JP2006511608A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006511608A5 JP2006511608A5 JP2005502535A JP2005502535A JP2006511608A5 JP 2006511608 A5 JP2006511608 A5 JP 2006511608A5 JP 2005502535 A JP2005502535 A JP 2005502535A JP 2005502535 A JP2005502535 A JP 2005502535A JP 2006511608 A5 JP2006511608 A5 JP 2006511608A5
- Authority
- JP
- Japan
- Prior art keywords
- thiophen
- chloro
- ylmethyl
- isoxazol
- pyrazole
- 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
Links
- -1 1H-pyrrolopyridyl Chemical group 0.000 claims 102
- GGURMRUSUXSEDS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrazole-3,5-dicarboxylic acid Chemical compound N1=C(C(=O)O)C=C(C(O)=O)N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GGURMRUSUXSEDS-UHFFFAOYSA-N 0.000 claims 30
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 18
- ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 229960000583 acetic acid Drugs 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 3
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical group N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 3
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical group C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical group C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical group C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical group N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 3
- 150000003536 tetrazoles Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 2
- SIQUSQWVAADNSH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-thiophen-2-ylpyrazole-3-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)O)C=C1C1=CC=CS1 SIQUSQWVAADNSH-UHFFFAOYSA-N 0.000 claims 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical group N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 2
- WWFRSWPBUNIUJR-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-1,3-oxazolidine-3-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(OCC2)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WWFRSWPBUNIUJR-UHFFFAOYSA-N 0.000 claims 2
- LTXWLSOMNVDSON-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(O)C2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LTXWLSOMNVDSON-UHFFFAOYSA-N 0.000 claims 2
- YKHIOPPDUVHGCL-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 YKHIOPPDUVHGCL-UHFFFAOYSA-N 0.000 claims 2
- WHYHFYNRCMGJPY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-thiophen-2-ylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(C=2SC=CC=2)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 WHYHFYNRCMGJPY-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
- IKJWKUWNJONWCL-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCC2)=C1 IKJWKUWNJONWCL-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- JPTAKWMQGRCRCT-UHFFFAOYSA-N ethyl 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)NC2CCN(CC2)C(C)C)=C1 JPTAKWMQGRCRCT-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims 1
- JOCCOIPBVWXHIU-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CC2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JOCCOIPBVWXHIU-UHFFFAOYSA-N 0.000 claims 1
- BXSLFHKFBUGMNX-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(C2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BXSLFHKFBUGMNX-UHFFFAOYSA-N 0.000 claims 1
- QOCNSCGBIFXKNQ-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CC2)C(O)=O)=C1 QOCNSCGBIFXKNQ-UHFFFAOYSA-N 0.000 claims 1
- VKDQXRGYAINZQX-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(C2)C(O)=O)=C1 VKDQXRGYAINZQX-UHFFFAOYSA-N 0.000 claims 1
- FHRDUPTZGUNXLD-UHFFFAOYSA-N 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CCC2)C(O)=O)=C1 FHRDUPTZGUNXLD-UHFFFAOYSA-N 0.000 claims 1
- LLATVTSYXRUZGU-UHFFFAOYSA-N 1-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC=2N=C(SC=2)C=2SC(Cl)=CC=2)C(C=2SC=CC=2)=C1 LLATVTSYXRUZGU-UHFFFAOYSA-N 0.000 claims 1
- OVVDMXKWFMNGLN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-n,5-n-bis(1-propan-2-ylpiperidin-4-yl)pyrazole-3,5-dicarboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)NC2CCN(CC2)C(C)C)=C1 OVVDMXKWFMNGLN-UHFFFAOYSA-N 0.000 claims 1
- NARHJPGTHAFNGW-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(2,4-dichlorophenyl)pyrazole-3-carboxylic acid Chemical compound C1=C(C=2C(=CC(Cl)=CC=2)Cl)C(C(=O)O)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 NARHJPGTHAFNGW-UHFFFAOYSA-N 0.000 claims 1
- ZDLWJPKJKIRKCL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=C(C#N)C(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 ZDLWJPKJKIRKCL-UHFFFAOYSA-N 0.000 claims 1
- IATLXOOKFSXVKJ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=C1C=2SC=CC=2)C#N)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IATLXOOKFSXVKJ-UHFFFAOYSA-N 0.000 claims 1
- FUDWOSJPMAUSHR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C(=C1)C#N)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 FUDWOSJPMAUSHR-UHFFFAOYSA-N 0.000 claims 1
- VKYPCYFLMMYWQE-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2,2-dimethylpyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CCC2)(C)C)=C1 VKYPCYFLMMYWQE-UHFFFAOYSA-N 0.000 claims 1
- RHTSVKCTKSQNAB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-1,3-oxazolidine-3-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(OCC2)=O)=C1 RHTSVKCTKSQNAB-UHFFFAOYSA-N 0.000 claims 1
- JPQGPWDWWPQYEU-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2OC(=O)NN=2)=C1 JPQGPWDWWPQYEU-UHFFFAOYSA-N 0.000 claims 1
- SYZNRFJJOOJACM-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(O)C2)=C1 SYZNRFJJOOJACM-UHFFFAOYSA-N 0.000 claims 1
- UNUMMFIBPNTOPT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxypyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(O)CC2)=C1 UNUMMFIBPNTOPT-UHFFFAOYSA-N 0.000 claims 1
- ACVGZLQAXQZWKY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-methylsulfonylpyrrolidine-1-carbonyl)pyrazole-3-carboxylic acid Chemical compound C1C(S(=O)(=O)C)CCN1C(=O)C1=CC(C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ACVGZLQAXQZWKY-UHFFFAOYSA-N 0.000 claims 1
- WUMLJYCGGKNFLS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-oxopiperazine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CC(=O)NCC2)=C1 WUMLJYCGGKNFLS-UHFFFAOYSA-N 0.000 claims 1
- IQZKHRHFWFGTTK-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4,4-difluoropiperidine-1-carbonyl)pyrazole-3-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)O)C=C1C(=O)N1CCC(F)(F)CC1 IQZKHRHFWFGTTK-UHFFFAOYSA-N 0.000 claims 1
- ZNHVVTLYJIFLQX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4-hydroxypiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCC(O)CC2)=C1 ZNHVVTLYJIFLQX-UHFFFAOYSA-N 0.000 claims 1
- CSWIFDWSGAPZQQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(furan-2-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2OC=CC=2)=C1 CSWIFDWSGAPZQQ-UHFFFAOYSA-N 0.000 claims 1
- IGFMAGLCUPICTQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(furan-2-yl)-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C(=CC(=N2)C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)C=2OC=CC=2)=NO1 IGFMAGLCUPICTQ-UHFFFAOYSA-N 0.000 claims 1
