JP2008540589A5 - - Google Patents
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- Publication number
- JP2008540589A5 JP2008540589A5 JP2008511587A JP2008511587A JP2008540589A5 JP 2008540589 A5 JP2008540589 A5 JP 2008540589A5 JP 2008511587 A JP2008511587 A JP 2008511587A JP 2008511587 A JP2008511587 A JP 2008511587A JP 2008540589 A5 JP2008540589 A5 JP 2008540589A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- unsubstituted
- independently
- heterocyclyl
- 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 biphenylyl Chemical group 0.000 claims 79
- 125000000623 heterocyclic group Chemical group 0.000 claims 59
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 33
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical group 0.000 claims 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 238000006467 substitution reaction Methods 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 4
- GHDARLKSYBCZRE-UHFFFAOYSA-N 1,4,3-oxathiazinane 4,4-dioxide Chemical compound O=S1(=O)CCOCN1 GHDARLKSYBCZRE-UHFFFAOYSA-N 0.000 claims 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 4
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 4
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims 4
- 125000002785 azepinyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 4
- 125000005493 quinolyl group Chemical group 0.000 claims 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- DNGMYXZLJGHHOM-UHFFFAOYSA-N thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCCCN1 DNGMYXZLJGHHOM-UHFFFAOYSA-N 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 2
- ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical compound C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 claims 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 2
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims 2
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 claims 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 2
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 2
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims 2
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 2
- GMQOZFVOGGIFIX-UHFFFAOYSA-N oxathiazolidine Chemical compound C1COSN1 GMQOZFVOGGIFIX-UHFFFAOYSA-N 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- IXAZIGSJNTYTGJ-UHFFFAOYSA-N 1,2,5-thiadiazinane 1,1-dioxide Chemical compound O=S1(=O)CNCCN1 IXAZIGSJNTYTGJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- PZODDSWUYWTGHR-UHFFFAOYSA-N 1,2,6-thiadiazepane 1,1-dioxide Chemical compound O=S1(=O)CNCCCN1 PZODDSWUYWTGHR-UHFFFAOYSA-N 0.000 claims 1
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 1
- YTBSOFLQSAXDKA-UHFFFAOYSA-N 1,3,2-dithiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCSN1 YTBSOFLQSAXDKA-UHFFFAOYSA-N 0.000 claims 1
- CFRCZLVPCCLZFG-UHFFFAOYSA-N 1,3,4-oxathiazinane 3,3-dioxide Chemical compound O=S1(=O)COCCN1 CFRCZLVPCCLZFG-UHFFFAOYSA-N 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 1
- 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims 1
- PTJGQWYPPWNJOF-UHFFFAOYSA-N 1,4,2-dithiazolidine 1,1-dioxide Chemical compound O=S1(=O)CSCN1 PTJGQWYPPWNJOF-UHFFFAOYSA-N 0.000 claims 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical group C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 1
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims 1
- 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims 1
- RMIIPFHXZBZULD-UHFFFAOYSA-N 1,5,2-dithiazinane 1,1-dioxide Chemical compound O=S1(=O)CSCCN1 RMIIPFHXZBZULD-UHFFFAOYSA-N 0.000 claims 1
- ARPNQFMNYLNSSQ-UHFFFAOYSA-N 1,6,2-dithiazepane 1,1-dioxide Chemical compound O=S1(=O)CSCCCN1 ARPNQFMNYLNSSQ-UHFFFAOYSA-N 0.000 claims 1
- OGOVCJUTZGZKOH-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole 1,1-dioxide Chemical compound O=S1(=O)NCC=C1 OGOVCJUTZGZKOH-UHFFFAOYSA-N 0.000 claims 1
