ES2873000T3 - Derivados del ácido borónico. - Google Patents
Derivados del ácido borónico. Download PDFInfo
- Publication number
- ES2873000T3 ES2873000T3 ES15780765T ES15780765T ES2873000T3 ES 2873000 T3 ES2873000 T3 ES 2873000T3 ES 15780765 T ES15780765 T ES 15780765T ES 15780765 T ES15780765 T ES 15780765T ES 2873000 T3 ES2873000 T3 ES 2873000T3
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- amino
- boronic acid
- acetyl
- benzofuran
- 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.)
- Active
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- 150000001642 boronic acid derivatives Chemical class 0.000 title description 5
- -1 monocyclic hydrocarbon Chemical class 0.000 claims abstract description 462
- 150000001875 compounds Chemical class 0.000 claims abstract description 456
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 85
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 65
- 239000012453 solvate Substances 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 102100030978 Cytochrome c oxidase assembly factor 1 homolog Human genes 0.000 claims abstract description 13
- 101000919635 Homo sapiens Cytochrome c oxidase assembly factor 1 homolog Proteins 0.000 claims abstract description 13
- 101100118680 Caenorhabditis elegans sec-61.G gene Proteins 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 239000004305 biphenyl Substances 0.000 claims abstract description 8
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 5
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 107
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 50
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 34
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 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 22
- 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 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 15
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 13
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 13
- 101001136986 Homo sapiens Proteasome subunit beta type-8 Proteins 0.000 claims description 12
- 102100035760 Proteasome subunit beta type-8 Human genes 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 241001103145 Pentas Species 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000004306 triazinyl group Chemical group 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 230000005856 abnormality Effects 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 230000004957 immunoregulator effect Effects 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 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 8
- 125000005620 boronic acid group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 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 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 239000003981 vehicle Substances 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 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 6
- 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 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 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 6
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 6
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
- 125000005917 3-methylpentyl group Chemical group 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- CIBBBLQQDLHWDY-KSSFIOAISA-N O1C[C@@H](C2=C1C=CC=C2)C[C@H](NC(CC1=CC=C(C=C1)OC)=O)B(O)O Chemical compound O1C[C@@H](C2=C1C=CC=C2)C[C@H](NC(CC1=CC=C(C=C1)OC)=O)B(O)O CIBBBLQQDLHWDY-KSSFIOAISA-N 0.000 claims description 6
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 6
- 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 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 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 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 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 6
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 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 5
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 5
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 5
- BTIQWBHXURATCK-IBGZPJMESA-N C(C)(=O)NC=1C=C(C=CC=1)CC(=O)N[C@@H](CC1=COC2=C1C=CC=C2)B(O)O Chemical compound C(C)(=O)NC=1C=C(C=CC=1)CC(=O)N[C@@H](CC1=COC2=C1C=CC=C2)B(O)O BTIQWBHXURATCK-IBGZPJMESA-N 0.000 claims description 5
- 208000010159 IgA glomerulonephritis Diseases 0.000 claims description 5
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
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- 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 4
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- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
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- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000004218 vascular function Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14003392 | 2014-10-01 | ||
