JP2019523297A5 - - Google Patents
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- Publication number
- JP2019523297A5 JP2019523297A5 JP2019524492A JP2019524492A JP2019523297A5 JP 2019523297 A5 JP2019523297 A5 JP 2019523297A5 JP 2019524492 A JP2019524492 A JP 2019524492A JP 2019524492 A JP2019524492 A JP 2019524492A JP 2019523297 A5 JP2019523297 A5 JP 2019523297A5
- Authority
- JP
- Japan
- Prior art keywords
- rotigotine
- behenate
- crystalline form
- peak
- rotigotine behenate
- 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
- 229960003179 rotigotine Drugs 0.000 claims description 161
- KFQYTPMOWPVWEJ-INIZCTEOSA-N rotigotine Chemical compound CCCN([C@@H]1CC2=CC=CC(O)=C2CC1)CCC1=CC=CS1 KFQYTPMOWPVWEJ-INIZCTEOSA-N 0.000 claims description 159
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 126
- 229940116224 behenate Drugs 0.000 claims description 84
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 claims description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 26
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 238000001704 evaporation Methods 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 14
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 14
- 230000008020 evaporation Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims description 6
- 235000021357 Behenic acid Nutrition 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 229940116226 behenic acid Drugs 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 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 3
- 238000000746 purification Methods 0.000 claims description 3
- 230000004580 weight loss Effects 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 102000015554 Dopamine receptor Human genes 0.000 claims description 2
- 108050004812 Dopamine receptor Proteins 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000008280 blood Substances 0.000 description 35
- 210000004369 blood Anatomy 0.000 description 35
- 241000700159 Rattus Species 0.000 description 32
- 229940079593 drug Drugs 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 7
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 7
- 238000010255 intramuscular injection Methods 0.000 description 7
- 239000007927 intramuscular injection Substances 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 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
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 6
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 6
- 229940049964 oleate Drugs 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 230000036962 time dependent Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000000691 measurement method 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
- 239000000126 substance Substances 0.000 description 2
- 230000002459 sustained effect Effects 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 230000002496 gastric 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
- 210000004185 liver Anatomy 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- ZACKOMADVCPUNP-UHFFFAOYSA-M n,n-dimethylpyridin-1-ium-1-amine;4-methylbenzenesulfonate Chemical compound CN(C)[N+]1=CC=CC=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZACKOMADVCPUNP-UHFFFAOYSA-M 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2019523297A JP2019523297A (ja) | 2019-08-22 |
| JP2019523297A5 true JP2019523297A5 (https=) | 2020-01-23 |
| JP6751208B2 JP6751208B2 (ja) | 2020-09-02 |
Family
ID=60992805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019524492A Active JP6751208B2 (ja) | 2016-07-21 | 2016-07-21 | ロチゴチンベヘネート及びその調製方法並びに用途 |
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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2239196T3 (es) * | 2002-12-02 | 2005-09-16 | Schwarz Pharma Ag | Suministro iontoforetico de rotigotina para el tratamiento de la enfermedad de parkinson. |
| DE10361259A1 (de) * | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von Rotigotine in einem Frühstadium von Morbus Parkinson zur Prävention des weiteren Neuronenverlustes |
| 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 |
| 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 |
| RU2717542C9 (ru) * | 2016-07-21 | 2020-08-12 | Шаньдун Луе Фармасьютикал Ко., Лтд. | Ротиготина бегенат, его способ получения и применение |
-
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
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