GB936902A - Quinazolinone derivatives - Google Patents
Quinazolinone derivativesInfo
- Publication number
- GB936902A GB936902A GB9836/62A GB983662A GB936902A GB 936902 A GB936902 A GB 936902A GB 9836/62 A GB9836/62 A GB 9836/62A GB 983662 A GB983662 A GB 983662A GB 936902 A GB936902 A GB 936902A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- methylphenyl
- isopropyl
- formula
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract 2
- -1 o-methylphenyl Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000002253 acid Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003434 antitussive agent Substances 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960004126 codeine Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003326 hypnotic agent Substances 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229960003893 phenacetin Drugs 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229960002189 propyphenazone Drugs 0.000 abstract 1
- PXWLVJLKJGVOKE-UHFFFAOYSA-N propyphenazone Chemical compound O=C1C(C(C)C)=C(C)N(C)N1C1=CC=CC=C1 PXWLVJLKJGVOKE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 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
- C07D239/94—Nitrogen atoms
-
- 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
-
- 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
-
- 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a quinazolinone derivative of the formula: <FORM:0936902/IV(a)/1> wherein R represents hydrogen, a methyl radical or an isopropyl radical, an R1 represents an o-methylphenyl, o-chlorophenyl, o-bromophenyl, o,o1 or o,p-dimethylphenyl radical when R is hydrogen, R1 represents an o-ethylphenyl, o-hydroxyphenyl, o-S-methylphenyl, or o,o1-chloro-methylphenyl radical when R is methyl and R1 represents an o-methylphenyl radical when R is isopropyl, or acid addition salts thereof which have therapeutically acceptable anions, and a process for the preparation thereof by condensing a compound of the formula: <FORM:0936902/IV(a)/2> in the presence of an acid condensing agent with a compound of the formula R1NH2. The condensation may be effected in the presence of phosphorus pentachloride in nitrobenzene as solvent. Specifications 642,134 and 843,073 are referred to.ALSO:Quinazolinone compounds having the formula <FORM:0936902/VI/1> wherein R represents hydrogen, a methyl radical or an isopropyl radical, and R1 represents o-methylphenyl, o-chlorophenyl, o-bromophenyl, o,o1- or o,p-dimethylphenyl radical, when R is hydrogen, R1 represents an o-ethylphenyl, o-hydroxyphenyl, o-S-methylphenyl, or o,o1-chloro-methylphenyl radical, when R is methyl and R1 represents an o-methylphenyl radical, when R is isopropyl or acid addition salts thereof which haved therapeutically acceptable anions, are employed as spasmolytics and hypnotics and may be used to intensify the analgesic action of weak analgesics, e.g. phenacetin, isopropyl phenazone and codeine, or the activity of known antitussive agents. Specifications 642,134 and 843,073 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB61759A DE1224316B (en) | 1961-03-18 | 1961-03-18 | Process for the preparation of 2-methyl-3- (o-aethylphenyl) -4-oxo-3, 4-dihydroquinazoline and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB936902A true GB936902A (en) | 1963-09-18 |
Family
ID=6973320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9836/62A Expired GB936902A (en) | 1961-03-18 | 1962-03-14 | Quinazolinone derivatives |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE615282A (en) |
| CH (1) | CH416653A (en) |
| DE (1) | DE1224316B (en) |
| GB (1) | GB936902A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462434A (en) * | 1965-05-05 | 1969-08-19 | Boehringer Sohn Ingelheim | 2-isopropyl-3-(p-amino-phenyl)-3h-4-quinazolone |
| US7960399B2 (en) | 2004-06-08 | 2011-06-14 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB642134A (en) * | 1945-04-07 | 1950-08-30 | Gen Aniline & Film Corp | Preparation of quinazolones |
| GB843073A (en) * | 1958-05-09 | 1960-08-04 | Toraude Lab | 2-methyl-3-orthotolyl-4-quinazolone and acid addition salts thereof |
-
1961
- 1961-03-18 DE DEB61759A patent/DE1224316B/en active Pending
-
1962
- 1962-03-14 GB GB9836/62A patent/GB936902A/en not_active Expired
- 1962-03-16 CH CH320962A patent/CH416653A/en unknown
- 1962-03-19 BE BE615282A patent/BE615282A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462434A (en) * | 1965-05-05 | 1969-08-19 | Boehringer Sohn Ingelheim | 2-isopropyl-3-(p-amino-phenyl)-3h-4-quinazolone |
| US7960399B2 (en) | 2004-06-08 | 2011-06-14 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US8211902B2 (en) | 2004-06-08 | 2012-07-03 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US8809528B2 (en) | 2004-06-08 | 2014-08-19 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US9102653B2 (en) | 2004-06-08 | 2015-08-11 | Novartis Ag | Substituted quinazolinones as vanilloid antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1224316B (en) | 1966-09-08 |
| CH416653A (en) | 1966-07-15 |
| BE615282A (en) | 1962-09-19 |
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