- FQRGFMDCLSIWKO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(hydroxymethyl)-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrazole-3-carboxamide Chemical compound OCC1=CC(C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 FQRGFMDCLSIWKO-UHFFFAOYSA-N 0.000 claims 1
- DDHMFDPHDZOZFN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(morpholine-4-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCOCC2)=C1 DDHMFDPHDZOZFN-UHFFFAOYSA-N 0.000 claims 1
- DYJQYACJLAYEQR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DYJQYACJLAYEQR-UHFFFAOYSA-N 0.000 claims 1
- KYTQHJJDSOTYPP-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[2-(hydroxymethyl)pyrrolidine-1-carbonyl]pyrazole-3-carboxylic acid Chemical compound OCC1CCCN1C(=O)C1=CC(C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 KYTQHJJDSOTYPP-UHFFFAOYSA-N 0.000 claims 1
- BBTWEWSWTYLJKA-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-methyl-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C)=C1 BBTWEWSWTYLJKA-UHFFFAOYSA-N 0.000 claims 1
- QDRSPPYZRUQRBQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(pyrrolidine-1-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCCC2)=C1 QDRSPPYZRUQRBQ-UHFFFAOYSA-N 0.000 claims 1
- WOZBYUXMCLGDEF-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(thiomorpholine-4-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2CCSCC2)=C1 WOZBYUXMCLGDEF-UHFFFAOYSA-N 0.000 claims 1
- UBLJZAIYKTXMGT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-[2-(trifluoromethyl)pyrrolidine-1-carbonyl]pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(=O)N2C(CCC2)C(F)(F)F)=C1 UBLJZAIYKTXMGT-UHFFFAOYSA-N 0.000 claims 1
- WRKCZKRSMVVCAC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 WRKCZKRSMVVCAC-UHFFFAOYSA-N 0.000 claims 1
- IUQSVRWEHBDOPQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C=2SC=CC=2)=C1 IUQSVRWEHBDOPQ-UHFFFAOYSA-N 0.000 claims 1
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 claims 1
- RWCRMRXVVDJHMG-UHFFFAOYSA-N 2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]oxyacetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)OCC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RWCRMRXVVDJHMG-UHFFFAOYSA-N 0.000 claims 1
- LNSAXVOIIHJKAG-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]-3,3,3-trifluoropropanoic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NC(C(O)=O)C(F)(F)F)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LNSAXVOIIHJKAG-UHFFFAOYSA-N 0.000 claims 1
- RWBUIRGINUPZMJ-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]-3-methylbutanoic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)NC(C(C)C)C(O)=O)C=C1C(=O)NC1CCN(C(C)C)CC1 RWBUIRGINUPZMJ-UHFFFAOYSA-N 0.000 claims 1
- YBIUGSBCWFNIKH-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-4-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C=2SC=CC=2)=NN1CC1=CSC(C=2SC(Cl)=CC=2)=N1 YBIUGSBCWFNIKH-UHFFFAOYSA-N 0.000 claims 1
- BGRNUUSNEHQNGB-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(2,4-dichlorophenyl)pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C(=CC(Cl)=CC=2)Cl)C=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 BGRNUUSNEHQNGB-UHFFFAOYSA-N 0.000 claims 1
- IAUKLYNBOHXCPI-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C(CCC)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 IAUKLYNBOHXCPI-UHFFFAOYSA-N 0.000 claims 1
- MWSZMNDLBBGRLJ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C(C=2SC=CC=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 MWSZMNDLBBGRLJ-UHFFFAOYSA-N 0.000 claims 1
- RVPWYEUJXQXLMA-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=C(C#N)C=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RVPWYEUJXQXLMA-UHFFFAOYSA-N 0.000 claims 1
- UJYSLQLGXWWMBS-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2,2-dimethylpyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CCC2)(C)C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 UJYSLQLGXWWMBS-UHFFFAOYSA-N 0.000 claims 1
- SWBMLZSWIROPSM-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-methoxyethoxymethyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(COCCOC)C=C1C(=O)NC1CCN(C(C)C)CC1 SWBMLZSWIROPSM-UHFFFAOYSA-N 0.000 claims 1
- FCFBDEQSQTZCKX-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C=2OC(=O)NN=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 FCFBDEQSQTZCKX-UHFFFAOYSA-N 0.000 claims 1
- OPWGMMQINUFSCR-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxypyrrolidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(O)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OPWGMMQINUFSCR-UHFFFAOYSA-N 0.000 claims 1
- BKESUWSQSTZJOH-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-methylsulfonylpyrrolidine-1-carbonyl)pyrazole-3-carboxylic acid Chemical compound C1C(S(=O)(=O)C)CCN1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 BKESUWSQSTZJOH-UHFFFAOYSA-N 0.000 claims 1
- KSTFHMLRHRQHPT-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-oxopiperazine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CC(=O)NCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 KSTFHMLRHRQHPT-UHFFFAOYSA-N 0.000 claims 1
- VULRIWHYXFKIIN-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4,4-difluoropiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC(F)(F)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 VULRIWHYXFKIIN-UHFFFAOYSA-N 0.000 claims 1
- SQPOLHIPQYMDAA-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4,4-difluoropiperidine-1-carbonyl)pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(C(=O)N2CCC(F)(F)CC2)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 SQPOLHIPQYMDAA-UHFFFAOYSA-N 0.000 claims 1
- YFQPTTHWCHRRNO-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(4-hydroxypiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC(O)CC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 YFQPTTHWCHRRNO-UHFFFAOYSA-N 0.000 claims 1
- ZASUCJSHSMJOBZ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(morpholine-4-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCOCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZASUCJSHSMJOBZ-UHFFFAOYSA-N 0.000 claims 1
- KHYGGKDGRBTBTN-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[2-(hydroxymethyl)pyrrolidine-1-carbonyl]pyrazole-3-carboxylic acid Chemical compound OCC1CCCN1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 KHYGGKDGRBTBTN-UHFFFAOYSA-N 0.000 claims 1
- CVJYQRRKJCKSJX-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[4-(hydroxymethyl)piperidine-1-carbonyl]pyrazole-3-carboxylic acid Chemical compound C1CC(CO)CCN1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 CVJYQRRKJCKSJX-UHFFFAOYSA-N 0.000 claims 1
- QHFCHZAABCKOPQ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-methyl-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QHFCHZAABCKOPQ-UHFFFAOYSA-N 0.000 claims 1
- RLLIVYAPBPIXDT-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(1,3-thiazolidine-3-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CSCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RLLIVYAPBPIXDT-UHFFFAOYSA-N 0.000 claims 1
- DGNUPCRLEZEJHY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(pyrrolidine-1-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DGNUPCRLEZEJHY-UHFFFAOYSA-N 0.000 claims 1
