SU509234A3 - Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидина - Google Patents
Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидинаInfo
- Publication number
- SU509234A3 SU509234A3 SU1953844A SU1953844A SU509234A3 SU 509234 A3 SU509234 A3 SU 509234A3 SU 1953844 A SU1953844 A SU 1953844A SU 1953844 A SU1953844 A SU 1953844A SU 509234 A3 SU509234 A3 SU 509234A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitro
- furyl
- thieno
- pyrimidine
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 5-nitro-2-furyl Chemical group 0.000 title description 11
- 150000003230 pyrimidines Chemical class 0.000 title description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JSQVISDWESOYOK-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidin-4-amine Chemical compound N=1C=2SC=CC=2C(N)=NC=1C1=CC=C([N+]([O-])=O)O1 JSQVISDWESOYOK-UHFFFAOYSA-N 0.000 description 1
- SOKYMWVLBPDOMH-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidine Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC=C(C=CS2)C2=N1 SOKYMWVLBPDOMH-UHFFFAOYSA-N 0.000 description 1
- OHMLBZKIUZTEOC-UHFFFAOYSA-N 2-aminothiophene-3-carboxylic acid Chemical compound NC=1SC=CC=1C(O)=O OHMLBZKIUZTEOC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical compound [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- NYSSVFLMKLATPY-UHFFFAOYSA-N 4-chloro-2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidine Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(Cl)=C(C=CS2)C2=N1 NYSSVFLMKLATPY-UHFFFAOYSA-N 0.000 description 1
- ZICBXQDJDHOBHH-UHFFFAOYSA-N 4-chloro-5-methyl-2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidine Chemical compound N=1C(Cl)=C2C(C)=CSC2=NC=1C1=CC=C([N+]([O-])=O)O1 ZICBXQDJDHOBHH-UHFFFAOYSA-N 0.000 description 1
- QIQRMINBGVUTOL-UHFFFAOYSA-N 4-chloro-6-ethyl-2-(5-nitrofuran-2-yl)thieno[2,3-d]pyrimidine Chemical compound N1=C2SC(CC)=CC2=C(Cl)N=C1C1=CC=C([N+]([O-])=O)O1 QIQRMINBGVUTOL-UHFFFAOYSA-N 0.000 description 1
- LRFIHWGUGBXFEC-UHFFFAOYSA-N 4-methylthiophene-3-carboxylic acid Chemical compound CC1=CSC=C1C(O)=O LRFIHWGUGBXFEC-UHFFFAOYSA-N 0.000 description 1
- CZLCRMYEULHMJE-UHFFFAOYSA-N 5,6-dimethyl-2-(5-nitrofuran-2-yl)-3h-thieno[2,3-d]pyrimidin-4-one Chemical compound N1C(=O)C=2C(C)=C(C)SC=2N=C1C1=CC=C([N+]([O-])=O)O1 CZLCRMYEULHMJE-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001481789 Rupicapra Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- MUHOWMSOHAQHBH-UHFFFAOYSA-N methyl 2,4-dimethylthiophene-3-carboxylate Chemical compound COC(=O)C=1C(C)=CSC=1C MUHOWMSOHAQHBH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117658 DE2117658A1 (de) | 1971-04-10 | 1971-04-10 | Neue 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 2,3-d eckige Klammer zu pyrimidine und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509234A3 true SU509234A3 (ru) | 1976-03-30 |
Family
ID=5804484
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1955919A SU474142A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3-пиримидина |
| SU1953845A SU501673A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-(5-нитро-2-фурил)-тиено(2,3- ) пиримидина |
| SU1953844A SU509234A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидина |
| SU1953843A SU500759A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3- д / пиримидина |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1955919A SU474142A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3-пиримидина |
| SU1953845A SU501673A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-(5-нитро-2-фурил)-тиено(2,3- ) пиримидина |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1953843A SU500759A3 (ru) | 1971-04-10 | 1973-07-31 | Способ получени производных 2-/5-нитро-2-фурил/-тиено/2,3- д / пиримидина |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3830813A (enExample) |
| AT (4) | AT318633B (enExample) |
| AU (1) | AU467357B2 (enExample) |
| BE (1) | BE781899A (enExample) |
| BG (4) | BG20605A3 (enExample) |
| CA (1) | CA972370A (enExample) |
| CH (4) | CH583736A5 (enExample) |
| DD (1) | DD98683A5 (enExample) |
| DE (1) | DE2117658A1 (enExample) |
| DK (1) | DK127854B (enExample) |
| ES (2) | ES401589A1 (enExample) |
| FR (1) | FR2132839B1 (enExample) |
| GB (1) | GB1384161A (enExample) |
| HU (1) | HU163362B (enExample) |
| IE (1) | IE36268B1 (enExample) |
| IL (1) | IL39173A (enExample) |
| NL (1) | NL7204782A (enExample) |
| NO (1) | NO129147B (enExample) |
| PH (1) | PH10479A (enExample) |
| PL (1) | PL83559B1 (enExample) |
| RO (5) | RO63034A (enExample) |
| SU (4) | SU474142A3 (enExample) |
| ZA (1) | ZA722415B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001412A (en) * | 1972-02-28 | 1977-01-04 | Sumitomo Chemical Company, Limited | 1-Substituted-1,2-dihydrothieno[2,3-d]-pyrimidin-2-one derivatives |
| FI54312C (fi) * | 1972-05-09 | 1978-11-10 | Sumitomo Chemical Co | Foerfarande foer framstaellning av tieno-(2,3-d)pyrimidinderivat med avsoendring av urinsyra i urin utoekande |
| US4054656A (en) * | 1975-09-10 | 1977-10-18 | Mead Johnson & Company | Thieno[2,3-d]pyrimidine antiallergic agents |
| GB1570494A (en) * | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| EP1425284A2 (en) * | 2001-09-11 | 2004-06-09 | Smithkline Beecham Corporation | Furo- and thienopyrimidine derivatives as angiogenesis inhibitors |
-
1971
- 1971-04-10 DE DE19712117658 patent/DE2117658A1/de active Pending
-
1972
- 1972-04-05 PH PH13419A patent/PH10479A/en unknown
- 1972-04-05 US US00241414A patent/US3830813A/en not_active Expired - Lifetime
- 1972-04-07 AT AT951773A patent/AT318633B/de not_active IP Right Cessation
- 1972-04-07 AT AT951573A patent/AT318632B/de not_active IP Right Cessation
- 1972-04-07 CA CA139,148A patent/CA972370A/en not_active Expired
- 1972-04-07 GB GB1621172A patent/GB1384161A/en not_active Expired
- 1972-04-07 DK DK170772AA patent/DK127854B/da unknown
- 1972-04-07 AT AT301272A patent/AT318618B/de not_active IP Right Cessation
- 1972-04-07 DD DD162149A patent/DD98683A5/xx unknown
- 1972-04-07 AT AT951673A patent/AT319255B/de not_active IP Right Cessation
- 1972-04-07 NO NO01196/72*[A patent/NO129147B/no unknown
- 1972-04-08 RO RO7200077451A patent/RO63034A/ro unknown
- 1972-04-08 RO RO7200077450A patent/RO63015A/ro unknown
- 1972-04-08 PL PL1972154623A patent/PL83559B1/pl unknown
- 1972-04-08 BG BG021464A patent/BG20605A3/xx unknown
- 1972-04-08 RO RO7200077449A patent/RO63033A/ro unknown
- 1972-04-08 BG BG021462A patent/BG20604A3/xx unknown
- 1972-04-08 RO RO7200070471A patent/RO62748A/ro unknown
- 1972-04-08 ES ES401589A patent/ES401589A1/es not_active Expired
- 1972-04-08 RO RO7200077448A patent/RO63014A/ro unknown
- 1972-04-08 BG BG021463A patent/BG19183A3/xx unknown
- 1972-04-08 BG BG20180A patent/BG20810A3/xx unknown
