JP2006511608A5 - - Google Patents
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- 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
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- -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
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- 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
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- 239000005977 Ethylene Chemical group 0.000 claims 1
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- 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
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| PCT/EP2003/013979 WO2004056815A1 (en) | 2002-12-23 | 2003-12-10 | PYRAZOLE-DERIVATIVES AS FACTOR Xa INHIBITORS |
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| 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 |
| US7446210B2 (en) | 2004-10-26 | 2008-11-04 | 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 |
| EP1814860B1 (en) * | 2004-10-29 | 2009-06-03 | Schering Corporation | Substituted 5-carboxyamide pyrazoles and [1,2,4]triazoles as antiviral agents |
| EP1833819A1 (en) | 2004-12-30 | 2007-09-19 | 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 |
| US8703805B2 (en) * | 2005-06-27 | 2014-04-22 | Exelixis Patent Company Llc | Modulators of LXR |
| EP1968579A1 (en) | 2005-12-30 | 2008-09-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
| EP2049119A2 (en) | 2006-06-29 | 2009-04-22 | Astex Therapeutics Limited | Pharmaceutical combinations of 1-cyclopropyl-3-[3-(5-morphoolin-4-ylmethyl-1h-benzoimidazol-2-yl)-1h-1-pyrazol-4-yl]-urea |
| WO2009080227A2 (en) * | 2007-12-26 | 2009-07-02 | Sanofi-Aventis | Pyrazole-carboxamide derivatives as p2y12 antagonists |
| EP2238128B1 (en) * | 2007-12-26 | 2012-08-22 | Sanofi | Heterocyclic pyrazole-carboxamides as p2y12 antagonists |
| CN102056907B (zh) | 2008-04-04 | 2014-12-31 | 武田药品工业株式会社 | 杂环衍生物及其用途 |
| MX2010011288A (es) * | 2008-04-23 | 2010-11-09 | Rigel Pharmaceuticals Inc | Compuestos de carboxamida para el tratamiento de trastornos metabolicos. |
| TWI532725B (zh) | 2010-01-26 | 2016-05-11 | 賽諾菲阿凡提斯公司 | 經氧取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| JP6155187B2 (ja) | 2010-03-30 | 2017-06-28 | ヴァーセオン コーポレイション | トロンビンの阻害剤としての多置換芳香族化合物 |
| AR085013A1 (es) | 2011-01-26 | 2013-08-07 | Sanofi Aventis | Derivados de acido 3-heteroaroilamino-propionico sustituidos y su uso como sustancias farmaceuticas |
| 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 |
| JP6021910B2 (ja) | 2011-07-26 | 2016-11-09 | サノフイ | ３−ヘテロアロイルアミノ−プロピオン酸誘導体及び医薬としてのそれらの使用 |
| MY162786A (en) | 2011-07-26 | 2017-07-14 | Sanofi Sa | Substituted 3-thiazoloamino-propionic acid derivatives and their use as pharmaceuticals |
| WO2013072328A1 (en) | 2011-11-14 | 2013-05-23 | Sanofi | 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 |
| CN110179795A (zh) | 2013-03-15 | 2019-08-30 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的多取代芳族化合物的制药用途 |
| CA2907903A1 (en) | 2013-03-28 | 2014-10-02 | Sanofi | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
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| EP3184095A1 (en) | 2013-05-23 | 2017-06-28 | IP Gesellschaft für Management mbH | Administration units comprising polymorph 1 of 2-(2-methylamino-pyrimidin-4-yl]-1h-indole-5-carboxylic acid [(s)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| CN107405333A (zh) | 2015-02-27 | 2017-11-28 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| WO2016202756A1 (en) | 2015-06-18 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | Substituted 2-(1h-pyrazol-1-yl)-1h-benzimidazole compounds |
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| 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 |
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| WO2001032628A1 (en) * | 1999-11-03 | 2001-05-10 | Bristol-Myers Squibb Pharma Company | Cyano compounds as factor xa inhibitors |
| AU2001268711A1 (en) * | 2000-06-23 | 2002-01-08 | Bristol-Myers Squibb Pharma Company | Heteroaryl-phenyl substituted factor xa inhibitors |
| WO2002000651A2 (en) * | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma 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 DE DE60329529T patent/DE60329529D1/de not_active Expired - Lifetime
- 2003-12-10 BR BR0317659-2A patent/BR0317659A/pt not_active IP Right Cessation
- 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 WO PCT/EP2003/013979 patent/WO2004056815A1/en not_active Ceased
- 2003-12-10 AU AU2003292218A patent/AU2003292218A1/en not_active Abandoned
- 2003-12-10 CA CA002511321A patent/CA2511321A1/en not_active Abandoned
- 2003-12-10 MX MXPA05006200A patent/MXPA05006200A/es unknown
- 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
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