NO831622L - Fremgangsmaate for fremstilling av 2-(4-substituert piperidino)4-amino-6,7-dimetoksykinazolin-derivater - Google Patents
Fremgangsmaate for fremstilling av 2-(4-substituert piperidino)4-amino-6,7-dimetoksykinazolin-derivaterInfo
- Publication number
- NO831622L NO831622L NO831622A NO831622A NO831622L NO 831622 L NO831622 L NO 831622L NO 831622 A NO831622 A NO 831622A NO 831622 A NO831622 A NO 831622A NO 831622 L NO831622 L NO 831622L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- compounds
- amino
- reacted
- Prior art date
Links
- -1 4-SUBSTITUTED PIPERIDINO Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- TUAHXRDDQSYUCY-UHFFFAOYSA-N cyclopentyl(piperidin-4-yl)methanol Chemical compound C1CNCCC1C(O)C1CCCC1 TUAHXRDDQSYUCY-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- SKBXVAOMEVOTGJ-UHFFFAOYSA-N xi-Pinol Chemical compound CC1=CCC2C(C)(C)OC1C2 SKBXVAOMEVOTGJ-UHFFFAOYSA-N 0.000 description 2
- NDJKRLGXVKYIGQ-UHFFFAOYSA-N 1-piperidin-4-ylethanol Chemical compound CC(O)C1CCNCC1 NDJKRLGXVKYIGQ-UHFFFAOYSA-N 0.000 description 1
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 description 1
- HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 description 1
- AFGXCIJBGLMDKI-UHFFFAOYSA-N 2-isothiocyanato-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N=C=S)=C(C#N)C=C1OC AFGXCIJBGLMDKI-UHFFFAOYSA-N 0.000 description 1
- DJJLZBAERKWDKG-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-phenylpiperidin-1-yl)quinazolin-4-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C1=CC=CC=C1 DJJLZBAERKWDKG-UHFFFAOYSA-N 0.000 description 1
- YQFGQRUVFDAPBW-UHFFFAOYSA-N C1=C(OC)C(OC)=CC(NC(=S)N2C(CCCC2)C(O)C2CCCC2)=C1C#N Chemical compound C1=C(OC)C(OC)=CC(NC(=S)N2C(CCCC2)C(O)C2CCCC2)=C1C#N YQFGQRUVFDAPBW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PNKLVCNYQMIOOW-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-cyclopentylmethanol;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(O)C1CCCC1 PNKLVCNYQMIOOW-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- OFFHOWWIQBWWQL-UHFFFAOYSA-N cyclohexyl(piperidin-4-yl)methanol Chemical compound C1CNCCC1C(O)C1CCCCC1 OFFHOWWIQBWWQL-UHFFFAOYSA-N 0.000 description 1
- WZJWFMLHYPEQQC-UHFFFAOYSA-N cyclopentyl(piperidin-4-yl)methanone Chemical compound C1CNCCC1C(=O)C1CCCC1 WZJWFMLHYPEQQC-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VOZHYVXIZRHIIY-UHFFFAOYSA-N methyl n-cyano-n'-(3,4-dimethoxyphenyl)carbamimidothioate Chemical compound COC1=CC=C(N=C(NC#N)SC)C=C1OC VOZHYVXIZRHIIY-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008177 pharmaceutical agent Substances 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI812796 | 1981-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831622L true NO831622L (no) | 1983-05-06 |
Family
ID=8514689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831622A NO831622L (no) | 1981-09-09 | 1983-05-06 | Fremgangsmaate for fremstilling av 2-(4-substituert piperidino)4-amino-6,7-dimetoksykinazolin-derivater |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0087456A1 (it) |
| JP (1) | JPS58501513A (it) |
| AU (1) | AU8906682A (it) |
| DK (1) | DK181083A (it) |
| ES (1) | ES515338A0 (it) |
| FI (1) | FI831585L (it) |
| IT (1) | IT1156319B (it) |
| NO (1) | NO831622L (it) |
| PT (1) | PT75525B (it) |
| WO (1) | WO1983000866A1 (it) |
| ZA (1) | ZA826596B (it) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517005A (en) * | 1967-10-26 | 1970-06-23 | Pfizer & Co C | Certain 2- and 4-substituted quinazolines |
| DK140695C (da) * | 1976-05-07 | 1980-05-12 | Synthelabo | Analogifremgangsmaade til fremstilling af 2,4-diamino-6,7-dimethoxyquinazolinderivater eller syreadditionssalte heraf |
| FR2389621A2 (en) * | 1977-05-05 | 1978-12-01 | Synthelabo | Antihypertensive 4-amino 2-piperidino-quinazoline(s) - prepd. from a 2-halo-quinazoline and a piperidine |
| IE800178L (en) * | 1979-01-31 | 1980-07-31 | Pfizer Ltd | Derivatives of 4-amino-2-piperidinoquinazoline |
| US4287341A (en) * | 1979-11-01 | 1981-09-01 | Pfizer Inc. | Alkoxy-substituted-6-chloro-quinazoline-2,4-diones |
| FI800481A (fi) * | 1980-02-19 | 1981-08-20 | Orion Yhtymae Oy | Foerfarande foer framstaellning av substituerade acylpiperidiner |
-
1982
- 1982-08-28 ES ES515338A patent/ES515338A0/es active Granted
- 1982-09-03 EP EP82902731A patent/EP0087456A1/en not_active Withdrawn
- 1982-09-03 WO PCT/FI1982/000034 patent/WO1983000866A1/en not_active Application Discontinuation
- 1982-09-03 AU AU89066/82A patent/AU8906682A/en not_active Abandoned
- 1982-09-03 JP JP57502713A patent/JPS58501513A/ja active Pending
- 1982-09-08 PT PT75525A patent/PT75525B/pt unknown
- 1982-09-08 IT IT23168/82A patent/IT1156319B/it active
- 1982-09-08 ZA ZA826596A patent/ZA826596B/xx unknown
-
1983
- 1983-04-25 DK DK181083A patent/DK181083A/da not_active Application Discontinuation
- 1983-05-06 NO NO831622A patent/NO831622L/no unknown
- 1983-05-09 FI FI831585A patent/FI831585L/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK181083D0 (da) | 1983-04-25 |
| AU8906682A (en) | 1983-03-28 |
| EP0087456A1 (en) | 1983-09-07 |
| ES8405389A1 (es) | 1983-11-01 |
| FI831585A0 (fi) | 1983-05-09 |
| FI831585L (fi) | 1983-05-09 |
| IT8223168A0 (it) | 1982-09-08 |
| IT1156319B (it) | 1987-02-04 |
| PT75525B (en) | 1984-12-12 |
| ES515338A0 (es) | 1983-11-01 |
| DK181083A (da) | 1983-04-25 |
| WO1983000866A1 (en) | 1983-03-17 |
| PT75525A (en) | 1982-10-01 |
| JPS58501513A (ja) | 1983-09-08 |
| ZA826596B (en) | 1983-11-30 |
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