SU578876A3 - Способ получени производных пиразин-4-оксида или их солей - Google Patents
Способ получени производных пиразин-4-оксида или их солейInfo
- Publication number
- SU578876A3 SU578876A3 SU7301908970A SU1908970A SU578876A3 SU 578876 A3 SU578876 A3 SU 578876A3 SU 7301908970 A SU7301908970 A SU 7301908970A SU 1908970 A SU1908970 A SU 1908970A SU 578876 A3 SU578876 A3 SU 578876A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- compound
- group
- pyrazin
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical class [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- OODLOWQIRCXDEN-UHFFFAOYSA-N 6-methyl-4-oxidopyrazin-4-ium-2-carboxamide Chemical compound CC1=C[N+]([O-])=CC(C(N)=O)=N1 OODLOWQIRCXDEN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
- -1 oxyl Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- VEAMIQACXBDBGD-UHFFFAOYSA-N 6-methyl-1h-pyrazine-2,2-dicarboxylic acid Chemical class CC1=CN=CC(C(O)=O)(C(O)=O)N1 VEAMIQACXBDBGD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 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
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epoxy Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2366372 | 1972-04-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU578876A3 true SU578876A3 (ru) | 1977-10-30 |
Family
ID=11208983
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU7301908970A SU578876A3 (ru) | 1972-04-28 | 1973-04-27 | Способ получени производных пиразин-4-оксида или их солей |
Country Status (21)
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1094287B (it) * | 1978-03-23 | 1985-07-26 | Erba Carlo Spa | Derivati della 2-idrossimetil-pirazina aventi attivita' ipolipemizzante |
NL8202105A (nl) * | 1981-05-28 | 1982-12-16 | Erba Farmitalia | Werkwijze voor het bereiden van pyrazinederivaten. |
IL68036A (en) * | 1982-03-08 | 1986-08-31 | Erba Farmitalia | Preparation of 5-methyl-pyrazine-4-oxide-2-carboxylic acid and ester and amide derivatives |
GB2133004B (en) * | 1982-11-04 | 1986-06-11 | Ici Plc | Process for the extraction of metal values and novel metal extractants |
IT1201417B (it) * | 1985-05-17 | 1989-02-02 | Montedison Spa | Procedimento per la preparazione di 2-carbossipirazine 4 ossido |
US4962111A (en) * | 1989-06-08 | 1990-10-09 | The Research Foundation Of State University Of New York | Pyrazinoic acid esters as antituberculosis agents |
US5643912A (en) * | 1993-12-17 | 1997-07-01 | The Research Foundation Of State University Of Ny | Pyrazinoic acid esters as anti-mycobacterium avium agents |
CN113493421A (zh) * | 2020-04-08 | 2021-10-12 | 鲁南制药集团股份有限公司 | 一种1,2-二(4-吡啶基)乙烷-阿昔莫司共晶 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3452014A (en) * | 1964-08-14 | 1969-06-24 | Upjohn Co | 2,5-dimethylpyrazine p-toluenesulfonate |
AT291264B (de) * | 1969-05-05 | 1971-07-12 | Daiichi Seiyaku Company Ltd | Verfahren zur Herstellung von neuen Pyrazincarbonsäurederivaten |
NL6907199A (en) * | 1969-05-09 | 1970-11-11 | Hypoglycaemic pyrazine derivs |
-
1973
- 1973-04-12 GB GB1764573A patent/GB1361967A/en not_active Expired
- 1973-04-12 AU AU54413/73A patent/AU470007B2/en not_active Expired
- 1973-04-13 IL IL42026A patent/IL42026A/en unknown
- 1973-04-18 AT AT345073A patent/AT326669B/de active Protection Beyond IP Right Term
- 1973-04-18 DE DE2319834A patent/DE2319834C3/de not_active Expired
- 1973-04-19 ZA ZA732712A patent/ZA732712B/xx unknown
- 1973-04-24 CS CS2929A patent/CS172972B2/cs unknown
- 1973-04-25 NO NO1705/73A patent/NO137728C/no unknown
- 1973-04-26 NL NLAANVRAGE7305867,A patent/NL178595C/xx not_active IP Right Cessation
- 1973-04-26 BE BE130442A patent/BE798752A/xx not_active IP Right Cessation
- 1973-04-26 FI FI1336/73A patent/FI55033C/fi active
- 1973-04-26 JP JP4832373A patent/JPS5535384B2/ja not_active Expired
- 1973-04-27 CA CA169,694A patent/CA1000278A/en not_active Expired
- 1973-04-27 SU SU7301908970A patent/SU578876A3/ru active
- 1973-04-27 FR FR7315308A patent/FR2183049B1/fr not_active Expired
- 1973-04-27 CH CH605873A patent/CH582161A5/xx active Protection Beyond IP Right Term
- 1973-04-27 SE SE7305965A patent/SE387344B/xx unknown
- 1973-04-27 HU HUEA129A patent/HU165674B/hu unknown
- 1973-04-27 DK DK232573AA patent/DK138796B/da not_active IP Right Cessation
-
1976
- 1976-10-28 HK HK668/76*UA patent/HK66876A/xx unknown
-
1977
- 1977-12-30 MY MY77/77A patent/MY7700077A/xx unknown
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