SA08280756B1 - معضدات gpcr تشتمل على بروبوكسى بنزاميد وبيوتوكسى بنزاميد - Google Patents
معضدات gpcr تشتمل على بروبوكسى بنزاميد وبيوتوكسى بنزاميد Download PDFInfo
- Publication number
- SA08280756B1 SA08280756B1 SA8280756A SA08280756A SA08280756B1 SA 08280756 B1 SA08280756 B1 SA 08280756B1 SA 8280756 A SA8280756 A SA 8280756A SA 08280756 A SA08280756 A SA 08280756A SA 08280756 B1 SA08280756 B1 SA 08280756B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- piperidin
- propoxy
- oxadiazol
- isopropyl
- hydroxy
- Prior art date
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- VPTQXJGFCHOGAN-UHFFFAOYSA-N 2-butoxybenzamide Chemical compound CCCCOC1=CC=CC=C1C(N)=O VPTQXJGFCHOGAN-UHFFFAOYSA-N 0.000 title abstract description 4
- 229940125633 GPCR agonist Drugs 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- 150000003839 salts Chemical class 0.000 claims abstract description 79
- 208000008589 Obesity Diseases 0.000 claims abstract description 22
- 235000020824 obesity Nutrition 0.000 claims abstract description 22
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 45
- -1 C1-3alkyl hydrogen Chemical compound 0.000 claims description 36
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 36
- 210000004369 blood Anatomy 0.000 claims description 16
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WWGQACDETXVZPY-UHFFFAOYSA-N 2-methyl-3-propan-2-ylbenzamide Chemical compound C(C)(C)C=1C(=C(C(=O)N)C=CC=1)C WWGQACDETXVZPY-UHFFFAOYSA-N 0.000 claims 1
- CEUMDONLYQNLQD-UHFFFAOYSA-N 2-methyl-4-[3-[1-[3-(2-methylpropyl)-1,2,4-oxadiazol-5-yl]piperidin-4-yl]propoxy]benzamide Chemical compound CC(C)CC1=NOC(N2CCC(CCCOC=3C=C(C)C(C(N)=O)=CC=3)CC2)=N1 CEUMDONLYQNLQD-UHFFFAOYSA-N 0.000 claims 1
- FVOAKYSSAARGKC-UHFFFAOYSA-N 3-methylbenzamide Chemical compound [CH2]C1=CC=CC(C(N)=O)=C1 FVOAKYSSAARGKC-UHFFFAOYSA-N 0.000 claims 1
- JTSXJHQYAMOGSA-UHFFFAOYSA-N 3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C=1N=CON=1 JTSXJHQYAMOGSA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/435—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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
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- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0700124A GB0700124D0 (en) | 2007-01-04 | 2007-01-04 | GPCR agonists |
| GB0708740A GB0708740D0 (en) | 2007-05-08 | 2007-05-08 | Gpcr agonists |
| GB0719762A GB0719762D0 (en) | 2007-10-10 | 2007-10-10 | GPCR agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA08280756B1 true SA08280756B1 (ar) | 2011-01-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA8280756A SA08280756B1 (ar) | 2007-01-04 | 2008-01-05 | معضدات gpcr تشتمل على بروبوكسى بنزاميد وبيوتوكسى بنزاميد |
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| Country | Link |
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| EP (2) | EP2383270A1 (OSRAM) |
| JP (1) | JP2010514829A (OSRAM) |
| KR (1) | KR20090104092A (OSRAM) |
| CN (1) | CN101627036A (OSRAM) |
| AR (1) | AR064736A1 (OSRAM) |
| AT (1) | ATE531710T1 (OSRAM) |
| AU (1) | AU2008203673A1 (OSRAM) |
| BR (1) | BRPI0806468A2 (OSRAM) |
| CA (1) | CA2674093A1 (OSRAM) |
| CL (1) | CL2008000017A1 (OSRAM) |
| DK (1) | DK2114931T3 (OSRAM) |
| EA (1) | EA015805B9 (OSRAM) |
| ES (1) | ES2376015T3 (OSRAM) |
| HR (1) | HRP20110964T1 (OSRAM) |
| IL (1) | IL199680A0 (OSRAM) |
| MA (1) | MA31084B1 (OSRAM) |
| MX (1) | MX2009007180A (OSRAM) |
| NZ (1) | NZ578144A (OSRAM) |
| PE (1) | PE20081849A1 (OSRAM) |
| PL (1) | PL2114931T3 (OSRAM) |
| PT (1) | PT2114931E (OSRAM) |
| RS (1) | RS52168B (OSRAM) |
| SA (1) | SA08280756B1 (OSRAM) |
| SI (1) | SI2114931T1 (OSRAM) |
| TW (1) | TWI380818B (OSRAM) |
| WO (1) | WO2008081205A1 (OSRAM) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| JP4980928B2 (ja) * | 2004-12-24 | 2012-07-18 | プロシディオン・リミテッド | Ｇタンパク質共役受容体（ｇｐｒ１１６）作動薬および肥満および糖尿病治療のためのその使用 |
