DE602004008100T2 - 4-biarylyl-1-phenylazetidin-2-one - Google Patents
4-biarylyl-1-phenylazetidin-2-one Download PDFInfo
- Publication number
- DE602004008100T2 DE602004008100T2 DE602004008100T DE602004008100T DE602004008100T2 DE 602004008100 T2 DE602004008100 T2 DE 602004008100T2 DE 602004008100 T DE602004008100 T DE 602004008100T DE 602004008100 T DE602004008100 T DE 602004008100T DE 602004008100 T2 DE602004008100 T2 DE 602004008100T2
- Authority
- DE
- Germany
- Prior art keywords
- fluorophenyl
- hydroxypropyl
- compound according
- biphenyl
- azetidin
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 209
- 235000000346 sugar Nutrition 0.000 claims description 193
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 181
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 166
- 229960002920 sorbitol Drugs 0.000 claims description 153
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 151
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 148
- 235000010356 sorbitol Nutrition 0.000 claims description 148
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 145
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 63
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 59
- 239000008194 pharmaceutical composition Substances 0.000 claims description 45
- 150000003254 radicals Chemical class 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 26
- 235000012000 cholesterol Nutrition 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 125000004442 acylamino group Chemical group 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000005518 carboxamido group Chemical group 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 22
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 22
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 22
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 229930182480 glucuronide Natural products 0.000 claims description 21
- 150000008134 glucuronides Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 229920005862 polyol Polymers 0.000 claims description 21
- 239000003112 inhibitor Substances 0.000 claims description 18
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 17
- 150000003077 polyols Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 230000002829 reductive effect Effects 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 8
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 8
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229940011871 estrogen Drugs 0.000 claims description 8
- 239000000262 estrogen Substances 0.000 claims description 8
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 235000001968 nicotinic acid Nutrition 0.000 claims description 7
- 239000011664 nicotinic acid Substances 0.000 claims description 7
- 239000003614 peroxisome proliferator Substances 0.000 claims description 7
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 6
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 6
- 229940123237 Taxane Drugs 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229960003512 nicotinic acid Drugs 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 6
- 230000003637 steroidlike Effects 0.000 claims description 6
- KCSGRODRMYTRTK-SSBOKUKZSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(3-hydroxyphenyl)phenyl]-1-phenylazetidin-2-one Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C=1C=C(O)C=CC=1)C1=CC=CC=C1 KCSGRODRMYTRTK-SSBOKUKZSA-N 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
- 239000003956 nonsteroidal anti androgen Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 4
- NKRDQHPPVRKANS-SSBOKUKZSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(3-hydroxyphenyl)phenyl]azetidin-2-one Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C=1C=C(O)C=CC=1)C1=CC=C(F)C=C1 NKRDQHPPVRKANS-SSBOKUKZSA-N 0.000 claims description 4
- RWKXJFHTJMEVSN-DDPNQRHQSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[2-hydroxy-4-[3-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]phenyl]-1-phenylazetidin-2-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=CC(C=2C=C(O)C([C@H]3N(C(=O)[C@@H]3CC[C@H](O)C=3C=CC(F)=CC=3)C=3C=CC=CC=3)=CC=2)=C1 RWKXJFHTJMEVSN-DDPNQRHQSA-N 0.000 claims description 4
