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

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 (The priority date 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 date listed.)

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
230000005764 inhibitory process Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical class OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
YTJFGRWEHHOCFZ-UHFFFAOYSA-N methyl 5-[(4,5-dibromothiophen-2-yl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC(Br)=C(Br)S1 YTJFGRWEHHOCFZ-UHFFFAOYSA-N 0.000 description 2
ZCFGHNXCKKIKCH-UHFFFAOYSA-N methyl 5-[[4-[2-(4-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(OC)=CC=2)C=C1 ZCFGHNXCKKIKCH-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical class ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
SFVICOPIKIEJRW-UHFFFAOYSA-N (1-oxo-1-propan-2-yloxypropan-2-yl) 5-[[3-[2-(cyclohexanecarbonylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)C2CCCCC2)=C1 SFVICOPIKIEJRW-UHFFFAOYSA-N 0.000 description 1
DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
GAZVSOQUFLIBJQ-BYNIDDHOSA-M (2s,3s,4s,5r,6s)-6-[(5-bromo-6-chloro-1h-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound O1[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CNC2=CC(Cl)=C(Br)C=C12 GAZVSOQUFLIBJQ-BYNIDDHOSA-M 0.000 description 1
WLTHWJXPJWPTHD-UHFFFAOYSA-N (4-methoxyphenyl)methyl 5-[[4-[2-[(2-phenoxyacetyl)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)COC=3C=CC=CC=3)=CC=2)C=N1 WLTHWJXPJWPTHD-UHFFFAOYSA-N 0.000 description 1
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
HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical class CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
VQKHYHWEHGVGHI-UHFFFAOYSA-N 2-chloro-5-methoxy-n-[2-(2-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=C(Cl)C(C(=O)NCCC=2C(=CC=CC=2)S(N)(=O)=O)=C1 VQKHYHWEHGVGHI-UHFFFAOYSA-N 0.000 description 1
AQHFCRYZABKUEV-UHFFFAOYSA-N 2-chloro-5-methoxybenzoic acid Chemical compound COC1=CC=C(Cl)C(C(O)=O)=C1 AQHFCRYZABKUEV-UHFFFAOYSA-N 0.000 description 1
BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
PZYDBENQSIISHX-UHFFFAOYSA-N 2-ethoxyethyl 5-[[4-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCOCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1CCCCC1 PZYDBENQSIISHX-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
WIWQDYZWXJKPKG-UHFFFAOYSA-N 2-methoxyethyl 5-[[4-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCOC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(F)C=C1 WIWQDYZWXJKPKG-UHFFFAOYSA-N 0.000 description 1
SGVJIIRXJVJBHQ-UHFFFAOYSA-N 2-methyl-1h-pyridine-2,5-dicarboxylic acid Chemical compound OC(=O)C1(C)NC=C(C(O)=O)C=C1 SGVJIIRXJVJBHQ-UHFFFAOYSA-N 0.000 description 1
BVEYVWFIIDOZSA-UHFFFAOYSA-N 2-methylbutyl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 BVEYVWFIIDOZSA-UHFFFAOYSA-N 0.000 description 1
YKHLPIKISWBNPX-UHFFFAOYSA-N 2-methylbutyl 5-[[4-(2-benzamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=CC=C1 YKHLPIKISWBNPX-UHFFFAOYSA-N 0.000 description 1
BTMKUOTVCXTHCE-UHFFFAOYSA-N 2-methylbutyl 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(C)CC)N=C1 BTMKUOTVCXTHCE-UHFFFAOYSA-N 0.000 description 1
SKDIKOISOYDTGD-UHFFFAOYSA-N 2-methylbutyl 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 SKDIKOISOYDTGD-UHFFFAOYSA-N 0.000 description 1
IHGSXLWUTKQCBI-UHFFFAOYSA-N 2-methylbutyl 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)OCC(C)CC)=C1 IHGSXLWUTKQCBI-UHFFFAOYSA-N 0.000 description 1
AYBREWCKQVLHAJ-UHFFFAOYSA-N 2-methylhexan-3-yl 5-[[4-[2-(3-methylbutanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(CCC)C(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(=O)CC(C)C)C=C1 AYBREWCKQVLHAJ-UHFFFAOYSA-N 0.000 description 1
UYLDITJVAPUYCD-UHFFFAOYSA-N 2-methylhexyl 5-[[2-chloro-4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCOC=2C=CC=CC=2)C=C1Cl UYLDITJVAPUYCD-UHFFFAOYSA-N 0.000 description 1
XVXQFPXVVKXPTL-UHFFFAOYSA-N 2-methylhexyl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 XVXQFPXVVKXPTL-UHFFFAOYSA-N 0.000 description 1
CPMDALVTIFZCIY-UHFFFAOYSA-N 2-methylhexyl 5-[[4-(butanoylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)CCC)C=C1 CPMDALVTIFZCIY-UHFFFAOYSA-N 0.000 description 1
APRASIYVFRYBSY-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[(2-phenoxyacetyl)amino]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)COC1=CC=CC=C1 APRASIYVFRYBSY-UHFFFAOYSA-N 0.000 description 1
QHSIADWINSTELO-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-(2-methylpropanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(=O)C(C)C)C=C1 QHSIADWINSTELO-UHFFFAOYSA-N 0.000 description 1
FXLLGHLSIPMYPZ-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-(cyclohexanecarbonylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1CCCCC1 FXLLGHLSIPMYPZ-UHFFFAOYSA-N 0.000 description 1
ACEKHCPRILCTSE-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1CCCCC1 ACEKHCPRILCTSE-UHFFFAOYSA-N 0.000 description 1
DAZXLMQMXAFWHM-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)COC1=CC=CC=C1 DAZXLMQMXAFWHM-UHFFFAOYSA-N 0.000 description 1
BEGWXEJITODABT-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1=CC=CC=C1 BEGWXEJITODABT-UHFFFAOYSA-N 0.000 description 1
WGTGZDZNLLHDNA-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-[(4-ethoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(OCC)C=C1 WGTGZDZNLLHDNA-UHFFFAOYSA-N 0.000 description 1
RMLNOGQRFYLGTA-UHFFFAOYSA-N 2-methylhexyl 5-[[4-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC(C)CCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=C(F)C=C1 RMLNOGQRFYLGTA-UHFFFAOYSA-N 0.000 description 1
ZVRCGNRSUOETIM-UHFFFAOYSA-N 2-methylpentyl 5-[[4-[2-[(4-butoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCC(C)CCC)C=C1 ZVRCGNRSUOETIM-UHFFFAOYSA-N 0.000 description 1
UOFVMZBKYNSCCV-UHFFFAOYSA-N 2-methylpropyl 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)OCC(C)C)N=C1 UOFVMZBKYNSCCV-UHFFFAOYSA-N 0.000 description 1
ODWZARPVTUZQDG-UHFFFAOYSA-N 2-methylpropyl 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(C)C)=C1 ODWZARPVTUZQDG-UHFFFAOYSA-N 0.000 description 1
UPWCZUPBXHWMBG-UHFFFAOYSA-N 2-methylpropyl 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(C)C)C=C1 UPWCZUPBXHWMBG-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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
RGOJCHYYBKMRLL-UHFFFAOYSA-N 4-(trifluoromethoxy)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 RGOJCHYYBKMRLL-UHFFFAOYSA-N 0.000 description 1
VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
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
GJCVWKPGGOMFQR-UHFFFAOYSA-N 4-butoxybenzenesulfonamide Chemical compound CCCCOC1=CC=C(S(N)(=O)=O)C=C1 GJCVWKPGGOMFQR-UHFFFAOYSA-N 0.000 description 1
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
MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 description 1
YRMQBYJRBZKYGC-UHFFFAOYSA-N 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(O)=O)N=C1 YRMQBYJRBZKYGC-UHFFFAOYSA-N 0.000 description 1
IFMLRXXFANGTJN-UHFFFAOYSA-N 5-[[3-[2-[(4-fluorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(CCNC(=O)C=2C=CC(F)=CC=2)=C1 IFMLRXXFANGTJN-UHFFFAOYSA-N 0.000 description 1
PYKTVFFGHLIOOB-UHFFFAOYSA-N 5-[[4-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCCC=2C=CC=CC=2)C=C1 PYKTVFFGHLIOOB-UHFFFAOYSA-N 0.000 description 1
ZKGXOUIMYNSABN-UHFFFAOYSA-N 5-[[4-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1 ZKGXOUIMYNSABN-UHFFFAOYSA-N 0.000 description 1
WJFJTXMQAMKGHW-UHFFFAOYSA-N 5-[[4-[2-(pentanoylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylic acid Chemical compound C1=CC(CCNC(=O)CCCC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(O)=O)N=C1 WJFJTXMQAMKGHW-UHFFFAOYSA-N 0.000 description 1
WDJARUKOMOGTHA-UHFFFAOYSA-N 5-aminopyridine-2-carboxylic acid Chemical class NC1=CC=C(C(O)=O)N=C1 WDJARUKOMOGTHA-UHFFFAOYSA-N 0.000 description 1
UNQYAAAWKOOBFQ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C=2C(=O)N(CCCO)C(=O)N(C)C=2N=C1OC1=CC=C(Cl)C(OC(F)(F)F)=C1 UNQYAAAWKOOBFQ-UHFFFAOYSA-N 0.000 description 1
ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
NSELGUIOELRYSA-UHFFFAOYSA-N BrC=1C=C(SC1Br)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC Chemical compound BrC=1C=C(SC1Br)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC NSELGUIOELRYSA-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FADCMNCJXYZFNU-UHFFFAOYSA-N C(C)NC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CC)CC Chemical compound C(C)NC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OC(CC)CC FADCMNCJXYZFNU-UHFFFAOYSA-N 0.000 description 1
