ZA200104081B - Chrystals of 5-[{6-(2-flourobenzyl)oxy-2-napthyl}methyl]-2,4-thiazolidinedione. - Google Patents
Chrystals of 5-[{6-(2-flourobenzyl)oxy-2-napthyl}methyl]-2,4-thiazolidinedione. Download PDFInfo
- Publication number
- ZA200104081B ZA200104081B ZA200104081A ZA200104081A ZA200104081B ZA 200104081 B ZA200104081 B ZA 200104081B ZA 200104081 A ZA200104081 A ZA 200104081A ZA 200104081 A ZA200104081 A ZA 200104081A ZA 200104081 B ZA200104081 B ZA 200104081B
- Authority
- ZA
- South Africa
- Prior art keywords
- crystal
- type
- powder
- thiazolidinedione
- ray diffraction
- Prior art date
Links
- 239000013078 crystal Substances 0.000 claims description 182
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 28
- 238000010438 heat treatment Methods 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 13
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 201000001431 Hyperuricemia Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 25
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 16
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- 150000001875 compounds Chemical class 0.000 description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 229940125396 insulin Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010022489 Insulin Resistance Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic alcohols Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
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- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 150000002790 naphthalenes Chemical class 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D277/34—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33054698 | 1998-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104081B true ZA200104081B (en) | 2002-05-20 |
Family
ID=18233859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104081A ZA200104081B (en) | 1998-11-20 | 2001-05-18 | Chrystals of 5-[{6-(2-flourobenzyl)oxy-2-napthyl}methyl]-2,4-thiazolidinedione. |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6541493B1 (xx) |
| EP (1) | EP1131310B1 (xx) |
| JP (1) | JP3784001B2 (xx) |
| KR (1) | KR100652326B1 (xx) |
| CN (1) | CN1326449A (xx) |
| AT (1) | ATE315552T1 (xx) |
| AU (1) | AU1185100A (xx) |
| BR (1) | BR9916795A (xx) |
| CA (1) | CA2351727C (xx) |
| CZ (1) | CZ20011763A3 (xx) |
| DE (1) | DE69929476T2 (xx) |
| ES (1) | ES2257104T3 (xx) |
| HU (1) | HUP0104139A3 (xx) |
| ID (1) | ID30064A (xx) |
| IL (1) | IL143177A0 (xx) |
| NO (1) | NO20012444L (xx) |
| NZ (1) | NZ512429A (xx) |
| PL (1) | PL348502A1 (xx) |
| PT (1) | PT1131310E (xx) |
| TR (4) | TR200202109T2 (xx) |
| TW (2) | TWI250156B (xx) |
| WO (1) | WO2000031055A1 (xx) |
| ZA (1) | ZA200104081B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3784001B2 (ja) * | 1998-11-20 | 2006-06-07 | 三菱化学株式会社 | ５−［｛６−（２−フルオロベンジル）オキシ−２−ナフチル｝メチル］−２，４−チアゾリジンジオンの結晶体 |
| BR0015702A (pt) * | 1999-11-19 | 2002-07-16 | Johnson & Johnson | Formas de estado sólido de 5-[[6-[(2-fluorofenil)metoxi]-2naftalenil] metil] 2,4-tiazolidinediona |
| JP4590159B2 (ja) * | 2001-04-04 | 2010-12-01 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | グルコース再吸収阻害剤およびｐｐａｒモジュレーターを含んで成る併用療法 |
| WO2007049050A2 (en) * | 2005-10-27 | 2007-05-03 | Heptahelix Ab | Modulators of gpr40 for the treatment of diabetes |
| PT2303267E (pt) * | 2008-02-04 | 2013-08-05 | Pfizer Ltd | Forma polimórfica de um derivado de [1, 2, 4]triazol[4, 3-a]piridina para tratar doenças inflamatórias |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5594016A (en) * | 1992-12-28 | 1997-01-14 | Mitsubishi Chemical Corporation | Naphthalene derivatives |
| JP2845743B2 (ja) * | 1992-12-28 | 1999-01-13 | 三菱化学株式会社 | 新規なナフタレン誘導体 |
| JP4023697B2 (ja) | 1996-11-14 | 2007-12-19 | 三菱化学株式会社 | ナフタレン誘導体の製造方法 |
| JP3784001B2 (ja) * | 1998-11-20 | 2006-06-07 | 三菱化学株式会社 | ５−［｛６−（２−フルオロベンジル）オキシ−２−ナフチル｝メチル］−２，４−チアゾリジンジオンの結晶体 |
-
1999
- 1999-11-19 JP JP2000583883A patent/JP3784001B2/ja not_active Expired - Fee Related
- 1999-11-19 TR TR2002/02109T patent/TR200202109T2/xx unknown
- 1999-11-19 ES ES99972628T patent/ES2257104T3/es not_active Expired - Lifetime
- 1999-11-19 AT AT99972628T patent/ATE315552T1/de not_active IP Right Cessation
- 1999-11-19 IL IL14317799A patent/IL143177A0/xx unknown
- 1999-11-19 PT PT99972628T patent/PT1131310E/pt unknown
- 1999-11-19 TR TR2001/01901T patent/TR200101901T2/xx unknown
- 1999-11-19 CZ CZ20011763A patent/CZ20011763A3/cs unknown
- 1999-11-19 DE DE69929476T patent/DE69929476T2/de not_active Expired - Fee Related
- 1999-11-19 TR TR2002/02103T patent/TR200202103T2/xx unknown
- 1999-11-19 HU HU0104139A patent/HUP0104139A3/hu unknown
- 1999-11-19 BR BR9916795-6A patent/BR9916795A/pt not_active IP Right Cessation
- 1999-11-19 EP EP99972628A patent/EP1131310B1/en not_active Expired - Lifetime
- 1999-11-19 CN CN99813380A patent/CN1326449A/zh active Pending
- 1999-11-19 AU AU11851/00A patent/AU1185100A/en not_active Abandoned
- 1999-11-19 ID IDW00200101331A patent/ID30064A/id unknown
- 1999-11-19 WO PCT/JP1999/006492 patent/WO2000031055A1/en active IP Right Grant
- 1999-11-19 PL PL99348502A patent/PL348502A1/xx unknown
- 1999-11-19 US US09/856,295 patent/US6541493B1/en not_active Expired - Fee Related
- 1999-11-19 NZ NZ512429A patent/NZ512429A/en unknown
- 1999-11-19 TR TR2002/02110T patent/TR200202110T2/xx unknown
- 1999-11-19 KR KR1020017006299A patent/KR100652326B1/ko not_active IP Right Cessation
- 1999-11-19 CA CA002351727A patent/CA2351727C/en not_active Expired - Fee Related
- 1999-11-20 TW TW088120305A patent/TWI250156B/zh not_active IP Right Cessation
- 1999-11-20 TW TW094136910A patent/TWI272944B/zh not_active IP Right Cessation
-
2001
- 2001-05-18 ZA ZA200104081A patent/ZA200104081B/en unknown
- 2001-05-18 NO NO20012444A patent/NO20012444L/no not_active Application Discontinuation
-
2003
- 2003-01-31 US US10/355,160 patent/US20030158241A1/en not_active Abandoned
-
2006
- 2006-02-21 US US11/357,208 patent/US20060149075A1/en not_active Abandoned
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