SI9111899B - Derivati žolčnih kislin, postopke za njihovo pripravo in uporaba teh spojin kot zdravila - Google Patents

Derivati žolčnih kislin, postopke za njihovo pripravo in uporaba teh spojin kot zdravila Download PDF

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SI9111899B
SI9111899B SI9111899A SI9111899A SI9111899B SI 9111899 B SI9111899 B SI 9111899B SI 9111899 A SI9111899 A SI 9111899A SI 9111899 A SI9111899 A SI 9111899A SI 9111899 B SI9111899 B SI 9111899B
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residue
alkyl
alkoxy
substituted
unsubstituted
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SI9111899A
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SI9111899A (sl
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Werner Kramer
Guenther Wess
Stefan Muellner
Horst Neubauer
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Hoechst Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • 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
    • A61P3/06—Antihyperlipidemics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0016—Oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Claims (7)

  1. Patentni zahtevki 1. Dimemi derivati žolčnih kislin s formulo Gl -X-G2 (1) v kateri pomenijo Gl spojino s splošno formulo O
    pri čemer Y pomeni prosto valenco za vezavo skupine X ali ima ta-le pomen -OL, -NHL, -NL2, pomeni preko araino skupine vezano amino kislino ali aminosulfonsko kislino, kot npr. -nhch2-co2h, -nh-ch2ch2-so3h, -n-ch2ch2-so3h I ch3 -n-ch2co2h, -nh-chco2h ch3 r6 in njihove (CrC4)-alkil estre in alkalijske in zemeljsko alkalijske soli, OKa, pri čemer Ka pomeni kation, kot npr. alkalijski ali zemeljsko alkalijski ion ali tudi kvartemi amonijev ion in pri čemer L pomeni 2 H, nasičen ali nenasičen alkilm ostanek z 1 do 10 atomi C, ki je razvejen ali nerazvejen, cikloalkilm ostanek s 3 do 8 atomi C, fenilni ostanek, ki je nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (Ci-C4)-alkilom ali (Ci-C4)-alkoksi, benzilni ostanek, ki je nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (CrC4)-alkilom ali (C]-C4)-alkoksi m R6 pomeni metil, izopropil, izobutil, 2-butil benzil, 4-hidroksibenzil, hidroksimetil, 1-hidroksietil, H3CSCH2CH2-, ho2cch2, HOCCH2CH2-, R1 pomeni prosto valenco za vezavo skupine X ali H, nasičen ali nenasičen alkilni ostanek z 1-10 atomi C, kije razvejen ali nerazvejen, cikloalkilni ostanek s 3-8 atomi C, fenilni ostanek, ki je nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (Q-C4)-alkilom ali (Ci-C4)-alkoksi, -fNH3, -0P03", benzilni ostanek, kije v jedru nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (Ci-C4)-alkilom, (CrC4)-alkoksi, -"NH3, -0P03~ ali fenilom, ki je lahko po svoji plati 1-3-krat substituiran s F, Cl, Br, (CrC4)-alkilom, (CrC4)-alkoksi, -+NH3, -OP03‘, bifenilmetilni ostanek, kije nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (Cr C4)-alkilom ali (CrC4)-alkoksi, - NH3, -0P03", trifenilmetilni ostanek, kije nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (CrC4)-alkilom ali (Ct-C4)-alkoksi, -’NH3, -0P03‘, 1- ali 2-naftil metilni ostanek, ki je nesubstituiran ali l- do 3-krat substituiran s F, Cl, Br, (Ci-C4)-alkilom ali (CrC4)-alkoksi, -"NH3, -0P03~ 9-fluorenilni ostanek, ki je nesubstituiran ali 1- do 3-krat substituiran s F, Cl, Br, (C|-C4)-alkilom, (CrC4)-alkoksi, - NH3, -0P03", 2-, 3- ali 4-piridilni ostanek, 0 0 0 II i II ostanek -P-OL, -S-OL ali _J 1 0 1 1 II OL 0 3 pri čemer ima L zgoraj navedeni pomen, R2 do R\ pri čemer R^ in R3 oz. R4 in R5 pomenijo skupaj vsakič kisik karbonilne skupine ali posamič in vsakič neodvisno drug od drugega 0 0 0 II H, OT, -ST, -NHT, O-C-T, -S-C-T, -NH-C-T, 0 0 -O-P-OT, -O-S-OT, -T OL 0 pri čemer ima L zgoraj navedeni pomen in ima T pomen L ali ima prosto valenco za vezavo skupine X, z omejitvijo, da izhaja v celem samo ena prosta valenca za vezavo skupine X, X enojno vez ali skupino s formulo III O -[-(N)s - A - N - C- (CH2)5 -L1 L2 O c -]r - N - Bt - (III) 1-3 pri čemer pomeni A alkilensko verigo, ki je razvejena ali nerazvejena, nasičena ali nenasičena in v verigi v danem primeru lahko prekinjena z -O-, -S- ali anlenom, zlasti femlenom, pri čemer se vrši povezava tako-le O' ' ~(3 ali' (°J" 4 in obsega veriga v celem 2 do 12, prednostno 2 do 6 verižnih členov p, B alkilensko verigo, kije razvejena ali nerazvejena, nasičena ali nenasičena in v verigi v danem primeru lahko prekinjena z -O-, -S- ali arilenom, zlasti fenilenom, pri čemer se vrši povezava tako-le O' * Ό ali w in obsega veriga v celem 2 do 18, prednostno 2 do 12 verižnih členov n, Ll, L2 in L3 so enaki ali različni in imajo enak pomen kot L, in pomenijo q 0-5, r 0 ali 1 in s 0 ali 1 in t 0 ali 1, G2 pomeni spojino s splošno formulo IV
    pri čemer imata Y in R1 pod Gl navedeni pomen kot tudi R7 do R10, pri čemer pomenijo R7 in R8 oz. R9 in R10 skupaj vsakič kisik karbonilne skupine ali posamič in vsakič neodvisno drug od drugega H, -OT, -ST, -NHT, 0 0 0 0 o o ^ O-C-T, -S-C-T, -NH-C-T, -O-P-OT, -O-S-OT, -S-OT, -P-OT, -T I »» · H OL 0 0 0 5 pri čemer imata L m T pod Gl navedeni pomen, prav tako z omejitvijo, da izhaja iz G2 v celem samo ena prosta valenca za vezavo skupine X, pri čemer so izključeni derivati žolčnih kislin z naslednjimi formulami: 6 ali
    u«
    7
  2. 2. Spojina po zahtevku 1, označena s tem, da se povezava ostankov Gl in G2 ne vrši simetrično, t.j. ne preko enakih obročev.
  3. 3. Spojina po zahtevkih 1 m 2, označena s tem, da se vrši povezava ostanka Gl preko C-24 (obroč D) preko X na eno od leg C-3 (obroč A), C-7 (obroč B) ali C-12 (obroč G) ostanka G2.
  4. 4. Postopek za pripravo spojine po enem ali več zahtevkih 1 do 3, označen s tem, da a) v primeru X = enojna vez presnovimo po načelno znanih postopkih primerne reakcije sposobne oblike Gl in G2 ali b) v primeru X = mostni člen presnovimo po načelno znanih postopkih, a) reakcijsko sposobne oblike Gl-X z G2 oz. β) reakcijsko sposobne oblike G2-X z Gl, c) pripravimo po znanih postopkih iz G1-X1 spojine s splošno formulo I (Gl-X-G2), pri čemer nastane X iz XI in X2 z izoblikovanjem kovalentne vezi, zlasti pri kondenzacijski ali substitucijski reakciji.
  5. 5. Uporaba spojine po zahtevkih 1 do 3 za pripravo zdravila.
  6. 6. Spojina po zahtevkih 1 do 3 kot zdravilo.
  7. 7. Farmacevtski pripravek, označen s tem, da vsebuje spojine po zahtevkih 1 do 3. Za HOECHST AKTIENGESELLSCHAFT: WSA?<HA, tf.ous. j <· , ;· :,i ^r-PPV* 1-S. 21857-ni-OO-mn
SI9111899A 1990-12-06 1991-12-06 Derivati žolčnih kislin, postopke za njihovo pripravo in uporaba teh spojin kot zdravila SI9111899B (sl)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4038833 1990-12-06
YU189991A YU48636B (sh) 1990-12-06 1991-12-06 Dimerni derivati žučnih kiselina i postupak za njihovo dobijanje

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SI9111899A SI9111899A (sl) 1998-04-30
SI9111899B true SI9111899B (sl) 2000-06-30

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US (1) US5250524A (sl)
EP (1) EP0489423B1 (sl)
JP (1) JP3237882B2 (sl)
KR (1) KR100221690B1 (sl)
AT (1) ATE144988T1 (sl)
AU (1) AU649089B2 (sl)
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DK (1) DK0489423T3 (sl)
ES (1) ES2096614T3 (sl)
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HR (1) HRP940751B1 (sl)
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IL (1) IL100240A (sl)
NO (1) NO304187B1 (sl)
NZ (1) NZ240846A (sl)
PT (1) PT99713B (sl)
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YU (1) YU48636B (sl)
ZA (1) ZA919605B (sl)

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ES2096614T3 (es) 1997-03-16
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