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WO1995013812A1 - Utilisation de dihydro-1,4 pyridine substituee pour reduire la pression intra-oculaire - Google Patents

Utilisation de dihydro-1,4 pyridine substituee pour reduire la pression intra-oculaire Download PDF

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Publication number
WO1995013812A1
WO1995013812A1 PCT/EP1994/003757 EP9403757W WO9513812A1 WO 1995013812 A1 WO1995013812 A1 WO 1995013812A1 EP 9403757 W EP9403757 W EP 9403757W WO 9513812 A1 WO9513812 A1 WO 9513812A1
Authority
WO
WIPO (PCT)
Prior art keywords
dimethyl
phenyl
dihydropyridine
dimethoxycarbonyl
nitroxyethoxy
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/EP1994/003757
Other languages
German (de)
English (en)
Inventor
Jan Bron
Geert Jan Sterk
Hendrik Timmerman
Jan Fetze Van Der Werf
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.)
Altana Pharma BV
Original Assignee
BYK Nederland BV
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
Application filed by BYK Nederland BV filed Critical BYK Nederland BV
Priority to AU81427/94A priority Critical patent/AU8142794A/en
Publication of WO1995013812A1 publication Critical patent/WO1995013812A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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

Definitions

  • the invention relates to the new use of substituted 1,4-dihydropyridines for the production of medicaments for the treatment of eye diseases.
  • the invention relates to the use of compounds of the formula I.
  • Rl is 1-4C-alkyl
  • R2 is 1-4C-alkyl or the radical -CH 2 -S-CH 2 CH 2 - H 2 ,
  • R3 means 1-4C-alkyl
  • R4 denotes 1-4C-alkyl or a menthyl radical
  • R5 and R6 are the same or different and are hydrogen (H), 1-4C-alkyl, 1-4C-alkoxy, cyano (CN), nitro (NQ ? ) Or halogen, X 0, NH, CO, 0 (CH 2 ) Represents -CO or S, Y represents 0, N, NH, S, CO, CONH, COO or a bond line with which
  • Y is not 0, NH or S when X is NH
  • - Y does not mean CO, COO or CONH when X represents CO
  • Y is not N, NH, CONH or COO when X is 0,
  • a l-15C-alkylene, 5-7C-cycloalkylene, di-1-4C-alkylene-5-7C-cycloalkane or a group of the formula [(CH 2 ) 2 0] (CH 2 ) 2 with q 1 or 2 means m denotes 1 or (if Y represents N) 2 represents Z represents 0 or NH and p represents a number from 1 to 6, and their pharmacologically acceptable salts for the production of medicaments for the treatment of the pathologically increased intraocular pressure.
  • 1-4C-A1kyl stands for straight-chain or branched alkyl radicals with 1 to 4 carbon atoms. Examples include butyl, iso-butyl, sec-butyl, tert. -Butyl -, propyl, isopropyl, ethyl and especially the methyl radical.
  • 1-4C-alkoxy radicals contain one of the 1-4C-alkyl radicals mentioned above.
  • the methoxy radical is preferred.
  • Halogen in the sense of the present invention is bromine, chlorine and fluorine.
  • 2-15C-Alkylene stands for straight-chain or branched alkylene radicals with 2 to 15 carbon atoms. Examples are ethylene (-CH 2 CH 2 -), trimethylene (-CH 2 CH 2 CH 2 -), tetramethylene (-CH 2 CH 2 CH 2 CH 2 -), pentamethylene (-CH 2 CH 2 CH 2 CH 2 CH 2 -), hexamethylene (-CH 2 - (CH 2 ) 4 -CH 2 -), octamethylene (-CH 2 - (CH 2 ) 6 -CH 2 -), decamethylene (-CH 2 - (CH 2 ) 8 -CH 2 -), tetradecamethylene (-CH 2 - (CH 2 ) 12 -CH 2 -), 1,2-dimethylethylene [-CH (CH 3 ) -CH (CH 3 ) -], 1,1-dimethyl - ethylene [-C (CH 3 ) 2 -CH 2 -], isopropyl idene [-C
  • 5-7C-Cycloalkylene stands for cycloalkylene radicals with 5 to 7 carbon atoms. Cyclohexylene radicals are preferred, the 1,2- and 1,4-cyclohexylene radicals being mentioned, for example.
  • Di-1-4C-alkylene-5-7C-cycloalkane stands for cyclic hydrocarbons with 5 to 7 carbon atoms which are substituted by two (identical or different) alkylene residues with 1 to 4 carbon atoms.
  • a preferred di-1-4C-alkylene-5-7C-cycloalkane radical is the 1,4-dimethylenecyclohexane radical.
  • Suitable pharmacologically acceptable salts for compounds of the formula I are preferably all acid addition salts with inorganic and organic acids commonly used in galenics. Suitable as such are water-soluble and water-insoluble acid addition salts with acids such as, for example, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, acetic acid, citric acid, D-gluconic acid, benzoic acid, 2- (4-hydroxybenzoyl) benzoic acid, butyric acid, sulfosalicylic acid, maleic acid, maleic acid Lauric acid, malic acid, fumaric acid, succinic acid, oxalic acid, tartaric acid, embonic acid, stearic acid, toluenesulfonic acid, methanesulfonic acid or 3-hydroxy-2-naphthoic acid, the acids in the salt production - depending on whether it is a mono- or polybasic acid and, depending on which salt is desired - be
  • the compounds of the formula I are used in particular in the form of those medicaments as are suitable for the treatment of eye diseases.
  • suitable pharmaceutical formulations include, for example, emulsions, suspensions, ointments or solutions (e.g. eye drops) in which the amount of hydrogen is advantageously between 0.01 and 99%.
  • auxiliaries which are suitable for the desired pharmaceutical formulations on the basis of his specialist knowledge.
  • antioxidants for example, to use antioxidants, dispersants, emulsifiers, preservatives, solubilizers or permeation promoters.
  • Compounds of the formula I which can be used according to the invention are mentioned in the claims. Particularly noteworthy here are those compounds that have only a low cardiac and / or circulatory activity systemically.
  • the compounds of formula I are known from WO92 / 02503.
  • the reduction in intraocular pressure in female New Zealand albino rabbits was determined using conventional methods.
  • the substances to be examined were dropped in 0.05% solution (50 ⁇ l) into one eye, while a solution of the control substance was dropped into the other eye.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Utilisation de composés selon la formule (I), où les substituants et les symboles ont la signification indiquée dans la description, et utilisation de leurs sels, compatibles sur le plan pharmacologique, pour la fabrication de produits pharmaceutiques destinés au traitement de l'élévation pathologique de la pression intra-oculaire.
PCT/EP1994/003757 1993-11-17 1994-11-12 Utilisation de dihydro-1,4 pyridine substituee pour reduire la pression intra-oculaire Ceased WO1995013812A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU81427/94A AU8142794A (en) 1993-11-17 1994-11-12 Use of substituted 1,4-dihydropyridine to reduce intraocular pressure