HEJZPQWILZADCF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OCC(CO)(C)C Chemical compound C(C1=CC=CC=C1)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)OCC(CO)(C)C HEJZPQWILZADCF-UHFFFAOYSA-N 0.000 description 1
NINAQLPLFZVFIF-UHFFFAOYSA-N C(CCCCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)O Chemical compound C(CCCCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1C=CC(=NC1)C(=O)O NINAQLPLFZVFIF-UHFFFAOYSA-N 0.000 description 1
DQNXMGCFVHEWGU-UHFFFAOYSA-N C1=CC(OCC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCCOC)C=C1 Chemical compound C1=CC(OCC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OCCOC)C=C1 DQNXMGCFVHEWGU-UHFFFAOYSA-N 0.000 description 1
GCBOYPZTWFAHNV-UHFFFAOYSA-N C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 Chemical compound C1=NC(C(=O)OC(CC)CC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 GCBOYPZTWFAHNV-UHFFFAOYSA-N 0.000 description 1
MAVYCHQCOAKBFD-UHFFFAOYSA-N C1=NC(C(=O)OC(CCC)CCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1 Chemical compound C1=NC(C(=O)OC(CCC)CCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1 MAVYCHQCOAKBFD-UHFFFAOYSA-N 0.000 description 1
NTYGJFXKWDXOKI-UHFFFAOYSA-N C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)CCC1=CC=C(F)C=C1 Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)CCC1=CC=C(F)C=C1 NTYGJFXKWDXOKI-UHFFFAOYSA-N 0.000 description 1
GSJMAIDGZAFRCZ-UHFFFAOYSA-N C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)CCOC1=CC=C(F)C=C1 Chemical compound C1=NC(C(=O)OCC)=CC=C1C(=O)NS(=O)(=O)CCOC1=CC=C(F)C=C1 GSJMAIDGZAFRCZ-UHFFFAOYSA-N 0.000 description 1
UKZHJBGLKLXKBH-UHFFFAOYSA-N C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 UKZHJBGLKLXKBH-UHFFFAOYSA-N 0.000 description 1
ORVPPCZMQCCDEA-UHFFFAOYSA-N C1=NC(C(=O)OCCCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 Chemical compound C1=NC(C(=O)OCCCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 ORVPPCZMQCCDEA-UHFFFAOYSA-N 0.000 description 1
229910014585 C2-Ce Inorganic materials 0.000 description 1
RJDTVKSZJYKZJK-UHFFFAOYSA-N CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C(C)C)=O Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)CCNC(C(C)C)=O RJDTVKSZJYKZJK-UHFFFAOYSA-N 0.000 description 1
JOSVZBJULOUOIT-UHFFFAOYSA-N CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C2=CC=C(C=C2)CCNC(=O)C(C)C Chemical compound CCC(CC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C2=CC=C(C=C2)CCNC(=O)C(C)C JOSVZBJULOUOIT-UHFFFAOYSA-N 0.000 description 1
JJGAIRDVDMVFCA-UHFFFAOYSA-N CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)C2CCCCC2)cc1 Chemical compound CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)C2CCCCC2)cc1 JJGAIRDVDMVFCA-UHFFFAOYSA-N 0.000 description 1
WTWDHXGLMKEROH-UHFFFAOYSA-N CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1cccc(CCNC(=O)C2CCCCC2)c1 Chemical compound CCC(CC)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1cccc(CCNC(=O)C2CCCCC2)c1 WTWDHXGLMKEROH-UHFFFAOYSA-N 0.000 description 1
XCJXYWKICMNRSC-UHFFFAOYSA-N CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCC Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)C(=O)NCC XCJXYWKICMNRSC-UHFFFAOYSA-N 0.000 description 1
MJNYMAPTEPCDPP-UHFFFAOYSA-N CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(=O)C1CCCCC1 Chemical compound CCCC(CCC)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC=C(C=C1)NC(=O)C1CCCCC1 MJNYMAPTEPCDPP-UHFFFAOYSA-N 0.000 description 1
FXARWTZATKWENV-UHFFFAOYSA-N CCCCC(C)CC1=CC(C(NS(C2=CC=C(CCNC(C(C)C)=O)C=C2)(=O)=O)=O)=CN=C1 Chemical compound CCCCC(C)CC1=CC(C(NS(C2=CC=C(CCNC(C(C)C)=O)C=C2)(=O)=O)=O)=CN=C1 FXARWTZATKWENV-UHFFFAOYSA-N 0.000 description 1
ZTBYSQILTSWCTK-UHFFFAOYSA-N CCCCOC(C=CC=C1)=C1C(NCCC(C=C1)=CC=C1S(NC(C1=CN(CC(C)(C)C)CC=C1)=O)(=O)=O)=O Chemical compound CCCCOC(C=CC=C1)=C1C(NCCC(C=C1)=CC=C1S(NC(C1=CN(CC(C)(C)C)CC=C1)=O)(=O)=O)=O ZTBYSQILTSWCTK-UHFFFAOYSA-N 0.000 description 1
IOMKCXYDSYTUEY-UHFFFAOYSA-N CCOC(C=C1)=CC=C1C(NCCC(C=C1)=CC=C1S(NC(C1=CN(CC(C)(C)C)CC=C1)=O)(=O)=O)=O Chemical compound CCOC(C=C1)=CC=C1C(NCCC(C=C1)=CC=C1S(NC(C1=CN(CC(C)(C)C)CC=C1)=O)(=O)=O)=O IOMKCXYDSYTUEY-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102000001187 Collagen Type III Human genes 0.000 description 1
108010069502 Collagen Type III Proteins 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
NMMIHXMBOZYNET-UHFFFAOYSA-N Methyl picolinate Chemical class COC(=O)C1=CC=CC=N1 NMMIHXMBOZYNET-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
