ES2338151T3 - Derivados de (sulfamoil alquil) amida del acido heteroaril-carboxilico como inhibidores del factor xa. - Google Patents

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Publication number

ES2338151T3

ES2338151T3 ES06753510T ES06753510T ES2338151T3 ES 2338151 T3 ES2338151 T3 ES 2338151T3 ES 06753510 T ES06753510 T ES 06753510T ES 06753510 T ES06753510 T ES 06753510T ES 2338151 T3 ES2338151 T3 ES 2338151T3

Authority

ES

Spain

Prior art keywords

alkylene

alkyl

substituted

acid

mono

Prior art date

2005-05-20

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.)

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• 239000002253 acid Substances 0.000 title claims description 360
• 239000003112 inhibitor Substances 0.000 title description 12
• -1 cetopiperazinilo Chemical group 0.000 claims abstract description 250
• 150000001875 compounds Chemical class 0.000 claims abstract description 151
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 105
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 61
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 59
• 239000000460 chlorine Substances 0.000 claims abstract description 52
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 51
• 150000002367 halogens Chemical group 0.000 claims abstract description 51
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
• 125000003118 aryl group Chemical group 0.000 claims abstract description 42
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
• 125000004429 atom Chemical group 0.000 claims abstract description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 22
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 21
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
• 239000001257 hydrogen Substances 0.000 claims abstract description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 15
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 13
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
• 239000011593 sulfur Substances 0.000 claims abstract description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 239000001301 oxygen Chemical group 0.000 claims abstract description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 12
• 239000004305 biphenyl Substances 0.000 claims abstract description 11
• 235000010290 biphenyl Nutrition 0.000 claims abstract description 11
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 11
• 125000002541 furyl group Chemical group 0.000 claims abstract description 11
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 10
• 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 9
• 125000005955 1H-indazolyl group Chemical group 0.000 claims abstract description 8
• 125000005602 azabenzimidazolyl group Chemical group 0.000 claims abstract description 8
• 125000002785 azepinyl group Chemical group 0.000 claims abstract description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 8
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 8
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 8
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 8
• 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 abstract description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 8
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 8
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims abstract description 8
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 8
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims abstract description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 8
• GMQOZFVOGGIFIX-UHFFFAOYSA-N oxathiazolidine Chemical compound C1COSN1 GMQOZFVOGGIFIX-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 8
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 8
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims abstract description 8
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims abstract description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 8
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 8
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract description 8
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims abstract description 7
• 125000005493 quinolyl group Chemical group 0.000 claims abstract description 7
• 125000001425 triazolyl group Chemical group 0.000 claims abstract description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 5
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims abstract description 5
• QYDWOMNEMGOSNN-UHFFFAOYSA-N 1,2,4-thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)CNCN1 QYDWOMNEMGOSNN-UHFFFAOYSA-N 0.000 claims abstract description 4
• OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 3
• 125000006091 1,3-dioxolane group Chemical group 0.000 claims abstract 2
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 187
• 238000000034 method Methods 0.000 claims description 82
• 239000000203 mixture Substances 0.000 claims description 75
• 150000003839 salts Chemical class 0.000 claims description 46
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
• ULWLOWQIWTUFBD-UHFFFAOYSA-N 2-amino-n-(1-propan-2-ylpiperidin-4-yl)ethanesulfonamide Chemical compound CC(C)N1CCC(NS(=O)(=O)CCN)CC1 ULWLOWQIWTUFBD-UHFFFAOYSA-N 0.000 claims description 41
• 108010074860 Factor Xa Proteins 0.000 claims description 31
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
