JP2012511054A5 - - Google Patents
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- JP2012511054A5 JP2012511054A5 JP2011540836A JP2011540836A JP2012511054A5 JP 2012511054 A5 JP2012511054 A5 JP 2012511054A5 JP 2011540836 A JP2011540836 A JP 2011540836A JP 2011540836 A JP2011540836 A JP 2011540836A JP 2012511054 A5 JP2012511054 A5 JP 2012511054A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- dihydro
- propyl
- methyl
- 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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- -1 -CONR 8 R 9 Chemical group 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 239000012453 solvate Substances 0.000 claims description 33
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 208000002193 Pain Diseases 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 13
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 101150111783 NTRK1 gene Proteins 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 claims description 8
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 208000011117 substance-related disease Diseases 0.000 claims description 8
- 208000024891 symptom Diseases 0.000 claims description 8
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 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 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 201000009032 substance abuse Diseases 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 208000016192 Demyelinating disease Diseases 0.000 claims description 5
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 239000003483 4 aminobutyric acid A receptor stimulating agent Substances 0.000 claims description 4
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 208000029147 Collagen-vascular disease Diseases 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims description 4
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 229940035676 analgesics Drugs 0.000 claims description 4
- 229940035674 anesthetics Drugs 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229940125717 barbiturate Drugs 0.000 claims description 4
- 229940049706 benzodiazepine Drugs 0.000 claims description 4
- 150000001557 benzodiazepines Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000011496 cAMP-mediated signaling Effects 0.000 claims description 4
- 238000002512 chemotherapy Methods 0.000 claims description 4
- 239000003193 general anesthetic agent Substances 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 239000003983 inhalation anesthetic agent Substances 0.000 claims description 4
- 239000003589 local anesthetic agent Substances 0.000 claims description 4
- 230000007246 mechanism Effects 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 4
- 150000003180 prostaglandins Chemical class 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 206010012305 Demyelination Diseases 0.000 claims description 3
- 102000003840 Opioid Receptors Human genes 0.000 claims description 3
- 108090000137 Opioid Receptors Proteins 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 239000000935 antidepressant agent Substances 0.000 claims description 3
- 229940005513 antidepressants Drugs 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 230000001788 irregular Effects 0.000 claims description 3
- 230000023105 myelination Effects 0.000 claims description 3
- 239000002858 neurotransmitter agent Substances 0.000 claims description 3
- CGJMVNVWQHPASW-UHFFFAOYSA-N quinoxaline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CN=C21 CGJMVNVWQHPASW-UHFFFAOYSA-N 0.000 claims description 3
- 229940044601 receptor agonist Drugs 0.000 claims description 3
- 239000000018 receptor agonist Substances 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- XPPBCXSMFHFWEJ-JGCGQSQUSA-N (12ar)-n-[2-(4-benzylpiperidin-1-yl)ethyl]-5-[(3-fluorophenyl)methyl]-6-oxo-7,9,10,11,12,12a-hexahydropyrido[1,2-d][1,4]benzodiazepine-3-carboxamide Chemical compound FC1=CC=CC(CN2C(CN3CCCC[C@@H]3C3=CC=C(C=C32)C(=O)NCCN2CCC(CC=3C=CC=CC=3)CC2)=O)=C1 XPPBCXSMFHFWEJ-JGCGQSQUSA-N 0.000 claims description 2
- JNVLDPFCQWJRQK-NJZRLIGZSA-N (2e)-2-[(4-ethoxy-3-methoxyphenyl)methylidene]-n-[3-[4-(2-fluorophenyl)piperazin-1-yl]propyl]-4-methyl-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=C(OC)C(OCC)=CC=C1\C=C\1C(=O)N(C)C2=CC(C(=O)NCCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2S/1 JNVLDPFCQWJRQK-NJZRLIGZSA-N 0.000 claims description 2
- GIUUODWOUQNAER-XHLNEMQHSA-N (2e)-n-[3-[4-(2-fluorophenyl)piperazin-1-yl]propyl]-2-[(2-methoxyphenyl)methylidene]-4-methyl-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound COC1=CC=CC=C1\C=C\1C(=O)N(C)C2=CC(C(=O)NCCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2S/1 GIUUODWOUQNAER-XHLNEMQHSA-N 0.000 claims description 2
- TUNCBIPYIJLOFJ-BWAHOGKJSA-N (2z)-2-benzylidene-3-oxo-n-[3-(2-propylpiperidin-1-yl)propyl]-4h-1,4-benzothiazine-6-carboxamide Chemical compound CCCC1CCCCN1CCCNC(=O)C1=CC=C(S\C(=C/C=2C=CC=CC=2)C(=O)N2)C2=C1 TUNCBIPYIJLOFJ-BWAHOGKJSA-N 0.000 claims description 2
- CKDUDHCDIRJFPB-FSGOGVSDSA-N (2z)-2-benzylidene-4-[(4-fluorophenyl)methyl]-n-[3-(3-methylpiperidin-1-yl)propyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1C(C)CCCN1CCCNC(=O)C1=CC=C(S\C(=C/C=2C=CC=CC=2)C(=O)N2CC=3C=CC(F)=CC=3)C2=C1 CKDUDHCDIRJFPB-FSGOGVSDSA-N 0.000 claims description 2
- UPPDGSAXSCZMIE-ULJHMMPZSA-N (2z)-2-benzylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-3-oxo-4h-1,4-benzoxazine-6-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C1=CC=C(O\C(=C/C=2C=CC=CC=2)C(=O)N2)C2=C1 UPPDGSAXSCZMIE-ULJHMMPZSA-N 0.000 claims description 2
- ZPTWWFUWWUIMJG-YQYKVWLJSA-N (2z)-2-benzylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C1=CC=C(S\C(=C/C=2C=CC=CC=2)C(=O)N2CC=3C=CC(F)=CC=3)C2=C1 ZPTWWFUWWUIMJG-YQYKVWLJSA-N 0.000 claims description 2
- ABKKAJMGWBGMKT-MZFJOGFUSA-N (2z)-2-benzylidene-n-[3-(3,5-dimethylpiperidin-1-yl)propyl]-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1C(C)CC(C)CN1CCCNC(=O)C1=CC=C(S\C(=C/C=2C=CC=CC=2)C(=O)N2CC=3C=C(C)C=CC=3)C2=C1 ABKKAJMGWBGMKT-MZFJOGFUSA-N 0.000 claims description 2
- URFNQMGOQKRVMA-MNBJERMJSA-N (2z)-2-benzylidene-n-[3-(3,5-dimethylpiperidin-1-yl)propyl]-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1C(C)CC(C)CN1CCCNC(=O)C1=CC=C(S\C(=C/C=2C=CC=CC=2)C(=O)N2CC=3C=CC(F)=CC=3)C2=C1 URFNQMGOQKRVMA-MNBJERMJSA-N 0.000 claims description 2
- WVSOIRKWHGSDBF-UOZKZNBHSA-N (2z)-2-benzylidene-n-[3-(4-benzylpiperidin-1-yl)propyl]-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(=CC=C3SC(/C2=O)=C\C=2C=CC=CC=2)C(=O)NCCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 WVSOIRKWHGSDBF-UOZKZNBHSA-N 0.000 claims description 2
- KRIXOKLRGDHBEF-LAKKEJQSSA-N (2z)-2-benzylidene-n-[3-(4-benzylpiperidin-1-yl)propyl]-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=CC(F)=CC=C1CN(C\1=O)C2=CC(C(=O)NCCCN3CCC(CC=4C=CC=CC=4)CC3)=CC=C2SC/1=C\C1=CC=CC=C1 KRIXOKLRGDHBEF-LAKKEJQSSA-N 0.000 claims description 2
- QLUVLAVLWYGIDK-QEOQBAOWSA-N (2z)-2-benzylidene-n-[3-[4-(2,5-dimethylphenyl)piperazin-1-yl]propyl]-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(=CC=C3SC(/C2=O)=C\C=2C=CC=CC=2)C(=O)NCCCN2CCN(CC2)C=2C(=CC=C(C)C=2)C)=C1 QLUVLAVLWYGIDK-QEOQBAOWSA-N 0.000 claims description 2
- AFKBYNLPCUGDNZ-JDCMOKTRSA-N (2z)-2-benzylidene-n-[3-[cyclohexyl(methyl)amino]propyl]-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1CCCCC1N(C)CCCNC(=O)C(C=C1N(CC=2C=C(C)C=CC=2)C2=O)=CC=C1S\C2=C/C1=CC=CC=C1 AFKBYNLPCUGDNZ-JDCMOKTRSA-N 0.000 claims description 2
- LJWIEDMDKQYRFI-YQYKVWLJSA-N (2z)-2-benzylidene-n-[3-[cyclohexyl(methyl)amino]propyl]-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1CCCCC1N(C)CCCNC(=O)C(C=C1N(CC=2C=CC(F)=CC=2)C2=O)=CC=C1S\C2=C/C1=CC=CC=C1 LJWIEDMDKQYRFI-YQYKVWLJSA-N 0.000 claims description 2
- YKGKLDCCJVPCMH-JNPMABBASA-N (2z)-4-benzyl-2-ethylidene-3-imino-n-(3-piperidin-1-ylpropyl)-1,4-benzothiazine-6-carboxamide Chemical compound N=C1C(=C/C)/SC2=CC=C(C(=O)NCCCN3CCCCC3)C=C2N1CC1=CC=CC=C1 YKGKLDCCJVPCMH-JNPMABBASA-N 0.000 claims description 2
- KMXBZHVWLSKBEV-UJOWUYHQSA-N (2z)-4-benzyl-2-ethylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C1=CC=C(S\C(=C/C)C(=O)N2CC=3C=CC=CC=3)C2=C1 KMXBZHVWLSKBEV-UJOWUYHQSA-N 0.000 claims description 2
- FCSGHIXIKQWVJQ-OFWBYEQRSA-N (2z)-n-[2-(azepan-1-yl)ethyl]-2-benzylidene-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(=CC=C3SC(/C2=O)=C\C=2C=CC=CC=2)C(=O)NCCN2CCCCCC2)=C1 FCSGHIXIKQWVJQ-OFWBYEQRSA-N 0.000 claims description 2
- SEDBWQZCSWCKCN-BRPDVVIDSA-N (2z)-n-[2-(azepan-1-yl)ethyl]-2-benzylidene-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=CC(F)=CC=C1CN(C\1=O)C2=CC(C(=O)NCCN3CCCCCC3)=CC=C2SC/1=C\C1=CC=CC=C1 SEDBWQZCSWCKCN-BRPDVVIDSA-N 0.000 claims description 2
- PKZGRULQWBETTD-XHPQRKPJSA-N (2z)-n-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethyl]-2-[2-(4-methoxyphenyl)-2-oxoethylidene]-3-oxo-1,4-dihydroquinoxaline-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C/1C(=O)NC2=CC(C(=O)NCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2N\1 PKZGRULQWBETTD-XHPQRKPJSA-N 0.000 claims description 2
- PRHVFPJWIANYKA-VAMRJTSQSA-N (2z)-n-[3-(azepan-1-yl)propyl]-2-benzylidene-4-[(3-methylphenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC(=CC=C3SC(/C2=O)=C\C=2C=CC=CC=2)C(=O)NCCCN2CCCCCC2)=C1 PRHVFPJWIANYKA-VAMRJTSQSA-N 0.000 claims description 2
- MCXJXPMWORNTRY-OFWBYEQRSA-N (2z)-n-[3-(azepan-1-yl)propyl]-2-benzylidene-4-[(4-fluorophenyl)methyl]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=CC(F)=CC=C1CN(C\1=O)C2=CC(C(=O)NCCCN3CCCCCC3)=CC=C2SC/1=C\C1=CC=CC=C1 MCXJXPMWORNTRY-OFWBYEQRSA-N 0.000 claims description 2
- CBEAGAZKXXEFFO-BRPDVVIDSA-N (2z)-n-[3-[4-(2-fluorophenyl)piperazin-1-yl]propyl]-4-methyl-2-[(3-methylphenyl)methylidene]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=C2N(C)C(=O)\C(=C\C=3C=C(C)C=CC=3)SC2=CC=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1F CBEAGAZKXXEFFO-BRPDVVIDSA-N 0.000 claims description 2
- REUPKBWPTUKOGH-ANYBSYGZSA-N (2z)-n-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-4-methyl-2-[(2-methylphenyl)methylidene]-3-oxo-1,4-benzothiazine-6-carboxamide Chemical compound C1=C2N(C)C(=O)\C(=C\C=3C(=CC=CC=3)C)SC2=CC=C1C(=O)NCCCN(CC1)CCN1C1=CC=C(F)C=C1 REUPKBWPTUKOGH-ANYBSYGZSA-N 0.000 claims description 2
- MLANGIZDTNVKMF-KJDXXRKVSA-N (3z)-1-(cyclohexylmethyl)-3-ethylidene-n-(3-piperidin-1-ylpropyl)-2-sulfanylidenepyrido[2,3-b][1,4]oxazine-7-carboxamide Chemical compound S=C1C(=C/C)/OC2=NC=C(C(=O)NCCCN3CCCCC3)C=C2N1CC1CCCCC1 MLANGIZDTNVKMF-KJDXXRKVSA-N 0.000 claims description 2
- RLWIGFXZNKSWNQ-QDPJQKAKSA-N (3z)-1-benzyl-3-ethylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-2-oxopyrido[2,3-b][1,4]oxazine-7-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C1=CN=C(O\C(=C/C)C(=O)N2CC=3C=CC=CC=3)C2=C1 RLWIGFXZNKSWNQ-QDPJQKAKSA-N 0.000 claims description 2
- UQPTYUAABLSMQJ-JCMHNJIXSA-N (3z)-3-benzylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-2-oxo-1h-pyrido[2,3-b][1,4]oxazine-7-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C1=CN=C(O\C(=C/C=2C=CC=CC=2)C(=O)N2)C2=C1 UQPTYUAABLSMQJ-JCMHNJIXSA-N 0.000 claims description 2
- LVZGCMDULWACTD-JCMHNJIXSA-N (3z)-3-benzylidene-n-[3-(2-ethylpiperidin-1-yl)propyl]-2-oxo-1h-pyrido[3,4-b][1,4]oxazine-7-carboxamide Chemical compound CCC1CCCCN1CCCNC(=O)C(N=C1)=CC(NC\2=O)=C1OC/2=C\C1=CC=CC=C1 LVZGCMDULWACTD-JCMHNJIXSA-N 0.000 claims description 2
- FDPCLZWXBWEYTK-KJDXXRKVSA-N (3z)-3-ethylidene-4-[(4-fluorophenyl)methyl]-n-(3-piperidin-1-ylpropyl)-2-sulfanylidene-1,4-benzoxazine-7-carboxamide Chemical compound C12=CC=C(C(=O)NCCCN3CCCCC3)C=C2OC(=S)C(=C/C)/N1CC1=CC=C(F)C=C1 FDPCLZWXBWEYTK-KJDXXRKVSA-N 0.000 claims description 2
- GPNKGXCKRXUKDC-DHIFEGFHSA-N (7as,11as)-n-[2-(4-benzylpiperidin-1-yl)ethyl]-5-[(2-chloro-5-fluorophenyl)methyl]-6-oxo-7a,8,9,10,11,11a-hexahydro-7h-benzo[d][1]benzazepine-3-carboxamide Chemical compound FC1=CC=C(Cl)C(CN2C(C[C@@H]3CCCC[C@@H]3C3=CC=C(C=C32)C(=O)NCCN2CCC(CC=3C=CC=CC=3)CC2)=O)=C1 GPNKGXCKRXUKDC-DHIFEGFHSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 2009-12-08 RU RU2011128013/04A patent/RU2586212C2/ru not_active IP Right Cessation
- 2009-12-08 US US13/133,565 patent/US9040508B2/en active Active
- 2009-12-08 MX MX2011006108A patent/MX2011006108A/es unknown
- 2009-12-08 BR BRPI0922224A patent/BRPI0922224A2/pt not_active IP Right Cessation
- 2009-12-08 EP EP09836726A patent/EP2376495A4/en active Pending
- 2009-12-08 RU RU2016116516A patent/RU2016116516A/ru unknown
- 2009-12-08 WO PCT/US2009/067197 patent/WO2010077680A2/en not_active Ceased
- 2009-12-08 JP JP2011540836A patent/JP5752601B2/ja not_active Expired - Fee Related
- 2009-12-08 NZ NZ593937A patent/NZ593937A/en not_active IP Right Cessation
- 2009-12-08 KR KR1020117015933A patent/KR101805754B1/ko not_active Ceased
- 2009-12-08 CN CN200980150091.4A patent/CN102292338B/zh not_active Expired - Fee Related
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2014
- 2014-04-18 US US14/256,094 patent/US8809530B1/en active Active
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2015
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2016
- 2016-01-11 AU AU2016200153A patent/AU2016200153A1/en not_active Abandoned
- 2016-07-08 JP JP2016135647A patent/JP2016180005A/ja not_active Withdrawn
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2017
- 2017-08-14 US US15/676,039 patent/US10421763B2/en active Active
- 2017-10-11 JP JP2017197589A patent/JP2018002741A/ja active Pending
- 2017-10-18 AU AU2017248456A patent/AU2017248456A1/en not_active Abandoned
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