ZA200203906B - Thiazolidinedione derivatives as antidiabetic agents. - Google Patents
Thiazolidinedione derivatives as antidiabetic agents. Download PDFInfo
- Publication number
- ZA200203906B ZA200203906B ZA200203906A ZA200203906A ZA200203906B ZA 200203906 B ZA200203906 B ZA 200203906B ZA 200203906 A ZA200203906 A ZA 200203906A ZA 200203906 A ZA200203906 A ZA 200203906A ZA 200203906 B ZA200203906 B ZA 200203906B
- Authority
- ZA
- South Africa
- Prior art keywords
- dione
- benzyl
- ethoxy
- compound
- thiazolidine
- Prior art date
Links
- 239000003472 antidiabetic agent Substances 0.000 title claims description 10
- 229940125708 antidiabetic agent Drugs 0.000 title claims description 7
- 150000001467 thiazolidinediones Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 2-Amino-6-chloropyrimidin-4-yl Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 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 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 102000004877 Insulin Human genes 0.000 claims description 5
- 108090001061 Insulin Proteins 0.000 claims description 5
- 229940125396 insulin Drugs 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 4
- 201000001421 hyperglycemia Diseases 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 201000001431 Hyperuricemia Diseases 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 230000002124 endocrine Effects 0.000 claims description 3
- 230000002503 metabolic effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- XXCBHCLZBCPZEG-UHFFFAOYSA-N 5-[[4-[2-[methyl-(4-oxo-1h-pyrimidin-6-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(O)=NC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O XXCBHCLZBCPZEG-UHFFFAOYSA-N 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 108090000362 Lymphotoxin-beta Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 102100033744 Troponin C, slow skeletal and cardiac muscles Human genes 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 206010012601 diabetes mellitus Diseases 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical class O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940123464 Thiazolidinedione Drugs 0.000 description 3
- 150000004283 biguanides Chemical class 0.000 description 3
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 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
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229950009226 ciglitazone Drugs 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 229950002375 englitazone Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- XHRJGHCQQPETRH-KQYNXXCUSA-N (2r,3r,4s,5r)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(Cl)=C2N=C1 XHRJGHCQQPETRH-KQYNXXCUSA-N 0.000 description 1
- SEZHLKZEWYFCRB-UHFFFAOYSA-N 1,2-dimethoxyethane;oxolane Chemical compound C1CCOC1.COCCOC SEZHLKZEWYFCRB-UHFFFAOYSA-N 0.000 description 1
- OYGISCNHSNIDFV-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfanyl-3-phenylpyridine Chemical compound ClC1=NC(SC)=CC(Cl)=C1C1=CC=CC=C1 OYGISCNHSNIDFV-UHFFFAOYSA-N 0.000 description 1
- SYZDNTMHIDTVBR-UHFFFAOYSA-N 4,6-dichloro-2,5-diphenylpyrimidine Chemical compound ClC1=NC(C=2C=CC=CC=2)=NC(Cl)=C1C1=CC=CC=C1 SYZDNTMHIDTVBR-UHFFFAOYSA-N 0.000 description 1
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 description 1
- JHNRTJRDRWKAIW-UHFFFAOYSA-N 4-chloro-2,6-dimethoxypyrimidine Chemical compound COC1=CC(Cl)=NC(OC)=N1 JHNRTJRDRWKAIW-UHFFFAOYSA-N 0.000 description 1
- DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 description 1
- NLHCHJVQLIKXJW-UHFFFAOYSA-N 5-[[4-[2-[(2,6-dimethoxypyrimidin-4-yl)-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=NC(OC)=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 NLHCHJVQLIKXJW-UHFFFAOYSA-N 0.000 description 1
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 1
- BNCVMSCKRXXWOD-UHFFFAOYSA-N C1=CC(=CC=C1CC2C(=O)NC(=O)S2)OCCNCC3=C(C(=NC=N3)Cl)[N+](=O)[O-] Chemical compound C1=CC(=CC=C1CC2C(=O)NC(=O)S2)OCCNCC3=C(C(=NC=N3)Cl)[N+](=O)[O-] BNCVMSCKRXXWOD-UHFFFAOYSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 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 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000002431 aminoalkoxy group Chemical group 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000002058 anti-hyperglycaemic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P3/08—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902533A ES2156574B1 (es) | 1999-11-18 | 1999-11-18 | Nuevos derivados de tiazolidindiona como agentes antidiabeticos |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200203906B true ZA200203906B (en) | 2004-03-26 |
Family
ID=8310628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200203906A ZA200203906B (en) | 1999-11-18 | 2002-05-16 | Thiazolidinedione derivatives as antidiabetic agents. |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US7001910B1 (zh) |
| EP (1) | EP1231211B1 (zh) |
| JP (1) | JP2003514817A (zh) |
| KR (1) | KR100518110B1 (zh) |
| CN (1) | CN1159314C (zh) |
| AP (1) | AP1330A (zh) |
| AR (1) | AR031080A1 (zh) |
| AT (1) | ATE241622T1 (zh) |
| AU (1) | AU770045B2 (zh) |
| BG (1) | BG106699A (zh) |
| BR (1) | BR0015613A (zh) |
| CA (1) | CA2391913A1 (zh) |
| CO (1) | CO5261560A1 (zh) |
| CR (1) | CR6640A (zh) |
| CZ (1) | CZ20021654A3 (zh) |
| DE (1) | DE60003072T2 (zh) |
| DK (1) | DK1231211T3 (zh) |
| EA (1) | EA004301B1 (zh) |
| EE (1) | EE200200254A (zh) |
| ES (2) | ES2156574B1 (zh) |
| GE (1) | GEP20043240B (zh) |
| HR (1) | HRP20020426A2 (zh) |
| HU (1) | HUP0203478A2 (zh) |
| IL (1) | IL149634A0 (zh) |
| IS (1) | IS2014B (zh) |
| MA (1) | MA26844A1 (zh) |
| MX (1) | MXPA02005011A (zh) |
| NO (2) | NO20022336L (zh) |
| NZ (1) | NZ519264A (zh) |
| OA (1) | OA12089A (zh) |
| PE (1) | PE20010858A1 (zh) |
| PL (1) | PL354877A1 (zh) |
| PT (1) | PT1231211E (zh) |
| SK (1) | SK6752002A3 (zh) |
| WO (1) | WO2001036416A1 (zh) |
| YU (1) | YU40202A (zh) |
| ZA (1) | ZA200203906B (zh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2174748B1 (es) * | 2001-01-31 | 2003-09-16 | Vita Lab | Nueva sal de tiazolidindiona y sus polimorfos como agentes antidiabeticos y procedimiento para la obtencion de los mismos. |
| KR100450700B1 (ko) * | 2002-03-22 | 2004-10-01 | 주식회사종근당 | 티아졸리딘디온 유도체 화합물 및 이를 함유하는 약제학적조성물 |
| US7713983B2 (en) | 2003-03-03 | 2010-05-11 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| US20050014732A1 (en) * | 2003-03-14 | 2005-01-20 | Pharmacia Corporation | Combination of an aldosterone receptor antagonist and an anti-diabetic agent |
| US7928107B2 (en) | 2004-09-02 | 2011-04-19 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| US8283354B2 (en) | 2004-09-02 | 2012-10-09 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| CZ297347B6 (cs) * | 2004-09-21 | 2006-11-15 | Zentiva, A. S. | Zpusob prípravy rosiglitazonu |
| JP5546372B2 (ja) * | 2010-06-30 | 2014-07-09 | 積水メディカル株式会社 | ベンジルヒダントイン化合物の製造法 |
| WO2016184895A1 (en) | 2015-05-18 | 2016-11-24 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Means for detecting or measuring a biological activity of a botulinum toxin |
| US10689374B1 (en) | 2019-07-12 | 2020-06-23 | United Arab Emirates University | Pyrimidine-thiazolidinone derivatives |
| US10702525B1 (en) | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| EP0842925A1 (en) * | 1987-09-04 | 1998-05-20 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
| GB9023583D0 (en) * | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
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1999
- 1999-11-18 ES ES009902533A patent/ES2156574B1/es not_active Expired - Fee Related
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2000
- 2000-11-06 AR ARP000105830A patent/AR031080A1/es unknown
- 2000-11-07 PE PE2000001189A patent/PE20010858A1/es not_active Application Discontinuation
- 2000-11-14 CO CO00086452A patent/CO5261560A1/es not_active Application Discontinuation
- 2000-11-15 AP APAP/P/2002/002512A patent/AP1330A/en active
- 2000-11-15 BR BR0015613-2A patent/BR0015613A/pt not_active IP Right Cessation
- 2000-11-15 IL IL14963400A patent/IL149634A0/xx unknown
- 2000-11-15 PT PT00974559T patent/PT1231211E/pt unknown
- 2000-11-15 SK SK675-2002A patent/SK6752002A3/sk unknown
- 2000-11-15 EP EP00974559A patent/EP1231211B1/en not_active Expired - Lifetime
- 2000-11-15 AT AT00974559T patent/ATE241622T1/de not_active IP Right Cessation
- 2000-11-15 ES ES00974559T patent/ES2199878T3/es not_active Expired - Lifetime
- 2000-11-15 CN CNB008166412A patent/CN1159314C/zh not_active Expired - Fee Related
- 2000-11-15 DK DK00974559T patent/DK1231211T3/da active
- 2000-11-15 YU YU40202A patent/YU40202A/sh unknown
- 2000-11-15 PL PL00354877A patent/PL354877A1/xx not_active IP Right Cessation
- 2000-11-15 HU HU0203478A patent/HUP0203478A2/hu unknown
- 2000-11-15 JP JP2001538905A patent/JP2003514817A/ja active Pending
- 2000-11-15 MX MXPA02005011A patent/MXPA02005011A/es active IP Right Grant
- 2000-11-15 AU AU12815/01A patent/AU770045B2/en not_active Ceased
- 2000-11-15 US US10/130,576 patent/US7001910B1/en not_active Expired - Fee Related
- 2000-11-15 EA EA200200470A patent/EA004301B1/ru not_active IP Right Cessation
- 2000-11-15 CA CA002391913A patent/CA2391913A1/en not_active Abandoned
- 2000-11-15 EE EEP200200254A patent/EE200200254A/xx unknown
- 2000-11-15 OA OA1200200148A patent/OA12089A/en unknown
- 2000-11-15 KR KR10-2002-7006298A patent/KR100518110B1/ko not_active IP Right Cessation
- 2000-11-15 NZ NZ519264A patent/NZ519264A/en unknown
- 2000-11-15 CZ CZ20021654A patent/CZ20021654A3/cs unknown
- 2000-11-15 GE GEAP20006452A patent/GEP20043240B/en unknown
- 2000-11-15 DE DE60003072T patent/DE60003072T2/de not_active Expired - Fee Related
- 2000-11-15 WO PCT/ES2000/000432 patent/WO2001036416A1/es not_active Application Discontinuation
-
2002
- 2002-05-14 BG BG106699A patent/BG106699A/bg unknown
- 2002-05-15 IS IS6386A patent/IS2014B/is unknown
- 2002-05-15 CR CR6640A patent/CR6640A/es not_active Application Discontinuation
- 2002-05-15 HR HR20020426A patent/HRP20020426A2/hr not_active Application Discontinuation
- 2002-05-15 NO NO20022336A patent/NO20022336L/no not_active Application Discontinuation
- 2002-05-15 MA MA26638A patent/MA26844A1/fr unknown
- 2002-05-16 NO NO20022379A patent/NO20022379D0/no unknown
- 2002-05-16 ZA ZA200203906A patent/ZA200203906B/en unknown
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