JP2004506041A5 - - Google Patents
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- Publication number
- JP2004506041A5 JP2004506041A5 JP2002519422A JP2002519422A JP2004506041A5 JP 2004506041 A5 JP2004506041 A5 JP 2004506041A5 JP 2002519422 A JP2002519422 A JP 2002519422A JP 2002519422 A JP2002519422 A JP 2002519422A JP 2004506041 A5 JP2004506041 A5 JP 2004506041A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkanoyl
- group
- formula
- aporphine
- 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.)
- Pending
Links
- 125000001589 carboacyl group Chemical group 0.000 description 16
- BZKUYNBAFQJRDM-UHFFFAOYSA-N aporphine Chemical compound C12=CC=CC=C2CC2N(C)CCC3=CC=CC1=C32 BZKUYNBAFQJRDM-UHFFFAOYSA-N 0.000 description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 150000008441 aporphines Chemical class 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- -1 phenylacetyl Chemical group 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QCMQEZNBBPGFKQ-UHFFFAOYSA-N Thalisopynine Natural products CN1CCC2=C(OC)C(OC)=C(OC)C3=C2C1CC1=C3C=C(OC)C(O)=C1 QCMQEZNBBPGFKQ-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 208000019695 Migraine disease Diseases 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 208000031424 hyperprolactinemia Diseases 0.000 description 3
- 206010027599 migraine Diseases 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 0 *N(CC1)[C@](C2)c3c1cccc3-c1c2ccc(O)c1O Chemical compound *N(CC1)[C@](C2)c3c1cccc3-c1c2ccc(O)c1O 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0002934A SE0002934D0 (sv) | 2000-08-17 | 2000-08-17 | New aporphine esters and in their use in therapy |
| PCT/SE2001/001658 WO2002014279A1 (en) | 2000-08-17 | 2001-07-20 | New aporphine esters and their use in therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506041A JP2004506041A (ja) | 2004-02-26 |
| JP2004506041A5 true JP2004506041A5 (enExample) | 2009-07-16 |
Family
ID=20280719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002519422A Pending JP2004506041A (ja) | 2000-08-17 | 2001-07-20 | 新規アポルフィンエステルおよび治療におけるそれらの使用 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7238705B2 (enExample) |
| EP (1) | EP1309553A1 (enExample) |
| JP (1) | JP2004506041A (enExample) |
| KR (1) | KR100865503B1 (enExample) |
| CN (1) | CN1242991C (enExample) |
| AU (2) | AU7122801A (enExample) |
| BR (1) | BR0113291A (enExample) |
| CA (1) | CA2419842C (enExample) |
| CZ (1) | CZ2003454A3 (enExample) |
| EA (1) | EA006388B1 (enExample) |
| HU (1) | HUP0301685A3 (enExample) |
| IL (2) | IL154096A0 (enExample) |
| MX (1) | MXPA03001465A (enExample) |
| NO (1) | NO324409B1 (enExample) |
| NZ (1) | NZ523893A (enExample) |
| PL (1) | PL360089A1 (enExample) |
| SE (1) | SE0002934D0 (enExample) |
| WO (1) | WO2002014279A1 (enExample) |
| ZA (1) | ZA200300828B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102036D0 (sv) * | 2001-06-08 | 2001-06-08 | Axon Biochemicals Bv | Pharmaceutical formulation for the efficient administration of apomorphine, 6aR- (-) -N- Propyl- norapomorphine and their derivatives and pro-drugs thereof |
| SE0002934D0 (sv) * | 2000-08-17 | 2000-08-17 | Axon Biochemicals Bv | New aporphine esters and in their use in therapy |
| WO2004110449A1 (en) * | 2003-06-19 | 2004-12-23 | Lotus Pharmaceutical Co., Ltd. | Aporphine and oxoaporphine and the medical use thereof |
| WO2004112723A2 (en) | 2003-06-20 | 2004-12-29 | Ronald Aung-Din | Tropical therapy for the treatment of migraines, muscle sprains, muscle spasm, spasticity and related conditions |
| US7648995B2 (en) | 2004-04-13 | 2010-01-19 | The Mclean Hospital Corporation | R(—)-11-hydroxyaporphine derivatives and uses thereof |
| GB2437488A (en) * | 2006-04-25 | 2007-10-31 | Optinose As | Pharmaceutical oily formulation for nasal or buccal administration |
| US20110111014A1 (en) * | 2007-06-26 | 2011-05-12 | Parkinson's Institute | Methods and compositions for treatment of neurological disorders |
| US8431591B2 (en) | 2007-07-12 | 2013-04-30 | The Mclean Hospital Corporation | R(−)-2-methoxy-11-hydroxyaporphine and derivatives thereof |
| US20090124651A1 (en) | 2007-08-31 | 2009-05-14 | H. Lundbeck A/S | Catecholamine derivatives and prodrugs thereof |
| TWI404702B (zh) | 2007-08-31 | 2013-08-11 | Lundbeck & Co As H | 兒茶酚胺衍生物和其前藥 |
| ES2315203B1 (es) * | 2007-09-11 | 2010-01-13 | Universidade De Santiago De Compostela | Uso de oxoisoaporfinas y sus derivados como inhibidores selectivos de la monoamino oxidasa a. |
| GB0721394D0 (en) * | 2007-10-31 | 2007-12-12 | Vectura Group Plc | Compositions for trating parkinson's disease |
| WO2010005507A1 (en) | 2008-06-30 | 2010-01-14 | Afgin Pharma, Llc | Topical regional neuro-affective therapy |
| WO2010121159A1 (en) * | 2009-04-17 | 2010-10-21 | Somalabs, Inc. | Method for the induction of a reward response by modulation of dopaminergic systems in the central nervous system |
| ES2699077T3 (es) | 2009-06-12 | 2019-02-07 | Sunovion Pharmaceuticals Inc | Apomorfina sublingual |
| EA031156B1 (ru) | 2010-12-16 | 2018-11-30 | Суновион Фармасьютикалз Инк. | Сублингвальные пленки |
| AU2012214283B2 (en) * | 2011-02-11 | 2016-01-28 | The Regents Of The University Of Michigan | Tripeptide compositions and methods for treatment of diabetes |
| WO2016172095A1 (en) | 2015-04-21 | 2016-10-27 | Cynapsus Therapeutics, Inc. | Methods of treating parkinson's disease by administration of apomorphine to an oral mucosa |
| WO2016207070A1 (en) | 2015-06-24 | 2016-12-29 | Koninklijke Philips N.V. | Sweat monitoring apparatus and monitoring method |
| TWI816716B (zh) | 2017-11-24 | 2023-10-01 | 丹麥商Ｈ 朗德貝克公司 | 用於治療帕金森病之新兒茶酚胺前驅藥 |
| HUE070062T2 (hu) * | 2018-01-18 | 2025-05-28 | Leukos Biotech S L | Apomorfin-palmitinsav kokristály szilárd részecske kristályos forma |
| CA3097568A1 (en) * | 2018-04-20 | 2019-10-24 | The General Hospital Corporation | Acetylated prodrugs for delivery across the blood-brain barrier |
| US11111263B2 (en) | 2019-05-20 | 2021-09-07 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11130775B2 (en) | 2019-05-20 | 2021-09-28 | H. Lundbeck A/S | Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11168056B2 (en) | 2019-05-20 | 2021-11-09 | H. Lundbeck A/S | Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol |
| US12319710B2 (en) | 2019-05-21 | 2025-06-03 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's diseases |
| US12384765B2 (en) | 2019-05-21 | 2025-08-12 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's Disease |
| EP3972959A1 (en) | 2019-05-21 | 2022-03-30 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's disease |
| CN113727712B (zh) | 2019-05-21 | 2024-11-15 | H.隆德贝克有限公司 | 用于治疗帕金森病的儿茶酚胺氨基甲酸酯前药 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080456A (en) * | 1971-10-26 | 1978-03-21 | Schering Aktiengesellschaft | Diacylapomorphines |
| AU3140577A (en) * | 1976-12-13 | 1979-06-14 | Sterling Drug Inc | N-propylnorapormorphine diesters |
| DE2717001C2 (de) * | 1977-04-18 | 1984-06-20 | Karl O. Helm Ag, 2000 Hamburg | Arzneimittel mit antithrombotischer Wirkung |
| EP0040074B1 (en) * | 1980-05-08 | 1985-07-31 | Northeastern University | N-substituted aporphines, a method of inducing emesis and a method of controlling psychosis utilising the same |
