JP2013539786A5 - - Google Patents
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- JP2013539786A5 JP2013539786A5 JP2013533917A JP2013533917A JP2013539786A5 JP 2013539786 A5 JP2013539786 A5 JP 2013539786A5 JP 2013533917 A JP2013533917 A JP 2013533917A JP 2013533917 A JP2013533917 A JP 2013533917A JP 2013539786 A5 JP2013539786 A5 JP 2013539786A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- optionally substituted
- benzamide
- sulfonyl
- alkyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 22
- -1 5-methyl-4-{[(4-methylphenyl) sulfonyl] methyl} -1,3-oxazol-2-yl Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 3
- OQFUNFPIPRUQAE-UHFFFAOYSA-N 1,4-thiazepane Chemical compound C1CNCCSC1 OQFUNFPIPRUQAE-UHFFFAOYSA-N 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- XOMGMYZLPAZWIP-UHFFFAOYSA-N N-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC=1OC(=C(N=1)CS(=O)(=O)C1=CC=C(C=C1)C)C XOMGMYZLPAZWIP-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003852 triazoles Chemical group 0.000 claims 2
- LWIZQCLTSXBCGW-UHFFFAOYSA-N 4-[4-(benzenesulfonylmethyl)-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=CC=C1 LWIZQCLTSXBCGW-UHFFFAOYSA-N 0.000 claims 1
- ORNTYDADYCUVLX-UHFFFAOYSA-N 4-[4-[(2,4-dimethylphenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1C ORNTYDADYCUVLX-UHFFFAOYSA-N 0.000 claims 1
- DBCKGZIZRSZKCH-UHFFFAOYSA-N 4-[4-[(3,4-dimethoxyphenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)CC1=C(C)OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=N1 DBCKGZIZRSZKCH-UHFFFAOYSA-N 0.000 claims 1
- IUIRGBTWZACWBQ-UHFFFAOYSA-N 4-[4-[(3-methoxyphenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound COC1=CC=CC(S(=O)(=O)CC2=C(OC(=N2)C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)C)=C1 IUIRGBTWZACWBQ-UHFFFAOYSA-N 0.000 claims 1
- VMIKXFRAUPWYAH-UHFFFAOYSA-N 4-[4-[(4-bromophenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(Br)C=C1 VMIKXFRAUPWYAH-UHFFFAOYSA-N 0.000 claims 1
- XNPNTDSOCDUJPS-UHFFFAOYSA-N 4-[4-[(4-chlorophenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(Cl)C=C1 XNPNTDSOCDUJPS-UHFFFAOYSA-N 0.000 claims 1
- NGPPYGLSGXBDOP-UHFFFAOYSA-N 4-[4-[(4-fluorophenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(F)C=C1 NGPPYGLSGXBDOP-UHFFFAOYSA-N 0.000 claims 1
- WUHLLEHRTVYPPE-UHFFFAOYSA-N 4-[4-[(4-methoxyphenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC1=C(C)OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=N1 WUHLLEHRTVYPPE-UHFFFAOYSA-N 0.000 claims 1
- AXWKXILTLBKMBT-UHFFFAOYSA-N 4-[4-[(4-methylphenyl)sulfonylmethyl]-1,3-thiazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=N1 AXWKXILTLBKMBT-UHFFFAOYSA-N 0.000 claims 1
- STRZWCVRJUENOO-UHFFFAOYSA-N 4-[4-[(4-tert-butylphenyl)sulfonylmethyl]-5-methyl-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 STRZWCVRJUENOO-UHFFFAOYSA-N 0.000 claims 1
- QZTDDAWEMYMTJN-UHFFFAOYSA-N 4-[5-methyl-4-[(3-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=CC(C)=C1 QZTDDAWEMYMTJN-UHFFFAOYSA-N 0.000 claims 1
- UGDHAMUOOAABCR-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(2-pyridin-3-ylethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 UGDHAMUOOAABCR-UHFFFAOYSA-N 0.000 claims 1
- WSLNTDSTAKTMES-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyrazin-2-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2N=CC=NC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 WSLNTDSTAKTMES-UHFFFAOYSA-N 0.000 claims 1
- XPHYQAGSIXLYRC-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-2-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2N=CC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 XPHYQAGSIXLYRC-UHFFFAOYSA-N 0.000 claims 1
- DLFCEZOMHBPDGI-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 DLFCEZOMHBPDGI-UHFFFAOYSA-N 0.000 claims 1
- YSFGQIVFZJVOKM-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=CN=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 YSFGQIVFZJVOKM-UHFFFAOYSA-N 0.000 claims 1
- LXMRDQNVMJTYTL-UHFFFAOYSA-N 4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-pyridin-3-ylbenzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NC=2C=NC=CC=2)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 LXMRDQNVMJTYTL-UHFFFAOYSA-N 0.000 claims 1
- DWAVVDQQRHMHBY-UHFFFAOYSA-N 4-[5-methyl-4-[(4-morpholin-4-ylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)=NC=1CS(=O)(=O)C(C=C1)=CC=C1N1CCOCC1 DWAVVDQQRHMHBY-UHFFFAOYSA-N 0.000 claims 1
- DGUQIBUQGAIIFP-UHFFFAOYSA-N 4-[5-methyl-4-[[4-(4-methylpiperazin-1-yl)phenyl]sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)CC2=C(OC(=N2)C=2C=CC(=CC=2)C(=O)NCC=2C=NC=CC=2)C)C=C1 DGUQIBUQGAIIFP-UHFFFAOYSA-N 0.000 claims 1
- 102000058063 Glucose Transporter Type 1 Human genes 0.000 claims 1
- 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 claims 1
- 102100022875 Hypoxia-inducible factor 1-alpha Human genes 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108091006296 SLC2A1 Proteins 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000002950 deficient Effects 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- DYNCFAWDKHSUQT-UHFFFAOYSA-N n-methyl-4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C=1C=C(C=2OC(C)=C(CS(=O)(=O)C=3C=CC(C)=CC=3)N=2)C=CC=1C(=O)N(C)CC1=CC=CN=C1 DYNCFAWDKHSUQT-UHFFFAOYSA-N 0.000 claims 1
- NQRBZSIEDWNLHS-UHFFFAOYSA-N n-methyl-4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]-n-pyridin-3-ylbenzamide Chemical compound C=1C=CN=CC=1N(C)C(=O)C(C=C1)=CC=C1C(OC=1C)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 NQRBZSIEDWNLHS-UHFFFAOYSA-N 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 208000006542 von Hippel-Lindau disease Diseases 0.000 claims 1
- 102100035070 von Hippel-Lindau disease tumor suppressor Human genes 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39195810P | 2010-10-11 | 2010-10-11 | |
| US61/391,958 | 2010-10-11 | ||
| US201161434976P | 2011-01-21 | 2011-01-21 | |
| US61/434,976 | 2011-01-21 | ||
| US201161475549P | 2011-04-14 | 2011-04-14 | |
| US61/475,549 | 2011-04-14 | ||
| PCT/US2011/055624 WO2012051117A2 (en) | 2010-10-11 | 2011-10-10 | Substituted benzamides and their uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013539786A JP2013539786A (ja) | 2013-10-28 |
| JP2013539786A5 true JP2013539786A5 (enExample) | 2014-11-27 |
Family
ID=45938912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013533917A Pending JP2013539786A (ja) | 2010-10-11 | 2011-10-10 | 置換ベンズアミドおよびその使用法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9085570B2 (enExample) |
| EP (1) | EP2627324A4 (enExample) |
| JP (1) | JP2013539786A (enExample) |
| KR (1) | KR20140027907A (enExample) |
| CN (1) | CN103327972A (enExample) |
| AU (1) | AU2011313853A1 (enExample) |
| BR (1) | BR112013008898A2 (enExample) |
| CA (1) | CA2814503A1 (enExample) |
| WO (1) | WO2012051117A2 (enExample) |
| ZA (1) | ZA201302854B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2712290A4 (en) * | 2011-05-19 | 2014-11-19 | Univ Leland Stanford Junior | ANTIPROLIFERATIVE COMPOUNDS AND METHOD FOR THEIR USE |
| SG11201406518XA (en) | 2012-04-12 | 2014-11-27 | Univ Leland Stanford Junior | Substituted benzamides and their uses |
| WO2013182612A1 (en) | 2012-06-07 | 2013-12-12 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| JP6423372B2 (ja) | 2013-02-28 | 2018-11-14 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ１およびｒｏｃｋ２阻害剤としてのフェニルピラゾール誘導体 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| WO2015078799A1 (en) * | 2013-11-27 | 2015-06-04 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| EP3083596A1 (en) | 2013-12-18 | 2016-10-26 | Basf Se | Azole compounds carrying an imine-derived substituent |
| WO2016202935A1 (en) | 2015-06-19 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| CA3166630A1 (en) | 2020-01-03 | 2021-07-08 | Berg Llc | Polycyclic amides as ube2k modulators for treating cancer |
