SU999974A3 - Способ получени конденсированных производных пиримидина или их солей - Google Patents
Способ получени конденсированных производных пиримидина или их солей Download PDFInfo
- Publication number
- SU999974A3 SU999974A3 SU782897009A SU2897009A SU999974A3 SU 999974 A3 SU999974 A3 SU 999974A3 SU 782897009 A SU782897009 A SU 782897009A SU 2897009 A SU2897009 A SU 2897009A SU 999974 A3 SU999974 A3 SU 999974A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- 4alkyl
- pyrimidine
- pyrido
- oxo
- tetrahydro
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 4
- 150000003230 pyrimidines Chemical class 0.000 title claims 2
- -1 sulfur anion Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 7
- 239000011593 sulfur Substances 0.000 claims abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- 238000000921 elemental analysis Methods 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 10
- 229910052760 oxygen Inorganic materials 0.000 abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 6
- 239000001301 oxygen Substances 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000001766 physiological effect Effects 0.000 abstract 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- UBOXAHWUKQXQEH-UHFFFAOYSA-N 2,3,4,6-tetrahydro-1h-pyrido[1,2-a]pyrimidine Chemical compound C1=CCN2CCCNC2=C1 UBOXAHWUKQXQEH-UHFFFAOYSA-N 0.000 description 1
- DZXWMORFICYADZ-UHFFFAOYSA-N 4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-3-carbonitrile Chemical compound O=C1C(C#N)=CN=C2CCCN12 DZXWMORFICYADZ-UHFFFAOYSA-N 0.000 description 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Anesthesiology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1793A HU185925B (en) | 1977-12-29 | 1977-12-29 | Process for preparing compounds with nitrogen bridge head |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU999974A3 true SU999974A3 (ru) | 1983-02-23 |
Family
ID=10994682
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782897009A SU999974A3 (ru) | 1977-12-29 | 1978-12-28 | Способ получени конденсированных производных пиримидина или их солей |
| SU782704102A SU1072807A3 (ru) | 1977-12-29 | 1978-12-28 | Способ получени производных пиридо/1,2-а/пиримидина или их кислотно-аддитивных солей,или их оптических изомеров |
| SU802897056A SU1082324A3 (ru) | 1977-12-29 | 1980-03-20 | Способ получени конденсированных производных пиримидина или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782704102A SU1072807A3 (ru) | 1977-12-29 | 1978-12-28 | Способ получени производных пиридо/1,2-а/пиримидина или их кислотно-аддитивных солей,или их оптических изомеров |
| SU802897056A SU1082324A3 (ru) | 1977-12-29 | 1980-03-20 | Способ получени конденсированных производных пиримидина или их солей |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54106496A (fr) |
| BE (1) | BE873193A (fr) |
| CH (1) | CH641456A5 (fr) |
| DE (1) | DE2854113A1 (fr) |
| FR (1) | FR2413388A1 (fr) |
| GB (1) | GB2011406B (fr) |
| HU (1) | HU185925B (fr) |
| SU (3) | SU999974A3 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU183330B (en) * | 1981-02-13 | 1984-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new of 2,4,8-triazaphenalenium-salts |
| AR046938A1 (es) * | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
| RU2750293C2 (ru) * | 2015-05-12 | 2021-06-25 | ЭфЭмСи Корпорейшн | Арилзамещенные бициклические соединения в качестве гербицидов |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU168014B (fr) * | 1973-03-30 | 1976-02-28 | ||
| US3898224A (en) * | 1974-09-09 | 1975-08-05 | Squibb & Sons Inc | 1,6,7,8-Tetrahydro-4-oxo-4H-pyrido {8 1,2-A{9 pyrimidine-9-carboalkoxy compounds |
| US3965100A (en) * | 1975-02-26 | 1976-06-22 | E. R. Squibb & Sons, Inc. | 2,3-Dihydrocyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one and its derivatives |
| HU174693B (hu) * | 1976-02-12 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija kondensirovannykh proizvodnykh pirimidina |
-
1977
- 1977-12-29 HU HU77CI1793A patent/HU185925B/hu unknown
-
1978
- 1978-12-15 DE DE19782854113 patent/DE2854113A1/de not_active Ceased
- 1978-12-27 FR FR7836460A patent/FR2413388A1/fr active Granted
- 1978-12-28 SU SU782897009A patent/SU999974A3/ru active
- 1978-12-28 GB GB7850104A patent/GB2011406B/en not_active Expired
- 1978-12-28 CH CH1323378A patent/CH641456A5/de not_active IP Right Cessation
- 1978-12-28 SU SU782704102A patent/SU1072807A3/ru active
- 1978-12-29 BE BE192658A patent/BE873193A/fr not_active IP Right Cessation
- 1978-12-29 JP JP16460478A patent/JPS54106496A/ja active Pending
-
1980
- 1980-03-20 SU SU802897056A patent/SU1082324A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1072807A3 (ru) | 1984-02-07 |
| BE873193A (fr) | 1979-04-17 |
| FR2413388B1 (fr) | 1982-03-26 |
| DE2854113A1 (de) | 1979-07-12 |
| JPS54106496A (en) | 1979-08-21 |
| CH641456A5 (de) | 1984-02-29 |
| HU185925B (en) | 1985-04-28 |
| GB2011406B (en) | 1982-09-08 |
| SU1082324A3 (ru) | 1984-03-23 |
| FR2413388A1 (fr) | 1979-07-27 |
| GB2011406A (en) | 1979-07-11 |
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