| PCT/EP2015/002008 WO2016050359A1 (en) | 2014-10-01 | 2015-10-01 | Boronic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2873000T3 true ES2873000T3 (es) | 2021-11-03 |
Family
ID=51690789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15780765T Active ES2873000T3 (es) | 2014-10-01 | 2015-10-01 | Derivados del ácido borónico. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10294246B2 (enExample) |
| EP (1) | EP3201207B1 (enExample) |
| JP (1) | JP6835711B2 (enExample) |
| KR (1) | KR102450583B1 (enExample) |
| CN (1) | CN107001390B (enExample) |
| AU (1) | AU2015327346B2 (enExample) |
| BR (1) | BR112017006420A2 (enExample) |
| CA (1) | CA2963205A1 (enExample) |
| ES (1) | ES2873000T3 (enExample) |
| IL (1) | IL251301B (enExample) |
| MX (1) | MX370336B (enExample) |
| RU (1) | RU2017115188A (enExample) |
| SG (1) | SG11201702623TA (enExample) |
| WO (1) | WO2016050359A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3201208B1 (en) | 2014-10-01 | 2021-03-24 | Merck Patent GmbH | Boronic acid derivatives |
| US10640520B2 (en) | 2014-10-01 | 2020-05-05 | Merck Patent Gmbh | Boronic acid derivatives |
| AU2015327345B9 (en) | 2014-10-01 | 2020-06-18 | Merck Patent Gmbh | Boronic acid derivatives |
| IL272806B2 (en) * | 2017-08-24 | 2023-09-01 | Merck Patent Gmbh | The history of boronic acid, its preparation and pharmaceutical preparations containing it |
| MX2021000214A (es) * | 2018-07-26 | 2021-03-31 | Merck Patent Gmbh | Derivados de acido boronico. |
| CN113135944A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 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 |
| US20250340577A1 (en) * | 2021-03-02 | 2025-11-06 | Case Western Reserve University | Beta-lactomase inhibitors and uses thereof |
| AU2022277401B2 (en) * | 2021-05-19 | 2025-08-14 | Syngenta Crop Protection Ag | Weed control method |
| US20240287102A1 (en) | 2021-07-29 | 2024-08-29 | Merck Patent Gmbh | Novel 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 |
| JP7734276B2 (ja) * | 2021-10-14 | 2025-09-04 | ショウヤオ ホールディングス（ベイジン） カンパニー， リミテッド | ボロン酸誘導体 |
| WO2023232830A1 (en) | 2022-06-02 | 2023-12-07 | Merck Patent Gmbh | Boronic acid adducts |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2001002424A2 (en) | 1999-07-07 | 2001-01-11 | Du Pont Pharmaceuticals Company | Peptide boronic acid inhibitors of hepatitis c virus protease |
| US7271186B1 (en) | 2002-12-09 | 2007-09-18 | Northwestern University | Nanomolar β-lactamase 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. |
| SG10201605152SA (en) * | 2011-12-22 | 2016-08-30 | Ares Trading Sa | Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors |
| EP3201208B1 (en) | 2014-10-01 | 2021-03-24 | Merck Patent GmbH | Boronic acid derivatives |
| US10640520B2 (en) | 2014-10-01 | 2020-05-05 | Merck Patent Gmbh | Boronic acid derivatives |
| AU2015327345B9 (en) | 2014-10-01 | 2020-06-18 | Merck Patent Gmbh | Boronic acid derivatives |
-
2015
- 2015-10-01 EP EP15780765.2A patent/EP3201207B1/en active Active
- 2015-10-01 ES ES15780765T patent/ES2873000T3/es active Active
- 2015-10-01 WO PCT/EP2015/002008 patent/WO2016050359A1/en not_active Ceased
- 2015-10-01 CN CN201580053425.1A patent/CN107001390B/zh not_active Expired - Fee Related
- 2015-10-01 CA CA2963205A patent/CA2963205A1/en active Pending
- 2015-10-01 RU RU2017115188A patent/RU2017115188A/ru not_active Application Discontinuation
- 2015-10-01 JP JP2017518100A patent/JP6835711B2/ja not_active Expired - Fee Related
- 2015-10-01 KR KR1020177011643A patent/KR102450583B1/ko not_active Expired - Fee Related
- 2015-10-01 AU AU2015327346A patent/AU2015327346B2/en not_active Ceased
- 2015-10-01 SG SG11201702623TA patent/SG11201702623TA/en unknown
- 2015-10-01 MX MX2017004046A patent/MX370336B/es active IP Right Grant
- 2015-10-01 BR BR112017006420A patent/BR112017006420A2/pt active Search and Examination
- 2015-10-01 US US15/516,424 patent/US10294246B2/en active Active
-
2017
- 2017-03-21 IL IL251301A patent/IL251301B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2017115188A (ru) | 2018-11-06 |
| AU2015327346A1 (en) | 2017-05-18 |
| SG11201702623TA (en) | 2017-04-27 |
| US20180105539A1 (en) | 2018-04-19 |
| AU2015327346B2 (en) | 2019-12-05 |
| CN107001390B (zh) | 2020-11-27 |
| RU2017115188A3 (enExample) | 2019-03-29 |
| JP2017536335A (ja) | 2017-12-07 |
| KR102450583B1 (ko) | 2022-10-04 |
| MX2017004046A (es) | 2017-06-19 |
| IL251301A0 (en) | 2017-05-29 |
| BR112017006420A2 (pt) | 2017-12-19 |
| EP3201207A1 (en) | 2017-08-09 |
| US10294246B2 (en) | 2019-05-21 |
| IL251301B (en) | 2022-02-01 |
| EP3201207B1 (en) | 2021-02-24 |
| MX370336B (es) | 2019-12-10 |
| WO2016050359A1 (en) | 2016-04-07 |
| CN107001390A (zh) | 2017-08-01 |
| KR20170062517A (ko) | 2017-06-07 |
| CA2963205A1 (en) | 2016-04-07 |
| JP6835711B2 (ja) | 2021-02-24 |
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