JP2009523141A - トリアジン誘導体およびＨＭＧ−ＣｏＡレダクターゼ阻害剤の組合せ - Google Patents
トリアジン誘導体およびＨＭＧ−ＣｏＡレダクターゼ阻害剤の組合せ Download PDFInfo
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- JP2009523141A JP2009523141A JP2008549782A JP2008549782A JP2009523141A JP 2009523141 A JP2009523141 A JP 2009523141A JP 2008549782 A JP2008549782 A JP 2008549782A JP 2008549782 A JP2008549782 A JP 2008549782A JP 2009523141 A JP2009523141 A JP 2009523141A
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- alkoxy
- alkyl
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- aryl
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 title claims abstract description 40
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 title claims abstract description 28
- 150000003918 triazines Chemical class 0.000 title claims abstract description 9
- -1 Amino, hydroxyl Chemical group 0.000 claims description 86
- 125000003545 alkoxy group Chemical group 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical group 0.000 claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 claims description 38
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims description 35
- 125000003282 alkyl amino group Chemical group 0.000 claims description 35
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 33
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 29
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 206010012601 diabetes mellitus Diseases 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 14
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229960004844 lovastatin Drugs 0.000 claims description 12
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 10
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 229960005370 atorvastatin Drugs 0.000 claims description 10
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 10
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 10
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 9
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 9
- 229960002965 pravastatin Drugs 0.000 claims description 9
- 229960003765 fluvastatin Drugs 0.000 claims description 8
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229960002855 simvastatin Drugs 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 6
- 229960000672 rosuvastatin Drugs 0.000 claims description 6
- 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 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000031773 Insulin resistance syndrome Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 208000037849 arterial hypertension Diseases 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229960002797 pitavastatin Drugs 0.000 claims description 2
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- GFICWFZTBXUVIG-UHFFFAOYSA-N 6-n,6-n,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine Chemical compound CC1N=C(N)NC(N(C)C)=N1 GFICWFZTBXUVIG-UHFFFAOYSA-N 0.000 claims 9
- 150000003840 hydrochlorides Chemical class 0.000 claims 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical class N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
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- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 abstract description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0600343A FR2896158B1 (fr) | 2006-01-13 | 2006-01-13 | Combinaison de derives de triazine et d'inhibiteurs de la hmg-coa reductase. |
| PCT/EP2006/012184 WO2007079916A2 (en) | 2006-01-13 | 2006-12-18 | Combination of triazine derivatives and hmg- coa reductase inhibitors for the treatment of diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009523141A true JP2009523141A (ja) | 2009-06-18 |
| JP2009523141A5 JP2009523141A5 (enExample) | 2010-02-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2008549782A Pending JP2009523141A (ja) | 2006-01-13 | 2006-12-18 | トリアジン誘導体およびＨＭＧ−ＣｏＡレダクターゼ阻害剤の組合せ |
Country Status (14)
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| US (1) | US20100158999A1 (enExample) |
| EP (1) | EP1978951A2 (enExample) |
| JP (1) | JP2009523141A (enExample) |
| KR (1) | KR20080085208A (enExample) |
| CN (1) | CN101355935A (enExample) |
| AR (1) | AR059031A1 (enExample) |
| AU (1) | AU2006334733A1 (enExample) |
| BR (1) | BRPI0621420A2 (enExample) |
| CA (1) | CA2636840A1 (enExample) |
| EA (1) | EA200801666A1 (enExample) |
| FR (1) | FR2896158B1 (enExample) |
| IL (1) | IL192594A0 (enExample) |
| WO (1) | WO2007079916A2 (enExample) |
