SI9300066B - Novi derivati amidinov, njihova priprava in uporaba - Google Patents

Novi derivati amidinov, njihova priprava in uporaba Download PDF

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SI9300066B
SI9300066B SI9300066A SI9300066A SI9300066B SI 9300066 B SI9300066 B SI 9300066B SI 9300066 A SI9300066 A SI 9300066A SI 9300066 A SI9300066 A SI 9300066A SI 9300066 B SI9300066 B SI 9300066B
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alkyl
halogen
acyl
formula
alkoxy
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Ralf Anderskewitz
Kurt Schromm
Ernst-Otto Renth
Frank Himmelsbach
Franz Birke
Armin Fuegner
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Boehringer Ingelheim Kg
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Priority claimed from DE4224289A external-priority patent/DE4224289A1/de
Priority claimed from DE4244241A external-priority patent/DE4244241A1/de
Application filed by Boehringer Ingelheim Kg filed Critical Boehringer Ingelheim Kg
Publication of SI9300066A publication Critical patent/SI9300066A/sl
Publication of SI9300066B publication Critical patent/SI9300066B/sl

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    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4

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Claims (9)

1 Patentni zahtevki 1. Spojine s formulo
v kateri Ri in R2, ki sta lahko enaka ali različna, stojita za CF3, halogen, R5, OR5, COR^, SR6, SOR& S02R6, SO2NR5R7, C(OH)R5R7 ali skupaj tudi za s sosednjimi atomi C benzenovega obroča povezane skupine z dvema vezema -CH=CH-CH=CH-, -CR8=CH-CH=CH-, -CH=CR8-CH=CH-, -O-CH2-CH2, -0-CH2-0-, -o-ch2-CH2-0-, -(CH2)3.4-, -NH-CO-O-, -NH-CO-CH2-0-, -C0-CH2-0- ali -CO-CH2-CH2-0-, pri čemer so lahko te skupine po svoji plati tudi substituirane s C1-C4-alkilom, R3 stoji za halogen, OH, CF3, R5, OR^, COR6, SR^, SOR^, S02R^, S02NR5R7, NR5R7 ali C(OH)R5R7 (pri čemer je, če je R3 enak R5, R5 lahko H samo takrat, če najmanj eden od substituentov Rj in R2 ne pomeni H), R4 za halogen, OH, CrC4-alkoksi, R5 za H, CrCi2-alkil ali fenil, v danem primeru s halogenom, Ci-C4-alkilom, Cr C4-alkoksi ali C2-C5-acilom substituiran fenil, R^ za C]-Ci2-alkil, fenil ali v danem primeru s halogenom, Ci-C4-alkilom, Ci-C4-alkoksi ali C2-C5-acilom substituiran fenil, R7 za H ali Ci-Cj2-alkil, R8 za C2-C5-acil, A za eno od skupin Xj-A,-X2 (II) 2 X2-A2-X3 (III) x4-a2-x2 (IV) (CH2) j _2-NH-CO-(CH2) i .3-X2 (V) -CH=CH-A2-X2 (VI) B za CH=CH, CH=N, S ali \LJ/ » A, za C2-C4-alkilen, cis- ali trans-CH2-CH=CH-CH2, CH2-C=C-CH2 ali
(VII) (Vila) A2 za Ci-C5-alkilen, X! za O, NH, S, SO, S02, CO ali CH2, X2 za O, NH ali S, X3 za NH-CO, CO-NH ali S02-NH, X4 za NH-CO, CO-NH, NH-S02 ali S02-NH, s pridržkom, da če pomenijo B -CH=CH- in X! kisik ali žveplo in X2 kisik ali žveplo in 3 Ai C2-C4-alkilen, cis- ali trans-CH2-CH=CH-CH2, CH2-C=C-CH2 ali 3 /
CH. 7 in eden od ostankov Rj, R2 ali R3 -0-CrCi2-alkil, vsaj eden od drugih ostankov Rls R2 ali R3 ne more biti vodik, halogen, CF3, OH, CrC12-alkil ali -0-C,-C12-alkil, kot tudi s pridržkom, da če pomenijo B -CH=CH- Rt vodik, Xi in X2 kisik, Α] C3- ali C4-alkilen, in stoji amidino skupina glede na ostanek A v legi meta, Ri, R2 ali R3 ne morejo pomeniti fenil, NH2, klor, metoksi ali CF3, kot racemati, v enantiomemo čisti oz. obogateni obliki, v danem primeru kot pari diastereomerov kot tudi v cis- ali trans-obliki in vsakokrat kot proste baze ali soli, prednostno s fiziološko prenesljivimi kislinami.
2. Spojine po zahtevku 1 s splošno formulo
v kateri Ri, R2, ki sta lahko enaka ali različna, lahko pomenita R7, OR7, COR* ali skupaj tudi s sosednjimi atomi C benzenovega obroča povezane skupine z dvema vezema -CR8=CH-CH=CH-, -CH=CRg-CH=CH-, -0-CH2-CH2- ali -C0-CH2-CH2-0-, pri čemer so lahko te skupine po svoji strani tudi substituirane s CrC4-alkilom, 4
NR5R7 ali C(OH)R5R7, (pri čemer je, če je R3 enak R5, R5 H le takrat, če najmanj eden od substituentov Ri in R2 ne pomeni H), R5 stoji za H, Ci-Ci2-alkil ali fenil, v danem primeru s halogenem CrC4-alkilom, CrC4-alkoksi ali C2-C5-acilom substituiran fenil, R6 stoji za Ci-Ci2-alkil, fenil ali v danem primeru s halogenom, Ci-C4-alkilom, Cp C4-alkoksi ali C2-C5-acilom substituiran fenil, R7 stoji za H ali CpCp-alkil, R8 stoji za C2-C5-acil, in stoji A za skupino XpArX2 (II), pri čemer Ai pomeni C2-C4-alkilen, cis- ali trans-CH2-CH=CH-CH2, CH2-C=C-CH2 ali
(VII) (Vila) Χι O, NH, S, SO, S02, CO ali CH2, X2 O, NH ali S, s pridržkom, da če pomenijo X! kisik ali žveplo in X2 kisik ali žveplo in A! C2-C4-alkilen, cis- ali trans-CH2-CH=CH-CH2, CH2-C=C-CH2 ali /
in eden od ostankov Ri, R2 ali R3 -O-CpCp-alkil, 5 vsaj eden od drugih ostankov Rl5 R2 ali R3 ne more biti vodik, halogen, CF3, OH, Cj-C,2-alkil ali -0-CrCi2-alkil, kot racemati, v enantiomemo čisti oz. obogateni obliki, v danem primeru kot pari diastereomerov kot tudi v cis- ali trans-obliki in vsakokrat kot proste baze ali soli, prednostno s fiziološko prenesljivimi kislinami.
3. Spojine po zahtevku 1 ali 2, v katerih imajo Ri/R2/R3 pomene C2-C5-acil/H/H; C6H5CO/H/H; C,-C4-alkil/OH/H; C2-C5-acil/Ci-C4-alkil/H; C2-C5-acil/OH/C,-C4-alkil; OH/C2-C5-acil/CrC4-alkil.
4. Spojine po zahtevku 1, 2 in 3, označene s tem, da A stoji za 0-(CH2)2-0, 0-(CH2)4-0 ali
5. Spojine po zahtevku 1, 2, 3 ali 4, označene s tem, daje skupina II acetilfenil.
6. Spojine po zahtevku 1, 3, 4 ali 5, označene s tem, da stoji skupina za R
NH
7. Zdravila, označena s tem, da vsebujejo spojino po zahtevkih 1 do 6. 6
8. Uporaba spojin po zahtevkih 1 do 6 pri pripravi zdravil za zdravljenje bolezni, pri katerih so pomembni vnetni in/ali alergijski procesi, zlasti astme, ulceroznega kolitisa, psoriaze, in za zdravljenje gastropatije, povzročene z nesteroidnimi antiflogistiki.
9. Postopek za pripravo spojin po zahtevkih 1 do 6, označen s tem, da a) imidoester s formulo
v kateri imajo Rt do R4, A in B gornji pomen in stoji R prednostno za CrC6-alkilni ostanek ali za benzil, presnovimo z amoniakom, ali da bi) fenol ali tiofenol s formulo
(XI) / v kateri Z predstavlja OH ali SH in imajo Rh R2 in R3 gornji pomen, presnovimo s spojino s formulo oz. L-Aj-Χ 2
(XIII), 7
•ΝΗ ΝΗ, v kateri imajo Ab Α2, Β, R4, Χ2 in Χ3 gornji pomen in stoji L za nukleofugno odhodno skupino, oz. (b2) fenol ali tiofenol s formulo
(XIV), v kateri imajo B, R4 in Z gornji pomen, presnovimo s spojino s formulo
(XV), oz. oz.
(XVI), (XVII) 8 OZ.
1-3 -Z
(XVIII), v katerih imajo Ai, A2, Ri, R2, R3 in Z gornji pomen, ali da c) amidoksim s formulo
(XIX), v kateri imajo A, B in Ri do R4 gornji pomen, reduciramo v ustrezni amidin.
SI9300066A 1992-02-05 1993-02-05 Novi derivati amidinov, njihova priprava in uporaba SI9300066B (sl)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4203201A DE4203201A1 (de) 1992-02-05 1992-02-05 Neue amidinderivate, ihre herstellung und verwendung
DE4224289A DE4224289A1 (de) 1992-07-23 1992-07-23 Neue Amidinderivate, ihre Herstellung und Verwendung
DE4244241A DE4244241A1 (de) 1992-12-24 1992-12-24 Neue Verbindungen, ihre Herstellung und ihre Verwendung

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SI9300066A SI9300066A (en) 1993-09-30
SI9300066B true SI9300066B (sl) 2003-02-28

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YU6393A (sh) 1996-10-09
EP0625138A1 (de) 1994-11-23
NO301540B1 (no) 1997-11-10
KR0163222B1 (ko) 1999-01-15
CZ188694A3 (en) 1995-03-15
UA43318C2 (uk) 2001-12-17
EP0625138B1 (de) 1999-06-02
ATE180770T1 (de) 1999-06-15
PL173789B1 (pl) 1998-04-30
DK0625138T3 (da) 1999-11-15
TW232005B (sl) 1994-10-11
JPH07503718A (ja) 1995-04-20
FI943618A (fi) 1994-08-04
ES2132216T3 (es) 1999-08-16
HRP930102A2 (en) 1998-12-31
DE59309630D1 (de) 1999-07-08
RU2124002C1 (ru) 1998-12-27
SK91494A3 (en) 1995-02-08
JP2002322143A (ja) 2002-11-08
SG44837A1 (en) 1997-12-19
SK281016B6 (sk) 2000-10-09
KR950700241A (ko) 1995-01-16
NZ246593A (en) 1997-07-27
MX9300630A (es) 1993-09-01
FI943618A0 (fi) 1994-08-04
HU216191B (hu) 1999-05-28
EP0902013A1 (de) 1999-03-17
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CA2427890A1 (en) 1993-08-19
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US20030130232A1 (en) 2003-07-10
AU3349793A (en) 1993-09-03
US6489365B1 (en) 2002-12-03
US6037377A (en) 2000-03-14
EP0902013B1 (de) 2001-12-12
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ATE210634T1 (de) 2001-12-15
CA2129526A1 (en) 1993-08-06
SI9300066A (en) 1993-09-30
JP3487851B2 (ja) 2004-01-19
DK0902013T3 (da) 2002-03-25
HUT68419A (en) 1995-06-28
RU94041836A (ru) 1997-02-20
DE59310252D1 (de) 2002-01-24
NO942903L (no) 1994-10-03
PT902013E (pt) 2002-06-28
AU673343B2 (en) 1996-11-07
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