DD150462A5 - Verfahren zur herstellung von in 3-stellung mit aromatischer gruppe substituierten 4(3h)-chinazolinonen - Google Patents

Verfahren zur herstellung von in 3-stellung mit aromatischer gruppe substituierten 4(3h)-chinazolinonen Download PDF

Info

Publication number: DD150462A5
Authority: DD; German Democratic Republic
Prior art keywords: group; compound; formula; hydrogen atom; acid
Prior art date: 1978-12-19

Application number

DD79217854A

Other languages

German (de)

English (en)

Inventor

Masayuki Ishikawa

Hiromichi Tanaka

Yukuo Eguchi

Shigeru Ito

Yoshimi Takashima

Masahiko Kobayashi

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

1981-09-02

1978-12-19 Priority claimed from JP15576478A external-priority patent/JPS5583761A/ja

1979-10-03 Priority claimed from JP12673879A external-priority patent/JPS5651461A/ja

1979-10-18 Priority claimed from JP13358279A external-priority patent/JPS5657768A/ja

1979-11-05 Priority claimed from JP14198779A external-priority patent/JPS5665877A/ja

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

1981-09-02 Publication of DD150462A5 publication Critical patent/DD150462A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 137
-1 3-substituted-4 (3H) -quinazolinones Chemical class 0.000 claims abstract description 48
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
238000000034 method Methods 0.000 claims abstract description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
230000008569 process Effects 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 8
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims description 31
239000000047 product Substances 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 8
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
125000006372 monohalo methyl group Chemical group 0.000 claims 1
201000001320 Atherosclerosis Diseases 0.000 abstract description 7
208000001953 Hypotension Diseases 0.000 abstract description 7
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 7
229910052739 hydrogen Inorganic materials 0.000 abstract description 7
208000021822 hypotensive Diseases 0.000 abstract description 7
230000001077 hypotensive effect Effects 0.000 abstract description 7
230000000304 vasodilatating effect Effects 0.000 abstract description 7
206010020772 Hypertension Diseases 0.000 abstract description 6
239000001257 hydrogen Substances 0.000 abstract description 6
230000000302 ischemic effect Effects 0.000 abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
208000018152 Cerebral disease Diseases 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
230000002048 spasmolytic effect Effects 0.000 abstract description 3
239000000812 cholinergic antagonist Substances 0.000 abstract description 2
208000031225 myocardial ischemia Diseases 0.000 abstract description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 152
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
235000019441 ethanol Nutrition 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 30
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 24
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
238000003756 stirring Methods 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 14
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
239000000284 extract Substances 0.000 description 13
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229910052757 nitrogen Inorganic materials 0.000 description 13
238000012360 testing method Methods 0.000 description 11
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238000005917 acylation reaction Methods 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000005457 ice water Substances 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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 8
238000010992 reflux Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003071 vasodilator agent Substances 0.000 description 7
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
230000010933 acylation Effects 0.000 description 6
210000001841 basilar artery Anatomy 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
229940124549 vasodilator Drugs 0.000 description 6
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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000003513 alkali Substances 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
210000004204 blood vessel Anatomy 0.000 description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
238000000746 purification Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
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
210000000709 aorta 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
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000002955 isolation Methods 0.000 description 4
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125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 4
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238000001953 recrystallisation Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 3
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
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241000699670 Mus sp. Species 0.000 description 3
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
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239000000969 carrier Substances 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
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210000003975 mesenteric artery Anatomy 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
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GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical compound NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
XGZNTUBWIASUQW-UHFFFAOYSA-N 2-amino-4-ethoxycarbonyl-3,5-dimethylbenzoic acid Chemical compound CCOC(=O)C1=C(C)C=C(C(O)=O)C(N)=C1C XGZNTUBWIASUQW-UHFFFAOYSA-N 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
WAIHFZPSLVDBRV-UHFFFAOYSA-N 3-phenylquinazolin-4-one Chemical class C1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1 WAIHFZPSLVDBRV-UHFFFAOYSA-N 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
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
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PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 2
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IXWUXVSEQHFPMI-UHFFFAOYSA-N ethyl 5,7-dimethyl-4-oxo-3-phenylquinazoline-6-carboxylate Chemical compound O=C1C2=C(C)C(C(=O)OCC)=C(C)C=C2N=CN1C1=CC=CC=C1 IXWUXVSEQHFPMI-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
NIPYIXMXODGEES-UHFFFAOYSA-N hexanoyl bromide Chemical compound CCCCCC(Br)=O NIPYIXMXODGEES-UHFFFAOYSA-N 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000010348 incorporation Methods 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
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000004994 m-toluidines Chemical class 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
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
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CJCNXAKLVTWRAO-UHFFFAOYSA-N n,n-bis(2,6-dichlorophenyl)methanimidamide Chemical compound ClC1=CC=CC(Cl)=C1N(C=N)C1=C(Cl)C=CC=C1Cl CJCNXAKLVTWRAO-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
GUKXELVADQQHQP-UHFFFAOYSA-N n,n-bis(3,4-dimethoxyphenyl)methanimidamide Chemical compound C1=C(OC)C(OC)=CC=C1N(C=N)C1=CC=C(OC)C(OC)=C1 GUKXELVADQQHQP-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
SMGHFKFQYWSQGL-UHFFFAOYSA-N n,n-bis(3-methylphenyl)methanimidamide Chemical compound CC1=CC=CC(N(C=N)C=2C=C(C)C=CC=2)=C1 SMGHFKFQYWSQGL-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
125000004433 nitrogen atom Chemical group 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
150000004993 o-toluidines Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical class 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
150000004995 p-toluidines Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 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
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
210000002460 smooth muscle Anatomy 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD79217854A 1978-12-19 1979-12-19 Verfahren zur herstellung von in 3-stellung mit aromatischer gruppe substituierten 4(3h)-chinazolinonen DD150462A5 (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP15576478A JPS5583761A (en)	1978-12-19	1978-12-19	Novel 3-phenyl-4-quinazolone derivative
JP12673879A JPS5651461A (en)	1979-10-03	1979-10-03	Novel 3-phenyl-4-quinazolone derivative
JP13358279A JPS5657768A (en)	1979-10-18	1979-10-18	Novel 4-quinazolone derivative substituted by aromatic residue at 3-position
JP14198779A JPS5665877A (en)	1979-11-05	1979-11-05	Preparation of 4-quinazolone derivative

