SI9600027B - Base-substituted benzoylguanidines, process for their preparation, use thereof as a medicament or diagnostic as well as a medicament containing them - Google Patents

Base-substituted benzoylguanidines, process for their preparation, use thereof as a medicament or diagnostic as well as a medicament containing them Download PDF

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SI9600027B
SI9600027B SI9600027A SI9600027A SI9600027B SI 9600027 B SI9600027 B SI 9600027B SI 9600027 A SI9600027 A SI 9600027A SI 9600027 A SI9600027 A SI 9600027A SI 9600027 B SI9600027 B SI 9600027B
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hydrogen
group
methyl
alkyl
replaced
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SI9600027A
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SI9600027A (en
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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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Priority claimed from DE19502795A external-priority patent/DE19502795A1/de
Priority claimed from DE1995104805 external-priority patent/DE19504805A1/de
Application filed by Hoechst Ag filed Critical Hoechst Ag
Publication of SI9600027A publication Critical patent/SI9600027A/sl
Publication of SI9600027B publication Critical patent/SI9600027B/sl

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Claims (19)

1 PATENTNI ZAHTEVKI 1. Spojine s formulo R(0 R C 2 ) R C 3 )
o nh2 R(0 kjer pomenijo: eden od treh substituentov R(l), R(2) in R(3) R(6)-A-B-D-; R(6) bazični ostanek, ki se ga da protonirati, t.j. amino skupina -NR(7)R(8), amidino skupina R(7)R(8)N-C[=N-R(9)]- ali gvanidino skupina R(7) R(10)
R(7), R(8), R(9) in R(10) neodvisno drug od drugega vodik ali alkil z 1, 2, 3 ali 4 C-atomi; ali R(7) in R(8) skupaj C H^; a 4, 5, 6 ali 7; pri čemer je lahko v primeru a = 5, 6 ali 7 ena metilenska skupina skupine CaH2a nadomeščena s heteroatomno skupino O, SOm ali NR(ll), ali R(8) in R(9) ali R(9) in R(10) ali R(7) in R(10) skupino CaH2a; a 2, 3, 4 ali 5; 2 pri čemer je lahko v primeru a = 3,4 ali 5 ena metilenska skupina skupine OH^ nadomeščena z eno heteroatomno skupino O, SOm ali NR(ll); m nič, 1 ali 2; R(ll) vodik ali metil; R(6) bazični heteroaromatski obročni sistem z 1-9 C-atomi; A CbH2b; b 1, 2, 3, 4, 5, 6, 7, 8, 9 ali 10; pri čemer sta lahko v skupini CbH2b ena ali dve metilenski skupini nadomeščeni z eno izmed skupin, izbrano iz skupine, ki sestoji iz -O-, -CO-, -CH[OR(20)]-, -SOm-, -NR(20)-, -NR(20)-CO-, -NR(20)-CO-NH-, -NR(20)-CO-NH-SO2- (°)ao II [ N R ( 1 9 ) 1 h b m -SOaa[NR(19)]bb- in pri čemer je lahko v skupini CbH2b ena metilenska skupina nadomeščena s -CH-R(99), pri čemer R(99) skupaj z R(7) tvori pirolidinski ali piperidinski obroč; aa 1 ali 2; bb 0 ali 1; aa + bb = 2; R(19) vodik ali alkil z 1, 2, 3 ali 4 C-atomi R(20) vodik ali metil; B fenilenski ali naftilenski ostanek Rf12) R(12)
R(13) 3 R(12) in R(13) neodvisno drug od drugega vodik, metil, F, Cl, Br, J, CF3 ali -SOw-R(l4); R(14) metil ali NR(15)R(16); R(15) in R(16) neodvisno drug od drugega vodik ali alkil z 1, 2, 3 ali 4 C-atomi; w nič, 1 ali 2; D -CdH2d-Xf-; d nič, 1, 2, 3 ali 4; X -O-, -C0-, -CH[0R(21)]-, -SOm- ali -NR(21)-; f 1; R(21) vodik ali metil; m nič, 1 ali 2; in vsakokrat drugačni substituenti R(l) in R(2) in R(3) pomenijo neodvisno drug od drugega vodik, F, Cl, Br, J, -CN, -(Cj-Cgj-alkil, -(C2-C8)-alkenil, -NR(35)R(36) ali R(17)-CH2g-Zh-; g nič, 1, 2, 3 ali 4; h nič ali 1; R(35) in R(36) neodvisno drug od drugega vodik ali alkil z 1, 2, 3, 4, 5 ali 6 C-atomi; ali R(35) in R(36) skupaj 4 - 7 metilenskih skupin, od katerih je lahko ena CH2 skupina nadomeščena s kisikom, -S-, -NH-, -NCH3 ali -N-benzilom; Z -O-, -C0-, -SOv, -NR(18)-, -NR(18)-C0-, -NR(18)-CO-NH- ali NR(18)-S02-; R(18) vodik ali metil; v nič, 1 ali 2; R(17) vodik, cikloalkil s 3,5 ali 6 C-atomi ali CkF2k+1+; k 1, 2 ali 3, ali R(17) pirol-l-il, pirol-2-il ali pirol-3-il, kije nesubstituiran ali substituiran z 1 - 4 substituenti, izbranimi iz skupine, ki sestoji iz F, Cl, Br, J, -CN, (C2-Cg)-alkanoila, (C2-Cg)-alkoksikarbonila, formila, karboksi, -CF3, 4 metila in metoksi; ali R(17) -(C3-Cg)-cikloalkil ali fenil kije nesubstituiran ali substituiran z 1 - 3 substituenti, izbranimi iz skupine, ki sestoji iz F in Cl, -CF3, metila, hidroksi, metoksi, -NR(37)R(38), CH3S02- in H2N02S-; R(37) in R(38) vodik ali -CH3; R(4) in R(5) neodvisno drug od drugega vodik, alkil z 1, 2, 3 ali 4 C-atomi, F, Cl, -OR(32), -NR(33)R(34) ali -CF2r+1; R(32), R(33) in R(34) neodvisno drug od drugega vodik ali alkil z 1, 2 ali 3 C-atomi; r 1, 2, 3 ali 4; kot tudi njihove farmakološko prenesljive soli.
2. Spojine s formulo I po zahtevku 1, označene s tem, da v njih pomenijo R(l) vodik, F, Cl, -(C^CJ-alkil, -(C2-C4)-alkenil, -NR(35)R(36) ali R(17)-CH2g-Zh; R(35) in R(36) neodvisno drug od drugega vodik, metil ali etil; ali R(35) in R(36) skupaj 4 - 5 metilenskih skupin, od katerih je lahko ena CH2-skupina nadomeščena s kisikom, -S-, -NH-, ali -NCH3; R(17) vodik, cikloalkil s 5 ali 6 C-atomi ali