HRP20010777A2 - INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF - Google Patents
INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF Download PDFInfo
- Publication number
- HRP20010777A2 HRP20010777A2 HR20010777A HRP20010777A HRP20010777A2 HR P20010777 A2 HRP20010777 A2 HR P20010777A2 HR 20010777 A HR20010777 A HR 20010777A HR P20010777 A HRP20010777 A HR P20010777A HR P20010777 A2 HRP20010777 A2 HR P20010777A2
- Authority
- HR
- Croatia
- Prior art keywords
- sulfide
- chlorophenyl
- amino
- chloro
- dichlorophenyl
- Prior art date
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- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 title claims description 126
- 230000027455 binding Effects 0.000 title claims description 91
- 238000009739 binding Methods 0.000 title claims description 90
- 102100022339 Integrin alpha-L Human genes 0.000 title claims 22
- 239000003112 inhibitor Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 133
- -1 3-Chloro-4-(2,4,5-trichlorophenylsulfanyl)-phenylamine hydrochloride 3-Chloro-4-(2,4-dichlorophenylsulfanyl)-phenylamine hydrochloride 3-Methoxy-4-(2,3-dichlorophenylsulfanyl)-phenylamine Chemical compound 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 68
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims description 32
- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 239000003446 ligand Substances 0.000 claims description 20
- 108010064600 Intercellular Adhesion Molecule-3 Proteins 0.000 claims description 16
- 102100037871 Intercellular adhesion molecule 3 Human genes 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- LKDFVWFXUKMAES-UHFFFAOYSA-N 3-chloro-4-(1-chloronaphthalen-2-yl)sulfanylaniline Chemical compound ClC1=CC(N)=CC=C1SC1=CC=C(C=CC=C2)C2=C1Cl LKDFVWFXUKMAES-UHFFFAOYSA-N 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- AWWAUERJMZWFTF-UHFFFAOYSA-N 4-[3-[3-(4-amino-2-chlorophenyl)-4-chloro-2-nitrophenyl]sulfanyl-6-chloro-2-nitrophenyl]-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=C(Cl)C=CC(SC=2C(=C(C=3C(=CC(N)=CC=3)Cl)C(Cl)=CC=2)[N+]([O-])=O)=C1[N+]([O-])=O AWWAUERJMZWFTF-UHFFFAOYSA-N 0.000 claims description 5
- BGHSZGBBNMTFHW-UHFFFAOYSA-N 4-[3-[3-[4-amino-2-(trifluoromethyl)phenyl]-2,4-dichlorophenyl]sulfanyl-2,6-dichlorophenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=C(Cl)C=CC(SC=2C(=C(C(Cl)=CC=2)C=2C(=CC(N)=CC=2)C(F)(F)F)Cl)=C1Cl BGHSZGBBNMTFHW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- XQFOAFCXFSNGPS-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylphenyl)sulfanylphenyl]pyrrole Chemical compound CC1=CC=CN1C1=CC=CC=C1SC1=CC=CC=C1C XQFOAFCXFSNGPS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- DALUHGHCPIAILI-UHFFFAOYSA-N 2,3-dichloro-1-(2-chloro-4-nitrophenyl)-4-[2,3-dichloro-4-(2-chloro-4-nitrophenyl)phenyl]sulfanylbenzene Chemical compound [O-][N+](=O)c1ccc(c(Cl)c1)-c1ccc(Sc2ccc(c(Cl)c2Cl)-c2ccc(cc2Cl)[N+]([O-])=O)c(Cl)c1Cl DALUHGHCPIAILI-UHFFFAOYSA-N 0.000 claims description 3
- HVFNXRUGFFJWSP-UHFFFAOYSA-N 1,3-dichloro-2-(3-chloro-5-nitrophenyl)-4-[2,4-dichloro-3-(3-chloro-5-nitrophenyl)phenyl]sulfanylbenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C=2C(=C(SC=3C(=C(C(Cl)=CC=3)C=3C=C(C=C(Cl)C=3)[N+]([O-])=O)Cl)C=CC=2Cl)Cl)=C1 HVFNXRUGFFJWSP-UHFFFAOYSA-N 0.000 claims description 2
- AGPSVGCVFYUNMZ-UHFFFAOYSA-N ClC1=C(C=C(C(=C1)N)NC)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C(=C1)NC)N)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1N(C)C)SC1=C(C(=C(C=C1)N(C)C)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl Chemical compound ClC1=C(C=C(C(=C1)N)NC)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C(=C1)NC)N)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1N(C)C)SC1=C(C(=C(C=C1)N(C)C)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl AGPSVGCVFYUNMZ-UHFFFAOYSA-N 0.000 claims 3
- FAOZWDNTZCLNIX-UHFFFAOYSA-N ClC=1C(=CC2=C(NC=N2)C1)SC1=C(C=C(C=C1)Cl)Cl.Cl.OC=1C=C(C=CC1SC1=C(C(=CC=C1)Cl)Cl)N.Cl.BrC=1C=C(C=CC1SC1=C(C=C(C=C1)Cl)Cl)N Chemical class ClC=1C(=CC2=C(NC=N2)C1)SC1=C(C=C(C=C1)Cl)Cl.Cl.OC=1C=C(C=CC1SC1=C(C(=CC=C1)Cl)Cl)N.Cl.BrC=1C=C(C=CC1SC1=C(C=C(C=C1)Cl)Cl)N FAOZWDNTZCLNIX-UHFFFAOYSA-N 0.000 claims 3
- ASWNXTJZIDXCRE-UHFFFAOYSA-N N-[3-chloro-4-(2,3-dichlorophenyl)sulfanylphenyl]acetamide 4-(2,4-dichlorophenyl)sulfanyl-3-methylaniline hydrochloride Chemical compound C(C)(=O)NC1=CC(=C(C=C1)SC1=C(C(=CC=C1)Cl)Cl)Cl.Cl.CC=1C=C(C=CC1SC1=C(C=C(C=C1)Cl)Cl)N ASWNXTJZIDXCRE-UHFFFAOYSA-N 0.000 claims 3
- GKIAMXUAQCGYOI-UHFFFAOYSA-N NC1=CC(=C(C=C1)C=1C(=C(C=CC1NC(C)=O)SC1=C(C(=C(C=C1)NC(C)=O)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.NC1(CC(C(C=C1)SC1C(CC(C=C1)(N)N)(Cl)Cl)(Cl)Cl)N Chemical compound NC1=CC(=C(C=C1)C=1C(=C(C=CC1NC(C)=O)SC1=C(C(=C(C=C1)NC(C)=O)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.NC1(CC(C(C=C1)SC1C(CC(C=C1)(N)N)(Cl)Cl)(Cl)Cl)N GKIAMXUAQCGYOI-UHFFFAOYSA-N 0.000 claims 3
- ZOHJFAWGRKUIGY-UHFFFAOYSA-N Cl.ClC=1C=C(C=CC1SC1=CC2=CC=CC=C2C=C1)N.[N+](=O)([O-])C1=CC(=C(C=C1)C1=C(C(=C(C=C1)SC1=C(C(=C(C=C1)C1=C(C=C(C=C1)[N+](=O)[O-])Cl)Cl)Cl)Cl)Cl)Cl.Cl.ClC=1C=C(C=CC1SC1=C(C=CC=C1)Cl)N Chemical compound Cl.ClC=1C=C(C=CC1SC1=CC2=CC=CC=C2C=C1)N.[N+](=O)([O-])C1=CC(=C(C=C1)C1=C(C(=C(C=C1)SC1=C(C(=C(C=C1)C1=C(C=C(C=C1)[N+](=O)[O-])Cl)Cl)Cl)Cl)Cl)Cl.Cl.ClC=1C=C(C=CC1SC1=C(C=CC=C1)Cl)N ZOHJFAWGRKUIGY-UHFFFAOYSA-N 0.000 claims 2
- AOGJILKTZCNARZ-UHFFFAOYSA-N ClC=1C=C(C=C(C1SC1=C(C=C(C=C1)Cl)Cl)Cl)N.ClC1=CC(=C(C=C1Cl)N)SC1=C(C=C(C=C1)Cl)Cl.NCC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)CN)Cl)Cl)Cl)Cl Chemical compound ClC=1C=C(C=C(C1SC1=C(C=C(C=C1)Cl)Cl)Cl)N.ClC1=CC(=C(C=C1Cl)N)SC1=C(C=C(C=C1)Cl)Cl.NCC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)CN)Cl)Cl)Cl)Cl AOGJILKTZCNARZ-UHFFFAOYSA-N 0.000 claims 2
- SKOBYTVFVNDCED-UHFFFAOYSA-N NC1=CC(=C(C=C1)C1=C(C=CC(=C1Cl)Cl)SC1=C(C(=C(C=C1)Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1[N+](=O)[O-])SC1=C(C(=C(C=C1)[N+](=O)[O-])C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl Chemical compound NC1=CC(=C(C=C1)C1=C(C=CC(=C1Cl)Cl)SC1=C(C(=C(C=C1)Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1[N+](=O)[O-])SC1=C(C(=C(C=C1)[N+](=O)[O-])C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl SKOBYTVFVNDCED-UHFFFAOYSA-N 0.000 claims 2
