HU187716B - Process for producing pyrazine derivatives - Google Patents
Process for producing pyrazine derivatives Download PDFInfo
- Publication number
- HU187716B HU187716B HU821712A HU171282A HU187716B HU 187716 B HU187716 B HU 187716B HU 821712 A HU821712 A HU 821712A HU 171282 A HU171282 A HU 171282A HU 187716 B HU187716 B HU 187716B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- acid
- compounds
- pyrazine derivatives
- hydroxy
- Prior art date
Links
- 150000003216 pyrazines Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002862 amidating effect Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- OTVZGAXESBAAQQ-UHFFFAOYSA-N pyrazine-2,3-dicarbonitrile Chemical compound N#CC1=NC=CN=C1C#N OTVZGAXESBAAQQ-UHFFFAOYSA-N 0.000 claims description 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 2
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 2
- 150000003222 pyridines Chemical class 0.000 abstract description 2
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YNONYHDIQPCCNE-UHFFFAOYSA-N 2,2-diaminopropanedinitrile Chemical compound N#CC(N)(N)C#N YNONYHDIQPCCNE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RBYJWCRKFLGNDB-UHFFFAOYSA-N 5-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)C=N1 RBYJWCRKFLGNDB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 2
- RHYUBLSWHDYKAO-UHFFFAOYSA-N 5-methylpyrazine-2,3-dicarbonitrile Chemical compound CC1=CN=C(C#N)C(C#N)=N1 RHYUBLSWHDYKAO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 1
- BTYKRSQVJNDFFF-UHFFFAOYSA-N 5-methyl-4-oxidopyrazin-4-ium-2-carboxamide Chemical compound CC1=CN=C(C(N)=O)C=[N+]1[O-] BTYKRSQVJNDFFF-UHFFFAOYSA-N 0.000 description 1
- OYBQCUZBVHFPBU-UHFFFAOYSA-N 5-methylpyrazine-2-carboxamide Chemical compound CC1=CN=C(C(N)=O)C=N1 OYBQCUZBVHFPBU-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000001816 cooling Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8116263 | 1981-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187716B true HU187716B (en) | 1986-02-28 |
Family
ID=10522093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821712A HU187716B (en) | 1981-05-28 | 1982-05-27 | Process for producing pyrazine derivatives |
Country Status (20)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1201417B (it) * | 1985-05-17 | 1989-02-02 | Montedison Spa | Procedimento per la preparazione di 2-carbossipirazine 4 ossido |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1361967A (en) * | 1972-04-28 | 1974-07-30 | Erba Carlo Spa | Pyrazine 4-oxide derivatives and process for their preparation |
| JPS565742B2 (enrdf_load_stackoverflow) * | 1973-09-29 | 1981-02-06 | ||
| JPS5134175A (en) * | 1974-09-18 | 1976-03-23 | Sagami Chem Res | Pirajinjudotai no seizohoho |
| JPS52153980A (en) * | 1976-06-17 | 1977-12-21 | Nippon Soda Co Ltd | Synthesis of 2,3-dicyanopyrazine |
| JPS5488280A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of dicyanopyradines |
| JPS5488281A (en) * | 1977-12-20 | 1979-07-13 | Nitsupou Kagaku Kk | Manufacture of pyrazine monocarboxylic acid |
-
1982
- 1982-05-21 NL NL8202105A patent/NL8202105A/nl active Search and Examination
- 1982-05-24 FI FI821832A patent/FI73669C/fi not_active IP Right Cessation
- 1982-05-24 IL IL65864A patent/IL65864A/xx not_active IP Right Cessation
- 1982-05-24 DE DE19823219407 patent/DE3219407A1/de active Granted
- 1982-05-24 AT AT0203682A patent/AT387217B/de not_active IP Right Cessation
- 1982-05-25 CS CS823842A patent/CS226741B2/cs unknown
- 1982-05-25 FR FR8209038A patent/FR2506768B1/fr not_active Expired
- 1982-05-25 CA CA000403636A patent/CA1237724A/en not_active Expired
- 1982-05-25 GR GR68246A patent/GR76417B/el unknown
- 1982-05-25 AU AU84126/82A patent/AU8412682A/en not_active Abandoned
- 1982-05-26 JP JP57088153A patent/JPS57200368A/ja active Granted
- 1982-05-26 SE SE8203273A patent/SE462971B/sv not_active IP Right Cessation
- 1982-05-26 IE IE1261/82A patent/IE52992B1/en not_active IP Right Cessation
- 1982-05-26 ZA ZA823660A patent/ZA823660B/xx unknown
- 1982-05-27 YU YU1131/82A patent/YU42766B/xx unknown
- 1982-05-27 DK DK239482A patent/DK155325C/da not_active IP Right Cessation
- 1982-05-27 IT IT8221517A patent/IT1210478B/it active Protection Beyond IP Right Term
- 1982-05-27 BE BE0/208187A patent/BE893317A/fr not_active IP Right Cessation
- 1982-05-27 CH CH3285/82A patent/CH649763A5/de not_active IP Right Cessation
- 1982-05-27 HU HU821712A patent/HU187716B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8221517A0 (it) | 1982-05-27 |
| YU42766B (en) | 1988-12-31 |
| FI821832A0 (fi) | 1982-05-24 |
| IE821261L (en) | 1982-11-28 |
| YU113182A (en) | 1985-03-20 |
| DK155325B (da) | 1989-03-28 |
| SE8203273L (sv) | 1982-11-29 |
| FR2506768A1 (fr) | 1982-12-03 |
| DE3219407C2 (enrdf_load_stackoverflow) | 1990-09-06 |
| ATA203682A (de) | 1988-05-15 |
| DK155325C (da) | 1989-09-18 |
| IT1210478B (it) | 1989-09-14 |
| BE893317A (fr) | 1982-11-29 |
| AU8412682A (en) | 1982-12-02 |
| CA1237724A (en) | 1988-06-07 |
| IL65864A0 (en) | 1982-08-31 |
| JPS57200368A (en) | 1982-12-08 |
| IL65864A (en) | 1985-08-30 |
| DK239482A (da) | 1982-11-29 |
| CH649763A5 (de) | 1985-06-14 |
| GR76417B (enrdf_load_stackoverflow) | 1984-08-10 |
| FI73669C (fi) | 1987-11-09 |
| CS226741B2 (en) | 1984-04-16 |
| NL8202105A (nl) | 1982-12-16 |
| FI73669B (fi) | 1987-07-31 |
| ZA823660B (en) | 1983-03-30 |
| FR2506768B1 (fr) | 1985-06-21 |
| AT387217B (de) | 1988-12-27 |
| SE462971B (sv) | 1990-09-24 |
| DE3219407A1 (de) | 1983-01-05 |
| IE52992B1 (en) | 1988-04-27 |
| JPH0456034B2 (enrdf_load_stackoverflow) | 1992-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |