NZ779310B2 - Solid polymorphs of a flna-binding compound and its hydrochloride salts - Google Patents
Solid polymorphs of a flna-binding compound and its hydrochloride saltsInfo
- Publication number
- NZ779310B2 NZ779310B2 NZ779310A NZ77931020A NZ779310B2 NZ 779310 B2 NZ779310 B2 NZ 779310B2 NZ 779310 A NZ779310 A NZ 779310A NZ 77931020 A NZ77931020 A NZ 77931020A NZ 779310 B2 NZ779310 B2 NZ 779310B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- crystalline
- triazaspiro
- dihydrochloride
- compound
- benzylmethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 5
- 239000007787 solid Substances 0.000 title claims 5
- 101100066898 Mus musculus Flna gene Proteins 0.000 title 1
- 150000003840 hydrochlorides Chemical class 0.000 title 1
- 239000012453 solvate Substances 0.000 claims abstract 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims 1
- 150000004682 monohydrates Chemical group 0.000 claims 1
- IRXSBNMGZYEZDX-UHFFFAOYSA-N n,n-dimethylacetamide;dihydrochloride Chemical compound Cl.Cl.CN(C)C(C)=O IRXSBNMGZYEZDX-UHFFFAOYSA-N 0.000 claims 1
- BSQPTZYKCAULBH-UHFFFAOYSA-N 4-benzyl-8-methyl-1,4,8-triazaspiro[4.5]decan-3-one Chemical compound C1CN(C)CCC21N(CC=1C=CC=CC=1)C(=O)CN2 BSQPTZYKCAULBH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940125306 simufilam Drugs 0.000 abstract 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Abstract
The preparation and properties of crystalline polymorphs and solvates of 1-benzyl-8-methyl-1,4,8-triazaspiro-[4.5]-decan-2-one free base and of the mono-and dihydrochloride salts and solvates thereof are disclosed, as is an amorphous polymorph of the dihydrochloride. A pharmaceutical composition containing one or more polymorphs and a method of using that composition are also disclosed.
Claims (4)
1. A solid state form of the compound of Formula III that is crystalline 1-benzylmethyl-1,4,8- triazaspiro-[4.5]-decanone dihydrochloride monohydrate, Crystalline monohydrate Form 1 terized by: an X-ray powder diffraction pattern having at least 3 peaks selected from 8.0, 9.2, 13.0, 13.8, 19.1 and 20.2 2? ± 0.2° 2?.
2. A solid state form of the compound of Formula III that is crystalline 1-benzylmethyl-1,4,8- triazaspiro-[4.5]-decanone dihydrochloride monohydrate, Crystalline drate Form 2 characterized by: an X-ray powder diffraction pattern 1004945647 having at least 3 peaks selected from 9.9, 11.9, 13.2, 14.2, 15.8, 20.0 and 20.4 2? ± 0.2° 2?.
3. A solid state form of the compound of Formula III that is crystalline 1-benzylmethyl-1,4,8-triazaspiro- [4.5]-decanone dihydrochloride dimethylacetamide solvate, Crystalline dimethylacetamide solvate Form 3 characterized by: an X-ray powder diffraction pattern having peaks at 5.5, 16.0 and 18.6 2? ± 0.2° 2?.
4. A solid state form of the compound of Formula III that is ous 1-benzylmethyl-1,4,8-triazaspiro-[4.5]- decanone dihydrochloride, amorphous Form 4 characterized by: an X-ray powder diffraction pattern ntially similar to
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962808609P | 2019-02-21 | 2019-02-21 | |
| PCT/US2020/019305 WO2020172584A1 (en) | 2019-02-21 | 2020-02-21 | Solid polymorphs of a flna-binding compound and its hydrochloride salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ779310A NZ779310A (en) | 2024-01-26 |
| NZ779310B2 true NZ779310B2 (en) | 2024-04-30 |
Family
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