ES2970361T3 - Sales de ácido tartárico de [2-(3-fluoro-5-metanosulfonilfenoxi)etil](propil)amina - Google Patents
Sales de ácido tartárico de [2-(3-fluoro-5-metanosulfonilfenoxi)etil](propil)amina Download PDFInfo
- Publication number
- ES2970361T3 ES2970361T3 ES20725728T ES20725728T ES2970361T3 ES 2970361 T3 ES2970361 T3 ES 2970361T3 ES 20725728 T ES20725728 T ES 20725728T ES 20725728 T ES20725728 T ES 20725728T ES 2970361 T3 ES2970361 T3 ES 2970361T3
- Authority
- ES
- Spain
- Prior art keywords
- salt
- tartaric acid
- formula
- formula iva
- fluoro
- 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.)
- Active
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- OSBPYFBXSLJHCR-UHFFFAOYSA-N n-[2-(3-fluoro-5-methylsulfonylphenoxy)ethyl]propan-1-amine Chemical class CCCNCCOC1=CC(F)=CC(S(C)(=O)=O)=C1 OSBPYFBXSLJHCR-UHFFFAOYSA-N 0.000 title description 15
- 150000003892 tartrate salts Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 21
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 235000002906 tartaric acid Nutrition 0.000 claims description 20
- 239000011975 tartaric acid Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 14
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- 239000001358 L(+)-tartaric acid Substances 0.000 claims description 6
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000001768 cations Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 208000012661 Dyskinesia Diseases 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 238000000634 powder X-ray diffraction Methods 0.000 description 8
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 6
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 208000018737 Parkinson disease Diseases 0.000 description 5
- -1 [2-(3-fluoro-5-methanesulfonylphenoxy)ethyl](propyl) amine Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229960004502 levodopa Drugs 0.000 description 3
- 230000007659 motor function Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SHWUYQDIJUWTPM-UHFFFAOYSA-N 2-chloro-n-propylacetamide Chemical compound CCCNC(=O)CCl SHWUYQDIJUWTPM-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical class NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- VUMAOVZBGJIIIH-UHFFFAOYSA-N 3-fluoro-5-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC(O)=CC(F)=C1 VUMAOVZBGJIIIH-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- BZWSXEONJMNNRO-UHFFFAOYSA-N FC=1C=C(OCC(=O)NCCC)C=C(C=1)S(=O)(=O)C Chemical compound FC=1C=C(OCC(=O)NCCC)C=C(C=1)S(=O)(=O)C BZWSXEONJMNNRO-UHFFFAOYSA-N 0.000 description 1
- 208000015592 Involuntary movements Diseases 0.000 description 1
- 206010030312 On and off phenomenon Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000013479 data entry Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000000848 glutamatergic effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/145—Maleic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/255—Tartaric acid
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19176514 | 2019-05-24 | ||
| EP20166361 | 2020-03-27 | ||
| PCT/EP2020/064046 WO2020239568A1 (en) | 2019-05-24 | 2020-05-20 | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2970361T3 true ES2970361T3 (es) | 2024-05-28 |
Family
ID=70682855
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES20725728T Active ES2970361T3 (es) | 2019-05-24 | 2020-05-20 | Sales de ácido tartárico de [2-(3-fluoro-5-metanosulfonilfenoxi)etil](propil)amina |
| ES23190702T Active ES3072819T3 (en) | 2019-05-24 | 2020-05-20 | Tartaric acid salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES23190702T Active ES3072819T3 (en) | 2019-05-24 | 2020-05-20 | Tartaric acid salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US12275694B2 (enExample) |
| EP (2) | EP3976581B1 (enExample) |
| JP (1) | JP7623958B2 (enExample) |
| KR (1) | KR102892833B1 (enExample) |
| CN (1) | CN113853369B (enExample) |
| AU (1) | AU2020286003B2 (enExample) |
| BR (1) | BR112021023563A2 (enExample) |
| CA (1) | CA3140805A1 (enExample) |
| CL (1) | CL2021003115A1 (enExample) |
| CO (1) | CO2021016556A2 (enExample) |
| DK (1) | DK3976581T3 (enExample) |
| ES (2) | ES2970361T3 (enExample) |
| FI (1) | FI3976581T3 (enExample) |
| IL (1) | IL288271B2 (enExample) |
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| US12275694B2 (en) | 2019-05-24 | 2025-04-15 | Irl 790 Ab | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
| JP7688690B2 (ja) | 2020-07-28 | 2025-06-04 | スーチュアン・コールン－バイオテック・バイオファーマシューティカル・カンパニー・リミテッド | ピリミジン系化合物の塩、結晶形およびその調製方法 |
| JP2023548429A (ja) * | 2020-11-10 | 2023-11-16 | インテグレイティブ・リサーチ・ラボラトリーズ・スウェーデン・アーベー | パーキンソン病、特にｌ－ｄｏｐａ誘発性ジスキネジアのための医薬品に対する感作の予防または軽減における使用のための［２－（３－フルオロ－５－メタンスルホニルフェノキシ）エチル］（プロピル）アミン（メスドペタム） |
| WO2024042540A1 (en) * | 2022-08-24 | 2024-02-29 | Alkem Laboratories Limited | Mesdopetam compositions |
| CA3268423A1 (en) | 2022-09-21 | 2024-03-28 | Assia Chemical Industries Ltd. | Solid state forms of mesdopetam and salts thereof |
| GB202312055D0 (en) | 2023-08-07 | 2023-09-20 | Ipsen Biopharm Ltd | Pharmaceutical compositions |
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| JPS51123821A (en) | 1975-04-18 | 1976-10-28 | Nippon Kayaku Co Ltd | An algicide and protective agent |
| US4128574A (en) * | 1976-10-04 | 1978-12-05 | General Electric Company | Method for making organic polycarboxylic acids |
| GB8823405D0 (en) | 1988-10-05 | 1988-11-09 | Erba Carlo Spa | Aryloxy-arythio-heteraryloxy-heteroarylthio-alkenylene derivatives of amines |
| ES2169102T3 (es) | 1994-10-14 | 2002-07-01 | Merck Patent Gmbh | (r)-(-)-2-(5-(4-fluorfenil)-3-piridilmetilaminometil)-cromano como agente activo sobre el sistema nervioso central. |
| SE9904723D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| DOP2001000189A (es) | 2000-06-30 | 2002-03-30 | Pfizer Prod Inc | Benzofenonas y sulfonas como inhibidores de la captación de glicina |
| JP2006193494A (ja) | 2005-01-17 | 2006-07-27 | Dainippon Ink & Chem Inc | ４級アンモニウム系化合物を有効成分とする心臓疾患治療剤 |
| CN101203511A (zh) | 2005-06-23 | 2008-06-18 | 阿斯利康(瑞典)有限公司 | 作为神经激肽受体拮抗剂用于治疗胃肠疾病的新氮杂环丁烷衍生物 |
| WO2007063789A1 (ja) | 2005-11-29 | 2007-06-07 | Kissei Pharmaceutical Co., Ltd. | 新規なカテコール誘導体、それを含有する医薬組成物およびそれらの用途 |
| WO2007072041A1 (en) | 2005-12-23 | 2007-06-28 | Astex Therapeutics Limited | Therapeutic compounds |
| AU2007218086A1 (en) * | 2006-02-15 | 2007-08-30 | M's Science Corporation | Piperazine derivatives |
| CA2687721A1 (en) * | 2007-06-08 | 2008-12-18 | Arena Pharmaceuticals, Inc. | Crystalline forms of (r)-1-{2-[4'-(3-methoxy-propane-1-sulfonyl)-biphenyl-4-yl]-ethyl}-2-methyl-pyrrolidine, and compositions, and methods related thereto |
| TW200932225A (en) * | 2007-12-14 | 2009-08-01 | Lundbeck & Co As H | 4-[2,3-difluoro-6-(2-fluoro-4-methyl-phenylsulfanyl)-phenyl]-piperidine |
| JP2011519839A (ja) | 2008-04-29 | 2011-07-14 | エヌエスエイビー、フィリアル アヴ ノイロサーチ スウェーデン エービー、スヴェーリエ | ドーパミン神経伝達のモジュレーター |
| WO2009133110A1 (en) | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
| MX2010011724A (es) | 2008-04-29 | 2010-11-30 | Nsab Af Neurosearch Sweden Ab | Moduladores de neurotransmision de dopamina. |
| US9006227B2 (en) * | 2011-04-19 | 2015-04-14 | Integrative Research Laboratories Sweden Ab | Modulators of cortical dopaminergic- and NMDA-receptor-mediated glutamatergic neurotransmission |
| WO2016106142A1 (en) | 2014-12-22 | 2016-06-30 | Teva Pharmaceuticals International Gmbh | L-tartrate salt of pridopidine |
| MX391727B (es) | 2016-02-08 | 2025-03-21 | Merck Patent Gmbh | Modificaciones cristalinas de clorhidrato de n-(4,5-bismetansulfonil-2-metilbenzoil)guanidina y sales de n-(4,5-bismetansulfonil-2-metilbenzoil)guanidina. |
| EP3625213B1 (en) | 2017-05-19 | 2023-03-08 | Integrative Research Laboratories Sweden AB | (+)-3-(2,3-difluorophenyl)-3-methoxypyrrolidine fumarate, a process for its preparation and uses thereof |
| SG11202000833YA (en) * | 2017-08-07 | 2020-02-27 | Suven Life Sciences Ltd | Fluoropiperidine compounds as pure 5-ht6 receptor antagonists |
| WO2020110128A1 (en) | 2018-11-29 | 2020-06-04 | Prilenia Neurotherapeutics Ltd. | Combination of pridopidine and an additional therapeutic agent for treating drug induced dyskinesia |
| US12275694B2 (en) | 2019-05-24 | 2025-04-15 | Irl 790 Ab | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
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