JP2012521401A5 - - Google Patents
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- Publication number
- JP2012521401A5 JP2012521401A5 JP2012501401A JP2012501401A JP2012521401A5 JP 2012521401 A5 JP2012521401 A5 JP 2012521401A5 JP 2012501401 A JP2012501401 A JP 2012501401A JP 2012501401 A JP2012501401 A JP 2012501401A JP 2012521401 A5 JP2012521401 A5 JP 2012521401A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxo
- pyrimidin
- acetamide
- tetrahydro
- thiazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 cyano, hydroxyl Chemical group 0.000 claims 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 10
- 208000002193 Pain Diseases 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 201000001119 neuropathy Diseases 0.000 claims 3
- 230000007823 neuropathy Effects 0.000 claims 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010011224 Cough Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 101000764872 Homo sapiens Transient receptor potential cation channel subfamily A member 1 Proteins 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 102100026186 Transient receptor potential cation channel subfamily A member 1 Human genes 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- PWFCNAOHVWWKNG-UHFFFAOYSA-N 2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)-n-[4-(2,3,4-trichlorophenyl)-1,3-thiazol-2-yl]acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(Cl)C(Cl)=C1Cl PWFCNAOHVWWKNG-UHFFFAOYSA-N 0.000 claims 1
- VJXIKTQSMMQMOO-UHFFFAOYSA-N 2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)-n-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(C(F)(F)F)C(F)=C1 VJXIKTQSMMQMOO-UHFFFAOYSA-N 0.000 claims 1
- HHGALMGKEXDRBM-UHFFFAOYSA-N 2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)-n-[4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(C)(C)C)C(F)=C1 HHGALMGKEXDRBM-UHFFFAOYSA-N 0.000 claims 1
- DTXASEKLDRHEQO-UHFFFAOYSA-N 2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)-n-[4-[4-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(F)C(C(F)(F)F)=C1 DTXASEKLDRHEQO-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 206010017886 Gastroduodenal ulcer Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000004454 Hyperalgesia Diseases 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000028389 Nerve injury Diseases 0.000 claims 1
- 206010030216 Oesophagitis Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 208000008469 Peptic Ulcer Diseases 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 208000008765 Sciatica Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 206010047700 Vomiting Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 150000005347 biaryls Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000006881 esophagitis Diseases 0.000 claims 1
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- XGDWUOTWCBUFBF-UHFFFAOYSA-N n-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(F)C=C1F XGDWUOTWCBUFBF-UHFFFAOYSA-N 0.000 claims 1
- QKIWOLBTEJUIKO-UHFFFAOYSA-N n-[4-[2,4-difluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[2,3-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1N(C)C=C2CC(=O)NC(SC=1)=NC=1C1=CC=C(F)C(C(F)(F)F)=C1F QKIWOLBTEJUIKO-UHFFFAOYSA-N 0.000 claims 1
- MIQCXSCTXQXGMO-UHFFFAOYSA-N n-[4-[3,5-dichloro-4-(2,2-dimethylpropoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(Cl)=C(OCC(C)(C)C)C(Cl)=C1 MIQCXSCTXQXGMO-UHFFFAOYSA-N 0.000 claims 1