231100000644 Toxic injury Toxicity 0.000 description 1
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
NGAGFXVCFAZIGP-CQSZACIVSA-N [(2R)-butan-2-yl] 5-[[4-(2-acetamidoethyl)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(C)=O NGAGFXVCFAZIGP-CQSZACIVSA-N 0.000 description 1
BWJCRDOKEORRCQ-GOSISDBHSA-N [(2R)-butan-2-yl] 5-[[4-(2-benzamidoethyl)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=CC=C1)=O BWJCRDOKEORRCQ-GOSISDBHSA-N 0.000 description 1
OCKMTRLGQNLCEW-MRXNPFEDSA-N [(2R)-butan-2-yl] 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)O[C@H](C)CC)N=C1 OCKMTRLGQNLCEW-MRXNPFEDSA-N 0.000 description 1
WQBJKSTWTHLHQN-GOSISDBHSA-N [(2R)-butan-2-yl] 5-[[4-[2-(cyclohexanecarbonylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CC[C@@H](C)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)C2CCCCC2)cc1 WQBJKSTWTHLHQN-GOSISDBHSA-N 0.000 description 1
KQEBNNOJGXLDBV-QGZVFWFLSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(2-chloro-5-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)OC)Cl)=O KQEBNNOJGXLDBV-QGZVFWFLSA-N 0.000 description 1
MEAKWNXFZVFSAU-LJQANCHMSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CC[C@@H](C)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)COc2ccccc2)cc1 MEAKWNXFZVFSAU-LJQANCHMSA-N 0.000 description 1
JGNRXFQGKYKHIT-LJQANCHMSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)O[C@H](C)CC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1=CC=CC=C1 JGNRXFQGKYKHIT-LJQANCHMSA-N 0.000 description 1
QVGMFZZFMWIXQS-QGZVFWFLSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound ClC1=CC=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)C=2C=CC(=NC2)C(=O)O[C@H](C)CC)C=C1 QVGMFZZFMWIXQS-QGZVFWFLSA-N 0.000 description 1
OGHANOPJNLOXMR-LJQANCHMSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(4-ethoxybenzoyl)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)OCC)=O OGHANOPJNLOXMR-LJQANCHMSA-N 0.000 description 1
AOEIVQOWWBKXNQ-QGZVFWFLSA-N [(2R)-butan-2-yl] 5-[[4-[2-[(4-fluorobenzoyl)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)F)=O AOEIVQOWWBKXNQ-QGZVFWFLSA-N 0.000 description 1
NGAGFXVCFAZIGP-AWEZNQCLSA-N [(2S)-butan-2-yl] 5-[[4-(2-acetamidoethyl)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(C)=O NGAGFXVCFAZIGP-AWEZNQCLSA-N 0.000 description 1
OCKMTRLGQNLCEW-INIZCTEOSA-N [(2S)-butan-2-yl] 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)O[C@@H](C)CC)N=C1 OCKMTRLGQNLCEW-INIZCTEOSA-N 0.000 description 1
WQBJKSTWTHLHQN-SFHVURJKSA-N [(2S)-butan-2-yl] 5-[[4-[2-(cyclohexanecarbonylamino)ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CC[C@H](C)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)C2CCCCC2)cc1 WQBJKSTWTHLHQN-SFHVURJKSA-N 0.000 description 1
MNVJDZRESWNVPF-IBGZPJMESA-N [(2S)-butan-2-yl] 5-[[4-[2-[(2-cyclohexylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)O[C@@H](C)CC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1CCCCC1 MNVJDZRESWNVPF-IBGZPJMESA-N 0.000 description 1
MEAKWNXFZVFSAU-IBGZPJMESA-N [(2S)-butan-2-yl] 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CC[C@H](C)OC(=O)c1ccc(cn1)C(=O)NS(=O)(=O)c1ccc(CCNC(=O)COc2ccccc2)cc1 MEAKWNXFZVFSAU-IBGZPJMESA-N 0.000 description 1
JGNRXFQGKYKHIT-IBGZPJMESA-N [(2S)-butan-2-yl] 5-[[4-[2-[(2-phenylacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)O[C@@H](C)CC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)CC1=CC=CC=C1 JGNRXFQGKYKHIT-IBGZPJMESA-N 0.000 description 1
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
OGHANOPJNLOXMR-IBGZPJMESA-N [(2S)-butan-2-yl] 5-[[4-[2-[(4-ethoxybenzoyl)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)OCC)=O OGHANOPJNLOXMR-IBGZPJMESA-N 0.000 description 1
AOEIVQOWWBKXNQ-KRWDZBQOSA-N [(2S)-butan-2-yl] 5-[[4-[2-[(4-fluorobenzoyl)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)F)=O AOEIVQOWWBKXNQ-KRWDZBQOSA-N 0.000 description 1
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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
ITFXMMKETJOMPG-UHFFFAOYSA-N benzyl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(CCNC(=O)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OCC=2C=CC=CC=2)N=C1 ITFXMMKETJOMPG-UHFFFAOYSA-N 0.000 description 1
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
SJAVXQYBKQAMPV-UHFFFAOYSA-N benzyl 5-[[4-[2-[(2-chloro-5-methoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate 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)OCC=2C=CC=CC=2)=C1 SJAVXQYBKQAMPV-UHFFFAOYSA-N 0.000 description 1
125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
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
239000006227 byproduct Substances 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
KOGXVUNFKRCHOC-UHFFFAOYSA-N phenyl 5-[[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC=2C=CC=CC=2)C=C1 KOGXVUNFKRCHOC-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
VNQDHRVGWILNFN-UHFFFAOYSA-N propan-2-yl 5-(benzenesulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 VNQDHRVGWILNFN-UHFFFAOYSA-N 0.000 description 1
KLJRGCUDLPBHJL-UHFFFAOYSA-N propan-2-yl 5-(butylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound CCCCS(=O)(=O)NC(=O)C1=CC=C(C(=O)OC(C)C)N=C1 KLJRGCUDLPBHJL-UHFFFAOYSA-N 0.000 description 1
IYVSBXAUBRWDCI-UHFFFAOYSA-N propan-2-yl 5-(naphthalen-1-ylsulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC2=CC=CC=C12 IYVSBXAUBRWDCI-UHFFFAOYSA-N 0.000 description 1
AVFDMCQZFOSEHA-UHFFFAOYSA-N propan-2-yl 5-[(2-phenylphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 AVFDMCQZFOSEHA-UHFFFAOYSA-N 0.000 description 1
XKMZJSIAHORYLR-UHFFFAOYSA-N propan-2-yl 5-[(4-fluorophenyl)sulfonylamino]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 XKMZJSIAHORYLR-UHFFFAOYSA-N 0.000 description 1
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
PFMXTGPMYNBUTH-UHFFFAOYSA-N propan-2-yl 5-[2-(4-fluorophenoxy)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)CCOC1=CC=C(F)C=C1 PFMXTGPMYNBUTH-UHFFFAOYSA-N 0.000 description 1
UZAPKFHVPRONRR-UHFFFAOYSA-N propan-2-yl 5-[2-(4-fluorophenyl)ethylsulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)CCC1=CC=C(F)C=C1 UZAPKFHVPRONRR-UHFFFAOYSA-N 0.000 description 1
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
AAXCGDIYANKIIF-UHFFFAOYSA-N propan-2-yl 5-[[2-chloro-4-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1Cl AAXCGDIYANKIIF-UHFFFAOYSA-N 0.000 description 1
COAYNDVBMUAXJY-UHFFFAOYSA-N propan-2-yl 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(C)C)N=C1 COAYNDVBMUAXJY-UHFFFAOYSA-N 0.000 description 1
XIVPSBYGBHXYMM-UHFFFAOYSA-N propan-2-yl 5-[[3-(2-ethoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CCOCCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)=C1 XIVPSBYGBHXYMM-UHFFFAOYSA-N 0.000 description 1
YDNGVAJKSZUAKU-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1 YDNGVAJKSZUAKU-UHFFFAOYSA-N 0.000 description 1
UBOZPNIMKMUYBM-UHFFFAOYSA-N propan-2-yl 5-[[3-(2-phenylethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC=CC=2)=C1 UBOZPNIMKMUYBM-UHFFFAOYSA-N 0.000 description 1
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
DTJNRGSHBAFNEY-UHFFFAOYSA-N propan-2-yl 5-[[3-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCC=2C=CC=CC=2)=C1 DTJNRGSHBAFNEY-UHFFFAOYSA-N 0.000 description 1
VCPPMMNLHWSWJP-UHFFFAOYSA-N propan-2-yl 5-[[3-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCCC=2C=CC=CC=2)=C1 VCPPMMNLHWSWJP-UHFFFAOYSA-N 0.000 description 1
HTCJTRMADAQIGM-UHFFFAOYSA-N propan-2-yl 5-[[3-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 HTCJTRMADAQIGM-UHFFFAOYSA-N 0.000 description 1
YYFYIZQVGUOPLT-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1 YYFYIZQVGUOPLT-UHFFFAOYSA-N 0.000 description 1
GZJSTZFBMNWTRR-UHFFFAOYSA-N propan-2-yl 5-[[3-(cyclohexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=NC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=CC=C1)C(=O)NC1CCCCC1 GZJSTZFBMNWTRR-UHFFFAOYSA-N 0.000 description 1
PIANZKHCFHVKKY-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1 PIANZKHCFHVKKY-UHFFFAOYSA-N 0.000 description 1
CVZIFGOUEVUELK-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1 CVZIFGOUEVUELK-UHFFFAOYSA-N 0.000 description 1
SUXCEXOUQAYCPX-UHFFFAOYSA-N propan-2-yl 5-[[3-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 SUXCEXOUQAYCPX-UHFFFAOYSA-N 0.000 description 1
YRDUFMBECSACSA-UHFFFAOYSA-N propan-2-yl 5-[[3-[2-(4-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=CC(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)=C1 YRDUFMBECSACSA-UHFFFAOYSA-N 0.000 description 1
JSQXTWBSESCHDR-UHFFFAOYSA-N propan-2-yl 5-[[4-(2-acetamidoethyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 JSQXTWBSESCHDR-UHFFFAOYSA-N 0.000 description 1
HJJAWYUPFQBPTP-UHFFFAOYSA-N propan-2-yl 5-[[4-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCOC=2C=CC=CC=2)C=C1 HJJAWYUPFQBPTP-UHFFFAOYSA-N 0.000 description 1
GAZJQTAVPTXBDB-UHFFFAOYSA-N propan-2-yl 5-[[4-(3-methoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(C(=O)NCCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C(=O)OC(C)C)N=C1 GAZJQTAVPTXBDB-UHFFFAOYSA-N 0.000 description 1
FAVNEKNMWWTBEO-UHFFFAOYSA-N propan-2-yl 5-[[4-(4-phenylbutylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCCCC=2C=CC=CC=2)C=C1 FAVNEKNMWWTBEO-UHFFFAOYSA-N 0.000 description 1
CETNKOHGMLOBBS-UHFFFAOYSA-N propan-2-yl 5-[[4-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1 CETNKOHGMLOBBS-UHFFFAOYSA-N 0.000 description 1
BBAGYHQWTGOIFD-UHFFFAOYSA-N propan-2-yl 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(C)C)N=C1 BBAGYHQWTGOIFD-UHFFFAOYSA-N 0.000 description 1
SYAXTCLVWYTMSZ-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)N=C1 SYAXTCLVWYTMSZ-UHFFFAOYSA-N 0.000 description 1
UMDXARGHYUZSSS-UHFFFAOYSA-N propan-2-yl 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(C)C)N=C1 UMDXARGHYUZSSS-UHFFFAOYSA-N 0.000 description 1
UNHPIXPZFRIMLR-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 UNHPIXPZFRIMLR-UHFFFAOYSA-N 0.000 description 1
PFQZLRHTJBJJKI-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NCCC=2C=CC(F)=CC=2)C=C1 PFQZLRHTJBJJKI-UHFFFAOYSA-N 0.000 description 1
CMMMLJSCTFUDNL-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)N=C1 CMMMLJSCTFUDNL-UHFFFAOYSA-N 0.000 description 1
WRBVJNVOZSODJR-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)N=C1 WRBVJNVOZSODJR-UHFFFAOYSA-N 0.000 description 1
ZCVDKZMLJGAHIQ-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-[(2-phenoxyacetyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)COC1=CC=CC=C1 ZCVDKZMLJGAHIQ-UHFFFAOYSA-N 0.000 description 1
OHWPRFOPCTWGDV-UHFFFAOYSA-N propan-2-yl 5-[[4-[2-[(4-ethoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=CC(OCC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)C=2C=NC(=CC=2)C(=O)OC(C)C)C=C1 OHWPRFOPCTWGDV-UHFFFAOYSA-N 0.000 description 1
PEWJZESHPKSRNB-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)C=C1 PEWJZESHPKSRNB-UHFFFAOYSA-N 0.000 description 1
FSHFCYFFMBJUJM-UHFFFAOYSA-N propan-2-yl 5-[[4-chloro-3-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(Cl)C(C(=O)NCCOC=2C=CC=CC=2)=C1 FSHFCYFFMBJUJM-UHFFFAOYSA-N 0.000 description 1
JDILXARCVRDVDN-UHFFFAOYSA-N propan-2-yl 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(C)C)=C1 JDILXARCVRDVDN-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
HZNGDENZZQXEKU-UHFFFAOYSA-N propyl 5-(benzenesulfonylcarbamoyl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 HZNGDENZZQXEKU-UHFFFAOYSA-N 0.000 description 1
NCXDCHMDYCWVCK-UHFFFAOYSA-N propyl 5-[(4-methoxyphenyl)sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(OC)C=C1 NCXDCHMDYCWVCK-UHFFFAOYSA-N 0.000 description 1
APDUKHWODMCSOX-UHFFFAOYSA-N propyl 5-[[3-(2-phenoxyethylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCOC=2C=CC=CC=2)=C1 APDUKHWODMCSOX-UHFFFAOYSA-N 0.000 description 1
QZBYAEVESHMAJM-UHFFFAOYSA-N propyl 5-[[3-(3-methoxypropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCOC)=C1 QZBYAEVESHMAJM-UHFFFAOYSA-N 0.000 description 1
CZSNQSGIMXWXLC-UHFFFAOYSA-N propyl 5-[[3-(3-phenylpropylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCCC=2C=CC=CC=2)=C1 CZSNQSGIMXWXLC-UHFFFAOYSA-N 0.000 description 1
FKDVNEKSGJTCOS-UHFFFAOYSA-N propyl 5-[[3-(4-phenylbutanoylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NC(=O)CCCC=2C=CC=CC=2)=C1 FKDVNEKSGJTCOS-UHFFFAOYSA-N 0.000 description 1
MJBMTWIXQVZFPR-UHFFFAOYSA-N propyl 5-[[3-(benzylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 MJBMTWIXQVZFPR-UHFFFAOYSA-N 0.000 description 1
GOYKDVMYMCJDMR-UHFFFAOYSA-N propyl 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)OCCC)=C1 GOYKDVMYMCJDMR-UHFFFAOYSA-N 0.000 description 1
JQYZSBNFAXMQLP-UHFFFAOYSA-N propyl 5-[[3-(cyclohexylcarbamoyl)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NC2CCCCC2)=C1 JQYZSBNFAXMQLP-UHFFFAOYSA-N 0.000 description 1
MTTYCTHISDOBQK-UHFFFAOYSA-N propyl 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)OCCC)=C1 MTTYCTHISDOBQK-UHFFFAOYSA-N 0.000 description 1
KCMQKGHCGBJNKZ-UHFFFAOYSA-N propyl 5-[[3-[2-(2-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C(=CC=CC=2)OC)=C1 KCMQKGHCGBJNKZ-UHFFFAOYSA-N 0.000 description 1
FZUHPIPTGYEPKY-UHFFFAOYSA-N propyl 5-[[3-[2-(3-methoxyphenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=C(OC)C=CC=2)=C1 FZUHPIPTGYEPKY-UHFFFAOYSA-N 0.000 description 1
HANFNJCOCSJZFZ-UHFFFAOYSA-N propyl 5-[[3-[2-(4-fluorophenyl)ethylcarbamoyl]phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC(C(=O)NCCC=2C=CC(F)=CC=2)=C1 HANFNJCOCSJZFZ-UHFFFAOYSA-N 0.000 description 1
JLXSMABUYZHWLW-UHFFFAOYSA-N propyl 5-[[4-(4-phenylbutanoylamino)phenyl]sulfonylcarbamoyl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCCC)=CC=C1C(=O)NS(=O)(=O)C(C=C1)=CC=C1NC(=O)CCCC1=CC=CC=C1 JLXSMABUYZHWLW-UHFFFAOYSA-N 0.000 description 1
XUXWZPNCALGOTJ-UHFFFAOYSA-N propyl 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)OCCC)N=C1 XUXWZPNCALGOTJ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000005412 pyrazyl group Chemical group 0.000 description 1
125000005495 pyridazyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Detergent Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10715593A 1992-10-02 1993-09-29 Esters of acylsulfonamide - and sulfonamidopyridine-2 carboxylic acid and their pyridine N-oxides, methods for their preparation and use as drugs IL107155A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4233124A DE4233124A1 (de)	1992-10-02	1992-10-02	Acylsulfonamido- und Sulfonamidopyridin-2-carbonsäureester sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel

Publications (2)

Publication Number	Publication Date
IL107155A0 IL107155A0 (en)	1993-12-28
IL107155A true IL107155A (en)	1999-09-22

Family

ID=6469456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10715593A IL107155A (en)	1992-10-02	1993-09-29	Esters of acylsulfonamide - and sulfonamidopyridine-2 carboxylic acid and their pyridine N-oxides, methods for their preparation and use as drugs

Country Status (25)

Country	Link
US (1)	US5428046A (es)
EP (1)	EP0590520B1 (es)
JP (1)	JPH06211795A (es)
KR (1)	KR940009156A (es)
CN (1)	CN1089603A (es)
AT (1)	ATE139227T1 (es)
AU (1)	AU662448B2 (es)
CA (1)	CA2107514A1 (es)
CZ (1)	CZ283869B6 (es)
DE (2)	DE4233124A1 (es)
DK (1)	DK0590520T3 (es)
ES (1)	ES2090806T3 (es)
FI (1)	FI103881B (es)
GR (1)	GR3020230T3 (es)
HK (1)	HK1006713A1 (es)
HU (1)	HUT67292A (es)
IL (1)	IL107155A (es)
MY (1)	MY110277A (es)
NO (1)	NO180085C (es)
NZ (1)	NZ248819A (es)
PH (1)	PH30677A (es)
PL (1)	PL176772B1 (es)
RU (1)	RU2117660C1 (es)
TW (1)	TW258733B (es)
ZA (1)	ZA937298B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL135495A (en) *	1995-09-28	2002-12-01	Hoechst Ag	Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid
DE19742951A1 (de) *	1997-09-29	1999-04-15	Hoechst Schering Agrevo Gmbh	Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung
DE19746287A1 (de) *	1997-10-20	1999-04-22	Hoechst Marion Roussel De Gmbh	Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
TW201512171A (zh)	2013-04-19	2015-04-01	Pfizer Ltd	化學化合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3432094A1 (de) *	1984-08-31	1986-03-06	Hoechst Ag, 6230 Frankfurt	Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase
DE3703963A1 (de) *	1987-02-10	1988-08-18	Hoechst Ag	Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen
DE3703959A1 (de) *	1987-02-10	1988-08-18	Hoechst Ag	Pyridin-2,4- und 2,5-dicarbonsaeureamide, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
DE3703962A1 (de) *	1987-02-10	1988-08-18	Hoechst Ag	Pyridin-2,4- und 2,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
DE3707429A1 (de) *	1987-03-07	1988-09-15	Hoechst Ag	Substituierte pyridin-2,4-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
DE4020570A1 (de) *	1990-06-28	1992-01-02	Hoechst Ag	2,4- und 2,5-substituierte pyridin-n-oxide, verfahren zu deren herstellung sowie deren verwendung
DE4031000A1 (de) *	1990-10-01	1992-04-09	Hoechst Ag	4- oder 5-substituierte pyridin-2-carbonsaeuren, verfahren zu deren herstellung sowie deren verwendung als arzneimittel

1992
- 1992-10-02 DE DE4233124A patent/DE4233124A1/de not_active Withdrawn
1993
- 1993-08-05 TW TW082106253A patent/TW258733B/zh active
- 1993-09-22 US US08/124,683 patent/US5428046A/en not_active Expired - Fee Related
- 1993-09-23 ES ES93115361T patent/ES2090806T3/es not_active Expired - Lifetime
- 1993-09-23 DE DE59302898T patent/DE59302898D1/de not_active Expired - Fee Related
- 1993-09-23 DK DK93115361.3T patent/DK0590520T3/da active
- 1993-09-23 EP EP93115361A patent/EP0590520B1/de not_active Expired - Lifetime
- 1993-09-23 AT AT93115361T patent/ATE139227T1/de not_active IP Right Cessation
- 1993-09-29 IL IL10715593A patent/IL107155A/en not_active IP Right Cessation
- 1993-09-29 CN CN93118248A patent/CN1089603A/zh active Pending
- 1993-09-30 PH PH46989A patent/PH30677A/en unknown
- 1993-09-30 NZ NZ248819A patent/NZ248819A/en unknown
- 1993-09-30 MY MYPI93001990A patent/MY110277A/en unknown
- 1993-09-30 CZ CZ932044A patent/CZ283869B6/cs not_active IP Right Cessation
- 1993-09-30 FI FI934303A patent/FI103881B/fi active
- 1993-10-01 HU HU9302778A patent/HUT67292A/hu unknown
- 1993-10-01 ZA ZA937298A patent/ZA937298B/xx unknown
- 1993-10-01 PL PL93300561A patent/PL176772B1/pl unknown
- 1993-10-01 RU RU93056156A patent/RU2117660C1/ru active
- 1993-10-01 CA CA002107514A patent/CA2107514A1/en not_active Abandoned
- 1993-10-01 NO NO933521A patent/NO180085C/no not_active IP Right Cessation
- 1993-10-01 AU AU48726/93A patent/AU662448B2/en not_active Ceased
- 1993-10-02 KR KR1019930020299A patent/KR940009156A/ko active IP Right Grant
- 1993-10-04 JP JP5247717A patent/JPH06211795A/ja active Pending
1996
- 1996-06-13 GR GR960401603T patent/GR3020230T3/el unknown
1998
- 1998-06-22 HK HK98105875A patent/HK1006713A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO180085B (no)	1996-11-04
PL176772B1 (pl)	1999-07-30
IL107155A0 (en)	1993-12-28
KR940009156A (ko)	1994-05-20
PH30677A (en)	1997-09-16
CZ204493A3 (en)	1994-05-18
CN1089603A (zh)	1994-07-20
GR3020230T3 (en)	1996-09-30
FI934303A (fi)	1994-04-03
HK1006713A1 (en)	1999-03-12
CA2107514A1 (en)	1994-04-03
US5428046A (en)	1995-06-27
EP0590520A1 (de)	1994-04-06
PL300561A1 (en)	1994-04-05
EP0590520B1 (de)	1996-06-12
NO180085C (no)	1997-02-12
DE4233124A1 (de)	1994-04-07
HUT67292A (en)	1995-03-28
DK0590520T3 (da)	1996-10-14
HU9302778D0 (en)	1993-12-28
ZA937298B (en)	1994-04-25
NO933521D0 (no)	1993-10-01
NO933521L (no)	1994-04-05
DE59302898D1 (de)	1996-07-18
FI103881B1 (fi)	1999-10-15
FI934303A0 (fi)	1993-09-30
AU4872693A (en)	1994-04-14
ES2090806T3 (es)	1996-10-16
CZ283869B6 (cs)	1998-06-17
ATE139227T1 (de)	1996-06-15
FI103881B (fi)	1999-10-15
AU662448B2 (en)	1995-08-31
MY110277A (en)	1998-03-31
RU2117660C1 (ru)	1998-08-20
NZ248819A (en)	1996-02-27
TW258733B (es)	1995-10-01
JPH06211795A (ja)	1994-08-02

Legal Events

Date	Code	Title
2000-01-31	FF	Patent granted
2000-08-13	KB	Patent renewed
2004-06-01	RH1	Patent not in force

Publication	Publication Date	Title
US5658933A (en)	1997-08-19	Substituted heterocyclic carboxamide esters, their preparation and their use as pharmaceuticals
CA2092276A1 (en)	1993-09-25	Sulfonamido- and sulfonamidocarbonylpyridine -2-carboxamides and their pyridine-n-oxides, process for their preparation and their use as pharmaceuticals
EP0650961B1 (de)	1997-03-05	Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
US5610172A (en)	1997-03-11	Sulfonamidocarbonylpyridine-2-carboxamides and pyridine-n-oxides which are useful as pharmaceuticals
US5620996A (en)	1997-04-15	Sulfonamidocarbonyl pyridine-2-carboxesteramides and their pyridine-N-oxide compounds and their use as pharmaceuticals
EP0661269B1 (de)	1997-03-26	Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
KR20100068453A (ko)	2010-06-23	치환된 니코틴아미드 화합물 및 약제학적 제품에서 이의 용도
CA2145473A1 (en)	1995-09-26	Substituted heterocyclic carboxamidoesters their preparation and their use as pharmaceuticals
CA2078590A1 (en)	1993-03-20	2-hydroxymethylpyridines, the corresponding pyridine n-oxides and their derivatives, processes for their preparation and their use
IL107155A (en)	1999-09-22	Esters of acylsulfonamide - and sulfonamidopyridine-2 carboxylic acid and their pyridine N-oxides, methods for their preparation and use as drugs
CA2095206A1 (en)	1993-10-31	4- or 5-(sulf)imido- and -(sulfon)amidopyridines and their pyridine n-oxides, processes for their preparation, and their use as medicaments
WO2014082737A1 (en)	2014-06-05	Specific carboxamides as kcnq2/3 modulators
CA2145472A1 (en)	1995-09-26	Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals
DE4433928A1 (de)	1996-03-28	Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
DE4410881A1 (de)	1995-10-12	Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
DE4434288A1 (de)	1996-03-28	Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel
DE4337270A1 (de)	1995-05-04	Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel