WO2003074511A1 - Quinoline derivatives - Google Patents

Quinoline derivatives Download PDF

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Publication number
WO2003074511A1
WO2003074511A1 PCT/EP2003/002321 EP0302321W WO03074511A1 WO 2003074511 A1 WO2003074511 A1 WO 2003074511A1 EP 0302321 W EP0302321 W EP 0302321W WO 03074511 A1 WO03074511 A1 WO 03074511A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
acid addition
treatment
free base
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.)
Ceased
Application number
PCT/EP2003/002321
Other languages
English (en)
French (fr)
Inventor
Peter Gull
Esteban Pombo Villar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis Pharma GmbH Austria
Novartis AG
Original Assignee
Novartis Pharma GmbH Austria
Novartis AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to IL16376903A priority Critical patent/IL163769A0/xx
Priority to HK05104122.8A priority patent/HK1071364B/en
Priority to EP03714784A priority patent/EP1480970B1/en
Priority to AU2003219023A priority patent/AU2003219023B2/en
Priority to JP2003572979A priority patent/JP2005519117A/ja
Priority to NZ534732A priority patent/NZ534732A/en
Priority to DK03714784T priority patent/DK1480970T3/da
Priority to MXPA04008666A priority patent/MXPA04008666A/es
Priority to CA2477720A priority patent/CA2477720C/en
Priority to DE60311233T priority patent/DE60311233T2/de
Priority to BR0308201-6A priority patent/BR0308201A/pt
Application filed by Novartis Pharma GmbH Austria, Novartis AG filed Critical Novartis Pharma GmbH Austria
Priority to US10/506,232 priority patent/US7399768B2/en
Priority to SI200330755T priority patent/SI1480970T1/sl
Priority to KR1020047012409A priority patent/KR101027977B1/ko
Priority to DK06121714T priority patent/DK1757601T3/da
Publication of WO2003074511A1 publication Critical patent/WO2003074511A1/en
Anticipated expiration legal-status Critical
Priority to NO20044117A priority patent/NO20044117L/no
Priority to CY20071100405T priority patent/CY1106409T1/el
Priority to US12/137,819 priority patent/US20080255176A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to novel benzo [g] quinoline derivatives, their preparation, their use as pharmaceuticals and pharmaceutical compositions containing them.
  • the present present invention pertains to a compound selected from the group consisting of compound of formula la,
  • a and Q are each H or form together an additional bond, and wherein the asymmetric center in position 3 may be racemic, or in form of an optically active form, and wherein R is of formula lb or lc,
  • R1 is alkyl, in free base or acid addition salt form.
  • a and Q are each H. In a further preferred aspect A and Q form together an additional bond.
  • the substituent CH2-R in position 3 of formula la is preferably in configuration 3R, provided A and Q are each H.
  • R1 is preferably selected from alkyl having from 1 to 4 carbon atoms. Accordingly, as used herein, alkyl is especially CrC ⁇ alkyl, e.g. n-butyl, sec-butyl, tert-butyl, n-propyl, isopropyl, or especially methyl or also ethyl.
  • R1 is Ci-alkyl e.g. methyl.
  • the present invention pertains to a compound selected from the group consisting of compound of formula I and compound of formula II,
  • Acid addition salts may be produced from the free bases in known manner, and vice versa.
  • Suitable acid addition salts for use in accordance with the present invention include for example the hydrochloride.
  • the compounds of formula la, I and II and their physiologically acceptable acid addition salts referred to hereinafter as compounds of the invention, exhibit valuable pharmacological properties in animal tests and are therefore useful as pharmaceuticals.
  • the compounds of the present invention exhibit favorable pharmacological properties vis-avis the closest prior art, e.g. EP 912'553.
  • Detailed description of the present invention is a part of the present invention.
  • the compounds according to the invention produce a decrease on the intraocular pressure (IOP) in rabbits, at concentrations of 10 to 100 ⁇ M.
  • IOP intraocular pressure
  • Male rabbits of ca. 2.5 kg are fixed in cages leaving their heads free.
  • the solutions with the compound to be tested are applied to the right eye and the placebo solutions to the left eye (2 drops each, i.e. ca. 40 ⁇ l).
  • the eyes are firstly anaesthetized with a solution containing Novesine (0.4 %) and Fluorescein (0.05 %) and the ocular pressure is determined at various intervals after administration (10, 20, 30, 60, 90, 120, 180 and 240 minutes), whereby an applanation tonometer according to Goldberg is used.
  • the compounds according to the invention exhibit a strong lOP-lowering efficacy, an excellent tolerability, and a long duration of action, and are therefore in particular useful in the treatment of glaucoma and myopia. In a preferred aspect it refers to the treatment of glaucoma.
  • the appropriate dosage will of course vary depending upon, for example, the compound employed, the host, the mode of administration and the severity of the condition being treated. However, in general, satisfactory results in animals are indicated to be obtained at a daily dosage of from about 0.1 to about 10 mg/kg animal body weight. In larger mammals, for example humans , an indicated daily dosage is in the range from about 5 to about 200 mg, preferably about 10 to about 100 mg of the compound conveniently administered in divided doses up to 4 times a day or in sustained release form.
  • the compounds of the invention may be administered in free form or in pharmaceutically acceptable salt form.
  • Such salts may be prepared in conventional manner and exhibit the same order of activity as the free compounds.
  • the present invention provides a compound of the invention for use as a pharmaceutical, e.g. in the treatment of glaucoma and myopia.
  • the present invention furthermore provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of the invention in association with at least one pharmaceutically acceptable diluent or carrier.
  • Such compositions may be formulated in conventional manner.
  • Unit dosage forms contain, for example, from about 0.25 to about 50 mg of a compound according to the invention.
  • Compounds according to the invention may be administered by any conventional route, for example parenterally e.g. in form of injectable solutions or suspensions, or enterally, preferably orally, e.g. in the form of tablets or capsules.
  • ophthalmological solutions More preferably, they are applied topically to the eye in ca. 0.002 to 0.02 % ophthalmological solutions.
  • the ophthalmic vehicle is such that the compound is maintained in contact with the ocular surface for a sufficient time period to allow the compound to penetrate the corneal and internal regions of the eye.
  • the pharmaceutically acceptable ophthalmic vehicle may be e.g. an ointment, vegetable oil, or an encapsulating material.
  • the present invention also provides a compound of the invention for use as a pharmaceutical in the treatment of glaucoma and myopia.
  • the present invention provides the use of a compound of the invention, for the manufacture of a medicament for the treatment of glaucoma and myopia.
  • the present invention provides a method for the treatment of glaucoma and myopia in a subject in need of such treatment, which comprises administering to such subject a therapeutically effective amount of a compound of the invention.
  • Example 1 f3R.4aR.10aR1-1-methyl-3 ⁇ -hvdroxymethyl-6-methoxy-1.2.3.4. 4aoc.5.10.
  • SDBA sodium dihydro-bis-(2-mthoxyethoxy) aluminate
  • 70 % in toluene, 42 mM sodium dihydro-bis-(2-mthoxyethoxy) aluminate
  • 10 ml NaOH (30 %) are added in drops to the ice cooled reaction mixture.
  • the precipitated crystals are filtered off, washed with water and toluene and dried.
  • Example 5 To a solution of 4 g (15.4 mM) of 1 ,2,4aS-trans-5,10,10a-hexahydro-6-methoxy-1-methyl-3- hydroxymethyl-benzo[g]quinoline (see Registry No. 201869-32-1, Chem. Abstr.) in 40 ml toluene, 1.3 ml (17.9 mM) thionylchloride are slowly added dropwise at a temperature of 0°C. The suspension is stirred for 12 hours at room temperature. The resulting chloride crystallizes spontaneously. After filtration and washing with toluene, the product is directly used in the next step.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
PCT/EP2003/002321 2002-03-07 2003-03-06 Quinoline derivatives Ceased WO2003074511A1 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BR0308201-6A BR0308201A (pt) 2002-03-07 2003-03-06 Derivados de quinolina
EP03714784A EP1480970B1 (en) 2002-03-07 2003-03-06 Quinoline derivatives
AU2003219023A AU2003219023B2 (en) 2002-03-07 2003-03-06 Quinoline derivatives
JP2003572979A JP2005519117A (ja) 2002-03-07 2003-03-06 キノリン誘導体
NZ534732A NZ534732A (en) 2002-03-07 2003-03-06 Quinoline derivatives
DK03714784T DK1480970T3 (da) 2002-03-07 2003-03-06 Quinolinderivater
MXPA04008666A MXPA04008666A (es) 2002-03-07 2003-03-06 Derivados de quinolina.
CA2477720A CA2477720C (en) 2002-03-07 2003-03-06 Quinoline derivatives
US10/506,232 US7399768B2 (en) 2002-03-07 2003-03-06 Quinoline derivatives
IL16376903A IL163769A0 (en) 2002-03-07 2003-03-06 Quinoline derivatives
HK05104122.8A HK1071364B (en) 2002-03-07 2003-03-06 Quinoline derivatives
DE60311233T DE60311233T2 (de) 2002-03-07 2003-03-06 Chinolinderivate
SI200330755T SI1480970T1 (sl) 2002-03-07 2003-03-06 Derivati kinolina
KR1020047012409A KR101027977B1 (ko) 2002-03-07 2003-03-06 퀴놀린 유도체
DK06121714T DK1757601T3 (da) 2002-03-07 2003-03-06 Quinolinderivater og deres anvendelse ved glaukom og myopi
NO20044117A NO20044117L (no) 2002-03-07 2004-09-28 Kinolinderivater
CY20071100405T CY1106409T1 (el) 2002-03-07 2007-03-22 Παραγωγα κινολινης
US12/137,819 US20080255176A1 (en) 2002-03-07 2008-06-12 Quinoline derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP02005117 2002-03-07
EP02005117.3 2002-03-07
EP02005115 2002-03-07
EP02005115.7 2002-03-07

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/137,819 Continuation US20080255176A1 (en) 2002-03-07 2008-06-12 Quinoline derivatives

Publications (1)

Publication Number Publication Date
WO2003074511A1 true WO2003074511A1 (en) 2003-09-12

Family

ID=27790094

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/002321 Ceased WO2003074511A1 (en) 2002-03-07 2003-03-06 Quinoline derivatives

Country Status (28)

Country Link
US (2) US7399768B2 (https=)
EP (1) EP1480970B1 (https=)
JP (2) JP2005519117A (https=)
KR (1) KR101027977B1 (https=)
CN (2) CN1939915A (https=)
AR (1) AR038730A1 (https=)
AU (1) AU2003219023B2 (https=)
BR (1) BR0308201A (https=)
CA (2) CA2477720C (https=)
CO (1) CO5611196A2 (https=)
CY (1) CY1106409T1 (https=)
DE (1) DE60311233T2 (https=)
DK (1) DK1480970T3 (https=)
EC (1) ECSP045271A (https=)
EG (1) EG24415A (https=)
ES (1) ES2279100T3 (https=)
IL (1) IL163769A0 (https=)
MX (1) MXPA04008666A (https=)
MY (1) MY134325A (https=)
NO (1) NO20044117L (https=)
NZ (1) NZ534732A (https=)
PE (1) PE20030927A1 (https=)
PL (2) PL210336B1 (https=)
PT (1) PT1480970E (https=)
RU (1) RU2345991C2 (https=)
SI (1) SI1480970T1 (https=)
TW (1) TW200406401A (https=)
WO (1) WO2003074511A1 (https=)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1757601A1 (en) * 2002-03-07 2007-02-28 Novartis AG Quinoline derivatives and their use in glaucoma and myopia
US11104697B2 (en) 2019-05-20 2021-08-31 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
US11110110B2 (en) 2017-11-24 2021-09-07 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's disease
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
US12391650B2 (en) 2019-05-21 2025-08-19 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's disease
US12398106B2 (en) 2019-05-21 2025-08-26 H. Lundbeck A/S Catecholamine carbamate prodrugs for use in the treatment of parkinson's disease

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001444A1 (en) * 1996-07-08 1998-01-15 Novartis Ag BENZO[g]QUINOLINE DERIVATIVES

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL100555A (en) * 1991-02-07 2000-08-31 Hoechst Marion Roussel Inc N-substituted quinoline derivatives their preparation their use for the preparation of medicaments and the pharmaceutical compositions containing them
GB9326010D0 (en) * 1993-12-21 1994-02-23 Sandoz Ltd Improvements in or relating to organic compounds
PE20030240A1 (es) * 2001-07-09 2003-04-16 Novartis Ag DERIVADOS DE BENZO [g] QUINOLINA

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001444A1 (en) * 1996-07-08 1998-01-15 Novartis Ag BENZO[g]QUINOLINE DERIVATIVES

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1757601A1 (en) * 2002-03-07 2007-02-28 Novartis AG Quinoline derivatives and their use in glaucoma and myopia
US11707476B2 (en) 2017-11-24 2023-07-25 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of parkinson's disease
US12226428B2 (en) 2017-11-24 2025-02-18 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's disease
US11110110B2 (en) 2017-11-24 2021-09-07 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's disease
US11858954B2 (en) 2019-05-20 2024-01-02 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
US11866410B2 (en) 2019-05-20 2024-01-09 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
US20220185839A1 (en) 2019-05-20 2022-06-16 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
US11827665B2 (en) 2019-05-20 2023-11-28 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
US11851456B2 (en) 2019-05-20 2023-12-26 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
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
US11104697B2 (en) 2019-05-20 2021-08-31 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
US12479801B2 (en) 2019-05-20 2025-11-25 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
US12421271B2 (en) 2019-05-20 2025-09-23 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
US12398169B2 (en) 2019-05-20 2025-08-26 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
US12398106B2 (en) 2019-05-21 2025-08-26 H. Lundbeck A/S Catecholamine carbamate prodrugs for use in the treatment of parkinson's disease
US12391650B2 (en) 2019-05-21 2025-08-19 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's disease
US12384765B2 (en) 2019-05-21 2025-08-12 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's Disease
US12319710B2 (en) 2019-05-21 2025-06-03 H. Lundbeck A/S Catecholamine prodrugs for use in the treatment of Parkinson's diseases

Also Published As

Publication number Publication date
ECSP045271A (es) 2004-10-26
PL210336B1 (pl) 2012-01-31
US20050234085A1 (en) 2005-10-20
DE60311233D1 (de) 2007-03-08
PL215012B1 (pl) 2013-10-31
AR038730A1 (es) 2005-01-26
PE20030927A1 (es) 2003-12-26
TW200406401A (en) 2004-05-01
DK1480970T3 (da) 2007-03-05
US7399768B2 (en) 2008-07-15
JP2005519117A (ja) 2005-06-30
PL394208A1 (pl) 2011-08-16
CA2477720C (en) 2010-09-21
CN1639148A (zh) 2005-07-13
MY134325A (en) 2007-12-31
ES2279100T3 (es) 2007-08-16
PL370915A1 (en) 2005-06-13
DE60311233T2 (de) 2007-11-15
CY1106409T1 (el) 2011-10-12
RU2004129767A (ru) 2005-06-27
PT1480970E (pt) 2007-03-30
EP1480970B1 (en) 2007-01-17
RU2345991C2 (ru) 2009-02-10
KR101027977B1 (ko) 2011-04-13
JP2010095550A (ja) 2010-04-30
IL163769A0 (en) 2005-12-18
MXPA04008666A (es) 2004-12-06
SI1480970T1 (sl) 2007-06-30
CN1939915A (zh) 2007-04-04
AU2003219023A1 (en) 2003-09-16
CA2477720A1 (en) 2003-09-12
CN1293070C (zh) 2007-01-03
CO5611196A2 (es) 2006-02-28
EG24415A (en) 2009-05-25
EP1480970A1 (en) 2004-12-01
KR20040089615A (ko) 2004-10-21
AU2003219023B2 (en) 2006-11-30
CA2706618A1 (en) 2003-09-12
BR0308201A (pt) 2005-01-04
US20080255176A1 (en) 2008-10-16
NZ534732A (en) 2006-05-26
NO20044117L (no) 2004-09-28
HK1071364A1 (en) 2005-07-15

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