CA2256631A1

CA2256631A1 - Compounds for and a method of inhibiting matrix metalloproteinases

Compounds for and a method of inhibiting matrix metalloproteinases Download PDF

Info

Publication number: CA2256631A1
Authority: CA; Canada
Prior art keywords: dibenzofuran; sulfonylamino; acid; phenyl; hexanoic acid
Prior art date: 1996-09-04
Legal status : Abandoned

Application number

CA002256631A

Other languages

English (en)

French (fr)

Inventor

Joseph Armand Picard

Drago Robert Sliskovic

Current Assignee

Warner Lambert Co LLC

Original Assignee

Individual

Priority date

1996-09-04

Filing date

1997-09-02

Publication date

1998-03-12

1997-09-02 Application filed by Individual filed Critical Individual

1998-03-12 Publication of CA2256631A1 publication Critical patent/CA2256631A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 124
238000000034 method Methods 0.000 title claims abstract description 85
102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 45
108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 45
230000002401 inhibitory effect Effects 0.000 title claims abstract description 6
208000025865 Ulcer Diseases 0.000 claims abstract description 17
231100000397 ulcer Toxicity 0.000 claims abstract description 17
206010028980 Neoplasm Diseases 0.000 claims abstract description 16
206010019280 Heart failures Diseases 0.000 claims abstract description 13
150000001413 amino acids Chemical class 0.000 claims abstract description 13
201000011510 cancer Diseases 0.000 claims abstract description 13
208000037260 Atherosclerotic Plaque Diseases 0.000 claims abstract description 12
208000027418 Wounds and injury Diseases 0.000 claims abstract description 12
208000037803 restenosis Diseases 0.000 claims abstract description 11
206010052428 Wound Diseases 0.000 claims abstract description 10
206010003246 arthritis Diseases 0.000 claims abstract description 10
230000001684 chronic effect Effects 0.000 claims abstract description 10
230000001419 dependent effect Effects 0.000 claims abstract description 10
206010064996 Ulcerative keratitis Diseases 0.000 claims abstract description 9
230000009545 invasion Effects 0.000 claims abstract description 9
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 9
230000005747 tumor angiogenesis Effects 0.000 claims abstract description 9
210000000265 leukocyte Anatomy 0.000 claims abstract description 8
230000001363 autoimmune Effects 0.000 claims abstract description 7
206010027476 Metastases Diseases 0.000 claims abstract description 6
230000009401 metastasis Effects 0.000 claims abstract description 6
208000028169 periodontal disease Diseases 0.000 claims abstract description 6
-1 -OC1-C6 alkyl Chemical group 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 13
229940024606 amino acid Drugs 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
229940002612 prodrug Drugs 0.000 claims description 9
239000000651 prodrug Substances 0.000 claims description 9
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
229910020008 S(O) Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
230000005764 inhibitory process Effects 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
230000003239 periodontal effect Effects 0.000 claims description 4
HDHGKKSSTJLVPS-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(2-phenylethylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCCC1=CC=CC=C1 HDHGKKSSTJLVPS-UHFFFAOYSA-N 0.000 claims description 3
KTBUWUJBOXSXNR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-methylpropoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)OCC(C)C)C(O)=O)=CC=C3OC2=C1 KTBUWUJBOXSXNR-UHFFFAOYSA-N 0.000 claims description 3
JQMYQNYDESVNOP-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(naphthalen-2-ylcarbamothioylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=S)NC=4C=C5C=CC=CC5=CC=4)C(=O)O)=CC=C3OC2=C1 JQMYQNYDESVNOP-UHFFFAOYSA-N 0.000 claims description 3
FZOUYLLHFHPZDI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-naphthalen-1-yloxyacetyl)amino]hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)COC=4C5=CC=CC=C5C=CC=4)C(=O)O)=CC=C3OC2=C1 FZOUYLLHFHPZDI-UHFFFAOYSA-N 0.000 claims description 3
HMHKHUNQFYTFFA-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-phenylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=C1 HMHKHUNQFYTFFA-UHFFFAOYSA-N 0.000 claims description 3
ATAVAGZOGOKAAC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-3-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CN=C1 ATAVAGZOGOKAAC-UHFFFAOYSA-N 0.000 claims description 3
AUZKCSRJKIJLNS-UHFFFAOYSA-N 2-(dibenzothiophen-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C=1C=C2SC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC1=CC=CC=C1 AUZKCSRJKIJLNS-UHFFFAOYSA-N 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
