OA12868A - Ring-substituted diphenyl azetidinones, method forthe production thereof, medicaments containing sa id compounds and use thereof. - Google Patents

Info

Publication number

OA12868A

OA12868A OA1200400330A OA1200400330A OA12868A OA 12868 A OA12868 A OA 12868A OA 1200400330 A OA1200400330 A OA 1200400330A OA 1200400330 A OA1200400330 A OA 1200400330A OA 12868 A OA12868 A OA 12868A

Authority

OA

OAPI

Prior art keywords

alkyl

phenyl

crc6

cooh

radical

Prior art date

2002-06-19

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 128
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
• 238000000034 method Methods 0.000 title abstract description 8
• 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 5
• 239000003814 drug Substances 0.000 title abstract description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 74
• -1 COO(CrC6)-alkyl Chemical group 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 239000000556 agonist Substances 0.000 claims description 32
• 229910052794 bromium Inorganic materials 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 229910052740 iodine Inorganic materials 0.000 claims description 20
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 20
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 17
• 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 claims description 16
• 235000000346 sugar Nutrition 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 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
• 235000001014 amino acid Nutrition 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
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
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• 238000010521 absorption reaction Methods 0.000 claims description 9
• 125000002015 acyclic group Chemical group 0.000 claims description 9
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
• 239000005557 antagonist Substances 0.000 claims description 8
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 229910006069 SO3H Inorganic materials 0.000 claims description 6
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• 102000015636 Oligopeptides Human genes 0.000 claims description 5
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• 125000000539 amino acid group Chemical group 0.000 claims description 5
• 150000002337 glycosamines Chemical class 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
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
• 229910018828 PO3H2 Inorganic materials 0.000 claims description 4
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• 239000003613 bile acid Substances 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 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
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
• 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
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• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 230000003178 anti-diabetic effect Effects 0.000 claims description 3
• 230000001419 dependent effect Effects 0.000 claims description 3
• 239000000122 growth hormone Substances 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
• 229940039781 leptin Drugs 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
• 108090000662 ATP citrate synthases Proteins 0.000 claims description 2
• 229940123208 Biguanide Drugs 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 101800002068 Galanin Proteins 0.000 claims description 2
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
• 102000000853 LDL receptors Human genes 0.000 claims description 2
• 108010001831 LDL receptors Proteins 0.000 claims description 2
• 102000004882 Lipase Human genes 0.000 claims description 2
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• 102000057248 Lipoprotein(a) Human genes 0.000 claims description 2
• 108010033266 Lipoprotein(a) Proteins 0.000 claims description 2
• 229940124757 MC-4 agonist Drugs 0.000 claims description 2
• 102000002512 Orexin Human genes 0.000 claims description 2
• 102000023984 PPAR alpha Human genes 0.000 claims description 2
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• 102000005630 Urocortins Human genes 0.000 claims description 2
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• 239000003392 amylase inhibitor Substances 0.000 claims description 2
• 239000003963 antioxidant agent Substances 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 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
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
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• 235000019421 lipase Nutrition 0.000 claims description 2
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• 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
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• 150000001467 thiazolidinediones Chemical class 0.000 claims description 2
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• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
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