UA76969C2 - Lactams and their pharmaceutical use - Google Patents

Info

Publication number

UA76969C2

UA76969C2 UA2003055026A UA2003055026A UA76969C2 UA 76969 C2 UA76969 C2 UA 76969C2 UA 2003055026 A UA2003055026 A UA 2003055026A UA 2003055026 A UA2003055026 A UA 2003055026A UA 76969 C2 UA76969 C2 UA 76969C2

Authority

UA

Ukraine

Prior art keywords

substituent

group

acyl

alkyl

carbamoyl

Prior art date

2000-12-01

Links

• Espacenet
• Global Dossier
• Discuss

• 150000003951 lactams Chemical class 0.000 title claims description 24
• -1 lactam compounds Chemical class 0.000 claims abstract description 98
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
• 239000004480 active ingredient Substances 0.000 claims abstract description 11
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 7
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 7
• 208000008589 Obesity Diseases 0.000 claims abstract description 7
• 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 7
• 235000020824 obesity Nutrition 0.000 claims abstract description 7
• 125000001424 substituent group Chemical group 0.000 claims description 144
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 125000002252 acyl group Chemical group 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 235000000346 sugar Nutrition 0.000 claims description 37
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 33
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 125000004423 acyloxy group Chemical group 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 125000004414 alkyl thio group Chemical group 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 238000012546 transfer Methods 0.000 claims description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 21
• 125000003277 amino group Chemical group 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 125000001931 aliphatic group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 150000004820 halides Chemical class 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 230000002093 peripheral effect Effects 0.000 claims description 8
• 125000001769 aryl amino group Chemical group 0.000 claims description 7
• 125000003609 aryl vinyl group Chemical group 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 206010063547 Diabetic macroangiopathy Diseases 0.000 claims description 6
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 239000003472 antidiabetic agent Substances 0.000 claims description 3
• 229940126904 hypoglycaemic agent Drugs 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 238000012876 topography Methods 0.000 claims 1
• 239000008103 glucose Substances 0.000 abstract description 9
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 6
• 239000003814 drug Substances 0.000 abstract description 6
• 229940079593 drug Drugs 0.000 abstract description 5
• 230000003389 potentiating effect Effects 0.000 abstract description 2
• 230000003449 preventive effect Effects 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 183
• 238000000034 method Methods 0.000 description 79
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 239000007858 starting material Substances 0.000 description 40
• 239000000243 solution Substances 0.000 description 38
• 230000000694 effects Effects 0.000 description 36
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• 230000015572 biosynthetic process Effects 0.000 description 32
• 239000000203 mixture Substances 0.000 description 32
• 238000003786 synthesis reaction Methods 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 30
• WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 30
• 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 29
• 238000005481 NMR spectroscopy Methods 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 150000001299 aldehydes Chemical class 0.000 description 23
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• 229940125396 insulin Drugs 0.000 description 15
• IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 14
• RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical compound OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 description 14
• 102000004877 Insulin Human genes 0.000 description 14
• 108090001061 Insulin Proteins 0.000 description 14
• 150000001923 cyclic compounds Chemical class 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 229910052740 iodine Inorganic materials 0.000 description 13
• 229910052700 potassium Inorganic materials 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 238000001914 filtration Methods 0.000 description 12
• 239000000047 product Substances 0.000 description 11
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• 239000008280 blood Substances 0.000 description 10
• 210000004369 blood Anatomy 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• ZBEGLEYBWGNZJA-UHFFFAOYSA-N 4-dodecoxybenzaldehyde Chemical compound CCCCCCCCCCCCOC1=CC=C(C=O)C=C1 ZBEGLEYBWGNZJA-UHFFFAOYSA-N 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 238000000605 extraction Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 239000004698 Polyethylene Substances 0.000 description 7
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
• 210000001789 adipocyte Anatomy 0.000 description 7
• 150000002081 enamines Chemical class 0.000 description 7
• 238000001308 synthesis method Methods 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• 230000032258 transport Effects 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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• 241000700159 Rattus Species 0.000 description 5
• 235000011054 acetic acid Nutrition 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 239000001257 hydrogen Substances 0.000 description 5
• 229910052739 hydrogen Inorganic materials 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 description 5
• DOQJUNNMZNNQAD-UHFFFAOYSA-N pyrrolidine-2,4-dione Chemical compound O=C1CNC(=O)C1 DOQJUNNMZNNQAD-UHFFFAOYSA-N 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052717 sulfur Inorganic materials 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
• NRKQMDLBMZFWDM-UHFFFAOYSA-N 4-tert-butyl-2-chlorobenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(Cl)=C1 NRKQMDLBMZFWDM-UHFFFAOYSA-N 0.000 description 4
• 235000010469 Glycine max Nutrition 0.000 description 4
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 241001424341 Tara spinosa Species 0.000 description 4
• 238000007792 addition Methods 0.000 description 4
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• 238000002560 therapeutic procedure Methods 0.000 description 4
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• 238000005406 washing Methods 0.000 description 4
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• AUTGLFSBJLERMV-UHFFFAOYSA-N 2-phenylpyrimidine-5-carbaldehyde Chemical compound N1=CC(C=O)=CN=C1C1=CC=CC=C1 AUTGLFSBJLERMV-UHFFFAOYSA-N 0.000 description 3
• SYCFYQFCFHKYPI-UHFFFAOYSA-N 4-(2-phenylethynyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C#CC1=CC=CC=C1 SYCFYQFCFHKYPI-UHFFFAOYSA-N 0.000 description 3
• MGHIIGWDUVNPPV-UHFFFAOYSA-N 4-(4-nitrophenyl)benzaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C=O)C=C1 MGHIIGWDUVNPPV-UHFFFAOYSA-N 0.000 description 3
• XVBUHGDSGIKMMT-UHFFFAOYSA-N 4-butoxy-2-methoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OC)=C1 XVBUHGDSGIKMMT-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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• PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
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• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
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