ES2291974T3 - 4-biarilil-1-fenilazetidin-2-onas. - Google Patents
4-biarilil-1-fenilazetidin-2-onas. Download PDFInfo
- Publication number
- ES2291974T3 ES2291974T3 ES04810780T ES04810780T ES2291974T3 ES 2291974 T3 ES2291974 T3 ES 2291974T3 ES 04810780 T ES04810780 T ES 04810780T ES 04810780 T ES04810780 T ES 04810780T ES 2291974 T3 ES2291974 T3 ES 2291974T3
- Authority
- ES
- Spain
- Prior art keywords
- fluorophenyl
- baselineskip
- hydroxypropyl
- compound according
- biphenyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 223
- -1 OCF2H Chemical group 0.000 claims description 214
- 238000006243 chemical reaction Methods 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 238000004519 manufacturing process Methods 0.000 claims description 73
- 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 72
- 239000000203 mixture Substances 0.000 claims description 69
- 235000000346 sugar Nutrition 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 47
- 239000008194 pharmaceutical composition Substances 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 235000012000 cholesterol Nutrition 0.000 claims description 36
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 32
- 125000002252 acyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000004442 acylamino group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000005518 carboxamido group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 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
- 229930182480 glucuronide Natural products 0.000 claims description 22
- 150000008134 glucuronides Chemical class 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
- 229960002920 sorbitol Drugs 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 20
- 229920005862 polyol Polymers 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 150000003077 polyols Chemical class 0.000 claims description 18
- 230000002265 prevention Effects 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 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 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 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 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 235000010356 sorbitol Nutrition 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 239000002699 waste material Substances 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002220 antihypertensive agent Substances 0.000 claims description 9
- 229940011871 estrogen Drugs 0.000 claims description 9
- 239000000262 estrogen Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229950003040 dalvastatin Drugs 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 7
- 239000003472 antidiabetic agent Substances 0.000 claims description 7
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 7
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 7
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 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
- 235000001968 nicotinic acid Nutrition 0.000 claims description 6
- 239000011664 nicotinic acid Substances 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 230000003637 steroidlike Effects 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 102000015694 estrogen receptors Human genes 0.000 claims description 5
- 108010038795 estrogen receptors Proteins 0.000 claims description 5
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 229960003512 nicotinic acid Drugs 0.000 claims description 5
- 239000003956 nonsteroidal anti androgen Substances 0.000 claims description 5
- 239000003614 peroxisome proliferator Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 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 4
- 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 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
- 108010064733 Angiotensins Proteins 0.000 claims description 4
- 102000015427 Angiotensins Human genes 0.000 claims description 4
- 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 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
- 239000000556 agonist Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 229940035811 conjugated estrogen Drugs 0.000 claims description 4
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 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
