IL107155A

IL107155A - Esters of acylsulfonamide - and sulfonamidopyridine-2 carboxylic acid and their pyridine N-oxides, methods for their preparation and use as drugs

Esters of acylsulfonamide - and sulfonamidopyridine-2 carboxylic acid and their pyridine N-oxides, methods for their preparation and use as drugs

Info

Publication number: IL107155A
Authority: IL; Israel
Prior art keywords: amino; pyridine; carbonyl; carboxylate example; ethyl
Prior art date: 1992-10-02

Application number

IL10715593A

Other languages

English (en)

Hebrew (he)

Other versions

IL107155A0 (en

Original Assignee

Hoechst Ag

Priority date

1992-10-02

Filing date

1993-09-29

Publication date

1999-09-22

1993-09-29 Application filed by Hoechst Ag filed Critical Hoechst Ag

1993-12-28 Publication of IL107155A0 publication Critical patent/IL107155A0/xx

1999-09-22 Publication of IL107155A publication Critical patent/IL107155A/en

Links

238000000034 method Methods 0.000 title claims description 62
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 90
239000003814 drug Substances 0.000 claims abstract description 11
230000003176 fibrotic effect Effects 0.000 claims abstract description 6
201000010099 disease Diseases 0.000 claims abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
-1 heteroaryl radical Chemical class 0.000 claims description 343
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 100
150000003254 radicals Chemical class 0.000 claims description 85
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 81
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
150000005840 aryl radicals Chemical class 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
229920001436 collagen Polymers 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
108010035532 Collagen Proteins 0.000 claims description 9
102000008186 Collagen Human genes 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 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000000939 carbamoylcarbamoyl group Chemical group C(N)(=O)NC(=O)* 0.000 claims 2
125000004475 heteroaralkyl group Chemical group 0.000 claims 2
230000001590 oxidative effect Effects 0.000 claims 2
125000004442 acylamino group Chemical group 0.000 claims 1
125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
125000004429 atom Chemical class 0.000 claims 1
125000004404 heteroalkyl group Chemical group 0.000 claims 1
230000004060 metabolic process Effects 0.000 claims 1
125000004344 phenylpropyl group Chemical group 0.000 claims 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 abstract description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 294
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 281
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 97
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
238000002844 melting Methods 0.000 description 62
230000008018 melting Effects 0.000 description 62
235000013350 formula milk Nutrition 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 47
239000000203 mixture Substances 0.000 description 34
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 23
239000000047 product Substances 0.000 description 23
239000000243 solution Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229910052736 halogen Inorganic materials 0.000 description 12
150000002367 halogens Chemical class 0.000 description 12
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 12
239000012043 crude product Substances 0.000 description 11
125000004093 cyano group Chemical group *C#N 0.000 description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
150000007942 carboxylates Chemical class 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 8
VUEDWFASDKQVGU-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-[(3,4-dimethoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)C=C1 VUEDWFASDKQVGU-UHFFFAOYSA-N 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 description 7
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
210000004185 liver Anatomy 0.000 description 6
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 5
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
102000004079 Prolyl Hydroxylases Human genes 0.000 description 5
108010043005 Prolyl Hydroxylases Proteins 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
CONFLANRPBHBBR-UHFFFAOYSA-N methyl 5-(benzenesulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 CONFLANRPBHBBR-UHFFFAOYSA-N 0.000 description 4
XVKHGHADCCNXBZ-UHFFFAOYSA-N methyl 5-(benzylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)CC1=CC=CC=C1 XVKHGHADCCNXBZ-UHFFFAOYSA-N 0.000 description 4
OGLMGRFLAQRPKX-UHFFFAOYSA-N methyl 5-(propan-2-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(C(=O)NS(=O)(=O)C(C)C)C=N1 OGLMGRFLAQRPKX-UHFFFAOYSA-N 0.000 description 4
