US3652567A - Quinazolinone derivative and process for the production thereof - Google Patents
Quinazolinone derivative and process for the production thereof Download PDFInfo
- Publication number
- US3652567A US3652567A US866719A US3652567DA US3652567A US 3652567 A US3652567 A US 3652567A US 866719 A US866719 A US 866719A US 3652567D A US3652567D A US 3652567DA US 3652567 A US3652567 A US 3652567A
- Authority
- US
- United States
- Prior art keywords
- methyl
- quinazoline
- hydroxypropyl
- phenylpiperazine
- compound
- 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 - Lifetime
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000000202 analgesic effect Effects 0.000 abstract description 6
- 230000000954 anitussive effect Effects 0.000 abstract description 6
- 229940124584 antitussives Drugs 0.000 abstract description 5
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract description 5
- -1 QUINAZOLINONE COMPOUND Chemical class 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 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 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960004126 codeine Drugs 0.000 description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
- FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 3
- SLBNBTYQYOJGTQ-UHFFFAOYSA-N 3-(3-bromo-2-hydroxypropyl)-2-methylquinazolin-4-one Chemical compound CC1=NC2=CC=CC=C2C(N1CC(CBr)O)=O SLBNBTYQYOJGTQ-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- LYTDCCLXRGTWMX-UHFFFAOYSA-N 2-methyl-3-(oxiran-2-ylmethyl)quinazolin-4-one Chemical compound CC1=NC2=CC=CC=C2C(N1CC1CO1)=O LYTDCCLXRGTWMX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002082 anti-convulsion Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 3H-quinazolinyl-4-one Natural products C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 1
- VWCUGCYZZGRKEE-UHFFFAOYSA-N Noracymethadol Chemical compound C=1C=CC=CC=1C(CC(C)NC)(C(OC(C)=O)CC)C1=CC=CC=C1 VWCUGCYZZGRKEE-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
- H01F27/00—Details of transformers or inductances, in general
Definitions
- This invention relates to a new quinazolinone derivative and to a process for the production thereof.
- the invention provides as a new chemical compound 2-methy1-3- ⁇ 3-[4-phenylpiperazinyl-(1)] 2 hydroxypropyl ⁇ -quinazoline-4-one (hereinafter referred to as I) having the following formula:
- the LD values with the mouse are very high, being mg./kg. intravenously and 710 mg./kg. per os; 500 mg./ kg. per os are tolerated without reaction by the rabbit. This shows a very low toxicity of the compound I.
- the compound according to the invention may be prepared by the condensation of l-phenylpiperazine with 2- methyl-3-[3-bromo-2-hydroxypropyl] quinazoline-4-one or by the addition to it of 2-methyl-3- [2,3-epoxypropyl1- quinazoline-4-one or by condensing 2-methylquinazoline- 4-one with epichlorhydrin and then adding to it l-phenylpiperazine preferably without isolation of the intermediate.
- the invention therefore also provides a process for the preparation of the 2-methyl-3- ⁇ 3 [4 phenylpiperazinyl- (1) ]-2-hydroxypropyl ⁇ -quinazo1ine-4-one in which (a) l-phenylpiperazine is condensed with 2-methyl-3- [3-bromo-2-hydroxypropyl]-quinazoline-4-one or (b) 2 methyl-3-[2,3-epoxypropyl]-quinazoline-4-one is reacted with l-phenylpiperazine; or
- the reactions can be carried out in the absence of solvents at temperatures above C. and also in the presence of organic solvents, such as ethyl alcohol, at room temperature or higher temperature.
- the compound according to the invention may be formulated with a pharmaceutical carrier to provide formulations adapted for the particular route of administration in particular the oral route, for example in the form of a syrup, elixir or the like or as a tablet or capsule.
- EXAMPLE 2 10.8 g. of 2-methyl-3-(2,3-epoxypropyl)-quinazoline-4- one and 8.1 g. of l-phenylpiperazine are boiled for 4 hours in 70 ml. of absolute ethanol and the solution is kept for several hours at room temperature and then in the cold. The substance which precipitates is filtered 01?, the contents of the filter are washed-with ether and then crystallised from ethanol. 14.2 g. of 2-methyl-3- ⁇ 3-[4- phenylpiperazinyl 1 ]-2-hydroxypropyl ⁇ -quinazoline-4- one are formed, corresponding to 75% of the theoretical.