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims description 4
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 4
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 4
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 239000002876 beta blocker Substances 0.000 claims description 4
- 239000000480 calcium channel blocker Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229940035811 conjugated estrogen Drugs 0.000 claims description 4
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical class C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 claims description 4
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 4
- 229960004427 isradipine Drugs 0.000 claims description 4
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims description 4
- AUFRRNVVUPDVLW-DYIKCSJPSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(3-methoxyphenyl)phenyl]azetidin-2-one Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)[C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 AUFRRNVVUPDVLW-DYIKCSJPSA-N 0.000 claims description 3
- FTJFTZVBCNJNGS-SSBOKUKZSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(3-nitrophenyl)phenyl]azetidin-2-one Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C=1C=C(C=CC=1)[N+]([O-])=O)C1=CC=C(F)C=C1 FTJFTZVBCNJNGS-SSBOKUKZSA-N 0.000 claims description 3
- OWJDJOYCABOPKZ-DYIKCSJPSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(4-methylsulfonylphenyl)phenyl]azetidin-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C([C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C=C1 OWJDJOYCABOPKZ-DYIKCSJPSA-N 0.000 claims description 3
- UXEGICXNVPRSBX-DYIKCSJPSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-[3-(hydroxymethyl)phenyl]phenyl]azetidin-2-one Chemical compound OCC1=CC=CC(C=2C=CC(=CC=2)[C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 UXEGICXNVPRSBX-DYIKCSJPSA-N 0.000 claims description 3
- WMMBKQAHXBYLLA-OMGMQEPBSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-phenyl-4-[4-[3-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]phenyl]azetidin-2-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=CC(C=2C=CC(=CC=2)[C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)=C1 WMMBKQAHXBYLLA-OMGMQEPBSA-N 0.000 claims description 3
- FMQSTJQOWDKSSI-DDPNQRHQSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[2-hydroxy-4-[4-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]phenyl]-1-phenylazetidin-2-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=CC=C(C=2C=C(O)C([C@H]3N(C(=O)[C@@H]3CC[C@H](O)C=3C=CC(F)=CC=3)C=3C=CC=CC=3)=CC=2)C=C1 FMQSTJQOWDKSSI-DDPNQRHQSA-N 0.000 claims description 3
- APDKZQRCHXCGTQ-RBLZTMRRSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-[3-[(1s,2r,3r,4r,5s)-1,2,3,4,5,6-hexahydroxyhexyl]phenyl]-2-hydroxyphenyl]-1-phenylazetidin-2-one Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C1=CC=CC(C=2C=C(O)C([C@H]3N(C(=O)[C@@H]3CC[C@H](O)C=3C=CC(F)=CC=3)C=3C=CC=CC=3)=CC=2)=C1 APDKZQRCHXCGTQ-RBLZTMRRSA-N 0.000 claims description 3
- DXUKYEJWVGYABZ-QUFBTCJSSA-N (3r,4s)-4-[4-(2-bromo-5-hydroxyphenyl)phenyl]-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C=1C(=CC=C(O)C=1)Br)C1=CC=C(F)C=C1 DXUKYEJWVGYABZ-QUFBTCJSSA-N 0.000 claims description 3
- AXMHSVPTKDZPHQ-SSBOKUKZSA-N (3r,4s)-4-[4-(4-aminophenyl)phenyl]-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound C1=CC(N)=CC=C1C1=CC=C([C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C=C1 AXMHSVPTKDZPHQ-SSBOKUKZSA-N 0.000 claims description 3
- XNFLDOIXWDXQOW-MJSOWUPRSA-N (3r,4s)-4-[4-[4-(dimethylamino)phenyl]phenyl]-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C([C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C=C1 XNFLDOIXWDXQOW-MJSOWUPRSA-N 0.000 claims description 3
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 3
- 208000035762 Disorder of lipid metabolism Diseases 0.000 claims description 3
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- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 3
- FBCJALRTDMIKNN-IUAQSZDVSA-N [3-[4-[(2s,3r)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl]-3-hydroxyphenyl]phenyl]phosphonic acid Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C(=CC(=CC=1)C=1C=C(C=CC=1)P(O)(O)=O)O)C1=CC=CC=C1 FBCJALRTDMIKNN-IUAQSZDVSA-N 0.000 claims description 3
- IAHZACNSMLSTHV-SSBOKUKZSA-N [3-[4-[(2s,3r)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl]phenyl]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC(=CC=2)[C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)=C1 IAHZACNSMLSTHV-SSBOKUKZSA-N 0.000 claims description 3
- FBABAJBEOJKIGD-SSBOKUKZSA-N [3-[4-[(2s,3r)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl]phenyl]phenyl]phosphonic acid Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C=1C=C(C=CC=1)P(O)(O)=O)C1=CC=CC=C1 FBABAJBEOJKIGD-SSBOKUKZSA-N 0.000 claims description 3
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- AQVJDHBPQCPTBT-MJSOWUPRSA-N n-[3-[4-[(2s,3r)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(=CC=2)[C@H]2N(C(=O)[C@@H]2CC[C@H](O)C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 AQVJDHBPQCPTBT-MJSOWUPRSA-N 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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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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- A—HUMAN NECESSITIES
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/10—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 aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
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Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51869803P | 2003-11-10 | 2003-11-10 | |
| US518698P | 2003-11-10 | ||
| US54957704P | 2004-03-03 | 2004-03-03 | |
| US549577P | 2004-03-03 | ||
| US59252904P | 2004-07-30 | 2004-07-30 | |
| US592529P | 2004-07-30 | ||
| US61400504P | 2004-09-28 | 2004-09-28 | |
| US614005P | 2004-09-28 | ||
| PCT/US2004/037715 WO2005047248A1 (en) | 2003-11-10 | 2004-11-10 | 4-biarylyl-1-phenylazetidin-2-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004008100D1 DE602004008100D1 (de) | 2007-09-20 |
| DE602004008100T2 true DE602004008100T2 (de) | 2008-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004008100T Expired - Lifetime DE602004008100T2 (de) | 2003-11-10 | 2004-11-10 | 4-biarylyl-1-phenylazetidin-2-one |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7320972B2 (https=) |
| EP (1) | EP1682499B1 (https=) |
| JP (1) | JP2007520453A (https=) |
| KR (1) | KR20070050861A (https=) |
| AT (1) | ATE369335T1 (https=) |
| AU (1) | AU2004288822A1 (https=) |
| BR (1) | BRPI0416361A (https=) |
| CA (1) | CA2545058A1 (https=) |
| CY (1) | CY1106982T1 (https=) |
| DE (1) | DE602004008100T2 (https=) |
| DK (1) | DK1682499T3 (https=) |
| EA (1) | EA010026B1 (https=) |
| ES (1) | ES2291974T3 (https=) |
| IL (1) | IL175414A0 (https=) |
| MA (1) | MA28216A1 (https=) |
| MX (1) | MXPA06005106A (https=) |
| NO (1) | NO20062665L (https=) |
| NZ (1) | NZ546940A (https=) |
| PL (2) | PL380414A1 (https=) |
| PT (1) | PT1682499E (https=) |
| WO (1) | WO2005047248A1 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0215579D0 (en) | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
| AU2004288822A1 (en) * | 2003-11-10 | 2005-05-26 | Microbia, Inc. | 4-Biarylyl-1-phenylazetidin-2-ones |
| EP1699759B1 (en) | 2003-12-23 | 2010-10-20 | AstraZeneca AB | Diphenylazetidinone derivates possessing cholesterol absorption inhibitory activity |
| US20090005321A1 (en) * | 2005-02-09 | 2009-01-01 | Microbia, Inc. | Phenylazetidinone Derivatives |
| US20090186834A1 (en) * | 2005-03-24 | 2009-07-23 | Microbia, Inc. | Diphenylheterocycle cholesterol absorption inhibitors |
| WO2006116499A1 (en) * | 2005-04-26 | 2006-11-02 | Microbia, Inc. | 4-biarylyl-1-phenylazetidin-2-one glucuronide derivatives for hypercholesterolemia |
| US20090131395A1 (en) * | 2005-05-05 | 2009-05-21 | Microbia, Inc. | Biphenylazetidinone cholesterol absorption inhibitors |
| TW200726746A (en) * | 2005-05-06 | 2007-07-16 | Microbia Inc | Processes for production of 4-biphenylylazetidin-2-ones |
| JP2008543744A (ja) * | 2005-05-09 | 2008-12-04 | マイクロビア インコーポレーテッド | 有機金属ベンゼンホスホナートカップリング剤 |
| CA2608075A1 (en) * | 2005-05-11 | 2006-11-16 | Microbia, Inc. | Processes for production of phenolic 4-biphenylylazetidin-2-ones |
| WO2006124713A2 (en) * | 2005-05-13 | 2006-11-23 | Microbia, Inc. | 4-biarylyl-1-phenylazetidin-2-ones |
| EA200702614A1 (ru) * | 2005-05-25 | 2008-04-28 | Майкробиа, Инк. | Способы получения 4-(бифенилил)азетидин-2-оналкилфосфиновых кислот |
| EP1893222A4 (en) * | 2005-06-15 | 2010-07-07 | Merck Sharp & Dohme | ANTI-HYPERCHOLESTERINAMIC COMPOUNDS |
| DE602006010870D1 (de) | 2005-06-20 | 2010-01-14 | Schering Corp | Als antagonisten von histamin h3 geeignete piperidinderivate |
| UY29607A1 (es) | 2005-06-20 | 2007-01-31 | Astrazeneca Ab | Compuestos quimicos |
| MY148538A (en) | 2005-06-22 | 2013-04-30 | Astrazeneca Ab | Novel 2-azetidinone derivatives as cholesterol absorption inhibitors for the treatment of hyperlipidaemic conditions |
| SA06270191B1 (ar) | 2005-06-22 | 2010-03-29 | استرازينيكا ايه بي | مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم |
| DE102005055726A1 (de) * | 2005-11-23 | 2007-08-30 | Sanofi-Aventis Deutschland Gmbh | Hydroxy-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| TW200811098A (en) | 2006-04-27 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2008057948A2 (en) * | 2006-11-01 | 2008-05-15 | Ironwood Pharmaceuticals, Inc. | Processes for production of diphenylylazetidin-2-ones and related compounds |
| EP2086324A2 (en) * | 2006-11-02 | 2009-08-12 | Merck & Co., Inc. | Heterocyclyl-substituted anti-hypercholesterolemic compounds |
| JPWO2008108486A1 (ja) | 2007-03-06 | 2010-06-17 | 帝人ファーマ株式会社 | １−ビアリールアゼチジノン誘導体 |
| US20080280836A1 (en) * | 2007-05-08 | 2008-11-13 | Morriello Gregori J | Anti-hypercholesterolemic biaryl azetidinone compounds |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| TW201000107A (en) * | 2008-04-09 | 2010-01-01 | Infinity Pharmaceuticals Inc | Inhibitors of fatty acid amide hydrolase |
| US20090312302A1 (en) * | 2008-06-17 | 2009-12-17 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating nonalcoholic fatty liver disease-associated disorders |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2757622A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| WO2010118155A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| MX2012001729A (es) | 2009-08-26 | 2012-06-13 | Sanofi Sa | Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo. |
| MX361692B (es) | 2010-02-03 | 2018-12-13 | Infinity Pharmaceuticals Inc | Inhibidores de amida hidrolasa de ácido graso. |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| DK3362462T3 (da) | 2015-10-12 | 2021-10-11 | Advanced Cell Diagnostics Inc | In situ-detektion af nukleotidvarianter i prøver med højt støjniveau, og sammensætninger og fremgangsmåder relateret dertil |
| KR102919209B1 (ko) | 2018-08-10 | 2026-01-28 | 다이아핀 테라퓨틱스, 엘엘씨 | 트리-펩타이드 그리고 대사, 심장혈관 및 염증성 장애의 치료 |
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| US37721A (en) * | 1863-02-17 | Improvement in hose-couplings | ||
| US5688787A (en) * | 1991-07-23 | 1997-11-18 | Schering Corporation | Substituted β-lactam compounds useful as hypochlesterolemic agents and processes for the preparation thereof |
| US5561227A (en) | 1991-07-23 | 1996-10-01 | Schering Corporation | Process for the stereospecific synthesis of azetidinones |
| US5688785A (en) * | 1991-07-23 | 1997-11-18 | Schering Corporation | Substituted azetidinone compounds useful as hypocholesterolemic agents |
| ES2107548T3 (es) * | 1991-07-23 | 1997-12-01 | Schering Corp | Compuestos de beta-lactama sustituidos utiles como agentes hipocolesterolemicos y procedimientos para su preparacion. |
| US5631365A (en) * | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
| US5656624A (en) * | 1994-12-21 | 1997-08-12 | Schering Corporation | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
| US5756470A (en) * | 1996-10-29 | 1998-05-26 | Schering Corporation | Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents |
| HRP20030498A2 (en) | 2000-12-21 | 2005-04-30 | Aventis Pharma Deutschland Gmbh | Novel 1,2-diphenzylazetidinones, method for producing the same, medicaments containing said compounds, and the use thereof for treating disorders of the lipid metabolism |
| WO2002058685A2 (en) * | 2001-01-26 | 2002-08-01 | Schering Corporation | Combinations of nicotinic acid and derivatives thereof and sterol absorption inhibitor(s) and treatments for vascular indications |
| TWI291957B (en) * | 2001-02-23 | 2008-01-01 | Kotobuki Pharmaceutical Co Ltd | Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same |
| HUP0401501A3 (en) * | 2001-09-21 | 2012-02-28 | Schering Corp | Treating or preventing vascular inflammation using pharmaceutical compositions containing sterol absorption inhibitor(s) |
| US20030119808A1 (en) * | 2001-09-21 | 2003-06-26 | Schering Corporation | Methods of treating or preventing cardiovascular conditions while preventing or minimizing muscular degeneration side effects |
| US7176194B2 (en) * | 2002-06-19 | 2007-02-13 | Sanofi-Aventis Deutschland Gmbh | Ring-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use |
| US7176193B2 (en) * | 2002-06-19 | 2007-02-13 | Sanofi-Aventis Deutschland Gmbh | Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use |
| AR040588A1 (es) | 2002-07-26 | 2005-04-13 | Schering Corp | Formulacion farmaceutica que comprende un inhibidor de la absorcion del colesterol y un inhibidor de una hmg- co a reductasa |
| EP1682117A1 (en) * | 2003-10-30 | 2006-07-26 | Merck & Co., Inc. | 2-azetidinones as anti-hypercholesterolemic agents |
| AU2004288822A1 (en) * | 2003-11-10 | 2005-05-26 | Microbia, Inc. | 4-Biarylyl-1-phenylazetidin-2-ones |
| CA2608075A1 (en) * | 2005-05-11 | 2006-11-16 | Microbia, Inc. | Processes for production of phenolic 4-biphenylylazetidin-2-ones |
| EA200702614A1 (ru) * | 2005-05-25 | 2008-04-28 | Майкробиа, Инк. | Способы получения 4-(бифенилил)азетидин-2-оналкилфосфиновых кислот |
| DE102005055726A1 (de) * | 2005-11-23 | 2007-08-30 | Sanofi-Aventis Deutschland Gmbh | Hydroxy-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| US20080280836A1 (en) * | 2007-05-08 | 2008-11-13 | Morriello Gregori J | Anti-hypercholesterolemic biaryl azetidinone compounds |
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- 2004-11-10 BR BRPI0416361-3A patent/BRPI0416361A/pt not_active IP Right Cessation
- 2004-11-10 US US10/986,570 patent/US7320972B2/en not_active Expired - Fee Related
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- 2004-11-10 NZ NZ546940A patent/NZ546940A/en unknown
- 2004-11-10 DK DK04810780T patent/DK1682499T3/da active
- 2004-11-10 MX MXPA06005106A patent/MXPA06005106A/es active IP Right Grant
- 2004-11-10 EA EA200600950A patent/EA010026B1/ru not_active IP Right Cessation
- 2004-11-10 KR KR1020067011344A patent/KR20070050861A/ko not_active Ceased
- 2004-11-10 JP JP2006539874A patent/JP2007520453A/ja active Pending
- 2004-11-10 PL PL380414A patent/PL380414A1/pl not_active Application Discontinuation
- 2004-11-10 EP EP04810780A patent/EP1682499B1/en not_active Expired - Lifetime
- 2004-11-10 PL PL04810780T patent/PL1682499T3/pl unknown
- 2004-11-10 PT PT04810780T patent/PT1682499E/pt unknown
- 2004-11-10 AT AT04810780T patent/ATE369335T1/de not_active IP Right Cessation
- 2004-11-10 DE DE602004008100T patent/DE602004008100T2/de not_active Expired - Lifetime
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2006
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2007
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Also Published As
| Publication number | Publication date |
|---|---|
| US20080167255A1 (en) | 2008-07-10 |
| CY1106982T1 (el) | 2012-09-26 |
| DK1682499T3 (da) | 2008-01-02 |
| US20050209165A1 (en) | 2005-09-22 |
| MXPA06005106A (es) | 2007-01-25 |
| PL380414A1 (pl) | 2007-01-22 |
| US7320972B2 (en) | 2008-01-22 |
| BRPI0416361A (pt) | 2007-05-08 |
| EP1682499B1 (en) | 2007-08-08 |
| WO2005047248A1 (en) | 2005-05-26 |
| CA2545058A1 (en) | 2005-05-26 |
| EA200600950A1 (ru) | 2006-10-27 |
| ES2291974T3 (es) | 2008-03-01 |
| AU2004288822A1 (en) | 2005-05-26 |
| DE602004008100D1 (de) | 2007-09-20 |
| NO20062665L (no) | 2006-08-09 |
| MA28216A1 (fr) | 2006-10-02 |
| NZ546940A (en) | 2008-11-28 |
| PL1682499T3 (pl) | 2008-01-31 |
| JP2007520453A (ja) | 2007-07-26 |
| IL175414A0 (en) | 2006-09-05 |
| PT1682499E (pt) | 2007-11-05 |
| HK1093974A1 (en) | 2007-03-16 |
| ATE369335T1 (de) | 2007-08-15 |
| KR20070050861A (ko) | 2007-05-16 |
| EA010026B1 (ru) | 2008-06-30 |
| EP1682499A1 (en) | 2006-07-26 |
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