• 230000015572 biosynthetic process Effects 0.000 claims description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 15
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 13
• 230000023555 blood coagulation Effects 0.000 claims description 13
• 239000002243 precursor Substances 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 238000002560 therapeutic procedure Methods 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
• 150000001721 carbon Chemical group 0.000 claims description 10
• CANQLFKETNFYAF-UHFFFAOYSA-N 1,4,3-oxathiazinane Chemical compound C1CSNCO1 CANQLFKETNFYAF-UHFFFAOYSA-N 0.000 claims description 9
• 208000037803 restenosis Diseases 0.000 claims description 9
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 239000011737 fluorine Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• DULCJHSHAUBUTC-JTQLQIEISA-N (2s)-2-amino-3-hydroxy-n-(1-propan-2-ylpiperidin-4-yl)propane-1-sulfonamide Chemical compound CC(C)N1CCC(NS(=O)(=O)C[C@@H](N)CO)CC1 DULCJHSHAUBUTC-JTQLQIEISA-N 0.000 claims description 6
• JKBUUYDKYUYZGM-UHFFFAOYSA-N 2-amino-2-methyl-n-(1-propan-2-ylpiperidin-4-yl)propane-1-sulfonamide Chemical compound CC(C)N1CCC(NS(=O)(=O)CC(C)(C)N)CC1 JKBUUYDKYUYZGM-UHFFFAOYSA-N 0.000 claims description 6
• WQEBWMQVVGVQQT-UHFFFAOYSA-N 2-amino-n-(1-cyclopropylpiperidin-4-yl)ethanesulfonamide Chemical compound C1CC(NS(=O)(=O)CCN)CCN1C1CC1 WQEBWMQVVGVQQT-UHFFFAOYSA-N 0.000 claims description 6
• VQFIVYCQNLSSBN-UHFFFAOYSA-N 2-amino-n-(1-propan-2-ylpiperidin-4-yl)-n-(1,3-thiazol-2-ylmethyl)ethanesulfonamide Chemical compound C1CN(C(C)C)CCC1N(S(=O)(=O)CCN)CC1=NC=CS1 VQFIVYCQNLSSBN-UHFFFAOYSA-N 0.000 claims description 6
• APOGXTQFDHCLNI-UHFFFAOYSA-N 2-amino-n-(4-benzylpiperazin-1-yl)ethanesulfonamide Chemical compound C1CN(NS(=O)(=O)CCN)CCN1CC1=CC=CC=C1 APOGXTQFDHCLNI-UHFFFAOYSA-N 0.000 claims description 6
• SJFSWZZKIHLRNW-UHFFFAOYSA-N 2-nitro-1,2-thiazolidine 1,1-dioxide Chemical compound [O-][N+](=O)N1CCCS1(=O)=O SJFSWZZKIHLRNW-UHFFFAOYSA-N 0.000 claims description 6
• YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 claims description 6
• VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• 208000007536 Thrombosis Diseases 0.000 claims description 6
• 238000002399 angioplasty Methods 0.000 claims description 6
• 239000003146 anticoagulant agent Substances 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 claims description 6
• 230000002792 vascular Effects 0.000 claims description 6
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 5
• WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims description 5
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 5
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 5
• LJOKCCXZRJEYTA-UHFFFAOYSA-N 2-[2-aminoethylsulfonyl-(1-propan-2-ylpiperidin-4-yl)amino]-N,N-dimethylacetamide Chemical compound CC(C)N1CCC(N(CC(=O)N(C)C)S(=O)(=O)CCN)CC1 LJOKCCXZRJEYTA-UHFFFAOYSA-N 0.000 claims description 5
• CDAPCDZEONRNEU-UHFFFAOYSA-N 2-[2-aminoethylsulfonyl-(1-propan-2-ylpiperidin-4-yl)amino]acetamide Chemical compound CC(C)N1CCC(N(CC(N)=O)S(=O)(=O)CCN)CC1 CDAPCDZEONRNEU-UHFFFAOYSA-N 0.000 claims description 5
• ZUVOUGOZAPUEGZ-UHFFFAOYSA-N 2-amino-N-(1-propan-2-ylpiperidin-4-yl)-N-(pyridin-3-ylmethyl)ethanesulfonamide Chemical compound C1CN(C(C)C)CCC1N(S(=O)(=O)CCN)CC1=CC=CN=C1 ZUVOUGOZAPUEGZ-UHFFFAOYSA-N 0.000 claims description 5
• IIXZGDXWYCJHPW-UHFFFAOYSA-N 2-amino-N-(2-hydroxyethyl)-N-(1-propan-2-ylpiperidin-4-yl)ethanesulfonamide Chemical compound CC(C)N1CCC(N(CCO)S(=O)(=O)CCN)CC1 IIXZGDXWYCJHPW-UHFFFAOYSA-N 0.000 claims description 5
• OCEFJXFCJUNZJW-UHFFFAOYSA-N 2-amino-N-(2-morpholin-4-yl-2-oxoethyl)-N-(1-propan-2-ylpiperidin-4-yl)ethanesulfonamide Chemical compound C1CN(C(C)C)CCC1N(S(=O)(=O)CCN)CC(=O)N1CCOCC1 OCEFJXFCJUNZJW-UHFFFAOYSA-N 0.000 claims description 5
• UMABUEWGZINDGG-UHFFFAOYSA-N 2-amino-N-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]-N-(1-propan-2-ylpiperidin-4-yl)ethanesulfonamide Chemical compound C1CN(C(C)C)CCC1N(S(=O)(=O)CCN)CC1=NN=C(C2CC2)S1 UMABUEWGZINDGG-UHFFFAOYSA-N 0.000 claims description 5
• IDXQQTUXADMGPR-UHFFFAOYSA-N 2-amino-n-methyl-n-(1-propan-2-ylpiperidin-4-yl)ethanesulfonamide Chemical compound CC(C)N1CCC(N(C)S(=O)(=O)CCN)CC1 IDXQQTUXADMGPR-UHFFFAOYSA-N 0.000 claims description 5
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 5
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 5
• MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 5
• USZBBMOYMDBVHL-UHFFFAOYSA-N 3-amino-n-(1-propan-2-ylpiperidin-4-yl)propane-1-sulfonamide Chemical compound CC(C)N1CCC(NS(=O)(=O)CCCN)CC1 USZBBMOYMDBVHL-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
• GJLOKYIYZIOIPN-UHFFFAOYSA-N 5-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)C=N1 GJLOKYIYZIOIPN-UHFFFAOYSA-N 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims description 5
• 229940127557 pharmaceutical product Drugs 0.000 claims description 5
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 5
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 5
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 5
• 238000001356 surgical procedure Methods 0.000 claims description 5
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 5
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
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