JP2017510564A5 - - Google Patents
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- JP2017510564A5 JP2017510564A5 JP2016554419A JP2016554419A JP2017510564A5 JP 2017510564 A5 JP2017510564 A5 JP 2017510564A5 JP 2016554419 A JP2016554419 A JP 2016554419A JP 2016554419 A JP2016554419 A JP 2016554419A JP 2017510564 A5 JP2017510564 A5 JP 2017510564A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- cyclohexyl
- bibenzimidazolyl
- alkyl
- ethyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 20
- -1 1-cyclohexyl-1H-benzimidazol-5-yl Chemical group 0.000 description 20
- 125000000623 heterocyclic group Chemical group 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 15
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 229940088710 antibiotic agent Drugs 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 4
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 244000000010 microbial pathogen Species 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108010015899 Glycopeptides Proteins 0.000 description 2
- 102000002068 Glycopeptides Human genes 0.000 description 2
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- 108010028921 Lipopeptides Proteins 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000001775 anti-pathogenic effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 230000015788 innate immune response Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- MYLFPYVBTQNYNC-VGSWGCGISA-N (3R,4R)-1-[7-(1-cyclohexylbenzimidazol-5-yl)-1H-imidazo[4,5-b]pyridin-5-yl]-4-(hydroxymethyl)piperidin-3-ol Chemical compound C1(CCCCC1)N1C=NC2=C1C=CC(=C2)C2=C1C(=NC(=C2)N2C[C@@H]([C@H](CC2)CO)O)NC=N1 MYLFPYVBTQNYNC-VGSWGCGISA-N 0.000 description 1
- HMLNROFPENVPSM-UHFFFAOYSA-N 2-[[7-(1-cyclohexylbenzimidazol-5-yl)-1H-imidazo[4,5-b]pyridin-5-yl]amino]ethanol Chemical compound C1(CCCCC1)N1C=NC2=C1C=CC(=C2)C2=C1C(=NC(=C2)NCCO)NC=N1 HMLNROFPENVPSM-UHFFFAOYSA-N 0.000 description 1
- NGGZPLMLAYBHRK-UHFFFAOYSA-N 4-(1-cyclohexylbenzimidazol-5-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide Chemical compound C1(CCCCC1)N1C=NC2=C1C=CC(=C2)C2=NC=C(C1=C2N=CN1)C(=O)N NGGZPLMLAYBHRK-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- DEDSYSQKGKSRLV-UHFFFAOYSA-N 5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl)-7-(1-cyclohexylbenzimidazol-5-yl)-1H-imidazo[4,5-b]pyridine Chemical compound C1(CCCCC1)N1C=NC2=C1C=CC(=C2)C2=C1C(=NC(=C2)N2CC3CNCC3C2)NC=N1 DEDSYSQKGKSRLV-UHFFFAOYSA-N 0.000 description 1
- PXVXDVDJIJEKKA-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl-methylamino]-7-(1-ethyl-2-oxopyridin-4-yl)-3H-benzimidazole-4-carboxamide Chemical compound CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C1=CC(N(C=C1)CC)=O)C(=O)N)C)C PXVXDVDJIJEKKA-UHFFFAOYSA-N 0.000 description 1
- GBCRUYLURFQWBO-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl-methylamino]-7-(9-oxa-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraen-6-yl)-3H-benzimidazole-4-carboxamide Chemical compound N1=CN2CCOC3=CC(=CC1=C23)C2=CC(=C(C3=C2N=CN3)C(=O)N)N(C)CCN(C)C GBCRUYLURFQWBO-UHFFFAOYSA-N 0.000 description 1
- VPCRDEHPHHOPII-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl-methylamino]-7-quinolin-7-yl-3H-benzimidazole-4-carboxamide Chemical compound CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C1=CC=C2C=CC=NC2=C1)C(=O)N)C)C VPCRDEHPHHOPII-UHFFFAOYSA-N 0.000 description 1
