KR20140123584A - Hiv 성숙 억제 활성을 갖는 c-3 시클로알케닐 트리테르페노이드 - Google Patents
Hiv 성숙 억제 활성을 갖는 c-3 시클로알케닐 트리테르페노이드 Download PDFInfo
- Publication number
- KR20140123584A KR20140123584A KR1020147025339A KR20147025339A KR20140123584A KR 20140123584 A KR20140123584 A KR 20140123584A KR 1020147025339 A KR1020147025339 A KR 1020147025339A KR 20147025339 A KR20147025339 A KR 20147025339A KR 20140123584 A KR20140123584 A KR 20140123584A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- group
- mmol
- cyclopenta
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
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- VAJIYEANEAPANC-MKCTVTTQSA-N CC(C)([C@@H]1CC2)C(C3=CCC(CC(O)=O)CC3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC[C@@H]2CCCC3)[C@H]1[C@H]2[C@@H]3C(C)=C Chemical compound CC(C)([C@@H]1CC2)C(C3=CCC(CC(O)=O)CC3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC[C@@H]2CCCC3)[C@H]1[C@H]2[C@@H]3C(C)=C VAJIYEANEAPANC-MKCTVTTQSA-N 0.000 description 1
- UJMLFPLYZBZHCA-YWCLNGIESA-N CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCC1S(C)(=O)=O Chemical compound CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCC1S(C)(=O)=O UJMLFPLYZBZHCA-YWCLNGIESA-N 0.000 description 1
- YTPZAONXHGDJAH-DDAHENIFSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)CCC4(C(OC(C)C)=O)C(OC(C)C)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)CCC4(C(OC(C)C)=O)C(OC(C)C)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O YTPZAONXHGDJAH-DDAHENIFSA-N 0.000 description 1
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- BICSCTZIBHHACN-UHFFFAOYSA-N CC1(OC2)OC2COC1=O Chemical compound CC1(OC2)OC2COC1=O BICSCTZIBHHACN-UHFFFAOYSA-N 0.000 description 1
- MCYIDKXGIRRGFT-UHFFFAOYSA-N CC1(OC2)OCC2OC1=O Chemical compound CC1(OC2)OCC2OC1=O MCYIDKXGIRRGFT-UHFFFAOYSA-N 0.000 description 1
- DEVLWHGFQZESFA-UHFFFAOYSA-N CCOC(C(C)(OC1)OCC1=O)=O Chemical compound CCOC(C(C)(OC1)OCC1=O)=O DEVLWHGFQZESFA-UHFFFAOYSA-N 0.000 description 1
- LQBPEOASDDDEIO-RPVKVZRISA-N CCOC(C(CC1)(CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)C(OCC)=O)=O Chemical compound CCOC(C(CC1)(CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)C(OCC)=O)=O LQBPEOASDDDEIO-RPVKVZRISA-N 0.000 description 1
- YSSYHHXCWCWCSI-UARHQHRTSA-N CCOC(C(CC1)=C(C)C=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21N)=O Chemical compound CCOC(C(CC1)=C(C)C=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21N)=O YSSYHHXCWCWCSI-UARHQHRTSA-N 0.000 description 1
- DQEUDNFRGHTQAK-HLNNRBTISA-N CCOC(CC(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@@]1(C)[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCC1S(C)(=O)=O)=O Chemical compound CCOC(CC(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@@]1(C)[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCC1S(C)(=O)=O)=O DQEUDNFRGHTQAK-HLNNRBTISA-N 0.000 description 1
- QIAHVZXOVXLJRI-UHFFFAOYSA-N CCOC(CC1CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O Chemical compound CCOC(CC1CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O QIAHVZXOVXLJRI-UHFFFAOYSA-N 0.000 description 1
- FGDURAPNHHCIEV-AWEZNQCLSA-N CCOC([C@@]1(C)OC=C(B2OC(C)(C)C(C)(C)O2)CO1)=O Chemical compound CCOC([C@@]1(C)OC=C(B2OC(C)(C)C(C)(C)O2)CO1)=O FGDURAPNHHCIEV-AWEZNQCLSA-N 0.000 description 1
- BQJIDJNXWCNGOW-WRXNHJIOSA-N CCOC([C@](C)(OC1)OC[C@H]1O)=O Chemical compound CCOC([C@](C)(OC1)OC[C@H]1O)=O BQJIDJNXWCNGOW-WRXNHJIOSA-N 0.000 description 1
- QRNMZLPPWURXQZ-VIFPVBQESA-N CC[O](C)C([C@](C)(OC1)OC=C1OS(C(F)(F)F)(=O)=O)=O Chemical compound CC[O](C)C([C@](C)(OC1)OC=C1OS(C(F)(F)F)(=O)=O)=O QRNMZLPPWURXQZ-VIFPVBQESA-N 0.000 description 1
- OMAUZVLEKOXTTR-UHFFFAOYSA-N CS(C1CCN(CCN)CC1)(=O)=O Chemical compound CS(C1CCN(CCN)CC1)(=O)=O OMAUZVLEKOXTTR-UHFFFAOYSA-N 0.000 description 1
- KWGFISNERABFPJ-UHFFFAOYSA-N O=S1(CCN(CCCl)CC1)=O Chemical compound O=S1(CCN(CCCl)CC1)=O KWGFISNERABFPJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
-
- 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261599040P | 2012-02-15 | 2012-02-15 | |
| US61/599,040 | 2012-02-15 | ||
| US13/760,726 US8906889B2 (en) | 2012-02-15 | 2013-02-06 | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US13/760,726 | 2013-02-06 | ||
| PCT/US2013/025897 WO2013123019A1 (en) | 2012-02-15 | 2013-02-13 | C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140123584A true KR20140123584A (ko) | 2014-10-22 |
Family
ID=48946098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147025339A Ceased KR20140123584A (ko) | 2012-02-15 | 2013-02-13 | Hiv 성숙 억제 활성을 갖는 c-3 시클로알케닐 트리테르페노이드 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8906889B2 (enExample) |
| EP (1) | EP2814834B1 (enExample) |
| JP (1) | JP6155285B2 (enExample) |
| KR (1) | KR20140123584A (enExample) |
| CN (2) | CN106046106A (enExample) |
| AR (1) | AR089996A1 (enExample) |
| AU (1) | AU2013221725B2 (enExample) |
| BR (1) | BR112014019672A8 (enExample) |
| CA (1) | CA2864656A1 (enExample) |
| CL (1) | CL2014002141A1 (enExample) |
| CO (1) | CO7061077A2 (enExample) |
| EA (1) | EA024361B1 (enExample) |
| ES (1) | ES2656984T3 (enExample) |
| HK (1) | HK1204608A1 (enExample) |
| IL (1) | IL234077A (enExample) |
| MX (1) | MX2014009235A (enExample) |
| MY (1) | MY166793A (enExample) |
| NZ (1) | NZ631408A (enExample) |
| PE (1) | PE20142315A1 (enExample) |
| PH (1) | PH12014501816A1 (enExample) |
| PT (1) | PT2814834T (enExample) |
| SG (1) | SG11201404748XA (enExample) |
| TW (1) | TW201336863A (enExample) |
| UY (1) | UY34627A (enExample) |
| WO (1) | WO2013123019A1 (enExample) |
| ZA (1) | ZA201406724B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180105229A (ko) * | 2016-02-04 | 2018-09-27 | 비브 헬스케어 유케이 (넘버5) 리미티드 | Hiv-1 억제제로서의 c-3 및 c-17 변형된 트리테르페노이드 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| JP6186010B2 (ja) | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| UY36070A (es) * | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| EP3218387A1 (en) * | 2014-11-14 | 2017-09-20 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| US9914747B2 (en) | 2014-11-14 | 2018-03-13 | VIIV Healthcare UK (No.5) Limited | Extended betulinic acid analogs |
| CN107250152A (zh) | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | C17‑芳基取代的桦木酸类似物 |
| KR20170135970A (ko) * | 2015-04-14 | 2017-12-08 | 비브 헬스케어 유케이 (넘버4) 리미티드 | Hiv 성숙화 억제제를 생산하는 방법 |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| KR20180028534A (ko) | 2015-07-28 | 2018-03-16 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 감염을 예방하거나 치료하기 위한 베투인 유도체 |
| WO2017051355A1 (en) | 2015-09-24 | 2017-03-30 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| CA3011616A1 (en) * | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| CN106905264B (zh) * | 2017-04-12 | 2019-06-07 | 连云港杰瑞药业有限公司 | 一种合成阿扎拉韦中间体的方法 |
| WO2019055280A1 (en) | 2017-09-13 | 2019-03-21 | Emmyon, Inc. | DIETHANOLAMINE SALTS AND URSOLIC ACID MORPHOLIN |
| JP7436385B2 (ja) | 2018-04-24 | 2024-02-21 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | Ｈｉｖ成熟阻害活性を有する化合物 |
| CN109705189B (zh) * | 2018-12-29 | 2020-06-05 | 中国医学科学院药用植物研究所 | 具有式i所示结构的三萜衍生物及其制备方法和应用 |
| HRP20231582T1 (hr) | 2019-02-11 | 2024-03-15 | Hetero Labs Limited | Novi derivati triterpena kao inhibitori hiv-a |
| WO2020229398A1 (de) | 2019-05-14 | 2020-11-19 | Bayer Aktiengesellschaft | (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| CA2560266A1 (en) | 2004-03-17 | 2005-09-29 | Panacos Pharmaceuticals, Inc. | Pharmaceutical salts of 3-o-(3',3'-dimethylsuccinyl) betulinic acid |
| 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 |
| US20110144069A1 (en) | 2006-10-16 | 2011-06-16 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| US20090062243A1 (en) | 2007-08-03 | 2009-03-05 | Advanced Life Sciences, Inc. | Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof |
| EP2250185A4 (en) * | 2008-01-03 | 2011-11-16 | Virochem Pharma Inc | NEW LUPANDERIVATE |
| CA2714049A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| US8551984B2 (en) | 2009-12-17 | 2013-10-08 | Merck Sharp & Dohme Corp. | Aminopyrimidines as SYK inhibitors |
| CN103038245B (zh) * | 2010-06-04 | 2015-03-25 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180105229A (ko) * | 2016-02-04 | 2018-09-27 | 비브 헬스케어 유케이 (넘버5) 리미티드 | Hiv-1 억제제로서의 c-3 및 c-17 변형된 트리테르페노이드 |
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