- 1972-04-10 BE BE781899A patent/BE781899A/xx unknown
- 1972-04-10 CH CH870575A patent/CH583736A5/xx not_active IP Right Cessation
- 1972-04-10 FR FR7212539A patent/FR2132839B1/fr not_active Expired
- 1972-04-10 NL NL7204782A patent/NL7204782A/xx unknown
- 1972-04-10 IL IL39173A patent/IL39173A/xx unknown
- 1972-04-10 HU HUTO871A patent/HU163362B/hu unknown
- 1972-04-10 CH CH870375A patent/CH575952A5/xx not_active IP Right Cessation
- 1972-04-10 ZA ZA722415A patent/ZA722415B/xx unknown
- 1972-04-10 IE IE460/72A patent/IE36268B1/xx unknown
- 1972-04-10 CH CH870675A patent/CH567510A5/xx not_active IP Right Cessation
- 1972-04-10 AU AU40957/72A patent/AU467357B2/en not_active Expired
- 1972-04-10 CH CH524972A patent/CH575951A5/xx not_active IP Right Cessation
- 1972-10-11 ES ES407519A patent/ES407519A1/es not_active Expired
-
1973
- 1973-07-31 SU SU1955919A patent/SU474142A3/ru active
- 1973-07-31 SU SU1953845A patent/SU501673A3/ru active
- 1973-07-31 SU SU1953844A patent/SU509234A3/ru active
- 1973-07-31 SU SU1953843A patent/SU500759A3/ru active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU493966A3 (ru) | Способ получени производных 4-/2имидазолин-2-иламино/-2,1,3-бензотиадиазола | |
| NO743777L (enExample) | ||
| US3910913A (en) | 4,5-Diamino-7H-pyrrolo{8 2,3-d{9 pyrimidine derivatives | |
| SU509234A3 (ru) | Способ получени производных2-(5-нитро-2-фурил)-тиено(2,3- )пиримидина | |
| JP2009542585A (ja) | キノリン誘導体、その調製方法、その使用、及びそれらを含んで成る医薬品 | |
| SU453830A3 (ru) | Способ получения соответственно замещенного фенацетилгуанидина | |
| SU1151205A3 (ru) | Способ получени 2-амино-4,6-диметоксипиримидина | |
| KR20080020613A (ko) | (치환된) (ｒ)- 또는 (ｓ)-만델산의 동적 분할 방법 | |
| SU419028A3 (ru) | Способ получения 2- | |
| RU2638928C1 (ru) | Производные 1Н-пиразоло[3,4-d]пиримидина и способ их получения | |
| CN101293854B (zh) | 培美曲塞的新中间体及制备方法与应用 | |
| NO883219L (no) | Framgangsmaate for framstilling av beta-lactam-forbindelse,mellomprodukt for framstilling av denne, og medisinske sammensetninger for behandling av bakteriologiske infeksjonssykdommer inneholdende denne. | |
| SU591150A3 (ru) | Способ получени производных нитроимидазолилтриазолопиридазина или их солей | |
| US4812574A (en) | Process for preparing thiazolobenzimidazoles and intermediates used therein | |
| US2389147A (en) | 4' methoxy 5 halogeno diphenylamino 2' carboxyl compound and process for producing the same | |
| US2724711A (en) | Method for the manufacture of 6-mercaptopurine | |
| JPS6322570A (ja) | １−メタンスルホニルオキシ−６−トリフルオロメチル−１ｈ−ベンゾトリアゾ−ル及びセファロスポリン誘導体の製造方法 | |
| SU437281A1 (ru) | Способ получени производных 2-(5нитро-2-фурил)-тиено/3,2- /пиримидина | |
| IE65279B1 (en) | Process for the preparation of dextrorotatory 3-(3-pyridyl)-1h,3h-pyrrolo[1,2-c]-7-thiazolecarbo xylic acid | |
| SU535806A1 (ru) | Способ получени пиридо (3,2- @ ) индолов или их солей | |
| SU898957A3 (ru) | Способ получени производных бензоксазола или бензотиазола или их кислотно-аддитивных солей | |
| Murakami et al. | Optical Resolution by Preferential Crystallization of 2-(3, 4-Carbonyldioxyphenyl)-2-(phthalimidooxy) acetic Acid, a Key Intermediate of Cephalosporin Antibiotic M-14659. | |
| JPS61178970A (ja) | 新規２−置換された１，４−ベンゾジアゼピンの製法 | |
| US2698846A (en) | Heterocyclic compounds | |
| RU1776261C (ru) | Способ получени производных триазолопиримидина или их смеси, или их фармацевтически приемлемых солей с металлами |