CN110305071A - A kind of synthetic method of Parecoxib Sodium intermediate SC 69124 - Google Patents
A kind of synthetic method of Parecoxib Sodium intermediate SC 69124 Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 24
- 229960003925 parecoxib sodium Drugs 0.000 title claims abstract description 21
- ICJGKYTXBRDUMV-UHFFFAOYSA-N trichloro(6-trichlorosilylhexyl)silane Chemical compound Cl[Si](Cl)(Cl)CCCCCC[Si](Cl)(Cl)Cl ICJGKYTXBRDUMV-UHFFFAOYSA-N 0.000 title claims abstract description 21
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 title abstract description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 235000021463 dry cake Nutrition 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 239000000126 substance Chemical group 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229960002004 valdecoxib Drugs 0.000 description 2
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- -1 5- methyl-isoxazolyl Chemical group 0.000 description 1
- UCGIIOJWRLQBRP-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole Chemical compound O1C(C)=CC(C=2C=CC=CC=2)=N1 UCGIIOJWRLQBRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000004550 Postoperative Pain Diseases 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- MQPZAQHEKNWMOR-UHFFFAOYSA-N [Na].C(CC)(=O)N Chemical compound [Na].C(CC)(=O)N MQPZAQHEKNWMOR-UHFFFAOYSA-N 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Abstract
The present invention provides a kind of synthetic method of Parecoxib Sodium intermediate SC 69124, SC 69124 high income, the purity is high obtained using the synthetic method.The problem of it is low that SC 69124 synthetic method of the present invention overcomes yield of the existing technology, high production cost.It is more advantageous to the industrialized production of SC 69124.
Description
Technical field
The present invention relates to a kind of synthetic methods of Parecoxib Sodium intermediate SC 69124.
Background technique
Entitled N- [[4- (- 3 phenyl of 5- methyl-isoxazolyl) phenyl] sulfonyl] the propionamide sodium of Parecoxib Sodium chemistry
Salt is a kind of non-steroidal anti-inflammatory drugs, can be used as COX-2 selective inhibitor.It is mainly used for controlling in short term for postoperative pain
It treats.
SC 69124 (Parocoxib) is the key intermediate for synthesizing Parecoxib Sodium, molecular formula C19H18N2O4S,
Molecular weight is 370.43, and structural formula is as follows:
It is recorded in patent CN97193747.8, the synthesis technology of SC 69124, which mainly passes through following technology paths, to be completed:
The route is that the DMAP of Parecoxib Sodium intermediate valdecoxib III and catalytic amount is added to dry tetrahydrofuran
The propionic andydride and triethylamine of filtering are added in solvent, after stirring.Room temperature reaction is concentrated to dryness after 18 hours, and it is molten that ethyl acetate is added
Solution successively uses 1N hydrochloric acid and saturated common salt water washing, and organic phase is dry with anhydrous sodium sulfate, and pa auspicious former times is obtained after being concentrated to dryness
Cloth.But this method reaction time is long, and it is at high cost, it is unfavorable for industrialized production.
Summary of the invention
To solve the above-mentioned problems, the present invention provides a kind of synthetic methods of Parecoxib Sodium intermediate SC 69124.
The present invention provides a kind of synthetic methods of Parecoxib Sodium intermediate, it includes the following steps:
Compound B, 4-dimethylaminopyridine, triethylamine, propionic andydride are dissolved in solvent, reacts, obtains reaction solution；It will reaction
Liquid purification, organic phase after purification are concentrated under reduced pressure, and solid A is precipitated, and are separated by solid-liquid separation, and by the liquid after separation in 10 DEG C of crystallizations,
Obtain solid B, by solid A and solid B mix to get.
Further, the compound B, 4-dimethylaminopyridine, triethylamine, propionic andydride molar ratio be 1:0.01~
0.05:1~1.5:1~1.5；The mass ratio of the compound B and solvent is 1:3~8；
Preferably, the compound B, 4-dimethylaminopyridine, triethylamine, propionic andydride molar ratio be 1:0.05:1.3:
1.2；The mass ratio of the compound B and solvent is 1:4.
Further, the solvent is methylene chloride.
