SU797575A3 - Способ получени окисей хиназолинона - Google Patents
Способ получени окисей хиназолинона Download PDFInfo
- Publication number
- SU797575A3 SU797575A3 SU782627504A SU2627504A SU797575A3 SU 797575 A3 SU797575 A3 SU 797575A3 SU 782627504 A SU782627504 A SU 782627504A SU 2627504 A SU2627504 A SU 2627504A SU 797575 A3 SU797575 A3 SU 797575A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- phenyl
- chloro
- quinazolinone
- ethanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- FTAHQVWNRWZINV-UHFFFAOYSA-N 1-hydroxyquinazolin-2-one Chemical class C1=CC=C2C=NC(=O)N(O)C2=C1 FTAHQVWNRWZINV-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- PZOZHMBWLDUJCP-UHFFFAOYSA-N 3-fluoro-1H-1,2-benzodiazepine Chemical class FC1=NNC2=C(C=C1)C=CC=C2 PZOZHMBWLDUJCP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- -1 2-benzoyl-4-chlorophenyl Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OKYIKPYUCUWSDO-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-3-phenylurea Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC=C1 OKYIKPYUCUWSDO-UHFFFAOYSA-N 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 1
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- LSDMQAUUESCBJN-UHFFFAOYSA-N (6-amino-3-chloro-6-fluorocyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound NC1(F)C=CC(Cl)=CC1C(=O)C1=CC=CC=C1 LSDMQAUUESCBJN-UHFFFAOYSA-N 0.000 description 1
- DYPCOCOEFYSJHP-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea Chemical compound C=1C=C(Cl)C=C(C(=O)C=2C=CC=CC=2)C=1N(C)C(=O)NC1=CC=CC=C1 DYPCOCOEFYSJHP-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- QIDCJFIPAIPVRT-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1 QIDCJFIPAIPVRT-UHFFFAOYSA-N 0.000 description 1
- YKTGQUPZGACWEI-UHFFFAOYSA-N 6-chloro-3-ethyl-4-(2-fluorophenyl)-4-hydroxy-1h-quinazolin-2-one Chemical compound CCN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1F YKTGQUPZGACWEI-UHFFFAOYSA-N 0.000 description 1
- PUOYDTRFCAVAPT-UHFFFAOYSA-N 6-chloro-4-hydroxy-1,3-dimethyl-4-phenylquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)N(C)C1(O)C1=CC=CC=C1 PUOYDTRFCAVAPT-UHFFFAOYSA-N 0.000 description 1
- AWSGAAUIGPHERF-UHFFFAOYSA-N 6-chloro-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 AWSGAAUIGPHERF-UHFFFAOYSA-N 0.000 description 1
- JRTXZECHXRHMEP-UHFFFAOYSA-N C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 JRTXZECHXRHMEP-UHFFFAOYSA-N 0.000 description 1
- PFNXVIDDDAFQRQ-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 PFNXVIDDDAFQRQ-UHFFFAOYSA-N 0.000 description 1
- VDKXMYMQSHUBMT-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1F Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1F VDKXMYMQSHUBMT-UHFFFAOYSA-N 0.000 description 1
- NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical compound C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- JXBPSENIJJPTCI-UHFFFAOYSA-N ethyl cyanate Chemical compound CCOC#N JXBPSENIJJPTCI-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- QBRSFUSGKXVSPM-UHFFFAOYSA-N hydroxylamine;hydrobromide Chemical compound Br.ON QBRSFUSGKXVSPM-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D239/78—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80707677A | 1977-06-16 | 1977-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU797575A3 true SU797575A3 (ru) | 1981-01-15 |
Family
ID=25195510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782627504A SU797575A3 (ru) | 1977-06-16 | 1978-06-15 | Способ получени окисей хиназолинона |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0000149A1 (es) |
| JP (1) | JPS545988A (es) |
| AT (1) | ATA436678A (es) |
| AU (1) | AU3709278A (es) |
| CA (1) | CA1094068A (es) |
| DK (1) | DK176378A (es) |
| ES (1) | ES470828A1 (es) |
| FI (1) | FI781928A7 (es) |
| GR (1) | GR64944B (es) |
| IT (1) | IT1098341B (es) |
| NO (1) | NO782087L (es) |
| NZ (1) | NZ187581A (es) |
| PL (1) | PL113420B1 (es) |
| PT (1) | PT68174A (es) |
| SU (1) | SU797575A3 (es) |
| ZA (1) | ZA783438B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3553062A1 (en) | 2018-04-09 | 2019-10-16 | Chemical Intelligence Limited | Antimicrobial and anticancer cationic phthalocyanine compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4946633B2 (es) * | 1971-08-17 | 1974-12-11 |
-
1978
- 1978-04-24 DK DK176378A patent/DK176378A/da unknown
- 1978-06-14 AU AU37092/78A patent/AU3709278A/en active Pending
- 1978-06-14 CA CA305,471A patent/CA1094068A/en not_active Expired
- 1978-06-15 EP EP78100163A patent/EP0000149A1/en not_active Withdrawn
- 1978-06-15 AT AT436678A patent/ATA436678A/de not_active Application Discontinuation
- 1978-06-15 NZ NZ187581A patent/NZ187581A/xx unknown
- 1978-06-15 ES ES470828A patent/ES470828A1/es not_active Expired
- 1978-06-15 IT IT24615/78A patent/IT1098341B/it active
- 1978-06-15 PT PT68174A patent/PT68174A/pt unknown
- 1978-06-15 SU SU782627504A patent/SU797575A3/ru active
- 1978-06-15 ZA ZA00783438A patent/ZA783438B/xx unknown
- 1978-06-15 NO NO782087A patent/NO782087L/no unknown
- 1978-06-16 GR GR56539A patent/GR64944B/el unknown
- 1978-06-16 FI FI781928A patent/FI781928A7/fi not_active Application Discontinuation
- 1978-06-16 PL PL1978207682A patent/PL113420B1/pl not_active IP Right Cessation
- 1978-06-16 JP JP7367978A patent/JPS545988A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS545988A (en) | 1979-01-17 |
| PT68174A (en) | 1978-07-01 |
| GR64944B (en) | 1980-06-10 |
| PL207682A1 (pl) | 1979-05-07 |
| AU3709278A (en) | 1979-12-20 |
| EP0000149A1 (en) | 1979-01-10 |
| NO782087L (no) | 1978-12-19 |
| FI781928A7 (fi) | 1978-12-17 |
| PL113420B1 (en) | 1980-12-31 |
| NZ187581A (en) | 1980-11-28 |
| DK176378A (da) | 1978-12-17 |
| ES470828A1 (es) | 1979-10-01 |
| ATA436678A (de) | 1981-01-15 |
| IT1098341B (it) | 1985-09-07 |
| ZA783438B (en) | 1979-06-27 |
| CA1094068A (en) | 1981-01-20 |
| IT7824615A0 (it) | 1978-06-15 |
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