KR20170049645A - 페미로라스트의 신규한 결정형 - Google Patents
페미로라스트의 신규한 결정형 Download PDFInfo
- Publication number
- KR20170049645A KR20170049645A KR1020177012036A KR20177012036A KR20170049645A KR 20170049645 A KR20170049645 A KR 20170049645A KR 1020177012036 A KR1020177012036 A KR 1020177012036A KR 20177012036 A KR20177012036 A KR 20177012036A KR 20170049645 A KR20170049645 A KR 20170049645A
- Authority
- KR
- South Korea
- Prior art keywords
- sodium
- disease
- salts
- compound
- water
- 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.)
- Ceased
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- HIANJWSAHKJQTH-UHFFFAOYSA-N pemirolast Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NNN=1 HIANJWSAHKJQTH-UHFFFAOYSA-N 0.000 title description 6
- 229960004439 pemirolast Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 100
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 68
- -1 Sodium salt compound Chemical class 0.000 claims description 49
- 239000013078 crystal Substances 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 46
- 239000011734 sodium Substances 0.000 claims description 46
- 229910052708 sodium Inorganic materials 0.000 claims description 43
- 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 claims description 39
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 25
- 238000002425 crystallisation Methods 0.000 claims description 24
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- 239000003814 drug Substances 0.000 claims description 22
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- 238000004090 dissolution Methods 0.000 claims description 20
- 229940079593 drug Drugs 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 208000006673 asthma Diseases 0.000 claims description 13
- 208000027866 inflammatory disease Diseases 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 230000036961 partial effect Effects 0.000 claims description 10
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 201000009273 Endometriosis Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
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- 206010027599 migraine Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 230000036571 hydration Effects 0.000 claims description 3
- 238000006703 hydration reaction Methods 0.000 claims description 3
- 239000012296 anti-solvent Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 28
- 150000004688 heptahydrates Chemical class 0.000 description 36
- 239000000203 mixture Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 239000003826 tablet Substances 0.000 description 27
- 239000002002 slurry Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 206010057190 Respiratory tract infections Diseases 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 108010074051 C-Reactive Protein Proteins 0.000 description 14
- 102100032752 C-reactive protein Human genes 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 14
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- 239000000126 substance Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910052700 potassium Inorganic materials 0.000 description 12
- 229960003975 potassium Drugs 0.000 description 12
- 239000011591 potassium Substances 0.000 description 12
- 206010061218 Inflammation Diseases 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 11
- 230000004054 inflammatory process Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 125000005490 tosylate group Chemical class 0.000 description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 10
- 239000000463 material Substances 0.000 description 9
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- 102000005862 Angiotensin II Human genes 0.000 description 8
- 101800000733 Angiotensin-2 Proteins 0.000 description 8
- 201000001320 Atherosclerosis Diseases 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 8
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229950006323 angiotensin ii Drugs 0.000 description 8
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- 235000019359 magnesium stearate Nutrition 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- 229940016286 microcrystalline cellulose Drugs 0.000 description 8
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- 239000011343 solid material Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 description 7
- 208000024172 Cardiovascular disease Diseases 0.000 description 7
- 238000005079 FT-Raman Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 6
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 6
- JACXUEYJJKTYSW-UHFFFAOYSA-N O.O.O.O.O.O.O.[Na] Chemical compound O.O.O.O.O.O.O.[Na] JACXUEYJJKTYSW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940125364 angiotensin receptor blocker Drugs 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 230000002526 effect on cardiovascular system Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 6
- 230000004968 inflammatory condition Effects 0.000 description 6
- 239000000905 isomalt Substances 0.000 description 6
- 235000010439 isomalt Nutrition 0.000 description 6
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Natural products CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 239000011541 reaction mixture Substances 0.000 description 6
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 5
- 230000009471 action Effects 0.000 description 5
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- 208000010668 atopic eczema Diseases 0.000 description 5
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- AJNPUGKXELKSHS-YOTINIEPSA-L disodium;(e)-but-2-enedioate;hydrate Chemical compound O.[Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O AJNPUGKXELKSHS-YOTINIEPSA-L 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 5
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- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 4
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- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 4
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- 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
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| MX2012005513A (es) * | 2009-11-13 | 2012-06-19 | Cardoz Ab | Pemirolast para el tratamiento de inflamacion sistemica de bajo grado. |
| EA034550B1 (ru) * | 2013-03-09 | 2020-02-19 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Способы лечения, снижения частоты и/или профилактики ишемических событий |
| WO2016063085A1 (en) | 2014-10-23 | 2016-04-28 | 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 |
| CN110267661B (zh) * | 2016-10-03 | 2021-08-03 | 布利本迅药业(上海)有限公司 | 包括trh类似物和丙基辛酸的组合的组合物和丙基辛酸的药学上可接受的盐 |
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| JP2504788B2 (ja) | 1987-11-10 | 1996-06-05 | 東京田辺製薬株式会社 | ９−メチル−３−（１Ｈ−テトラゾ―ル−５−イル）−４Ｈ−ピリド［１，２−ａ］ピリミジン−４−オンカリウム塩の水性製剤 |
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| ITMI20011764A1 (it) | 2001-08-10 | 2003-02-10 | Dinamite Dipharma Spa | Metodo per l'ottenimento del pemirolast ad elevata purezza |
| HUE029336T2 (en) | 2005-09-16 | 2017-02-28 | Daiichi Sankyo Co Ltd | For the preparation of an optically active diamine derivative and process |
| CN101610765A (zh) * | 2006-12-18 | 2009-12-23 | 卡多兹公司 | 用于治疗炎症的新组合物 |
| EP2107907B1 (en) * | 2006-12-20 | 2012-02-01 | Cardoz AB | Combination of pemirolast and ramatroban for use in the treatment of inflammatory disorders |
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