JPWO2019152809A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2019152809A5 JPWO2019152809A5 JP2020541908A JP2020541908A JPWO2019152809A5 JP WO2019152809 A5 JPWO2019152809 A5 JP WO2019152809A5 JP 2020541908 A JP2020541908 A JP 2020541908A JP 2020541908 A JP2020541908 A JP 2020541908A JP WO2019152809 A5 JPWO2019152809 A5 JP WO2019152809A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- hexane
- pyridazine
- amine
- pharmaceutically acceptable
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- -1 heteroallylen Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 208000012661 Dyskinesia Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- HDUZTFUKPGWCKE-NWMVZANLSA-N (1R,5S)-3-(1,3-benzodioxol-5-ylmethyl)-N-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound O1COC2=C1C=CC(=C2)CN1C[C@H]2C([C@H]2C1)NC=1N=NC(=CC=1)C1=C(C=CC(=C1)F)F HDUZTFUKPGWCKE-NWMVZANLSA-N 0.000 claims description 2
- ZEAFXVDVXUZGBJ-NWMVZANLSA-N (1R,5S)-3-(1,3-benzodioxol-5-ylmethyl)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound O1COC2=C1C=CC(=C2)CN1C[C@H]2C([C@H]2C1)NC=1N=NC(=CC=1)C1=C(C=CC(=C1)F)Cl ZEAFXVDVXUZGBJ-NWMVZANLSA-N 0.000 claims description 2
- RHKVBINBSIFKNN-LIMIJEPZSA-N (1R,5S)-3-[(1,5-dimethylpyrazol-3-yl)methyl]-N-[6-(2-methylindazol-5-yl)pyridazin-3-yl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound CN1N=C(C=C1C)CN1C[C@H]2C([C@H]2C1)NC=1N=NC(=CC=1)C1=CC2=CN(N=C2C=C1)C RHKVBINBSIFKNN-LIMIJEPZSA-N 0.000 claims description 2
- MLDIEIATPLTZJH-GWTOYCKXSA-N (1R,5S)-N-[6-(2,3-difluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=CC=C1F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 MLDIEIATPLTZJH-GWTOYCKXSA-N 0.000 claims description 2
- WBMGPWTWWLOIFE-QRTHJKPMSA-N (1R,5S)-N-[6-(2,4-difluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=CC(=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 WBMGPWTWWLOIFE-QRTHJKPMSA-N 0.000 claims description 2
- DTINNFOQJBRXFN-NYTJIUQPSA-N (1R,5S)-N-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3-(3,3-dimethylbutyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CCC(C)(C)C DTINNFOQJBRXFN-NYTJIUQPSA-N 0.000 claims description 2
- IHZKBWZLOQMOHS-QRTHJKPMSA-N (1R,5S)-N-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 IHZKBWZLOQMOHS-QRTHJKPMSA-N 0.000 claims description 2
- RRPNIBSPICTVRF-QRTHJKPMSA-N (1R,5S)-N-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3-(pyridin-2-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=NC=CC=C1 RRPNIBSPICTVRF-QRTHJKPMSA-N 0.000 claims description 2
- QHLLFYIIMGGIRK-GWTOYCKXSA-N (1R,5S)-N-[6-(2-chloro-3-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=CC=C1F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 QHLLFYIIMGGIRK-GWTOYCKXSA-N 0.000 claims description 2
- TVPKPMAHUNWJLM-QRTHJKPMSA-N (1R,5S)-N-[6-(2-chloro-4-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=CC(=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 TVPKPMAHUNWJLM-QRTHJKPMSA-N 0.000 claims description 2
- QLJASFVHRLHMMQ-NYTJIUQPSA-N (1R,5S)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-(3,3-dimethylbutyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CCC(C)(C)C QLJASFVHRLHMMQ-NYTJIUQPSA-N 0.000 claims description 2
- QFJLETHKVQVNRO-QRTHJKPMSA-N (1R,5S)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 QFJLETHKVQVNRO-QRTHJKPMSA-N 0.000 claims description 2
- GCQNQOGCOQTOKH-QRTHJKPMSA-N (1R,5S)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-(pyridin-2-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=NC=CC=C1 GCQNQOGCOQTOKH-QRTHJKPMSA-N 0.000 claims description 2
- ORRPMTCADOGUCX-QRTHJKPMSA-N (1R,5S)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-[(1,5-dimethylpyrazol-3-yl)methyl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=NN(C(=C1)C)C ORRPMTCADOGUCX-QRTHJKPMSA-N 0.000 claims description 2
- MEXPLCYCBSJXPT-LIMIJEPZSA-N (1R,5S)-N-[6-(2-methylindazol-5-yl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound CN1N=C2C=CC(=CC2=C1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 MEXPLCYCBSJXPT-LIMIJEPZSA-N 0.000 claims description 2
- CVNGSARVBMYURR-HTZLVSCSSA-N (1S,5R)-3-(oxan-4-ylmethyl)-N-(6-phenylpyridazin-3-yl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1(=CC=CC=C1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 CVNGSARVBMYURR-HTZLVSCSSA-N 0.000 claims description 2
- NFTHWVKKGOXHPM-VXMMSVGHSA-N (1S,5R)-3-(oxan-4-ylmethyl)-N-(6-quinolin-6-ylpyridazin-3-yl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound N1=CC=CC2=CC(=CC=C12)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 NFTHWVKKGOXHPM-VXMMSVGHSA-N 0.000 claims description 2
- RAFCHKUKILSMFD-OFFJZUQKSA-N (1S,5R)-N-(6-naphthalen-2-ylpyridazin-3-yl)-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 RAFCHKUKILSMFD-OFFJZUQKSA-N 0.000 claims description 2
- FVSIYBGHGAFTCB-AQKKSAQBSA-N (1S,5R)-N-[6-(1,3-benzodioxol-5-yl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound O1COC2=C1C=CC(=C2)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 FVSIYBGHGAFTCB-AQKKSAQBSA-N 0.000 claims description 2
- PBTGSRQWGOVBRR-AQKKSAQBSA-N (1S,5R)-N-[6-(2,5-difluorophenyl)pyridazin-3-yl]-3-[(2-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=C(C=CC=C1)F PBTGSRQWGOVBRR-AQKKSAQBSA-N 0.000 claims description 2
- NOUYSUSABILXEW-VSOVRNOCSA-N (1S,5R)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-[(3-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=CC(=CC=C1)F NOUYSUSABILXEW-VSOVRNOCSA-N 0.000 claims description 2
- IRDOIEZXWRDSSU-VSOVRNOCSA-N (1S,5R)-N-[6-(2-chloro-5-fluorophenyl)pyridazin-3-yl]-3-[(4-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=C(C=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1=CC=C(C=C1)F IRDOIEZXWRDSSU-VSOVRNOCSA-N 0.000 claims description 2
- QAJQVOXBBAPQCX-YLQYIJTPSA-N (1S,5R)-N-[6-(2-chloro-6-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C(=CC=C1)F)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 QAJQVOXBBAPQCX-YLQYIJTPSA-N 0.000 claims description 2
- OKIQYVNYTGZEJI-QRTHJKPMSA-N (1S,5R)-N-[6-(2-chlorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound ClC1=C(C=CC=C1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 OKIQYVNYTGZEJI-QRTHJKPMSA-N 0.000 claims description 2
- LZVNBHRQXHEFFT-QRTHJKPMSA-N (1S,5R)-N-[6-(2-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=C(C=CC=C1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 LZVNBHRQXHEFFT-QRTHJKPMSA-N 0.000 claims description 2
- GWTWGACGOBOYFR-HTZLVSCSSA-N (1S,5R)-N-[6-(3-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC=1C=C(C=CC=1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 GWTWGACGOBOYFR-HTZLVSCSSA-N 0.000 claims description 2
