SI9500282B - Benzoylguanidines substituted with amino acid, process for their preparation, their use as a medicine or diagnostic agent and also a medicine containing them - Google Patents

Benzoylguanidines substituted with amino acid, process for their preparation, their use as a medicine or diagnostic agent and also a medicine containing them Download PDF

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SI9500282B
SI9500282B SI9500282A SI9500282A SI9500282B SI 9500282 B SI9500282 B SI 9500282B SI 9500282 A SI9500282 A SI 9500282A SI 9500282 A SI9500282 A SI 9500282A SI 9500282 B SI9500282 B SI 9500282B
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hydrogen
independently
alkyl
another
phenyl
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Heinz-Werner Kleemann
Hans-Jochen Lang
Jan-Robert Schwark
Andreas Weichert
Wolfgang Scholz
Udo Albus
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Hoechst Ag
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Claims (16)

  1. i PA 11 N ΓΝΙ ΖΛΙΠΈΥΚΙ 1. Spojina s formulo I
    R(4) o kjer pomenijo: eden od treh substituentov R(l), R(2) in R(3) -Y-[4-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil], -Y-[3-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil] ali -Y-[2-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil], pri čemer je fenil vsakokrat nesubstituiran ali substituiran z 1 do 2 substituentoma iz skupine F, Cl, -CF3, metila, hidroksi, metoksi ali -NR(37)R(38); R(37) in R(38) neodvisno drug od drugega vodik ali -CH?; Y vez, kisik, -S- ali -NR(9); R(9) vodik ali -(Cj-C4)-alkil; R(7) -OR( 10) ali -NR( 10)R( 11); R( 10) in R(11) neodvisno drug od drugega vodik, -(Ci-Cg)-alkil, -(CrCg)-alkanoil, -(CrCg)- alkoksikarbonil, benzil. benziloksikarbonil; ali R(10) tritil; R(8) -OR( 12) ali -NR( 12)R( 13); R( 12)in R( 13) neodvisno drug od drugega vodik. -(C]-Cs)-alkil ali benzil: k 0, 1,2. 3 ali 4; in vsakokrat drugi ostanki R(l), R(2) in R(3) 2 neodvisno drug od drugega -(Ci-Cx)-alkil, -(C2-Cx)-alkenil ali -(CII2)mR( 14): m 0. I ali 2; R(I4) -(C3-Cx)-cikloalkil ali fenil, ki ni substituiran ali je substituiran z 1 do 3 substituenti. izbranimi iz skupine, ki obstoji iz F, Cl. -CF3, metila, metoksi in -NR(15)R(16): R( 15) in R( 16) vodik ali -CH3; ali vsakokrat drugi ostanki Ril). R(2) in R(3) neodvisno drug od drugega R(18)R(19)N-(C=Y')-NH-S02-; Y' kisik. -S- ali -N-R(20); R( 18) in R( 19) neodvisno drug od drugega vodik, -(CrC8)-alkil, -(C3-C6)-alkenil ali -(CH2)t-R(21): t 0, 1,2. 3 ali 4: R(21) -(C5-C7)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1 do 3 substituenti. izbranimi iz skupine, ki obstoji iz F. Cl. -CF3, metoksi in -(CrC4)-alkila; ali R( 18) in R(19) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena skupina CH2 nadomeščena s kisikom. -S-, -NH-, -N-CH; ali -N-benzilom; R(20) definiran kot R( 18) ali amidin; ali vsakokrat drugi ostanki R( 1), R(2) in R(3) neodvisno drug od drugega vodik, F. Cl, Br, J, -C^N, X-(CH2)P-(CqF2q_,). R(22)-SOu-, R(23)R(24)N-CO-, R(25)-CO- ali R(26)R(27)N-S02-, pri čemer je perfluoralkilna skupina ravna ali razvejena; X vez. kisik. -S- ali -NR(28); u 0, 1 ali 2: p 0. 1 ali 2; q 1. 2. 3.4. 5 ali 6; R(22). R(23), R(25) in R(26) neodvisno drug od drugega -(C|-Cx)-alkil. -(C3-Cft)-alkenil. -(CH2)„R(29) ali -CI;3: n 0, 1,2, 3 ali 4; R(28) vodik ali -(CrC3)-alkil; R(29) -(C3-C7)-cikloalkil ali fenil; ki ni substituiran ali je substituiran z 1 do 3 substituenti, izbranimi iz skupine, ki obstoji iz F, Cl, -CF3, metila, metoksi in -NR(30)R(31); R(30) in R(31) vodik ali -(Ci-C4)-alkil; ali R(23), R(25) in R(26) vodik; R(24) in R(27) neodvisno drug od drugega vodik ali -(Ci-Cjj-alkil; ali R(23) in R(24) kot tudi R(26) in R(27) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena skupina CH2 nadomeščena s kisikom, -S-, -NH-, -N-CH3 ali -N-benzilom; ali vsakokrat drugi ostanki R(l), R(2) in R(3) neodvisno drug od drugega -OR(35) ali -NR(35)R(36); R(35) in R(36) neodvisno drug od drugega vodik ali -(Ci-Cej-alkil: ali R(35) in R(36) skupaj 4 do 7 metilenskih skupin, od katerih je lahko ena skupina CFI2 nadomeščena s kisikom, -S-, -NH-, -N-CH3 ali -N-benzilom; R(4)in R(5) neodvisno drug od drugega vodik. -(CrC4)-alkil, F, Cl, -OR(32), - NR(33)R(34) ali -CrF2r+l; R(32). R(33) in R(34) 4 neodvisno drug od drugega vodik ali -(Ct-C-,)-alki 1; r 1.2. 3 ali 4 kot tudi njene farmacevtsko sprejemljive soli.
  2. 2. Spojina po zahtevku 1. označena s tem. da v njej pomenijo R(l) -(C,-C4)-alkil, -(C2-C4)-alkenil ali -(CH2)mR( 14); m 0, 1 ali 2; R( 14) -(C5-C6)-cikloalkil ali fenil, ki ni substituiran ali je substituiran z 1 do 2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, -CF3, metila, metoksi in -NR(15)R(16); R( 15) in R( 16) neodvisno drug od drugega vodik ali -CH3; ali R(l) R(18)R(19)N-(C=Y')-NH-S02-; Y' kisik, -S- ali -N-R(20); R( 18) in R( 19) neodvisno drug od drugega vodik, -(C|-C4)-alkil, -(C3-C4)-alkenil, ali -(CH2)tR(21); t 0, 1 ali 2; R(21) -(C5-C6)-cikloalkil ali fenil. ki je nesubstituiran ali substituiran z 1 do 2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, -CF3, metoksi in metila; ali R(18)in R( 19) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena skupina CH2 nadomeščena s kisikom, -S-. -NH-, -N-CF13 ali -N-benzilom; R(20) definiran kot R( 18) ali amidin; ali R( 1) vodik. F, Cl. Br. J. -C=N, R(22)-SOr. R(23)R(24)N-CO-, R(25)-CO-ali R(26)R(27)N-SOr; R(22). R(23), R(25) in R(26) neodvisno drug od drugega -(C|-C.|)-alkil. -(C,-C t)-alkenil. -(CH2)MR(29) ali -CF3: n 0, 1 ali 2; R(29) -(C5-C6)-cikloalkil ali fenil; ki ni substituiran ali je substituiran z 1 do 2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, -CF3, metila, metoksi in -NR(30)R(31); R(30) in R(31) neodvisno drug od drugega vodik ali metil; ali R(23), R(25) in R(26) vodik; R(24) in R(27) neodvisno drug od drugega vodik ali metil; ali R(23) in R(24) kot tudi R(26) in R(27) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena skupina CFF nadomeščena s kisikom, -S-, -NH-, -N-CH3 ali -N-benzilom; ali R( 1) -OR(35) ali -NR(35)R(36); R(35) in R(36) neodvisno drug od drugega vodik ali -(C|-C4)-alkil; ali R(35) in R(36) skupaj 4 do 5 metilenskih skupin, od katerih je lahko ena skupina CFL· nadomeščena s kisikom. -S-. -NFI-, -N-CFF ali -N-benzilom; eden od substituentov R(2) ali R(3) -Y-[4-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil]. -Y-[3-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil] ali -Y-[2-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil], pri čemer je fenil vsakokrat nesubstituiran ali substituiran z 1 do 2 substituentoma iz skupine, ki obstoji iz F. Cl. -CF3, metila, hidroksi, metoksi ali -NR(37)R(38); R(37) in R(38) 6 neodvisno drug od drugega vodik ali -O h; Y vez, kisik, -S- ali -NR(9); R(9) vodik ali metil; R(7) -OR(IO) ali -NR(10)R( 11); R(10)in R( 11) neodvisno drug od drugega vodik, -(Ci-C.sj-alkil, -(CrC5)-alkanoil, -(C|-C4)- alkoksikarbonil, benzil ali benziloksikarbonil; ali R(10) tritil; R(8) -OR( 12) ali -NR( 12 )R( 13); R(12) in R(13) neodvisno drug od drugega vodik, -(CrC4)-alkil ali benzil; k 0, 1 ali 2; in vsakokrat drugi substituent R(2) in R(3) neodvisno drug od drugega -(CrC4)-alkil, vodik, F, Cl, Br ali J; R(4) in R(5) neodvisno drug od drugega vodik, metil, F, Cl, -OR(32)-, NR(33)R(34) ali -CF3; R(32), R(33) in R(34) neodvisno drug od drugega vodik ali metil.
