NO126022B - - Google Patents
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- Publication number
- NO126022B NO126022B NO2611/70A NO261170A NO126022B NO 126022 B NO126022 B NO 126022B NO 2611/70 A NO2611/70 A NO 2611/70A NO 261170 A NO261170 A NO 261170A NO 126022 B NO126022 B NO 126022B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- compounds
- acid addition
- double bond
- pyrimidine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 nitro- Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000002905 alkanoylamido group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 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
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CTOPNSVRZAUZGA-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-phenylprop-2-en-1-one Chemical compound ClC1=CC=CC(C(=O)C=CC=2C=CC=CC=2)=C1 CTOPNSVRZAUZGA-UHFFFAOYSA-N 0.000 description 1
- OLPPSDMJGDTGJV-UHFFFAOYSA-N 3-(2-bromophenyl)-1-phenylprop-2-en-1-one Chemical compound BrC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 OLPPSDMJGDTGJV-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33646/69A GB1275804A (en) | 1969-07-03 | 1969-07-03 | Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126022B true NO126022B (xx) | 1972-12-11 |
Family
ID=10355612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2611/70A NO126022B (xx) | 1969-07-03 | 1970-07-02 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3740394A (xx) |
| AT (1) | AT299223B (xx) |
| BE (1) | BE752863A (xx) |
| CA (1) | CA926398A (xx) |
| CH (1) | CH527212A (xx) |
| DE (1) | DE2033145A1 (xx) |
| DK (1) | DK131863C (xx) |
| ES (1) | ES382110A1 (xx) |
| FR (1) | FR2054608B1 (xx) |
| GB (1) | GB1275804A (xx) |
| IE (1) | IE34356B1 (xx) |
| LU (1) | LU61235A1 (xx) |
| NL (1) | NL7009682A (xx) |
| NO (1) | NO126022B (xx) |
| OA (1) | OA03306A (xx) |
| SE (1) | SE375102B (xx) |
| ZA (1) | ZA704471B (xx) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1306558A (en) * | 1970-08-14 | 1973-02-14 | Seperic | Derivatives of thiazolino-pyrimidin-5-ones their preparation and applications |
| FR2195426B1 (xx) * | 1972-08-09 | 1975-10-17 | Lipha | |
| US3875162A (en) * | 1973-07-26 | 1975-04-01 | Squibb & Sons Inc | Certain 6H-pyrimido{8 1,2-c{9 {8 1,3,5{9 benzothiadiaza compounds |
| US3966733A (en) * | 1973-07-26 | 1976-06-29 | E. R. Squibb & Sons, Inc. | Intermediates for certain benzothiadiazepine and benzothiadiazocine compounds |
| US4041167A (en) * | 1976-01-19 | 1977-08-09 | Diamond Shamrock Corporation | Antiinflammatory imidazothiazoles |
| US4529727A (en) * | 1982-04-21 | 1985-07-16 | Janssen Pharmaceutical, N.V. | Pyrimido[2,1-b][1,3]-thiazines |
| HU203878B (en) * | 1989-07-19 | 1991-10-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing tetrahydro-pyrimidine carboxylic acid derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933497A (en) * | 1958-01-29 | 1960-04-19 | Searle & Co | Bicyclic thiazole derivatives |
-
1969
- 1969-07-03 GB GB33646/69A patent/GB1275804A/en not_active Expired
-
1970
- 1970-06-19 FR FR7022788A patent/FR2054608B1/fr not_active Expired
- 1970-06-23 CH CH949170A patent/CH527212A/fr not_active IP Right Cessation
- 1970-06-29 US US00050715A patent/US3740394A/en not_active Expired - Lifetime
- 1970-06-29 OA OA53965A patent/OA03306A/xx unknown
- 1970-06-30 IE IE852/70A patent/IE34356B1/xx unknown
- 1970-06-30 NL NL7009682A patent/NL7009682A/xx unknown
- 1970-06-30 ZA ZA704471*A patent/ZA704471B/xx unknown
- 1970-06-30 CA CA086954A patent/CA926398A/en not_active Expired
- 1970-06-30 ES ES382110A patent/ES382110A1/es not_active Expired
- 1970-07-01 SE SE7009115A patent/SE375102B/xx unknown
- 1970-07-01 LU LU61235D patent/LU61235A1/xx unknown
- 1970-07-02 NO NO2611/70A patent/NO126022B/no unknown
- 1970-07-02 BE BE752863D patent/BE752863A/xx unknown
- 1970-07-02 DK DK346470A patent/DK131863C/da active
- 1970-07-02 AT AT600270A patent/AT299223B/de not_active IP Right Cessation
- 1970-07-03 DE DE19702033145 patent/DE2033145A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK131863B (da) | 1975-09-15 |
| FR2054608A1 (xx) | 1971-04-23 |
| ES382110A1 (es) | 1972-11-01 |
| SE375102B (xx) | 1975-04-07 |
| CA926398A (en) | 1973-05-15 |
| DE2033145A1 (de) | 1971-01-14 |
| US3740394A (en) | 1973-06-19 |
| AT299223B (de) | 1972-06-12 |
| IE34356L (en) | 1971-01-03 |
| ZA704471B (en) | 1971-05-27 |
| IE34356B1 (en) | 1975-04-16 |
| OA03306A (fr) | 1970-12-15 |
| GB1275804A (en) | 1972-05-24 |
| FR2054608B1 (xx) | 1974-08-30 |
| BE752863A (fr) | 1970-12-16 |
| CH527212A (fr) | 1972-08-31 |
| LU61235A1 (xx) | 1970-09-10 |
| NL7009682A (xx) | 1971-01-05 |
| DK131863C (da) | 1976-02-16 |
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