LV11029B - Benzoxazinone and benzothiazinone derivatives endowed with cardiovascular activity - Google Patents
Benzoxazinone and benzothiazinone derivatives endowed with cardiovascular activity Download PDFInfo
- Publication number
- LV11029B LV11029B LVP-95-218A LV950218A LV11029B LV 11029 B LV11029 B LV 11029B LV 950218 A LV950218 A LV 950218A LV 11029 B LV11029 B LV 11029B
- Authority
- LV
- Latvia
- Prior art keywords
- compound
- formula
- dihydro
- hydrogen
- benzoxazin
- Prior art date
Links
- 230000005792 cardiovascular activity Effects 0.000 title abstract description 3
- MJNPHLBKHKJDEF-UHFFFAOYSA-N 2h-1$l^{4},2-benzothiazine 1-oxide Chemical class C1=CC=C2S(=O)NC=CC2=C1 MJNPHLBKHKJDEF-UHFFFAOYSA-N 0.000 title abstract 2
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000011593 sulfur Substances 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 10
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- 239000000203 mixture Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- -1 methylenedioxyphenyl Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 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 description 5
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- 239000002243 precursor Substances 0.000 claims description 5
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- 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
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- POVFCWQCRHXYAB-UHFFFAOYSA-N 2-(4-oxo-2h-1,3-benzoxazin-3-yl)ethyl nitrate Chemical compound C1=CC=C2C(=O)N(CCO[N+](=O)[O-])COC2=C1 POVFCWQCRHXYAB-UHFFFAOYSA-N 0.000 claims description 2
- ARIHTIVOSBBWHL-UHFFFAOYSA-N 2-(7-chloro-4-oxo-2h-1,3-benzoxazin-3-yl)ethyl nitrate Chemical compound ClC1=CC=C2C(=O)N(CCO[N+](=O)[O-])COC2=C1 ARIHTIVOSBBWHL-UHFFFAOYSA-N 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000000204 (C2-C4) acyl group Chemical group 0.000 claims 2
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
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- JCKFVYYCSDOULV-UHFFFAOYSA-N 2-(7-methyl-4-oxo-2h-1,3-benzoxazin-3-yl)ethyl nitrate Chemical compound O=C1N(CCO[N+]([O-])=O)COC2=CC(C)=CC=C21 JCKFVYYCSDOULV-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
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- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- YBYIZRPBXCCDQW-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazin-4-one Chemical class C1=CC=C2C(=O)NCOC2=C1 YBYIZRPBXCCDQW-UHFFFAOYSA-N 0.000 description 3
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- 230000000304 vasodilatating effect Effects 0.000 description 3
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- 102400000059 Arg-vasopressin Human genes 0.000 description 2
- 101800001144 Arg-vasopressin Proteins 0.000 description 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 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 1
- 206010022998 Irritability Diseases 0.000 description 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- BAQGCWNPCFABAY-UHFFFAOYSA-N methyl 2-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S BAQGCWNPCFABAY-UHFFFAOYSA-N 0.000 description 1
- QXDWMJQRXWLSDP-UHFFFAOYSA-N methyl 4-chloro-2-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1O QXDWMJQRXWLSDP-UHFFFAOYSA-N 0.000 description 1
- KJWHRMZKJXOWFC-UHFFFAOYSA-N methyl 5-chloro-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1O KJWHRMZKJXOWFC-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (11)
- LV 11029 IZGUDROJUMA FORMULA 1. Savienojumi ar vispārējo formulukur R ir ūdeņradis, (Cļ_5)alkil-, ciklopentil-, cikloheksil-, cikloheptil-, fenilgrupa pēc izvēles aizvietota ar 1 vai 2 neatkarīgi izvēlētām hidroksi-, halogen-, nitro-, (Cļ_4)alkil-un (Cļ_4)alkoksi-, metilēndioksifenil- grupām; Rļ un R2 neatkarīgi satur ūdeņradi, halogen-, (Cļ_4)-alkil-, (Cļ_4)alkoksi- vai trifluormetil-grupu; X ir skābekļa vai sēra atoms, Y ir (^-Cgjalkilēnķēde vai ciklopentilēna, cikloheksilēna vai cikloheptilēna grupa; un to farmaceitiski pieņemamie sāļi.
- 2. Savienojumi saskaņā ar 1. punktu, kas atšķiras ar to, ka R ir ūdeņradis, (Cļ_4)alkil-, ciklopentil-, cikloheksil- vai cikloheptilgrupa; Rļ un R2 neatkarīgi ir ūdeņradis, halogen-, (Cļ_4)alkil- vai (Cļ_4)alkoksigrupa; X ir skābekļa vai sēra atoms un Y ir (C2-6)alkilēnķēde vai ciklopentilēna, cikloheksilēna vai cikloheptilēna daļa; un to farmaceitiski pieņemamie sāļi.