| ZA (1) | ZA200806937B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021117861A1 (ja) * | 2019-12-13 | 2021-06-17 | 大日本住友製薬株式会社 | 製造性及び溶出性に優れた小型錠剤 |
| JP2021526506A (ja) * | 2018-06-14 | 2021-10-07 | ポクセルＰｏｘｅｌ | 糖尿病の治療において使用するためのトリアジン誘導体を含むフィルムコーティング錠剤 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949245B1 (en) * | 1999-06-25 | 2005-09-27 | Genentech, Inc. | Humanized anti-ErbB2 antibodies and treatment with anti-ErbB2 antibodies |
| JP5320399B2 (ja) * | 2007-08-31 | 2013-10-23 | ハナル バイオファーマ カンパニーリミテッド | １，３，５−トリアジン−２，４，６−トリアミン化合物またはその薬学的に許容可能な塩と、それを含む薬学組成物 |
| CA2745854A1 (en) * | 2008-12-12 | 2010-06-17 | Daniel Cravo | Tetrahydrotriazine compounds for treating diseases associated with ampk activity |
| FR2948028B1 (fr) * | 2009-07-17 | 2011-12-02 | Merck Sante Sas | Association d'un inhibiteur de l'echangeur sodium-proton et d'un derive amine de dihydro-1,3,5-triazine |
| EP2602249B1 (en) * | 2011-12-06 | 2015-08-12 | F.I.S. Fabbrica Italiana Sintetici S.p.A. | Synthesis of rosuvastatin by means of co-crystals |
| CA3102412A1 (en) | 2018-06-06 | 2019-12-12 | Metavant Sciences Gmbh | Methods of treating subjects having diabetes with chronic kidney disease |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0971540A (ja) * | 1995-07-03 | 1997-03-18 | Sankyo Co Ltd | 動脈硬化症予防および治療剤 |
| JP2003520858A (ja) * | 2000-01-26 | 2003-07-08 | リファ | ジヒドロ−１，３，５−トリアジンのアミン含有誘導体およびそれらの治療用用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2853650B1 (fr) * | 2003-04-10 | 2006-07-07 | Merck Sante Sas | Procede de dedoublement d'amines utiles pour le traitement de desordres associes au syndrome d'insulino-resistance |
| EP1510208A1 (en) * | 2003-08-22 | 2005-03-02 | Fournier Laboratories Ireland Limited | Pharmaceutical composition comprising a combination of metformin and statin |
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2006
- 2006-01-13 FR FR0600343A patent/FR2896158B1/fr not_active Expired - Fee Related
- 2006-12-18 WO PCT/EP2006/012184 patent/WO2007079916A2/en not_active Ceased
- 2006-12-18 BR BRPI0621420-7A patent/BRPI0621420A2/pt not_active IP Right Cessation
- 2006-12-18 US US12/160,504 patent/US20100158999A1/en not_active Abandoned
- 2006-12-18 EP EP06829705A patent/EP1978951A2/en not_active Withdrawn
- 2006-12-18 CN CNA2006800508489A patent/CN101355935A/zh active Pending
- 2006-12-18 EA EA200801666A patent/EA200801666A1/ru unknown
- 2006-12-18 CA CA002636840A patent/CA2636840A1/en not_active Abandoned
- 2006-12-18 AU AU2006334733A patent/AU2006334733A1/en not_active Abandoned
- 2006-12-18 JP JP2008549782A patent/JP2009523141A/ja active Pending
- 2006-12-18 KR KR1020087019392A patent/KR20080085208A/ko not_active Withdrawn
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2007
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2008
- 2008-07-02 IL IL192594A patent/IL192594A0/en unknown
- 2008-08-12 ZA ZA200806937A patent/ZA200806937B/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0971540A (ja) * | 1995-07-03 | 1997-03-18 | Sankyo Co Ltd | 動脈硬化症予防および治療剤 |
| JP2003520858A (ja) * | 2000-01-26 | 2003-07-08 | リファ | ジヒドロ−１，３，５−トリアジンのアミン含有誘導体およびそれらの治療用用途 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021526506A (ja) * | 2018-06-14 | 2021-10-07 | ポクセルＰｏｘｅｌ | 糖尿病の治療において使用するためのトリアジン誘導体を含むフィルムコーティング錠剤 |
| JP7266616B2 (ja) | 2018-06-14 | 2023-04-28 | ポクセル | 糖尿病の治療において使用するためのトリアジン誘導体を含むフィルムコーティング錠剤 |
| WO2021117861A1 (ja) * | 2019-12-13 | 2021-06-17 | 大日本住友製薬株式会社 | 製造性及び溶出性に優れた小型錠剤 |
| JPWO2021117861A1 (enExample) * | 2019-12-13 | 2021-06-17 | ||
| JP7093473B2 (ja) | 2019-12-13 | 2022-06-29 | 住友ファーマ株式会社 | 製造性及び溶出性に優れた小型錠剤 |
| JP2022123069A (ja) * | 2019-12-13 | 2022-08-23 | 住友ファーマ株式会社 | 製造性及び溶出性に優れた小型錠剤 |
| JP7671265B2 (ja) | 2019-12-13 | 2025-05-01 | 住友ファーマ株式会社 | 製造性及び溶出性に優れた小型錠剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2896158B1 (fr) | 2008-09-12 |
| ZA200806937B (en) | 2009-07-29 |
| EP1978951A2 (en) | 2008-10-15 |
| US20100158999A1 (en) | 2010-06-24 |
| AU2006334733A1 (en) | 2007-07-19 |
| AR059031A1 (es) | 2008-03-12 |
| KR20080085208A (ko) | 2008-09-23 |
| WO2007079916A2 (en) | 2007-07-19 |
| CN101355935A (zh) | 2009-01-28 |
| IL192594A0 (en) | 2009-09-22 |
| EA200801666A1 (ru) | 2008-12-30 |
| BRPI0621420A2 (pt) | 2011-12-06 |
| FR2896158A1 (fr) | 2007-07-20 |
| WO2007079916A3 (en) | 2007-12-06 |
| CA2636840A1 (en) | 2007-07-19 |
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