SU564811A3 - Способ получени производных 3-(2,5-дигидро-5-оксо-3-фурил) -мочевины или их солей - Google Patents
Способ получени производных 3-(2,5-дигидро-5-оксо-3-фурил) -мочевины или их солейInfo
- Publication number
- SU564811A3 SU564811A3 SU7502123082A SU2123082A SU564811A3 SU 564811 A3 SU564811 A3 SU 564811A3 SU 7502123082 A SU7502123082 A SU 7502123082A SU 2123082 A SU2123082 A SU 2123082A SU 564811 A3 SU564811 A3 SU 564811A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- methylene
- urea
- ethyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000004202 carbamide Substances 0.000 title description 6
- 150000003839 salts Chemical class 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 alkanoyl acetic acid Chemical compound 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- XAHIFKKNNMEBNY-UHFFFAOYSA-N (5-oxo-2h-furan-3-yl)urea Chemical class NC(=O)NC1=CC(=O)OC1 XAHIFKKNNMEBNY-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 5
- PTZOHYHZVZONMS-UHFFFAOYSA-N 1-tert-butyl-3-(5-oxo-2h-furan-3-yl)urea Chemical compound CC(C)(C)NC(=O)NC1=CC(=O)OC1 PTZOHYHZVZONMS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WHSVYFAUHAUURG-UHFFFAOYSA-N benzene;ethyl acetate;methanol Chemical compound OC.CCOC(C)=O.C1=CC=CC=C1 WHSVYFAUHAUURG-UHFFFAOYSA-N 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- BDAOVJXWRKUWIE-UHFFFAOYSA-N (1-methylcyclohexyl)urea Chemical compound NC(=O)NC1(C)CCCCC1 BDAOVJXWRKUWIE-UHFFFAOYSA-N 0.000 description 1
- SOPWCEFXKLAPKS-UHFFFAOYSA-N (1-methylcyclopentyl)urea Chemical compound NC(=O)NC1(C)CCCC1 SOPWCEFXKLAPKS-UHFFFAOYSA-N 0.000 description 1
- NABKXCLVIQJWTD-UHFFFAOYSA-N 1,1-dimethyl-3-prop-2-ynylurea Chemical compound CN(C)C(=O)NCC#C NABKXCLVIQJWTD-UHFFFAOYSA-N 0.000 description 1
- DEKMHQPVTQYSHW-UHFFFAOYSA-N 1-(1-methylcyclohexyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C=1C(=O)OCC=1NC(=O)NC1(C)CCCCC1 DEKMHQPVTQYSHW-UHFFFAOYSA-N 0.000 description 1
- WZIXYVZOQVYGGI-UHFFFAOYSA-N 1-tert-butyl-3-(2-butyl-5-oxo-2h-furan-3-yl)urea Chemical compound CCCCC1OC(=O)C=C1NC(=O)NC(C)(C)C WZIXYVZOQVYGGI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OVUWGANMOQIFHZ-UHFFFAOYSA-N 2-methylbutan-2-ylurea Chemical compound CCC(C)(C)NC(N)=O OVUWGANMOQIFHZ-UHFFFAOYSA-N 0.000 description 1
- YNTARSQYHLHBGV-UHFFFAOYSA-N 2-methylpentan-2-ylurea Chemical compound CCCC(C)(C)NC(N)=O YNTARSQYHLHBGV-UHFFFAOYSA-N 0.000 description 1
- DOQQXIWKNZBIKS-UHFFFAOYSA-N 5-butyloxolane-2,4-dione Chemical compound CCCCC1OC(=O)CC1=O DOQQXIWKNZBIKS-UHFFFAOYSA-N 0.000 description 1
- LSBLXOBUVTZZPG-UHFFFAOYSA-N 5-propyloxolane-2,4-dione Chemical compound CCCC1OC(=O)CC1=O LSBLXOBUVTZZPG-UHFFFAOYSA-N 0.000 description 1
- ATPFRGQBOVFFQM-WJIDAKASSA-N [(1s,3r,7r,8r,8as)-3-(hydroxymethyl)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate Chemical compound C([C@@H]1[C@H](C)C=CC2=C[C@H](CO)C[C@@H]([C@@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 ATPFRGQBOVFFQM-WJIDAKASSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CZRWOPRGDPUSDE-UHFFFAOYSA-N methyl 4-bromo-3-oxobutanoate Chemical compound COC(=O)CC(=O)CBr CZRWOPRGDPUSDE-UHFFFAOYSA-N 0.000 description 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or 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
- C07D307/66—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46169874A | 1974-04-17 | 1974-04-17 | |
| US46170074A | 1974-04-17 | 1974-04-17 | |
| US05/555,306 US3969370A (en) | 1974-04-17 | 1975-03-11 | 1-Tertiary-alkyl-3-(substituted furyl)ureas as antihypertensive agents |
| US05/555,309 US4001425A (en) | 1974-04-17 | 1975-03-11 | Methods of treating hypertension and pharmaceutical compositions comprising 1-tertiary-alkyl-3-(substituted furyl)ureas as antihypertensive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU564811A3 true SU564811A3 (ru) | 1977-07-05 |
Family
ID=27504072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502123082A SU564811A3 (ru) | 1974-04-17 | 1975-04-16 | Способ получени производных 3-(2,5-дигидро-5-оксо-3-фурил) -мочевины или их солей |
Country Status (16)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6016989A (ja) * | 1983-07-06 | 1985-01-28 | Shionogi & Co Ltd | オキソ飽和異項環カルボンアミドセフエム化合物 |
| CO4970714A1 (es) * | 1997-09-05 | 2000-11-07 | Boehringer Mannheim Gmbh | Derivados ureido y tioureido de 4-amino-2(5h)-furanonas y 4-amino-2(5h) tiofenonas como agentes antitumorales |
-
1975
- 1975-01-01 AR AR258394A patent/AR206143A1/es active
- 1975-03-26 SE SE7503524A patent/SE418613B/xx unknown
- 1975-04-10 DD DD185483A patent/DD119784A5/xx unknown
- 1975-04-16 SU SU7502123082A patent/SU564811A3/ru active
- 1975-04-16 DE DE19752516555 patent/DE2516555A1/de not_active Withdrawn
- 1975-04-16 ES ES436649A patent/ES436649A1/es not_active Expired
- 1975-04-16 NO NO751352A patent/NO144070C/no unknown
- 1975-04-16 YU YU00962/75A patent/YU96275A/xx unknown
- 1975-04-16 DK DK164075A patent/DK164075A/da not_active IP Right Cessation
- 1975-04-16 GB GB1567375A patent/GB1463043A/en not_active Expired
- 1975-04-16 FI FI751129A patent/FI751129A7/fi not_active Application Discontinuation
- 1975-04-16 FR FR7511795A patent/FR2267771B1/fr not_active Expired
- 1975-04-17 LU LU72307A patent/LU72307A1/xx unknown
- 1975-04-17 IE IE863/75A patent/IE41112B1/xx unknown
- 1975-04-17 JP JP50045922A patent/JPS50148352A/ja active Pending
- 1975-04-17 CH CH494675A patent/CH614202A5/xx not_active IP Right Cessation
-
1979
- 1979-02-19 CH CH160679A patent/CH615672A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AR206143A1 (es) | 1976-06-30 |
| IE41112L (en) | 1975-10-17 |
| LU72307A1 (enrdf_load_stackoverflow) | 1976-03-17 |
| ES436649A1 (es) | 1977-05-01 |
| NO144070C (no) | 1981-06-17 |
| FR2267771B1 (enrdf_load_stackoverflow) | 1978-08-18 |
| NO751352L (enrdf_load_stackoverflow) | 1975-10-20 |
| JPS50148352A (enrdf_load_stackoverflow) | 1975-11-27 |
| DD119784A5 (enrdf_load_stackoverflow) | 1976-05-12 |
| DE2516555A1 (de) | 1975-10-30 |
| FR2267771A1 (enrdf_load_stackoverflow) | 1975-11-14 |
| YU96275A (en) | 1983-04-27 |
| DK164075A (da) | 1975-10-18 |
| GB1463043A (en) | 1977-02-02 |
| SE7503524L (sv) | 1975-10-20 |
| SE418613B (sv) | 1981-06-15 |
| FI751129A7 (enrdf_load_stackoverflow) | 1975-10-18 |
| CH615672A5 (en) | 1980-02-15 |
| CH614202A5 (en) | 1979-11-15 |
| IE41112B1 (en) | 1979-10-24 |
| AU8013675A (en) | 1976-10-21 |
| NO144070B (no) | 1981-03-09 |
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