CA2381630A1 - Method for preventing dyskinesias - Google Patents
Method for preventing dyskinesias Download PDFInfo
- Publication number
- CA2381630A1 CA2381630A1 CA002381630A CA2381630A CA2381630A1 CA 2381630 A1 CA2381630 A1 CA 2381630A1 CA 002381630 A CA002381630 A CA 002381630A CA 2381630 A CA2381630 A CA 2381630A CA 2381630 A1 CA2381630 A1 CA 2381630A1
- Authority
- CA
- Canada
- Prior art keywords
- benzooxazol
- ethanesulfinyl
- piperidin
- hydroxy
- group
- 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.)
- Abandoned
Links
- 208000012661 Dyskinesia Diseases 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims abstract description 12
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims abstract description 10
- 108091008757 nuclear thyroid hormone receptors Proteins 0.000 claims abstract description 10
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 69
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- FCBQJNCAKZSIAH-UHFFFAOYSA-N 6-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 FCBQJNCAKZSIAH-UHFFFAOYSA-N 0.000 claims description 26
- 208000018737 Parkinson disease Diseases 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 17
- -1 aldehyde amine Chemical class 0.000 claims description 15
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229960003638 dopamine Drugs 0.000 claims description 7
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims description 5
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- JUDKOGFHZYMDMF-UHFFFAOYSA-N 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol Chemical compound C1=2C=C(O)C(O)=CC=2CCNCC1C1=CC=CC=C1 JUDKOGFHZYMDMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
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- GYKUUMXOJROSLM-UHFFFAOYSA-N 6-[2-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 GYKUUMXOJROSLM-UHFFFAOYSA-N 0.000 claims description 3
- GPQLQRXXSSFLBP-UHFFFAOYSA-N 6-[2-[4-[(2-fluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 GPQLQRXXSSFLBP-UHFFFAOYSA-N 0.000 claims description 3
- BAOSFSQHJIWEEW-UHFFFAOYSA-N 6-[2-[4-[(4-methylphenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(C)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 BAOSFSQHJIWEEW-UHFFFAOYSA-N 0.000 claims description 3
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- BWHPNJVKFAPVOG-QYFJGNGUSA-N (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol hydrochloride Chemical compound Cl.C1C(C2)CC(C3)CC2CC13[C@H]1O[C@@H](CN)C2=CC=C(O)C(O)=C2C1 BWHPNJVKFAPVOG-QYFJGNGUSA-N 0.000 claims description 2
- WFFZHKKSIDENAJ-UHFFFAOYSA-N 1-[2-(4-hydroxyphenoxy)ethyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1CC1(O)CCN(CCOC=2C=CC(O)=CC=2)CC1 WFFZHKKSIDENAJ-UHFFFAOYSA-N 0.000 claims description 2
- KKVORRHRBZQCMY-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-1-[2-(4-hydroxyphenoxy)ethyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1OCCN1CCC(O)(CC=2C=CC(F)=CC=2)CC1 KKVORRHRBZQCMY-UHFFFAOYSA-N 0.000 claims description 2
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- RXYVUTNKSXMMJS-UHFFFAOYSA-N 6-[2-(4-benzylpiperidin-1-yl)ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C=1C=C2NC(=O)OC2=CC=1S(=O)CCN(CC1)CCC1CC1=CC=CC=C1 RXYVUTNKSXMMJS-UHFFFAOYSA-N 0.000 claims description 2
- DWRLXEBQOCRDPS-UHFFFAOYSA-N 6-[2-(4-benzylpiperidin-1-yl)ethylsulfinyl]-5-chloro-3h-1,3-benzoxazol-2-one Chemical compound ClC1=CC=2NC(=O)OC=2C=C1S(=O)CCN(CC1)CCC1CC1=CC=CC=C1 DWRLXEBQOCRDPS-UHFFFAOYSA-N 0.000 claims description 2
- ISVNVERJTYNQIU-UHFFFAOYSA-N 6-[2-[4-[(2,3-difluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC=CC(CC2CCN(CCS(=O)C=3C=C4OC(=O)NC4=CC=3)CC2)=C1F ISVNVERJTYNQIU-UHFFFAOYSA-N 0.000 claims description 2
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- BHQBKMBBHVRTNH-UHFFFAOYSA-N 6-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(Cl)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 BHQBKMBBHVRTNH-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- 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