- IJRYAAARUAZFRM-UHFFFAOYSA-N 7-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)-5-[2-(dimethylamino)ethoxy]-3H-benzimidazole-4-carboxamide Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OCCN(C)C IJRYAAARUAZFRM-UHFFFAOYSA-N 0.000 description 1
- BQIJIBLZNXVMGV-UHFFFAOYSA-N 7-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)-5-[2-(dimethylamino)ethyl-methylamino]-3H-benzimidazole-4-carboxamide Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)N(C)CCN(C)C BQIJIBLZNXVMGV-UHFFFAOYSA-N 0.000 description 1
- FBCCTOXLYHBZFI-UHFFFAOYSA-N 7-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-yl)-5-[methyl(2-pyrrolidin-1-ylethyl)amino]-3H-benzimidazole-4-carboxamide Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)N(CCN1CCCC1)C FBCCTOXLYHBZFI-UHFFFAOYSA-N 0.000 description 1
- BUEWHORURWJKBU-UHFFFAOYSA-N 7-(3-carbamoyl-4-methoxyphenyl)-5-[2-(dimethylamino)ethyl-methylamino]-3H-benzimidazole-4-carboxamide Chemical compound C(N)(=O)C=1C=C(C=CC1OC)C1=CC(=C(C2=C1N=CN2)C(=O)N)N(C)CCN(C)C BUEWHORURWJKBU-UHFFFAOYSA-N 0.000 description 1
- UGDNDOCUZFCATI-UHFFFAOYSA-N C1(CC1)C=1C=C(C=NC=1)C1=CC(=C(C=2NC=NC=21)C(=O)N)N(C)CCN(C)C Chemical compound C1(CC1)C=1C=C(C=NC=1)C1=CC(=C(C=2NC=NC=21)C(=O)N)N(C)CCN(C)C UGDNDOCUZFCATI-UHFFFAOYSA-N 0.000 description 1
- DPFVLNXOYPRINQ-UHFFFAOYSA-N C1=NC2=C(N1C1CCCCC1)C=CC(C1=C3N=CNC3=C(C(F)(F)F)C(N3CCC(CC3)CO)=C1)=C2 Chemical compound C1=NC2=C(N1C1CCCCC1)C=CC(C1=C3N=CNC3=C(C(F)(F)F)C(N3CCC(CC3)CO)=C1)=C2 DPFVLNXOYPRINQ-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- LDZCAHZVXGPGBL-UHFFFAOYSA-N CN(CCN(C1=C(C2=C(C(=N1)C1=CC3=C(N(C=N3)CC)C=C1)N=CN2)C(=O)N)C)C Chemical compound CN(CCN(C1=C(C2=C(C(=N1)C1=CC3=C(N(C=N3)CC)C=C1)N=CN2)C(=O)N)C)C LDZCAHZVXGPGBL-UHFFFAOYSA-N 0.000 description 1
- RVEDVHRGUBDXEH-UHFFFAOYSA-N CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2=CC=CC=C2)C=C1)C(=O)N)C)C Chemical compound CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2=CC=CC=C2)C=C1)C(=O)N)C)C RVEDVHRGUBDXEH-UHFFFAOYSA-N 0.000 description 1
- LQSXOZDBYGXRQD-UHFFFAOYSA-N CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C=1C=NC(=CC=1)N(C)C)C(=O)N)C)C Chemical compound CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C=1C=NC(=CC=1)N(C)C)C(=O)N)C)C LQSXOZDBYGXRQD-UHFFFAOYSA-N 0.000 description 1
- ZIGLWSRPWRLDTR-UHFFFAOYSA-N CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C=1C=NC=C(C1)N1CCCC1)C(=O)N)C)C Chemical compound CN(CCN(C1=C(C2=C(N=CN2)C(=C1)C=1C=NC=C(C1)N1CCCC1)C(=O)N)C)C ZIGLWSRPWRLDTR-UHFFFAOYSA-N 0.000 description 1
- ZNMKIJKDWSNECL-QNSVNVJESA-N CN1[C@H](CCC1)COC1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2COCCC2)C=C1)C(=O)N Chemical compound CN1[C@H](CCC1)COC1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2COCCC2)C=C1)C(=O)N ZNMKIJKDWSNECL-QNSVNVJESA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000194031 Enterococcus faecium Species 0.000 description 1
- 101001110286 Homo sapiens Ras-related C3 botulinum toxin substrate 1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- RAIVFRRGCHJKBV-YVWKXTFCSA-N NC(=O)C1=C(OC[C@H]2CCCN2)C=C(C2=C1NC=N2)C1=CC=C2N(C=NC2=C1)[C@@H]1CCCC[C@H]1F Chemical compound NC(=O)C1=C(OC[C@H]2CCCN2)C=C(C2=C1NC=N2)C1=CC=C2N(C=NC2=C1)[C@@H]1CCCC[C@H]1F RAIVFRRGCHJKBV-YVWKXTFCSA-N 0.000 description 1
