NO321308B1 - Polymorfe modifikasjoner av 2-(3-cyano-4-isobutyloksyfenyl)-4-metyl-5-tiazol-karboksylsyre, amorf forbindelse, og fremgangsmater for fremstilling derav - Google Patents
Polymorfe modifikasjoner av 2-(3-cyano-4-isobutyloksyfenyl)-4-metyl-5-tiazol-karboksylsyre, amorf forbindelse, og fremgangsmater for fremstilling derav Download PDFInfo
- Publication number
- NO321308B1 NO321308B1 NO20000789A NO20000789A NO321308B1 NO 321308 B1 NO321308 B1 NO 321308B1 NO 20000789 A NO20000789 A NO 20000789A NO 20000789 A NO20000789 A NO 20000789A NO 321308 B1 NO321308 B1 NO 321308B1
- Authority
- NO
- Norway
- Prior art keywords
- crystal
- cyano
- methyl
- carboxylic acid
- thiazole
- Prior art date
Links
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title description 17
- 238000012986 modification Methods 0.000 title description 2
- 230000004048 modification Effects 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 165
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000010438 heat treatment Methods 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 239000012046 mixed solvent Substances 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 16
- 239000013078 crystal Substances 0.000 claims description 187
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 230000009102 absorption Effects 0.000 claims description 23
- 238000010521 absorption reaction Methods 0.000 claims description 23
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 14
- 238000012844 infrared spectroscopy analysis Methods 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000007605 air drying Methods 0.000 claims description 7
- YSTPVFAPIHYRBV-UHFFFAOYSA-N CC(C)COC(C=CC(C1=NC(C)=C[S+]1C([O-])=O)=C1)=C1C#N Chemical compound CC(C)COC(C=CC(C1=NC(C)=C[S+]1C([O-])=O)=C1)=C1C#N YSTPVFAPIHYRBV-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 15
- 238000003860 storage Methods 0.000 description 15
- 238000002441 X-ray diffraction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000004566 IR spectroscopy Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000009466 transformation Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- -1 2-{3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiol-carboxylic acid Chemical compound 0.000 description 1
- 201000001431 Hyperuricemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
- 229960001768 buspirone hydrochloride Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical group CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002386 prazosin hydrochloride Drugs 0.000 description 1
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17307998 | 1998-06-19 | ||
PCT/JP1999/003258 WO1999065885A1 (en) | 1998-06-19 | 1999-06-18 | Polymorphic modifications of 2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazole-carboxylic acid and processes for the preparation thereof |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20000789D0 NO20000789D0 (no) | 2000-02-17 |
NO20000789L NO20000789L (no) | 2000-02-17 |
NO321308B1 true NO321308B1 (no) | 2006-04-24 |
Family
ID=15953825
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20000789A NO321308B1 (no) | 1998-06-19 | 2000-02-17 | Polymorfe modifikasjoner av 2-(3-cyano-4-isobutyloksyfenyl)-4-metyl-5-tiazol-karboksylsyre, amorf forbindelse, og fremgangsmater for fremstilling derav |
Country Status (39)
Country | Link |
---|---|
US (1) | US6225474B1 (lt) |
EP (4) | EP2404910A3 (lt) |
JP (1) | JP3547707B2 (lt) |
KR (1) | KR100511183B1 (lt) |
CN (3) | CN102659712A (lt) |
AT (2) | ATE449765T1 (lt) |
AU (1) | AU748026B2 (lt) |
BE (1) | BE2010C024I2 (lt) |
BG (1) | BG64734B1 (lt) |
BR (1) | BR9906539A (lt) |
CA (2) | CA2566652C (lt) |
CY (3) | CY1109720T1 (lt) |
CZ (1) | CZ298170B6 (lt) |
DE (2) | DE122010000013I1 (lt) |
DK (3) | DK1020454T4 (lt) |
ES (3) | ES2371786T5 (lt) |
FR (1) | FR10C0022I2 (lt) |
GT (1) | GT199900216A (lt) |
HK (2) | HK1029788A1 (lt) |
HR (2) | HRP20000092C1 (lt) |
HU (2) | HU229405B1 (lt) |
ID (1) | ID25775A (lt) |
IL (1) | IL134594A (lt) |
IN (1) | IN191537B (lt) |
IS (4) | IS9020A (lt) |
LT (1) | LT1956014T (lt) |
LU (1) | LU91682I2 (lt) |
NO (1) | NO321308B1 (lt) |
NZ (1) | NZ503326A (lt) |
PL (1) | PL200710B1 (lt) |
PT (3) | PT1956014T (lt) |
RU (1) | RU2198169C3 (lt) |
SI (3) | SI1956015T2 (lt) |
SK (2) | SK287946B6 (lt) |
TR (1) | TR200000458T1 (lt) |
TW (1) | TWI248439B (lt) |
UA (1) | UA57611C2 (lt) |
WO (1) | WO1999065885A1 (lt) |
ZA (1) | ZA200000737B (lt) |
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MXPA04000294A (es) * | 2001-07-10 | 2004-05-04 | Pharmacia & Upjhon Company | Tiacin oxazolidinonas cristalinas. |
CA2455050C (en) | 2001-08-15 | 2007-02-20 | Pharmacia & Upjohn Company | Crystals including a malic acid salt of n-[2-(diethylamino) ethyl]-5-[(5-fluoro-2-oxo-3h-indole-3-ylidene) methyl]-2, 4-dimethyl-1h-pyrrole-3-carboxamide, processes for its preparation and compositions thereof |
EP1469827B1 (en) | 2002-01-09 | 2017-12-27 | Emisphere Technologies, Inc. | Polymorphs of sodium 4- (4-chloro-2-hydroxybenzoyl)amino butanoate |
JP2003261548A (ja) * | 2002-03-07 | 2003-09-19 | Teijin Ltd | 2−(3−シアノ−4−イソブチルオキシフェニル)−4−メチル−5−チアゾールカルボン酸の結晶多形体の製造方法 |
AU2003220909B2 (en) * | 2002-03-28 | 2008-09-18 | Teijin Limited | Solid preparation containing single crystal form |
US8841333B2 (en) * | 2005-05-09 | 2014-09-23 | Takeda Pharmaceuticals U.S.A., Inc. | Methods for treating nephrolithiasis |
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CN101386605B (zh) * | 2008-10-23 | 2010-09-08 | 中国科学院上海药物研究所 | 非布司他新型晶体及其制备方法 |
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AU2003220909B2 (en) | 2002-03-28 | 2008-09-18 | Teijin Limited | Solid preparation containing single crystal form |
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