CA2212047C - Triglycerides and ethyl esters of phenylalkanoic acid and phenylalkenoic acid useful in treatment of various disorders - Google Patents
Triglycerides and ethyl esters of phenylalkanoic acid and phenylalkenoic acid useful in treatment of various disorders Download PDFInfo
- Publication number
- CA2212047C CA2212047C CA2212047A CA2212047A CA2212047C CA 2212047 C CA2212047 C CA 2212047C CA 2212047 A CA2212047 A CA 2212047A CA 2212047 A CA2212047 A CA 2212047A CA 2212047 C CA2212047 C CA 2212047C
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- Canada
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- Expired - Fee Related
Links
- 125000004494 ethyl ester group Chemical group 0.000 title claims abstract description 8
- 238000011282 treatment Methods 0.000 title claims description 29
- 239000002253 acid Substances 0.000 title abstract description 22
- 150000003626 triacylglycerols Chemical class 0.000 title description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 208000034737 hemoglobinopathy Diseases 0.000 claims abstract description 14
- 208000018337 inherited hemoglobinopathy Diseases 0.000 claims abstract description 12
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 238000009825 accumulation Methods 0.000 claims abstract description 9
- 208000007502 anemia Diseases 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 44
- 208000030159 metabolic disease Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims description 4
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 4
- 102000003951 Erythropoietin Human genes 0.000 claims description 3
- 108090000394 Erythropoietin Proteins 0.000 claims description 3
- 229940105423 erythropoietin Drugs 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 6
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract description 25
- 229940049953 phenylacetate Drugs 0.000 abstract description 25
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 15
- 150000007513 acids Chemical class 0.000 abstract description 15
- 239000003814 drug Substances 0.000 abstract description 13
- 229940079593 drug Drugs 0.000 abstract description 8
- 239000002552 dosage form Substances 0.000 abstract description 4
- 239000000651 prodrug Substances 0.000 abstract description 4
- 229940002612 prodrug Drugs 0.000 abstract description 4
- 239000000039 congener Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 11
- 229950009215 phenylbutanoic acid Drugs 0.000 description 11
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 9
- 229960002232 sodium phenylbutyrate Drugs 0.000 description 8
- VPZRWNZGLKXFOE-UHFFFAOYSA-M sodium phenylbutyrate Chemical compound [Na+].[O-]C(=O)CCCC1=CC=CC=C1 VPZRWNZGLKXFOE-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000002354 daily effect Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 229940124597 therapeutic agent Drugs 0.000 description 5
- 108010044495 Fetal Hemoglobin Proteins 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 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 3
- 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 3
- 208000002903 Thalassemia Diseases 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229940006198 sodium phenylacetate Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- 102000001554 Hemoglobins Human genes 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000028547 Inborn Urea Cycle disease Diseases 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000004069 differentiation Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- -1 phenylbutyrate Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000004143 urea cycle Effects 0.000 description 2
- 208000030954 urea cycle disease Diseases 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000015781 Dietary Proteins Human genes 0.000 description 1
- 108010010256 Dietary Proteins Proteins 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010019663 Hepatic failure Diseases 0.000 description 1
- 206010062904 Hormone-refractory prostate cancer Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 201000011252 Phenylketonuria Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 208000005980 beta thalassemia Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 201000007455 central nervous system cancer Diseases 0.000 description 1
- 208000025997 central nervous system neoplasm Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000021245 dietary protein Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000007386 hepatic encephalopathy Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000006371 metabolic abnormality Effects 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- SIENSFABYFDZCL-UHFFFAOYSA-N phenyl decanoate Chemical compound CCCCCCCCCC(=O)OC1=CC=CC=C1 SIENSFABYFDZCL-UHFFFAOYSA-N 0.000 description 1
- SOOXQKVMQBCEGW-UHFFFAOYSA-N phenyl hexanoate Chemical compound CCCCCC(=O)OC1=CC=CC=C1 SOOXQKVMQBCEGW-UHFFFAOYSA-N 0.000 description 1
- ZBZSVGXZAPNCSY-UHFFFAOYSA-N phenyl octanoate Chemical compound CCCCCCCC(=O)OC1=CC=CC=C1 ZBZSVGXZAPNCSY-UHFFFAOYSA-N 0.000 description 1
- 210000005267 prostate cell Anatomy 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 208000007056 sickle cell anemia Diseases 0.000 description 1
- 235000021023 sodium intake Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US384,935 | 1982-06-04 | ||
| US38493595A | 1995-02-07 | 1995-02-07 | |
| PCT/US1996/000940 WO1996024571A1 (en) | 1995-02-07 | 1996-02-06 | Triglycerides and ethyl esters of phenylalkanoic acid and phenylalkenoic acid useful in treatment of various disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2212047A1 CA2212047A1 (en) | 1996-08-15 |
| CA2212047C true CA2212047C (en) | 2010-11-16 |
Family
ID=23519346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2212047A Expired - Fee Related CA2212047C (en) | 1995-02-07 | 1996-02-06 | Triglycerides and ethyl esters of phenylalkanoic acid and phenylalkenoic acid useful in treatment of various disorders |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5968979A (https=) |
| EP (1) | EP0858441B1 (https=) |
| AT (1) | ATE201013T1 (https=) |
| AU (1) | AU4858796A (https=) |
| CA (1) | CA2212047C (https=) |
| DE (1) | DE69612755T2 (https=) |
| ES (1) | ES2157422T3 (https=) |
| FR (1) | FR16C0003I2 (https=) |
| WO (1) | WO1996024571A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6642543B1 (en) | 2000-09-26 | 2003-11-04 | The Board Of Trustees Of The Leland Stanford Junior University | Thin and thick gate oxide transistors on a functional block of a CMOS circuit residing within the core of an IC chip |
| US7842727B2 (en) | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US7314953B2 (en) * | 2001-03-27 | 2008-01-01 | Errant Gene Therapeutics, Llc | Treatment of lung cells with histone deacetylase inhibitors |
| US8026280B2 (en) | 2001-03-27 | 2011-09-27 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US6495719B2 (en) | 2001-03-27 | 2002-12-17 | Circagen Pharmaceutical | Histone deacetylase inhibitors |
| US7312247B2 (en) | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US20040229948A1 (en) * | 2002-04-12 | 2004-11-18 | Summar Marshall L. | Method for preventing hepatic encephalopathic episodes |
| US20030195255A1 (en) * | 2002-04-12 | 2003-10-16 | Summar Marshall L. | Method for treating hepatic encephalopathies |
| EP1511477A4 (en) | 2002-05-22 | 2008-04-09 | Errant Gene Therapeutics Llc | HISTONE DEACETYLASE INHIBITORS BASED ON ALPHA-KETO-EPOXYDE COMPOUNDS |
| US20090260743A1 (en) * | 2003-11-21 | 2009-10-22 | William David Mawby | Tire manufacturing method for improving the uniformity of a tire |
| US20060160902A1 (en) * | 2004-11-08 | 2006-07-20 | Wiech Norbert L | Histone deacetylase inhibitors |
| WO2009134460A1 (en) | 2008-04-29 | 2009-11-05 | Hyperion Therapeutics | Methods of treatment using ammonia-scavenging drugs |
| ES2695534T3 (es) * | 2008-08-29 | 2019-01-08 | Horizon Therapeutics Llc | Métodos de tratamiento usando fármacos de captación de amoniaco |
| EP3263102A1 (en) | 2011-09-30 | 2018-01-03 | Horizon Therapeutics, LLC | Methods of therapeutic monitoring of nitrogen scavenging drugs |
| PT2846791T (pt) | 2012-04-20 | 2017-05-25 | Horizon Therapeutics Llc | Métodos de monitorização terapêutica de profármacos de ácido fenilacético |
| PT2922576T (pt) | 2012-11-21 | 2018-01-24 | Horizon Therapeutics Llc | Métodos de administração e avaliação de fármacos sequestradores de azoto para o tratamento de encefalopatia hepática |
| HUE045106T2 (hu) | 2013-10-14 | 2019-12-30 | Immedica Pharma Ab | Eljárások a karbamidciklus rendellenességeinek kezelésére |
| WO2015063659A1 (en) | 2013-10-30 | 2015-05-07 | Lupin Limited | Process for the preparation of glycerol phenylbutyrate |
| CN105764497A (zh) | 2013-11-14 | 2016-07-13 | 奥特吉尼克斯制药公司 | 三酸甘油酯的固体组合物及其用途 |
| CA2946422C (en) | 2014-04-30 | 2019-03-05 | The Johns Hopkins University | Dendrimer compositions and their use in treatment of diseases of the eye |
| JP6342575B2 (ja) | 2014-08-13 | 2018-06-13 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 脳腫瘍への選択的デンドリマー送達 |
| CA3003589C (en) | 2015-10-29 | 2021-12-07 | The Johns Hopkins University | Dendrimer compositions and methods for treatment of peroxisomal disorders and leukodystrophies |
| US9914692B2 (en) | 2016-05-25 | 2018-03-13 | Horizon Therapeutics, Llc | Procedure for the preparation of 4-phenyl butyrate and uses thereof |
| US10668040B2 (en) | 2017-09-11 | 2020-06-02 | Horizon Therapeutics, Llc | Treatment of urea cycle disorders in neonates and infants |
| JP7759322B2 (ja) | 2019-12-04 | 2025-10-23 | アシュバッタ セラピューティクス， インコーポレイテッド | 眼に薬物送達するためのデンドリマー組成物および方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5879657A (en) * | 1993-03-30 | 1999-03-09 | The Dupont Merck Pharmaceutical Company | Radiolabeled platelet GPIIb/IIIa receptor antagonists as imaging agents for the diagnosis of thromboembolic disorders |
-
1996
- 1996-02-06 DE DE69612755T patent/DE69612755T2/de not_active Expired - Lifetime
- 1996-02-06 AT AT96904495T patent/ATE201013T1/de not_active IP Right Cessation
- 1996-02-06 WO PCT/US1996/000940 patent/WO1996024571A1/en not_active Ceased
- 1996-02-06 AU AU48587/96A patent/AU4858796A/en not_active Abandoned
- 1996-02-06 EP EP96904495A patent/EP0858441B1/en not_active Expired - Lifetime
- 1996-02-06 CA CA2212047A patent/CA2212047C/en not_active Expired - Fee Related
- 1996-02-06 ES ES96904495T patent/ES2157422T3/es not_active Expired - Lifetime
-
1998
- 1998-01-13 US US09/006,432 patent/US5968979A/en not_active Expired - Lifetime
-
1999
- 1999-05-25 US US09/317,901 patent/US6060510A/en not_active Expired - Lifetime
- 1999-05-25 US US09/317,900 patent/US6083984A/en not_active Expired - Lifetime
-
2016
- 2016-02-03 FR FR16C0003C patent/FR16C0003I2/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ATE201013T1 (de) | 2001-05-15 |
| US6083984A (en) | 2000-07-04 |
| FR16C0003I1 (https=) | 2016-03-25 |
| AU4858796A (en) | 1996-08-27 |
| WO1996024571A1 (en) | 1996-08-15 |
| US5968979A (en) | 1999-10-19 |
| US6060510A (en) | 2000-05-09 |
| EP0858441A1 (en) | 1998-08-19 |
| ES2157422T3 (es) | 2001-08-16 |
| DE69612755D1 (de) | 2001-06-13 |
| EP0858441A4 (https=) | 1998-08-19 |
| CA2212047A1 (en) | 1996-08-15 |
| DE69612755T2 (de) | 2001-08-23 |
| FR16C0003I2 (fr) | 2016-06-24 |
| EP0858441B1 (en) | 2001-05-09 |
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| FZDC | Discontinued application reinstated | ||
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Effective date: 20160208 |