ZA200209364B - Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. - Google Patents
Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. Download PDFInfo
- Publication number
- ZA200209364B ZA200209364B ZA200209364A ZA200209364A ZA200209364B ZA 200209364 B ZA200209364 B ZA 200209364B ZA 200209364 A ZA200209364 A ZA 200209364A ZA 200209364 A ZA200209364 A ZA 200209364A ZA 200209364 B ZA200209364 B ZA 200209364B
- Authority
- ZA
- South Africa
- Prior art keywords
- thiazol
- chloro
- phenyl
- dichloro
- benzenesulfonamide
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 10
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title description 2
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title description 2
- -1 1-benzothien-3-yl Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229940124530 sulfonamide Drugs 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 21
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 12
- 208000008589 Obesity Diseases 0.000 claims description 11
- 208000001132 Osteoporosis Diseases 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000002519 immonomodulatory effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 6
- 201000008980 hyperinsulinism Diseases 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 201000008827 tuberculosis Diseases 0.000 claims description 6
- KSSWUCOOEXHNBU-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 KSSWUCOOEXHNBU-UHFFFAOYSA-N 0.000 claims description 5
- ZJIZQFTYZLTSMM-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 ZJIZQFTYZLTSMM-UHFFFAOYSA-N 0.000 claims description 5
- OUIVYFVLHUTHFJ-UHFFFAOYSA-N 4-propyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 OUIVYFVLHUTHFJ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 241000700605 Viruses Species 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CLJQXQIYLDQWKS-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(OC)=CC=2)=CS1 CLJQXQIYLDQWKS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- MEMVIEZXBZFXRS-UHFFFAOYSA-N 2,3,4-trichloro-n-[4-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 MEMVIEZXBZFXRS-UHFFFAOYSA-N 0.000 claims description 4
- HJQRULUFRSMPIA-UHFFFAOYSA-N 2,3,4-trichloro-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 HJQRULUFRSMPIA-UHFFFAOYSA-N 0.000 claims description 4
- YJNNVTABROTHKU-UHFFFAOYSA-N 2,4,6-trichloro-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 YJNNVTABROTHKU-UHFFFAOYSA-N 0.000 claims description 4
- RCLKVEKOOWMTKR-UHFFFAOYSA-N 2,4,6-trichloro-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 RCLKVEKOOWMTKR-UHFFFAOYSA-N 0.000 claims description 4
- DYXBPGZNZNQXCN-UHFFFAOYSA-N 2,4,6-trichloro-n-(7,8-dimethoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound N=1C=2C=3C=C(OC)C(OC)=CC=3CCC=2SC=1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl DYXBPGZNZNQXCN-UHFFFAOYSA-N 0.000 claims description 4
- WJZGIBDJVQHZBI-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 WJZGIBDJVQHZBI-UHFFFAOYSA-N 0.000 claims description 4
- JNCDGKHJBKFXGQ-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 JNCDGKHJBKFXGQ-UHFFFAOYSA-N 0.000 claims description 4
- CWIDMGITMTWNFN-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 CWIDMGITMTWNFN-UHFFFAOYSA-N 0.000 claims description 4
- NHHKXWPXAPBQTL-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 NHHKXWPXAPBQTL-UHFFFAOYSA-N 0.000 claims description 4
- CMOQLUAPPPUJTM-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 CMOQLUAPPPUJTM-UHFFFAOYSA-N 0.000 claims description 4
- QHMZLUSHIXCCKP-UHFFFAOYSA-N 3-chloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 QHMZLUSHIXCCKP-UHFFFAOYSA-N 0.000 claims description 4
- 241000236488 Lepra Species 0.000 claims description 4
- 206010024229 Leprosy Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- QSNHYHIQRJKESU-UHFFFAOYSA-N n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 QSNHYHIQRJKESU-UHFFFAOYSA-N 0.000 claims description 4
- ARSMOHDWKMRMGC-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 ARSMOHDWKMRMGC-UHFFFAOYSA-N 0.000 claims description 4
- KSRJVDSZGGXISO-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 KSRJVDSZGGXISO-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- PZWRBNYWPNGEOO-UHFFFAOYSA-N 2,4,6-trichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl PZWRBNYWPNGEOO-UHFFFAOYSA-N 0.000 claims description 3
- LIAGCTWNDQEDEI-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1 LIAGCTWNDQEDEI-UHFFFAOYSA-N 0.000 claims description 3
- YWBBSEJKRWJKJL-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1 YWBBSEJKRWJKJL-UHFFFAOYSA-N 0.000 claims description 3
- LCKJEXQICKJFLG-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 LCKJEXQICKJFLG-UHFFFAOYSA-N 0.000 claims description 3
- DBDBNQRSYCPEBX-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 DBDBNQRSYCPEBX-UHFFFAOYSA-N 0.000 claims description 3
- YQBHFLUUYULGOK-UHFFFAOYSA-N 3-bromo-5-chloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound S1C(Cl)=CC(Br)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 YQBHFLUUYULGOK-UHFFFAOYSA-N 0.000 claims description 3
- DTFUYISNOGWKOH-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 DTFUYISNOGWKOH-UHFFFAOYSA-N 0.000 claims description 3
- UCOUPNQDIFHKSL-UHFFFAOYSA-N 3-chloro-n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)[N+]([O-])=O)Cl)=CS1 UCOUPNQDIFHKSL-UHFFFAOYSA-N 0.000 claims description 3
- OFGHBOOJNFEGPN-UHFFFAOYSA-N 3-chloro-n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=C(Cl)C=CC=3)C)SC=2)=C1 OFGHBOOJNFEGPN-UHFFFAOYSA-N 0.000 claims description 3
- QVLPVUZEELMXSD-UHFFFAOYSA-N 4-bromo-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=CC(Br)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 QVLPVUZEELMXSD-UHFFFAOYSA-N 0.000 claims description 3
- AMTZPKVOGGMRFE-UHFFFAOYSA-N 4-bromo-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-2,5-difluorobenzenesulfonamide Chemical compound C1=C(Br)C(F)=CC(S(=O)(=O)NC=2SC=C(N=2)C2=C(C=CS2)Cl)=C1F AMTZPKVOGGMRFE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- ZYALIHXSDIOPAD-UHFFFAOYSA-N n-[4-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 ZYALIHXSDIOPAD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- HLHHCFJYGNAZNK-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1Cl HLHHCFJYGNAZNK-UHFFFAOYSA-N 0.000 claims description 2
- FWYULONVWHMSTF-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 FWYULONVWHMSTF-UHFFFAOYSA-N 0.000 claims description 2
- XZCBMBTUYMYVPQ-UHFFFAOYSA-N 2,5-dichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=CC=C(Cl)C=3)Cl)SC=2)=C1Cl XZCBMBTUYMYVPQ-UHFFFAOYSA-N 0.000 claims description 2
- QDBFZVJMCHTGFQ-UHFFFAOYSA-N 2,6-dichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=CC=CC=3Cl)Cl)SC=2)=C1Cl QDBFZVJMCHTGFQ-UHFFFAOYSA-N 0.000 claims description 2
