KR20170045308A - 인간 면역결핍 바이러스 복제의 억제제로서 이미다조[1,2-a]피리딘 유도체 - Google Patents
인간 면역결핍 바이러스 복제의 억제제로서 이미다조[1,2-a]피리딘 유도체 Download PDFInfo
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- KR20170045308A KR20170045308A KR1020177008130A KR20177008130A KR20170045308A KR 20170045308 A KR20170045308 A KR 20170045308A KR 1020177008130 A KR1020177008130 A KR 1020177008130A KR 20177008130 A KR20177008130 A KR 20177008130A KR 20170045308 A KR20170045308 A KR 20170045308A
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- Prior art keywords
- alkyl
- hiv
- mmol
- phenyl
- haloalkyl
- Prior art date
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- 230000005764 inhibitory process Effects 0.000 description 1
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229940111682 isentress Drugs 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229960004525 lopinavir Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- KHBXQEWQBGGSLL-UHFFFAOYSA-N methyl 2-[2-(3-bromophenyl)-5-chloro-7-methylimidazo[1,2-a]pyridin-6-yl]-2-oxoacetate Chemical compound BrC=1C=C(C=CC1)C=1N=C2N(C(=C(C(=C2)C)C(C(=O)OC)=O)Cl)C1 KHBXQEWQBGGSLL-UHFFFAOYSA-N 0.000 description 1
- 229960001238 methylnicotinate Drugs 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 108700004028 nef Genes Proteins 0.000 description 1
- 101150023385 nef gene Proteins 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960002814 rilpivirine Drugs 0.000 description 1
- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- STKQJGNQQYWQEE-UHFFFAOYSA-N tert-butyl 2,6-dichloro-4-methylpyridine-3-carboxylate Chemical compound Cc1cc(Cl)nc(Cl)c1C(=O)OC(C)(C)C STKQJGNQQYWQEE-UHFFFAOYSA-N 0.000 description 1
- ODNICMBXRCONSC-UHFFFAOYSA-N tert-butyl 2-(3-bromophenyl)-5-chloro-7-methylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound BrC=1C=C(C=CC1)C=1N=C2N(C(=C(C(=C2)C)C(=O)OC(C)(C)C)Cl)C1 ODNICMBXRCONSC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462042300P | 2014-08-27 | 2014-08-27 | |
| US62/042,300 | 2014-08-27 | ||
| PCT/US2015/046648 WO2016033009A1 (en) | 2014-08-27 | 2015-08-25 | Imidazo[1,2-a]pyridine derivatives for use as inhibitors of human immunodeficiency virus replication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20170045308A true KR20170045308A (ko) | 2017-04-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177008130A Withdrawn KR20170045308A (ko) | 2014-08-27 | 2015-08-25 | 인간 면역결핍 바이러스 복제의 억제제로서 이미다조[1,2-a]피리딘 유도체 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10065953B2 (enExample) |
| EP (1) | EP3186254B1 (enExample) |
| JP (1) | JP2017526748A (enExample) |
| KR (1) | KR20170045308A (enExample) |
| CN (1) | CN107001357A (enExample) |
| AU (1) | AU2015306779B2 (enExample) |
| BR (1) | BR112017003663A2 (enExample) |
| CA (1) | CA2958591A1 (enExample) |
| CL (1) | CL2017000428A1 (enExample) |
| IL (1) | IL250561A0 (enExample) |
| RU (1) | RU2017107715A (enExample) |
| WO (1) | WO2016033009A1 (enExample) |
| ZA (1) | ZA201701214B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する３環性複素環誘導体 |
| CA2987384A1 (en) | 2015-05-29 | 2016-12-08 | Shionogi & Co., Ltd. | Nitrogen-containing tricyclic derivative having hiv replication inhibitory activity |
| CN109232562A (zh) * | 2018-10-24 | 2019-01-18 | 康化（上海）新药研发有限公司 | 一种7-氮杂吲哚-5-氯-6-羧酸的合成方法 |
| PE20211781A1 (es) * | 2018-10-24 | 2021-09-08 | Viiv Healthcare Uk No 5 Ltd | Inhibidores de la replicacion del virus de la inmunodeficiencia humana |
| WO2020197991A1 (en) | 2019-03-22 | 2020-10-01 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use |
| IL295677A (en) | 2020-02-24 | 2022-10-01 | Gilead Sciences Inc | Tetracyclic compounds for treating hiv infection |
| US12421235B2 (en) | 2020-09-30 | 2025-09-23 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| PT4196479T (pt) | 2021-01-19 | 2024-01-03 | Gilead Sciences Inc | Compostos de piridotriazinas substituídos e suas utilizações |
| TWI856796B (zh) | 2022-04-06 | 2024-09-21 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8338441B2 (en) * | 2009-05-15 | 2012-12-25 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
| US8633200B2 (en) * | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| WO2012145728A1 (en) * | 2011-04-21 | 2012-10-26 | Gilead Sciences, Inc. | Benzothiazole compounds and their pharmaceutical use |
| US9034882B2 (en) | 2012-03-05 | 2015-05-19 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP3070081B1 (en) * | 2012-04-20 | 2018-02-28 | Gilead Sciences, Inc. | Benzothiazol-6-yl acetic acid derivatives and their use for treating an hiv infection |
| ES2623777T3 (es) * | 2013-03-13 | 2017-07-12 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
-
2015
- 2015-08-25 CN CN201580058209.6A patent/CN107001357A/zh active Pending
- 2015-08-25 CA CA2958591A patent/CA2958591A1/en not_active Abandoned
- 2015-08-25 KR KR1020177008130A patent/KR20170045308A/ko not_active Withdrawn
- 2015-08-25 EP EP15760003.2A patent/EP3186254B1/en active Active
- 2015-08-25 WO PCT/US2015/046648 patent/WO2016033009A1/en not_active Ceased
- 2015-08-25 RU RU2017107715A patent/RU2017107715A/ru not_active Application Discontinuation
- 2015-08-25 AU AU2015306779A patent/AU2015306779B2/en not_active Ceased
- 2015-08-25 BR BR112017003663A patent/BR112017003663A2/pt not_active IP Right Cessation
- 2015-08-25 US US15/505,955 patent/US10065953B2/en not_active Expired - Fee Related
- 2015-08-25 JP JP2017530959A patent/JP2017526748A/ja active Pending
-
2017
- 2017-02-12 IL IL250561A patent/IL250561A0/en unknown
- 2017-02-17 ZA ZA2017/01214A patent/ZA201701214B/en unknown
- 2017-02-22 CL CL2017000428A patent/CL2017000428A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016033009A1 (en) | 2016-03-03 |
| JP2017526748A (ja) | 2017-09-14 |
| RU2017107715A3 (enExample) | 2019-03-04 |
| US20180222901A1 (en) | 2018-08-09 |
| EP3186254A1 (en) | 2017-07-05 |
| AU2015306779A1 (en) | 2017-03-16 |
| CL2017000428A1 (es) | 2017-08-18 |
| IL250561A0 (en) | 2017-03-30 |
| AU2015306779B2 (en) | 2017-11-02 |
| CA2958591A1 (en) | 2016-03-03 |
| EP3186254B1 (en) | 2019-03-06 |
| US10065953B2 (en) | 2018-09-04 |
| BR112017003663A2 (pt) | 2017-11-28 |
| CN107001357A (zh) | 2017-08-01 |
| RU2017107715A (ru) | 2018-09-27 |
| ZA201701214B (en) | 2019-07-31 |
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Patent event date: 20170324 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination |