HUP0202548A2

HUP0202548A2 - Faggyútermelés gátlásánál alkalmazható viaszészter- és koleszterilészter-szintézist gátló kettős inhibitorok és ezeket tartalmazó gyógyszerkészítmények

Faggyútermelés gátlásánál alkalmazható viaszészter- és koleszterilészter-szintézist gátló kettős inhibitorok és ezeket tartalmazó gyógyszerkészítmények Download PDF

Info

Publication number: HUP0202548A2
Authority: HU; Hungary
Prior art keywords: phenyl; group; bis; methylethyl; straight
Prior art date: 2001-08-01

Application number

HU0202548A

Other languages

English (en)

Hungarian (hu)

Inventor

Reynold Homan

Original Assignee

Warner-Lambert Company

Priority date

2001-08-01

Filing date

2002-07-31

Publication date

2003-02-28

2002-07-31 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2002-10-28 Publication of HU0202548D0 publication Critical patent/HU0202548D0/hu

2003-02-28 Publication of HUP0202548A2 publication Critical patent/HUP0202548A2/hu

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210000002374 sebum Anatomy 0.000 title claims abstract description 40
238000004519 manufacturing process Methods 0.000 title claims abstract description 30
-1 cholesteryl ester Chemical class 0.000 title claims description 259
230000002401 inhibitory effect Effects 0.000 title claims description 41
239000008194 pharmaceutical composition Substances 0.000 title claims description 30
239000003112 inhibitor Substances 0.000 title description 13
230000015572 biosynthetic process Effects 0.000 title description 10
239000004164 Wax ester Substances 0.000 title description 8
235000019386 wax ester Nutrition 0.000 title description 8
238000003786 synthesis reaction Methods 0.000 title description 7
230000009977 dual effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 181
125000000217 alkyl group Chemical group 0.000 claims abstract description 99
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 62
206010000496 acne Diseases 0.000 claims abstract description 51
238000000034 method Methods 0.000 claims abstract description 48
208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 45
210000001732 sebaceous gland Anatomy 0.000 claims abstract description 33
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 30
230000006589 gland dysfunction Effects 0.000 claims abstract description 24
108090000790 Enzymes Proteins 0.000 claims abstract description 19
102000004190 Enzymes Human genes 0.000 claims abstract description 19
206010039792 Seborrhoea Diseases 0.000 claims abstract description 15
239000005516 coenzyme A Substances 0.000 claims abstract description 8
229940093530 coenzyme a Drugs 0.000 claims abstract description 8
208000008742 seborrheic dermatitis Diseases 0.000 claims abstract description 8
230000037312 oily skin Effects 0.000 claims abstract description 7
230000003902 lesion Effects 0.000 claims abstract description 6
201000004624 Dermatitis Diseases 0.000 claims abstract description 5
241001303601 Rosacea Species 0.000 claims abstract description 5
239000003246 corticosteroid Substances 0.000 claims abstract description 5
108010083294 ethanol acyltransferase Proteins 0.000 claims abstract description 5
150000002191 fatty alcohols Chemical class 0.000 claims abstract description 5
230000008569 process Effects 0.000 claims abstract description 5
201000004700 rosacea Diseases 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 178
125000004432 carbon atom Chemical group C* 0.000 claims description 132
125000001424 substituent group Chemical group 0.000 claims description 73
150000003839 salts Chemical class 0.000 claims description 60
239000012453 solvate Substances 0.000 claims description 49
