NO317977B1 - Sulfonylaminoderivater som hemmer matriks-nedbrytende metalloproteinaser - Google Patents
Sulfonylaminoderivater som hemmer matriks-nedbrytende metalloproteinaser Download PDFInfo
- Publication number
- NO317977B1 NO317977B1 NO20003565A NO20003565A NO317977B1 NO 317977 B1 NO317977 B1 NO 317977B1 NO 20003565 A NO20003565 A NO 20003565A NO 20003565 A NO20003565 A NO 20003565A NO 317977 B1 NO317977 B1 NO 317977B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- compound
- formula
- sulfonylamino
- chlorobiphenyl
- Prior art date
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- 102000002274 Matrix Metalloproteinases Human genes 0.000 title claims description 11
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title claims description 11
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 210
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 63
- -1 tetrahydroquinazolinyl Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001424 substituent group Chemical group 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 4
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- DOWDJFVLAJDWNC-OAQYLSRUSA-N (2r)-2-[(4-phenoxyphenyl)sulfonylamino]-5-(1,1,3-trioxo-1,2-benzothiazol-2-yl)pentanoic acid Chemical compound N([C@H](CCCN1S(C2=CC=CC=C2C1=O)(=O)=O)C(=O)O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 DOWDJFVLAJDWNC-OAQYLSRUSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- WJAPVQNVNVTVLB-JOCHJYFZSA-N (2r)-5-(1-methyl-2,4-dioxoquinazolin-3-yl)-2-[(4-phenoxyphenyl)sulfonylamino]pentanoic acid Chemical compound N([C@H](CCCN1C(=O)C2=CC=CC=C2N(C1=O)C)C(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 WJAPVQNVNVTVLB-JOCHJYFZSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
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- KQNIMTMBOOKZKI-HSZRJFAPSA-N (2r)-2-[[4-(4-chlorophenyl)phenyl]sulfonylamino]-5-[(4-methylphenyl)sulfonylamino]pentanoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCC[C@H](C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 KQNIMTMBOOKZKI-HSZRJFAPSA-N 0.000 claims 1
- VENUYGVWTPYHER-OAQYLSRUSA-N (2r)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-5-(1,1,3-trioxo-1,2-benzothiazol-2-yl)pentanoic acid Chemical compound N([C@H](CCCN1S(C2=CC=CC=C2C1=O)(=O)=O)C(=O)O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 VENUYGVWTPYHER-OAQYLSRUSA-N 0.000 claims 1
- OJVGANDYUNIVCR-JOCHJYFZSA-N (2r)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-5-(1-methyl-2,4-dioxoquinazolin-3-yl)pentanoic acid Chemical compound N([C@H](CCCN1C(=O)C2=CC=CC=C2N(C1=O)C)C(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 OJVGANDYUNIVCR-JOCHJYFZSA-N 0.000 claims 1
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07C311/16—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 hydrogen atoms or to an acyclic carbon atom
- C07C311/19—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 hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- 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
- C07D239/96—Two oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1881998A | 1998-02-04 | 1998-02-04 | |
PCT/EP1999/000646 WO1999042443A1 (en) | 1998-02-04 | 1999-02-02 | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
Publications (3)
Publication Number | Publication Date |
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NO20003565D0 NO20003565D0 (no) | 2000-07-11 |
NO20003565L NO20003565L (no) | 2000-10-03 |
NO317977B1 true NO317977B1 (no) | 2005-01-17 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20003565A NO317977B1 (no) | 1998-02-04 | 2000-07-11 | Sulfonylaminoderivater som hemmer matriks-nedbrytende metalloproteinaser |
Country Status (18)
Country | Link |
---|---|
US (1) | US6277987B1 (ko) |
EP (2) | EP1918278A1 (ko) |
JP (1) | JP4750272B2 (ko) |
KR (1) | KR20010040698A (ko) |
CN (1) | CN1195735C (ko) |
AU (1) | AU747911B2 (ko) |
BR (1) | BR9909322A (ko) |
CA (1) | CA2318145C (ko) |
HU (1) | HUP0101176A3 (ko) |
ID (1) | ID24957A (ko) |
IL (1) | IL137465A0 (ko) |
NO (1) | NO317977B1 (ko) |
NZ (1) | NZ505968A (ko) |
PL (1) | PL342009A1 (ko) |
RU (1) | RU2208609C2 (ko) |
SK (1) | SK11692000A3 (ko) |
TR (1) | TR200002224T2 (ko) |
WO (1) | WO1999042443A1 (ko) |
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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 |
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GB0412553D0 (en) | 2004-06-04 | 2004-07-07 | Univ Aberdeen | Therapeutic agents for the treatment of bone conditions |
SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
US7648992B2 (en) | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
US20080187508A1 (en) * | 2004-09-08 | 2008-08-07 | Boys Town National Research Hospital | Treatment of Golmerular Basement Membrane Disease Involving Matrix Metalloproteinase-12 |
US20100003276A1 (en) * | 2004-12-07 | 2010-01-07 | Hermes Jeffery D | Methods for treating anthrax and inhibiting lethal factor |
SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
US7576222B2 (en) * | 2004-12-28 | 2009-08-18 | Wyeth | Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase |
US20100247512A1 (en) * | 2006-03-31 | 2010-09-30 | The Regents Of The University Of Michigan | Pericellular Collagenase Directs the 3-Dimensional Development of White Adipose Tissue |
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GB0705400D0 (en) | 2007-03-21 | 2007-05-02 | Univ Aberdeen | Therapeutic compounds andm their use |
PL2268612T3 (pl) | 2008-03-24 | 2015-02-27 | Novartis Ag | Arylosulfonamidowe inhibitory metaloproteinaz macierzy |
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-
1999
- 1999-02-02 BR BR9909322-7A patent/BR9909322A/pt not_active IP Right Cessation
- 1999-02-02 IL IL13746599A patent/IL137465A0/xx unknown
- 1999-02-02 EP EP07120827A patent/EP1918278A1/en not_active Withdrawn
- 1999-02-02 NZ NZ505968A patent/NZ505968A/xx unknown
- 1999-02-02 PL PL99342009A patent/PL342009A1/xx not_active Application Discontinuation
- 1999-02-02 CA CA002318145A patent/CA2318145C/en not_active Expired - Fee Related
- 1999-02-02 CN CNB998027154A patent/CN1195735C/zh not_active Expired - Fee Related
- 1999-02-02 SK SK1169-2000A patent/SK11692000A3/sk unknown
- 1999-02-02 ID IDW20001501A patent/ID24957A/id unknown
- 1999-02-02 RU RU2000123166/04A patent/RU2208609C2/ru not_active IP Right Cessation
- 1999-02-02 TR TR2000/02224T patent/TR200002224T2/xx unknown
- 1999-02-02 AU AU29235/99A patent/AU747911B2/en not_active Ceased
- 1999-02-02 KR KR1020007008576A patent/KR20010040698A/ko not_active Application Discontinuation
- 1999-02-02 JP JP2000532395A patent/JP4750272B2/ja not_active Expired - Fee Related
- 1999-02-02 EP EP99910174A patent/EP1053226A1/en not_active Ceased
- 1999-02-02 HU HU0101176A patent/HUP0101176A3/hu unknown
- 1999-02-02 WO PCT/EP1999/000646 patent/WO1999042443A1/en not_active Application Discontinuation
- 1999-02-03 US US09/243,854 patent/US6277987B1/en not_active Expired - Fee Related
-
2000
- 2000-07-11 NO NO20003565A patent/NO317977B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
TR200002224T2 (tr) | 2000-12-21 |
KR20010040698A (ko) | 2001-05-15 |
NO20003565L (no) | 2000-10-03 |
JP2002503720A (ja) | 2002-02-05 |
SK11692000A3 (sk) | 2001-02-12 |
JP4750272B2 (ja) | 2011-08-17 |
IL137465A0 (en) | 2001-07-24 |
HUP0101176A3 (en) | 2002-06-28 |
CN1195735C (zh) | 2005-04-06 |
AU747911B2 (en) | 2002-05-30 |
US6277987B1 (en) | 2001-08-21 |
PL342009A1 (en) | 2001-05-07 |
WO1999042443A1 (en) | 1999-08-26 |
CA2318145C (en) | 2009-10-27 |
EP1918278A1 (en) | 2008-05-07 |
AU2923599A (en) | 1999-09-06 |
HUP0101176A2 (hu) | 2001-09-28 |
BR9909322A (pt) | 2000-12-05 |
CA2318145A1 (en) | 1999-08-26 |
RU2208609C2 (ru) | 2003-07-20 |
ID24957A (id) | 2000-08-31 |
NZ505968A (en) | 2003-03-28 |
EP1053226A1 (en) | 2000-11-22 |
CN1290250A (zh) | 2001-04-04 |
NO20003565D0 (no) | 2000-07-11 |
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