SDDNPFAIQSIZEX-UHFFFAOYSA-N methyl 5-(quinolin-8-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC2=CC=CN=C12 SDDNPFAIQSIZEX-UHFFFAOYSA-N 0.000 description 4
DKMIXUMECJPSAZ-UHFFFAOYSA-N methyl 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(OC)C=C1 DKMIXUMECJPSAZ-UHFFFAOYSA-N 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
JLJVRSJAJDFDMN-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-[(2,5-dimethoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC1=CC=C(OC)C(C(=O)NCCC=2C=CC(=CC=2)S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)=C1 JLJVRSJAJDFDMN-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
102000008490 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Human genes 0.000 description 3
108010020504 2-Oxoglutarate 5-Dioxygenase Procollagen-Lysine Proteins 0.000 description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
VXCNNKUETLEVAO-UHFFFAOYSA-N 5-(benzenesulfonylcarbamoyl)pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 VXCNNKUETLEVAO-UHFFFAOYSA-N 0.000 description 3
102000004266 Collagen Type IV Human genes 0.000 description 3
108010042086 Collagen Type IV Proteins 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000003510 anti-fibrotic effect Effects 0.000 description 3
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
229940113088 dimethylacetamide Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
PMICCTSYSCQHMS-UHFFFAOYSA-N methyl 5-(methylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(C(=O)NS(C)(=O)=O)C=N1 PMICCTSYSCQHMS-UHFFFAOYSA-N 0.000 description 3
CYVRIOICNJKKPY-UHFFFAOYSA-N methyl 5-(naphthalen-1-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 CYVRIOICNJKKPY-UHFFFAOYSA-N 0.000 description 3
WXTYQQDIOHKUMM-UHFFFAOYSA-N methyl 5-[(5-chlorothiophen-2-yl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(Cl)S1 WXTYQQDIOHKUMM-UHFFFAOYSA-N 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
229940124530 sulfonamide Drugs 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
GCPKGKSZGKZEKL-UHFFFAOYSA-N 5-[[4-[2-[(2-chloro-5-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound COC1=CC=C(Cl)C(C(=O)NCCC=2C=CC(=CC=2)S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(O)=O)=C1 GCPKGKSZGKZEKL-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
206010016654 Fibrosis Diseases 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
241001024304 Mino Species 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
108010050808 Procollagen Proteins 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003862 amino acid derivatives Chemical class 0.000 description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000003556 assay Methods 0.000 description 2
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000036570 collagen biosynthesis Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
210000001723 extracellular space Anatomy 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229960002591 hydroxyproline Drugs 0.000 description 2
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QPJVONKHWWAEBF-UHFFFAOYSA-N (4-methoxyphenyl)methyl 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)C1=CC=C(C(=O)NS(=O)(=O)C=2C=CC(CCNC(=O)CC=3C=CC=CC=3)=CC=2)C=N1 QPJVONKHWWAEBF-UHFFFAOYSA-N 0.000 description 1
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125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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ODBIQKJCWOBXAM-UHFFFAOYSA-N 3-methoxypropyl 5-[[4-[2-(2-methylpropanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCCOC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(=O)C(C)C)C=C1 ODBIQKJCWOBXAM-UHFFFAOYSA-N 0.000 description 1
FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 1
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KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
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HGKWMUBXVMFXNC-UHFFFAOYSA-N 4-butoxybenzenesulfonyl chloride Chemical compound CCCCOC1=CC=C(S(Cl)(=O)=O)C=C1 HGKWMUBXVMFXNC-UHFFFAOYSA-N 0.000 description 1
LFLSATHZMYYIAQ-UHFFFAOYSA-N 4-flourobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1 LFLSATHZMYYIAQ-UHFFFAOYSA-N 0.000 description 1
BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
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QVGMFZZFMWIXQS-KRWDZBQOSA-N [(2S)-butan-2-yl] 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C[C@@H](CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=CC=C(C=C1)Cl)=O QVGMFZZFMWIXQS-KRWDZBQOSA-N 0.000 description 1
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CTFXHOGBQCAGPE-KRWDZBQOSA-N [(2S)-butan-2-yl] 5-[[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C[C@@H](CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=C(C=CC(=C1)Cl)OC)=O CTFXHOGBQCAGPE-KRWDZBQOSA-N 0.000 description 1
