OA11142A - Arylsulfonyl hydroxamic acid derivatives - Google Patents

Arylsulfonyl hydroxamic acid derivatives Download PDF

Info

Publication number: OA11142A
Authority: OA; OAPI
Prior art keywords: aryl; alkyl; heteroaryl; alkoxy; crc6
Prior art date: 1997-02-11

Application number

OA9900174A

Other languages

English (en)

Inventor

Kim Francis Mcclure

Original Assignee

Pfizer

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.)

1997-02-11

Filing date

1999-08-06

Publication date

2003-04-25

1999-08-06 Application filed by Pfizer filed Critical Pfizer

2003-04-25 Publication of OA11142A publication Critical patent/OA11142A/en

Links

-1 Arylsulfonyl hydroxamic Chemical compound 0.000 title claims abstract description 71
239000002253 acid Substances 0.000 title description 87
150000001875 compounds Chemical class 0.000 claims abstract description 116
238000011282 treatment Methods 0.000 claims abstract description 18
102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 14
108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 14
201000010099 disease Diseases 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 13
230000000694 effects Effects 0.000 claims abstract description 11
206010028980 Neoplasm Diseases 0.000 claims abstract description 9
206010003246 arthritis Diseases 0.000 claims abstract description 8
201000011510 cancer Diseases 0.000 claims abstract description 8
206010040047 Sepsis Diseases 0.000 claims abstract description 7
208000028169 periodontal disease Diseases 0.000 claims abstract description 7
208000030507 AIDS Diseases 0.000 claims abstract description 6
231100000433 cytotoxic Toxicity 0.000 claims abstract description 6
230000001472 cytotoxic effect Effects 0.000 claims abstract description 6
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 6
208000037803 restenosis Diseases 0.000 claims abstract description 6
206010040070 Septic Shock Diseases 0.000 claims abstract description 5
230000036303 septic shock Effects 0.000 claims abstract description 5
206010014989 Epidermolysis bullosa Diseases 0.000 claims abstract description 4
206010039705 Scleritis Diseases 0.000 claims abstract description 4
208000002780 macular degeneration Diseases 0.000 claims abstract description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 112
125000003118 aryl group Chemical group 0.000 claims description 98
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 91
125000001072 heteroaryl group Chemical group 0.000 claims description 66
125000003545 alkoxy group Chemical group 0.000 claims description 63
239000001257 hydrogen Substances 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
239000001301 oxygen Chemical group 0.000 claims description 34
229910052760 oxygen Inorganic materials 0.000 claims description 34
229910052757 nitrogen Inorganic materials 0.000 claims description 30
229910052799 carbon Inorganic materials 0.000 claims description 29
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 27
102000003390 tumor necrosis factor Human genes 0.000 claims description 27
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
125000005842 heteroatom Chemical group 0.000 claims description 24
229910052684 Cerium Inorganic materials 0.000 claims description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
125000004104 aryloxy group Chemical group 0.000 claims description 20
229910052717 sulfur Chemical group 0.000 claims description 20
239000011593 sulfur Chemical group 0.000 claims description 20
125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
230000005764 inhibitory process Effects 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000005110 aryl thio group Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000001769 aryl amino group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000005241 heteroarylamino group Chemical group 0.000 claims description 5
125000005936 piperidyl group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000005035 acylthio group Chemical group 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
150000008575 L-amino acids Chemical class 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 35
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
125000002393 azetidinyl group Chemical group 0.000 claims 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
125000004414 alkyl thio group Chemical group 0.000 claims 4
125000005368 heteroarylthio group Chemical group 0.000 claims 4
125000002252 acyl group Chemical group 0.000 claims 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 3
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
CSLDBJUJDSYAKG-FPOVZHCZSA-N (2r,3s)-1-[4-(1,3-benzothiazol-2-ylmethoxy)phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=NC2=CC=CC=C2S1 CSLDBJUJDSYAKG-FPOVZHCZSA-N 0.000 claims 1
VFMQGJQJUNCZDG-FPOVZHCZSA-N (2r,3s)-1-[4-[2-(4-fluorophenyl)ethoxy]phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 VFMQGJQJUNCZDG-FPOVZHCZSA-N 0.000 claims 1
UFIPRXRNECOZCM-ZWKOTPCHSA-N (2r,3s)-n,3-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 UFIPRXRNECOZCM-ZWKOTPCHSA-N 0.000 claims 1
LTXMNGNZBGPTLR-LSDHHAIUSA-N (2r,3s)-n,3-dihydroxy-1-[4-(1,3-thiazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CN=CS1 LTXMNGNZBGPTLR-LSDHHAIUSA-N 0.000 claims 1
UFIMUQYMICWLMR-WCQYABFASA-N (2r,3s)-n,3-dihydroxy-1-[4-(2h-tetrazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=NN=NN1 UFIMUQYMICWLMR-WCQYABFASA-N 0.000 claims 1
SLKKVBIPVXPLEG-DLBZAZTESA-N (2r,3s)-n,3-dihydroxy-1-[4-(pyridin-4-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=NC=C1 SLKKVBIPVXPLEG-DLBZAZTESA-N 0.000 claims 1
WOQSKGWYPFEBIZ-RDJZCZTQSA-N (2r,3s)-n,3-dihydroxy-3-methyl-1-[4-(1,3-thiazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CN=CS1 WOQSKGWYPFEBIZ-RDJZCZTQSA-N 0.000 claims 1
DOOZILOLHOKUGO-HKUYNNGSSA-N (2r,3s)-n,3-dihydroxy-3-methyl-1-[4-(pyridin-4-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=NC=C1 DOOZILOLHOKUGO-HKUYNNGSSA-N 0.000 claims 1
JMBOAEVTEXTTPO-BXUZGUMPSA-N (2r,4r)-1-[3-(4-fluorophenoxy)propylsulfonyl]-2-(hydroxycarbamoyl)piperidine-4-carboxylic acid Chemical compound ONC(=O)[C@H]1C[C@H](C(O)=O)CCN1S(=O)(=O)CCCOC1=CC=C(F)C=C1 JMBOAEVTEXTTPO-BXUZGUMPSA-N 0.000 claims 1
ACEUKQZDNBIUHG-CRAIPNDOSA-N (2r,4r)-n,4-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ACEUKQZDNBIUHG-CRAIPNDOSA-N 0.000 claims 1
KEVSGIPPEHZMGV-OALZAMAHSA-N (2r,4r)-n-hydroxy-1-(4-methoxyphenyl)sulfonyl-4-(piperazine-1-carbonyl)piperidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1S(=O)(=O)N1[C@@H](C(=O)NO)C[C@H](C(=O)N2CCNCC2)CC1 KEVSGIPPEHZMGV-OALZAMAHSA-N 0.000 claims 1
FCLQINRREQAAHO-MAUKXSAKSA-N (2r,4s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,4-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 FCLQINRREQAAHO-MAUKXSAKSA-N 0.000 claims 1
ACEUKQZDNBIUHG-MAUKXSAKSA-N (2r,4s)-n,4-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ACEUKQZDNBIUHG-MAUKXSAKSA-N 0.000 claims 1
UUSUIALWMWHMSS-CRAIPNDOSA-N (2r,5r)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,5-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 UUSUIALWMWHMSS-CRAIPNDOSA-N 0.000 claims 1
UUSUIALWMWHMSS-MAUKXSAKSA-N (2r,5s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,5-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 UUSUIALWMWHMSS-MAUKXSAKSA-N 0.000 claims 1
GIGWICZCQGBJDH-MAUKXSAKSA-N (2r,5s)-n,5-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GIGWICZCQGBJDH-MAUKXSAKSA-N 0.000 claims 1
125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
WOZBOFIMMNNBIE-LEWJYISDSA-N propan-2-yl n-[(2r,3s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-2-(hydroxycarbamoyl)piperidin-3-yl]carbamate Chemical compound ONC(=O)[C@H]1[C@@H](NC(=O)OC(C)C)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 WOZBOFIMMNNBIE-LEWJYISDSA-N 0.000 claims 1
239000004576 sand Substances 0.000 claims 1
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 abstract description 4
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Classifications

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- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
- 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
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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

OA9900174A 1997-02-11 1999-08-06 Arylsulfonyl hydroxamic acid derivatives OA11142A (en)

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Application Number	Priority Date	Filing Date	Title
US3760097P	1997-02-11	1997-02-11

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OA11142A true OA11142A (en)	2003-04-25

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OA9900174A OA11142A (en)	1997-02-11	1999-08-06	Arylsulfonyl hydroxamic acid derivatives

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US (1)	US6599890B1 (id)
EP (1)	EP0960098A1 (id)
JP (1)	JP3710489B2 (id)
KR (1)	KR20000070923A (id)
CN (1)	CN1247531A (id)
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CO (1)	CO4950619A1 (id)
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EA (1)	EA002546B1 (id)
GT (1)	GT199800026A (id)
HN (1)	HN1998000020A (id)
HR (1)	HRP980070B1 (id)
HU (1)	HUP0000657A3 (id)
ID (1)	ID22809A (id)
IL (1)	IL131123A0 (id)
IS (1)	IS5130A (id)
MA (1)	MA24469A1 (id)
NO (1)	NO993836L (id)
NZ (1)	NZ336836A (id)
OA (1)	OA11142A (id)
PA (1)	PA8446101A1 (id)
PE (1)	PE58699A1 (id)
PL (1)	PL334997A1 (id)
SA (1)	SA98180856A (id)
SK (1)	SK101399A3 (id)
TN (1)	TNSN98025A1 (id)
TR (1)	TR199901926T2 (id)
TW (1)	TW502020B (id)
UY (1)	UY24880A1 (id)
WO (1)	WO1998034918A1 (id)
YU (1)	YU37499A (id)
ZA (1)	ZA981061B (id)

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Publication number	Priority date	Publication date	Assignee	Title
EP0960098A1 (en) *	1997-02-11	1999-12-01	Pfizer Inc.	Arylsulfonyl hydroxamic acid derivatives
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1998
- 1998-01-16 EP EP98900124A patent/EP0960098A1/en not_active Withdrawn
- 1998-01-16 YU YU37499A patent/YU37499A/sh unknown
- 1998-01-16 EA EA199900641A patent/EA002546B1/ru not_active IP Right Cessation
- 1998-01-16 IL IL13112398A patent/IL131123A0/xx not_active IP Right Cessation
- 1998-01-16 KR KR1019997007188A patent/KR20000070923A/ko not_active Ceased
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- 1998-01-16 TR TR1999/01926T patent/TR199901926T2/xx unknown
- 1998-01-16 BR BR9807678-7A patent/BR9807678A/pt not_active Application Discontinuation
- 1998-01-16 JP JP53404098A patent/JP3710489B2/ja not_active Expired - Fee Related
- 1998-01-16 WO PCT/IB1998/000064 patent/WO1998034918A1/en not_active Ceased
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- 1998-01-16 CN CN98802460A patent/CN1247531A/zh active Pending
- 1998-01-16 AU AU53366/98A patent/AU722784B2/en not_active Ceased
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- 1998-02-09 TW TW087101709A patent/TW502020B/zh not_active IP Right Cessation
- 1998-02-10 TN TNTNSN98025A patent/TNSN98025A1/fr unknown
- 1998-02-10 AR ARP980100582A patent/AR011123A1/es not_active Application Discontinuation
- 1998-02-10 MA MA24960A patent/MA24469A1/fr unknown
- 1998-02-10 ZA ZA9801061A patent/ZA981061B/xx unknown
- 1998-02-10 DZ DZ980026A patent/DZ2416A1/xx active
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- 1998-02-15 SA SA98180856A patent/SA98180856A/ar unknown
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1999
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- 1999-08-06 OA OA9900174A patent/OA11142A/en unknown
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2000
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Also Published As