- HMVSSZRUJOAIER-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-(thiomorpholine-4-carbonyl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCSCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HMVSSZRUJOAIER-UHFFFAOYSA-N 0.000 claims 1
- JDAJKZAZEKHTPQ-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-[2-(trifluoromethyl)pyrrolidine-1-carbonyl]pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2C(CCC2)C(F)(F)F)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JDAJKZAZEKHTPQ-UHFFFAOYSA-N 0.000 claims 1
- DBKQWBAGGQFKIM-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-propylpyrazole-3-carboxamide Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(CCC)C=C1C(=O)NC1CCN(C(C)C)CC1 DBKQWBAGGQFKIM-UHFFFAOYSA-N 0.000 claims 1
- RDBUONFQFSETIY-UHFFFAOYSA-N 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)-5-thiophen-2-ylpyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C=2SC=CC=2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RDBUONFQFSETIY-UHFFFAOYSA-N 0.000 claims 1
- DECGKHKHBIAIRZ-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)OCCO)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DECGKHKHBIAIRZ-UHFFFAOYSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 1
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 1
- SWWNEEARDBKZJW-UHFFFAOYSA-N 3-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]propanoic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)NCCC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SWWNEEARDBKZJW-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 1
- PUYQOTUFNYIXRF-UHFFFAOYSA-N 5-(8-azaspiro[4.5]decane-8-carbonyl)-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(C(=O)N2CCC3(CCCC3)CC2)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 PUYQOTUFNYIXRF-UHFFFAOYSA-N 0.000 claims 1
- RPRYVADYLZGDNO-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(=O)N2CCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RPRYVADYLZGDNO-UHFFFAOYSA-N 0.000 claims 1
- DMFHWXMIXBAURI-UHFFFAOYSA-N 5-[2,5-bis(methoxymethyl)pyrrolidine-1-carbonyl]-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrazole-3-carboxylic acid Chemical compound COCC1CCC(COC)N1C(=O)C1=CC(C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DMFHWXMIXBAURI-UHFFFAOYSA-N 0.000 claims 1
- GTWHBMRBFLNEEA-UHFFFAOYSA-N 5-[2,5-bis(methoxymethyl)pyrrolidine-1-carbonyl]-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrazole-3-carboxylic acid Chemical compound COCC1CCC(COC)N1C(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(O)=O)=C1 GTWHBMRBFLNEEA-UHFFFAOYSA-N 0.000 claims 1
- AMBCWOHRSPLMOP-UHFFFAOYSA-N 5-tert-butyl-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C(C(C)(C)C)=C1 AMBCWOHRSPLMOP-UHFFFAOYSA-N 0.000 claims 1
- BGPXQDRSXPTAIS-UHFFFAOYSA-N 5-tert-butyl-2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC(C(C)(C)C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 BGPXQDRSXPTAIS-UHFFFAOYSA-N 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- LTORGPPRBRMWNA-UHFFFAOYSA-N C1CC1NC(=O)C1=NN(C(=C1)C(=O)O)CC1=NOC(=C1)C=1SC(=CC1)Cl Chemical compound C1CC1NC(=O)C1=NN(C(=C1)C(=O)O)CC1=NOC(=C1)C=1SC(=CC1)Cl LTORGPPRBRMWNA-UHFFFAOYSA-N 0.000 claims 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Chemical group 0.000 claims 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- AXEWDBITUNKKHA-UHFFFAOYSA-N ethyl 1-[2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)C1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 AXEWDBITUNKKHA-UHFFFAOYSA-N 0.000 claims 1
- BIOMNDTWRIMQGV-UHFFFAOYSA-N ethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)OCC)C=C1C(=O)NC1CCN(C(C)C)CC1 BIOMNDTWRIMQGV-UHFFFAOYSA-N 0.000 claims 1
