JP2005529079A - 細胞増殖性疾患を処置する化合物および方法 - Google Patents
細胞増殖性疾患を処置する化合物および方法 Download PDFInfo
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- JP2005529079A JP2005529079A JP2003572976A JP2003572976A JP2005529079A JP 2005529079 A JP2005529079 A JP 2005529079A JP 2003572976 A JP2003572976 A JP 2003572976A JP 2003572976 A JP2003572976 A JP 2003572976A JP 2005529079 A JP2005529079 A JP 2005529079A
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- pyran
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- pentyloxy
- tetrahydro
- indol
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- 238000000034 method Methods 0.000 title abstract description 55
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- -1 polycyclic hydrocarbon Chemical class 0.000 claims description 141
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 94
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 239000000460 chlorine Substances 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
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- 125000001424 substituent group Chemical group 0.000 claims description 13
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- 229910052794 bromium Inorganic materials 0.000 claims description 10
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
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- 239000000546 pharmaceutical excipient Substances 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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- KVNLVXHNZGHFKY-RUDMXATFSA-N 5-[5-(3,4-dichloro-2-propylphenoxy)pentoxy]-4-oxo-6-[(e)-prop-1-enyl]pyran-2-carboxylic acid Chemical compound C1=CC(Cl)=C(Cl)C(CCC)=C1OCCCCCOC1=C(\C=C\C)OC(C(O)=O)=CC1=O KVNLVXHNZGHFKY-RUDMXATFSA-N 0.000 claims description 4
- FHWFEEJJISOSEQ-QHHAFSJGSA-N 5-[5-(3,4-dichlorophenoxy)pentoxy]-4-oxo-6-[(e)-prop-1-enyl]pyran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C(OCCCCCOC=2C=C(Cl)C(Cl)=CC=2)=C1/C=C/C FHWFEEJJISOSEQ-QHHAFSJGSA-N 0.000 claims description 4
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- WPFZBDPDUYZDJV-UHFFFAOYSA-N 2-(hydroxymethyl)-5-(5-phenoxypentoxy)pyran-4-one Chemical compound O1C(CO)=CC(=O)C(OCCCCCOC=2C=CC=CC=2)=C1 WPFZBDPDUYZDJV-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
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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 3
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- NDYUXUXEQPEYGN-UHFFFAOYSA-N 5-(5-indol-1-ylhexoxy)-2-(oxan-2-yloxymethyl)pyran-4-one Chemical compound C1=CC2=CC=CC=C2N1C(C)CCCCOC(C(C=1)=O)=COC=1COC1CCCCO1 NDYUXUXEQPEYGN-UHFFFAOYSA-N 0.000 claims description 3
- SYLFNJPOIVEHDD-UHFFFAOYSA-N 5-(5-indol-1-ylpentoxy)-2-(oxan-2-yloxymethyl)pyran-4-one Chemical compound O1C=C(OCCCCCN2C3=CC=CC=C3C=C2)C(=O)C=C1COC1CCCCO1 SYLFNJPOIVEHDD-UHFFFAOYSA-N 0.000 claims description 3
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- HGWNLSFHGVOKLU-UHFFFAOYSA-N [5-(5-indol-1-ylpentoxy)-4-oxopyran-2-yl]methyl n-cyclohexylcarbamate Chemical compound C=1C(=O)C(OCCCCCN2C3=CC=CC=C3C=C2)=COC=1COC(=O)NC1CCCCC1 HGWNLSFHGVOKLU-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
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Images
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)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| 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 |
| PCT/IB2003/001050 WO2003074508A1 (en) | 2002-03-01 | 2003-02-28 | Compounds and methods of treating cell proliferative diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529079A true JP2005529079A (ja) | 2005-09-29 |
| JP2005529079A5 JP2005529079A5 (enExample) | 2006-04-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2003572976A Pending JP2005529079A (ja) | 2002-03-01 | 2003-02-28 | 細胞増殖性疾患を処置する化合物および方法 |
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| 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006519221A (ja) * | 2003-02-28 | 2006-08-24 | エグゾニ・テラピューティック・ソシエテ・アノニム | 化合物並びに細胞増殖性疾患、網膜症及び関節炎を処置する方法 |
| JP2019524797A (ja) * | 2016-08-23 | 2019-09-05 | ニューリム・ファーマシューティカルズ・リミテッドNeurim Pharmaceuticals Ltd. | 掻痒症および/または痒みの治療方法 |
Families Citing this family (4)
| 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 |
| WO2005110399A2 (en) * | 2004-04-29 | 2005-11-24 | The Regents Of The University Of California | Zinc-binding groups for metalloprotein inhibitors |
| EP1755586A2 (en) * | 2004-04-29 | 2007-02-28 | The Regents of the University of California | Hydroxypyridinone, hydroxypyridinethione, pyrone, and thiopyrone 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4644071A (en) * | 1984-07-11 | 1987-02-17 | G. D. Searle & Co. | Aralkoxy and aryloxyalkoxy kojic acid derivatives |
| 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 |
| 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 US US10/502,625 patent/US20050054629A1/en not_active Abandoned
- 2003-02-28 EP EP03743474A patent/EP1480966A1/en not_active Withdrawn
- 2003-02-28 WO PCT/IB2003/001050 patent/WO2003074508A1/en not_active Ceased
- 2003-02-28 AU AU2003209924A patent/AU2003209924A1/en not_active Abandoned
- 2003-02-28 JP JP2003572976A patent/JP2005529079A/ja active Pending
- 2003-02-28 CA CA002477003A patent/CA2477003A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006519221A (ja) * | 2003-02-28 | 2006-08-24 | エグゾニ・テラピューティック・ソシエテ・アノニム | 化合物並びに細胞増殖性疾患、網膜症及び関節炎を処置する方法 |
| JP2019524797A (ja) * | 2016-08-23 | 2019-09-05 | ニューリム・ファーマシューティカルズ・リミテッドNeurim Pharmaceuticals Ltd. | 掻痒症および/または痒みの治療方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050054629A1 (en) | 2005-03-10 |
| AU2003209924A1 (en) | 2003-09-16 |
| CA2477003A1 (en) | 2003-09-12 |
| US6552073B1 (en) | 2003-04-22 |
| WO2003074508A1 (en) | 2003-09-12 |
| WO2003074508B1 (en) | 2003-11-27 |
| EP1480966A1 (en) | 2004-12-01 |
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