ES2347177T3 - Combinacion de derivados de triazina y sensibilizadores de insulina. - Google Patents
Combinacion de derivados de triazina y sensibilizadores de insulina. Download PDFInfo
- Publication number
- ES2347177T3 ES2347177T3 ES06829706T ES06829706T ES2347177T3 ES 2347177 T3 ES2347177 T3 ES 2347177T3 ES 06829706 T ES06829706 T ES 06829706T ES 06829706 T ES06829706 T ES 06829706T ES 2347177 T3 ES2347177 T3 ES 2347177T3
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- ES
- Spain
- Prior art keywords
- alkoxy
- alkyl
- aryl
- carboxy
- carboxymethyl
- Prior art date
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- 229940122355 Insulin sensitizer Drugs 0.000 title claims abstract description 29
- 150000003918 triazines Chemical class 0.000 title claims description 10
- -1 amino, hydroxy Chemical group 0.000 claims abstract description 152
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 113
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 74
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 150000002367 halogens Chemical group 0.000 claims abstract description 57
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 5
- 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 abstract description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 3
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims abstract 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 claims description 32
- 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 32
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- 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 15
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 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 description 12
- 238000011282 treatment Methods 0.000 claims description 12
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- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 10
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 10
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 9
- 229960003105 metformin Drugs 0.000 claims description 8
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- IRLWJILLXJGJTD-UHFFFAOYSA-N Muraglitazar Chemical compound C1=CC(OC)=CC=C1OC(=O)N(CC(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 IRLWJILLXJGJTD-UHFFFAOYSA-N 0.000 claims description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- 125000000304 alkynyl group Chemical group 0.000 claims description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 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 4
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- 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 4
- 229940123208 Biguanide Drugs 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 2
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- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
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- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000003840 hydrochlorides Chemical class 0.000 claims 4
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical group C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- 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
- A61K31/42—Oxazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- 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
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- 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
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Landscapes
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- Pharmacology & Pharmacy (AREA)
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- Obesity (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0600344A FR2896159B1 (fr) | 2006-01-13 | 2006-01-13 | Combinaison de derives de triazine et d'agents sensibilisateurs a l'insuline. |
| FR0600344 | 2006-01-13 |
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| ES2347177T3 true ES2347177T3 (es) | 2010-10-26 |
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| ES06829706T Active ES2347177T3 (es) | 2006-01-13 | 2006-12-18 | Combinacion de derivados de triazina y sensibilizadores de insulina. |
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| EP (1) | EP1971330B1 (enExample) |
| JP (1) | JP5249782B2 (enExample) |
| KR (2) | KR20140033498A (enExample) |
| CN (1) | CN101355933A (enExample) |
| AR (1) | AR059032A1 (enExample) |
| AT (1) | ATE476179T1 (enExample) |
| AU (1) | AU2006334734B2 (enExample) |
| BR (1) | BRPI0620985B8 (enExample) |
| CA (1) | CA2640897C (enExample) |
| CY (1) | CY1110789T1 (enExample) |
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| EA (1) | EA015576B1 (enExample) |
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| FR (1) | FR2896159B1 (enExample) |
| IL (1) | IL192558A (enExample) |
| PL (1) | PL1971330T3 (enExample) |
| PT (1) | PT1971330E (enExample) |
| SI (1) | SI1971330T1 (enExample) |
| WO (1) | WO2007079917A2 (enExample) |
| ZA (1) | ZA200806947B (enExample) |
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| FR2896159B1 (fr) * | 2006-01-13 | 2008-09-12 | Merck Sante Soc Par Actions Si | Combinaison de derives de triazine et d'agents sensibilisateurs a l'insuline. |
| JP5667985B2 (ja) * | 2008-12-12 | 2015-02-12 | ポクセル | インスリンとトリアジンの組合せ及び糖尿病を治療するためのその使用 |
| CA2745854A1 (en) * | 2008-12-12 | 2010-06-17 | Daniel Cravo | Tetrahydrotriazine compounds for treating diseases associated with ampk activity |
| FR2948027A1 (fr) * | 2009-07-17 | 2011-01-21 | Merck Sante Sas | Derives amines de dihydro-1,3,5-triazine pour leur utilisation dans le traitement des maladies associees a une ischemie et/ou une reperfusion |
| FR2948026B1 (fr) * | 2009-07-17 | 2011-12-02 | Merck Sante Sas | Derives amines de dihydro-1,3,5-triazine |
| TWI436768B (zh) * | 2010-06-09 | 2014-05-11 | Poxel | 第２型糖尿病之治療 |
| KR20120011667A (ko) | 2010-07-29 | 2012-02-08 | 광주과학기술원 | 당뇨병 치료제의 스크리닝 방법 |
| KR101271218B1 (ko) * | 2012-12-07 | 2013-06-07 | 광주과학기술원 | 당뇨병 치료제의 스크리닝 방법 |
| JP2020536121A (ja) | 2017-10-02 | 2020-12-10 | ポクセルＰｏｘｅｌ | 駆出率が保持された心不全を治療する方法 |
| CA3102412A1 (en) | 2018-06-06 | 2019-12-12 | Metavant Sciences Gmbh | Methods of treating subjects having diabetes with chronic kidney disease |
| WO2019238647A1 (en) | 2018-06-14 | 2019-12-19 | Poxel | Film-coated tablet comprising a triazine derivative for use in the treatment of diabetes |
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| US5885980A (en) * | 1996-06-25 | 1999-03-23 | Enrique G. Gutierrez | Composition and method for treating diabetes |
| US6011049A (en) | 1997-02-19 | 2000-01-04 | Warner-Lambert Company | Combinations for diabetes |
| TW200514783A (en) | 1999-09-22 | 2005-05-01 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| AR030920A1 (es) | 1999-11-16 | 2003-09-03 | Smithkline Beecham Plc | Composiciones farmaceuticas para el tratamiento de la diabetes mellitus y condiciones asociadas con la diabetes mellitus, y procedimientos para preparar dichas composiciones |
| FR2804113B1 (fr) * | 2000-01-26 | 2004-06-18 | Lipha | Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique |
| AU2001257456B2 (en) * | 2000-05-01 | 2006-02-09 | Aeropharm Technology, Inc. | A core formulation |
| 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 |
| TW200526678A (en) * | 2003-08-01 | 2005-08-16 | Janssen Pharmaceutica Nv | Substituted indole-O-glucosides |
| FR2863484B1 (fr) * | 2003-12-11 | 2007-04-13 | Oreal | Utilisation de composes capables d'agir sur la voie metabolique controlee par la dopachrome tautomerase trp-2 comme agent protecteur des melanocytes du follicule pileux et applications |
| EP1841414A1 (en) * | 2003-12-31 | 2007-10-10 | Alpharma, Inc. | Rosiglitazone and metformin formulations |
| FR2896159B1 (fr) * | 2006-01-13 | 2008-09-12 | Merck Sante Soc Par Actions Si | Combinaison de derives de triazine et d'agents sensibilisateurs a l'insuline. |
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2006
- 2006-01-13 FR FR0600344A patent/FR2896159B1/fr not_active Expired - Fee Related
- 2006-12-18 EA EA200801676A patent/EA015576B1/ru not_active IP Right Cessation
- 2006-12-18 BR BRPI0620985A patent/BRPI0620985B8/pt not_active IP Right Cessation
- 2006-12-18 PT PT06829706T patent/PT1971330E/pt unknown
- 2006-12-18 EP EP06829706A patent/EP1971330B1/en active Active
- 2006-12-18 DE DE602006016014T patent/DE602006016014D1/de active Active
- 2006-12-18 AU AU2006334734A patent/AU2006334734B2/en not_active Ceased
- 2006-12-18 DK DK06829706.8T patent/DK1971330T3/da active
- 2006-12-18 CA CA2640897A patent/CA2640897C/en not_active Expired - Fee Related
- 2006-12-18 PL PL06829706T patent/PL1971330T3/pl unknown
- 2006-12-18 AT AT06829706T patent/ATE476179T1/de active
- 2006-12-18 JP JP2008549783A patent/JP5249782B2/ja active Active
- 2006-12-18 WO PCT/EP2006/012185 patent/WO2007079917A2/en not_active Ceased
- 2006-12-18 KR KR1020147002582A patent/KR20140033498A/ko not_active Ceased
- 2006-12-18 ES ES06829706T patent/ES2347177T3/es active Active
- 2006-12-18 CN CNA2006800509443A patent/CN101355933A/zh active Pending
- 2006-12-18 KR KR20087019624A patent/KR101482685B1/ko not_active Expired - Fee Related
- 2006-12-18 SI SI200630793T patent/SI1971330T1/sl unknown
- 2006-12-18 US US12/160,664 patent/US8791115B2/en active Active
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2007
- 2007-01-12 AR ARP070100138A patent/AR059032A1/es unknown
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2008
- 2008-07-01 IL IL192558A patent/IL192558A/en active IP Right Grant
- 2008-08-12 ZA ZA200806947A patent/ZA200806947B/xx unknown
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2010
- 2010-09-16 CY CY20101100840T patent/CY1110789T1/el unknown
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2013
- 2013-10-25 US US14/063,530 patent/US20140050786A1/en not_active Abandoned
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