DE1265754B - Verfahren zur Herstellung von Salzen von substituierten 1, 8-Dihydro-1, 3, 6, 8-tetraazapyrenen - Google Patents
Verfahren zur Herstellung von Salzen von substituierten 1, 8-Dihydro-1, 3, 6, 8-tetraazapyrenenInfo
- Publication number
- DE1265754B DE1265754B DEF41884A DEF0041884A DE1265754B DE 1265754 B DE1265754 B DE 1265754B DE F41884 A DEF41884 A DE F41884A DE F0041884 A DEF0041884 A DE F0041884A DE 1265754 B DE1265754 B DE 1265754B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- salts
- dihydro
- substituted
- tetraazapyrenes
- 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
- 150000003839 salts Chemical class 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- ZYRKCVFEURPISS-UHFFFAOYSA-N 5,7,12,14-tetrazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),5,8,10,12-heptaene Chemical class N1C=NC2=CC=C3N=CNC4=CC=C1C2=C34 ZYRKCVFEURPISS-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- LJYJFKXQKHSSEB-UHFFFAOYSA-N naphthalene-1,4,5,8-tetramine Chemical compound C1=CC(N)=C2C(N)=CC=C(N)C2=C1N LJYJFKXQKHSSEB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 231100001274 therapeutic index Toxicity 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 231100000816 toxic dose Toxicity 0.000 description 4
- -1 1,8-dihydro-1,3,6,8-tetraazapyren-dihydrochloride Chemical compound 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZUTCJXFCHHDFJS-UHFFFAOYSA-N 1,5-dinitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1[N+]([O-])=O ZUTCJXFCHHDFJS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JTFMQSMLMROVHQ-UHFFFAOYSA-N 6,13-dimethyl-5,7,12,14-tetrazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),5,8,10,12-heptaene Chemical compound N1C(C)=NC2=CC=C3NC(C)=NC4=CC=C1C2=C43 JTFMQSMLMROVHQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical class [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000224421 Heterolobosea Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 210000003001 amoeba Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ULUIRSHKJWANPP-UHFFFAOYSA-N n-(5-acetamidonaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1NC(C)=O ULUIRSHKJWANPP-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical compound N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41884A DE1265754B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von Salzen von substituierten 1, 8-Dihydro-1, 3, 6, 8-tetraazapyrenen |
| DEF41883A DE1263775B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von neuen substituierten 1, 3, 6, 8-Tetraazapyrenen |
| FR3787A FR1447183A (fr) | 1964-01-31 | 1965-01-27 | Procédé de fabrication de 1, 8-dihydro-1, 3, 6, 8-tétraazapyrènes substitués etde 1, 3, 6, 8-tétraazapyrènes substitués |
| NL6501197A NL6501197A (en, 2012) | 1964-01-31 | 1965-01-29 | |
| GB4020/65A GB1022660A (en) | 1964-01-31 | 1965-01-29 | Substituted 1,8-dihydro-1,3,6,8-tetra-azapyrenes and dehydrogenation products thereof |
| BE659016D BE659016A (en, 2012) | 1964-01-31 | 1965-01-29 | |
| FR15042A FR4367M (en, 2012) | 1964-01-31 | 1965-04-28 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41884A DE1265754B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von Salzen von substituierten 1, 8-Dihydro-1, 3, 6, 8-tetraazapyrenen |
| DEF41883A DE1263775B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von neuen substituierten 1, 3, 6, 8-Tetraazapyrenen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1265754B true DE1265754B (de) | 1968-04-11 |
Family
ID=25976125
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF41884A Pending DE1265754B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von Salzen von substituierten 1, 8-Dihydro-1, 3, 6, 8-tetraazapyrenen |
| DEF41883A Pending DE1263775B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von neuen substituierten 1, 3, 6, 8-Tetraazapyrenen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF41883A Pending DE1263775B (de) | 1964-01-31 | 1964-01-31 | Verfahren zur Herstellung von neuen substituierten 1, 3, 6, 8-Tetraazapyrenen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE659016A (en, 2012) |
| DE (2) | DE1265754B (en, 2012) |
| FR (2) | FR1447183A (en, 2012) |
| GB (1) | GB1022660A (en, 2012) |
| NL (1) | NL6501197A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8901300B2 (en) | 2011-02-18 | 2014-12-02 | Basf Se | Tetraazapyrene compounds and their use as N-type semiconductors |
| RU2561506C1 (ru) * | 2014-04-04 | 2015-08-27 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | СПОСОБ ПОЛУЧЕНИЯ 2,7-ДИАЛКИЛ-2,3а,5а,7,8а,10а-ГЕКСААЗАПЕРГИДРОПИРЕНОВ |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005520B (de) * | 1953-07-18 | 1957-04-04 | Hoechst Ag | Verfahren zur Herstellung von Derivaten des Naphthophenazins |
-
1964
- 1964-01-31 DE DEF41884A patent/DE1265754B/de active Pending
- 1964-01-31 DE DEF41883A patent/DE1263775B/de active Pending
-
1965
- 1965-01-27 FR FR3787A patent/FR1447183A/fr not_active Expired
- 1965-01-29 BE BE659016D patent/BE659016A/xx unknown
- 1965-01-29 GB GB4020/65A patent/GB1022660A/en not_active Expired
- 1965-01-29 NL NL6501197A patent/NL6501197A/xx unknown
- 1965-04-28 FR FR15042A patent/FR4367M/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005520B (de) * | 1953-07-18 | 1957-04-04 | Hoechst Ag | Verfahren zur Herstellung von Derivaten des Naphthophenazins |
Also Published As
| Publication number | Publication date |
|---|---|
| FR4367M (en, 2012) | 1966-08-22 |
| BE659016A (en, 2012) | 1965-07-29 |
| DE1263775B (de) | 1968-03-21 |
| NL6501197A (en, 2012) | 1965-08-02 |
| FR1447183A (fr) | 1966-07-29 |
| GB1022660A (en) | 1966-03-16 |
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