SK25799A3 - Heterocyclic metalloprotease inhibitors - Google Patents

Heterocyclic metalloprotease inhibitors Download PDF

Info

Publication number: SK25799A3
Authority: SK; Slovakia
Prior art keywords: alkyl; group; compounds; heteroatom; aromatic heterocycle
Prior art date: 1996-08-28

Application number

SK257-99A

Other languages

English (en)

Slovak (sk)

Inventor

Stanislaw Pikul

Kelly L Mcdow-Dunham

Biswanath De

Yetunde O Taiwo

Neil G Almstead

Rimma S Bradley

Michael G Natchus

Thomas L Cupps

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

1999-12-10

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

1999-12-10 Publication of SK25799A3 publication Critical patent/SK25799A3/sk

Links

125000000623 heterocyclic group Chemical group 0.000 title claims description 29
239000003475 metalloproteinase inhibitor Substances 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 170
102000005741 Metalloproteases Human genes 0.000 claims abstract description 74
108010006035 Metalloproteases Proteins 0.000 claims abstract description 74
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 63
201000010099 disease Diseases 0.000 claims abstract description 37
230000000694 effects Effects 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 10
150000002148 esters Chemical class 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
150000001408 amides Chemical class 0.000 claims abstract description 7
150000003949 imides Chemical class 0.000 claims abstract description 6
-1 heteroatom-alkyl Chemical group 0.000 claims description 62
125000000217 alkyl group Chemical group 0.000 claims description 53
238000011282 treatment Methods 0.000 claims description 42
125000003118 aryl group Chemical group 0.000 claims description 41
238000002360 preparation method Methods 0.000 claims description 28
125000005842 heteroatom Chemical group 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 15
125000004104 aryloxy group Chemical group 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000001769 aryl amino group Chemical group 0.000 claims description 11
125000004947 alkyl aryl amino group Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
229910052727 yttrium Inorganic materials 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004986 diarylamino group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000003003 spiro group Chemical group 0.000 claims description 3
206010006895 Cachexia Diseases 0.000 claims description 2
101710170181 Metalloproteinase inhibitor Proteins 0.000 claims description 2
229910052736 halogen Chemical group 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
229940126170 metalloproteinase inhibitor Drugs 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
208000035475 disorder Diseases 0.000 abstract description 27
239000003112 inhibitor Substances 0.000 abstract description 26
230000003287 optical effect Effects 0.000 abstract description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000000753 cycloalkyl group Chemical group 0.000 description 18
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241000282414 Homo sapiens Species 0.000 description 8
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206010028980 Neoplasm Diseases 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
239000003937 drug carrier Substances 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
239000000600 sorbitol Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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125000003277 amino group Chemical group 0.000 description 7
239000003446 ligand Substances 0.000 description 7
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LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
102000002274 Matrix Metalloproteinases Human genes 0.000 description 6
108010000684 Matrix Metalloproteinases Proteins 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
229930006000 Sucrose Natural products 0.000 description 6
230000033228 biological regulation Effects 0.000 description 6
125000002837 carbocyclic group Chemical group 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000003086 colorant Substances 0.000 description 6
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235000019634 flavors Nutrition 0.000 description 6
235000013355 food flavoring agent Nutrition 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
102000029816 Collagenase Human genes 0.000 description 5
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QXXUBPGYFQRIOA-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3h-diazepine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1N(C(O)=O)CC=CC=C1 QXXUBPGYFQRIOA-UHFFFAOYSA-N 0.000 description 4
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239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 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
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WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
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Classifications

- 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/06—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK257-99A 1996-08-28 1997-08-22 Heterocyclic metalloprotease inhibitors SK25799A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2484696P	1996-08-28	1996-08-28
PCT/US1997/014553 WO1998008823A1 (en)	1996-08-28	1997-08-22	Heterocyclic metalloprotease inhibitors

Publications (1)

