IE33186L - Quinazoline-thiones - Google Patents
Quinazoline-thionesInfo
- Publication number
- IE33186L IE33186L IE690891A IE89169A IE33186L IE 33186 L IE33186 L IE 33186L IE 690891 A IE690891 A IE 690891A IE 89169 A IE89169 A IE 89169A IE 33186 L IE33186 L IE 33186L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- alkoxy
- compounds
- reacting
- prepared
- Prior art date
Links
- MHBPJMUAIOKJNL-UHFFFAOYSA-N 1h-quinazoline-2-thione Chemical class C1=CC=CC2=NC(S)=NC=C21 MHBPJMUAIOKJNL-UHFFFAOYSA-N 0.000 title 1
- 229910052794 bromium Inorganic materials 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 229910052731 fluorine Inorganic materials 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- -1 dialkylamino compounds Chemical class 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 2
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- IGDKJXXPUDSVMV-UHFFFAOYSA-N 3-methyl-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC(C)=C1 IGDKJXXPUDSVMV-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 150000003585 thioureas Chemical class 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- 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
-
- 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L13/00—Devices or apparatus for measuring differences of two or more fluid pressure values
- G01L13/02—Devices or apparatus for measuring differences of two or more fluid pressure values using elastically-deformable members or pistons as sensing elements
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- General Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
Abstract
1,265,548. Quinazeline-thione derivatives. SANDOZ Ltd. 13 June, 1969 [1 July, 1968; 15 April, 1969; 25 April, 1969], No. 30195/69. Heading C2C. Novel compounds I (including salts of the dialkylamino compounds) wherein x y signifies -CR 2 = N- or R is H, F, Cl, Br, C 1 to C 5 alkyl, C 1 to C, alkoxy or alkylthio, NO 2 , CF 3 or di -C 1 to C 4 alkylamino, n is 1 or 2 provided that when n is 2 the R's (may be same or different) signify H, F, Cl, Br, C 1 to C 5 alkyl or C 1 to C 4 alkoxy, R 1 is C 1 to C 5 alkyl, allyl or propargyl and R 2 is phenyl or Y,Y i -substituted phenyl (Y is F, Cl, Br, C 1 to C 4 alkyl, C 1 to C 4 alkoxy or CF 3 and Y 1 is H, F, Cl, Br, C 1 to C 4 alkyl or C 1 to C 4 alkoxy), are obtained: (a) by interacting phosphorus pentasulphide and compounds III (prepared by reacting compounds IV with a urethane; IV are obtained by alkylation of corresponding primary amines ) ; (b) by reacting IV with a carboxylic acid chloride or bromide and MNCS (M is alkali or alkaline earth metal cation or the ammonium cation) or with the reaction product thereof or with isothiocyanic acid (conveniently prepared in situ); (c) by reacting isothiocyanic acid with compounds VI (prepared by interaction of IV and, e.g. sodium borohydride); or (d) by interacting an aldehyde, Y<SP>1</SP> 1 C 6 H 4 .CHO, and compounds IX (prepared by saponification of appropriate acylated thioureas; R<SP>1</SP> is H, F, Cl, Br, C 1 to C 5 alkyl or C 1 to C 4 alkoxy, R<SP>1</SP> 1 is C 1 to C 5 alkyl, n<SP>1</SP> is 1 or 2 provided that when n<SP>1</SP> is 2 no more than one R<SP>1</SP> is halogen or a branched chain substituent and provided that R<SP>1</SP> is other than a branched chain substituent when in the 5- or 8-position, and Y<SP>1</SP> 1 is H, F, Cl, Br, C 1 to C 3 alkyl or C 1 or C 2 alkoxy). N - Isopropyl - N - (m - tolyl) - N<SP>1</SP> - benzoylthiourea is obtained by reacting N-isopropyl-3- methylaniline with benzoyl chloride in the presence of ammonium thiocyanate. Pharmaceutical preparations showing, in particular, activity contain I as active ingredient; administration is orally or parenterally.