- KCYLYUSKPIMYGP-UHFFFAOYSA-N ethyl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]-3-methylbutanoate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)NC(C(=O)OCC)C(C)C)C=C1C(=O)NC1CCN(C(C)C)CC1 KCYLYUSKPIMYGP-UHFFFAOYSA-N 0.000 claims 1
- FGJPGGDLBPGGNS-UHFFFAOYSA-N ethyl 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 FGJPGGDLBPGGNS-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 1
- CNJGKWDHDUQANJ-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)OC)C=C1C(=O)NC1CCN(C(C)C)CC1 CNJGKWDHDUQANJ-UHFFFAOYSA-N 0.000 claims 1
- YCCAZWMOIWVKTG-UHFFFAOYSA-N methyl 2-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carboxylate Chemical compound COC(=O)C1=CC(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 YCCAZWMOIWVKTG-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims 1
- UPXNUDZXDSQQMG-UHFFFAOYSA-N propan-2-yl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrazole-3-carbonyl]amino]acetate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1N=C(C(=O)NCC(=O)OC(C)C)C=C1C(=O)NC1CCN(C(C)C)CC1 UPXNUDZXDSQQMG-UHFFFAOYSA-N 0.000 claims 1
- 125000005494 pyridonyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 0 CC(N(*)C#N)=O Chemical compound CC(N(*)C#N)=O 0.000 description 5
- YGLFALRUNLRHTL-UHFFFAOYSA-N CC(C(COC(C)=O)O1)OC1=O Chemical compound CC(C(COC(C)=O)O1)OC1=O YGLFALRUNLRHTL-UHFFFAOYSA-N 0.000 description 1
- PYUQCOIVVOLGJK-UHFFFAOYSA-N CC(C1)=NOC1=O Chemical compound CC(C1)=NOC1=O PYUQCOIVVOLGJK-UHFFFAOYSA-N 0.000 description 1
- RKRLQDJTVWZXMM-UHFFFAOYSA-N CC(N1)=NOC1=O Chemical compound CC(N1)=NOC1=O RKRLQDJTVWZXMM-UHFFFAOYSA-N 0.000 description 1
- XLSXXXARCKJHOR-UHFFFAOYSA-N CC(NN1)=NC1=O Chemical compound CC(NN1)=NC1=O XLSXXXARCKJHOR-UHFFFAOYSA-N 0.000 description 1
- NNXROHRFMWHXNH-UHFFFAOYSA-N CC(O1)=NNC1=O Chemical compound CC(O1)=NNC1=O NNXROHRFMWHXNH-UHFFFAOYSA-N 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N CC(ON1)=CC1=O Chemical compound CC(ON1)=CC1=O KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02028915A EP1433788A1 (en) | 2002-12-23 | 2002-12-23 | Pyrazole-derivatives as factor Xa inhibitors |
| EP03011308A EP1479678A1 (en) | 2003-05-19 | 2003-05-19 | Pyrazole-derivatives as factor xa inhibitors |
| PCT/EP2003/013979 WO2004056815A1 (en) | 2002-12-23 | 2003-12-10 | PYRAZOLE-DERIVATIVES AS FACTOR Xa INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511608A JP2006511608A (ja) | 2006-04-06 |
| JP2006511608A5 true JP2006511608A5 (enExample) | 2007-01-11 |
| JP4585448B2 JP4585448B2 (ja) | 2010-11-24 |
Family
ID=32683809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005502535A Expired - Fee Related JP4585448B2 (ja) | 2002-12-23 | 2003-12-10 | 第Ｘａ因子阻害剤としてのピラゾール−誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1581523B1 (enExample) |
| JP (1) | JP4585448B2 (enExample) |
| AR (1) | AR042648A1 (enExample) |
| AT (1) | ATE444292T1 (enExample) |
| AU (1) | AU2003292218A1 (enExample) |
| BR (1) | BR0317659A (enExample) |
| CA (1) | CA2511321A1 (enExample) |
| DE (1) | DE60329529D1 (enExample) |
| IL (1) | IL169323A0 (enExample) |
| MX (1) | MXPA05006200A (enExample) |
| PE (1) | PE20040925A1 (enExample) |
| TW (1) | TW200505914A (enExample) |
| WO (1) | WO2004056815A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| ITMI20041032A1 (it) | 2004-05-24 | 2004-08-24 | Neuroscienze S C A R L | Compositi farmaceutici |
| DE102004047255A1 (de) * | 2004-09-29 | 2006-04-13 | Merck Patent Gmbh | Prolinderivate |
| AU2005299693B2 (en) | 2004-10-26 | 2012-07-05 | Janssen Pharmaceutica, N.V. | Factor Xa compounds |
| US7381732B2 (en) | 2004-10-26 | 2008-06-03 | Bristol-Myers Squibb Company | Pyrazolobenzamides and derivatives as factor Xa inhibitors |
