JP2006518746A5 - - Google Patents
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- Publication number
- JP2006518746A5 JP2006518746A5 JP2006503737A JP2006503737A JP2006518746A5 JP 2006518746 A5 JP2006518746 A5 JP 2006518746A5 JP 2006503737 A JP2006503737 A JP 2006503737A JP 2006503737 A JP2006503737 A JP 2006503737A JP 2006518746 A5 JP2006518746 A5 JP 2006518746A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- pyridinyl
- methyl
- oct
- carboxamide
- 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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- 229910052717 sulfur Chemical group 0.000 claims 398
- -1 oct-3-yl Chemical group 0.000 claims 211
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 40
- 239000004202 carbamide Substances 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 24
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 13
- 239000003814 drug Substances 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 6
- 208000015114 central nervous system disease Diseases 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- LIQVEXOTZPWBDF-UHFFFAOYSA-N 1-benzofuran-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=COC2=C1 LIQVEXOTZPWBDF-UHFFFAOYSA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 2
- 239000002525 vasculotropin inhibitor Substances 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- PVICREAWTADNSB-UHFFFAOYSA-N (2,4-dimethoxyphenyl)carbamic acid Chemical compound COC1=CC=C(NC(O)=O)C(OC)=C1 PVICREAWTADNSB-UHFFFAOYSA-N 0.000 claims 1
- FTEZEFRVMRFCJL-UHFFFAOYSA-N (2-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1Br FTEZEFRVMRFCJL-UHFFFAOYSA-N 0.000 claims 1
- OAQKFULUNYIBBR-UHFFFAOYSA-N (2-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1Cl OAQKFULUNYIBBR-UHFFFAOYSA-N 0.000 claims 1
- QXAICYQHORWBRC-UHFFFAOYSA-N (2-cyanophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1C#N QXAICYQHORWBRC-UHFFFAOYSA-N 0.000 claims 1
- FTLCLAFMYWOANF-UHFFFAOYSA-N (2-fluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1F FTLCLAFMYWOANF-UHFFFAOYSA-N 0.000 claims 1
- DBLSJJAIARSHKC-UHFFFAOYSA-N (2-methoxyphenyl)carbamic acid Chemical compound COC1=CC=CC=C1NC(O)=O DBLSJJAIARSHKC-UHFFFAOYSA-N 0.000 claims 1
- AXVPVXHGWJWEPI-UHFFFAOYSA-N (2-methylphenyl)carbamic acid Chemical compound CC1=CC=CC=C1NC(O)=O AXVPVXHGWJWEPI-UHFFFAOYSA-N 0.000 claims 1
- QBTMBDZBQWTSIH-UHFFFAOYSA-N (2-methylsulfanylphenyl)carbamic acid Chemical compound CSC1=CC=CC=C1NC(O)=O QBTMBDZBQWTSIH-UHFFFAOYSA-N 0.000 claims 1
- CCBMTBNWUDKADX-UHFFFAOYSA-N (2-phenoxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 CCBMTBNWUDKADX-UHFFFAOYSA-N 0.000 claims 1
- RKZNZYKONLPRCE-UHFFFAOYSA-N (2-phenylsulfanylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1SC1=CC=CC=C1 RKZNZYKONLPRCE-UHFFFAOYSA-N 0.000 claims 1
- OAYMUOAVUHJSNG-UHFFFAOYSA-N (3-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Br)=C1 OAYMUOAVUHJSNG-UHFFFAOYSA-N 0.000 claims 1
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 claims 1
- LOYXEARIHRYZDG-UHFFFAOYSA-N (3-cyanophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(C#N)=C1 LOYXEARIHRYZDG-UHFFFAOYSA-N 0.000 claims 1
- VZAZTNWSVRVMDP-UHFFFAOYSA-N (3-fluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(F)=C1 VZAZTNWSVRVMDP-UHFFFAOYSA-N 0.000 claims 1
- LQMWWRSOANZFNV-UHFFFAOYSA-N (3-methoxyphenyl)carbamic acid Chemical compound COC1=CC=CC(NC(O)=O)=C1 LQMWWRSOANZFNV-UHFFFAOYSA-N 0.000 claims 1
- HNAXBZUMENBWSX-UHFFFAOYSA-N (3-methylphenyl)carbamic acid Chemical compound CC1=CC=CC(NC(O)=O)=C1 HNAXBZUMENBWSX-UHFFFAOYSA-N 0.000 claims 1
