EP1397327A2 - Aminoalkylesters d'acide diphenylalcoxy-acetique n et alpha-substitues deuterises et medicaments contenant lesdits composes - Google Patents

Aminoalkylesters d'acide diphenylalcoxy-acetique n et alpha-substitues deuterises et medicaments contenant lesdits composes

Info

Publication number
EP1397327A2
EP1397327A2 EP02752970A EP02752970A EP1397327A2 EP 1397327 A2 EP1397327 A2 EP 1397327A2 EP 02752970 A EP02752970 A EP 02752970A EP 02752970 A EP02752970 A EP 02752970A EP 1397327 A2 EP1397327 A2 EP 1397327A2
Authority
EP
European Patent Office
Prior art keywords
acetic acid
ester
diphenyl
perdeuteropropyloxy
piperidinyl
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.)
Withdrawn
Application number
EP02752970A
Other languages
German (de)
English (en)
Inventor
Rudolf-Giesbert Alken
Johann Roither
Wolf-Dietrich Hübner
Werner Hrachowina
Thomas Stabingis
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.)
Turicum Drug Development AG
Original Assignee
Turicum Drug Development 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
Application filed by Turicum Drug Development AG filed Critical Turicum Drug Development AG
Publication of EP1397327A2 publication Critical patent/EP1397327A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • 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
    • C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
    • Y10T436/145555—Hetero-N

Definitions

  • the invention relates to deuterated N- and ⁇ -substituted Diphenylalkoxyessigklaklarea inoalkylester and medicaments containing these compounds.
  • Diphenylalkoxyacetic acid amino alkyl ester is propiverin (DD 106643, DD 139212 and DE 2937489). This compound is used to treat detrusor hyperactivity.
  • the object of the present invention is to provide N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters which have improved pharmokinetic and / or pharmacodynamic properties compared to the already known compounds.
  • the object is therefore achieved by providing deuterated N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters of the general formula I.
  • Ri represents hydrogen, deuterium, an n-propyl radical or a single, multiple or a perdeuterated n-propyl radical
  • R 2 is oxygen, a methyl group or a mono-, di- or trideuteromethyl group and
  • R 3 are, independently of one another, H or deuterium, at least one of the radicals R 1, R 2 or R 3 being, independently of one another, deuterium or containing deuterium, and their physiologically tolerable salts.
  • Ri represents an n-propyl radical or a single, multiple or a perdeuterated n-propyl radical
  • R 2 is a methyl group or a mono-, di- or trideuteromethyl group
  • R 3 are, independently of one another, H or deuterium, at least one of the radicals R 1, R 2 or R 3 being, independently of one another, deuterium or containing deuterium, and their physiologically tolerable salts.
  • R 1 is an n-propyl radical or a single, multiple or a perdeuterated n-propyl radical
  • R 2 is oxygen
  • R 3 is independently H or deuterium, wherein at least one of the radicals R lr R 2 and R 3 are independently deuterium or contains deuterium, as well as their physiologically acceptable salts.
  • N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters are particularly preferred:
  • deuterated N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters and their physiologically used salts for the production of medicaments for Treatment of hypertonic functional states in the urinary bladder.
  • compositions which contain the deuterated N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters and their physiologically tolerable salts for the treatment of hypertonic functional states of the bladder in addition to pharmaceutically acceptable auxiliaries and / or additives.
  • the present invention furthermore relates to pharmaceutical compositions for percutaneous and / or transdermal application of interpreted N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters and their physiologically tolerable salts
  • N- and ⁇ -substituted diphenylalkoxyacetic acid aminoalkyl esters are known per se and can be carried out as described in DD 106643.
  • methyl benzilate is transesterified in the presence of a catalytically active strong base with an N-substituted aminol alcohol with simultaneous azeotropic removal of methanol and converted into the ⁇ -chloro compound by reaction with thionyl chloride.
  • the halogen compound is reacted with an alcohol, water or D 2 0 and, after a reaction time of up to 10 hours, gives the desired N- and ⁇ -substituted aminoalkyl diphenylalkoxyacetate in the form of its acid chloride.
  • Typical physiologically compatible inorganic and organic acids are, for example, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, malic acid, citric acid, salicylic acid, adipic acid and benzoic acid.
  • Other acids that can be used are described, for example, in Progress in Pharmaceutical Research, vol. 10, pages 224-225, Birkhauser Verlag, Basel and Stuttgart, 1966, and Journal of Pharmaceutical Sciences, vol. 66, pages 1-5 (1977).
  • the acid addition salts are generally in a manner known per se by mixing the free base or its solutions with the corresponding acid or its solutions in an organic solvent, for example a lower alcohol such as methanol, ethanol, n-propanol or isopropanol or a lower ketone such as Acetone, methyl ethyl ketone or methyl isobutyl ketone or an ether such as diethyl ether, tetrahydrofuran or dioxane. Mixtures of the solvents mentioned can also be used for better crystal deposition.
  • physiologically compatible aqueous solutions of acid addition salts of the compounds used according to the invention can be prepared in an aqueous acid solution.
  • the acid addition salts of the compounds according to the invention can be carried out in a manner known per se, e.g. B. with alkalis or ion exchangers, are converted into the free base.
  • the free base can be reacted with Chen, which are suitable for the formation of therapeutically usable salts, win further salts.
  • These or other salts of the new compound, such as. B. the picrate can also be used to purify the free base by converting the free base into a salt, separating this and in turn releasing the base from the salt.
  • the present invention also relates to pharmaceuticals for oral, rectal, subcutaneous, intravenous or intramuscular application which, in addition to conventional carriers and diluents, contain a compound of the general formula I or its acid addition salt as active ingredient.
  • the medicaments of the invention are produced in a known manner with the customary solid or liquid carriers or diluents and the commonly used pharmaceutical-technical auxiliaries in accordance with the desired type of application with a suitable dosage.
  • the preferred preparations are in a dosage form which is suitable for oral administration.
  • dosage forms are, for example, tablets, film-coated tablets, coated tablets, capsules, pills, powders, solutions or suspensions or depot forms.
  • parenteral preparations such as injection solutions are also suitable. Suppositories may also be mentioned as preparations.
  • Corresponding tablets can be obtained, for example, by mixing the active ingredient with known auxiliaries, for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as corn starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate or such as carboxyl polymethylene, carboxylmethyl cellulose, cellulose acetate phthalate or polyvinyl acetate.
  • auxiliaries for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as corn starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate or such as carboxyl polymethylene, carboxylmethyl cellulose, cellulose acetate phthalate or polyvinyl acetate.
  • Coated tablets can accordingly be produced by coating cores produced analogously to the tablets with agents conventionally used in tablet coatings, for example polyvinylpyrrolidone or shellac, gum arabic, talc, titanium dioxide or sugar.
  • the coated tablet can also consist of several layers, wherein the auxiliaries mentioned above for the tablets can be used.
  • Solutions or suspensions with the active ingredient used according to the invention can additionally taste-improving agents such as saccharin, cyclamate or sugar and z.
  • B. contain flavorings such as vanillin or orange extract. They can also contain suspending agents such as sodium carboxymethyl cellulose or preservatives such as p-hydroxybenzoates.
  • Capsules containing active ingredients can be produced, for example, by mixing the active ingredient with an inert carrier such as milk sugar or sorbitol and encapsulating it in gelatin capsules.
  • Suitable suppositories can be produced, for example, by mixing them with carriers such as neutral fats or polyethylene glycol or their derivatives.
  • the preparation of the pharmaceuticals according to the invention for percutaneous application is known to the person skilled in the art.
  • the auxiliary agents known per se are The preparation of the pharmaceutical preparations according to the invention and is described in the manuals known to the person skilled in the art, for example Hager's Handbuch (5.) 2, 622-1045; List et al. , Drug form theory, Stuttgart: Wiss. Verlagsges. , 1985; Sucker et al., Pharmaceutical Technology, Stuttgart: Thieme 1991; Ulimann's Encyclopedia (5th) A 19, 241-271; Voigt, Pharmaceutical Technology, Berlin: Ullstein Mosby 1995.
  • the pharmaceuticals thus produced can be used to treat hypertensive functional states in the urinary bladder.
  • Symptoms include uncontrolled urine leakage (enuresis), pathological urination (urge incontinence) and painful bladder cramps (tenesmen).
  • the compounds according to the invention have a number of advantages over the compounds known in the prior art which do not have deuterium.
  • the deuteration changes the metabolism in the organism.
  • the hydroxylation on the phenyl radical is made more difficult, which leads to a reduced first-pass effect. This makes it possible to change the dosage and create longer-lasting preparations, which can also improve compliance in the form of depot preparations.
  • the pharmacodynamics have also changed because the deuterated compounds form completely different hydration shells, so that the distribution in the organism differs significantly from that of the undeuterated compounds. This makes it possible to develop completely new forms of preparation.
  • activated carbon is added and the solution is filtered hot. The solution is then cooled and the product filtered and washed with a little n-propanol and dried.
  • Additional product is obtained from the mother liquor by adding n-hexane and is recrystallized from a small amount of n-propanol with a little activated carbon.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des aminoalkylesters d'acide alpha , alpha -diphényl- alpha -alcoxy-acétique N-substitués deutérisés, ainsi que leurs sels physiologiquement compatibles. L'invention concerne en outre l'utilisation d'aminoalkylesters d'acide alpha , alpha -diphényl- alpha -alcoxy-acétique N-substitués deutérisés, pour traiter des états fonctionnels d'hypertonie dans la zone de la vessie, ainsi que la production de médicaments pour traiter des états fonctionnels d'hypertonie dans la région de la vessie, en plus d'auxiliaires et/ou d'additifs pharmaceutiquement compatibles.
EP02752970A 2001-06-17 2002-06-17 Aminoalkylesters d'acide diphenylalcoxy-acetique n et alpha-substitues deuterises et medicaments contenant lesdits composes Withdrawn EP1397327A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10129832 2001-06-17
DE10129832A DE10129832A1 (de) 2001-06-17 2001-06-17 Deuterierte N- und alpha-substituierte Diphenylalkoxyessigsäureaminoalkylester sowie diese Verbindungen enthaltende Arzneimittel
PCT/DE2002/002260 WO2002102743A2 (fr) 2001-06-17 2002-06-17 Aminoalkylesters d'acide diphenylalcoxy-acetique n et alpha-substitues deuterises et medicaments contenant lesdits composes

