CH556847A - Verfahren zur herstellung neuer chinazolinon-derivate. - Google Patents
Verfahren zur herstellung neuer chinazolinon-derivate.Info
- Publication number
- CH556847A CH556847A CH491971A CH491971A CH556847A CH 556847 A CH556847 A CH 556847A CH 491971 A CH491971 A CH 491971A CH 491971 A CH491971 A CH 491971A CH 556847 A CH556847 A CH 556847A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- pyridyl
- solvent
- mol
- vinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 150000002390 heteroarenes Chemical class 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 8
- 231100000111 LD50 Toxicity 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- -1 o-Carboxyphenyl Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QSACCXVHEVWNMX-UHFFFAOYSA-N N-acetylanthranilic acid Chemical compound CC(=O)NC1=CC=CC=C1C(O)=O QSACCXVHEVWNMX-UHFFFAOYSA-N 0.000 description 4
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 3
- NTTMMVLSCIRXNE-UHFFFAOYSA-N 3-(2-methylphenyl)-2-(2-pyridin-3-ylethenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C=CC1=CC=CN=C1 NTTMMVLSCIRXNE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZPIQVUKIGDXDAD-UHFFFAOYSA-N N1=CC(=CC=C1)C=CC1=NC2=C(C(O1)=O)C=CC=C2 Chemical compound N1=CC(=CC=C1)C=CC1=NC2=C(C(O1)=O)C=CC=C2 ZPIQVUKIGDXDAD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- FUHPIGAAVQUXFH-UHFFFAOYSA-N benzene;hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC.C1=CC=CC=C1 FUHPIGAAVQUXFH-UHFFFAOYSA-N 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 108700001232 mouse P Proteins 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- GSRJPZPYIFRNAW-UHFFFAOYSA-N 2-(2-pyridin-2-ylethenyl)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1C=CC1=CC=CC=N1 GSRJPZPYIFRNAW-UHFFFAOYSA-N 0.000 description 1
- KJOLAZDWVDOTSF-UHFFFAOYSA-N 2-(prop-2-enoylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)C=C KJOLAZDWVDOTSF-UHFFFAOYSA-N 0.000 description 1
- OITIZRGEAFHLKE-UHFFFAOYSA-N 2-pyridin-3-ylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CN=C1 OITIZRGEAFHLKE-UHFFFAOYSA-N 0.000 description 1
- 241001366015 Desis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002936 tranquilizing effect Effects 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00078142A US3748325A (en) | 1970-04-06 | 1970-10-05 | Process for the preparation of quinazolinone derivatives |
| GB47210/70A GB1298603A (en) | 1970-04-06 | 1970-10-05 | Quinazolinone derivatives |
| CA108,437A CA940927A (en) | 1970-04-06 | 1971-03-23 | Process for the preparation of quinazolinone compounds |
| DE19712114607 DE2114607A1 (de) | 1970-04-06 | 1971-03-26 | Neue Chinazolinon-Derivate und Verfahren zu ihrer Herstellung |
| FR7111081A FR2131843B1 (cg-RX-API-DMAC10.html) | 1970-04-06 | 1971-03-30 | |
| CH491971A CH556847A (de) | 1970-04-06 | 1971-04-05 | Verfahren zur herstellung neuer chinazolinon-derivate. |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN126066 | 1970-04-06 | ||
| DE19712114607 DE2114607A1 (de) | 1970-04-06 | 1971-03-26 | Neue Chinazolinon-Derivate und Verfahren zu ihrer Herstellung |
| FR7111081A FR2131843B1 (cg-RX-API-DMAC10.html) | 1970-04-06 | 1971-03-30 | |
| CH491971A CH556847A (de) | 1970-04-06 | 1971-04-05 | Verfahren zur herstellung neuer chinazolinon-derivate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH556847A true CH556847A (de) | 1974-12-13 |
Family
ID=27428832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH491971A CH556847A (de) | 1970-04-06 | 1971-04-05 | Verfahren zur herstellung neuer chinazolinon-derivate. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3748325A (cg-RX-API-DMAC10.html) |
| CA (1) | CA940927A (cg-RX-API-DMAC10.html) |
| CH (1) | CH556847A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2114607A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2131843B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1298603A (cg-RX-API-DMAC10.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4832879A (en) * | 1980-03-04 | 1989-05-23 | Basf Aktiengesellchaft | Substituted 3-fluoroalkoxybenzoyl halides and their preparation |
| JPH064584B2 (ja) * | 1984-02-29 | 1994-01-19 | 沢井製薬株式会社 | 新規アニリド誘導体 |
| WO1992013535A1 (en) * | 1991-02-06 | 1992-08-20 | Research Corporation Technologies, Inc. | Anticonvulsant substituted quinazolones |
| US5283247A (en) * | 1991-02-06 | 1994-02-01 | Research Corporation Technologies, Inc. | Anticonvulsant substituted quinazolones |
| TR199802296T2 (xx) | 1996-05-15 | 1999-02-22 | Pfizer Inc. | Yeni 2,3 dis�bstit�te-4 (3H)-kinazolinonlar |
| DE69716810T2 (de) * | 1996-05-15 | 2003-02-27 | Pfizer Inc., New York | 2,3-Disubstituierte-(5,6)-heteroarylkondensierte-pyrimidin-4-one |
| AU732448B2 (en) * | 1997-02-28 | 2001-04-26 | Pfizer Products Inc. | Atropisomers of 3-heteroaryl-4(3H)-quinazolinones for the treatment of neurodegenerative and CNS-trauma related conditions |
| ATE267817T1 (de) * | 1997-02-28 | 2004-06-15 | Pfizer Prod Inc | Atropisomere von 3-aryl-4(3h)-chinazolinonen und ihre verwendung als ampa-rezeptor |
| US6323208B1 (en) | 1997-09-05 | 2001-11-27 | Pfizer Inc | Atropisomers of 2,3-disubstituted-(5.6)-heteroaryl fused-pyrimidin-4-ones |
| ITMI20050261A1 (it) * | 2005-02-21 | 2006-08-22 | Carlo Ghisalberti | Analoghi strutturali di avenatramidi loro uso in composizioni utili nel trattamento di disordini dermatologici |
| US9216177B2 (en) | 2011-02-28 | 2015-12-22 | Drexel University | Small molecular inhibitors of RAD51 recombinase and methods thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH430733A (de) * | 1963-04-25 | 1967-02-28 | Eprova Ag | Verfahren zur Herstellung von neuen Chinazolinon-Derivaten |
-
1970
- 1970-10-05 US US00078142A patent/US3748325A/en not_active Expired - Lifetime
- 1970-10-05 GB GB47210/70A patent/GB1298603A/en not_active Expired
-
1971
- 1971-03-23 CA CA108,437A patent/CA940927A/en not_active Expired
- 1971-03-26 DE DE19712114607 patent/DE2114607A1/de active Pending
- 1971-03-30 FR FR7111081A patent/FR2131843B1/fr not_active Expired
- 1971-04-05 CH CH491971A patent/CH556847A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1298603A (en) | 1972-12-06 |
| DE2114607A1 (de) | 1972-10-05 |
| US3748325A (en) | 1973-07-24 |
| FR2131843B1 (cg-RX-API-DMAC10.html) | 1974-05-24 |
| FR2131843A1 (cg-RX-API-DMAC10.html) | 1972-11-17 |
| CA940927A (en) | 1974-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |