JP5837085B2 - ヘテロアリールスルホンアミド誘導体、それらの製造およびヒト治療におけるそれらの応用 - Google Patents
ヘテロアリールスルホンアミド誘導体、それらの製造およびヒト治療におけるそれらの応用 Download PDFInfo
- Publication number
- JP5837085B2 JP5837085B2 JP2013540331A JP2013540331A JP5837085B2 JP 5837085 B2 JP5837085 B2 JP 5837085B2 JP 2013540331 A JP2013540331 A JP 2013540331A JP 2013540331 A JP2013540331 A JP 2013540331A JP 5837085 B2 JP5837085 B2 JP 5837085B2
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- JP
- Japan
- Prior art keywords
- phenyl
- sulfonamide
- pyridine
- thiazol
- carbonyl
- 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.)
- Expired - Fee Related
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- 238000002560 therapeutic procedure Methods 0.000 title description 2
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- 238000000034 method Methods 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- -1 Ha androgenic Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 102000003734 Voltage-Gated Potassium Channels Human genes 0.000 claims description 9
- 108090000013 Voltage-Gated Potassium Channels Proteins 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- AUCJMIWMOYNWAS-UHFFFAOYSA-N N1=C(C=CC=C1)S(=O)(=O)NC1=CC=C(C=C1)C(=O)N1CCNCC1C=1SC2=C(N1)C(=CC=C2)F Chemical compound N1=C(C=CC=C1)S(=O)(=O)NC1=CC=C(C=C1)C(=O)N1CCNCC1C=1SC2=C(N1)C(=CC=C2)F AUCJMIWMOYNWAS-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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- ADXGZLMYJHQLJG-UHFFFAOYSA-N n-[2-[4-(4-methyl-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 ADXGZLMYJHQLJG-UHFFFAOYSA-N 0.000 claims description 6
- LAEYSTYZGLGKBE-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide;hydrochloride Chemical compound Cl.S1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 LAEYSTYZGLGKBE-UHFFFAOYSA-N 0.000 claims description 6
- UKYIUMLFJHIALD-UHFFFAOYSA-N n-[2-[[1-(4-methoxy-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(OC)=CC=CC=2SC=1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 UKYIUMLFJHIALD-UHFFFAOYSA-N 0.000 claims description 6
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- CHSGLAMFRYTPKF-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4S3)Br)=CC=CC2=C1 CHSGLAMFRYTPKF-UHFFFAOYSA-N 0.000 claims description 5
- XETPZJGILMXLCR-UHFFFAOYSA-N n-[2-[4-(7-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C=2C(Cl)=CC=CC=2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 XETPZJGILMXLCR-UHFFFAOYSA-N 0.000 claims description 5
- HQUPVOAZJDPSBO-UHFFFAOYSA-N n-[3-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]-6-methylpyridine-2-sulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C(C=CC=2)C(=O)N2CCN(CC2)C=2SC3=CC(Cl)=CC=C3N=2)=N1 HQUPVOAZJDPSBO-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
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- HWXWKKJZWGZDJU-UHFFFAOYSA-M [Na+].BrC1=CC=C2N=C(SC2=C1)N1CCN(CC1)C(=O)C1=C([N-]S(=O)(=O)C2=NC=CC=C2)C=CC=C1 Chemical compound [Na+].BrC1=CC=C2N=C(SC2=C1)N1CCN(CC1)C(=O)C1=C([N-]S(=O)(=O)C2=NC=CC=C2)C=CC=C1 HWXWKKJZWGZDJU-UHFFFAOYSA-M 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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- FTCLFVJBYJJMOU-UHFFFAOYSA-N n-[2-[1-(1,3-benzothiazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC=C(OC2CCN(CC2)C=2SC3=CC=CC=C3N=2)C=1NS(=O)(=O)C1=CC=CC=N1 FTCLFVJBYJJMOU-UHFFFAOYSA-N 0.000 claims description 4
- KGWRAHTZPPVCNC-UHFFFAOYSA-N n-[2-[1-(5-chloro-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound N=1C2=CC(Cl)=CC=C2OC=1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 KGWRAHTZPPVCNC-UHFFFAOYSA-N 0.000 claims description 4
- PQUJIYDNCVIJHF-UHFFFAOYSA-N n-[2-[1-(6-methyl-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(C)=CC=C2N=C1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 PQUJIYDNCVIJHF-UHFFFAOYSA-N 0.000 claims description 4
