SK25499A3 - Phosphinic acid amides as matrix metalloprotease inhibitors - Google Patents

Phosphinic acid amides as matrix metalloprotease inhibitors Download PDF

Info

Publication number: SK25499A3
Authority: SK; Slovakia
Prior art keywords: alkyl; hydroxy; methylphenylphosphinyl; compound; compounds
Prior art date: 1996-08-28

Application number

SK254-99A

Other languages

English (en)

Slovak (sk)

Inventor

Stanislaw Pikul

Kelly L Mcdow-Dunham

Biswanath De

Yetunde O Taiwo

Original Assignee

Procter & Gamble

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.)

1996-08-28

Filing date

1997-08-22

Publication date

2000-03-13

1997-08-22 Application filed by Procter & Gamble filed Critical Procter & Gamble

2000-03-13 Publication of SK25499A3 publication Critical patent/SK25499A3/sk

Links

239000011159 matrix material Substances 0.000 title abstract description 7
239000003475 metalloproteinase inhibitor Substances 0.000 title description 6
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title 1
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108010006035 Metalloproteases Proteins 0.000 claims abstract description 75
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238000000034 method Methods 0.000 claims abstract description 53
230000000694 effects Effects 0.000 claims abstract description 40
201000010099 disease Diseases 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 13
150000003949 imides Chemical class 0.000 claims abstract description 7
-1 cycloheteroalkyl Chemical group 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
125000002837 carbocyclic group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
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125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
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125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
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OWBJNSLROHEGOK-UHFFFAOYSA-N 2-[diphenylphosphoryl(2-phenylethyl)amino]-n-hydroxyacetamide Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N(CC(=O)NO)CCC1=CC=CC=C1 OWBJNSLROHEGOK-UHFFFAOYSA-N 0.000 claims description 3
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JRHJGNASVCSYMA-UHFFFAOYSA-N methyl 2-[diphenylphosphoryl(2-phenylethyl)amino]acetate Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N(CC(=O)OC)CCC1=CC=CC=C1 JRHJGNASVCSYMA-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
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HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
206010033103 otosclerosis Diseases 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000007967 peppermint flavor Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
125000005541 phosphonamide group Chemical group 0.000 description 1
125000005499 phosphonyl group Chemical group 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007634 remodeling Methods 0.000 description 1
230000008439 repair process Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000037380 skin damage Effects 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
210000004988 splenocyte Anatomy 0.000 description 1
229940032147 starch Drugs 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000003718 tetrahydrofuranyl 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
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
239000010409 thin film Substances 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
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125000003944 tolyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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239000001993 wax Substances 0.000 description 1
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Classifications

- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
- 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
- A61K31/66—Phosphorus compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Biomedical Technology (AREA)
Dermatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK254-99A 1996-08-28 1997-08-22 Phosphinic acid amides as matrix metalloprotease inhibitors SK25499A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2476596P	1996-08-28	1996-08-28
PCT/US1997/014556 WO1998008853A1 (en)	1996-08-28	1997-08-22	Phosphinic acid amides as matrix metalloprotease inhibitors

Publications (1)

Publication Number	Publication Date
SK25499A3 true SK25499A3 (en)	2000-03-13

Family

ID=21822291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK254-99A SK25499A3 (en)	1996-08-28	1997-08-22	Phosphinic acid amides as matrix metalloprotease inhibitors

Country Status (27)

Country	Link
US (1)	US5830915A (de)
EP (1)	EP0925303B1 (de)
JP (1)	JP3539736B2 (de)
KR (1)	KR20000035925A (de)
CN (1)	CN1228780A (de)
AR (1)	AR009357A1 (de)
AT (1)	ATE226590T1 (de)
AU (1)	AU732653B2 (de)
BR (1)	BR9713182A (de)
CA (1)	CA2264254C (de)
CO (1)	CO4900033A1 (de)
CZ (1)	CZ63699A3 (de)
DE (1)	DE69716619T2 (de)
DK (1)	DK0925303T3 (de)
HU (1)	HUP9903916A3 (de)
ID (1)	ID18145A (de)
IL (1)	IL128668A (de)
NO (1)	NO990857L (de)
NZ (1)	NZ334258A (de)
PE (1)	PE107698A1 (de)
PL (1)	PL331854A1 (de)
RU (1)	RU2170232C2 (de)
SK (1)	SK25499A3 (de)
TR (1)	TR199900399T2 (de)
TW (1)	TW518338B (de)
WO (1)	WO1998008853A1 (de)
ZA (1)	ZA977700B (de)