Further, it is under stirring condition in solvent that the compound B, 4-dimethylaminopyridine, triethylamine, which are dissolved in solvent,
In sequentially add compound B, 4-dimethylaminopyridine and triethylamine；The propionic andydride is dissolved in solvent for compound B, 4- bis- is added
After methylamino pyridine and triethylamine, propionic andydride is added dropwise；Preferably, temperature is 15~35 DEG C when propionic andydride is added dropwise；It is highly preferred that drop
Temperature is 25 DEG C when adding propionic andydride.
Further, the reaction temperature of the reaction is 15~35 DEG C, and the reaction time is 1~3h；Preferably, the reaction
Reaction temperature be 25 DEG C；Reaction time is 1h.
Further, the purification is not dripped for reaction solution is concentrated under reduced pressure into condensate liquid at line, and ethyl acetate is added, obtains
Ethyl acetate solution, pure water agitator treating ethyl acetate solution, takes organic phase.
Further, 5 times that quality is compound B mass are added in the ethyl acetate；And/or the pure water stirring is washed
Wash ethyl acetate solution three times, each agitator treating 10 minutes stands 20 minutes.
Further, solid A is precipitated to constant weight for 45 DEG C of reduced pressures in described be concentrated under reduced pressure.
Further, the crystallization time is 1~3 hour；And/or the crystallization is to be added in liquid after isolation
N-hexane；Wherein, the mass ratio of the n-hexane and compound B are 2:1；
Preferably, the crystallization time is 2 hours.
It further, further include following step: centrifugation, filtering, dry cake after the mixing by solid A and solid B；
Preferably, the drying is that filter cake is 8 hours dry in 55~65 DEG C of hot-air ovens.
The present invention provides a kind of synthetic methods of Parecoxib Sodium intermediate SC 69124, are obtained using the synthetic method
SC 69124 high income, purity is high.It is low that SC 69124 synthetic method of the present invention overcomes yield of the existing technology,
The problem of high production cost.It is more advantageous to the industrialized production of SC 69124.
Obviously, above content according to the present invention is not being departed from according to the ordinary technical knowledge and customary means of this field
Under the premise of the above-mentioned basic fundamental thought of the present invention, the modification, replacement or change of other diversified forms can also be made.
The specific embodiment of form by the following examples remakes further specifically above content of the invention
It is bright.But the range that this should not be interpreted as to the above-mentioned theme of the present invention is only limitted to example below.It is all to be based on above content of the present invention
The technology realized all belongs to the scope of the present invention.
Specific embodiment
Raw material, equipment used in the specific embodiment of the invention are known product, are obtained by purchase commercial product.
The synthesis of embodiment 1, Parecoxib Sodium intermediate SC 69124 of the present invention
1, raw material and the reagent for synthesizing Parecoxib Sodium intermediate SC 69124 of the present invention are as shown in table 1.
Table 1 synthesizes the raw material and reagent of Parecoxib Sodium intermediate SC 69124 of the present invention
| Name of material | Inventory g |
| Compound B | 1000 |
| Propionic andydride | 497 |
| Methylene chloride | 4000 |
| Triethylamine | 418 |
| 4-dimethylaminopyridine | 19.4 |
| Ethyl acetate | 5000 |
| N-hexane | 2000 |
Compound B is valdecoxib, chemical entitled 4- (5- methyl -3- phenyl -1,2-oxazole -4- base) benzsulfamide,
Molecular formula is C16H14N2O3S, molecular weight 314.4, structural formula is as follows:
2, the preparation method of Parecoxib Sodium intermediate SC 69124 of the present invention:
(1) 4000g methylene chloride is added in reaction kettle, by 1000g compound B, 19.4g 4- diformazan under stirring condition
Aminopyridine, 418g triethylamine are sequentially added in reaction kettle, and then kettle collet leads to cooling water, are controlled interior 25 ± 10 DEG C of temperature, are added dropwise
497g propionic andydride.
(2) charging finishes, and reacts in 25 DEG C of insulated and stirreds, time of every 0.5 hour record and temperature；Insulation reaction 1
The monitoring of hour TLC is primary, and later every 0.5 hour sampling monitoring is primary, and TLC monitors (ethyl acetate: petroleum ether/EA:PE=1:1)
Until it is reaction end that intermediate B, which disappears, the reaction time 1 hour, end of reaction obtained reaction solution.
