NO324792B1 - Farmasoytisk aktive sulfonamidderivater - Google Patents

Info

Publication number

NO324792B1

NO324792B1 NO20021530A NO20021530A NO324792B1 NO 324792 B1 NO324792 B1 NO 324792B1 NO 20021530 A NO20021530 A NO 20021530A NO 20021530 A NO20021530 A NO 20021530A NO 324792 B1 NO324792 B1 NO 324792B1

Authority

NO

Norway

Prior art keywords

sulfonyl

methyl

thien

piperidin

benzamide

Prior art date

1999-09-28

Links

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• Global Dossier
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• 229940124530 sulfonamide Drugs 0.000 title claims description 38
• 150000003456 sulfonamides Chemical class 0.000 title claims description 28
• -1 cyano, hydroxyl Chemical group 0.000 claims description 118
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 89
• 238000000034 method Methods 0.000 claims description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
• 208000035475 disorder Diseases 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 238000005859 coupling reaction Methods 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 150000001263 acyl chlorides Chemical class 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
• 125000005493 quinolyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• RCLZUQSDCHJJLX-UHFFFAOYSA-N n-[[5-[4-(benzimidazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=C2)S1 RCLZUQSDCHJJLX-UHFFFAOYSA-N 0.000 claims description 3
• ZWTZHPSNRRFOAF-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 ZWTZHPSNRRFOAF-UHFFFAOYSA-N 0.000 claims description 3
• QDHJPQKWODVHIM-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 QDHJPQKWODVHIM-UHFFFAOYSA-N 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• NITIZPRHXHKHKE-UHFFFAOYSA-N 2-[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]benzotriazole-5-carboxylic acid Chemical compound N1=C2C=C(C(=O)O)C=CC2=NN1C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 NITIZPRHXHKHKE-UHFFFAOYSA-N 0.000 claims description 2
• HYJJWJZEQVCURL-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,6-dichlorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C(=CC=CC=2Cl)Cl)S1 HYJJWJZEQVCURL-UHFFFAOYSA-N 0.000 claims description 2
• YWCKRKNLKAJANS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(6-chlorobenzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC(Cl)=CC=C3N=N2)S1 YWCKRKNLKAJANS-UHFFFAOYSA-N 0.000 claims description 2
• KVXNWEQMXWXTRN-UHFFFAOYSA-N 4-chloro-n-[[5-[[4-(2-phenylacetyl)-1,4-diazepan-1-yl]sulfonyl]thiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CCC2)C(=O)CC=2C=CC=CC=2)S1 KVXNWEQMXWXTRN-UHFFFAOYSA-N 0.000 claims description 2
• OTGAXMANQKRURD-UHFFFAOYSA-N 4-nitro-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)[N+]([O-])=O)S1 OTGAXMANQKRURD-UHFFFAOYSA-N 0.000 claims description 2
• UUOKRQSYOPPSIK-UHFFFAOYSA-N 4-nitro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=C1 UUOKRQSYOPPSIK-UHFFFAOYSA-N 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
• 208000026310 Breast neoplasm Diseases 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
• 206010019196 Head injury Diseases 0.000 claims description 2
• 208000023105 Huntington disease Diseases 0.000 claims description 2
• 208000007201 Myocardial reperfusion injury Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 208000017442 Retinal disease Diseases 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
• 208000006673 asthma Diseases 0.000 claims description 2
• AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical group N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 2
• 229960003529 diazepam Drugs 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 206010015037 epilepsy Diseases 0.000 claims description 2
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• CXCWQSZCTXWQSY-UHFFFAOYSA-N methyl 3-[[1-[5-[[(3-methoxybenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 CXCWQSZCTXWQSY-UHFFFAOYSA-N 0.000 claims description 2
• 201000006417 multiple sclerosis Diseases 0.000 claims description 2
• 208000010125 myocardial infarction Diseases 0.000 claims description 2
• FONJJKKVKBISOP-UHFFFAOYSA-N n-[[5-[4-(3-benzylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(CC=3C=CC=CC=3)C=CC=2)=C1 FONJJKKVKBISOP-UHFFFAOYSA-N 0.000 claims description 2
• JHFYWRCGTMMJHX-UHFFFAOYSA-N n-[[5-[4-(3-benzylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(CC=3C=CC=CC=3)C=CC=2)S1 JHFYWRCGTMMJHX-UHFFFAOYSA-N 0.000 claims description 2
• XSDVWTHVEGXZQE-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3,4-dihydroxybenzamide Chemical compound C1=C(O)C(O)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 XSDVWTHVEGXZQE-UHFFFAOYSA-N 0.000 claims description 2
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 230000036303 septic shock Effects 0.000 claims description 2
• HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 12
• 125000005843 halogen group Chemical group 0.000 claims 4
• QQQGBUXUGKEYGK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 QQQGBUXUGKEYGK-UHFFFAOYSA-N 0.000 claims 1
• MHGWSCDALBVNDX-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-methoxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 MHGWSCDALBVNDX-UHFFFAOYSA-N 0.000 claims 1
• UHKZTGCTYZBBKT-UHFFFAOYSA-N 4-chloro-N-[[5-[4-(quinolin-5-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide 4-chloro-N-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C3C=CC=NC3=CC=C2)C=C1.NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)Cl)=O)C=CC1 UHKZTGCTYZBBKT-UHFFFAOYSA-N 0.000 claims 1
• CZSHQDKLMREPIH-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,4-difluorobenzoyl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)C1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 CZSHQDKLMREPIH-UHFFFAOYSA-N 0.000 claims 1
• MYISFLPEOBBFKR-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-propylanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 MYISFLPEOBBFKR-UHFFFAOYSA-N 0.000 claims 1
• XVUHXWCAMOYWOY-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chloroanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC1CCN(S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 XVUHXWCAMOYWOY-UHFFFAOYSA-N 0.000 claims 1
• YMAQMFMFCZDCBD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(naphthalene-1-carbonyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide;4-chloro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1.C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C3=CC=CC=C3C=CC=2)S1 YMAQMFMFCZDCBD-UHFFFAOYSA-N 0.000 claims 1
• UWZVGIBPCUQWRW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(quinolin-8-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C3=NC=CC=C3C=CC=2)S1 UWZVGIBPCUQWRW-UHFFFAOYSA-N 0.000 claims 1
• ACBBNXWLABVBQR-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[3-(2-hydroxyethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OCCS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 ACBBNXWLABVBQR-UHFFFAOYSA-N 0.000 claims 1
• LGAAEFJZLLETLT-UHFFFAOYSA-N C(C)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1.C(CCC)NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1 Chemical compound C(C)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1.C(CCC)NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1 LGAAEFJZLLETLT-UHFFFAOYSA-N 0.000 claims 1
• HVBGARUVAXPEPG-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)N1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=C1 HVBGARUVAXPEPG-UHFFFAOYSA-N 0.000 claims 1
• HLEZAOUYMDNPGJ-UHFFFAOYSA-N ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=C(C=CC=C2)[N+](=O)[O-])=O)C=C1.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(=O)C2=CC=CC3=CC=CC=C23)C=C1 Chemical compound ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=C(C=CC=C2)[N+](=O)[O-])=O)C=C1.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(=O)C2=CC=CC3=CC=CC=C23)C=C1 HLEZAOUYMDNPGJ-UHFFFAOYSA-N 0.000 claims 1
• ZQJHRBLAJVRVJG-UHFFFAOYSA-N ClC1=CC=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1.[N+](=O)([O-])C=1C=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C(C=CC=C2)[N+](=O)[O-])C=CC1 Chemical compound ClC1=CC=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1.[N+](=O)([O-])C=1C=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C(C=CC=C2)[N+](=O)[O-])C=CC1 ZQJHRBLAJVRVJG-UHFFFAOYSA-N 0.000 claims 1
• NPUSVCYOOTYAJO-UHFFFAOYSA-N OCCS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=CC1.N(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC(=CC=C1)[N+](=O)[O-])=O Chemical compound OCCS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=CC1.N(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC(=CC=C1)[N+](=O)[O-])=O NPUSVCYOOTYAJO-UHFFFAOYSA-N 0.000 claims 1
• 206010052779 Transplant rejections Diseases 0.000 claims 1
• 201000011510 cancer Diseases 0.000 claims 1
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