125000003545 alkoxy group Chemical group 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 38
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
239000000460 chlorine Substances 0.000 claims description 35
229910052801 chlorine Inorganic materials 0.000 claims description 35
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
239000011737 fluorine Substances 0.000 claims description 31
229910052731 fluorine Inorganic materials 0.000 claims description 31
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
239000001301 oxygen Substances 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
125000004434 sulfur atom Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 17
229930195733 hydrocarbon Natural products 0.000 claims description 14
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
150000002430 hydrocarbons Chemical class 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
150000001721 carbon Chemical group 0.000 claims description 11
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 10
229930195734 saturated hydrocarbon Natural products 0.000 claims description 10
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
LXLYXCFZXXKURC-UHFFFAOYSA-N [2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]sulfamic acid Chemical compound CC(C)C1=CC(C(C)C)=C(CC(=O)NS(O)(=O)=O)C(C(C)C)=C1 LXLYXCFZXXKURC-UHFFFAOYSA-N 0.000 claims description 9
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 9
125000001622 2-naphthyl group Chemical class [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
208000009675 Perioral Dermatitis Diseases 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000001637 1-naphthyl group Chemical class [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QLCRUODBCQNCBH-UHFFFAOYSA-N [3-(3-methyl-2-phenylpentanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(C(C)CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C QLCRUODBCQNCBH-UHFFFAOYSA-N 0.000 claims description 3
IJRXOUMLHZGJCS-UHFFFAOYSA-N (2,6-ditert-butyl-4-methoxyphenyl)-(2,2-diphenylethylsulfamoyl)carbamic acid Chemical compound CC(C)(C)C1=CC(OC)=CC(C(C)(C)C)=C1N(C(O)=O)S(=O)(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 IJRXOUMLHZGJCS-UHFFFAOYSA-N 0.000 claims description 2
LBIKPQCDUJUPIH-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(2,2-diphenylethylsulfamoyl)carbamic acid Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1N(C(O)=O)S(=O)(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 LBIKPQCDUJUPIH-UHFFFAOYSA-N 0.000 claims description 2
XKVVSRGHCRFQFX-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(dibutylsulfamoyl)carbamic acid Chemical compound CCCCN(CCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C XKVVSRGHCRFQFX-UHFFFAOYSA-N 0.000 claims description 2
HSJJPZPIIHWRRC-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(dihexylsulfamoyl)carbamic acid Chemical compound CCCCCCN(CCCCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C HSJJPZPIIHWRRC-UHFFFAOYSA-N 0.000 claims description 2
OLRGZODWXXXDQN-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(dioctylsulfamoyl)carbamic acid Chemical compound CCCCCCCCN(CCCCCCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C OLRGZODWXXXDQN-UHFFFAOYSA-N 0.000 claims description 2
WYFDUAYDHXQLHY-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(dipentylsulfamoyl)carbamic acid Chemical compound CCCCCN(CCCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C WYFDUAYDHXQLHY-UHFFFAOYSA-N 0.000 claims description 2
HZGQCZLAQBYNAH-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(dodecylsulfamoyl)carbamic acid Chemical compound CCCCCCCCCCCCNS(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C HZGQCZLAQBYNAH-UHFFFAOYSA-N 0.000 claims description 2
WNXCQAPZQXPDOT-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-(hexylsulfamoyl)carbamic acid Chemical compound CCCCCCNS(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C WNXCQAPZQXPDOT-UHFFFAOYSA-N 0.000 claims description 2
BGUMMVXPFGVPAS-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-[di(propan-2-yl)sulfamoyl]carbamic acid Chemical compound CC(C)N(C(C)C)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C BGUMMVXPFGVPAS-UHFFFAOYSA-N 0.000 claims description 2
WYEBEEAGEYOSCI-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-[methyl(2-phenylethyl)sulfamoyl]carbamic acid Chemical compound CC(C)(C)C=1C=C(C)C=C(C(C)(C)C)C=1N(C(O)=O)S(=O)(=O)N(C)CCC1=CC=CC=C1 WYEBEEAGEYOSCI-UHFFFAOYSA-N 0.000 claims description 2
IMAWEALFTLNBAL-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-[methyl(octyl)sulfamoyl]carbamic acid Chemical compound CCCCCCCCN(C)S(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C IMAWEALFTLNBAL-UHFFFAOYSA-N 0.000 claims description 2
XELCPVBZTQVBJQ-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-hexoxysulfonylcarbamic acid Chemical compound CCCCCCOS(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C XELCPVBZTQVBJQ-UHFFFAOYSA-N 0.000 claims description 2
UWZKZFULRQWXMY-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)-phenoxysulfonylcarbamic acid Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1N(C(O)=O)S(=O)(=O)OC1=CC=CC=C1 UWZKZFULRQWXMY-UHFFFAOYSA-N 0.000 claims description 2
DHFNCAWRGCSBGZ-UHFFFAOYSA-N (2,6-ditert-butylphenyl)-(2,2-diphenylethylsulfamoyl)carbamic acid Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1N(C(O)=O)S(=O)(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 DHFNCAWRGCSBGZ-UHFFFAOYSA-N 0.000 claims description 2
BAHZBEPJTGWNBI-UHFFFAOYSA-N (2,6-ditert-butylphenyl)-[2,6-di(propan-2-yl)phenoxy]sulfonylcarbamic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1OS(=O)(=O)N(C(O)=O)C1=C(C(C)(C)C)C=CC=C1C(C)(C)C BAHZBEPJTGWNBI-UHFFFAOYSA-N 0.000 claims description 2
HZILKBOATJZGNW-UHFFFAOYSA-N 1-(dicyclohexylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NS(=O)(=O)N(C1CCCCC1)C1CCCCC1 HZILKBOATJZGNW-UHFFFAOYSA-N 0.000 claims description 2
LZVGQASTEBPKJE-UHFFFAOYSA-N 1-(didecylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CCCCCCCCCCN(CCCCCCCCCC)S(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C LZVGQASTEBPKJE-UHFFFAOYSA-N 0.000 claims description 2
RISJQXIPSGBIDZ-UHFFFAOYSA-N 1-(didodecylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)S(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C RISJQXIPSGBIDZ-UHFFFAOYSA-N 0.000 claims description 2
WGHVMHGDKKTPNI-UHFFFAOYSA-N 1H-benzimidazol-2-ylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(O)=O)S(=O)(=O)NC1=NC2=CC=CC=C2N1 WGHVMHGDKKTPNI-UHFFFAOYSA-N 0.000 claims description 2
KMFMMPZPOCFFTK-UHFFFAOYSA-N 2,2-diphenylethylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(O)=O)S(=O)(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 KMFMMPZPOCFFTK-UHFFFAOYSA-N 0.000 claims description 2
SVISWFVZGCSHEK-UHFFFAOYSA-N 2-[2,6-di(propan-2-yl)phenyl]-n-[[2,4,6-tri(propan-2-yl)phenyl]methylsulfonyl]acetamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CS(=O)(=O)NC(=O)CC1=C(C(C)C)C=CC=C1C(C)C SVISWFVZGCSHEK-UHFFFAOYSA-N 0.000 claims description 2
FTUPHZDPMFYSPM-UHFFFAOYSA-N 2-[2,6-di(propan-2-yl)phenyl]-n-[[2,4,6-tri(propan-2-yl)phenyl]methylsulfonyl]acetamide;sodium Chemical compound [Na].CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CS(=O)(=O)NC(=O)CC1=C(C(C)C)C=CC=C1C(C)C FTUPHZDPMFYSPM-UHFFFAOYSA-N 0.000 claims description 2
