corporation | Method of pulsatile drug infusion |
| IL110040A (en) * | 1993-06-29 | 2000-07-16 | Nissan Chemical Ind Ltd | Pyridazinone derivatives their preparation and pharmaceutical compositions comprising them |
| JP3080131B2 (ja) | 1993-06-29 | 2000-08-21 | 日産化学工業株式会社 | ピリダジノン誘導体 |
| AU681694B2 (en) * | 1993-09-06 | 1997-09-04 | Ishihara Sangyo Kaisha Ltd. | Pyridazinone derivatives or their salts, processes for theirproduction, and anti-shock agents containing them |
| NZ270130A (en) * | 1993-12-16 | 1995-12-21 | Nihon Nohyaku Co Ltd | Pyridazinone derivatives, preparation and pharmaceutical compositions thereof |
| DK0742211T3 (da) * | 1994-01-25 | 2000-08-14 | Nissan Chemical Ind Ltd | Pyridazinonderivater |
| IL112695A (en) * | 1994-02-22 | 1999-04-11 | Green Cross Corp | Pharmaceutical compositions containing pyridazinone derivatives |
| GB9514160D0 (en) * | 1994-07-25 | 1995-09-13 | Zeneca Ltd | Aromatic compounds |
| US5670504A (en) * | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| TW434240B (en) | 1995-06-20 | 2001-05-16 | Zeneca Ltd | Aromatic compounds, preparation thereof and pharmaceutical composition comprising same |
| CN1102593C (zh) | 1996-06-27 | 2003-03-05 | 詹森药业有限公司 | N－[4－(杂芳基甲基)苯基]－杂芳基胺类化合物 |
| TW482675B (en) * | 1997-01-31 | 2002-04-11 | Green Cross Corp | Compositions for oral administration containing pyridazinone compounds technical field of the invention |
| US6284758B1 (en) * | 1997-08-28 | 2001-09-04 | Welfide Corporation | Angiogenesis promoters and angiogenesis potentiators |
| DE69919191T2 (de) * | 1998-09-01 | 2005-07-28 | Nissan Chemical Industries, Ltd. | Heilmittel für die stenose des rückenmarkkanals |
| WO2000033845A1 (en) * | 1998-12-07 | 2000-06-15 | Nissan Chemical Industries, Ltd. | Remedial agent for erectile dysfunction |
| US20050101631A1 (en) * | 2002-08-01 | 2005-05-12 | Otsuka Pharmaceuticals Company | Process for producing carbostyril derivatives |
| US7399864B2 (en) * | 2001-05-02 | 2008-07-15 | Otsuka Pharmaceutical Co., Ltd. | Process for producing carbostyril derivatives |
| CN1537018A (zh) | 2001-05-23 | 2004-10-13 | 田边制药株式会社 | 一种用于软骨疾病再生治疗的组合物 |
| EP1389468A4 (en) | 2001-05-23 | 2007-01-10 | Tanabe Seiyaku Co | COMPOSITIONS FOR PROMOTING BONE FRACTURE HEALING |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| CA2526586C (en) * | 2003-09-09 | 2010-03-16 | Biogen International Gmbh | The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma |
| CN1897952B (zh) * | 2003-12-26 | 2010-12-08 | 日产化学工业株式会社 | 中性白细胞增多抑制剂 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| EP2374805A4 (en) * | 2008-12-25 | 2012-06-27 | Nissan Chemical Ind Ltd | PYRIDAZINE-3 (2H) -ONE HYDROCHLORIDE COMPOUND CRYSTALS AND METHOD FOR THE PRODUCTION THEREOF |
| KR101763656B1 (ko) | 2009-06-29 | 2017-08-01 | 인사이트 홀딩스 코포레이션 | Ｐｉ3ｋ 저해물질로서의 피리미디논 |
| US8759359B2 (en) * | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| TW201130842A (en) * | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| WO2011099573A1 (ja) | 2010-02-12 | 2011-08-18 | 大正製薬株式会社 | 徐放性製剤 |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EP3660016A1 (en) | 2010-12-20 | 2020-06-03 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| DK2681236T3 (en) | 2011-03-01 | 2018-04-16 | Synergy Pharmaceuticals Inc | PROCEDURE FOR MANUFACTURING GUANYLATE CYCLASE-C-AGONISTS |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| PT3513793T (pt) | 2011-09-02 | 2021-05-10 | Incyte Holdings Corp | Heterociclilaminas como inibidores de pi3k |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235215A1 (en) | 2013-03-15 | 2015-10-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| BR112015030326A2 (pt) | 2013-06-05 | 2017-08-29 | Synergy Pharmaceuticals Inc | Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos |
| AU2014305843B2 (en) | 2013-08-09 | 2019-08-29 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| SI3030549T1 (sl) | 2013-09-12 | 2019-08-30 | Janssen Biopharma, Inc. | Spojine piridazinona in njihove uporabe |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| SG10201907576SA (en) | 2015-02-27 | 2019-09-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| CN107793362B (zh) * | 2016-08-30 | 2022-04-22 | 江苏恩华药业股份有限公司 | 一种苯基哒嗪酮类衍生物的合成及其应用 |
| SG11202011680YA (en) | 2018-06-01 | 2020-12-30 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
| EP4706758A3 (en) | 2019-05-21 | 2026-05-06 | Ardelyx, Inc. | Methods for inhibiting phosphate transport |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534893A1 (de) * | 1975-08-05 | 1977-02-17 | Bayer Ag | (thiono)(thiol)pyridazinonalkanphosphonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
| EP0186817B1 (en) * | 1984-12-10 | 1989-08-02 | Nissan Chemical Industries Ltd. | 3(2h)pyridazinone, process for its preparation and anti-allergic agent containing it |
| ES2031821T3 (es) * | 1985-10-17 | 1993-01-01 | Smith Kline & French Laboratories Limited | Procedimiento para preparar derivados de 4(4-oxo-1,4-dihidropiridin-1-il)fenilo. |
| US4978665A (en) * | 1987-01-20 | 1990-12-18 | Nissan Chemical Industries Ltd. | 3(2H)pyridazinone, and antagonistic agent against SRS-A containing it |
| JP2550631B2 (ja) * | 1987-01-20 | 1996-11-06 | 日産化学工業株式会社 | ピリダジノン誘導体 |
| IE62890B1 (en) * | 1988-12-06 | 1995-03-08 | Hafslund Nycomed Pharma | New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure |
| JPH02256668A (ja) * | 1988-12-20 | 1990-10-17 | Nissan Chem Ind Ltd | ピリダジノン誘導体 |
| ES2149761T3 (es) * | 1990-04-25 | 2000-11-16 | Nissan Chemical Ind Ltd | Derivado de piridazinona. |
-
1991
- 1991-04-19 ES ES91907712T patent/ES2149761T3/es not_active Expired - Lifetime
- 1991-04-19 DK DK91907712T patent/DK0482208T3/da active
- 1991-04-19 US US07/768,182 patent/US5202323A/en not_active Expired - Fee Related
- 1991-04-19 RU SU915010505A patent/RU2054004C1/ru active
- 1991-04-19 CA CA002053863A patent/CA2053863C/en not_active Expired - Lifetime
- 1991-04-19 WO PCT/JP1991/000517 patent/WO1991016314A1/ja not_active Ceased
- 1991-04-19 AU AU76511/91A patent/AU634655B2/en not_active Expired
- 1991-04-19 DE DE69132329T patent/DE69132329T2/de not_active Expired - Lifetime
- 1991-04-19 UA UA5010505A patent/UA27031A1/uk unknown
- 1991-04-19 JP JP3-507543A patent/JPH07107055B2/ja not_active Expired - Lifetime
- 1991-04-19 EP EP91907712A patent/EP0482208B1/en not_active Expired - Lifetime
- 1991-04-19 KR KR1019910701537A patent/KR970002876B1/ko not_active Expired - Lifetime
- 1991-04-19 HU HU913497A patent/HU208124B/hu unknown
- 1991-04-19 AT AT91907712T patent/ATE194835T1/de not_active IP Right Cessation
- 1991-04-23 TW TW080103191A patent/TW204348B/zh not_active IP Right Cessation
- 1991-04-25 ZA ZA913134A patent/ZA913134B/xx unknown
-
1992
- 1992-12-21 US US07/994,404 patent/US5314883A/en not_active Expired - Lifetime
- 1992-12-21 US US07/994,413 patent/US5318968A/en not_active Expired - Fee Related
-
2000
- 2000-09-05 GR GR20000402019T patent/GR3034331T3/el not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Европейская заявка ЕР N 0275997, кл. C 07D 237/22, 1988. Европейская заявка ЕP N 155798, кл. A 61K 31/50, 1985. Европейская заявка ЕР N 220044, кл. C 07D 401/10, 1987. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2211217C2 (ru) * | 1998-06-05 | 2003-08-27 | Эгиш Дьёдьсердьяр Рт. | Способ получения 5-хлор-4-аминозамещенного производного 3(2н)-пиридазинона |
| RU2237468C2 (ru) * | 2000-05-31 | 2004-10-10 | Фит-Иммун Гмбх | Назальная мазь на основе вазелина |
| RU2291154C2 (ru) * | 2001-04-05 | 2007-01-10 | Торрент Фармасьютикалз Лтд | Гетероциклические соединения для возрастных и диабетических сосудистых осложнений |
| RU2339381C2 (ru) * | 2004-02-09 | 2008-11-27 | Ниссан Кемикал Индастриз, Лтд. | Ингибитор гиперплазии интимы сосудов |
| RU2855516C1 (ru) * | 2020-06-26 | 2026-02-02 | Нихон Нохияку Ко., Лтд. | Производное арилтетрагидропиридазина или его соль, инсектидный агент, содержащий соединение, и способ его применения |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0482208A1 (en) | 1992-04-29 |
| AU634655B2 (en) | 1993-02-25 |
| HU208124B (en) | 1993-08-30 |
| DE69132329D1 (de) | 2000-08-24 |
| AU7651191A (en) | 1991-11-11 |
| WO1991016314A1 (en) | 1991-10-31 |
| HU913497D0 (en) | 1992-01-28 |
| UA27031A1 (uk) | 2000-02-28 |
| DE69132329T2 (de) | 2000-11-30 |
| TW204348B (https=) | 1993-04-21 |
| DK0482208T3 (da) | 2000-09-18 |
| US5314883A (en) | 1994-05-24 |
| ES2149761T3 (es) | 2000-11-16 |
| ATE194835T1 (de) | 2000-08-15 |
| CA2053863C (en) | 1996-10-29 |
| ZA913134B (en) | 1992-04-29 |
| KR920701169A (ko) | 1992-08-11 |
| HUT60253A (en) | 1992-08-28 |
| EP0482208B1 (en) | 2000-07-19 |
| CA2053863A1 (en) | 1991-10-26 |
| US5318968A (en) | 1994-06-07 |
| KR970002876B1 (ko) | 1997-03-12 |
| JPH07107055B1 (https=) | 1995-11-15 |
| GR3034331T3 (en) | 2000-12-29 |
| US5202323A (en) | 1993-04-13 |
| EP0482208A4 (en) | 1992-10-07 |
| JPH07107055B2 (ja) | 1995-11-15 |
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