MX367769B - Nuevo derivado de acido 3-(4-(benciloxi)fenil)hex-4-inoico, metodo de preparacion del mismo y composicion farmaceutica para la prevencion y tratamiento de la enfermedad metabolica que incluye el mismo como ingrediente activo. - Google Patents
Nuevo derivado de acido 3-(4-(benciloxi)fenil)hex-4-inoico, metodo de preparacion del mismo y composicion farmaceutica para la prevencion y tratamiento de la enfermedad metabolica que incluye el mismo como ingrediente activo.Info
- Publication number
- MX367769B MX367769B MX2015013893A MX2015013893A MX367769B MX 367769 B MX367769 B MX 367769B MX 2015013893 A MX2015013893 A MX 2015013893A MX 2015013893 A MX2015013893 A MX 2015013893A MX 367769 B MX367769 B MX 367769B
- Authority
- MX
- Mexico
- Prior art keywords
- benzyloxy
- hex
- phenyl
- novel
- acid derivative
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 4
- 208000016097 disease of metabolism Diseases 0.000 title abstract 3
- 208000030159 metabolic disease Diseases 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 239000004615 ingredient Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 abstract 2
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 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 abstract 2
- 230000003287 optical effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 208000032928 Dyslipidaemia Diseases 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 208000035150 Hypercholesterolemia Diseases 0.000 abstract 1
- 208000031226 Hyperlipidaemia Diseases 0.000 abstract 1
- 102000004877 Insulin Human genes 0.000 abstract 1
- 108090001061 Insulin Proteins 0.000 abstract 1
- 208000017170 Lipid metabolism disease Diseases 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 230000004913 activation Effects 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 201000001421 hyperglycemia Diseases 0.000 abstract 1
- 208000006575 hypertriglyceridemia Diseases 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 229940125396 insulin Drugs 0.000 abstract 1
- 230000003914 insulin secretion Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 208000011580 syndromic disease Diseases 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
Classifications
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- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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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
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- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
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- 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
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Abstract
La presente invención se refiere a un nuevo derivado del ácido 3-(4-(benciloxi) fenil) hex-4-inoico, a un método de preparación del mismo, y a una composición farmacéutica para la prevención y el tratamiento de una enfermedad metabólica que incluye el mismo como ingrediente efectivo. El nuevo derivado del ácido 3-(4-(benciloxi) fenil) hex-4-inoico, el isómero óptico del mismo, o la sal del mismo farmacéuticamente aceptable, de acuerdo con la presente invención, tienen un excelente efecto sobre la activación de la proteína de GPR40 y por consiguiente tienen un efecto promotor excelente de secreción de insulina; no son tóxicos cuando son co-administrados