125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
NVCAXWLFXNFPRF-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-2-ylacetyl)phenyl] sulfamate Chemical compound S1C(=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C NVCAXWLFXNFPRF-UHFFFAOYSA-N 0.000 claims description 2
BOGOAOVZHJYIRZ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-3-ylacetyl)phenyl] sulfamate Chemical compound S1C=C(C=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C BOGOAOVZHJYIRZ-UHFFFAOYSA-N 0.000 claims description 2
RNYUYZOQGFPICG-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethoxyphenyl)acetyl]phenyl] sulfamate Chemical compound COC1=CC(OC)=CC(OC)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C RNYUYZOQGFPICG-UHFFFAOYSA-N 0.000 claims description 2
LXSBEGRJNHLGJI-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethylphenyl)acetyl]phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=C(C)C=C(C)C=C1C LXSBEGRJNHLGJI-UHFFFAOYSA-N 0.000 claims description 2
WQRMTMWIXSZJNP-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]prop-2-enoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C=CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WQRMTMWIXSZJNP-UHFFFAOYSA-N 0.000 claims description 2
KKSWLSQKFBJGQJ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]propanoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C KKSWLSQKFBJGQJ-UHFFFAOYSA-N 0.000 claims description 2
MHCQGCLTFBMETG-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl] n-[2,6-di(propan-2-yl)phenoxy]sulfonylcarbamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1OC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C MHCQGCLTFBMETG-UHFFFAOYSA-N 0.000 claims description 2
OYLSQFMMVVAVCP-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-(hexylsulfamoyl)carbamic acid Chemical compound CCCCCCNS(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C OYLSQFMMVVAVCP-UHFFFAOYSA-N 0.000 claims description 2
LPSLDTRJJRBXNB-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-[[2,4,6-tri(propan-2-yl)phenyl]methylsulfonyl]carbamic acid Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CS(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C LPSLDTRJJRBXNB-UHFFFAOYSA-N 0.000 claims description 2
MJIIGCHIMUDXRH-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-[di(propan-2-yl)sulfamoyl]carbamic acid Chemical compound CC(C)N(C(C)C)S(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C MJIIGCHIMUDXRH-UHFFFAOYSA-N 0.000 claims description 2
VMMUOQUDMIHIDC-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-[methyl(octyl)sulfamoyl]carbamic acid Chemical compound CCCCCCCCN(C)S(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C VMMUOQUDMIHIDC-UHFFFAOYSA-N 0.000 claims description 2
AMBYPSSUCCWDNM-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-dodecoxysulfonylcarbamic acid Chemical compound CCCCCCCCCCCCOS(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C AMBYPSSUCCWDNM-UHFFFAOYSA-N 0.000 claims description 2
IRRVJWQOURBZNZ-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]-hexoxysulfonylcarbamic acid Chemical compound CCCCCCOS(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C IRRVJWQOURBZNZ-UHFFFAOYSA-N 0.000 claims description 2
FNQIZEQUAUEZSA-UHFFFAOYSA-N [2,6-diphenyl-3-[2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)C(C(=C1OS(N)(=O)=O)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 FNQIZEQUAUEZSA-UHFFFAOYSA-N 0.000 claims description 2
IBHZMFUKPWDNEH-UHFFFAOYSA-N [2-[2,4-di(propan-2-yl)-3-sulfamoyloxyphenyl]-2-oxo-1-[2,4,6-tri(propan-2-yl)phenyl]ethyl] acetate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(OC(C)=O)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C IBHZMFUKPWDNEH-UHFFFAOYSA-N 0.000 claims description 2
QNRBLGKOBXBNQA-UHFFFAOYSA-N [3-(1-phenylcyclopentanecarbonyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C1(C=2C=CC=CC=2)CCCC1 QNRBLGKOBXBNQA-UHFFFAOYSA-N 0.000 claims description 2
LHGJDLJINRPFDO-UHFFFAOYSA-N [3-(2-cyclohexyl-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)C1CCCCC1 LHGJDLJINRPFDO-UHFFFAOYSA-N 0.000 claims description 2
GRWVKVSNGVJKET-UHFFFAOYSA-N [3-(2-cyclopentyl-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)C1CCCC1 GRWVKVSNGVJKET-UHFFFAOYSA-N 0.000 claims description 2
MWMRVLOOUQKYSS-UHFFFAOYSA-N [3-(2-oxo-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(=O)C1=CC=CC=C1 MWMRVLOOUQKYSS-UHFFFAOYSA-N 0.000 claims description 2
LVUYWXXLGSVQEH-UHFFFAOYSA-N [3-(2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=CC=CC=C1 LVUYWXXLGSVQEH-UHFFFAOYSA-N 0.000 claims description 2
WUHZAAZJJIQGBP-UHFFFAOYSA-N [3-(3,3-diphenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 WUHZAAZJJIQGBP-UHFFFAOYSA-N 0.000 claims description 2
YKPBDXIXQLCDMW-UHFFFAOYSA-N [3-(3-phenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CCC1=CC=CC=C1 YKPBDXIXQLCDMW-UHFFFAOYSA-N 0.000 claims description 2
IEUKVMHUFHMJNZ-UHFFFAOYSA-N [3-(9h-fluorene-9-carbonyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C1C2=CC=CC=C2C2=CC=CC=C21 IEUKVMHUFHMJNZ-UHFFFAOYSA-N 0.000 claims description 2
COLDWNCECCAUKF-UHFFFAOYSA-N [3-[2-(1-adamantyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C12(CC3CC(CC(C1)C3)C2)CC(=O)C=1C(=C(C(=CC=1)C(C)C)OS(N)(=O)=O)C(C)C COLDWNCECCAUKF-UHFFFAOYSA-N 0.000 claims description 2
VUKGWEPYJTUIFU-UHFFFAOYSA-N [3-[2-(2,5-dimethoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=C(OC)C(CC(=O)C=2C(=C(OS(N)(=O)=O)C(C(C)C)=CC=2)C(C)C)=C1 VUKGWEPYJTUIFU-UHFFFAOYSA-N 0.000 claims description 2
VWMCJIVWYXESEB-UHFFFAOYSA-N [3-[2-(2-methoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=CC=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C VWMCJIVWYXESEB-UHFFFAOYSA-N 0.000 claims description 2
ODLHXSJZGOAYGM-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,4,6-tri(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=C(C(C)C)C=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C ODLHXSJZGOAYGM-UHFFFAOYSA-N 0.000 claims description 2
XBVKHCGXRZSBCL-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C XBVKHCGXRZSBCL-UHFFFAOYSA-N 0.000 claims description 2
SBRVUELQHAZESK-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate;sodium Chemical compound [Na].CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C SBRVUELQHAZESK-UHFFFAOYSA-N 0.000 claims description 2
DDHOUTXDEJOEFF-UHFFFAOYSA-N [3-[2-fluoro-2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(F)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C DDHOUTXDEJOEFF-UHFFFAOYSA-N 0.000 claims description 2
UVDBZLKUTRQIEF-UHFFFAOYSA-N [3-[2-hydroxy-2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(O)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C UVDBZLKUTRQIEF-UHFFFAOYSA-N 0.000 claims description 2
DXHYZVZSMDLNBQ-UHFFFAOYSA-N [3-decanoyl-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CCCCCCCCCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C DXHYZVZSMDLNBQ-UHFFFAOYSA-N 0.000 claims description 2
SDKIUQCUWFKCBF-UHFFFAOYSA-N [3-dodecanoyl-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CCCCCCCCCCCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C SDKIUQCUWFKCBF-UHFFFAOYSA-N 0.000 claims description 2
QIJRRLIZAUONKL-UHFFFAOYSA-N [cyclohexyl(propan-2-yl)sulfamoyl]-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CC(C)C=1C=CC=C(C(C)C)C=1N(C(O)=O)S(=O)(=O)N(C(C)C)C1CCCCC1 QIJRRLIZAUONKL-UHFFFAOYSA-N 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
MFMSTMVAHIXTQD-UHFFFAOYSA-N benzhydrylsulfamoyl-(2,6-ditert-butylphenyl)carbamic acid Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1N(C(O)=O)S(=O)(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 MFMSTMVAHIXTQD-UHFFFAOYSA-N 0.000 claims description 2
QLMBCUBWSRGMNC-UHFFFAOYSA-N benzhydrylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(O)=O)S(=O)(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 QLMBCUBWSRGMNC-UHFFFAOYSA-N 0.000 claims description 2
YRBVQXMIHCGKIB-UHFFFAOYSA-N decyl n-[[2,6-di(propan-2-yl)phenyl]carbamoyl]sulfamate Chemical compound CCCCCCCCCCOS(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C YRBVQXMIHCGKIB-UHFFFAOYSA-N 0.000 claims description 2
BRKQJLXWMPVCLN-UHFFFAOYSA-N dibutylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CCCCN(CCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C BRKQJLXWMPVCLN-UHFFFAOYSA-N 0.000 claims description 2
RNWNSODRKRHXCE-UHFFFAOYSA-N dihexylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CCCCCCN(CCCCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C RNWNSODRKRHXCE-UHFFFAOYSA-N 0.000 claims description 2
MCGVAFYNFOLDEK-UHFFFAOYSA-N dioctylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CCCCCCCCN(CCCCCCCC)S(=O)(=O)N(C(O)=O)C1=C(C(C)C)C=CC=C1C(C)C MCGVAFYNFOLDEK-UHFFFAOYSA-N 0.000 claims description 2
CANYLDWVMNQAOQ-UHFFFAOYSA-N diphenylsulfamoyl-[2,6-di(propan-2-yl)phenyl]carbamic acid Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(O)=O)S(=O)(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 CANYLDWVMNQAOQ-UHFFFAOYSA-N 0.000 claims description 2
NOEVVTBECLBEFJ-UHFFFAOYSA-N dodecan-2-yl n-[[2,6-di(propan-2-yl)phenyl]carbamoyl]sulfamate Chemical compound CCCCCCCCCCC(C)OS(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C NOEVVTBECLBEFJ-UHFFFAOYSA-N 0.000 claims description 2
AACIOBUVHVAPJZ-UHFFFAOYSA-N dodecyl n-[[2,6-di(propan-2-yl)phenyl]carbamoyl]sulfamate Chemical compound CCCCCCCCCCCCOS(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C AACIOBUVHVAPJZ-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
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CSMSEBHVGQHVQW-UHFFFAOYSA-N octadecyl n-[[2,6-di(propan-2-yl)phenyl]carbamoyl]sulfamate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C CSMSEBHVGQHVQW-UHFFFAOYSA-N 0.000 claims description 2
YNHXNUJRUYIHST-UHFFFAOYSA-N octan-2-yl n-[[2,6-di(propan-2-yl)phenyl]carbamoyl]sulfamate Chemical compound CCCCCCC(C)OS(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C YNHXNUJRUYIHST-UHFFFAOYSA-N 0.000 claims description 2
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CUGUAVRIHDMHEF-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl) n-dodecoxysulfonylcarbamate Chemical compound CCCCCCCCCCCCOS(=O)(=O)NC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C CUGUAVRIHDMHEF-UHFFFAOYSA-N 0.000 claims 1
TVUVBASDYPOVBJ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)sulfonylcarbamic acid;hydrochloride Chemical compound Cl.CN1CCN(S(=O)(=O)NC(O)=O)CC1 TVUVBASDYPOVBJ-UHFFFAOYSA-N 0.000 claims 1
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WERGUDHVRRAQIA-UHFFFAOYSA-N [3-(2-phenylbutanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WERGUDHVRRAQIA-UHFFFAOYSA-N 0.000 claims 1
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BKIZTHMHKWZOPD-UHFFFAOYSA-N [3-(3-methyl-2-phenylpentanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate;sodium Chemical compound [Na].C=1C=CC=CC=1C(C(C)CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C BKIZTHMHKWZOPD-UHFFFAOYSA-N 0.000 claims 1
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