(3) reaction solution is concentrated under reduced pressure into condensate liquid and not dripped at line by logical 45 ± 5 DEG C of hot water of kettle collet.
(4) add 5000g ethyl acetate, the ethyl acetate solution of formation with purified water agitator treating three times: it is pure every time
Change 4 times of volumes that water consumption is ethyl acetate solution, each agitator treating 10 minutes stands 20 minutes, takes organic phase.
(5) the logical 45 DEG C of hot water of kettle collet are concentrated under reduced pressure step (4) resulting organic phase and solid A are extremely precipitated to constant weight.
(6) concentration finishes, and by step (5) resulting separation of solid and liquid, the liquid after separation is transferred in crystallization bucket, is added
2000g n-hexane, crystallization, crystallization temperature are 10 DEG C, time of every 0.5 hour record and temperature, crystallization 2 ± 0.5 hours, analysis
It is slightly agitated for during crystalline substance, obtains solid B.
(7) solid A and solid B is mixed, centrifuge 10 minutes, filtering, gained filter cake is done in 60 ± 5 DEG C of hot-air ovens
Dry, temperature and time of every 1 hour record is 8 hours dry.It obtains faint yellow to off-white powder, pa auspicious former times as of the present invention
Cloth sodium intermediate SC 69124.
Repeat above-mentioned " preparation method of SC 69124 " 3 times, obtained SC 69124 is respectively sample 1, sample 2 and sample
3。
The preparation of comparative example 1, Parecoxib Sodium intermediate SC 69124
The raw material and reagent of comparative example 1 are identical with embodiment 1.
The preparation method of comparative example 1 is identical with embodiment 1, is only changed to the crystallization temperature of step (6) crystallization condition:
Crystallization temperature is 25 DEG C.Obtained SC 69124 is reference substance.
The yield and purity of Parecoxib Sodium intermediate SC 69124 prepared by embodiment 1 and comparative example 1 are as shown in table 2.
The yield and purity of the Parecoxib Sodium intermediate SC 69124 of 2 distinct methods of table preparation
| Crystallization temperature DEG C | Receive to obtain product g | Yield % | Purity % | |
| Reference substance | 25 | 748 | 74.8 | 93.1 |
| Sample 1 | 10 | 849 | 84.9 | 93.2 |
| Sample 2 | 10 | 853 | 85.3 | 92.9 |
| Sample 3 | 10 | 857 | 85.7 | 93.0 |
Yield %=receives to obtain product/Parecoxib Sodium intermediate B input amount × 100%
As shown in Table 2: Parecoxib Sodium intermediate SC 69124 being prepared using synthetic method of the present invention, not only purity is very
Height, and yield has the raising of conspicuousness.
To sum up, the present invention provides a kind of synthetic method of Parecoxib Sodium intermediate SC 69124, the synthesis side is utilized
SC 69124 high income, the purity is high that method obtains.SC 69124 synthetic method of the present invention overcomes production of the existing technology
The problem of yield is low, high production cost.It is more advantageous to the industrialized production of SC 69124.
Claims (10)
1. a kind of synthetic method of Parecoxib Sodium intermediate, it is characterised in that: it includes the following steps:
Compound B, 4-dimethylaminopyridine, triethylamine, propionic andydride are dissolved in solvent, reacts, obtains reaction solution；Reaction solution is mentioned
Pure, the organic phase after purification is concentrated under reduced pressure, and solid A is precipitated, and is separated by solid-liquid separation, and the liquid after separation is obtained in 10 DEG C of crystallizations
Solid B, by solid A and solid B mix to get.
2. synthetic method according to claim 1, it is characterised in that: the compound B, 4-dimethylaminopyridine, three second
Amine, propionic andydride molar ratio be 1:0.01~0.05:1~1.5:1~1.5；The mass ratio of the compound B and solvent is 1:3
~8；
Preferably, the compound B, 4-dimethylaminopyridine, triethylamine, propionic andydride molar ratio be 1:0.05:1.3:1.2；
The mass ratio of the compound B and solvent is 1:4.
3. synthetic method according to claim 1 or 2, it is characterised in that: the solvent is methylene chloride.
