CA2477003A1 - Compounds and methods of treating cell proliferative diseases - Google Patents
Compounds and methods of treating cell proliferative diseases Download PDFInfo
- Publication number
- CA2477003A1 CA2477003A1 CA002477003A CA2477003A CA2477003A1 CA 2477003 A1 CA2477003 A1 CA 2477003A1 CA 002477003 A CA002477003 A CA 002477003A CA 2477003 A CA2477003 A CA 2477003A CA 2477003 A1 CA2477003 A1 CA 2477003A1
- Authority
- CA
- Canada
- Prior art keywords
- pyran
- group
- eht
- pentyloxy
- tetrahydro
- 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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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title abstract description 92
- 230000002062 proliferating effect Effects 0.000 title description 5
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
- 201000011510 cancer Diseases 0.000 claims abstract description 25
- 230000004663 cell proliferation Effects 0.000 claims abstract description 13
- 230000002159 abnormal effect Effects 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- -1 propen-1-yl group Chemical group 0.000 claims description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000005647 linker group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
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- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 20
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- 239000001301 oxygen Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
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- 125000001424 substituent group Chemical group 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
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- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- VOLMSPGWNYJHQQ-UHFFFAOYSA-N Pyranone Natural products CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 4
- ATLXOZZZXNJWFG-UHFFFAOYSA-N 2-(hydroxymethyl)-5-(4-indol-1-ylbutoxy)pyran-4-one Chemical compound O1C(CO)=CC(=O)C(OCCCCN2C3=CC=CC=C3C=C2)=C1 ATLXOZZZXNJWFG-UHFFFAOYSA-N 0.000 claims description 3
- MBKYUHQVYXHKDQ-UHFFFAOYSA-N 2-(hydroxymethyl)-5-(5-phenylsulfanylpentoxy)pyran-4-one Chemical compound O1C(CO)=CC(=O)C(OCCCCCSC=2C=CC=CC=2)=C1 MBKYUHQVYXHKDQ-UHFFFAOYSA-N 0.000 claims description 3
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- GPMGCSJJUBLSPP-UHFFFAOYSA-N [5-(5-indol-1-ylpentoxy)-4-oxopyran-2-yl]methyl 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OCC1=CC(=O)C(OCCCCCN2C3=CC=CC=C3C=C2)=CO1 GPMGCSJJUBLSPP-UHFFFAOYSA-N 0.000 claims description 3
- IKYCCVMWIGMMNE-UHFFFAOYSA-N [5-(5-indol-1-ylpentoxy)-4-oxopyran-2-yl]methyl n-ethylcarbamate Chemical compound O1C(COC(=O)NCC)=CC(=O)C(OCCCCCN2C3=CC=CC=C3C=C2)=C1 IKYCCVMWIGMMNE-UHFFFAOYSA-N 0.000 claims description 3
- DICYANPOGCKGFJ-UHFFFAOYSA-N [5-(5-indol-1-ylpentoxy)-4-oxopyran-2-yl]methyl n-phenylcarbamate Chemical compound C=1C(=O)C(OCCCCCN2C3=CC=CC=C3C=C2)=COC=1COC(=O)NC1=CC=CC=C1 DICYANPOGCKGFJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
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- 238000002360 preparation method Methods 0.000 claims description 3
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- MUKUURPJHRJMOF-UHFFFAOYSA-N 2-(oxan-2-yloxymethyl)-5-(5-pyrrolo[2,3-b]pyridin-1-ylpentoxy)pyran-4-one Chemical compound O1C=C(OCCCCCN2C3=NC=CC=C3C=C2)C(=O)C=C1COC1CCCCO1 MUKUURPJHRJMOF-UHFFFAOYSA-N 0.000 claims description 2
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- QGDINGHTQSXITG-UHFFFAOYSA-N 2-(oxan-2-yloxymethyl)-5-[5-[5-(trifluoromethyl)pyridin-2-yl]oxypentoxy]pyran-4-one Chemical compound N1=CC(C(F)(F)F)=CC=C1OCCCCCOC1=COC(COC2OCCCC2)=CC1=O QGDINGHTQSXITG-UHFFFAOYSA-N 0.000 claims description 2
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- HIUHFPFCMURAGO-QHHAFSJGSA-N 3-[5-[3,5-bis(trifluoromethyl)phenoxy]pentoxy]-6-(hydroxymethyl)-2-[(e)-prop-1-enyl]pyran-4-one Chemical compound O1C(CO)=CC(=O)C(OCCCCCOC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1/C=C/C HIUHFPFCMURAGO-QHHAFSJGSA-N 0.000 claims description 2
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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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/085,141 US6552073B1 (en) | 2002-03-01 | 2002-03-01 | Compounds and methods of treating cell proliferative diseases |
| US10/085,141 | 2002-03-01 | ||
| PCT/IB2003/001050 WO2003074508A1 (en) | 2002-03-01 | 2003-02-28 | Compounds and methods of treating cell proliferative diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2477003A1 true CA2477003A1 (en) | 2003-09-12 |
Family
ID=22189708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002477003A Abandoned CA2477003A1 (en) | 2002-03-01 | 2003-02-28 | Compounds and methods of treating cell proliferative diseases |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6552073B1 (enExample) |
| EP (1) | EP1480966A1 (enExample) |
| JP (1) | JP2005529079A (enExample) |
| AU (1) | AU2003209924A1 (enExample) |
| CA (1) | CA2477003A1 (enExample) |
| WO (1) | WO2003074508A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6552073B1 (en) * | 2002-03-01 | 2003-04-22 | Exonhit Therapeutics Sa | Compounds and methods of treating cell proliferative diseases |
| EP1471063A1 (en) * | 2003-02-28 | 2004-10-27 | Exonhit Therapeutics S.A. | Compounds and methods of treating cell proliferative diseases, retinopathies and arthritis |
| WO2006028523A2 (en) * | 2004-04-29 | 2006-03-16 | THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, SAN DIEGO USDC Technology Transfer Office | Hydroxypyridinone, hydroxypyridinethione, pyrone, and thiopyrone metalloprotein inhibitors |
| WO2005110399A2 (en) | 2004-04-29 | 2005-11-24 | The Regents Of The University Of California | Zinc-binding groups for metalloprotein inhibitors |
| DE102007002260A1 (de) | 2007-01-16 | 2008-07-31 | Sanofi-Aventis | Verwendung von substituierten Pyranonsäurederivaten zur Herstellung von Medikamenten zur Behandlung des Metabolischen Syndroms |
| EP3503884B1 (en) * | 2016-08-23 | 2021-07-21 | Neurim Pharmaceuticals Ltd. | Pharmaceutical composition for use in treating pruritus and/or itch |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705871A (en) * | 1984-07-11 | 1987-11-10 | G. D. Searle & Co. | Aralkoxy and aryloxyalkoxy kojic acid derivatives |
| US4812584A (en) * | 1984-07-11 | 1989-03-14 | G. D. Searle & Co. | Aralkoxy and aryloxyalkoxy kojic acid derivatives |
| US4644071A (en) * | 1984-07-11 | 1987-02-17 | G. D. Searle & Co. | Aralkoxy and aryloxyalkoxy kojic acid derivatives |
| PH22520A (en) * | 1984-11-12 | 1988-10-17 | Yamanouchi Pharma Co Ltd | Heterocyclic compounds having 4-lover alkyl-3-hydroxy-2-lower alkyl phenoxy-lower alkylene-y-group, and process of producing them |
| US6552073B1 (en) * | 2002-03-01 | 2003-04-22 | Exonhit Therapeutics Sa | Compounds and methods of treating cell proliferative diseases |
-
2002
- 2002-03-01 US US10/085,141 patent/US6552073B1/en not_active Expired - Fee Related
-
2003
- 2003-02-28 EP EP03743474A patent/EP1480966A1/en not_active Withdrawn
- 2003-02-28 US US10/502,625 patent/US20050054629A1/en not_active Abandoned
- 2003-02-28 AU AU2003209924A patent/AU2003209924A1/en not_active Abandoned
- 2003-02-28 WO PCT/IB2003/001050 patent/WO2003074508A1/en not_active Ceased
- 2003-02-28 CA CA002477003A patent/CA2477003A1/en not_active Abandoned
- 2003-02-28 JP JP2003572976A patent/JP2005529079A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20050054629A1 (en) | 2005-03-10 |
| JP2005529079A (ja) | 2005-09-29 |
| WO2003074508B1 (en) | 2003-11-27 |
| US6552073B1 (en) | 2003-04-22 |
| WO2003074508A1 (en) | 2003-09-12 |
| EP1480966A1 (en) | 2004-12-01 |
| AU2003209924A1 (en) | 2003-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |