OA11081A - Arylsulfonylamino hydroxamic acid derivatives - Google Patents

Arylsulfonylamino hydroxamic acid derivatives Download PDF

Info

Publication number: OA11081A
Authority: OA; OAPI
Prior art keywords: aryl; heteroaryl; alkyl; aryloxy; daim
Prior art date: 1997-02-03

Application number

OA9900168A

Other languages

English (en)

Inventor

Kim Francis Mcclure

Robinson Ralph Pelton Jr

Original Assignee

Pfizer Prod Inc

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.)

1997-02-03

Filing date

1999-07-30

Publication date

2002-03-14

1999-07-30 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2002-03-14 Publication of OA11081A publication Critical patent/OA11081A/en

Links

-1 Arylsulfonylamino hydroxamic Chemical compound 0.000 title abstract description 22
239000002253 acid Substances 0.000 title description 23
150000001875 compounds Chemical class 0.000 claims abstract description 60
201000010099 disease Diseases 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
238000004519 manufacturing process Methods 0.000 claims abstract description 12
238000011282 treatment Methods 0.000 claims abstract description 11
102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 10
108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 10
206010028980 Neoplasm Diseases 0.000 claims abstract description 8
206010003246 arthritis Diseases 0.000 claims abstract description 8
201000011510 cancer Diseases 0.000 claims abstract description 8
208000030507 AIDS Diseases 0.000 claims abstract description 6
206010040047 Sepsis Diseases 0.000 claims abstract description 6
206010040070 Septic Shock Diseases 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
230000036303 septic shock Effects 0.000 claims abstract description 6
206010014989 Epidermolysis bullosa Diseases 0.000 claims abstract description 5
206010039705 Scleritis Diseases 0.000 claims abstract description 4
231100000433 cytotoxic Toxicity 0.000 claims abstract description 4
230000001472 cytotoxic effect Effects 0.000 claims abstract description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 4
208000002780 macular degeneration Diseases 0.000 claims abstract 2
125000003118 aryl group Chemical group 0.000 claims description 81
125000001072 heteroaryl group Chemical group 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 37
125000004104 aryloxy group Chemical group 0.000 claims description 27
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 25
102000003390 tumor necrosis factor Human genes 0.000 claims description 25
230000005764 inhibitory process Effects 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910014585 C2-Ce Inorganic materials 0.000 claims description 12
125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 8
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000011159 matrix material Substances 0.000 claims description 4
229940080818 propionamide Drugs 0.000 claims description 4
206010028851 Necrosis Diseases 0.000 claims description 3
239000002246 antineoplastic agent Substances 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
230000017074 necrotic cell death Effects 0.000 claims description 3
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
HGASXDLSPHLKGB-UHFFFAOYSA-N 1-[[4-(4-fluorophenyl)phenyl]sulfonylamino]-n-hydroxycyclopentane-1-carboxamide Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCCC1 HGASXDLSPHLKGB-UHFFFAOYSA-N 0.000 claims description 2
XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 10
VYRRHXZZTGOPBI-UHFFFAOYSA-N 1-[[4-(4-fluorophenyl)phenyl]sulfonylamino]-n-hydroxycyclopropane-1-carboxamide Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CC1 VYRRHXZZTGOPBI-UHFFFAOYSA-N 0.000 claims 1
GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims 1
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
XPWGEUXPCQVZKF-UHFFFAOYSA-N n-hydroxy-1-[(5-pyridin-2-ylthiophen-2-yl)sulfonylamino]cyclopentane-1-carboxamide Chemical compound C=1C=C(C=2N=CC=CC=2)SC=1S(=O)(=O)NC1(C(=O)NO)CCCC1 XPWGEUXPCQVZKF-UHFFFAOYSA-N 0.000 claims 1
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OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 abstract description 2
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 2
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229940079593 drug Drugs 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
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150000003460 sulfonic acids Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom 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
- 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
- C07D211/66—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 having a hetero atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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Organic Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
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Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Immunology (AREA)
Communicable Diseases (AREA)
AIDS & HIV (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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OA9900168A 1997-02-03 1999-07-30 Arylsulfonylamino hydroxamic acid derivatives OA11081A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3685797P	1997-02-03	1997-02-03

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OA11081A true OA11081A (en)	2002-03-14

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ID=21891041

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OA9900168A OA11081A (en)	1997-02-03	1999-07-30	Arylsulfonylamino hydroxamic acid derivatives

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US (1)	US6303636B1 (de)
EP (1)	EP0977733B1 (de)
JP (1)	JP3765584B2 (de)
KR (1)	KR100317146B1 (de)
CN (1)	CN1113862C (de)
AP (1)	AP826A (de)
AR (1)	AR011101A1 (de)
AT (1)	ATE248812T1 (de)
AU (1)	AU721748B2 (de)
BG (1)	BG64308B1 (de)
BR (1)	BR9807815A (de)
CA (1)	CA2279276C (de)
CO (1)	CO4920234A1 (de)
DE (1)	DE69817801T2 (de)
DK (1)	DK0977733T3 (de)
DZ (1)	DZ2410A1 (de)
EA (1)	EA002594B1 (de)
ES (1)	ES2202796T3 (de)
GT (1)	GT199800025A (de)
HN (1)	HN1998000011A (de)
HR (1)	HRP980058B1 (de)
HU (1)	HUP0000852A2 (de)
ID (1)	ID22799A (de)
IL (2)	IL131042A (de)
IS (1)	IS1950B (de)
MA (1)	MA26471A1 (de)
MY (1)	MY121754A (de)
NO (1)	NO313631B1 (de)
NZ (1)	NZ336840A (de)
OA (1)	OA11081A (de)
PA (1)	PA8445801A1 (de)
PE (1)	PE57799A1 (de)
PL (1)	PL335027A1 (de)
PT (1)	PT977733E (de)
SK (1)	SK283963B6 (de)
TN (1)	TNSN98019A1 (de)
TR (1)	TR199901849T2 (de)
TW (1)	TW509668B (de)
UA (1)	UA63935C2 (de)
UY (1)	UY24866A1 (de)
WO (1)	WO1998033768A1 (de)
ZA (1)	ZA98823B (de)

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Publication number	Publication date
CO4920234A1 (es)	2000-05-29
AU721748B2 (en)	2000-07-13
WO1998033768A1 (en)	1998-08-06
DK0977733T3 (da)	2003-11-24
AP9801191A0 (en)	1998-03-31
IS5129A (is)	1999-07-23
IS1950B (is)	2004-10-13
EP0977733B1 (de)	2003-09-03
MA26471A1 (fr)	2004-12-20
HRP980058B1 (en)	2002-04-30
CN1249743A (zh)	2000-04-05
AU8191798A (en)	1998-08-25
KR20000070721A (ko)	2000-11-25
TW509668B (en)	2002-11-11
EP0977733A1 (de)	2000-02-09
PA8445801A1 (es)	2000-05-24
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ZA98823B (en)	1999-08-02
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UA63935C2 (uk)	2004-02-16
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US6303636B1 (en)	2001-10-16
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