BE880720A - Nouveaux derives de 4(3h)-quinazolinone substitues en position 3 par une portion aromatique, leur preparation et leur utilisation - Google Patents

Nouveaux derives de 4(3h)-quinazolinone substitues en position 3 par une portion aromatique, leur preparation et leur utilisation Download PDF

Info

Publication number: BE880720A
Authority: BE; Belgium
Prior art keywords: group; emi; groups; compound; formula
Prior art date: 1978-12-19

Application number

BE0/198633A

Other languages

English (en)

French (fr)

Original Assignee

Masayuki Ishikawa

Priority date (The priority date 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 date listed.)

1978-12-19

Filing date

1979-12-19

Publication date

1980-06-19

1979-12-19 Application filed by Masayuki Ishikawa filed Critical Masayuki Ishikawa

1980-06-19 Publication of BE880720A publication Critical patent/BE880720A/fr

Links

QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical group C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 125
239000000203 mixture Substances 0.000 claims description 48
239000002253 acid Substances 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
239000000047 product Substances 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 21
-1 acetoxymethyl group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
239000007795 chemical reaction product Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
230000000879 anti-atherosclerotic effect Effects 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
208000001953 Hypotension Diseases 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
208000021822 hypotensive Diseases 0.000 claims description 5
230000001077 hypotensive effect Effects 0.000 claims description 5
125000004953 trihalomethyl group Chemical group 0.000 claims description 5
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000006372 monohalo methyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
JGICPIBJMZIJOF-UHFFFAOYSA-N ethyl 3-(2-chlorophenyl)-2,5,7-trimethyl-4-oxoquinazoline-6-carboxylate Chemical compound O=C1C2=C(C)C(C(=O)OCC)=C(C)C=C2N=C(C)N1C1=CC=CC=C1Cl JGICPIBJMZIJOF-UHFFFAOYSA-N 0.000 claims description 2
108090000623 proteins and genes Proteins 0.000 claims description 2
230000000304 vasodilatating effect Effects 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
KTPBRBKPQFPNCN-UHFFFAOYSA-N ethyl 2,5,7-trimethyl-3-(2-nitrophenyl)-4-oxoquinazoline-6-carboxylate Chemical compound O=C1C2=C(C)C(C(=O)OCC)=C(C)C=C2N=C(C)N1C1=CC=CC=C1[N+]([O-])=O KTPBRBKPQFPNCN-UHFFFAOYSA-N 0.000 claims 1
MCWQYUQZBJXMRL-UHFFFAOYSA-N ethyl 3-(2-chlorophenyl)-5,7-dimethyl-4-oxoquinazoline-6-carboxylate Chemical compound O=C1C2=C(C)C(C(=O)OCC)=C(C)C=C2N=CN1C1=CC=CC=C1Cl MCWQYUQZBJXMRL-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 28
239000010410 layer Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000003756 stirring Methods 0.000 description 21
239000002904 solvent Substances 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
239000000284 extract Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
229940124549 vasodilator Drugs 0.000 description 11
239000003071 vasodilator agent Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
238000005917 acylation reaction Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000005457 ice water Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
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 6
206010020772 Hypertension Diseases 0.000 description 6
230000010933 acylation Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
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 6
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 5
GNGNMHQUAACNST-UHFFFAOYSA-N 6-amino-3-ethoxycarbonyl-2,4-dimethylbenzoic acid Chemical compound CCOC(=O)C1=C(C)C=C(N)C(C(O)=O)=C1C GNGNMHQUAACNST-UHFFFAOYSA-N 0.000 description 5
201000001320 Atherosclerosis Diseases 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000003513 alkali Substances 0.000 description 4
210000004204 blood vessel Anatomy 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000000302 ischemic effect Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
210000003975 mesenteric artery Anatomy 0.000 description 4
CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
238000000746 purification Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 3
229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
210000000709 aorta Anatomy 0.000 description 3
210000001841 basilar artery Anatomy 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
XRCRCNXSQYQLAQ-UHFFFAOYSA-N methyl 2-amino-3,5-dimethylbenzoate Chemical compound COC(=O)C1=CC(C)=CC(C)=C1N XRCRCNXSQYQLAQ-UHFFFAOYSA-N 0.000 description 3
229960001789 papaverine Drugs 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000008096 xylene Substances 0.000 description 3
LYUPJHVGLFETDG-UHFFFAOYSA-N 1-phenylbutan-2-ol Chemical compound CCC(O)CC1=CC=CC=C1 LYUPJHVGLFETDG-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
238000011047 acute toxicity test Methods 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000003287 bathing Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
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238000006482 condensation reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
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238000011067 equilibration Methods 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
CWLKGDAVCFYWJK-UHFFFAOYSA-N m-Aminophenol Natural products NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000155 melt Substances 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
XXTISPYPIAPDGY-UHFFFAOYSA-N n,n-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1N(C=N)C1=CC=CC=C1 XXTISPYPIAPDGY-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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229920000137 polyphosphoric acid Polymers 0.000 description 2
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235000011164 potassium chloride Nutrition 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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239000011780 sodium chloride Substances 0.000 description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
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XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
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GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
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208000023589 ischemic disease Diseases 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical class CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
210000001363 mesenteric artery superior Anatomy 0.000 description 1
OEBNORXUIYOXGB-UHFFFAOYSA-N methyl 2-amino-4,5-dimethylbenzoate Chemical compound COC(=O)C1=CC(C)=C(C)C=C1N OEBNORXUIYOXGB-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
UKTHBCMHYFIUQD-UHFFFAOYSA-N n,n-bis(2,4-dimethylphenyl)methanimidamide Chemical compound CC1=CC(C)=CC=C1N(C=N)C1=CC=C(C)C=C1C UKTHBCMHYFIUQD-UHFFFAOYSA-N 0.000 description 1
VOOMGKLPBCQVAD-UHFFFAOYSA-N n,n-bis(2,6-difluorophenyl)methanimidamide Chemical compound FC1=CC=CC(F)=C1N(C=N)C1=C(F)C=CC=C1F VOOMGKLPBCQVAD-UHFFFAOYSA-N 0.000 description 1
MREQWMQNIBUQJW-UHFFFAOYSA-N n,n-bis(2-chlorophenyl)methanimidamide Chemical compound ClC1=CC=CC=C1N(C=N)C1=CC=CC=C1Cl MREQWMQNIBUQJW-UHFFFAOYSA-N 0.000 description 1
OHDYVFCQZVNDDL-UHFFFAOYSA-N n,n-bis(2-methylphenyl)methanimidamide Chemical compound CC1=CC=CC=C1N(C=N)C1=CC=CC=C1C OHDYVFCQZVNDDL-UHFFFAOYSA-N 0.000 description 1
DQQIPYLWUQWZAF-UHFFFAOYSA-N n,n-bis(3,4,5-trimethoxyphenyl)methanimidamide Chemical compound COC1=C(OC)C(OC)=CC(N(C=N)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 DQQIPYLWUQWZAF-UHFFFAOYSA-N 0.000 description 1
BZDAUNDIDZFYNB-UHFFFAOYSA-N n,n-bis(3,4-diethoxy-2-methylphenyl)methanimidamide Chemical compound CC1=C(OCC)C(OCC)=CC=C1N(C=N)C1=CC=C(OCC)C(OCC)=C1C BZDAUNDIDZFYNB-UHFFFAOYSA-N 0.000 description 1
STPJLGADMKQCMC-UHFFFAOYSA-N n,n-bis(3,4-dimethoxy-2-methylphenyl)methanimidamide Chemical compound CC1=C(OC)C(OC)=CC=C1N(C=N)C1=CC=C(OC)C(OC)=C1C STPJLGADMKQCMC-UHFFFAOYSA-N 0.000 description 1
VPUPOKLIZDNYRZ-UHFFFAOYSA-N n,n-bis(3,4-dimethylphenyl)methanimidamide Chemical compound C1=C(C)C(C)=CC=C1N(C=N)C1=CC=C(C)C(C)=C1 VPUPOKLIZDNYRZ-UHFFFAOYSA-N 0.000 description 1
QJAVKDDEZVOPJN-UHFFFAOYSA-N n,n-bis(4-ethoxy-2-methylphenyl)methanimidamide Chemical compound CC1=CC(OCC)=CC=C1N(C=N)C1=CC=C(OCC)C=C1C QJAVKDDEZVOPJN-UHFFFAOYSA-N 0.000 description 1
ZEGNGIRBYAVBDL-UHFFFAOYSA-N n,n-bis(4-methoxy-2-methylphenyl)methanimidamide Chemical compound CC1=CC(OC)=CC=C1N(C=N)C1=CC=C(OC)C=C1C ZEGNGIRBYAVBDL-UHFFFAOYSA-N 0.000 description 1
JJPVPZCTSPHRIR-UHFFFAOYSA-N n,n-bis(4-methylphenyl)methanimidamide Chemical compound C1=CC(C)=CC=C1N(C=N)C1=CC=C(C)C=C1 JJPVPZCTSPHRIR-UHFFFAOYSA-N 0.000 description 1
GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000002245 particle Substances 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000003944 tolyl group Chemical group 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
PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- 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
- 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
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BE0/198633A 1978-12-19 1979-12-19 Nouveaux derives de 4(3h)-quinazolinone substitues en position 3 par une portion aromatique, leur preparation et leur utilisation BE880720A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15576478A JPS5583761A (en)	1978-12-19	1978-12-19	Novel 3-phenyl-4-quinazolone derivative

Publications (1)

Publication Number	Publication Date
BE880720A true BE880720A (fr)	1980-06-19

Family

ID=15612890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/198633A BE880720A (fr)	1978-12-19	1979-12-19	Nouveaux derives de 4(3h)-quinazolinone substitues en position 3 par une portion aromatique, leur preparation et leur utilisation

Country Status (4)

Country	Link
JP (1)	JPS5583761A (de)
AT (1)	AT375651B (de)
BE (1)	BE880720A (de)
ZA (1)	ZA796892B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59106195A (ja) *	1982-12-10	1984-06-19	富士通株式会社	厚膜パタ−ン印刷回数表示方法

1978
- 1978-12-19 JP JP15576478A patent/JPS5583761A/ja active Pending
1979
- 1979-12-19 AT AT0801179A patent/AT375651B/de not_active IP Right Cessation
- 1979-12-19 BE BE0/198633A patent/BE880720A/fr not_active IP Right Cessation
- 1979-12-19 ZA ZA00796892A patent/ZA796892B/xx unknown

Also Published As

Publication number	Publication date
JPS5583761A (en)	1980-06-24
AT375651B (de)	1984-08-27
ZA796892B (en)	1980-12-31
ATA801179A (de)	1984-01-15

Legal Events

Date

Code

Title

Description

1985-06-30

RE

Patent lapsed

Owner name: ISHIKAWA MASAYUKI

Effective date: 19841219

Publication	Publication Date	Title
US4490371A (en)	1984-12-25	N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides
FR2529547A1 (fr)	1984-01-06	Derives n-imidazolyliques de composes bicycliques, leur procede de preparation et leur utilisation dans le reglage de l'hemostase vasculaire
CA1152507A (fr)	1983-08-23	PROCEDE DE PREPARATION DES ARYL-1 ARYLSULFONYL-4 .alpha.-AMINO-PROPOXY-3 1H-PYRAZOLES
FR2534257A1 (fr)	1984-04-13	Nouveaux derives de la 6-amino 7-hydroxy 4,5,6,7-tetrahydro-imidazo/4,5,1-j-k/ /1/ benzazepin-2(1h)-one, leurs sels, application a titre de medicaments, compositions les renfermant et un intermediaire
CH653025A5 (fr)	1985-12-13	Oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique.
CH624952A5 (de)	1981-08-31
CA1208226A (fr)	1986-07-22	Procede de preparation de nouveaux derives du 4h-1,2, 4-triazole
MC1333A1 (fr)	1981-04-21	Derives de quinazoline
EP0049555A1 (de)	1982-04-14	Derivate von 2-Trifluormethyl-4-hydroxy-3-chinolin-carbonsäuren und Verfahren zu ihrer Herstellung
FR2647676A1 (fr)	1990-12-07	Nouveaux derives de pyridazinone, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase
CH646967A5 (fr)	1984-12-28	Composes de pyranone et compositions pharmaceutiques les comprenant.
MC1706A1 (fr)	1986-09-22	Dérivés de tétrahydronaphtalène
CA1097647A (fr)	1981-03-17	Procede de preparation de nouvelles imidazoquinoleines et de leurs sels
EP0040573A2 (de)	1981-11-25	2-Substituierte 4-Hydroxy-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel, diese enthaltende Zubereitungen und Zwischenprodukte
EP0269599B1 (de)	1993-12-15	Substituierte 1H-Imidazole
EP0021940B1 (de)	1983-01-19	Aminoderivate von Benzothiazol, Verfahren zu ihrer Herstellung und ihre Anwendung in der Heilkunde
EP0022408A1 (de)	1981-01-14	Alpha-Phenyl-2-pyrrolidinmethanol-Derivate und ihre Salze, Verfahren zur Herstellung, Verwendung als Arzneimittel und sie enthaltende Zusammensetzungen
EP0028959B1 (de)	1985-01-30	5,8,13,13a -Tetrahydro-6H-dibenzo(a,g)chinolizin-Derivate, Verfahren zur Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
BE880720A (fr)	1980-06-19	Nouveaux derives de 4(3h)-quinazolinone substitues en position 3 par une portion aromatique, leur preparation et leur utilisation
CH623053A5 (en)	1981-05-15	Processes for the preparation of new imidazobenzoxazines
CA1313871C (fr)	1993-02-23	Derives de l'acide (dihydro-2,3 oxo-2 benzofurannyl-3)-2 acetique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
FR2599033A1 (fr)	1987-11-27	Derives des 3-(hydroxymethyl)-isoquinoleine, procede pour les preparer et compositions pharmaceutiques les contenant
EP0362006A1 (de)	1990-04-04	Chinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0233801B1 (de)	1990-05-23	Substituierte Amide, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0281471B1 (de)	1990-05-02	2,3-Dihydro-3-phenyl-benzofuran-2-on-Acetamidderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel