BG104118A - Производни на арилоксиарилсулфониламино хидроксамова киселина - Google Patents

Производни на арилоксиарилсулфониламино хидроксамова киселина Download PDF

Info

Publication number: BG104118A
Authority: BG; Bulgaria
Prior art keywords: compound; fluorophenoxy; benzenesulfonyl; amino; hydrogen
Prior art date: 1997-08-08

Application number

BG104118A

Other languages

Bulgarian (bg)

English (en)

Inventor

Ralph Robinson

Original Assignee

Pfizer Products 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.)

1997-08-08

Filing date

2000-02-01

Publication date

2000-09-29

2000-02-01 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2000-09-29 Publication of BG104118A publication Critical patent/BG104118A/bg

Links

239000002253 acid Substances 0.000 title claims description 25
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 73
-1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims abstract description 46
150000003839 salts Chemical class 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 8
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
150000002431 hydrogen Chemical group 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 12
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 10
238000000034 method Methods 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 9
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
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206010003246 arthritis Diseases 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
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LLMCVPDKPNDQCK-UHFFFAOYSA-N ethyl 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxycarbamoyl)cyclopentyl]amino]propanoate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(=O)NO)CCCC1 LLMCVPDKPNDQCK-UHFFFAOYSA-N 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
VHHGUBHZBLPTKL-UHFFFAOYSA-N Cp-471358 Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCCC1 VHHGUBHZBLPTKL-UHFFFAOYSA-N 0.000 claims description 3
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125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
NMDUJEUWNLCXSB-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]amino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N(CCC(O)=O)C(C)(C)C(=O)NO)=CC=C1OC1=CC=C(F)C=C1 NMDUJEUWNLCXSB-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
102000011722 Matrix Metalloproteinase 13 Human genes 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
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239000000243 solution Substances 0.000 description 19
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238000006243 chemical reaction Methods 0.000 description 15
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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239000002904 solvent Substances 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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239000012267 brine Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
239000000758 substrate Substances 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
239000011159 matrix material Substances 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
231100000252 nontoxic Toxicity 0.000 description 6
230000003000 nontoxic effect Effects 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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239000002798 polar solvent Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
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210000001519 tissue Anatomy 0.000 description 5
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KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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102000004142 Trypsin Human genes 0.000 description 4
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150000001447 alkali salts Chemical class 0.000 description 4
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150000007514 bases Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
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239000010452 phosphate Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000012588 trypsin Substances 0.000 description 4
231100000397 ulcer Toxicity 0.000 description 4
HGMRCAGQEDXAGL-UHFFFAOYSA-N 1-[(3-ethoxy-3-oxopropyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(O)=O)CCCC1 HGMRCAGQEDXAGL-UHFFFAOYSA-N 0.000 description 3
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 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
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
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- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen 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 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
- C07D309/14—Nitrogen atoms not forming part of a nitro radical

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BG104118A 1997-08-08 2000-02-01 Производни на арилоксиарилсулфониламино хидроксамова киселина BG104118A (bg)

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US5520797P	1997-08-08	1997-08-08
PCT/IB1998/001113 WO1999007675A1 (fr)	1997-08-08	1998-07-21	Derives de l'acide aryloxyarylsulfonylamino hydroxamique

