WO1993012796A1 - Utilisation des inhibiteurs de la renine pour le traitement du glaucome - Google Patents

Utilisation des inhibiteurs de la renine pour le traitement du glaucome Download PDF

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Publication number
WO1993012796A1
WO1993012796A1 PCT/JP1992/001656 JP9201656W WO9312796A1 WO 1993012796 A1 WO1993012796 A1 WO 1993012796A1 JP 9201656 W JP9201656 W JP 9201656W WO 9312796 A1 WO9312796 A1 WO 9312796A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
acyl
lower alkyl
group
hydrogen
Prior art date
Application number
PCT/JP1992/001656
Other languages
English (en)
Inventor
Yoko Tanaka
Akira Kagayama
Takehisa Hata
Original Assignee
Fujisawa Pharmaceutical Co., Ltd.
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 Fujisawa Pharmaceutical Co., Ltd. filed Critical Fujisawa Pharmaceutical Co., Ltd.
Priority to KR1019940702038A priority Critical patent/KR940703665A/ko
Priority to AU31712/93A priority patent/AU661748B2/en
Priority to JP5511545A priority patent/JPH07506807A/ja
Priority to EP93900396A priority patent/EP0617622A1/fr
Publication of WO1993012796A1 publication Critical patent/WO1993012796A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/55—Protease inhibitors
    • A61K38/553—Renin inhibitors
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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

Definitions

  • Glaucoma is a condition characterized by an increase in intraocular pressure. Increased intraocular pressure can lead to optic nerve damage and defects in the visual field. Blindness can result if the condition is left untreated.
  • This invention relates to new use of amino acid derivatives which inhibit renin for treating glaucoma or reducing and/or controlling intraocular pressure.
  • this invention provides new use of said amino acid derivatives for treating glaucoma or reducing and/or controlling intraocular pressure.
  • this invention provides an agent and a pharmaceutical composition for treating glaucoma or reducing and/or controlling intraocular pressure, which comprises said amino acid derivatives.
  • this invention provides a method for treating glaucoma or reducing and/or controlling intraocular pressure, which comprises administering said amino acid derivatives to mammals.
  • amino acid derivatives used in this invention are known as renin inhibiting compounds and disclosed in
  • amino acid derivatives used in this invention can be represented by the following general formula [I].
  • R 3 O H wherein R 1 is lower alkyl optionally substituted with
  • a substituent selected from the group consisting of acyl, hydroxy, lower alkoxy, aryl, lower alkylthio and a group of the formula :
  • R 5 is hydrogen or acyl
  • R 6 is hydrogen or lower alkyl
  • R 2 is hydrogen or lower alkyl
  • R 3 is hydrogen or lower alkyl
  • R 4 is lower alkyl
  • lower is intended to mean a group having to 7 carbon atom(s), unless otherwise provided.
  • Suitable “lower alkyl” may be a straight or branched one such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl,
  • acyl (lower)alkyl may be a group of the formula :
  • R 9 -CO- and R 9 -SO 2 - wherein R 7 and R 8 are each hydrogen, aryl, cyclo(lower)- alkyl, a heterocyclic group or lower alkyl optionally substituted with a substituent selected from the group consisting of lower alkoxycarbonyl, lower alkoxy, aryl and a heterocyclic group, or
  • R 7 and R 8 are taken together with the attached nitrogen atom to form a heterocyclic group optionally substituted with lower alkyl
  • R 9 is aryl, cyclo(lower)alkyl, lower alkyl optionally substituted with a substituent selected from the group consisting of lower alkoxy and mono- or di(lower)alkylamino, or lower alkoxy optionally substituted with a substituent selected from the group
  • Suitable "aryl” may be phenyl, naphthyl, tolyl, xylyl, mesityl, cumenyl, and the like, in which preferabl one is phenyl.
  • Suitable "cyclo(lower)alkyl” is cyclopropyl
  • Suitable "heterocyclic group" for R 7 and R 8 and one as a substituent on lower alkyl for R 7 and R 8 may include saturated or unsaturated, monocyclic or polycyclic one containing at least one hetero atom such as nitrogen atom, oxygen atom or sulfur atom, preferably N, O and/or S containing 5 or 6 membered heterocyclic group, in which the most preferable ones are morpholino, pyridyl and thiazolyl.
  • Suitable "lower alkoxy” and “lower alkoxy” moiety in the term “lower alkoxycarbonyl” may be a straight or branched one such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, and the like, in which more preferable one may be C 1 -C 4 alkoxy.
  • Suitable "heterocyclic group" formed by R 7 , R 8 and the attached nitrogen atom may be morpholino
  • Suitable "mono- or di(lower)alkylamino” may be methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, dimethylamino,
  • Suitable “lower alkanoyl” may be formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, 4-methylvaleryl, or the like.
  • Suitable "amino-protected or unprotected amino acid residue” may be glycyl, alanyl, b-alanyl, valyl, leucyl, isoleucyl, histidyl, prolyl, seryl, threonyl, cystyl, phenylalanyl, aspartyl, glutamyl, triptophyl, or the like each amino group of which may be protected by N-protectiv group such as substituted or unsubstituted lower alkanoyl [e.g. formyl, acetyl, propionyl, trifluoroacetyl, etc.], phthaloyl, lower alkoxycarbonyl [e.g. tert-butoxycarbonyl tert-amyloxycarbonyl, etc.], substituted or unsubstituted aralkyloxycarbonyl [e.g. benzyloxycarbonyl,
  • unsubstituted arenesulfonyl e.g. benzenesulfonyl, tosyl, etc.
  • nitrophenylsulfenyl e.g. benzenesulfonyl, tosyl, etc.
  • aralkyl e.g. trityl, benzyl, etc.
  • acyl group may be lower alkanoyl [e.g. formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl,
  • amino-protected or unprotected amino acid residue e.g. glycyl, benzoylglycyl, t-butoxycarbonylglycyl,
  • heterocyclic(lower)- alkylcarbamoyl e.g. picolylcarbamoyl, pyridylethylcarbamoyl, thiazolylmethylcarbamoyl, morpholinomethylcarbamoyl, morpholinoethylcarbamoyl, etc.
  • N-heterocyclic(lower)alkyl-N-lower alkylcarbamoyl e.g. N-picolyl-N-methylcarbamoyl, N-pyridylethyl- N-methylcarbamoyl, N-morpholinomethyl-N-ethylcarbamoyl, N-morpholinoethyl-N-methylcarbamoyl, etc.
  • ar(lower)alkylcarbamoyl e.g. benzylcarbamoyl
  • N-ar(lower)alkyl-N-lower alkylcarbamoyl e.g.
  • aroylcarbamoyl e.g. benzoylcarbamoyl, toluoylcarbamoyl, etc.
  • heterocycliccarbamoyl e.g. pyridylcarbamoyl, morpholinocarbamoyl, thiazolylcarbamoyl, etc.
  • N-heterocyclic-N-lower alkylcarbamoyl e.g. N-pyridyl- N-methylcarbamoyl, N-thiazolyl-N-methylcarbamoyl, etc.
  • heterocycliccarbonyl preferably N-containing
  • heterocyclic-N-ylcarbonyl which may be substituted with lower alkyl [e.g. morpholinocarbonyl,
  • hydroxy(lower)alkoxycarbonyl e.g. hydroxymethoxycarbonyl hydroxyethoxycarbonyl, hydroxypropoxycarbonyl,
  • benzhydryloxycarbonyl, etc. lower alkenyloxycarbonyl [e.g. vinyloxycarbonyl, allyloxycarbonyl, etc.], lower alkanoyl (lower)alkoxycarbonyl [e.g. acetylmethoxycarbonyl propionylmethoxycarbonyl, acetylethoxycarbonyl, etc.], lower alkylsulfonyl [e.g. mesyl, ethylsulfonyl,
  • propylsulfonyl isopropylsulfonyl, butylsulfonyl,
  • Suitable "lower alkylthio" may be a straight or branched one such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, tert-butylthio, pentylthio, hexylthio, and the like, in which more preferable one may be C 1 -C 4 alkylthio.
  • Suitable "heterocyclic group" formed by R 1 , R 2 and the attached nitrogen atom can be referred to the ones formed by R 7 , R 8 and the attached nitrogen atom as exemplified above.
  • Suitable "hydroxy(lower)alkyl” may be hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl,
  • Suitable "lower alkoxy(lower)alkyl” may be methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxypropyl, and the like.
  • Suitable pharmaceutically acceptable salts of the compounds [I] are conventional non-toxic salts and includ an organic acid addition salt [e.g. formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, benzenesulfonate, toluenesulfonate, etc.], an inorganic acid addition salt [e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.], a salt with an amino acid [e.g. aspartic acid salt, glutamic acid salt, etc.], or the like.
  • organic acid addition salt e.g. formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, benzenesulfonate, toluenesulfonate, etc.
  • an inorganic acid addition salt e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.
  • controlling intraocular pressure means the regulation, attenuation and modulation of increased intraocular tension.
  • the term also means that the
  • R 1 is lower alkyl substituted with a substituent selected from the group consisting of a group of the formula :
  • R 7 and R 8 are each hydrogen or lower alkyl, or
  • R 6 is hydrogen or lower alkyl
  • R 2 is hydrogen or lower alkyl
  • R 3 is hydrogen or lower alkyl
  • R 4 is lower alkyl.
  • R 1 is C 1 -C 4 alkyl substituted with a group of the
  • R 6 is C 1 -C 4 alkyl
  • R 2 is C 1 -C 4 alkyl
  • R 3 is C 1 -C 4 alkyl
  • R 4 is C 1 -C 5 alkyl.
  • the most interesting compounds are 2(S)-[N ⁇ -[2(S)- ⁇ N-(2-morpholinocarbonylethyl)-N- methylaminocarbonyloxy ⁇ -3-phenylpropionyl]-N ⁇ -methyl-L- histidyl]amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane or its hydrochloride,
  • the compound [I] may include one or more stereoisomers due to asymmetric carbon atoms, and all of such isomers and mixture thereof are included within the scope of this invention.
  • test data of the representative compound of this invention is shown in the following.
  • the total volume of 50 ⁇ l was applied in two portion of 25 ⁇ l , maintaining a waiting period of 5 minutes before the next administration.
  • Intraocular pressure was measured using Alcon pneumatonograph . 10 ⁇ l of 0 .4% oxybuprocaine
  • hydrochloride was applied to the cornea to minimize discomfort during IOP measurements. IOP measurements were made at 0 (pretreat) and 1 hour after instillation of the test compound or vehicle.
  • the compounds [I] and pharmaceutically acceptable salts thereof of the present invention can be used in a form of pharmaceutical
  • compositions may be capsules, tablets, dragees, granules, solution (including ophthalmic solution), suspension, emulsion, ointment, or the like. If desired, there may be included in these preparations, auxiliary substances, stabilizing agents, wetting or emulsifying agents, buffers and other commonly used additives.
  • the compound [I] and pharmaceutically acceptable salts thereof of the present invention may be used in combination with other ingredients which control intraocular pressure such as beta-adrenergic antagonist [e.g. timolol, etc.], angiotensin converting enzyme inhibitor [e.g. captopril, enalapril, etc.], or the like.
  • beta-adrenergic antagonist e.g. timolol, etc.
  • angiotensin converting enzyme inhibitor e.g. captopril, enalapril, etc.
  • an average single dose of about 0.001 mg, 0.01 mg, 0.1 mg, 1 mg, 10 mg, 50 mg, 100 mg, 250 mg, 500 mg and 1000 mg of the compound [I] may be effective for treating glaucoma or reducing and/or controlling intraocular pressure. In general, amounts between 0.1 mg/body and about 1,000 mg/body may be administered per day.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Utilisation d'un composé de la formule (I) dans laquelle chaque symbole est tel que défini dans la description, ou utilisation d'un sel de ce composé pharmaceutiquement acceptable pour le traitement du glaucome ou l'atténuation de la pression intraoculaire.
PCT/JP1992/001656 1991-12-20 1992-12-18 Utilisation des inhibiteurs de la renine pour le traitement du glaucome WO1993012796A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1019940702038A KR940703665A (ko) 1991-12-20 1992-12-18 녹내장 치료를 위한 레닌 저해제의 용도
AU31712/93A AU661748B2 (en) 1991-12-20 1992-12-18 Use of renin inhibitors for the treatment of glaucoma
JP5511545A JPH07506807A (ja) 1991-12-20 1992-12-18 緑内障治療のためのレニン阻害剤の使用
EP93900396A EP0617622A1 (fr) 1991-12-20 1992-12-18 Utilisation des inhibiteurs de la renine pour le traitement du glaucome

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9127041.3 1991-12-20
GB919127041A GB9127041D0 (en) 1991-12-20 1991-12-20 New use

Publications (1)

Publication Number Publication Date
WO1993012796A1 true WO1993012796A1 (fr) 1993-07-08

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ID=10706572

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1992/001656 WO1993012796A1 (fr) 1991-12-20 1992-12-18 Utilisation des inhibiteurs de la renine pour le traitement du glaucome

Country Status (11)

Country Link
EP (1) EP0617622A1 (fr)
JP (1) JPH07506807A (fr)
KR (1) KR940703665A (fr)
AU (1) AU661748B2 (fr)
CA (1) CA2126211A1 (fr)
GB (1) GB9127041D0 (fr)
HU (2) HUT68175A (fr)
MX (1) MX9207429A (fr)
RU (1) RU94031479A (fr)
WO (1) WO1993012796A1 (fr)
ZA (1) ZA929738B (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025062A1 (fr) * 1993-04-28 1994-11-10 Fujisawa Pharmaceutical Co., Ltd. Composition pharmaceutique administree par voie orale inhibitrice de la renine
US6476046B1 (en) 2000-12-04 2002-11-05 Sepracor, Inc. Diazabicyclo[4.3.0]nonanes, and methods of use thereof
US6720315B2 (en) 2000-06-15 2004-04-13 Pharmacia Corporation Dihydrostilbene alkanoic acid derivatives
US7504392B2 (en) 2002-05-29 2009-03-17 Glaxo Group Limited 2,3,4,5-tetrahydro-1H-3-benzazepines and their medical use
US8710043B2 (en) 2011-06-24 2014-04-29 Amgen Inc. TRPM8 antagonists and their use in treatments
US8778941B2 (en) 2011-06-24 2014-07-15 Amgen Inc. TRPM8 antagonists and their use in treatments
US8952009B2 (en) 2012-08-06 2015-02-10 Amgen Inc. Chroman derivatives as TRPM8 inhibitors
US11851422B2 (en) 2021-07-09 2023-12-26 Aligos Therapeutics, Inc. Anti-viral compounds
US11952365B2 (en) 2020-06-10 2024-04-09 Aligos Therapeutics, Inc. Anti-viral compounds

