ES2803513T3 - Derivados de quinazolin-4-ona sustituidos - Google Patents
Derivados de quinazolin-4-ona sustituidos Download PDFInfo
- Publication number
- ES2803513T3 ES2803513T3 ES14829331T ES14829331T ES2803513T3 ES 2803513 T3 ES2803513 T3 ES 2803513T3 ES 14829331 T ES14829331 T ES 14829331T ES 14829331 T ES14829331 T ES 14829331T ES 2803513 T3 ES2803513 T3 ES 2803513T3
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- ES
- Spain
- Prior art keywords
- fluoro
- methyl
- amino
- substituted
- phenyl
- 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.)
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- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 352
- -1 methoxy, difluoromethoxy, cyclopropyl Chemical group 0.000 claims abstract description 137
- 125000001424 substituent group Chemical group 0.000 claims abstract description 134
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 92
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims abstract description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 102
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- 239000003795 chemical substances by application Substances 0.000 claims description 19
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- 201000001976 pemphigus vulgaris Diseases 0.000 claims description 18
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- 206010012438 Dermatitis atopic Diseases 0.000 claims description 13
- 206010012442 Dermatitis contact Diseases 0.000 claims description 13
- 208000010247 contact dermatitis Diseases 0.000 claims description 13
- 201000003278 cryoglobulinemia Diseases 0.000 claims description 13
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 12
- 201000009961 allergic asthma Diseases 0.000 claims description 12
- 230000007815 allergy Effects 0.000 claims description 12
- 201000008937 atopic dermatitis Diseases 0.000 claims description 12
- 208000002267 Anti-neutrophil cytoplasmic antibody-associated vasculitis Diseases 0.000 claims description 11
- 208000024869 Goodpasture syndrome Diseases 0.000 claims description 11
- 206010063344 microscopic polyangiitis Diseases 0.000 claims description 11
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- 206010043561 Thrombocytopenic purpura Diseases 0.000 claims description 5
- 208000013633 acquired hemophilia Diseases 0.000 claims description 5
- 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 4
- GSRNNPHHTAAGGS-AVRDEDQJSA-N Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3ccc(F)c(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3ccc(F)c(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N GSRNNPHHTAAGGS-AVRDEDQJSA-N 0.000 claims description 4
- 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 4
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 4
- YNMJTXBAOVVQJU-AVRDEDQJSA-N COc1ncc(cn1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound COc1ncc(cn1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 YNMJTXBAOVVQJU-AVRDEDQJSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- GVQUTCQPZXNVNN-CPJSRVTESA-N 2-amino-4-[(2s,4s)-4-hydroxy-2-[5-(5-methoxypyridin-3-yl)-4-oxo-3-phenylquinazolin-2-yl]pyrrolidin-1-yl]-6-methylpyrimidine-5-carbonitrile Chemical compound COC1=CN=CC(C=2C=3C(=O)N(C=4C=CC=CC=4)C([C@H]4N(C[C@@H](O)C4)C=4C(=C(C)N=C(N)N=4)C#N)=NC=3C=CC=2)=C1 GVQUTCQPZXNVNN-CPJSRVTESA-N 0.000 claims description 2
- MRGAOHCEZOSOKZ-CVDCTZTESA-N CCOc1ncc(cn1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound CCOc1ncc(cn1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 MRGAOHCEZOSOKZ-CVDCTZTESA-N 0.000 claims description 2
- WZXBBABDWLSRIN-RDPSFJRHSA-N CO[C@H]1C[C@H](N(C1)c1nc(N)nc(C)c1C#N)c1nc2cccc(-c3cnc(OC)nc3)c2c(=O)n1-c1ccccc1 Chemical compound CO[C@H]1C[C@H](N(C1)c1nc(N)nc(C)c1C#N)c1nc2cccc(-c3cnc(OC)nc3)c2c(=O)n1-c1ccccc1 WZXBBABDWLSRIN-RDPSFJRHSA-N 0.000 claims description 2
