ZA200300828B - New aporphine esters and their use in therapy. - Google Patents
New aporphine esters and their use in therapy. Download PDFInfo
- Publication number
- ZA200300828B ZA200300828B ZA200300828A ZA200300828A ZA200300828B ZA 200300828 B ZA200300828 B ZA 200300828B ZA 200300828 A ZA200300828 A ZA 200300828A ZA 200300828 A ZA200300828 A ZA 200300828A ZA 200300828 B ZA200300828 B ZA 200300828B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- group
- alkanoyl
- formula
- aporphine
- Prior art date
Links
- 150000008441 aporphines Chemical class 0.000 title claims description 21
- 238000002560 therapeutic procedure Methods 0.000 title description 4
- -1 trifluoromethanesulphonyloxy Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001589 carboacyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- BZKUYNBAFQJRDM-UHFFFAOYSA-N aporphine Chemical compound C12=CC=CC=C2CC2N(C)CCC3=CC=CC1=C32 BZKUYNBAFQJRDM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000005690 diesters Chemical class 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 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 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000007920 subcutaneous administration Methods 0.000 claims description 7
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 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 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 208000005793 Restless legs syndrome Diseases 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 3
- 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 claims 2
- 206010019233 Headaches Diseases 0.000 claims 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 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 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
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- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
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- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 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 25
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- 229960004502 levodopa Drugs 0.000 description 25
- 230000000694 effects Effects 0.000 description 18
- 229960004046 apomorphine Drugs 0.000 description 14
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 13
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- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- 206010044565 Tremor Diseases 0.000 description 2
- 108010035075 Tyrosine decarboxylase Proteins 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000002714 alpha-linolenoyl 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])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])[H] 0.000 description 1
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- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 description 1
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- FGXWKSZFVQUSTL-UHFFFAOYSA-N domperidone Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2NC1=O FGXWKSZFVQUSTL-UHFFFAOYSA-N 0.000 description 1
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- 125000003696 stearoyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300828B true ZA200300828B (en) | 2004-05-17 |
Family
ID=20280719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300828A ZA200300828B (en) | 2000-08-17 | 2003-01-30 | New aporphine esters and their use in therapy. |
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) | AU2001271228B2 (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 |
|---|---|---|---|---|
| SE0002934D0 (sv) | 2000-08-17 | 2000-08-17 | Axon Biochemicals Bv | New aporphine esters and in their use in therapy |
| 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 |
| EP1634596A4 (en) * | 2003-06-19 | 2006-06-21 | Lotus Pharmaceutical Co Ltd | APORPHINE AND OXOPHORPHINE AND ITS MEDICAL USE |
| EP1644004A4 (en) | 2003-06-20 | 2010-10-06 | Ronald Aung-Din | LOCAL THERAPY FOR THE TREATMENT OF MIGRAINS, MUSCLE CLARIFICATIONS, MUSCLE SPASMS, SPASTICITY AND RELATED CONDITIONS |
| JP2007532670A (ja) | 2004-04-13 | 2007-11-15 | ザ マクレーン ホスピタル コーポレーション | Ｒ（−）−１１−ヒドロキシアポルフィン誘導体およびその使用方法 |
| GB2437488A (en) * | 2006-04-25 | 2007-10-31 | Optinose As | Pharmaceutical oily formulation for nasal or buccal administration |
| GB2463833B (en) * | 2007-06-26 | 2012-02-08 | Parkinson S Inst | Compositions that prevent or reverse alpha-synuclein fibrillation for use in the treatment of neurological disorders |
| WO2009009083A1 (en) * | 2007-07-12 | 2009-01-15 | The Mclean Hospital Corporation | R(-)-2-methoxy-11-hydroxyaporphine and derivatives thereof |
