CA2527583C - Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases - Google Patents
Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases Download PDFInfo
- Publication number
- CA2527583C CA2527583C CA2527583A CA2527583A CA2527583C CA 2527583 C CA2527583 C CA 2527583C CA 2527583 A CA2527583 A CA 2527583A CA 2527583 A CA2527583 A CA 2527583A CA 2527583 C CA2527583 C CA 2527583C
- Authority
- CA
- Canada
- Prior art keywords
- nhr14
- alkyl
- nhc
- nr14c
- phenyl
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 63
- 239000000203 mixture Substances 0.000 title claims abstract 11
- 206010028980 Neoplasm Diseases 0.000 title claims abstract 7
- 201000011510 cancer Diseases 0.000 title claims abstract 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 201000010099 disease Diseases 0.000 title 1
- 230000003612 virological effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 101100240520 Caenorhabditis elegans nhr-14 gene Proteins 0.000 claims 299
- 125000000623 heterocyclic group Chemical group 0.000 claims 73
- 125000000217 alkyl group Chemical group 0.000 claims 62
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 59
- 125000001624 naphthyl group Chemical group 0.000 claims 51
- 229910052736 halogen Inorganic materials 0.000 claims 48
- 150000002367 halogens Chemical class 0.000 claims 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 46
- 229910052799 carbon Inorganic materials 0.000 claims 21
- 150000001721 carbon Chemical group 0.000 claims 21
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 239000003960 organic solvent Substances 0.000 claims 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 239000003981 vehicle Substances 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 150000003892 tartrate salts Chemical group 0.000 claims 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 229910052792 caesium Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 102220024746 rs199473444 Human genes 0.000 claims 2
- 229910052701 rubidium Inorganic materials 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- 229910002666 PdCl2 Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical group [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical group Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 210000005170 neoplastic cell Anatomy 0.000 abstract 1
- 230000001613 neoplastic effect Effects 0.000 abstract 1
- 230000010076 replication Effects 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47474103P | 2003-05-30 | 2003-05-30 | |
| US60/474,741 | 2003-05-30 | ||
| PCT/CA2004/000793 WO2004106328A1 (en) | 2003-05-30 | 2004-05-28 | Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2527583A1 CA2527583A1 (en) | 2004-12-09 |
| CA2527583C true CA2527583C (en) | 2013-12-17 |
Family
ID=33490730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2527583A Expired - Fee Related CA2527583C (en) | 2003-05-30 | 2004-05-28 | Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US7425553B2 (OSRAM) |
| EP (1) | EP1644363B1 (OSRAM) |
| JP (1) | JP4980715B2 (OSRAM) |
| KR (1) | KR101168441B1 (OSRAM) |
| CN (1) | CN1832939B (OSRAM) |
| AT (1) | ATE546456T1 (OSRAM) |
| AU (1) | AU2004242928B2 (OSRAM) |
| BR (1) | BRPI0410870A (OSRAM) |
| CA (1) | CA2527583C (OSRAM) |
| CY (1) | CY1113038T1 (OSRAM) |
| DK (1) | DK1644363T3 (OSRAM) |
| ES (1) | ES2382377T3 (OSRAM) |
| HR (1) | HRP20120379T1 (OSRAM) |
| IL (1) | IL172189A (OSRAM) |
| MX (1) | MXPA05012799A (OSRAM) |
| NO (1) | NO333006B1 (OSRAM) |
| NZ (1) | NZ543897A (OSRAM) |
| PL (1) | PL1644363T3 (OSRAM) |
| PT (1) | PT1644363E (OSRAM) |
| RU (1) | RU2360913C2 (OSRAM) |
| SI (1) | SI1644363T1 (OSRAM) |
| WO (1) | WO2004106328A1 (OSRAM) |
| ZA (1) | ZA200509718B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8946445B2 (en) | 2011-10-12 | 2015-02-03 | Nanjing Allgen Pharma Co., Ltd. | Heterocyclic molecules as apoptosis inducers |
Families Citing this family (144)
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|---|---|---|---|---|
| SI1644363T1 (sl) * | 2003-05-30 | 2012-07-31 | Gemin X Pharmaceuticals Canada Inc | Triheterociklične spojine sestavki in postopki za zdravljenje raka |
| US20060035945A1 (en) * | 2003-05-30 | 2006-02-16 | Giorgio Attardo | Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases |
| WO2005112640A2 (en) * | 2004-05-13 | 2005-12-01 | Viropharma Incorporated | Compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| US8420693B2 (en) * | 2004-12-28 | 2013-04-16 | Gemin X Pharmaceuticals Canada Inc. | Dipyrrole compounds, compositions, and methods for treating cancer or viral diseases |
| EP1853255A4 (en) * | 2005-02-22 | 2009-07-08 | Gemin X Pharmaceuticals Canada | METHOD FOR TREATING ARTHRITIS WITH TRIHETEROCYCLIC COMPOUNDS |
| US7994360B2 (en) | 2005-05-16 | 2011-08-09 | Xtl Biopharmaceuticals Ltd. | Benzofuran compounds |
| US20080051400A1 (en) * | 2006-07-06 | 2008-02-28 | Gemin X Biotechnologies Inc. | Methods for treating or preventing anemia or thrombocytopenia using a triheterocyclic compound |
| ATE543808T1 (de) | 2006-12-22 | 2012-02-15 | Schering Corp | 5,6-ring-annelierte indolderivate und ihre verwendung |
| WO2008082488A1 (en) | 2006-12-22 | 2008-07-10 | Schering Corporation | 4, 5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections |
| WO2008082484A1 (en) | 2006-12-22 | 2008-07-10 | Schering Corporation | 4,5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections |
| US9649499B2 (en) * | 2007-03-28 | 2017-05-16 | Medtronic ATS Medical, Inc. | Method for inhibiting platelet interaction with biomaterial surfaces |
| JP5272008B2 (ja) | 2007-08-29 | 2013-08-28 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換インドール誘導体およびその使用の方法 |
| PE20090995A1 (es) | 2007-08-29 | 2009-08-03 | Schering Corp | Derivados indolicos 2,3-sustituidos como inhibidores del virus de la hepatitis c (vhc) |
| ATE541845T1 (de) | 2007-08-29 | 2012-02-15 | Schering Corp | 2,3-substituierte azaindolderivate zur behandlung von virusinfektionen |
| CN101130539B (zh) * | 2007-09-26 | 2012-05-30 | 浙江大学 | 吲哚取代咪唑啉-2-酮类衍生物及其制备方法和用途 |
| US20090098118A1 (en) | 2007-10-15 | 2009-04-16 | Thomas Friess | Combination therapy of a type ii anti-cd20 antibody with an anti-bcl-2 active agent |
| JP5416708B2 (ja) | 2007-11-16 | 2014-02-12 | メルク・シャープ・アンド・ドーム・コーポレーション | ３−アミノスルホニル置換インドール誘導体およびそれらの使用方法 |
| JP5249344B2 (ja) | 2007-11-16 | 2013-07-31 | メルク・シャープ・アンド・ドーム・コーポレーション | ヘテロ環の３位が置換されたインドール誘導体およびその使用 |
| MX2010013630A (es) | 2008-06-13 | 2010-12-21 | Schering Corp | Derivados triciclicos de indol y metodos de uso de los mismos. |
| CN103648491B (zh) * | 2011-04-08 | 2017-07-14 | 法国国家健康医学研究院 | 用于抑制流感病毒复制的方法和药物组合物 |
| WO2014100080A1 (en) * | 2012-12-19 | 2014-06-26 | Glaxosmithkline Llc | Combination |
| CN103044311B (zh) * | 2012-12-26 | 2015-04-22 | 山东大学 | 一种多取代吲哚类化合物及其制备方法和应用 |
| US20160022708A1 (en) * | 2013-03-14 | 2016-01-28 | St. Jude Children's Research Hospital | Methods and compositions for the treatment of glutamine-addicted cancers |
| CA2940666C (en) | 2014-02-28 | 2022-08-23 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| US11331328B2 (en) | 2014-05-05 | 2022-05-17 | Bioventures, Llc | Compositions and methods for inhibiting antiapoptotic Bcl-2 proteins as anti-aging agents |
| AU2015292710A1 (en) | 2014-07-22 | 2017-02-16 | Bioventures, Llc. | Compositions and methods for selectively depleting senescent cells |
| CN106715456B (zh) | 2014-08-12 | 2023-08-29 | 莫纳什大学 | 定向淋巴的前药 |
| SI3215518T1 (sl) | 2014-10-29 | 2021-08-31 | Bicyclerd Limited | Biciklični peptidni ligandi, značilni za MT1-MMP |
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