KR20050100655A - 티에노〔2,3-ｃ〕피리딘 유도체를 함유하는 약제학적조성물 및 그의 용도 - Google Patents

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Publication number

KR20050100655A

KR20050100655A KR1020057014345A KR20057014345A KR20050100655A KR 20050100655 A KR20050100655 A KR 20050100655A KR 1020057014345 A KR1020057014345 A KR 1020057014345A KR 20057014345 A KR20057014345 A KR 20057014345A KR 20050100655 A KR20050100655 A KR 20050100655A

Authority

KR

South Korea

Prior art keywords

pyridine

amino

benzoyl

sulfonyl

tetrahydrothieno

Prior art date

2003-02-05

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.)

Withdrawn

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 72
• GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical class C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 79
• 238000000034 method Methods 0.000 claims abstract description 71
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 70
• 230000003993 interaction Effects 0.000 claims abstract description 48
• 230000001404 mediated effect Effects 0.000 claims abstract description 40
• 201000010099 disease Diseases 0.000 claims abstract description 35
• 208000035475 disorder Diseases 0.000 claims abstract description 35
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
• 230000003612 virological effect Effects 0.000 claims abstract description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• -1 4-methyl-1-piperazinyl Chemical group 0.000 claims description 109
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 97
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 97
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 93
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 70
• 229920000669 heparin Polymers 0.000 claims description 67
• 229960002897 heparin Drugs 0.000 claims description 64
• 108010092694 L-Selectin Proteins 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 55
• 239000004480 active ingredient Substances 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 210000004027 cell Anatomy 0.000 claims description 35
• 210000000265 leukocyte Anatomy 0.000 claims description 33
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 32
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 108010035766 P-Selectin Proteins 0.000 claims description 23
• 102100023472 P-selectin Human genes 0.000 claims description 23
• 210000000440 neutrophil Anatomy 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 230000004054 inflammatory process Effects 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 229920002971 Heparan sulfate Polymers 0.000 claims description 20
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 20
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 20
• 230000021164 cell adhesion Effects 0.000 claims description 20
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 201000011510 cancer Diseases 0.000 claims description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 230000008595 infiltration Effects 0.000 claims description 14
• 238000001764 infiltration Methods 0.000 claims description 14
• 201000006417 multiple sclerosis Diseases 0.000 claims description 14
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 125000001589 carboacyl group Chemical group 0.000 claims description 12
• 230000012292 cell migration Effects 0.000 claims description 12
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 12
• 238000001727 in vivo Methods 0.000 claims description 12
• 206010027476 Metastases Diseases 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 238000000338 in vitro Methods 0.000 claims description 11
• 230000009401 metastasis Effects 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• VPEMNPODXCXJJF-UHFFFAOYSA-N 2-[[4-[benzyl(ethyl)sulfamoyl]benzoyl]amino]-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=C(C=3CCN(CC)CC=3S2)C(N)=O)C=CC=1S(=O)(=O)N(CC)CC1=CC=CC=C1 VPEMNPODXCXJJF-UHFFFAOYSA-N 0.000 claims description 10
• YRSSRCFBMMLSLW-UHFFFAOYSA-N 6-ethyl-2-[[4-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C1N(CC)CCC(C=2C(N)=O)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 YRSSRCFBMMLSLW-UHFFFAOYSA-N 0.000 claims description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• XTNPTCYECQYVTN-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(C)C2)=C2S1 XTNPTCYECQYVTN-UHFFFAOYSA-N 0.000 claims description 10
• CVAIQWZNGNUDNR-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[methyl(phenyl)sulfamoyl]benzamide Chemical compound C=1C=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=CC=1S(=O)(=O)N(C)C1=CC=CC=C1 CVAIQWZNGNUDNR-UHFFFAOYSA-N 0.000 claims description 10
• 235000005152 nicotinamide Nutrition 0.000 claims description 10
• 239000011570 nicotinamide Substances 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• GQIDNMVCAHJPCE-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(CC)C2)=C2S1 GQIDNMVCAHJPCE-UHFFFAOYSA-N 0.000 claims description 9
• BQHHKCLXPYGPGT-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[butyl(ethyl)sulfamoyl]benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CCCC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(CC)C2)=C2S1 BQHHKCLXPYGPGT-UHFFFAOYSA-N 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 230000001363 autoimmune Effects 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 206010053567 Coagulopathies Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
• 125000005002 aryl methyl group Chemical group 0.000 claims description 6
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
• 239000012634 fragment Substances 0.000 claims description 6
• 235000012054 meals Nutrition 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• XFPAWXVMVIZPDA-UHFFFAOYSA-N 2-[[4-(cyclohexylmethylsulfamoyl)benzoyl]amino]-5,5,7,7-tetramethyl-4,6-dihydrothieno[2,3-c]pyridine-3-carboxamide Chemical compound CC1(C)NC(C)(C)CC(C=2C(N)=O)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)NCC1CCCCC1 XFPAWXVMVIZPDA-UHFFFAOYSA-N 0.000 claims description 5
• SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 5
• ZOMTULULPOPWSY-UHFFFAOYSA-N 6-ethyl-n-methyl-2-[[4-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical compound C1N(CC)CCC(C=2C(=O)NC)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 ZOMTULULPOPWSY-UHFFFAOYSA-N 0.000 claims description 5
• PYMLRHLGNABFST-UHFFFAOYSA-N 6-ethyl-n-methyl-2-[[4-[methyl(phenyl)sulfamoyl]benzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxamide Chemical class C1N(CC)CCC(C=2C(=O)NC)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N(C)C1=CC=CC=C1 PYMLRHLGNABFST-UHFFFAOYSA-N 0.000 claims description 5
• PLHDAQZIQCLSKN-UHFFFAOYSA-N C(C)OC(=O)C1=C(SC2=C(N=C(C(=C21)C)C)C)C Chemical compound C(C)OC(=O)C1=C(SC2=C(N=C(C(=C21)C)C)C)C PLHDAQZIQCLSKN-UHFFFAOYSA-N 0.000 claims description 5
• ZEHCXKNEKXAUTO-UHFFFAOYSA-N CC=1N=C(C(=C2C1SC(=C2C(=O)N)C)C)C Chemical compound CC=1N=C(C(=C2C1SC(=C2C(=O)N)C)C)C ZEHCXKNEKXAUTO-UHFFFAOYSA-N 0.000 claims description 5
• 229920001287 Chondroitin sulfate Polymers 0.000 claims description 5
• 229920000045 Dermatan sulfate Polymers 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 229940059329 chondroitin sulfate Drugs 0.000 claims description 5
• AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 5
• 229940051593 dermatan sulfate Drugs 0.000 claims description 5
• USKFCOOWLKKDLE-UHFFFAOYSA-N ethyl 2-[[4-(4-ethoxycarbonylpiperazin-1-yl)sulfonylbenzoyl]amino]-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(CC=3S2)C(C)C)C(=O)OCC)C=C1 USKFCOOWLKKDLE-UHFFFAOYSA-N 0.000 claims description 5
• ADQQLSYRNOPLSQ-UHFFFAOYSA-N ethyl 2-[[4-[butyl(methyl)sulfamoyl]benzoyl]amino]-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carboxylate Chemical compound C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1C(=O)NC1=C(C(=O)OCC)C(CCN(C2)C(C)C)=C2S1 ADQQLSYRNOPLSQ-UHFFFAOYSA-N 0.000 claims description 5
• KLFOEZXNHITOJP-UHFFFAOYSA-N ethyl 3-(1,3-benzothiazol-2-yl)-2-[[4-(diethylsulfamoyl)benzoyl]amino]-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C1=CC=C(S(=O)(=O)N(CC)CC)C=C1 KLFOEZXNHITOJP-UHFFFAOYSA-N 0.000 claims description 5
• FLQYXSJREWKIED-UHFFFAOYSA-N ethyl 4-[4-[(3-carbamoyl-5,5,7,7-tetramethyl-4,6-dihydrothieno[2,3-c]pyridin-2-yl)carbamoyl]phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C3=C(C(NC(C)(C)C3)(C)C)S2)C(N)=O)C=C1 FLQYXSJREWKIED-UHFFFAOYSA-N 0.000 claims description 5
• KMJHAJQYFYDERS-UHFFFAOYSA-N ethyl 4-[4-[[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]carbamoyl]phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=C1 KMJHAJQYFYDERS-UHFFFAOYSA-N 0.000 claims description 5
• 208000014674 injury Diseases 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
• 208000017169 kidney disease Diseases 0.000 claims description 5
• UATBAWDREQQTDE-UHFFFAOYSA-N methyl 2,4,5,7-tetramethylthieno[2,3-c]pyridine-3-carboxylate Chemical compound N1=C(C)C(C)=C2C(C(=O)OC)=C(C)SC2=C1C UATBAWDREQQTDE-UHFFFAOYSA-N 0.000 claims description 5
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 5
• CBSHUWKSSHJYPZ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-ethyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(4-methylpiperazin-1-yl)sulfonylbenzamide Chemical compound C1N(CC)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 CBSHUWKSSHJYPZ-UHFFFAOYSA-N 0.000 claims description 5
• YMDJVTMDUDKYKZ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(4-methylpiperazin-1-yl)sulfonylbenzamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C(=O)NC2=C(C=3CCN(C)CC=3S2)C=2SC3=CC=CC=C3N=2)C=C1 YMDJVTMDUDKYKZ-UHFFFAOYSA-N 0.000 claims description 5
• VXXJBJRWVMMHRU-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]benzamide Chemical compound C1=CC=C2SC(C3=C(NC(=O)C=4C=CC(=CC=4)S(=O)(=O)N4C5CC(CC(C)(C)C5)(C)C4)SC4=C3CCN(C4)C)=NC2=C1 VXXJBJRWVMMHRU-UHFFFAOYSA-N 0.000 claims description 5
• FLSOXNKHAMQZIN-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-morpholin-4-ylsulfonylbenzamide Chemical compound C1N(C)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 FLSOXNKHAMQZIN-UHFFFAOYSA-N 0.000 claims description 5
• VIYWMMCQNUKAEQ-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-(diethylsulfamoyl)benzamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C(=O)NC1=C(C=2SC3=CC=CC=C3N=2)C(CCN(C2)C(C)C)=C2S1 VIYWMMCQNUKAEQ-UHFFFAOYSA-N 0.000 claims description 5
• UQKSAQVUELOLQL-UHFFFAOYSA-N n-[3-(1,3-benzothiazol-2-yl)-6-propan-2-yl-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-4-morpholin-4-ylsulfonylbenzamide Chemical compound C1N(C(C)C)CCC(C=2C=3SC4=CC=CC=C4N=3)=C1SC=2NC(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 UQKSAQVUELOLQL-UHFFFAOYSA-N 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
• NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical group CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 claims description 4
• JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical group CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 4
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical group CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 229920000288 Keratan sulfate Polymers 0.000 claims description 4
• 208000004852 Lung Injury Diseases 0.000 claims description 4
• 206010069363 Traumatic lung injury Diseases 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 208000038016 acute inflammation Diseases 0.000 claims description 4
• 230000006022 acute inflammation Effects 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 208000015294 blood coagulation disease Diseases 0.000 claims description 4
• 229920005556 chlorobutyl Polymers 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 230000006020 chronic inflammation Effects 0.000 claims description 4
• 230000009852 coagulant defect Effects 0.000 claims description 4
• 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 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 4
• KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 claims description 4
• 231100000515 lung injury Toxicity 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 208000030507 AIDS Diseases 0.000 claims description 3
• 208000035143 Bacterial infection Diseases 0.000 claims description 3
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
• 208000005176 Hepatitis C Diseases 0.000 claims description 3
• 206010033645 Pancreatitis Diseases 0.000 claims description 3
• 206010033647 Pancreatitis acute Diseases 0.000 claims description 3
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