- HNLSHAHMWRQASX-UHFFFAOYSA-N O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)N1CC(CCC1)N(C)C Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)N1CC(CCC1)N(C)C HNLSHAHMWRQASX-UHFFFAOYSA-N 0.000 description 1
- GRNYXVHDNJVYFL-UHFFFAOYSA-N O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OC1CN(CCC1)C Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OC1CN(CCC1)C GRNYXVHDNJVYFL-UHFFFAOYSA-N 0.000 description 1
- DEGIASFEDQNETG-UHFFFAOYSA-N O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OCC1N(CCC1)C Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OCC1N(CCC1)C DEGIASFEDQNETG-UHFFFAOYSA-N 0.000 description 1
- DEGIASFEDQNETG-OAHLLOKOSA-N O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OC[C@@H]1N(CCC1)C Chemical compound O1CCCC=2C1=NC=C(C2)C2=CC(=C(C1=C2N=CN1)C(=O)N)OC[C@@H]1N(CCC1)C DEGIASFEDQNETG-OAHLLOKOSA-N 0.000 description 1
- CYHIIJXAPLSUIC-UHFFFAOYSA-N OCC1(CCN(CC1)C1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2CCCCC2)C=C1)C(=O)N)CO Chemical compound OCC1(CCN(CC1)C1=C(C2=C(N=CN2)C(=C1)C1=CC2=C(N(C=N2)C2CCCCC2)C=C1)C(=O)N)CO CYHIIJXAPLSUIC-UHFFFAOYSA-N 0.000 description 1
- 102100022122 Ras-related C3 botulinum toxin substrate 1 Human genes 0.000 description 1
- 101100170580 Staphylococcus aureus dltA gene Proteins 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14305285.0 | 2014-02-27 | ||
| EP14305285.0A EP2913330A1 (en) | 2014-02-27 | 2014-02-27 | Condensed derivatives of imidazole useful as pharmaceuticals |
| PCT/EP2015/053857 WO2015128333A1 (en) | 2014-02-27 | 2015-02-24 | Heteroaromatic derivatives and their use as pharmaceuticals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017510564A JP2017510564A (ja) | 2017-04-13 |
| JP2017510564A5 true JP2017510564A5 (enExample) | 2018-03-08 |
Family
ID=50231103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016554419A Pending JP2017510564A (ja) | 2014-02-27 | 2015-02-24 | 新規なヘテロ芳香族誘導体およびそれらの医薬としての使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10301305B2 (enExample) |
| EP (2) | EP2913330A1 (enExample) |
| JP (1) | JP2017510564A (enExample) |
| WO (1) | WO2015128333A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA40532A (fr) | 2014-08-28 | 2021-04-28 | Asceneuron Sa | Inhibiteurs de glycosidases |
| CN108689945A (zh) * | 2015-12-01 | 2018-10-23 | 江苏理工学院 | 一种苯并咪唑衍生物的制备方法 |
| US11261183B2 (en) | 2016-02-25 | 2022-03-01 | Asceneuron Sa | Sulfoximine glycosidase inhibitors |
| WO2017144633A1 (en) | 2016-02-25 | 2017-08-31 | Asceneuron S. A. | Glycosidase inhibitors |
| JP2019506430A (ja) | 2016-02-25 | 2019-03-07 | エースニューロン・ソシエテ・アノニム | グリコシダーゼ阻害剤 |
| US10696668B2 (en) | 2016-02-25 | 2020-06-30 | Asceneuron Sa | Acid addition salts of piperazine derivatives |
| CN106588818B (zh) * | 2016-11-30 | 2019-07-26 | 兰州大学 | 一种医药中间体2,6-二氟-3-吗啉苯基甲胺及其制备方法 |
| EP3585790A1 (en) | 2017-02-27 | 2020-01-01 | Janssen Pharmaceutica NV | [1,2,4]-triazolo [1,5-a]-pyrimidinyl derivatives substituted with piperidine, morpholine or piperazine as oga inhibitors |
| WO2019018186A1 (en) | 2017-07-17 | 2019-01-24 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors and methods of use thereof |
| US11213525B2 (en) | 2017-08-24 | 2022-01-04 | Asceneuron Sa | Linear glycosidase inhibitors |
