EA020540B1 - Агонисты gpr119 - Google Patents
Агонисты gpr119 Download PDFInfo
- Publication number
- EA020540B1 EA020540B1 EA201270169A EA201270169A EA020540B1 EA 020540 B1 EA020540 B1 EA 020540B1 EA 201270169 A EA201270169 A EA 201270169A EA 201270169 A EA201270169 A EA 201270169A EA 020540 B1 EA020540 B1 EA 020540B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- mmol
- compound
- mixture
- added
- methanesulfonyl
- Prior art date
Links
- 229940100607 GPR119 agonist Drugs 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 208000008589 Obesity Diseases 0.000 claims abstract description 4
- 235000020824 obesity Nutrition 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 153
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 7
- MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 claims description 7
- 229960004034 sitagliptin Drugs 0.000 claims description 7
- RDTBTUCYZYOHAM-UHFFFAOYSA-N 1-methylsulfonyl-4-[4-[[1-[[1-(trifluoromethyl)cyclopropyl]methyl]piperidin-4-yl]methoxy]phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1N(S(=O)(=O)C)CCC(C=2C=CC(OCC3CCN(CC4(CC4)C(F)(F)F)CC3)=CC=2)=C1 RDTBTUCYZYOHAM-UHFFFAOYSA-N 0.000 claims description 5
- LAGIBLSAFMGIJY-UHFFFAOYSA-N 5-[[1-(2-fluoro-2-methylpropyl)piperidin-4-yl]methoxy]-2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)pyridine Chemical group C1CN(CC(C)(F)C)CCC1COC1=CC=C(C=2CCN(CC=2)S(C)(=O)=O)N=C1 LAGIBLSAFMGIJY-UHFFFAOYSA-N 0.000 claims description 5
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 3
- 229960003105 metformin Drugs 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 1
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 1
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- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- AJJISMLYIMQAKP-OAHLLOKOSA-N 5-[4-[(2r)-4-(3-fluoro-4-methylsulfonylphenoxy)butan-2-yl]piperidin-1-yl]-3-propan-2-yl-1,2,4-oxadiazole Chemical class CC(C)C1=NOC(N2CCC(CC2)[C@H](C)CCOC=2C=C(F)C(=CC=2)S(C)(=O)=O)=N1 AJJISMLYIMQAKP-OAHLLOKOSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
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- -1 s Chemical class 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
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- 238000000034 method Methods 0.000 description 14
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000556 agonist Substances 0.000 description 10
- 230000037396 body weight Effects 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
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- 241001465754 Metazoa Species 0.000 description 8
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 6
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
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- 230000001404 mediated effect Effects 0.000 description 1
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- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000013116 obese mouse model Methods 0.000 description 1
- 238000007410 oral glucose tolerance test Methods 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- OHEDMAIVEXQCOZ-UHFFFAOYSA-N piperidine;dihydrochloride Chemical compound Cl.Cl.C1CCNCC1 OHEDMAIVEXQCOZ-UHFFFAOYSA-N 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KLAXGNDJPAQPPU-UHFFFAOYSA-N tert-butyl 4-[[2-fluoro-4-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)phenoxy]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1COC1=CC=C(C=2CCN(CC=2)S(C)(=O)=O)C=C1F KLAXGNDJPAQPPU-UHFFFAOYSA-N 0.000 description 1
- JYUQEWCJWDGCRX-UHFFFAOYSA-N tert-butyl 4-formylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)CC1 JYUQEWCJWDGCRX-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09382114 | 2009-07-15 | ||
| US24544509P | 2009-09-24 | 2009-09-24 | |
| PCT/US2010/041645 WO2011008663A1 (en) | 2009-07-15 | 2010-07-12 | Gpr119 agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201270169A1 EA201270169A1 (ru) | 2012-06-29 |
| EA020540B1 true EA020540B1 (ru) | 2014-11-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201270169A EA020540B1 (ru) | 2009-07-15 | 2010-07-12 | Агонисты gpr119 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8207344B2 (enExample) |
| EP (1) | EP2454251A1 (enExample) |
| JP (1) | JP5715127B2 (enExample) |
| KR (1) | KR101365854B1 (enExample) |
| CN (1) | CN102471313B (enExample) |
| AR (1) | AR077638A1 (enExample) |
| AU (1) | AU2010273642B2 (enExample) |
| BR (1) | BRPI1015921A2 (enExample) |
| CA (1) | CA2764906C (enExample) |
| CO (1) | CO6480977A2 (enExample) |
| CR (1) | CR20120012A (enExample) |
| DO (1) | DOP2012000006A (enExample) |
| EA (1) | EA020540B1 (enExample) |
| EC (1) | ECSP12011606A (enExample) |
| IL (1) | IL216776A0 (enExample) |
| MA (1) | MA33428B1 (enExample) |
| MX (1) | MX2012000704A (enExample) |
| NZ (1) | NZ597125A (enExample) |
| PE (1) | PE20121045A1 (enExample) |
| SG (1) | SG177646A1 (enExample) |
| TN (1) | TN2012000002A1 (enExample) |
| TW (1) | TWI429634B (enExample) |
| WO (1) | WO2011008663A1 (enExample) |