CfcF2k+1; k 1, 2 ali 3, g nič, 1, 2, 3 ali 4; h nič ali 1; Z -O-, -CO-, -SOv-, -NR(18)-, -NR(l8)-CO-, -NR(18)-CO-NH- ali -NR(18)-S02-; R(18) vodik ali metil; v nič, 1 ali 2; ali, kadar sta g in h enaka nič, R(17) pirol-l-il, pirol-2-il ali pirol-3-il, kije nesubstituiran ali substituiran z 1 - 2 substituentoma, izbranima iz skupine, ki sestoji iz F, Cl, (C2-C5)-alkanoila, 5 (C2-C5)-alkoksikarbonila, formila, karboksi, -CF3, metila in metoksi; ali R(17) -(C3-C8)-cikloalkil ali fenil, ki je nesubstituiran ali substituiran z 1 - 2 substituentoma, izbranima iz skupine, ki sestoji iz F in Cl, -CF3, metila, metoksi, -NR(37)R(38), CH3S02- in H2N02S-; R(37) in R(38) neodvisno drug od drugega vodik ali -CH3; je eden od substituentov R(2) in R(3) R(6)-A-B-D-; R(6) -NR(7)R(8), amidino skupina R(7)R(8)N-C[ = N-R(9)]- ali gvanidino skupina R(7) R ( 1 0 )
R(7), R(8), R(9) in R(10) neodvisno drug od drugega vodik ali alkil z 1, 2, 3 ali 4 C-atomi; ali R(7) in R(8) skupaj CH2a; a 4, 5, 6 ali 7; pri čemer je lahko v primeru a = 5, 6 ali 7 ena metilenska skupina skupine CaH2a nadomeščena s heteroatomno skupino O, SO ali NR(ll); R(ll) vodik ali metil; ali R(8) in R(9) skupaj C H^; a 2, 3, 4 ali 5; pri čemer je lahko v primeru a = 3, 4 ali 5 ena metilenska skupina skupine OH^ nadomeščena s heteroatomno skupino O, SOm ali NR(ll), 6 m nič, 1 ali 2; ali R(6) imidazolil-, piridil-, kinolinil ali izokinolinil; ^ ^b^2b’ b 1, 2, 3, 4 ali 5, pri čemer sta lahko v skupini CbH2b ena ali dve metilenski skupini nadomeščeni z eno od skupin, izbrano iz skupine, ki sestoji iz -O-, -C0-, -CH[OR(20)]-. -SOm-, NR(20), -NR(20)-CO-, -NR(20)-CO-NH-, -NR(20)-CO-NH-SO2-,
a o - R ( 2 O ) N -S - CNR(19)lbb in-SOaa[NR(19)]bb-; in pri čemer je lahko v skupini CbH2b ena metilenska skupina nadomeščena s -CH-R(99), pri čemer tvori R(99) skupaj z R(7) pirolidinski ali piperidinski obroč; aa 1 ali 2; bb O ali 1; aa + bb = 2; B R(19) vodik ali alkil z 1, 2,3 ali 4 C-atomi R(20) vodik ali metil; fenilenski ali naftilenski ostanek R ( * 2 )
R(13) R( l 2)
R(12) in R(13) pomenita neodvisno drug od drugega vodik, metil, F, Cl, CF, ali -S02-R(14); 7 R(14) metil ali NR(15)R(16); R(15) in R(16) neodvisno drug od drugega vodik ali alkil z 1, 2, 3 ali 4 C-atomi; d nič, 1, 2, 3 ali 4; X -O-, -CO-, -CH[OR(21)], -SOm- ali -NR(21)-; f i; R(21) vodik ali metil; m nič, 1 ali 2; in pomeni vsakokrat drug ostanek R(2) in R(3) vodik, alkil z 1, 2, 3 ali 4 C-atomi, F, C1 ali CF3; R(4) in R(5) neodvisno drug od drugega vodik, alkil z 1,2 ali 3 C-atomi, F, C1 ali -CF3.
3. Spojine s formulo I po zahtevku 1, označene s tem, da v njih pomenijo: R(l) vodik, F, Cl, alkil z 1, 2, 3 ali 4 C-atomi, -NR(35)R(36) ali R(17)-CH2g-Zh-; g nič, 1, 2, 3 ali 4; h nič ali 1; Z -0-, -CO-, -SOv-, -NR(18)-, -NR(18)-C0-, -NR(18)-CO-NH-, ali -NR(18)-S02-; R(18) vodik ali metil; v nič, 1 ali 2; R(17) vodik, cikloalkil z 5 ali 6 C-atomi ali CF3-; ali kadar sta g in h enaka nič, R(17) pirol-l-il, ki je nesubstituiran ali substituiran z 1 - 2 substituentoma, izbranima iz skupine, ki sestoji iz F, Cl, (C2C.)-alkanoila, (C2-C5)-aIkoksikarbonila, -CF3 in metila; ali R(17) -(C5-C6)-cikloalkil ali fenil, kije nesubstituiran ali substituiran s substituentom, izbranim iz skupine, ki sestoji iz F in Cl, -CF3, metila, CH3S02- in H2N02S-; R(35) in R(36) pomenita neodvisno drug od drugega vodik, metil ali etil; 8 ali R(35) in R(36) skupaj 4 - 5 metilenskih skupin, od katerih je lahko ena CH2 skupina nadomeščena s kisikom, -S-, -NH-, ali -NCH3; eden od substituentov R(2) in R(3) R(6)-A-B-D-; R(6) -NR(7)R(8), amidino skupina R(7)R(8)N-C[ = N-R(9)]- ali gvanidino skupina
R(7 ) R('°) R(7) vodik ali alkil z 1,2, 3 ali 4 C-atomi; R(8), R(9) in R(10) neodvisno drug od drugega vodik, metil ali etil; ali R(7) in R(8) skupaj C H2a; a 4 ali 5; pri čemer je lahko v primeru a = 5 ena metilenska skupina skupine C nadomeščena z NR(ll), R(ll) vodik ali metil; ali R(6) imidazolil- ali piridil; A b 1,2, 3, 4 ali 5, pri čemer sta lahko v skupini CbH2b ena ali dve metilenski skupini nadomeščeni z eno od skupin, izbrano iz skupine, ki sestoji iz -CO-, -CH[OR(20)]-, -NR(20)-CO-,
- R ( 2 0 ) N -S - I! t N R ( 1 9 ) 1bb 9 -S0aa[NR(19)]bbin-S02-; in pri čemer je lahko v skupini C2bH2b ena metilenska skupina nadomeščena s -CH-R(99), pri čemer R(99) skupaj z R(7) tvori pirolidinski ali piperidinski obroč; aa 1 ali 2; bb 0 ali 1; aa + bb = 2; R(19) vodik ali alkil z 1, 2, 3 ali 4 C-atomi R(20) vodik ali metil; ali kadar je b enak 2, 3, 4 ali 5 je lahko en C-atom v CbH2b nadomeščen s skupino -O-, -S-, NR(20)-, -NR(20)-CO- ali -NR(20)-CO-NH-; B fenilenski ostanek R(12)
R(13) R(12) in R(13) neodvisno drug od drugega vodik, metil, F, Cl, CF3 ali -S02R(14); R(14) metil ali NH2; D -CH2-, -O-, -CO-, -SOm- ali -NR(21)-; m nič ali 2; R(21) vodik ali metil; in vsakokrat drug ostanek R(2) in R(3) vodik; R(4) in R(5) neodvisno drug od drugega vodik, alkil z 1, 2 ali 3 C-atomi, F, Cl, ali -CF3.
4. Spojine s formulo I po zahtevku 1, označene s tem, da v njih pomenijo: R(l) vodik, F, Cl, alkil z 1,2, 3 ali 4 C-atomi, -NR(35)R(36) ali
g nič ali 1; 10 h nič ali 1; Z -O-, -CO-, -NR(18)-CO-, -NR(18)-CO-NH-, ali -NR(18)-SC>2-; R(18) vodik ali metil; ali kadar je g enak 1; pomenijo Z -S02-; R(17) vodik ali CF3-; R(35) in R(36) neodvisno drug od drugega vodik, metil ali etil; ali R(35) in R(36) skupaj 4 - 5 metilenskih skupin od katerih je lahko ena CH2 skupina nadomeščena s kisikom, -S-, -NH-, ali -NCH3; eden od substituentov R(2) in R(3) R(6)-A-B-0-; R(6) -NR(7)R(8) ali gvanidino skupina R ( 7 ) R(10) «to R ( 9 )/N R(7) vodik ali alkil z 1, 2, 3 ali 4 C-atomi; R(8), R(9) in R(10) neodvisno drug od drugega vodik, metil ali etil; ali R(7) in R(8) skupaj C H2a; a 4 ali 5; pri čemer je lahko v primeru a = 5 ena metilenska skupina skupine CH^ nadomeščena z -NH- ali -NCH3-, ali R(6) imidazolil-; A CbH2b; b 1,2, 3 ali 4; pri čemer sta lahko v skupini CbH„b ena ali dve metilenski skupini nadomeščeni z eno od skupin, izbrano iz skupine, ki sestoji iz -CO-, 11
- R ( 2 Ο ) N -s - II I NR( 1 9 ) ] bb -SOaa[NR(19)]bb- in -S02- in pri čemer je lahko v skupini ena metilenska skupina nadomeščena s -CH-R(99), pri čemer lahko tvori R(99) skupaj z R(7) pirolidinski ali piperidinski obroč; ali kadar je b enak 2,3 ali 4, je lahko ena metilenska skupina skupine CfeH2b nadomeščena s skupino -O-, -S-; aa 1 ali 2; bb O ali 1; aa + bb = 2; R(19) vodik ali alkil z 1, 2, 3 ali 4 C-atomi R(20) vodik ali metil; B fenilenski ostanek, R(t2)
R C1 3) R(12) in R(13) vodik, in vsakokrat drug ostanek R(2) in R(3) vodik; R(4) in R(5) vodik.
5. Spojina s formulo I po zahtevku 1, označena s tem, da je izbrana iz skupine, v kateri so 4-[4-N-(dimetilaminoetil)-metilsulfamoil]fenoksi-3-trifluormetil-benzoil-gvanidin, dihidroklorid; 4-[4-(4-metilpiperazinosulfonil)fenoksi]-3-trifluormetil-benzoilgvanidin, dihidroklorid; 4-[4-(2-pirolidinetilaminosulfonil)fenoksi]-3-trifluormetil-benzoilgvanidin,. dimaleinat; 12 4-[4-(2-piperidinetilaminosulfonil)fenoksi]-3-trifluormetil-benzoilgvanidin, dimaleinat; 4-[4-(N-dimetilamino-n-propil)sulfamoil]fenoksi-3-trifluormetil-benzoilgvanidin; 4-[4-(N-dimetilaminoetil)sulfamoil]fenoksi-3-trifluormetil-benzoilgvanidin; 3- metil-4-(4-(l-metilpiperazin-4-ilsulfonil)fenoksi)-benzoilgvanidin; 4- (4-gvanidinosulfonil)fenoksi-3-trifluormetil-benzoilgvanidin; 4-[4-(2-imidazoliltio-acetil)fenoksi]-3-metilsult'onil-benzoil-gvanidin dihidroklorid; 4-[4-(N,N’-dimetil-S-izotiuronil-acetil)fenoksi]-3-metilsulfonil-benzoilgvanidin dihidroklorid; 4-[4-(2-benzimidazoliltio-acetil)fenoksi]-3-metilsulfonil-benzoilgvanidin dihidroklorid; 4-[4-(2-N-imidazolil-l-hidroksietil)fenoksi]-3-metilsulfonil-benzoilgvanidin dihidroklorid; 4-[4-(N,N-dimetilglicilamino)fenoksi]-3-metilsulfonilbenzoil-gvanidin dihidroklorid; 4-[4-(N,N-dietilaminoetil)aminosulfonilfenoksi]-3-metilsulfonilbenzoil-gvanidin dihidroklorid; 4-[4-(4-imidazoliletil)aminosulfonil-fenoksi]-3-metilsulfonil-benzoil-gvanidin dihidroklorid; 4-[4-(3-N-imidazolil-l-propil)aminosulfonil-fenoksi]-3-metilsulfonilbenzoil-gvanidin dihidroklorid; 4-[4-(l-metil-2-pirolidiniletil)aminosulfonil-fenoksi]-3-metilsulfonilbenzoil-gvanidin dihidroklorid; 4-[4-(N-piperidinoetil)aminosulfonil-fenoksi]-3-metilsulfonil-benzoil-gvanidin dihidroklorid; 4-[4-(2-dimetilaminoetil)sulfonilmetil-fenoksi]-3-metilsulfonilbenzoil-gvanidin dihidroklorid; 4-[4-(2-dimetilaminoetil)sulfonilmetil-fenoksi]-3-trifluormetilbenzoil-gvanidin dihidroklorid. 13
6. Postopek za pripravo spojine I po zahtevku 1, označen s tem, da spojino s formulo II R(1)
kjer imajo R(l) do R(5) podani pomen in stoji L za odhodno skupino, ki se jo da zlahka nukleofilno substituirati, presnovimo z gvanidinom, in v danem primeru prevedemo v farmakološko prenesljivo sol.
7. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje aritmij.
8. Uporaba učinkovite količine spojine I po zahtevku 1 skupaj z običajnimi dodatki za pripravo primernih dajalnih oblik za zdravljenje aritmij.
9. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso srčnega infarkta.
10. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso angine pektoris.
11. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih stanj srca.
12. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih stanj perifernega in centralnega živčnega sistema in srčne kapi.
13. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ali profilakso ishemičnih stanj perifernih organov in okončnin. 14
14. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje stanj v šoku.
15. Uporaba spojine I po zahtevku 1 za pripravo zdravila za uporabo pri kirurških operacijah in transplantacijah organov.
16. Uporaba spojine I po zahtevku 1 za pripravo zdravila za konzerviranje in skladiščenje transplantatov za kirurške ukrepe.
17. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje bolezni, pri katerih predstavlja proliferacija celic primarni ali sekundarni vzrok in s tem njena uporaba kot antiarterosklerotika, sredstva proti kasnejšim diabetičnim komplikacijam, rakavim obolenjem, fibrotičnim obolenjem, kot pljučni fibrozi, jetrni fibrozi ali ledvični fibrozi, hiperplaziji prostate.
18. Uporaba spojine I po zahtevku 1 za pripravo znanstvenega orodja za inhibicijo Na+/H+-izmenjevalca za diagnozo hipertonije in proliferativnih obolenj.
19. Farmacevtik, ki obsega učinkovito količino spojine I kot je zahtevana v zahtevku 1.
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EP0723956A1 (de) 1996-07-31
IL116940A (en) 2005-06-19
FI960369A (fi) 1996-07-31
NO960364D0 (no) 1996-01-29
EP0723956B1 (de) 1999-10-13
NO960364L (no) 1996-07-31
ATE185557T1 (de) 1999-10-15
PL183422B1 (pl) 2002-06-28
HUP9600192A1 (en) 1997-04-28
JP3860619B2 (ja) 2006-12-20
CZ26596A3 (en) 1996-08-14
DK0723956T3 (da) 2000-04-17
SK13196A3 (en) 1996-09-04
AU699406B2 (en) 1998-12-03
CN1137035A (zh) 1996-12-04
CN1087285C (zh) 2002-07-10
IL116940A0 (en) 1996-05-14
HRP960041A2 (en) 1997-08-31
KR100457122B1 (ko) 2005-02-02
MY117715A (en) 2004-07-31
NO305948B1 (no) 1999-08-23
PL312491A1 (en) 1996-08-05
CA2168315A1 (en) 1996-07-31
FI960369A0 (fi) 1996-01-26
CZ290268B6 (cs) 2002-06-12
JPH08259515A (ja) 1996-10-08
KR960029320A (ko) 1996-08-17
SI9600027A (en) 1996-10-31
NZ280887A (en) 1997-10-24
DE59603311D1 (de) 1999-11-18
AU4221896A (en) 1996-08-08
ES2139965T3 (es) 2000-02-16
BR9600254A (pt) 1997-12-23
GR3032221T3 (en) 2000-04-27
HRP960041B1 (en) 2000-08-31
AR001073A1 (es) 1997-09-24
SK281567B6 (sk) 2001-05-10

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