SU449487A3 - Способ получени 4-амино-6,7,8-триалкоксихиназолинов - Google Patents
Способ получени 4-амино-6,7,8-триалкоксихиназолиновInfo
- Publication number
- SU449487A3 SU449487A3 SU1785908A SU1785908A SU449487A3 SU 449487 A3 SU449487 A3 SU 449487A3 SU 1785908 A SU1785908 A SU 1785908A SU 1785908 A SU1785908 A SU 1785908A SU 449487 A3 SU449487 A3 SU 449487A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- hydrogen
- trialkoxy
- quinazolines
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- -1 (2-hydroxyethyl) aminopropyl amino-6,7,8-trimethoxyquinazoline Chemical compound 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKPCKRQHKIAKMH-UHFFFAOYSA-N 2-(2-amino-6,7,8-trimethoxyquinazolin-4-yl)ethanol Chemical compound OCCC1=NC(=NC2=C(C(=C(C=C12)OC)OC)OC)N HKPCKRQHKIAKMH-UHFFFAOYSA-N 0.000 description 1
- BIICRHXSGPYQOV-UHFFFAOYSA-N 4-chloro-6,7,8-trimethoxyquinazoline Chemical compound N1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1Cl BIICRHXSGPYQOV-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- OJDLZXRWADEOKZ-UHFFFAOYSA-N 5-(2-amino-6,7,8-trimethoxyquinazolin-4-yl)pentan-1-ol Chemical compound OCCCCCC1=NC(=NC2=C(C(=C(C=C12)OC)OC)OC)N OJDLZXRWADEOKZ-UHFFFAOYSA-N 0.000 description 1
- CVMNMRDYAQCGND-UHFFFAOYSA-N 6,7,8-triethoxyquinazoline Chemical compound C(C)OC=1C=C2C=NC=NC2=C(C=1OCC)OCC CVMNMRDYAQCGND-UHFFFAOYSA-N 0.000 description 1
- VQTMHRLFVXHMFU-UHFFFAOYSA-N 6,7,8-trimethoxyquinazolin-2-amine Chemical compound NC1=NC2=C(C(=C(C=C2C=N1)OC)OC)OC VQTMHRLFVXHMFU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87043969A | 1969-12-05 | 1969-12-05 | |
| SE1157870 | 1970-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU449487A3 true SU449487A3 (ru) | 1974-11-05 |
Family
ID=26655842
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1785908A SU449487A3 (ru) | 1969-12-05 | 1970-12-04 | Способ получени 4-амино-6,7,8-триалкоксихиназолинов |
| SU1785910A SU439091A3 (ru) | 1969-12-05 | 1970-12-04 | Способ получения 4-амино-6,7,8- триалкоксихиназолинов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1785910A SU439091A3 (ru) | 1969-12-05 | 1970-12-04 | Способ получения 4-амино-6,7,8- триалкоксихиназолинов |
Country Status (17)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793371A (fr) * | 1971-12-27 | 1973-06-27 | Sandoz Sa | Nouveaux derives de la 4-amino-quinazoline, leur preparation etmedicaments contenant ces |
| JPS5416626U (enrdf_load_stackoverflow) * | 1977-07-05 | 1979-02-02 | ||
| IE51802B1 (en) * | 1979-12-03 | 1987-04-01 | Fujisawa Pharmaceutical Co | Quinazoline derivatives,processes for their preparation and pharmaceutical compositions containing them |
| US4510307A (en) * | 1980-08-20 | 1985-04-09 | Asahi Kasei Kogyo Kabushiki Kaisha | 6-Quinazolinesulfonyl derivatives and process for preparation thereof |
| WO1995007267A1 (fr) * | 1993-09-10 | 1995-03-16 | Eisai Co., Ltd. | Compose de quinazoline |