- XOCJQSABCJSYCX-HTZLVSCSSA-N (1S,5R)-N-[6-(4-fluorophenyl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound FC1=CC=C(C=C1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 XOCJQSABCJSYCX-HTZLVSCSSA-N 0.000 claims description 2
- PGLJXJZMYGUVNL-LIMIJEPZSA-N (1S,5R)-N-[6-(6-cyclopropylpyridin-3-yl)pyridazin-3-yl]-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1(CC1)C1=CC=C(C=N1)C1=CC=C(N=N1)NC1[C@H]2CN(C[C@@H]12)CC1CCOCC1 PGLJXJZMYGUVNL-LIMIJEPZSA-N 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 2
- 208000014094 Dystonic disease Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- MPRZIGYQAMQNFH-DETIRCLXSA-N N-[4-[6-[[(1R,5S)-3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]amino]pyridazin-3-yl]phenyl]acetamide Chemical compound O1CCC(CC1)CN1C[C@H]2C([C@H]2C1)NC1=CC=C(N=N1)C1=CC=C(C=C1)NC(C)=O MPRZIGYQAMQNFH-DETIRCLXSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010034010 Parkinsonism Diseases 0.000 claims description 2
- 206010041349 Somnolence Diseases 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 206010008129 cerebral palsy Diseases 0.000 claims description 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000010118 dystonia Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000000034 method Methods 0.000 description 6
- WBBAZRCDYWDMIF-VSOVRNOCSA-N (1S,5R)-3-(3,3-dimethylbutyl)-N-[6-(2-methylindazol-5-yl)pyridazin-3-yl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound CC(CCN1C[C@H]2C([C@H]2C1)NC=1N=NC(=CC=1)C1=CC2=CN(N=C2C=C1)C)(C)C WBBAZRCDYWDMIF-VSOVRNOCSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862625656P | 2018-02-02 | 2018-02-02 | |
| US62/625,656 | 2018-02-02 | ||
| PCT/US2019/016300 WO2019152809A1 (en) | 2018-02-02 | 2019-02-01 | Antagonists of the muscarinic acetylcholine receptor m4 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021513519A JP2021513519A (ja) | 2021-05-27 |
| JP2021513519A5 JP2021513519A5 (https=) | 2022-02-16 |
| JPWO2019152809A5 true JPWO2019152809A5 (https=) | 2022-02-16 |
| JP7352294B2 JP7352294B2 (ja) | 2023-09-28 |
Family
ID=67480022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020541908A Active JP7352294B2 (ja) | 2018-02-02 | 2019-02-01 | 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 (10)
| Country | Link |
|---|---|
| US (1) | US11414406B2 (https=) |
| EP (1) | EP3746421B1 (https=) |
| JP (1) | JP7352294B2 (https=) |
| KR (1) | KR20200116945A (https=) |
| CN (1) | CN111788182B (https=) |
| AU (1) | AU2019216492A1 (https=) |
| CA (1) | CA3090130A1 (https=) |
| IL (1) | IL276411B2 (https=) |
| WO (1) | WO2019152809A1 (https=) |
| ZA (1) | ZA202004638B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12600726B2 (en) | 2017-07-12 | 2026-04-14 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| IL310346A (en) | 2017-10-20 | 2024-03-01 | Univ Vanderbilt | Muscarinic acetylcholine M4 receptor antagonists |
| EP3728228A1 (en) | 2017-12-22 | 2020-10-28 | Ravenna Pharmaceuticals, Inc. | Aminopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| WO2020243423A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| KR20220030222A (ko) | 2019-05-31 | 2022-03-10 | 이케나 온콜로지, 인코포레이티드 | Tead 억제제 및 이의 용도 |
| 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 |
| AU2020358000A1 (en) * | 2019-10-04 | 2022-04-07 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2021174176A1 (en) * | 2020-02-28 | 2021-09-02 | Remix Therapeutics Inc. | Pyridazine dervatives for modulating nucleic acid splicing |
