ES2404348T3 - Procedimiento para la preparación de ácidos 1, 2, 4-oxadiazol-benzoicos - Google Patents
Procedimiento para la preparación de ácidos 1, 2, 4-oxadiazol-benzoicos Download PDFInfo
- Publication number
- ES2404348T3 ES2404348T3 ES07837899T ES07837899T ES2404348T3 ES 2404348 T3 ES2404348 T3 ES 2404348T3 ES 07837899 T ES07837899 T ES 07837899T ES 07837899 T ES07837899 T ES 07837899T ES 2404348 T3 ES2404348 T3 ES 2404348T3
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- Spain
- Prior art keywords
- approximately
- substituted
- steps
- butanol
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- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 54
- DGFURIPMSCLLMY-UHFFFAOYSA-N 2-(1,2,4-oxadiazol-3-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=NOC=N1 DGFURIPMSCLLMY-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title description 5
- 239000002904 solvent Substances 0.000 claims abstract description 49
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- -1 halobenzoyl chloride Chemical compound 0.000 claims abstract description 23
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- 230000010933 acylation Effects 0.000 claims abstract description 9
- 238000005917 acylation reaction Methods 0.000 claims abstract description 9
- 238000009833 condensation Methods 0.000 claims abstract description 9
- 230000005494 condensation Effects 0.000 claims abstract description 9
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 8
- RAMPDACRJWTXEV-UHFFFAOYSA-N methyl 2-cyanobenzoate Chemical compound COC(=O)C1=CC=CC=C1C#N RAMPDACRJWTXEV-UHFFFAOYSA-N 0.000 claims abstract description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000002955 isolation Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical group FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims description 9
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical group CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000008213 purified water Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 239000012065 filter cake Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- OOUGLTULBSNHNF-UHFFFAOYSA-N 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 OOUGLTULBSNHNF-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- XPBHWSMZTSSEJE-UHFFFAOYSA-N methyl 3-cyanobenzoate Chemical compound COC(=O)C1=CC=CC(C#N)=C1 XPBHWSMZTSSEJE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 108020004485 Nonsense Codon Proteins 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 230000037434 nonsense mutation Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PRAYXRLPTMXYEZ-UHFFFAOYSA-N methyl 3-carbamimidoylbenzoate Chemical compound COC(=O)C1=CC=CC(C(N)=N)=C1 PRAYXRLPTMXYEZ-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 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 description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- GYLKKXHEIIFTJH-UHFFFAOYSA-N 3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC(C#N)=C1 GYLKKXHEIIFTJH-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000694440 Colpidium aqueous Species 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
- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 208000016361 genetic disease Diseases 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LFJJTHGQRVVGGN-UHFFFAOYSA-N methyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 LFJJTHGQRVVGGN-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 |
|---|---|---|---|
| US84359506P | 2006-09-08 | 2006-09-08 | |
| US843595P | 2006-09-08 | ||
| PCT/US2007/019561 WO2008030570A1 (en) | 2006-09-08 | 2007-09-06 | Processes for the preparation of 1,2,4-oxadiazole benzoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2404348T3 true ES2404348T3 (es) | 2013-05-27 |
Family
ID=38935880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07837899T Active ES2404348T3 (es) | 2006-09-08 | 2007-09-06 | Procedimiento para la preparación de ácidos 1, 2, 4-oxadiazol-benzoicos |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7678922B2 (enExample) |
| EP (1) | EP2059513B1 (enExample) |
| JP (2) | JP5955494B2 (enExample) |
| KR (1) | KR101466368B1 (enExample) |
| CN (1) | CN101535284B (enExample) |
| AR (3) | AR062715A1 (enExample) |
| AU (1) | AU2007292915B2 (enExample) |
| BR (1) | BRPI0716996B8 (enExample) |
| CA (2) | CA2662749C (enExample) |
| CL (1) | CL2007002606A1 (enExample) |
| DK (1) | DK2059513T3 (enExample) |
| ES (1) | ES2404348T3 (enExample) |
| IL (1) | IL197445A (enExample) |
| MX (1) | MX2009002439A (enExample) |
| MY (1) | MY148598A (enExample) |
| NZ (2) | NZ598012A (enExample) |
| PE (2) | PE20080771A1 (enExample) |
| PL (1) | PL2059513T3 (enExample) |
| PT (1) | PT2059513E (enExample) |
| RU (1) | RU2495030C2 (enExample) |
| TW (1) | TWI482761B (enExample) |
| UA (1) | UA99265C2 (enExample) |
| WO (1) | WO2008030570A1 (enExample) |
| ZA (1) | ZA200901782B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2910551T3 (pl) | 2003-04-11 | 2017-09-29 | Ptc Therapeutics, Inc. | Związki kwasu 1,2,4-oksadiazolobenzoesowego i ich zastosowanie do supresji mutacji nonsensownych i leczenia choroby |
| PT2402002T (pt) | 2005-04-08 | 2018-10-08 | Ptc Therapeutics Inc | Composições de 1,2,4-oxadiazole oralmente activo para terapia de supressão de mutações nonsense |
| CA2647903C (en) | 2006-03-30 | 2016-12-13 | Ptc Therapeutics, Inc. | Methods for the production of functional protein from dna having a nonsense mutation and the treatment of disorders associated therewith |
| WO2008030570A1 (en) * | 2006-09-08 | 2008-03-13 | Ptc Therapeutics, Inc. | Processes for the preparation of 1,2,4-oxadiazole benzoic acids |
| EP2068871B1 (en) | 2006-09-25 | 2013-12-25 | PTC Therapeutics, Inc. | Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, compositions thereof and the use for nonsense suppression |
| SI2076501T1 (sl) * | 2006-09-25 | 2016-05-31 | Ptc Therapeutics, Inc. | Kristalinične oblike 3-(5-(2-florofenil)-1,2,4) oksadiazol-3-il)-benzojske kisline |
| ES2538359T3 (es) | 2006-10-12 | 2015-06-19 | Ptc Therapeutics, Inc. | Métodos para administrar un 1,2,4-oxadiazol activo por vía oral para terapia de supresión de mutación sin sentido |
| CN101714009A (zh) * | 2009-05-14 | 2010-05-26 | 翁印嵩 | 集成通用电话功能的计算机 |
| ES2610362T3 (es) | 2011-01-25 | 2017-04-27 | Viviabiotech, S.L. | Derivados de 1,2,4-oxadiazol como fármacos moduladores del receptor para el péptido glp-1 |
| UA114915C2 (uk) | 2012-07-02 | 2017-08-28 | Монсанто Текнолоджи Ллс | Спосіб одержання 3,5-дизаміщених 1,2,4-оксадіазолів (варіанти) |
| TWI695717B (zh) | 2014-03-06 | 2020-06-11 | 美商 Ptc 治療公司 | １,２,４-二唑苯甲酸之鹽及醫藥組合物 |
| CN105461650B (zh) * | 2014-09-12 | 2018-04-13 | 杭州普晒医药科技有限公司 | 一种噁二唑化合物的溶剂化物及其制备方法 |
| CN106316885B (zh) * | 2015-07-03 | 2019-02-12 | 普济生物科技（台州）有限公司 | 一种3-[5-(2-氟苯基)-1,2,4-噁二唑-3-基]苯甲酸的制备方法 |
| MX2018005361A (es) | 2015-10-30 | 2018-06-07 | Ptc Therapeutics Inc | Metodos para tratar epilepsia. |
| TW201808922A (zh) | 2016-06-20 | 2018-03-16 | 台灣神隆股份有限公司 | 製備阿塔魯仁及其中間體的方法 |
| US12268669B2 (en) | 2018-12-20 | 2025-04-08 | Pfizer Inc. | Pharmaceutical compositions and methods comprising a combination of a benzoxazole transthyretin stabilizer and an additional therapeutic agent |
