ZA200104378B - 3,4,5-Trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same. - Google Patents
3,4,5-Trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same. Download PDFInfo
- Publication number
- ZA200104378B ZA200104378B ZA200104378A ZA200104378A ZA200104378B ZA 200104378 B ZA200104378 B ZA 200104378B ZA 200104378 A ZA200104378 A ZA 200104378A ZA 200104378 A ZA200104378 A ZA 200104378A ZA 200104378 B ZA200104378 B ZA 200104378B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- alkyl
- group
- cycloalkyl
- tert
- Prior art date
Links
- -1 aryl nitrone compounds Chemical class 0.000 title claims description 78
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 116
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 96
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 56
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 206010061218 Inflammation Diseases 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 13
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 230000004054 inflammatory process Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 16
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 10
- 125000004442 acylamino group Chemical group 0.000 description 10
- 125000004423 acyloxy group Chemical group 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000005415 substituted alkoxy group Chemical group 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- 229930194542 Keto Natural products 0.000 description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000000468 ketone group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 125000005323 thioketone group Chemical group 0.000 description 9
- 125000005296 thioaryloxy group Chemical group 0.000 description 8
- 206010003246 arthritis Diseases 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000037976 chronic inflammation Diseases 0.000 description 3
- 230000006020 chronic inflammation Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 2
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010568 chiral column chromatography Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
- 229960001123 epoprostenol Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- PVMBWGUNDZTWEY-UHFFFAOYSA-N n-tert-butylmethanimine oxide Chemical compound CC(C)(C)[N+]([O-])=C PVMBWGUNDZTWEY-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11054198P | 1998-12-02 | 1998-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104378B true ZA200104378B (en) | 2002-08-28 |
Family
ID=22333591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104378A ZA200104378B (en) | 1998-12-02 | 2001-05-28 | 3,4,5-Trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6342523B1 (pt) |
| EP (1) | EP1135367A1 (pt) |
| JP (1) | JP2002531435A (pt) |
| KR (1) | KR20010087407A (pt) |
| CN (1) | CN1334800A (pt) |
| AU (1) | AU773343B2 (pt) |
| BR (1) | BR9915886A (pt) |
| CA (1) | CA2353402A1 (pt) |
| CZ (1) | CZ20011830A3 (pt) |
| EA (1) | EA004931B1 (pt) |
| HK (1) | HK1044147A1 (pt) |
| HU (1) | HUP0104576A3 (pt) |
| IL (1) | IL143506A0 (pt) |
| IS (1) | IS5958A (pt) |
| NO (1) | NO20012727L (pt) |
| NZ (1) | NZ512032A (pt) |
| PL (1) | PL349916A1 (pt) |
| SK (1) | SK7502001A3 (pt) |
| UA (1) | UA66401C2 (pt) |
| WO (1) | WO2000032567A1 (pt) |
| ZA (1) | ZA200104378B (pt) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050107366A1 (en) * | 1991-06-18 | 2005-05-19 | Carney John M. | Spin trapping pharmaceutical compositions and methods for use thereof |
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| US7115666B2 (en) * | 2002-10-15 | 2006-10-03 | Renovis, Inc. | Nitrone compounds, pharmaceutical compositions containing the same and methods for treating inflammation and neuropathic pain |
| US20050059638A1 (en) * | 2003-08-04 | 2005-03-17 | Kelly Michael G. | Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders |
| US20050182060A1 (en) * | 2004-02-13 | 2005-08-18 | Kelly Michael G. | 2-Substituted and 4-substituted aryl nitrone compounds |
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| US8227517B2 (en) | 2008-02-12 | 2012-07-24 | Tosk, Incorporated | Doxorubicin adjuvants to reduce toxicity and methods for using the same |
| CN101468970B (zh) | 2008-04-25 | 2011-05-11 | 暨南大学 | 一种硝酮类化合物及其制备方法和在制药中的应用 |
| CN102311396B (zh) * | 2010-07-05 | 2015-01-07 | 暨南大学 | 一种吡嗪类衍生物和其制备方法及在制药中的应用 |
| WO2013067084A1 (en) * | 2011-11-01 | 2013-05-10 | The Florida International University Board Of Trustees | Silylated azulenyl nitrone spin traps as chromotropic superoxide detectors |
| CN104803880B (zh) * | 2014-01-23 | 2017-11-21 | 广州喜鹊医药有限公司 | 一种具有神经保护作用的化合物及其制备方法和应用 |
| CN109438288B (zh) * | 2018-10-22 | 2021-05-07 | 河南中医药大学 | 一种n-硝酮取代芳香酰胺衍生物及其制备方法 |
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| US4224340A (en) | 1977-10-06 | 1980-09-23 | William H. Rorer, Inc. | Anti-inflammatory compositions containing α-phenyl-N-phenylnitrone compounds |
| GB2137619A (en) * | 1983-03-30 | 1984-10-10 | Gerald Scott | Nitrone compounds and stabilised rubber compositions containing them |
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| US5025032A (en) * | 1989-10-17 | 1991-06-18 | Oklahoma Medical Research Foundation | Phenyl butyl nitrone compositions and methods for treatment of oxidative tissue damage |
| US5036097A (en) | 1989-10-17 | 1991-07-30 | Oklahoma Medical Research Foundation | Phenylbutyl nitrone compositions and methods for prevention of gastric ulceration |
| EP0496796B1 (en) | 1989-10-17 | 1994-08-31 | Oklahoma Medical Research Foundation | Method and compositions for inhibition of disorders associated with oxidative damage |
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| US6002001A (en) | 1991-06-18 | 1999-12-14 | Oklahoma Medical Research Foundation | Spin trapping pharmaceutical compositions and methods for use thereof |
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| EP1021430A1 (en) | 1996-07-19 | 2000-07-26 | Centaur Pharmaceuticals, Inc. | Furan nitrone compounds |
| TW429241B (en) * | 1996-09-26 | 2001-04-11 | Sumitomo Pharma | Nitrone derivatives |
| US5994396A (en) | 1997-08-18 | 1999-11-30 | Centaur Pharmaceuticals, Inc. | Furansulfonic acid derivatives and pharmaceutical compositions containing the same |
| MA26553A1 (fr) | 1997-10-17 | 2004-12-20 | Centaur Pharmaceuticals Inc | Alpha-aryl-n-alkylnitrones et compositions pharmaceutiques contenant ceux-la |
| DE69904018D1 (en) | 1998-01-16 | 2003-01-02 | Centaur Pharmaceuticals Inc | Thiophennitronderivate |
| ZA99252B (en) | 1998-01-16 | 1999-07-14 | Centaur Pharmaceuticals Inc | Thioether furan nitrone compounds. |
| WO1999045909A2 (en) | 1998-03-13 | 1999-09-16 | Centaur Pharmaceuticals | Use of nitrone compounds for the inhibition of angiogenesis |
| ATE271384T1 (de) | 1998-05-19 | 2004-08-15 | Renovis Inc | Arylnitron therapeutische mittel zur behandlung von entzündlichen darmerkrankungen |
-
1999
- 1999-01-12 UA UA2001064521A patent/UA66401C2/uk unknown
- 1999-12-01 EA EA200100607A patent/EA004931B1/ru not_active IP Right Cessation
- 1999-12-01 BR BR9915886-8A patent/BR9915886A/pt not_active IP Right Cessation
- 1999-12-01 WO PCT/US1999/028479 patent/WO2000032567A1/en not_active Application Discontinuation
- 1999-12-01 AU AU19298/00A patent/AU773343B2/en not_active Ceased
- 1999-12-01 NZ NZ512032A patent/NZ512032A/xx unknown
- 1999-12-01 HU HU0104576A patent/HUP0104576A3/hu unknown
- 1999-12-01 JP JP2000585209A patent/JP2002531435A/ja not_active Withdrawn
- 1999-12-01 EP EP99962967A patent/EP1135367A1/en not_active Withdrawn
- 1999-12-01 KR KR1020017006908A patent/KR20010087407A/ko not_active Application Discontinuation
- 1999-12-01 SK SK750-2001A patent/SK7502001A3/sk unknown
- 1999-12-01 IL IL14350699A patent/IL143506A0/xx unknown
- 1999-12-01 CZ CZ20011830A patent/CZ20011830A3/cs unknown
- 1999-12-01 CA CA002353402A patent/CA2353402A1/en not_active Abandoned
- 1999-12-01 US US09/452,529 patent/US6342523B1/en not_active Expired - Fee Related
- 1999-12-01 CN CN99815924A patent/CN1334800A/zh active Pending
- 1999-12-01 PL PL99349916A patent/PL349916A1/xx unknown
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2001
- 2001-05-28 ZA ZA200104378A patent/ZA200104378B/en unknown
- 2001-05-31 IS IS5958A patent/IS5958A/is unknown
- 2001-06-01 NO NO20012727A patent/NO20012727L/no not_active Application Discontinuation
-
2002
- 2002-08-05 HK HK02105710.6A patent/HK1044147A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010087407A (ko) | 2001-09-15 |
| CA2353402A1 (en) | 2000-06-08 |
| AU773343B2 (en) | 2004-05-20 |
| EP1135367A1 (en) | 2001-09-26 |
| CN1334800A (zh) | 2002-02-06 |
| EA200100607A1 (ru) | 2001-12-24 |
| AU1929800A (en) | 2000-06-19 |
| HUP0104576A2 (hu) | 2002-05-29 |
| IS5958A (is) | 2001-05-31 |
| SK7502001A3 (en) | 2002-02-05 |
| HUP0104576A3 (en) | 2002-11-28 |
| CZ20011830A3 (cs) | 2001-10-17 |
| PL349916A1 (en) | 2002-10-07 |
| NZ512032A (en) | 2004-02-27 |
| EA004931B1 (ru) | 2004-10-28 |
| NO20012727D0 (no) | 2001-06-01 |
| WO2000032567A1 (en) | 2000-06-08 |
| UA66401C2 (en) | 2004-05-17 |
| US6342523B1 (en) | 2002-01-29 |
| IL143506A0 (en) | 2002-04-21 |
| NO20012727L (no) | 2001-07-26 |
| HK1044147A1 (zh) | 2002-10-11 |
| BR9915886A (pt) | 2001-08-21 |
| JP2002531435A (ja) | 2002-09-24 |
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