HRP20151212T1 - C-28 AMINI C-3 MODIFICIRANIH DERIVATA BETULINSKE KISELINE KAO INHIBITORI SAZRIJEVANJA HIV-a P - Google Patents
C-28 AMINI C-3 MODIFICIRANIH DERIVATA BETULINSKE KISELINE KAO INHIBITORI SAZRIJEVANJA HIV-a P Download PDFInfo
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- HRP20151212T1 HRP20151212T1 HRP20151212TT HRP20151212T HRP20151212T1 HR P20151212 T1 HRP20151212 T1 HR P20151212T1 HR P20151212T T HRP20151212T T HR P20151212TT HR P20151212 T HRP20151212 T HR P20151212T HR P20151212 T1 HRP20151212 T1 HR P20151212T1
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- alkyl
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- substituted
- cycloalkyl
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- 150000001412 amines Chemical class 0.000 title 1
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 230000035800 maturation Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- -1 -hydroxyl Chemical group 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (15)
1. Spoj, uključujući njegove farmaceutski prihvatljive soli, koji je izabran iz grupe od:
spoja formule I
[image]
spoja formule II
[image]
spoja formule III
[image]
gdje je R1 izopropenil ili izopropil;
J i E su nezavisno -H ili -CH3 i E je odsutan kada je prisutna dvoguba veza;
X je fenil ili heteroaril prsten supstituiran sa A, gdje je A najmanje jedan član izabran iz grupe koju čine -H, -halo, -hidroksil, -C1-6 alkil, -C1-6 alkoksi i -COOR2;
R2 je -H, -C1-6 alkil ili –alkil supstituiran C1-6 alkil ili –aril supstituiran C1-6 alkil;
Y je izabran iz grupe koju čine -COOR2, -C(O)NR2SO2R3, -C(O)NHSO2NR2R2, -NR2SO2R2, -SO2NR2R2, -C3-6 cikloalkil-COOR2, -C1-6 alkenil-COOR2, -C1-6 alkinil-COOR2, -C1-6 alkil-COOR2, -NHC(O)(CH2)n-COOR2, -SO2NR2C(O)R2, -tetrazol i -CONHOH, pri čemu je n=1-6;
R3 je -C1-6 alkil ili alkil supstituiran C1-6alkil;
R4 je izabran iz grupe koju čine H, -C1-6 alkil, -C3-6 cikloalkil, -C1-6 supstituiran alkil, -C1-6 alkil-heteroaril, -C1-6 alkil-supstituiran heteroaril, -C1-6alkil-NR6R7, - C1-6 alkil-CONR8R9, - C3-6 cikloalkil-CONR8R9, -C3-6 cikloalkil-(CH2)1-3-NR6R7, -(CH2)1-3-C3-6 cikloalkil-NR6R7; -(CH2)1-3-C3-6 cikloalkil-(CH2)1-3-NR6R7; -C1-6alkil-Q1, C3-6 cikloalkil-Q1, -COR10,-SO2R3 i -SO2NR2R2;
Q1 = -hidroksi, -COOR2, -halo, -SO2Ra;
Ra= C1-6alkil, NR2R2,
[image]
Rb= -H, -C1-6 alkil, -COR3, -SO2R3, -SONR3R3;
R4 također može biti izabran iz grupe koju čine :
[image]
[image]
i
[image]
R5 je izabran iz grupe koju čine -H, -C1-6 alkil, -C3-6 cikloalkil, -C1-6 alkil supstituiran alkil, - COR10,-SO2R3 i -SO2NR2R2;
uz uvjet da samo jedan od R4 ili R5 može biti izabran iz grupe koju čine -COR10,-SO2R3 i -SO2NR2R2;
ili R4 i R5 su uzeti zajedno sa susjednim N tako da formiraju ciklus kao što je
[image]
ili
[image]
R10 je izabran iz grupe koju čine -H, -C1-6 alkil, -C1-6 alkil-NR6R7, -NR11R12, -OR13, -C1-6 alkil-Q2, -C3-6 cikloalkil-Q2, aril-Q2, gdje je n =1-6,
pri čemu Q2 = hidroksi, -COOR2, -halo, SO2Ra, -CONHSO2R3, -CONHSO2NR2R2;
R10 također može biti izabran iz grupe koju čine:
[image]
[image]
i
[image]
R6 i R7 su nezavisno izabrani iz grupe koju čine -H, -C1-6 alkil, -C1-6 supstituiran alkil, aril, heteroaril, supstituiran aril, supstituiran heteroaril i -C1-6 alkil-Q1,
ili R6 i R7 su uzeti zajedno sa susjednim N tako da formiraju ciklus izabran iz grupe koju čine
[image]
[image]
[image]
i
[image]
RC = C1-6 alkil, NR2R2, -COOR3;
R8 i R9 su nezavisno izabrani iz grupe koju čine -H, -C1-6 alkil, -C3-6 cikloalkil, -C1-6 supstituiran alkil, -C1-6alkil-heteroaril, -C1-6 alkil-supstituiran heteroaril, -C1-6 alkil-NR2R2, C1-6 alkil-CONR2R2, -C1-6 alkil-Q1, C3-6 cikloalkil-Q1,
ili R8 i R9 također mogu biti nezavisno izabrani iz grupe koju čine
[image]
i
[image]
ili R8 i R9 su uzeti zajedno sa susjednim N tako da formiraju ciklus izabran iz grupe koju čine:
[image]
[image]
[image]
i
[image]
i R11 i R12 su nezavisno izabrani iz grupe koju čine -H, -C1-6 alkil, -C3-6 cikloalkil i -C1-6 alkil supstituiran alkil;
ili R11 i R12 su uzeti zajedno sa susjednim N tako da formiraju ciklus izabran iz grupe koju čine
[image]
i
[image]
i
R13 je izabran iz grupe koju čine -H, C1-6 alkil, -C1-6 alkil supstituiran alkil i -C1-6 alkil NR14R15, gdje
R14 i R15 su nezavisno izabrani iz grupe koju čine -H,-C1-6 alkil i -C1-6 alkil supstituiran alkil, ili R14 i R15 su uzeti zajedno sa susjednim N tako da formiraju ciklus izabran iz grupe koju čine
[image]
i
[image]
2. Spoj prema patentnom zahtjevu 1, naznačen time što navedeni spoj ima formulu I.
3. Spoj prema patentnom zahtjevu 2, naznačen time što X je fenil prsten i Y je u para položaju.
4. Spoj prema patentnom zahtjevu 3, naznačen time što X je supstituiran fenil prsten.
5. Spoj prema patentnom zahtjevu 4, naznačen time što navedeni fenil prsten je supstituiran sa A, i A je najmanje jedan član izabran iz grupe koju čine -H, -OH i -F.
6. Spoj prema patentnom zahtjevu 5, naznačen time što Y je -COOH.
7. Spoj prema patentnom zahtjevu 4, naznačen time što X je fenil prsten i Y je -COOH u para položaju prema formuli Ia:
[image]
8. Spoj prema patentnom zahtjevu 7, naznačen time što A je najmanje jedan član izabran iz grupe koju čine -H, -OH i -F.
9. Spoj prema patentnom zahtjevu 8, naznačen time što A je -H ili -F.
10. Spoj prema patentnom zahtjevu 1, uključujući njegove farmaceutski prihvatljive soli, koji je izabran iz grupe koja se sastoji od:
[image]
i
[image]
11. Spoj prema patentnom zahtjevu 1 koji je izabran iz grupe koja se sastoji od:
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
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[image]
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[image]
[image]
[image]
[image]
[image]
i
[image]
12. Farmaceutska kompozicija koja sadrži antivirusno efikasnu količinu jednog ili više spojeva prema bilo kojem od patentnih zahtjeva 1 do 11, zajedno sa jednim ili više farmaceutski prihvatljivih nosača, ekscipijenata ili razblaživača.
13. Farmaceutska kompozicija prema patentnom zahtjevu 12, korisna za liječenje HIV infekcije, koja dodatno sadrži antivirusno efikasnu količinu sredstva za liječenje SIDA-e izabranog iz grupe koja se sastoji od:
(a) antivirusnog sredstva protiv SIDA-e;
(b) anti-infektivnog sredstva;
(c) imunomodulatora; i
(d) drugog inhibitora ulaska HIV-a.
14. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 za uporabu u postupku za liječenje sisavca inficiranog HIV virusom.
15. Intermedijerni spoj koji je izabran iz grupe od:
[image]
gdje je R3 kao što je definiran u patentnom zahtjevu 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437870P | 2011-01-31 | 2011-01-31 | |
| PCT/US2012/022847 WO2012106188A1 (en) | 2011-01-31 | 2012-01-27 | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
| EP12702946.0A EP2670764B1 (en) | 2011-01-31 | 2012-01-27 | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151212T1 true HRP20151212T1 (hr) | 2015-12-04 |
Family
ID=45567146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151212TT HRP20151212T1 (hr) | 2011-01-31 | 2015-11-11 | C-28 AMINI C-3 MODIFICIRANIH DERIVATA BETULINSKE KISELINE KAO INHIBITORI SAZRIJEVANJA HIV-a P |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8748415B2 (hr) |
| EP (1) | EP2670764B1 (hr) |
| JP (1) | JP6000283B2 (hr) |
| CN (1) | CN103339141B (hr) |
| BR (1) | BR112014010105A2 (hr) |
| CA (1) | CA2826257A1 (hr) |
| CY (1) | CY1116989T1 (hr) |
| DK (1) | DK2670764T3 (hr) |
| EA (1) | EA023578B1 (hr) |
| ES (1) | ES2552512T3 (hr) |
| HR (1) | HRP20151212T1 (hr) |
| HU (1) | HUE026371T2 (hr) |
| MX (1) | MX2013008359A (hr) |
| PL (1) | PL2670764T3 (hr) |
| PT (1) | PT2670764E (hr) |
| RS (1) | RS54352B1 (hr) |
| SI (1) | SI2670764T1 (hr) |
| SM (1) | SMT201500303B (hr) |
| WO (1) | WO2012106188A1 (hr) |
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| RU2516952C1 (ru) * | 2012-11-09 | 2014-05-20 | Леонид Леонидович Клопотенко | Фармацевтическая композиция, содержащая инкапсулированную тритерпеновую кислоту или ее производные |
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| WO2017051355A1 (en) | 2015-09-24 | 2017-03-30 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| JP2019502728A (ja) | 2016-01-20 | 2019-01-31 | グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | Ｈｉｖ成熟阻害活性を有するルパンのアミン誘導体 |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
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| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| US20090105203A1 (en) | 2006-10-16 | 2009-04-23 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| WO2009100532A1 (en) * | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | NOVEL 17ß LUPANE DERIVATIVES |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| US8802661B2 (en) * | 2010-06-04 | 2014-08-12 | Bristol-Myers Squibb Company | C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| US8754068B2 (en) * | 2010-06-04 | 2014-06-17 | Bristol-Myers Squibb Company | Modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| PT2670765T (pt) * | 2011-01-31 | 2018-01-08 | Viiv Healthcare Uk No 4 Ltd | Triterpenoides modificados em c-17 e c-3 com atividade inibidora da maturação do vih |
-
2012
- 2012-01-27 PT PT127029460T patent/PT2670764E/pt unknown
- 2012-01-27 CA CA2826257A patent/CA2826257A1/en not_active Abandoned
- 2012-01-27 EA EA201391098A patent/EA023578B1/ru not_active IP Right Cessation
- 2012-01-27 PL PL12702946T patent/PL2670764T3/pl unknown
- 2012-01-27 MX MX2013008359A patent/MX2013008359A/es active IP Right Grant
- 2012-01-27 ES ES12702946.0T patent/ES2552512T3/es active Active
- 2012-01-27 CN CN201280007020.0A patent/CN103339141B/zh not_active Expired - Fee Related
- 2012-01-27 US US13/359,680 patent/US8748415B2/en not_active Expired - Fee Related
- 2012-01-27 WO PCT/US2012/022847 patent/WO2012106188A1/en active Application Filing
- 2012-01-27 DK DK12702946.0T patent/DK2670764T3/en active
- 2012-01-27 EP EP12702946.0A patent/EP2670764B1/en active Active
- 2012-01-27 BR BR112014010105A patent/BR112014010105A2/pt unknown
- 2012-01-27 SI SI201230354T patent/SI2670764T1/sl unknown
- 2012-01-27 JP JP2013551360A patent/JP6000283B2/ja not_active Expired - Fee Related
- 2012-01-27 HU HUE12702946A patent/HUE026371T2/en unknown
- 2012-01-27 RS RS20150740A patent/RS54352B1/en unknown
-
2015
- 2015-11-11 HR HRP20151212TT patent/HRP20151212T1/hr unknown
- 2015-12-01 SM SM201500303T patent/SMT201500303B/it unknown
- 2015-12-01 CY CY20151101099T patent/CY1116989T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA201391098A1 (ru) | 2013-12-30 |
| EP2670764B1 (en) | 2015-09-02 |
| CN103339141B (zh) | 2016-08-24 |
| ES2552512T3 (es) | 2015-11-30 |
| US8748415B2 (en) | 2014-06-10 |
| RS54352B1 (en) | 2016-02-29 |
| WO2012106188A1 (en) | 2012-08-09 |
| DK2670764T3 (en) | 2015-12-07 |
| JP2014507422A (ja) | 2014-03-27 |
| HUE026371T2 (en) | 2016-05-30 |
| CY1116989T1 (el) | 2017-04-05 |
| PL2670764T3 (pl) | 2016-02-29 |
| CA2826257A1 (en) | 2012-08-09 |
| CN103339141A (zh) | 2013-10-02 |
| PT2670764E (pt) | 2015-11-20 |
| JP6000283B2 (ja) | 2016-09-28 |
| MX2013008359A (es) | 2013-08-27 |
| EA023578B1 (ru) | 2016-06-30 |
| US20130029954A1 (en) | 2013-01-31 |
| SMT201500303B (it) | 2016-01-08 |
| SI2670764T1 (sl) | 2016-03-31 |
| BR112014010105A2 (pt) | 2017-06-13 |
| EP2670764A1 (en) | 2013-12-11 |
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