NO820320L - Fremgangsmaate for fremstilling av farmakologisk aktive imidazo(1,5-d)-as-triazin-derivater - Google Patents
Fremgangsmaate for fremstilling av farmakologisk aktive imidazo(1,5-d)-as-triazin-derivaterInfo
- Publication number
- NO820320L NO820320L NO820320A NO820320A NO820320L NO 820320 L NO820320 L NO 820320L NO 820320 A NO820320 A NO 820320A NO 820320 A NO820320 A NO 820320A NO 820320 L NO820320 L NO 820320L
- Authority
- NO
- Norway
- Prior art keywords
- propyl
- triazin
- approx
- methylimidazo
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- UAOOBKAGZAHSNJ-UHFFFAOYSA-N imidazo[1,5-d][1,2,4]triazine Chemical class C1=NN=CC2=CN=CN21 UAOOBKAGZAHSNJ-UHFFFAOYSA-N 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- -1 1,8-dimethyl-6-n-propyl-imidazo[1,5-d]-as-triazin-4(3H)-one monohydrochloride Chemical compound 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- GYRNWWWCIUGQRS-UHFFFAOYSA-N 8-methyl-1,6-dipropyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CCCC1=NN=C(O)N2C(CCC)=NC(C)=C21 GYRNWWWCIUGQRS-UHFFFAOYSA-N 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229960001340 histamine Drugs 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 239000007787 solid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- PQQJTBGWBNXLAY-UHFFFAOYSA-N 1,8-dimethyl-6-propyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CC1=NNC(=O)N2C(CCC)=NC(C)=C21 PQQJTBGWBNXLAY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- WXFQRFAPEICWRJ-UHFFFAOYSA-N 1-(5-methyl-2-propyl-1h-imidazol-4-yl)ethanone Chemical compound CCCC1=NC(C)=C(C(C)=O)N1 WXFQRFAPEICWRJ-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 235000001050 hortel pimenta Nutrition 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
- 239000003701 inert diluent Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 229940062713 mite extract Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000009637 wintergreen oil Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/231,196 US4447603A (en) | 1981-02-04 | 1981-02-04 | Substituted-6-n-propyl-8-methylimidazo[1,5-d]-as-triazin-4-(3H)-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO820320L true NO820320L (no) | 1982-08-05 |
Family
ID=22868148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO820320A NO820320L (no) | 1981-02-04 | 1982-02-03 | Fremgangsmaate for fremstilling av farmakologisk aktive imidazo(1,5-d)-as-triazin-derivater |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4447603A (pt) |
| EP (1) | EP0057289A1 (pt) |
| JP (1) | JPS57146781A (pt) |
| KR (1) | KR830009101A (pt) |
| AR (1) | AR227703A1 (pt) |
| AU (1) | AU8015682A (pt) |
| CA (1) | CA1156230A (pt) |
| DD (1) | DD201596A5 (pt) |
| DE (1) | DE3202366A1 (pt) |
| DK (1) | DK46982A (pt) |
| ES (1) | ES509298A0 (pt) |
| FI (1) | FI820341L (pt) |
| GR (1) | GR75170B (pt) |
| IE (1) | IE820237L (pt) |
| IL (1) | IL64646A0 (pt) |
| NO (1) | NO820320L (pt) |
| PL (1) | PL234938A1 (pt) |
| PT (1) | PT74374B (pt) |
| ZA (1) | ZA82698B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085756A1 (en) * | 1982-02-10 | 1983-08-17 | American Cyanamid Company | Process for preparing 1-substituted-6-n-propyl-8-methylimidazo(1,5-d)-as-triazin-4(3H)-ones |
| CA2163399A1 (en) * | 1994-11-24 | 1996-05-25 | Katsuhiro Kawano | Triazine derivative, chymase activity inhibitor and nitric oxide production inhibitor |
| EP2550374A1 (en) | 2010-03-23 | 2013-01-30 | Siemens Aktiengesellschaft | Metallic bondcoat or alloy with a high / ' transition temperature and a component |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115572A (en) * | 1977-02-03 | 1978-09-19 | American Cyanamid Company | Imidazo-[1,5-d]-as-triazin-1(2H)-ones and method of ameliorating asthma |
| US4107307A (en) * | 1977-02-03 | 1978-08-15 | American Cyanamid Company | Imidazo [1,5-d]-as-triazine-4(3H)-ones and thiones |
| US4096257A (en) * | 1977-05-23 | 1978-06-20 | American Cyanamid Company | Substituted imidazo [1,2-d]-as-triazines |
| US4107308A (en) * | 1977-10-18 | 1978-08-15 | American Cyanamid Company | Imidazo[1,5-d]-as-triazines |
-
1981
- 1981-02-04 US US06/231,196 patent/US4447603A/en not_active Expired - Fee Related
- 1981-12-24 EP EP81110776A patent/EP0057289A1/en not_active Ceased
- 1981-12-25 IL IL64646A patent/IL64646A0/xx unknown
- 1981-12-30 CA CA000393430A patent/CA1156230A/en not_active Expired
-
1982
- 1982-01-26 DE DE19823202366 patent/DE3202366A1/de not_active Withdrawn
- 1982-02-01 JP JP57013413A patent/JPS57146781A/ja active Pending
- 1982-02-01 GR GR67202A patent/GR75170B/el unknown
- 1982-02-02 PT PT74374A patent/PT74374B/pt unknown
- 1982-02-02 AR AR288324A patent/AR227703A1/es active
- 1982-02-03 FI FI820341A patent/FI820341L/fi not_active Application Discontinuation
- 1982-02-03 AU AU80156/82A patent/AU8015682A/en not_active Abandoned
- 1982-02-03 PL PL23493882A patent/PL234938A1/xx unknown
- 1982-02-03 ES ES509298A patent/ES509298A0/es active Granted
- 1982-02-03 IE IE820237A patent/IE820237L/xx unknown
- 1982-02-03 ZA ZA82698A patent/ZA82698B/xx unknown
- 1982-02-03 DK DK46982A patent/DK46982A/da not_active Application Discontinuation
- 1982-02-03 KR KR1019820000441A patent/KR830009101A/ko unknown
- 1982-02-03 NO NO820320A patent/NO820320L/no unknown
- 1982-02-04 DD DD82237183A patent/DD201596A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL64646A0 (en) | 1982-03-31 |
| PT74374B (en) | 1983-08-24 |
| PL234938A1 (en) | 1983-01-31 |
| DD201596A5 (de) | 1983-07-27 |
| FI820341L (fi) | 1982-08-05 |
| US4447603A (en) | 1984-05-08 |
| EP0057289A1 (en) | 1982-08-11 |
| IE820237L (en) | 1982-08-04 |
| ES8302458A1 (es) | 1982-12-16 |
| KR830009101A (ko) | 1983-12-17 |
| ES509298A0 (es) | 1982-12-16 |
| GR75170B (pt) | 1984-07-13 |
| ZA82698B (en) | 1983-01-26 |
| DK46982A (da) | 1982-08-05 |
| JPS57146781A (en) | 1982-09-10 |
| CA1156230A (en) | 1983-11-01 |
| AR227703A1 (es) | 1982-11-30 |
| PT74374A (en) | 1982-03-01 |
| DE3202366A1 (de) | 1982-09-23 |
| AU8015682A (en) | 1982-08-12 |
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