- 239000003352 sequestering agent Substances 0.000 claims description 4
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 3
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 3
- 108010069236 Goserelin Proteins 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 claims description 3
- 108010000817 Leuprolide Proteins 0.000 claims description 3
- 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
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 3
- 230000002280 anti-androgenic effect Effects 0.000 claims description 3
- 239000000051 antiandrogen Substances 0.000 claims description 3
- 229920000080 bile acid sequestrant Polymers 0.000 claims description 3
- 239000000480 calcium channel blocker Substances 0.000 claims description 3
- 230000007423 decrease Effects 0.000 claims description 3
- 229950004203 droloxifene Drugs 0.000 claims description 3
- 239000002532 enzyme inhibitor Substances 0.000 claims description 3
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 3
- QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 claims description 3
- 229940125753 fibrate Drugs 0.000 claims description 3
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims description 3
- 229950002248 idoxifene Drugs 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 229940127084 other anti-cancer agent Drugs 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 229960004622 raloxifene Drugs 0.000 claims description 3
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 3
- 229940044601 receptor agonist Drugs 0.000 claims description 3
- 239000000018 receptor agonist Substances 0.000 claims description 3
- 229960001603 tamoxifen Drugs 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims description 2
- FXAAOALUHHXBSO-ILDUYXDCSA-N (3,3,5-trimethylcyclohexyl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)[C@H]1NC(=O)CC1 FXAAOALUHHXBSO-ILDUYXDCSA-N 0.000 claims description 2
- QTVBOXYABZYUNX-IUAQSZDVSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[2-hydroxy-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)O)C1=CC=C(F)C=C1 QTVBOXYABZYUNX-IUAQSZDVSA-N 0.000 claims description 2
- HVFSQDFXKQAUJZ-WDRHAOIDSA-N (3r,4s)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-[3-[(2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexoxy]phenyl]phenyl]azetidin-2-one Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)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 HVFSQDFXKQAUJZ-WDRHAOIDSA-N 0.000 claims description 2
- IPRFMZNOGZWMGY-IUAQSZDVSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[2-hydroxy-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)O)C1=CC=CC=C1 IPRFMZNOGZWMGY-IUAQSZDVSA-N 0.000 claims description 2
- IUVGMYZWEOMOTR-IUAQSZDVSA-N (3r,4s)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[2-hydroxy-4-(4-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=CC(O)=CC=1)O)C1=CC=CC=C1 IUVGMYZWEOMOTR-IUAQSZDVSA-N 0.000 claims description 2
- QIZJALLUDDHKGH-CKIYMEHHSA-N (3r,4s)-4-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)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=C2OCCOC2=CC=1)C1=CC=C(F)C=C1 QIZJALLUDDHKGH-CKIYMEHHSA-N 0.000 claims description 2
- RABYQMYFOVJDTB-SSBOKUKZSA-N (3r,4s)-4-[4-(3,5-dihydroxyphenyl)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=C(O)C=C(O)C=1)C1=CC=C(F)C=C1 RABYQMYFOVJDTB-SSBOKUKZSA-N 0.000 claims description 2
- HUEKYIANWVBUAM-MJSOWUPRSA-N (3r,4s)-4-[4-(3,5-dimethoxyphenyl)phenyl]-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound COC1=CC(OC)=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 HUEKYIANWVBUAM-MJSOWUPRSA-N 0.000 claims description 2
- WAAWTRFXXXWGKO-DYIKCSJPSA-N (3r,4s)-4-[4-(3-fluoro-5-methoxyphenyl)phenyl]-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound COC1=CC(F)=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 WAAWTRFXXXWGKO-DYIKCSJPSA-N 0.000 claims description 2
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims description 2
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 2
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- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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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- 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
- A61K31/397—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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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- 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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- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
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- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (8)
| 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 |
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| ES2291974T3 true ES2291974T3 (es) | 2008-03-01 |
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| ES04810780T Expired - Lifetime ES2291974T3 (es) | 2003-11-10 | 2004-11-10 | 4-biarilil-1-fenilazetidin-2-onas. |
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| 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=) |
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| ES (1) | ES2291974T3 (https=) |
| IL (1) | IL175414A0 (https=) |
| MA (1) | MA28216A1 (https=) |
| MX (1) | MXPA06005106A (https=) |
| NO (1) | NO20062665L (https=) |
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| PT (1) | PT1682499E (https=) |
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| GB0215579D0 (en) | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
| ATE369335T1 (de) * | 2003-11-10 | 2007-08-15 | Microbia Inc | 4-biarylyl-1-phenylazetidin-2-one |
| ATE485267T1 (de) | 2003-12-23 | 2010-11-15 | Astrazeneca Ab | Diphenylazetidinonderivate mit die cholesterinabsorption hemmender wirkung |
| WO2006086562A2 (en) * | 2005-02-09 | 2006-08-17 | Microbia, Inc. | Phenylazetidinone derivatives |
| WO2006102674A2 (en) * | 2005-03-24 | 2006-09-28 | Microbia, Inc. | Diphenylheterocycle cholesterol absorption inhibitors |
| US20080194494A1 (en) * | 2005-04-26 | 2008-08-14 | 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 |
| MX2007014162A (es) * | 2005-05-09 | 2008-04-04 | Microbia Inc | Agentes de acoplamiento de bencenfosfonatos organometalicos. |
| MX2007014172A (es) * | 2005-05-11 | 2008-04-02 | Microbia Inc | Procedimiento para la produccion de 4-bifenililacetidina-2-onas fenolicos. |
| TW200740752A (en) * | 2005-05-13 | 2007-11-01 | Microbia Inc | 4-Biarylyl-1-phenylazetidin-2-ones |
| JP2008545700A (ja) * | 2005-05-25 | 2008-12-18 | マイクロビア インコーポレーテッド | ４−（ビフェニリル）アゼチジン−２−オンホスホン酸類の製造方法 |
| US7696177B2 (en) * | 2005-06-15 | 2010-04-13 | Merck Sharp & Dohme Corp. | Anti-hypercholesterolemic compounds |
| TW200738676A (en) | 2005-06-20 | 2007-10-16 | Schering Corp | Heteroatom-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists |
| UY29607A1 (es) | 2005-06-20 | 2007-01-31 | Astrazeneca Ab | Compuestos quimicos |
| 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 |
| AR057072A1 (es) | 2005-06-22 | 2007-11-14 | Astrazeneca Ab | Compuestos quimicos derivados de 2-azetidinona, formulacion farmaceutica y un proceso de preparacion del compuesto |
| 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 |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| 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 |
| AU2007318058A1 (en) * | 2006-11-02 | 2008-05-15 | Merck Sharp & Dohme Corp. | Heterocyclyl-substituted anti-hypercholesterolemic compounds |
| US20100125059A1 (en) * | 2007-03-06 | 2010-05-20 | Teijin Pharma Limited | 1-biarylazetidinone derivative |
| 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 |
| CA2721060A1 (en) * | 2008-04-09 | 2009-10-15 | 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 |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| 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 |
| WO2010118159A1 (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 |
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| RU2015143910A (ru) | 2010-02-03 | 2018-12-28 | Инфинити Фармасьютикалз, Инк. | Ингибиторы амид-гидролазы жирных кислот |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
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| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
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| US37721A (en) * | 1863-02-17 | Improvement in hose-couplings | ||
| US5688785A (en) * | 1991-07-23 | 1997-11-18 | Schering Corporation | Substituted azetidinone compounds useful as hypocholesterolemic agents |
