CA2513115A1

CA2513115A1 - Amide and ester matrix metalloproteinase inhibitors

Amide and ester matrix metalloproteinase inhibitors Download PDF

Info

Publication number: CA2513115A1
Authority: CA; Canada
Prior art keywords: alkylenyl; alkyl; membered; compound; phenyl
Prior art date: 2003-01-17
Legal status : Abandoned

Application number

CA002513115A

Other languages

English (en)

French (fr)

Inventor

Amy Mae Bunker

Joseph Armand Picard

Current Assignee

Warner Lambert Co LLC

Original Assignee

Individual

Priority date

2003-01-17

Filing date

2004-01-06

Publication date

2004-08-05

2004-01-06 Application filed by Individual filed Critical Individual

2004-08-05 Publication of CA2513115A1 publication Critical patent/CA2513115A1/en

Status Abandoned legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title description 8
239000003771 matrix metalloproteinase inhibitor Substances 0.000 title description 4
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title description 4
150000002148 esters Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 390
150000003839 salts Chemical class 0.000 claims abstract description 110
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
201000010099 disease Diseases 0.000 claims abstract description 47
201000008482 osteoarthritis Diseases 0.000 claims abstract description 24
206010006187 Breast cancer Diseases 0.000 claims abstract description 14
208000026310 Breast neoplasm Diseases 0.000 claims abstract description 14
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 14
125000005466 alkylenyl group Chemical group 0.000 claims description 152
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 67
229910052757 nitrogen Inorganic materials 0.000 claims description 54
239000003814 drug Substances 0.000 claims description 47
229910020008 S(O) Inorganic materials 0.000 claims description 45
125000001424 substituent group Chemical group 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 34
229910052799 carbon Inorganic materials 0.000 claims description 33
229910052717 sulfur Inorganic materials 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 27
150000001721 carbon Chemical group 0.000 claims description 24
125000005842 heteroatom Chemical group 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 21
125000004434 sulfur atom Chemical group 0.000 claims description 19
125000004430 oxygen atom Chemical group O* 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 13
206010019280 Heart failures Diseases 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 8
208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 5
JNIUBAKGLCSMHL-UHFFFAOYSA-N 4-[[7-[[2-(4-methoxyphenyl)acetyl]amino]-1-oxoisoquinolin-2-yl]methyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(C=CN(CC=2C=CC(=CC=2)C(O)=O)C2=O)C2=C1 JNIUBAKGLCSMHL-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
FNOKXUZNEZKTID-UHFFFAOYSA-N 4-[[7-fluoro-6-[[2-(3-methoxyphenyl)acetyl]amino]-4-oxoquinazolin-3-yl]methyl]benzoic acid Chemical compound COC1=CC=CC(CC(=O)NC=2C(=CC3=C(C(N(CC=4C=CC(=CC=4)C(O)=O)C=N3)=O)C=2)F)=C1 FNOKXUZNEZKTID-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 2
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 2
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MGMNVFVZLKLAKI-UHFFFAOYSA-N 4-[[6-[[2-(3-methoxyphenyl)acetyl]amino]-4-oxoquinazolin-3-yl]methyl]benzoic acid Chemical compound COC1=CC=CC(CC(=O)NC=2C=C3C(=O)N(CC=4C=CC(=CC=4)C(O)=O)C=NC3=CC=2)=C1 MGMNVFVZLKLAKI-UHFFFAOYSA-N 0.000 claims description 2
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CWIDGUXFPGDYMT-UHFFFAOYSA-N 4-[[7-fluoro-6-[[2-(4-methoxyphenyl)acetyl]amino]-4-oxoquinazolin-3-yl]methyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC(C(N(CC=2C=CC(=CC=2)C(O)=O)C=N2)=O)=C2C=C1F CWIDGUXFPGDYMT-UHFFFAOYSA-N 0.000 claims description 2
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VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 2
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JDYPXRRUKLBIFN-UHFFFAOYSA-N 4-[[7-[[2-(4-fluorophenyl)acetyl]amino]-1-oxoisoquinolin-2-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(=O)C2=CC(NC(=O)CC=3C=CC(F)=CC=3)=CC=C2C=C1 JDYPXRRUKLBIFN-UHFFFAOYSA-N 0.000 claims 1
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