CA2392580A1 - A process for the preparation of high purity pemirolast - Google Patents
A process for the preparation of high purity pemirolast Download PDFInfo
- Publication number
- CA2392580A1 CA2392580A1 CA002392580A CA2392580A CA2392580A1 CA 2392580 A1 CA2392580 A1 CA 2392580A1 CA 002392580 A CA002392580 A CA 002392580A CA 2392580 A CA2392580 A CA 2392580A CA 2392580 A1 CA2392580 A1 CA 2392580A1
- Authority
- CA
- Canada
- Prior art keywords
- pemirolast
- preparation
- high purity
- amines
- purification
- 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.)
- Abandoned
Links
- HIANJWSAHKJQTH-UHFFFAOYSA-N pemirolast Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NNN=1 HIANJWSAHKJQTH-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 13
- 229960004439 pemirolast Drugs 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000000746 purification Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000005266 diarylamine group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- -1 aliphatic amines Chemical class 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 230000003266 anti-allergic effect Effects 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 229940127557 pharmaceutical product Drugs 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960004811 pemirolast potassium Drugs 0.000 description 2
- NMMVKSMGBDRONO-UHFFFAOYSA-N potassium;9-methyl-3-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound [K+].CC1=CC=CN(C2=O)C1=NC=C2C1=NN=N[N-]1 NMMVKSMGBDRONO-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI001764A ITMI20011764A1 (it) | 2001-08-10 | 2001-08-10 | Metodo per l'ottenimento del pemirolast ad elevata purezza |
| ITMI2001A001764 | 2001-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2392580A1 true CA2392580A1 (en) | 2003-02-10 |
Family
ID=11448273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002392580A Abandoned CA2392580A1 (en) | 2001-08-10 | 2002-07-08 | A process for the preparation of high purity pemirolast |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6703505B2 (enExample) |
| EP (1) | EP1285921B1 (enExample) |
| JP (1) | JP2003073378A (enExample) |
| KR (1) | KR20030014619A (enExample) |
| AT (1) | ATE267827T1 (enExample) |
| CA (1) | CA2392580A1 (enExample) |
| DE (1) | DE60200535T2 (enExample) |
| IT (1) | ITMI20011764A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20011764A1 (it) * | 2001-08-10 | 2003-02-10 | Dinamite Dipharma Spa | Metodo per l'ottenimento del pemirolast ad elevata purezza |
| KR100762373B1 (ko) * | 2006-03-14 | 2007-10-04 | 주식회사 엘지화학 | 인쇄용 반사시트 |
| WO2008074975A1 (en) * | 2006-12-18 | 2008-06-26 | Cardoz Ab | New combination for use in the treatment of inflammatory disorders |
| EP2107907B1 (en) * | 2006-12-20 | 2012-02-01 | Cardoz AB | Combination of pemirolast and ramatroban for use in the treatment of inflammatory disorders |
| WO2009007675A2 (en) * | 2007-07-11 | 2009-01-15 | Cardoz Ab | Combination for use in the treatment of atherosclerosis comprising a mast cell inhibitor and a p2 gamma 12 antagonist |
| EP2175845A2 (en) * | 2007-07-11 | 2010-04-21 | Cardoz AB | New combination for use in the treatment of inflammatory disorders |
| WO2009007679A2 (en) * | 2007-07-11 | 2009-01-15 | Cardoz Ab | Combination for use in the treatment of atherosclerosis comprising a mast cell inhibitor and a thromboxane a2 antagonist |
| PT2443120T (pt) | 2009-06-16 | 2017-02-08 | Rspr Pharma Ab | Forma cristalina de pemirolast |
| US20160243122A1 (en) | 2014-10-23 | 2016-08-25 | Rspr Pharma Ab | Use of pemirolast in the treatment of acute asthma |
| WO2016102941A1 (en) | 2014-12-22 | 2016-06-30 | Rspr Pharma Ab | New combination of pemirolast and montelukast |
| GB201518831D0 (en) | 2015-10-23 | 2015-12-09 | Rspr Pharma Ab | New use |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE243821C (enExample) | ||||
| US4122274A (en) * | 1977-05-25 | 1978-10-24 | Bristol-Myers Company | 3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones |
| US4474953A (en) * | 1982-09-09 | 1984-10-02 | Riker Laboratories, Inc. | Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones |
| DD243821A3 (de) * | 1984-04-11 | 1987-03-18 | Dresden Arzneimittel | Verfahren zur reinigung von n-(4-(ss- 2-methoxy-5-chlor-benzamido -ethyl)-phenylsulfonyl)-n'-cyclohexyl-harnstoff |
| JPS63183581A (ja) * | 1985-10-03 | 1988-07-28 | Tokyo Tanabe Co Ltd | ピリド〔１，２−ａ〕ピリミジン誘導体、その製造法及びそれを有効成分とするアレルギ−疾患治療薬 |
| CA2044796C (en) * | 1990-06-21 | 2001-10-16 | Atsunori Sano | Process for producing pyrido[1,2-a] pyrimidine derivative |
| HUT64064A (en) * | 1992-02-13 | 1993-11-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing puyrido/1,2-a/pyrimidine derivatives and pharmaceutical compositions comprising same as active ingredient |
| SI9300296B (sl) * | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| ITMI20011764A1 (it) * | 2001-08-10 | 2003-02-10 | Dinamite Dipharma Spa | Metodo per l'ottenimento del pemirolast ad elevata purezza |
-
2001
- 2001-08-10 IT IT2001MI001764A patent/ITMI20011764A1/it unknown
-
2002
- 2002-06-25 EP EP02014148A patent/EP1285921B1/en not_active Expired - Lifetime
- 2002-06-25 AT AT02014148T patent/ATE267827T1/de not_active IP Right Cessation
- 2002-06-25 DE DE60200535T patent/DE60200535T2/de not_active Expired - Fee Related
- 2002-07-08 CA CA002392580A patent/CA2392580A1/en not_active Abandoned
- 2002-07-17 US US10/196,260 patent/US6703505B2/en not_active Expired - Fee Related
- 2002-08-07 KR KR1020020046538A patent/KR20030014619A/ko not_active Ceased
- 2002-08-09 JP JP2002233207A patent/JP2003073378A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60200535D1 (de) | 2004-07-01 |
| EP1285921A1 (en) | 2003-02-26 |
| JP2003073378A (ja) | 2003-03-12 |
| KR20030014619A (ko) | 2003-02-19 |
| ATE267827T1 (de) | 2004-06-15 |
| DE60200535T2 (de) | 2004-09-23 |
| EP1285921B1 (en) | 2004-05-26 |
| ITMI20011764A0 (it) | 2001-08-10 |
| US20030032805A1 (en) | 2003-02-13 |
| ITMI20011764A1 (it) | 2003-02-10 |
| US6703505B2 (en) | 2004-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |