SK73898A3 - Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation - Google Patents

Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation Download PDF

Info

Publication number: SK73898A3
Authority: SK; Slovakia
Prior art keywords: group; formula; compound; salt; solvate
Prior art date: 1995-12-08

Application number

SK738-98A

Other languages

English (en)

Slovak (sk)

Inventor

Scott E Zook

Raymond Dagnino Jr

Michael E Deason

Steven L Bender

Michael J Melnick

Original Assignee

Agouron Pharma

Priority date (The priority date 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 date listed.)

1995-12-08

Filing date

1996-12-05

Publication date

1999-01-11

1996-12-05 Application filed by Agouron Pharma filed Critical Agouron Pharma

1999-01-11 Publication of SK73898A3 publication Critical patent/SK73898A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 93
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims description 30
239000000543 intermediate Substances 0.000 title abstract description 19
239000003475 metalloproteinase inhibitor Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 384
150000003839 salts Chemical class 0.000 claims abstract description 188
239000012453 solvate Substances 0.000 claims abstract description 153
125000003118 aryl group Chemical group 0.000 claims abstract description 131
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 95
229910052717 sulfur Inorganic materials 0.000 claims abstract description 92
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 89
229910052760 oxygen Inorganic materials 0.000 claims abstract description 49
229940002612 prodrug Drugs 0.000 claims abstract description 49
239000000651 prodrug Substances 0.000 claims abstract description 49
125000001424 substituent group Chemical group 0.000 claims abstract description 37
230000000694 effects Effects 0.000 claims abstract description 19
102000005741 Metalloproteases Human genes 0.000 claims abstract description 17
108010006035 Metalloproteases Proteins 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
125000006413 ring segment Chemical group 0.000 claims abstract description 12
125000005842 heteroatom Chemical group 0.000 claims abstract description 7
230000002401 inhibitory effect Effects 0.000 claims abstract description 7
-1 atom halogen Chemical group 0.000 claims description 149
125000000217 alkyl group Chemical group 0.000 claims description 135
229910052739 hydrogen Inorganic materials 0.000 claims description 135
125000000753 cycloalkyl group Chemical group 0.000 claims description 112
229910052799 carbon Inorganic materials 0.000 claims description 111
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 100
238000006243 chemical reaction Methods 0.000 claims description 85
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 6
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125000002883 imidazolyl group Chemical group 0.000 claims description 3
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QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
229940126062 Compound A Drugs 0.000 claims description 2
YZPAAVWSSLURLW-SFHVURJKSA-N FC1=CC=C(C=C1)SC1=CC=C(C=C1)S(=O)(=O)N1[C@H](C(N(CC1)C)(C)C)C(=O)NO Chemical compound FC1=CC=C(C=C1)SC1=CC=C(C=C1)S(=O)(=O)N1[C@H](C(N(CC1)C)(C)C)C(=O)NO YZPAAVWSSLURLW-SFHVURJKSA-N 0.000 claims description 2
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206010064390 Tumour invasion Diseases 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
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125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 2
BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
WKTXPBWQJVRRAX-QGZVFWFLSA-N (2r)-1-[4-(4-fluorophenoxy)phenyl]sulfonyl-n-hydroxy-4-methylsulfonylpiperazine-2-carboxamide Chemical compound ONC(=O)[C@H]1CN(S(=O)(=O)C)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 WKTXPBWQJVRRAX-QGZVFWFLSA-N 0.000 claims 1
ISTJVAJHLXMVBD-UHFFFAOYSA-N CN1C(CCCS1)(C(=O)N)S(=O)(=O)C2=CC=CC=C2 Chemical compound CN1C(CCCS1)(C(=O)N)S(=O)(=O)C2=CC=CC=C2 ISTJVAJHLXMVBD-UHFFFAOYSA-N 0.000 claims 1
FMPVEIUPAZXXEY-SFHVURJKSA-N ClC1=CC=C(C=C1)SC1=CC=C(C=C1)S(=O)(=O)N1[C@H](C(N(CC1)C)(C)C)C(=O)NO Chemical compound ClC1=CC=C(C=C1)SC1=CC=C(C=C1)S(=O)(=O)N1[C@H](C(N(CC1)C)(C)C)C(=O)NO FMPVEIUPAZXXEY-SFHVURJKSA-N 0.000 claims 1
VXNFIOQAEMVPSG-KRWDZBQOSA-N ONC(=O)[C@H]1C(C)(C)NCCN1S(=O)(=O)C(C=C1)=CC=C1SC1=CC=C(F)C=C1 Chemical compound ONC(=O)[C@H]1C(C)(C)NCCN1S(=O)(=O)C(C=C1)=CC=C1SC1=CC=C(F)C=C1 VXNFIOQAEMVPSG-KRWDZBQOSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 360
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000003134 recirculating effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000002165 resonance energy transfer Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
150000005376 secondary alkyl halides Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
210000002435 tendon Anatomy 0.000 description 1
NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
GGYHHNNUXVNXOD-FQEVSTJZSA-N tert-butyl (2s)-2-[[4-(4-bromophenoxy)phenyl]sulfonylamino]-3-(2-hydroxyethylsulfanyl)-3-methylbutanoate Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(=O)OC(C)(C)C)C(C)(C)SCCO)=CC=C1OC1=CC=C(Br)C=C1 GGYHHNNUXVNXOD-FQEVSTJZSA-N 0.000 description 1
KLNGJOPYFVWJDS-LJQANCHMSA-N tert-butyl (3r)-4-[4-(4-fluorophenoxy)phenyl]sulfonyl-3-(hydroxycarbamoyl)piperazine-1-carboxylate Chemical compound ONC(=O)[C@H]1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 KLNGJOPYFVWJDS-LJQANCHMSA-N 0.000 description 1
SUXHUKREMWJVSY-UHFFFAOYSA-N tert-butyl thiomorpholine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1CSCCN1 SUXHUKREMWJVSY-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical class OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
230000008354 tissue degradation Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000002993 trophoblast Anatomy 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000007966 viscous suspension Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- C07D417/02—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

