RU2717542C9 - Ротиготина бегенат, его способ получения и применение - Google Patents
Ротиготина бегенат, его способ получения и применение Download PDFInfo
- Publication number
- RU2717542C9 RU2717542C9 RU2018146096A RU2018146096A RU2717542C9 RU 2717542 C9 RU2717542 C9 RU 2717542C9 RU 2018146096 A RU2018146096 A RU 2018146096A RU 2018146096 A RU2018146096 A RU 2018146096A RU 2717542 C9 RU2717542 C9 RU 2717542C9
- Authority
- RU
- Russia
- Prior art keywords
- rotigotine
- crystalline form
- behenate
- rotigotine behenate
- ray powder
- Prior art date
Links
- 229960003179 rotigotine Drugs 0.000 title claims abstract description 161
- KFQYTPMOWPVWEJ-INIZCTEOSA-N rotigotine Chemical compound CCCN([C@@H]1CC2=CC=CC(O)=C2CC1)CCC1=CC=CS1 KFQYTPMOWPVWEJ-INIZCTEOSA-N 0.000 title claims abstract description 160
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 title claims abstract description 74
- 229940116224 behenate Drugs 0.000 title claims abstract description 74
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 230000005855 radiation Effects 0.000 claims abstract description 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 138
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 239000011259 mixed solution Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000843 powder Substances 0.000 claims description 13
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 12
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 12
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 235000021357 Behenic acid Nutrition 0.000 claims description 6
- 229940116226 behenic acid Drugs 0.000 claims description 6
- OAOSXODRWGDDCV-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine;4-methylbenzenesulfonic acid Chemical compound CN(C)C1=CC=NC=C1.CC1=CC=C(S(O)(=O)=O)C=C1 OAOSXODRWGDDCV-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 102000015554 Dopamine receptor Human genes 0.000 claims description 5
- 108050004812 Dopamine receptor Proteins 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 238000001757 thermogravimetry curve Methods 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000008280 blood Substances 0.000 description 43
- 210000004369 blood Anatomy 0.000 description 43
- 241000700159 Rattus Species 0.000 description 33
- 229940079593 drug Drugs 0.000 description 20
- 239000007787 solid Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 238000010255 intramuscular injection Methods 0.000 description 7
- 239000007927 intramuscular injection Substances 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- QZZGJDVWLFXDLK-UHFFFAOYSA-M tetracosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O QZZGJDVWLFXDLK-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 6
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 6
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 238000010171 animal model Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 229940049964 oleate Drugs 0.000 description 5
- 238000013268 sustained release Methods 0.000 description 5
- 239000012730 sustained-release form Substances 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 210000000744 eyelid Anatomy 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- CEXBONHIOKGWNU-NTISSMGPSA-N hydron;(6s)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol;chloride Chemical compound [Cl-].CCC[NH+]([C@@H]1CC2=CC=CC(O)=C2CC1)CCC1=CC=CS1 CEXBONHIOKGWNU-NTISSMGPSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229940098778 Dopamine receptor agonist Drugs 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- -1 rotigotine ester Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/090803 WO2018014277A1 (zh) | 2016-07-21 | 2016-07-21 | 罗替戈汀山嵛酸酯及其制备方法和用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2717542C1 RU2717542C1 (ru) | 2020-03-24 |
| RU2717542C9 true RU2717542C9 (ru) | 2020-08-12 |
Family
ID=60992805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018146096A RU2717542C9 (ru) | 2016-07-21 | 2016-07-21 | Ротиготина бегенат, его способ получения и применение |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10669249B2 (https=) |
| EP (1) | EP3489227B1 (https=) |
| JP (1) | JP6751208B2 (https=) |
| KR (1) | KR20190031314A (https=) |
| CN (1) | CN109415335B (https=) |
| AU (1) | AU2016415408B2 (https=) |
| BR (1) | BR112019001035A2 (https=) |
| CA (1) | CA3030043C (https=) |
| ES (1) | ES2855976T3 (https=) |
| MY (1) | MY195897A (https=) |
| PH (1) | PH12018550212A1 (https=) |
| PL (1) | PL3489227T3 (https=) |
| RU (1) | RU2717542C9 (https=) |
| SG (1) | SG11201811543XA (https=) |
| WO (1) | WO2018014277A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2717542C9 (ru) * | 2016-07-21 | 2020-08-12 | Шаньдун Луе Фармасьютикал Ко., Лтд. | Ротиготина бегенат, его способ получения и применение |
| CN108341798B (zh) * | 2017-01-23 | 2021-05-25 | 沈阳药科大学 | 罗替戈汀衍生物及其制备和应用 |
| CN114423746A (zh) * | 2019-09-30 | 2022-04-29 | 山东绿叶制药有限公司 | 化合物及其制备方法和用途 |
| JP7621009B2 (ja) * | 2020-10-27 | 2025-01-24 | ▲広▼州市恒▲諾▼康医▲薬▼科技有限公司 | テトラヒドロナフタレン系化合物、その医薬組成物及びその使用 |
| WO2024208226A1 (zh) * | 2023-04-04 | 2024-10-10 | 广州市恒诺康医药科技有限公司 | 四氢萘类化合物、其药物组合物及其用途 |
| CN119504742B (zh) * | 2024-11-18 | 2025-10-28 | 陕西师范大学 | 一种娃儿藤碱和安托芬的全合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA200601227A1 (ru) * | 2003-12-24 | 2006-12-29 | Шварц Фарма Аг | Применение ротиготина для лечения или предотвращения гибели дофаминергических нейронов |
| RU2478383C2 (ru) * | 2002-12-02 | 2013-04-10 | Уцб Фарма Гмбх | Ионофоретическая доставка ротиготина для лечения болезни паркинсона |
| WO2016014242A1 (en) * | 2014-07-21 | 2016-01-28 | Spriaso Llc | Compositions comprising bioreversible derivatives of hydroxy n-substituted-2-aminotetralins, dosage forms, and related methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101481643B1 (ko) | 2010-11-25 | 2015-01-12 | 산동 루예 파마슈티칼 컴파니 리미티드 | 로티고틴, 이의 유도체 또는 로티고틴 또는 이의 유도체의 약제학적으로 허용가능한 염의 조성물 |
| WO2013168033A1 (en) * | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neurologic diseases |
| US9956201B2 (en) * | 2014-07-21 | 2018-05-01 | Spriaso Llc | Compositions comprising bioreversible derivatives of hydroxy N-substituted-2-aminotetralins, and related dosage forms |
| RU2717542C9 (ru) * | 2016-07-21 | 2020-08-12 | Шаньдун Луе Фармасьютикал Ко., Лтд. | Ротиготина бегенат, его способ получения и применение |
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2016
- 2016-07-21 RU RU2018146096A patent/RU2717542C9/ru active
- 2016-07-21 SG SG11201811543XA patent/SG11201811543XA/en unknown
- 2016-07-21 PL PL16909205T patent/PL3489227T3/pl unknown
- 2016-07-21 US US16/309,807 patent/US10669249B2/en active Active
- 2016-07-21 KR KR1020197005257A patent/KR20190031314A/ko not_active Abandoned
- 2016-07-21 AU AU2016415408A patent/AU2016415408B2/en active Active
- 2016-07-21 ES ES16909205T patent/ES2855976T3/es active Active
- 2016-07-21 CN CN201680087177.7A patent/CN109415335B/zh active Active
- 2016-07-21 JP JP2019524492A patent/JP6751208B2/ja active Active
- 2016-07-21 CA CA3030043A patent/CA3030043C/en not_active Expired - Fee Related
- 2016-07-21 BR BR112019001035-1A patent/BR112019001035A2/pt not_active IP Right Cessation
- 2016-07-21 MY MYPI2018002909A patent/MY195897A/en unknown
- 2016-07-21 WO PCT/CN2016/090803 patent/WO2018014277A1/zh not_active Ceased
- 2016-07-21 EP EP16909205.3A patent/EP3489227B1/en active Active
-
2018
- 2018-12-26 PH PH12018550212A patent/PH12018550212A1/en unknown
-
2020
- 2020-04-27 US US16/860,037 patent/US11111227B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2478383C2 (ru) * | 2002-12-02 | 2013-04-10 | Уцб Фарма Гмбх | Ионофоретическая доставка ротиготина для лечения болезни паркинсона |
| EA200601227A1 (ru) * | 2003-12-24 | 2006-12-29 | Шварц Фарма Аг | Применение ротиготина для лечения или предотвращения гибели дофаминергических нейронов |
| WO2016014242A1 (en) * | 2014-07-21 | 2016-01-28 | Spriaso Llc | Compositions comprising bioreversible derivatives of hydroxy n-substituted-2-aminotetralins, dosage forms, and related methods |
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| BR112019001035A2 (pt) | 2019-04-30 |
| PL3489227T3 (pl) | 2021-05-04 |
| JP2019523297A (ja) | 2019-08-22 |
| MY195897A (en) | 2023-02-27 |
| US20200255396A1 (en) | 2020-08-13 |
| RU2717542C1 (ru) | 2020-03-24 |
| PH12018550212A1 (en) | 2019-10-28 |
| AU2016415408B2 (en) | 2019-04-11 |
| EP3489227B1 (en) | 2020-10-21 |
| US10669249B2 (en) | 2020-06-02 |
| CN109415335A (zh) | 2019-03-01 |
| AU2016415408A1 (en) | 2019-01-17 |
| CA3030043C (en) | 2021-01-19 |
| JP6751208B2 (ja) | 2020-09-02 |
| SG11201811543XA (en) | 2019-02-27 |
| WO2018014277A1 (zh) | 2018-01-25 |
| CN109415335B (zh) | 2020-06-05 |
| US20190330177A1 (en) | 2019-10-31 |
| EP3489227A4 (en) | 2020-01-22 |
| ES2855976T3 (es) | 2021-09-27 |
| EP3489227A1 (en) | 2019-05-29 |
| US11111227B2 (en) | 2021-09-07 |
| CA3030043A1 (en) | 2018-01-25 |
| KR20190031314A (ko) | 2019-03-25 |
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