SU528032A3 - Способ получени 1-алкил-4-фенилили-4-(2"-тиенил)-2(1н)-хиназолинонов - Google Patents
Способ получени 1-алкил-4-фенилили-4-(2"-тиенил)-2(1н)-хиназолиноновInfo
- Publication number
- SU528032A3 SU528032A3 SU1808956A SU1808956A SU528032A3 SU 528032 A3 SU528032 A3 SU 528032A3 SU 1808956 A SU1808956 A SU 1808956A SU 1808956 A SU1808956 A SU 1808956A SU 528032 A3 SU528032 A3 SU 528032A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- added
- solution
- phenyl
- isopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 18
- 239000000243 solution Substances 0.000 claims 17
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- 238000006356 dehydrogenation reaction Methods 0.000 claims 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 9
- -1 alkyl chlorocarbonate Chemical compound 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 5
- 239000008096 xylene Substances 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 4
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000002808 molecular sieve Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims 2
- 229940043279 diisopropylamine Drugs 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910003002 lithium salt Inorganic materials 0.000 claims 2
- 159000000002 lithium salts Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000012044 organic layer Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 229910052727 yttrium Inorganic materials 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OYTYIOQIELBZKA-UHFFFAOYSA-N 4-methyl-n-propan-2-ylcyclohexan-1-imine Chemical compound CC(C)N=C1CCC(C)CC1 OYTYIOQIELBZKA-UHFFFAOYSA-N 0.000 claims 1
- JAPCFGJAINHVJK-UHFFFAOYSA-N 5,7-dimethyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC(C)=C2C=1C1=CC=CC=C1 JAPCFGJAINHVJK-UHFFFAOYSA-N 0.000 claims 1
- RRWXXCGCGFAXAF-UHFFFAOYSA-N 6-methyl-4-phenyl-1-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C=2CCC(C)CC=2C=1C1=CC=CC=C1 RRWXXCGCGFAXAF-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229940037003 alum Drugs 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 235000014121 butter Nutrition 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000007928 solubilization Effects 0.000 claims 1
- 238000005063 solubilization Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 claims 1
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16096071A | 1971-07-08 | 1971-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU528032A3 true SU528032A3 (ru) | 1976-09-05 |
Family
ID=22579209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1808956A SU528032A3 (ru) | 1971-07-08 | 1972-07-06 | Способ получени 1-алкил-4-фенилили-4-(2"-тиенил)-2(1н)-хиназолинонов |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4066665A (en, 2012) |
| JP (4) | JPS577150B1 (en, 2012) |
| AT (1) | AT338270B (en, 2012) |
| BE (1) | BE785937A (en, 2012) |
| BG (1) | BG19170A3 (en, 2012) |
| CA (1) | CA1002953A (en, 2012) |
| CH (2) | CH602668A5 (en, 2012) |
| CS (1) | CS189583B2 (en, 2012) |
| DD (3) | DD106171A5 (en, 2012) |
| DE (3) | DE2254326A1 (en, 2012) |
| ES (1) | ES404598A1 (en, 2012) |
| FI (1) | FI57401C (en, 2012) |
| FR (2) | FR2144753B1 (en, 2012) |
| GB (1) | GB1383255A (en, 2012) |
| IE (1) | IE36541B1 (en, 2012) |
| IL (1) | IL39845A (en, 2012) |
| NL (1) | NL7209322A (en, 2012) |
| NO (1) | NO136838C (en, 2012) |
| OA (1) | OA04129A (en, 2012) |
| PH (1) | PH13454A (en, 2012) |
| PL (1) | PL89011B1 (en, 2012) |
| RO (1) | RO63336A (en, 2012) |
| SE (1) | SE406196B (en, 2012) |
| SU (1) | SU528032A3 (en, 2012) |
| YU (1) | YU177672A (en, 2012) |
| ZA (1) | ZA724688B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996227A (en) * | 1971-07-08 | 1976-12-07 | Sandoz, Inc. | 7-Methyl-1-isopropyl-4-phenyl-5,6,7,8-tetrahydro-2(1H)-quinazolinone |
| JPS5271483A (en) | 1975-12-11 | 1977-06-14 | Sumitomo Chem Co Ltd | Synthesis of 2(1h)-quinazolinone derivatives |
| CH642638A5 (de) * | 1977-09-06 | 1984-04-30 | Sandoz Ag | Verfahren zur herstellung von chinazolin-2(1h)-onen. |
| JPS5661198A (en) * | 1979-10-24 | 1981-05-26 | Shinto Paint Co Ltd | Method of painting board for wiring conductive print |
| JPS5878495A (ja) * | 1981-11-05 | 1983-05-12 | セイコーエプソン株式会社 | プリント配線板の製造方法 |
| JPS5878494A (ja) * | 1981-11-05 | 1983-05-12 | セイコーエプソン株式会社 | プリント配線板の製造方法 |
| JPS58222593A (ja) * | 1982-02-24 | 1983-12-24 | 日立化成工業株式会社 | 金属芯入りプリント配線板用基板の製造法 |
| US4601916A (en) * | 1984-07-18 | 1986-07-22 | Kollmorgen Technologies Corporation | Process for bonding metals to electrophoretically deposited resin coatings |
| JPS6133463U (ja) * | 1984-07-30 | 1986-02-28 | 三菱電線工業株式会社 | 金属ベ−ス基板 |
| JPS61156000U (en, 2012) * | 1985-03-19 | 1986-09-27 | ||
| US6951707B2 (en) * | 2001-03-08 | 2005-10-04 | Ppg Industries Ohio, Inc. | Process for creating vias for circuit assemblies |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553199A (en) * | 1967-03-17 | 1971-01-05 | Hoffmann La Roche | Reaction of 2-aminobenzophenone amines and benzhydryl amines with di-leaveing group-substituted ethane |
| US3723432A (en) * | 1968-11-12 | 1973-03-27 | Sandoz Ag | 1-substituted-4-aryl-2(1h)-quinazolinones and their preparation |
| US3549635A (en) * | 1968-07-01 | 1970-12-22 | Sandoz Ag | Preparation of substituted-2(1h)-quinazolinones |
| US3563990A (en) * | 1969-03-18 | 1971-02-16 | Sandoz Ag | 1-substituted-4-aryl-2(1h)-quinazolinones |
| DD202218A5 (de) * | 1982-04-27 | 1983-08-31 | Orion Radio | Verfahren und schaltungsanordnung zur erzeugung einer phasengetasteten kohaerenten traegerfrequenz |
-
0
- BE BE785937D patent/BE785937A/xx unknown
-
1972
- 1972-06-28 CH CH967772A patent/CH602668A5/xx not_active IP Right Cessation
- 1972-06-28 CH CH1000775A patent/CH587804A5/xx not_active IP Right Cessation
- 1972-06-29 SE SE7208555A patent/SE406196B/xx unknown
- 1972-06-30 FI FI1870/72A patent/FI57401C/fi active
- 1972-06-30 PH PH13677A patent/PH13454A/en unknown
- 1972-06-30 NO NO2357/72A patent/NO136838C/no unknown
- 1972-07-03 NL NL7209322A patent/NL7209322A/xx not_active Application Discontinuation
- 1972-07-04 FR FR7224092A patent/FR2144753B1/fr not_active Expired
- 1972-07-04 GB GB3116172A patent/GB1383255A/en not_active Expired
- 1972-07-04 CS CS724738A patent/CS189583B2/cs unknown
