MXPA04012236A - Difenilazetidinonas sustituidas en anillo, metodo para su produccion, medicamentos que comprenden estos compuestos y su uso. - Google Patents
Difenilazetidinonas sustituidas en anillo, metodo para su produccion, medicamentos que comprenden estos compuestos y su uso.Info
- Publication number
- MXPA04012236A MXPA04012236A MXPA04012236A MXPA04012236A MXPA04012236A MX PA04012236 A MXPA04012236 A MX PA04012236A MX PA04012236 A MXPA04012236 A MX PA04012236A MX PA04012236 A MXPA04012236 A MX PA04012236A MX PA04012236 A MXPA04012236 A MX PA04012236A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- phenyl
- radical
- cooh
- agonists
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 239000003814 drug Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 11
- VDOXIAUNJCHYRC-UHFFFAOYSA-N 1,3-diphenylazetidin-2-one Chemical class O=C1C(C=2C=CC=CC=2)CN1C1=CC=CC=C1 VDOXIAUNJCHYRC-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 4
- -1 COO-alkyl (Ci-C6) Chemical group 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- 239000000556 agonist Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 235000000346 sugar Nutrition 0.000 claims description 15
- 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 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000002015 acyclic group Chemical group 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 102000004877 Insulin Human genes 0.000 claims description 7
- 108090001061 Insulin Proteins 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000005557 antagonist Substances 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000539 amino acid group Chemical group 0.000 claims description 5
- 150000002016 disaccharides Chemical group 0.000 claims description 5
- 150000002337 glycosamines Chemical class 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 150000004044 tetrasaccharides Chemical group 0.000 claims description 5
- 150000004043 trisaccharides Chemical group 0.000 claims description 5
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
- 102000015636 Oligopeptides Human genes 0.000 claims description 4
- 108010038807 Oligopeptides Proteins 0.000 claims description 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 4
- 239000000122 growth hormone Substances 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 102000018997 Growth Hormone Human genes 0.000 claims description 3
- 108010051696 Growth Hormone Proteins 0.000 claims description 3
- 102000016267 Leptin Human genes 0.000 claims description 3
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- 102000004257 Potassium Channel Human genes 0.000 claims description 3
- 230000003178 anti-diabetic effect Effects 0.000 claims description 3
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 3
- 230000001906 cholesterol absorption Effects 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 229940039781 leptin Drugs 0.000 claims description 3
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 3
- 230000037356 lipid metabolism Effects 0.000 claims description 3
- 229950004994 meglitinide Drugs 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 108020001213 potassium channel Proteins 0.000 claims description 3
- 102000004146 ATP citrate synthases Human genes 0.000 claims description 2
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- 102000013585 Bombesin Human genes 0.000 claims description 2
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
- 102000000853 LDL receptors Human genes 0.000 claims description 2
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- 239000004367 Lipase Substances 0.000 claims description 2
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- 108010013563 Lipoprotein Lipase Proteins 0.000 claims description 2
- 102100022119 Lipoprotein lipase Human genes 0.000 claims description 2
- 102000002512 Orexin Human genes 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims description 2
- 102000005630 Urocortins Human genes 0.000 claims description 2
- 108010059705 Urocortins Proteins 0.000 claims description 2
- 239000003392 amylase inhibitor Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 claims description 2
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims description 2
- 229960002802 bromocriptine Drugs 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
- 230000001771 impaired effect Effects 0.000 claims description 2
- 239000000411 inducer Substances 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 claims description 2
- 230000002474 noradrenergic effect Effects 0.000 claims description 2
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- 239000004059 squalene synthase inhibitor Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- 229940127470 Lipase Inhibitors Drugs 0.000 claims 2
- 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 claims 2
- 229940123208 Biguanide Drugs 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 102000019432 Galanin Human genes 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
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- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 claims 1
- 102000023984 PPAR alpha Human genes 0.000 claims 1
- 108010028924 PPAR alpha Proteins 0.000 claims 1
- 102000000536 PPAR gamma Human genes 0.000 claims 1
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- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 150000004283 biguanides Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
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- 239000004026 insulin derivative Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 abstract description 2
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- 208000035150 Hypercholesterolemia Diseases 0.000 abstract 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 81
- 239000000047 product Substances 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
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- 239000007787 solid Substances 0.000 description 19
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 13
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- 150000001768 cations Chemical class 0.000 description 12
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- SDOFMBGMRVAJNF-UHFFFAOYSA-N 6-aminohexane-1,2,3,4,5-pentol Chemical compound NCC(O)C(O)C(O)C(O)CO SDOFMBGMRVAJNF-UHFFFAOYSA-N 0.000 description 10
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- 239000007937 lozenge Substances 0.000 description 1
- 239000002697 lyase inhibitor Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960000299 mazindol Drugs 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960001110 miglitol Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZICFPEHQRZAFBZ-UHFFFAOYSA-N n-(4-fluorophenyl)-1-(4-methoxyphenyl)methanimine Chemical compound C1=CC(OC)=CC=C1C=NC1=CC=C(F)C=C1 ZICFPEHQRZAFBZ-UHFFFAOYSA-N 0.000 description 1
- LYAUICDWKQJAGX-UHFFFAOYSA-N n-(7-hydroxy-2,2,4,6-tetramethyl-1,3-dihydroinden-1-yl)-2-[4-(3-methoxyphenyl)piperazin-1-yl]acetamide Chemical compound COC1=CC=CC(N2CCN(CC(=O)NC3C(CC4=C3C(=C(C)C=C4C)O)(C)C)CC2)=C1 LYAUICDWKQJAGX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- HSNZZMHEPUFJNZ-SHUUEZRQSA-N sedoheptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-SHUUEZRQSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229950004437 tiqueside Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- SIOVKLKJSOKLIF-CMDGGOBGSA-N trimethylsilyl (1e)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N/[Si](C)(C)C SIOVKLKJSOKLIF-CMDGGOBGSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- JPZXHKDZASGCLU-LBPRGKRZSA-N β-(2-naphthyl)-alanine Chemical compound C1=CC=CC2=CC(C[C@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-LBPRGKRZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10227506A DE10227506A1 (de) | 2002-06-19 | 2002-06-19 | Ringsubstituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| PCT/EP2003/005815 WO2004000804A1 (de) | 2002-06-19 | 2003-06-04 | Ringsubstituierte diphenylazetidinone, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04012236A true MXPA04012236A (es) | 2005-02-25 |
