AU2022400780A1 - Antagonists of the muscarinic acetylcholine receptor m4 - Google Patents
Antagonists of the muscarinic acetylcholine receptor m4 Download PDFInfo
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- AU2022400780A1 AU2022400780A1 AU2022400780A AU2022400780A AU2022400780A1 AU 2022400780 A1 AU2022400780 A1 AU 2022400780A1 AU 2022400780 A AU2022400780 A AU 2022400780A AU 2022400780 A AU2022400780 A AU 2022400780A AU 2022400780 A1 AU2022400780 A1 AU 2022400780A1
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- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QIHGTLIUPKYMJQ-SMASLZHESA-N tert-butyl (3aS,5R,6aR)-3a-methyl-5-[[6-[4-(trifluoromethyl)pyridin-3-yl]pyridazin-3-yl]amino]-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(N1C[C@@](C)(C[C@@H](C2)NC3=CC=C(C4=C(C(F)(F)F)C=CN=C4)N=N3)[C@@H]2C1)=O QIHGTLIUPKYMJQ-SMASLZHESA-N 0.000 description 1
- SKRMNISZKHTUAZ-PXIJXODZSA-N tert-butyl (3aS,5R,6aR)-5-(1,3-dioxoisoindol-2-yl)-3a-methyl-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(N1C[C@@](C)(C[C@@H](C2)N(C(C3=CC=CC=C33)=O)C3=O)[C@@H]2C1)=O SKRMNISZKHTUAZ-PXIJXODZSA-N 0.000 description 1
- YASOGRAIPGIMOY-XWCIJXRUSA-N tert-butyl (3aS,5R,6aR)-5-[(6-chloropyridazin-3-yl)amino]-3a-methyl-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(N1C[C@@](C)(C[C@@H](C2)NC(N=N3)=CC=C3Cl)[C@@H]2C1)=O YASOGRAIPGIMOY-XWCIJXRUSA-N 0.000 description 1
- OLKXXAPHAMWRET-OPQQBVKSSA-N tert-butyl (3aS,5R,6aR)-5-amino-3a-methyl-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(N1C[C@@](C)(C[C@@H](C2)N)[C@@H]2C1)=O OLKXXAPHAMWRET-OPQQBVKSSA-N 0.000 description 1
- TWHGMPBHIQULRG-OUJBWJOFSA-N tert-butyl (3aS,5S,6aR)-5-hydroxy-3a-methyl-1,3,4,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(N1C[C@@](C)(C[C@H](C2)O)[C@@H]2C1)=O TWHGMPBHIQULRG-OUJBWJOFSA-N 0.000 description 1
- XOEPWIVMAMTUIJ-TVQRCGJNSA-N tert-butyl (3aS,6aR)-3a-methyl-5-oxo-3,4,6,6a-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate Chemical compound C1C(=O)C[C@]2(C)CN(C(=O)OC(C)(C)C)C[C@@H]21 XOEPWIVMAMTUIJ-TVQRCGJNSA-N 0.000 description 1
- DIDQRACXWWEPDZ-ULKQDVFKSA-N tert-butyl (3as,6ar)-5-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxylate Chemical compound C1C(O)C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@@H]21 DIDQRACXWWEPDZ-ULKQDVFKSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940100616 topical oil Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PHTUQLWOUWZIMZ-GZTJUZNOSA-N trans-dothiepin Chemical compound C1SC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 PHTUQLWOUWZIMZ-GZTJUZNOSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 229960002431 trimipramine Drugs 0.000 description 1
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000001030 ventral striatum Anatomy 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163284750P | 2021-12-01 | 2021-12-01 | |
| US63/284,750 | 2021-12-01 | ||
| PCT/US2022/051493 WO2023102100A1 (en) | 2021-12-01 | 2022-12-01 | Antagonists of the muscarinic acetylcholine receptor m4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2022400780A1 true AU2022400780A1 (en) | 2024-06-20 |
Family
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|---|---|---|---|
| AU2022400780A Pending AU2022400780A1 (en) | 2021-12-01 | 2022-12-01 | Antagonists of the muscarinic acetylcholine receptor m4 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20250145595A1 (https=) |
| EP (1) | EP4441046A1 (https=) |
| JP (1) | JP2024543973A (https=) |
| KR (1) | KR20240112343A (https=) |
| CN (2) | CN116669737A (https=) |
| AU (1) | AU2022400780A1 (https=) |
| CA (1) | CA3241298A1 (https=) |
| IL (1) | IL313219A (https=) |
| MX (1) | MX2024006718A (https=) |
| WO (1) | WO2023102100A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2018300980A1 (en) | 2017-07-12 | 2020-01-02 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| IL273924B2 (en) | 2017-10-20 | 2024-07-01 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| CA3155864A1 (en) | 2019-10-04 | 2021-04-08 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| EP4491228A3 (en) * | 2020-12-22 | 2025-04-23 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112018003417B1 (pt) * | 2016-06-22 | 2023-10-24 | Vanderbilt University | Composto modulador alostérico positivo do receptor muscarínico de acetilcolina m4 e composição farmacêutica que o compreende |
| JP2020530451A (ja) * | 2017-08-08 | 2020-10-22 | 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 |
| IL273924B2 (en) * | 2017-10-20 | 2024-07-01 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| WO2021119254A1 (en) * | 2019-12-10 | 2021-06-17 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| US20230183218A1 (en) * | 2020-04-24 | 2023-06-15 | Vanderbilt University | Condensed substituted hydropyrroles as antagonists of the muscarinic acetylcholine receptor m4 |
| EP4139303A1 (en) * | 2020-04-24 | 2023-03-01 | Vanderbilt University | Condensed substituted hydropyrroles as antagonists of the muscarinic acetylcholine receptor m4 |
-
2021
- 2021-12-22 CN CN202180087480.8A patent/CN116669737A/zh active Pending
-
2022
- 2022-12-01 AU AU2022400780A patent/AU2022400780A1/en active Pending
- 2022-12-01 EP EP22843543.4A patent/EP4441046A1/en active Pending
- 2022-12-01 CA CA3241298A patent/CA3241298A1/en active Pending
- 2022-12-01 JP JP2024532491A patent/JP2024543973A/ja active Pending
- 2022-12-01 KR KR1020247021498A patent/KR20240112343A/ko active Pending
- 2022-12-01 IL IL313219A patent/IL313219A/en unknown
- 2022-12-01 US US18/715,048 patent/US20250145595A1/en active Pending
- 2022-12-01 MX MX2024006718A patent/MX2024006718A/es unknown
- 2022-12-01 WO PCT/US2022/051493 patent/WO2023102100A1/en not_active Ceased
- 2022-12-01 CN CN202280088712.6A patent/CN118541365A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN118541365A (zh) | 2024-08-23 |
| MX2024006718A (es) | 2024-08-09 |
| JP2024543973A (ja) | 2024-11-26 |
| EP4441046A1 (en) | 2024-10-09 |
| CA3241298A1 (en) | 2023-06-08 |
| KR20240112343A (ko) | 2024-07-18 |
| IL313219A (en) | 2024-07-01 |
| US20250145595A1 (en) | 2025-05-08 |
| CN116669737A (zh) | 2023-08-29 |
| WO2023102100A1 (en) | 2023-06-08 |
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