| US20100063081A1 (en) * | 2005-06-30 | 2010-03-11 | Stuart Edward Bradly | CPCR Agonists |
| DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| AU2007247190A1 (en) | 2006-05-04 | 2007-11-15 | Boehringer Ingelheim International Gmbh | Polymorphs |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| PE20081659A1 (es) * | 2007-01-04 | 2008-10-24 | Prosidion Ltd | Agonistas de gpcr |
| US20100286112A1 (en) | 2007-09-10 | 2010-11-11 | Oscar Barba | Compounds for the treatment of metabolic disorders |
| CN101868452B (zh) | 2007-10-10 | 2014-08-06 | 诺华股份有限公司 | 螺环吡咯烷类与其对抗hcv和hiv感染的应用 |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| GB0812642D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| GB0812649D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| GB0812648D0 (en) * | 2008-07-10 | 2008-08-20 | Prosidion Ltd | Compounds |
| WO2010006191A1 (en) * | 2008-07-11 | 2010-01-14 | Irm Llc | 4-phenoxymethylpiperidines as modulators of gpr119 activity |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| KR20200118243A (ko) | 2008-08-06 | 2020-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| KR20110067096A (ko) | 2008-09-10 | 2011-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 및 관련 상태를 치료하기 위한 병용 요법 |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| TWI508965B (zh) | 2008-12-23 | 2015-11-21 | Boehringer Ingelheim Int | 有機化合物的鹽形式 |
| TW201036975A (en) | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
| GB0904287D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB0904285D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB0904284D0 (en) | 2009-03-12 | 2009-04-22 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| TW201113269A (en) | 2009-06-24 | 2011-04-16 | Boehringer Ingelheim Int | New compounds, pharmaceutical composition and methods relating thereto |
| TW201111361A (en) | 2009-06-24 | 2011-04-01 | Boehringer Ingelheim Int | New compounds, pharmaceutical composition and methods relating thereto |
| WO2011019538A1 (en) | 2009-08-13 | 2011-02-17 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| EA034869B1 (ru) | 2009-11-27 | 2020-03-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2547339A1 (en) | 2010-03-18 | 2013-01-23 | Boehringer Ingelheim International GmbH | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
| GB201006167D0 (en) | 2010-04-14 | 2010-05-26 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| GB201006166D0 (en) | 2010-04-14 | 2010-05-26 | Prosidion Ltd | Compounds for the treatment of metabolic disorders |
| ITMI20100770A1 (it) | 2010-05-03 | 2011-11-04 | Dipharma Francis Srl | Procedimento per la preparazione di 3-(4-piridinil)-propanolo e suoi intermedi |
| NZ602921A (en) | 2010-05-05 | 2016-01-29 | Boehringer Ingelheim Int | Combination therapy comprising the administration of a glp-1 receptor agonist and a ddp-4 inhibitor |
| TW201209054A (en) | 2010-05-28 | 2012-03-01 | Prosidion Ltd | Novel compounds |
| ITMI20100984A1 (it) | 2010-05-31 | 2011-12-01 | Dipharma Francis Srl | Procedimento per la preparazione di ossadiazoli |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| KR20220025926A (ko) | 2010-06-24 | 2022-03-03 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| AR083904A1 (es) | 2010-11-18 | 2013-04-10 | Prosidion Ltd | Derivados de 1,4-pirrolidinas disustituidos y 3-il-aminas y sus usos en el tratamiento de desordenes metabolicos |
| GB201114389D0 (en) | 2011-08-22 | 2011-10-05 | Prosidion Ltd | Novel compounds |
| EP2693882B1 (en) | 2011-04-08 | 2017-06-28 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| US9181214B2 (en) | 2011-06-09 | 2015-11-10 | Rhizen Pharmaceuticals Sa | Bicyclic compounds as modulators of GPR-119 |
| EP2720544B1 (en) | 2011-06-16 | 2016-12-21 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds, and methods of treatment |
| CA2841552C (en) | 2011-07-15 | 2020-06-23 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760855B1 (en) | 2011-09-30 | 2017-03-15 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds as well as their use in treating type-2 diabetes |
| EP2771000B1 (en) | 2011-10-24 | 2016-05-04 | Merck Sharp & Dohme Corp. | Substituted piperidinyl compounds useful as gpr119 agonists |
| CA2855009C (en) | 2011-11-15 | 2019-07-09 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds useful as gpr119 agonists |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| EP2849754B1 (en) | 2012-05-14 | 2022-09-14 | Boehringer Ingelheim International GmbH | Linagliptin, a xanthine derivative as dpp-4 inhibitor, for use in the treatment of sirs and/or sepsis |
| WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
| KR101726819B1 (ko) * | 2014-10-27 | 2017-04-13 | 동아에스티 주식회사 | Gpr119 작용 활성을 갖는 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물 |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
| EP3421455B1 (en) * | 2017-06-29 | 2019-03-27 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of chiral 3-amino-piperidins, useful intermediates for the preparation of tofacitinib |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576810A (en) * | 1968-06-20 | 1971-04-27 | Robins Co Inc A H | 1-substituted-3-(-4)-aroylpiperidines |
| US5252586A (en) * | 1990-09-28 | 1993-10-12 | The Du Pont Merck Pharmaceutical Company | Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents |
| FR2713225B1 (fr) | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| DE4222565A1 (de) * | 1992-07-09 | 1994-01-13 | Hoechst Ag | Meta-substituierte Sechsringaromaten zur Verwendung in Flüssigkristallmischungen |
| US6100042A (en) * | 1993-03-31 | 2000-08-08 | Cadus Pharmaceutical Corporation | Yeast cells engineered to produce pheromone system protein surrogates, and uses therefor |
| DE4311967A1 (de) * | 1993-04-10 | 1994-10-13 | Hoechst Ag | Smektische Flüssigkristallmischung |
| DE4311968A1 (de) * | 1993-04-10 | 1994-10-20 | Hoechst Ag | Smektische Flüssigkristallmischung |
| US5338738A (en) * | 1993-04-19 | 1994-08-16 | Bristol-Myers Squibb Company | Cerebral function enhancers: acyclic amide derivatives of pyrimidinylpiperidines |
| FR2705346B1 (fr) * | 1993-05-18 | 1995-08-11 | Union Pharma Scient Appl | Nouveaux dérivés de pipéridinyl thio indole, leurs procédés de préparation, compositions pharmaceutiques les contenant, utiles notamment comme antalgiques . |
| EP0664798B1 (en) | 1993-08-13 | 1999-12-29 | Zeneca Limited | Thiadiazole derivatives and their use as fungicides or insecticides |
| JPH11513382A (ja) * | 1995-10-20 | 1999-11-16 | ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ５員複素環化合物、これらの化合物を含む医薬品、それらの使用及びそれらの調製方法 |
| ZA977103B (en) | 1996-08-09 | 1999-02-08 | Eisai Co Ltd | Benzopiperidine derivatives |
| GB9719496D0 (en) | 1997-09-13 | 1997-11-19 | Glaxo Group Ltd | G protien chimeras |
| WO2000012704A2 (en) | 1998-09-01 | 2000-03-09 | Basf Aktiengesellschaft | Enhanced functional expression of g protein-coupled receptors |
| US6221660B1 (en) | 1999-02-22 | 2001-04-24 | Synaptic Pharmaceutical Corporation | DNA encoding SNORF25 receptor |
| AU2001292255A1 (en) * | 2000-11-21 | 2002-06-03 | Mitsubishi Chemical Corporation | Process for producing 2-(4-pyridyl)ethanethiol |
| FR2829027A1 (fr) | 2001-08-29 | 2003-03-07 | Aventis Pharma Sa | Association avec un antagoniste du recepteur cb1, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de parkinson |
| FR2829028B1 (fr) | 2001-08-29 | 2004-12-17 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et d'un produit qui active la neurotransmission dopaminergique dans le cerveau, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de |
| AU2002331766A1 (en) | 2001-08-31 | 2003-03-18 | University Of Connecticut | Novel pyrazole analogs acting on cannabinoid receptors |
| MXPA04002583A (es) | 2001-09-21 | 2004-06-18 | Solvay Pharm Bv | Derivados de 4,5-dihidro-1h-pirazol novedosos que tienen actividad antagonistica del canabinoide (cb1). |
| NZ528280A (en) | 2001-09-21 | 2005-11-25 | Solvay Pharmaceuticals B | 4,5-dihydro-1H-pyrazole derivatives having potent CB1-antagonistic activity |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| FR2831883B1 (fr) | 2001-11-08 | 2004-07-23 | Sanofi Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| SE0104332D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| SE0104330D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| FR2833842B1 (fr) | 2001-12-21 | 2004-02-13 | Aventis Pharma Sa | Compositions pharmaceutiques a base de derives d'azetidine |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| WO2003075660A1 (en) | 2002-03-06 | 2003-09-18 | Merck & Co., Inc. | Method of treatment or prevention of obesity |
| DE60334787D1 (de) | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Substituierte amide |
| AR038966A1 (es) | 2002-03-18 | 2005-02-02 | Solvay Pharm Bv | Derivados de tiazol que tienen actividad antagonista, agonista o agonista parcial de cb1 |
| JP2005528366A (ja) | 2002-03-26 | 2005-09-22 | メルク エンド カムパニー インコーポレーテッド | カンナビノイド受容体モジュレータとしてのスピロ環式アミド |
| ES2192494B1 (es) | 2002-03-27 | 2005-02-16 | Consejo Superior De Investigaciones Cientificas | Derivados de 1,2,4-triazol con propiedades cannabinoides. |
| CA2479744A1 (en) | 2002-03-28 | 2003-10-09 | Paul E. Finke | Substituted 2,3-diphenyl pyridines |
| EP1494997A4 (en) | 2002-04-05 | 2007-04-11 | Merck & Co Inc | SUBSTITUTED ARYLAMID |
| FR2838439B1 (fr) | 2002-04-11 | 2005-05-20 | Sanofi Synthelabo | Derives de terphenyle, leur preparation, les compositions pharmaceutqiues en contenant |
| FR2838438A1 (fr) | 2002-04-11 | 2003-10-17 | Sanofi Synthelabo | Derives de diphenylpyridine,leur preparation, les compositions pharmaceutiques en contenant |
| US7667053B2 (en) | 2002-04-12 | 2010-02-23 | Merck & Co., Inc. | Bicyclic amides |
| US6825209B2 (en) | 2002-04-15 | 2004-11-30 | Research Triangle Institute | Compounds having unique CB1 receptor binding selectivity and methods for their production and use |
| HRP20050044A2 (en) | 2002-07-29 | 2005-10-31 | F. Hoffmann - La Roche Ag | Novel benzodioxoles |
| ES2294330T3 (es) | 2002-08-02 | 2008-04-01 | MERCK & CO., INC. | Derivados de furo(2,3-b)piridina sustituidos. |
| AU2003296895A1 (en) | 2002-08-20 | 2004-05-04 | The Regents Of The University Of California | Combination therapy for controlling appetites |
| HRP20050053A2 (en) | 2002-09-19 | 2005-04-30 | Solvay Pharmaceuticals B.V. | 1 h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
| WO2004029204A2 (en) | 2002-09-27 | 2004-04-08 | Merck & Co., Inc. | Substituted pyrimidines |
| EP1556373A1 (en) | 2002-10-18 | 2005-07-27 | Pfizer Products Inc. | Cannabinoid receptor ligands and uses thereof |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| CN1747926A (zh) | 2002-12-19 | 2006-03-15 | 麦克公司 | 取代酰胺化合物 |
| GB0230087D0 (en) | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| EP1583762B1 (en) | 2003-01-02 | 2008-07-09 | F. Hoffmann-La Roche Ag | Pyrrolyl-thiazoles and their use as cb 1 receptor inverse agonists |
| KR100704097B1 (ko) | 2003-01-02 | 2007-04-06 | 에프. 호프만-라 로슈 아게 | 신규 ｃｂ 1 수용체 역작용제 |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| DE502004007000D1 (de) | 2003-02-13 | 2008-06-12 | Sanofi Aventis Deutschland | Stickstoff substituierte hexahydro-pyrazino 1,2-a pyrimidin-4,7-dionderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| ATE472548T1 (de) | 2003-02-13 | 2010-07-15 | Sanofi Aventis Deutschland | Substituierte hexahydro-pyrazino(1,2-a)pyrimidin- 4,7-dionderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US20040167188A1 (en) * | 2003-02-14 | 2004-08-26 | Zhili Xin | Protein-tyrosine phosphatase inhibitors and uses thereof |