Family
ID=29719281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04012236A MXPA04012236A (es) | 2002-06-19 | 2003-06-04 | Difenilazetidinonas sustituidas en anillo, metodo para su produccion, medicamentos que comprenden estos compuestos y su uso. |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1517892B1 (enExample) |
| JP (1) | JP2005533072A (enExample) |
| CN (1) | CN1662493A (enExample) |
| AR (1) | AR039689A1 (enExample) |
| AT (1) | ATE478842T1 (enExample) |
| AU (1) | AU2003242616B2 (enExample) |
| BR (1) | BR0311940A (enExample) |
| CA (1) | CA2490109A1 (enExample) |
| DE (2) | DE10227506A1 (enExample) |
| EC (1) | ECSP045498A (enExample) |
| HN (1) | HN2003000183A (enExample) |
| HR (1) | HRP20041203A2 (enExample) |
| IL (1) | IL165791A0 (enExample) |
| MA (1) | MA27252A1 (enExample) |
| MX (1) | MXPA04012236A (enExample) |
| MY (1) | MY135850A (enExample) |
| NO (1) | NO20050073L (enExample) |
| NZ (1) | NZ537304A (enExample) |
| OA (1) | OA12868A (enExample) |
| PA (1) | PA8576001A1 (enExample) |
| PE (1) | PE20040577A1 (enExample) |
| PL (1) | PL372690A1 (enExample) |
| RS (1) | RS108504A (enExample) |
| RU (1) | RU2315754C2 (enExample) |
| SV (1) | SV2004001549A (enExample) |
| TN (1) | TNSN04255A1 (enExample) |
| TW (1) | TW200404774A (enExample) |
| UY (1) | UY27851A1 (enExample) |
| WO (1) | WO2004000804A1 (enExample) |
| ZA (1) | ZA200409381B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0215579D0 (en) | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
| US7447226B2 (en) * | 2003-10-31 | 2008-11-04 | International Business Machines Corporation | Methods and apparatus for continuous connectivity between mobile device and network using dynamic connection spreading |
| EP1699759B1 (en) | 2003-12-23 | 2010-10-20 | AstraZeneca AB | Diphenylazetidinone derivates possessing cholesterol absorption inhibitory activity |
| ES2435790T3 (es) | 2004-12-03 | 2013-12-23 | Intervet International B.V. | Piperazinas sustituidas como antagonistas de CB1 |
| US8361999B2 (en) | 2005-04-04 | 2013-01-29 | Pontificia Universidad Catolica De Chile | Methods of treating cholesterol gallstone disease with ezetimibe |
| ATE450526T1 (de) | 2005-06-20 | 2009-12-15 | Schering Corp | Als antagonisten von histamin h3 geeignete piperidinderivate |
| 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 |
| AR060623A1 (es) | 2006-04-27 | 2008-07-02 | Astrazeneca Ab | Compuestos derivados de 2-azetidinona y un metodo de preparacion |
| MX2009001043A (es) | 2006-08-08 | 2009-02-06 | Sanofi Aventis | Imidazolidina-2,4-dionas sustituidas con arilaminoarilalquilo, procedimiento para preparalas, medicamentos que comprenden estos compuestos y su uso. |
| RU2009120679A (ru) * | 2006-11-02 | 2010-12-10 | Санофи-Авентис Дойчланд Гмбх (De) | Новый дифенилазетидинон, замещенный пиперазин-1-сульфокислотой, обладающий улучшенными фармакологическими свойствами |
| DE102007002260A1 (de) | 2007-01-16 | 2008-07-31 | Sanofi-Aventis | Verwendung von substituierten Pyranonsäurederivaten zur Herstellung von Medikamenten zur Behandlung des Metabolischen Syndroms |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007063671A1 (de) | 2007-11-13 | 2009-06-25 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| EP2310372B1 (en) | 2008-07-09 | 2012-05-23 | Sanofi | 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 |
| WO2010100255A1 (en) | 2009-03-06 | 2010-09-10 | Lipideon Biotechnology Ag | Pharmaceutical hypocholesterolemic compositions |
| CN101993403B (zh) | 2009-08-11 | 2012-07-11 | 浙江海正药业股份有限公司 | 氮杂环丁酮类化合物及医药应用 |
| US8785608B2 (en) | 2009-08-26 | 2014-07-22 | Sanofi | Crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| 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 |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte 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 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2235943C (en) * | 1995-10-31 | 2002-10-01 | Schering Corporation | Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents |
| DE10042447A1 (de) * | 2000-08-29 | 2002-03-28 | Aventis Pharma Gmbh | Protein aus dem Darm von Wirbeltieren, welches Cholesterin absorbiert, sowie Verwendung dieses Proteins zur Identifizierung von Inhibitoren des intestinalen Cholesterintransports |
-
2002
- 2002-06-19 DE DE10227506A patent/DE10227506A1/de not_active Withdrawn
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2003
- 2003-01-17 HN HN2003000183A patent/HN2003000183A/es unknown
- 2003-06-02 SV SV2003001549A patent/SV2004001549A/es not_active Application Discontinuation
- 2003-06-04 OA OA1200400330A patent/OA12868A/en unknown
- 2003-06-04 MX MXPA04012236A patent/MXPA04012236A/es active IP Right Grant
- 2003-06-04 AU AU2003242616A patent/AU2003242616B2/en not_active Ceased
- 2003-06-04 NZ NZ537304A patent/NZ537304A/en unknown
- 2003-06-04 PL PL03372690A patent/PL372690A1/xx not_active Application Discontinuation
- 2003-06-04 AT AT03760591T patent/ATE478842T1/de active
- 2003-06-04 CN CN03814087XA patent/CN1662493A/zh active Pending
- 2003-06-04 BR BR0311940-8A patent/BR0311940A/pt not_active IP Right Cessation
- 2003-06-04 JP JP2004514660A patent/JP2005533072A/ja not_active Abandoned
- 2003-06-04 RU RU2005101091/04A patent/RU2315754C2/ru not_active IP Right Cessation
- 2003-06-04 RS YUP-1085/04A patent/RS108504A/sr unknown
- 2003-06-04 EP EP03760591A patent/EP1517892B1/de not_active Expired - Lifetime
- 2003-06-04 CA CA002490109A patent/CA2490109A1/en not_active Abandoned
- 2003-06-04 HR HR20041203A patent/HRP20041203A2/xx not_active Application Discontinuation
- 2003-06-04 DE DE50313017T patent/DE50313017D1/de not_active Expired - Lifetime
- 2003-06-04 WO PCT/EP2003/005815 patent/WO2004000804A1/de not_active Ceased
- 2003-06-16 UY UY27851A patent/UY27851A1/es unknown
- 2003-06-17 AR ARP030102142A patent/AR039689A1/es unknown
- 2003-06-17 TW TW092116319A patent/TW200404774A/zh unknown
- 2003-06-18 PE PE2003000613A patent/PE20040577A1/es not_active Application Discontinuation
- 2003-06-18 MY MYPI20032289A patent/MY135850A/en unknown
- 2003-06-18 PA PA20038576001A patent/PA8576001A1/es unknown
-
2004
- 2004-11-22 ZA ZA200409381A patent/ZA200409381B/xx unknown
- 2004-12-08 MA MA27990A patent/MA27252A1/fr unknown
- 2004-12-15 IL IL16579104A patent/IL165791A0/xx unknown
- 2004-12-16 EC EC2004005498A patent/ECSP045498A/es unknown
- 2004-12-17 TN TNP2004000255A patent/TNSN04255A1/en unknown
-
2005
- 2005-01-06 NO NO20050073A patent/NO20050073L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2005101091A (ru) | 2005-07-10 |
| TW200404774A (en) | 2004-04-01 |
| RS108504A (sr) | 2007-02-05 |
| HRP20041203A2 (en) | 2005-06-30 |
| RU2315754C2 (ru) | 2008-01-27 |
| PA8576001A1 (es) | 2004-02-07 |
| DE10227506A1 (de) | 2004-01-08 |
| MA27252A1 (fr) | 2005-03-01 |
| EP1517892B1 (de) | 2010-08-25 |
| TNSN04255A1 (en) | 2007-03-12 |
| JP2005533072A (ja) | 2005-11-04 |
| NO20050073L (no) | 2005-01-06 |
| AR039689A1 (es) | 2005-03-09 |
| UY27851A1 (es) | 2003-12-31 |
| PL372690A1 (en) | 2005-07-25 |
| CN1662493A (zh) | 2005-08-31 |
| EP1517892A1 (de) | 2005-03-30 |
| IL165791A0 (en) | 2006-01-15 |
| WO2004000804A1 (de) | 2003-12-31 |
| BR0311940A (pt) | 2005-04-05 |
| ZA200409381B (en) | 2006-05-31 |
| AU2003242616B2 (en) | 2008-12-11 |
| HN2003000183A (es) | 2003-08-01 |
| ATE478842T1 (de) | 2010-09-15 |
| AU2003242616A1 (en) | 2004-01-06 |
| DE50313017D1 (de) | 2010-10-07 |
| MY135850A (en) | 2008-07-31 |
| PE20040577A1 (es) | 2004-10-11 |
| OA12868A (en) | 2006-09-15 |
| CA2490109A1 (en) | 2003-12-31 |
| SV2004001549A (es) | 2004-03-19 |
| ECSP045498A (es) | 2005-03-10 |
| NZ537304A (en) | 2005-10-28 |
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| FG | Grant or registration |