| TWI404702B (zh) * | 2007-08-31 | 2013-08-11 | Lundbeck & Co As H | 兒茶酚胺衍生物和其前藥 |
| US20090124651A1 (en) | 2007-08-31 | 2009-05-14 | H. Lundbeck A/S | Catecholamine derivatives and prodrugs thereof |
| 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 |
| CA2729346A1 (en) | 2008-06-30 | 2010-01-14 | Afgin Pharma, Llc | Topical regional neuro-affective therapy |
| CA2758948A1 (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 |
| PT2952191T (pt) | 2009-06-12 | 2018-11-30 | Sunovion Pharmaceuticals Inc | Apomorfina sublingual |
| EP2651357B1 (en) | 2010-12-16 | 2020-04-01 | Sunovion Pharmaceuticals Inc. | Sublingual films |
| CA2827029C (en) * | 2011-02-11 | 2019-07-02 | The Regents Of The University Of Michigan | Tripeptide compositions and methods |
| CA3127926A1 (en) | 2015-04-21 | 2016-10-27 | Sunovion Pharmaceuticals Inc. | Methods of treating parkinson's disease by administration of apomorphine to an oral mucosa |
| EP3314251A1 (en) | 2015-06-24 | 2018-05-02 | Koninklijke Philips N.V. | Sweat monitoring apparatus and monitoring method |
| PT3713933T (pt) | 2017-11-24 | 2026-05-19 | H Lundbeck As | Novos profrmacos de catecolamina para utilizao no tratamento de doena de parkinson |
| BR112020014598A2 (pt) * | 2018-01-18 | 2020-12-08 | Leukos Biotech, S. L. | Forma cristalina de partículas sólidas cocristalinas de apomorfina·ácido palmítico |
| CN112930180A (zh) * | 2018-04-20 | 2021-06-08 | 通用医疗公司 | 用于跨血脑屏障递送的乙酰化前药 |
| 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 |
| 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 |
| 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 |
| US12391650B2 (en) | 2019-05-21 | 2025-08-19 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's disease |
| WO2020234275A1 (en) | 2019-05-21 | 2020-11-26 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's diseases |
| EP3972600B1 (en) | 2019-05-21 | 2026-02-18 | H. Lundbeck A/S | Catecholamine carbamate prodrugs for use in the treatment of parkinson s disease |
| JP7641234B2 (ja) | 2019-05-21 | 2025-03-06 | ハー・ルンドベック・アクチエゼルスカベット | パーキンソン病の治療に使用するための新規なカテコールアミンプロドラッグ |
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 |
| KR20030036157A (ko) * | 2000-04-07 | 2003-05-09 | 탭 파마슈티칼 프로덕츠 인코포레이티드 | 아포모르핀 유도체 및 이의 사용 방법 |
| 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 WO PCT/SE2001/001658 patent/WO2002014279A1/en not_active Ceased
- 2001-07-20 CA CA2419842A patent/CA2419842C/en not_active Expired - Fee Related
- 2001-07-20 JP JP2002519422A patent/JP2004506041A/ja active Pending
- 2001-07-20 CZ CZ2003454A patent/CZ2003454A3/cs unknown
- 2001-07-20 EP EP01950203A patent/EP1309553A1/en not_active Withdrawn
- 2001-07-20 MX MXPA03001465A patent/MXPA03001465A/es active IP Right Grant
- 2001-07-20 BR BR0113291-1A patent/BR0113291A/pt not_active Application Discontinuation
- 2001-07-20 HU HU0301685A patent/HUP0301685A3/hu unknown
- 2001-07-20 CN CNB018142222A patent/CN1242991C/zh not_active Expired - Fee Related
- 2001-07-20 US US10/344,420 patent/US7238705B2/en not_active Expired - Lifetime
- 2001-07-20 AU AU2001271228A patent/AU2001271228B2/en not_active Ceased
- 2001-07-20 IL IL15409601A patent/IL154096A0/xx 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 AU AU7122801A patent/AU7122801A/xx active Pending
- 2001-07-20 KR KR1020037002274A patent/KR100865503B1/ko not_active Expired - Fee Related
- 2001-07-20 PL PL36008901A patent/PL360089A1/xx not_active Application Discontinuation
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| NO20030677L (no) | 2003-03-05 |
| HUP0301685A3 (en) | 2010-03-29 |
| NO324409B1 (no) | 2007-10-08 |
| JP2004506041A (ja) | 2004-02-26 |
| US7238705B2 (en) | 2007-07-03 |
| KR20030036703A (ko) | 2003-05-09 |
| US20080119504A1 (en) | 2008-05-22 |
| AU2001271228B2 (en) | 2006-02-02 |
| NO20030677D0 (no) | 2003-02-11 |
| MXPA03001465A (es) | 2004-12-13 |
| EA006388B1 (ru) | 2005-12-29 |
| EA200300266A1 (ru) | 2003-08-28 |
| IL154096A (en) | 2009-11-18 |
| SE0002934D0 (sv) | 2000-08-17 |
| NZ523893A (en) | 2003-10-31 |
| EP1309553A1 (en) | 2003-05-14 |
| CA2419842C (en) | 2011-10-18 |
| BR0113291A (pt) | 2004-01-06 |
| CN1447792A (zh) | 2003-10-08 |
| PL360089A1 (en) | 2004-09-06 |
| KR100865503B1 (ko) | 2008-10-28 |
| CN1242991C (zh) | 2006-02-22 |
| US7332503B2 (en) | 2008-02-19 |
| HUP0301685A2 (hu) | 2003-08-28 |
| WO2002014279A1 (en) | 2002-02-21 |
| IL154096A0 (en) | 2003-07-31 |
| AU7122801A (en) | 2002-02-25 |
| US20050143408A1 (en) | 2005-06-30 |
| CA2419842A1 (en) | 2002-02-21 |
| US20040018956A1 (en) | 2004-01-29 |
| CZ2003454A3 (cs) | 2003-06-18 |
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