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JP (1)	JP3448275B2 (fr)
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CN (1)	CN1171866C (fr)
AP (1)	AP1220A (fr)
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AT (1)	ATE263147T1 (fr)
AU (1)	AU730248B2 (fr)
BG (1)	BG104118A (fr)
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GT (1)	GT199800124A (fr)
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UA (1)	UA61963C2 (fr)
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WO (1)	WO1999007675A1 (fr)
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- 1998-08-04 PE PE1998000696A patent/PE110899A1/es not_active Application Discontinuation
- 1998-08-05 DZ DZ980191A patent/DZ2581A1/fr active
- 1998-08-05 PA PA19988456801A patent/PA8456801A1/es unknown
- 1998-08-05 TW TW087112896A patent/TW426662B/zh not_active IP Right Cessation
- 1998-08-06 AP APAP/P/1998/001313A patent/AP1220A/en active
- 1998-08-06 CO CO98045260A patent/CO4960658A1/es unknown
- 1998-08-06 MY MYPI98003591A patent/MY120235A/en unknown
- 1998-08-07 HR HR980438A patent/HRP980438B1/xx not_active IP Right Cessation
- 1998-08-07 MA MA25207A patent/MA26530A1/fr unknown
- 1998-08-07 AR ARP980103929A patent/AR015419A1/es unknown
- 1998-08-07 TN TNTNSN98150A patent/TNSN98150A1/fr unknown
- 1998-08-07 GT GT199800124A patent/GT199800124A/es unknown
- 1998-08-07 ZA ZA9807126A patent/ZA987126B/xx unknown
- 1998-08-10 UY UY25131A patent/UY25131A1/es not_active IP Right Cessation
2000
- 2000-01-14 IS IS5340A patent/IS5340A/is unknown
- 2000-02-01 BG BG104118A patent/BG104118A/bg unknown
- 2000-02-04 OA OA1200000028A patent/OA11284A/en unknown
- 2000-02-07 NO NO20000604A patent/NO313189B1/no not_active IP Right Cessation
- 2000-04-04 UY UY26098A patent/UY26098A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
TW426662B (en)	2001-03-21
WO1999007675A1 (fr)	1999-02-18
ATE263147T1 (de)	2004-04-15
DK1003720T3 (da)	2004-05-10
DZ2581A1 (fr)	2003-02-22
SK1362000A3 (en)	2000-10-09
IL134300A0 (en)	2001-04-30
ES2216293T3 (es)	2004-10-16
CA2299355C (fr)	2005-09-27
CN1265646A (zh)	2000-09-06
NO313189B1 (no)	2002-08-26
GT199800124A (es)	2000-01-29
HRP980438B1 (en)	2003-04-30
DE69822839T2 (de)	2004-08-19
UY26098A1 (es)	2001-12-28
PL338633A1 (en)	2000-11-06
EP1003720A1 (fr)	2000-05-31
PA8456801A1 (es)	2000-05-24
EA002490B1 (ru)	2002-06-27
US6214872B1 (en)	2001-04-10
AU8125398A (en)	1999-03-01
ZA987126B (en)	2000-02-07
IS5340A (is)	2000-01-14
DE69822839D1 (de)	2004-05-06
HK1029575A1 (en)	2001-04-06
PE110899A1 (es)	1999-11-12
HUP0002960A3 (en)	2001-12-28
EA200000096A1 (ru)	2000-10-30
PT1003720E (pt)	2004-07-30
IL134300A (en)	2004-07-25
UA61963C2 (en)	2003-12-15
OA11284A (en)	2003-07-30
AR015419A1 (es)	2001-05-02
CA2299355A1 (fr)	1999-02-18
HUP0002960A2 (hu)	2001-07-30
MY120235A (en)	2005-09-30
JP2001512713A (ja)	2001-08-28
JP3448275B2 (ja)	2003-09-22
ID23668A (id)	2000-05-11
NZ502309A (en)	2002-02-01
KR100372138B1 (ko)	2003-02-14
CO4960658A1 (es)	2000-09-25
EP1003720B1 (fr)	2004-03-31
NO20000604L (no)	2000-02-07
AU730248B2 (en)	2001-03-01
BR9811868A (pt)	2000-08-15
NO20000604D0 (no)	2000-02-07
HRP980438A2 (en)	1999-12-31
MA26530A1 (fr)	2004-12-20
TR200000368T2 (tr)	2000-07-21
AP1220A (en)	2003-10-24
TNSN98150A1 (fr)	2005-03-15
UY25131A1 (es)	2000-12-29
KR20010022707A (ko)	2001-03-26
YU1900A (sh)	2002-08-12
AP9801313A0 (en)	1998-09-30
CN1171866C (zh)	2004-10-20

Publication	Publication Date	Title
EP1003720B1 (fr)	2004-03-31	Derives de l'acide aryloxyarylsulfonylamino hydroxamique
AP826A (en)	2000-04-28	Arysulfonylamino hydroxamic acid derivatives.
AP733A (en)	1999-02-12	Arylsulfonylamino hydroxamic acid derivatives.
EP0895988B1 (fr)	2002-05-22	Dérivés de l'acide arylsulfonamino-hydroxamique
WO1998034915A1 (fr)	1998-08-13	Derives du n-hxdroxy-beta-sulfonyl-propionamide et leur utilisation comme inhibiteurs des metalloproteases matrices
US20020006920A1 (en)	2002-01-17	Arylsulfonylamino hydroxamic acid derivatives
US6107337A (en)	2000-08-22	Arylsulfonylamino hydroxamic acid derivatives
EP1415984A1 (fr)	2004-05-06	Dérivés de l'acide aryloxyarylsulfonylaminohydroxamique
MXPA00001349A (en)	2001-05-07	Aryloxyarylsulfonylamino hydroxamic acid derivatives
CZ2000306A3 (cs)	2000-07-12	Deriváty aryloxyarylsulfonylaminohydroxamové kyseliny
HK1029575B (en)	2005-04-01	Aryloxyarylsulfonylamino hydroxamic acid derivatives
CZ267699A3 (cs)	2000-09-13	Deriváty arylsulfonylaminohydroxamové kyseliny, farmaceutický prostředek, způsob inhibice matričních metalloproteinas nebo produkce faktoru nekrosy nádorů a způsob léčení