SK9552003A3 - New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them - Google Patents

New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them Download PDF

Info

Publication number: SK9552003A3
Authority: SK; Slovakia
Prior art keywords: compound; solution; polymorph; solvent; preparing
Prior art date: 2001-01-31

Application number

SK955-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Castillo Nieto Juan Carlos Del

Olondriz Francisco Marquillas

Ramon Amat Elisabet De

Original Assignee

Vita Lab

Priority date (The priority date 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 date listed.)

2001-01-31

Filing date

2002-01-21

Publication date

2004-05-04

2002-01-21 Application filed by Vita Lab filed Critical Vita Lab

2004-05-04 Publication of SK9552003A3 publication Critical patent/SK9552003A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 12
239000003472 antidiabetic agent Substances 0.000 title claims description 4
229940125708 antidiabetic agent Drugs 0.000 title claims description 4
150000003839 salts Chemical class 0.000 title abstract description 8
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 title description 9
229940123464 Thiazolidinedione Drugs 0.000 title description 3
238000011282 treatment Methods 0.000 claims abstract description 9
-1 6-methoxy-pyrimidin-4-yl Chemical group 0.000 claims abstract description 8
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 6
238000011321 prophylaxis Methods 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
239000000243 solution Substances 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
159000000000 sodium salts Chemical class 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
235000019441 ethanol Nutrition 0.000 claims description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 7
238000001816 cooling Methods 0.000 claims description 6
238000001704 evaporation Methods 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 5
238000002441 X-ray diffraction Methods 0.000 claims description 5
230000008020 evaporation Effects 0.000 claims description 5
201000001421 hyperglycemia Diseases 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000012047 saturated solution Substances 0.000 claims description 5
NVIVKAGMJLHDTR-UHFFFAOYSA-N 5-[[4-[2-[(6-methoxypyrimidin-4-yl)-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=NC(OC)=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 NVIVKAGMJLHDTR-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
239000003791 organic solvent mixture Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
229910001415 sodium ion Inorganic materials 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 3
201000001431 Hyperuricemia Diseases 0.000 claims description 3
206010022489 Insulin Resistance Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
230000002526 effect on cardiovascular system Effects 0.000 claims description 3
230000002124 endocrine Effects 0.000 claims description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 2
102000004877 Insulin Human genes 0.000 claims description 2
108090001061 Insulin Proteins 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
229940100389 Sulfonylurea Drugs 0.000 claims description 2
239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 2
229940125388 beta agonist Drugs 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
229940125396 insulin Drugs 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
229940122355 Insulin sensitizer Drugs 0.000 claims 1
239000003524 antilipemic agent Substances 0.000 claims 1
235000014121 butter Nutrition 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 2
230000004075 alteration Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 24
238000002083 X-ray spectrum Methods 0.000 description 14
WOKWRTYYPDBXRY-UHFFFAOYSA-N sodium;1,3-thiazolidine-2,4-dione Chemical compound [Na].O=C1CSC(=O)N1 WOKWRTYYPDBXRY-UHFFFAOYSA-N 0.000 description 12
238000002329 infrared spectrum Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002585 base Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000001467 thiazolidinediones Chemical class 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
230000005855 radiation Effects 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002218 hypoglycaemic effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VVNGXLBYKHTCHK-UHFFFAOYSA-N COC1=CC(=NC=N1)N(CCOC1=CC=C(CC2CNCS2)C=C1)C Chemical compound COC1=CC(=NC=N1)N(CCOC1=CC=C(CC2CNCS2)C=C1)C VVNGXLBYKHTCHK-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CFVSUEWXOBAYKD-UHFFFAOYSA-N [Na].C1=NC(OC)=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 Chemical compound [Na].C1=NC(OC)=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 CFVSUEWXOBAYKD-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002891 organic anions Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SK955-2003A 2001-01-31 2002-01-21 New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them SK9552003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES200100273A ES2174748B1 (es)	2001-01-31	2001-01-31	Nueva sal de tiazolidindiona y sus polimorfos como agentes antidiabeticos y procedimiento para la obtencion de los mismos.
PCT/IB2002/000229 WO2002060899A1 (en)	2001-01-31	2002-01-21	New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them

Publications (1)

Publication Number	Publication Date
SK9552003A3 true SK9552003A3 (en)	2004-05-04

Family

ID=8496644

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK955-2003A SK9552003A3 (en)	2001-01-31	2002-01-21	New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them

Country Status (27)

Country	Link
US (1)	US20040106632A1 (cs)
EP (1)	EP1355908A1 (cs)
JP (1)	JP2004529870A (cs)
KR (1)	KR20030078893A (cs)
CN (1)	CN1694881A (cs)
AP (1)	AP1281A (cs)
AR (1)	AR042584A1 (cs)
BG (1)	BG108047A (cs)
BR (1)	BR0206850A (cs)
CA (1)	CA2436556A1 (cs)
CZ (1)	CZ20032015A3 (cs)
EA (1)	EA200300842A1 (cs)
EE (1)	EE200300356A (cs)
ES (1)	ES2174748B1 (cs)
HU (1)	HUP0302871A2 (cs)
IL (1)	IL157028A0 (cs)
IS (1)	IS6896A (cs)
MA (1)	MA26988A1 (cs)
MX (1)	MXPA03006722A (cs)
NO (1)	NO20033375L (cs)
NZ (1)	NZ527677A (cs)
PE (1)	PE20020969A1 (cs)
PL (1)	PL362527A1 (cs)
SK (1)	SK9552003A3 (cs)
WO (1)	WO2002060899A1 (cs)
YU (1)	YU60303A (cs)
ZA (1)	ZA200305873B (cs)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE186724T1 (de) *	1987-09-04	1999-12-15	Beecham Group Plc	Substituierte thiazolidindionderivate
CN1183130C (zh) *	1999-09-24	2005-01-05	中国人民解放军军事医学科学院毒物药物研究所	噻唑烷类衍生物及其医药用途
ES2156574B1 (es) *	1999-11-18	2002-02-01	Vita Invest Sa	Nuevos derivados de tiazolidindiona como agentes antidiabeticos

2001
- 2001-01-31 ES ES200100273A patent/ES2174748B1/es not_active Expired - Fee Related
2002
- 2002-01-21 US US10/470,980 patent/US20040106632A1/en not_active Abandoned
- 2002-01-21 IL IL15702802A patent/IL157028A0/xx unknown
- 2002-01-21 WO PCT/IB2002/000229 patent/WO2002060899A1/en not_active Ceased
- 2002-01-21 ZA ZA200305873A patent/ZA200305873B/en unknown
- 2002-01-21 SK SK955-2003A patent/SK9552003A3/sk not_active Application Discontinuation
- 2002-01-21 BR BR0206850-8A patent/BR0206850A/pt not_active IP Right Cessation
- 2002-01-21 PL PL02362527A patent/PL362527A1/xx not_active Application Discontinuation
- 2002-01-21 AP APAP/P/2003/002832A patent/AP1281A/en active
- 2002-01-21 HU HU0302871A patent/HUP0302871A2/hu unknown
- 2002-01-21 NZ NZ527677A patent/NZ527677A/en unknown
- 2002-01-21 JP JP2002561467A patent/JP2004529870A/ja active Pending
- 2002-01-21 CZ CZ20032015A patent/CZ20032015A3/cs unknown
- 2002-01-21 CN CNA028043863A patent/CN1694881A/zh active Pending
- 2002-01-21 EE EEP200300356A patent/EE200300356A/xx unknown
- 2002-01-21 EP EP02716216A patent/EP1355908A1/en not_active Withdrawn
- 2002-01-21 MX MXPA03006722A patent/MXPA03006722A/es not_active Application Discontinuation
- 2002-01-21 CA CA002436556A patent/CA2436556A1/en not_active Abandoned
- 2002-01-21 KR KR10-2003-7009880A patent/KR20030078893A/ko not_active Withdrawn
- 2002-01-21 YU YU60303A patent/YU60303A/sh unknown
- 2002-01-21 EA EA200300842A patent/EA200300842A1/ru unknown
- 2002-01-24 PE PE2002000054A patent/PE20020969A1/es not_active Application Discontinuation
- 2002-01-28 AR ARP020100291A patent/AR042584A1/es not_active Application Discontinuation
2003
- 2003-07-28 IS IS6896A patent/IS6896A/is unknown
- 2003-07-28 NO NO20033375A patent/NO20033375L/no not_active Application Discontinuation
- 2003-07-31 MA MA27262A patent/MA26988A1/fr unknown
- 2003-08-01 BG BG108047A patent/BG108047A/bg unknown