- YVUGSLBLCWYKER-UHFFFAOYSA-N 3-chloro-n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2SC(Cl)=CC=2)=CS1 YVUGSLBLCWYKER-UHFFFAOYSA-N 0.000 claims description 2
- WGVIRWKBCWZWRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(SC=1)=NC=1C1=CC=CC=C1 WGVIRWKBCWZWRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- AQBXFURRFAKIAK-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)sulfonylamino]-4-phenyl-1,3-thiazole-5-carboxylate Chemical compound N=1C(C=2C=CC=CC=2)=C(C(=O)OCC)SC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 AQBXFURRFAKIAK-UHFFFAOYSA-N 0.000 claims description 2
- YGNYHKCTKPHZIG-UHFFFAOYSA-N n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)SC=2)=C1 YGNYHKCTKPHZIG-UHFFFAOYSA-N 0.000 claims description 2
- ATERRQIYRKISJZ-UHFFFAOYSA-N n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound S1C(Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 ATERRQIYRKISJZ-UHFFFAOYSA-N 0.000 claims description 2
- WRZMEKKUQVDTEW-UHFFFAOYSA-N n-[4-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 WRZMEKKUQVDTEW-UHFFFAOYSA-N 0.000 claims description 2
- NRIPBFUCPSYOOW-UHFFFAOYSA-N n-[4-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 NRIPBFUCPSYOOW-UHFFFAOYSA-N 0.000 claims description 2
- JLXGDPCQFPZCKR-UHFFFAOYSA-N n-[4-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 JLXGDPCQFPZCKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims description 2
- XWMIRFXHIDTQJJ-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)[N+]([O-])=O)Cl)=CS1 XWMIRFXHIDTQJJ-UHFFFAOYSA-N 0.000 claims 3
- VUQXWOCNCDSVII-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 VUQXWOCNCDSVII-UHFFFAOYSA-N 0.000 claims 3
- KDUZPXUSQALCPA-UHFFFAOYSA-N 2,4-dichloro-n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3C)Cl)SC=2)=C1 KDUZPXUSQALCPA-UHFFFAOYSA-N 0.000 claims 3
- FAJVFLCPMDOACN-UHFFFAOYSA-N 2,4-dichloro-n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2SC(Cl)=CC=2)=CS1 FAJVFLCPMDOACN-UHFFFAOYSA-N 0.000 claims 3
- DWNOOXPCHYSFIE-UHFFFAOYSA-N 3-chloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C DWNOOXPCHYSFIE-UHFFFAOYSA-N 0.000 claims 3
- JFZAERHZXDAYOG-UHFFFAOYSA-N 3-chloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C2=C(C=CS2)Cl)=CS1 JFZAERHZXDAYOG-UHFFFAOYSA-N 0.000 claims 3
- FHZYYBRSQSLFKS-UHFFFAOYSA-N 4,5-dichloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 FHZYYBRSQSLFKS-UHFFFAOYSA-N 0.000 claims 3
- ARGPPKRCIPMUKS-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3SC(Cl)=C(Br)C=3)SC=2)=C1Cl ARGPPKRCIPMUKS-UHFFFAOYSA-N 0.000 claims 3
- HUPOREXJXWSXEX-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound BrC1=C(Cl)SC(S(=O)(=O)NC=2SC=C(N=2)C=2C(=CC(OC=3C=CC(Cl)=CC=3)=CC=2)Cl)=C1 HUPOREXJXWSXEX-UHFFFAOYSA-N 0.000 claims 3
- ZSDKYIALVTXWOK-UHFFFAOYSA-N 4-bromo-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]-2,5-difluorobenzenesulfonamide Chemical compound C1=C(Br)C(F)=CC(S(=O)(=O)NC=2SC=C(N=2)C=2C(=CC(OC=3C=CC(Cl)=CC=3)=CC=2)Cl)=C1F ZSDKYIALVTXWOK-UHFFFAOYSA-N 0.000 claims 3
- WCGMZEPQPWRBEM-UHFFFAOYSA-N ethyl 2-[(3-chloro-2-methylphenyl)sulfonylamino]-4-phenyl-1,3-thiazole-5-carboxylate Chemical compound N=1C(C=2C=CC=CC=2)=C(C(=O)OCC)SC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C WCGMZEPQPWRBEM-UHFFFAOYSA-N 0.000 claims 3
- LMWSVFYPBGCDNG-UHFFFAOYSA-N n-[4-(1-benzothiophen-3-yl)-1,3-thiazol-2-yl]-2,4-dichloro-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C3=CC=CC=C3SC=2)=CS1 LMWSVFYPBGCDNG-UHFFFAOYSA-N 0.000 claims 3
- XFSPRFGBEXCDSK-UHFFFAOYSA-N n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)[N+]([O-])=O)Cl)=CS1 XFSPRFGBEXCDSK-UHFFFAOYSA-N 0.000 claims 3
- PYXWIQIFUOTQGV-UHFFFAOYSA-N n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C)C(F)=CC=2)=CS1 PYXWIQIFUOTQGV-UHFFFAOYSA-N 0.000 claims 3
- HPIGZGUJLIQAQZ-UHFFFAOYSA-N n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2SC(Cl)=CC=2)=CS1 HPIGZGUJLIQAQZ-UHFFFAOYSA-N 0.000 claims 3
- GJXCRMNFCPLYHK-UHFFFAOYSA-N n-[4-[2-[(2,4,5-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 GJXCRMNFCPLYHK-UHFFFAOYSA-N 0.000 claims 3
- DFJRULZVAINKHJ-UHFFFAOYSA-N 2,3,4-trichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1Cl DFJRULZVAINKHJ-UHFFFAOYSA-N 0.000 claims 2
- AETBUEDTDDAPHZ-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 AETBUEDTDDAPHZ-UHFFFAOYSA-N 0.000 claims 2
- OEFLRNMNICOWET-UHFFFAOYSA-N 2,4-dichloro-n-(6-chloro-8-methylsulfonyl-4,5-dihydrothieno[3,4-e][1,3]benzothiazol-2-yl)-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C(Cl)SC(S(C)(=O)=O)=C21 OEFLRNMNICOWET-UHFFFAOYSA-N 0.000 claims 2
- IYBVNOCVQJXETB-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2,5-dimethylfuran-3-yl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound O1C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3C)Cl)SC=2)=C1C IYBVNOCVQJXETB-UHFFFAOYSA-N 0.000 claims 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
- FLLKOCYXRBYTCX-UHFFFAOYSA-N 3-bromo-5-chloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)thiophene-2-sulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C=1SC(Cl)=CC=1Br FLLKOCYXRBYTCX-UHFFFAOYSA-N 0.000 claims 2
- YNOQFQLDZODJFO-UHFFFAOYSA-N 3-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YNOQFQLDZODJFO-UHFFFAOYSA-N 0.000 claims 2
- LXXRUQRDBHMNOA-UHFFFAOYSA-N 4,5-dichloro-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound FC1=CC=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 LXXRUQRDBHMNOA-UHFFFAOYSA-N 0.000 claims 2
- MGRVIPJHIXBGFN-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 MGRVIPJHIXBGFN-UHFFFAOYSA-N 0.000 claims 2
- YAPWIIYQMOFZIP-UHFFFAOYSA-N 4-bromo-n-[4-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-2,5-difluorobenzenesulfonamide Chemical compound C1=C(Br)C(F)=CC(S(=O)(=O)NC=2SC=C(N=2)C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)=C1F YAPWIIYQMOFZIP-UHFFFAOYSA-N 0.000 claims 2
- BCAOCGDSOGDAQA-UHFFFAOYSA-N ethyl 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 BCAOCGDSOGDAQA-UHFFFAOYSA-N 0.000 claims 2
- JWGBLRGWKGFLNS-UHFFFAOYSA-N n-(4-phenyl-1,3-thiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 JWGBLRGWKGFLNS-UHFFFAOYSA-N 0.000 claims 2
- OYGSUBKAKZFLIY-UHFFFAOYSA-N n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=CC(OC)=CC=C21 OYGSUBKAKZFLIY-UHFFFAOYSA-N 0.000 claims 2
- TXIFSWBQGDCPIK-UHFFFAOYSA-N n-(8-nitro-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=CC=C([N+]([O-])=O)C=C21 TXIFSWBQGDCPIK-UHFFFAOYSA-N 0.000 claims 2
- OBTIINLBOJFNKM-UHFFFAOYSA-N n-(8-nitro-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound N=1C=2C3=CC([N+](=O)[O-])=CC=C3CCC=2SC=1NS(=O)(=O)C1=CC=CC=C1 OBTIINLBOJFNKM-UHFFFAOYSA-N 0.000 claims 2
