SK9172001A3 - A combination of fbpase inhibitors and insulin sensitizers for the treatment of diabetes - Google Patents
A combination of fbpase inhibitors and insulin sensitizers for the treatment of diabetes Download PDFInfo
- Publication number
- SK9172001A3 SK9172001A3 SK917-2001A SK9172001A SK9172001A3 SK 9172001 A3 SK9172001 A3 SK 9172001A3 SK 9172001 A SK9172001 A SK 9172001A SK 9172001 A3 SK9172001 A3 SK 9172001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- hydrogen
- aryl
- alicyclic
- Prior art date
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- 229940122355 Insulin sensitizer Drugs 0.000 title claims abstract description 57
- 239000003112 inhibitor Substances 0.000 title claims abstract description 52
- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 45
- 238000011282 treatment Methods 0.000 title description 40
- 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 abstract description 166
- 102000004877 Insulin Human genes 0.000 claims abstract description 80
- 108090001061 Insulin Proteins 0.000 claims abstract description 80
- 229940125396 insulin Drugs 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 57
- 101710099475 3'-phosphoadenosine 5'-phosphate phosphatase Proteins 0.000 claims abstract description 51
- 101710196411 Fructose-1,6-bisphosphatase Proteins 0.000 claims abstract description 51
- 101710186733 Fructose-1,6-bisphosphatase, chloroplastic Proteins 0.000 claims abstract description 51
- 101710109119 Fructose-1,6-bisphosphatase, cytosolic Proteins 0.000 claims abstract description 51
- 101710198902 Fructose-1,6-bisphosphate aldolase/phosphatase Proteins 0.000 claims abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 407
- 229910052739 hydrogen Inorganic materials 0.000 claims description 398
- 239000001257 hydrogen Substances 0.000 claims description 384
- 125000003118 aryl group Chemical group 0.000 claims description 315
- 150000001875 compounds Chemical class 0.000 claims description 268
- -1 Gl-262570 Chemical compound 0.000 claims description 243
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 240
- 125000002723 alicyclic group Chemical group 0.000 claims description 198
- 125000004122 cyclic group Chemical group 0.000 claims description 162
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 161
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 149
- 125000004429 atom Chemical group 0.000 claims description 118
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- 229910052736 halogen Inorganic materials 0.000 claims description 118
- 150000002367 halogens Chemical class 0.000 claims description 111
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 106
- 125000001072 heteroaryl group Chemical group 0.000 claims description 99
- 229910052721 tungsten Inorganic materials 0.000 claims description 86
- 150000002148 esters Chemical group 0.000 claims description 85
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 78
- 125000005842 heteroatom Chemical group 0.000 claims description 76
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 229940002612 prodrug Drugs 0.000 claims description 66
- 239000000651 prodrug Substances 0.000 claims description 66
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 229910052698 phosphorus Inorganic materials 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 55
- 125000003107 substituted aryl group Chemical group 0.000 claims description 54
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 231100000489 sensitizer Toxicity 0.000 claims description 39
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052720 vanadium Inorganic materials 0.000 claims description 31
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 28
- 125000004423 acyloxy group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004437 phosphorous atom Chemical group 0.000 claims description 28
- 239000011574 phosphorus Substances 0.000 claims description 28
- 150000001721 carbon Chemical group 0.000 claims description 27
- 239000003446 ligand Substances 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 23
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 108010016731 PPAR gamma Proteins 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 102000000536 PPAR gamma Human genes 0.000 claims description 17
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 17
- 239000011593 sulfur Chemical group 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 14
- 125000006366 methylene oxy carbonyl group Chemical group [H]C([H])([*:1])OC([*:2])=O 0.000 claims description 14
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 239000000556 agonist Substances 0.000 claims description 12
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 238000001727 in vivo Methods 0.000 claims description 11
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 11
- 150000003462 sulfoxides Chemical class 0.000 claims description 11
- 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 claims description 11
- 229960001641 troglitazone Drugs 0.000 claims description 11
- 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 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 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 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 8
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
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- 210000003494 hepatocyte Anatomy 0.000 claims description 8
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 229960005095 pioglitazone Drugs 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 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 claims description 6
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P3/04—Anorexiants; Antiobesity 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11471898P | 1998-12-24 | 1998-12-24 | |
| PCT/US1999/030713 WO2000038666A2 (en) | 1998-12-24 | 1999-12-22 | A COMBINATION OF FBPase INHIBITORS AND INSULIN SENSITIZERS FOR THE TREATMENT OF DIABETES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK9172001A3 true SK9172001A3 (en) | 2002-04-04 |
Family
ID=22357016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK917-2001A SK9172001A3 (en) | 1998-12-24 | 1999-12-22 | A combination of fbpase inhibitors and insulin sensitizers for the treatment of diabetes |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1143955B1 (enExample) |
| JP (1) | JP2003515523A (enExample) |
| KR (3) | KR100689943B1 (enExample) |
| CN (3) | CN101164618A (enExample) |
| AT (1) | ATE300288T1 (enExample) |
| AU (1) | AU771039B2 (enExample) |
| BR (1) | BR9917005A (enExample) |
| CA (1) | CA2354053A1 (enExample) |
| CZ (1) | CZ20012353A3 (enExample) |
| DE (1) | DE69926400T2 (enExample) |
| DK (1) | DK1143955T3 (enExample) |
| ES (1) | ES2246586T3 (enExample) |
| HK (1) | HK1046863B (enExample) |
| HU (1) | HUP0402506A3 (enExample) |
| ID (1) | ID30237A (enExample) |
| IL (2) | IL143569A0 (enExample) |
| MX (1) | MXPA01006511A (enExample) |
| NO (1) | NO20013115L (enExample) |
| NZ (1) | NZ512219A (enExample) |
| PL (1) | PL352756A1 (enExample) |
| PT (1) | PT1143955E (enExample) |
| RU (2) | RU2227749C2 (enExample) |
| SK (1) | SK9172001A3 (enExample) |
| WO (1) | WO2000038666A2 (enExample) |
| ZA (1) | ZA200105016B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6452098A (en) | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| DE69910045T2 (de) | 1998-09-09 | 2004-04-22 | Metabasis Therapeutics Inc., San Diego | Neue heteroaromatische fructose 1,6-bisphosphatase inhibitoren |
| AU784370B2 (en) | 1999-12-22 | 2006-03-23 | Metabasis Therapeutics, Inc. | Novel bisamidate phosphonate prodrugs |
| MXPA02008722A (es) | 2000-03-08 | 2004-05-05 | Metabasis Therapeutics Inc | Inhibidores novedosos de aril fructosa-1,6-bisfosfatasa. |
| US7563774B2 (en) | 2000-06-29 | 2009-07-21 | Metabasis Therapeutics, Inc. | Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes |
| HUP0301830A3 (en) * | 2000-07-06 | 2007-10-29 | Metabasis Therapeutics Inc | Pharmaceutical composition containing a combination of fbpase inhibitors and antidiabetic agents useful for the treatment of diabetes |
| CA2429426A1 (en) | 2000-11-17 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Isoxazole derivatives |
| JP4476811B2 (ja) | 2002-05-13 | 2010-06-09 | メタバシス・セラピューティクス・インコーポレイテッド | Ｐｍｅａおよびそのアナログの新規ホスホン酸系プロドラッグ |
| JP4332496B2 (ja) | 2002-05-13 | 2009-09-16 | メタバシス・セラピューティクス・インコーポレイテッド | Ｐｍｅａおよびｐｍｐａ環生成合成 |
| AU2003264256A1 (en) * | 2002-09-04 | 2004-03-29 | Dsm Ip Assets B.V. | A nutritional and therapeutic composition of an insulin sensitizer and a peptide fraction |
| UA80991C2 (en) | 2002-10-07 | 2007-11-26 | Solid preparation containing an insulin resistance improving drug and an active ingredient useful as a remedy for diabetes | |
| MXPA05008335A (es) * | 2003-02-11 | 2006-05-04 | Vernalis Cambridge Ltd | Compuestos de isoxazol como inhibidores de las proteinas de choque por calor. |
| CA2551611C (en) * | 2003-12-26 | 2013-06-25 | Kyowa Hakko Kogyo Co., Ltd. | Thiazole derivatives for treating or preventing parkinson's disease |
| KR20070053764A (ko) * | 2004-08-18 | 2007-05-25 | 메타베이시스 테라퓨틱스, 인크. | 프럭토스 1,6-비스포스파타제의 신규한 티아졸 억제제들 |
| TW200633720A (en) * | 2004-12-13 | 2006-10-01 | Sankyo Co | Medicinal composition for diabetic |
| TW200633702A (en) * | 2004-12-15 | 2006-10-01 | Sankyo Co | Medicinal composition containing fbpase inhibitor |
| US20090227493A1 (en) * | 2005-05-27 | 2009-09-10 | Daiichi Sankyo Company, Limited | Combined drug for treating diabetes |
| EP1894930A4 (en) | 2005-06-23 | 2010-06-23 | Kyowa Hakko Kirin Co Ltd | THIAZOLE DERIVATIVE |
| EP2089017A2 (en) | 2006-11-02 | 2009-08-19 | Aestus Therapeutics, Inc. | Methods of treating neuropathic pain by modulation of glycogenolysis or glycolysis pathways |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| US9631825B2 (en) | 2012-12-18 | 2017-04-25 | Nortek Air Solutions, Llc | Air filter assembly |
| WO2015123352A1 (en) | 2014-02-13 | 2015-08-20 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| WO2016003812A1 (en) | 2014-07-02 | 2016-01-07 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and uses therof |
| CN105481896A (zh) * | 2015-12-03 | 2016-04-13 | 浙江大学 | 一种地马格列的制备方法 |
| CN113416739B (zh) * | 2021-06-24 | 2022-04-19 | 黑龙江八一农垦大学 | 鲁氏酵母菌基因在提高微生物产hdmf的产量中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968790A (en) * | 1988-08-12 | 1990-11-06 | American Cyanamid Company | Antidiabetic phosphates |
| JPH03157377A (ja) * | 1988-11-18 | 1991-07-05 | Takeda Chem Ind Ltd | チオ尿素誘導体及びａｇｅ生成阻害剤 |
| DE69014562T2 (de) * | 1989-01-24 | 1995-06-22 | Gensia Pharma | Verfahren und verbindungen zur verabreichung von aica ribosiden und zur erniedrigung des blutglucose gehaltes. |
| TWI238064B (en) * | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| US5859037A (en) * | 1997-02-19 | 1999-01-12 | Warner-Lambert Company | Sulfonylurea-glitazone combinations for diabetes |
| WO1998039342A1 (en) * | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| AU6452098A (en) * | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| ZA981936B (en) * | 1997-03-07 | 1999-09-06 | Metabasis Therapeutics Inc | Novel benzimidazole inhibitors of fructose 1,6-bisphosphatase. |
-
1999
- 1999-12-22 AT AT99964313T patent/ATE300288T1/de active
- 1999-12-22 ID IDW00200101612A patent/ID30237A/id unknown
- 1999-12-22 AU AU20583/00A patent/AU771039B2/en not_active Ceased
- 1999-12-22 ES ES99964313T patent/ES2246586T3/es not_active Expired - Lifetime
- 1999-12-22 DK DK99964313T patent/DK1143955T3/da active
- 1999-12-22 RU RU2001120726/15A patent/RU2227749C2/ru not_active IP Right Cessation
- 1999-12-22 CN CNA2007101628889A patent/CN101164618A/zh active Pending
- 1999-12-22 CN CNA2005100806150A patent/CN1714866A/zh active Pending
- 1999-12-22 HK HK02108475.5A patent/HK1046863B/zh not_active IP Right Cessation
- 1999-12-22 EP EP99964313A patent/EP1143955B1/en not_active Expired - Lifetime
- 1999-12-22 BR BR9917005-1A patent/BR9917005A/pt not_active Application Discontinuation
- 1999-12-22 HU HU0402506A patent/HUP0402506A3/hu active IP Right Revival
- 1999-12-22 IL IL14356999A patent/IL143569A0/xx active IP Right Grant
- 1999-12-22 SK SK917-2001A patent/SK9172001A3/sk unknown
- 1999-12-22 CA CA002354053A patent/CA2354053A1/en not_active Abandoned
- 1999-12-22 PT PT99964313T patent/PT1143955E/pt unknown
- 1999-12-22 KR KR1020017008102A patent/KR100689943B1/ko not_active Expired - Fee Related
- 1999-12-22 MX MXPA01006511A patent/MXPA01006511A/es active IP Right Grant
- 1999-12-22 PL PL99352756A patent/PL352756A1/xx not_active Application Discontinuation
- 1999-12-22 JP JP2000590620A patent/JP2003515523A/ja active Pending
- 1999-12-22 WO PCT/US1999/030713 patent/WO2000038666A2/en not_active Ceased
- 1999-12-22 NZ NZ512219A patent/NZ512219A/xx not_active IP Right Cessation
- 1999-12-22 CN CNB998163562A patent/CN100352505C/zh not_active Expired - Fee Related
- 1999-12-22 CZ CZ20012353A patent/CZ20012353A3/cs unknown
- 1999-12-22 DE DE69926400T patent/DE69926400T2/de not_active Expired - Lifetime
- 1999-12-22 KR KR1020067022095A patent/KR20060114724A/ko not_active Ceased
- 1999-12-22 KR KR1020077008649A patent/KR20070046210A/ko not_active Ceased
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2001
- 2001-06-05 IL IL143569A patent/IL143569A/en not_active IP Right Cessation
- 2001-06-19 ZA ZA200105016A patent/ZA200105016B/en unknown
- 2001-06-21 NO NO20013115A patent/NO20013115L/no not_active Application Discontinuation
-
2003
- 2003-10-31 RU RU2003132054/14A patent/RU2003132054A/ru not_active Application Discontinuation
Also Published As
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| SK9172001A3 (en) | A combination of fbpase inhibitors and insulin sensitizers for the treatment of diabetes | |
| US20080004226A1 (en) | Combination of FBPase Inhibitors and Insulin Sensitizers for the Treatment of Diabetes | |
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