SI9500280B - Benzoylguanidines substituted with n-oxide of heterocyclic, process for their preparation, their use as a medicine or diagnostic agent, a medicine containing them and also intermediate products for their preparation - Google Patents

Benzoylguanidines substituted with n-oxide of heterocyclic, process for their preparation, their use as a medicine or diagnostic agent, a medicine containing them and also intermediate products for their preparation Download PDF

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SI9500280B
SI9500280B SI9500280A SI9500280A SI9500280B SI 9500280 B SI9500280 B SI 9500280B SI 9500280 A SI9500280 A SI 9500280A SI 9500280 A SI9500280 A SI 9500280A SI 9500280 B SI9500280 B SI 9500280B
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hydrogen
alkyl
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methyl
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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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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C07D215/60—N-oxides

Claims (15)

  1. i 1 PATENTNI ZAHTEVKI i 1 1. Benzoilgvanidin s formulo I R(l)
    K v kateri je eden od treh substituentov R(l), R(2) in R(3) (Ci-Cgj-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni z S, NH ali O, ki je povezan preko C ali N in je nesubstituiran ali substituiran z 1-3 substituenti, izbranimi iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila, amino, metilamino in dimetilamo; ali je eden od treh substituentov R(l), R(2) in R(3) -SR(10), -OR(IO), -NR(10)R(11) ali -CR(10)R(11)-R(12); R(10) je -CaH2a-(Ci-C9)-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni z S, NH ali O, kije nesubstituiran ali substituiran z 1-3 substituenti, izbranimi iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila, amino, metilamino in dimetilamino; a je 0, 1 ali 2; R(ll) in R(12) sta neodvisno drug od drugega, kot je definirano za R(10), vodik ali (CrC4)-alkil; in so drugi posamezni substituenti R(l), R(2) in R(3) neodvisno drug od drugega (Cp C8)-alkil, (C2-C8)-alkenil ali -CmH2mR(14); m je 0, 1 ali 2; R(14) je (C3-Cg)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1-3 substituenti, izbranimi iz skupine, ki obstoji iz F, Cl, CF3, metila, metoksi in NR(15)R(16), 2 R(15) in R(16) sta vodik ali CH3; ali so drugi posamezni substituenti R(l), R(2) in R(3) neodvisno drug od drugega vodik, F, Cl, Br, J, -ON, X-(CH2)p-(CqF2q+,), R(22)-SOu, R(23) R(24)N-CO, R(25)-CO- ali R(26)R(27)N-SOr, kjer je perfluoroalkilna skupina ravna ali razvejena; X je vez, kisik, S ali NR(28); uje 0, 1 ali 2; p je 0, 1 ali 2; q je 0, 1,2,3,4, 5 ali 6; R(22), R(23), R(25) in R(26) so neodvisno drug od drugega (Ci-Cg)-alkil, (C2-C6)-alkenil, -CnH2n-R(29) ali CF3; nje 0, 1, 2, 3 ali 4; R(28) je vodik ali (CrC3)-alkil; R(29) je (C3-C7)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1-3 substituenti, izbranimi iz skupine, ki obstoji iz F, Cl, CF3, metila, metoksi in NR(30)R(31); R(30) in R(31) sta vodik ali Ci-C4-alkil, ali so R(23), R(25) in R(26) tudi vodik; R(24) in R(27) sta neodvisno drug od drugega vodik ali (Ci-C4)-alkil; ali so R(23) in R(24) ter R(26) in R(27) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena CH2 skupina nadomeščena s kisikom, S, NH, N-CH3 ali N-benzilom; ali so drugi posamezni substituenti R(l), R(2) in R(3) neodvisno drug od drugega OR(35) ali NR(35)R(36); R(35) in R(36) sta neodvisno drug od drugega vodik ali (Ci-C^j-alkil; ali sta R(35) in R(36) skupaj 4-7 metilenskih skupin, od katerih je lahko ena CH2 skupina, nadomeščena s kisikom, S, NH, N-CH3 ali N-benzilom, R(4) in R(5) sta neodvisno vodik, (Ci-C4)-alkil, F, Cl, -OR(32), -NR(33)R(34) ali 3 -CrF2r+i; R(32), R(33) in R(34) so neodvisno vodik ali (Ci-C3)-alkil; rje 1, 2, 3 ali 4; in njegove farmacevtsko sprejemljive soli.
  2. 2. Spojina s formulo I po zahtevku 1, označena s tem, daje R(l) (CrC4)-alkil, (C2-C4)-alkenil ali -CmH2mR(14), m je 0, 1 ali 2; R(14) je (C5-C6)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, metila, metoksi in NR(15)R(16); R(15) in R(16) sta vodik ali CH3, ali je 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) so neodvisno (CrC4)-alkil, (C2-C4)-alkenil, -CnH2n-R(29) ali CF3; n je 0, 1 ali 2; R(29) je (C5-C6)-cikloalkil ali fenil, ki je nesubstituiran ali 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) sta vodik ali metil; ali so R(23), R(25) in R(26) vodik; R(24) in R(27) sta neodvisno drug od drugega vodik ali metil; ali so R(23) in R(24) ter R(26) in R(27) skupaj 4 ali 5 metilenskih skupin, od katerih je lahko ena CFI2 skupina nadomeščena s kisikom, S, NH, N-CH3 ali N-benzilom; ali je R(l) OR(35) ali NR(35)R(36); R(35) in R(36) sta neodvisno drug od drugega vodik ali (Ci-C4)-alkil; ali sta R(35) in R(36) skupaj 4-5 metilenskih skupin, od katerih je lahko ena CH2 skupina nadomeščena s kisikom, S, NH, N-CH3 ali N-benzilom; 4 eden od substituentov R(2) in R(3) je (Ci-C9)-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni s S, NH ali O, ki je vezan preko C ali N in je nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila, amino, metil-amino in dimetilamino; ali je eden od substituentov R(2) in R(3) -SR(10), -OR(IO), -NR(10)R(11) ali -R(10)R(11)-R(12); R(10) je -CaH2a-(Ci-C9)-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni z S, NH ali O, kije nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila, amino, metilamino in dimetilamino; a je 0 ali 1; R(11) in R(12) sta vodik ali metil; in so drugi posamezni substituenti R(2) in R(3) neodvisno drug od drugega (CrC4)-alkil, vodik, F, Cl, Br ali J; R(4) in R(5) sta neodvisno drug od drugega vodik, metil, F, Cl, -OR(32), -NR(33)R(34) ali CF3; R(32), R(33) in R(34) so neodvisno drug od drugega vodik ali metil.
  3. 3. Spojina s formulo I po zahtevku 1, označena s tem, daje R(l) (CrC4)-alkil, (C2-C4)-alkenil ali -CmH2mR(14); m je 0, 1 ali 2; R(14) je (C5-C6)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, metila, metoksi in NR(15)-R(16); R(15) in R(16) sta vodik ali CH3; ali je 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) so neodvisno drug od drugega metil ali CF3; ali so 5 R(23), R(25), R(26) vodik; R(24) in R(27) sta neodvisno drug od drugega vodik ali metil; ali je R(l) OR(35) ali NR(35)R(36); R(35) in R(36) sta neodvisno drug od drugega vodik ali (CrC4)-alkil; ali sta R(35) in R(36) skupaj 4 do 5 metilenskih skupin, od katerih je lahko ena CH2 skupina nadomeščena s kisikom, S, NH, N-CH3 ali N-benzilom, eden od substituentov R(2) in R(3) je (CrC9)-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni s S, NH ali O, ki je vezan preko C in N in je nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila in dimetilamino; eden od substituentov R(2) in R(3) je -SR(10), -OR(10), -NR(10)R(11) ali -CR(10)R(11)-R( 12); R(10) je (Ci-C9)-heteroaril-N-oksid, izveden iz fenila ali naftila, kjer je ena ali več CH skupin N in/ali kjer sta vsaj dve sosednji CH skupini nadomeščeni s S, NH ali O, ki je nesubstituiran ali substituiran z 1-2 substituentoma, izbranima iz skupine, ki obstoji iz F, Cl, CF3, CH3, metoksi, hidroksila in dimetilamina; R(11) in R(12) sta neodvisno drug od drugega vodik ali metil; in so drugi posamezni substituenti R(2) in R(3) neodvisno drug od drugega (C1-C4)- alkil, vodik, F, Cl, Br ali J; R(4) in R(5) sta neodvisno drug od drugega vodik, metil, F, Cl, -OR(32), -NR(33)R(34) ali CF3; R(32), R(33) in R(34) so neodvisno drug od drugega vodik ali metil.
  4. 4. Postopek za pripravo spojin s formulo I po zahtevku 1, označen s tem, da spojino s formulo II 6 R(l) (Π)
    v kateri imajo R(l) do R(5) v zahtevku 1 navedeni pomen, presnovimo z gvanidinom, kjer stoji L za lahko nukleofilno izmenljivo odhodno skupino.
  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 srčnega infarkta.
  7. 7. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje angine pektoris.
  8. 8. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih staj srca.
  9. 9. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih stanj perifernega in centralnega živčnega sistema in kapi.
  10. 10. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih 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. 7
  14. 14. Farmacevtski sestavek za uporabo pri kirurških operacijah in presaditvah organov, označen s tem, da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevsko sprejemljivim nosilcem.
  15. 15. Farmacevtski sestavek za zdravljenje srčnega infarkta, angine pektoris, ishemičnih stanj srca, ishemičnih stanj perifernega in centralnega živčnega sistema, kapi, perifernih organov in okončin in stanj šoka, označen s tem, da obsega spojino s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim nosilcem.
SI9500280A 1994-09-09 1995-09-08 Benzoylguanidines substituted with n-oxide of heterocyclic, process for their preparation, their use as a medicine or diagnostic agent, a medicine containing them and also intermediate products for their preparation SI9500280B (en)

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FI954190A (fi) 1996-03-10
DE4432106A1 (de) 1996-03-14
PL310346A1 (en) 1996-03-18
CA2157855A1 (en) 1996-03-10
DK0700904T3 (da) 2002-03-18
CN1119643A (zh) 1996-04-03
KR960010619A (ko) 1996-04-20
JPH0892215A (ja) 1996-04-09
PT700904E (pt) 2002-05-31
ATE210121T1 (de) 2001-12-15
CZ291188B6 (cs) 2003-01-15
JP4113262B2 (ja) 2008-07-09
AU3050495A (en) 1996-03-21
FI954190A0 (fi) 1995-09-07
CA2157855C (en) 2009-04-21
IL115196A (en) 2003-01-12
CZ231595A3 (en) 1996-04-17
DE59509899D1 (de) 2002-01-17
US5641792A (en) 1997-06-24
EP0700904B1 (de) 2001-12-05
SI9500280A (en) 1996-04-30
HUT72630A (en) 1996-05-28
HU219976B (hu) 2001-10-28
NO953555L (no) 1996-03-11
EP0700904A1 (de) 1996-03-13
NO953555D0 (no) 1995-09-08
HU9502634D0 (en) 1995-11-28
ZA957548B (en) 1996-04-17
ES2168324T3 (es) 2002-06-16
RU2160727C2 (ru) 2000-12-20
AU695342B2 (en) 1998-08-13
IL115196A0 (en) 1995-12-31
NZ272946A (en) 1996-12-20
NO305202B1 (no) 1999-04-19

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