CA2447803C - Synthesis of 4-phenylbutyric acid - Google Patents
Synthesis of 4-phenylbutyric acid Download PDFInfo
- Publication number
- CA2447803C CA2447803C CA002447803A CA2447803A CA2447803C CA 2447803 C CA2447803 C CA 2447803C CA 002447803 A CA002447803 A CA 002447803A CA 2447803 A CA2447803 A CA 2447803A CA 2447803 C CA2447803 C CA 2447803C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- compound
- formula
- mixture
- benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229950009215 phenylbutanoic acid Drugs 0.000 title claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 33
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 18
- 229930188620 butyrolactone Natural products 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000002841 Lewis acid Substances 0.000 claims abstract description 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 6
- 230000000171 quenching effect Effects 0.000 claims description 6
- -1 alkali metal cation Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 5
- 239000012074 organic phase Substances 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 1
- 239000002585 base Substances 0.000 abstract description 7
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 229950005499 carbon tetrachloride Drugs 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- VPZRWNZGLKXFOE-UHFFFAOYSA-M sodium phenylbutyrate Chemical compound [Na+].[O-]C(=O)CCCC1=CC=CC=C1 VPZRWNZGLKXFOE-UHFFFAOYSA-M 0.000 description 3
- 229960002232 sodium phenylbutyrate Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 108010044495 Fetal Hemoglobin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 208000007056 sickle cell anemia Diseases 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 102000012215 HSC70 Heat-Shock Proteins Human genes 0.000 description 1
- 108010036652 HSC70 Heat-Shock Proteins Proteins 0.000 description 1
- 206010020575 Hyperammonaemia Diseases 0.000 description 1
- 208000028547 Inborn Urea Cycle disease Diseases 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- JFLIEFSWGNOPJJ-JTQLQIEISA-N N(2)-phenylacetyl-L-glutamine Chemical compound NC(=O)CC[C@@H](C(O)=O)NC(=O)CC1=CC=CC=C1 JFLIEFSWGNOPJJ-JTQLQIEISA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000000599 Ornithine Carbamoyltransferase Deficiency Disease Diseases 0.000 description 1
- 208000035903 Ornithine transcarbamylase deficiency Diseases 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 210000001552 airway epithelial cell Anatomy 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001667 episodic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 208000029824 high grade glioma Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010189 intracellular transport Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 201000011614 malignant glioma Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 201000011278 ornithine carbamoyltransferase deficiency Diseases 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 108010033586 polyethylene glycol-glutaminase-asparaginase Proteins 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000030954 urea cycle disease Diseases 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/862,074 US6372938B1 (en) | 2001-05-21 | 2001-05-21 | Synthesis of 4-phenylbutyric acid |
| US09/862,074 | 2001-05-21 | ||
| PCT/US2002/013946 WO2002094756A1 (en) | 2001-05-21 | 2002-05-02 | Synthesis of 4-phenylbutyric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2447803A1 CA2447803A1 (en) | 2002-11-28 |
| CA2447803C true CA2447803C (en) | 2009-04-07 |
Family
ID=25337569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002447803A Expired - Lifetime CA2447803C (en) | 2001-05-21 | 2002-05-02 | Synthesis of 4-phenylbutyric acid |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6372938B1 (enExample) |
| EP (1) | EP1404638B1 (enExample) |
| JP (1) | JP4338401B2 (enExample) |
| KR (1) | KR100905139B1 (enExample) |
| CN (1) | CN1266105C (enExample) |
| AT (1) | ATE517857T1 (enExample) |
| CA (1) | CA2447803C (enExample) |
| HU (1) | HU229996B1 (enExample) |
| IL (2) | IL158914A0 (enExample) |
| PL (1) | PL201802B1 (enExample) |
| RU (1) | RU2297998C2 (enExample) |
| WO (1) | WO2002094756A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1291015A1 (en) * | 2001-09-10 | 2003-03-12 | Lunamed AG | Dosage forms having prolonged active ingredient release |
| US7115782B2 (en) * | 2002-06-03 | 2006-10-03 | Showa Denko K.K. | Process for producing aromatic compounds by Friedel-Crafts reaction |
| US20060045912A1 (en) * | 2004-08-30 | 2006-03-02 | Peter Truog | 4-phenylbutyric acid controlled-release formulations for therapeutic use |
| US20070004805A1 (en) * | 2005-07-01 | 2007-01-04 | Navinta Llc | Process for preparation of liquid dosage form containing sodium 4-phenylbutyrate |
| WO2007035029A1 (en) * | 2005-09-23 | 2007-03-29 | Sk Holdings Co., Ltd. | Pharmaceutical composition for prevention and treatment of drug or alcohol addiction or bipolar disorder using sodium phenylbutyrate |
| BR112012025714A2 (pt) * | 2010-04-06 | 2015-09-08 | Bayer Ip Gmbh | uso de ácido 4-fenilbutírico e/ou sais do mesmo para aumentar a tolerância a estresse de plantas |
| KR101374241B1 (ko) * | 2010-11-17 | 2014-03-14 | 전북대학교병원 | 페닐부틸산（４－ｐｈｅｎｙｌｂｕｔｙｒｉｃ ａｃｉｄ）또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는, 천식 치료용 약학적 조성물 |
| EP2599477A1 (en) | 2011-11-30 | 2013-06-05 | Lunamed AG | 4-Phenylbutyric acid sustained release formulation |
| FR2993141B1 (fr) | 2012-07-11 | 2014-11-28 | Inst Rech Developpement Ird | Utilisation de l'acide 4-phenylbutyrique pour ameliorer la tolerance des plantes aux bioagresseurs |
| CN103304402B (zh) * | 2013-05-24 | 2015-04-22 | 苏州诚和医药化学有限公司 | 一种制备4-苯-1-丁酸的方法 |
| CN103304403B (zh) * | 2013-05-24 | 2015-04-22 | 苏州诚和医药化学有限公司 | 一种4-苯-1-丁酸的合成方法 |
| US9914692B2 (en) * | 2016-05-25 | 2018-03-13 | Horizon Therapeutics, Llc | Procedure for the preparation of 4-phenyl butyrate and uses thereof |
| CN106117045A (zh) * | 2016-06-22 | 2016-11-16 | 北京阳光诺和药物研究有限公司 | 一种苯基丁酸的纯化方法 |
| CN108530290A (zh) * | 2018-06-04 | 2018-09-14 | 福州华博立乐新材料科技有限公司 | 一种4-苯基-1-丁酸的合成方法 |
| CN110317132B (zh) * | 2019-07-26 | 2021-09-10 | 南京工业大学 | 一种苯丁酸钠的制备方法 |
| FR3110336B1 (fr) | 2020-05-20 | 2022-12-23 | Inst Des Sciences Et Industries Du Vivant Et De Lenvir | Utilisation de l’Acide 4-phénylbutyrique et/ou de l’Acide 3-phénylbutyrique et/ou de l’Acide 2-phénylbutyrique pour la Prévention et le Traitement des Maladies Cryptogamiques |
| WO2024200617A1 (en) * | 2023-03-28 | 2024-10-03 | Dipharma Francis S.R.L. | Process and intermediates for preparing a drug for the treatment of urea cycle disorders |
| IT202300019125A1 (it) * | 2023-09-18 | 2025-03-18 | Dipharma Francis Srl | Metodo di purificazione di un farmaco usato per il trattamento di disturbi del ciclo dell’urea |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6037376A (en) | 1991-10-21 | 2000-03-14 | The United States Of America As Represented By The Department Of Health And Human Services | Methods for therapy of cancer |
-
2001
- 2001-05-21 US US09/862,074 patent/US6372938B1/en not_active Expired - Lifetime
-
2002
- 2002-05-02 RU RU2003136765/04A patent/RU2297998C2/ru active
- 2002-05-02 HU HU0400053A patent/HU229996B1/hu not_active IP Right Cessation
- 2002-05-02 IL IL15891402A patent/IL158914A0/xx unknown
- 2002-05-02 AT AT02729112T patent/ATE517857T1/de not_active IP Right Cessation
- 2002-05-02 KR KR1020037014983A patent/KR100905139B1/ko not_active Expired - Fee Related
- 2002-05-02 CN CNB028102649A patent/CN1266105C/zh not_active Expired - Fee Related
- 2002-05-02 JP JP2002591431A patent/JP4338401B2/ja not_active Expired - Fee Related
- 2002-05-02 WO PCT/US2002/013946 patent/WO2002094756A1/en not_active Ceased
- 2002-05-02 CA CA002447803A patent/CA2447803C/en not_active Expired - Lifetime
- 2002-05-02 PL PL364646A patent/PL201802B1/pl unknown
- 2002-05-02 EP EP02729112A patent/EP1404638B1/en not_active Expired - Lifetime
-
2003
- 2003-11-17 IL IL158914A patent/IL158914A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP4338401B2 (ja) | 2009-10-07 |
| WO2002094756A1 (en) | 2002-11-28 |
| HUP0400053A3 (en) | 2006-01-30 |
| PL201802B1 (pl) | 2009-05-29 |
| IL158914A0 (en) | 2004-05-12 |
| RU2003136765A (ru) | 2005-04-10 |
| ATE517857T1 (de) | 2011-08-15 |
| PL364646A1 (en) | 2004-12-13 |
| EP1404638B1 (en) | 2011-07-27 |
| EP1404638A1 (en) | 2004-04-07 |
| KR20040025679A (ko) | 2004-03-24 |
| CN1511133A (zh) | 2004-07-07 |
| HK1065996A1 (en) | 2005-03-11 |
| KR100905139B1 (ko) | 2009-06-29 |
| CN1266105C (zh) | 2006-07-26 |
| HUP0400053A2 (hu) | 2004-04-28 |
| JP2004527577A (ja) | 2004-09-09 |
| US6372938B1 (en) | 2002-04-16 |
| RU2297998C2 (ru) | 2007-04-27 |
| CA2447803A1 (en) | 2002-11-28 |
| IL158914A (en) | 2010-04-29 |
| HU229996B1 (hu) | 2015-04-28 |
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