con otros fármacos y posiblemente son co-administrados con otros fármacos; y tienen un excelente efecto de eficacia de la activación de la proteína de GPR40 in vivo. Por lo tanto, una composición que incluye el nuevo derivado del ácido 3-(4-(benciloxi) fenil) hex-4-inoico, el isómero óptico del mismo, o la sal del mismo farmacéuticamente aceptable, pueden ser utilizados adecuadamente en una composición farmacéutica para prevenir y tratar una enfermedad metabólica tal como la obesidad, la diabetes del tipo I, la diabetes del tipo II, la tolerancia a la glucosa incompatible, la tolerancia a la insulina, la hiperglucemia, la hiperlipidemia, la hipertrigliceridemia, la hipercolesterolemia, la dislipidemia, el síndrome X, etc.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20130043100 | 2013-04-18 | ||
KR1020140045343A KR101569522B1 (ko) | 2013-04-18 | 2014-04-16 | 신규한 3-(4-(벤질옥시)페닐)헥스-4-이노익 산 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 대사성 질환의 예방 또는 치료용 약학적 조성물 |
PCT/KR2014/003355 WO2014171762A1 (ko) | 2013-04-18 | 2014-04-17 | 신규한 3-(4-(벤질옥시)페닐)헥스-4-이노익 산 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 대사성 질환의 예방 또는 치료용 약학적 조성물 |
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MX2015013893A MX2015013893A (es) | 2015-12-11 |
MX367769B true MX367769B (es) | 2019-09-05 |
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MX2015013893A MX367769B (es) | 2013-04-18 | 2014-04-17 | Nuevo derivado de acido 3-(4-(benciloxi)fenil)hex-4-inoico, metodo de preparacion del mismo y composicion farmaceutica para la prevencion y tratamiento de la enfermedad metabolica que incluye el mismo como ingrediente activo. |
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US (1) | US9969723B2 (es) |
EP (1) | EP2987791B1 (es) |
JP (2) | JP6174784B2 (es) |
KR (1) | KR101569522B1 (es) |
CN (1) | CN105121423B (es) |
AU (1) | AU2014254555B2 (es) |
BR (1) | BR112015025072B1 (es) |
CA (1) | CA2908398C (es) |
DK (1) | DK2987791T3 (es) |
ES (1) | ES2745746T3 (es) |
HK (1) | HK1214822A1 (es) |
MX (1) | MX367769B (es) |
PL (1) | PL2987791T3 (es) |
PT (1) | PT2987791T (es) |
RU (1) | RU2628077C2 (es) |
WO (1) | WO2014171762A1 (es) |
Families Citing this family (14)
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EA201690888A1 (ru) * | 2013-11-14 | 2016-10-31 | Кадила Хелзкэр Лимитед | Новые гетероциклические соединения |
CN111423408A (zh) | 2014-10-17 | 2020-07-17 | 现代药品株式会社 | 代谢性疾病的预防或治疗用复合制剂 |
CN109516914A (zh) * | 2017-09-20 | 2019-03-26 | 华东师范大学 | 苯丙炔酸类小分子有机化合物及其合成方法和用途 |
SG11202004891PA (en) * | 2017-12-01 | 2020-06-29 | Hyundai Pharm Co Ltd | Novel use of 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative |
CN110092774B (zh) * | 2018-01-29 | 2022-04-08 | 中国科学院上海药物研究所 | 芳香丙酸类衍生物、及其制备方法和用途 |
PE20210640A1 (es) | 2018-02-13 | 2021-03-23 | Gilead Sciences Inc | Inhibidores pd-1/pd-l1 |
TWI712412B (zh) | 2018-04-19 | 2020-12-11 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
ES2962674T3 (es) | 2018-07-13 | 2024-03-20 | Gilead Sciences Inc | Inhibidores PD-1/PD-L1 |
CN112955435B (zh) | 2018-10-24 | 2024-09-06 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
JP7297199B2 (ja) | 2019-02-04 | 2023-06-26 | 美里工業株式会社 | 電動格納式車両用周辺視認装置 |
MX2021014751A (es) * | 2019-05-31 | 2022-01-18 | Hyundai Pharm Co Ltd | Forma cristalina novedosa de derivado de acido 3-(4-(benciloxi)fenil)hex-4-inoico. |
KR102270026B1 (ko) * | 2020-01-31 | 2021-06-28 | 현대약품 주식회사 | (3s)-3-(4-(3-(1,4-다이옥사스파이로[4,5]데스-7-엔-8-일)벤질옥시)페닐)헥스-4-이노익산의 품질 평가 방법 |
CN116829542A (zh) * | 2021-01-29 | 2023-09-29 | 韩国化学研究院 | 苯并噻唑及苯并咪唑衍生物、药学上可接受的盐、其制备方法以及包含其作为活性成分的药物组合物 |
KR102699076B1 (ko) * | 2021-04-01 | 2024-08-27 | 현대약품 주식회사 | 3-(4-(벤질옥시)페닐)헥스-4-이노익산 유도체의 신규 용도 |
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DE69941777D1 (de) | 1998-03-10 | 2010-01-21 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
GB0214149D0 (en) | 2002-06-19 | 2002-07-31 | Glaxo Group Ltd | Chemical compounds |
EP1737809B1 (en) * | 2004-02-27 | 2013-09-18 | Amgen, Inc | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders |
JP4859665B2 (ja) | 2004-03-30 | 2012-01-25 | 武田薬品工業株式会社 | アルコキシフェニルプロパン酸誘導体 |
US7687526B2 (en) * | 2006-09-07 | 2010-03-30 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
CA2662305C (en) * | 2006-09-07 | 2012-04-17 | Amgen Inc. | Heterocyclic gpr40 modulators |
JP2010524932A (ja) * | 2007-04-16 | 2010-07-22 | アムジエン・インコーポレーテツド | 置換ビフェニルフェノキシ−、チオフェニル−及びアミノフェニルプロパン酸gpr40調節物質 |
WO2009048527A1 (en) * | 2007-10-10 | 2009-04-16 | Amgen Inc. | Substituted biphenyl gpr40 modulators |
WO2009054479A1 (ja) * | 2007-10-26 | 2009-04-30 | Japan Tobacco Inc. | スピロ環化合物及びその医薬用途 |
CA2716352C (en) * | 2008-03-06 | 2013-05-28 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
AR078522A1 (es) * | 2009-10-15 | 2011-11-16 | Lilly Co Eli | Compuesto de espiropiperidina, composicion farmaceutica que lo comprende, su uso para preparar un medicamento util para tratar diabetes y compuesto intermediario para su sintesis |
EA201690888A1 (ru) * | 2013-11-14 | 2016-10-31 | Кадила Хелзкэр Лимитед | Новые гетероциклические соединения |
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- 2014-04-17 PL PL14786040T patent/PL2987791T3/pl unknown
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- 2014-04-17 MX MX2015013893A patent/MX367769B/es active IP Right Grant
- 2014-04-17 RU RU2015141278A patent/RU2628077C2/ru active
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- 2014-04-17 DK DK14786040.7T patent/DK2987791T3/da active
- 2014-04-17 AU AU2014254555A patent/AU2014254555B2/en active Active
- 2014-04-17 CN CN201480019721.5A patent/CN105121423B/zh active Active
- 2014-04-17 PT PT147860407T patent/PT2987791T/pt unknown
- 2014-04-17 JP JP2016508871A patent/JP6174784B2/ja active Active
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RU2628077C2 (ru) | 2017-08-14 |
US20160024063A1 (en) | 2016-01-28 |
WO2014171762A1 (ko) | 2014-10-23 |
CN105121423A (zh) | 2015-12-02 |
JP2017149747A (ja) | 2017-08-31 |
CA2908398A1 (en) | 2014-10-23 |
BR112015025072A2 (pt) | 2017-07-18 |
RU2015141278A (ru) | 2017-05-25 |
KR20140126248A (ko) | 2014-10-30 |
ES2745746T3 (es) | 2020-03-03 |
CN105121423B (zh) | 2017-06-09 |
DK2987791T3 (da) | 2019-10-14 |
AU2014254555A1 (en) | 2015-10-29 |
AU2014254555B2 (en) | 2016-11-10 |
BR112015025072B1 (pt) | 2022-03-15 |
PT2987791T (pt) | 2019-10-24 |
CA2908398C (en) | 2019-01-15 |
PL2987791T3 (pl) | 2020-03-31 |
US9969723B2 (en) | 2018-05-15 |
KR101569522B1 (ko) | 2015-11-17 |
JP6174784B2 (ja) | 2017-08-02 |
EP2987791B1 (en) | 2019-07-17 |
EP2987791A4 (en) | 2016-11-23 |
JP2016518366A (ja) | 2016-06-23 |
EP2987791A1 (en) | 2016-02-24 |
HK1214822A1 (zh) | 2016-08-05 |
MX2015013893A (es) | 2015-12-11 |
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