Publications (1)

Publication Number	Publication Date
DD150462A5 true DD150462A5 (de)	1981-09-02

Family

ID=27471233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79217854A DD150462A5 (de)	1978-12-19	1979-12-19	Verfahren zur herstellung von in 3-stellung mit aromatischer gruppe substituierten 4(3h)-chinazolinonen

Country Status (16)

Country	Link
US (1)	US4276295A (it)
AR (1)	AR225028A1 (it)
AU (1)	AU526309B2 (it)
CH (1)	CH644112A5 (it)
DD (1)	DD150462A5 (it)
DE (1)	DE2950376A1 (it)
DK (1)	DK539979A (it)
FR (1)	FR2444671A1 (it)
GB (1)	GB2040927B (it)
HU (1)	HU182733B (it)
IT (1)	IT1126577B (it)
NL (1)	NL7909118A (it)
NO (1)	NO794135L (it)
NZ (1)	NZ192392A (it)
SE (1)	SE7910376L (it)
YU (1)	YU306379A (it)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1161036A (en) *	1980-05-15	1984-01-24	Masayuki Ishikawa	Quinazoline-dione compounds, process for production thereof and pharmaceutical use thereof
AU543928B2 (en) *	1981-01-16	1985-05-09	Masayuki Ishikawa	4(311)-quinazolinone derivatives
US4419357A (en) *	1982-01-18	1983-12-06	The Dow Chemical Company	3-(1H-Tetrazol-5-yl)-4(3H)-quinazolinones
US4684654A (en) *	1985-08-14	1987-08-04	American Cyanamid Company	3-heteroalkyl-2,4-quinzaolinediones
EP0293500A1 (en) *	1987-06-01	1988-12-07	American Cyanamid Company	3-heteroalkyl-2,4.quinzaoline-diones
JPH05504969A (ja) *	1990-02-13	1993-07-29	メルク・エンド・カムパニー・インコーポレーテツド	置換ベンジル要素を含有するアンギオテンシン２アンタゴニスト類
US5075313A (en) *	1990-09-13	1991-12-24	Eli Lilly And Company	3-aryl-4(3H)quinazolinone CCK antagonists and pharmaceutical formulations thereof
US5283247A (en) *	1991-02-06	1994-02-01	Research Corporation Technologies, Inc.	Anticonvulsant substituted quinazolones
WO1992013535A1 (en) *	1991-02-06	1992-08-20	Research Corporation Technologies, Inc.	Anticonvulsant substituted quinazolones
WO1994026722A1 (en) *	1993-05-12	1994-11-24	E.I. Du Pont De Nemours And Company	Fungicidal fused bicyclic pyrimidinones
US5756502A (en) *	1994-08-08	1998-05-26	Warner-Lambert Company	Quinazolinone derivatives as cholyecystokinin (CCK) ligands
US6255311B1 (en) *	1998-01-14	2001-07-03	E. I. Du Pont De Nemours And Company	Fungicidal fused bicyclic pyrimidinones
AU2002214546A1 (en) *	2000-09-29	2002-04-08	Cor Therapeutics, Inc.	Bicyclic pyrimidin-4-one based inhibitors of factor xa
TW200306839A (en) *	2002-02-06	2003-12-01	Novartis Ag	Quinazolinone derivatives and their use as CB agonists
AU2007202781B2 (en) *	2002-02-06	2010-09-09	Novartis Ag	Quinazolinone derivatives and their use as CB agonists
RU2358969C2 (ru) *	2004-02-13	2009-06-20	Баниу Фармасьютикал Ко., Лтд.	Конденсированное 4-оксопиримидиновое производное
AU2013246278B2 (en) *	2012-04-10	2016-11-03	Annji Pharmaceutical Co., Ltd.	Histone deacetylases (HDAC) inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3047462A (en) *	1959-03-06	1962-07-31	Lab Jacques Logeais Soc D Expl	Quinazolone anti-inflammatory composition
DE1695799C3 (de) *	1967-01-23	1974-10-17	Sumitomo Chemical Co., Ltd., Osaka (Japan)	5-Chlor-3- eckige Klammer auf pyridin-2'-yl eckige Klammer zu -4-(3H)- chinazolinone
JPS5516425B2 (it) *	1972-09-19	1980-05-01
JPS5521748B2 (it) *	1972-09-19	1980-06-12

1979
- 1979-12-13 NZ NZ192392A patent/NZ192392A/xx unknown
- 1979-12-14 US US06/103,841 patent/US4276295A/en not_active Expired - Lifetime
- 1979-12-14 YU YU03063/79A patent/YU306379A/xx unknown
- 1979-12-14 DE DE19792950376 patent/DE2950376A1/de not_active Withdrawn
- 1979-12-17 IT IT28062/79A patent/IT1126577B/it active
- 1979-12-17 AU AU53932/79A patent/AU526309B2/en not_active Ceased
- 1979-12-17 SE SE7910376A patent/SE7910376L/xx not_active Application Discontinuation
- 1979-12-17 AR AR279316A patent/AR225028A1/es active
- 1979-12-18 DK DK539979A patent/DK539979A/da not_active Application Discontinuation
- 1979-12-18 NL NL7909118A patent/NL7909118A/nl not_active Application Discontinuation
- 1979-12-18 GB GB7943565A patent/GB2040927B/en not_active Expired
- 1979-12-18 NO NO794135A patent/NO794135L/no unknown
- 1979-12-19 FR FR7931059A patent/FR2444671A1/fr active Granted
- 1979-12-19 CH CH1125779A patent/CH644112A5/de not_active IP Right Cessation
- 1979-12-19 HU HU79II311A patent/HU182733B/hu unknown
- 1979-12-19 DD DD79217854A patent/DD150462A5/de unknown

Also Published As

Publication number	Publication date
AR225028A1 (es)	1982-02-15
GB2040927A (en)	1980-09-03
CH644112A5 (de)	1984-07-13
US4276295A (en)	1981-06-30
NL7909118A (nl)	1980-06-23
FR2444671B1 (it)	1983-06-10
IT7928062A0 (it)	1979-12-17
NZ192392A (en)	1983-02-15
NO794135L (no)	1980-06-20
GB2040927B (en)	1983-01-26
YU306379A (en)	1983-12-31
IT1126577B (it)	1986-05-21
AU526309B2 (en)	1983-01-06
AU5393279A (en)	1980-06-26
SE7910376L (sv)	1980-06-20
DK539979A (da)	1980-06-20
FR2444671A1 (fr)	1980-07-18
HU182733B (en)	1984-03-28
DE2950376A1 (de)	1980-07-10

Publication	Publication Date	Title
DD150462A5 (de)	1981-09-02	Verfahren zur herstellung von in 3-stellung mit aromatischer gruppe substituierten 4(3h)-chinazolinonen
DE69232060T2 (de)	2002-04-18	Stickstoff enthaltende bicyclische Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zusammensetzungen
EP0004279B1 (de)	1982-12-29	Verfahren zur Herstellung von 4-Pyridon-3-carbonsäuren, 1-Cyclopropyl-4-Pyridon-3-Carbonsäurederivate und diese enthaltende Arzneimittel
CH650782A5 (de)	1985-08-15	Carbostyrilverbindungen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten.
DE3224512A1 (de)	1984-01-05	Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel
DE2559509A1 (de)	1976-12-30	Benzcyloamidderivate und verfahren zu ihrer herstellung sowie pharmazeutische mittel, worin sie enthalten sind
DE3033157A1 (de)	1982-04-01	7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE69015541T2 (de)	1995-06-01	Chinolinderivate, deren Herstellung und Verwendung.
EP0022078B1 (de)	1984-07-25	Pyrazolochinoline, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate enthaltend diese Verbindungen
EP0557879A1 (de)	1993-09-01	4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
EP0019172A1 (de)	1980-11-26	6-Substituierte 11-Alkylen-morphantridine, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel
US5900426A (en)	1999-05-04	Benzothiazole derivatives
DE2064520C3 (de)	1980-05-22	In 2-Stellung substituierte 4,5-Diarylimidazole, Verfahren zu ihrer Herstellung und therapeutische Präparate mit einem Gehalt an diesen Verbindungen
EP0121490B1 (de)	1988-03-02	Substituierte 6-Aryl-1,2,4-triazolo[4,3-b]pyridazine, ihre Herstellung und Verwendung
DE2424671A1 (de)	1974-12-12	Triazoloisochinolinderivate und verfahren zu deren herstellung
DE2832358C2 (it)	1989-12-07
DE2903850A1 (de)	1980-08-07	2-amino-8-cyclopropyl-5-oxo-5,8- dihydro-pyrido eckige klammer auf 2,3-d eckige klammer zu -pyrimidin-6-carnonsaeuren, verfahren zu ihrer herstellung sowie ihrer verwendung als antibakterielle mittel
AT398075B (de)	1994-09-26	Verfahren zur herstellung von chinazolinderivaten
DE3027619A1 (de)	1981-02-19	6-alkyl-7-phenyl-1,6-naphtyradin- 5(6h)-on-derivate
IE49469B1 (en)	1985-10-16	Substituted quinazolines
CH461489A (de)	1968-08-31	Verfahren zur Herstellung von neuen Oxazolderivaten
DE2811361A1 (de)	1979-09-27	Neue isochinolinaldehyde und verfahren zu ihrer herstellung
EP0439766A2 (de)	1991-08-07	Verfahren zur Herstellung von N-Acyl-4-phenyl-pyrrolidin-2-onen mit cerebroprotektiver Wirkung
US4371543A (en)	1983-02-01	Bis-amidine indene ketones, compositions containing same and method of use
DE2448259A1 (de)	1976-04-22	Verfahren zur herstellung von 2-halogenmethyl-1,4-benzodiazepinen