- MSAYCLQQORKAFC-UHFFFAOYSA-N n-[4-[3,5-dichloro-4-(3,3,3-trifluoropropoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(Cl)=C(OCCC(F)(F)F)C(Cl)=C1 MSAYCLQQORKAFC-UHFFFAOYSA-N 0.000 claims 1
- MJKVMFJIWCAVBS-UHFFFAOYSA-N n-[4-[3,5-dichloro-4-(3,3,4,4,4-pentafluorobutoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(Cl)=C(OCCC(F)(F)C(F)(F)F)C(Cl)=C1 MJKVMFJIWCAVBS-UHFFFAOYSA-N 0.000 claims 1
- PNDMPMPPVJPCBO-UHFFFAOYSA-N n-[4-[3,5-dichloro-4-(cyclobutylmethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C(C=C1Cl)=CC(Cl)=C1OCC1CCC1 PNDMPMPPVJPCBO-UHFFFAOYSA-N 0.000 claims 1
- QMTNZUVGQYBRTR-UHFFFAOYSA-N n-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(F)(F)F)C(F)=C1 QMTNZUVGQYBRTR-UHFFFAOYSA-N 0.000 claims 1
- MMHXOTLTEZVHSY-UHFFFAOYSA-N n-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[2,3-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1N(C)C=C2CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(F)(F)F)C(F)=C1 MMHXOTLTEZVHSY-UHFFFAOYSA-N 0.000 claims 1
- NLQAMAXKCHXKCL-UHFFFAOYSA-N n-[4-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(F)(F)F)C(F)=C1 NLQAMAXKCHXKCL-UHFFFAOYSA-N 0.000 claims 1
- OKQXLYYFMPXFAX-UHFFFAOYSA-N n-[4-[3,5-difluoro-4-(3,3,3-trifluoropropoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCCC(F)(F)F)C(F)=C1 OKQXLYYFMPXFAX-UHFFFAOYSA-N 0.000 claims 1
- HMHDLTBMXATXHH-UHFFFAOYSA-N n-[4-[3,5-difluoro-4-(3-methylbutoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=C(F)C(OCCC(C)C)=C(F)C=C1C1=CSC(NC(=O)CN2C=3C(=O)N(C)C(=O)N(C)C=3C=C2)=N1 HMHDLTBMXATXHH-UHFFFAOYSA-N 0.000 claims 1
- FAGOKVRNGXRBLZ-UHFFFAOYSA-N n-[4-[3-bromo-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(OCC(F)(F)F)C(Br)=C1 FAGOKVRNGXRBLZ-UHFFFAOYSA-N 0.000 claims 1
- MPFSSCWDMILAOW-UHFFFAOYSA-N n-[4-[3-chloro-4-(2,2-dimethylpropoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C1=CC=C(OCC(C)(C)C)C(Cl)=C1 MPFSSCWDMILAOW-UHFFFAOYSA-N 0.000 claims 1
- SLOZYXXAOWEARH-UHFFFAOYSA-N n-[4-[3-chloro-5-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(F)(F)F)C(Cl)=C1 SLOZYXXAOWEARH-UHFFFAOYSA-N 0.000 claims 1
- DVEXKZCKMAEQGO-UHFFFAOYSA-N n-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C1=CC=C(C(F)(F)F)C(F)=C1 DVEXKZCKMAEQGO-UHFFFAOYSA-N 0.000 claims 1
- JPMLQKMNYAURPB-UHFFFAOYSA-N n-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[2,3-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1N(C)C=C2CC(=O)NC(SC=1)=NC=1C1=CC=C(C(F)(F)F)C(F)=C1 JPMLQKMNYAURPB-UHFFFAOYSA-N 0.000 claims 1
- HYUWZKXSCQQPNU-UHFFFAOYSA-N n-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1C(C)=CN2CC(=O)NC(SC=1)=NC=1C1=CC=C(C(F)(F)F)C(F)=C1 HYUWZKXSCQQPNU-UHFFFAOYSA-N 0.000 claims 1
- AZAOVWSEIOTYCH-UHFFFAOYSA-N n-[4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(C)(C)C)C(F)=C1 AZAOVWSEIOTYCH-UHFFFAOYSA-N 0.000 claims 1
- MOBOEILXZWMKQG-UHFFFAOYSA-N n-[4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[2,3-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1N(C)C=C2CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(C)(C)C)C(F)=C1 MOBOEILXZWMKQG-UHFFFAOYSA-N 0.000 claims 1
- MROYRQVEHRGXHI-UHFFFAOYSA-N n-[4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3,7-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CN1C(=O)N(C)C(=O)C2=C1C(C)=CN2CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OCC(C)(C)C)C(F)=C1 MROYRQVEHRGXHI-UHFFFAOYSA-N 0.000 claims 1