| US5688787A (en) * | 1991-07-23 | 1997-11-18 | Schering Corporation | Substituted β-lactam compounds useful as hypochlesterolemic agents and processes for the preparation thereof |
| JP2525125B2 (ja) * | 1991-07-23 | 1996-08-14 | シェリング・コーポレーション | 血清コレステロ―ル低下薬として有用な置換β−ラクタム化合物およびそれらの製法 |
| US5561227A (en) * | 1991-07-23 | 1996-10-01 | Schering Corporation | Process for the stereospecific synthesis of azetidinones |
| 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 |
| EP1345895B1 (de) * | 2000-12-21 | 2006-12-27 | Sanofi-Aventis Deutschland GmbH | Neue diphenzylazetidinone, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung zur behandlung von lipidstoffwechselstörungen |
| US20020183305A1 (en) * | 2001-01-26 | 2002-12-05 | 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 |
| AU2002335770B2 (en) * | 2001-09-21 | 2005-08-18 | Merck Sharp & Dohme Corp. | Methods for treating or preventing vascular inflammation using 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 |
| WO2005044256A1 (en) * | 2003-10-30 | 2005-05-19 | Merck & Co., Inc. | 2-azetidinones as anti-hypercholesterolemic agents |
| ATE369335T1 (de) * | 2003-11-10 | 2007-08-15 | Microbia Inc | 4-biarylyl-1-phenylazetidin-2-one |
| MX2007014172A (es) * | 2005-05-11 | 2008-04-02 | Microbia Inc | Procedimiento para la produccion de 4-bifenililacetidina-2-onas fenolicos. |
| JP2008545700A (ja) * | 2005-05-25 | 2008-12-18 | マイクロビア インコーポレーテッド | ４−（ビフェニリル）アゼチジン−２−オンホスホン酸類の製造方法 |
| 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 |
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-
2004
- 2004-11-10 AT AT04810780T patent/ATE369335T1/de not_active IP Right Cessation
- 2004-11-10 AU AU2004288822A patent/AU2004288822A1/en not_active Abandoned
- 2004-11-10 EA EA200600950A patent/EA010026B1/ru not_active IP Right Cessation
- 2004-11-10 BR BRPI0416361-3A patent/BRPI0416361A/pt not_active IP Right Cessation
- 2004-11-10 EP EP04810780A patent/EP1682499B1/en not_active Expired - Lifetime
- 2004-11-10 DK DK04810780T patent/DK1682499T3/da active
- 2004-11-10 KR KR1020067011344A patent/KR20070050861A/ko not_active Ceased
- 2004-11-10 PL PL380414A patent/PL380414A1/pl not_active Application Discontinuation
- 2004-11-10 MX MXPA06005106A patent/MXPA06005106A/es active IP Right Grant
- 2004-11-10 WO PCT/US2004/037715 patent/WO2005047248A1/en not_active Ceased
- 2004-11-10 JP JP2006539874A patent/JP2007520453A/ja active Pending
- 2004-11-10 DE DE602004008100T patent/DE602004008100T2/de not_active Expired - Lifetime
- 2004-11-10 ES ES04810780T patent/ES2291974T3/es not_active Expired - Lifetime
- 2004-11-10 CA CA002545058A patent/CA2545058A1/en not_active Abandoned
- 2004-11-10 US US10/986,570 patent/US7320972B2/en not_active Expired - Fee Related
- 2004-11-10 NZ NZ546940A patent/NZ546940A/en unknown
- 2004-11-10 PL PL04810780T patent/PL1682499T3/pl unknown
- 2004-11-10 PT PT04810780T patent/PT1682499E/pt unknown
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2006
- 2006-05-04 IL IL175414A patent/IL175414A0/en unknown
- 2006-05-05 MA MA29006A patent/MA28216A1/fr unknown
- 2006-06-09 NO NO20062665A patent/NO20062665L/no not_active Application Discontinuation
-
2007
- 2007-11-08 CY CY20071101429T patent/CY1106982T1/el unknown
- 2007-12-11 US US11/954,170 patent/US20080167255A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070050861A (ko) | 2007-05-16 |
| US20050209165A1 (en) | 2005-09-22 |
| DK1682499T3 (da) | 2008-01-02 |
| CA2545058A1 (en) | 2005-05-26 |
| US7320972B2 (en) | 2008-01-22 |
| US20080167255A1 (en) | 2008-07-10 |
| WO2005047248A1 (en) | 2005-05-26 |
| DE602004008100D1 (de) | 2007-09-20 |
| MXPA06005106A (es) | 2007-01-25 |
| IL175414A0 (en) | 2006-09-05 |
| ATE369335T1 (de) | 2007-08-15 |
| DE602004008100T2 (de) | 2008-04-30 |
| PT1682499E (pt) | 2007-11-05 |
| JP2007520453A (ja) | 2007-07-26 |
| AU2004288822A1 (en) | 2005-05-26 |
| PL380414A1 (pl) | 2007-01-22 |
| NO20062665L (no) | 2006-08-09 |
| EA200600950A1 (ru) | 2006-10-27 |
| MA28216A1 (fr) | 2006-10-02 |
| NZ546940A (en) | 2008-11-28 |
| HK1093974A1 (en) | 2007-03-16 |
| EP1682499B1 (en) | 2007-08-08 |
| CY1106982T1 (el) | 2012-09-26 |
| BRPI0416361A (pt) | 2007-05-08 |
| PL1682499T3 (pl) | 2008-01-31 |
| EP1682499A1 (en) | 2006-07-26 |
| EA010026B1 (ru) | 2008-06-30 |
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