Publication number	Publication date
US6599890B1 (en)	2003-07-29
UY24880A1 (es)	2000-09-29
NZ336836A (en)	2001-02-23
NO993836D0 (no)	1999-08-10
JP2000510162A (ja)	2000-08-08
PE58699A1 (es)	1999-06-21
SK101399A3 (en)	2001-09-11
MA24469A1 (fr)	1998-10-01
HRP980070A2 (en)	1998-12-31
BG63430B1 (bg)	2002-01-31
ZA981061B (en)	1999-08-10
BG103641A (en)	2000-02-29
AP958A (en)	2001-04-17
CO4950619A1 (es)	2000-09-01
CA2280151C (en)	2005-12-13
TW502020B (en)	2002-09-11
DZ2416A1 (fr)	2003-01-04
CA2280151A1 (en)	1998-08-13
JP3710489B2 (ja)	2005-10-26
EA199900641A1 (ru)	2000-04-24
NO993836L (no)	1999-10-08
KR20000070923A (ko)	2000-11-25
YU37499A (sh)	2002-09-19
ID22809A (id)	1999-12-09
CN1247531A (zh)	2000-03-15
BR9807678A (pt)	2000-02-15
PL334997A1 (en)	2000-03-27
IL131123A0 (en)	2001-01-28
EA002546B1 (ru)	2002-06-27
SA98180856A (ar)	2005-12-03
PA8446101A1 (es)	2000-05-24
TNSN98025A1 (fr)	2005-03-15
HUP0000657A2 (hu)	2000-09-28
GT199800026A (es)	1999-07-27
IS5130A (is)	1999-07-23
HRP980070B1 (en)	2002-10-31
HUP0000657A3 (en)	2000-10-30
AU722784B2 (en)	2000-08-10
EP0960098A1 (en)	1999-12-01
WO1998034918A1 (en)	1998-08-13
TR199901926T2 (xx)	1999-12-21
HN1998000020A (es)	1999-01-08
AR011123A1 (es)	2000-08-02
AU5336698A (en)	1998-08-26

Publication	Publication Date	Title
OA11142A (en)	2003-04-25	Arylsulfonyl hydroxamic acid derivatives
AP733A (en)	1999-02-12	Arylsulfonylamino hydroxamic acid derivatives.
OA11081A (en)	2002-03-14	Arylsulfonylamino hydroxamic acid derivatives
RU2146671C1 (ru)	2000-03-20	Производные арилсульфонилгидроксамовой кислоты
IL134300A (en)	2004-07-25	Derivatives of aryloxyacrylylsulfonaminoaminoxamic acid derivatives, pharmaceutical preparations containing them and their use in the preparation of drugs for the treatment of arthritis, cancer and other diseases characterized by the activity of metalloproteinase-13 of matrix
KR20080109915A (ko)	2008-12-17	유기 화합물
NZ520656A (en)	2004-05-28	Heterocyclic side chain containing metalloprotease inhibitors
GB2321641A (en)	1998-08-05	Amino-sulphonamides as Metalloprotease inhibitors
CA2264044A1 (en)	1998-03-05	Spirocyclic metalloprotease inhibitors
US6509337B1 (en)	2003-01-21	Arylsulfonyl Hydroxamic Acid derivatives as MMP and TNF inhibitors
MXPA99007385A (en)	2000-07-01	Arylsulfonyl hydroxamic acid derivatives
CZ9902833A3 (cs)	2000-10-11	Deriváty arylsulfonylhydroxamových kyselin, farmaceutický prostředek, způsob inhibice matričních metalloproteinas nebo produkce faktoru nekrosy nádorů a způsob léčení
MXPA99001808A (en)	1999-09-20	Arylsulfonylamino hydroxamic acid derivatives
KR100194258B1 (ko)	1999-06-15	아릴설포닐 하이드록삼산 유도체
CZ58999A3 (cs)	2000-03-15	Deriváty arylsulfonylaminohydroxamové kyseliny, farmaceutický prostředek, způsob inhibice matričních metalloproteinas nebo produkce faktoru nekrosy nádorů a způsob léčení