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KNNWXCVRPCARQM-UHFFFAOYSA-N benzyl 5-[[4-(2-benzamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=CC=CC=1C(=O)NCCC(C=C1)=CC=C1S(=O)(=O)NC(=O)C(C=N1)=CC=C1C(=O)OCC1=CC=CC=C1 KNNWXCVRPCARQM-UHFFFAOYSA-N 0.000 description 1
DWLVBCZYQWOGTK-UHFFFAOYSA-N benzyl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=CC=1C(=O)NCCOC1=CC=CC=C1 DWLVBCZYQWOGTK-UHFFFAOYSA-N 0.000 description 1
QRILWZQJSAHCKU-UHFFFAOYSA-N benzyl 5-[[4-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=CC=1C(=O)NCCCC1=CC=CC=C1 QRILWZQJSAHCKU-UHFFFAOYSA-N 0.000 description 1
DYQJXPRCSQGPGC-UHFFFAOYSA-N benzyl 5-[[4-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=CC=1C(=O)NCC1=CC=CC=C1 DYQJXPRCSQGPGC-UHFFFAOYSA-N 0.000 description 1
UYXJKWGACQAWAQ-UHFFFAOYSA-N benzyl 5-[[4-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC1=CC=CC=C1CCNC(=O)C1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=C1 UYXJKWGACQAWAQ-UHFFFAOYSA-N 0.000 description 1
JGSQHMBNAOVDKI-UHFFFAOYSA-N benzyl 5-[[4-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC1=CC=CC(CCNC(=O)C=2C=CC(=CC=2)S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)=C1 JGSQHMBNAOVDKI-UHFFFAOYSA-N 0.000 description 1
GEOZWQXYKCTGBP-UHFFFAOYSA-N benzyl 5-[[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=C1 GEOZWQXYKCTGBP-UHFFFAOYSA-N 0.000 description 1
WATHFJSSTCFHCP-UHFFFAOYSA-N benzyl 5-[[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=C1 WATHFJSSTCFHCP-UHFFFAOYSA-N 0.000 description 1
YMPDHJDXCWVQNC-UHFFFAOYSA-N benzyl 5-[[4-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC=2C=CC=CC=2)C=C1 YMPDHJDXCWVQNC-UHFFFAOYSA-N 0.000 description 1
SHOSJEAMAFDDFJ-UHFFFAOYSA-N benzyl 5-[[4-[2-(butanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OCC=2C=CC=CC=2)N=C1 SHOSJEAMAFDDFJ-UHFFFAOYSA-N 0.000 description 1
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CQFJWDOZLZYOCQ-UHFFFAOYSA-N butyl 5-(naphthalen-1-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 CQFJWDOZLZYOCQ-UHFFFAOYSA-N 0.000 description 1
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238000004113 cell culture Methods 0.000 description 1
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QEZYNCXSHKYOLK-UHFFFAOYSA-N cyclohexyl 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 QEZYNCXSHKYOLK-UHFFFAOYSA-N 0.000 description 1
ATBGCHZSAYVNGT-UHFFFAOYSA-N cyclohexyl 5-[(4-phenoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(C(=O)OC2CCCCC2)N=CC=1C(=O)NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 ATBGCHZSAYVNGT-UHFFFAOYSA-N 0.000 description 1
HYNURPNOJFRABC-UHFFFAOYSA-N cyclohexyl 5-[[4-(2-ethoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 HYNURPNOJFRABC-UHFFFAOYSA-N 0.000 description 1
RZZMLTDFWXNGDP-UHFFFAOYSA-N cyclohexyl 5-[[4-(2-methoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 RZZMLTDFWXNGDP-UHFFFAOYSA-N 0.000 description 1
UIBQUQVOLYBMEY-UHFFFAOYSA-N cyclohexyl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1C(=O)NCCOC1=CC=CC=C1 UIBQUQVOLYBMEY-UHFFFAOYSA-N 0.000 description 1
HDFJYGADGKFIBB-UHFFFAOYSA-N cyclohexyl 5-[[4-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1C(=O)NCCC1=CC=CC=C1 HDFJYGADGKFIBB-UHFFFAOYSA-N 0.000 description 1
MOGFQBFOLWIHEN-UHFFFAOYSA-N cyclohexyl 5-[[4-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 MOGFQBFOLWIHEN-UHFFFAOYSA-N 0.000 description 1
QGMUGWPPYFJCFJ-UHFFFAOYSA-N cyclohexyl 5-[[4-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1C(=O)NCCCCC1=CC=CC=C1 QGMUGWPPYFJCFJ-UHFFFAOYSA-N 0.000 description 1
PFGIRLCWKRQYOH-UHFFFAOYSA-N cyclohexyl 5-[[4-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1C(=O)NCC1=CC=CC=C1 PFGIRLCWKRQYOH-UHFFFAOYSA-N 0.000 description 1
IVXYFLSNRBMJDK-UHFFFAOYSA-N cyclohexyl 5-[[4-(butylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 IVXYFLSNRBMJDK-UHFFFAOYSA-N 0.000 description 1
IMWRZBBXNQDQRY-UHFFFAOYSA-N cyclohexyl 5-[[4-(ethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 IMWRZBBXNQDQRY-UHFFFAOYSA-N 0.000 description 1
UHGXINONXGQZRU-UHFFFAOYSA-N cyclohexyl 5-[[4-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 UHGXINONXGQZRU-UHFFFAOYSA-N 0.000 description 1
VGNNCUORHKVGKH-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC1=CC=CC(CCNC(=O)C=2C=CC(=CC=2)S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)=C1 VGNNCUORHKVGKH-UHFFFAOYSA-N 0.000 description 1
MLZLGKWYOCMJED-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-(3-methylbutanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CC(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 MLZLGKWYOCMJED-UHFFFAOYSA-N 0.000 description 1
RTPQRDGLEZAYEU-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=C1 RTPQRDGLEZAYEU-UHFFFAOYSA-N 0.000 description 1