YPOJAHGDLHWILP-IBGZPJMESA-N (2s)-2-(dibenzofuran-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)CC1=CC=CC=C1 YPOJAHGDLHWILP-IBGZPJMESA-N 0.000 claims description 2
XDLSSXYTUMNOHY-AWEZNQCLSA-N (3s)-3-[(dibenzofuran-2-ylsulfonylamino)methyl]-5-methylhexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC[C@@H](CC(C)C)CC(O)=O)=CC=C3OC2=C1 XDLSSXYTUMNOHY-AWEZNQCLSA-N 0.000 claims description 2
JENZVHXFRQGOFL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-2-phenylacetic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)C1=CC=CC=C1 JENZVHXFRQGOFL-UHFFFAOYSA-N 0.000 claims description 2
SJPXJSANXSAHSU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(4-fluorophenyl)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=C(F)C=C1 SJPXJSANXSAHSU-UHFFFAOYSA-N 0.000 claims description 2
OPOAKKGPPSNINL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(4-hydroxyphenyl)sulfanylpropanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CSC1=CC=C(O)C=C1 OPOAKKGPPSNINL-UHFFFAOYSA-N 0.000 claims description 2
YJHTYBHIRIYXAV-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(COC(C)(C)C)C(O)=O)=CC=C3OC2=C1 YJHTYBHIRIYXAV-UHFFFAOYSA-N 0.000 claims description 2
XUBNWLNTKGEZDX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-(3-oxo-1h-isoindol-2-yl)butanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCN4C(C5=CC=CC=C5C4)=O)C(=O)O)=CC=C3OC2=C1 XUBNWLNTKGEZDX-UHFFFAOYSA-N 0.000 claims description 2
ISOSRAWGMUBUMK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-methoxy-4-oxobutanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CC(=O)OC)C(O)=O)=CC=C3OC2=C1 ISOSRAWGMUBUMK-UHFFFAOYSA-N 0.000 claims description 2
SJNIHFRNNSGCOI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-pyridin-3-ylbutanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC1=CC=CN=C1 SJNIHFRNNSGCOI-UHFFFAOYSA-N 0.000 claims description 2
ROCYKAXXYZPTDJ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(1,3-dioxoisoindol-2-yl)pentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCN4C(C5=CC=CC=C5C4=O)=O)C(=O)O)=CC=C3OC2=C1 ROCYKAXXYZPTDJ-UHFFFAOYSA-N 0.000 claims description 2
AKGOCXPAZXSPOW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(2-methylbutylamino)-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NCC(C)CC)C(O)=O)=CC=C3OC2=C1 AKGOCXPAZXSPOW-UHFFFAOYSA-N 0.000 claims description 2
MGVBRGIBDNQMJT-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(3-oxo-1h-isoindol-2-yl)pentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCN4C(C5=CC=CC=C5C4)=O)C(=O)O)=CC=C3OC2=C1 MGVBRGIBDNQMJT-UHFFFAOYSA-N 0.000 claims description 2
MTRHSROQRITLBQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(4-methylpentan-2-ylamino)-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NC(C)CC(C)C)C(O)=O)=CC=C3OC2=C1 MTRHSROQRITLBQ-UHFFFAOYSA-N 0.000 claims description 2
RYZILWLNJLGPOW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(4-propylphenyl)pentanoic acid Chemical compound C1=CC(CCC)=CC=C1CCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 RYZILWLNJLGPOW-UHFFFAOYSA-N 0.000 claims description 2
WGWURNSXKJRMJU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[(2-methoxyphenyl)methylamino]-5-oxopentanoic acid Chemical compound COC1=CC=CC=C1CNC(=O)CCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 WGWURNSXKJRMJU-UHFFFAOYSA-N 0.000 claims description 2
PUWFHONXMCBSPN-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[(4-methylphenyl)sulfonylamino]pentanoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 PUWFHONXMCBSPN-UHFFFAOYSA-N 0.000 claims description 2
HDXHPZRRHOAZES-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[2-(dimethylamino)ethylamino]-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NCCN(C)C)C(O)=O)=CC=C3OC2=C1 HDXHPZRRHOAZES-UHFFFAOYSA-N 0.000 claims description 2
RGNKVAABSWEEKX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-phenylpentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCC1=CC=CC=C1 RGNKVAABSWEEKX-UHFFFAOYSA-N 0.000 claims description 2
SPMXDDSXZOVALA-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-pyridin-3-ylpentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCC1=CC=CN=C1 SPMXDDSXZOVALA-UHFFFAOYSA-N 0.000 claims description 2
YEPAWRGTEBVAEZ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenoxybutanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(O)=O)CCCCNC(=O)C(CC)OC1=CC=CC=C1 YEPAWRGTEBVAEZ-UHFFFAOYSA-N 0.000 claims description 2
NRXAXCZPWVAPDR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenylbutanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(O)=O)CCCCNC(=O)C(CC)C1=CC=CC=C1 NRXAXCZPWVAPDR-UHFFFAOYSA-N 0.000 claims description 2
KJFFSAMWNSAFLX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenylethenylsulfonylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C=CC1=CC=CC=C1 KJFFSAMWNSAFLX-UHFFFAOYSA-N 0.000 claims description 2
