ES2876287T3 - Derivados del ácido borónico. - Google Patents
Derivados del ácido borónico. Download PDFInfo
- Publication number
- ES2876287T3 ES2876287T3 ES15800714T ES15800714T ES2876287T3 ES 2876287 T3 ES2876287 T3 ES 2876287T3 ES 15800714 T ES15800714 T ES 15800714T ES 15800714 T ES15800714 T ES 15800714T ES 2876287 T3 ES2876287 T3 ES 2876287T3
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- amino
- indicates
- boronic acid
- 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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- 150000001642 boronic acid derivatives Chemical class 0.000 title description 3
- -1 bicyclic hydrocarbon Chemical class 0.000 claims abstract description 578
- 150000001875 compounds Chemical class 0.000 claims abstract description 230
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 60
- 239000012453 solvate Substances 0.000 claims abstract description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 13
- 239000004305 biphenyl Substances 0.000 claims abstract description 10
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 10
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 23
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 21
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
- 101001136986 Homo sapiens Proteasome subunit beta type-8 Proteins 0.000 claims description 16
- 102100035760 Proteasome subunit beta type-8 Human genes 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 9
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 9
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 9
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 9
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 9
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 9
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 9
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 9
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 9
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 8
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 8
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 8
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 8
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 8
- 125000005917 3-methylpentyl group Chemical group 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 8
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 8
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 8
- 125000005620 boronic acid group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 8
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000003944 tolyl group Chemical group 0.000 claims description 8
- 239000003981 vehicle Substances 0.000 claims description 8
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 7
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004799 bromophenyl group Chemical group 0.000 claims description 7
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 7
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 7
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
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- OHELUJZPYHXZDO-ZDUSSCGKSA-N C(C)C=1C=C(C=CC=1)C[C@H](NC(CCS(=O)(=O)C)=O)B(O)O Chemical compound C(C)C=1C=C(C=CC=1)C[C@H](NC(CCS(=O)(=O)C)=O)B(O)O OHELUJZPYHXZDO-ZDUSSCGKSA-N 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- A61K31/69—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Oncology (AREA)
- Hematology (AREA)
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- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
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| EP14003391 | 2014-10-01 | ||
| PCT/EP2015/001931 WO2016050356A1 (en) | 2014-10-01 | 2015-10-01 | Boronic acid derivatives |
Publications (1)
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| ES2876287T3 true ES2876287T3 (es) | 2021-11-12 |
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| EP (1) | EP3201208B1 (enExample) |
| JP (1) | JP6896618B2 (enExample) |
| KR (1) | KR20170062518A (enExample) |
| CN (1) | CN107074885B (enExample) |
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| SG (1) | SG11201702620SA (enExample) |
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| SG11201702623TA (en) | 2014-10-01 | 2017-04-27 | Merck Patent Gmbh | Boronic acid derivatives |
| AU2015327411B2 (en) | 2014-10-01 | 2020-01-02 | Merck Patent Gmbh | Boronic acid derivatives |
| JP6662865B2 (ja) | 2014-10-01 | 2020-03-11 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ボロン酸誘導体 |
| SI3571208T1 (sl) * | 2017-01-18 | 2021-06-30 | Principia Biopharma Inc. | Zaviralci imunoproteasomov |
| WO2019038250A1 (en) | 2017-08-24 | 2019-02-28 | Merck Patent Gmbh | Boronic acid derivatives |
| WO2019060651A1 (en) | 2017-09-21 | 2019-03-28 | Kezar Life Sciences | POLY THERAPY FOR IMMUNOLOGICAL DISEASES |
| CN112469480A (zh) | 2018-07-26 | 2021-03-09 | 默克专利股份公司 | 硼酸衍生物 |
| CN113135943A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 硼酸衍生物 |
| CN113135944A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 硼酸衍生物 |
| IL310390A (en) | 2021-07-29 | 2024-03-01 | Merck Patent Gmbh | Crystalline forms of [(1r)-2-(1-benzofuran-3-yl)-1-{[(1s,2r,4r)-7- oxabicyclo[2.2.1]heptan-2-yl]formamido}ethyl]boronic acid, adducts thereof, and processes to obtain |
| KR20240090392A (ko) * | 2021-10-14 | 2024-06-21 | 쇼우야오 홀딩스 (베이징) 코., 엘티디. | 보론산 유도체 |
| CN117003776A (zh) * | 2022-04-29 | 2023-11-07 | 科辉智药生物科技(深圳)有限公司 | 一种硼酸类蛋白酶体抑制剂及其用途 |
| WO2023232830A1 (en) | 2022-06-02 | 2023-12-07 | Merck Patent Gmbh | Boronic acid adducts |
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| IL111175A0 (en) * | 1993-10-07 | 1994-12-29 | Du Pont Merck Pharma | Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them |
| US6083903A (en) * | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
| EP1196436A2 (en) * | 1999-07-07 | 2002-04-17 | Bristol-Myers Squibb Pharma Company | Peptide boronic acid inhibitors of hepatitis c virus protease |
| EP1863513A2 (en) * | 2005-03-11 | 2007-12-12 | The University of North Carolina at Chapel Hill | Potent and specific immunoproteasome inhibitors |
| EA201000774A1 (ru) * | 2007-11-13 | 2010-12-30 | Новартис Интернэшнл Фармасьютикл Лтд. | Ингибиторы бета-лактамазы |
| AR075090A1 (es) * | 2008-09-29 | 2011-03-09 | Millennium Pharm Inc | Derivados de acido 1-amino-2-ciclobutiletilboronico inhibidores de proteosoma,utiles como agentes anticancerigenos, y composiciones farmaceuticas que los comprenden. |
| US9359398B2 (en) * | 2010-03-01 | 2016-06-07 | Onyx Therapeutics, Inc. | Compounds for immunoproteasome inhibition |
| SG10201605152SA (en) * | 2011-12-22 | 2016-08-30 | Ares Trading Sa | Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors |
| JP6018319B2 (ja) * | 2012-12-03 | 2016-11-02 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 置換トリアゾールボロン酸化合物 |
| AU2015327411B2 (en) | 2014-10-01 | 2020-01-02 | Merck Patent Gmbh | Boronic acid derivatives |
| JP6662865B2 (ja) | 2014-10-01 | 2020-03-11 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ボロン酸誘導体 |
| SG11201702623TA (en) | 2014-10-01 | 2017-04-27 | Merck Patent Gmbh | Boronic acid derivatives |
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- 2015-10-01 MX MX2017004043A patent/MX2017004043A/es unknown
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| RU2017115191A3 (enExample) | 2019-02-12 |
| JP6896618B2 (ja) | 2021-06-30 |
| EP3201208B1 (en) | 2021-03-24 |
| BR112017006349A2 (pt) | 2017-12-12 |
| KR20170062518A (ko) | 2017-06-07 |
| CN107074885B (zh) | 2020-11-27 |
| RU2017115191A (ru) | 2018-11-06 |
| US20180105538A1 (en) | 2018-04-19 |
| MX2017004043A (es) | 2017-07-04 |
| SG11201702620SA (en) | 2017-04-27 |
| EP3201208A1 (en) | 2017-08-09 |
| IL251299A0 (en) | 2017-05-29 |
| CA2963198A1 (en) | 2016-04-07 |
| AU2015327412B2 (en) | 2020-01-16 |
| WO2016050356A1 (en) | 2016-04-07 |
| US10253049B2 (en) | 2019-04-09 |
| JP2018502048A (ja) | 2018-01-25 |
| CN107074885A (zh) | 2017-08-18 |
| AU2015327412A1 (en) | 2017-05-18 |
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