Also Published As

Publication number	Publication date
CN1694881A (zh)	2005-11-09
WO2002060899A1 (en)	2002-08-08
ES2174748B1 (es)	2003-09-16
NO20033375D0 (no)	2003-07-28
CZ20032015A3 (cs)	2004-02-18
PL362527A1 (en)	2004-11-02
MA26988A1 (fr)	2004-12-20
IL157028A0 (en)	2004-02-08
EA200300842A1 (ru)	2004-04-29
EP1355908A1 (en)	2003-10-29
US20040106632A1 (en)	2004-06-03
HUP0302871A2 (hu)	2003-12-29
ES2174748A1 (es)	2002-11-01
NZ527677A (en)	2005-01-28
IS6896A (is)	2003-07-28
AP2003002832A0 (en)	2003-09-30
YU60303A (sh)	2006-05-25
CA2436556A1 (en)	2002-08-08
NO20033375L (no)	2003-08-22
AP1281A (en)	2004-05-25
BG108047A (bg)	2004-08-31
AR042584A1 (es)	2005-06-29
MXPA03006722A (es)	2004-10-15
JP2004529870A (ja)	2004-09-30
PE20020969A1 (es)	2002-12-04
KR20030078893A (ko)	2003-10-08
BR0206850A (pt)	2004-01-13
ZA200305873B (en)	2004-07-30
EE200300356A (et)	2003-10-15

Legal Events

Date	Code	Title	Description
2010-08-09	FC9A	Refused patent application

Publication	Publication Date	Title
EP0193256B1 (en)	1989-04-05	Thiazolidinedione derivatives, their production and use
SK13302002A3 (sk)	2003-02-04	V podstate nehydratovaná a nehygroskopická alebo iba mierne hygroskopická hydrochloridová soľ 5-[4-[2-(N-metyl-N-(2- pyridyl)amino) etoxy]benzyl]tiazolidín-2,4-diónu, spôsob jej prípravy, farmaceutický prostriedok s jej obsahom a jej použitie
CA2195559A1 (en)	1996-02-22	Thiazolidinedione derivatives, their production and use
IL280841B1 (en)	2024-08-01	Succinate and fumarate acid addition salts of piperazine derivatives used as glycosidase inhibitors
SK286427B6 (sk)	2008-09-05	Polymorfná forma soli 5-[4-[2-(N-metyl-N-(2- pyridyl)amino)etoxy]benzyl]tiazolidín-2,4-diónu s kyselinou maleínovu, spôsob jej prípravy, farmaceutický prostriedok s jej obsahom a jej použitie
DE69430348T2 (de)	2002-11-21	Oxazolidinedion-Derivate und ihre Anwendung als hypoglykämisches Mittel
SK286422B6 (sk)	2008-09-05	Hydrát 5-[4-[2-(N-metyl-N-(2- pyridyl)amino)etoxy]benzyl]tiazolidín-2,4-dión maleínanu, spôsob jehovýroby, farmaceutický prípravok s jeho obsahom a jeho použitie
WO2009102226A1 (en)	2009-08-20	Malonic acid salt of 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- 2,4-thiazolidinedione
RS60303B1 (sr)	2020-07-31	Postupak za pripremu rastopa silicijumdioksida
SK14932001A3 (sk)	2002-02-05	Polymorfná forma 5-[4-[2-(N-metyl-N-(2-pyridyl)amino)etoxy] benzyl]tiazolidín-2,4-diónu s kyselinou maleínovou, spôsob jej prípravy, farmaceutický prostriedok s jej obsahom a jej použitie
EP1844027A1 (de)	2007-10-17	Thiazolidinone als inhibitoren der polo like kinase (plk) als arzneimittel
DE69625795T2 (de)	2003-08-14	Thiazolidinedionderivate mit antidiabetischen, hypolipidämischen und antihypertensiven Eigenschaften, Verfahren zu deren Herstellung und pharmazeutischen Zusammenstellungen, die sie enthalten
CZ20032015A3 (cs)	2004-02-18	Nová sůl thiazolidindionu a její polymorfy jako antidiabetická činidla a metoda jejich získávání
EP0702015B1 (en)	1997-09-24	Bicyclic oxazole and thiazole substituted ethers
AU2002226609A1 (en)	2002-08-12	New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them
OA12492A (en)	2006-05-24	New salt of thiazolidinedione and its polymorphs as antidiabetic agents and method for obtaining them.
CZ2003849A3 (cs)	2004-03-17	Derivát thiazolidindionu a jeho použití jako antidiabetika
CZ302181B6 (cs)	2010-12-01	Sodná sul 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidin-2,4-dionu a farmaceutický prostredek s jejím obsahem
CZ2004844A3 (cs)	2006-03-15	Sul kyseliny stavelové s 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidin-2,4-dionu azpusob její prípravy a její pouzití