- DDFVHLMUMIPKNA-UHFFFAOYSA-N NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)N)N)Cl.NC1=CC(=C(C=C1)C=1C(=C(C(=CC1Cl)Cl)SC1=C(C(=C(C=C1Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1F)SC1=C(C(=C(C=C1)F)C1=C(C=C(C=C1)N)Cl)F)F)Cl Chemical compound NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)N)N)Cl.NC1=CC(=C(C=C1)C=1C(=C(C(=CC1Cl)Cl)SC1=C(C(=C(C=C1Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl)Cl)Cl.Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1F)SC1=C(C(=C(C=C1)F)C1=C(C=C(C=C1)N)Cl)F)F)Cl DDFVHLMUMIPKNA-UHFFFAOYSA-N 0.000 claims 2
- OKNHUZXOTSZJAE-UHFFFAOYSA-N NC=1C=C(C=C(C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=CC(=CC(=C1)N)Cl)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)F)Cl)Cl)F.ClC1=C(C=CC(=C1Cl)SC1=C(C=C(C=C1)Cl)Cl)N Chemical compound NC=1C=C(C=C(C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=CC(=CC(=C1)N)Cl)Cl)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)F)Cl)Cl)F.ClC1=C(C=CC(=C1Cl)SC1=C(C=C(C=C1)Cl)Cl)N OKNHUZXOTSZJAE-UHFFFAOYSA-N 0.000 claims 2
- BXVGZOOKBYBVLT-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C=1C(=C(C=CC1)SC1=C(C(=CC=C1)C1=CC=C(C=C1)[N+](=O)[O-])Cl)Cl.NC1=CC=CC(=C1C1=C(C=CC(=C1)C)SC1=C(C=C(C=C1)C)C1=C(C=CC=C1N)Cl)Cl.[N+](=O)([O-])C1=C(C=CC(=C1)Cl)C=1C(=C(C=CC1)SC1=C(C(=CC=C1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-])N)N.S1C(=NC2=C1C=CC=C2)SC2=C(C=C(C=C2)N)Cl Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C=1C(=C(C=CC1)SC1=C(C(=CC=C1)C1=CC=C(C=C1)[N+](=O)[O-])Cl)Cl.NC1=CC=CC(=C1C1=C(C=CC(=C1)C)SC1=C(C=C(C=C1)C)C1=C(C=CC=C1N)Cl)Cl.[N+](=O)([O-])C1=C(C=CC(=C1)Cl)C=1C(=C(C=CC1)SC1=C(C(=CC=C1)C1=C(C=C(C=C1)Cl)[N+](=O)[O-])N)N.S1C(=NC2=C1C=CC=C2)SC2=C(C=C(C=C2)N)Cl BXVGZOOKBYBVLT-UHFFFAOYSA-N 0.000 claims 2
- 150000002923 oximes Chemical class 0.000 claims 2
- HWQGVCVGHMCDPD-UHFFFAOYSA-N 3-chloro-4-(2-chlorophenyl)sulfanylaniline 3-chloro-4-(2,3-dichlorophenyl)sulfanylaniline 3-chloro-4-naphthalen-2-ylsulfanylaniline trihydrochloride Chemical compound Cl.ClC=1C=C(C=CC1SC1=C(C(=CC=C1)Cl)Cl)N.Cl.ClC=1C=C(C=CC1SC1=CC2=CC=CC=C2C=C1)N.Cl.ClC=1C=C(C=CC1SC1=C(C=CC=C1)Cl)N HWQGVCVGHMCDPD-UHFFFAOYSA-N 0.000 claims 1
- USNLTCAOPBUNAL-UHFFFAOYSA-N NC1=CC(=C(C=C1)C1=C(C=CC(=C1Cl)Cl)SC1=C(C(=C(C=C1)Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl Chemical compound NC1=CC(=C(C=C1)C1=C(C=CC(=C1Cl)Cl)SC1=C(C(=C(C=C1)Cl)Cl)C1=C(C=C(C=C1)N)Cl)Cl.NC1=CC(=C(C=C1)C=1C(=C(C=CC1Cl)SC1=C(C(=C(C=C1)Cl)C1=C(C=C(C=C1)N)Cl)[N+](=O)[O-])[N+](=O)[O-])Cl USNLTCAOPBUNAL-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
- C07C323/37—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/36—Sulfur atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
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- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Control Of El Displays (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US28532599A | 1999-04-02 | 1999-04-02 | |
PCT/US2000/008840 WO2000059878A2 (en) | 1999-04-02 | 2000-04-03 | INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF |
Publications (1)
Publication Number | Publication Date |
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HRP20010777A2 true HRP20010777A2 (en) | 2002-12-31 |
Family
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Family Applications (1)
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HR20010777A HRP20010777A2 (en) | 1999-04-02 | 2001-10-23 | INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF |
Country Status (21)
Country | Link |
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EP (1) | EP1165504A2 (ja) |
JP (1) | JP2002541141A (ja) |
KR (1) | KR20020003559A (ja) |
CN (2) | CN1351588A (ja) |
AU (2) | AU774054B2 (ja) |
BG (1) | BG106019A (ja) |
BR (1) | BR0009421A (ja) |
CA (1) | CA2369005A1 (ja) |
CZ (1) | CZ20013524A3 (ja) |
EA (1) | EA200101017A1 (ja) |
EE (1) | EE200100514A (ja) |
HR (1) | HRP20010777A2 (ja) |
HU (1) | HUP0201904A3 (ja) |
IL (1) | IL145528A0 (ja) |
IS (1) | IS6096A (ja) |
MX (1) | MXPA01009915A (ja) |
NO (1) | NO20014768L (ja) |
NZ (1) | NZ515238A (ja) |
PL (1) | PL351323A1 (ja) |
SK (1) | SK14022001A3 (ja) |
WO (1) | WO2000059878A2 (ja) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6515124B2 (en) * | 2000-02-09 | 2003-02-04 | Hoffman-La Roche Inc. | Dehydroamino acids |
WO2002002539A1 (en) | 2000-06-29 | 2002-01-10 | Abbott Laboratories | Aryl phenylheterocyclyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents |
US7064180B2 (en) | 2000-07-31 | 2006-06-20 | The General Hospital Corporation | High affinity integrin polypeptides and uses thereof |
US7153944B2 (en) | 2000-07-31 | 2006-12-26 | The General Hospital Corporation | High affinity integrin polypeptides and uses thereof |
US7323552B2 (en) | 2000-07-31 | 2008-01-29 | The General Hospital Corporation | Variant integrin polypeptides and uses thereof |
AU2001286403A1 (en) * | 2000-07-31 | 2002-02-13 | The General Hospital Corporation | High affinity integrin polypeptides and uses thereof |
UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
CA2492035A1 (en) | 2002-07-11 | 2004-01-15 | Vicuron Pharmaceuticals, Inc. | N-hydroxyamide derivatives possessing antibacterial activity |
DE602004016316D1 (de) | 2003-04-04 | 2008-10-16 | Lundbeck & Co As H | 4-(2-phenylsulfanyl-phenyl)-piperidin-derivate als serotonin-wiederaufnahme-hemmer |
DE602004014190D1 (de) | 2003-12-23 | 2008-07-10 | Lundbeck As Valby H | 2-(1h-indolylsulfanyl)-benzylaminderivate als ssri |
ATE545413T1 (de) * | 2004-03-15 | 2012-03-15 | Lilly Co Eli | Antagonisten des opioidrezeptors |
AR052308A1 (es) | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
AR054393A1 (es) | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
US7629473B2 (en) | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
JP2007008877A (ja) * | 2005-06-30 | 2007-01-18 | Sato Pharmaceutical Co Ltd | 2−ピリドン誘導体を有効成分とする医薬組成物 |
KR20080056221A (ko) * | 2005-10-18 | 2008-06-20 | 시그마타우 인두스트리에 파르마슈티케 리우니테 에스.피.에이. | 베타 아밀로이드 응집의 나프틸 유도체 억제제 |
US8436025B2 (en) * | 2008-09-19 | 2013-05-07 | CompleGen Partners, Inc. | Compounds and methods for PKC theta inhibition |
US9884046B1 (en) * | 2017-06-26 | 2018-02-06 | Macau University Of Science And Technology | Method of treating lung cancer |
NL2026714B1 (en) | 2020-10-20 | 2022-06-16 | Lumicks Ca Holding B V | Improved detection of lymphocyte - target cell interaction |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1493728A1 (de) * | 1965-07-20 | 1969-08-28 | Lauterbach Dr Rudolf | Verfahren zur Herstellung von Aminophenylthioaethern |
US3576872A (en) * | 1968-05-03 | 1971-04-27 | Exxon Research Engineering Co | Herbicidal s-aryl arylamides |
DE2313721A1 (de) * | 1973-03-20 | 1974-10-03 | Bayer Ag | Neue 1-phenylsubstituierte 1,3,5triazine, verfahren zu ihrer herstellung, sowie ihre verwendung als arzneimittel |
GR73690B (ja) * | 1979-01-15 | 1984-04-02 | Celamerck Gmbh & Co Kg | |
US4973599A (en) * | 1989-03-14 | 1990-11-27 | Hoffman-La Roche Inc. | Phenylthioheterocyclic derivatives |
GB9403408D0 (en) * | 1994-02-23 | 1994-04-13 | Wellcome Found | Therapeutic benzonitriles |
TW574214B (en) | 1994-06-08 | 2004-02-01 | Pfizer | Corticotropin releasing factor antagonists |
US6110922A (en) * | 1998-12-29 | 2000-08-29 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
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2000
- 2000-04-03 PL PL00351323A patent/PL351323A1/xx not_active Application Discontinuation
- 2000-04-03 BR BR0009421-8A patent/BR0009421A/pt not_active Application Discontinuation
- 2000-04-03 KR KR1020017012479A patent/KR20020003559A/ko not_active Application Discontinuation
- 2000-04-03 MX MXPA01009915A patent/MXPA01009915A/es unknown
- 2000-04-03 AU AU41919/00A patent/AU774054B2/en not_active Ceased
- 2000-04-03 WO PCT/US2000/008840 patent/WO2000059878A2/en not_active Application Discontinuation
- 2000-04-03 CA CA002369005A patent/CA2369005A1/en not_active Abandoned
- 2000-04-03 EE EEP200100514A patent/EE200100514A/xx unknown
- 2000-04-03 CZ CZ20013524A patent/CZ20013524A3/cs unknown
- 2000-04-03 JP JP2000609391A patent/JP2002541141A/ja active Pending
- 2000-04-03 SK SK1402-2001A patent/SK14022001A3/sk unknown
- 2000-04-03 EA EA200101017A patent/EA200101017A1/ru unknown
- 2000-04-03 CN CN00807734A patent/CN1351588A/zh active Pending
- 2000-04-03 EP EP00921626A patent/EP1165504A2/en not_active Withdrawn
- 2000-04-03 IL IL14552800A patent/IL145528A0/xx unknown
- 2000-04-03 NZ NZ515238A patent/NZ515238A/en unknown
- 2000-04-03 HU HU0201904A patent/HUP0201904A3/hu unknown
- 2000-04-03 CN CNA2005100794026A patent/CN1721401A/zh active Pending
-
2001
- 2001-09-28 IS IS6096A patent/IS6096A/is unknown
- 2001-10-01 NO NO20014768A patent/NO20014768L/no not_active Application Discontinuation
- 2001-10-16 BG BG106019A patent/BG106019A/xx unknown
- 2001-10-23 HR HR20010777A patent/HRP20010777A2/hr not_active Application Discontinuation
-
2004
- 2004-08-24 AU AU2004205210A patent/AU2004205210A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CZ20013524A3 (cs) | 2002-06-12 |
EE200100514A (et) | 2002-12-16 |
KR20020003559A (ko) | 2002-01-12 |
BR0009421A (pt) | 2002-03-26 |
BG106019A (en) | 2002-06-28 |
WO2000059878A3 (en) | 2001-08-09 |
AU2004205210A1 (en) | 2004-09-23 |
CA2369005A1 (en) | 2000-10-12 |
HUP0201904A2 (en) | 2002-09-28 |
WO2000059878A2 (en) | 2000-10-12 |
IL145528A0 (en) | 2002-06-30 |
JP2002541141A (ja) | 2002-12-03 |
NO20014768D0 (no) | 2001-10-01 |
CN1351588A (zh) | 2002-05-29 |
EP1165504A2 (en) | 2002-01-02 |
NZ515238A (en) | 2005-02-25 |
NO20014768L (no) | 2001-11-29 |
IS6096A (is) | 2001-09-28 |
HUP0201904A3 (en) | 2003-04-28 |
CN1721401A (zh) | 2006-01-18 |
AU4191900A (en) | 2000-10-23 |
MXPA01009915A (es) | 2003-08-20 |
SK14022001A3 (sk) | 2002-03-05 |
PL351323A1 (en) | 2003-04-07 |
EA200101017A1 (ru) | 2002-04-25 |
AU774054B2 (en) | 2004-06-17 |
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