| ZA (1) | ZA201200227B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0406761A (pt) | 2003-01-14 | 2005-12-20 | Arena Pharm Inc | Derivados de arila e heteroarila 1,2,3-trissubstituìdos como moduladores do metabolismo e a profilaxia e tratamento de distúrbios relacionados a estes tais como diabetes e hiper-glicemia |
| EP2108960A1 (en) | 2008-04-07 | 2009-10-14 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditons modulated by PYY |
| US20130109703A1 (en) | 2010-03-18 | 2013-05-02 | 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 |
| SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012135570A1 (en) * | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| US8957062B2 (en) | 2011-04-08 | 2015-02-17 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds and methods of treatment |
| WO2012170702A1 (en) * | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012170867A1 (en) | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| WO2012173917A1 (en) | 2011-06-16 | 2012-12-20 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds, compositions containing such compounds, and methods of treatment |
| 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 |
| US9018200B2 (en) | 2011-10-24 | 2015-04-28 | Merck Sharp & Dohme Corp. | Substituted piperidinyl compounds useful as GPR119 agonists |
| WO2013062835A1 (en) * | 2011-10-24 | 2013-05-02 | Merck Sharp & Dohme Corp. | Substituted piperidinyl compounds useful as gpr119 agonists |
| US9018224B2 (en) | 2011-11-15 | 2015-04-28 | Merck Sharp & Dohme Corp. | Substituted cyclopropyl compounds useful as GPR119 agonists |
| CA2867114C (en) * | 2012-06-12 | 2016-02-23 | Chong Kun Dang Pharmaceutical Corp. | Piperidine derivatives for gpr119 agonist |
| EP2872127A1 (en) | 2012-07-11 | 2015-05-20 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| WO2014052619A1 (en) * | 2012-09-27 | 2014-04-03 | Irm Llc | Piperidine derivatives and compositions as modulators of gpr119 activity |
| RU2642429C2 (ru) * | 2013-11-26 | 2018-01-25 | Чон Кун Тан Фармасьютикал Корп. | Амидные производные в качестве агонистов grp119 |
| KR101651505B1 (ko) * | 2014-05-02 | 2016-08-29 | 현대약품 주식회사 | 싸이클로 헥센 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 대사성 질환의 예방 또는 치료용 약학적 조성물 |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| CA3002551A1 (en) | 2015-06-22 | 2016-12-29 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(com pound 1)for use in s1p1 receptor-associated disorders |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| TW202140440A (zh) | 2020-02-28 | 2021-11-01 | 美商克力歐普股份有限公司 | Gpr40激動劑 |
| AU2021275038A1 (en) | 2020-05-19 | 2022-12-22 | Kallyope, Inc. | AMPK activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
Citations (2)
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|---|---|---|---|---|
| WO2008025798A1 (en) * | 2006-08-30 | 2008-03-06 | Biovitrum Ab (Publ) | Pyridine compounds for treating gpr119 related disorders |
| WO2009038974A1 (en) * | 2007-09-20 | 2009-03-26 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
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| BRPI0406761A (pt) * | 2003-01-14 | 2005-12-20 | Arena Pharm Inc | Derivados de arila e heteroarila 1,2,3-trissubstituìdos como moduladores do metabolismo e a profilaxia e tratamento de distúrbios relacionados a estes tais como diabetes e hiper-glicemia |
| US7638541B2 (en) * | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
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2010
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- 2010-07-12 PE PE2012000041A patent/PE20121045A1/es not_active Application Discontinuation
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- 2012-01-11 ZA ZA2012/00227A patent/ZA201200227B/en unknown
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008025798A1 (en) * | 2006-08-30 | 2008-03-06 | Biovitrum Ab (Publ) | Pyridine compounds for treating gpr119 related disorders |
| WO2009038974A1 (en) * | 2007-09-20 | 2009-03-26 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
Also Published As
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|---|---|
| MA33428B1 (fr) | 2012-07-03 |
| MX2012000704A (es) | 2012-03-07 |
| CA2764906C (en) | 2014-06-10 |
| CR20120012A (es) | 2012-03-28 |
| EA201270169A1 (ru) | 2012-06-29 |
| JP5715127B2 (ja) | 2015-05-07 |
| ZA201200227B (en) | 2013-06-26 |
| NZ597125A (en) | 2013-08-30 |
| TW201114757A (en) | 2011-05-01 |
| IL216776A0 (en) | 2012-03-01 |
| JP2012533546A (ja) | 2012-12-27 |
| SG177646A1 (en) | 2012-02-28 |
| TWI429634B (zh) | 2014-03-11 |
| KR101365854B1 (ko) | 2014-02-21 |
| CN102471313B (zh) | 2014-06-04 |
| KR20120024964A (ko) | 2012-03-14 |
| CO6480977A2 (es) | 2012-07-16 |
| AU2010273642A1 (en) | 2012-01-19 |
| TN2012000002A1 (en) | 2013-09-19 |
| CA2764906A1 (en) | 2011-01-20 |
| WO2011008663A1 (en) | 2011-01-20 |
| AR077638A1 (es) | 2011-09-14 |
| AU2010273642B2 (en) | 2014-03-13 |
| EP2454251A1 (en) | 2012-05-23 |
| BRPI1015921A2 (pt) | 2016-04-26 |
| CN102471313A (zh) | 2012-05-23 |
| US8207344B2 (en) | 2012-06-26 |
| ECSP12011606A (es) | 2012-02-29 |
| DOP2012000006A (es) | 2012-01-31 |
| PE20121045A1 (es) | 2012-08-09 |
| US20110015199A1 (en) | 2011-01-20 |
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