- AJUZHBIWIUGLOE-UHFFFAOYSA-N n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C2=C(C=CS2)Cl)=CS1 AJUZHBIWIUGLOE-UHFFFAOYSA-N 0.000 claims 2
- SDNVLYKBFAOEMD-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 SDNVLYKBFAOEMD-UHFFFAOYSA-N 0.000 claims 2
- BOIGAJAKSOYMNU-UHFFFAOYSA-N n-[4-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(NC(C)=O)=CC=2)=CS1 BOIGAJAKSOYMNU-UHFFFAOYSA-N 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- RCFDQFMMYFHCDN-UHFFFAOYSA-N 2,3,4-trichloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 RCFDQFMMYFHCDN-UHFFFAOYSA-N 0.000 claims 1
- LUJMZSBENYHLCG-UHFFFAOYSA-N 2,3,4-trichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=C(Cl)C(Cl)=CC=3)Cl)SC=2)=C1Cl LUJMZSBENYHLCG-UHFFFAOYSA-N 0.000 claims 1
- RYIARRMIANIOSW-UHFFFAOYSA-N 2,4,5-trichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=C(Cl)C=3)Cl)SC=2)=C1Cl RYIARRMIANIOSW-UHFFFAOYSA-N 0.000 claims 1
- UQQMUUNYGNDIPZ-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1 UQQMUUNYGNDIPZ-UHFFFAOYSA-N 0.000 claims 1
- SMYNKXCLCLKPOC-UHFFFAOYSA-N 2,4-dichloro-n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C2C=CS1 SMYNKXCLCLKPOC-UHFFFAOYSA-N 0.000 claims 1
- JJWMKRNBYQJEHX-UHFFFAOYSA-N 2,4-dichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-6-methylbenzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl JJWMKRNBYQJEHX-UHFFFAOYSA-N 0.000 claims 1
- BNSBTDSZLWMSSK-UHFFFAOYSA-N 2,4-dichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C2=C(C=CS2)Cl)=CS1 BNSBTDSZLWMSSK-UHFFFAOYSA-N 0.000 claims 1
- WGJFORGGQDOUAV-UHFFFAOYSA-N 2,4-dichloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WGJFORGGQDOUAV-UHFFFAOYSA-N 0.000 claims 1
- OWXGPEDUOJJGNH-UHFFFAOYSA-N 3-chloro-n-(6-chloro-8-methylsulfonyl-4,5-dihydrothieno[3,4-e][1,3]benzothiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C(Cl)SC(S(C)(=O)=O)=C21 OWXGPEDUOJJGNH-UHFFFAOYSA-N 0.000 claims 1
- MARPDDXUBWNKFF-UHFFFAOYSA-N 4,5-dichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)thiophene-2-sulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=CC(Cl)=C(Cl)S1 MARPDDXUBWNKFF-UHFFFAOYSA-N 0.000 claims 1
- UVJIGTAIUQXSPE-UHFFFAOYSA-N 4-chloro-n-[4-(4,5-dichlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(Cl)=C(Cl)C=C1C1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 UVJIGTAIUQXSPE-UHFFFAOYSA-N 0.000 claims 1
- ZYDKFFBEDBXPRV-UHFFFAOYSA-N ethyl 4-phenyl-2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazole-5-carboxylate Chemical compound N=1C(C=2C=CC=CC=2)=C(C(=O)OCC)SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZYDKFFBEDBXPRV-UHFFFAOYSA-N 0.000 claims 1
- NPWLGEAARUTBIP-UHFFFAOYSA-N n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound N=1C(C=2C=CSC=2CC2)=C2SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 NPWLGEAARUTBIP-UHFFFAOYSA-N 0.000 claims 1
- BLTIIVURSXLRMW-UHFFFAOYSA-N n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound N=1C(C=2C=CSC=2CC2)=C2SC=1NS(=O)(=O)C1=CC=CC=C1 BLTIIVURSXLRMW-UHFFFAOYSA-N 0.000 claims 1
- OMAMNIZLTOWNOM-UHFFFAOYSA-N n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OMAMNIZLTOWNOM-UHFFFAOYSA-N 0.000 claims 1
- INOGCCHVCWPGMI-UHFFFAOYSA-N n-(8-nitro-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound N=1C=2C3=CC([N+](=O)[O-])=CC=C3CCC=2SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 INOGCCHVCWPGMI-UHFFFAOYSA-N 0.000 claims 1
- QMVYTPAQDNNMEF-UHFFFAOYSA-N n-[2-[(4-propylphenyl)sulfonylamino]-4,5-dihydrobenzo[e][1,3]benzothiazol-6-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C(NC(C)=O)C=CC=C21 QMVYTPAQDNNMEF-UHFFFAOYSA-N 0.000 claims 1
- XMHYLNOKGUOPNR-UHFFFAOYSA-N n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)SC=2)=C1 XMHYLNOKGUOPNR-UHFFFAOYSA-N 0.000 claims 1
- SZLCFTOXPJWYOV-UHFFFAOYSA-N n-[4-[2-[(4-bromo-2,5-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Br)=C(F)C=2)F)=N1 SZLCFTOXPJWYOV-UHFFFAOYSA-N 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 13
- 108090000790 Enzymes Proteins 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 229940037128 systemic glucocorticoids Drugs 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 230000002440 hepatic effect Effects 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 102000004277 11-beta-hydroxysteroid dehydrogenases Human genes 0.000 description 4
- 108090000874 11-beta-hydroxysteroid dehydrogenases Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 229960004544 cortisone Drugs 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 230000037406 food intake Effects 0.000 description 4
- 230000009229 glucose formation Effects 0.000 description 4
- 229960000890 hydrocortisone Drugs 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 210000000987 immune system Anatomy 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 238000002821 scintillation proximity assay Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 3
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 3
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 3
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 241000235058 Komagataella pastoris Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 229960000530 carbenoxolone Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- 238000001952 enzyme assay Methods 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000008348 humoral response Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 208000026278 immune system disease Diseases 0.000 description 3
- 230000004410 intraocular pressure Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- AMNURQPTXNTGRJ-UHFFFAOYSA-N 1,2,3a,4-tetrahydro-[1,3]thiazolo[5,4-c]pyridine Chemical class C1=NCC2SCNC2=C1 AMNURQPTXNTGRJ-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 208000004611 Abdominal Obesity Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010065941 Central obesity Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 102100036264 Glucose-6-phosphatase catalytic subunit 1 Human genes 0.000 description 2
- 101710099339 Glucose-6-phosphatase catalytic subunit 1 Proteins 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 description 2
- 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- 230000009118 appropriate response Effects 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000004110 gluconeogenesis Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000003914 insulin secretion Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 210000004185 liver Anatomy 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
- 239000000463 material Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 230000002123 temporal effect Effects 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- AYTPIVIDHMVGSX-UHFFFAOYSA-N 2,1,3-benzoselenadiazole Chemical compound C1=CC=CC2=N[se]N=C21 AYTPIVIDHMVGSX-UHFFFAOYSA-N 0.000 description 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
- GVXOMWVQNODSOD-UHFFFAOYSA-N 2,4,6-trichloro-n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C2C=CS1 GVXOMWVQNODSOD-UHFFFAOYSA-N 0.000 description 1
- MIECVJDZXBUVSN-UHFFFAOYSA-N 2,4-diphenyl-1,3-thiazole Chemical class C=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MIECVJDZXBUVSN-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- OODAPEFTXCQBDJ-UHFFFAOYSA-N 2-bromo-n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=N1 OODAPEFTXCQBDJ-UHFFFAOYSA-N 0.000 description 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108091007914 CDKs Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- 102400000321 Glucagon Human genes 0.000 description 1
- 108060003199 Glucagon Proteins 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 101000958041 Homo sapiens Musculin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010022489 Insulin Resistance Diseases 0.000 description 1
- 108010044467 Isoenzymes Proteins 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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 101710151321 Melanostatin Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 1
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102400000064 Neuropeptide Y Human genes 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 240000006711 Pistacia vera Species 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 101100095563 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SEO1 gene Proteins 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000029662 T-helper 1 type immune response Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- VFRROHXSMXFLSN-KCDKBNATSA-N aldehydo-D-galactose 6-phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O VFRROHXSMXFLSN-KCDKBNATSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001837 anti-cortisol effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 210000000270 basal cell Anatomy 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 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 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000008846 dynamic interplay Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000004821 effect on bone Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000000871 endothelium corneal Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 210000003560 epithelium corneal Anatomy 0.000 description 1
- 239000002329 esterase inhibitor Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
- 229960004666 glucagon Drugs 0.000 description 1
- 201000003617 glucocorticoid-induced osteoporosis Diseases 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000004116 glycogenolysis Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 102000046949 human MSC Human genes 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000002660 insulin-secreting cell Anatomy 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006993 memory improvement Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UOJHJBJPZSSQJN-UHFFFAOYSA-N n-(5-nitro-1,3-thiazol-2-yl)benzenesulfonamide Chemical class S1C([N+](=O)[O-])=CN=C1NS(=O)(=O)C1=CC=CC=C1 UOJHJBJPZSSQJN-UHFFFAOYSA-N 0.000 description 1
- JELWQGMQFGGMCZ-UHFFFAOYSA-N n-[2-(benzenesulfonamido)-4,5-dihydrobenzo[e][1,3]benzothiazol-6-yl]acetamide Chemical compound S1C=2CCC=3C(NC(=O)C)=CC=CC=3C=2N=C1NS(=O)(=O)C1=CC=CC=C1 JELWQGMQFGGMCZ-UHFFFAOYSA-N 0.000 description 1
- VATOYJIUMWMLLX-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound ClC1=CC=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 VATOYJIUMWMLLX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000003955 neuronal function Effects 0.000 description 1
- 230000006576 neuronal survival Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000024121 nodulation Effects 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 210000002997 osteoclast Anatomy 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
- DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000000229 preadipocyte Anatomy 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000006965 reversible inhibition Effects 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000012488 skeletal system development Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 210000002536 stromal cell Anatomy 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200209364B true ZA200209364B (en) | 2004-02-18 |
Family
ID=20279781
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200209362A ZA200209362B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
ZA200209360A ZA200209360B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
ZA200209359A ZA200209359B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
ZA200209364A ZA200209364B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200209362A ZA200209362B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
ZA200209360A ZA200209360B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
ZA200209359A ZA200209359B (en) | 2000-05-22 | 2002-11-18 | Inhibitors of 11-Beta-hydroxy steroid dehydrogenase type 1. |
Country Status (24)
Country | Link |
---|---|
US (7) | US7618961B2 (ru) |
EP (4) | EP1283831A1 (ru) |
JP (4) | JP2003534337A (ru) |
KR (4) | KR20030016272A (ru) |
CN (4) | CN1437588A (ru) |
AR (1) | AR033534A1 (ru) |
AT (2) | ATE485283T1 (ru) |
AU (6) | AU6093101A (ru) |
BR (1) | BR0111099A (ru) |
CA (4) | CA2408144C (ru) |
DE (3) | DE60139931D1 (ru) |
EA (1) | EA005274B1 (ru) |
ES (1) | ES2333846T3 (ru) |
HK (1) | HK1056878A1 (ru) |
HU (1) | HUP0302435A3 (ru) |
IL (4) | IL152753A0 (ru) |
MX (1) | MXPA02011632A (ru) |
NO (4) | NO20025588L (ru) |
NZ (4) | NZ522538A (ru) |
PE (1) | PE20020100A1 (ru) |
PL (1) | PL360137A1 (ru) |
SE (1) | SE0001899D0 (ru) |
WO (5) | WO2001090090A1 (ru) |
ZA (4) | ZA200209362B (ru) |
Families Citing this family (185)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
JP2004502432A (ja) * | 2000-07-05 | 2004-01-29 | バイエル アクチェンゲゼルシャフト | ヒト11β−ヒドロキシステロイドデヒドロゲナーゼ1様酵素の調節 |
GB0107383D0 (en) * | 2001-03-23 | 2001-05-16 | Univ Edinburgh | Lipid profile modulation |
AU2007205749B2 (en) * | 2001-11-22 | 2009-04-23 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
US7094792B2 (en) * | 2001-11-22 | 2006-08-22 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
EA200400708A1 (ru) * | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
US20030130279A1 (en) * | 2001-11-22 | 2003-07-10 | Guido Kurz | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
BR0214342A (pt) * | 2001-11-22 | 2004-09-14 | Biovitrum Ab | Inibidores de 11 - beta - hidroxi esteróide desidrogenase tipo 1 |
PL370111A1 (en) | 2001-11-22 | 2005-05-16 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
US7485655B2 (en) | 2002-01-16 | 2009-02-03 | University Of Virginia Patent Foundation | 2-Aminothiazole allosteric enhancers of A1 adenosine receptors |
EP1474139B1 (en) * | 2002-02-01 | 2007-11-21 | Merck & Co., Inc. | 11-beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia |
US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
CN100343240C (zh) * | 2002-03-29 | 2007-10-17 | 先灵公司 | 手性2-甲基-4-保护的哌嗪的立体选择性烷基化 |
SE0201194D0 (sv) * | 2002-04-19 | 2002-04-19 | Astrazeneca Ab | New compounds |
US20030198965A1 (en) | 2002-04-19 | 2003-10-23 | Isis Pharmaceuticals Inc. | Antisense modulation of hydroxysteroid 11-beta dehydrogenase 1 expression |
AR040241A1 (es) * | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
AU2003275195A1 (en) * | 2002-09-18 | 2004-04-08 | Hartmut M. Hanauske-Abel | INHIBITORS OF 11Beta-HYDROXYSTEROID DEHYDROGENASE AND USES THEREFOR |
JP2006506451A (ja) * | 2002-10-11 | 2006-02-23 | アストラゼネカ アクチボラグ | 1,4−ジ置換ピペリジン誘導体および11−βHSD1阻害薬としてのそれらの使用 |
CA2501228A1 (en) * | 2002-10-24 | 2004-05-06 | Sterix Limited | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 and type 2 |
GB0224830D0 (en) | 2002-10-24 | 2002-12-04 | Sterix Ltd | Compound |
US20060058315A1 (en) * | 2002-11-07 | 2006-03-16 | Astrazeneca Ab | 2-Oxo-ethanesulfonamide derivates |
PE20040693A1 (es) * | 2002-11-14 | 2004-11-23 | Novartis Ag | N-sulfonilaminotiazol como mediadores de la sulfatasa de esteroides |
GB0226602D0 (en) * | 2002-11-14 | 2002-12-24 | Novartis Ag | Organic compounds |
JO2397B1 (en) * | 2002-12-20 | 2007-06-17 | ميرك شارب اند دوم كوربوريشن | Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors |
WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
FR2849598B1 (fr) * | 2003-01-07 | 2006-09-22 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete, par augmentation du nombre de cellules des ilots de langerhans |
FR2849599B1 (fr) * | 2003-01-07 | 2006-12-29 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete |
TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
DE10314610A1 (de) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | Neues Diphenylazetidinon mit verbesserten physiologischen Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindungen enthaltende Arzneimittel und dessen Verwendung |
US7501405B2 (en) | 2003-04-11 | 2009-03-10 | High Point Pharmaceuticals, Llc | Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders |
EP1785424A3 (en) * | 2003-04-11 | 2009-12-23 | High Point Pharmaceuticals, LLC | Fused 1,2,4-triazoles and pharmaceutical uses thereof |
US7700583B2 (en) | 2003-04-11 | 2010-04-20 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
EP1618090A1 (en) | 2003-04-11 | 2006-01-25 | Novo Nordisk A/S | 11ß-HYDROXYSTEROID DEHYDROGENASE TYPE 1 ACTIVE COMPOUNDS |
DK1615647T3 (da) | 2003-04-11 | 2010-04-06 | High Point Pharmaceuticals Llc | Farmaceutisk anvendelse af kondenserede 1,2,4-triazoler |
US7173030B2 (en) | 2003-05-21 | 2007-02-06 | Biovitrum Ab | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
AU2004240885A1 (en) * | 2003-05-21 | 2004-12-02 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type I |
CA2526712A1 (en) | 2003-05-29 | 2004-12-09 | Merck & Co., Inc. | Triazole derivatives as inhibitors of 11-beta hydroxysteroid dehydrogenase-1 |
SE0301884D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use III |
SE0301885D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use IV |
SE0301882D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use I |
SE0301883D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use II |
WO2004113310A1 (en) * | 2003-06-25 | 2004-12-29 | Biovitrum Ab | Use of an inhibitor of 11-b-hydroxysteroid dehydrogenase type 1 compounds for promoting wound healing |
JP4765627B2 (ja) | 2003-09-22 | 2011-09-07 | Msd株式会社 | 新規ピペリジン誘導体 |
GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
GB0325745D0 (en) * | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
OA13344A (en) * | 2003-12-19 | 2007-04-13 | Pfizer | Benzenesulfonylamino-pyridin-2-yl derivatives and related compounds as inhibitors of 11-beta-hydroxysteroid dehydrogenase type 1 (11-beta-HSD-1) for the treatment of diabetes and obesity. |
US7365075B2 (en) | 2003-12-22 | 2008-04-29 | Amgen Inc. | Aryl sulfonamide compounds and uses related thereto |
WO2005073200A1 (en) | 2004-01-26 | 2005-08-11 | Merck & Co., Inc. | Novel crystalline forms of an inhibitor of 11-beta-hydroxysteroid dehydrogenase type 1 |
EP2305352A1 (en) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-reductase inhibitors for use in the treatment of men with metabolic and anthropometric disorders |
JP2007261945A (ja) * | 2004-04-07 | 2007-10-11 | Taisho Pharmaceut Co Ltd | チアゾール誘導体 |
EP1735275B1 (en) | 2004-04-14 | 2010-08-18 | Amgen Inc. | Aryl sulfones and uses related thereto |
CA2561858A1 (en) | 2004-04-20 | 2005-12-15 | Amgen Inc. | Arylsulfonamides and uses related thereto |
GB0408771D0 (en) * | 2004-04-20 | 2004-05-26 | Sterix Ltd | Compound |
CA2565630C (en) | 2004-05-07 | 2013-05-28 | Janssen Pharmaceutica N.V. | Pyrrolidin-2-one and piperidin-2-one derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
WO2005116002A2 (en) | 2004-05-24 | 2005-12-08 | Amgen Inc. | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
US8686011B2 (en) | 2004-05-24 | 2014-04-01 | Amgen Inc. | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
EP1763517B1 (en) * | 2004-06-28 | 2011-05-11 | F. Hoffmann-La Roche AG | Pyrimidine derivatives as 11beta-hsd1 inhibitors |
AU2005268899B2 (en) * | 2004-08-05 | 2009-09-24 | F. Hoffmann-La Roche Ag | Substituted N-acyl-2-aminothiazoles |
MX2007002449A (es) | 2004-08-30 | 2007-10-10 | Janssen Pharmaceutica Nv | Derivados de n-2 adamantanil-2-fenoxi-acetamida como inhibidores de deshidrogenasa 11-beta hidroxiesteroide. |
DE602005017159D1 (de) | 2004-08-30 | 2009-11-26 | Janssen Pharmaceutica Nv | Oxysteroid-dehydrogenase-inhibitoren |
WO2006024628A1 (en) | 2004-08-30 | 2006-03-09 | Janssen Pharmaceutica N.V. | Tricyclic lactam derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
EP1797042B1 (en) * | 2004-09-29 | 2009-01-07 | F.Hoffmann-La Roche Ag | Indozolone derivatives as 11b-hsd1 inhibitors |
JP5414990B2 (ja) * | 2004-10-04 | 2014-02-12 | エフ.ホフマン−ラ ロシュ アーゲー | 糖尿病のための11−β阻害剤としてのアルキルピリジン |
CN103073460B (zh) * | 2004-10-14 | 2015-09-09 | Abbvie德国有限责任两合公司 | 适用于治疗对于多巴胺d3受体的调节有反应的疾病的芳基磺酰基甲基或芳基磺酰胺取代的芳族化合物 |
JP2008517930A (ja) | 2004-10-21 | 2008-05-29 | トランス テック ファーマ,インコーポレイテッド | GalR1のアゴニストとしてのビススルホンアミド化合物、組成物、及び使用法 |
EP1666467A1 (en) * | 2004-11-08 | 2006-06-07 | Evotec AG | 11Beta-HSD1 Inhibitors |
EP1659113A1 (en) * | 2004-11-08 | 2006-05-24 | Evotec AG | Inhibitors of 11beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1) |
WO2006051662A1 (ja) * | 2004-11-09 | 2006-05-18 | Taisho Pharmaceutical Co., Ltd. | チアゾール誘導体 |
WO2006059507A1 (ja) * | 2004-11-30 | 2006-06-08 | Sankyo Company, Limited | 11β-HSD1アンチセンス化合物 |
WO2006066109A2 (en) * | 2004-12-17 | 2006-06-22 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
GB0506133D0 (en) * | 2005-03-24 | 2005-05-04 | Sterix Ltd | Compound |
EP1866298A2 (en) | 2005-03-31 | 2007-12-19 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
PT1928840E (pt) | 2005-04-05 | 2011-10-03 | Hoffmann La Roche | 1h-pirazole-4-carboxamidas, a sua preparação e a sua utilização a título de inibidores de 11-betahidroxiesteróide desidrogenase |
EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
WO2006134481A1 (en) * | 2005-06-16 | 2006-12-21 | Pfizer Inc. | Inhibitors of 11-beta hydroxysteroid dehydrogenase type 1 |
BRPI0611853A2 (pt) * | 2005-06-16 | 2010-10-05 | Pfizer | derivados de n-(piridin-2-il)-sulfonamida |
JPWO2007018248A1 (ja) | 2005-08-10 | 2009-02-19 | 萬有製薬株式会社 | ピリドン化合物 |
WO2007024004A1 (ja) | 2005-08-24 | 2007-03-01 | Banyu Pharmaceutical Co., Ltd. | フェニルピリドン誘導体 |
US7622492B2 (en) | 2005-08-31 | 2009-11-24 | Hoffmann-La Roche Inc. | Pyrazolones as inhibitors of 11β-hydroxysteroid dehydrogenase |
AU2006288153A1 (en) | 2005-09-07 | 2007-03-15 | Msd K.K. | Bicyclic aromatic substituted pyridone derivative |
RU2008116844A (ru) | 2005-09-29 | 2009-11-10 | Мерк энд Ко., Инк. (US) | Ацилированные производные спиропиперидина как модуляторы рецептора меланокортина-4 |
JP2007099659A (ja) * | 2005-10-03 | 2007-04-19 | Toray Fine Chemicals Co Ltd | ピペラジンカルボン酸エステルの製造法 |
ATE551333T1 (de) * | 2005-10-12 | 2012-04-15 | Vertex Pharma | Biphenylderivate als modulatoren von spannungsabhängigen ionenkanälen |
EP2332526A3 (en) | 2005-10-21 | 2011-10-12 | Novartis AG | Combination of a renin-inhibitor and an anti-dyslipidemic agent and/or an antiobesity agent |
EP1944301A4 (en) | 2005-10-27 | 2012-01-04 | Msd Kk | NEW BENZOXATHIIN DERIVATIVES |
JP4371164B2 (ja) | 2005-11-10 | 2009-11-25 | 萬有製薬株式会社 | アザ置換スピロ誘導体 |
US20070110802A1 (en) * | 2005-11-15 | 2007-05-17 | Janan Jona | Wet granulation process |
AU2006316867A1 (en) | 2005-11-22 | 2007-05-31 | Amgen Inc. | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
CN101365686A (zh) | 2005-12-21 | 2009-02-11 | 沃泰克斯药物股份有限公司 | 作为离子通道调节剂的杂环衍生物 |
WO2007076875A2 (en) * | 2006-01-06 | 2007-07-12 | Aarhus Universitet | Compounds acting on the serotonin transporter |
CA2636826C (en) | 2006-01-18 | 2011-11-29 | F.Hoffmann-La Roche Ag | Thiazoles as 11 beta-hsd1 inhibitors |
DK2029529T3 (da) * | 2006-04-24 | 2010-09-20 | Lilly Co Eli | Substitueret pyrrolidinone som inhibitor af 11-beta-hydroxysteroiddehydrogenase 1 |
CA2649111C (en) * | 2006-04-24 | 2013-09-10 | Eli Lilly And Company | Cyclohexyl substituted pyrrolidinones as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
CN101096363B (zh) * | 2006-06-27 | 2011-05-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途 |
JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−2,4−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
WO2008039327A2 (en) | 2006-09-22 | 2008-04-03 | Merck & Co., Inc. | Method of treatment using fatty acid synthesis inhibitors |
JPWO2008038692A1 (ja) | 2006-09-28 | 2010-01-28 | 萬有製薬株式会社 | ジアリールケチミン誘導体 |
DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
CN101668524B (zh) * | 2007-02-12 | 2012-10-24 | 阿斯利康(瑞典)有限公司 | 作为11-β-HSD1抑制剂的吡唑衍生物 |
US20110003856A1 (en) | 2007-02-23 | 2011-01-06 | Soren Ebdrup | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
CN101679217A (zh) | 2007-02-23 | 2010-03-24 | 高点制药有限责任公司 | 作为11β-羟基类固醇脱氢酶抑制剂的N-金刚烷基苯甲酰胺 |
US20110003852A1 (en) | 2007-02-23 | 2011-01-06 | Soren Ebdrup | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
ATE461177T1 (de) | 2007-03-23 | 2010-04-15 | Icagen Inc | Ionenkanal-hemmer |
WO2008120653A1 (ja) | 2007-04-02 | 2008-10-09 | Banyu Pharmaceutical Co., Ltd. | インドールジオン誘導体 |
CN101677562A (zh) * | 2007-04-11 | 2010-03-24 | 高点制药有限责任公司 | 新化合物 |
CA2688161C (en) | 2007-06-04 | 2020-10-20 | Kunwar Shailubhai | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
US8222417B2 (en) | 2007-06-27 | 2012-07-17 | Taisho Pharmaceutical Co., Ltd | Compound having 11β-HSD1 inhibitory activity |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
JPWO2009110510A1 (ja) | 2008-03-06 | 2011-07-14 | Msd株式会社 | アルキルアミノピリジン誘導体 |
CN101981025A (zh) | 2008-03-28 | 2011-02-23 | 万有制药株式会社 | 具有黑色素浓缩激素受体拮抗作用的二芳基甲基酰胺衍生物 |
JP2011522828A (ja) | 2008-06-04 | 2011-08-04 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
AU2009261248A1 (en) | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diarylketoxime derivative |
TW201014822A (en) | 2008-07-09 | 2010-04-16 | Sanofi Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
JP2011528375A (ja) | 2008-07-16 | 2011-11-17 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
WO2010013595A1 (ja) | 2008-07-30 | 2010-02-04 | 萬有製薬株式会社 | 5員-5員又は5員-6員縮環シクロアルキルアミン誘導体 |
CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
CN102272103B (zh) | 2008-10-30 | 2015-10-21 | 默沙东公司 | 异烟酰胺食欲素受体拮抗剂 |
US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
KR200452117Y1 (ko) * | 2008-11-10 | 2011-02-08 | 대성공업주식회사 | 휠체어용 브레이크 와이어 케이블 지지 브래킷 |
BRPI0921299A2 (pt) | 2008-11-21 | 2015-08-25 | High Point Pharmaceuticals Llc | Compostos de benzamida adamantila |
WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
ES2350077B1 (es) | 2009-06-04 | 2011-11-04 | Laboratorios Salvat, S.A. | Compuestos inhibidores de 11beta-hidroxiesteroide deshidrogenasa de tipo 1. |
CN102482312A (zh) | 2009-08-26 | 2012-05-30 | 赛诺菲 | 新颖的杂芳族氟代糖苷结晶水合物、含有这些化合物的药物和它们的用途 |
WO2011106273A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
WO2012015715A1 (en) * | 2010-07-27 | 2012-02-02 | High Point Pharmaceuticals, Llc | Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta hsd1 modulators |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
WO2012116145A1 (en) | 2011-02-25 | 2012-08-30 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
MX357121B (es) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Proceso de preparacion de agonistas c de guanilato ciclasa. |
US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
EP2683700B1 (de) | 2011-03-08 | 2015-02-18 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
CN103204824B (zh) * | 2012-01-12 | 2015-04-08 | 清华大学深圳研究生院 | 2-氨基噻唑-4-酰胺类衍生物及其制备方法与应用 |
JP2015525782A (ja) | 2012-08-02 | 2015-09-07 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | 抗糖尿病性三環式化合物 |
CA2898482A1 (en) | 2013-02-22 | 2014-08-28 | Linda L. Brockunier | Antidiabetic bicyclic compounds |
WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
CA2913737A1 (en) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
US9708272B2 (en) | 2014-08-29 | 2017-07-18 | Tes Pharma S.R.L. | Inhibitors of α-amino-β-carboxymuconic acid semialdehyde decarboxylase |
