ME02436B - Derivati sterola, metodi njihovog pripremanja, farmaceutske smeše koje ih sadrže, i njihova upotreba u lečenju multiplih glioblastoma - Google Patents
Derivati sterola, metodi njihovog pripremanja, farmaceutske smeše koje ih sadrže, i njihova upotreba u lečenju multiplih glioblastomaInfo
- Publication number
- ME02436B ME02436B MEP-2016-134A MEP2016134A ME02436B ME 02436 B ME02436 B ME 02436B ME P2016134 A MEP2016134 A ME P2016134A ME 02436 B ME02436 B ME 02436B
- Authority
- ME
- Montenegro
- Prior art keywords
- group
- formula
- compound
- dimethyl
- substituted
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 208000005017 glioblastoma Diseases 0.000 title claims 4
- 201000010915 Glioblastoma multiforme Diseases 0.000 title claims 3
- 229930182558 Sterol Natural products 0.000 title 1
- 238000004519 manufacturing process Methods 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
- 125000000217 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
- 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
- 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 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical class 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
- 238000010511 deprotection reaction Methods 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
- 238000000034 method Methods 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
- OZPFVBLDYBXHAF-UHFFFAOYSA-M 2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound CC1(C)OCC(C([O-])=O)O1 OZPFVBLDYBXHAF-UHFFFAOYSA-M 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
- 125000003368 amide group Chemical group 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
- 210000001130 astrocyte Anatomy 0.000 claims 1
- 230000003140 astrocytic effect Effects 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 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
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
-
- 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
-
- 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
-
- 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
Landscapes
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Claims (16)
1. Jedinjenje formule (I) ,naznačeno time, što- A je-(R1)n- grupa u kojoj je R1 aminokiselinska rezidua vezana svojim C-terminalnim krajem i n = 1 do 3, svaki R1 je identičan ili različit, gde je N-terminalni kraj pomenute amino-kiseline nesupstituisan ili supstituisan sa -C-(O)-R2 grupom u kojoj je R2 mono- ili policiklična C6-C14 arilalkil grupa; mono- ili policiklična C5-C14 heteroarilalkil grupa koja može sadržati jedan ili više heteroatoma, koji mogu biti identični ili različiti; mono- ili policiklična C6-C14 arilalkiloksi grupa ili mono- ili policiklična C5-C14 heteroarilalkiloksi grupa koja može sadržati jedan ili više heteroatoma koji mogu biti identični ili različiti, -C(O)-NH-R3 ili -C(S)-NH-R3 grupa u kojoj je R3 vodonik; C1-C12 alkil grupa, linearna ili granata, nesupstituisana ili supstituisana grupom koja se bira između OR, NRR’, NHR i SR, gde su R i R’, nezavisno, vodonik, linearni C1-C12 alkil ili nesupstituisani aril; aril grupa, nesupstituisana ili supstituisana grupom koja se bira između OR, NRR’, NHR i SR kako je definisano gore; acil grupa; formil grupa; sulfonil grupa; sulfinil grupa, silil grupa, nesupstituisana ili supstituisana mono- ili policikličnom C6-C14 aril grupom, nesupstituisanom ili supstituisanom najmanje jednim linearnim ili granatim C1-C6 alkilom; alil grupa; šećerna rezidua; -C(O)-OR4 grupa u kojoj je R4 linearni ili granati C1-C12 alkil, nesupstituisan ili supstituisan grupom koja se bira između OR, NRR’, NHR i SR, kako je definisano gore; amidna grupa; tioamidna grupa; sulfonamidna grupa,-C(O)-R5 grupa u kojoj je R5 zasićeni C5-C14 heterocikl koji uključuje 1 ili 2 heteroatoma, nesupstituisan ili supstituisan najmanje jednim linearnim ili granatim C1-C6 alkilom ili grupom koja se bira između OR, NRR’, NHR i SR, kako je definisano gore, gde su R i R’, nezavisno, vodonik, C1-C12 alkil ili nesupstituisani aril. - B je -C(O)-R6 grupa gde je R6 vodonik; C1-C12, poželjno C1-C6, alkil, linearni ili granati, nesupstituisan ili supstituisan grupom koja se bira između OR, NRR', NHR i SR, kako je definisano gore; aril grupa, nesupstituisana ili supstituisana grupom koja se bira između OR, NRR', NHR i SR, kako je definisano gore; ili R6 predstavlja OR7, gde je R7 linearni ili granati C1-C12, poželjno C1-C6, alkil.
2. Jedinjenje formule (I) prema zahtevu 1, naznačeno time, što je ispunjen najmanje jedan od sledećih uslova: - A je -(R1)n- grupa, gde je R1 aminokiselinska rezidua i n = 2; - A je -(R1)n- grupa, gde je R1 aminokiselinska rezidua, n = 2 i N-terminalni kraj pomenute amino-kiseline je supstituisan arilalkoksikarbonil grupom, posebno benziloksikarbonil grupom; - A je alanil radikal povezan sa glicinil radikalom, opciono supstituisan na N-terminalnom kraju arilalkoksikarbonil grupom, posebno benziloksikarbonil grupom; - A je metionil radikal povezan sa glicinil radikalom, opciono supstituisan na N-terminalnom kraju arilalkoksikarbonil grupom, posebno benziloksikarbonil grupom;
3. Jedinjenje formule (I) prema zahtevu 1, naznačeno time, što je A -C(O)-R5 grupa u kojoj je R5 2,2-dimetil-1,3-dioksolanska grupa.
4. Jedinjenje formule (I) prema jednom od zahteva 1 do 3, naznačeno time, što je B acil grupa u kojoj je alkil grupa C1-C6, posebno acetil, ili alkoksikarbonil grupa u kojoj je alkil grupa C1-C6, posebno tert-butoksikarbonil grupa.
5. Jedinjenje formule (I) prema zahtevu 1, naznačeno time, što se bira između sledećih jedinjenja: - 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-(((benzil-oksi) karbonil)amino)-acetamido)propanoat (molekul 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-1H-ciklopenta[a]fenantren-3-il 2-(2-(((benziloksi)karbonil)amino)-aceta-mido)propanoat (molekul 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-dio-ksolan-4-karboksilat (molekul 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-1H-ciklopenta[a]fenantren-3-il 2,2-dimetil-1,3-dioksolan-4-karboksilat (molekul 2.b).
6. Metod pripremanja jedinjenja formule (I) prema bilo kojem od zahteva 1 do 5, naznačen time, što uključuje sledeće korake: - protektovanje hidroksilne funkcije na poziciji 3 holesterola protektivnom grupom, - uvođenje ketonske funkcije na poziciji 7, - redukcija ketonske funkcije u hidroksilnu funkciju, - uvođenje protektivne grupe na hidroksilnoj funkciji na poziciji 7, koja odgovara B grupi, i - deprotektovanje hidroksilne funkcije na poziciji 3.
7. Metod prema zahtevu 6, naznačen time, što posle deprotektovanja, hidroksilna funkcija na poziciji 3 može biti supstituisana željenom A grupom.
8. Farmaceutska smeša, naznačena time, što sadrži najmanje jedno jedinjenje formule (I) prema bilo kojem od zahteva 1 do 5 i farmaceutski prihvatljivi prenosnik.
9. Farmaceutska smeša prema zahtevu 8, naznačena time, što se pomenuto jedinjenje formule (I) koristi kao jedini aktivni sastojak, ili u kombinaciji sa antikancerskim sredstvom.
10. Farmaceutska smeša prema bilo kojem od zahteva 8 ili 9, naznačena time, što se sastoji od lipozomskog ili alkoholnog rastvora najmanje jednog jedinjenja formule (I), samog ili u mešavini sa još jednim aktivnim sastojkom.
11. Jedinjenje formule (I) prema bilo kojem od zahteva 1 do 5, naznačeno time, što se koristi u lečenju bolesti u koje su uključene transformisane astrocitne ćelije.