YXCUPVJSRBXQQZ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-phenylprop-2-enoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)C=CC1=CC=CC=C1 YXCUPVJSRBXQQZ-UHFFFAOYSA-N 0.000 claims description 2
GPSMOFOMKBFFPD-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-phenylpropanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCC1=CC=CC=C1 GPSMOFOMKBFFPD-UHFFFAOYSA-N 0.000 claims description 2
OOWMSOXRLQBHJU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-pyridin-4-ylpropanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCC1=CC=NC=C1 OOWMSOXRLQBHJU-UHFFFAOYSA-N 0.000 claims description 2
WMSIPIBCOFPIEL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(6-phenylhexanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCCCC1=CC=CC=C1 WMSIPIBCOFPIEL-UHFFFAOYSA-N 0.000 claims description 2
MKGITNAOWOTDLE-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(9h-fluoren-9-ylmethoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)OCC4C5=CC=CC=C5C5=CC=CC=C54)C(=O)O)=CC=C3OC2=C1 MKGITNAOWOTDLE-UHFFFAOYSA-N 0.000 claims description 2
MVDDWKMEAQHMRK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(phenylcarbamoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)NC1=CC=CC=C1 MVDDWKMEAQHMRK-UHFFFAOYSA-N 0.000 claims description 2
ALMQENWFOJJCQE-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(pyridin-3-ylcarbamothioylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=S)NC1=CC=CN=C1 ALMQENWFOJJCQE-UHFFFAOYSA-N 0.000 claims description 2
HOSXXBOASBEGAM-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-phenoxyacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=CC=C1 HOSXXBOASBEGAM-UHFFFAOYSA-N 0.000 claims description 2
SNDIGWWLXHMQSH-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-2-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=N1 SNDIGWWLXHMQSH-UHFFFAOYSA-N 0.000 claims description 2
JKSGPZSPMJSVPL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-4-ylsulfanylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CSC1=CC=NC=C1 JKSGPZSPMJSVPL-UHFFFAOYSA-N 0.000 claims description 2
WGQVBWGGZAEWDN-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-thiophen-2-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CS1 WGQVBWGGZAEWDN-UHFFFAOYSA-N 0.000 claims description 2
RXOISJMDLIMNAM-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(4-fluorophenyl)sulfonylamino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C1=CC=C(F)C=C1 RXOISJMDLIMNAM-UHFFFAOYSA-N 0.000 claims description 2
NNIRCQIXFDXRIO-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(4-methoxyphenyl)sulfonylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 NNIRCQIXFDXRIO-UHFFFAOYSA-N 0.000 claims description 2
DWHWANYQSULZPQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(2-methoxyphenyl)propanoylamino]hexanoic acid Chemical compound COC1=CC=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 DWHWANYQSULZPQ-UHFFFAOYSA-N 0.000 claims description 2
JAVKOMHYDZLWAO-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(3,4-dimethoxyphenyl)propanoylamino]hexanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 JAVKOMHYDZLWAO-UHFFFAOYSA-N 0.000 claims description 2
CUFKDYVIEIYECR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(4-methoxyphenyl)propanoylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 CUFKDYVIEIYECR-UHFFFAOYSA-N 0.000 claims description 2
GINOMQNFRZQUEU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(4-methylphenyl)propanoylamino]hexanoic acid Chemical compound C1=CC(C)=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 GINOMQNFRZQUEU-UHFFFAOYSA-N 0.000 claims description 2
KPBBBCKEUARNPU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[4-(1h-indol-3-yl)butanoylamino]hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)CCCC=4C5=CC=CC=C5NC=4)C(=O)O)=CC=C3OC2=C1 KPBBBCKEUARNPU-UHFFFAOYSA-N 0.000 claims description 2
OIRSIUQPVKOKCW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[[2-(3,4-dimethoxyphenyl)acetyl]amino]hexanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 OIRSIUQPVKOKCW-UHFFFAOYSA-N 0.000 claims description 2
BNMRYRLUFBNYFI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[[2-[2-(trifluoromethyl)phenyl]acetyl]amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=C1C(F)(F)F BNMRYRLUFBNYFI-UHFFFAOYSA-N 0.000 claims description 2
VPMDDYLEWAHAIQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-methoxy-6-oxohexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCC(=O)OC)C(O)=O)=CC=C3OC2=C1 VPMDDYLEWAHAIQ-UHFFFAOYSA-N 0.000 claims description 2
RUDZSTWVUDPCHC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-phenylhexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCC1=CC=CC=C1 RUDZSTWVUDPCHC-UHFFFAOYSA-N 0.000 claims description 2
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125000001425 triazolyl group Chemical group 0.000 description 1
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