4. synthetic method according to claim 1, it is characterised in that: the compound B, 4-dimethylaminopyridine, three second
It is to sequentially add compound B, 4-dimethylaminopyridine and triethylamine in a solvent under stirring condition that amine, which is dissolved in solvent,；The propionic acid
After acid anhydride is dissolved in solvent for compound B, 4-dimethylaminopyridine and triethylamine is added, propionic andydride is added dropwise；Preferably, propionic andydride is added dropwise
Shi Wendu is 15~35 DEG C；It is highly preferred that temperature is 25 DEG C when propionic andydride is added dropwise.
5. synthetic method according to claim 1, it is characterised in that: the reaction temperature of the reaction is 15~35 DEG C, instead
It is 1~3h between seasonable；Preferably, the reaction temperature of the reaction is 25 DEG C；Reaction time is 1h.
6. synthetic method according to claim 1, it is characterised in that: the purification is that reaction solution is concentrated under reduced pressure into condensation
Liquid is not dripped at line, and ethyl acetate is added, obtains ethyl acetate solution, pure water agitator treating ethyl acetate solution takes organic phase, i.e.,
It can.
7. synthetic method according to claim 6, it is characterised in that: it is compound B matter that quality, which is added, in the ethyl acetate
5 times of amount；And/or the pure water agitator treating ethyl acetate solution is three times, each agitator treating 10 minutes, stands 20 minutes.
8. synthetic method according to claim 1, it is characterised in that: described be concentrated under reduced pressure is precipitated admittedly for 45 DEG C of reduced pressures
Body A is to constant weight.
9. synthetic method according to claim 1, it is characterised in that: the crystallization time is 1~3 hour；And/or institute
Crystallization is stated as n-hexane is added in liquid after isolation；Wherein, the mass ratio of the n-hexane and compound B are 2:1；
Preferably, the crystallization time is 2 hours.
10. synthetic method according to claim 1, it is characterised in that: after the mixing by solid A and solid B, further include
Following step: centrifugation, filtering, dry cake；Preferably, the drying is that filter cake drying 8 in 55~65 DEG C of hot-air ovens is small
When.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1216043A (en) * | 1996-04-12 | 1999-05-05 | G·D·瑟尔公司 | Substd. benzenesulfonamide derivs as prodrugs of COX-2 inhibitors |
| US20050182113A1 (en) * | 2003-12-30 | 2005-08-18 | Venkataraman Sundaram | Method for preparing diaryl-substituted isoxazole compounds |
| WO2005123701A1 (en) * | 2004-06-14 | 2005-12-29 | Pharmacia Corporation | Method for the preparation of diarylisoxazole sulfonamide compounds and intermediates |
| CN104592141A (en) * | 2015-01-04 | 2015-05-06 | 成都克莱蒙医药科技有限公司 | Synthesis method of parecoxib sodium |
| CN105859647A (en) * | 2016-05-25 | 2016-08-17 | 王晓岳 | Preparation method of cyclooxygenase-2 inhibitor parecoxib |
-
2019
- 2019-07-23 CN CN201910667402.XA patent/CN110305071A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1216043A (en) * | 1996-04-12 | 1999-05-05 | G·D·瑟尔公司 | Substd. benzenesulfonamide derivs as prodrugs of COX-2 inhibitors |
| US20050182113A1 (en) * | 2003-12-30 | 2005-08-18 | Venkataraman Sundaram | Method for preparing diaryl-substituted isoxazole compounds |
| WO2005123701A1 (en) * | 2004-06-14 | 2005-12-29 | Pharmacia Corporation | Method for the preparation of diarylisoxazole sulfonamide compounds and intermediates |
| CN104592141A (en) * | 2015-01-04 | 2015-05-06 | 成都克莱蒙医药科技有限公司 | Synthesis method of parecoxib sodium |
| CN105859647A (en) * | 2016-05-25 | 2016-08-17 | 王晓岳 | Preparation method of cyclooxygenase-2 inhibitor parecoxib |
Non-Patent Citations (3)
| Title |
|---|
| JOHN J. TALLEY ET AL.: ""N-[[(5-Methyl-3-phenylisoxazol-4-yl)- phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: a potent and selective inhibitor of COX-2 for parenteral administration"", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
| 吴继洲 等: "《天然药物化学》", 31 August 2008, 中国医药科技出版社 * |
| 王凯 等: ""帕瑞昔布的合成"", 《中国医药工业杂志》 * |
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Application publication date: 20191008 |