- WHHSFLNHWGCVNC-UHFFFAOYSA-N 2,5,6,7-tetrahydrothiazepine 1,1-dioxide Chemical compound O=S1(=O)CCCC=CN1 WHHSFLNHWGCVNC-UHFFFAOYSA-N 0.000 claims 1
- JVOUGZZPWYEQBE-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole 1,1-dioxide Chemical compound O=S1(=O)CN=CN1 JVOUGZZPWYEQBE-UHFFFAOYSA-N 0.000 claims 1
- PKWBYLAKTCTAIC-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole 1,1-dioxide Chemical compound O=S1(=O)CC=CN1 PKWBYLAKTCTAIC-UHFFFAOYSA-N 0.000 claims 1
- SPGMUHLIDPQYRI-UHFFFAOYSA-N 2,5-dihydrothiazepine 1,1-dioxide Chemical compound O=S1(=O)NC=CCC=C1 SPGMUHLIDPQYRI-UHFFFAOYSA-N 0.000 claims 1
- XEEQRAURRRPUEY-UHFFFAOYSA-N 2,7-dihydrothiazepine 1,1-dioxide Chemical compound O=S1(=O)CC=CC=CN1 XEEQRAURRRPUEY-UHFFFAOYSA-N 0.000 claims 1
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 claims 1
- NWWJFMCCTZLKNT-UHFFFAOYSA-N 3,4-dihydro-2h-thiazine Chemical compound C1CC=CSN1 NWWJFMCCTZLKNT-UHFFFAOYSA-N 0.000 claims 1
- MZWVWPPWTUXGIY-UHFFFAOYSA-N 3-chloro-n-[2-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]ethyl]benzamide Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)CCNC(=O)C1=CC=CC(Cl)=C1 MZWVWPPWTUXGIY-UHFFFAOYSA-N 0.000 claims 1
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims 1
- GSWFKJMUUIJRNK-UHFFFAOYSA-N 4-[(5-chlorothiophene-2-carbonyl)amino]-3-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]butanoic acid Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)C(CC(O)=O)CNC(=O)C1=CC=C(Cl)S1 GSWFKJMUUIJRNK-UHFFFAOYSA-N 0.000 claims 1
- MDVIHNLQBRMGJY-UHFFFAOYSA-N 4-chloro-n-[2-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]ethyl]benzamide Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)CCNC(=O)C1=CC=C(Cl)C=C1 MDVIHNLQBRMGJY-UHFFFAOYSA-N 0.000 claims 1
- MBOWKPOSFWRNOS-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)CCC=CN1 MBOWKPOSFWRNOS-UHFFFAOYSA-N 0.000 claims 1
- JVWHLTPHJJXPOT-UHFFFAOYSA-N 5-bromo-n-[2-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]ethyl]furan-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)CCNC(=O)C1=CC=C(Br)O1 JVWHLTPHJJXPOT-UHFFFAOYSA-N 0.000 claims 1
- VKLLIJCXGSGDIM-UHFFFAOYSA-N 5-bromo-n-[2-[(1-propan-2-ylpiperidin-4-yl)sulfamoyl]ethyl]thiophene-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NS(=O)(=O)CCNC(=O)C1=CC=C(Br)S1 VKLLIJCXGSGDIM-UHFFFAOYSA-N 0.000 claims 1
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| EP05010929A EP1724269A1 (en) | 2005-05-20 | 2005-05-20 | Heteroaryl-carboxylic acid (sulfamoyl alkyl) amide - derivatives as factor Xa inhibitors |
| EP05010929.7 | 2005-05-20 | ||
| PCT/EP2006/004255 WO2006122661A1 (en) | 2005-05-20 | 2006-05-06 | Heteroaryl-carboxylic acid (sulfamoyl alkyl) amide - derivatives as factor xa inhibitors |
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| JP2008540589A JP2008540589A (ja) | 2008-11-20 |
| JP2008540589A5 true JP2008540589A5 (https=) | 2009-06-25 |
| JP5027802B2 JP5027802B2 (ja) | 2012-09-19 |
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| US (1) | US8088925B2 (https=) |
| EP (2) | EP1724269A1 (https=) |
| JP (1) | JP5027802B2 (https=) |
| KR (1) | KR101373533B1 (https=) |
| CN (1) | CN101180296B (https=) |
| AR (1) | AR053730A1 (https=) |
| AT (1) | ATE452133T1 (https=) |
| AU (1) | AU2006246669B2 (https=) |
| BR (1) | BRPI0610320A2 (https=) |
| CA (1) | CA2609288C (https=) |
| DE (1) | DE602006011156D1 (https=) |
| DK (1) | DK1888567T3 (https=) |
| DO (1) | DOP2006000119A (https=) |
| ES (1) | ES2338151T3 (https=) |
| GT (1) | GT200600211A (https=) |
| IL (1) | IL187430A (https=) |
| MX (1) | MX2007014274A (https=) |
| MY (1) | MY150693A (https=) |
| PA (1) | PA8675301A1 (https=) |
| PE (1) | PE20061452A1 (https=) |
| PT (1) | PT1888567E (https=) |
