RU2016151973A - Пиридиноны, замещенные фенилом и трет-бутилуксусной кислотой, обладающие анти-вич эффектами - Google Patents
Пиридиноны, замещенные фенилом и трет-бутилуксусной кислотой, обладающие анти-вич эффектами Download PDFInfo
- Publication number
- RU2016151973A RU2016151973A RU2016151973A RU2016151973A RU2016151973A RU 2016151973 A RU2016151973 A RU 2016151973A RU 2016151973 A RU2016151973 A RU 2016151973A RU 2016151973 A RU2016151973 A RU 2016151973A RU 2016151973 A RU2016151973 A RU 2016151973A
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- Prior art keywords
- phenyl
- paragraphs
- compound according
- compound
- cyclohexyl
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims 8
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical group CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 title 1
- 230000036436 anti-hiv Effects 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 150000005299 pyridinones Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- 208000036142 Viral infection Diseases 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- -1 2 -cyclohexyl Chemical group 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000002651 drug therapy Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 241001430294 unidentified retrovirus Species 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Claims (20)
1. Соединение формулы I:
где:
R1 представляет собой фенил, возможно замещенный 1-4 заместителями, выбранными из C1-3алкила, галогена или -СН2СН2СН2О-, где эта группа связана с соседними атомами углерода на фениле с образованием кольца;
L представляет собой связь, C1-3алкилен, -SO2-, -SO2CH2-, -NHSO2-, -NHSO2CH2-, -С(О)-, -C(O)NH-, -C(O)NHCH2-, -С(O)ОСН2-, -С(O)С(O)-, -СН2С(O)-, С3-7гетероарил или -С3-7гетероарилNН-, где каждый гетероарил содержит от одного до трех гетероатомов, выбранных из S, N и О;
R2 представляет собой Н, циклогексил или фенил, где указанные циклогексил и фенил возможно замещены 1-3 заместителями, выбранными из С1-3алкила и галогена;
R3 представляет собой Н или -NHSO2R4, где R4 представляет собой С1-8алкил, и где указанный алкил может включать циклоалкильные фрагменты.
2. Соединение по п. 1, где R1 представляет собой фенил, возможно замещенный метильной группой.
3. Соединение по п. 1 или 2, где L представляет собой связь, -оксадиазолил-NH-, -C(O)NH- или -C(O)NHCH2-.
4. Соединение по любому из пп. 1-3, где R2 представляет собой Н, циклогексил или фенил, где указанные циклогексил и фенил возможно замещены 1 или 2 метильными группами.
5. Соединение по любому из пп. 1-4, где R3 представляет собой Н, -NHSO2CH3 или -NНSО2СН2циклогексил.
6. Соединение по любому из пп. 1-5, где стереохимическая конфигурация атома углерода, с которым связана трет-бутильная группа, является такой, как изображено ниже:
7. Соединение, представляющее собой фармацевтически приемлемую соль соединения по любому из пп. 1-6.
8. Фармацевтическая композиция, содержащая соединение по любому из пп. 1-7.
9. Способ лечения вирусной инфекции у пациента, опосредованной по меньшей мере частично вирусом из семейства ретровирусов, включающий введение указанному пациенту композиции по п. 8.
10. Способ по п. 9, где указанная вирусная инфекция опосредована вирусом ВИЧ.
11. Соединение по любому из пп. 1-7 для применения в лекарственной терапии.
12. Соединение по любому из пп. 1-7 для применения в лечении вирусной инфекции у человека.
13. Применение соединения по любому из пп. 1-7 в изготовлении лекарственного средства для использования в лечении вирусной инфекции у человека.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462026782P | 2014-07-21 | 2014-07-21 | |
| US62/026,782 | 2014-07-21 | ||
| PCT/IB2015/055385 WO2016012913A1 (en) | 2014-07-21 | 2015-07-16 | Phenyl and tertbutylacetic acid substituted pyridinones having anti-hiv effects |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2016151973A true RU2016151973A (ru) | 2018-08-22 |
| RU2016151973A3 RU2016151973A3 (ru) | 2018-11-09 |
Family
ID=53718072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016151973A RU2016151973A (ru) | 2014-07-21 | 2015-07-16 | Пиридиноны, замещенные фенилом и трет-бутилуксусной кислотой, обладающие анти-вич эффектами |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9802898B2 (ru) |
| EP (1) | EP3172189A1 (ru) |
| JP (1) | JP2017521455A (ru) |
| KR (1) | KR20170032324A (ru) |
| CN (1) | CN106536482A (ru) |
| AR (1) | AR101222A1 (ru) |
| AU (1) | AU2015293578B2 (ru) |
| CA (1) | CA2954724A1 (ru) |
| CL (1) | CL2017000151A1 (ru) |
| IL (1) | IL249560A0 (ru) |
| MA (1) | MA40220A (ru) |
| RU (1) | RU2016151973A (ru) |
| TW (1) | TW201617317A (ru) |
| UY (1) | UY36217A (ru) |
| WO (1) | WO2016012913A1 (ru) |
| ZA (1) | ZA201608598B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019522014A (ja) | 2016-07-25 | 2019-08-08 | ヴィーブ ヘルスケア ユーケー リミテッド | インドリン誘導体 |
| WO2018190350A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
| US10293012B2 (en) | 2017-05-04 | 2019-05-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Methods of using extracts of melissa officinalis against filoviruses |
| WO2018208739A1 (en) * | 2017-05-08 | 2018-11-15 | Thomas Cahill | Pharmaceutical compositions comprising caffeic acid chelates |
| EP3636636B1 (en) | 2017-06-08 | 2022-07-06 | Mitsui Chemicals Agro, Inc. | Pyridone compound and agricultural and horticultural fungicide |
| TWI828725B (zh) | 2018-07-25 | 2024-01-11 | 日商三井化學植保股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1026826C2 (nl) * | 2003-08-13 | 2007-01-04 | Pharmacia Corp | Gesubstitueerde pyridinonen. |
| US7939545B2 (en) * | 2006-05-16 | 2011-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| US8338441B2 (en) * | 2009-05-15 | 2012-12-25 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
| GB0913636D0 (en) * | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| WO2013002357A1 (ja) * | 2011-06-30 | 2013-01-03 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害剤 |
| WO2013043553A1 (en) | 2011-09-22 | 2013-03-28 | Glaxosmithkline Llc | Pyrrolopyridinone compounds and methods for treating hiv |
| EP2877468B1 (en) | 2012-07-12 | 2017-08-23 | ViiV Healthcare UK Limited | Compounds and methods for treating hiv |
-
2015
- 2015-07-16 WO PCT/IB2015/055385 patent/WO2016012913A1/en active Application Filing
- 2015-07-16 EP EP15741363.4A patent/EP3172189A1/en not_active Withdrawn
- 2015-07-16 AU AU2015293578A patent/AU2015293578B2/en not_active Ceased
- 2015-07-16 JP JP2017503126A patent/JP2017521455A/ja not_active Ceased
- 2015-07-16 CA CA2954724A patent/CA2954724A1/en not_active Abandoned
- 2015-07-16 MA MA040220A patent/MA40220A/fr unknown
- 2015-07-16 UY UY0001036217A patent/UY36217A/es not_active Application Discontinuation
- 2015-07-16 KR KR1020177002216A patent/KR20170032324A/ko unknown
- 2015-07-16 CN CN201580039443.4A patent/CN106536482A/zh active Pending
- 2015-07-16 US US15/326,070 patent/US9802898B2/en not_active Expired - Fee Related
- 2015-07-16 AR ARP150102265A patent/AR101222A1/es unknown
- 2015-07-16 TW TW104123125A patent/TW201617317A/zh unknown
- 2015-07-16 RU RU2016151973A patent/RU2016151973A/ru not_active Application Discontinuation
-
2016
- 2016-12-13 ZA ZA2016/08598A patent/ZA201608598B/en unknown
- 2016-12-14 IL IL249560A patent/IL249560A0/en unknown
-
2017
- 2017-01-19 CL CL2017000151A patent/CL2017000151A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015293578B2 (en) | 2017-10-05 |
| US9802898B2 (en) | 2017-10-31 |
| RU2016151973A3 (ru) | 2018-11-09 |
| AR101222A1 (es) | 2016-11-30 |
| US20170217890A1 (en) | 2017-08-03 |
| MA40220A (fr) | 2017-05-31 |
| IL249560A0 (en) | 2017-02-28 |
| CN106536482A (zh) | 2017-03-22 |
| EP3172189A1 (en) | 2017-05-31 |
| KR20170032324A (ko) | 2017-03-22 |
| AU2015293578A1 (en) | 2017-01-19 |
| WO2016012913A1 (en) | 2016-01-28 |
| CL2017000151A1 (es) | 2017-07-28 |
| UY36217A (es) | 2016-02-29 |
| TW201617317A (zh) | 2016-05-16 |
| ZA201608598B (en) | 2019-06-26 |
| CA2954724A1 (en) | 2016-01-28 |
| JP2017521455A (ja) | 2017-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20190226 |