| IL303128A (en) | 2020-11-26 | 2023-07-01 | Rezubio Pharmaceuticals Co Ltd | Anticholinergic agents |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2676444B1 (fr) * | 1991-05-16 | 1995-03-10 | Sanofi Elf | Nouveaux derives d'amino-3 pyridazines actifs sur le systeme nerveux central, procede de preparation et compositions pharmaceutiques en contenant. |
| EP2280003B1 (en) | 2002-07-15 | 2014-04-02 | Symphony Evolution, Inc. | Process for preparing receptor-type kinase modulators |
| US20040044029A1 (en) | 2002-08-14 | 2004-03-04 | Dart Michael J. | Azabicyclic compounds are central nervous system active agents |
| EP1581522B1 (en) * | 2002-12-23 | 2008-02-20 | Ranbaxy Laboratories Limited | Flavaxate derivatives as muscarinic receptor antagonists |
| WO2004089898A1 (en) * | 2003-04-09 | 2004-10-21 | Ranbaxy Laboratories Limited | Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists |
| PT2213661E (pt) | 2003-09-26 | 2011-12-15 | Exelixis Inc | Moduladores de c-met e métodos de uso |
| DE102004039789A1 (de) | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP1796667A2 (en) * | 2004-09-27 | 2007-06-20 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| WO2006035280A1 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | 3,4-dihydroisoquinoline compounds as muscrinic receptor antagonists for the treatment of respiratory, urinary and gastrointestinal diseases |
| GB0510204D0 (en) | 2005-05-19 | 2005-06-22 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| EP1904495A2 (en) * | 2005-07-11 | 2008-04-02 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| GB0521508D0 (en) * | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| WO2008065500A2 (en) | 2006-11-30 | 2008-06-05 | Pfizer Products Inc. | Heteroaryl amides as type i glycine transport inhibitors |
| EP2129660A2 (en) * | 2006-12-19 | 2009-12-09 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| CN101230058A (zh) | 2007-01-23 | 2008-07-30 | 上海恒瑞医药有限公司 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| CN103102352B (zh) | 2011-11-15 | 2015-08-12 | 山东亨利医药科技有限责任公司 | 酪氨酸激酶抑制剂吲哚满酮衍生物 |
| AU2014224975B2 (en) * | 2013-03-05 | 2017-09-14 | Merck Patent Gmbh | Triazolo(4,5-d)pyrimidine derivatives for the treatment of diseases such as cancer |
| TW201444820A (zh) | 2013-03-13 | 2014-12-01 | Abbvie Inc | 吡啶ｃｄｋ９激酶抑制劑 |
| MA39838B1 (fr) | 2014-04-04 | 2019-05-31 | Pfizer | Composés bicycliques hétéroaryle ou aryle fusionnés et leur utilisation en tant qu'inhibiteurs irak4 |
| PE20211782A1 (es) | 2014-05-23 | 2021-09-08 | Hoffmann La Roche | Compuestos de 5-cloro-2-difluorometoxifenil pirazolopirimidina, composiciones y metodos de uso de los mismos |
| JO3579B1 (ar) | 2014-09-26 | 2020-07-05 | Luc Therapeutics Inc | مُعدِلات تفاغرية سالبة لمستقبل nr2b من المركب n-ألكيل أريل-5-أوكسي أريل-ثامن هيدرو-خماسي الحلقة [c] بيرول |
| EP3371164B1 (en) | 2015-11-06 | 2022-03-16 | Neurocrine Biosciences, Inc. | N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1-carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
| EA201800367A1 (ru) * | 2015-12-10 | 2019-02-28 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения болезни хантингтона |
| KR20180110132A (ko) | 2016-02-16 | 2018-10-08 | 반더빌트유니버시티 | 무스카린성 아세틸콜린 수용체 m1의 양성 알로스테릭 조절제 |
