AU2006271375A1 - Use of thiazole derivatives and analogues in the treatment of cancer - Google Patents
Use of thiazole derivatives and analogues in the treatment of cancer Download PDFInfo
- Publication number
- AU2006271375A1 AU2006271375A1 AU2006271375A AU2006271375A AU2006271375A1 AU 2006271375 A1 AU2006271375 A1 AU 2006271375A1 AU 2006271375 A AU2006271375 A AU 2006271375A AU 2006271375 A AU2006271375 A AU 2006271375A AU 2006271375 A1 AU2006271375 A1 AU 2006271375A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- thiazolidin
- alkyl
- title compound
- 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
- 206010028980 Neoplasm Diseases 0.000 title claims description 74
- 201000011510 cancer Diseases 0.000 title claims description 47
- 238000011282 treatment Methods 0.000 title claims description 29
- 150000007979 thiazole derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 415
- 238000000034 method Methods 0.000 claims description 104
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- -1 5-(3-(trifluoromethyl)benzyl)-2-(4-chlorophenylimino)thiazolidin Chemical compound 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 239000002671 adjuvant Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 210000000481 breast Anatomy 0.000 claims description 6
- MGJFLAHLODASKL-UHFFFAOYSA-N 2-(4-chloroanilino)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-4-one Chemical compound FC(F)(F)C1=CC=CC(CC2C(N=C(NC=3C=CC(Cl)=CC=3)S2)=O)=C1 MGJFLAHLODASKL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 210000001072 colon Anatomy 0.000 claims description 4
- 239000013066 combination product Substances 0.000 claims description 4
- 229940127555 combination product Drugs 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- LKJFEVJLZCHMNR-UHFFFAOYSA-N 2-(4-methylanilino)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1NC(S1)=NC(=O)C1CC1=CC=CC(C(F)(F)F)=C1 LKJFEVJLZCHMNR-UHFFFAOYSA-N 0.000 claims description 3
- LTLCFQDQBAXULG-UHFFFAOYSA-N 2-anilino-5-[2-(4-methoxyphenyl)ethyl]-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1CCC(S1)C(=O)NC1=NC1=CC=CC=C1 LTLCFQDQBAXULG-UHFFFAOYSA-N 0.000 claims description 3
- OJOXIPILLXOGHW-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-2-(pyridin-2-ylamino)-1,3-thiazol-4-one Chemical compound C1=CC(F)=CC=C1CC1C(=O)N=C(NC=2N=CC=CC=2)S1 OJOXIPILLXOGHW-UHFFFAOYSA-N 0.000 claims description 3
- MAPMLWITJFLOHM-UHFFFAOYSA-N 5-[2-(4-methoxyphenyl)ethyl]-2-(4-methylanilino)-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1CCC(S1)C(=O)NC1=NC1=CC=C(C)C=C1 MAPMLWITJFLOHM-UHFFFAOYSA-N 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- LCBASURTTNEAPL-UHFFFAOYSA-N 2-(4-chloroanilino)-5-[(4-methylphenyl)methyl]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1CC1C(=O)N=C(NC=2C=CC(Cl)=CC=2)S1 LCBASURTTNEAPL-UHFFFAOYSA-N 0.000 claims description 2
- CYCZYGRIZJUNBZ-UHFFFAOYSA-N 2-(4-methoxyanilino)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1N=C1SC(CC=2C=C(C=CC=2)C(F)(F)F)C(=O)N1 CYCZYGRIZJUNBZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- KXPAJSAIUIKHHH-UHFFFAOYSA-N 4-chloro-n-[4-oxo-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC(CC2C(NC(S2)=NC(=O)C=2C=CC(Cl)=CC=2)=O)=C1 KXPAJSAIUIKHHH-UHFFFAOYSA-N 0.000 claims description 2
- HVTYXFRFLWCHNY-UHFFFAOYSA-N 4-chloro-n-[4-oxo-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(CC2C(NC(S2)=NS(=O)(=O)C=2C=CC(Cl)=CC=2)=O)=C1 HVTYXFRFLWCHNY-UHFFFAOYSA-N 0.000 claims description 2
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
- ACQMGTBEKGXGJU-UHFFFAOYSA-N 2-(4-propan-2-ylanilino)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-4-one Chemical compound C1=CC(C(C)C)=CC=C1N=C1SC(CC=2C=C(C=CC=2)C(F)(F)F)C(=O)N1 ACQMGTBEKGXGJU-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- WDLCSKLLZQXZRZ-UHFFFAOYSA-N phenyl n-[4-oxo-5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]carbamate Chemical compound FC(F)(F)C1=CC=CC(CC2C(NC(S2)=NC(=O)OC=2C=CC=CC=2)=O)=C1 WDLCSKLLZQXZRZ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 69
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- 210000004027 cell Anatomy 0.000 description 48
- 239000000203 mixture Substances 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 40
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 38
- 238000005481 NMR spectroscopy Methods 0.000 description 38
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 37
- 238000003818 flash chromatography Methods 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000843 powder Substances 0.000 description 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
- 239000012043 crude product Substances 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 206010006187 Breast cancer Diseases 0.000 description 13
- 208000026310 Breast neoplasm Diseases 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 229960004488 linolenic acid Drugs 0.000 description 12
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 229940002612 prodrug Drugs 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 230000035755 proliferation Effects 0.000 description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 206010027476 Metastases Diseases 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 230000009401 metastasis Effects 0.000 description 7
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- 239000011734 sodium Substances 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 6
- 201000008980 hyperinsulinism Diseases 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 206010060862 Prostate cancer Diseases 0.000 description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
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- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- 230000004797 therapeutic response Effects 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59562005P | 2005-07-21 | 2005-07-21 | |
| SE0501721-5 | 2005-07-21 | ||
| US60/595,620 | 2005-07-21 | ||
| SE0501721 | 2005-07-21 | ||
| US74442206P | 2006-04-07 | 2006-04-07 | |
| US60/744,422 | 2006-04-07 | ||
| PCT/GB2006/002730 WO2007010273A2 (en) | 2005-07-21 | 2006-07-21 | Use of thiazole derivatives and analogues in the treatment of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006271375A2 AU2006271375A2 (en) | 2007-01-25 |
| AU2006271375A1 true AU2006271375A1 (en) | 2007-01-25 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006271383A Abandoned AU2006271383A1 (en) | 2005-07-21 | 2006-07-21 | Use of thiazole derivatives and analogues in disorders caused by free fatty acids |
| AU2006271375A Abandoned AU2006271375A1 (en) | 2005-07-21 | 2006-07-21 | Use of thiazole derivatives and analogues in the treatment of cancer |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006271383A Abandoned AU2006271383A1 (en) | 2005-07-21 | 2006-07-21 | Use of thiazole derivatives and analogues in disorders caused by free fatty acids |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20090156644A1 (enExample) |
| EP (2) | EP1906955A2 (enExample) |
| JP (2) | JP2009501775A (enExample) |
| KR (2) | KR20080034436A (enExample) |
| AU (2) | AU2006271383A1 (enExample) |
| CA (2) | CA2614327A1 (enExample) |
| EA (2) | EA200800303A1 (enExample) |
| IL (2) | IL188031A0 (enExample) |
| NO (2) | NO20076333L (enExample) |
| WO (2) | WO2007010281A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005024012A1 (de) * | 2005-05-20 | 2006-11-23 | Grünenthal GmbH | Verwendung von 2,5-disubstituierten Thiazol-4-on-Derivaten in Arzneimitteln |
| WO2008065409A2 (en) * | 2006-12-01 | 2008-06-05 | Betagenon Ab | Combination for use in the treatment of cancer, comprising tamoxifen or an aromatase inhibitor |
| WO2008090327A1 (en) * | 2007-01-22 | 2008-07-31 | Betagenon Ab | New combination for use in the treatment of cancer |
| JP2010522163A (ja) * | 2007-03-20 | 2010-07-01 | キュリス，インコーポレイテッド | 亜鉛結合部位を含むＲａｆキナーゼインヒビター |
| CN101274918A (zh) * | 2007-03-30 | 2008-10-01 | 中国科学院上海药物研究所 | 一类取代五元杂环化合物,其制备方法和医学用途 |
| WO2009019446A1 (en) * | 2007-08-03 | 2009-02-12 | Betagenon Ab | Compounds useful as medicaments |
| AU2008310097B2 (en) | 2007-10-09 | 2013-05-16 | Merck Patent Gmbh | Pyridine derivatives useful as glucokinase activators |
| US20110263664A1 (en) * | 2007-11-15 | 2011-10-27 | Musc Foundation For Research Development | Inhibitors of PIM-1 Protein Kinases, Compositions and Methods for Treating Prostate Cancer |
| KR100998572B1 (ko) * | 2007-12-14 | 2010-12-07 | 한국생명공학연구원 | 단백질 포스파타제의 활성을 억제하는 페닐아미노티아졸론유도체 또는 이의 약학적으로 허용가능한 염을유효성분으로 함유하는 암 예방 및 치료용 조성물 |
| WO2010073011A2 (en) | 2008-12-23 | 2010-07-01 | Betagenon Ab | Compounds useful as medicaments |
| WO2010086613A1 (en) | 2009-01-30 | 2010-08-05 | Betagenon Ab | Compounds useful as inhibitors as ampk |
| WO2011004162A2 (en) | 2009-07-08 | 2011-01-13 | Betagenon Ab | Compounds useful as medicaments |
| WO2011079036A1 (en) * | 2009-12-22 | 2011-06-30 | The Translational Genomics Research Institute | Benzamide derivatives |
| US8865754B2 (en) | 2011-03-03 | 2014-10-21 | Proteotech Inc. | Compounds for the treatment of neurodegenerative diseases |
| EP2760856B1 (en) * | 2011-09-30 | 2016-09-14 | Bristol-Myers Squibb Company | Selective nr2b antagonists |
| WO2013108026A1 (en) | 2012-01-17 | 2013-07-25 | Baltic Bio Ab | Thiadiazolone derivatives useful in the treatment of diabetes |
| CN104059060B (zh) * | 2014-05-30 | 2017-08-01 | 西安交通大学 | 一种5‑(1h‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用 |
| MX2022001861A (es) * | 2019-08-15 | 2022-03-11 | Bayer Ag | Procedimiento para la preparacion de 2-(fenilimino)-3-alquil-1,3-t iazolidin-4-onas. |
| US12404242B2 (en) | 2021-12-17 | 2025-09-02 | Reglagene, Inc. | Compositions and methods for making and using small molecules in the treatment of cancer |
| US12215102B2 (en) | 2023-02-28 | 2025-02-04 | Reglagene, Inc. | Compositions and methods for making and using small molecules for tubulin-targeted therapy in the treatment of cancers and related conditions |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3345374A (en) * | 1962-09-04 | 1967-10-03 | Bayer Ag | Certain oxathiazole and dithiazole derivatives |
| US3671537A (en) * | 1969-06-05 | 1972-06-20 | Gyogyszerkutato Intezet | Certain 3-(2,6-dichlorophenyl)-2-iminothiazolidines |
| US4103018A (en) * | 1976-10-12 | 1978-07-25 | Schering Corporation | 2-[4-(Polyhalo-2-hydroxy-2-propyl)anilino]-2-oxazolin-4-ones and thiazolin-4-ones corresponding thereto |
| HU191408B (en) * | 1984-04-25 | 1987-02-27 | Egis Gyogyszergyar,Hu | Process for preparing new imino-thiazolidine derivatives |
| DD246541A1 (de) * | 1986-01-27 | 1987-06-10 | Univ Halle Wittenberg | Verfahren zur herstellung von 5-arylidenthiazolidin-4-onen |