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987002581A1 (fr) * 1985-11-05 1987-05-07 Schering Corporation Inhibiteurs de la renine et procedes d'utilisation de ces inhibiteurs
EP0300189A2 (fr) * 1987-06-22 1989-01-25 Fujisawa Pharmaceutical Co., Ltd. Dérivés d'acides aminés, leurs procédés de préparation et compositions pharmaceutiques les contenant
EP0311012A2 (fr) * 1987-10-06 1989-04-12 Abbott Laboratories Traitement du glaucome
EP0341481A1 (fr) * 1988-04-29 1989-11-15 E.R. Squibb & Sons, Inc. Dérivés N-hétérocycliques d'alcohol
EP0476515A1 (fr) * 1990-09-17 1992-03-25 Fujisawa Pharmaceutical Co., Ltd. Nouveaux derivés d'amino-acides, procédé de leur préparation et composition pharmaceutique les contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987002581A1 (fr) * 1985-11-05 1987-05-07 Schering Corporation Inhibiteurs de la renine et procedes d'utilisation de ces inhibiteurs
EP0300189A2 (fr) * 1987-06-22 1989-01-25 Fujisawa Pharmaceutical Co., Ltd. Dérivés d'acides aminés, leurs procédés de préparation et compositions pharmaceutiques les contenant
EP0311012A2 (fr) * 1987-10-06 1989-04-12 Abbott Laboratories Traitement du glaucome
EP0341481A1 (fr) * 1988-04-29 1989-11-15 E.R. Squibb & Sons, Inc. Dérivés N-hétérocycliques d'alcohol
EP0476515A1 (fr) * 1990-09-17 1992-03-25 Fujisawa Pharmaceutical Co., Ltd. Nouveaux derivés d'amino-acides, procédé de leur préparation et composition pharmaceutique les contenant

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025062A1 (fr) * 1993-04-28 1994-11-10 Fujisawa Pharmaceutical Co., Ltd. Composition pharmaceutique administree par voie orale inhibitrice de la renine
US6720315B2 (en) 2000-06-15 2004-04-13 Pharmacia Corporation Dihydrostilbene alkanoic acid derivatives
US6833366B1 (en) 2000-06-15 2004-12-21 Pharmacia Corporation Dihydrostilbene alkanoic acid derivatives
US6476046B1 (en) 2000-12-04 2002-11-05 Sepracor, Inc. Diazabicyclo[4.3.0]nonanes, and methods of use thereof
US7504392B2 (en) 2002-05-29 2009-03-17 Glaxo Group Limited 2,3,4,5-tetrahydro-1H-3-benzazepines and their medical use
US8710043B2 (en) 2011-06-24 2014-04-29 Amgen Inc. TRPM8 antagonists and their use in treatments
US8778941B2 (en) 2011-06-24 2014-07-15 Amgen Inc. TRPM8 antagonists and their use in treatments
US9096527B2 (en) 2011-06-24 2015-08-04 Amgen Inc. TRPM8 antagonists and their use in treatments
US8952009B2 (en) 2012-08-06 2015-02-10 Amgen Inc. Chroman derivatives as TRPM8 inhibitors
US11952365B2 (en) 2020-06-10 2024-04-09 Aligos Therapeutics, Inc. Anti-viral compounds
US11851422B2 (en) 2021-07-09 2023-12-26 Aligos Therapeutics, Inc. Anti-viral compounds

Also Published As

Publication number Publication date
EP0617622A1 (fr) 1994-10-05
MX9207429A (es) 1993-06-01
RU94031479A (ru) 1996-10-20
GB9127041D0 (en) 1992-02-19
ZA929738B (en) 1993-06-17
HU211939A9 (en) 1996-01-29
CA2126211A1 (fr) 1993-07-08
AU661748B2 (en) 1995-08-03
AU3171293A (en) 1993-07-28
JPH07506807A (ja) 1995-07-27
HU9401833D0 (en) 1994-09-28
KR940703665A (ko) 1994-12-12
HUT68175A (en) 1995-05-29

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