DE102005018191A1 - Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln - Google Patents
Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln Download PDFInfo
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- DE102005018191A1 DE102005018191A1 DE102005018191A DE102005018191A DE102005018191A1 DE 102005018191 A1 DE102005018191 A1 DE 102005018191A1 DE 102005018191 A DE102005018191 A DE 102005018191A DE 102005018191 A DE102005018191 A DE 102005018191A DE 102005018191 A1 DE102005018191 A1 DE 102005018191A1
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- butyl
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- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000003814 drug Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 221
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 8
- -1 methylenedioxy Chemical group 0.000 claims description 210
- 125000001424 substituent group Chemical group 0.000 claims description 116
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 113
- 150000003254 radicals Chemical class 0.000 claims description 85
- 239000000460 chlorine Substances 0.000 claims description 83
- 239000012429 reaction media Substances 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 71
- 229910052801 chlorine Inorganic materials 0.000 claims description 70
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 68
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 63
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 55
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 54
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 52
- 239000002585 base Substances 0.000 claims description 52
- 208000002193 Pain Diseases 0.000 claims description 51
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 50
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 40
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 40
- 229910052740 iodine Inorganic materials 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 208000011117 substance-related disease Diseases 0.000 claims description 38
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 34
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
- 238000002156 mixing Methods 0.000 claims description 26
- 206010013663 drug dependence Diseases 0.000 claims description 25
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 23
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 23
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 239000012312 sodium hydride Substances 0.000 claims description 23
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 229910052987 metal hydride Inorganic materials 0.000 claims description 21
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 20
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 20
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 20
- 235000009518 sodium iodide Nutrition 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000011591 potassium Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 108010025083 TRPV1 receptor Proteins 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 206010013654 Drug abuse Diseases 0.000 claims description 13
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 13
- 150000005840 aryl radicals Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 12
- 125000006023 1-pentenyl group Chemical group 0.000 claims description 12
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 12
- 125000006024 2-pentenyl group Chemical group 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 12
- 208000007848 Alcoholism Diseases 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 12
- 208000000094 Chronic Pain Diseases 0.000 claims description 12
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 12
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 12
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 208000020629 overactive bladder Diseases 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000006017 1-propenyl group Chemical group 0.000 claims description 11
- 208000005298 acute pain Diseases 0.000 claims description 11
- 229960002504 capsaicin Drugs 0.000 claims description 11
- 235000017663 capsaicin Nutrition 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- MKTBNEVNQZSLKZ-UHFFFAOYSA-N n-[4-[[2-oxo-3-[[4-(trifluoromethoxy)phenyl]methyl]benzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CN1C(=O)N(CC=2C=CC(OC(F)(F)F)=CC=2)C2=CC=CC=C21 MKTBNEVNQZSLKZ-UHFFFAOYSA-N 0.000 claims description 11
- YQCAHQCLQBFUAR-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxobenzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)C2=CC=CC=C21 YQCAHQCLQBFUAR-UHFFFAOYSA-N 0.000 claims description 11
- 208000004296 neuralgia Diseases 0.000 claims description 11
- 208000021722 neuropathic pain Diseases 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 108050004388 Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- WBCBMZUWDPQZTE-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxoimidazolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 WBCBMZUWDPQZTE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 10
- 208000009935 visceral pain Diseases 0.000 claims description 10
- 206010046543 Urinary incontinence Diseases 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000011161 development Methods 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- SFBOPJGETMJNNI-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-sulfanylidenebenzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=S)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)C2=CC=CC=C21 SFBOPJGETMJNNI-UHFFFAOYSA-N 0.000 claims description 9
- PBSTZASQOWSHIK-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-sulfanylideneimidazolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=S)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CC1 PBSTZASQOWSHIK-UHFFFAOYSA-N 0.000 claims description 9
- RCZMUSLCJGVJAG-UHFFFAOYSA-N n-[4-[[3-[[4-(methanesulfonamido)phenyl]methyl]-2-oxobenzimidazol-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)C2=CC=CC=C21 RCZMUSLCJGVJAG-UHFFFAOYSA-N 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 9
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 238000005304 joining Methods 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- CQHFJJKPVBEQPR-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-oxo-1,3-diazinan-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CCC1 CQHFJJKPVBEQPR-UHFFFAOYSA-N 0.000 claims description 7
- NHBDEQGHBWNKCL-UHFFFAOYSA-N n-[4-[[3-[(4-tert-butylphenyl)methyl]-2-sulfanylidene-1,3-diazinan-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=S)N(CC=2C=CC(NS(C)(=O)=O)=CC=2)CCC1 NHBDEQGHBWNKCL-UHFFFAOYSA-N 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 7
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- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
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- 229940005483 opioid analgesics Drugs 0.000 claims description 6
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 6
- 125000005543 phthalimide group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- OUEKLNJUMVZULZ-UHFFFAOYSA-N 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-n-[3-(3,4-dimethylphenyl)propyl]acetamide;hydron;chloride Chemical compound Cl.C1=C(OCCN)C(OC)=CC(CC(=O)NCCCC=2C=C(C)C(C)=CC=2)=C1 OUEKLNJUMVZULZ-UHFFFAOYSA-N 0.000 claims description 5
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- 208000003251 Pruritus Diseases 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 210000000748 cardiovascular system Anatomy 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 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 5
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims description 5
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- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 5
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- RLWGDRLXZSLGHV-UHFFFAOYSA-N 1-[[4-(2-aminoethoxy)-3-methoxyphenyl]methyl]-3-[(4-tert-butylphenyl)methyl]urea Chemical compound C1=C(OCCN)C(OC)=CC(CNC(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1 RLWGDRLXZSLGHV-UHFFFAOYSA-N 0.000 claims description 4
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- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 claims description 4
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- OPZKBPQVWDSATI-KHPPLWFESA-N N-Vanillyloleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-KHPPLWFESA-N 0.000 claims description 4
- QVLMCRFQGHWOPM-ZKWNWVNESA-N N-arachidonoyl vanillylamine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC1=CC=C(O)C(OC)=C1 QVLMCRFQGHWOPM-ZKWNWVNESA-N 0.000 claims description 4
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Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005018191A DE102005018191A1 (de) | 2005-04-19 | 2005-04-19 | Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
| EP06742597A EP1874733B1 (de) | 2005-04-19 | 2006-04-18 | Substituierte zyklische harnstoff-derivate und deren verwendung als vanilloid-rezeptor 1 modulatoren |
| ES06742597T ES2386796T3 (es) | 2005-04-19 | 2006-04-18 | Derivados de urea cíclicos sustituidos y su utilización como moduladores del receptor vainilloide 1 |
| JP2008506989A JP5214436B2 (ja) | 2005-04-19 | 2006-04-18 | 置換された環状尿素誘導体及び医薬の製造へのその使用 |
| PCT/EP2006/003519 WO2006111346A1 (de) | 2005-04-19 | 2006-04-18 | Substituierte zyklische harnstoff-derivate und deren verwendung als vanilloid-rezeptor 1 modulatoren |
| PL06742597T PL1874733T3 (pl) | 2005-04-19 | 2006-04-18 | Podstawione cykliczne pochodne mocznika i ich zastosowanie jako modulatory receptora vaniloidowego 1 |
| CA2605144A CA2605144C (en) | 2005-04-19 | 2006-04-18 | Substituted cyclic urea derivatives and the use thereof as vanilloid receptor 1 modulators |
| US11/875,570 US8207182B2 (en) | 2005-04-19 | 2007-10-19 | Substituted cyclic urea derivatives and the use thereof as vanilloid receptor 1 modulators |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005018191A DE102005018191A1 (de) | 2005-04-19 | 2005-04-19 | Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005018191A1 true DE102005018191A1 (de) | 2006-10-26 |
Family
ID=36764431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005018191A Withdrawn DE102005018191A1 (de) | 2005-04-19 | 2005-04-19 | Substituierte zyklische Harnstoff-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8207182B2 (https=) |
| EP (1) | EP1874733B1 (https=) |
| JP (1) | JP5214436B2 (https=) |
| CA (1) | CA2605144C (https=) |
| DE (1) | DE102005018191A1 (https=) |
| ES (1) | ES2386796T3 (https=) |
| PL (1) | PL1874733T3 (https=) |
| WO (1) | WO2006111346A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008029168A3 (en) * | 2006-09-08 | 2008-05-02 | Summit Corp Plc | Treatment of duchenne muscular dystrophy |
| WO2011018790A1 (en) * | 2009-08-12 | 2011-02-17 | Technion Research & Development Foundation Ltd. | Polycyclic compounds, termed calixurenes, and uses thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8557872B2 (en) | 2008-01-28 | 2013-10-15 | Amorepacific Corporation | Compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and pharmaceutical compositions containing the same |
| US8691855B2 (en) | 2008-07-02 | 2014-04-08 | Amorepacific Corporation | Compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist and pharmaceutical compositions containing the same |
| US8815265B2 (en) | 2010-06-30 | 2014-08-26 | Avon Products, Inc. | Cosmetic use of N-substituted sulfonyloxybenzylamines and related compounds |
| KR102505374B1 (ko) * | 2016-10-06 | 2023-03-02 | 닛산 가가쿠 가부시키가이샤 | 디아민, 중합체, 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| US20240287019A1 (en) * | 2021-06-07 | 2024-08-29 | Kinki University | T-type calcium channel blocker |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4300912A1 (de) * | 1993-01-15 | 1994-07-21 | Merck Patent Gmbh | Chinazolinderivate |
| EP0694536A1 (fr) * | 1994-07-05 | 1996-01-31 | Sanofi | Dérivés de 1-benzyl-1,3-dihydro-2H-benzimidazol-2-one, leur préparation, et compositions pharmaceutiques les contenant |
| WO1996038421A1 (en) * | 1995-06-02 | 1996-12-05 | Berlex Laboratories, Inc. | N,n-di(arylmethyl)cyclic urea derivatives as anti-coagulants |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670368A1 (de) * | 1966-07-16 | 1970-11-05 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung aralkylsubstituierter Lactame und Cyclischer Harnstoffe |
| JPS588503B2 (ja) * | 1974-12-27 | 1983-02-16 | 富士写真フイルム株式会社 | カラ−シヤシンカンコウザイリヨウ |
| JPS58203976A (ja) * | 1982-05-24 | 1983-11-28 | Sumitomo Chem Co Ltd | ベンズイミダゾリン−２−チオン誘導体の製造法 |
| JPS63170011A (ja) * | 1987-01-07 | 1988-07-13 | Mitsubishi Monsanto Chem Co | アミド系樹脂成形品およびその製造法 |
| GB8724912D0 (en) | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
| WO1997008150A1 (en) * | 1995-08-22 | 1997-03-06 | The Du Pont Merck Pharmaceutical Company | Substituted cyclic ureas and derivatives thereof useful as retroviral protease inhibitors |
| AU2001280229B2 (en) * | 2000-08-21 | 2006-12-07 | Pacific Corporation | Novel thiourea derivatives and the pharmaceutical compositions containing the same |
| WO2004103281A2 (en) * | 2003-05-16 | 2004-12-02 | Georgetown University | Vanilloid receptor antagonists, and methods of making and using them |
| US20090264650A1 (en) | 2005-03-31 | 2009-10-22 | Nobuo Cho | Prophylactic/Therapeutic Agent for Diabetes |
-
2005
- 2005-04-19 DE DE102005018191A patent/DE102005018191A1/de not_active Withdrawn
-
2006
- 2006-04-18 EP EP06742597A patent/EP1874733B1/de not_active Expired - Lifetime
- 2006-04-18 PL PL06742597T patent/PL1874733T3/pl unknown
- 2006-04-18 ES ES06742597T patent/ES2386796T3/es not_active Expired - Lifetime
- 2006-04-18 CA CA2605144A patent/CA2605144C/en not_active Expired - Fee Related
- 2006-04-18 WO PCT/EP2006/003519 patent/WO2006111346A1/de not_active Ceased
- 2006-04-18 JP JP2008506989A patent/JP5214436B2/ja not_active Expired - Fee Related
-
2007
- 2007-10-19 US US11/875,570 patent/US8207182B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4300912A1 (de) * | 1993-01-15 | 1994-07-21 | Merck Patent Gmbh | Chinazolinderivate |
| EP0694536A1 (fr) * | 1994-07-05 | 1996-01-31 | Sanofi | Dérivés de 1-benzyl-1,3-dihydro-2H-benzimidazol-2-one, leur préparation, et compositions pharmaceutiques les contenant |
| WO1996038421A1 (en) * | 1995-06-02 | 1996-12-05 | Berlex Laboratories, Inc. | N,n-di(arylmethyl)cyclic urea derivatives as anti-coagulants |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008029168A3 (en) * | 2006-09-08 | 2008-05-02 | Summit Corp Plc | Treatment of duchenne muscular dystrophy |
| WO2011018790A1 (en) * | 2009-08-12 | 2011-02-17 | Technion Research & Development Foundation Ltd. | Polycyclic compounds, termed calixurenes, and uses thereof |
| US8962605B2 (en) | 2009-08-12 | 2015-02-24 | Technion Research & Development Foundation Limited | Polycyclic compounds, termed calixurenes, and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080090855A1 (en) | 2008-04-17 |
| CA2605144C (en) | 2014-05-27 |
| WO2006111346A1 (de) | 2006-10-26 |
| US8207182B2 (en) | 2012-06-26 |
| CA2605144A1 (en) | 2006-10-26 |
| JP5214436B2 (ja) | 2013-06-19 |
| PL1874733T3 (pl) | 2012-09-28 |
| EP1874733A1 (de) | 2008-01-09 |
| JP2008538366A (ja) | 2008-10-23 |
| ES2386796T3 (es) | 2012-08-30 |
| EP1874733B1 (de) | 2012-06-20 |
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