| CN116462606B (zh) * | 2022-01-12 | 2025-11-28 | 南京宁丹新药技术股份有限公司 | 一类酰胺衍生化合物及其用途 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172896A (en) | 1978-06-05 | 1979-10-30 | Dainippon Pharmaceutical Co., Ltd. | Methane-sulfonamide derivatives, the preparation thereof and composition comprising the same |
| GB9217295D0 (en) | 1992-08-14 | 1992-09-30 | Wellcome Found | Controlled released tablets |
| GB9315856D0 (en) | 1993-07-30 | 1993-09-15 | Wellcome Found | Stabilized pharmaceutical |
| US5358970A (en) | 1993-08-12 | 1994-10-25 | Burroughs Wellcome Co. | Pharmaceutical composition containing bupropion hydrochloride and a stabilizer |
| US5541231A (en) | 1993-07-30 | 1996-07-30 | Glaxo Wellcome Inc. | Stabilized Pharmaceutical |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| AU707748B2 (en) | 1994-03-25 | 1999-07-22 | Isotechnika Inc. | Enhancement of the efficacy of drugs by deuteration |
| JP2002501892A (ja) | 1998-01-29 | 2002-01-22 | セプラコア インコーポレーテッド | 光学的に純粋な（−）−ビュープロピオンの薬学的使用 |
| NZ524421A (en) | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| IL159002A0 (en) * | 2001-06-07 | 2004-05-12 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors (ppar) |
| EP1369420A1 (en) * | 2002-06-06 | 2003-12-10 | Aventis Pharma Deutschland GmbH | Inhibitors of the GPib - vWF interaction |
| US7235558B2 (en) * | 2002-06-06 | 2007-06-26 | Sanofi-Aventis Deutschland Gmbh | Inhibitors of the GPIb—vWF interaction, their preparation and use |
| AU2003900207A0 (en) * | 2003-01-17 | 2003-01-30 | Fujisawa Pharmaceutical Co., Ltd. | New compounds |
| TW200505446A (en) | 2003-01-17 | 2005-02-16 | Fuj Isawa Pharmaceutical Co Ltd | Inhibitor of cox |
| EP1655283A1 (en) * | 2004-11-08 | 2006-05-10 | Evotec OAI AG | 11beta-HSD1 Inhibitors |
| WO2008112156A1 (en) | 2007-03-08 | 2008-09-18 | Altiris Therapeutics | Chemokine receptor modulators |
| US8252823B2 (en) | 2008-01-28 | 2012-08-28 | New York University | Oxazole and thiazole compounds as beta-catenin modulators and uses thereof |
| US20110105436A1 (en) * | 2008-03-10 | 2011-05-05 | Auckland Uniservices Limited | Heteroaryl compounds, compositions, and methods of use in cancer treatment |
| CN106243100B (zh) | 2008-10-10 | 2019-04-09 | Vm生物医药公司 | 治疗酒精使用障碍，疼痛和其他疾病的药物组合与方法 |
| JP2012514044A (ja) * | 2008-12-30 | 2012-06-21 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | Ｒａｆキナーゼ阻害剤として有用なヘテロアリール化合物 |
| EP2456435B1 (en) * | 2009-07-21 | 2015-06-24 | The Board of Trustees of the Leland Stanford Junior University | Heteroaryl benzamides, compositions and methods of use |
| EP2305643A1 (en) * | 2009-10-02 | 2011-04-06 | Ikerchem, S.L. | New histone deacetylase inhibitors based simultaneously on trisubstituted 1h-pyrroles and aromatic and heteroaromatic spacers |
| US9079859B2 (en) * | 2011-01-21 | 2015-07-14 | Auckland Uniservices Limited | Synthetic lethal targeting of glucose transport |
| EP2712290A4 (en) * | 2011-05-19 | 2014-11-19 | Univ Leland Stanford Junior | ANTIPROLIFERATIVE COMPOUNDS AND METHOD FOR THEIR USE |
| SG11201406518XA (en) * | 2012-04-12 | 2014-11-27 | Univ Leland Stanford Junior | Substituted benzamides and their uses |
-
2011
- 2011-10-10 CN CN2011800595100A patent/CN103327972A/zh active Pending
- 2011-10-10 AU AU2011313853A patent/AU2011313853A1/en not_active Abandoned
- 2011-10-10 JP JP2013533917A patent/JP2013539786A/ja active Pending
- 2011-10-10 KR KR1020137012143A patent/KR20140027907A/ko not_active Withdrawn
- 2011-10-10 US US13/878,682 patent/US9085570B2/en not_active Expired - Fee Related
- 2011-10-10 EP EP11833208.9A patent/EP2627324A4/en not_active Withdrawn
- 2011-10-10 WO PCT/US2011/055624 patent/WO2012051117A2/en not_active Ceased
- 2011-10-10 CA CA2814503A patent/CA2814503A1/en not_active Abandoned
- 2011-10-10 BR BR112013008898A patent/BR112013008898A2/pt not_active IP Right Cessation
-
2013
- 2013-04-19 ZA ZA2013/02854A patent/ZA201302854B/en unknown
-
2015
- 2015-07-20 US US14/803,771 patent/US20150329503A1/en not_active Abandoned
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