JP2003515523A5 - - Google Patents
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- JP2003515523A5 JP2003515523A5 JP2000590620A JP2000590620A JP2003515523A5 JP 2003515523 A5 JP2003515523 A5 JP 2003515523A5 JP 2000590620 A JP2000590620 A JP 2000590620A JP 2000590620 A JP2000590620 A JP 2000590620A JP 2003515523 A5 JP2003515523 A5 JP 2003515523A5
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- JP
- Japan
- Prior art keywords
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- alkyl
- substituted
- unsubstituted
- aryl
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 description 183
- 125000003118 aryl group Chemical group 0.000 description 119
- 125000004122 cyclic group Chemical group 0.000 description 113
- 125000001931 aliphatic group Chemical group 0.000 description 78
- 150000001875 compounds Chemical class 0.000 description 74
- 125000003710 aryl alkyl group Chemical group 0.000 description 66
- 229910052736 halogen Inorganic materials 0.000 description 66
- 150000002367 halogens Chemical class 0.000 description 65
- 239000008194 pharmaceutical composition Substances 0.000 description 59
- 238000000034 method Methods 0.000 description 54
- 125000004093 cyano group Chemical group *C#N 0.000 description 53
- 229940122355 Insulin sensitizer Drugs 0.000 description 47
- -1 dalglitazone Chemical compound 0.000 description 39
- 125000003342 alkenyl group Chemical group 0.000 description 35
- 125000000304 alkynyl group Chemical group 0.000 description 35
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 24
- 125000004429 atom Chemical group 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 20
- 125000005842 heteroatom Chemical group 0.000 description 19
- 125000006165 cyclic alkyl group Chemical group 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 17
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 16
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 16
- 229940123464 Thiazolidinedione Drugs 0.000 description 16
- 239000003446 ligand Substances 0.000 description 16
- 125000001188 haloalkyl group Chemical group 0.000 description 15
- 125000006366 methylene oxy carbonyl group Chemical group [H]C([H])([*:1])OC([*:2])=O 0.000 description 14
- 239000000651 prodrug Substances 0.000 description 14
- 229940002612 prodrug Drugs 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 101710099475 3'-phosphoadenosine 5'-phosphate phosphatase Proteins 0.000 description 11
- 101710196411 Fructose-1,6-bisphosphatase Proteins 0.000 description 11
- 101710186733 Fructose-1,6-bisphosphatase, chloroplastic Proteins 0.000 description 11
- 101710109119 Fructose-1,6-bisphosphatase, cytosolic Proteins 0.000 description 11
- 101710198902 Fructose-1,6-bisphosphate aldolase/phosphatase Proteins 0.000 description 11
- 125000004437 phosphorous atom Chemical group 0.000 description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- 229910006069 SO3H Inorganic materials 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 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 8
- 150000003462 sulfoxides Chemical class 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 7
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 6
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
- 150000001409 amidines Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 4
- AFSHNJLKCYAWRX-UHFFFAOYSA-N 4-[(5-chloronaphthalen-2-yl)methyl]-5h-1,2,3,5-oxathiadiazole 2-oxide Chemical compound C=1C=C2C(Cl)=CC=CC2=CC=1CC1=NS(=O)ON1 AFSHNJLKCYAWRX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YVQKIDLSVHRBGZ-UHFFFAOYSA-N 5-[[4-[2-hydroxy-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O YVQKIDLSVHRBGZ-UHFFFAOYSA-N 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 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 4
- 229950009226 ciglitazone Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 229950002375 englitazone Drugs 0.000 description 4
- ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 229960005095 pioglitazone Drugs 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 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 4
- 229960001641 troglitazone Drugs 0.000 description 4
- 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 4
- IRAAJHYKQDFNFO-SFHVURJKSA-N (2s)-3-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-(2,2,2-trifluoroethoxy)propanoic acid Chemical compound N=1C2=CC=CC=C2OC=1N(C)CCOC1=CC=C(C[C@H](OCC(F)(F)F)C(O)=O)C=C1 IRAAJHYKQDFNFO-SFHVURJKSA-N 0.000 description 3
- 0 C*c([n]1*)nc2c1nc(*)nc2* Chemical compound C*c([n]1*)nc2c1nc(*)nc2* 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 2
- 229940123073 Angiotensin antagonist Drugs 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 229960001445 alitretinoin Drugs 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000002461 renin inhibitor Substances 0.000 description 2
- 229940086526 renin-inhibitors Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
- KGNRGVBNMVXFTL-UHFFFAOYSA-N CCOC(C(C)(C)[N]P(C)=O)=O Chemical compound CCOC(C(C)(C)[N]P(C)=O)=O KGNRGVBNMVXFTL-UHFFFAOYSA-N 0.000 description 1
- BYKBUQDQTLDNLE-KBPBESRZSA-N CCOC([C@H](C)NP(c1ccc(-c2c(CC(C)C)[s]c(N)n2)[o]1)(N[C@@H](C)C(OCC)=O)=O)=O Chemical compound CCOC([C@H](C)NP(c1ccc(-c2c(CC(C)C)[s]c(N)n2)[o]1)(N[C@@H](C)C(OCC)=O)=O)=O BYKBUQDQTLDNLE-KBPBESRZSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000005750 substituted cyclic group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11471898P | 1998-12-24 | 1998-12-24 | |
| US60/114,718 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2003515523A JP2003515523A (ja) | 2003-05-07 |
| JP2003515523A5 true JP2003515523A5 (https=) | 2007-02-15 |
Family
ID=22357016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000590620A Pending JP2003515523A (ja) | 1998-12-24 | 1999-12-22 | 糖尿病治療のためのｆｂｐアーゼ阻害物質とインスリンセンシタイザの組み合わせ |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1143955B1 (https=) |
| JP (1) | JP2003515523A (https=) |
| KR (3) | KR20070046210A (https=) |
| CN (3) | CN1714866A (https=) |
| AT (1) | ATE300288T1 (https=) |
| AU (1) | AU771039B2 (https=) |
| BR (1) | BR9917005A (https=) |
| CA (1) | CA2354053A1 (https=) |
| CZ (1) | CZ20012353A3 (https=) |
| DE (1) | DE69926400T2 (https=) |
| DK (1) | DK1143955T3 (https=) |
| ES (1) | ES2246586T3 (https=) |
| HK (1) | HK1046863B (https=) |
| HU (1) | HUP0402506A3 (https=) |
| ID (1) | ID30237A (https=) |
| IL (2) | IL143569A0 (https=) |
| MX (1) | MXPA01006511A (https=) |
| NO (1) | NO20013115L (https=) |
| NZ (1) | NZ512219A (https=) |
| PL (1) | PL352756A1 (https=) |
| PT (1) | PT1143955E (https=) |
| RU (2) | RU2227749C2 (https=) |
| SK (1) | SK9172001A3 (https=) |
| WO (1) | WO2000038666A2 (https=) |
| ZA (1) | ZA200105016B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6284748B1 (en) | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| KR100818845B1 (ko) | 1998-09-09 | 2008-04-01 | 메타베이시스 테라퓨틱스, 인크. | 신규한 프럭토스 1,6-비스포스파타제의 헤테로방향족 억제제 |
| AU784370B2 (en) * | 1999-12-22 | 2006-03-23 | Metabasis Therapeutics, Inc. | Novel bisamidate phosphonate prodrugs |
| JP2003525944A (ja) | 2000-03-08 | 2003-09-02 | メタバシス・セラピューティクス・インコーポレイテッド | 新規アリールフルクトース−１，６−ビスホスファターゼ阻害剤 |
| US7563774B2 (en) | 2000-06-29 | 2009-07-21 | Metabasis Therapeutics, Inc. | Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes |
| EP1372660A2 (en) * | 2000-07-06 | 2004-01-02 | Metabasis Therapeutics, Inc. | A combination of fbpase inhibitors and antidiabetic agents useful for the treatment of diabetes |
| EP1340749A4 (en) * | 2000-11-17 | 2007-09-05 | Takeda Pharmaceutical | ISOXAZOLE DERIVATIVES |
| EP2223927B1 (en) | 2002-05-13 | 2014-10-15 | Metabasis Therapeutics, Inc. | Salts of a phosphonic acid based prodrug of PMEA |
| WO2003095665A2 (en) | 2002-05-13 | 2003-11-20 | Metabasis Therapeutics, Inc. | Pmea and pmpa cyclic producing synthesis |
| 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 | |
| SI1611112T1 (sl) * | 2003-02-11 | 2012-12-31 | Vernalis (R&D) Limited | Izoksazolne spojine kot inhibitorji vroäśinskih ĺ ok proteinov |
| JP4638355B2 (ja) * | 2003-12-26 | 2011-02-23 | 協和発酵キリン株式会社 | チアゾール誘導体 |
| JP2008510018A (ja) * | 2004-08-18 | 2008-04-03 | メタバシス・セラピューティクス・インコーポレイテッド | フルクトース−１，６−ビスホスファターゼの新規チアゾール阻害物質 |
| BRPI0519006A2 (pt) * | 2004-12-13 | 2008-12-23 | Daiichi Sankyo Co Ltd | uso de um inibidor de fbpase, kit de uma composiÇço farmacÊutica, uso de uma preparaÇço de biguanida e um inibidor de fbpase, agente terapÊutico para diabetes melito, e, combinaÇço de agentes terapÊuticos |
| EP1825854A1 (en) * | 2004-12-15 | 2007-08-29 | Daiichi Sankyo Company, Limited | MEDICINAL COMPOSITION CONTAINING FBPase INHIBITOR |
| EP1889618A4 (en) * | 2005-05-27 | 2010-11-24 | Daiichi Sankyo Co Ltd | Combined drug for treating diabetes |
| EP1894930A4 (en) | 2005-06-23 | 2010-06-23 | Kyowa Hakko Kirin Co Ltd | THIAZOLE DERIVATIVE |
| US20100076037A1 (en) | 2006-11-02 | 2010-03-25 | Chiang Lillian W | Methods of Treating Neuropathic Pain with Agonists of PPAR-gamma |
| 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 |
| AU2015217221A1 (en) | 2014-02-13 | 2016-08-11 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| 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 |
| US6284748B1 (en) * | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| DE69819311T2 (de) * | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
| US6054587A (en) * | 1997-03-07 | 2000-04-25 | Metabasis Therapeutics, Inc. | Indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
-
1999
- 1999-12-22 PL PL99352756A patent/PL352756A1/xx not_active Application Discontinuation
- 1999-12-22 AU AU20583/00A patent/AU771039B2/en not_active Ceased
- 1999-12-22 BR BR9917005-1A patent/BR9917005A/pt not_active Application Discontinuation
- 1999-12-22 JP JP2000590620A patent/JP2003515523A/ja active Pending
- 1999-12-22 MX MXPA01006511A patent/MXPA01006511A/es active IP Right Grant
- 1999-12-22 ES ES99964313T patent/ES2246586T3/es not_active Expired - Lifetime
- 1999-12-22 CZ CZ20012353A patent/CZ20012353A3/cs unknown
- 1999-12-22 IL IL14356999A patent/IL143569A0/xx active IP Right Grant
- 1999-12-22 KR KR1020077008649A patent/KR20070046210A/ko not_active Ceased
- 1999-12-22 ID IDW00200101612A patent/ID30237A/id unknown
- 1999-12-22 CA CA002354053A patent/CA2354053A1/en not_active Abandoned
- 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 CN CNB998163562A patent/CN100352505C/zh not_active Expired - Fee Related
- 1999-12-22 KR KR1020067022095A patent/KR20060114724A/ko not_active Ceased
- 1999-12-22 HU HU0402506A patent/HUP0402506A3/hu active IP Right Revival
- 1999-12-22 EP EP99964313A patent/EP1143955B1/en not_active Expired - Lifetime
- 1999-12-22 AT AT99964313T patent/ATE300288T1/de active
- 1999-12-22 DK DK99964313T patent/DK1143955T3/da active
- 1999-12-22 NZ NZ512219A patent/NZ512219A/xx not_active IP Right Cessation
- 1999-12-22 KR KR1020017008102A patent/KR100689943B1/ko not_active Expired - Fee Related
- 1999-12-22 DE DE69926400T patent/DE69926400T2/de not_active Expired - Lifetime
- 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 WO PCT/US1999/030713 patent/WO2000038666A2/en not_active Ceased
- 1999-12-22 SK SK917-2001A patent/SK9172001A3/sk unknown
- 1999-12-22 PT PT99964313T patent/PT1143955E/pt unknown
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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
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