HUE034557T2 - 2-Pyridone Compound - Google Patents
2-Pyridone Compound Download PDFInfo
- Publication number
- HUE034557T2 HUE034557T2 HUE13855534A HUE13855534A HUE034557T2 HU E034557 T2 HUE034557 T2 HU E034557T2 HU E13855534 A HUE13855534 A HU E13855534A HU E13855534 A HUE13855534 A HU E13855534A HU E034557 T2 HUE034557 T2 HU E034557T2
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- ethyl
- compounds
- cyclopropyl
- present
- Prior art date
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- -1 2-pyridone compound Chemical class 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 62
- 239000013078 crystal Substances 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 46
- 239000003814 drug Substances 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 238000000862 absorption spectrum Methods 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 230000000704 physical effect Effects 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims 2
- 241001424309 Arita Species 0.000 claims 1
- 102000018779 Replication Protein C Human genes 0.000 claims 1
- 108010027647 Replication Protein C Proteins 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 125000006001 difluoroethyl group Chemical group 0.000 claims 1
- 210000000981 epithelium Anatomy 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 230000003442 weekly effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 239000000243 solution Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 238000004519 manufacturing process Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
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- 239000003112 inhibitor Substances 0.000 description 21
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- ABERLDAQFUZISG-SJLPKXTDSA-N 3-cyclopropyl-6-[(1r)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2r)-5-oxopyrrolidin-2-yl]ethyl]-1h-pyridin-2-one Chemical compound C1=CC(C(F)(F)C)=CC=C1[C@H](C=1NC(=O)C(C2CC2)=CC=1)C[C@@H]1NC(=O)CC1 ABERLDAQFUZISG-SJLPKXTDSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
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- 229910052763 palladium Inorganic materials 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 238000010511 deprotection reaction Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 10
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- 238000001914 filtration Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229960004756 ethanol Drugs 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
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- 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 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 4
- WXFUCIUQPOVNPU-QGZVFWFLSA-N COC1=C(C=CC(=N1)C(=C[C@H]1CCC(=O)N1)C1=CC=C(C=C1)C(C)(F)F)C1CC1 Chemical compound COC1=C(C=CC(=N1)C(=C[C@H]1CCC(=O)N1)C1=CC=C(C=C1)C(C)(F)F)C1CC1 WXFUCIUQPOVNPU-QGZVFWFLSA-N 0.000 description 4
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
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- OWCOWYGJWMOVKV-UHFFFAOYSA-N (5-cyclopropyl-6-methoxypyridin-2-yl)-[4-(1,1-difluoroethyl)phenyl]methanone Chemical compound COC1=NC(C(=O)C=2C=CC(=CC=2)C(C)(F)F)=CC=C1C1CC1 OWCOWYGJWMOVKV-UHFFFAOYSA-N 0.000 description 3
- WXFUCIUQPOVNPU-HNMKQIAWSA-N (5r)-5-[(e)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethenyl]pyrrolidin-2-one Chemical compound COC1=NC(C(=C\[C@@H]2NC(=O)CC2)\C=2C=CC(=CC=2)C(C)(F)F)=CC=C1C1CC1 WXFUCIUQPOVNPU-HNMKQIAWSA-N 0.000 description 3
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- NAQMPKWVHXYOMG-DUSLRRAJSA-N (5r)-5-[2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethyl]pyrrolidin-2-one Chemical compound COC1=NC(C(C[C@@H]2NC(=O)CC2)C=2C=CC(=CC=2)C(C)(F)F)=CC=C1C1CC1 NAQMPKWVHXYOMG-DUSLRRAJSA-N 0.000 description 3
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- WGRQANOPCQRCME-PMACEKPBSA-N teneligliptin Chemical compound O=C([C@H]1NC[C@H](C1)N1CCN(CC1)C1=CC(=NN1C=1C=CC=CC=1)C)N1CCSC1 WGRQANOPCQRCME-PMACEKPBSA-N 0.000 description 1
- 229950000034 teneligliptin Drugs 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 229950006667 tofogliflozin Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000003383 uricosuric agent Substances 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic 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
- A61P3/04—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
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012249792 | 2012-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE034557T2 true HUE034557T2 (en) | 2018-02-28 |