| US20170355708A1 (en) * | 2016-06-09 | 2017-12-14 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| AU2018313802A1 (en) * | 2017-08-08 | 2020-02-20 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2019079410A1 (en) * | 2017-10-17 | 2019-04-25 | Vanderbilt University | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
| IL310346A (en) | 2017-10-20 | 2024-03-01 | Univ Vanderbilt | Muscarinic acetylcholine M4 receptor antagonists |
| AU2018360581A1 (en) | 2017-10-31 | 2020-06-11 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| EP3732163A4 (en) * | 2017-12-20 | 2021-07-14 | Vanderbilt University | MUSCARIN M4 ACETYLCHOLIN RECEPTOR ANTAGONISTS |
-
2019
- 2019-02-01 CN CN201980012827.5A patent/CN111788182B/zh not_active Expired - Fee Related
- 2019-02-01 JP JP2020541908A patent/JP7352294B2/ja active Active
- 2019-02-01 WO PCT/US2019/016300 patent/WO2019152809A1/en not_active Ceased
- 2019-02-01 KR KR1020207023725A patent/KR20200116945A/ko not_active Ceased
- 2019-02-01 EP EP19747509.8A patent/EP3746421B1/en active Active
- 2019-02-01 US US16/966,306 patent/US11414406B2/en active Active
- 2019-02-01 IL IL276411A patent/IL276411B2/en unknown
- 2019-02-01 AU AU2019216492A patent/AU2019216492A1/en not_active Abandoned
- 2019-02-01 CA CA3090130A patent/CA3090130A1/en active Pending
-
2020
- 2020-07-27 ZA ZA2020/04638A patent/ZA202004638B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2021513519A5 (https=) | ||
| JP6585158B2 (ja) | ヤヌスキナーゼの阻害に有用なピロロ［２，３−ｄ］ピリミジン誘導体 | |
| KR101961500B1 (ko) | 세린/트레오닌 키나제 억제제 | |
| JP6503386B2 (ja) | ＭＤＭ２−ｐ５３阻害剤としての新しいスピロ［３Ｈ−インドール−３，２’−ピロリジン］−２（１Ｈ）−オン化合物および誘導体 | |
| CN104093720B (zh) | 具有咪唑并三嗪酮骨架的pde9抑制剂 | |
| JP6474166B2 (ja) | 化合物及び使用方法 | |
| JP6505023B2 (ja) | Ｃｎｓおよび他の障害を治療するための、ｐｄｅ４アイソザイムの阻害薬としてのアザベンゾイミダゾール化合物 | |
| CN112154145B (zh) | 哌嗪氮杂螺衍生物 | |
| JP2000507966A (ja) | 療法、特に良性前立腺過形成の治療において有用なキノリンおよびキナゾリン化合物 | |
| AU2007329064C1 (en) | 2-Aminoquinolines as 5-HT(5A) receptor antagonists | |
| RU2009136299A (ru) | Новые производные 3-({1,2,4}триазоло{4,3-а}пиридин-7-ил)бензамида | |
| BR122023004130B1 (pt) | Compostos heteroaromáticos, composição farmacêutica e uso dos referidos compostos no tratamento de distúrbios mediados ou associados a dopamina d1 | |
| PH12015502685B1 (en) | 6,7-DIHYDROPYRAZOLO[1,5-a]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS | |
| JP2020514377A (ja) | ピリミジニル−ピリジルオキシ−ナフチル化合物及びｉｒｅ１関連疾患及び障害を治療する方法 | |
| CA2954222C (en) | 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5h)-one compounds and their use as negative allosteric modulators of mglur2 receptors | |
| CA2611530A1 (en) | Tyrosine kinase inhibitors | |
| CA2954093A1 (en) | 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5h)-one compounds and their use as negative allosteric modulators of mglur2 receptors | |
| KR20200074971A (ko) | 헤테로사이클릭 화합물, 헤테로사이클릭 화합물을 포함하는 조성물 및 그의 사용 방법 | |
| JPWO2019152809A5 (https=) | ||
| AU2017208119B2 (en) | 6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine dopamine D3 ligands | |
| AU2021299200A1 (en) | Processes for making SERD tricyclic compounds having a substituted phenyl or pyridinyl moiety | |
| AU2015212495A1 (en) | Antibacterial combinations comprising polymyxin | |
| CN114805351A (zh) | 作为pi3k/mtor抑制剂的带有酰胺基的吡啶基取代的稠合喹啉化合物 | |
| JP2017513910A (ja) | 複素環式化合物およびそのドーパミンｄ１リガンドとしての使用 | |
| CN105189485B (zh) | 作为抗疟剂的新型丙烯酰胺衍生物 |