HRP20040508A2 - 1,3-diarylprop-2-en-1-ones, compositions containing the same and use thereof - Google Patents
1,3-diarylprop-2-en-1-ones, compositions containing the same and use thereof Download PDFInfo
- Publication number
- HRP20040508A2 HRP20040508A2 HR20040508A HRP20040508A HRP20040508A2 HR P20040508 A2 HRP20040508 A2 HR P20040508A2 HR 20040508 A HR20040508 A HR 20040508A HR P20040508 A HRP20040508 A HR P20040508A HR P20040508 A2 HRP20040508 A2 HR P20040508A2
- Authority
- HR
- Croatia
- Prior art keywords
- propenone
- amino
- methoxy
- methyl
- trimethoxyphenyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title description 56
- -1 COO(R4) Chemical group 0.000 claims description 70
- 239000002253 acid Substances 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 19
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- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
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- 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 5
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- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 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
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- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
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- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- VPXSIAALWZMEKG-UHFFFAOYSA-N Cl.C1=C(NC(=O)C2N(CCC2)C)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 Chemical compound Cl.C1=C(NC(=O)C2N(CCC2)C)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 VPXSIAALWZMEKG-UHFFFAOYSA-N 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
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- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
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- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 159
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- 238000000034 method Methods 0.000 description 34
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- 238000003818 flash chromatography Methods 0.000 description 25
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 24
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- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- KDMYWOVAHWERQN-UHFFFAOYSA-N tert-butyl 5-formylindole-1-carboxylate Chemical compound O=CC1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 KDMYWOVAHWERQN-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0115739A FR2833008B1 (fr) | 2001-12-05 | 2001-12-05 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
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 |
---|---|
HRP20040508A2 true HRP20040508A2 (en) | 2005-08-31 |
Family
ID=26213287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20040508A HRP20040508A2 (en) | 2001-12-05 | 2004-06-04 | 1,3-diarylprop-2-en-1-ones, compositions containing the 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 |
CN1172476A (zh) * | 1995-12-01 | 1998-02-04 | 协和发酵工业株式会社 | 丙烯酮衍生物 |
EP0996432A2 (fr) * | 1997-06-26 | 2000-05-03 | Statens Seruminstitut | 1,3-bis-aromatique-prop-2-en-1-ones, 1,3-bis-aromatique-propane-1-ones et 1,3-bis-aromatique-prop-2-yn-1-ones a action biologique |
-
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 BR BR0214694-0A patent/BR0214694A/pt not_active IP Right Cessation
- 2002-12-03 EP EP02804242A patent/EP1453790A2/fr not_active Withdrawn
- 2002-12-03 JP JP2003549299A patent/JP2005531494A/ja not_active Abandoned
- 2002-12-03 EA EA200400764A patent/EA006803B1/ru not_active IP Right Cessation
- 2002-12-03 CN CNA028268601A patent/CN1612856A/zh active Pending
- 2002-12-03 HU HU0500100A patent/HUP0500100A2/hu unknown
- 2002-12-03 CA CA002469193A patent/CA2469193A1/fr not_active Abandoned
- 2002-12-03 AU AU2002365644A patent/AU2002365644A1/en not_active Abandoned
- 2002-12-03 PL PL02370676A patent/PL370676A1/xx unknown
- 2002-12-03 RS YU47804A patent/RS47804A/sr unknown
- 2002-12-03 KR KR1020047008656A patent/KR20050044712A/ko 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 WO PCT/FR2002/004143 patent/WO2003048106A2/fr not_active Application Discontinuation
-
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 |
---|---|
MA27351A1 (fr) | 2005-06-01 |
NZ533224A (en) | 2006-03-31 |
IL162223A0 (en) | 2005-11-20 |
HUP0500100A2 (hu) | 2005-05-30 |
CN1612856A (zh) | 2005-05-04 |
WO2003048106A3 (fr) | 2004-03-25 |
MXPA04005226A (es) | 2004-10-11 |
JP2005531494A (ja) | 2005-10-20 |
PE20030758A1 (es) | 2003-10-07 |
PA8558501A1 (es) | 2003-09-05 |
EP1453790A2 (fr) | 2004-09-08 |
WO2003048106A2 (fr) | 2003-06-12 |
PL370676A1 (en) | 2005-05-30 |
AR037479A1 (es) | 2004-11-10 |
AU2002365644A1 (en) | 2003-06-17 |
TW200300685A (en) | 2003-06-16 |
EA006803B1 (ru) | 2006-04-28 |
KR20050044712A (ko) | 2005-05-12 |
CO5580759A2 (es) | 2005-11-30 |
EA200400764A1 (ru) | 2004-12-30 |
BR0214694A (pt) | 2004-12-14 |
SV2003001422A (es) | 2003-07-10 |
CA2469193A1 (fr) | 2003-06-12 |
RS47804A (en) | 2006-12-15 |
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