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US6693099B2 (en) *	2000-10-17	2004-02-17	The Procter & Gamble Company	Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
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1997
- 1997-08-22 AT AT97939444T patent/ATE226590T1/de not_active IP Right Cessation
- 1997-08-22 SK SK254-99A patent/SK25499A3/sk unknown
- 1997-08-22 EP EP97939444A patent/EP0925303B1/de not_active Expired - Lifetime
- 1997-08-22 PL PL97331854A patent/PL331854A1/xx unknown
- 1997-08-22 TR TR1999/00399T patent/TR199900399T2/xx unknown
- 1997-08-22 BR BR9713182-2A patent/BR9713182A/pt unknown
- 1997-08-22 CA CA002264254A patent/CA2264254C/en not_active Expired - Fee Related
- 1997-08-22 KR KR1019997001661A patent/KR20000035925A/ko not_active Abandoned
- 1997-08-22 JP JP51171698A patent/JP3539736B2/ja not_active Expired - Fee Related
- 1997-08-22 CN CN97197546A patent/CN1228780A/zh active Pending
- 1997-08-22 DE DE69716619T patent/DE69716619T2/de not_active Expired - Fee Related
- 1997-08-22 CZ CZ99636A patent/CZ63699A3/cs unknown
- 1997-08-22 AU AU41531/97A patent/AU732653B2/en not_active Ceased
- 1997-08-22 RU RU99106245/04A patent/RU2170232C2/ru active
- 1997-08-22 WO PCT/US1997/014556 patent/WO1998008853A1/en not_active Ceased
- 1997-08-22 NZ NZ334258A patent/NZ334258A/xx unknown
- 1997-08-22 HU HU9903916A patent/HUP9903916A3/hu unknown
- 1997-08-22 DK DK97939444T patent/DK0925303T3/da active
- 1997-08-22 IL IL12866897A patent/IL128668A/en not_active IP Right Cessation
- 1997-08-26 US US08/918,950 patent/US5830915A/en not_active Expired - Fee Related
- 1997-08-27 CO CO97049512A patent/CO4900033A1/es unknown
- 1997-08-27 ZA ZA9707700A patent/ZA977700B/xx unknown
- 1997-08-27 AR ARP970103898A patent/AR009357A1/es unknown
- 1997-08-28 ID IDP972999A patent/ID18145A/id unknown
- 1997-08-28 PE PE1997000765A patent/PE107698A1/es not_active Application Discontinuation
1998
- 1998-02-03 TW TW087101222A patent/TW518338B/zh active
1999
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Also Published As

Publication number	Publication date
JP2000515167A (ja)	2000-11-14
CA2264254C (en)	2003-03-11
RU2170232C2 (ru)	2001-07-10
TR199900399T2 (xx)	1999-06-21
DE69716619D1 (en)	2002-11-28
ATE226590T1 (de)	2002-11-15
CN1228780A (zh)	1999-09-15
NZ334258A (en)	2000-11-24
HUP9903916A2 (hu)	2001-05-28
AR009357A1 (es)	2000-04-12
TW518338B (en)	2003-01-21
NO990857L (no)	1999-04-28
DE69716619T2 (de)	2003-06-26
CA2264254A1 (en)	1998-03-05
EP0925303B1 (de)	2002-10-23
IL128668A (en)	2002-02-10
ID18145A (id)	1998-03-05
JP3539736B2 (ja)	2004-07-07
WO1998008853A1 (en)	1998-03-05
AU4153197A (en)	1998-03-19
IL128668A0 (en)	2000-01-31
BR9713182A (pt)	1999-11-03
ZA977700B (en)	1998-02-23
CO4900033A1 (es)	2000-03-27
DK0925303T3 (da)	2003-02-24
AU732653B2 (en)	2001-04-26
EP0925303A1 (de)	1999-06-30
PL331854A1 (en)	1999-08-16
PE107698A1 (es)	1999-02-11
CZ63699A3 (cs)	1999-07-14
NO990857D0 (no)	1999-02-23
US5830915A (en)	1998-11-03
HUP9903916A3 (en)	2001-06-28
KR20000035925A (ko)	2000-06-26

Publication	Publication Date	Title
EP0925303B1 (de)	2002-10-23	Phosphinsäureamide als matrix metalloprotease inhibitoren
US6469000B1 (en)	2002-10-22	1,3-diheterocyclic metalloprotease inhibitors
JP3347331B2 (ja)	2002-11-20	複素環式メタロプロテアーゼ阻害剤
AU731319B2 (en)	2001-03-29	Heterocyclic metalloprotease inhibitors
WO1998008853A9 (en)	1998-08-06	Phosphinic acid amides as matrix metalloprotease inhibitors
KR100352316B1 (ko)	2002-09-12	메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체
AU4074097A (en)	1998-03-19	Bidentate metalloprotease inhibitors
MXPA99002064A (en)	1999-09-20	Heterocyclic metalloprotease inhibitors
MXPA99002067A (en)	1999-09-20	Heterocyclic metalloprotease inhibitors
MXPA99002065A (en)	1999-09-20	Bidentate metalloprotease inhibitors
MXPA99002066A (en)	1999-09-20	1,3-diheterocyclic metalloprotease inhibitors