JP2009521417A5 - - Google Patents
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- Publication number
- JP2009521417A5 JP2009521417A5 JP2008546171A JP2008546171A JP2009521417A5 JP 2009521417 A5 JP2009521417 A5 JP 2009521417A5 JP 2008546171 A JP2008546171 A JP 2008546171A JP 2008546171 A JP2008546171 A JP 2008546171A JP 2009521417 A5 JP2009521417 A5 JP 2009521417A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ethyl
- methoxy
- hydrogen
- fluoro
- 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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- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 35
- -1 2-propyn-1-yl Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 241000534944 Thia Species 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 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 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 108010052164 Sodium Channels Proteins 0.000 claims 6
- 102000018674 Sodium Channels Human genes 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 4
- 230000004064 dysfunction Effects 0.000 claims 4
- 102000038650 voltage-gated calcium channel activity Human genes 0.000 claims 4
- 108091023044 voltage-gated calcium channel activity Proteins 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- CHDGDDDVSLMZMW-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl-(2-methylpropyl)amino]-n-methylacetamide Chemical compound COC1=CC(CCN(CC(=O)NC)CC(C)C)=CC=C1OCC1=CC=CC(F)=C1 CHDGDDDVSLMZMW-UHFFFAOYSA-N 0.000 claims 2
- SDNXCGUYOQGANK-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl-(oxolan-3-ylmethyl)amino]-n-methylacetamide Chemical compound C1COCC1CN(CC(=O)NC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 SDNXCGUYOQGANK-UHFFFAOYSA-N 0.000 claims 2
- UKMKLUFLCSKXBV-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-1-pyrrolidin-1-ylethanone Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC=1C=CC=CC=1)CC(=O)N1CCCC1 UKMKLUFLCSKXBV-UHFFFAOYSA-N 0.000 claims 2
- CWKUKNFDLVJHRQ-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n-[2-(1-methylpyrrolidin-2-yl)ethyl]acetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC=1C=CC=CC=1)CC(=O)NCCC1CCCN1C CWKUKNFDLVJHRQ-UHFFFAOYSA-N 0.000 claims 2
- ZLTXAXQFAACBOF-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC(=O)NCCN(C)C)CC1=CC=CC=C1 ZLTXAXQFAACBOF-UHFFFAOYSA-N 0.000 claims 2
- JQTQIYUGFVPIJV-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n-ethylacetamide Chemical compound C1CC1CN(CC(=O)NCC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 JQTQIYUGFVPIJV-UHFFFAOYSA-N 0.000 claims 2
- HJZLNGPRJYSQFU-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n-methylacetamide Chemical compound C1CC1CN(CC(=O)NC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 HJZLNGPRJYSQFU-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 108090000312 Calcium Channels Proteins 0.000 claims 2
- 102000003922 Calcium Channels Human genes 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- GDLFGGXPILNFIS-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-2-[2-[3-[(3-fluorophenyl)methoxy]phenyl]ethyl-(furan-2-ylmethyl)amino]acetamide Chemical compound C=1C=COC=1CN(CC(=O)NCC(C)(N)C)CCC(C=1)=CC=CC=1OCC1=CC=CC(F)=C1 GDLFGGXPILNFIS-UHFFFAOYSA-N 0.000 claims 2
- WGADHETXYPKGJR-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]acetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC(=O)NCC(C)(C)N)CC1=CC=CC=C1 WGADHETXYPKGJR-UHFFFAOYSA-N 0.000 claims 2
- XYZGEXCERRUYCU-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[2-[3-[(3-fluorophenyl)methoxy]phenyl]ethyl-(furan-2-ylmethyl)amino]acetamide Chemical compound C=1C=COC=1CN(CC(=O)NCCN(C)C)CCC(C=1)=CC=CC=1OCC1=CC=CC(F)=C1 XYZGEXCERRUYCU-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- ZMTXXDXSTAMMGX-UHFFFAOYSA-N 2-[2-(3-butoxyphenyl)ethyl-(furan-2-ylmethyl)amino]-n-methylacetamide Chemical compound CCCCOC1=CC=CC(CCN(CC(=O)NC)CC=2OC=CC=2)=C1 ZMTXXDXSTAMMGX-UHFFFAOYSA-N 0.000 claims 1
- ZKDHFQPTAYMLAC-UHFFFAOYSA-N 2-[2-(3-butoxyphenyl)ethyl-(oxolan-3-ylmethyl)amino]-n,n-dimethylacetamide Chemical compound CCCCOC1=CC=CC(CCN(CC2COCC2)CC(=O)N(C)C)=C1 ZKDHFQPTAYMLAC-UHFFFAOYSA-N 0.000 claims 1
- OTLQHUJQPLEXOC-UHFFFAOYSA-N 2-[2-[3-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]ethyl-(oxolan-3-yl)amino]-n,n-dimethylacetamide Chemical compound C1COCC1N(CC(=O)N(C)C)CCC(C=1)=CC=CC=1C=1C(C)=NOC=1C OTLQHUJQPLEXOC-UHFFFAOYSA-N 0.000 claims 1
- XGZGDCZLYATHIX-UHFFFAOYSA-N 2-[2-[3-(3-fluorophenyl)phenyl]ethyl-(furan-2-ylmethyl)amino]-n-methylacetamide Chemical compound C=1C=COC=1CN(CC(=O)NC)CCC(C=1)=CC=CC=1C1=CC=CC(F)=C1 XGZGDCZLYATHIX-UHFFFAOYSA-N 0.000 claims 1
- QMBIMQBLVIZLDK-UHFFFAOYSA-N 2-[2-[3-[(2-fluorophenyl)methoxy]phenyl]ethyl-(furan-2-ylmethyl)amino]-n-methylacetamide Chemical compound C=1C=COC=1CN(CC(=O)NC)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1F QMBIMQBLVIZLDK-UHFFFAOYSA-N 0.000 claims 1
- IQHFCTKLHPTBJT-UHFFFAOYSA-N 2-[2-[3-[(3-fluorophenyl)methoxy]phenyl]ethyl-(furan-2-ylmethyl)amino]acetamide Chemical compound C=1C=COC=1CN(CC(=O)N)CCC(C=1)=CC=CC=1OCC1=CC=CC(F)=C1 IQHFCTKLHPTBJT-UHFFFAOYSA-N 0.000 claims 1
- STTVJGXMPRQHSJ-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl-(furan-3-ylmethyl)amino]-n-methylacetamide Chemical compound C1=COC=C1CN(CC(=O)NC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 STTVJGXMPRQHSJ-UHFFFAOYSA-N 0.000 claims 1
- HDLYNPUXEIEJJC-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl-[(6-methoxypyridin-3-yl)methyl]amino]-n-methylacetamide Chemical compound C=1C=C(OC)N=CC=1CN(CC(=O)NC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 HDLYNPUXEIEJJC-UHFFFAOYSA-N 0.000 claims 1
- MGRDJWRFGWKOAN-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethylamino]-1-morpholin-4-yl-2-phenylethanone Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCNC(C=1C=CC=CC=1)C(=O)N1CCOCC1 MGRDJWRFGWKOAN-UHFFFAOYSA-N 0.000 claims 1
- BXNZJECUEURCQU-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethylamino]-n,n-dimethyl-2-phenylacetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCNC(C(=O)N(C)C)C1=CC=CC=C1 BXNZJECUEURCQU-UHFFFAOYSA-N 0.000 claims 1
- IDYXIOXSNSPCPT-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethylamino]-n,n-dimethylacetamide Chemical compound COC1=CC(CCNCC(=O)N(C)C)=CC=C1OCC1=CC=CC(F)=C1 IDYXIOXSNSPCPT-UHFFFAOYSA-N 0.000 claims 1