- EXAMPLE 3 29.2 g. of 2-methylquinazoline-4-one and 70 m1. 82.5 g.) of epichlorhydrin are dissolved in methanol and then an equimolar quantity of sodium methylate in methanol is added. After standing for 12 hours at room temperature, the viscous mass which forms (39.6 g.) is filtered off, removed from the filter and maintained with 44.5 g. of l-phenylpiperazine for 30 minutes in an oil bath at 110 C. The mass (84 g. crude yield) is then worked up as previously described.
- wa 2-methyl-3- ⁇ 3-[4-phenylpiperaziny1-(1) ]-2-hydroxypropyl ⁇ quinazolin-4-one.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A QUINAZOLINONE COMPOUND OF THE FORMULA:
2-(CH3-),3-((4-PHENYL-PIPERAZINO)-CH2-CH(-OH)-CH2-),4-(O=)
-QUINAZOLINE
2-METHYL-3-(3-(4-PHENYLPIPERAZINYL-(1)-2-HYDROXYPROPYL)-QUINAZOLINE-4-ONE. THIS COMPOUND HAS ANTITUSSIVE AND ANALGESIC ACTIVITY.
2-(CH3-),3-((4-PHENYL-PIPERAZINO)-CH2-CH(-OH)-CH2-),4-(O=)
-QUINAZOLINE
2-METHYL-3-(3-(4-PHENYLPIPERAZINYL-(1)-2-HYDROXYPROPYL)-QUINAZOLINE-4-ONE. THIS COMPOUND HAS ANTITUSSIVE AND ANALGESIC ACTIVITY.
Description
US. Cl. 260---256.4 Q 1 Claim ABSTRACT OF THE DISCLOSURE A quinazolinone compound of the formula:
N-oH,( H-CHt-N 2-methyl-3-{3-[4-phenylpiperazinyl-(1)] 2 hydroxypropyl}-quinazoline-4-one. This compound 'has antitussive and analgesic activity.
on N a This invention relates to a new quinazolinone derivative and to a process for the production thereof.
The invention provides as a new chemical compound 2-methy1-3-{3-[4-phenylpiperazinyl-(1)] 2 hydroxypropyl}-quinazoline-4-one (hereinafter referred to as I) having the following formula:
This compound is effective as an analgesic and antitussive, as more fully described below.
Quinazolinone derivatives are already known and common as drugs for use in human medicine.
As examples of such derivatives there may be mentioned 2-methyl-3-o-tolylquinazoline 4- one, which has anti-convulsive, sedative and hypnotic activity and 2- methyl-3-o-ethylphenylquinazoline -4 one, which has a hypnotic action. In addition certain other quinazolinone derivatives are reputed to be active against malaria.
It has now been found that the aforementioned pharmacological efiects are completely overshadowed in favour of an antitussive and analgesic quality, if the substituted phenyl ring on the quinazolinone skeleton in the 3-position is replaced by a 3-[4-phenylpiperazinyl-(1)]-2- hydroxypropyl group. For example, in the hotplate test on the mouse, the ED (i.e. the dose with which 50% of the animals are protected from pain), amounts to 25 mg./kg. with oral administration, which corresponds in this test approximately to the analgesic effect which results from codeine. In the benzoquinone test (chemical irritation on the peritoneum of the mouse), an ED' of 97 mg./ kg. on oral administration was found, corresponding approximately to the effective strength of the known 1-ethyl-4-methylamino-2,2-diphenylpentyl acetate (dextropropoxyphene). After doses of 25-250 mg./kg. per 0s, and using electrical irritation of the tooth pulp of the rabbit as the test method, the' irritation threshold of the pain was increased by 60-500% with long-lasting effect. In this test, I is even more strongly active than morphine or codeine.
United States Pate 0159c 3,652,567 Patented Mar. 28, 1972 The antitussive eflicacy of the compound was tested on the guinea pig and thecat. With the former, using a sulphuric acid spray as cough irritant, and ED of mg./ kg. was produced with subcutaneous administration, this once again corresponding approximately to the effectiveness of codeine. With the cat (electric stimulation of the laryngicus cranialis nerve) the effectiveness of codeine was reached, with an ED of -l.7 mg./k-g. (intravenous) and 10-20 mg./kg. (enteral). By contrast with the opium alkaloids, when I is used in doses of 5 mg./kg-. intravenously on the unnarcotised rabbit, the respiration (breath intake/breathing phase) is not impaired but it is even improved.
Since sedative, anticonvulsive and hypnotic active components extending into the sub-toxic dose range were not to be found in the appropriate tests, the analgesic and antitussive action cannot be caused by a general central sedation.
The LD values with the mouse are very high, being mg./kg. intravenously and 710 mg./kg. per os; 500 mg./ kg. per os are tolerated without reaction by the rabbit. This shows a very low toxicity of the compound I.
The compound according to the invention may be prepared by the condensation of l-phenylpiperazine with 2- methyl-3-[3-bromo-2-hydroxypropyl] quinazoline-4-one or by the addition to it of 2-methyl-3- [2,3-epoxypropyl1- quinazoline-4-one or by condensing 2-methylquinazoline- 4-one with epichlorhydrin and then adding to it l-phenylpiperazine preferably without isolation of the intermediate.
The invention therefore also provides a process for the preparation of the 2-methyl-3-{3 [4 phenylpiperazinyl- (1) ]-2-hydroxypropyl}-quinazo1ine-4-one in which (a) l-phenylpiperazine is condensed with 2-methyl-3- [3-bromo-2-hydroxypropyl]-quinazoline-4-one or (b) 2 methyl-3-[2,3-epoxypropyl]-quinazoline-4-one is reacted with l-phenylpiperazine; or
(c) 2-methylquinazoline-4-one is first condensed with epichlorhydrin and the product reacted with 1-phenylpiperazine if desired without intermediate isolation.
The reactions can be carried out in the absence of solvents at temperatures above C. and also in the presence of organic solvents, such as ethyl alcohol, at room temperature or higher temperature.
For administration, the compound according to the invention may be formulated with a pharmaceutical carrier to provide formulations adapted for the particular route of administration in particular the oral route, for example in the form of a syrup, elixir or the like or as a tablet or capsule.
The following examples illustrate the invention:
EXAMPLE 1 2.5 g. of 2-methyl-3-(3-bromo-2-hydroxypropyl)-quinazoline-4-one and 2.7 g. of l-phenylpiperazine are maintained for 5 minutes in an oil bath at The melt which is obtained is cooled and chloroform is added to it. The precipitate which is formed (l-phenylpiperazine dihydrobromide) is filtered off, the filtrate is evaporated and the residue crystallised from 96% ethanol. The 2- methy1-3-{3-[4-phenylpiperazinyl-( 1 ]-2-hydroxypropyl}- quinazoline-4-one which is formed melts at 145-144 C.; the yield is 2. 6 g., corresponding to 82% of the theoretical.
For C H N O .--Calculated (percent): C, 69.81; H, 6.93; N, 14.80. Found (percent): C, 70.25; H, 6.66; N, 14.60.
EXAMPLE 2 10.8 g. of 2-methyl-3-(2,3-epoxypropyl)-quinazoline-4- one and 8.1 g. of l-phenylpiperazine are boiled for 4 hours in 70 ml. of absolute ethanol and the solution is kept for several hours at room temperature and then in the cold. The substance which precipitates is filtered 01?, the contents of the filter are washed-with ether and then crystallised from ethanol. 14.2 g. of 2-methyl-3-{3-[4- phenylpiperazinyl 1 ]-2-hydroxypropyl}-quinazoline-4- one are formed, corresponding to 75% of the theoretical.
EXAMPLE 3 29.2 g. of 2-methylquinazoline-4-one and 70 m1. 82.5 g.) of epichlorhydrin are dissolved in methanol and then an equimolar quantity of sodium methylate in methanol is added. After standing for 12 hours at room temperature, the viscous mass which forms (39.6 g.) is filtered off, removed from the filter and maintained with 44.5 g. of l-phenylpiperazine for 30 minutes in an oil bath at 110 C. The mass (84 g. crude yield) is then worked up as previously described.
What is claimed is: wa 1. 2-methyl-3-{3-[4-phenylpiperaziny1-(1) ]-2-hydroxypropyl}quinazolin-4-one.
References Cited 7 UNITED STATES PATENTS 1/1966 Hayao 260-2564 OTHER REFERENCES Morrison et al.: Organic Chemistry1959, Allyn & Bacon, pp. 367, 423.
ALEX MAZEL, Primary Examiner R. V. RUSH, Assistant Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681803210 DE1803210A1 (en) | 1968-10-16 | 1968-10-16 | 2-Methyl-3- (3- [4-phenylpiperazinyl- (1)] -2-hydroxypropyl) -quinazolinone- (4) and process for its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3652567A true US3652567A (en) | 1972-03-28 |
Family
ID=5710568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US866719A Expired - Lifetime US3652567A (en) | 1968-10-16 | 1969-10-15 | Quinazolinone derivative and process for the production thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3652567A (en) |
| CH (1) | CH531524A (en) |
| DE (1) | DE1803210A1 (en) |
| FI (1) | FI52725C (en) |
| FR (1) | FR2020814B1 (en) |
| GB (1) | GB1245316A (en) |
| SE (1) | SE378422B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879393A (en) * | 1973-06-18 | 1975-04-22 | Miles Lab | Derivatives of 1,3-disubstituted 2,4(1h,3h)-quinazolinediones |
| DE4203050A1 (en) * | 1992-02-04 | 1992-12-10 | Heiko Delecate | Combined low voltage solar with compressed air engine - can be operated with solar power or pneumatic motor or as hybrid combination of both |
| WO2005123694A3 (en) * | 2004-06-17 | 2006-04-13 | Novartis Ag | Quinazolinone compounds for the treatment of cough |
| US8552015B2 (en) | 2002-02-06 | 2013-10-08 | Novartis Ag | Quinazolinone derivatives and their use as CB agonists |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1936588A1 (en) * | 1969-07-18 | 1971-02-18 | Troponwerke Dinklage & Co | Pharmacologically active quinazolinone compound, its use in pharmacological preparations and process for its manufacture |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3231572A (en) * | 1963-08-05 | 1966-01-25 | Miles Lab | 3-substituted-4-quinazolones |
-
1968
- 1968-10-16 DE DE19681803210 patent/DE1803210A1/en active Pending
-
1969
- 1969-10-06 CH CH1496969A patent/CH531524A/en not_active IP Right Cessation
- 1969-10-07 GB GB49142/69A patent/GB1245316A/en not_active Expired
- 1969-10-13 FI FI692935A patent/FI52725C/en active
- 1969-10-14 FR FR6935205A patent/FR2020814B1/fr not_active Expired
- 1969-10-15 US US866719A patent/US3652567A/en not_active Expired - Lifetime
- 1969-10-16 SE SE6914231A patent/SE378422B/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879393A (en) * | 1973-06-18 | 1975-04-22 | Miles Lab | Derivatives of 1,3-disubstituted 2,4(1h,3h)-quinazolinediones |
| DE4203050A1 (en) * | 1992-02-04 | 1992-12-10 | Heiko Delecate | Combined low voltage solar with compressed air engine - can be operated with solar power or pneumatic motor or as hybrid combination of both |
| US8552015B2 (en) | 2002-02-06 | 2013-10-08 | Novartis Ag | Quinazolinone derivatives and their use as CB agonists |
| WO2005123694A3 (en) * | 2004-06-17 | 2006-04-13 | Novartis Ag | Quinazolinone compounds for the treatment of cough |
| US20080004296A1 (en) * | 2004-06-17 | 2008-01-03 | Christine Charman | Organic Compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| SE378422B (en) | 1975-09-01 |
| CH531524A (en) | 1972-12-15 |
| GB1245316A (en) | 1971-09-08 |
| FR2020814A1 (en) | 1970-07-17 |
| FR2020814B1 (en) | 1974-02-01 |
| FI52725B (en) | 1977-08-01 |
| DE1803210A1 (en) | 1970-05-14 |
| FI52725C (en) | 1977-11-10 |
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