OA11142A - Arylsulfonyl hydroxamic acid derivatives - Google Patents
Arylsulfonyl hydroxamic acid derivatives Download PDFInfo
- Publication number
- OA11142A OA11142A OA9900174A OA9900174A OA11142A OA 11142 A OA11142 A OA 11142A OA 9900174 A OA9900174 A OA 9900174A OA 9900174 A OA9900174 A OA 9900174A OA 11142 A OA11142 A OA 11142A
- Authority
- OA
- OAPI
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- alkoxy
- crc6
- Prior art date
Links
- -1 Arylsulfonyl hydroxamic Chemical compound 0.000 title claims abstract description 71
- 239000002253 acid Substances 0.000 title description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 14
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 11
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 206010003246 arthritis Diseases 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 206010040047 Sepsis Diseases 0.000 claims abstract description 7
- 208000028169 periodontal disease Diseases 0.000 claims abstract description 7
- 208000030507 AIDS Diseases 0.000 claims abstract description 6
- 231100000433 cytotoxic Toxicity 0.000 claims abstract description 6
- 230000001472 cytotoxic effect Effects 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
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 5
- 230000036303 septic shock Effects 0.000 claims abstract description 5
- 206010014989 Epidermolysis bullosa Diseases 0.000 claims abstract description 4
- 206010039705 Scleritis Diseases 0.000 claims abstract description 4
- 208000002780 macular degeneration Diseases 0.000 claims abstract description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 125000003118 aryl group Chemical group 0.000 claims description 98
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001301 oxygen Chemical group 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 27
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 229910052684 Cerium Inorganic materials 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 229910052717 sulfur Chemical group 0.000 claims description 20
- 239000011593 sulfur Chemical group 0.000 claims description 20
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
- 230000005764 inhibitory process Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 150000008575 L-amino acids Chemical class 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- CSLDBJUJDSYAKG-FPOVZHCZSA-N (2r,3s)-1-[4-(1,3-benzothiazol-2-ylmethoxy)phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=NC2=CC=CC=C2S1 CSLDBJUJDSYAKG-FPOVZHCZSA-N 0.000 claims 1
- VFMQGJQJUNCZDG-FPOVZHCZSA-N (2r,3s)-1-[4-[2-(4-fluorophenyl)ethoxy]phenyl]sulfonyl-n,3-dihydroxy-3-methylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 VFMQGJQJUNCZDG-FPOVZHCZSA-N 0.000 claims 1
- UFIPRXRNECOZCM-ZWKOTPCHSA-N (2r,3s)-n,3-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 UFIPRXRNECOZCM-ZWKOTPCHSA-N 0.000 claims 1
- LTXMNGNZBGPTLR-LSDHHAIUSA-N (2r,3s)-n,3-dihydroxy-1-[4-(1,3-thiazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CN=CS1 LTXMNGNZBGPTLR-LSDHHAIUSA-N 0.000 claims 1
- UFIMUQYMICWLMR-WCQYABFASA-N (2r,3s)-n,3-dihydroxy-1-[4-(2h-tetrazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=NN=NN1 UFIMUQYMICWLMR-WCQYABFASA-N 0.000 claims 1
- SLKKVBIPVXPLEG-DLBZAZTESA-N (2r,3s)-n,3-dihydroxy-1-[4-(pyridin-4-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=NC=C1 SLKKVBIPVXPLEG-DLBZAZTESA-N 0.000 claims 1
- WOQSKGWYPFEBIZ-RDJZCZTQSA-N (2r,3s)-n,3-dihydroxy-3-methyl-1-[4-(1,3-thiazol-5-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CN=CS1 WOQSKGWYPFEBIZ-RDJZCZTQSA-N 0.000 claims 1
- DOOZILOLHOKUGO-HKUYNNGSSA-N (2r,3s)-n,3-dihydroxy-3-methyl-1-[4-(pyridin-4-ylmethoxy)phenyl]sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@](C)(O)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=NC=C1 DOOZILOLHOKUGO-HKUYNNGSSA-N 0.000 claims 1
- JMBOAEVTEXTTPO-BXUZGUMPSA-N (2r,4r)-1-[3-(4-fluorophenoxy)propylsulfonyl]-2-(hydroxycarbamoyl)piperidine-4-carboxylic acid Chemical compound ONC(=O)[C@H]1C[C@H](C(O)=O)CCN1S(=O)(=O)CCCOC1=CC=C(F)C=C1 JMBOAEVTEXTTPO-BXUZGUMPSA-N 0.000 claims 1
- ACEUKQZDNBIUHG-CRAIPNDOSA-N (2r,4r)-n,4-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ACEUKQZDNBIUHG-CRAIPNDOSA-N 0.000 claims 1
- KEVSGIPPEHZMGV-OALZAMAHSA-N (2r,4r)-n-hydroxy-1-(4-methoxyphenyl)sulfonyl-4-(piperazine-1-carbonyl)piperidine-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1S(=O)(=O)N1[C@@H](C(=O)NO)C[C@H](C(=O)N2CCNCC2)CC1 KEVSGIPPEHZMGV-OALZAMAHSA-N 0.000 claims 1
- FCLQINRREQAAHO-MAUKXSAKSA-N (2r,4s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,4-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 FCLQINRREQAAHO-MAUKXSAKSA-N 0.000 claims 1
- ACEUKQZDNBIUHG-MAUKXSAKSA-N (2r,4s)-n,4-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1C[C@@H](O)CCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ACEUKQZDNBIUHG-MAUKXSAKSA-N 0.000 claims 1
- UUSUIALWMWHMSS-CRAIPNDOSA-N (2r,5r)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,5-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 UUSUIALWMWHMSS-CRAIPNDOSA-N 0.000 claims 1
- UUSUIALWMWHMSS-MAUKXSAKSA-N (2r,5s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-n,5-dihydroxypiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 UUSUIALWMWHMSS-MAUKXSAKSA-N 0.000 claims 1
- GIGWICZCQGBJDH-MAUKXSAKSA-N (2r,5s)-n,5-dihydroxy-1-(4-phenylmethoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1CC[C@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GIGWICZCQGBJDH-MAUKXSAKSA-N 0.000 claims 1
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- WOZBOFIMMNNBIE-LEWJYISDSA-N propan-2-yl n-[(2r,3s)-1-[4-[(4-fluorophenyl)methoxy]phenyl]sulfonyl-2-(hydroxycarbamoyl)piperidin-3-yl]carbamate Chemical compound ONC(=O)[C@H]1[C@@H](NC(=O)OC(C)C)CCCN1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(F)C=C1 WOZBOFIMMNNBIE-LEWJYISDSA-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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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- 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
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- 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
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- 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
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
Applications Claiming Priority (1)
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US3760097P | 1997-02-11 | 1997-02-11 |
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OA9900174A OA11142A (en) | 1997-02-11 | 1999-08-06 | Arylsulfonyl hydroxamic acid derivatives |
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US (1) | US6599890B1 (pt) |
EP (1) | EP0960098A1 (pt) |
JP (1) | JP3710489B2 (pt) |
KR (1) | KR20000070923A (pt) |
CN (1) | CN1247531A (pt) |
AP (1) | AP958A (pt) |
AR (1) | AR011123A1 (pt) |
AU (1) | AU722784B2 (pt) |
BG (1) | BG63430B1 (pt) |
BR (1) | BR9807678A (pt) |
CA (1) | CA2280151C (pt) |
CO (1) | CO4950619A1 (pt) |
DZ (1) | DZ2416A1 (pt) |
EA (1) | EA002546B1 (pt) |
GT (1) | GT199800026A (pt) |
HN (1) | HN1998000020A (pt) |
HR (1) | HRP980070B1 (pt) |
HU (1) | HUP0000657A3 (pt) |
ID (1) | ID22809A (pt) |
IL (1) | IL131123A0 (pt) |
IS (1) | IS5130A (pt) |
MA (1) | MA24469A1 (pt) |
NO (1) | NO993836L (pt) |
NZ (1) | NZ336836A (pt) |
OA (1) | OA11142A (pt) |
PA (1) | PA8446101A1 (pt) |
PE (1) | PE58699A1 (pt) |
PL (1) | PL334997A1 (pt) |
SA (1) | SA98180856A (pt) |
SK (1) | SK101399A3 (pt) |
TN (1) | TNSN98025A1 (pt) |
TR (1) | TR199901926T2 (pt) |
TW (1) | TW502020B (pt) |
UY (1) | UY24880A1 (pt) |
WO (1) | WO1998034918A1 (pt) |
YU (1) | YU37499A (pt) |
ZA (1) | ZA981061B (pt) |
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- 1998-02-10 ZA ZA9801061A patent/ZA981061B/xx unknown
- 1998-02-10 TN TNTNSN98025A patent/TNSN98025A1/fr unknown
- 1998-02-10 DZ DZ980026A patent/DZ2416A1/xx active
- 1998-02-10 AR ARP980100582A patent/AR011123A1/es not_active Application Discontinuation
- 1998-02-10 MA MA24960A patent/MA24469A1/fr unknown
- 1998-02-11 CO CO98007136A patent/CO4950619A1/es unknown
- 1998-02-12 HR HR980070A patent/HRP980070B1/xx not_active IP Right Cessation
- 1998-02-15 SA SA98180856A patent/SA98180856A/ar unknown
- 1998-02-18 PA PA19988446101A patent/PA8446101A1/es unknown
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1999
- 1999-07-23 IS IS5130A patent/IS5130A/is unknown
- 1999-08-05 BG BG103641A patent/BG63430B1/bg active Active
- 1999-08-06 OA OA9900174A patent/OA11142A/en unknown
- 1999-08-10 NO NO993836A patent/NO993836L/no not_active Application Discontinuation
-
2000
- 2000-11-08 US US09/708,328 patent/US6599890B1/en not_active Expired - Fee Related
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