ES2526660T3 - Glucósido enólico de ácido fenilpirúvico antidiabético - Google Patents
Glucósido enólico de ácido fenilpirúvico antidiabético Download PDFInfo
- Publication number
- ES2526660T3 ES2526660T3 ES10771690.4T ES10771690T ES2526660T3 ES 2526660 T3 ES2526660 T3 ES 2526660T3 ES 10771690 T ES10771690 T ES 10771690T ES 2526660 T3 ES2526660 T3 ES 2526660T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- group
- ylcarbonyl
- piperazin
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 title 2
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 title 1
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 title 1
- 230000003178 anti-diabetic effect Effects 0.000 title 1
- 239000003472 antidiabetic agent Substances 0.000 title 1
- 229930182470 glycoside Natural products 0.000 title 1
- 150000002338 glycosides Chemical class 0.000 title 1
- -1 pyrrolidin-1-yl-carbonyl Chemical group 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005163 aryl sulfanyl group Chemical group 0.000 abstract 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 abstract 1
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 abstract 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Compuesto de fórmula I o una sal fisiológicamente aceptable del mismo:**Fórmula** en la que, Ar es benceno; n es 1; R1, R2, R3 y R4 están seleccionados, de manera independiente, del grupo que consiste en hidrógeno, flúor, cloro, bromo, yodo, arilo, alquilo C1-6, alquinilo C2-6, alquenilo C2-6, cicloalquilo C3-10, cicloalquil C3-10-alquilo C1-3, cicloalquenilo C5-10, cicloalquenil C5-10-alquilo C1-3, alquilcarbonilo C1-4, arilcarbonilo, heteroarilcarbonilo, aminocarbonilo, alquilaminocarbonilo C1-4, di-(alquil C1-3)aminocarbonilo, pirrolidin-1-il-carbonilo, piperidin-1- ilcarbonilo, morfolin-4-ilcarbonilo, piperazin-1-ilcarbonilo, 4-(alquil C1-4)piperizin-1-ilcarbonilo, alcoxicarbonilo C1-4, amino, alquilamino C1-4, di-(alquil C1-3)amino, pirrolidin-1-ilo, piperidin-1-ilo, morfolin-4-ilo, piperazin-1-ilo, 4-(alquil C1-4)piperazin-1-ilo, alquilcarbonilamino C1-4, alquiloxi C1-6, cicloalquiloxi C3-10, cicloalqueniloxi C5-10, ariloxi, alquilsulfanilo C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4, cicloalquilsulfanilo C3-10, cicloalquilsulfinilo C3-10, cicloalquilsulfonilo C3-10, cicloalquenilsulfanilo C5-10, cicloalquenilsulfinilo C5-10, cicloalquenilsulfonilo C5-10, arilsulfanilo, arilsulfinilo, arilsulfonilo, hidroxi, ciano y nitro, X1 está seleccionado, de manera independiente, del grupo que consiste en -OH, -CH2OR5, H, -OR5 y -C(O)R5; X2 está seleccionado del grupo que consiste en -OH, -CH2OR5, H, -OR5 y -C(O)R520 ; X3 es -O-; X4 es -O-; X5 >= (-CH2)m-; m es 0, 1, 2 o 3. A está seleccionado del grupo que consiste en -CO2H, -CO2R5, -SO3H; -SO2HNR5; -PO(OH)2; -CONH(CO)R5; -CONH(CO)H, -CONHSO2R5; -CONHCN; y**Fórmula** donde el enlace marcado con * está unido al etileno; y R5 está seleccionado del grupo que consiste en cadena alquilo C1-C6 lineal o ramificada, cadena alquenilo C2-C6 lineal o ramificada, o alquinilo, arilo, aralquilo, heteroarilo, carbociclo y heterociclo; con la condición de que: * X2 es diferente de -OH, cuando X3 es -O- y al menos un X1 es OH; * Si R1, R2, R3 y R4 son -H, A no es -CO2H ni -CO2R5, cuando X1 es -OH, X3 y X4 son -O-, X2 es -CH2OH, n es 1 y X5 es (-CH2)m-, donde m es 0; y * R1, R2 o R3 no están en posición para con respecto a X5 si R1, R2 o R3 están seleccionados entre alquiloxi C1- 6, cicloalquiloxi C3-10, cicloalqueniloxi C5-10, ariloxi e hidroxi.
Description
Claims (1)
-
imagen1 imagen2 imagen3 imagen4 imagen5 imagen6
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2010/065052 WO2012045363A1 (en) | 2010-10-07 | 2010-10-07 | Antidiabetic enolic glucoside of phenylpyruvic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2526660T3 true ES2526660T3 (es) | 2015-01-14 |
Family
ID=43496931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10771690.4T Active ES2526660T3 (es) | 2010-10-07 | 2010-10-07 | Glucósido enólico de ácido fenilpirúvico antidiabético |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9221860B2 (es) |
| EP (1) | EP2625184B1 (es) |
| JP (1) | JP2013538862A (es) |
| CN (1) | CN103228668B (es) |
| CA (1) | CA2813617C (es) |
| ES (1) | ES2526660T3 (es) |
| WO (1) | WO2012045363A1 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101913619B1 (ko) | 2011-06-09 | 2018-12-28 | 리젠 파마슈티컬스 소시에떼 아노님 | Gpr-119의 조절제로서의 신규한 화합물 |
| CN104610390A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 一种含氨基葡萄糖和腈基吡啶结构的gpr119激动剂及其用途 |
| CN104610392A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 含氨基葡萄糖和卤代吡啶结构的gpr119激动剂及其用途 |
| CN104610393A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 一类含氨基葡萄糖和卤代吡啶结构化合物及其用途 |
| CN104610389A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 一种含氨基葡萄糖和硝基吡啶结构的gpr119激动剂及其用途 |
| CN104628795A (zh) * | 2015-02-13 | 2015-05-20 | 佛山市赛维斯医药科技有限公司 | 一种含氨基葡萄糖和腈基吡啶结构衍生物及其用途 |
| CN104610391A (zh) * | 2015-02-13 | 2015-05-13 | 佛山市赛维斯医药科技有限公司 | 含氨基葡萄糖结构的gpr119激动剂、制备方法及其用途 |
| JP2016026208A (ja) * | 2015-10-28 | 2016-02-12 | サズセ アーペーエスＺａｄｅｃ Ａｐｓ | フェニルピルビン酸の抗糖尿病エノール型グルコシド |
| JP6297621B2 (ja) * | 2016-06-08 | 2018-03-20 | サズセ アーペーエスＺａｄｅｃ Ａｐｓ | フェニルピルビン酸の抗糖尿病エノール型グルコシド |
| KR102295300B1 (ko) | 2018-09-12 | 2021-08-30 | 동아에스티 주식회사 | Gpr119 리간드를 유효성분으로 포함하는 비알콜성 지방간 질환의 예방 또는 치료용 약학적 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3308763B2 (ja) | 1995-02-14 | 2002-07-29 | カネボウ株式会社 | アルコール刺激緩和剤及びアルコール水溶液 |
| JP2003084391A (ja) | 2001-09-13 | 2003-03-19 | Konica Corp | 熱現像感光材料及び画像記録方法 |
| JP2003121964A (ja) | 2001-10-16 | 2003-04-23 | Konica Corp | 熱現像感光材料及びその処理方法 |
| NZ563604A (en) * | 2001-11-29 | 2009-04-30 | Theracos Inc | Compounds for treatment of inflammation, diabetes and related disorders |
| CN1679706A (zh) | 2005-01-28 | 2005-10-12 | 北京阜康仁生物制药科技有限公司 | 一种由三七、红景天制成的治疗心脑血管疾病的药物制剂及其制备方法 |
| JP2006316020A (ja) | 2005-05-16 | 2006-11-24 | Nicca Chemical Co Ltd | レプチン産生抑制剤 |
| JP2008156264A (ja) | 2006-12-22 | 2008-07-10 | Daishoo:Kk | ルイボスティーの食後高血糖および血中尿酸低下作用 |
| US8877717B2 (en) | 2007-03-12 | 2014-11-04 | Zadec Aps | Anti-diabetic extract of rooibos |
-
2010
- 2010-10-07 ES ES10771690.4T patent/ES2526660T3/es active Active
- 2010-10-07 JP JP2013532054A patent/JP2013538862A/ja not_active Withdrawn
- 2010-10-07 CN CN201080070135.5A patent/CN103228668B/zh not_active Expired - Fee Related
- 2010-10-07 EP EP10771690.4A patent/EP2625184B1/en active Active
- 2010-10-07 WO PCT/EP2010/065052 patent/WO2012045363A1/en not_active Ceased
- 2010-10-07 US US13/878,158 patent/US9221860B2/en not_active Expired - Fee Related
- 2010-10-07 CA CA2813617A patent/CA2813617C/en active Active
-
2015
- 2015-11-18 US US14/945,109 patent/US10174065B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20160083411A1 (en) | 2016-03-24 |
| CA2813617C (en) | 2016-01-19 |
| WO2012045363A1 (en) | 2012-04-12 |
| CN103228668B (zh) | 2016-04-27 |
| US20130310331A1 (en) | 2013-11-21 |
| US10174065B2 (en) | 2019-01-08 |
| CA2813617A1 (en) | 2012-04-12 |
| EP2625184B1 (en) | 2014-10-01 |
| JP2013538862A (ja) | 2013-10-17 |
| CN103228668A (zh) | 2013-07-31 |
| EP2625184A1 (en) | 2013-08-14 |
| US9221860B2 (en) | 2015-12-29 |
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