AU2002365644A1 - 1,3-diarylprop-2-en-1-ones, compositions containing same and use thereof - Google Patents
1,3-diarylprop-2-en-1-ones, compositions containing same and use thereof Download PDFInfo
- Publication number
- AU2002365644A1 AU2002365644A1 AU2002365644A AU2002365644A AU2002365644A1 AU 2002365644 A1 AU2002365644 A1 AU 2002365644A1 AU 2002365644 A AU2002365644 A AU 2002365644A AU 2002365644 A AU2002365644 A AU 2002365644A AU 2002365644 A1 AU2002365644 A1 AU 2002365644A1
- Authority
- AU
- Australia
- Prior art keywords
- propenone
- amino
- methoxy
- methyl
- trimethoxyphenyl
- 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
Links
- 239000000203 mixture Substances 0.000 title description 57
- -1 COO(R4) Chemical group 0.000 claims description 552
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 167
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 28
- XDSHNNRBLSBDAP-UHFFFAOYSA-N (2E)-3-(3,4,5-trimethoxyphenyl)-2-propenal Natural products COC1=CC(C=CC=O)=CC(OC)=C1OC XDSHNNRBLSBDAP-UHFFFAOYSA-N 0.000 claims description 25
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 150000001413 amino acids Chemical class 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 210000002889 endothelial cell Anatomy 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- CWLQUGTUXBXTLF-UHFFFAOYSA-N 1-methylpyrrolidin-1-ium-2-carboxylate Chemical compound CN1CCCC1C(O)=O CWLQUGTUXBXTLF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 6
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims description 5
- 206010054094 Tumour necrosis Diseases 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
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- 230000002401 inhibitory effect Effects 0.000 claims description 5
- IJZPOXAXZULTDR-NTISSMGPSA-N (2S)-2-amino-3-hydroxy-N-[2-methoxy-5-[2-methyl-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl]propanamide hydrochloride Chemical compound Cl.C1=C(NC(=O)[C@@H](N)CO)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 IJZPOXAXZULTDR-NTISSMGPSA-N 0.000 claims description 4
- SPLCKLJETOKHHO-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[2-methyl-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl]acetamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)CN)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 SPLCKLJETOKHHO-UHFFFAOYSA-N 0.000 claims description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229940126601 medicinal product Drugs 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- CWLQUGTUXBXTLF-YFKPBYRVSA-N N-methylproline Chemical compound CN1CCC[C@H]1C(O)=O CWLQUGTUXBXTLF-YFKPBYRVSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- ZVBNZRPCQQPVLU-TXEPZDRESA-N Cl.Cl.C1=C(NC(=O)[C@@H](N)CCCCN)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 Chemical compound Cl.Cl.C1=C(NC(=O)[C@@H](N)CCCCN)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZVBNZRPCQQPVLU-TXEPZDRESA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000000047 product Substances 0.000 description 50
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 45
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 210000004027 cell Anatomy 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 25
- 235000005513 chalcones Nutrition 0.000 description 25
- 238000003818 flash chromatography Methods 0.000 description 25
- 239000002609 medium Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 150000001789 chalcones Chemical class 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
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- 238000000921 elemental analysis Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
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- 230000008018 melting Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 229940024606 amino acid Drugs 0.000 description 13
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
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- 239000000460 chlorine Substances 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- 206010028851 Necrosis Diseases 0.000 description 9
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- LRUWUXUUQXNWOM-UHFFFAOYSA-N 3-(3-amino-4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound C1=C(N)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 LRUWUXUUQXNWOM-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
- C07C279/32—N-nitroguanidines
- C07C279/36—Substituted N-nitroguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Bending Of Plates, Rods, And Pipes (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR01/15739 | 2001-12-05 | ||
FR0115739A FR2833008B1 (fr) | 2001-12-05 | 2001-12-05 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
FR02/14217 | 2002-11-14 | ||
FR0214217 | 2002-11-14 | ||
PCT/FR2002/004143 WO2003048106A2 (fr) | 2001-12-05 | 2002-12-03 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2002365644A1 true AU2002365644A1 (en) | 2003-06-17 |
Family
ID=26213287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2002365644A Abandoned AU2002365644A1 (en) | 2001-12-05 | 2002-12-03 | 1,3-diarylprop-2-en-1-ones, compositions containing same and use thereof |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP1453790A2 (fr) |
JP (1) | JP2005531494A (fr) |
KR (1) | KR20050044712A (fr) |
CN (1) | CN1612856A (fr) |
AR (1) | AR037479A1 (fr) |
AU (1) | AU2002365644A1 (fr) |
BR (1) | BR0214694A (fr) |
CA (1) | CA2469193A1 (fr) |
CO (1) | CO5580759A2 (fr) |
EA (1) | EA006803B1 (fr) |
HR (1) | HRP20040508A2 (fr) |
HU (1) | HUP0500100A2 (fr) |
IL (1) | IL162223A0 (fr) |
MA (1) | MA27351A1 (fr) |
MX (1) | MXPA04005226A (fr) |
NZ (1) | NZ533224A (fr) |
PA (1) | PA8558501A1 (fr) |
PE (1) | PE20030758A1 (fr) |
PL (1) | PL370676A1 (fr) |
RS (1) | RS47804A (fr) |
SV (1) | SV2003001422A (fr) |
TW (1) | TW200300685A (fr) |
WO (1) | WO2003048106A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2854399B1 (fr) * | 2003-04-30 | 2006-11-17 | Aventis Pharma Sa | 1-aryl-3-(indol-5-yl)-prop-2-en-1-ones, compositions les contenant et utilisation |
EP1598353A1 (fr) | 2004-05-17 | 2005-11-23 | Boehringer Ingelheim International GmbH | Pyrrolobenzimidazolones et leur utilisation en tant qu'agents antiproliferatifs |
WO2017103637A1 (fr) | 2015-12-18 | 2017-06-22 | Blirt S.A. | Composés de diphénylpropane et leur activité cytotoxique |
CN109467549B (zh) * | 2018-12-07 | 2021-02-09 | 中国药科大学 | 喹啉取代查尔酮类化合物、其制备方法及用途 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
JPH08277242A (ja) * | 1995-02-08 | 1996-10-22 | Kyowa Hakko Kogyo Co Ltd | プロペノン誘導体 |
EP0812825B1 (fr) * | 1995-12-01 | 2004-02-11 | Kyowa Hakko Kogyo Co., Ltd. | Derives du propenone |
AU7908098A (en) * | 1997-06-26 | 1999-01-19 | Statens Serum Institut | Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones |
-
2002
- 2002-11-21 PE PE2002001118A patent/PE20030758A1/es not_active Application Discontinuation
- 2002-11-22 PA PA20028558501A patent/PA8558501A1/es unknown
- 2002-11-26 TW TW091134346A patent/TW200300685A/zh unknown
- 2002-11-29 AR ARP020104618A patent/AR037479A1/es unknown
- 2002-12-02 SV SV2002001422A patent/SV2003001422A/es not_active Application Discontinuation
- 2002-12-03 EP EP02804242A patent/EP1453790A2/fr not_active Withdrawn
- 2002-12-03 WO PCT/FR2002/004143 patent/WO2003048106A2/fr not_active Application Discontinuation
- 2002-12-03 IL IL16222302A patent/IL162223A0/xx unknown
- 2002-12-03 NZ NZ533224A patent/NZ533224A/xx unknown
- 2002-12-03 MX MXPA04005226A patent/MXPA04005226A/es unknown
- 2002-12-03 AU AU2002365644A patent/AU2002365644A1/en not_active Abandoned
- 2002-12-03 JP JP2003549299A patent/JP2005531494A/ja not_active Abandoned
- 2002-12-03 PL PL02370676A patent/PL370676A1/xx unknown
- 2002-12-03 CA CA002469193A patent/CA2469193A1/fr not_active Abandoned
- 2002-12-03 HU HU0500100A patent/HUP0500100A2/hu unknown
- 2002-12-03 BR BR0214694-0A patent/BR0214694A/pt not_active IP Right Cessation
- 2002-12-03 EA EA200400764A patent/EA006803B1/ru not_active IP Right Cessation
- 2002-12-03 KR KR1020047008656A patent/KR20050044712A/ko not_active Application Discontinuation
- 2002-12-03 RS YU47804A patent/RS47804A/sr unknown
- 2002-12-03 CN CNA028268601A patent/CN1612856A/zh active Pending
-
2004
- 2004-06-01 MA MA27708A patent/MA27351A1/fr unknown
- 2004-06-03 CO CO04052091A patent/CO5580759A2/es not_active Application Discontinuation
- 2004-06-04 HR HR20040508A patent/HRP20040508A2/hr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
MXPA04005226A (es) | 2004-10-11 |
BR0214694A (pt) | 2004-12-14 |
EP1453790A2 (fr) | 2004-09-08 |
TW200300685A (en) | 2003-06-16 |
CN1612856A (zh) | 2005-05-04 |
JP2005531494A (ja) | 2005-10-20 |
AR037479A1 (es) | 2004-11-10 |
IL162223A0 (en) | 2005-11-20 |
KR20050044712A (ko) | 2005-05-12 |
WO2003048106A2 (fr) | 2003-06-12 |
HUP0500100A2 (hu) | 2005-05-30 |
EA200400764A1 (ru) | 2004-12-30 |
EA006803B1 (ru) | 2006-04-28 |
SV2003001422A (es) | 2003-07-10 |
PA8558501A1 (es) | 2003-09-05 |
PL370676A1 (en) | 2005-05-30 |
MA27351A1 (fr) | 2005-06-01 |
RS47804A (en) | 2006-12-15 |
HRP20040508A2 (en) | 2005-08-31 |
PE20030758A1 (es) | 2003-10-07 |
CA2469193A1 (fr) | 2003-06-12 |
NZ533224A (en) | 2006-03-31 |
WO2003048106A3 (fr) | 2004-03-25 |
CO5580759A2 (es) | 2005-11-30 |
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NB | Applications allowed - extensions of time section 223(2) |
Free format text: THE TIME IN WHICH TO FILE THE PRESCRIBED DOCUMENTS HAS BEEN EXTENDED TO 05 AUG 2004. |
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MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |