DD283624A5 - Verfahren zur herstellung von neuartigem 5-(substituiertes-amino)-8-(phenyl oder substituiertes-phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one - Google Patents
Verfahren zur herstellung von neuartigem 5-(substituiertes-amino)-8-(phenyl oder substituiertes-phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Download PDFInfo
- Publication number
- DD283624A5 DD283624A5 DD89325854A DD32585489A DD283624A5 DD 283624 A5 DD283624 A5 DD 283624A5 DD 89325854 A DD89325854 A DD 89325854A DD 32585489 A DD32585489 A DD 32585489A DD 283624 A5 DD283624 A5 DD 283624A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phenyl
- trifluoromethyl
- stirred
- mixture
- tetraazaacenaphthylene
- Prior art date
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- HGOQXPTZTZPWMD-UHFFFAOYSA-N 1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-5-one Chemical compound C1C=CN2N=CC3=C2N1C=NC3=O HGOQXPTZTZPWMD-UHFFFAOYSA-N 0.000 title claims abstract description 22
- -1 AMINO Chemical class 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 91
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
- 239000011541 reaction mixture Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 238000003756 stirring Methods 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 17
- 239000012312 sodium hydride Substances 0.000 claims description 17
- 229960000583 acetic acid Drugs 0.000 claims description 14
- 239000012362 glacial acetic acid Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 239000000047 product Substances 0.000 description 56
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 23
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- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 description 14
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 10
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- 241000699670 Mus sp. Species 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 9
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 235000011089 carbon dioxide Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 206010021143 Hypoxia Diseases 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 230000001146 hypoxic effect Effects 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
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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
- C07D487/12—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 three hetero rings
- C07D487/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15844888A | 1988-02-22 | 1988-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283624A5 true DD283624A5 (de) | 1990-10-17 |
Family
ID=22568168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89325854A DD283624A5 (de) | 1988-02-22 | 1989-02-20 | Verfahren zur herstellung von neuartigem 5-(substituiertes-amino)-8-(phenyl oder substituiertes-phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0329940B1 (cs) |
| JP (1) | JP2641556B2 (cs) |
| KR (1) | KR970009226B1 (cs) |
| AR (1) | AR247211A1 (cs) |
| AT (1) | ATE99686T1 (cs) |
| AU (1) | AU611769B2 (cs) |
| CA (1) | CA1329594C (cs) |
| CZ (1) | CZ284273B6 (cs) |
| DD (1) | DD283624A5 (cs) |
| DE (1) | DE68911951T2 (cs) |
| DK (1) | DK172397B1 (cs) |
| ES (1) | ES2061739T3 (cs) |
| FI (1) | FI89922C (cs) |
| HU (1) | HU203554B (cs) |
| IE (1) | IE64147B1 (cs) |
| IL (1) | IL88974A (cs) |
| NO (1) | NO169589C (cs) |
| NZ (1) | NZ228009A (cs) |
| PH (1) | PH26358A (cs) |
| PL (1) | PL158865B1 (cs) |
| PT (1) | PT89766B (cs) |
| SK (1) | SK105589A3 (cs) |
| ZA (1) | ZA891310B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013737A (en) * | 1988-02-22 | 1991-05-07 | American Cyanamid Company | 2,4,8-Trisubstituted-3H,6H-1,4,5A,8A-tetraazaacenaphtylene-3,5-(4H)-diones and 2,4-8-trisubstituted-4,5-dihydro-5-thioxo-3H,6H-1,4,5A,8A-tetrazaacenaphthylen-3-ones |
| SG47588A1 (en) * | 1992-03-26 | 1998-04-17 | American Cyanamid Co | An improved process for the synthesis of 5-[(substituted) amino] -8- [phenyl or substituted-phenyl]-3H, 6H-1, 4, 5A, 8A-tetraazaacenaphtylen-3- ones |
| AU5611398A (en) * | 1996-12-19 | 1998-07-15 | American Cyanamid Company | Method of treating or inhibiting neutropenia |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4236005A (en) * | 1979-07-02 | 1980-11-25 | American Cyanamid Company | Imidazo[1,5-a]pyrimidines |
| US4713383A (en) * | 1984-10-01 | 1987-12-15 | Ciba-Geigy Corporation | Triazoloquinazoline compounds, and their methods of preparation, pharmaceutical compositions, and uses |
| US4576943A (en) * | 1984-10-09 | 1986-03-18 | American Cyanamid Company | Pyrazolo[1,5-a]pyrimidines |
| EP0264773A1 (en) * | 1986-10-16 | 1988-04-27 | American Cyanamid Company | 4,5-dihydro and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidines |
-
1989
- 1989-01-16 AT AT89100657T patent/ATE99686T1/de active
- 1989-01-16 DE DE68911951T patent/DE68911951T2/de not_active Expired - Fee Related
- 1989-01-16 ES ES89100657T patent/ES2061739T3/es not_active Expired - Lifetime
- 1989-01-16 EP EP89100657A patent/EP0329940B1/en not_active Expired - Lifetime
- 1989-01-17 IL IL88974A patent/IL88974A/xx not_active IP Right Cessation
- 1989-02-16 NZ NZ228009A patent/NZ228009A/xx unknown
- 1989-02-17 CZ CS891055A patent/CZ284273B6/cs not_active IP Right Cessation
- 1989-02-17 SK SK1055-89A patent/SK105589A3/sk unknown
- 1989-02-20 JP JP1038480A patent/JP2641556B2/ja not_active Expired - Lifetime
- 1989-02-20 PT PT89766A patent/PT89766B/pt not_active IP Right Cessation
- 1989-02-20 DD DD89325854A patent/DD283624A5/de unknown
- 1989-02-20 PH PH38218A patent/PH26358A/en unknown
- 1989-02-20 CA CA000591526A patent/CA1329594C/en not_active Expired - Fee Related
- 1989-02-21 DK DK079589A patent/DK172397B1/da not_active IP Right Cessation
- 1989-02-21 IE IE54389A patent/IE64147B1/en not_active IP Right Cessation
- 1989-02-21 KR KR89002051A patent/KR970009226B1/ko not_active Expired - Fee Related
- 1989-02-21 ZA ZA891310A patent/ZA891310B/xx unknown
- 1989-02-21 AU AU30172/89A patent/AU611769B2/en not_active Ceased
- 1989-02-21 NO NO890724A patent/NO169589C/no not_active IP Right Cessation
- 1989-02-21 FI FI890826A patent/FI89922C/fi not_active IP Right Cessation
- 1989-02-21 PL PL1989277837A patent/PL158865B1/pl unknown
- 1989-02-21 AR AR89313253A patent/AR247211A1/es active
- 1989-02-22 HU HU89856A patent/HU203554B/hu not_active IP Right Cessation
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