| CN101087762A (zh) * | 2004-10-29 | 2007-12-12 | 先灵公司 | 作为抗病毒剂的取代的5－甲酰胺吡唑和[1,2,4]三唑 |
| US8110573B2 (en) | 2004-12-30 | 2012-02-07 | Astex Therapeutics Limited | Pyrazole compounds that modulate the activity of CDK, GSK and aurora kinases |
| EP1724269A1 (en) * | 2005-05-20 | 2006-11-22 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-carboxylic acid (sulfamoyl alkyl) amide - derivatives as factor Xa inhibitors |
| MX2008000141A (es) * | 2005-06-27 | 2008-04-07 | Exelixis Inc | Moduladores de lxr basados en imidazol. |
| EP1968579A1 (en) | 2005-12-30 | 2008-09-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
| JP5523829B2 (ja) | 2006-06-29 | 2014-06-18 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| JP5560202B2 (ja) * | 2007-12-26 | 2014-07-23 | サノフイ | Ｐ２ｙ１２拮抗薬としてのピラゾール−カルボキサミド誘導体 |
| JP5504171B2 (ja) * | 2007-12-26 | 2014-05-28 | サノフイ | Ｐ２ｙ１２アンタゴニストとしてのヘテロサイクリックピラゾール−カルボキサミド |
| CA2720343A1 (en) | 2008-04-04 | 2009-10-08 | Takeda Pharmaceutical Company Limited | Heterocyclic derivative and use thereof |
| AU2009240643B2 (en) * | 2008-04-23 | 2014-03-06 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| AR079967A1 (es) | 2010-01-26 | 2012-02-29 | Sanofi Aventis | Derivados de acido 3-heteroaroilamino-propionico sustituidos con oxigeno y su uso como productos farmaceuticos |
| SG10201502484SA (en) | 2010-03-30 | 2015-05-28 | Verseon Corp | Multisubstituted aromatic compounds as inhibitors of thrombin |
| TWI523844B (zh) | 2011-01-26 | 2016-03-01 | 賽諾菲公司 | 經胺基取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| US8669370B2 (en) | 2011-01-26 | 2014-03-11 | Sanofi | Substituted 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
| CN103827098B (zh) | 2011-07-26 | 2016-06-15 | 赛诺菲 | 取代的3-(噻唑-4-羰基)-或者3-(噻唑-2-羰基)-氨基丙酸衍生物及其作为药物的用途 |
| WO2013014204A2 (en) | 2011-07-26 | 2013-01-31 | Sanofi | 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
| US20130123276A1 (en) | 2011-11-14 | 2013-05-16 | Sven Ruf | Use of telaprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases |
| US20130123325A1 (en) | 2011-11-14 | 2013-05-16 | Sven Ruf | Use of boceprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases |
| HK1214252A1 (zh) | 2013-03-15 | 2016-07-22 | Verseon Corporation | 作為凝血酶抑制劑的鹵代吡唑 |
| ES2702182T3 (es) * | 2013-03-15 | 2019-02-27 | Verseon Corp | Compuestos aromáticos multisustituidos como inhibidores de la serina proteasa |
| AU2014243070B2 (en) | 2013-03-28 | 2017-12-21 | Sanofi | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
| WO2014154726A1 (en) | 2013-03-28 | 2014-10-02 | Sanofi | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
| EP2805705B1 (en) | 2013-05-23 | 2016-11-09 | IP Gesellschaft für Management mbH | Packaging with one or more administration units comprising a sodium salt of (R)-3-[6-amino-pyridin-3-yl]-2-(1-cyclohexyl-1 H-imidazol-4-yl)-propionic acid |
| BR112017004704A2 (pt) | 2014-09-17 | 2018-01-23 | Verseon Corp | composto, composição farmacêutica, e, método para tratar uma doença ou distúrbio em um indivíduo |
| SG11201706411YA (en) | 2015-02-27 | 2017-09-28 | Verseon Corp | Substituted pyrazole compounds as serine protease inhibitors |
| WO2016202756A1 (en) | 2015-06-18 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | Substituted 2-(1h-pyrazol-1-yl)-1h-benzimidazole compounds |
| JOP20190192A1 (ar) * | 2017-03-01 | 2019-08-08 | Glaxosmithkline Ip No 2 Ltd | مشتقات بيرازول بوصفها مثبطات برومودومين |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| US5998424A (en) * | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| EP1045846B1 (en) * | 1997-11-28 | 2003-05-02 | Lg Chemical Limited | Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof |
| JP2001526268A (ja) * | 1997-12-22 | 2001-12-18 | デュポン ファーマシューティカルズ カンパニー | Ｘａ因子阻害剤としての、オルト−置換Ｐ１を有する、窒素含有複素環式芳香族化合物 |
| WO2000039131A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | Nitrogen containing heterobicycles as factor xa inhibitors |
| MXPA02000537A (es) * | 1999-07-16 | 2004-09-10 | Bristol Myers Squibb Pharma Co | Heterobiciclos que contienen nitrogeno como inhibidores del factor xa. |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| NZ517828A (en) * | 1999-09-17 | 2003-10-31 | Millennium Pharm Inc | Inhibitors having activity against mammalian factor Xa |
| WO2001032628A1 (en) * | 1999-11-03 | 2001-05-10 | Bristol-Myers Squibb Pharma Company | Cyano compounds as factor xa inhibitors |
| CA2409762A1 (en) * | 2000-06-23 | 2002-01-03 | Donald J.P. Pinto | Heteroaryl-phenyl substituted factor xa inhibitors |
| AU2001273040A1 (en) * | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| CA2444571A1 (en) * | 2001-04-18 | 2002-10-31 | Bristol-Myers Squibb Company | 1, 4, 5, 6-tetrahydropyrazolo-¬3, 4-c|-pyridin-7-ones as factor xa inhi bitors |
-
2003
- 2003-12-10 JP JP2005502535A patent/JP4585448B2/ja not_active Expired - Fee Related
- 2003-12-10 WO PCT/EP2003/013979 patent/WO2004056815A1/en not_active Ceased
- 2003-12-10 DE DE60329529T patent/DE60329529D1/de not_active Expired - Lifetime
- 2003-12-10 EP EP03767776A patent/EP1581523B1/en not_active Expired - Lifetime
- 2003-12-10 AT AT03767776T patent/ATE444292T1/de not_active IP Right Cessation
- 2003-12-10 AU AU2003292218A patent/AU2003292218A1/en not_active Abandoned
- 2003-12-10 MX MXPA05006200A patent/MXPA05006200A/es unknown
- 2003-12-10 BR BR0317659-2A patent/BR0317659A/pt not_active IP Right Cessation
- 2003-12-10 CA CA002511321A patent/CA2511321A1/en not_active Abandoned
- 2003-12-19 TW TW092136068A patent/TW200505914A/zh unknown
- 2003-12-22 AR ARP030104773A patent/AR042648A1/es unknown
-
2004
- 2004-01-05 PE PE2004000015A patent/PE20040925A1/es not_active Application Discontinuation
-
2005
- 2005-06-21 IL IL169323A patent/IL169323A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006511608A5 (enExample) | ||
| JP2006528942A5 (enExample) | ||
| JP4585448B2 (ja) | 第Ｘａ因子阻害剤としてのピラゾール−誘導体 | |
| JP2006528940A5 (enExample) | ||
| CA2624749A1 (en) | Pyrimidine amide compounds as pgds inhibitors | |
| JP2008503497A5 (enExample) | ||
| AU2003282006B2 (en) | Pyrimidinone derivatives as therapeutic agents against acute and chronic inflammatory ischaemic and remodelling processes | |
| JP2009510170A5 (enExample) | ||
| US20070244088A1 (en) | New Pyridine Analogues II | |
| JP4764418B2 (ja) | アルツハイマー病の治療のためのβ−セクレターゼ阻害剤として有用な２，４，６−置換ピリジル誘導体化合物 | |
| JP4861306B2 (ja) | Ｘａ因子阻害剤としてのピロール誘導体 | |
| WO2008086188A2 (en) | Thiophene carboxamides as factor xa inhibitors | |
| CA2674924A1 (en) | Factor xa inhibitors | |
| WO2006002099A2 (en) | Factor xa inhibitors | |
| KR20060136457A (ko) | 인자 Ｘａ 억제제로서의 피롤-유도체 | |
| EP2016072A1 (en) | Factor xa inhibitors | |
| JP2006500369A5 (enExample) | ||
| WO2008130021A2 (en) | Heterocyclic hydrazide compound and pesticidal use of the same | |
| JP2006528942A (ja) | 第Ｘａ因子阻害剤としてのインダゾール誘導体 | |
| KR20070083939A (ko) | 아릴옥시 치환된 벤즈이미다졸 유도체 | |
| TW201300380A (zh) | 抑制β－分泌酶活性之噁二唑化合物及其使用方法 | |
| RU2006141246A (ru) | Производные имидазола в качестве ингибиторов tafia | |
| JP2008526840A5 (enExample) | ||
| US20090227555A2 (en) | Novel Pyridine Compounds | |
| JP2006504674A (ja) | 新規のチオフェン誘導体、該誘導体の製造方法、及び該誘導体を含む医薬組成物 |