- 1972-07-05 DE DE2254326*A patent/DE2254326A1/de not_active Withdrawn
- 1972-07-05 DE DE2254325*A patent/DE2254325A1/de not_active Withdrawn
- 1972-07-05 DE DE2232919A patent/DE2232919A1/de not_active Withdrawn
- 1972-07-06 RO RO7200071526A patent/RO63336A/ro unknown
- 1972-07-06 YU YU01776/72A patent/YU177672A/xx unknown
- 1972-07-06 IL IL39845A patent/IL39845A/xx unknown
- 1972-07-06 IE IE961/72A patent/IE36541B1/xx unknown
- 1972-07-06 ES ES404598A patent/ES404598A1/es not_active Expired
- 1972-07-06 OA OA54634A patent/OA04129A/xx unknown
- 1972-07-06 PL PL1972156542A patent/PL89011B1/pl unknown
- 1972-07-06 BG BG020905A patent/BG19170A3/xx unknown
- 1972-07-06 SU SU1808956A patent/SU528032A3/ru active
- 1972-07-07 DD DD170839*A patent/DD106171A5/xx unknown
- 1972-07-07 DD DD164258A patent/DD101400A5/xx unknown
- 1972-07-07 JP JP6762772A patent/JPS577150B1/ja active Pending
- 1972-07-07 AT AT582972A patent/AT338270B/de not_active IP Right Cessation
- 1972-07-07 CA CA146,572A patent/CA1002953A/en not_active Expired
- 1972-07-07 DD DD170837*A patent/DD106175A5/xx unknown
- 1972-07-07 ZA ZA724688A patent/ZA724688B/xx unknown
-
1974
- 1974-02-07 FR FR7404125A patent/FR2208681B1/fr not_active Expired
- 1974-06-19 US US05/480,626 patent/US4066665A/en not_active Expired - Lifetime
-
1980
- 1980-06-26 JP JP55086000A patent/JPS585198B2/ja not_active Expired
- 1980-06-26 JP JP55085999A patent/JPS58422B2/ja not_active Expired
- 1980-06-26 JP JP8599880A patent/JPS56115758A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5298657A (en) | Preparation of substituted guanidines | |
| SU528032A3 (ru) | Способ получени 1-алкил-4-фенилили-4-(2"-тиенил)-2(1н)-хиназолинонов | |
| SU493966A3 (ru) | Способ получени производных 4-/2имидазолин-2-иламино/-2,1,3-бензотиадиазола | |
| JPH01211567A (ja) | 新規なスルホンアミド化合物 | |
| JPS61286371A (ja) | ５−オキソ−イミダゾリニル安息香酸類、ニコチン酸類及びキノリンカルボン酸類の製造法 | |
| HU176881B (en) | Process for producing derivatives of urea | |
| US4419355A (en) | Condensed as-triazine derivatives and method of using the same | |
| HU197322B (en) | Process for producing pyridyl and quinolyl imidazolinones | |
| RU2295521C2 (ru) | Фотохромные оксазиновые соединения и способы их производства | |
| NO132800B (en, 2012) | ||
| US4207237A (en) | Preparation of pyrrole-2-acetates | |
| US3956301A (en) | Process for bromination of pyrimidine | |
| US3433802A (en) | 3-(n-lower-alkylanilino)pyrrolidines | |
| JPS607987B2 (ja) | ヒダントイン誘導体 | |
| US4394514A (en) | Processes for preparing 4-substituted indoles | |
| US4186132A (en) | Isatin products | |
| US3978126A (en) | N-hydroxy-amidine compounds | |
| US4188325A (en) | Isatin process and products | |
| SU417945A3 (ru) | Способ получения производных хиназолинона-2 | |
| US4760158A (en) | Nitriles | |
| US4727149A (en) | Preparation of nitriles of fused ring pyridine derivatives | |
| JPS5834465B2 (ja) | トリフルオロトルアニリド類及びその製法 | |
| US2459111A (en) | Pantoyltauramides and preparation of the same | |
| JPH0320391B2 (en, 2012) | ||
| SU458977A3 (ru) | Способ получени -(аминофенил)-алифатических производных карбоновых кислот, или их солей, или их -окисей |