| AU2019318115B2 (en) | 2018-08-09 | 2024-04-18 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| US11905286B2 (en) | 2018-08-09 | 2024-02-20 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| US11795165B2 (en) | 2018-08-22 | 2023-10-24 | Asceneuron Sa | Tetrahydro-benzoazepine glycosidase inhibitors |
| US11731972B2 (en) | 2018-08-22 | 2023-08-22 | Asceneuron Sa | Spiro compounds as glycosidase inhibitors |
| KR102839500B1 (ko) | 2018-08-22 | 2025-07-28 | 아셰뉴론 에스아 | 글리코시다제 억제제로서 유용한 피페라진 유도체의 숙시네이트 및 푸마레이트 산 부가염 |
| US12016852B2 (en) | 2018-08-22 | 2024-06-25 | Asceneuron Sa | Pyrrolidine glycosidase inhibitors |
| US11787775B2 (en) | 2020-07-24 | 2023-10-17 | Genentech, Inc. | Therapeutic compounds and methods of use |
| WO2022166468A1 (zh) * | 2021-02-03 | 2022-08-11 | 药雅科技(上海)有限公司 | Bruton's酪氨酸激酶抑制剂及其应用 |
| CN114957241B (zh) * | 2021-02-23 | 2023-08-22 | 药雅科技(上海)有限公司 | 杂环类化合物作为激酶抑制剂的制备及其应用 |
| MX2023012039A (es) * | 2021-04-12 | 2024-03-05 | Impact Therapeutics Shanghai Inc | Compuestos bicíclicos fusionados sustituidos como inhibidores de parp y uso de estos. |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59126140A (ja) | 1982-12-30 | 1984-07-20 | Aisin Warner Ltd | 車両用自動変速機のトランスミツシヨン |
| US5523408A (en) * | 1994-03-25 | 1996-06-04 | The Dupont Merck Pharmaceutical Company | 2-carbocyclic and 2-heterocyclic quinoline-4-carboxylic acids and salts thereof useful as immunosuppressive agents |
| CA2196792A1 (en) | 1994-08-04 | 1996-02-15 | Yoon T. Jeon | Novel benzimidazole derivatives |
| DE60305446D1 (de) | 2002-01-07 | 2006-06-29 | Eisai Co Ltd | Desazapurine und deren verwendung |
| AR042956A1 (es) * | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| JP5002851B2 (ja) | 2005-01-20 | 2012-08-15 | 独立行政法人理化学研究所 | イミダゾピリジン誘導体 |
| US20060247263A1 (en) | 2005-04-19 | 2006-11-02 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| US20080139608A1 (en) * | 2006-12-06 | 2008-06-12 | Universiteit Leiden | 2,6,8, Trisubstituted 1-deazapurines and their different uses |
| JP2009046435A (ja) | 2007-08-21 | 2009-03-05 | Mitsubishi Tanabe Pharma Corp | グルココルチコイド受容体モジュレーター |
| SI2575968T1 (sl) * | 2010-06-01 | 2016-06-30 | Summit Therapeutics Plc | Spojine za zdravljenje bolezni, ki je povezana s clostridium difficile |
| GB2480816A (en) * | 2010-06-01 | 2011-12-07 | Summit Corp Plc | Compounds for the treatment of Clostridium difficile associated diseases |
| WO2012172043A1 (en) | 2011-06-15 | 2012-12-20 | Laboratoire Biodim | Purine derivatives and their use as pharmaceuticals for prevention or treatment of bacterial infections |
| US9572809B2 (en) * | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| DE102013009415A1 (de) * | 2013-06-05 | 2014-12-11 | Man Diesel & Turbo Se | Kolben einer Brennkraftmaschine |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| PE20210470A1 (es) * | 2014-01-31 | 2021-03-08 | Bristol Myers Squibb Co | Macrociclos con grupos p2' heterociclicos como inhibidores del factor xia |
-
2014
- 2014-02-27 EP EP14305285.0A patent/EP2913330A1/en not_active Withdrawn
-
2015
- 2015-02-24 JP JP2016554419A patent/JP2017510564A/ja active Pending
- 2015-02-24 WO PCT/EP2015/053857 patent/WO2015128333A1/en not_active Ceased
- 2015-02-24 EP EP15708148.0A patent/EP3110803B1/en not_active Not-in-force
- 2015-02-24 US US15/121,103 patent/US10301305B2/en not_active Expired - Fee Related
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