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US28587001P | 2001-04-23 | 2001-04-23 | |
| US60/285,870 | 2001-04-23 |
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| CN (1) | CN1382442A (forum.php) |
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| CA (1) | CA2381630A1 (forum.php) |
| HK (1) | HK1048071A1 (forum.php) |
| HU (1) | HUP0201336A3 (forum.php) |
| IL (1) | IL149148A0 (forum.php) |
| PL (1) | PL353582A1 (forum.php) |
| ZA (1) | ZA200203180B (forum.php) |
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| US7005432B2 (en) | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| DE10338174A1 (de) | 2003-08-20 | 2005-03-24 | Lts Lohmann Therapie-Systeme Ag | Transdermale Arzneimittelzubereitungen mit Wirkstoffkombinationen zur Behandlung der Parkinson-Krankheit |
| US8252321B2 (en) | 2004-09-13 | 2012-08-28 | Chrono Therapeutics, Inc. | Biosynchronous transdermal drug delivery for longevity, anti-aging, fatigue management, obesity, weight loss, weight management, delivery of nutraceuticals, and the treatment of hyperglycemia, alzheimer's disease, sleep disorders, parkinson's disease, aids, epilepsy, attention deficit disorder, nicotine addiction, cancer, headache and pain control, asthma, angina, hypertension, depression, cold, flu and the like |
| CA2580329C (en) | 2004-09-13 | 2015-01-06 | Chrono Therapeutics Inc. | Biosynchronous transdermal drug delivery |
| US20100092554A1 (en) * | 2007-04-24 | 2010-04-15 | Boehringer Ingelheim International Gmbh | Combination with an extended release tablet formulation containing pramipexole or a pharmaceutically acceptable salt thereof |
| DE102007047737A1 (de) * | 2007-10-05 | 2009-04-30 | Merck Patent Gmbh | Piperidin- und Piperazinderivate |
| US20130017259A1 (en) | 2011-07-06 | 2013-01-17 | The Parkinson's Institute | Compositions and Methods for Treatment of Symptoms in Parkinson's Disease Patients |
| US10105487B2 (en) | 2013-01-24 | 2018-10-23 | Chrono Therapeutics Inc. | Optimized bio-synchronous bioactive agent delivery system |
| WO2016100940A1 (en) | 2014-12-19 | 2016-06-23 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3250258A4 (en) | 2015-01-28 | 2018-09-05 | Chrono Therapeutics, Inc. | Drug delivery methods and systems |
| EP3267875A4 (en) | 2015-03-12 | 2018-12-05 | Chrono Therapeutics Inc. | Craving input and support system |
| KR101657420B1 (ko) * | 2015-08-31 | 2016-10-14 | 고려공업검사 주식회사 | 열교환기 튜브 검사용 홀더 |
| US11285306B2 (en) | 2017-01-06 | 2022-03-29 | Morningside Venture Investments Limited | Transdermal drug delivery devices and methods |
| CA3101966A1 (en) | 2018-05-29 | 2019-12-05 | Morningside Venture Investments Limited | Drug delivery methods and systems |
| EP3880175A4 (en) | 2018-11-16 | 2022-08-17 | Morningside Venture Investments Limited | TEMPERATURE-REGULATING TRANSDERMAL DRUG DELIVERY SYSTEM |
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| BR9814867A (pt) * | 1997-10-24 | 2000-10-03 | Warner Lambert Co | Método para tratar discinesias relacionadas a doenças ou induzidas por drogas |
| PE20000728A1 (es) * | 1998-06-26 | 2000-08-21 | Cocensys Inc | Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda |
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- 2002-04-11 CA CA002381630A patent/CA2381630A1/en not_active Abandoned
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- 2002-04-18 AU AU34396/02A patent/AU3439602A/en not_active Abandoned
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Also Published As
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| EP1254661A1 (en) | 2002-11-06 |
| AU3439602A (en) | 2002-10-24 |
| HU0201336D0 (forum.php) | 2002-06-29 |
| HUP0201336A3 (en) | 2004-07-28 |
| HUP0201336A2 (hu) | 2004-04-28 |
| PL353582A1 (en) | 2002-11-04 |
| CN1382442A (zh) | 2002-12-04 |
| IL149148A0 (en) | 2002-11-10 |
| US20030004187A1 (en) | 2003-01-02 |
| HK1048071A1 (zh) | 2003-03-21 |
| KR20020082151A (ko) | 2002-10-30 |
| JP2002332246A (ja) | 2002-11-22 |
| ZA200203180B (en) | 2003-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |