KR20080040665A - 항종양 제제로 유용한 신남산, 페닐프로피올산 및페닐프로판산 유도체 - Google Patents
항종양 제제로 유용한 신남산, 페닐프로피올산 및페닐프로판산 유도체 Download PDFInfo
- Publication number
- KR20080040665A KR20080040665A KR1020087000035A KR20087000035A KR20080040665A KR 20080040665 A KR20080040665 A KR 20080040665A KR 1020087000035 A KR1020087000035 A KR 1020087000035A KR 20087000035 A KR20087000035 A KR 20087000035A KR 20080040665 A KR20080040665 A KR 20080040665A
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- South Korea
- Prior art keywords
- phenyl
- aryl
- methyl
- compound
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- 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.)
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- 239000002246 antineoplastic agent Substances 0.000 title claims description 18
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 title abstract description 4
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title description 3
- 229930016911 cinnamic acid Natural products 0.000 title description 3
- 235000013985 cinnamic acid Nutrition 0.000 title description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
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- -1 nitro halogen Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 31
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- LBOUHDMYVURTMA-AATRIKPKSA-N (e)-3-(4-formylphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(C=O)C=C1 LBOUHDMYVURTMA-AATRIKPKSA-N 0.000 claims description 11
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 11
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
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- IHHUORPGTIDVFD-VRDSVTSBSA-N methyl 4-[[[4-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methylideneamino]oxymethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CON=CC1=CC=C(\C=C\C(=O)NO)C=C1 IHHUORPGTIDVFD-VRDSVTSBSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- KKMCPDKFGBXVNL-VALNIMGKSA-N (e)-n-hydroxy-3-[4-(2-morpholin-4-ylethoxyiminomethyl)phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)NO)=CC=C1C=NOCCN1CCOCC1 KKMCPDKFGBXVNL-VALNIMGKSA-N 0.000 claims description 5
- NRCCSDVEUWXOMG-UHFFFAOYSA-N 3-(4-formylphenyl)propanoic acid Chemical class OC(=O)CCC1=CC=C(C=O)C=C1 NRCCSDVEUWXOMG-UHFFFAOYSA-N 0.000 claims description 5
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- GYYUWFNCIFKBEJ-HFWQAORDSA-N (E)-N-(2-aminophenyl)-3-[4-(2-morpholin-4-ylethoxyiminomethyl)phenyl]prop-2-enamide hydrochloride Chemical compound Cl.NC1=CC=CC=C1NC(=O)\C=C\C(C=C1)=CC=C1C=NOCCN1CCOCC1 GYYUWFNCIFKBEJ-HFWQAORDSA-N 0.000 claims description 4
- VRNRFXXEURJIAZ-SWYYNQHESA-N (E)-N-(2-aminophenyl)-3-[4-[(4-nitrophenyl)methoxyiminomethyl]phenyl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C(C=C1)=CC=C1C=NOCC1=CC=C([N+]([O-])=O)C=C1 VRNRFXXEURJIAZ-SWYYNQHESA-N 0.000 claims description 4
- WNSMZNNXMAXKHW-CUFFHGBCSA-N (e)-n-hydroxy-3-[3-(2-morpholin-4-ylethoxyiminomethyl)phenyl]prop-2-enamide;hydrochloride Chemical compound Cl.ONC(=O)\C=C\C1=CC=CC(C=NOCCN2CCOCC2)=C1 WNSMZNNXMAXKHW-CUFFHGBCSA-N 0.000 claims description 4
- DHSYUAULSBHRPH-RVOOOTTKSA-N (e)-n-hydroxy-3-[4-(phenylmethoxyiminomethyl)phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)NO)=CC=C1C=NOCC1=CC=CC=C1 DHSYUAULSBHRPH-RVOOOTTKSA-N 0.000 claims description 4
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- SHGAZHPCJJPHSC-YCNIQYBTSA-N retinoic acid group Chemical group C\C(=C/C(=O)O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 4
- LJTDURKDHMOLIM-OPUQBVRYSA-N (e)-3-[4-[(4-nitrophenyl)methoxyiminomethyl]phenyl]-n-sulfanylprop-2-enamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CON=CC1=CC=C(\C=C\C(=O)NS)C=C1 LJTDURKDHMOLIM-OPUQBVRYSA-N 0.000 claims description 3
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- 206010039491 Sarcoma Diseases 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000003147 glycosyl group Chemical group 0.000 claims description 3
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- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 229940123237 Taxane Drugs 0.000 claims description 2
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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- 239000002168 alkylating agent Substances 0.000 claims description 2
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- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 238000009830 intercalation Methods 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 229930014626 natural product Natural products 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 2
- YNBOWUIQBRECPS-PFMZDYLOSA-N (e)-3-[4-[(e)-(4-nitrophenyl)methoxyiminomethyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1\C=N\OCC1=CC=C([N+]([O-])=O)C=C1 YNBOWUIQBRECPS-PFMZDYLOSA-N 0.000 claims 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C313/28—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05012561 | 2005-06-10 | ||
| EP05012561.6 | 2005-06-10 |
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| KR20080040665A true KR20080040665A (ko) | 2008-05-08 |
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| KR1020087000035A Ceased KR20080040665A (ko) | 2005-06-10 | 2006-05-31 | 항종양 제제로 유용한 신남산, 페닐프로피올산 및페닐프로판산 유도체 |
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| EP (1) | EP1893561A1 (enExample) |
| JP (1) | JP2008545772A (enExample) |
| KR (1) | KR20080040665A (enExample) |
| CN (1) | CN101193854A (enExample) |
| AR (1) | AR053894A1 (enExample) |
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| BR (1) | BRPI0611730A2 (enExample) |
| CA (1) | CA2607184A1 (enExample) |
| EA (1) | EA013845B1 (enExample) |
| MX (1) | MX2007015293A (enExample) |
| TW (1) | TW200718691A (enExample) |
| WO (1) | WO2006131482A1 (enExample) |
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| TWI429628B (zh) | 2010-03-29 | 2014-03-11 | Univ Taipei Medical | 吲哚基或吲哚啉基羥肟酸化合物 |
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| US3763213A (en) * | 1971-11-10 | 1973-10-02 | R Heck | Introduction of organic groups into ethylenically unsaturated carboxylic nitriles using a group viii metal salt |
| US6248752B1 (en) * | 1998-02-27 | 2001-06-19 | Charles Duane Smith | Azabicyclooctane compositions and methods for enhancing chemotherapy |
| TWI311133B (en) | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
| US6800618B2 (en) | 2001-05-07 | 2004-10-05 | The United States Of America As Represented By The Secretary Of The Army | Chemosensitizing agents against chloroquine resistant plasmodium falciparum and methods of making and using thereof |
| DE10225635C1 (de) * | 2002-06-07 | 2003-12-24 | Aventis Pharma Gmbh | N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
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2006
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- 2006-05-31 AU AU2006256769A patent/AU2006256769A1/en not_active Abandoned
- 2006-06-09 AR ARP060102416A patent/AR053894A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080194659A1 (en) | 2008-08-14 |
| JP2008545772A (ja) | 2008-12-18 |
| EP1893561A1 (en) | 2008-03-05 |
| EA200702668A1 (ru) | 2008-04-28 |
| WO2006131482A1 (en) | 2006-12-14 |
| BRPI0611730A2 (pt) | 2010-09-28 |
| MX2007015293A (es) | 2008-02-22 |
| AR053894A1 (es) | 2007-05-23 |
| US7816386B2 (en) | 2010-10-19 |
| AU2006256769A1 (en) | 2006-12-14 |
| TW200718691A (en) | 2007-05-16 |
| CA2607184A1 (en) | 2006-12-14 |
| EA013845B1 (ru) | 2010-08-30 |
| CN101193854A (zh) | 2008-06-04 |
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