NO132760B - - Google Patents
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- Publication number
- NO132760B NO132760B NO3028/71A NO302871A NO132760B NO 132760 B NO132760 B NO 132760B NO 3028/71 A NO3028/71 A NO 3028/71A NO 302871 A NO302871 A NO 302871A NO 132760 B NO132760 B NO 132760B
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- phenyl
- pyrimidin
- general formula
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 17
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SILRNKZBMNSABG-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1CSC(N)=N1 SILRNKZBMNSABG-UHFFFAOYSA-N 0.000 description 1
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000282941 Rangifer tarandus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- UVRHPZOOCXESOY-UHFFFAOYSA-N pyrimidine;1,3-thiazole Chemical class C1=CSC=N1.C1=CN=CN=C1 UVRHPZOOCXESOY-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3918970 | 1970-08-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132760B true NO132760B (enrdf_load_stackoverflow) | 1975-09-22 |
| NO132760C NO132760C (enrdf_load_stackoverflow) | 1975-12-29 |
Family
ID=10408188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3028/71A NO132760C (enrdf_load_stackoverflow) | 1970-08-14 | 1971-08-13 |
Country Status (21)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL129612B1 (en) * | 1980-07-24 | 1984-05-31 | Rhone Poulenc Ind | Process for preparing novel derivatives of 2,3,6,7-tetrahydrothiazole/3,2-a/pirymidin-5-one |
| US4443451A (en) * | 1981-07-15 | 1984-04-17 | Janssen Pharmaceutica N.V. | Bicyclic pyrimidin-5-one derivatives |
| JPS5980072U (ja) * | 1982-11-19 | 1984-05-30 | 株式会社東洋製作所 | 倉庫の扉開閉装置 |
| JPS6354797U (enrdf_load_stackoverflow) * | 1986-09-29 | 1988-04-12 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1275804A (en) * | 1969-07-03 | 1972-05-24 | Seperic | Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications |
-
1970
- 1970-08-14 GB GB3918970A patent/GB1306558A/en not_active Expired
-
1971
- 1971-07-08 FR FR7125051A patent/FR2102254B1/fr not_active Expired
- 1971-08-03 IS IS2024A patent/IS918B6/is unknown
- 1971-08-03 BE BE770873A patent/BE770873A/xx unknown
- 1971-08-03 IL IL37431A patent/IL37431A/en unknown
- 1971-08-04 IE IE986/71A patent/IE35491B1/xx unknown
- 1971-08-04 ZA ZA715194A patent/ZA715194B/xx unknown
- 1971-08-05 SE SE7110021A patent/SE380271B/xx unknown
- 1971-08-05 CH CH1155771A patent/CH542231A/fr not_active IP Right Cessation
- 1971-08-09 OA OA54327A patent/OA03905A/xx unknown
- 1971-08-11 FI FI712245A patent/FI52096C/fi active
- 1971-08-11 LU LU63700D patent/LU63700A1/xx unknown
- 1971-08-12 ES ES394727A patent/ES394727A1/es not_active Expired
- 1971-08-12 AU AU32310/71A patent/AU3231071A/en not_active Expired
- 1971-08-13 NL NL717111222A patent/NL149177B/xx not_active IP Right Cessation
- 1971-08-13 NO NO3028/71A patent/NO132760C/no unknown
- 1971-08-13 JP JP46061591A patent/JPS5116437B1/ja active Pending
- 1971-08-13 DK DK398471AA patent/DK129718B/da unknown
- 1971-08-13 AT AT711771A patent/AT305279B/de active
- 1971-08-13 CA CA120534A patent/CA925868A/en not_active Expired
- 1971-08-13 DE DE2140601A patent/DE2140601C3/de not_active Expired
-
1976
- 1976-01-28 NL NL7600885A patent/NL7600885A/xx not_active Application Discontinuation
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