CA2080228A1 - Phosphonopeptides with collagenase inhibiting activity - Google Patents
Phosphonopeptides with collagenase inhibiting activityInfo
- Publication number
- CA2080228A1 CA2080228A1 CA002080228A CA2080228A CA2080228A1 CA 2080228 A1 CA2080228 A1 CA 2080228A1 CA 002080228 A CA002080228 A CA 002080228A CA 2080228 A CA2080228 A CA 2080228A CA 2080228 A1 CA2080228 A1 CA 2080228A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- leucyl
- phosphonopropyl
- hydrogen
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 108060005980 Collagenase Proteins 0.000 title description 11
- 102000029816 Collagenase Human genes 0.000 title description 11
- 229960002424 collagenase Drugs 0.000 title description 5
- 230000002401 inhibitory effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 136
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- -1 C2-6alkanoyl Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
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- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
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- RQNKISSEPZPZDA-BZSNNMDCSA-N [(1s)-1-[[(2s)-4-methyl-1-oxo-1-[[(9s)-8-oxo-1,7-diazacyclotridec-9-yl]amino]pentan-2-yl]amino]propyl]phosphonic acid Chemical compound CC[C@H](P(O)(O)=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CCCCNCCCCCNC1=O RQNKISSEPZPZDA-BZSNNMDCSA-N 0.000 claims 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 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
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB909008065A GB9008065D0 (en) | 1990-04-10 | 1990-04-10 | Novel compounds |
GB9008065.6 | 1990-04-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2080228A1 true CA2080228A1 (en) | 1991-10-11 |
Family
ID=10674178
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002080228A Abandoned CA2080228A1 (en) | 1990-04-10 | 1991-04-05 | Phosphonopeptides with collagenase inhibiting activity |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0527761A1 (de) |
JP (1) | JPH05506651A (de) |
AU (1) | AU637903B2 (de) |
CA (1) | CA2080228A1 (de) |
GB (1) | GB9008065D0 (de) |
IE (1) | IE911165A1 (de) |
NZ (1) | NZ237732A (de) |
PT (1) | PT97281A (de) |
WO (1) | WO1991015506A1 (de) |
ZA (1) | ZA912574B (de) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0520573A1 (de) * | 1991-06-27 | 1992-12-30 | Glaxo Inc. | Derivate von cyclischen Imiden |
GB9122859D0 (en) * | 1991-10-28 | 1991-12-11 | Smithkline Beecham Plc | Novel compounds |
US5326760A (en) * | 1992-06-29 | 1994-07-05 | Glaxo, Inc. | Aminobutanoic acid compounds having metalloprotease inhibiting properties |
US5831004A (en) * | 1994-10-27 | 1998-11-03 | Affymax Technologies N.V. | Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use |
US5840698A (en) * | 1994-10-27 | 1998-11-24 | Affymax Technologies N.V. | Inhibitors of collagenase-1 and stormelysin-I metalloproteases, pharmaceutical compositions comprising same and methods of their use |
US5827840A (en) * | 1996-08-01 | 1998-10-27 | The Research Foundation Of State University Of New York | Promotion of wound healing by chemically-modified tetracyclines |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8726714D0 (en) * | 1987-11-14 | 1987-12-16 | Beecham Group Plc | Compounds |
EP0401963A1 (de) * | 1989-04-13 | 1990-12-12 | Beecham Group p.l.c. | Phosphonopeptide mit kollagenase-inhibitierender Wirkung |
-
1990
- 1990-04-10 GB GB909008065A patent/GB9008065D0/en active Pending
-
1991
- 1991-04-05 WO PCT/GB1991/000529 patent/WO1991015506A1/en not_active Application Discontinuation
- 1991-04-05 JP JP91506973A patent/JPH05506651A/ja active Pending
- 1991-04-05 CA CA002080228A patent/CA2080228A1/en not_active Abandoned
- 1991-04-05 EP EP91907169A patent/EP0527761A1/de not_active Ceased
- 1991-04-05 AU AU76502/91A patent/AU637903B2/en not_active Ceased
- 1991-04-08 NZ NZ237732A patent/NZ237732A/xx unknown
- 1991-04-08 PT PT97281A patent/PT97281A/pt not_active Application Discontinuation
- 1991-04-08 ZA ZA912574A patent/ZA912574B/xx unknown
- 1991-04-08 IE IE116591A patent/IE911165A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
EP0527761A1 (de) | 1993-02-24 |
WO1991015506A1 (en) | 1991-10-17 |
NZ237732A (en) | 1993-08-26 |
GB9008065D0 (en) | 1990-06-06 |
ZA912574B (en) | 1992-10-28 |
AU637903B2 (en) | 1993-06-10 |
PT97281A (pt) | 1992-01-31 |
IE911165A1 (en) | 1991-10-23 |
AU7650291A (en) | 1991-10-30 |
JPH05506651A (ja) | 1993-09-30 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Dead |