JP2021500345A5 - - Google Patents
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- Publication number
- JP2021500345A5 JP2021500345A5 JP2020521971A JP2020521971A JP2021500345A5 JP 2021500345 A5 JP2021500345 A5 JP 2021500345A5 JP 2020521971 A JP2020521971 A JP 2020521971A JP 2020521971 A JP2020521971 A JP 2020521971A JP 2021500345 A5 JP2021500345 A5 JP 2021500345A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrole
- hexahydro
- pyridazine
- cyclopentane
- amine
- 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.)
- Granted
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- -1 C 1- C 4 alkoxy Chemical group 0.000 claims description 620
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 claims description 237
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 212
- 150000003839 salts Chemical class 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 28
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 claims description 12
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
- 208000016285 Movement disease Diseases 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 208000014644 Brain disease Diseases 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 claims description 3
- DAIOMBQXJJLAGP-WHUJAJFLSA-N (3aR,6aS)-5-[[6-(1,3-dimethylpyrazol-4-yl)pyridazin-3-yl]oxymethyl]-2-(2-methylpentyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=C(C(=C1)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC(CCC)C)C1)C DAIOMBQXJJLAGP-WHUJAJFLSA-N 0.000 claims description 2
- VVSRMUFLDWLPAO-YQQQUEKLSA-N (3aR,6aS)-5-[[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxymethyl]-2-(pyridin-2-ylmethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=CC(=C1C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=NC=CC=C2)C1)C VVSRMUFLDWLPAO-YQQQUEKLSA-N 0.000 claims description 2
- YKWOCPFTGFDRAE-IHWFROFDSA-N (3aR,6aS)-5-[[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxymethyl]-2-[(3-methylpyridin-2-yl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=CC(=C1C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=NC=CC=C2C)C1)C YKWOCPFTGFDRAE-IHWFROFDSA-N 0.000 claims description 2
- KRGLJABYDQQAKG-OWCVQMPJSA-N (3aR,6aS)-5-[[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]oxymethyl]-2-(2-methylbutyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC(CC)C)C1 KRGLJABYDQQAKG-OWCVQMPJSA-N 0.000 claims description 2
- IQCLDUKZKHIUJE-YQQQUEKLSA-N (3aS,6aR)-2-(1,3-benzodioxol-5-ylmethyl)-5-[[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]oxymethyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound O1COC2=C1C=CC(=C2)CN2C[C@@H]1[C@H](C2)CC(C1)COC=1N=NC(=CC1)C1=C(C=CC(=C1)F)Cl IQCLDUKZKHIUJE-YQQQUEKLSA-N 0.000 claims description 2
- JRBVCAZRMVVUEA-IUPNCAOTSA-N (3aS,6aR)-2-(1-adamantylmethyl)-5-[[6-(1,3-dimethylpyrazol-4-yl)pyridazin-3-yl]oxymethyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound C12(CC3CC(CC(C1)C3)C2)CN2C[C@@H]3[C@H](C2)CC(C3)COC=3N=NC(=CC3)C=3C(=NN(C3)C)C JRBVCAZRMVVUEA-IUPNCAOTSA-N 0.000 claims description 2
- GQWMIXXHURUTLX-IUPNCAOTSA-N (3aS,6aR)-2-(1-adamantylmethyl)-5-[[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxymethyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound C12(CC3CC(CC(C1)C3)C2)CN2C[C@@H]3[C@H](C2)CC(C3)COC=3N=NC(=CC3)C=3N(N=CC3C)C GQWMIXXHURUTLX-IUPNCAOTSA-N 0.000 claims description 2
- UJQGCNPXKKRHAE-YQQQUEKLSA-N (3aS,6aR)-5-[[6-(1,3-dimethylpyrazol-4-yl)pyridazin-3-yl]oxymethyl]-2-(pyridin-2-ylmethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=C(C(=C1)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=NC=CC=C2)C1)C UJQGCNPXKKRHAE-YQQQUEKLSA-N 0.000 claims description 2
- PUFWQVPXAXLXPK-IHWFROFDSA-N (3aS,6aR)-5-[[6-(1,3-dimethylpyrazol-4-yl)pyridazin-3-yl]oxymethyl]-2-[(3-methylpyridin-2-yl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=C(C(=C1)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=NC=CC=C2C)C1)C PUFWQVPXAXLXPK-IHWFROFDSA-N 0.000 claims description 2
- SYUFWNRIRULXJE-WHUJAJFLSA-N (3aS,6aR)-5-[[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxymethyl]-2-(2-methylpentyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound CN1N=CC(=C1C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC(CCC)C)C1)C SYUFWNRIRULXJE-WHUJAJFLSA-N 0.000 claims description 2
- QMERANYUOVTPRO-JLYLLQBASA-N (3aS,6aR)-5-[[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]oxymethyl]-2-[(2-fluorophenyl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=C(C=CC=C2)F)C1 QMERANYUOVTPRO-JLYLLQBASA-N 0.000 claims description 2
- YMHFAZSOMKSRGU-YQQQUEKLSA-N (3aS,6aR)-5-[[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]oxymethyl]-2-[(3-methylpyridin-2-yl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=NC=CC=C2C)C1 YMHFAZSOMKSRGU-YQQQUEKLSA-N 0.000 claims description 2
- RTNFURHJDNAKPS-YQQQUEKLSA-N (3aS,6aR)-5-[[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]oxymethyl]-2-[(4-fluorophenyl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)OCC1C[C@@H]2[C@@H](CN(C2)CC2=CC=C(C=C2)F)C1 RTNFURHJDNAKPS-YQQQUEKLSA-N 0.000 claims description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000006622 cycloheptylmethyl group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 229910000870 Weathering steel Inorganic materials 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 5
- 201000000980 schizophrenia Diseases 0.000 description 4
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- 208000014094 Dystonic disease Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 206010034010 Parkinsonism Diseases 0.000 description 2
- 206010041349 Somnolence Diseases 0.000 description 2
- 206010008129 cerebral palsy Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000010118 dystonia Diseases 0.000 description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- ZUWJIYXVNJOAQZ-UHFFFAOYSA-N 4-(2,4-dimethylpyrazol-3-yl)pyridazin-3-amine Chemical compound CN1N=CC(=C1C1=C(N=NC=C1)N)C ZUWJIYXVNJOAQZ-UHFFFAOYSA-N 0.000 description 1
- 0 CC*=C(N=*C(*(C)C)=S)SI Chemical compound CC*=C(N=*C(*(C)C)=S)SI 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762574912P | 2017-10-20 | 2017-10-20 | |
| US62/574,912 | 2017-10-20 | ||
| PCT/US2018/056803 WO2019079783A1 (en) | 2017-10-20 | 2018-10-20 | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021500345A JP2021500345A (ja) | 2021-01-07 |
| JP2021500345A5 true JP2021500345A5 (enExample) | 2021-12-02 |
| JP7270989B2 JP7270989B2 (ja) | 2023-05-11 |
Family
ID=66173904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020521971A Active JP7270989B2 (ja) | 2017-10-20 | 2018-10-20 | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US11299481B2 (enExample) |
| EP (1) | EP3697759B1 (enExample) |
| JP (1) | JP7270989B2 (enExample) |
| KR (2) | KR20250037575A (enExample) |
| CN (2) | CN118063442A (enExample) |
| AU (2) | AU2018351651B2 (enExample) |
| CA (1) | CA3079617A1 (enExample) |
| IL (2) | IL273924B2 (enExample) |
| WO (1) | WO2019079783A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA202092442A3 (ru) | 2016-06-07 | 2021-08-31 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| AU2018239542C1 (en) | 2017-03-23 | 2021-02-11 | Jacobio Pharmaceuticals Co., Ltd. | Novel heterocyclic derivatives useful as SHP2 inhibitors |
| BR112020005489A2 (pt) | 2017-09-22 | 2020-09-24 | Jubilant Epipad Llc, | composto da fórmula (i), composto de fórmula (ii), composto de fórmula (iii), processo de preparação de compostos de fórmula (i), processo de preparação de compostos de fórmula (ii), processo de preparação de compostos de fórmula (iii), composição farmacêutica, método para inibir uma ou mais famílias pad em uma célula, método para tratar uma afeção mediada por um ou mais pads, utilização do composto, método para o tratamento e/ou prevenção de uma afeção mediada por um ou mais distúrbios da família pad, método para o tratamento de artrite reumatoide e método de tratamento de câncer |
| CN111225915B (zh) | 2017-10-18 | 2023-03-07 | 朱比兰特埃皮帕德有限公司 | 作为pad抑制剂的咪唑并吡啶化合物 |
| US11299481B2 (en) | 2017-10-20 | 2022-04-12 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| EP3703680B1 (en) | 2017-10-31 | 2024-05-15 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| EP3707135A1 (en) | 2017-11-06 | 2020-09-16 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as prmt5 inhibitors |
| MX2020006587A (es) | 2017-12-22 | 2020-12-10 | Ravenna Pharmaceuticals Inc | Derivados de aminopiridina como inhibidores de fosfatidilinositol fosfato cinasa. |
| JP7352294B2 (ja) * | 2018-02-02 | 2023-09-28 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
| EP3765453A1 (en) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| US20210393623A1 (en) | 2018-09-26 | 2021-12-23 | Jacobio Pharmaceuticals Co., Ltd. | Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| JP7572734B2 (ja) * | 2019-10-04 | 2024-10-24 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
| US20230122344A1 (en) * | 2019-12-10 | 2023-04-20 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| WO2021119265A1 (en) * | 2019-12-10 | 2021-06-17 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| CA3169667A1 (en) * | 2020-02-28 | 2021-09-02 | Dominic Reynolds | Pyridazine derivatives for modulating nucleic acid splicing |
| US20230183219A1 (en) * | 2020-04-24 | 2023-06-15 | Vanderbilt University | Condensed substituted hydropyrroles as antagonists of the muscarinic acetylcholine receptor m4 |
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