| GB0307333D0 (en) * | 2003-03-29 | 2003-05-07 | Astrazeneca Ab | Therapeutic agent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1199768A (en) * | 1966-10-31 | 1970-07-22 | Pfizer & Co C | Nitrogen Heterocycles and process for their preparation |
| US3470182A (en) * | 1967-02-09 | 1969-09-30 | Sandoz Ag | 4-amino-substituted quinazolines |
-
0
- BE BE759842D patent/BE759842R/xx active
-
1970
- 1970-11-23 CH CH1519173A patent/CH552601A/xx not_active IP Right Cessation
- 1970-11-23 CH CH1735770A patent/CH549581A/xx unknown
- 1970-12-02 GB GB3491073A patent/GB1349140A/en not_active Expired
- 1970-12-02 GB GB2616273A patent/GB1349137A/en not_active Expired
- 1970-12-02 DE DE19702059164 patent/DE2059164A1/de active Pending
- 1970-12-02 GB GB2616373A patent/GB1349138A/en not_active Expired
- 1970-12-02 GB GB5722170A patent/GB1349136A/en not_active Expired
- 1970-12-02 GB GB3059973A patent/GB1349139A/en not_active Expired
- 1970-12-02 IE IE1541/70A patent/IE34780B1/xx unknown
- 1970-12-03 NL NL7017669A patent/NL7017669A/xx unknown
- 1970-12-03 ES ES0386121A patent/ES386121A1/es not_active Expired
- 1970-12-03 RO RO7000074397A patent/RO62627A/ro unknown
- 1970-12-03 HU HUSA2281A patent/HU162867B/hu unknown
- 1970-12-03 HU HUSA2280A patent/HU162866B/hu unknown
- 1970-12-03 IL IL35779A patent/IL35779A/xx unknown
- 1970-12-03 BG BG016189A patent/BG17598A3/xx unknown
- 1970-12-03 PL PL1970144794A patent/PL81227B1/pl unknown
- 1970-12-03 RO RO7000074396A patent/RO62626A/ro unknown
- 1970-12-04 OA OA54108A patent/OA03536A/xx unknown
- 1970-12-04 SU SU1785908A patent/SU449487A3/ru active
- 1970-12-04 SU SU1785910A patent/SU439091A3/ru active
- 1970-12-04 FR FR7043720A patent/FR2081329B2/fr not_active Expired
- 1970-12-13 BG BG017324A patent/BG17599A3/xx unknown
-
1972
- 1972-04-14 JP JP47037000A patent/JPS4837035B1/ja active Pending
-
1973
- 1973-08-13 AU AU59188/73A patent/AU5918873A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1349140A (en) | 1974-03-27 |
| AU5918873A (en) | 1974-02-14 |
| JPS4837035B1 (enrdf_load_stackoverflow) | 1973-11-08 |
| IE34780B1 (en) | 1975-08-20 |
| HU162867B (enrdf_load_stackoverflow) | 1973-04-28 |
| BG17598A3 (bg) | 1973-11-10 |
| GB1349138A (en) | 1974-03-27 |
| RO62627A (fr) | 1978-05-15 |
| IE34780L (en) | 1971-06-05 |
| FR2081329A2 (enrdf_load_stackoverflow) | 1971-12-03 |
| NL7017669A (enrdf_load_stackoverflow) | 1971-06-08 |
| BE759842R (fr) | 1971-06-03 |
| GB1349136A (en) | 1974-03-27 |
| ES386121A1 (es) | 1973-12-16 |
| CH549581A (de) | 1974-05-31 |
| GB1349139A (en) | 1974-03-27 |
| PL81227B1 (en) | 1975-08-30 |
| FR2081329B2 (enrdf_load_stackoverflow) | 1975-06-06 |
| RO62626A (fr) | 1978-05-15 |
| HU162866B (enrdf_load_stackoverflow) | 1973-04-28 |
| CH552601A (de) | 1974-08-15 |
| SU439091A3 (ru) | 1974-08-05 |
| BG17599A3 (bg) | 1973-11-10 |
| DE2059164A1 (de) | 1971-06-09 |
| OA03536A (fr) | 1971-03-30 |
| IL35779A (en) | 1974-06-30 |
| GB1349137A (en) | 1974-03-27 |
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