| SV (1) | SV2007002534A (https=) |
| TW (1) | TWI376377B (https=) |
| UY (1) | UY29550A1 (https=) |
| WO (1) | WO2006122661A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012149102A1 (en) * | 2011-04-29 | 2012-11-01 | Glaxosmithkline Llc | Novel compounds as wip1 inhibitors |
| EP3078378B1 (en) | 2015-04-08 | 2020-06-24 | Vaiomer | Use of factor xa inhibitors for regulating glycemia |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9520044B (sl) | 1994-04-26 | 2004-08-31 | Aventis Pharmaceuticals Inc. | Inhibitorji Xa faktorja |
| GB0030305D0 (en) * | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
| EP1217000A1 (en) * | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| HUP0304058A2 (hu) * | 2001-01-30 | 2004-04-28 | Bristol-Myers Squibb Company | Xa faktor szulfonamid-laktám inhibitorok és alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények |
| DE10254336A1 (de) * | 2002-11-21 | 2004-06-03 | Merck Patent Gmbh | Carbonsäureamide |
| EP1590327A1 (en) * | 2002-12-23 | 2005-11-02 | Millennium Pharmaceuticals, Inc. | Ccr8 inhibitors |
| TW200510311A (en) * | 2002-12-23 | 2005-03-16 | Millennium Pharm Inc | CCr8 inhibitors |
| EP1479678A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Pyrazole-derivatives as factor xa inhibitors |
| US7491827B2 (en) * | 2002-12-23 | 2009-02-17 | Millennium Pharmaceuticals, Inc. | Aryl sulfonamides useful as inhibitors of chemokine receptor activity |
| JP4585448B2 (ja) * | 2002-12-23 | 2010-11-24 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 第Ｘａ因子阻害剤としてのピラゾール−誘導体 |
| DE10322469A1 (de) * | 2003-05-19 | 2004-12-16 | Bayer Healthcare Ag | Heterocyclische Verbindungen |
| US7169795B2 (en) * | 2003-09-30 | 2007-01-30 | Bristol Myers Squibb Company | Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors |
-
2005
- 2005-05-20 EP EP05010929A patent/EP1724269A1/en not_active Withdrawn
-
2006
- 2006-05-06 BR BRPI0610320-0A patent/BRPI0610320A2/pt not_active IP Right Cessation
- 2006-05-06 AT AT06753510T patent/ATE452133T1/de active
- 2006-05-06 MX MX2007014274A patent/MX2007014274A/es active IP Right Grant
- 2006-05-06 JP JP2008511587A patent/JP5027802B2/ja not_active Expired - Fee Related
- 2006-05-06 ES ES06753510T patent/ES2338151T3/es active Active
- 2006-05-06 WO PCT/EP2006/004255 patent/WO2006122661A1/en not_active Ceased
- 2006-05-06 DK DK06753510.4T patent/DK1888567T3/da active
- 2006-05-06 AU AU2006246669A patent/AU2006246669B2/en not_active Ceased
- 2006-05-06 CN CN2006800172463A patent/CN101180296B/zh not_active Expired - Fee Related
- 2006-05-06 CA CA2609288A patent/CA2609288C/en not_active Expired - Fee Related
- 2006-05-06 DE DE602006011156T patent/DE602006011156D1/de active Active
- 2006-05-06 EP EP06753510A patent/EP1888567B1/en not_active Not-in-force
- 2006-05-06 PT PT06753510T patent/PT1888567E/pt unknown
- 2006-05-06 KR KR1020077027048A patent/KR101373533B1/ko not_active Expired - Fee Related
- 2006-05-16 PE PE2006000516A patent/PE20061452A1/es not_active Application Discontinuation
- 2006-05-18 GT GT200600211A patent/GT200600211A/es unknown
- 2006-05-18 TW TW095117566A patent/TWI376377B/zh not_active IP Right Cessation
- 2006-05-18 AR ARP060102004A patent/AR053730A1/es not_active Application Discontinuation
- 2006-05-18 MY MYPI20062281 patent/MY150693A/en unknown
- 2006-05-18 SV SV2006002534A patent/SV2007002534A/es unknown
- 2006-05-18 PA PA20068675301A patent/PA8675301A1/es unknown
- 2006-05-19 DO DO2006000119A patent/DOP2006000119A/es unknown
- 2006-05-19 UY UY29550A patent/UY29550A1/es unknown
-
2007
- 2007-11-15 IL IL187430A patent/IL187430A/en not_active IP Right Cessation
- 2007-11-15 US US11/940,654 patent/US8088925B2/en not_active Expired - Fee Related
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