- JHMDXRSCMBWCAH-UHFFFAOYSA-N n-[2-[4-(4-methyl-1,3-benzothiazol-2-yl)-1,4-diazepane-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(CC1)CCCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 JHMDXRSCMBWCAH-UHFFFAOYSA-N 0.000 claims description 4
- PGMZZQSBSZSDSF-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]-6-methylpyridine-2-sulfonamide;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(S(=O)(=O)NC=2C(=CC=CC=2)C(=O)N2CCN(CC2)C=2SC3=CC(Br)=CC=C3N=2)=N1 PGMZZQSBSZSDSF-UHFFFAOYSA-N 0.000 claims description 4
- BLJDLAIEKBEZBH-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4O3)Cl)=CC=CC2=C1 BLJDLAIEKBEZBH-UHFFFAOYSA-N 0.000 claims description 4
- VPQNZNHSRCYEJF-UHFFFAOYSA-N n-[2-[4-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2SC=1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 VPQNZNHSRCYEJF-UHFFFAOYSA-N 0.000 claims description 4
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- VXTMDNUGGBANEZ-UHFFFAOYSA-N n-[2-[[1-(1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC=C(OCC2CN(CC2)C=2SC3=CC=CC=C3N=2)C=1NS(=O)(=O)C1=CC=CC=N1 VXTMDNUGGBANEZ-UHFFFAOYSA-N 0.000 claims description 4
- FWKRHEQNUAHZOB-UHFFFAOYSA-N n-[2-[[1-(4-methyl-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 FWKRHEQNUAHZOB-UHFFFAOYSA-N 0.000 claims description 4
- HSCTZILYCPRWKA-UHFFFAOYSA-N n-[2-[[1-(6-chloro-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Cl)=CC=C2N=C1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 HSCTZILYCPRWKA-UHFFFAOYSA-N 0.000 claims description 4
- QZTXJRUCNBJKHI-UHFFFAOYSA-N n-[2-[[1-(6-fluoro-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(F)=CC=C2N=C1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 QZTXJRUCNBJKHI-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- 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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- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
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- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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| FR1059634A FR2967674B1 (fr) | 2010-11-23 | 2010-11-23 | Derives d'heteroarylsulfonamides, leur preparation et leur application en therapeutique humaine |
| FR1059634 | 2010-11-23 | ||
| PCT/EP2011/070736 WO2012069503A1 (en) | 2010-11-23 | 2011-11-23 | Derivatives of heteroarylsulfonamides, their preparation and their application in human therapy |
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| NZ597379A (en) | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
| WO2012151452A1 (en) * | 2011-05-03 | 2012-11-08 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use in therapy |
| PH12017501176B1 (en) | 2011-05-03 | 2023-03-08 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| CN105705495A (zh) * | 2013-10-17 | 2016-06-22 | 巴斯夫欧洲公司 | 制备取代靛红酸酐化合物及其衍生物的方法 |
| WO2015095111A1 (en) * | 2013-12-18 | 2015-06-25 | Merck Sharp & Dohme Corp. | Diazepane orexin receptor antagonists |
| CN104292179A (zh) * | 2014-10-19 | 2015-01-21 | 湖南华腾制药有限公司 | 一种2-氯苯并[d]恶唑-5-甲醛的制备方法 |
| FR3029112A1 (fr) * | 2014-12-02 | 2016-06-03 | Pf Medicament | Dispersion solide a base de derives d'heteroarylsulfonamides a usage pharmaceutique |
| SI3307271T1 (sl) | 2015-06-11 | 2023-11-30 | Agios Pharmaceuticals, Inc. | Postopki za uporabo aktivatorjev piruvat kinaze |
| EP3601273B1 (en) * | 2017-03-24 | 2021-12-01 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| CN107556266B (zh) * | 2017-09-12 | 2021-04-23 | 华南农业大学 | 一种2-巯基-4-取代-6-氟苯并噻唑及其制法、应用 |
| US20200131156A1 (en) * | 2018-10-30 | 2020-04-30 | H. Lundbeck A/S | ARYLSULFONYLPYROLECARBOXAMIDE DERIVATIVES AS Kv3 POTASSIUM CHANNEL ACTIVATORS |
| CN113200934B (zh) * | 2021-05-18 | 2022-05-31 | 郑州大学 | 含苯并吗啉酮-联苯骨架化合物及其制备方法和应用 |
| CN113912595B (zh) * | 2021-10-12 | 2024-03-15 | 中国药科大学 | 一类含有噻唑或噻二唑结构的化合物及其应用 |
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| US5149700A (en) * | 1990-05-30 | 1992-09-22 | American Home Products Corporation | Substituted arylsulfonamides and benzamides |
| DE10128331A1 (de) * | 2001-06-12 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
| ATE430142T1 (de) * | 2004-12-09 | 2009-05-15 | Hoffmann La Roche | Phenylpiperazin-methanon-derivate |
| EP1902051A1 (en) * | 2005-06-09 | 2008-03-26 | Merck Frosst Canada Ltd. | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2007023882A1 (ja) * | 2005-08-26 | 2007-03-01 | Shionogi & Co., Ltd. | Ｐｐａｒアゴニスト活性を有する誘導体 |
| WO2009055357A1 (en) * | 2007-10-25 | 2009-04-30 | Boehringer Ingelheim International Gmbh | Diazepane compounds which modulate the cb2 receptor |
| CA2727780A1 (en) * | 2008-06-13 | 2009-12-17 | Bionomics Limited | Novel potassium channel blockers and uses thereof |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| CN101503392B (zh) * | 2009-03-31 | 2010-12-29 | 中国药科大学 | 芳甲胺类化合物、其制备方法及其医药用途 |
| WO2010130638A1 (en) * | 2009-05-14 | 2010-11-18 | Evotec Ag | Sulfonamide compounds, pharmaceutical compositions and uses thereof |
| NZ597379A (en) * | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
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2010
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2011
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- 2011-11-17 AR ARP110104287A patent/AR083903A1/es unknown
- 2011-11-23 AU AU2011333772A patent/AU2011333772B2/en not_active Ceased
- 2011-11-23 CA CA2817531A patent/CA2817531A1/en not_active Abandoned
- 2011-11-23 CN CN201180055123.XA patent/CN103209980B/zh not_active Expired - Fee Related
- 2011-11-23 JP JP2013540331A patent/JP5837085B2/ja not_active Expired - Fee Related
- 2011-11-23 WO PCT/EP2011/070736 patent/WO2012069503A1/en not_active Ceased
- 2011-11-23 EP EP11785690.6A patent/EP2643318A1/en not_active Withdrawn
- 2011-11-23 US US13/822,406 patent/US8846930B2/en not_active Expired - Fee Related
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- 2011-11-23 MX MX2013005734A patent/MX352396B/es active IP Right Grant
- 2011-11-23 KR KR1020137015172A patent/KR101838326B1/ko not_active Expired - Fee Related
- 2011-11-23 NZ NZ610700A patent/NZ610700A/en not_active IP Right Cessation
- 2011-11-23 UA UAA201307746A patent/UA109295C2/uk unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2011333772A1 (en) | 2013-06-06 |
| US9156834B2 (en) | 2015-10-13 |
| CN103209980B (zh) | 2015-06-03 |
| JP2014502268A (ja) | 2014-01-30 |
| WO2012069503A1 (en) | 2012-05-31 |
| RU2013126251A (ru) | 2014-12-27 |
| IL226495A0 (en) | 2013-07-31 |
| RU2582995C2 (ru) | 2016-04-27 |
| UA109295C2 (uk) | 2015-08-10 |
| TWI576106B (zh) | 2017-04-01 |
| HK1187345A1 (en) | 2014-04-04 |
| EP2643318A1 (en) | 2013-10-02 |
| AU2011333772B2 (en) | 2016-08-18 |
| US8846930B2 (en) | 2014-09-30 |
| KR20130119943A (ko) | 2013-11-01 |
| MX352396B (es) | 2017-11-22 |
| KR101838326B1 (ko) | 2018-03-13 |
| CA2817531A1 (en) | 2012-05-31 |
| MX2013005734A (es) | 2013-08-01 |
| AR083903A1 (es) | 2013-04-10 |
| FR2967674B1 (fr) | 2012-12-14 |
| US20130172326A1 (en) | 2013-07-04 |
| NZ610700A (en) | 2014-12-24 |
| IL226495A (en) | 2017-06-29 |
| FR2967674A1 (fr) | 2012-05-25 |
| MA34658B1 (fr) | 2013-11-02 |
| BR112013012615A2 (pt) | 2016-09-06 |
| US20140357624A1 (en) | 2014-12-04 |
| TW201225951A (en) | 2012-07-01 |
| CN103209980A (zh) | 2013-07-17 |
| MY168283A (en) | 2018-10-19 |
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