- GJYCAYLNRYZYBQ-RDPSFJRHSA-N CO[C@H]1C[C@H](N(C1)c1nc(N)nc(C)c1C#N)c1nc2cccc(-c3cnn(C)c3)c2c(=O)n1-c1ccccc1 Chemical compound CO[C@H]1C[C@H](N(C1)c1nc(N)nc(C)c1C#N)c1nc2cccc(-c3cnn(C)c3)c2c(=O)n1-c1ccccc1 GJYCAYLNRYZYBQ-RDPSFJRHSA-N 0.000 claims description 2
- GYWXIKDPRMQFAY-CYFREDJKSA-N COc1ccncc1-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound COc1ccncc1-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 GYWXIKDPRMQFAY-CYFREDJKSA-N 0.000 claims description 2
- CYUGZUDFXIAMCN-CVDCTZTESA-N COc1ncc(cn1)-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound COc1ncc(cn1)-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 CYUGZUDFXIAMCN-CVDCTZTESA-N 0.000 claims description 2
- OPNRYAQJSHIIBL-JXFKEZNVSA-N COc1ncc(s1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound COc1ncc(s1)-c1c(F)ccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 OPNRYAQJSHIIBL-JXFKEZNVSA-N 0.000 claims description 2
- WNMCVILJGJDETC-MBSDFSHPSA-N Cc1nc(N)nc(N2C[C@@H](F)C[C@H]2c2nc3cccc(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](F)C[C@H]2c2nc3cccc(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N WNMCVILJGJDETC-MBSDFSHPSA-N 0.000 claims description 2
- WZIIFLLKOMHMBA-JTSKRJEESA-N Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3ccc(F)c(-c4cn(C)cn4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3ccc(F)c(-c4cn(C)cn4)c3c(=O)n2-c2ccccc2)c1C#N WZIIFLLKOMHMBA-JTSKRJEESA-N 0.000 claims description 2
- HZTQYQPMSVQRGX-RDPSFJRHSA-N Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cccnc4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cccnc4)c3c(=O)n2-c2ccccc2)c1C#N HZTQYQPMSVQRGX-RDPSFJRHSA-N 0.000 claims description 2
- BKXGAUFMADTWDC-CVDCTZTESA-N Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cncnc4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cncnc4)c3c(=O)n2-c2ccccc2)c1C#N BKXGAUFMADTWDC-CVDCTZTESA-N 0.000 claims description 2
- VMLVXCSOPRPIDI-CVDCTZTESA-N Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N Chemical compound Cc1nc(N)nc(N2C[C@@H](O)C[C@H]2c2nc3cccc(-c4cnn(C)c4)c3c(=O)n2-c2ccccc2)c1C#N VMLVXCSOPRPIDI-CVDCTZTESA-N 0.000 claims description 2
- YHDPTDRJMLQNJJ-RDPSFJRHSA-N Cc1ncc(cn1)-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 Chemical compound Cc1ncc(cn1)-c1cccc2nc([C@@H]3C[C@H](O)CN3c3nc(N)nc(C)c3C#N)n(-c3ccccc3)c(=O)c12 YHDPTDRJMLQNJJ-RDPSFJRHSA-N 0.000 claims description 2
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
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- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
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Classifications
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- 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
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- 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
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- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
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Landscapes
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- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| PCT/CN2014/082946 WO2015010641A1 (en) | 2013-07-24 | 2014-07-24 | Substituted quinazolin-4-one derivatives |
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| WO2009088990A1 (en) | 2008-01-04 | 2009-07-16 | Intellikine, Inc. | Certain chemical entities, compositions and methods |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| US8604032B2 (en) | 2010-05-21 | 2013-12-10 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| NZ612909A (en) | 2011-01-10 | 2015-09-25 | Infinity Pharmaceuticals Inc | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
