SK101399A3 - Arylsulfonyl hydroxamic acid derivatives - Google Patents
Arylsulfonyl hydroxamic acid derivatives Download PDFInfo
- Publication number
- SK101399A3 SK101399A3 SK1013-99A SK101399A SK101399A3 SK 101399 A3 SK101399 A3 SK 101399A3 SK 101399 A SK101399 A SK 101399A SK 101399 A3 SK101399 A3 SK 101399A3
- Authority
- SK
- Slovakia
- Prior art keywords
- carbon atoms
- alkyl
- aryl
- heteroaryl
- moiety
- Prior art date
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- -1 Arylsulfonyl hydroxamic Chemical compound 0.000 title claims abstract description 145
- 239000002253 acid Substances 0.000 title claims description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 13
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 10
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 208000025865 Ulcer Diseases 0.000 claims abstract description 8
- 206010003246 arthritis Diseases 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 230000036269 ulceration Effects 0.000 claims abstract description 8
- 206010040047 Sepsis Diseases 0.000 claims abstract description 7
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 7
- 208000028169 periodontal disease Diseases 0.000 claims abstract description 7
- 230000036303 septic shock Effects 0.000 claims abstract description 7
- 208000030507 AIDS Diseases 0.000 claims abstract description 6
- 229940035676 analgesics Drugs 0.000 claims abstract description 6
- 239000000730 antalgic agent Substances 0.000 claims abstract description 6
- 208000037803 restenosis Diseases 0.000 claims abstract description 6
- 206010039705 Scleritis Diseases 0.000 claims abstract description 5
- 231100000433 cytotoxic Toxicity 0.000 claims abstract description 5
- 230000001472 cytotoxic effect Effects 0.000 claims abstract description 5
- 208000002780 macular degeneration Diseases 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 235
- 125000003118 aryl group Chemical group 0.000 claims description 144
- 125000001072 heteroaryl group Chemical group 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 125000003545 alkoxy group Chemical group 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 25
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 24
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 24
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 17
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
- 241000282414 Homo sapiens Species 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000002393 azetidinyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000006537 (C6-C10)-aryl alkyl group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 6
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 6
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000005035 acylthio group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000005418 aryl aryl group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 150000008575 L-amino acids Chemical class 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 241000282412 Homo Species 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims description 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 3
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- DCNAGTIFBSSTEQ-CZUORRHYSA-N (2R,4R)-1-(4-methoxyphenyl)sulfonyl-4-(piperazine-1-carbonyl)piperidine-2-carboxylic acid Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N2CC[C@H](C[C@@H]2C(=O)O)C(=O)N3CCNCC3 DCNAGTIFBSSTEQ-CZUORRHYSA-N 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
- DFFFQSWTAXMMBT-UHFFFAOYSA-N n-hydroxypiperidine-2-carboxamide Chemical compound ONC(=O)C1CCCCN1 DFFFQSWTAXMMBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
- 125000004149 thio group Chemical group *S* 0.000 claims 2
- KCBCIFNWFHZSGL-QFBILLFUSA-N (2r,3s)-1-[4-(1,3-benzothiazol-2-ylmethoxy)phenyl]sulfonyl-n,3-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=NC2=CC=CC=C2S1 KCBCIFNWFHZSGL-QFBILLFUSA-N 0.000 claims 1
- JOLNGWZCQMJSCD-ZWKOTPCHSA-N (2r,3s)-n,3-dihydroxy-1-[4-(2-pyridin-4-ylethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCCC1=CC=NC=C1 JOLNGWZCQMJSCD-ZWKOTPCHSA-N 0.000 claims 1
- JMBOAEVTEXTTPO-BXUZGUMPSA-N (2r,4r)-1-[3-(4-fluorophenoxy)propylsulfonyl]-2-(hydroxycarbamoyl)piperidine-4-carboxylic acid Chemical compound ONC(=O)[C@H]1C[C@H](C(O)=O)CCN1S(=O)(=O)CCCOC1=CC=C(F)C=C1 JMBOAEVTEXTTPO-BXUZGUMPSA-N 0.000 claims 1
- ACEUKQZDNBIUHG-CRAIPNDOSA-N (2r,4r)-n,4-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ACEUKQZDNBIUHG-CRAIPNDOSA-N 0.000 claims 1
- UUSUIALWMWHMSS-CRAIPNDOSA-N (2r,5r)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,5-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 UUSUIALWMWHMSS-CRAIPNDOSA-N 0.000 claims 1
- GIGWICZCQGBJDH-MAUKXSAKSA-N (2r,5s)-n,5-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GIGWICZCQGBJDH-MAUKXSAKSA-N 0.000 claims 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- PDFDFBYWRAAPBF-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-2-(hydroxycarbamoyl)piperidine-4-carboxylic acid Chemical compound ONC(=O)C1CC(C(O)=O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 PDFDFBYWRAAPBF-UHFFFAOYSA-N 0.000 claims 1
- UAISREBYDOFHJY-UHFFFAOYSA-N 4-oxopiperidin-1-ium-2-carboxylate Chemical compound OC(=O)C1CC(=O)CCN1 UAISREBYDOFHJY-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 206010053177 Epidermolysis Diseases 0.000 claims 1
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 claims 1
- 102000010750 Metalloproteins Human genes 0.000 claims 1
- 108010063312 Metalloproteins Proteins 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000006430 alkyl cyclopropyl group Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 102000057041 human TNF Human genes 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 abstract description 4
- 206010014989 Epidermolysis bullosa Diseases 0.000 abstract description 4
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 abstract description 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 abstract description 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 abstract description 2
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- 229910052697 platinum Inorganic materials 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 53
- 239000000243 solution Substances 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 125000006239 protecting group Chemical group 0.000 description 22
- 238000003556 assay Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 108060005980 Collagenase Proteins 0.000 description 17
- 102000029816 Collagenase Human genes 0.000 description 17
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- CNCJXVCCTNQTQC-ZEQKJWHPSA-N tert-butyl 4-[(2r,4r)-1-(4-methoxyphenyl)sulfonyl-2-(phenylmethoxycarbamoyl)piperidine-4-carbonyl]piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1[C@@H](C(=O)NOCC=2C=CC=CC=2)C[C@H](C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)CC1 CNCJXVCCTNQTQC-ZEQKJWHPSA-N 0.000 description 1
- UIXPAFTUPFSJII-VQIMIIECSA-N tert-butyl 4-[(2r,4r)-2-(hydroxycarbamoyl)-1-(4-methoxyphenyl)sulfonylpiperidine-4-carbonyl]piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1[C@@H](C(=O)NO)C[C@H](C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)CC1 UIXPAFTUPFSJII-VQIMIIECSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3760097P | 1997-02-11 | 1997-02-11 | |
| PCT/IB1998/000064 WO1998034918A1 (en) | 1997-02-11 | 1998-01-16 | Arylsulfonyl hydroxamic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK101399A3 true SK101399A3 (en) | 2001-09-11 |
Family
ID=21895216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1013-99A SK101399A3 (en) | 1997-02-11 | 1998-01-16 | Arylsulfonyl hydroxamic acid derivatives |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US6599890B1 (hu) |
| EP (1) | EP0960098A1 (hu) |
| JP (1) | JP3710489B2 (hu) |
| KR (1) | KR20000070923A (hu) |
| CN (1) | CN1247531A (hu) |
| AP (1) | AP958A (hu) |
| AR (1) | AR011123A1 (hu) |
| AU (1) | AU722784B2 (hu) |
| BG (1) | BG63430B1 (hu) |
| BR (1) | BR9807678A (hu) |
| CA (1) | CA2280151C (hu) |
| CO (1) | CO4950619A1 (hu) |
| DZ (1) | DZ2416A1 (hu) |
| EA (1) | EA002546B1 (hu) |
| GT (1) | GT199800026A (hu) |
| HN (1) | HN1998000020A (hu) |
| HR (1) | HRP980070B1 (hu) |
| HU (1) | HUP0000657A3 (hu) |
| ID (1) | ID22809A (hu) |
| IL (1) | IL131123A0 (hu) |
| IS (1) | IS5130A (hu) |
| MA (1) | MA24469A1 (hu) |
| NO (1) | NO993836L (hu) |
| NZ (1) | NZ336836A (hu) |
| OA (1) | OA11142A (hu) |
| PA (1) | PA8446101A1 (hu) |
| PE (1) | PE58699A1 (hu) |
| PL (1) | PL334997A1 (hu) |
| SA (1) | SA98180856A (hu) |
| SK (1) | SK101399A3 (hu) |
| TN (1) | TNSN98025A1 (hu) |
| TR (1) | TR199901926T2 (hu) |
| TW (1) | TW502020B (hu) |
| UY (1) | UY24880A1 (hu) |
| WO (1) | WO1998034918A1 (hu) |
| YU (1) | YU37499A (hu) |
| ZA (1) | ZA981061B (hu) |
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- 1998-01-16 SK SK1013-99A patent/SK101399A3/sk unknown
- 1998-01-16 KR KR1019997007188A patent/KR20000070923A/ko not_active Application Discontinuation
- 1998-01-16 CA CA002280151A patent/CA2280151C/en not_active Expired - Fee Related
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- 1998-01-16 CN CN98802460A patent/CN1247531A/zh active Pending
- 1998-01-16 TR TR1999/01926T patent/TR199901926T2/xx unknown
- 1998-01-16 NZ NZ336836A patent/NZ336836A/en unknown
- 1998-01-16 EA EA199900641A patent/EA002546B1/ru not_active IP Right Cessation
- 1998-01-16 EP EP98900124A patent/EP0960098A1/en not_active Withdrawn
- 1998-01-16 IL IL13112398A patent/IL131123A0/xx not_active IP Right Cessation
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- 1998-01-16 JP JP53404098A patent/JP3710489B2/ja not_active Expired - Fee Related
- 1998-01-26 HN HN1998000020A patent/HN1998000020A/es unknown
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- 1998-02-05 AP APAP/P/1998/001179A patent/AP958A/en active
- 1998-02-06 UY UY24880A patent/UY24880A1/es not_active IP Right Cessation
- 1998-02-06 PE PE1998000087A patent/PE58699A1/es not_active Application Discontinuation
- 1998-02-09 TW TW087101709A patent/TW502020B/zh not_active IP Right Cessation
- 1998-02-10 DZ DZ980026A patent/DZ2416A1/xx active
- 1998-02-10 TN TNTNSN98025A patent/TNSN98025A1/fr unknown
- 1998-02-10 MA MA24960A patent/MA24469A1/fr unknown
- 1998-02-10 AR ARP980100582A patent/AR011123A1/es not_active Application Discontinuation
- 1998-02-10 ZA ZA9801061A patent/ZA981061B/xx unknown
- 1998-02-11 CO CO98007136A patent/CO4950619A1/es unknown
- 1998-02-12 HR HR980070A patent/HRP980070B1/xx not_active IP Right Cessation
- 1998-02-15 SA SA98180856A patent/SA98180856A/ar unknown
- 1998-02-18 PA PA19988446101A patent/PA8446101A1/es unknown
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1999
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- 1999-08-05 BG BG103641A patent/BG63430B1/bg active Active
- 1999-08-06 OA OA9900174A patent/OA11142A/en unknown
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2000
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