| US4353912A (en) * | 1980-05-08 | 1982-10-12 | Northeastern University | N-Haloalkyl nor apomorphines and method of inactivating dopamine receptor sites and enhancing dopaminergic activity therewith |
| WO1990012574A1 (en) * | 1989-04-25 | 1990-11-01 | Northeastern University | Dopamine agonist compounds |
| GB9517062D0 (en) | 1995-08-18 | 1995-10-25 | Scherer Ltd R P | Pharmaceutical compositions |
| GB9700878D0 (en) | 1997-01-17 | 1997-03-05 | Scherer Ltd R P | Dosage forms and method for ameliorating male erectile dysfunction |
| US6403605B1 (en) | 1998-05-29 | 2002-06-11 | Queen's University At Kingston | Methods for the normalization of sexual response and amelioration of long term genital tissue degradation |
| IT1299566B1 (it) * | 1998-07-17 | 2000-03-16 | Ifi Istituto Farmacoterapico I | Cerotto transdermico e composizioni farmaceutiche comprendenti r (-)- norapropilapomorfina cloridrato e/o s (+) - norapropilapomorfina |
| EP1175206A1 (en) * | 1999-05-13 | 2002-01-30 | Unihart Corporation | Pharmaceutical compositions comprising apocodeine and/or its derivatives |
| AU2001255818A1 (en) * | 2000-04-07 | 2001-10-23 | Tap Pharmaceutical Products Inc. | Apomorphine derivatives and methods for their use |
| SE0102036D0 (sv) * | 2001-06-08 | 2001-06-08 | Axon Biochemicals Bv | Pharmaceutical formulation for the efficient administration of apomorphine, 6aR- (-) -N- Propyl- norapomorphine and their derivatives and pro-drugs thereof |
| SE0002934D0 (sv) | 2000-08-17 | 2000-08-17 | Axon Biochemicals Bv | New aporphine esters and in their use in therapy |
| EP1950203A1 (en) | 2007-01-24 | 2008-07-30 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds with ACAT, their preparation and use as medicaments |
-
2000
- 2000-08-17 SE SE0002934A patent/SE0002934D0/xx unknown
-
2001
- 2001-07-20 AU AU7122801A patent/AU7122801A/xx active Pending
- 2001-07-20 JP JP2002519422A patent/JP2004506041A/ja active Pending
- 2001-07-20 CN CNB018142222A patent/CN1242991C/zh not_active Expired - Fee Related
- 2001-07-20 WO PCT/SE2001/001658 patent/WO2002014279A1/en not_active Ceased
- 2001-07-20 CZ CZ2003454A patent/CZ2003454A3/cs unknown
- 2001-07-20 EA EA200300266A patent/EA006388B1/ru not_active IP Right Cessation
- 2001-07-20 NZ NZ523893A patent/NZ523893A/en not_active IP Right Cessation
- 2001-07-20 EP EP01950203A patent/EP1309553A1/en not_active Withdrawn
- 2001-07-20 PL PL36008901A patent/PL360089A1/xx not_active Application Discontinuation
- 2001-07-20 KR KR1020037002274A patent/KR100865503B1/ko not_active Expired - Fee Related
- 2001-07-20 MX MXPA03001465A patent/MXPA03001465A/es active IP Right Grant
- 2001-07-20 IL IL15409601A patent/IL154096A0/xx unknown
- 2001-07-20 HU HU0301685A patent/HUP0301685A3/hu unknown
- 2001-07-20 BR BR0113291-1A patent/BR0113291A/pt not_active Application Discontinuation
- 2001-07-20 US US10/344,420 patent/US7238705B2/en not_active Expired - Lifetime
- 2001-07-20 CA CA2419842A patent/CA2419842C/en not_active Expired - Fee Related
- 2001-07-20 AU AU2001271228A patent/AU2001271228B2/en not_active Ceased
-
2003
- 2003-01-23 IL IL154096A patent/IL154096A/en active IP Right Grant
- 2003-01-30 ZA ZA200300828A patent/ZA200300828B/en unknown
- 2003-02-11 NO NO20030677A patent/NO324409B1/no not_active IP Right Cessation
-
2005
- 2005-02-22 US US11/061,881 patent/US7332503B2/en not_active Expired - Lifetime
-
2008
- 2008-01-29 US US12/021,560 patent/US20080119504A1/en not_active Abandoned
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