| RU2014111823A (ru) | 2011-08-29 | 2015-10-10 | Инфинити Фармасьютикалз, Инк. | Гетероциклические соединения и их применения |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| CA2890105C (en) | 2012-11-01 | 2023-03-21 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG10201902074UA (en) | 2013-10-04 | 2019-04-29 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| ES2763103T3 (es) | 2014-06-13 | 2020-05-27 | Gilead Sciences Inc | Inhibidor de la fosfatidilinositol 3-quinasa |
| CN106458932A (zh) | 2014-06-13 | 2017-02-22 | 吉利德科学公司 | 磷脂酰肌醇3‑激酶抑制剂 |
| NZ726360A (en) | 2014-06-13 | 2018-04-27 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
| EA201692266A1 (ru) | 2014-06-13 | 2017-06-30 | Джилид Сайэнс, Инк. | Ингибиторы фосфатидилинозитол-3-киназы |
| AR100975A1 (es) * | 2014-06-24 | 2016-11-16 | Gilead Sciences Inc | Inhibidores de fosfatidilinositol 3-quinasa |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| CN106995438B (zh) * | 2016-01-22 | 2019-09-20 | 中国科学院上海药物研究所 | 一类取代喹唑啉-4-酮类化合物及其制备方法和医药用途 |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2017223422A1 (en) | 2016-06-24 | 2017-12-28 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| JOP20190052A1 (ar) | 2016-09-22 | 2019-03-21 | Astrazeneca Ab | 5-[2-(بيريدين-2-يلامينو )-3،1 ثيازول-5-يال]-3،2 – ثنائي هيدرو- 1h- إيزوإندول 1--مشتق واحد واستخدامها كمثبطات مزدوجة للدلتا وغاما فوسفاتيديلينوسيتول 3-كيناز |
| US10751339B2 (en) | 2018-01-20 | 2020-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| US10442799B1 (en) | 2018-04-07 | 2019-10-15 | Fuqiang Ruan | Heterocyclic compounds and uses thereof |
| KR101973074B1 (ko) * | 2018-11-30 | 2019-04-26 | 주식회사 티움바이오 | 퓨로피리미딘 화합물의 염 및 결정형, 및 이를 포함하는 약학적 조성물 |
| CN118373824A (zh) * | 2020-04-09 | 2024-07-23 | 成都赜灵生物医药科技有限公司 | 取代喹唑啉-4-酮类化合物及其制备方法和用途 |
| KR20240045472A (ko) * | 2022-09-30 | 2024-04-08 | 주식회사 베노바이오 | 퀴나졸린염 화합물을 포함하는 관절염 치료용 조성물 및 이의 제조 방법 |
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| US3301855A (en) | 1963-04-22 | 1967-01-31 | Ciba Geigy Corp | Derivatives of 4-nu-(2-nu, nu-dimethylaminolower alkyl)-amino quinazoline |
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-
2014
- 2014-07-22 UY UY35675A patent/UY35675A/es not_active Application Discontinuation
- 2014-07-23 AR ARP140102728A patent/AR097024A1/es unknown
- 2014-07-24 EP EP14829331.9A patent/EP3024827B1/en active Active
- 2014-07-24 MX MX2016001011A patent/MX368066B/es active IP Right Grant
- 2014-07-24 US US14/907,225 patent/US9840498B2/en active Active
- 2014-07-24 PL PL14829331T patent/PL3024827T3/pl unknown
- 2014-07-24 AU AU2014295538A patent/AU2014295538B2/en not_active Ceased
- 2014-07-24 JP JP2016528336A patent/JP6437544B2/ja active Active
- 2014-07-24 WO PCT/CN2014/082946 patent/WO2015010641A1/en not_active Ceased
- 2014-07-24 EA EA201690268A patent/EA031430B1/ru not_active IP Right Cessation
- 2014-07-24 ES ES14829331T patent/ES2803513T3/es active Active
- 2014-07-24 PT PT148293319T patent/PT3024827T/pt unknown
- 2014-07-24 TW TW103125395A patent/TW201534598A/zh unknown
- 2014-07-24 CA CA2917433A patent/CA2917433A1/en not_active Abandoned
- 2014-07-24 KR KR1020167001639A patent/KR20160033697A/ko not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| CN105452235B (zh) | 2019-08-09 |
| US9840498B2 (en) | 2017-12-12 |
| AU2014295538A1 (en) | 2016-01-21 |
| PL3024827T3 (pl) | 2020-10-19 |
| CA2917433A1 (en) | 2015-01-29 |
| EA031430B1 (ru) | 2018-12-28 |
| EP3024827B1 (en) | 2020-04-15 |
| JP6437544B2 (ja) | 2018-12-12 |
| US20160168131A1 (en) | 2016-06-16 |
| CN105452235A (zh) | 2016-03-30 |
| EP3024827A1 (en) | 2016-06-01 |
| EA201690268A1 (ru) | 2016-05-31 |
| MX368066B (es) | 2019-09-18 |
| AR097024A1 (es) | 2016-02-10 |
| PT3024827T (pt) | 2020-07-15 |
| KR20160033697A (ko) | 2016-03-28 |
| JP2016527238A (ja) | 2016-09-08 |
| TW201534598A (zh) | 2015-09-16 |
| MX2016001011A (es) | 2016-05-09 |
| AU2014295538B2 (en) | 2016-07-28 |
| UY35675A (es) | 2015-02-27 |
| WO2015010641A1 (en) | 2015-01-29 |
| EP3024827A4 (en) | 2017-04-26 |
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