| EA202192767A1 (ru) | 2019-04-10 | 2021-12-29 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способ лечения опосредуемой нонсенс-мутацией мышечной дистрофии дюшенна у педиатрических пациентов |
| WO2022112919A1 (en) | 2020-11-25 | 2022-06-02 | Pfizer Inc. | (aza)benzothiazolyl substituted pyrazole compounds |
| CN113045510B (zh) * | 2021-03-31 | 2022-05-27 | 北京大学生命科学华东产业研究院 | 一种阿塔鲁伦的制备方法 |
| CN114920667B (zh) * | 2022-06-30 | 2024-06-21 | 湖南大学 | 一种阿塔鲁伦酯的电化学制备方法 |
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| DE2801509A1 (de) * | 1978-01-12 | 1979-07-19 | Schering Ag | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| DE3905242A1 (de) * | 1989-02-21 | 1990-08-23 | Basf Ag | Verfahren zur herstellung von phenyloxdiazolylanilinen |
| NZ234760A (en) * | 1989-08-18 | 1991-09-25 | Sterling Drug Inc | Antiviral oxazole compounds and compositions |
| DE4425794A1 (de) * | 1994-07-21 | 1996-01-25 | Basf Ag | Nitrofarbstoffe |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2449544A1 (en) * | 2001-06-08 | 2002-12-19 | Cytovia, Inc. | Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs |
| MY151199A (en) * | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| US20040132726A1 (en) * | 2002-08-09 | 2004-07-08 | Astrazeneca Ab And Nps Pharmaceuticals, Inc. | New compounds |
| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| PL2910551T3 (pl) * | 2003-04-11 | 2017-09-29 | Ptc Therapeutics, Inc. | Związki kwasu 1,2,4-oksadiazolobenzoesowego i ich zastosowanie do supresji mutacji nonsensownych i leczenia choroby |
| US20050075375A1 (en) * | 2003-05-14 | 2005-04-07 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis C virus |
| PT2402002T (pt) * | 2005-04-08 | 2018-10-08 | Ptc Therapeutics Inc | Composições de 1,2,4-oxadiazole oralmente activo para terapia de supressão de mutações nonsense |
| WO2008030570A1 (en) * | 2006-09-08 | 2008-03-13 | Ptc Therapeutics, Inc. | Processes for the preparation of 1,2,4-oxadiazole benzoic acids |
-
2007
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- 2007-09-06 KR KR1020097007202A patent/KR101466368B1/ko not_active Expired - Fee Related
- 2007-09-06 AU AU2007292915A patent/AU2007292915B2/en active Active
- 2007-09-06 RU RU2009113019/04A patent/RU2495030C2/ru active
- 2007-09-06 DK DK07837899.9T patent/DK2059513T3/da active
- 2007-09-06 MX MX2009002439A patent/MX2009002439A/es active IP Right Grant
- 2007-09-06 PT PT78378999T patent/PT2059513E/pt unknown
- 2007-09-06 NZ NZ598012A patent/NZ598012A/xx unknown
- 2007-09-06 US US11/899,813 patent/US7678922B2/en active Active - Reinstated
- 2007-09-06 ES ES07837899T patent/ES2404348T3/es active Active
- 2007-09-06 NZ NZ575511A patent/NZ575511A/en unknown
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- 2007-09-06 CA CA2662749A patent/CA2662749C/en active Active
- 2007-09-06 JP JP2009527430A patent/JP5955494B2/ja active Active
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- 2007-09-06 CN CN200780041169.XA patent/CN101535284B/zh active Active
- 2007-09-06 BR BRPI0716996A patent/BRPI0716996B8/pt active IP Right Grant
- 2007-09-07 AR ARP070103975A patent/AR062715A1/es not_active Application Discontinuation
- 2007-09-07 TW TW096133607A patent/TWI482761B/zh active
- 2007-09-07 PE PE2007001203A patent/PE20080771A1/es active IP Right Grant
- 2007-09-07 PE PE2011001405A patent/PE20120669A1/es active IP Right Grant
- 2007-09-07 CL CL200702606A patent/CL2007002606A1/es unknown
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- 2009-11-13 US US12/617,757 patent/US8367841B2/en active Active
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