TW200819446A - Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor - Google Patents
Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor Download PDFInfo
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- TW200819446A TW200819446A TW096130026A TW96130026A TW200819446A TW 200819446 A TW200819446 A TW 200819446A TW 096130026 A TW096130026 A TW 096130026A TW 96130026 A TW96130026 A TW 96130026A TW 200819446 A TW200819446 A TW 200819446A
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 15
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 title claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title abstract description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 title abstract description 9
- 150000003891 oxalate salts Chemical class 0.000 title abstract description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 57
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- HAFWELDDNUXLCK-ODZAUARKSA-N (z)-but-2-enedioic acid;hydrate Chemical group O.OC(=O)\C=C/C(O)=O HAFWELDDNUXLCK-ODZAUARKSA-N 0.000 claims description 21
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- 239000007787 solid Substances 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- -1 dibutyl methyl Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 7
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000706 filtrate Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- FDYKGJFSAUBIOO-UHFFFAOYSA-N 1h-indene-1-sulfonic acid Chemical group C1=CC=C2C(S(=O)(=O)O)C=CC2=C1 FDYKGJFSAUBIOO-UHFFFAOYSA-N 0.000 claims 1
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical group O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83766106P | 2006-08-14 | 2006-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200819446A true TW200819446A (en) | 2008-05-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096130026A TW200819446A (en) | 2006-08-14 | 2007-08-14 | Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7956189B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2069337A1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP2010500406A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101522671A (cg-RX-API-DMAC7.html) |
| AR (1) | AR062373A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2660703A1 (cg-RX-API-DMAC7.html) |
| CL (1) | CL2007002366A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2009001770A (cg-RX-API-DMAC7.html) |
| PE (1) | PE20080424A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW200819446A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008021271A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2609659C (en) | 2005-05-26 | 2014-01-28 | Neuron Systems, Inc. | Azanaphthalenes, compositions and methods for treating retinal disease |
| CA2782015C (en) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Topical ophthalmic compositions and methods for the treatment of macular degeneration |
| WO2014012859A1 (en) * | 2012-07-19 | 2014-01-23 | Boehringer Ingelheim International Gmbh | Fumaric acid salt of 9-[4-(3-chloro-2-fluoro-phenylamino)-7-methoxy- chinazolin-6-yloxy]-1,4-diaza-spiro[5.5]undecan-5-one, its use as medicament and the preparation thereof |
| AU2014209387B2 (en) | 2013-01-23 | 2018-11-01 | Aldeyra Therapeutics, Inc. | Toxic aldehyde related diseases and treatment |
| EP4400106A1 (en) | 2015-08-21 | 2024-07-17 | Aldeyra Therapeutics, Inc. | Deuterated compounds and uses thereof |
| WO2019075136A1 (en) | 2017-10-10 | 2019-04-18 | Aldeyra Therapeutics, Inc. | TREATMENT OF INFLAMMATORY DISORDERS |
| US12006298B2 (en) | 2018-08-06 | 2024-06-11 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| CN113784954A (zh) | 2019-05-02 | 2021-12-10 | 奥尔德拉医疗公司 | 多晶型化合物和其用途 |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| CA3175856A1 (en) | 2020-05-13 | 2021-11-18 | Todd Brady | Pharmaceutical formulations and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2417993C9 (ru) * | 2004-05-18 | 2011-10-10 | Шеринг Корпорейшн | Замещенные 2-хинолилоксазолы, пригодные в качестве ингибиторов фдэ4 |
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2007
- 2007-08-10 MX MX2009001770A patent/MX2009001770A/es active IP Right Grant
- 2007-08-10 EP EP07811264A patent/EP2069337A1/en not_active Withdrawn
- 2007-08-10 WO PCT/US2007/017848 patent/WO2008021271A1/en not_active Ceased
- 2007-08-10 US US11/891,351 patent/US7956189B2/en not_active Expired - Fee Related
- 2007-08-10 JP JP2009524638A patent/JP2010500406A/ja not_active Withdrawn
- 2007-08-10 CA CA002660703A patent/CA2660703A1/en not_active Abandoned
- 2007-08-10 CN CNA2007800382818A patent/CN101522671A/zh active Pending
- 2007-08-14 PE PE2007001088A patent/PE20080424A1/es not_active Application Discontinuation
- 2007-08-14 CL CL200702366A patent/CL2007002366A1/es unknown
- 2007-08-14 TW TW096130026A patent/TW200819446A/zh unknown
- 2007-08-14 AR ARP070103601A patent/AR062373A1/es not_active Application Discontinuation
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2012
- 2012-06-19 JP JP2012137788A patent/JP2012176989A/ja not_active Withdrawn
- 2012-11-09 JP JP2012247215A patent/JP2013032394A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008021271A1 (en) | 2008-02-21 |
| PE20080424A1 (es) | 2008-04-28 |
| US7956189B2 (en) | 2011-06-07 |
| CN101522671A (zh) | 2009-09-02 |
| AR062373A1 (es) | 2008-11-05 |
| JP2012176989A (ja) | 2012-09-13 |
| JP2013032394A (ja) | 2013-02-14 |
| JP2010500406A (ja) | 2010-01-07 |
| CL2007002366A1 (es) | 2008-03-14 |
| CA2660703A1 (en) | 2008-02-21 |
| MX2009001770A (es) | 2009-02-25 |
| US20080108818A1 (en) | 2008-05-08 |
| EP2069337A1 (en) | 2009-06-17 |
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