IKDABWPWNLIYKP-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-(4-methylpentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCC(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 IKDABWPWNLIYKP-UHFFFAOYSA-N 0.000 description 1
UJIPHDUSBHYKHK-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-(pentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCCC2)N=C1 UJIPHDUSBHYKHK-UHFFFAOYSA-N 0.000 description 1
OGHISDVIRRWEQZ-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1CCNC(=O)COC1=CC=CC=C1 OGHISDVIRRWEQZ-UHFFFAOYSA-N 0.000 description 1
QWHKXTWDHWXTRR-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=CC=1CCNC(=O)CC1=CC=CC=C1 QWHKXTWDHWXTRR-UHFFFAOYSA-N 0.000 description 1
AMKLULFUBLFVOV-UHFFFAOYSA-N cyclohexyl 5-[[4-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(F)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCCC2)C=C1 AMKLULFUBLFVOV-UHFFFAOYSA-N 0.000 description 1
NSAFJPSMBHMQJK-UHFFFAOYSA-N cyclopentyl 5-[[4-(2-methoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCC2)N=C1 NSAFJPSMBHMQJK-UHFFFAOYSA-N 0.000 description 1
UWVIHRGXNKUAQE-UHFFFAOYSA-N cyclopentyl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCC2)C=CC=1C(=O)NCCOC1=CC=CC=C1 UWVIHRGXNKUAQE-UHFFFAOYSA-N 0.000 description 1
ZQKWXEJJYIVSLO-UHFFFAOYSA-N cyclopentyl 5-[[4-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCC2)C=CC=1C(=O)NCCC1=CC=CC=C1 ZQKWXEJJYIVSLO-UHFFFAOYSA-N 0.000 description 1
ZAGRVCJJLIKXKC-UHFFFAOYSA-N cyclopentyl 5-[[4-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCC2)N=C1 ZAGRVCJJLIKXKC-UHFFFAOYSA-N 0.000 description 1
UKNMGGIQZHSRHV-UHFFFAOYSA-N cyclopentyl 5-[[4-(butylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCC2)N=C1 UKNMGGIQZHSRHV-UHFFFAOYSA-N 0.000 description 1
QRJUQDHNSIKZIW-UHFFFAOYSA-N cyclopentyl 5-[[4-(cyclohexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C=1C=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCC2)C=CC=1C(=O)NC1CCCCC1 QRJUQDHNSIKZIW-UHFFFAOYSA-N 0.000 description 1
LCWCVPGJDUGDHS-UHFFFAOYSA-N cyclopentyl 5-[[4-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC2CCCC2)N=C1 LCWCVPGJDUGDHS-UHFFFAOYSA-N 0.000 description 1
GKFVBYGFEVVFOT-UHFFFAOYSA-N cyclopentyl 5-[[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC2CCCC2)C=C1 GKFVBYGFEVVFOT-UHFFFAOYSA-N 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
ZWMFAVOLNIOFBS-UHFFFAOYSA-N ethyl 5-(naphthalen-1-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 ZWMFAVOLNIOFBS-UHFFFAOYSA-N 0.000 description 1
KVRDHBYRKMPBNF-UHFFFAOYSA-N ethyl 5-(naphthalen-2-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 KVRDHBYRKMPBNF-UHFFFAOYSA-N 0.000 description 1
UTURMNVDTBRAFQ-UHFFFAOYSA-N ethyl 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(OC)C=C1 UTURMNVDTBRAFQ-UHFFFAOYSA-N 0.000 description 1
HNLBNCXAESMNNY-UHFFFAOYSA-N ethyl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 HNLBNCXAESMNNY-UHFFFAOYSA-N 0.000 description 1
XGCJKEVBJGBVHF-UHFFFAOYSA-N ethyl 5-[[4-(2-methoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCOC)C=C1 XGCJKEVBJGBVHF-UHFFFAOYSA-N 0.000 description 1
AJNMPJLZAIJXJA-UHFFFAOYSA-N ethyl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCOC=2C=CC=CC=2)C=C1 AJNMPJLZAIJXJA-UHFFFAOYSA-N 0.000 description 1
RDCVMOSSQUGYTI-UHFFFAOYSA-N ethyl 5-[[4-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1 RDCVMOSSQUGYTI-UHFFFAOYSA-N 0.000 description 1
JKYHIPBIKISUFW-UHFFFAOYSA-N ethyl 5-[[4-(dibutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)N(CCCC)CCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OCC)N=C1 JKYHIPBIKISUFW-UHFFFAOYSA-N 0.000 description 1
WYCLZSINFLTYBE-UHFFFAOYSA-N ethyl 5-[[4-[2-(butanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OCC)N=C1 WYCLZSINFLTYBE-UHFFFAOYSA-N 0.000 description 1
WDQZTGGGJOSSFH-UHFFFAOYSA-N ethyl 5-[[4-[2-(pentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OCC)N=C1 WDQZTGGGJOSSFH-UHFFFAOYSA-N 0.000 description 1
SWJXXAOCJBUVJQ-UHFFFAOYSA-N ethyl 5-[[4-[2-[(2-chloro-5-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC(OC)=CC=C1Cl SWJXXAOCJBUVJQ-UHFFFAOYSA-N 0.000 description 1
JKUNCLIFBYTEJR-UHFFFAOYSA-N ethyl 5-[[4-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1CCCCC1 JKUNCLIFBYTEJR-UHFFFAOYSA-N 0.000 description 1
KXQHGVBUEUSNGT-UHFFFAOYSA-N ethyl 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)COC1=CC=CC=C1 KXQHGVBUEUSNGT-UHFFFAOYSA-N 0.000 description 1
ZIPZTGLFACQCEW-UHFFFAOYSA-N ethyl 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1=CC=CC=C1 ZIPZTGLFACQCEW-UHFFFAOYSA-N 0.000 description 1
YGVGYCBOOZOGJX-UHFFFAOYSA-N ethyl 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 YGVGYCBOOZOGJX-UHFFFAOYSA-N 0.000 description 1
FJEYFLMHSWCSDO-UHFFFAOYSA-N ethyl 5-[[4-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(F)C=C1 FJEYFLMHSWCSDO-UHFFFAOYSA-N 0.000 description 1
OQBGKLZYFYTQGY-UHFFFAOYSA-N ethyl 5-[[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC OQBGKLZYFYTQGY-UHFFFAOYSA-N 0.000 description 1
230000004761 fibrosis Effects 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PDGKGWJWNLENGS-UHFFFAOYSA-N heptan-4-yl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CCC)CCC PDGKGWJWNLENGS-UHFFFAOYSA-N 0.000 description 1
AMGMWHHMYXKCSS-UHFFFAOYSA-N heptan-4-yl 5-[[4-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1(=CC=CC=C1)CCCCNC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CCC)CCC AMGMWHHMYXKCSS-UHFFFAOYSA-N 0.000 description 1
PCTNKCYUIZATGL-UHFFFAOYSA-N heptan-4-yl 5-[[4-(cyclohexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(CCC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(cc1)C(=O)NC1CCCCC1 PCTNKCYUIZATGL-UHFFFAOYSA-N 0.000 description 1
ZNZKMZGKEWDZBL-UHFFFAOYSA-N heptan-4-yl 5-[[4-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCCCCC ZNZKMZGKEWDZBL-UHFFFAOYSA-N 0.000 description 1
KKQRBDARGAPXRK-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CCC)CCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C(=CC=CC=2)OC)C=C1 KKQRBDARGAPXRK-UHFFFAOYSA-N 0.000 description 1
WXTSEVFGAACMEW-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CCC)CCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=C(OC)C=CC=2)C=C1 WXTSEVFGAACMEW-UHFFFAOYSA-N 0.000 description 1
VFGWCLJFKUFUEX-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCC1=CC=C(C=C1)Cl VFGWCLJFKUFUEX-UHFFFAOYSA-N 0.000 description 1
WAPBYYIDVLXSKK-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCC1=CC=C(C=C1)F WAPBYYIDVLXSKK-UHFFFAOYSA-N 0.000 description 1
ZAASRBBJSVGZBX-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CCC)CCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC(OC)=CC=2)C=C1 ZAASRBBJSVGZBX-UHFFFAOYSA-N 0.000 description 1
FALXLZQYTGJKKN-UHFFFAOYSA-N heptan-4-yl 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=CC=C(C=C1)Cl)=O FALXLZQYTGJKKN-UHFFFAOYSA-N 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
DDNQFJVQVXVMJZ-UHFFFAOYSA-N methyl 5-(butylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound CCCCS(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 DDNQFJVQVXVMJZ-UHFFFAOYSA-N 0.000 description 1
HUKXMZINFXQUTA-UHFFFAOYSA-N methyl 5-(naphthalen-1-ylsulfonylamino)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CC=C12 HUKXMZINFXQUTA-UHFFFAOYSA-N 0.000 description 1
XTWMAJJRXZTUMW-UHFFFAOYSA-N methyl 5-[(2-phenylphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 XTWMAJJRXZTUMW-UHFFFAOYSA-N 0.000 description 1
HEBCGCFJIKKBJA-UHFFFAOYSA-N methyl 5-[(4-acetamidophenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 HEBCGCFJIKKBJA-UHFFFAOYSA-N 0.000 description 1
KYVHKQCPCYSPFL-UHFFFAOYSA-N methyl 5-[(4-benzamidophenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 KYVHKQCPCYSPFL-UHFFFAOYSA-N 0.000 description 1
QLTAXQQUVOHYGJ-UHFFFAOYSA-N methyl 5-[(4-butoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 QLTAXQQUVOHYGJ-UHFFFAOYSA-N 0.000 description 1
OYIFEASRXPQYBD-UHFFFAOYSA-N methyl 5-[(4-fluorophenyl)sulfonylamino]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 OYIFEASRXPQYBD-UHFFFAOYSA-N 0.000 description 1
SWEJDWNLCXQYON-UHFFFAOYSA-N methyl 5-[(4-phenoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 SWEJDWNLCXQYON-UHFFFAOYSA-N 0.000 description 1
SOUGZXAICFWPRB-UHFFFAOYSA-N methyl 5-[2-(4-fluorophenoxy)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)CCOC1=CC=C(F)C=C1 SOUGZXAICFWPRB-UHFFFAOYSA-N 0.000 description 1
LIBXRBCAPKWMKG-UHFFFAOYSA-N methyl 5-[2-(4-fluorophenyl)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)CCC1=CC=C(F)C=C1 LIBXRBCAPKWMKG-UHFFFAOYSA-N 0.000 description 1
VUKDXRKUMJEUBM-UHFFFAOYSA-N methyl 5-[2-(4-methoxyphenyl)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)CCC1=CC=C(OC)C=C1 VUKDXRKUMJEUBM-UHFFFAOYSA-N 0.000 description 1
HKTFOLVCIZZPNL-UHFFFAOYSA-N methyl 5-[[2-chloro-4-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1Cl HKTFOLVCIZZPNL-UHFFFAOYSA-N 0.000 description 1
CCMNTNHXAJRDOT-UHFFFAOYSA-N methyl 5-[[2-chloro-4-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound ClC1=CC(C(=O)NCCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 CCMNTNHXAJRDOT-UHFFFAOYSA-N 0.000 description 1
FJJZPMTVPCHIKE-UHFFFAOYSA-N methyl 5-[[3-(2-methoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 FJJZPMTVPCHIKE-UHFFFAOYSA-N 0.000 description 1
JAFPMZJISAISPK-UHFFFAOYSA-N methyl 5-[[3-(3-methoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COCCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 JAFPMZJISAISPK-UHFFFAOYSA-N 0.000 description 1
IBWHJIAZTMYLLW-UHFFFAOYSA-N methyl 5-[[3-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCC=2C=CC=CC=2)=C1 IBWHJIAZTMYLLW-UHFFFAOYSA-N 0.000 description 1
JFXGRAZOAWHWJX-UHFFFAOYSA-N methyl 5-[[3-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCCC=2C=CC=CC=2)=C1 JFXGRAZOAWHWJX-UHFFFAOYSA-N 0.000 description 1
RJGQPCSHJJGYPE-UHFFFAOYSA-N methyl 5-[[3-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 RJGQPCSHJJGYPE-UHFFFAOYSA-N 0.000 description 1
MDDIEYPSNFJXGR-UHFFFAOYSA-N methyl 5-[[3-(butylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 MDDIEYPSNFJXGR-UHFFFAOYSA-N 0.000 description 1
GHWVCPRQEPAWFT-UHFFFAOYSA-N methyl 5-[[3-(cyclohexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NC2CCCCC2)=C1 GHWVCPRQEPAWFT-UHFFFAOYSA-N 0.000 description 1
CAPJDZJZXCEZLV-UHFFFAOYSA-N methyl 5-[[3-(ethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 CAPJDZJZXCEZLV-UHFFFAOYSA-N 0.000 description 1
IPGHJHIWTFVHNE-UHFFFAOYSA-N methyl 5-[[3-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCCCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 IPGHJHIWTFVHNE-UHFFFAOYSA-N 0.000 description 1
ZVLAILSYYLSQSV-UHFFFAOYSA-N methyl 5-[[3-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C(=CC=CC=2)OC)=C1 ZVLAILSYYLSQSV-UHFFFAOYSA-N 0.000 description 1
GJLAVZGWMAUOKK-UHFFFAOYSA-N methyl 5-[[3-[2-(2-methylpropanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)C(C)C)=C1 GJLAVZGWMAUOKK-UHFFFAOYSA-N 0.000 description 1
BTPXDIWQTCEMIN-UHFFFAOYSA-N methyl 5-[[3-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=C(OC)C(OC)=CC=2)=C1 BTPXDIWQTCEMIN-UHFFFAOYSA-N 0.000 description 1
XMEWNYGHKGIQCB-UHFFFAOYSA-N methyl 5-[[3-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=C(OC)C=CC=2)=C1 XMEWNYGHKGIQCB-UHFFFAOYSA-N 0.000 description 1
XEHFULSSZRHWKH-UHFFFAOYSA-N methyl 5-[[3-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 XEHFULSSZRHWKH-UHFFFAOYSA-N 0.000 description 1
GTOJBLCXQKWJMH-UHFFFAOYSA-N methyl 5-[[3-[2-(cyclohexanecarbonylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)C2CCCCC2)=C1 GTOJBLCXQKWJMH-UHFFFAOYSA-N 0.000 description 1
BZQYMDSIGJTEIX-UHFFFAOYSA-N methyl 5-[[3-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)CC2CCCCC2)=C1 BZQYMDSIGJTEIX-UHFFFAOYSA-N 0.000 description 1
HUPNWXVDCIOPJL-UHFFFAOYSA-N methyl 5-[[3-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)COC=2C=CC=CC=2)=C1 HUPNWXVDCIOPJL-UHFFFAOYSA-N 0.000 description 1
FEVOYFCPGNRUDU-UHFFFAOYSA-N methyl 5-[[3-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound COC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C1=CC=C(C=C1)Cl)=O FEVOYFCPGNRUDU-UHFFFAOYSA-N 0.000 description 1
NVAIWTSEWDEAGC-UHFFFAOYSA-N methyl 5-[[4-(2-benzamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=CC=C1 NVAIWTSEWDEAGC-UHFFFAOYSA-N 0.000 description 1
ZPBSHNSYUUSLIL-UHFFFAOYSA-N methyl 5-[[4-(2-ethoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 ZPBSHNSYUUSLIL-UHFFFAOYSA-N 0.000 description 1
WEVKIXXOFGTNOC-UHFFFAOYSA-N methyl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCOC=2C=CC=CC=2)C=C1 WEVKIXXOFGTNOC-UHFFFAOYSA-N 0.000 description 1
OQWWOEPWJASTJT-UHFFFAOYSA-N methyl 5-[[4-(3-chloro-2-cyanophenoxy)phenyl]sulfonylamino]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1C#N OQWWOEPWJASTJT-UHFFFAOYSA-N 0.000 description 1
LOOQSVGUEURASS-UHFFFAOYSA-N methyl 5-[[4-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCOCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 LOOQSVGUEURASS-UHFFFAOYSA-N 0.000 description 1
IXCXPUFLKNJHOV-UHFFFAOYSA-N methyl 5-[[4-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCCC=2C=CC=CC=2)C=C1 IXCXPUFLKNJHOV-UHFFFAOYSA-N 0.000 description 1
AOANTNGWYUGGCI-UHFFFAOYSA-N methyl 5-[[4-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCCCC=2C=CC=CC=2)C=C1 AOANTNGWYUGGCI-UHFFFAOYSA-N 0.000 description 1
VTTXAGQAOLSPET-UHFFFAOYSA-N methyl 5-[[4-(butanoylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(NC(=O)CCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 VTTXAGQAOLSPET-UHFFFAOYSA-N 0.000 description 1
HWEMCVQIDMTPRJ-UHFFFAOYSA-N methyl 5-[[4-(butylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 HWEMCVQIDMTPRJ-UHFFFAOYSA-N 0.000 description 1
RTBFXXCZFSGLCD-UHFFFAOYSA-N methyl 5-[[4-(cyclohexanecarbonylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)C1CCCCC1 RTBFXXCZFSGLCD-UHFFFAOYSA-N 0.000 description 1
SCKCXCHWDYDHOM-UHFFFAOYSA-N methyl 5-[[4-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 SCKCXCHWDYDHOM-UHFFFAOYSA-N 0.000 description 1
PBHZZTWDENTRKL-UHFFFAOYSA-N methyl 5-[[4-(trifluoromethoxy)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 PBHZZTWDENTRKL-UHFFFAOYSA-N 0.000 description 1
WLQUFMJUPWKCDR-UHFFFAOYSA-N methyl 5-[[4-[2-(2-ethylbutanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)C(CC)CC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 WLQUFMJUPWKCDR-UHFFFAOYSA-N 0.000 description 1
CTHDRKNASCIRKI-UHFFFAOYSA-N methyl 5-[[4-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C(=CC=CC=2)OC)C=C1 CTHDRKNASCIRKI-UHFFFAOYSA-N 0.000 description 1
DEZBEVPGIHUWMO-UHFFFAOYSA-N methyl 5-[[4-[2-(2-methylpropanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(=O)C(C)C)C=C1 DEZBEVPGIHUWMO-UHFFFAOYSA-N 0.000 description 1
UOCGDGYDGAYVFX-UHFFFAOYSA-N methyl 5-[[4-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=C(OC)C(OC)=CC=2)C=C1 UOCGDGYDGAYVFX-UHFFFAOYSA-N 0.000 description 1
ZEUOFSXTGKMQRI-UHFFFAOYSA-N methyl 5-[[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC(F)=CC=2)C=C1 ZEUOFSXTGKMQRI-UHFFFAOYSA-N 0.000 description 1
VMQFDBJCMNWAJF-UHFFFAOYSA-N methyl 5-[[4-[2-(heptanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 VMQFDBJCMNWAJF-UHFFFAOYSA-N 0.000 description 1
MNKKEDPVTBAFEO-UHFFFAOYSA-N methyl 5-[[4-[2-(octanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCCCCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 MNKKEDPVTBAFEO-UHFFFAOYSA-N 0.000 description 1
QFAPNNPVYMUMOT-UHFFFAOYSA-N methyl 5-[[4-[2-(pentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)CCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC)N=C1 QFAPNNPVYMUMOT-UHFFFAOYSA-N 0.000 description 1
AEBLFYGLUKYNQS-UHFFFAOYSA-N methyl 5-[[4-[2-[[2-(3,4-dimethoxyphenyl)acetyl]amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1=CC=C(OC)C(OC)=C1 AEBLFYGLUKYNQS-UHFFFAOYSA-N 0.000 description 1
JHHRZPZGYXSXRY-UHFFFAOYSA-N methyl 5-[[4-chloro-3-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(Cl)C(C(=O)NCCOC=2C=CC=CC=2)=C1 JHHRZPZGYXSXRY-UHFFFAOYSA-N 0.000 description 1
QHMQQRAIIGLGGR-UHFFFAOYSA-N methyl 5-[[4-chloro-3-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=C(Cl)C(C(=O)NCCCOCC)=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC)=C1 QHMQQRAIIGLGGR-UHFFFAOYSA-N 0.000 description 1
DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
SQEWOGSRDKIZIH-UHFFFAOYSA-N pentan-3-yl 5-(benzenesulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 SQEWOGSRDKIZIH-UHFFFAOYSA-N 0.000 description 1
PUGCLXRLPKNFKP-UHFFFAOYSA-N pentan-3-yl 5-(butylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound CCCCS(=O)(=O)NC(=O)c1ccc(nc1)C(=O)OC(CC)CC PUGCLXRLPKNFKP-UHFFFAOYSA-N 0.000 description 1
QMVFRDCMFIMQQH-UHFFFAOYSA-N pentan-3-yl 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(OC)cc1 QMVFRDCMFIMQQH-UHFFFAOYSA-N 0.000 description 1
UMTBZOCCIUGIOY-UHFFFAOYSA-N pentan-3-yl 5-[[3-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C(C)(=O)NCCC=1C=C(C=CC1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CC)CC UMTBZOCCIUGIOY-UHFFFAOYSA-N 0.000 description 1
AISAEJUSGQMKDY-UHFFFAOYSA-N pentan-3-yl 5-[[3-(2-benzamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C1=CC=CC=C1)=O AISAEJUSGQMKDY-UHFFFAOYSA-N 0.000 description 1
IPKCEENIFAUSDZ-UHFFFAOYSA-N pentan-3-yl 5-[[3-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1cccc(c1)C(=O)NCCCc1ccccc1 IPKCEENIFAUSDZ-UHFFFAOYSA-N 0.000 description 1
IVMAVUGHLRIMOF-UHFFFAOYSA-N pentan-3-yl 5-[[3-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)C(=O)NCCCCC1=CC=CC=C1 IVMAVUGHLRIMOF-UHFFFAOYSA-N 0.000 description 1
ZNMZGQZEURHJAY-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=C(OC)C=CC=2)=C1 ZNMZGQZEURHJAY-UHFFFAOYSA-N 0.000 description 1
GDDYPGCAFWGQGQ-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(OC)=CC=2)=C1 GDDYPGCAFWGQGQ-UHFFFAOYSA-N 0.000 description 1
QMQFZFOIVMFYCQ-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-(butanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(=O)NCCc1cccc(c1)S(=O)(=O)NC(=O)c1ccc(nc1)C(=O)OC(CC)CC QMQFZFOIVMFYCQ-UHFFFAOYSA-N 0.000 description 1
MIHZKQYZDFOGBJ-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1(CCCCC1)CC(=O)NCCC=1C=C(C=CC1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CC)CC MIHZKQYZDFOGBJ-UHFFFAOYSA-N 0.000 description 1
RAGZLIOBXBMMBK-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1cccc(CCNC(=O)COc2ccccc2)c1 RAGZLIOBXBMMBK-UHFFFAOYSA-N 0.000 description 1
INQACPYHNDDKBT-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)CC=2C=CC=CC=2)=C1 INQACPYHNDDKBT-UHFFFAOYSA-N 0.000 description 1
JKGFXXGHEFNJLG-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(4-ethoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C1=CC=C(C=C1)OCC)=O JKGFXXGHEFNJLG-UHFFFAOYSA-N 0.000 description 1
OTHKKJSOALJMQS-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C1=CC=C(C=C1)F)=O OTHKKJSOALJMQS-UHFFFAOYSA-N 0.000 description 1
VXRABIALJCYGGO-UHFFFAOYSA-N pentan-3-yl 5-[[3-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C1=C(C=CC(=C1)Cl)OC)=O VXRABIALJCYGGO-UHFFFAOYSA-N 0.000 description 1
VFGUDHMNKXJAQZ-UHFFFAOYSA-N pentan-3-yl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C)=O VFGUDHMNKXJAQZ-UHFFFAOYSA-N 0.000 description 1
BSCHDWBCDTUCAE-UHFFFAOYSA-N pentan-3-yl 5-[[4-(2-benzamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=CC=CC=C1)=O BSCHDWBCDTUCAE-UHFFFAOYSA-N 0.000 description 1
DUXWICGKUUYZAF-UHFFFAOYSA-N pentan-3-yl 5-[[4-(2-ethoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCOCC DUXWICGKUUYZAF-UHFFFAOYSA-N 0.000 description 1
WTDPOKGQTISDHC-UHFFFAOYSA-N pentan-3-yl 5-[[4-(2-methylpentanoylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(C(CCC)C)=O WTDPOKGQTISDHC-UHFFFAOYSA-N 0.000 description 1
HCTPVOCVPRBBML-UHFFFAOYSA-N pentan-3-yl 5-[[4-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCCC=2C=CC=CC=2)C=C1 HCTPVOCVPRBBML-UHFFFAOYSA-N 0.000 description 1
KUICSSKSMKDXBZ-UHFFFAOYSA-N pentan-3-yl 5-[[4-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCCCC1=CC=CC=C1 KUICSSKSMKDXBZ-UHFFFAOYSA-N 0.000 description 1
REPLMXUFTMSOEH-UHFFFAOYSA-N pentan-3-yl 5-[[4-(butylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCCC REPLMXUFTMSOEH-UHFFFAOYSA-N 0.000 description 1
XJECDGKPJJPVCN-UHFFFAOYSA-N pentan-3-yl 5-[[4-(hexanoylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(CCCCC)=O XJECDGKPJJPVCN-UHFFFAOYSA-N 0.000 description 1
QVDIDIWRXXGCQM-UHFFFAOYSA-N pentan-3-yl 5-[[4-(hexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCCCCC QVDIDIWRXXGCQM-UHFFFAOYSA-N 0.000 description 1
WJUFRKNBTLNBJE-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(2-ethylbutanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C(CC)CC)=O WJUFRKNBTLNBJE-UHFFFAOYSA-N 0.000 description 1
WXEDUGNPNOHTNZ-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C(=CC=CC=2)OC)C=C1 WXEDUGNPNOHTNZ-UHFFFAOYSA-N 0.000 description 1
GLWHTNXGAUBADW-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCC1=CC(=C(C=C1)OC)OC GLWHTNXGAUBADW-UHFFFAOYSA-N 0.000 description 1
VKTPEXLBSKZVSC-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCC1=CC=C(C=C1)Cl VKTPEXLBSKZVSC-UHFFFAOYSA-N 0.000 description 1
KLQOMLSELHWVJU-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCCC1=CC=C(C=C1)F KLQOMLSELHWVJU-UHFFFAOYSA-N 0.000 description 1
OMBQANHKBCCOCK-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC(OC)=CC=2)C=C1 OMBQANHKBCCOCK-UHFFFAOYSA-N 0.000 description 1
RRRPWYLARXPVGF-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(4-methylpentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(CCC(C)C)=O RRRPWYLARXPVGF-UHFFFAOYSA-N 0.000 description 1
MHEOKHJMZJKSCZ-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(butanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCC(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)c1ccc(nc1)C(=O)OC(CC)CC MHEOKHJMZJKSCZ-UHFFFAOYSA-N 0.000 description 1
BNYNNMAYVUDMFG-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-(pentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCCCC(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)c1ccc(nc1)C(=O)OC(CC)CC BNYNNMAYVUDMFG-UHFFFAOYSA-N 0.000 description 1
YOTWXECESPNTIH-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-[(2-chloro-5-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=C(C=CC(=C1)OC)Cl)=O YOTWXECESPNTIH-UHFFFAOYSA-N 0.000 description 1
WCKPTCBQBGMWHJ-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1(CCCCC1)CC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CC)CC WCKPTCBQBGMWHJ-UHFFFAOYSA-N 0.000 description 1
PEJXZMXELGBJGR-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(CC1=CC=CC=C1)=O PEJXZMXELGBJGR-UHFFFAOYSA-N 0.000 description 1
PFHIHNBIQNBKBR-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=CC=C(C=C1)Cl)=O PFHIHNBIQNBKBR-UHFFFAOYSA-N 0.000 description 1
KLXOIRMJMSDQCP-UHFFFAOYSA-N pentan-3-yl 5-[[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)CCNC(C1=C(C=CC(=C1)Cl)OC)=O KLXOIRMJMSDQCP-UHFFFAOYSA-N 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
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125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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NDYZJZGJHDRYQU-UHFFFAOYSA-N propan-2-yl 5-[(4-phenoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 NDYZJZGJHDRYQU-UHFFFAOYSA-N 0.000 description 1
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VXTYMTWVLNJWPV-UHFFFAOYSA-N propan-2-yl 5-[2-(4-methoxyphenyl)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1CCS(=O)(=O)NC(=O)C1=CC=C(C(=O)OC(C)C)N=C1 VXTYMTWVLNJWPV-UHFFFAOYSA-N 0.000 description 1
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KKIZDKCMHYZXOK-UHFFFAOYSA-N propan-2-yl 5-[[3-(3-ethoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCOCCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)=C1 KKIZDKCMHYZXOK-UHFFFAOYSA-N 0.000 description 1
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