CN105017135A (zh) * | 2015-07-19 | 2015-11-04 | 佛山市赛维斯医药科技有限公司 | 一类二吡啶叔醇结构的11β-HSD1抑制剂、制备方法及其用途 |
CN105001152A (zh) * | 2015-07-19 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 一类二甲胺基二吡啶叔醇结构的11β-HSD1抑制剂及其用途 |
EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
MX2019004321A (es) | 2016-10-14 | 2019-06-12 | Tes Pharma S R L | Inhibidores de la acido alfa-amino-beta-carboximuconico semialdehido descarboxilasa. |
CN107663204A (zh) * | 2016-10-19 | 2018-02-06 | 首都医科大学附属北京世纪坛医院 | 一种化合物的抗结核应用 |
EP3551176A4 (en) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | ANTIDIABETIC HETEROCYCLIC COMPOUNDS |
WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
US11655246B2 (en) * | 2017-11-30 | 2023-05-23 | Step Pharma S.A.S. | Aminothiazole compounds as inhibitors of CTPS1 |
US11505547B2 (en) | 2017-11-30 | 2022-11-22 | Step Pharma S.A.S. | Compounds |
SI3752510T1 (sl) | 2018-02-15 | 2023-03-31 | Vertex Pharmaceuticals Incorporated | Makrocikli kot modulatorji regulatorja transmembranske prevodnosti pri cistični fibrozi, farmacevtski sestavki iz le-teh, njihova uporaba pri zdravljenju cistične fibroze in postopek za njihovo proizvodnjo |
CN108358869B (zh) * | 2018-03-27 | 2019-09-10 | 河北师范大学 | 一种n-苯并噻唑基苯磺酰胺类衍生物、制备方法及用途 |
CN108659219B (zh) * | 2018-06-08 | 2021-02-09 | 扬州大学 | 一种聚苯胺的制备方法 |
CA3119509A1 (en) | 2018-11-20 | 2020-05-28 | Tes Pharma S.R.L | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxxylase |
CN109748831A (zh) * | 2018-12-17 | 2019-05-14 | 南通正达农化有限公司 | 一种三氟甲磺酸三氟乙酯的制备方法 |
EP3924058A1 (en) | 2019-02-13 | 2021-12-22 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
WO2021026047A1 (en) | 2019-08-08 | 2021-02-11 | Merck Sharp & Dohme Corp. | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
TW202120517A (zh) | 2019-08-14 | 2021-06-01 | 美商維泰克斯製藥公司 | 製備cftr調節劑之方法 |
TW202115092A (zh) | 2019-08-14 | 2021-04-16 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白之調節劑 |
EP4013760A1 (en) | 2019-08-14 | 2022-06-22 | Vertex Pharmaceuticals Incorporated | Crystalline forms of cftr modulators |
CN111620837B (zh) * | 2020-06-29 | 2022-02-15 | 郑州大学 | 香柏酮噻唑酰胺类化合物、及其制备方法和应用 |
KR20230053639A (ko) | 2020-08-18 | 2023-04-21 | 머크 샤프 앤드 돔 엘엘씨 | 비시클로헵탄 피롤리딘 오렉신 수용체 효능제 |
US20230373974A1 (en) * | 2020-10-07 | 2023-11-23 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
CN112451514A (zh) * | 2020-11-26 | 2021-03-09 | 江西农业大学 | 二氢杨梅素纳米硒及其制备方法和应用 |
CN113461635A (zh) * | 2021-07-07 | 2021-10-01 | 上海毕得医药科技股份有限公司 | 4-(2-氯乙基)噻唑-2-羧酸乙酯及其制备方法和应用 |
US20230143250A1 (en) * | 2021-08-20 | 2023-05-11 | Enanta Pharmaceuticals, Inc. | 17-beta-hydroxysteroid dehydrogenase type 13 inhibitors and methods of use thereof |
Family Cites Families (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB517272A (en) | 1938-06-03 | 1940-01-25 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
GB620654A (en) | 1939-10-03 | 1949-03-29 | Chinoin Gyogyszer Es Vegyeszet | A process for the preparation of sulphonamide derivatives of 2-amino-thiazole |
US2611770A (en) | 1949-04-16 | 1952-09-23 | American Cyanamid Co | N-(2-thiazolyl)-2-hydroxypyridine-5-sulfonamides |
GB822947A (en) | 1957-01-25 | 1959-11-04 | Smith & Nephew | Improvements in and relating to sulphonamides |
DE1620508A1 (de) * | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
CA1088049A (en) | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
FR2384498A1 (fr) * | 1975-11-26 | 1978-10-20 | Parcor | Nouveaux derives sulfonylamino thiazoliques et leurs applications en medecine humaine et veterinaire |
EP0246749A3 (en) * | 1986-05-17 | 1988-08-31 | AgrEvo UK Limited | Triazole herbicides |
US5591761A (en) | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5962490A (en) * | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
US5594021A (en) | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
JPH021483A (ja) | 1988-03-10 | 1990-01-05 | Nippon Tokushu Noyaku Seizo Kk | 農業用殺菌剤 |
JPH078863B2 (ja) | 1989-09-21 | 1995-02-01 | 久光製薬株式会社 | 新規なジフェニルチアゾール誘導体 |
DE69206725T2 (de) * | 1991-09-10 | 1996-05-02 | Zeneca Ltd | Benzolsulfonamidderivate als 5-Lipoxygenasehemmer |
JPH0670024B2 (ja) | 1993-04-13 | 1994-09-07 | 塩野義製薬株式会社 | グルタコン酸エステル誘導体の製法 |
US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
JPH07149745A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な2−アミノチアゾール誘導体 |
JPH07149746A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な2−置換アミノチアゾール誘導体 |
JPH07309757A (ja) * | 1994-05-18 | 1995-11-28 | Asahi Chem Ind Co Ltd | βアミロイド蛋白神経細胞毒性低減剤 |
CA2196174C (en) | 1994-08-09 | 2005-03-01 | Per Marin | Use of ketoconazole and related substances in medicaments for treatment of type ii diabetes |
DE69526958T2 (de) | 1994-11-29 | 2003-01-16 | Hisamitsu Pharmaceutical Co., Inc. | Antibakterielle oder bakterizide mittel, die 2-aminothiazolderivate und deren salze enthalten |
SE505391C2 (sv) | 1995-05-30 | 1997-08-18 | Cortendo Ab | Användning av kortisol-agonister för framställning av ett system för diagnostisering av det metabola syndromet |
GB9512697D0 (en) | 1995-06-22 | 1995-08-23 | Zeneca Ltd | Heterocyclic compounds |
GB9517622D0 (en) * | 1995-08-29 | 1995-11-01 | Univ Edinburgh | Regulation of intracellular glucocorticoid concentrations |
WO1997047299A1 (en) * | 1996-06-12 | 1997-12-18 | 3-Dimensional Pharmaceuticals, Inc. | Amidino and guanidino heterocyclic protease inhibitors |
US5877193A (en) | 1996-07-19 | 1999-03-02 | Hoffmann-La Roche Inc. | Use of N-(4-aryl-thiazol-2-yl)-sulfonamides |
NZ335029A (en) | 1996-10-16 | 2000-10-27 | American Cyanamid Co | Ortho-sulfonamido heteroaryl hydroxamic acids as matrix metalloproteinase (MMP) and TACE (tumor necrosis factor, TNF, alpha converting enzyme) inhibitors |
DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
SE9700642D0 (sv) | 1997-02-24 | 1997-02-24 | Kronvall Stefan Med Ab | Medel och sätt för förebyggande och behandling av det metabola syndromet |
US5783597A (en) * | 1997-03-04 | 1998-07-21 | Ortho Pharmaceutical Corporation | 2,5-disubstituted thiophenes: inhibitors of 5-lipoxygenase and inducible cyclooxygenase (COX-2) enzymes, composition and use |
WO1999002502A2 (en) | 1997-07-11 | 1999-01-21 | Smithkline Beecham Plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
GB9725141D0 (en) * | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Benzenesulfonamide compounds |
WO1999065884A1 (en) | 1998-06-18 | 1999-12-23 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
DE69928260T2 (de) | 1998-07-08 | 2006-07-20 | Sanofi-Aventis Deutschland Gmbh | Schwefel-substituierte sulfonylaminocarbonsäure n-arylamide, ihre herstellung, ihre anwendung und diese enthaltende pharmazeutische zusammensetzungen |
GB9915625D0 (en) | 1999-07-02 | 1999-09-01 | Cortendo Ab | Method |
GB0001449D0 (en) | 2000-01-21 | 2000-03-08 | Cortendo Ab | Compositions |
IT1317735B1 (it) | 2000-01-26 | 2003-07-15 | Nicox Sa | Sali di agenti antimicrobici. |
SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
AU2002213048A1 (en) | 2000-10-05 | 2002-04-15 | Smith Kline Beecham Corporation | Phosphate transport inhibitors |
GB0118300D0 (en) | 2001-07-26 | 2001-09-19 | Cortendo Ab | Formulations |
US7094792B2 (en) * | 2001-11-22 | 2006-08-22 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
US20030130279A1 (en) * | 2001-11-22 | 2003-07-10 | Guido Kurz | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
PL370111A1 (en) | 2001-11-22 | 2005-05-16 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
EA200400708A1 (ru) * | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
-
2000
- 2000-05-22 SE SE0001899A patent/SE0001899D0/xx unknown
-
2001
- 2001-05-18 PE PE2001000450A patent/PE20020100A1/es not_active Application Discontinuation
- 2001-05-22 AU AU6093101A patent/AU6093101A/xx not_active Withdrawn
- 2001-05-22 AU AU6093201A patent/AU6093201A/xx not_active Withdrawn
- 2001-05-22 DE DE60139931T patent/DE60139931D1/de not_active Expired - Lifetime
- 2001-05-22 BR BR0111099-3A patent/BR0111099A/pt not_active IP Right Cessation
- 2001-05-22 WO PCT/SE2001/001155 patent/WO2001090090A1/en active IP Right Grant
- 2001-05-22 WO PCT/SE2001/001157 patent/WO2001090094A1/en active IP Right Grant
- 2001-05-22 IL IL15275301A patent/IL152753A0/xx unknown
- 2001-05-22 AT AT01934782T patent/ATE485283T1/de not_active IP Right Cessation
- 2001-05-22 CA CA002408144A patent/CA2408144C/en not_active Expired - Fee Related
- 2001-05-22 NZ NZ522538A patent/NZ522538A/en unknown
- 2001-05-22 ES ES01937063T patent/ES2333846T3/es not_active Expired - Lifetime
- 2001-05-22 EP EP01934781A patent/EP1283831A1/en not_active Withdrawn
- 2001-05-22 US US10/296,553 patent/US7618961B2/en not_active Expired - Fee Related
- 2001-05-22 AU AU6445601A patent/AU6445601A/xx not_active Withdrawn
- 2001-05-22 NZ NZ522506A patent/NZ522506A/en unknown
- 2001-05-22 IL IL15267001A patent/IL152670A0/xx unknown
- 2001-05-22 US US10/276,954 patent/US7125900B2/en not_active Expired - Fee Related
- 2001-05-22 JP JP2001586279A patent/JP2003534337A/ja not_active Abandoned
- 2001-05-22 CN CN01811609A patent/CN1437588A/zh active Pending
- 2001-05-22 AU AU2001262831A patent/AU2001262831B9/en not_active Ceased
- 2001-05-22 DE DE60143293T patent/DE60143293D1/de not_active Expired - Lifetime
- 2001-05-22 KR KR1020027015743A patent/KR20030016272A/ko not_active Application Discontinuation
- 2001-05-22 WO PCT/SE2001/001154 patent/WO2001090093A1/en active Application Filing
- 2001-05-22 PL PL36013701A patent/PL360137A1/xx not_active IP Right Cessation
- 2001-05-22 EP EP01934782A patent/EP1283832B1/en not_active Expired - Lifetime
- 2001-05-22 CN CN01809979A patent/CN1430614A/zh active Pending
- 2001-05-22 KR KR1020027015703A patent/KR20030016269A/ko not_active Application Discontinuation
- 2001-05-22 AT AT01937063T patent/ATE443055T1/de not_active IP Right Cessation
- 2001-05-22 EA EA200201271A patent/EA005274B1/ru not_active IP Right Cessation
- 2001-05-22 IL IL15266901A patent/IL152669A0/xx unknown
- 2001-05-22 EP EP01938885A patent/EP1283833A1/en not_active Withdrawn
- 2001-05-22 MX MXPA02011632A patent/MXPA02011632A/es active IP Right Grant
- 2001-05-22 WO PCT/SE2001/001156 patent/WO2001090091A1/en active IP Right Grant
- 2001-05-22 HU HU0302435A patent/HUP0302435A3/hu unknown
- 2001-05-22 JP JP2001586280A patent/JP2003534338A/ja not_active Abandoned
- 2001-05-22 CA CA2409697A patent/CA2409697C/en not_active Expired - Fee Related
- 2001-05-22 US US10/296,552 patent/US7132436B2/en not_active Expired - Fee Related
- 2001-05-22 KR KR1020027015741A patent/KR20030011341A/ko not_active Application Discontinuation
- 2001-05-22 JP JP2001586278A patent/JP2003534336A/ja not_active Abandoned
- 2001-05-22 JP JP2001586282A patent/JP2003534339A/ja not_active Abandoned
- 2001-05-22 NZ NZ522591A patent/NZ522591A/en unknown
- 2001-05-22 US US10/296,132 patent/US7030135B2/en not_active Expired - Fee Related
- 2001-05-22 WO PCT/SE2001/001158 patent/WO2001090092A1/en active IP Right Grant
- 2001-05-22 CA CA002408783A patent/CA2408783A1/en not_active Abandoned
- 2001-05-22 EP EP01937063A patent/EP1283834B1/en not_active Expired - Lifetime
- 2001-05-22 KR KR1020027015742A patent/KR20030016271A/ko not_active Application Discontinuation
- 2001-05-22 DE DE1283831T patent/DE1283831T1/de active Pending
- 2001-05-22 CN CNB018116787A patent/CN1249039C/zh not_active Expired - Fee Related
- 2001-05-22 IL IL15279001A patent/IL152790A0/xx unknown
- 2001-05-22 AU AU6283101A patent/AU6283101A/xx active Pending
- 2001-05-22 AR ARP010102421A patent/AR033534A1/es not_active Application Discontinuation
- 2001-05-22 CA CA002408142A patent/CA2408142C/en not_active Expired - Fee Related
- 2001-05-22 CN CNB018099661A patent/CN1188403C/zh not_active Expired - Fee Related
- 2001-05-22 NZ NZ522507A patent/NZ522507A/en unknown
- 2001-05-22 AU AU2001262830A patent/AU2001262830A1/en not_active Abandoned
-
2002
- 2002-11-18 ZA ZA200209362A patent/ZA200209362B/en unknown
- 2002-11-18 ZA ZA200209360A patent/ZA200209360B/en unknown
- 2002-11-18 ZA ZA200209359A patent/ZA200209359B/en unknown
- 2002-11-18 ZA ZA200209364A patent/ZA200209364B/en unknown
- 2002-11-21 NO NO20025588A patent/NO20025588L/no not_active Application Discontinuation
- 2002-11-21 NO NO20025586A patent/NO323832B1/no not_active IP Right Cessation
- 2002-11-21 NO NO20025587A patent/NO323779B1/no not_active IP Right Cessation
- 2002-11-21 NO NO20025585A patent/NO323831B1/no not_active IP Right Cessation
-
2003
- 2003-12-19 HK HK03109254A patent/HK1056878A1/xx not_active IP Right Cessation
-
2005
- 2005-11-30 US US11/289,634 patent/US20060160797A1/en not_active Abandoned
-
2006
- 2006-08-29 US US11/511,224 patent/US20060287374A1/en not_active Abandoned
-
2009
- 2009-11-16 US US12/619,216 patent/US20100113435A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1283832B1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
EP1461325B1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
AU2001262831A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
EP1461327A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
US7671051B2 (en) | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 | |
AU2001260932B2 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
AU2001264456B2 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
AU2001260932A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
AU2001264456A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
AU2007205749A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |