HK24295A - Mercapto- or acylthio-trifluoromethyl amide derivatives and their use - Google Patents

Mercapto- or acylthio-trifluoromethyl amide derivatives and their use

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Publication number
HK24295A
HK24295A HK24295A HK24295A HK24295A HK 24295 A HK24295 A HK 24295A HK 24295 A HK24295 A HK 24295A HK 24295 A HK24295 A HK 24295A HK 24295 A HK24295 A HK 24295A
Authority
HK
Hong Kong
Prior art keywords
ethyl acetate
hydrogen
compound
mmol
zero
Prior art date
Application number
HK24295A
Other languages
German (de)
English (en)
Inventor
A. Delaney Norma
C. Rovnyak George
Loots Melanie
Original Assignee
E.R. Squibb & Sons, Inc.
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 E.R. Squibb & Sons, Inc. filed Critical E.R. Squibb & Sons, Inc.
Publication of HK24295A publication Critical patent/HK24295A/en

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Claims (25)

  1. Composé de formule dans laquelle    X est    Y est -COR₂, un groupe phényle, phényle substitué par un groupe alkyle de 1 à 4 atomes de carbone, alcoxy de 1 à 4 atomes de carbone, alkylthio de 1 à 4 atomes de carbone, hydroxy, halo, nitro ou trifluorométhyle, ou bien un groupe hétérocyclique choisi entre les groupes thiazolyle, 4,5-dihydrothiazolyle, pyridyle, oxazolyle, isoxazolyle, imidazolyle, tétrazolyle, benzimidazolyle, benzothiazolyle et benzoxazolyle, y compris les groupes hétérocycliques substitués dont les substituants sont choisis entre halo, alkyle et phényle;    Z est    m est égal à zéro ou 1;    n est égal à zéro, 1 ou 2;    p est égal à zéro ou est un nombre de 1 à 6;    t est égal à 2, 3 ou 4;    à cette condition que m et p soient tous deux égaux à zéro quand Y est et à cette condition que m et p ne soient pas tous deux égaux à zéro quand Y est -COR₂;    R₁ et R₈ sont, indépendamment, l'hydrogène, un groupe alkyle inférieur, alkyle inférieur halo-substitué, -(CH₂)r-COR₉, -(CH₂)r-cycloalkyle, -(CH₂)r-(α-naphtyle), -(CH₂)r-(β-naphtyle), -(CH₂)r-NH₂, -(CH₂)r-SH, -(CH₂)r-S-alkyle inférieur, -(CH₂)r-OH, -(CH₂)r-O-alkyle inférieur,    R₂ et R₉ sont, indépendamment, un groupe hydroxy, alcoxy inférieur, (phényl) alcoxy inférieur, -O⊖M⊕ où M⁺ est un ion métallique formateur de sel , ou -NRR′ où R et R′ sont choisis indépendamment entre l'hydrogène et les groupes alkyle et    R₃ est l'hydrogène,    R₄ est l'hydrogène ou un groupe alkyle inférieur de 1 à 4 atomes de carbone, alcoxy inférieur de 1 à 4 atomes de carbone, alkylthio inférieur de 1 à 4 atomes de carbone, halo, hydroxy, CF₃, phényle,    R₅ est un groupe alkyle inférieur, -(CH₂)q-(α-naphtyle), -CH₂)q-(β-naphtyle), -(CH₂)q-cycloalkyle,    R₆ est l'hydrogène ou un groupe alkyle inférieur, cycloalkyle ou phényle;    R₇ est l'hydrogène ou un groupe alkyle inférieur, alcoxy inférieur ou phényle;    r est un nombre entier de 1 à 4; et    q est égal à zéro ou est un nombre entier de 1 à 7.
  2. Composé selon la revendication 1, dans lequel    R₃ est l'hydrogène ou et    X est
  3. Composé selon la revendication 2, dans lequel    R₃ est l'hydrogène;    n est égal à zéro; et    X est
  4. Composé selon la revendication 2, dans lequel    R₃ est l'hydrogène;    n est égal à zéro; et    X est
  5. Composé de formule dans laquelle    X est    Y est -COR₂, ou un groupe phényle, phényle substitué par un groupe alkyle de 1 à 4 atomes de carbone, alcoxy de 1 à 4 atomes de carbone, alkylthio de 1 à 4 atomes de carbone, hydroxy, halo, nitro ou trifluorométhyle, ou bien un groupe hétérocyclique choisi entre les groupes thiazolyle, 4,5-dihydrothiazolyle, pyridyle, oxazolyle, isoxazolyle, imidazolyle, tétrazolyle, benzimidazolyle, benzothiazolyle et benzoxazolyle, y compris les groupes hétérocycliques substitués dont les substituants sont choisis entre halo, alkyle et phényle;    Z est    m est égal à zéro ou 1;    n est égal à zéro, 1 ou 2;    p est égal à zéro ou est un nombre de 1 à 6;    t est égal à 2, 3 ou 4;    à cette condition que m et p soient tous deux égaux à zéro quand Y est et à cette condition que m et p ne soient pas tous deux égaux à zéro quand Y est COR₂;    R₁ et R₈ sont, indépendamment, l'hydrogène ou un groupe alkyle inférieur, alkyle inférieur halo-substitué, -(CH₂)r-COR₉, -(CH₂)r-cycloalkyle, -(CH₂)r-(α-naphtyle), -(CH₂)r-(β-naphtyle), -(CH₂)r-NH₂, -(CH₂)r-SH, -(CH₂)r-S-alkyle inférieur, -(CH₂)r-OH, -(CH₂)r-O-alkyle inférieur, ou    R₂ et R₉ sont indépendamment un groupe hydroxy, alcoxy inférieur, (phényl) alcoxy inférieur, -O⊖M⊕ où M⁺ est un ion métallique formateur de sel, ou -NRR′ où R et R′ sont choisis indépendamment entre l'hydrogène et les groupes alkyle et    R₃ est l'hydrogène ou    R₄ est l'hydrogène ou un groupe alkyle inférieur de 1 à 4 atomes de carbone, alcoxy inférieur de 1 à 4 atomes de carbone, alkylthio inférieur de 1 à 4 atomes de carbone, halo, hydroxy, CF₃, phényle,    R₅ est un groupe alkyle inférieur, -(CH₂)q-(α-naphtyle), -(CH₂)q-(β-naphtyle), -(CH₂)q-cycloalkyle,    R₆ est l'hydrogène ou un groupe alkyle inférieur, cycloalkyle ou phényle;    R₇ est l'hydrogène ou un groupe alkyle inférieur, alcoxy inférieur ou phényle;    r est un nombre entier de 1 à 4; et    q est égal à zéro ou est un nombre entier de 1 à 7.
  6. Composé selon la revendication 5, dans lequel Y est -COR₂.
  7. Composé selon la revendication 6, dans lequel    R₃ est l'hydrogène ou ou et    X est ou
  8. Composé selon la revendication 7, dans lequel    X est    n est égal à zéro; et    R₃ est l'hydrogène ou
  9. Composé selon la revendication 8, qui est l'isomère A du N-[3,3,3-trifluoro-2-(mercaptométhyl)-1-oxopropyl]-L-tryptophane ou l'isomère B du N-[3,3,3-trifluoro-2-(mercaptométhyl)-1-oxopropyl]-L-tryptophane.
  10. Composé selon la revendication 7, dans lequel    n est égal à zéro;    X est et    R₃ est l'hydrogène ou
  11. Composé selon la revendication 10, qui est l'isomère A de la N-[3,3,3-trifluoro-2-(mercaptométhyl)-1-oxopropyl]-L-leucine ou l'isomère B de la N-[3,3,3-trifluoro-2-(mercaptométhyl)-1-oxopropyl]-L-leucine.
  12. Composé selon la revendication 5, dans lequel Y est ou un groupe phényle, phényle substitué par un groupe alkyle de 1 à 4 atomes de carbone, alcoxy de 1 à 4 atomes de carbone, alkylthio de 1 à 4 atomes de carbone, hydroxy, halo, nitro ou trifluorométhyle, ou bien un groupe hétérocyclique choisi entre les groupes thiazolyle, 4,5-dihydrothiazolyle, pyridyle, oxazolyle, isoxazolyle, imidazolyle, tétrazolyle, benzimidazolyle, benzothiazolyle et benzoxazolyle, y compris les groupes hétérocycliques substitués dont les substituants sont choisis entre halo, alkyle et phényle.
  13. Composé selon la revendication 12, dans lequel    R₃ est l'hydrogène ou et    X est
  14. Composé selon la revendication 13, dans lequel    X est    n est égal à zéro; et    R₃ est l'hydrogène ou
  15. Composé selon la revendication 14, qui est le (S,S)-3,3,3-trifluoro-2-(mercaptométhyl)-N-[2-(1H-indol-3-yl)-1-(1H-tétrazol-5-yl)éthyl]propanamide ou le (S,R)-3,3,3-trifluoro-2-(mercaptométhyl)-N-[2-(1H-indol-3-yl)-1-(1H-tétrazol-5-yl)éthyl]propanamide.
  16. Composé selon la revendication 13, dans lequel    X est    n est égal à zéro; et    R₃ est l'hydrogène ou
  17. Composé selon la revendication 6, dans lequel    R₃ est l'hydrogène ou    n est égal à zéro; et    X est
  18. Composé selon la revendication 7, dans lequel    R₃ est l'hydrogène;    n est égal à un; et    X est
  19. Composé selon la revendication 12, dans lequel    R₃ est l'hydrogène ou    n est égal à zéro; et    X est
  20. Composé selon la revendication 5, dans lequel    R₃ est l'hydrogène ou    n est égal à zéro; et    X est
  21. Composition pharmaceutique utilisable pour réduire la pression sanguine et/ou produire une diurèse et/ou une natriurie ainsi que pour traiter une insuffisance cardiaque, une insuffisance rénale ou une cirrhose hépatique, comprenant un porteur pharmaceutiquement acceptable et une quantité efficace d'un composé inhibiteur de l'endopeptidase, de formule dans laquelle X, n et R₃ sont tels que définis dans la revendication 1.
  22. Procédé de préparation de composés de formule qui consiste à combiner une forme activée de l'acide carboxylique de formule avec l'intermédiaire de formule         H₂N-X ou avec son chlorhydrate, où X est    Y est -COR₂, ou un groupe phényle, phényle substitué par un groupe alkyle de 1 à 4 atomes de carbone, alcoxy de 1 à 4 atomes de carbone, alkylthio de 1 à 4 atomes de carbone, hydroxy, halo, nitro ou trifluorométhyle, ou bien un groupe hétérocyclique choisi entre les groupes thiazolyle, 4,5-dihydrothiazolyle, pyridyle, oxazolyle, isoxazolyle, imidazolyle, tétrazolyle, benzimidazolyle, benzothiazolyle et benzoxazolyle, y compris les groupes hétérocycliques substitués dont les substituants sont choisis entre halo, alkyle et phényle;    Z est    m est égal à zéro ou 1;    n est égal à zéro, 1 ou 2;    p est égal à zéro ou est un nombre de 1 à 6;    t est égal à 2, 3 ou 4;    à cette condition que m et p soient tous deux égaux à zéro quand Y est et à cette condition que m et p ne soient pas tous deux égaux à zéro quand Y est -COR₂;    R₁ et R₈ sont, indépendamment, l'hydrogène, un groupe alkyle inférieur, alkyle inférieur halo-substitué, -(CH₂)r-COR₉, -(CH₂)r-cycloalkyle, -(CH₂)r-(α-naphtyle), -(CH₂)r-(β-naphtyle), -(CH₂)r-NH₂, -(CH₂)r-SH, -(CH₂)r-S-alkyle inférieur, -(CH₂)r-OH, -(CH₂)r-O-alkyle inférieur,    R₂ et R₉ sont, indépendamment, un groupe hydroxy, alcoxy inférieur, (phényl) alcoxy inférieur, -O⊖M⊕ où M⁺ est un ion métallique formateur de sel , ou -NRR′ où R et R′ sont choisis indépendamment entre l'hydrogène et les groupes alkyle et    R₃ est l'hydrogène,    R₄ est l'hydrogène ou un groupe alkyle inférieur de 1 à 4 atomes de carbone, alcoxy inférieur de 1 à 4 atomes de carbone, alkylthio inférieur de 1 à 4 atomes de carbone, halo, hydroxy, CF₃, phényle,    R₅ est un groupe alkyle inférieur, -(CH₂)q-(α-naphtyle), -CH₂)q-(β-naphtyle), -(CH₂)q-cycloalkyle,    R₆ est l'hydrogène ou un groupe alkyle inférieur, cycloalkyle ou phényle;    R₇ est l'hydrogène ou un groupe alkyle inférieur, alcoxy inférieur ou phényle;    r est un nombre entier de 1 à 4; et    q est égal à zéro ou est un nombre entier de 1 à 7.
  23. Procédé selon la revendication 22, de préparation de composés de formule qui consiste à combiner un chlorure d'acide de formule avec un intermédiaire aminé de formule         H₂N-X ou avec son chlorhydrate, pour obtenir puis à traiter par une base pour obtenir comme produits les mercaptans voulus dans lesquels    X est
  24. Composé selon l'une quelconque des revendications 1 à 20, destiné à être utilisé dans une méthode de réduction de la pression sanguine et/ou de production d'une diurèse et/ou d'une natriurie ainsi que dans une méthode de traitement d'une insuffisance cardiaque, d'une insuffisance rénale ou d'une cirrhose hépatique.
  25. Utilisation d'un composé selon l'une quelconque des revendications 1 à 20 pour la fabrication d'un médicament permettant de réduire la pression sanguine et/ou de produire une diurèse et/ou une natriurie, ainsi que de traiter une insuffisance cardiaque, une insuffisance rénale ou une cirrhose hépatique.
HK24295A 1990-03-22 1995-02-23 Mercapto- or acylthio-trifluoromethyl amide derivatives and their use HK24295A (en)

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FR2805259B1 (fr) * 2000-02-17 2002-03-29 Inst Nat Sante Rech Med Nouveaux derives d'aminoacides n-mercaptoacyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
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US4333943A (en) * 1980-04-24 1982-06-08 Miles Laboratories, Inc. Ethyl 3-(3-indolyl)-3-(5-tetrazolyl) propionate compounds used as anti-hypertensive agents
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HU210313B (en) 1995-07-28
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IL97626A (en) 1995-08-31
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EP0449523B1 (fr) 1994-08-17
KR0184876B1 (ko) 1999-05-15
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KR910016693A (ko) 1991-11-05
IE910941A1 (en) 1991-09-25
NO175147B (no) 1994-05-30
JP2955051B2 (ja) 1999-10-04
CN1055735A (zh) 1991-10-30
CY1820A (en) 1995-10-20
DK0449523T3 (da) 1994-09-19
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EG19711A (en) 1995-09-30
DE69103454T2 (de) 1995-03-16
CA2038379A1 (fr) 1991-09-23
IL97626A0 (en) 1992-06-21
IE65539B1 (en) 1995-11-01
CN1038505C (zh) 1998-05-27
CS9100765A2 (en) 1991-10-15
NO175147C (no) 1994-09-07
SG165394G (en) 1995-04-28
HU910956D0 (en) 1991-10-28
ATE110056T1 (de) 1994-09-15
AU632408B2 (en) 1992-12-24
EP0449523A1 (fr) 1991-10-02
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CA2038379C (fr) 2002-11-05
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