Family
ID=50731146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE13855534A HUE034557T2 (en) | 2012-11-13 | 2013-11-12 | 2-Pyridone Compound |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9695148B2 (Direct) |
| EP (1) | EP2921489B1 (Direct) |
| JP (1) | JP5963025B2 (Direct) |
| KR (1) | KR102160841B1 (Direct) |
| CN (1) | CN104768944B (Direct) |
| AU (1) | AU2013345930B2 (Direct) |
| BR (1) | BR112015010823A2 (Direct) |
| CA (1) | CA2891406C (Direct) |
| DK (1) | DK2921489T3 (Direct) |
| ES (1) | ES2641469T3 (Direct) |
| HU (1) | HUE034557T2 (Direct) |
| IL (1) | IL238701B (Direct) |
| IN (1) | IN2015DN03869A (Direct) |
| MX (1) | MX361479B (Direct) |
| MY (1) | MY173812A (Direct) |
| NO (1) | NO2921489T3 (Direct) |
| NZ (1) | NZ707832A (Direct) |
| PH (1) | PH12015501056B1 (Direct) |
| PL (1) | PL2921489T3 (Direct) |
| PT (1) | PT2921489T (Direct) |
| RU (1) | RU2662157C2 (Direct) |
| SG (1) | SG11201503716RA (Direct) |
| TW (1) | TWI591064B (Direct) |
| WO (1) | WO2014077235A1 (Direct) |
| ZA (1) | ZA201503323B (Direct) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6048533B2 (ja) * | 2014-05-12 | 2016-12-21 | 日産化学工業株式会社 | ２−ピリドン化合物を含有する医薬 |
| EP3144305A4 (en) * | 2014-05-13 | 2017-12-27 | Nissan Chemical Industries, Ltd. | Method for producing 2-pyridone compound |
| LT3804714T (lt) * | 2018-05-31 | 2025-03-10 | Hua Medicine (Shanghai) Ltd. | Farmacinis derinys ir kompozicija, ir derinio preparatas, kurio sudėtyje yra gliukokinazės aktyvatorius ir biguanido hipoglikeminis vaistas, taip pat jų gamybos būdas ir panaudojimas |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275069A (en) | 1979-01-22 | 1981-06-23 | The Upjohn Company | Anti-diabetic 1,2-dihydro-2-oxo-6-alkyl-nicotinic acids |
| CZ301366B6 (cs) | 1999-03-29 | 2010-02-03 | F. Hoffmann-La Roche Ag | 2-Fenyl-3-cykloalkylpropionamidová sloucenina, zpusob její prípravy a farmaceutický prostredek s jejím obsahem |
| US6353111B1 (en) | 1999-12-15 | 2002-03-05 | Hoffmann-La Roche Inc. | Trans olefinic glucokinase activators |
| EP2076502B1 (en) | 2006-06-08 | 2011-05-18 | Eli Lilly And Company | Substituted carboxamides as group i metabotropic receptor antagonists |
| JP5419706B2 (ja) | 2006-12-20 | 2014-02-19 | タケダ カリフォルニア インコーポレイテッド | グルコキナーゼアクチベーター |
| TW200904440A (en) * | 2007-07-17 | 2009-02-01 | Bristol Myers Squibb Co | Method for modulating GPR119 G protein-coupled receptor and selected compounds |
| EP2318370A1 (en) | 2008-07-29 | 2011-05-11 | Pfizer Inc. | Fluorinated heteroaryls |
| KR101737151B1 (ko) * | 2009-12-04 | 2017-05-17 | 닛산 가가쿠 고교 가부시키 가이샤 | 2-피리돈 화합물 |
| JP2013010750A (ja) * | 2011-06-02 | 2013-01-17 | Taisho Pharmaceutical Co Ltd | ２−ピリドン化合物を含有する医薬 |
-
2013
- 2013-11-12 EP EP13855534.7A patent/EP2921489B1/en active Active
- 2013-11-12 RU RU2015122717A patent/RU2662157C2/ru active
- 2013-11-12 BR BR112015010823A patent/BR112015010823A2/pt not_active Application Discontinuation
- 2013-11-12 SG SG11201503716RA patent/SG11201503716RA/en unknown
- 2013-11-12 DK DK13855534.7T patent/DK2921489T3/en active
- 2013-11-12 MY MYPI2015701491A patent/MY173812A/en unknown
- 2013-11-12 AU AU2013345930A patent/AU2013345930B2/en not_active Ceased
- 2013-11-12 PL PL13855534T patent/PL2921489T3/pl unknown
- 2013-11-12 MX MX2015005884A patent/MX361479B/es active IP Right Grant
- 2013-11-12 NO NO13855534A patent/NO2921489T3/no unknown
- 2013-11-12 NZ NZ707832A patent/NZ707832A/en not_active IP Right Cessation
- 2013-11-12 ES ES13855534.7T patent/ES2641469T3/es active Active
- 2013-11-12 WO PCT/JP2013/080517 patent/WO2014077235A1/ja not_active Ceased
- 2013-11-12 CA CA2891406A patent/CA2891406C/en not_active Expired - Fee Related
- 2013-11-12 IN IN3869DEN2015 patent/IN2015DN03869A/en unknown
- 2013-11-12 CN CN201380059272.2A patent/CN104768944B/zh not_active Expired - Fee Related
- 2013-11-12 US US14/442,157 patent/US9695148B2/en not_active Expired - Fee Related
- 2013-11-12 PT PT138555347T patent/PT2921489T/pt unknown
- 2013-11-12 JP JP2014546982A patent/JP5963025B2/ja not_active Expired - Fee Related
- 2013-11-12 KR KR1020157012117A patent/KR102160841B1/ko not_active Expired - Fee Related
- 2013-11-12 HU HUE13855534A patent/HUE034557T2/en unknown
- 2013-11-13 TW TW102141288A patent/TWI591064B/zh not_active IP Right Cessation
-
2015
- 2015-05-07 IL IL238701A patent/IL238701B/en active IP Right Grant
- 2015-05-12 PH PH12015501056A patent/PH12015501056B1/en unknown
- 2015-05-13 ZA ZA2015/03323A patent/ZA201503323B/en unknown
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