HRP20160624T1 - Derivati sterola, postupci njihove pripreme, farmaceutski pripravci koji ih sadrže i njihova uporaba za liječenje multiplih glioblastoma - Google Patents
Derivati sterola, postupci njihove pripreme, farmaceutski pripravci koji ih sadrže i njihova uporaba za liječenje multiplih glioblastoma Download PDFInfo
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- HRP20160624T1 HRP20160624T1 HRP20160624TT HRP20160624T HRP20160624T1 HR P20160624 T1 HRP20160624 T1 HR P20160624T1 HR P20160624T T HRP20160624T T HR P20160624TT HR P20160624 T HRP20160624 T HR P20160624T HR P20160624 T1 HRP20160624 T1 HR P20160624T1
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- 208000005017 glioblastoma Diseases 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 3
- 229930182558 Sterol Natural products 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003432 sterols Chemical class 0.000 title 1
- 235000003702 sterols Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000003367 polycyclic group Chemical group 0.000 claims 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- CCIBGDNXMPNUHL-UHFFFAOYSA-N 2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoic acid Chemical compound OC(=O)C(C)NC(=O)CNC(=O)OCC1=CC=CC=C1 CCIBGDNXMPNUHL-UHFFFAOYSA-N 0.000 claims 3
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 claims 3
- 125000000539 amino acid group Chemical group 0.000 claims 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 210000001130 astrocyte Anatomy 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- MCLPGRDSFRGNHK-UHFFFAOYSA-N phenanthren-3-yl 2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound CC1(OCC(O1)C(=O)OC=1C=CC=2C=CC3=CC=CC=C3C=2C=1)C MCLPGRDSFRGNHK-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical group CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- -1 substituted Chemical class 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001391 thioamide group Chemical group 0.000 claims 1
Classifications
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- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Claims (16)
1. Spoj formule (I)
[image]
u kojem
- A predstavlja
-(R1)n- skupinu gdje je R1 aminokiselinski ostatak vezan svojim C-terminalnim krajem i n = 1 do 3, svaki R1 je identičan ili različit, gdje je N-terminalni kraj te aminokiseline nesupstituiran ili supstituiran -C-(O)-R2 skupinom gdje je R2 mono- ili policiklička C6-C14 arilalkil skupina; mono- ili policiklička C5-C14 heteroarilalkil skupina koja može sadržavati jedan ili više heteroatoma, koji mogu biti identični ili različiti, mono- ili policiklička C6-C14 arilalkiloksi skupina ili mono- ili policiklička C5-C14 heteroarilalkiloksi skupina koja može sadržavati jedan ili više heteroatoma, koji mogu biti identični ili različiti,
-C(O)-NH-R3 ili -C(S)-NH-R3 skupinu gdje je R3 vodik; C1-C12 alkil skupina, linearna ili razgranata, nesupstituirana ili supstituirana skupinom odabranom između OR, NRR’, NHR i SR, gdje R i R’ nezavisno predstavljaju vodik, linearni C1-C12 alkil ili nesupstituirani aril; aril skupina nesupstituirana ili supstituirana skupinom odabranom između OR, NRR’, NHR i SR kako su prethodno definirane; acil skupina; formil skupina; sulfonil skupina; sulfinil skupina, silil skupina, nesupstituirana ili supstituirana, nesupstituirana ili supstituirana mono- ili policikličkom C6-C14 aril skupinom, nesupstituirana ili supstituirana barem jednim linearnim ili razgranatim C1-C6 alkilom; alil skupina; šećerni ostatak; -C(O)-OR4 skupina gdje je R4 linearni ili razgranati C1-C12 alkil nesupstituiran ili supstituiran skupinom odabranom između OR, NRR’, NHR i SR, kako su prethodno definirane; amidna skupina; tioamidna skupina; sulfonamidna skupina,
-C(O)-R5 skupinu gdje je R5 zasićeni C5-C14 heterocikl koji sadrži 1 ili 2 heteroatoma, nesupstituiran ili supstituiran barem jednim linearnim ili razgranatim C1-C6 alkilom ili skupinom odabranom između OR, NRR’, NHR i SR, gdje R i R’ nezavisno predstavljaju vodik, C1-C12 alkil ili nesupstituirani aril.
- B predstavlja -C(O)-R6 skupinu gdje je R6 vodik; C1-C12, poželjno C1-C6 alkil, linearan ili razgranat, nesupstituiran ili supstituiran skupinom odabranom između OR, NRR’, NHR i SR, kako su prethodno definirane; aril skupina, nesupstituirana ili supstituirana skupinom odabranom između OR, NRR’, NHR i SR, kako su prethodno definirane; ili pak R6 predstavlja OR7, gdje je R7 linearni ili razgranati C1-C12, poželjno C1-C6 alkil.
2. Spoj formule (I) prema zahtjevu 1, gdje je ispunjen barem jedan od sljedećih uvjeta:
- A predstavlja -(R1)n- skupinu gdje je R1 aminokiselinski ostatak i n = 2;
- A predstavlja -(R1)n- skupinu gdje je R1 aminokiselinski ostatak, n = 2 i N-terminalni kraj te aminokiseline je supstituiran arilalkoksikarbonil skupinom, posebno benziloksikarbonilom;
- A predstavlja alanil radikal vezan za glicinil radikal, po izboru supstituiran na svom N-terminalnom kraju arilalkoksikarbonil skupinom, posebno benziloksikarbonilom;
- A predstavlja metionil radikal vezan za glicinil radikal, po izboru supstituiran na svom N-terminalnom kraju arilalkoksikarbonil skupinom, posebno benziloksikarbonilom.
3. Spoj formule (I) prema zahtjevu 1, gdje A predstavlja -C(O)-R5 skupinu gdje R5 je 2,2-dimetil-1,3-dioksolan skupina.
4. Spoj formule (I) prema jednom od zahtjeva 1 do 3, gdje B predstavlja acil skupinu gdje alkil skupina jest C1-C6, posebno acetil, ili alkoksikarbonil skupinu gdje alkil skupina jest C1-C6, posebno tert-butoksikarbonil skupina.
5. Spoj formule (I), naznačen time što se odabire između sljedećih spojeva:
- 7-((tert-butoksikarbonil)oksi)-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1H-ciklopenta[a]fenantren-3-il 2-(2-(((benziloksi)karbonil)amino)-acetamido)propanoat (molekula 1.a);
- 7-acetoksi-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1Hciklopenta[a]fenantren-3-il 2-(2-(((benziloksi)karbonil)amino)-acetamido)propanoat (molekula 1.b);
- 7-((tert-butoksikarbonil)oksi)-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1H-ciklopenta[a]fenantren-3-il 2,2-dimetil-1,3-dioksolan-4-karboksilat (molekula 2.a);
- 7-acetoksi-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1Hciklopenta[a]-fenantren-3-il 2,2-dimetil-1,3-dioksolan-4-karboksilat (molekula 2.b).
6. Postupak za pripremu spoja formule (I) prema bilo kojem od zahtjeva 1 do 5, naznačen time što obuhvaća sljedeće korake:
- zaštita hidroksilne funkcije na položaju 3 kolesterola zaštitnom skupinom,
- uvođenje funkcije ketona na položaj 7,
- redukcija funkcije ketona u hidroksilnu funkciju,
- uvođenje zaštitne skupine na hidroksilnu funkciju na položaju 7, što odgovara B skupini, i
- uklanjanje zaštite hidroksilne funkcije na položaju 3.
7. Postupak prema zahtjevu 6, naznačen time što nakon uklanjanja zaštite, hidroksilna funkcija na položaju 3 može biti supstituirana željenom A skupinom.
8. Farmaceutski pripravak koji sadrži barem jedan spoj formule (I) prema bilo kojem od zahtjeva 1 do 5 i farmaceutski prikladan nosač.
9. Farmaceutski pripravak prema zahtjevu 8, naznačen time što se navedeni spoj formule (I) koristi kao jedina djelatna tvar ili u kombinaciji sa sredstvom protiv raka.
10. Farmaceutski pripravak prema bilo kojem od zahtjeva 8 ili 9, naznačen time što se sastoji od liposoma ili alkoholne otopine barem jednog spoja formule (I), samog ili u smjesi s drugom djelatnom tvari.
11. Spoj formule (I) prema bilo kojem od zahtjeva 1 do 5, za uporabu u liječenju bolesti koje obuhvaćaju transformirane astrocitne stanice.
12. Spoj formule (I) prema bilo kojem od zahtjeva 1 do 5, za uporabu u liječenju multiformnog glioblastoma.
13. Spoj formule (I) prema bilo kojem od zahtjeva 1 do 5, za uporabu u liječenju bolesti koje obuhvaćaju transformirane astrocitne stanice, to liječenje je sekvencijsko liječenje koje obuhvaća barem jedan korak primjene prvog spoja formule (I) i barem jedan korak primjene drugog spoja formule (I), koji je različit od prvog.
14. Spoj formule (I) prema bilo kojem od zahtjeva 1 do 5, za uporabu u liječenju multiformnog glioblastoma, to liječenje je sekvencijsko liječenje koje obuhvaća barem jedan korak primjene prvog spoja formule (I) i barem jedan korak primjene drugog spoja formule (I), koji je različit od prvog.