  3. 3. Spojina s formulo I po zahtevku 1, označena s tem, da v njej pomenijo R(l) -(C,-C4)-alkil, -(C2-C4)-alkenil ali -(CH2)mR(14); m 0, 1 ali 2; R( 14) -(C5-C6)-cikloalkil ali fenil, ki ni substituiran ali je substituiran z 1 do 2 substituentoma. izbranima iz skupine, ki obstoji iz F, Cl. -CF3, metila, metoksi in -NR(15)R(16); R( 15) in R(16) neodvisno drug od drugega vodik ali -CH3; ali R(l) vodik. F. Cl, Br. J, -C=N. R(22)-S02-, R(23)R(24)N-CO-. R(25)-CO-ali R(26)R(27)N-S02-; / R(22), R(23), R(25) in R(26) neodvisno drug od drugega metil ali -CF3. ali R(23), R(25) in R(26) vodik; R(24) in R(27) neodvisno drug od drugega vodik ali metil; ali R(l) -OR(35) ali -NR(35;R(36); R(35) in R(36) neodvisno drug od drugega vodik ali -(CrC4)-alkil; ali R(35) in R(36) skupaj 4 do 5 metilenskih skupin, od katerih je ena skupina CH2 lahko nadomeščena s kisikom, -S-, -NH-, -N-CH3 ali -N-benzilom; eden od substituentov R(2) in R(3) -Y-[4-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil]. -Y-[3-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil] ali -Y-[2-[(CH2)k-CHR(7)-(C=0)R(8)]-fenil], pri čemer je fenil vsakokrat nesubstituiran ali substituiran s substituentom, izbranim iz skupine, ki obstoji iz F, Cl. -CF3, metila, hidroksi, metoksi in -NR(37)R(38); R(37) in R(38) neodvisno drug od drugega vodik ali -CH3; Y vez, kisik. -S- ali -NR(9); R(9) vodik ali metil; R(7) -NR(10)R(11); R( 10) inR(ll) neodvisno drug od drugega vodik, -(CrC4)-alkil. -(CrC5)-alkanoil. -(C i-C4>- alkoksikarbonil. benzil ali benziloksikarbonil; ali R( 10) tritil; 8 R(8) -OR( 12) ali -NR( 12>R( 13); R( 12)in R(13) neodvisno drug od drugega vodik. -(Ci-CjJ-alkil ali benzil: in vsakokrat drugi substituent R(2) in R(3) neodvisno drug od drugega -(C|-C4)-alkil, vodik. F ali Cl; R(4) in R(5) neodvisno drug od drugega vodik, metil, F, Cl. -OR(32)-, NR(33)R(34) ali -CF;: R(32), R(33) in R(34) neodvisno drug od drugega vodik ali metil.
  4. 4. Postopek za pripravo spojine s formulo I po zahtevku 1, označen s tem, da spojino s formulo II R(l)
    R(4) O (Π) kjer imajo R(l) do R(5) v zahtevku 1 navedene pomene in stoji L za lahko nukleofilno nadomestljivo odhodno skupino, presnovimo z gvanidinom.
  5. 5. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje aritmij.
  6. 6. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje angine pectoris.
  7. 7. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje srčnega infarkta.
  8. 8. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih stanj srca.
  9. 9. Uporaba spojine 1 po zahtevku 1 za priprao zdravila za zdravljenje ali profilakso ishemičnih stanj perifernega in centralnega živčnega sistema in kapi.
  10. K). Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali prolilakso ishemienih stanj perifernih organov in okončin.
  11. 11. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje stanj šoka.
  12. 12. Uporaba spojine I po zahtevku 1 za pripravo zdravila za uporabo pri kirurških operacijah in transplantacijah organov.
  13. 13. Farmacevtski sestavek za zdravljenje aritmij, označen s tem, da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim nosilcem.
  14. 14. Farmacevtski sestavek za zdravljenje angine pektoris. označen s tem. da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim nosilcem.
  15. 15. Farmacevtski sestavek za uporabo pri kirurških operacijah in presaditvah organov, označen s tem, da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim nosilcem.
  16. 16. Farmacevtski sestavek za zdravljenje srčnega infarkta, ishemičnih stanj srca. ishemienih stanj perifernega in centralnega živčnega sistema, kapi. perifernih organov in okončin ter stanj šoka. označen s tem. da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim nosilcem.
SI9500282A 1994-09-09 1995-09-08 Benzoylguanidines substituted with amino acid, process for their preparation, their use as a medicine or diagnostic agent and also a medicine containing them SI9500282B (en)

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DE4432101A DE4432101A1 (de) 1994-09-09 1994-09-09 Aminosäure-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

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EP0765867A1 (de) * 1995-09-27 1997-04-02 Hoechst Aktiengesellschaft Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Antiarrhytmika oder Diagnostikum sowie sie enthaltendes Medikament
DE19540995A1 (de) * 1995-11-03 1997-05-07 Hoechst Ag Substituierte Sulfonimidamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19542306A1 (de) * 1995-11-14 1997-05-15 Hoechst Ag Sulfonylamino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
PL316439A1 (en) * 1995-11-20 1997-05-26 Hoechst Ag Novel substituted derivatives of benzoyloguanidine, method of obtaining them, their application in production of pharmaceutic and diagnostic agents and pharmaceutic agent as such
DE19546736A1 (de) * 1995-12-14 1997-06-19 Hoechst Ag Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate
DE19621319A1 (de) * 1996-05-28 1997-12-04 Hoechst Ag Bis-ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
US6852739B1 (en) 1999-02-26 2005-02-08 Nitromed Inc. Methods using proton pump inhibitors and nitric oxide donors
DE10059418A1 (de) 2000-11-30 2002-06-20 Aventis Pharma Gmbh Ortho, meta-substituierte Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
JP4634144B2 (ja) * 2002-08-01 2011-02-16 ニコックス エスエー ニトロソ化プロトンポンプ阻害剤、組成物および使用方法
US6794401B2 (en) * 2003-01-17 2004-09-21 Bexel Pharmaceuticals, Inc. Amino acid phenoxy ethers
DE10338554A1 (de) * 2003-08-22 2005-03-31 Aventis Pharma Deutschland Gmbh Pentafluorosulfanylphenyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
US20080103169A1 (en) 2006-10-27 2008-05-01 The Curators Of The University Of Missouri Compositions comprising acid labile proton pump inhibiting agents, at least one other pharmaceutically active agent and methods of using same
US20080194307A1 (en) * 2007-02-13 2008-08-14 Jeff Sanger Sports-based game of chance
EP2252274A4 (en) 2008-02-20 2011-05-11 Univ Missouri COMPOSITION COMPRISING A COMBINATION OF OMEPRAZOLE AND LANSOPRAZOLE, AND A BUFFER AGENT, AND METHODS OF USING THE SAME

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DE3929582A1 (de) 1989-09-06 1991-03-07 Hoechst Ag Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament
CZ284456B6 (cs) * 1992-02-15 1998-12-16 Hoechst Aktiengesellschaft Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje
ATE139526T1 (de) 1992-02-15 1996-07-15 Hoechst Ag 3,5-substituierte benzoylguanidine, mit antiarrythmischer wirkung und inhibierender wirkung auf die proliferationen von zellen
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ATE147375T1 (de) * 1992-09-22 1997-01-15 Hoechst Ag Benzoylguanidine, verfahren zu ihrer herstellung, sowie ihre verwendung als antiarrhythmika
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HUT72629A (en) 1996-05-28
AU3050695A (en) 1996-03-21
JP3828597B2 (ja) 2006-10-04
DE59505487D1 (de) 1999-05-06
DK0700899T3 (da) 1999-10-18
TW419455B (en) 2001-01-21
HU9502632D0 (en) 1995-11-28
GR3030365T3 (en) 1999-09-30
CN1127749A (zh) 1996-07-31
SI9500282A (en) 1996-04-30
CA2157859A1 (en) 1996-03-10
EP0700899A1 (de) 1996-03-13
US5631293A (en) 1997-05-20
IL115195A (en) 2001-06-14
NO953553L (no) 1996-03-11
HU220762B1 (hu) 2002-05-28
CZ231795A3 (en) 1996-03-13
KR960010618A (ko) 1996-04-20
ATE178315T1 (de) 1999-04-15
CA2157859C (en) 2007-11-13
NZ272947A (en) 1996-10-28
EP0700899B1 (de) 1999-03-31
IL115195A0 (en) 1995-12-31
PL310343A1 (en) 1996-03-18
ES2131241T3 (es) 1999-07-16
JPH0892196A (ja) 1996-04-09
CN1057760C (zh) 2000-10-25
FI954192A0 (fi) 1995-09-07
NO953553D0 (no) 1995-09-08
FI954192A (fi) 1996-03-10
AU695234B2 (en) 1998-08-06
CZ289760B6 (cs) 2002-04-17
PL180244B1 (pl) 2001-01-31
ZA957550B (en) 1996-04-17
NO305164B1 (no) 1999-04-12
RU2154055C2 (ru) 2000-08-10
DE4432101A1 (de) 1996-03-14

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