- 3. Savienojumi saskaņā ar 1. un 2. punktu, kas atšķiras ar to, ka R ir ūdeņradis, Rļ un R2 neatkarīgi ir ūdeņradis, halogen-, (Cļ_4)alkil- vai (Cļ_4)alkoksigrupa; X ir skābekļa vai sēra atoms; un Y ir (C2-6)alkilēnķēde; un to farmaceitiski pieņemamie sāļi.
- 4. Savienojums saskaņā ar 1. punktu, kas atšķiras ar to, ka savienojums ir 2,3-dihidro-3-(2 -nitrooksietil)-4H-1,3-benzoksazīn-4-ons.
- 5. Savienojums saskaņā ar l. punktu, kas atšķiras ar to, ka savienojums ir 2,3-dihidro-6-metil-3-(2 -nitrooksietil)-4H-1,3-benzoksazīn-4-ons.
- 6. Savienojums saskaņā ar 1. punktu, kas atšķiras ar to, ka savienojums ir 2,3-dihidro-7-hloro-3-(2 -nitrooksietil)-4H-1,3-benzoksazīn-4-ons.
- 7. Savienojums saskaņā ar 1. punktu, kas atšķiras ar to, ka savienojums ir 2,3-dihidro-7-metil-3-(2 -nitrooksietil)-4H-1,3-benzoksazīn-4-ons.
- 8. Savienojums saskaņā ar 1. punktu, kas atšķiras ar to, ka savienojums ir 2,3- 1 ( dihidro-3-(2 -nitrooksietil)-4H-l ,3-benzotiazīn-4-ons. -2-
- 9. Farmaceitisks sastāvs, izmantojams sirds-asinsvadu terapijā, kas satur vismaz viena savienojuma, kas uzrādīts 1. punktā terapeitiski efektīgu daudzumu kopā ar vismaz farmakoloģiski pieņemamu inerto pildvielu.
- 10. Sastāva saskaņā ar 1. punktu izmantošana medikamentu ražošanai, kas izmantojami sirds-asinsvadu terapijā.
- 11. Sastāvu, kuri atbilst formulai I,izgatavošanas paņēmiens, kur R, Rj, R2, X un Y ir saskaņā ar 1. punktu, atšķiras ar to,ka amīdu, kura formula II irΝΗ-Υ-ΟΗ II kondensē ar aldehīdu, kurš atbilst formulai III, R-CHO III vai ar tā atvasinājumu vai priekšteci, skābā vidē, kura satur stipru minerālskābi un (C2-C4) alkanskābi vai molekulārā sietā sulfoskābes klātbūtnē, organiskā šķīdinātājā, tādā veidā iegūstot sastāvu, kura formula IV R,-3 - LV 11029 kur R3 ir (C2-4)acilgrupa vai ūdeņradis, kuru, ja R3 ir (C2_4)acilgrupa, pārvērš atbilstošā sastāvā, kura formula ir V,ar hidrolīzi; minētais paņēmiens tālāk raksturojas ar to, ka izraisa reakciju starp sastāvu, kura formula IV, kur R3 ir ūdeņradis vai sastāvs, kura formula ir V, un halogenēšanas aģentu, lai iegūtu sastāvu, kura formula ir VIkur halo ir halogēna atoms, ko pārvērš gala sastāvā, kura formula ir I, apstrādājot ar nitrēšanas aģentu, tādu kā sudraba nitrāts organiskā šķīdinātāja klātbūtnē pie temperatūras starp reakcijas maisījuma flegmas temperatūru un istabas temperatūru.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02239490A IT1244472B (it) | 1990-12-14 | 1990-12-14 | Benzossazinoni e benzotiazinoni ad attivita' cardiovascolare |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV11029A LV11029A (lv) | 1996-02-20 |
| LV11029B true LV11029B (en) | 1996-06-20 |
Family
ID=11195702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-95-218A LV11029B (en) | 1990-12-14 | 1995-07-20 | Benzoxazinone and benzothiazinone derivatives endowed with cardiovascular activity |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5189034A (lv) |
| EP (1) | EP0490183B1 (lv) |
| JP (1) | JP2512845B2 (lv) |
| KR (1) | KR960016124B1 (lv) |
| AT (1) | ATE121392T1 (lv) |
| AU (1) | AU644254B2 (lv) |
| CA (1) | CA2056814C (lv) |
| DE (2) | DE69109066T2 (lv) |
| DK (1) | DK0490183T3 (lv) |
| ES (1) | ES2051674T3 (lv) |
| FI (1) | FI95796C (lv) |
| GR (2) | GR920300088T1 (lv) |
| HU (1) | HUT63398A (lv) |
| IE (1) | IE67625B1 (lv) |
| IT (1) | IT1244472B (lv) |
| LV (1) | LV11029B (lv) |
| MX (1) | MX9102540A (lv) |
| NO (1) | NO180585C (lv) |
| NZ (1) | NZ240978A (lv) |
| PT (1) | PT99790B (lv) |
| TW (1) | TW233296B (lv) |
| ZA (1) | ZA919496B (lv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1245351B (it) * | 1991-03-19 | 1994-09-20 | Italfarmaco Spa | Isoindoli ad attivita' cardiovascolare |