Publication Number	Publication Date
SK25799A3 true SK25799A3 (en)	1999-12-10

Family

ID=21822698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK257-99A SK25799A3 (en)	1996-08-28	1997-08-22	Heterocyclic metalloprotease inhibitors

Country Status (25)

Country	Link
US (2)	US6121258A (tr)
EP (1)	EP0923561B1 (tr)
JP (1)	JP3347331B2 (tr)
KR (1)	KR20000035920A (tr)
CN (1)	CN1228772A (tr)
AR (1)	AR009457A1 (tr)
AT (1)	ATE226573T1 (tr)
AU (1)	AU734834B2 (tr)
BR (1)	BR9712085A (tr)
CA (1)	CA2263917A1 (tr)
CO (1)	CO4920240A1 (tr)
CZ (1)	CZ62699A3 (tr)
DE (1)	DE69716615T2 (tr)
DK (1)	DK0923561T3 (tr)
HU (1)	HUP0000210A3 (tr)
ID (1)	ID18416A (tr)
IL (1)	IL128664A (tr)
NO (1)	NO314934B1 (tr)
NZ (1)	NZ334254A (tr)
PE (1)	PE2599A1 (tr)
PL (1)	PL331795A1 (tr)
SK (1)	SK25799A3 (tr)
TR (1)	TR199900382T2 (tr)
WO (1)	WO1998008823A1 (tr)
ZA (1)	ZA977696B (tr)

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US6340691B1 (en)	1999-01-27	2002-01-22	American Cyanamid Company	Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors
US6358980B1 (en)	1999-01-27	2002-03-19	American Cyanamid Company	Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
US6544984B1 (en)	1999-01-27	2003-04-08	American Cyanamid Company	2,3,4,5-tetrahydro-1H-(1,4)benzodiazepine-3-hydroxamic acids
MXPA01008857A (es)	1999-03-03	2002-07-02	Procter & Gamble	Inhibidores de metaloproteasa dihetero sustituidos.
BR0008716A (pt)	1999-03-03	2002-09-24	Procter & Gamble	Inibidores de metaloprotease contendo alquenil ou alquinil
CA2400862A1 (en) *	2000-02-21	2001-08-23	Noriko Mukai	Thiazepinyl hydroxamic acid derivatives as matrix metalloproteinase inhibitors
US8283135B2 (en)	2000-06-30	2012-10-09	The Procter & Gamble Company	Oral care compositions containing combinations of anti-bacterial and host-response modulating agents
MXPA03000043A (es)	2000-06-30	2003-10-15	Procter & Gamble	Promocion de la salud en todo el cuerpo.
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1997
- 1997-08-22 AT AT97939443T patent/ATE226573T1/de not_active IP Right Cessation
- 1997-08-22 PL PL97331795A patent/PL331795A1/xx unknown
- 1997-08-22 DK DK97939443T patent/DK0923561T3/da active
- 1997-08-22 CZ CZ99626A patent/CZ62699A3/cs unknown
- 1997-08-22 WO PCT/US1997/014553 patent/WO1998008823A1/en not_active Ceased
- 1997-08-22 CN CN97197544A patent/CN1228772A/zh active Pending
- 1997-08-22 TR TR1999/00382T patent/TR199900382T2/tr unknown
- 1997-08-22 IL IL12866497A patent/IL128664A/xx not_active IP Right Cessation
- 1997-08-22 JP JP51171398A patent/JP3347331B2/ja not_active Expired - Fee Related
- 1997-08-22 BR BR9712085-5A patent/BR9712085A/pt unknown
- 1997-08-22 KR KR1019997001656A patent/KR20000035920A/ko not_active Ceased
- 1997-08-22 CA CA002263917A patent/CA2263917A1/en not_active Abandoned
- 1997-08-22 SK SK257-99A patent/SK25799A3/sk unknown
- 1997-08-22 HU HU0000210A patent/HUP0000210A3/hu unknown
- 1997-08-22 AU AU41530/97A patent/AU734834B2/en not_active Ceased
- 1997-08-22 NZ NZ334254A patent/NZ334254A/xx unknown
- 1997-08-22 DE DE69716615T patent/DE69716615T2/de not_active Expired - Fee Related
- 1997-08-22 EP EP97939443A patent/EP0923561B1/en not_active Expired - Lifetime
- 1997-08-26 US US08/918,957 patent/US6121258A/en not_active Expired - Fee Related
- 1997-08-27 AR ARP970103902A patent/AR009457A1/es unknown
- 1997-08-27 ZA ZA9707696A patent/ZA977696B/xx unknown
- 1997-08-27 CO CO97049501A patent/CO4920240A1/es unknown
- 1997-08-28 PE PE1997000767A patent/PE2599A1/es not_active Application Discontinuation
- 1997-08-28 ID IDP972993A patent/ID18416A/id unknown
1999
- 1999-02-18 NO NO19990759A patent/NO314934B1/no not_active IP Right Cessation
2000
- 2000-03-01 US US09/516,726 patent/US6399598B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP3347331B2 (ja)	2002-11-20
PE2599A1 (es)	1999-03-03
WO1998008823A1 (en)	1998-03-05
AR009457A1 (es)	2000-04-26
HUP0000210A2 (hu)	2001-04-28
CZ62699A3 (cs)	1999-07-14
DE69716615T2 (de)	2003-06-18
ID18416A (id)	1998-04-09
US6121258A (en)	2000-09-19
PL331795A1 (en)	1999-08-02
AU4153097A (en)	1998-03-19
EP0923561B1 (en)	2002-10-23
US6399598B1 (en)	2002-06-04
CA2263917A1 (en)	1998-03-05
NZ334254A (en)	2000-11-24
NO990759L (no)	1999-04-27
NO314934B1 (no)	2003-06-16
BR9712085A (pt)	2000-10-24
ZA977696B (en)	1998-02-23
KR20000035920A (ko)	2000-06-26
IL128664A0 (en)	2000-01-31
CN1228772A (zh)	1999-09-15
AU734834B2 (en)	2001-06-21
DK0923561T3 (da)	2003-02-24
HUP0000210A3 (en)	2001-07-30
NO990759D0 (no)	1999-02-18
DE69716615D1 (de)	2002-11-28
TR199900382T2 (tr)	1999-05-21
IL128664A (en)	2003-07-06
ATE226573T1 (de)	2002-11-15
JP2000516953A (ja)	2000-12-19
CO4920240A1 (es)	2000-05-29
EP0923561A1 (en)	1999-06-23

Publication	Publication Date	Title
SK25799A3 (en)	1999-12-10	Heterocyclic metalloprotease inhibitors
KR100352316B1 (ko)	2002-09-12	메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체
DE69716934T2 (de)	2003-07-31	1,3-diheterozyklische metalloprotease inhibitoren
KR100339296B1 (ko)	2002-06-03	헤테로고리성 메탈로프로테아제 억제제
SK25099A3 (en)	2000-02-14	Substituted cyclic amine metalloprotease inhibitors
EP0927183B1 (en)	2004-07-28	Spirocyclic metalloprotease inhibitors
SK15462000A3 (sk)	2001-06-11	Substituované pyrolidínové hydroxamáty ako inhibítory metaloproteázy
KR20000035925A (ko)	2000-06-26	매트릭스 메탈로프로테아제 저해제인 포스핀산 아미드
SK24899A3 (en)	2000-04-10	Bidentate metalloprotease inhibitors
MXPA99002064A (en)	1999-09-20	Heterocyclic metalloprotease inhibitors
MXPA00001147A (en)	2001-12-04	Acyclic metalloprotease inhibitors
CZ20003734A3 (cs)	2001-04-11	Substituované pyrrolidinové hydroxamáty jako inhibitory metaloproteázy
CZ2000325A3 (cs)	2000-06-14	Acyklické inhibitory metalloproteinas
HK1021184B (en)	2005-04-29	Spirocyclic metalloprotease inhibitors