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3427/93-2 1993-11-17
CH342793 1993-11-17

Publications (1)

Publication Number Publication Date
WO1995013812A1 true WO1995013812A1 (fr) 1995-05-26

Family

ID=4255749

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/003757 Ceased WO1995013812A1 (fr) 1993-11-17 1994-11-12 Utilisation de dihydro-1,4 pyridine substituee pour reduire la pression intra-oculaire

Country Status (2)

Country Link
AU (1) AU8142794A (fr)
WO (1) WO1995013812A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2585574A1 (fr) * 1985-07-31 1987-02-06 Corbiere Jerome Nouvelles compositions pharmaceutiques anti-glaucomateuses a base de 1,4-dihydropyridines et leur procede d'obtention
EP0289746A2 (fr) * 1987-03-12 1988-11-09 Kyoto Pharmaceutical Industries, Ltd. Dérivés de 1,4-dihydropyridine et compositions pharmaceutiques les contenant
WO1992002503A1 (fr) * 1990-08-02 1992-02-20 Cedona Pharmaceuticals Bv Nouveaux derives de dihydropyridine-1,4

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2585574A1 (fr) * 1985-07-31 1987-02-06 Corbiere Jerome Nouvelles compositions pharmaceutiques anti-glaucomateuses a base de 1,4-dihydropyridines et leur procede d'obtention
EP0289746A2 (fr) * 1987-03-12 1988-11-09 Kyoto Pharmaceutical Industries, Ltd. Dérivés de 1,4-dihydropyridine et compositions pharmaceutiques les contenant
WO1992002503A1 (fr) * 1990-08-02 1992-02-20 Cedona Pharmaceuticals Bv Nouveaux derives de dihydropyridine-1,4

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J.A. NATHANSON: "Nitrovasodilators as a new class of ocular hypotensive agents.", J. PHARMACOL. EXP. THER., vol. 260, no. 3, 1992, pages 956 - 965 *

Also Published As

Publication number Publication date
AU8142794A (en) 1995-06-06

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