[GB1265548A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74180568A | 1968-07-01 | 1968-07-01 | |
| US81638369A | 1969-04-15 | 1969-04-15 | |
| US81947769A | 1969-04-25 | 1969-04-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33186L true IE33186L (en) | 1970-01-01 |
| IE33186B1 IE33186B1 (en) | 1974-04-17 |
Family
ID=27419277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE891/69A IE33186B1 (en) | 1968-07-01 | 1969-06-30 | Quinazoline-thione derivatives |
Country Status (15)
| Country | Link |
|---|---|
| BE (1) | BE735343A (en) |
| BG (1) | BG16035A3 (en) |
| CA (1) | CA956950A (en) |
| CH (1) | CH514596A (en) |
| DE (1) | DE1932401C3 (en) |
| DK (1) | DK131151B (en) |
| ES (3) | ES368945A1 (en) |
| FR (1) | FR2012060A1 (en) |
| GB (1) | GB1265548A (en) |
| IE (1) | IE33186B1 (en) |
| IL (1) | IL32504A (en) |
| NL (1) | NL6909804A (en) |
| NO (1) | NO128998B (en) |
| RO (1) | RO56665A (en) |
| SE (1) | SE376421B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2037693C3 (en) * | 1969-08-02 | 1975-01-16 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 1-Cyclopropylmethyl-2 (1 H) -quinazolinone derivatives |
| US9834525B2 (en) | 2014-02-04 | 2017-12-05 | University Of Tennessee Research Foundation | Inhibitors of paxillin function and related compositions and methods |
-
1969
- 1969-05-26 RO RO62704A patent/RO56665A/ro unknown
- 1969-06-11 CH CH889269A patent/CH514596A/en not_active IP Right Cessation
- 1969-06-13 GB GB1265548D patent/GB1265548A/en not_active Expired
- 1969-06-13 NO NO02447/69A patent/NO128998B/no unknown
- 1969-06-16 DK DK323069AA patent/DK131151B/en unknown
- 1969-06-19 SE SE6908762A patent/SE376421B/xx unknown
- 1969-06-26 DE DE1932401A patent/DE1932401C3/en not_active Expired
- 1969-06-26 NL NL6909804A patent/NL6909804A/xx not_active Application Discontinuation
- 1969-06-27 BE BE735343D patent/BE735343A/xx unknown
- 1969-06-28 BG BG012548A patent/BG16035A3/en unknown
- 1969-06-29 IL IL32504A patent/IL32504A/en unknown
- 1969-06-30 CA CA055,705A patent/CA956950A/en not_active Expired
- 1969-06-30 FR FR6921993A patent/FR2012060A1/fr not_active Withdrawn
- 1969-06-30 ES ES368945A patent/ES368945A1/en not_active Expired
- 1969-06-30 IE IE891/69A patent/IE33186B1/en unknown
-
1970
- 1970-05-16 ES ES379709A patent/ES379709A1/en not_active Expired
- 1970-05-16 ES ES379708A patent/ES379708A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH514596A (en) | 1971-10-31 |
| IL32504A0 (en) | 1969-08-27 |
| IL32504A (en) | 1973-06-29 |
| DE1932401B2 (en) | 1979-08-16 |
| ES379709A1 (en) | 1973-01-16 |
| IE33186B1 (en) | 1974-04-17 |
| NL6909804A (en) | 1970-01-05 |
| NO128998B (en) | 1974-02-11 |
| DK131151C (en) | 1975-10-27 |
| BG16035A3 (en) | 1972-05-20 |
| GB1265548A (en) | 1972-03-01 |
| SE376421B (en) | 1975-05-26 |
| CA956950A (en) | 1974-10-29 |
| ES368945A1 (en) | 1971-07-16 |
| DK131151B (en) | 1975-06-02 |
| ES379708A1 (en) | 1973-02-01 |
| BE735343A (en) | 1969-12-29 |
| FR2012060A1 (en) | 1970-03-13 |
| DE1932401A1 (en) | 1970-01-08 |
| RO56665A (en) | 1974-06-01 |
| DE1932401C3 (en) | 1980-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1425810A (en) | Method of combating helminthic infestation in animals | |
| GB1260460A (en) | Method for selectively combating weeds in cereal, rice and sugar cane cultures | |
| GB1189915A (en) | Carbamic Acid Fluorides | |
| IE33186B1 (en) | Quinazoline-thione derivatives | |
| SE326336B (en) | ||
| GB1274668A (en) | Pesticidal compositions comprising aminoguanidines | |
| GB1191112A (en) | New Benzimidazoles, their production and use | |
| GB1252329A (en) | ||
| GB1252953A (en) | ||
| GB1252487A (en) | ||
| GB1159748A (en) | Thiol-Type Thiamine Thionocarbonates | |
| GB1290662A (en) | ||
| GB1314494A (en) | Pyridazinothionophosphoric phosphonic acid esters process for their preparation and their use as insecticides and acaricides | |
| GB1227967A (en) | ||
| GB1318859A (en) | Imidazo-4,5-b-pyridine derivatives | |
| GB1439631A (en) | Pesticidal thiolphosphoric acid esters | |
| GB1441637A (en) | Preparation of morphanthridin-6-5h-ones | |
| GB1437788A (en) | Therapeutic compositions | |
| GB1497723A (en) | Octahydrobenzo-(c)(1,6)-naphthyridine derivative | |
| GB1189267A (en) | Sulphenic Acid Derivatives | |
| GB1509778A (en) | Pharmaceutical composition and dosage units thereof | |
| GB1356901A (en) | Rodenticidal compositions | |
| GB1341612A (en) | Theophylline isobutyrate salts and process for the preparation thereof | |
| GB1426603A (en) | Amidine derivatives | |
| GB1172953A (en) | Isothiazoles |