| US7169797B2 (en) * | 2003-02-14 | 2007-01-30 | Abbott Laboratories | Protein-tyrosine phosphatase inhibitors and uses thereof |
| EP1606019A1 (en) | 2003-03-07 | 2005-12-21 | The University Court of The University of Aberdeen | Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| AR045496A1 (es) * | 2003-08-29 | 2005-11-02 | Schering Corp | Analolgos de benzimidazolpiperidinas 2- substiyuidas como antagonistas de los receptores de la hormona que concentra melanina selectivos para el tratamiento de la obesidad y trastornos relacionados |
| JP4958560B2 (ja) | 2003-12-24 | 2012-06-20 | プロシディオン・リミテッド | Ｇｐｃｒ受容体作動薬としてのヘテロ環誘導体 |
| JP4980928B2 (ja) * | 2004-12-24 | 2012-07-18 | プロシディオン・リミテッド | Ｇタンパク質共役受容体（ｇｐｒ１１６）作動薬および肥満および糖尿病治療のためのその使用 |
| WO2006067532A1 (en) | 2004-12-24 | 2006-06-29 | Prosidion Ltd | G-protein coupled receptor agonists |
| GB0428514D0 (en) | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| DOP2006000008A (es) * | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
| KR20080025190A (ko) | 2005-06-30 | 2008-03-19 | 프로시디온 리미티드 | Ｇ-단백질 결합된 수용체 효능제 |
| US20090221644A1 (en) | 2005-06-30 | 2009-09-03 | Stuart Edward Bradley | Gpcr Agonists |
| EP1907383A1 (en) | 2005-06-30 | 2008-04-09 | Prosidion Limited | Gpcr agonists |
| US20100063081A1 (en) | 2005-06-30 | 2010-03-11 | Stuart Edward Bradly | CPCR Agonists |
| JP2009532453A (ja) * | 2006-04-06 | 2009-09-10 | プロシディオン・リミテッド | ヘテロサイクリックｇｐｃｒアゴニスト |
| JP5330260B2 (ja) * | 2006-12-06 | 2013-10-30 | スミスクライン ビーチャム コーポレーション | 二環式化合物ならびに抗糖尿病薬としての使用 |
| EP2377863A1 (en) * | 2007-01-04 | 2011-10-19 | Prosidion Limited | Piperidine GPCR agonists |
| WO2008081208A1 (en) * | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| PE20081659A1 (es) * | 2007-01-04 | 2008-10-24 | Prosidion Ltd | Agonistas de gpcr |
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- 2008-01-04 US US12/522,018 patent/US20100022591A1/en not_active Abandoned
- 2008-01-04 RS RS20120031A patent/RS52168B/sr unknown
- 2008-01-04 CN CN200880007091A patent/CN101627036A/zh active Pending
- 2008-01-04 EA EA200900796A patent/EA015805B9/ru not_active IP Right Cessation
- 2008-01-04 HR HR20110964T patent/HRP20110964T1/hr unknown
- 2008-01-04 ES ES08700184T patent/ES2376015T3/es active Active
- 2008-01-04 PT PT08700184T patent/PT2114931E/pt unknown
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- 2008-01-04 SI SI200830517T patent/SI2114931T1/sl unknown
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| RS52168B (sr) | 2012-08-31 |
| AR064736A1 (es) | 2009-04-22 |
| TW200835489A (en) | 2008-09-01 |
| MX2009007180A (es) | 2009-07-15 |
| NZ578144A (en) | 2011-03-31 |
| CA2674093A1 (en) | 2008-07-10 |
| BRPI0806468A2 (pt) | 2011-09-27 |
| PL2114931T3 (pl) | 2012-03-30 |
| EA015805B9 (ru) | 2012-03-30 |
| TWI380818B (zh) | 2013-01-01 |
| PT2114931E (pt) | 2012-01-12 |
| AU2008203673A1 (en) | 2008-07-10 |
| EP2383270A1 (en) | 2011-11-02 |
| CN101627036A (zh) | 2010-01-13 |
| ES2376015T3 (es) | 2012-03-08 |
| CL2008000017A1 (es) | 2008-08-01 |
| MA31084B1 (fr) | 2010-01-04 |
| SI2114931T1 (sl) | 2012-02-29 |
| HK1135704A1 (en) | 2010-06-11 |
| EP2114931A1 (en) | 2009-11-11 |
| US20100022591A1 (en) | 2010-01-28 |
| ATE531710T1 (de) | 2011-11-15 |
| KR20090104092A (ko) | 2009-10-05 |
| HRP20110964T1 (hr) | 2012-01-31 |
| EA015805B1 (ru) | 2011-12-30 |
| IL199680A0 (en) | 2010-04-15 |
| JP2010514829A (ja) | 2010-05-06 |
| PE20081849A1 (es) | 2009-01-26 |
| EA200900796A1 (ru) | 2010-02-26 |
| WO2008081205A1 (en) | 2008-07-10 |
| EP2114931B1 (en) | 2011-11-02 |
| DK2114931T3 (da) | 2012-02-13 |
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