SK738-98A 1995-12-08 1996-12-05 Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation SK73898A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US56976695A	1995-12-08	1995-12-08
PCT/US1996/019328 WO1997020824A1 (en)	1995-12-08	1996-12-05	Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation

Publications (1)

Publication Number	Publication Date
SK73898A3 true SK73898A3 (en)	1999-01-11

Family

ID=24276764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK738-98A SK73898A3 (en)	1995-12-08	1996-12-05	Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation

Country Status (39)

Country	Link
US (1)	US6153757A (xx)
EP (2)	EP0874830B1 (xx)
JP (1)	JP2000502330A (xx)
KR (1)	KR19990072009A (xx)
CN (2)	CN1542002A (xx)
AP (2)	AP1288A (xx)
AT (2)	ATE283264T1 (xx)
AU (1)	AU725831C (xx)
BG (1)	BG64279B1 (xx)
BR (1)	BR9611929A (xx)
CA (1)	CA2238306A1 (xx)
CO (1)	CO4790150A1 (xx)
CZ (1)	CZ292942B6 (xx)
DE (2)	DE69626684T2 (xx)
DK (1)	DK0874830T3 (xx)
EA (1)	EA003294B1 (xx)
ES (2)	ES2195034T3 (xx)
GE (1)	GEP20012388B (xx)
GT (2)	GT199700015AA (xx)
HR (1)	HRP970031A2 (xx)
HU (1)	HUP9902092A3 (xx)
ID (1)	ID17624A (xx)
IL (6)	IL138027A (xx)
MX (1)	MX9804457A (xx)
MY (1)	MY117290A (xx)
NO (1)	NO311360B1 (xx)
NZ (1)	NZ325559A (xx)
OA (1)	OA10794A (xx)
PA (1)	PA8431301A1 (xx)
PE (1)	PE69298A1 (xx)
PL (1)	PL327275A1 (xx)
PT (1)	PT874830E (xx)
SI (1)	SI0874830T1 (xx)
SK (1)	SK73898A3 (xx)
SV (1)	SV1997000008A (xx)
TR (1)	TR199800990T2 (xx)
TW (1)	TW546293B (xx)
WO (1)	WO1997020824A1 (xx)
YU (1)	YU21597A (xx)

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US6087359A (en) *	1997-03-04	2000-07-11	Getman; Daniel P.	Thioaryl sulfonamide hydroxamic acid compounds
JP2002513409A (ja) *	1997-03-04	2002-05-08	モンサントカンパニー	アミド芳香環スルホンアミドヒドロキサム酸化合物
US7115632B1 (en)	1999-05-12	2006-10-03	G. D. Searle & Co.	Sulfonyl aryl or heteroaryl hydroxamic acid compounds
US6638952B1 (en)	1997-03-04	2003-10-28	Pharmacia Corporation	Aromatic sulfonyl alpha-cycloamino hydroxamic acid compounds
ES2206903T3 (es)	1997-03-04	2004-05-16	Monsanto Company	Compuestos sulfonilicos divalentes de acido aril o heteroaril-hidroxamco.
NZ338082A (en) *	1997-04-01	2000-06-23	Agouron Pharma	Metalloproteinase and Tumor Necrosis Factor-alpha convertase inhibitors, pharmaceutical compositions and their use in treating disease mediated by metalloproteinase activity.
US5985900A (en) *	1997-04-01	1999-11-16	Agouron Pharmaceuticals, Inc.	Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses
AU7294098A (en) *	1997-05-09	1998-11-27	Agouron Pharmaceuticals, Inc.	Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses
JP2004137284A (ja) *	1997-06-17	2004-05-13	Kaken Pharmaceut Co Ltd	２−スルファモイル安息香酸誘導体
CN1265647A (zh)	1997-07-31	2000-09-06	普罗克特和甘保尔公司	无环金属蛋白酶抑制剂
US6403632B1 (en) *	2000-03-01	2002-06-11	Bristol Myers Squibb Pharma Co	Lactam metalloprotease inhibitors
JPH11199512A (ja) *	1997-10-24	1999-07-27	Pfizer Prod Inc	変形性関節症および他のｍｍｐ媒介疾患の治療のためのｍｍｐ−１３選択的阻害剤の使用
US20010039287A1 (en)	1997-11-14	2001-11-08	Thomas E Barta	Aromatic sulfone hydroxamic acid metalloprotease inhibitor
RU2250105C2 (ru)	1997-11-14	2005-04-20	Дж.Д.Сёрл ЛЛС	Ароматическая сульфонгидроксамовая кислота в качестве ингибитора металлопротеаз
US6750228B1 (en)	1997-11-14	2004-06-15	Pharmacia Corporation	Aromatic sulfone hydroxamic acid metalloprotease inhibitor
KR20010034406A (ko) *	1998-01-27	2001-04-25	아메리칸 사이아나미드 컴파니	매트릭스 메탈로프로테인아제 억제제로서의2,3,4,5-테트라하이드로-1ｈ-[1,4]-벤조디아제핀-3-하이드록삼산
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1996
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Also Published As

Publication number	Publication date
HUP9902092A3 (en)	2000-12-28
SV1997000008A (es)	1999-02-15
PT874830E (pt)	2003-06-30
AU725831B2 (en)	2000-10-19
PL327275A1 (en)	1998-12-07
AU725831C (en)	2002-10-17
NO982590D0 (no)	1998-06-05
EP0874830B1 (en)	2003-03-12
DE69626684D1 (de)	2003-04-17
OA10794A (en)	2001-07-05
EA199800541A1 (ru)	1998-12-24
US6153757A (en)	2000-11-28
AU1409197A (en)	1997-06-27
EP1095936A1 (en)	2001-05-02
ATE234291T1 (de)	2003-03-15
BG102510A (en)	1999-08-31
JP2000502330A (ja)	2000-02-29
TW546293B (en)	2003-08-11
ATE283264T1 (de)	2004-12-15
DE69633947D1 (de)	2004-12-30
DE69626684T2 (de)	2004-04-29
BR9611929A (pt)	1999-05-18
IL138028A0 (en)	2001-10-31
IL124559A0 (en)	1998-12-06
KR19990072009A (ko)	1999-09-27
CN1542002A (zh)	2004-11-03
IL124559A (en)	2004-07-25
DK0874830T3 (da)	2003-04-22
CO4790150A1 (es)	1999-05-31
PE69298A1 (es)	1998-11-13
ID17624A (id)	1998-01-15
MX9804457A (es)	1998-09-30
TR199800990T2 (xx)	1998-07-21
IL134816A (en)	2003-02-12
EA003294B1 (ru)	2003-04-24
GT199700015A (es)	1998-07-23
DE69633947T2 (de)	2005-12-01
CA2238306A1 (en)	1997-06-12
IL138027A (en)	2004-08-31
CN1207289C (zh)	2005-06-22
AP2001002270A0 (en)	2001-09-30
BG64279B1 (bg)	2004-08-31
HRP970031A2 (en)	1998-08-31
GT199700015AA (es)	1998-07-23
MY117290A (en)	2004-06-30
NO982590L (no)	1998-08-05
WO1997020824A1 (en)	1997-06-12
IL143674A0 (en)	2002-04-21
NZ325559A (en)	2000-01-28
SI0874830T1 (en)	2003-08-31
ES2195034T3 (es)	2003-12-01
GEP20012388B (en)	2001-03-25
CN1207734A (zh)	1999-02-10
EP1095936B1 (en)	2004-11-24
ES2233275T3 (es)	2005-06-16
CZ173398A3 (cs)	1998-11-11
HUP9902092A2 (hu)	1999-09-28
AP1288A (en)	2004-07-21
IL134816A0 (en)	2001-05-20
AP1368A (en)	2005-04-21
PA8431301A1 (es)	2000-05-24
IL138027A0 (en)	2001-10-31
AP9801284A0 (en)	1998-09-30
NO311360B1 (no)	2001-11-19
EP0874830A1 (en)	1998-11-04
YU21597A (en)	1999-11-22
CZ292942B6 (cs)	2004-01-14

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