- NLDCRIGVFPWIIR-UHFFFAOYSA-N n-[4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(F)C(OCC(C)(C)C)=C(F)C=2)=C1 NLDCRIGVFPWIIR-UHFFFAOYSA-N 0.000 claims 1
- ZVGKXJDRPSRLQF-UHFFFAOYSA-N n-[4-[4-(2,2-dimethylpropoxy)-3-fluorophenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C1=CC=C(OCC(C)(C)C)C(F)=C1 ZVGKXJDRPSRLQF-UHFFFAOYSA-N 0.000 claims 1
- OYHGLGOLPALEOM-UHFFFAOYSA-N n-[4-[4-(cyclobutylmethoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound CC1=CC=2N(C)C(=O)N(C)C(=O)C=2N1CC(=O)NC(SC=1)=NC=1C(C=C1F)=CC(F)=C1OCC1CCC1 OYHGLGOLPALEOM-UHFFFAOYSA-N 0.000 claims 1
- RHMISVBJYQSDSS-UHFFFAOYSA-N n-[4-[4-(cyclopropylmethoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C(C=C1F)=CC(F)=C1OCC1CC1 RHMISVBJYQSDSS-UHFFFAOYSA-N 0.000 claims 1
- IAZLFUFODLEFKX-UHFFFAOYSA-N n-[4-[4-(difluoromethoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC(F)=C(OC(F)F)C(F)=C1 IAZLFUFODLEFKX-UHFFFAOYSA-N 0.000 claims 1
- UZCBRKYSYQOZEM-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,4-dioxopyrrolo[3,2-d]pyrimidin-5-yl)acetamide Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2C=CN1CC(=O)NC(SC=1)=NC=1C1=CC=C(Cl)C(C(F)(F)F)=C1 UZCBRKYSYQOZEM-UHFFFAOYSA-N 0.000 claims 1
- 230000008764 nerve damage Effects 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000003349 osteoarthritic effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
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- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
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- 150000003852 triazoles Chemical class 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
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| US17135509P | 2009-04-21 | 2009-04-21 | |
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| US61/300,241 | 2010-02-01 | ||
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| KR101591153B1 (ko) | 2010-12-20 | 2016-02-02 | 그렌마크 파머수티칼스 에스. 아. | Trpa1 길항제로서의 2-아미노-4-아릴티아졸 화합물 |
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| EP2520566A1 (en) | 2011-05-06 | 2012-11-07 | Orion Corporation | New Pharmaceutical Compounds |
| WO2012172475A1 (en) | 2011-06-13 | 2012-12-20 | Glenmark Pharmaceuticals S.A. | Treatment of respiratory disorders using trpa1 antagonists |
| WO2012176143A1 (en) | 2011-06-22 | 2012-12-27 | Glenmark Pharmaceuticals Sa | Pharmaceutical composition comprising a trpa1 antagonist and a beta-2 agonist |
| WO2012176105A1 (en) | 2011-06-22 | 2012-12-27 | Glenmark Pharmaceuticals Sa | Pharmaceutical composition comprising a trpa1 antagonist and a leukotriene receptor antagonist |
| CA2841417A1 (en) | 2011-07-25 | 2013-01-31 | Glenmark Pharmaceuticals Sa | Pharmaceutical composition comprising a trpa1 antagonist and a steroid |
| MX2014001551A (es) | 2011-08-09 | 2014-09-15 | Hydra Biosciences Inc | Inhibicion de canal ionico del potencial receptor transitorio a1 (trpa1). |
| WO2013084153A1 (en) | 2011-12-05 | 2013-06-13 | Glenmark Pharmaceuticals S.A. | Pharmaceutical composition comprising a trpa1 antagonist and an anticholinergic agent |
| JP6182072B2 (ja) | 2012-01-17 | 2017-08-16 | Ｅａファーマ株式会社 | 複素環アミド誘導体及びそれを含有する医薬 |
| AU2013273118B2 (en) | 2012-06-08 | 2015-11-05 | Glenmark Pharmaceuticals S.A. | Amides of 2-amino-4-arylthiazole compounds and their salts |
| KR102164756B1 (ko) | 2012-10-01 | 2020-10-14 | 오리온 코포레이션 | N-프로프-2-이닐 카복스아미드 유도체 및 trpa1 길항제로서의 이의 용도 |