15. Farmaceutski pripravak prema bilo kojem od zahtjeva 8 do 10, naznačen time što je taj spoj formule (I) 7-acetoksi-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1H-ciklopenta[a]-fenantren-3-il 2,2-dimetil-1,3-dioksolan-4-karboksilat (molekula 2.b).
16. Spoj formule (I) prema zahtjevu 5, za uporabu prema zahtjevu 14, naznačen time što je prvi spoj formule (I) 7-((tert-butoksikarbonil)oksil)-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1H-ciklopenta[a]fenantren-3-il 2-(2-(((benziloksi)karbonil)amino)-acetamido) propanoat (molekula 1.a) i drugi spoj formule (I) je 7-((tert-butoksikarbonil)oksi)-10,13-dimetil-17-(6-metilheptan-2-il)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradekahidro-1H-ciklopenta[a]fenantren-3-il 2,2-dimetil-1,3-dioksolan-4-karboksilat (molekula 2.a).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12305518.8A EP2662382B1 (fr) | 2012-05-10 | 2012-05-10 | Dérivés de stérol, leur procédé de préparation, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement du glioblastome multiple |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160624T1 true HRP20160624T1 (hr) | 2016-08-12 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160624TT HRP20160624T1 (hr) | 2012-05-10 | 2016-06-07 | Derivati sterola, postupci njihove pripreme, farmaceutski pripravci koji ih sadrže i njihova uporaba za liječenje multiplih glioblastoma |
| HRP20180345TT HRP20180345T1 (hr) | 2012-05-10 | 2018-02-26 | Derivati sterola i njihova upotreba u liječenju bolesti koje uključuju transformirane astrocitne stanice, ili u liječenju zloćudnih hemopatija |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| HRP20180345TT HRP20180345T1 (hr) | 2012-05-10 | 2018-02-26 | Derivati sterola i njihova upotreba u liječenju bolesti koje uključuju transformirane astrocitne stanice, ili u liječenju zloćudnih hemopatija |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US10800806B2 (hr) |
| EP (2) | EP2662382B1 (hr) |
| JP (1) | JP6270823B2 (hr) |
| KR (1) | KR102160316B1 (hr) |
| CN (1) | CN104302655B (hr) |
| BR (1) | BR112014026948B1 (hr) |
| CA (1) | CA2871714C (hr) |
| CY (2) | CY1117723T1 (hr) |
| DK (2) | DK2662382T3 (hr) |
| ES (2) | ES2580331T3 (hr) |
| HK (2) | HK1191654A1 (hr) |
| HR (2) | HRP20160624T1 (hr) |
| HU (2) | HUE029243T2 (hr) |
| IN (1) | IN2014DN09437A (hr) |
| LT (1) | LT2847204T (hr) |
| ME (1) | ME02436B (hr) |
| PL (2) | PL2662382T3 (hr) |
| PT (2) | PT2662382T (hr) |
| RS (2) | RS54926B1 (hr) |
| RU (1) | RU2627710C2 (hr) |
| SI (2) | SI2662382T1 (hr) |
| SM (1) | SMT201600215B (hr) |
| TR (1) | TR201802700T4 (hr) |
| WO (1) | WO2013168096A1 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3013048A1 (fr) * | 2013-11-12 | 2015-05-15 | Beta Innov | Derive de sterol, son procede de preparation, composition pharmaceutique le contenant et son utilisation pour le traitement du glioblastome multiforme |
| EP3593789A1 (fr) * | 2018-07-11 | 2020-01-15 | Beta Innov | Composition contenant un dérivé de 7beta-hydroxycholestérol et un véhicule lipidique, et son utilisation dans le traitement de pathologies néoplasiques |
| KR20220156177A (ko) * | 2021-05-18 | 2022-11-25 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| WO2022245122A1 (ko) * | 2021-05-18 | 2022-11-24 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| WO2024030660A2 (en) * | 2022-08-04 | 2024-02-08 | University Of Massachusetts | Cholesterol-modified hyaluronic acids |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9602100D0 (sv) * | 1996-05-30 | 1996-05-30 | Magnus Axelson | New pharmaceuticals |
| JP2006503840A (ja) * | 2002-09-25 | 2006-02-02 | フォーブス メディ−テック インコーポレーテッド | ステロール及び／又はスタノール及び抗炎症剤の特定の種類を含有する新規構造体及び組成物、並びに、心血管疾患、その根底にある高脂血症を含む病気、及び原因又は症状の一部として炎症を有する他の障害の治療又は予防におけるそれらの使用 |
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2012
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