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US4099002A
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Quinazolinone derivatives and a process for production thereof
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1974-08-08
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Granted: 1978-07-04
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Expires: 1994-08-08
Abstract
Abstract 3,4-Dihydro-2(1H)-quinazolinone derivatives of the formula, ##STR1## wherein R 1 and R 2 signify individually a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group, a lower alkylthio group, a lower alkylsulfonyl group or a halogen atom; R 3 signifies a phenyl group, a halophenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a trifluoromethylphenyl group, a lower cycloalkyl group, a lower cycloalkenyl group, a pyridyl group, a pyrrolyl group, a furyl group, a thienyl group or a naphthyl group; R 4 signifies a lower alkyl group, a lower alkenyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower cycloalkyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, a lower hydroxyalkyl group, a lower alkanoyloxyalkyl group, a phenyl group, a halophenyl group, a trifluoromethylphenyl group, a lower alkylphenyl group a lower alkoxyphenyl group, a pyridyl group or a group of the formula ##STR2## wherein n signifies an integer of 1 to 4; and R 5 and R 6 signify individually a lower alkyl group, provided that they may form together with the adjacent nitorgen atom an optionally substituted 5- or 6-membered heterocyclic ring, which may further contain a hetero atom); and R signifies a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower trihalomethylalkyl group or a group of the formula ##STR3## (wherein n, R 5 and R 6 signify the same as defined above), which have excellent pharmacological properties such as central nervous system depressant, anti-inflammatory, analgestic and anti-microbial activities, can be produced by reducing a compound of the formula, ##STR4## wherein R, R 1 , R 2 , R 3 and R 4 have the same meanings as defined above; and X 1 , X 2 and X 3 signify individually a halogen atom, or by the substitution reaction of the ring nitrogen atom of a 1 or 3-unsubstituted 3,4-dihydro-2(1H)-quinazolinone derivative.
Inventors
- 👤 Shigeho Inaba
- 👤 Michihiro Yamamoto
- 👤 Kikuo Ishizumi
- 👤 Kazuo Mori
- 👤 Masao Koshiba
- 👤 Hisao Yamamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:08
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/06; C07D239/00; C07D239/70; C07D239/72; C07D239/78; C07D239/80; C07D239/82; C07D413/00; C07D413/02; C07D413/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
86 words
A 3,4-dihydro-2(1H)-quinazolinone derivative represented by the formula, ##STR15## wherein R 1 and R 2 signify individually a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group, a lower alkylthio group, a lower alkylsulfonyl group or a halogen atom; R 3 is phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, trifluoromethylphenyl or naphthyl; and R" 4 is a group of the formula ##STR16## wherein n signifies an integer of 1 to 4, and R 5 and R 6 signify individually lower alkyl.
Claim 2
Dependent Claim
86 words
A 3,4-dihydro-2(1H)-quinazolinone derivative represented by the formula, ##STR15## wherein R 1 and R 2 signify individually a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group, a lower alkylthio group, a lower alkylsulfonyl group or a halogen atom; R 3 is phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, trifluoromethylphenyl or naphthyl; and R" 4 is a group of the formula ##STR16## wherein n signifies an integer of 1 to 4, and R 5 and R 6 signify individually lower alkyl.
Claim 3
Dependent Claim
65 words
A quinazolinone derivative of the formula, ##STR17## wherein R 1 and R 2 are independently hydrogen, lower alkyl, lower alkoxy, nitro, trifluoromethyl, lower alkylthio, lower alkylsulfonyl or halogen; R 3 is phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, trifluoromethylphenyl or naphthyl; and R" 4 is a group of the formula ##STR18## wherein n signifies an integer of 1 to 4 and ##STR19## forms piperidino or morpholino.
Claim 4
Dependent Claim
65 words
A quinazolinone derivative of the formula, ##STR17## wherein R 1 and R 2 are independently hydrogen, lower alkyl, lower alkoxy, nitro, trifluoromethyl, lower alkylthio, lower alkylsulfonyl or halogen; R 3 is phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, trifluoromethylphenyl or naphthyl; and R" 4 is a group of the formula ##STR18## wherein n signifies an integer of 1 to 4 and ##STR19## forms piperidino or morpholino.
Claim 5
Dependent Claim
10 words
A quinazolinone derivative according to claim 1 which is 3-(β-diethylaminoethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone.
Claim 6
Dependent Claim
53 words
3,4-Dihydro-2(1H)-quinazolinone derivatives represented by the formula, ##STR20## wherein R 1 and R 2 are individually a hydrogen atom or a halogen atom; R 3 is a phenyl group; and R" 4 is a group of the formula ##STR21## wherein n signifies an integer of 1 to 4 and ##STR22## forms piperidino or morpholino.
Claim 7
Dependent Claim
53 words
3,4-Dihydro-2(1H)-quinazolinone derivatives represented by the formula, ##STR20## wherein R 1 and R 2 are individually a hydrogen atom or a halogen atom; R 3 is a phenyl group; and R" 4 is a group of the formula ##STR21## wherein n signifies an integer of 1 to 4 and ##STR22## forms piperidino or morpholino.
Claim 8
Dependent Claim
16 words
A compound according to claim 4 wherein R 1 is hydrogen and R 2 is 6-halogeno.
Claim 9
Dependent Claim
16 words
A compound according to claim 4 wherein R 1 is hydrogen and R 2 is 6-chloro.
Claim 10
Dependent Claim
2 words
3-(β -Morpholinoethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone.
Claim 11
Dependent Claim
2 words
3-(β -Morpholinoethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinone.
Claim 12
Dependent Claim
325 words
A process for preparing 3,4-dihydro-2(1H)-quinazolinone drivatives represented by the formula, ##STR23## wherein R 1 and R 2 signify individually a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group, a lower alkylthio group, a lower alkylsulfonyl group or a halogen atom; R 3 signifies a phenyl group, a halophenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a trifluoromethylphenyl group, a lower cycloalkyl group, a lower cycloalkenyl group, a pyridyl group, a pyrrolyl group, a furyl group, a thienyl group or a naphthyl group; R 4 signifies a lower alkyl group, a lower alkenyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower cycloalkyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, a lower hydroxyalkyl group, a lower alkanoyloxyalkyl group, a phenyl group, a halophenyl group, a trifluoromethylphenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a pyridyl group or a group of the formula ##STR24## (wherein n signifies an integer of 1 to 4; and R 5 and R 6 signify individually a lower alkyl group, provided that they may form together with the adjacent nitrogen atom an optionally substituted 5- or 6-membered heterocyclic ring, which may further contain a hetero atom); and R signifies a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower trihalomethylalkyl group or a group of the formula ##STR25## (wherein n, R 5 and R 6 signify the same as defined above), which comprises reducing in a solvent with a reducing agent selected from the group consisting of (a) complex metal hydrides and (b) hydrogen together with a catalyst, a compound represented by the formula, ##STR26## wherein R, R 1 , R 2 , R 3 and R 4 have the same meanings as defined above; and X 1 , X 2 and X 3 signify individually a halogen atom.
Claim 13
Dependent Claim
325 words
A process for preparing 3,4-dihydro-2(1H)-quinazolinone drivatives represented by the formula, ##STR23## wherein R 1 and R 2 signify individually a hydrogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group, a lower alkylthio group, a lower alkylsulfonyl group or a halogen atom; R 3 signifies a phenyl group, a halophenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a trifluoromethylphenyl group, a lower cycloalkyl group, a lower cycloalkenyl group, a pyridyl group, a pyrrolyl group, a furyl group, a thienyl group or a naphthyl group; R 4 signifies a lower alkyl group, a lower alkenyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower cycloalkyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, a lower hydroxyalkyl group, a lower alkanoyloxyalkyl group, a phenyl group, a halophenyl group, a trifluoromethylphenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a pyridyl group or a group of the formula ##STR24## (wherein n signifies an integer of 1 to 4; and R 5 and R 6 signify individually a lower alkyl group, provided that they may form together with the adjacent nitrogen atom an optionally substituted 5- or 6-membered heterocyclic ring, which may further contain a hetero atom); and R signifies a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxyalkyl group, a lower alkylthioalkyl group, an aralkyl group, a lower cycloalkylalkyl group, a lower trihalomethylalkyl group or a group of the formula ##STR25## (wherein n, R 5 and R 6 signify the same as defined above), which comprises reducing in a solvent with a reducing agent selected from the group consisting of (a) complex metal hydrides and (b) hydrogen together with a catalyst, a compound represented by the formula, ##STR26## wherein R, R 1 , R 2 , R 3 and R 4 have the same meanings as defined above; and X 1 , X 2 and X 3 signify individually a halogen atom.
Claim 14
Dependent Claim
76 words
Process according to claim 8, wherein R 1 and R 2 are as defined in claim 8; R 3 is phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, trifluoromethylphenyl or naphthyl; R 4 is a group of the formula ##STR27## wherein n signifies an integer of 1 to 4, and R 5 and R 6 signify individually lower alkyl group; and R is hydrogen, lower alkyl, lower alkenyl, lower alkoxyalkyl, lower alkylthioalkyl, aralkyl, lower cycloalkylalkyl, or lower trihalomethylalkyl.
Claim 15
Dependent Claim
39 words
A process according to claim 8, wherein the solvent is at least one member selected from the group consisting of methanol, ethanol, isopropanol, methylene chloride, chloroform, carbon terachloride, ether, tetrahydrofuran, dimethylformamide, diethylformamide, dimethylacetamide, water, acetic acid and formic acid.
Claim 16
Dependent Claim
37 words
A process according to claim 8, wherein in the starting material of the formula [II] R is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower cycloalkylalkyl group or a lower alkoxyalkyl group.
References Cited (Backward Citations)
US3819627A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-03 | 1982-01-02 | 1982-07-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-03 | 1986-01-02 | 1986-07-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-03 | 1990-01-02 | 1990-07-04 | $7700.00 | Window Closed / Lapsed |