| US9394308B2 (en) | 2013-01-18 | 2016-07-19 | Merck Sharp & Dohme Corp. | Inhibiting the transient receptor potential A1 ion channel |
| RU2016115093A (ru) | 2013-10-15 | 2017-11-21 | Гленмарк Фармасьютикалс С.А. | Фармацевтическая композиция, содержащая антагонист trpa1 и анальгетический агент |
| ES2747839T3 (es) | 2013-10-30 | 2020-03-11 | Shanghai hengrui pharmaceutical co ltd | Derivados de pirazolopirimidona o de pirrolotriazona, método de preparación de los mismos, y aplicaciones farmacéuticas de los mismos |
| CN103755705B (zh) * | 2014-02-17 | 2017-02-15 | 上海佰特因医药科技有限公司 | 一种天然产物四甲基尿酸的全合成方法 |
| JP6667092B2 (ja) * | 2014-08-11 | 2020-03-18 | ハイドラ・バイオサイエンシーズ・リミテッド・ライアビリティ・カンパニーＨｙｄｒａ Ｂｉｏｓｃｉｅｎｃｅｓ， ＬＬＣ | ピロロ［３，２−ｄ］ピリミジン−２，４（３Ｈ，５Ｈ）−ジオン誘導体 |
| WO2016042501A1 (en) | 2014-09-16 | 2016-03-24 | Glenmark Pharmaceuticals S.A. | Trpa1 antagonist for the treatment of pain associated to diabetic neuropathic pain |
| CN105001170A (zh) * | 2015-07-13 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 末端腈基取代的三氮唑亚砜类化合物、其制备方法及其用途 |
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| CN109422749B (zh) * | 2017-08-21 | 2023-01-24 | 重庆医药工业研究院有限责任公司 | 一种抑制单羧酸转运蛋白的嘧啶二酮衍生物 |
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| CN108558836A (zh) * | 2018-05-14 | 2018-09-21 | 东南大学 | 一类具有双重作用机制的dpp-4抑制剂及其用途 |
| WO2023096915A1 (en) * | 2021-11-24 | 2023-06-01 | Slap Pharmaceuticals Llc | Multicyclic compounds |
| CR20240352A (es) * | 2022-02-03 | 2024-09-18 | De Shaw Res Llc | Compuestos de uracilo sustituidos por n3 como inhibidores de trpa1 |
| JP2025510646A (ja) | 2022-03-14 | 2025-04-15 | スラップ ファーマシューティカルズ エルエルシー | 多環式化合物 |
| CN114656473B (zh) * | 2022-04-27 | 2023-09-29 | 成都施贝康生物医药科技有限公司 | 吡咯并嘧啶类化合物、异构体或盐及其制备方法和用途 |
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2010
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- 2010-03-17 DK DK10755503.9T patent/DK2411393T3/da active
- 2010-03-17 CA CA2756518A patent/CA2756518A1/en not_active Abandoned
- 2010-03-17 EA EA201190143A patent/EA023857B1/ru not_active IP Right Cessation
- 2010-03-17 PL PL10755503T patent/PL2411393T3/pl unknown
- 2010-03-17 PE PE2011001707A patent/PE20120774A1/es not_active Application Discontinuation
- 2010-03-17 SI SI201030523T patent/SI2411393T1/sl unknown
- 2010-03-17 EP EP13005523.9A patent/EP2708538B1/en not_active Not-in-force
- 2010-03-17 CN CN201080013471.6A patent/CN102361873B/zh not_active Expired - Fee Related
- 2010-03-17 UA UAA201111147A patent/UA108069C2/uk unknown
- 2010-03-17 AU AU2010227245A patent/AU2010227245B2/en not_active Ceased
- 2010-03-17 MX MX2011009824A patent/MX2011009824A/es unknown
- 2010-03-17 SG SG2011066487A patent/SG174402A1/en unknown
- 2010-03-17 JP JP2012501401A patent/JP5657638B2/ja not_active Expired - Fee Related
- 2010-03-17 ES ES13005523.9T patent/ES2551085T3/es active Active
- 2010-03-17 ES ES10755503.9T patent/ES2456515T3/es active Active
- 2010-03-17 PT PT107555039T patent/PT2411393E/pt unknown
- 2010-03-17 AP AP2011005887A patent/AP3280A/xx active
- 2010-03-17 WO PCT/IB2010/000553 patent/WO2010109287A1/en not_active Ceased
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2011
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2013
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2014
- 2014-06-02 CL CL2014001447A patent/CL2014001447A1/es unknown
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