Publications (1)

Publication Number Publication Date
EP1397327A2 true EP1397327A2 (fr) 2004-03-17

Family

ID=7688891

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02752970A Withdrawn EP1397327A2 (fr) 2001-06-17 2002-06-17 Aminoalkylesters d'acide diphenylalcoxy-acetique n et alpha-substitues deuterises et medicaments contenant lesdits composes

Country Status (16)

Country Link
US (1) US20040242887A1 (fr)
EP (1) EP1397327A2 (fr)
JP (1) JP2004534802A (fr)
KR (1) KR20040020926A (fr)
CN (1) CN1516684A (fr)
CA (1) CA2451638A1 (fr)
CZ (1) CZ20033365A3 (fr)
DE (1) DE10129832A1 (fr)
HU (1) HUP0400213A3 (fr)
IL (1) IL159410A0 (fr)
IS (1) IS7061A (fr)
NO (1) NO20035599D0 (fr)
NZ (1) NZ530352A (fr)
PL (1) PL367218A1 (fr)
RU (1) RU2004101229A (fr)
WO (1) WO2002102743A2 (fr)

Families Citing this family (16)

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Publication number Priority date Publication date Assignee Title
US20080146573A1 (en) * 2006-12-04 2008-06-19 Auspex Pharmaceuticals, Inc. Preparation and utility of substituted oxzolidinones
US20090209608A1 (en) * 2007-08-29 2009-08-20 Protia, Llc Deuterium-enriched asenapine
US20090062185A1 (en) * 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched anidulafungin
US20090069219A1 (en) * 2007-09-09 2009-03-12 Protia, Llc Deuterium-enriched telavancin
US20090076158A1 (en) * 2007-09-13 2009-03-19 Protia, Llc Deuterium-enriched bicalutamide
US20090075870A1 (en) * 2007-09-17 2009-03-19 Protia, Llc Deuterium-enriched caspofungin
US20090082419A1 (en) * 2007-09-26 2009-03-26 Protia, Llc Deuterium-enriched tegaserod
AR075584A1 (es) 2009-02-27 2011-04-20 Intermune Inc COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO.
WO2010138889A1 (fr) * 2009-05-28 2010-12-02 Concert Pharmaceuticals, Inc. Peptides destinés au traitement des infections par le vhc
EP2483273A4 (fr) * 2009-09-28 2013-05-01 Hoffmann La Roche Nouveaux inhibiteurs macrocycliques de réplication du virus de l'hépatite c
CN102584592B (zh) * 2011-12-28 2014-10-15 李进 一种氘代的拟除虫菊酯化合物及其制备方法和应用
CA2862990C (fr) * 2012-01-30 2017-10-24 Taiho Pharmaceutical Co., Ltd. Nouveau compose ester d'acide acetique ou sel de ce compose
KR102240999B1 (ko) * 2012-08-09 2021-04-15 체이스 파마슈티칼스 코포레이션 피페리디늄 4급 염들
WO2014192847A1 (fr) * 2013-05-30 2014-12-04 大鵬薬品工業株式会社 Nouveau composé d'ester d'acide benzilique fluoré et son sel
CN107445798B (zh) * 2016-06-01 2020-11-03 中国农业大学 一种α,α‐二氘代醇类化合物的合成方法
CN116078377B (zh) * 2023-03-06 2023-06-27 泽升科技(广州)有限公司 一种负载催化剂催化制备氘代苯的生产工艺

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DD139212A1 (de) * 1978-10-09 1979-12-19 Christian Starke Verfahren zur herstellung eines neuen arzneimittels aus alpha,alpha-diphenyl-alpha-alkoxyessigsaeure-1-methylpiperidyl-4-ester-derivaten
JPS6439873A (en) * 1987-08-05 1989-02-10 Sharp Kk Synchronizing signal generating circuit
ATE170506T1 (de) * 1993-01-28 1998-09-15 Univ Iowa Res Found Deuteriertes sevofluran als inhalationsbetäubungsmittel
DE4343838C2 (de) * 1993-12-22 1998-07-09 Lohmann Therapie Syst Lts Deuteriertes Arzneimittel in transdermaler Applikation und Verfahren zu seiner Herstellung

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Also Published As

Publication number Publication date
US20040242887A1 (en) 2004-12-02
KR20040020926A (ko) 2004-03-09
JP2004534802A (ja) 2004-11-18
IL159410A0 (en) 2004-06-01
IS7061A (is) 2003-11-28
PL367218A1 (en) 2005-02-21
WO2002102743A3 (fr) 2003-03-13
HUP0400213A3 (en) 2005-08-29
WO2002102743A9 (fr) 2004-03-11
CZ20033365A3 (cs) 2004-09-15
WO2002102743A2 (fr) 2002-12-27
DE10129832A1 (de) 2003-07-10
RU2004101229A (ru) 2005-06-27
CA2451638A1 (fr) 2002-12-27
HUP0400213A2 (hu) 2004-07-28
CN1516684A (zh) 2004-07-28
NZ530352A (en) 2004-12-24
NO20035599D0 (no) 2003-12-16

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