- DREFJWNEYPRVCO-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethylamino]-n,n-dimethylpropanamide Chemical compound COC1=CC(CCNC(C)C(=O)N(C)C)=CC=C1OCC1=CC=CC(F)=C1 DREFJWNEYPRVCO-UHFFFAOYSA-N 0.000 claims 1
- MCGCVSJLZDQXNI-UHFFFAOYSA-N 2-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethylamino]-n-methylacetamide Chemical compound COC1=CC(CCNCC(=O)NC)=CC=C1OCC1=CC=CC(F)=C1 MCGCVSJLZDQXNI-UHFFFAOYSA-N 0.000 claims 1
- FPMSYWAPQIKMDK-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(2,2,2-trifluoroethoxy)phenyl]ethyl-(oxolan-3-ylmethyl)amino]-n,n-dimethylacetamide Chemical compound C1COCC1CN(CC(=O)N(C)C)CCC1=CC=C(F)C(OCC(F)(F)F)=C1 FPMSYWAPQIKMDK-UHFFFAOYSA-N 0.000 claims 1
- RXTAKOUJBRJDQC-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n,n-dimethylacetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC(=O)N(C)C)CC1=CC=CC=C1 RXTAKOUJBRJDQC-UHFFFAOYSA-N 0.000 claims 1
- JMEBXRRKXHQQBB-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]-n-ethylacetamide Chemical compound C=1C=CC=CC=1CN(CC(=O)NCC)CCC(C=C1OC)=CC=C1OCC1=CC=CC(F)=C1 JMEBXRRKXHQQBB-UHFFFAOYSA-N 0.000 claims 1
- DDSSOOVRWNROTL-UHFFFAOYSA-N 2-[benzyl-[2-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]ethyl]amino]acetamide Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1CCN(CC(N)=O)CC1=CC=CC=C1 DDSSOOVRWNROTL-UHFFFAOYSA-N 0.000 claims 1
- CEVSPUZVBKXFQG-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-(3-methoxy-4-phenylmethoxyphenyl)ethyl]amino]-n-methylacetamide Chemical compound C1CC1CN(CC(=O)NC)CCC(C=C1OC)=CC=C1OCC1=CC=CC=C1 CEVSPUZVBKXFQG-UHFFFAOYSA-N 0.000 claims 1
- OXHXQWRDRUSNNF-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-(3-phenylmethoxyphenyl)ethyl]amino]-n-methylacetamide Chemical compound C1CC1CN(CC(=O)NC)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 OXHXQWRDRUSNNF-UHFFFAOYSA-N 0.000 claims 1
- RRWNJZUEWLDYHR-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-(3-phenylmethoxyphenyl)ethyl]amino]-n-methylpropanamide Chemical compound C1CC1CN(C(C)C(=O)NC)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 RRWNJZUEWLDYHR-UHFFFAOYSA-N 0.000 claims 1
- HTRJGVMTESRNOP-UHFFFAOYSA-N 2-[cyclopropylmethyl-[2-[3-methoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethyl]amino]-n-methylacetamide Chemical compound C1CC1CN(CC(=O)NC)CCC1=CC=C(OCC(F)(F)F)C(OC)=C1 HTRJGVMTESRNOP-UHFFFAOYSA-N 0.000 claims 1
- XPXAHFDXEVRUDF-UHFFFAOYSA-N 2-[furan-2-ylmethyl-[2-(3-phenylmethoxyphenyl)ethyl]amino]-n-methylacetamide Chemical compound C=1C=COC=1CN(CC(=O)NC)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 XPXAHFDXEVRUDF-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 241001279686 Allium moly Species 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 206010060860 Neurological symptom Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- PUTWHLMMZAMMCK-UHFFFAOYSA-N n,n-dimethyl-2-[oxolan-3-yl-[2-[3-(2,2,2-trifluoroethoxy)phenyl]ethyl]amino]acetamide Chemical compound C1COCC1N(CC(=O)N(C)C)CCC1=CC=CC(OCC(F)(F)F)=C1 PUTWHLMMZAMMCK-UHFFFAOYSA-N 0.000 claims 1
- UMQXRXHYGCCQFM-UHFFFAOYSA-N n,n-dimethyl-2-[oxolan-3-ylmethyl-[2-(3-phenylmethoxyphenyl)ethyl]amino]acetamide Chemical compound C1COCC1CN(CC(=O)N(C)C)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 UMQXRXHYGCCQFM-UHFFFAOYSA-N 0.000 claims 1
- RYQBJXRLVNLLOZ-UHFFFAOYSA-N n,n-dimethyl-2-[oxolan-3-ylmethyl-[2-(3-piperidin-1-ylphenyl)ethyl]amino]acetamide Chemical compound C1COCC1CN(CC(=O)N(C)C)CCC(C=1)=CC=CC=1N1CCCCC1 RYQBJXRLVNLLOZ-UHFFFAOYSA-N 0.000 claims 1
- NNFXNHAKUFWTHD-UHFFFAOYSA-N n,n-dimethyl-2-[oxolan-3-ylmethyl-[2-[3-(2,2,2-trifluoroethoxy)phenyl]ethyl]amino]acetamide Chemical compound C1COCC1CN(CC(=O)N(C)C)CCC1=CC=CC(OCC(F)(F)F)=C1 NNFXNHAKUFWTHD-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05028147 | 2005-12-22 | ||
| EP05028147.6 | 2005-12-22 | ||
| PCT/EP2006/011443 WO2007071311A1 (en) | 2005-12-22 | 2006-11-29 | 2 -phenylethylamino derivatives as calcium and/or sodium channel modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009521417A JP2009521417A (ja) | 2009-06-04 |
| JP2009521417A5 true JP2009521417A5 (https=) | 2012-04-19 |
| JP5271087B2 JP5271087B2 (ja) | 2013-08-21 |
Family
ID=36178203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008546171A Active JP5271087B2 (ja) | 2005-12-22 | 2006-11-29 | カルシウム及び／又はナトリウムチャネル調節物質としての２−フェニルエチルアミノ誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US7855227B2 (https=) |
| EP (1) | EP1963280B1 (https=) |
| JP (1) | JP5271087B2 (https=) |
| KR (1) | KR101380137B1 (https=) |
| CN (1) | CN101309909B (https=) |
| AR (1) | AR058720A1 (https=) |
| AU (1) | AU2006329040C1 (https=) |
| BR (1) | BRPI0620239B8 (https=) |
| CA (1) | CA2629065C (https=) |
| CY (1) | CY1117094T1 (https=) |
| DK (1) | DK1963280T3 (https=) |
| ES (1) | ES2556937T3 (https=) |
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| HU (1) | HUE028329T2 (https=) |
| IL (1) | IL191255A (https=) |
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| SI (1) | SI1963280T1 (https=) |
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| DK1658062T3 (da) * | 2003-08-25 | 2010-05-31 | Newron Pharm Spa | Alfa-aminoamid-derivater anvendelige som anti-inflammatoriske midler |
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| PT2723710T (pt) * | 2011-06-27 | 2016-11-14 | Newron Pharm Spa | Derivados fluorados de arilalquilaminocarboxamida |
| CA2850925C (en) | 2011-10-26 | 2017-01-10 | Pfizer Limited | (4-phenylimidazol-2-yl) ethylamine derivatives useful as sodium channel modulators |
| CN103804341B (zh) * | 2012-11-13 | 2018-04-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 酰胺衍生物及其医药用途 |
| CN104761531B (zh) * | 2014-01-03 | 2017-12-01 | 中国人民解放军军事医学科学院毒物药物研究所 | 镇痛活性化合物及其医药用途 |
| CN106795098B (zh) * | 2014-10-02 | 2020-07-14 | 默加拜奥伍德有限公司 | α-氨基酰胺衍生化合物及包含其的药物组合物 |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| EP3723807B1 (en) | 2017-12-14 | 2021-10-20 | H. Lundbeck A/S | Combination treatments comprising administration of 1h-pyrazolo[4,3-b]pyridines |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| WO2019121840A1 (en) | 2017-12-20 | 2019-06-27 | H. Lundbeck A/S | Pyrazolo[3,4-b]pyridines and imidazo[1,5-b]pyridazines as pde1 inhibitors |
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| EP3725768A1 (en) * | 2019-04-17 | 2020-10-21 | Newron Pharmaceuticals S.p.A. | Process for the production of substituted 2-[2-(phenyl) ethylamino]alkaneamide derivatives |
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