CA2814503A1 - Substituted benzamides and their uses - Google Patents
Substituted benzamides and their uses Download PDFInfo
- Publication number
- CA2814503A1 CA2814503A1 CA2814503A CA2814503A CA2814503A1 CA 2814503 A1 CA2814503 A1 CA 2814503A1 CA 2814503 A CA2814503 A CA 2814503A CA 2814503 A CA2814503 A CA 2814503A CA 2814503 A1 CA2814503 A1 CA 2814503A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- optionally substituted
- pyridinyl
- benzamide
- 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.)
- Abandoned
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title abstract description 3
- 150000003936 benzamides Chemical class 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 126
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 557
- -1 2-pyridinyl Chemical group 0.000 claims description 328
- 150000001875 compounds Chemical class 0.000 claims description 325
- 125000000217 alkyl group Chemical group 0.000 claims description 194
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 164
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 141
- 150000003839 salts Chemical class 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 100
- 125000001072 heteroaryl group Chemical group 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 55
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 50
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 37
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 239000012453 solvate Substances 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 201000010099 disease Diseases 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000651 prodrug Substances 0.000 claims description 27
- 229940002612 prodrug Drugs 0.000 claims description 27
- 230000001404 mediated effect Effects 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 108091006296 SLC2A1 Proteins 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 230000004190 glucose uptake Effects 0.000 claims description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 230000002950 deficient Effects 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- 102100035070 von Hippel-Lindau disease tumor suppressor Human genes 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- 230000006536 aerobic glycolysis Effects 0.000 claims description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 12
- 238000012360 testing method Methods 0.000 claims description 12
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 11
- 231100000433 cytotoxic Toxicity 0.000 claims description 11
- 230000001472 cytotoxic effect Effects 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 11
- 230000004076 epigenetic alteration Effects 0.000 claims description 11
- 230000004077 genetic alteration Effects 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 9
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 9
- OQFUNFPIPRUQAE-UHFFFAOYSA-N 1,4-thiazepane Chemical compound C1CNCCSC1 OQFUNFPIPRUQAE-UHFFFAOYSA-N 0.000 claims description 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 9
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 9
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 8
- 101000600756 Homo sapiens 3-phosphoinositide-dependent protein kinase 1 Proteins 0.000 claims description 8
- 101001117146 Homo sapiens [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Proteins 0.000 claims description 8
- 102100024148 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Human genes 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 230000034659 glycolysis Effects 0.000 claims description 8
- 230000006698 induction Effects 0.000 claims description 8
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 8
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 230000008685 targeting Effects 0.000 claims description 8
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
- 231100000135 cytotoxicity Toxicity 0.000 claims description 7
- 230000003013 cytotoxicity Effects 0.000 claims description 7
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 150000003852 triazoles Chemical class 0.000 claims description 7
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 6
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 230000002147 killing effect Effects 0.000 claims description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
- 102100023536 Solute carrier family 2, facilitated glucose transporter member 1 Human genes 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
- 208000006542 von Hippel-Lindau disease Diseases 0.000 claims description 5
- 102100032742 Histone-lysine N-methyltransferase SETD2 Human genes 0.000 claims description 4
- 101000654725 Homo sapiens Histone-lysine N-methyltransferase SETD2 Proteins 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 108091006299 SLC2A2 Proteins 0.000 claims description 4
- 102100023537 Solute carrier family 2, facilitated glucose transporter member 2 Human genes 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 4
- 238000011275 oncology therapy Methods 0.000 claims description 4
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000005305 thiadiazolinyl group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000006377 glucose transport Effects 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
- PUQBLXZNROYLHF-UHFFFAOYSA-N 4-[(furan-2-ylsulfonylamino)methyl]-n-pyridin-3-ylbenzamide Chemical compound C=1C=C(CNS(=O)(=O)C=2OC=CC=2)C=CC=1C(=O)NC1=CC=CN=C1 PUQBLXZNROYLHF-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 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
- KQXAUXXHBJFNGF-UHFFFAOYSA-N 4-[[(2,3-dimethylimidazol-4-yl)sulfonylamino]methyl]-n-pyridin-3-ylbenzamide Chemical compound CN1C(C)=NC=C1S(=O)(=O)NCC1=CC=C(C(=O)NC=2C=NC=CC=2)C=C1 KQXAUXXHBJFNGF-UHFFFAOYSA-N 0.000 claims 1
- NIKRIJYVXLJCDV-UHFFFAOYSA-N 4-[[(6-chloropyridin-3-yl)sulfonylamino]methyl]-n-pyridin-3-ylbenzamide Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)NCC1=CC=C(C(=O)NC=2C=NC=CC=2)C=C1 NIKRIJYVXLJCDV-UHFFFAOYSA-N 0.000 claims 1
- RURZEPJYVGVRCB-UHFFFAOYSA-N 4-[[[4-(4-methylpiperazin-1-yl)cyclohexyl]sulfonylamino]methyl]-n-pyridin-3-ylbenzamide Chemical compound C1CN(C)CCN1C1CCC(S(=O)(=O)NCC=2C=CC(=CC=2)C(=O)NC=2C=NC=CC=2)CC1 RURZEPJYVGVRCB-UHFFFAOYSA-N 0.000 claims 1
- BXNGKNWSDPHIEK-UHFFFAOYSA-N n-[(3-methylimidazol-4-yl)methyl]-4-[5-methyl-4-[(4-methylphenyl)sulfonylmethyl]-1,3-oxazol-2-yl]benzamide Chemical compound CC=1OC(C=2C=CC(=CC=2)C(=O)NCC=2N(C=NC=2)C)=NC=1CS(=O)(=O)C1=CC=C(C)C=C1 BXNGKNWSDPHIEK-UHFFFAOYSA-N 0.000 claims 1
- DJEFWZBLCMVOGQ-UHFFFAOYSA-N n-pyridin-3-yl-4-[(1h-1,2,4-triazol-5-ylsulfonylamino)methyl]benzamide Chemical compound C=1C=C(CNS(=O)(=O)C=2NC=NN=2)C=CC=1C(=O)NC1=CC=CN=C1 DJEFWZBLCMVOGQ-UHFFFAOYSA-N 0.000 claims 1
- KWFWTYUGAZDJNF-UHFFFAOYSA-N n-pyridin-3-yl-4-[(pyridin-3-ylsulfonylamino)methyl]benzamide Chemical compound C=1C=C(CNS(=O)(=O)C=2C=NC=CC=2)C=CC=1C(=O)NC1=CC=CN=C1 KWFWTYUGAZDJNF-UHFFFAOYSA-N 0.000 claims 1
- BSJYBFQJKBLXOH-UHFFFAOYSA-N n-pyridin-3-yl-4-[(thiophen-2-ylsulfonylamino)methyl]benzamide Chemical compound C=1C=C(CNS(=O)(=O)C=2SC=CC=2)C=CC=1C(=O)NC1=CC=CN=C1 BSJYBFQJKBLXOH-UHFFFAOYSA-N 0.000 claims 1
- UFMDPNABJNPTKM-UHFFFAOYSA-N n-pyridin-3-yl-4-[(thiophen-3-ylsulfonylamino)methyl]benzamide Chemical compound C=1C=C(CNS(=O)(=O)C2=CSC=C2)C=CC=1C(=O)NC1=CC=CN=C1 UFMDPNABJNPTKM-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 140
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- 229960004355 vindesine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229950004393 visilizumab Drugs 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2814503A1 true CA2814503A1 (en) | 2012-04-19 |
Family
ID=45938912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2814503A Abandoned CA2814503A1 (en) | 2010-10-11 | 2011-10-10 | Substituted benzamides and their uses |
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 |
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| 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 |
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| 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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012051117A3 (en) | 2012-06-14 |
| WO2012051117A2 (en) | 2012-04-19 |
| KR20140027907A (ko) | 2014-03-07 |
| EP2627324A2 (en) | 2013-08-21 |
| US9085570B2 (en) | 2015-07-21 |
| CN103327972A (zh) | 2013-09-25 |
| US20150329503A1 (en) | 2015-11-19 |
| JP2013539786A (ja) | 2013-10-28 |
| US20140024649A1 (en) | 2014-01-23 |
| BR112013008898A2 (pt) | 2016-06-28 |
| EP2627324A4 (en) | 2014-05-07 |
| ZA201302854B (en) | 2014-07-25 |
| AU2011313853A1 (en) | 2013-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171011 |