12. Jedinjenje formule (I) prema bilo kojem od zahteva 1 do 5, naznačeno time, što se koristi u lečenju multiformnog glioblastoma.
13. Jedinjenje formule (I) prema bilo kojem od zahteva 1 do 5, naznačeno time, što se koristi u lečenju bolesti u koje su uključene transformisane astrocitne ćelije, pomenuto lečenje je sekvencijalno lečenje koje uključuje najmanje jedan korak primene prvog jedinjenja formule (I) i najmanje jedan korak primene drugog jedinjenja formule (I), različitog od prvog.
14. Jedinjenje formule (I) prema bilo kojem od zahteva 1 do 5, naznačeno time, što se koristi u lečenju multiformnog glioblastoma, pomenuto lečenje je sekvencijalno lečenje koje uključuje najmanje jedan korak primene prvog jedinjenja formule (I) i najmanje jedan korak primene drugog jedinjenja formule (I), različitog od prvog.
15. Farmaceutska smeša prema bilo kojem od zahteva 8 do 10, naznačena time, što je pomenuto jedinjenje 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 (molekul 2.b).
16. Jedinjenje formule (I) prema zahtevu 5, za upotrebu prema zahtevu 14, naznačeno time, što je prvo jedinjenje 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-(((benzil-oksi) karbonil)amino)-acetamido) propanoat (molekul 1.a) i drugo jedinjenje 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 (molekul 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 |
|---|---|
| ME02436B true ME02436B (me) | 2016-09-20 |
Family
ID=46149353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-134A ME02436B (me) | 2012-05-10 | 2012-05-10 | Derivati sterola, metodi njihovog pripremanja, farmaceutske smeše koje ih sadrže, i njihova upotreba u lečenju multiplih glioblastoma |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US10800806B2 (me) |
| EP (2) | EP2662382B1 (me) |
| JP (1) | JP6270823B2 (me) |
| KR (1) | KR102160316B1 (me) |
| CN (1) | CN104302655B (me) |
| BR (1) | BR112014026948B1 (me) |
| CA (1) | CA2871714C (me) |
| CY (2) | CY1117723T1 (me) |
| DK (2) | DK2662382T3 (me) |
| ES (2) | ES2580331T3 (me) |
| HR (2) | HRP20180345T1 (me) |
| HU (2) | HUE029243T2 (me) |
| IN (1) | IN2014DN09437A (me) |
| LT (1) | LT2847204T (me) |
| ME (1) | ME02436B (me) |
| PL (2) | PL2662382T3 (me) |
| PT (2) | PT2662382T (me) |
| RS (2) | RS54926B1 (me) |
| RU (1) | RU2627710C2 (me) |
| SI (2) | SI2662382T1 (me) |
| SM (2) | SMT201800147T1 (me) |
| TR (1) | TR201802700T4 (me) |
| WO (1) | WO2013168096A1 (me) |
Families Citing this family (5)
| 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 |
| KR102748745B1 (ko) * | 2021-05-18 | 2025-01-03 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| KR102689231B1 (ko) * | 2021-05-18 | 2024-07-30 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| WO2024030660A2 (en) * | 2022-08-04 | 2024-02-08 | University Of Massachusetts | Cholesterol-modified hyaluronic acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9602100D0 (sv) * | 1996-05-30 | 1996-05-30 | Magnus Axelson | New pharmaceuticals |
| RU2005112247A (ru) * | 2002-09-25 | 2006-01-20 | Форбз Меди-Тек Инк. (Ca) | Новые структуры и композиции, содержащие стеролы и/или станолы и определенные классы противовоспалительных средств, и их применение для лечения или предупреждения сердечно-сосудистого заболевания, лежащих в его основе состояний, включая гиперлипидемию, и других нарушений, при которых воспаление является частью их этиологии или проявления |
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2012
- 2012-05-10 RS RS20160499A patent/RS54926B1/sr unknown
- 2012-05-10 SI SI201230585A patent/SI2662382T1/sl unknown
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