| DD270072A1 (de) * | 1988-03-14 | 1989-07-19 | Univ Halle Wittenberg | Verfahren zur herstellung von 5-aryliden- hoch 2-thiazolin-4-onen |
| US6353006B1 (en) * | 1999-01-14 | 2002-03-05 | Bayer Corporation | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| WO2004037250A1 (en) * | 2002-10-23 | 2004-05-06 | Beyond Genomics, Inc. | 4-alkenylthiazoles comprising epoxide functionality, and methods of use thereof |
| WO2005082363A1 (en) * | 2004-02-20 | 2005-09-09 | Board Of Regents, The University Of Texas System | Thiazolone compounds for treatment of cancer |
| JP2007535549A (ja) * | 2004-04-30 | 2007-12-06 | シェーリング コーポレイション | 神経ペプチドレセプターモジュレーター |
| WO2006002829A1 (en) * | 2004-07-01 | 2006-01-12 | F. Hoffmann-La Roche Ag | Thiazolinone unsubstituted quinolines |
| EP1776112A4 (en) * | 2004-08-10 | 2009-11-25 | Exelixis Inc | HETEROCYCLIC COMPOUNDS AS PHARMACEUTICAL AGENTS |
| CA2583311A1 (en) * | 2004-10-14 | 2006-04-20 | F. Hoffmann-La Roche Ag | Quinazolinylmethylenethiazolinones as cdk1 inhibitors |
| CN100525929C (zh) * | 2005-04-20 | 2009-08-12 | 郭文礼 | 喷水枪出水控制装置 |
| EP1907369A4 (en) * | 2005-07-04 | 2009-07-22 | Reddys Lab Ltd Dr | THIAZOLE DERIVATIVES USEFUL AS AMPK ACTIVATORS |
-
2006
- 2006-07-21 KR KR1020087001174A patent/KR20080034436A/ko not_active Withdrawn
- 2006-07-21 EA EA200800303A patent/EA200800303A1/ru unknown
- 2006-07-21 WO PCT/GB2006/002743 patent/WO2007010281A2/en not_active Ceased
- 2006-07-21 US US11/989,029 patent/US20090156644A1/en not_active Abandoned
- 2006-07-21 KR KR1020087001175A patent/KR20080032096A/ko not_active Withdrawn
- 2006-07-21 JP JP2008522062A patent/JP2009501775A/ja not_active Withdrawn
- 2006-07-21 CA CA002614327A patent/CA2614327A1/en not_active Abandoned
- 2006-07-21 EA EA200800302A patent/EA200800302A1/ru unknown
- 2006-07-21 EP EP06765059A patent/EP1906955A2/en not_active Withdrawn
- 2006-07-21 AU AU2006271383A patent/AU2006271383A1/en not_active Abandoned
- 2006-07-21 WO PCT/GB2006/002730 patent/WO2007010273A2/en not_active Ceased
- 2006-07-21 EP EP06765072A patent/EP1906956A2/en not_active Withdrawn
- 2006-07-21 JP JP2008522065A patent/JP2009501776A/ja not_active Withdrawn
- 2006-07-21 CA CA002615752A patent/CA2615752A1/en not_active Abandoned
- 2006-07-21 AU AU2006271375A patent/AU2006271375A1/en not_active Abandoned
- 2006-07-21 US US11/989,001 patent/US20090136472A1/en not_active Abandoned
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2007
- 2007-12-10 IL IL188031A patent/IL188031A0/en unknown
- 2007-12-11 NO NO20076333A patent/NO20076333L/no not_active Application Discontinuation
- 2007-12-13 NO NO20076420A patent/NO20076420L/no not_active Application Discontinuation
- 2007-12-16 IL IL188163A patent/IL188163A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006271375A2 (en) | 2007-01-25 |
| EA200800303A1 (ru) | 2008-10-30 |
| CA2615752A1 (en) | 2007-01-25 |
| AU2006271383A1 (en) | 2007-01-25 |
| US20090156644A1 (en) | 2009-06-18 |
| IL188031A0 (en) | 2011-08-01 |
| WO2007010273A2 (en) | 2007-01-25 |
| WO2007010281A3 (en) | 2007-06-07 |
| KR20080032096A (ko) | 2008-04-14 |
| CA2614327A1 (en) | 2007-01-25 |
| JP2009501776A (ja) | 2009-01-22 |
| JP2009501775A (ja) | 2009-01-22 |
| WO2007010281A2 (en) | 2007-01-25 |
| NO20076420L (no) | 2008-04-09 |
| EA200800302A1 (ru) | 2008-08-29 |
| EP1906956A2 (en) | 2008-04-09 |
| US20090136472A1 (en) | 2009-05-28 |
| EP1906955A2 (en) | 2008-04-09 |
| WO2007010273A3 (en) | 2007-05-10 |
| NO20076333L (no) | 2008-04-01 |
| IL188163A0 (en) | 2008-03-20 |
| KR20080034436A (ko) | 2008-04-21 |
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