DE2101275A1 - Neue Chinazolinen-Verbindungen und Verfahren zu ihrer Herstellung - Google Patents
Neue Chinazolinen-Verbindungen und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2101275A1 DE2101275A1 DE19712101275 DE2101275A DE2101275A1 DE 2101275 A1 DE2101275 A1 DE 2101275A1 DE 19712101275 DE19712101275 DE 19712101275 DE 2101275 A DE2101275 A DE 2101275A DE 2101275 A1 DE2101275 A1 DE 2101275A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- pyridyl
- methyl
- compounds
- acid addition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 125000003790 chinazolinyl group Chemical group 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- -1 3-methyl-2-pyridyl Chemical group 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 229960004979 fampridine Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 231100000111 LD50 Toxicity 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LZORTVCIUAAACZ-UHFFFAOYSA-N 2-methyl-3-(3-methylpyridin-2-yl)quinazolin-4-one Chemical compound CC1=CC=CN=C1N1C(=O)C2=CC=CC=C2N=C1C LZORTVCIUAAACZ-UHFFFAOYSA-N 0.000 description 3
- AVQUANDWSGLIIP-UHFFFAOYSA-N 2-propan-2-yl-3-pyridin-4-ylquinazolin-4-one Chemical compound CC(C)C1=NC2=CC=CC=C2C(=O)N1C1=CC=NC=C1 AVQUANDWSGLIIP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- HTWMTDKMOSSPMU-UHFFFAOYSA-N 1,2-benzoxazin-4-one Chemical class C1=CC=C2C(=O)C=NOC2=C1 HTWMTDKMOSSPMU-UHFFFAOYSA-N 0.000 description 1
- MFQIGFQXUBKVSJ-UHFFFAOYSA-N 2-acetamido-5-chlorobenzoic acid Chemical compound CC(=O)NC1=CC=C(Cl)C=C1C(O)=O MFQIGFQXUBKVSJ-UHFFFAOYSA-N 0.000 description 1
- VFHSJTHAMJFUCK-UHFFFAOYSA-N 2-acetamido-6-chlorobenzoic acid Chemical compound CC(=O)NC1=CC=CC(Cl)=C1C(O)=O VFHSJTHAMJFUCK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LBJORARPTAMYBO-UHFFFAOYSA-N 2-propan-2-yl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C(C)C)=NC2=C1 LBJORARPTAMYBO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- DVXONVZXNCMEMS-UHFFFAOYSA-N 5-chloro-2-methyl-3-(3-methylpyridin-2-yl)quinazolin-4-one Chemical compound CC1=CC=CN=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1C DVXONVZXNCMEMS-UHFFFAOYSA-N 0.000 description 1
- KLQIQAQXHDSJFH-UHFFFAOYSA-N 7-chloro-2-methyl-3,1-benzoxazin-4-one Chemical compound ClC1=CC=C2C(=O)OC(C)=NC2=C1 KLQIQAQXHDSJFH-UHFFFAOYSA-N 0.000 description 1
- MGZKBWGZFJSTSQ-UHFFFAOYSA-N 8-chloro-2-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=C1Cl MGZKBWGZFJSTSQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QSACCXVHEVWNMX-UHFFFAOYSA-N N-acetylanthranilic acid Chemical compound CC(=O)NC1=CC=CC=C1C(O)=O QSACCXVHEVWNMX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 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
- C07D401/04—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1297043D GB1297043A (enrdf_load_stackoverflow) | 1970-01-15 | 1970-08-03 | |
| CA102,459A CA939670A (en) | 1970-01-15 | 1971-01-07 | Process for the preparation of quinazolinone compounds |
| DE19712101275 DE2101275A1 (de) | 1970-01-15 | 1971-01-13 | Neue Chinazolinen-Verbindungen und Verfahren zu ihrer Herstellung |
| CH56171A CH552598A (de) | 1970-01-15 | 1971-01-14 | Verfahren zur herstellung neuer chinazolinon-verbindungen. |
| FR7101263A FR2081437B1 (enrdf_load_stackoverflow) | 1970-01-15 | 1971-01-15 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN124860 | 1970-01-15 | ||
| IN126566 | 1970-05-08 | ||
| DE19712101275 DE2101275A1 (de) | 1970-01-15 | 1971-01-13 | Neue Chinazolinen-Verbindungen und Verfahren zu ihrer Herstellung |
| CH56171A CH552598A (de) | 1970-01-15 | 1971-01-14 | Verfahren zur herstellung neuer chinazolinon-verbindungen. |
| FR7101263A FR2081437B1 (enrdf_load_stackoverflow) | 1970-01-15 | 1971-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2101275A1 true DE2101275A1 (de) | 1972-07-27 |
Family
ID=27508858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712101275 Pending DE2101275A1 (de) | 1970-01-15 | 1971-01-13 | Neue Chinazolinen-Verbindungen und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA939670A (enrdf_load_stackoverflow) |
| CH (1) | CH552598A (enrdf_load_stackoverflow) |
| DE (1) | DE2101275A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2081437B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1297043A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283247A (en) * | 1991-02-06 | 1994-02-01 | Research Corporation Technologies, Inc. | Anticonvulsant substituted quinazolones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3086910A (en) * | 1960-03-09 | 1963-04-23 | Wallace & Tiernan Inc | Central nervous system depressants 3-(2'-pyridyl)-4-quinazolones |
| DE1168435B (de) * | 1961-12-09 | 1964-04-23 | Kali Chemie Ag | Verfahren zur Herstellung von 4-Oxo-3, 4-dihydrochinazolinen |
| FR1396640A (fr) * | 1963-04-25 | 1965-04-23 | Eprova Ag | Procédé pour la préparation de nouveaux dérivés de quinazolinone |
| DE1695799C3 (de) * | 1967-01-23 | 1974-10-17 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 5-Chlor-3- eckige Klammer auf pyridin-2'-yl eckige Klammer zu -4-(3H)- chinazolinone |
-
1970
- 1970-08-03 GB GB1297043D patent/GB1297043A/en not_active Expired
-
1971
- 1971-01-07 CA CA102,459A patent/CA939670A/en not_active Expired
- 1971-01-13 DE DE19712101275 patent/DE2101275A1/de active Pending
- 1971-01-14 CH CH56171A patent/CH552598A/de not_active IP Right Cessation
- 1971-01-15 FR FR7101263A patent/FR2081437B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA939670A (en) | 1974-01-08 |
| GB1297043A (enrdf_load_stackoverflow) | 1972-11-22 |
| FR2081437B1 (enrdf_load_stackoverflow) | 1975-06-06 |
| FR2081437A1 (enrdf_load_stackoverflow) | 1971-12-03 |
| CH552598A (de) | 1974-08-15 |
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