AU2005323435A1 - Anti-coronavirus compounds - Google Patents
Anti-coronavirus compounds Download PDFInfo
- Publication number
- AU2005323435A1 AU2005323435A1 AU2005323435A AU2005323435A AU2005323435A1 AU 2005323435 A1 AU2005323435 A1 AU 2005323435A1 AU 2005323435 A AU2005323435 A AU 2005323435A AU 2005323435 A AU2005323435 A AU 2005323435A AU 2005323435 A1 AU2005323435 A1 AU 2005323435A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- aryl
- heterocycloalkyl
- independently
- heteroaryl
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims description 115
- 238000000034 method Methods 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 208000015181 infectious disease Diseases 0.000 claims description 27
- 241000711573 Coronaviridae Species 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 241000315672 SARS coronavirus Species 0.000 claims description 23
- 239000004365 Protease Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 108091005804 Peptidases Proteins 0.000 claims description 15
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 15
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 8
- 241000713800 Feline immunodeficiency virus Species 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- 238000012417 linear regression Methods 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
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- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
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- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- UPSFMJHZUCSEHU-JYGUBCOQSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@H](OC=2C=C3OC(=O)C=C(C)C3=CC=2)O[C@@H]1CO UPSFMJHZUCSEHU-JYGUBCOQSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 238000003752 polymerase chain reaction Methods 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
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- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003441 thioacyl group Chemical group 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
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Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56808004P | 2004-05-04 | 2004-05-04 | |
| US60/568,080 | 2004-05-04 | ||
| PCT/US2005/015227 WO2006073456A2 (en) | 2004-05-04 | 2005-05-03 | Anti-coronavirus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005323435A1 true AU2005323435A1 (en) | 2006-07-13 |
Family
ID=36647910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005323435A Abandoned AU2005323435A1 (en) | 2004-05-04 | 2005-05-03 | Anti-coronavirus compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8481571B2 (https=) |
| JP (1) | JP2007536240A (https=) |
| CN (1) | CN1949977B (https=) |
| AU (1) | AU2005323435A1 (https=) |
| NZ (1) | NZ550945A (https=) |
| TW (1) | TWI372048B (https=) |
| WO (1) | WO2006073456A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2782922T (pt) * | 2011-11-25 | 2018-02-05 | The Kitasato Inst | Derivados antibacterianos de tilosina e processos para a sua preparação |
| IN2014MN02539A (https=) * | 2012-06-06 | 2015-07-24 | Unither Virology Llc | |
| WO2017059118A1 (en) * | 2015-09-29 | 2017-04-06 | Duke University | Compositions and methods for identifying and treating dystonia disorders |
| WO2017201052A1 (en) * | 2016-05-16 | 2017-11-23 | Emergent Virology Llc | Methods of treating zika virus infection |
| CN107595906B (zh) * | 2017-11-10 | 2020-10-30 | 中国药科大学 | 常春藤皂苷元及其糖苷在制备抗病毒的药物中的应用 |
| EA202193251A1 (ru) | 2019-06-05 | 2022-03-10 | Эмори Юниверсити | Пептидомиметики для лечения коронавирусной и пикорнавирусной инфекций |
| CN115698035A (zh) * | 2020-04-10 | 2023-02-03 | 共晶制药公司 | 诺如病毒及冠状病毒复制的抑制剂 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5142056A (en) | 1989-05-23 | 1992-08-25 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| JPH0778021B2 (ja) * | 1988-04-13 | 1995-08-23 | 太陽化学株式会社 | 下痢症ウイルス感染阻害剤 |
| US5156973A (en) | 1988-11-23 | 1992-10-20 | Edward Shanbrom | Antiviral blood sampling process and apparatus |
| HUT64738A (en) | 1990-06-01 | 1994-02-28 | Du Pont Merck Pharma | Process for preparing 1,4-diamino-2,3-dihydroxi-butane compounds and pharmaceutical compositions contianing them |
| JPH04297475A (ja) * | 1991-03-26 | 1992-10-21 | Yamanouchi Pharmaceut Co Ltd | 抗ウイルス剤 |
| US6803466B1 (en) | 1997-12-08 | 2004-10-12 | The Scripps Research Institute | HIV/FIV protease inhibitors having a small P3 residue |
-
2005
- 2005-05-03 US US11/121,314 patent/US8481571B2/en not_active Expired - Fee Related
- 2005-05-03 NZ NZ550945A patent/NZ550945A/en not_active IP Right Cessation
- 2005-05-03 CN CN2005800143095A patent/CN1949977B/zh not_active Expired - Fee Related
- 2005-05-03 AU AU2005323435A patent/AU2005323435A1/en not_active Abandoned
- 2005-05-03 JP JP2007511484A patent/JP2007536240A/ja active Pending
- 2005-05-03 WO PCT/US2005/015227 patent/WO2006073456A2/en not_active Ceased
- 2005-05-04 TW TW094114468A patent/TWI372048B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200600084A (en) | 2006-01-01 |
| US8481571B2 (en) | 2013-07-09 |
| CN1949977B (zh) | 2010-09-29 |
| NZ550945A (en) | 2010-04-30 |
| JP2007536240A (ja) | 2007-12-13 |
| TWI372048B (en) | 2012-09-11 |
| US20060160866A1 (en) | 2006-07-20 |
| CN1949977A (zh) | 2007-04-18 |
| WO2006073456A2 (en) | 2006-07-13 |
| WO2006073456A3 (en) | 2006-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |