ZA200106966B - Dihetero-substituted metalloprotease inhibitors. - Google Patents
Dihetero-substituted metalloprotease inhibitors. Download PDFInfo
- Publication number
- ZA200106966B ZA200106966B ZA200106966A ZA200106966A ZA200106966B ZA 200106966 B ZA200106966 B ZA 200106966B ZA 200106966 A ZA200106966 A ZA 200106966A ZA 200106966 A ZA200106966 A ZA 200106966A ZA 200106966 B ZA200106966 B ZA 200106966B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- hydrogen
- cycloalkyl
- aryl
- alkyl
- Prior art date
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- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- 239000001257 hydrogen Substances 0.000 claims description 128
- 125000003118 aryl group Chemical group 0.000 claims description 124
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 115
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 114
- 125000001072 heteroaryl group Chemical group 0.000 claims description 110
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 107
- 150000002431 hydrogen Chemical class 0.000 claims description 99
- 125000003342 alkenyl group Chemical group 0.000 claims description 85
- 125000000304 alkynyl group Chemical group 0.000 claims description 84
- 125000001188 haloalkyl group Chemical group 0.000 claims description 79
- -1 2-thiazolyl Chemical group 0.000 claims description 69
- 125000005842 heteroatom Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 29
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- 108010006035 Metalloproteases Proteins 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 13
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- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 39
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 30
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 24
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 20
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
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- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims 1
- ZVNMJJMOWZKUGU-UHFFFAOYSA-N 2-amino-2-[4-(4-methoxyphenyl)phenyl]sulfonyl-3-[2-(phenoxymethyl)-1,3-dioxan-2-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)C(N)(CC2(COC=3C=CC=CC=3)OCCCO2)C(O)=O)C=C1 ZVNMJJMOWZKUGU-UHFFFAOYSA-N 0.000 claims 1
- WSCJTTLXCPWKHC-UHFFFAOYSA-N 2-amino-2-[4-(4-methoxyphenyl)phenyl]sulfonyl-3-[2-[(2-oxoazepan-1-yl)methyl]-1,3-dioxan-2-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)C(N)(CC2(CN3C(CCCCC3)=O)OCCCO2)C(O)=O)C=C1 WSCJTTLXCPWKHC-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- CNCKXDJGYWPCIS-UHFFFAOYSA-N 4-hydroxy-2-[(4-phenyldiazenylphenyl)sulfonylamino]-5-(1,3-thiazol-2-ylsulfanyl)pentanoic acid Chemical compound C=1C=C(N=NC=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(C(O)=O)CC(O)CSC1=NC=CS1 CNCKXDJGYWPCIS-UHFFFAOYSA-N 0.000 claims 1
- VXVHSAVDKNOUGS-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-3-phenylmethoxy-5-(1,3-thiazol-2-ylsulfanyl)pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(C(OCC=2C=CC=CC=2)C(O)CSC=2SC=CN=2)C(O)=O)C=C1 VXVHSAVDKNOUGS-UHFFFAOYSA-N 0.000 claims 1
- FVJPUGQXZLHPNS-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-(1-methyltetrazol-5-yl)sulfanylpentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2N(N=NN=2)C)C(O)=O)C=C1 FVJPUGQXZLHPNS-UHFFFAOYSA-N 0.000 claims 1
- RKVIAGFOESNVSS-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-(2-methylfuran-3-yl)sulfanylpentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC2=C(OC=C2)C)C(O)=O)C=C1 RKVIAGFOESNVSS-UHFFFAOYSA-N 0.000 claims 1
- ZPUYIKJVCWURQG-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-(4-methyl-2-oxochromen-7-yl)sulfanylpentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2C=C3OC(=O)C=C(C)C3=CC=2)C(O)=O)C=C1 ZPUYIKJVCWURQG-UHFFFAOYSA-N 0.000 claims 1
- ZJAVLPMVRDWYNC-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2SC(C)=NN=2)C(O)=O)C=C1 ZJAVLPMVRDWYNC-UHFFFAOYSA-N 0.000 claims 1
- TXNKDZGTXUTUMD-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-[(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2SC(SC)=NN=2)C(O)=O)C=C1 TXNKDZGTXUTUMD-UHFFFAOYSA-N 0.000 claims 1
- NIIKIRZSWPTVFN-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-[(5-phenyl-1h-1,2,4-triazol-3-yl)sulfanyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2N=C(NN=2)C=2C=CC=CC=2)C(O)=O)C=C1 NIIKIRZSWPTVFN-UHFFFAOYSA-N 0.000 claims 1
- ROJDZHSYNYVWOY-UHFFFAOYSA-N 4-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-phenylsulfanylpentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2C=CC=CC=2)C(O)=O)C=C1 ROJDZHSYNYVWOY-UHFFFAOYSA-N 0.000 claims 1
- UZONUSJWNVIMRQ-UHFFFAOYSA-N 4-hydroxy-5-(1h-imidazol-2-ylsulfanyl)-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(CC(O)CSC=2NC=CN=2)C(O)=O)C=C1 UZONUSJWNVIMRQ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D235/28—Sulfur atoms
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
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- C07D277/70—Sulfur atoms
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/36—Sulfur atom
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- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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EP (1) | EP1165530A2 (de) |
JP (1) | JP2002538146A (de) |
KR (1) | KR20010102485A (de) |
CN (1) | CN1362951A (de) |
AR (1) | AR022824A1 (de) |
AU (1) | AU767344B2 (de) |
BR (1) | BR0009244A (de) |
CA (1) | CA2366954A1 (de) |
CO (1) | CO5180578A1 (de) |
CZ (1) | CZ20013155A3 (de) |
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HU (1) | HUP0201714A3 (de) |
IL (1) | IL145085A0 (de) |
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MX (1) | MXPA01008857A (de) |
NO (1) | NO20014243L (de) |
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TR (1) | TR200102524T2 (de) |
WO (1) | WO2000051993A2 (de) |
ZA (1) | ZA200106966B (de) |
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Publication number | Priority date | Publication date | Assignee | Title |
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CZ20013155A3 (cs) * | 1999-03-03 | 2002-01-16 | The Procter & Gamble Company | Inhibitory metaloproteas |
US6696456B1 (en) | 1999-10-14 | 2004-02-24 | The Procter & Gamble Company | Beta disubstituted metalloprotease inhibitors |
KR20020038951A (ko) * | 1999-10-14 | 2002-05-24 | 데이비드 엠 모이어 | 베타 이치환된 메탈로프로테아제 저해제 |
AU2001245863A1 (en) * | 2000-03-21 | 2001-10-03 | The Procter & Gamble Company | Heterocyclic side chain containing metalloprotease inhibitors |
JP2003528082A (ja) | 2000-03-21 | 2003-09-24 | ザ プロクター アンド ギャンブル カンパニー | ニフッ化酪酸メタロプロテアーゼ阻害物質 |
NZ520657A (en) | 2000-03-21 | 2004-11-26 | Procter & Gamble | Heterocyclic side chain containing, N-substituted metalloprotease inhibitors |
US6897237B2 (en) | 2000-04-28 | 2005-05-24 | Shionogi & Co. Ltd. | MMP-12 inhibitors |
WO2002033087A2 (en) * | 2000-10-17 | 2002-04-25 | Curagen Corporation | Proteins and nucleic acids encoding same |
GB0108097D0 (en) * | 2001-03-30 | 2001-05-23 | Pfizer Ltd | Compounds |
US6645993B2 (en) | 2001-03-30 | 2003-11-11 | Warner-Lambert Company | 3-heterocyclylpropanohydroxamic acid PCP inhibitors |
AU2003221160A1 (en) * | 2002-03-27 | 2003-10-08 | Shionogi And Co., Ltd. | Decomposition inhibitor for extracellular matrix of cartilage |
WO2004089294A2 (en) | 2003-04-04 | 2004-10-21 | Incyte Corporation | Compositions, methods and kits relating to her-2 cleavage |
US20040258769A1 (en) * | 2003-06-20 | 2004-12-23 | Barker Ronnie C. | Use of ocular vitamins in conjunction with other treatment methods for AMD |
EP1692124B1 (de) * | 2003-12-04 | 2008-10-15 | Wyeth | Biarylsulfonamide als mmp-inhibitoren |
BR0318625A (pt) | 2003-12-04 | 2006-10-31 | Wyeth Corp | biaril sulfonamidas e métodos para usar as mesmas |
US20080119513A1 (en) * | 2004-09-06 | 2008-05-22 | Fumihiko Watanabe | Sulfonamide Derivative Selectively Inhibiting Mmp-13 |
KR101827333B1 (ko) | 2008-09-19 | 2018-02-09 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 반도체장치 |
WO2017152114A1 (en) * | 2016-03-04 | 2017-09-08 | Jeffrey Alan Klein | Tumescent contravenom drug delivery |
CN108238981A (zh) * | 2016-12-23 | 2018-07-03 | 宁波爱诺医药科技有限公司 | 一种lcz-696关键中间体的制备方法 |
CN114014824B (zh) * | 2020-12-09 | 2023-06-13 | 上海科技大学 | 一种杂环化合物的应用 |
Family Cites Families (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1985184U (de) | 1965-06-26 | 1968-05-09 | Detlef Schaffer | Kolbenmaschine. |
GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
DE4011172A1 (de) | 1990-04-06 | 1991-10-10 | Degussa | Verbindungen zur bekaempfung von pflanzenkrankheiten |
GB9102635D0 (en) | 1991-02-07 | 1991-03-27 | British Bio Technology | Compounds |
GB9107368D0 (en) | 1991-04-08 | 1991-05-22 | Smithkline Beecham Plc | Novel compounds |
IL98681A (en) | 1991-06-30 | 1997-06-10 | Yeda Rehovot And Dev Company L | Pharmaceutical compositions comprising hydroxamate derivatives for iron removal from mammalian cells and from pathogenic organisms and some novel hydroxamate derivatives |
JPH05125029A (ja) | 1991-11-06 | 1993-05-21 | Yamanouchi Pharmaceut Co Ltd | 新規なアミド化合物又はその塩 |
GB9200245D0 (en) | 1992-01-07 | 1992-02-26 | British Bio Technology | Compounds |
US5552419A (en) | 1993-01-06 | 1996-09-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
US5506242A (en) | 1993-01-06 | 1996-04-09 | Ciba-Geigy Corporation | Arylsufonamido-substituted hydroxamic acids |
DK0766665T3 (da) | 1994-06-22 | 1999-12-06 | British Biotech Pharm | Metalloproteinaseinhibitorer |
JP3053222B2 (ja) | 1995-04-20 | 2000-06-19 | ファイザー・インコーポレーテッド | Mmpおよびtnf抑制剤としてのアリールスルホニルヒドロキサム酸誘導体 |
IL118325A0 (en) * | 1995-05-25 | 1996-10-31 | Pont Merck And Pharmaceutical | Integrin receptor antagonists and pharmaceutical compositions containing them |
KR980009238A (ko) | 1995-07-28 | 1998-04-30 | 우에노 도시오 | 설포닐아미노산 유도체 |
EP0845987A4 (de) | 1995-08-08 | 2000-05-24 | Fibrogen Inc | C - proteinaseinhibitoren zur behandlung von störungen, die mit einer kollagenüberproduktion zusammenhängen |
DK0874830T3 (da) | 1995-12-08 | 2003-04-22 | Agouron Pharma | Metalloproteinaseinhibitor, farmaceutisk præparat indeholdende denne og den farmaceutiske anvendelse samt en fremgangsmåde til fremstilling deraf |
US6136834A (en) | 1995-12-27 | 2000-10-24 | Ono Pharmaceutical Co., Ltd. | Tetrazole compounds and pharmaceutical agents containing such derivative |
FR2743562B1 (fr) | 1996-01-11 | 1998-04-03 | Sanofi Sa | Derives de n-(arylsulfonyl) aminoacides, leur preparation, les compositions pharmaceutiques en contenant |
SK282995B6 (sk) * | 1996-01-23 | 2003-01-09 | Shionogi And Co., Ltd. | Zlúčenina na inhibíciu metaloproteázy a prostriedok s jej obsahom |
TW448172B (en) | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
EP0915086A4 (de) | 1996-05-24 | 2001-01-17 | Ono Pharmaceutical Co | Phenylsulfonamidderivate |
US5861861A (en) | 1996-06-28 | 1999-01-19 | Microchip Technology Incorporated | Microcontroller chip with integrated LCD control module and switched capacitor driver circuit |
NZ334252A (en) | 1996-08-28 | 2000-11-24 | Procter & Gamble | Heterocyclic metalloprotease inhibitors |
BR9712792A (pt) | 1996-08-28 | 1999-12-14 | Procter & Gamble | Inibidores de metaloprotease bidentada. |
TR199900383T2 (xx) | 1996-08-28 | 1999-05-21 | The Procter & Gamble Company | 1,3-Diheterosiklik metaloproteaz inhibit�rleri. |
ES2225983T3 (es) | 1996-08-28 | 2005-03-16 | THE PROCTER & GAMBLE COMPANY | Inhibidores de metaloproteasas espirociclicos. |
ES2201318T3 (es) | 1996-08-28 | 2004-03-16 | THE PROCTER & GAMBLE COMPANY | Inhibidores de metaloproteasas de aminas ciclicas substituidas. |
DK0923561T3 (da) | 1996-08-28 | 2003-02-24 | Procter & Gamble | Heterocykliske metalloproteaseinhibitorer |
AU4812697A (en) | 1996-10-22 | 1998-05-15 | Pharmacia & Upjohn Company | Alpha-amino sulfonyl hydroxamic acids as matrix metalloproteinase inhibitors |
AU720615B2 (en) | 1997-01-17 | 2000-06-08 | Pharmacia & Upjohn Company | Bis-sulfonomides hydroxamic acids as MMP inhibitors |
JPH10204054A (ja) | 1997-01-21 | 1998-08-04 | Ono Pharmaceut Co Ltd | フェニルスルホンアミド誘導体 |
DE69817801T2 (de) | 1997-02-03 | 2004-03-11 | Pfizer Products Inc., Groton | Arylsulfonylhydroxamsäurederivate |
GB9706255D0 (en) | 1997-03-26 | 1997-05-14 | Smithkline Beecham Plc | Novel compounds |
CA2285372A1 (en) | 1997-04-01 | 1998-10-08 | Melwyn A. Abreo | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
US5756545A (en) * | 1997-04-21 | 1998-05-26 | Warner-Lambert Company | Biphenysulfonamide matrix metal alloproteinase inhibitors |
DK0877019T3 (da) | 1997-05-09 | 2002-04-08 | Hoechst Ag | Substituerede diaminocarboxylsyrer |
DE19719621A1 (de) | 1997-05-09 | 1998-11-12 | Hoechst Ag | Sulfonylaminocarbonsäuren |
WO1998050348A1 (en) | 1997-05-09 | 1998-11-12 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
BR9810841A (pt) | 1997-07-31 | 2001-07-10 | Procter & Gamble | Inibidores de metaloprotease alicìclicos |
DK1047450T3 (da) * | 1997-12-23 | 2003-01-27 | Warner Lambert Co | Kombinationer af ACE-inhibitorer og MMP-inhibitorer |
CN1195735C (zh) | 1998-02-04 | 2005-04-06 | 诺瓦提斯公司 | 抑制使基质退化的金属蛋白酶的磺酰氨基衍生物 |
JPH11246527A (ja) * | 1998-03-02 | 1999-09-14 | Shionogi & Co Ltd | Mmp−8阻害剤 |
CN1304402A (zh) | 1998-04-03 | 2001-07-18 | 三共株式会社 | 磺酰胺衍生物 |
EP0967201A1 (de) * | 1998-05-20 | 1999-12-29 | Roche Diagnostics GmbH | Sulphonamide enthaltende Arzneimittel als Matrix Metalloproteinase Inhibitoren |
IL142958A0 (en) * | 1998-12-18 | 2002-04-21 | Du Pont Pharm Co | Vitronectin receptor antagonist pharmaceuticals |
CZ20013155A3 (cs) * | 1999-03-03 | 2002-01-16 | The Procter & Gamble Company | Inhibitory metaloproteas |
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- 2000-03-01 BR BR0009244-4A patent/BR0009244A/pt not_active IP Right Cessation
- 2000-03-01 CN CN00806920A patent/CN1362951A/zh active Pending
- 2000-03-01 EP EP00915936A patent/EP1165530A2/de not_active Withdrawn
- 2000-03-01 RU RU2001126719/04A patent/RU2001126719A/ru unknown
- 2000-03-03 AR ARP000100950A patent/AR022824A1/es unknown
- 2000-03-03 CO CO00015569A patent/CO5180578A1/es not_active Application Discontinuation
- 2000-03-22 PE PE2000000247A patent/PE20001640A1/es not_active Application Discontinuation
-
2001
- 2001-08-23 ZA ZA200106966A patent/ZA200106966B/en unknown
- 2001-08-31 NO NO20014243A patent/NO20014243L/no not_active Application Discontinuation
- 2001-09-03 MA MA26311A patent/MA26775A1/fr unknown
-
2002
- 2002-06-24 HK HK02104690.3A patent/HK1044935A1/zh unknown
-
2003
- 2003-03-25 US US10/396,775 patent/US6762198B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CN1362951A (zh) | 2002-08-07 |
KR20010102485A (ko) | 2001-11-15 |
RU2001126719A (ru) | 2004-02-20 |
CZ20013155A3 (cs) | 2002-01-16 |
PL350452A1 (en) | 2002-12-16 |
TR200102524T2 (tr) | 2002-02-21 |
WO2000051993A2 (en) | 2000-09-08 |
WO2000051993A3 (en) | 2000-12-21 |
NO20014243L (no) | 2001-10-17 |
AU767344B2 (en) | 2003-11-06 |
HUP0201714A2 (en) | 2002-10-28 |
AR022824A1 (es) | 2002-09-04 |
EP1165530A2 (de) | 2002-01-02 |
SK12462001A3 (sk) | 2002-04-04 |
PE20001640A1 (es) | 2001-02-01 |
NO20014243D0 (no) | 2001-08-31 |
HK1044935A1 (zh) | 2002-11-08 |
US6566381B1 (en) | 2003-05-20 |
CA2366954A1 (en) | 2000-09-08 |
IL145085A0 (en) | 2002-06-30 |
CO5180578A1 (es) | 2002-07-30 |
HUP0201714A3 (en) | 2003-05-28 |
JP2002538146A (ja) | 2002-11-12 |
NZ513830A (en) | 2001-09-28 |
US6762198B2 (en) | 2004-07-13 |
US20030225074A1 (en) | 2003-12-04 |
BR0009244A (pt) | 2002-04-16 |
MXPA01008857A (es) | 2002-07-02 |
MA26775A1 (fr) | 2004-12-20 |
AU3711800A (en) | 2000-09-21 |
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