AP826A - Arysulfonylamino hydroxamic acid derivatives. - Google Patents
Arysulfonylamino hydroxamic acid derivatives. Download PDFInfo
- Publication number
- AP826A AP826A APAP/P/1998/001191A AP9801191A AP826A AP 826 A AP826 A AP 826A AP 9801191 A AP9801191 A AP 9801191A AP 826 A AP826 A AP 826A
- Authority
- AP
- ARIPO
- Prior art keywords
- aryl
- heteroaryl
- alkyl
- carboxylic acid
- aryloxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 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 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 13
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- 230000000694 effects Effects 0.000 claims abstract description 10
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- 208000025865 Ulcer Diseases 0.000 claims abstract description 7
- 206010003246 arthritis Diseases 0.000 claims abstract description 7
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 7
- 230000036269 ulceration Effects 0.000 claims abstract description 7
- 206010040047 Sepsis Diseases 0.000 claims abstract description 6
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 6
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- 230000036303 septic shock Effects 0.000 claims abstract description 6
- 208000030507 AIDS Diseases 0.000 claims abstract description 5
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- 229940035676 analgesics Drugs 0.000 claims abstract description 5
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- 231100000433 cytotoxic Toxicity 0.000 claims abstract description 5
- 230000001472 cytotoxic effect Effects 0.000 claims abstract description 5
- 208000037803 restenosis Diseases 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052684 Cerium Inorganic materials 0.000 claims description 26
- 125000004104 aryloxy group Chemical group 0.000 claims description 25
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 24
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 24
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 24
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 230000005764 inhibitory process Effects 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229940080818 propionamide Drugs 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- OMAOBBMMKLNINP-UHFFFAOYSA-N 1-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-n-hydroxycyclopropane-1-carboxamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CC1 OMAOBBMMKLNINP-UHFFFAOYSA-N 0.000 claims description 2
- LVYWHFWCJMTOJI-UHFFFAOYSA-N 2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxy-1,3-dihydroindene-2-carboxamide Chemical compound C1C2=CC=CC=C2CC1(C(=O)NO)NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 LVYWHFWCJMTOJI-UHFFFAOYSA-N 0.000 claims description 2
- WNLSBYSBOXDYRG-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxyazetidine-3-carboxamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CNC1 WNLSBYSBOXDYRG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 2
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- 229910014585 C2-Ce Inorganic materials 0.000 claims 5
- GLDRXIBLBZWPFO-UHFFFAOYSA-N 1-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-n-hydroxycyclobutane-1-carboxamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCC1 GLDRXIBLBZWPFO-UHFFFAOYSA-N 0.000 claims 1
- OCDVFODZPZVZMF-UHFFFAOYSA-N 1-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxycyclopropane-1-carboxamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CC1 OCDVFODZPZVZMF-UHFFFAOYSA-N 0.000 claims 1
- KXPJDYSBWNHMTI-UHFFFAOYSA-N 1-[[4-(4-fluorophenyl)phenyl]sulfonylamino]-n-hydroxycyclobutane-1-carboxamide Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCC1 KXPJDYSBWNHMTI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- 230000007850 degeneration Effects 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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- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 abstract description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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]
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Communicable Diseases (AREA)
- Dermatology (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3685797P | 1997-02-03 | 1997-02-03 |
Publications (2)
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| AP9801191A0 AP9801191A0 (en) | 1998-03-31 |
| AP826A true AP826A (en) | 2000-04-28 |
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| APAP/P/1998/001191A AP826A (en) | 1997-02-03 | 1998-01-29 | Arysulfonylamino hydroxamic acid derivatives. |
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| JP (1) | JP3765584B2 (id) |
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| CN (1) | CN1113862C (id) |
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| GT (1) | GT199800025A (id) |
| HN (1) | HN1998000011A (id) |
| HR (1) | HRP980058B1 (id) |
| HU (1) | HUP0000852A2 (id) |
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| IL (2) | IL131042A (id) |
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| KR100352316B1 (ko) | 1997-07-31 | 2002-09-12 | 더 프록터 앤드 갬블 캄파니 | 메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체 |
| PA8469301A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Procedimientos para la preparacion de acidos hidroxamicos. |
| PA8469601A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Procedimiento para alquilar sulfonamidas impedidas estericamente |
| GT199900044A (es) * | 1998-04-10 | 2000-09-14 | Procedimientos para preparar haluros de fenoxifenilsulfonilo. | |
| UA59453C2 (uk) * | 1998-08-12 | 2003-09-15 | Пфайзер Продактс Інк. | Похідні гідроксипіпеколат гідроксамової кислоти як інгібітори матричних металопротеїназ |
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6753337B2 (en) | 1999-01-27 | 2004-06-22 | Wyeth Holdings Corporation | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
| US6946473B2 (en) | 1999-01-27 | 2005-09-20 | Wyeth Holdings Corporation | Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors |
| US6225311B1 (en) | 1999-01-27 | 2001-05-01 | American Cyanamid Company | Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors |
| US6340691B1 (en) | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| US6200996B1 (en) | 1999-01-27 | 2001-03-13 | American Cyanamid Company | Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors |
| CN1178915C (zh) | 1999-01-27 | 2004-12-08 | 惠氏控股有限公司 | 含有炔基的异羟肟酸衍生物、其制备及其作为基质金属蛋白酶抑制剂/TNF-α转变酶抑制剂的用途 |
| US6326516B1 (en) | 1999-01-27 | 2001-12-04 | American Cyanamid Company | Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors |
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