| IT1254884B (it) * | 1992-04-16 | 1995-10-11 | Italfarmaco Spa | Benzossazinoni e benzotiazinoni ad attivita' cardiovascolare |
| IT1256023B (it) * | 1992-06-10 | 1995-11-20 | Italfarmaco Spa | Derivati benzossazinonici e benzotiazinonici ad attivita' cardiovascolare |
| CH685700A5 (fr) * | 1993-03-16 | 1995-09-15 | Cermol Sa | Esters nitriques de 1,2-benzo-isothiazolyl-3(2H)one-1,1-dioxyde, procédé de préparation de ces esters et médicaments contenant ces esters. |
| IT1264812B1 (it) * | 1993-07-28 | 1996-10-10 | Italfarmaco Spa | Derivati benzossazinonici e benzotiazinonici terapeuticamente attivi |
| JP4613082B2 (ja) | 2005-03-14 | 2011-01-12 | ヤンマー株式会社 | 作業車両のボンネット構造 |
| US8148368B2 (en) * | 2010-09-07 | 2012-04-03 | Shaikh Riazuddin | 7-nitro-2-(3-nitro phenyl)-4H-3,1-benzoxazin-4-one or derivatives thereof for treating or preventing antiviral infections |
| EP2707354B1 (en) * | 2011-10-24 | 2015-04-29 | Nicox Science Ireland | Quinone based nitric oxide donating compounds |
| KR102288434B1 (ko) * | 2018-10-18 | 2021-08-12 | 에이치케이이노엔 주식회사 | 신규한 (이소프로필-트리아졸릴)피리디닐 치환된 벤조옥사지논 또는 벤조티아지논 유도체 및 이의 용도 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459748A (en) * | 1967-04-28 | 1969-08-05 | Squibb & Sons Inc | Hydroxyalkylene-substituted benzoxazines and benzothiazines |
| US3513166A (en) * | 1967-05-22 | 1970-05-19 | Robins Co Inc A H | 3-(omega-aminoalkyl)-4-substituted-1,3-benzoxazine-2-ones |
| GB1274553A (en) * | 1969-05-06 | 1972-05-17 | Squibb & Sons Inc | Hydroxyalkylene-substituted benzoxazines and benzothiazines |
| JPS6137766A (ja) * | 1984-07-31 | 1986-02-22 | Sankyo Co Ltd | フタルイミド誘導体およびその製造法 |
| FR2636065B1 (fr) * | 1988-09-08 | 1993-05-07 | Fabre Sa Pierre | Nouveaux derives de dihydro-2,3 arylacoylaminoalcoyl-3 4h-benzoxazine-1,3 ones-4, leur preparation et leur application en tant que medicaments utiles en therapeutique |
-
1990
- 1990-12-14 IT IT02239490A patent/IT1244472B/it active IP Right Grant
-
1991
- 1991-11-29 AT AT91120471T patent/ATE121392T1/de not_active IP Right Cessation
- 1991-11-29 DK DK91120471.7T patent/DK0490183T3/da active
- 1991-11-29 DE DE69109066T patent/DE69109066T2/de not_active Expired - Fee Related
- 1991-11-29 ES ES91120471T patent/ES2051674T3/es not_active Expired - Lifetime
- 1991-11-29 EP EP91120471A patent/EP0490183B1/en not_active Expired - Lifetime
- 1991-11-29 DE DE199191120471T patent/DE490183T1/de active Pending
- 1991-12-02 TW TW080109468A patent/TW233296B/zh active
- 1991-12-02 ZA ZA919496A patent/ZA919496B/xx unknown
- 1991-12-05 CA CA002056814A patent/CA2056814C/en not_active Expired - Fee Related
- 1991-12-10 US US07/804,396 patent/US5189034A/en not_active Expired - Lifetime
- 1991-12-13 HU HU913950A patent/HUT63398A/hu unknown
- 1991-12-13 JP JP3330713A patent/JP2512845B2/ja not_active Expired - Fee Related
- 1991-12-13 NO NO914938A patent/NO180585C/no not_active IP Right Cessation
- 1991-12-13 NZ NZ240978A patent/NZ240978A/xx unknown
- 1991-12-13 AU AU89722/91A patent/AU644254B2/en not_active Ceased
- 1991-12-13 PT PT99790A patent/PT99790B/pt not_active IP Right Cessation
- 1991-12-13 FI FI915875A patent/FI95796C/fi active IP Right Grant
- 1991-12-13 IE IE434391A patent/IE67625B1/en not_active IP Right Cessation
- 1991-12-13 MX MX9102540A patent/MX9102540A/es not_active IP Right Cessation
- 1991-12-14 KR KR1019910023016A patent/KR960016124B1/ko not_active Expired - Fee Related
-
1992
- 1992-12-30 GR GR92300088T patent/GR920300088T1/el unknown
-
1995
- 1995-04-20 GR GR950400783T patent/GR3015901T3/el unknown
- 1995-07-20 LV LVP-95-218A patent/LV11029B/en unknown
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