BRPI0610320A2 - derivados de ácido (sulfamoil-alquil)-amida heteroaril-carboxìlico como inibidores de fator xa - Google Patents

Info

Publication number

BRPI0610320A2

BRPI0610320A2 BRPI0610320-0A BRPI0610320A BRPI0610320A2 BR PI0610320 A2 BRPI0610320 A2 BR PI0610320A2 BR PI0610320 A BRPI0610320 A BR PI0610320A BR PI0610320 A2 BRPI0610320 A2 BR PI0610320A2

Authority

BR

Brazil

Prior art keywords

alkylene

alkyl

unsubstituted

independently

mono

Prior art date

2005-05-20

Links

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• -1 heteroaryl carboxylic acid Chemical class 0.000 title claims description 333
• 150000001408 amides Chemical class 0.000 title description 10
• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 153
• 238000000034 method Methods 0.000 claims abstract description 76
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 28
• 230000005764 inhibitory process Effects 0.000 claims abstract description 17
• 230000023555 blood coagulation Effects 0.000 claims abstract description 13
• 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 13
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 13
• 239000003814 drug Substances 0.000 claims abstract description 10
• 208000037803 restenosis Diseases 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 130
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 239000000203 mixture Substances 0.000 claims description 76
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
• 229910052736 halogen Inorganic materials 0.000 claims description 65
• 150000002367 halogens Chemical group 0.000 claims description 65
• 125000002947 alkylene group Chemical group 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 150000003254 radicals Chemical class 0.000 claims description 49
• 239000000460 chlorine Substances 0.000 claims description 47
• 229910052801 chlorine Inorganic materials 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 45
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 40
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 230000015572 biosynthetic process Effects 0.000 claims description 20
• 150000001721 carbon Chemical group 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 239000011593 sulfur Substances 0.000 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 239000001301 oxygen Chemical group 0.000 claims description 16
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 15
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002541 furyl group Chemical group 0.000 claims description 14
• 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 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 239000002243 precursor Substances 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-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
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• GHDARLKSYBCZRE-UHFFFAOYSA-N 1,4,3-oxathiazinane 4,4-dioxide Chemical compound O=S1(=O)CCOCN1 GHDARLKSYBCZRE-UHFFFAOYSA-N 0.000 claims description 9
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 9
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 9
• 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 9
• 125000002785 azepinyl group Chemical group 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 9
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
• DNGMYXZLJGHHOM-UHFFFAOYSA-N thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCCCN1 DNGMYXZLJGHHOM-UHFFFAOYSA-N 0.000 claims description 9
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 8
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
• 208000007536 Thrombosis Diseases 0.000 claims description 8
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 8
• XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical group O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims description 7
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 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 description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 7
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
• 230000002792 vascular Effects 0.000 claims description 7
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 6
• WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims description 6
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 6
• 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 239000003146 anticoagulant agent Substances 0.000 claims description 6
• 230000020764 fibrinolysis Effects 0.000 claims description 6
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• GMQOZFVOGGIFIX-UHFFFAOYSA-N oxathiazolidine Chemical compound C1COSN1 GMQOZFVOGGIFIX-UHFFFAOYSA-N 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 125000005493 quinolyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000002053 thietanyl group Chemical group 0.000 claims description 6
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 5
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-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
• 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
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-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
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 5
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
• 238000001356 surgical procedure Methods 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 5
• 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 4
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
• ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical compound C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 claims description 4
• 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims description 4
• FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 claims description 4
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
• 238000002399 angioplasty Methods 0.000 claims description 4
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
• 230000002537 thrombolytic effect Effects 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 210000003462 vein Anatomy 0.000 claims description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
• QYDWOMNEMGOSNN-UHFFFAOYSA-N 1,2,4-thiadiazolidine 1,1-dioxide Chemical compound O=S1(=O)CNCN1 QYDWOMNEMGOSNN-UHFFFAOYSA-N 0.000 claims description 3
• 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 3
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
• IXAZIGSJNTYTGJ-UHFFFAOYSA-N 1,2,5-thiadiazinane 1,1-dioxide Chemical compound O=S1(=O)CNCCN1 IXAZIGSJNTYTGJ-UHFFFAOYSA-N 0.000 claims description 3
• PZODDSWUYWTGHR-UHFFFAOYSA-N 1,2,6-thiadiazepane 1,1-dioxide Chemical compound O=S1(=O)CNCCCN1 PZODDSWUYWTGHR-UHFFFAOYSA-N 0.000 claims description 3
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 3
• YTBSOFLQSAXDKA-UHFFFAOYSA-N 1,3,2-dithiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCSN1 YTBSOFLQSAXDKA-UHFFFAOYSA-N 0.000 claims description 3
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
• CFRCZLVPCCLZFG-UHFFFAOYSA-N 1,3,4-oxathiazinane 3,3-dioxide Chemical compound O=S1(=O)COCCN1 CFRCZLVPCCLZFG-UHFFFAOYSA-N 0.000 claims description 3
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 3
• PTJGQWYPPWNJOF-UHFFFAOYSA-N 1,4,2-dithiazolidine 1,1-dioxide Chemical compound O=S1(=O)CSCN1 PTJGQWYPPWNJOF-UHFFFAOYSA-N 0.000 claims description 3
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 3
• 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 3
• 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims description 3
• RMIIPFHXZBZULD-UHFFFAOYSA-N 1,5,2-dithiazinane 1,1-dioxide Chemical compound O=S1(=O)CSCCN1 RMIIPFHXZBZULD-UHFFFAOYSA-N 0.000 claims description 3
• ARPNQFMNYLNSSQ-UHFFFAOYSA-N 1,6,2-dithiazepane 1,1-dioxide Chemical compound O=S1(=O)CSCCCN1 ARPNQFMNYLNSSQ-UHFFFAOYSA-N 0.000 claims description 3
• OGOVCJUTZGZKOH-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole 1,1-dioxide Chemical compound O=S1(=O)NCC=C1 OGOVCJUTZGZKOH-UHFFFAOYSA-N 0.000 claims description 3
• WHHSFLNHWGCVNC-UHFFFAOYSA-N 2,5,6,7-tetrahydrothiazepine 1,1-dioxide Chemical compound O=S1(=O)CCCC=CN1 WHHSFLNHWGCVNC-UHFFFAOYSA-N 0.000 claims description 3
• JVOUGZZPWYEQBE-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole 1,1-dioxide Chemical compound O=S1(=O)CN=CN1 JVOUGZZPWYEQBE-UHFFFAOYSA-N 0.000 claims description 3
• PKWBYLAKTCTAIC-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole 1,1-dioxide Chemical compound O=S1(=O)CC=CN1 PKWBYLAKTCTAIC-UHFFFAOYSA-N 0.000 claims description 3
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