- FQZDHCYPOORVCD-UHFFFAOYSA-N (3-methylsulfanylphenyl)carbamic acid Chemical compound CSC1=CC=CC(NC(O)=O)=C1 FQZDHCYPOORVCD-UHFFFAOYSA-N 0.000 claims 1
- DMRVIRJPXTULLZ-UHFFFAOYSA-N (3-phenoxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(OC=2C=CC=CC=2)=C1 DMRVIRJPXTULLZ-UHFFFAOYSA-N 0.000 claims 1
- JZEVJAGOTSXSSV-UHFFFAOYSA-N (3-phenylsulfanylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC(SC2=CC=CC=C2)=CC=C1 JZEVJAGOTSXSSV-UHFFFAOYSA-N 0.000 claims 1
- PHVSUUGFGMGZPE-UHFFFAOYSA-N (4-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Br)C=C1 PHVSUUGFGMGZPE-UHFFFAOYSA-N 0.000 claims 1
- GAWCRULEMQFHTI-UHFFFAOYSA-N (4-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C=C1 GAWCRULEMQFHTI-UHFFFAOYSA-N 0.000 claims 1
- AGLXPSZYQNIRPU-UHFFFAOYSA-N (4-cyanophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(C#N)C=C1 AGLXPSZYQNIRPU-UHFFFAOYSA-N 0.000 claims 1
- QVVJZHVEBUNKBZ-UHFFFAOYSA-N (4-fluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(F)C=C1 QVVJZHVEBUNKBZ-UHFFFAOYSA-N 0.000 claims 1
- VZQDNZQCQKJHNO-UHFFFAOYSA-N (4-methoxyphenyl)carbamic acid Chemical compound COC1=CC=C(NC(O)=O)C=C1 VZQDNZQCQKJHNO-UHFFFAOYSA-N 0.000 claims 1
- RHNSSYGTJAAVCR-UHFFFAOYSA-N (4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1 RHNSSYGTJAAVCR-UHFFFAOYSA-N 0.000 claims 1
- OSQOGASVZHDGKF-UHFFFAOYSA-N (4-methylsulfanylphenyl)carbamic acid Chemical compound CSC1=CC=C(NC(O)=O)C=C1 OSQOGASVZHDGKF-UHFFFAOYSA-N 0.000 claims 1
- ULOGWKQPJOGCDK-UHFFFAOYSA-N (4-phenoxyphenyl)carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1OC1=CC=CC=C1 ULOGWKQPJOGCDK-UHFFFAOYSA-N 0.000 claims 1
- SXQANJUOAWVEPB-UHFFFAOYSA-N (4-phenylsulfanylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(SC2=CC=CC=C2)C=C1 SXQANJUOAWVEPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 claims 1
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
- RASGVORPWAYILQ-UHFFFAOYSA-N 1-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCN1CCC2 RASGVORPWAYILQ-UHFFFAOYSA-N 0.000 claims 1
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 claims 1
- QAVSAAADWVRRHO-UHFFFAOYSA-N 1-benzothiophen-3-ylcarbamic acid Chemical compound C1=CC=C2C(NC(=O)O)=CSC2=C1 QAVSAAADWVRRHO-UHFFFAOYSA-N 0.000 claims 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 1
- QXJDOADTRZGPJZ-UHFFFAOYSA-N 1-benzothiophene-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CSC2=C1 QXJDOADTRZGPJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims 1
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 206010036631 Presenile dementia Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- RCFJOIDKQQRXHU-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC(C(F)(F)F)=C1 RCFJOIDKQQRXHU-UHFFFAOYSA-N 0.000 claims 1
- OSIDHOSKWJZDAH-UHFFFAOYSA-N [4-(dimethylamino)phenyl]carbamic acid Chemical compound CN(C)C1=CC=C(NC(O)=O)C=C1 OSIDHOSKWJZDAH-UHFFFAOYSA-N 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000001147 anti-toxic effect Effects 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 201000007201 aphasia Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- VQMXMQWQEILHQK-UHFFFAOYSA-N benzo[e][1]benzofuran-2-carboxamide Chemical compound C1=CC=C2C(C=C(O3)C(=O)N)=C3C=CC2=C1 VQMXMQWQEILHQK-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
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- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
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| PL4041733T3 (pl) | 2019-11-15 | 2024-09-23 | Yuhan Corporation | Pochodne mające ugrupowanie 2,3-dihydro-1h-indenu lub 2,3-dihydrobenzofuranu lub ich farmaceutycznie dopuszczalne sole oraz kompozycje farmaceutyczne je zawierające |
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