SU489325A3 - Способ получени производных фенилбутазона - Google Patents
Способ получени производных фенилбутазонаInfo
- Publication number
- SU489325A3 SU489325A3 SU1257954A SU1257954A SU489325A3 SU 489325 A3 SU489325 A3 SU 489325A3 SU 1257954 A SU1257954 A SU 1257954A SU 1257954 A SU1257954 A SU 1257954A SU 489325 A3 SU489325 A3 SU 489325A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- preparing
- acetone
- mol
- oxobutyl
- butyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical class O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 title description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- -1 4-butyl-1,2-diphenylpyrazolol Chemical compound 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 1
- OKDGPOCKHMGDQY-UHFFFAOYSA-N 3,4-dihydropyrrol-2-one Chemical compound O=C1CCC=N1 OKDGPOCKHMGDQY-UHFFFAOYSA-N 0.000 description 1
- PNDQJXRHBSZULV-UHFFFAOYSA-N 4-butyl-1,2-diphenyl-3H-pyrazole Chemical compound C(CCC)C1=CN(N(C1)C1=CC=CC=C1)C1=CC=CC=C1 PNDQJXRHBSZULV-UHFFFAOYSA-N 0.000 description 1
- UNBPKAKPNOMMQM-RAHXUVGXSA-N C1(=CC=CC=C1)N1N(C(C(C1[2H])CCCC)[2H])C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N1N(C(C(C1[2H])CCCC)[2H])C1=CC=CC=C1 UNBPKAKPNOMMQM-RAHXUVGXSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003500 enol ether group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- LGYTZKPVOAIUKX-UHFFFAOYSA-N kebuzone Chemical compound O=C1C(CCC(=O)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 LGYTZKPVOAIUKX-UHFFFAOYSA-N 0.000 description 1
- 101150055025 ksh1 gene Proteins 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RDPLOLUNEKBWBR-UHFFFAOYSA-L magnesium;sodium;sulfate Chemical compound [Na+].[Mg+2].[O-]S([O-])(=O)=O RDPLOLUNEKBWBR-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical compound O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings 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
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR109213A FR6505M (enExample) | 1967-06-06 | 1967-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU489325A3 true SU489325A3 (ru) | 1975-10-25 |
Family
ID=8632382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1257954A SU489325A3 (ru) | 1967-06-06 | 1968-06-06 | Способ получени производных фенилбутазона |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3607881A (enExample) |
| BE (1) | BE716160A (enExample) |
| CH (1) | CH476734A (enExample) |
| DE (1) | DE1767702A1 (enExample) |
| DK (1) | DK120491B (enExample) |
| ES (1) | ES353634A1 (enExample) |
| FR (1) | FR6505M (enExample) |
| GB (1) | GB1223875A (enExample) |
| SE (1) | SE361885B (enExample) |
| SU (1) | SU489325A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117232A (en) * | 1976-03-08 | 1978-09-26 | Interx Research Corporation | Transient pro-drug forms of phenylbutazone |
| GB1589816A (en) * | 1977-06-02 | 1981-05-20 | Sterwin Ag | Pharmacologically active esters of alkyl-dioxo-pyrazotidine derivatives |
| US5098477A (en) * | 1988-12-14 | 1992-03-24 | Ciba-Geigy Corporation | Inks, particularly for ink printing |
-
1967
- 1967-06-06 FR FR109213A patent/FR6505M/fr not_active Expired
-
1968
- 1968-04-27 ES ES353634A patent/ES353634A1/es not_active Expired
- 1968-05-02 GB GB20890/68A patent/GB1223875A/en not_active Expired
- 1968-05-05 US US734528A patent/US3607881A/en not_active Expired - Lifetime
- 1968-05-30 DK DK252268AA patent/DK120491B/da unknown
- 1968-05-31 CH CH806768A patent/CH476734A/fr not_active IP Right Cessation
- 1968-06-06 BE BE716160D patent/BE716160A/xx not_active IP Right Cessation
- 1968-06-06 DE DE19681767702 patent/DE1767702A1/de not_active Withdrawn
- 1968-06-06 SE SE07571/68A patent/SE361885B/xx unknown
- 1968-06-06 SU SU1257954A patent/SU489325A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1223875A (en) | 1971-03-03 |
| SE361885B (enExample) | 1973-11-19 |
| DE1767702A1 (de) | 1970-01-02 |
| FR6505M (enExample) | 1968-12-02 |
| US3607881A (en) | 1971-09-21 |
| CH476734A (fr) | 1969-08-15 |
| BE716160A (enExample) | 1968-11-04 |
| DK120491B (da) | 1971-06-07 |
| ES353634A1 (es) | 1969-10-16 |
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