CN113646319A - C11-环取代的13元大环内酯及其用途 - Google Patents
C11-环取代的13元大环内酯及其用途 Download PDFInfo
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- CN113646319A CN113646319A CN201980087585.6A CN201980087585A CN113646319A CN 113646319 A CN113646319 A CN 113646319A CN 201980087585 A CN201980087585 A CN 201980087585A CN 113646319 A CN113646319 A CN 113646319A
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- optionally substituted
- alkyl
- compound
- pharmaceutically acceptable
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- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 66
- 229940041033 macrolides Drugs 0.000 title abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 216
- 208000035473 Communicable disease Diseases 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 576
- -1 heteroalkenyl Chemical group 0.000 claims description 315
- 229910052739 hydrogen Inorganic materials 0.000 claims description 206
- 125000005842 heteroatom Chemical group 0.000 claims description 169
- 150000003839 salts Chemical class 0.000 claims description 151
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 110
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- 229910052717 sulfur Inorganic materials 0.000 claims description 88
- 229910052760 oxygen Inorganic materials 0.000 claims description 87
- 229920006395 saturated elastomer Polymers 0.000 claims description 77
- 125000004429 atom Chemical group 0.000 claims description 74
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 50
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- 150000003254 radicals Chemical class 0.000 claims description 47
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 41
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 30
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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- 208000030852 Parasitic disease Diseases 0.000 claims description 5
- 208000032536 Pseudomonas Infections Diseases 0.000 claims description 5
- 229910005965 SO 2 Inorganic materials 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 208000034950 Acinetobacter Infections Diseases 0.000 claims description 4
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- 125000005275 alkylenearyl group Chemical group 0.000 claims description 4
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
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- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 175
- 150000004675 formic acid derivatives Chemical class 0.000 description 161
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 141
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 109
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- 125000004432 carbon atom Chemical group C* 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 86
- 239000011541 reaction mixture Substances 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 49
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 37
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 34
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 21
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
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- 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
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- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
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| US201862769413P | 2018-11-19 | 2018-11-19 | |
| US62/769,413 | 2018-11-19 | ||
| PCT/US2019/062045 WO2020106636A1 (en) | 2018-11-19 | 2019-11-18 | C11-cyclic substituted 13-membered macrolides and uses thereof |
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| CN113646319A true CN113646319A (zh) | 2021-11-12 |
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| Country | Link |
|---|---|
| US (1) | US20220177508A1 (https=) |
| EP (1) | EP3883945A1 (https=) |
| JP (1) | JP2022507795A (https=) |
| KR (1) | KR20210123288A (https=) |
| CN (1) | CN113646319A (https=) |
| AU (2) | AU2019385383B2 (https=) |
| BR (1) | BR112021009607A2 (https=) |
| CA (1) | CA3120235A1 (https=) |
| IL (2) | IL310280A (https=) |
| MX (1) | MX2021005421A (https=) |
| SG (1) | SG11202105228SA (https=) |
| WO (1) | WO2020106636A1 (https=) |
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| TW202313065A (zh) * | 2021-05-28 | 2023-04-01 | 美商季卡尼醫療公司 | 用於治療遺傳疾病之化合物 |
| WO2023235380A1 (en) * | 2022-06-01 | 2023-12-07 | Zikani Therapeutics, Inc. | Macrolides for treating genetic diseases |
| WO2023250513A1 (en) * | 2022-06-24 | 2023-12-28 | Zikani Therapeutics, Inc. | 13-membered macrolide compounds for treating diseases mediated by abnormal protein translation |
| KR20250048331A (ko) * | 2022-08-11 | 2025-04-08 | 지카니 테라퓨틱스, 인크. | 치료용 아자케톨라이드 제조용 합성 공정 및 중간체 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329345B1 (en) * | 1998-11-20 | 2001-12-11 | Pfizer Inc | 13-membered azalides and their use as antibiotic agents |
| WO2004108744A2 (en) * | 2003-05-19 | 2004-12-16 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| US20090281292A1 (en) * | 2006-02-07 | 2009-11-12 | Tomohiro Sugimoto | 10a-Azalide Compound |
| CN106998685A (zh) * | 2014-10-08 | 2017-08-01 | 哈佛大学的校长及成员们 | 14‑元酮内酯及其制备和使用方法 |
| CN107530365A (zh) * | 2015-03-25 | 2018-01-02 | 哈佛大学的校长及成员们 | 具有修饰的脱氧糖胺糖的大环内酯及其用途 |
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|---|---|---|---|---|
| BRPI0017013B1 (pt) * | 2000-01-27 | 2015-07-14 | Zoetis P Llc | Composição de antibiótico azalídeo e método para sua obtenção |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| US20130102551A1 (en) * | 2010-07-01 | 2013-04-25 | Andreas Hotte | Antibiotic compositions |
| JP6437523B2 (ja) * | 2013-04-04 | 2018-12-12 | プレジデント アンド フェローズ オブ ハーバード カレッジ | マクロライドならびにそれらの調製および使用の方法 |
-
2019
- 2019-11-18 MX MX2021005421A patent/MX2021005421A/es unknown
- 2019-11-18 IL IL310280A patent/IL310280A/en unknown
- 2019-11-18 WO PCT/US2019/062045 patent/WO2020106636A1/en not_active Ceased
- 2019-11-18 AU AU2019385383A patent/AU2019385383B2/en active Active
- 2019-11-18 IL IL283185A patent/IL283185B2/en unknown
- 2019-11-18 US US17/294,918 patent/US20220177508A1/en not_active Abandoned
- 2019-11-18 SG SG11202105228SA patent/SG11202105228SA/en unknown
- 2019-11-18 BR BR112021009607-8A patent/BR112021009607A2/pt not_active IP Right Cessation
- 2019-11-18 JP JP2021527866A patent/JP2022507795A/ja active Pending
- 2019-11-18 KR KR1020217018877A patent/KR20210123288A/ko not_active Ceased
- 2019-11-18 CA CA3120235A patent/CA3120235A1/en active Pending
- 2019-11-18 CN CN201980087585.6A patent/CN113646319A/zh active Pending
- 2019-11-18 EP EP19824030.1A patent/EP3883945A1/en not_active Withdrawn
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2023
- 2023-09-13 AU AU2023229518A patent/AU2023229518A1/en not_active Abandoned
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|---|---|
| BR112021009607A2 (pt) | 2021-08-10 |
| IL283185B2 (en) | 2024-06-01 |
| IL310280A (en) | 2024-03-01 |
| MX2021005421A (es) | 2021-09-21 |
| IL283185B1 (en) | 2024-02-01 |
| EP3883945A1 (en) | 2021-09-29 |
| SG11202105228SA (en) | 2021-06-29 |
| US20220177508A1 (en) | 2022-06-09 |
| WO2020106636A1 (en) | 2020-05-28 |
| JP2022507795A (ja) | 2022-01-18 |
| AU2019385383A1 (en) | 2021-07-01 |
| AU2019385383B2 (en) | 2023-06-15 |
| KR20210123288A (ko) | 2021-10-13 |
| IL283185A (en) | 2021-06-30 |
| AU2023229518A1 (en) | 2023-09-28 |
| CA3120235A1 (en) | 2020-05-28 |
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