UA66401C2 - 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same - Google Patents

3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same Download PDF

Info

Publication number: UA66401C2
Authority: UA; Ukraine
Prior art keywords: alkyl; group; substituted; cycloalkyl; tert
Prior art date: 1998-12-02

Application number

UA2001064521A

Other languages

English (en)

Ukrainian (uk)

Inventor

John M Karni

Original Assignee

Sentor Pharmaceuticals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-12-02

Filing date

1999-01-12

Publication date

2004-05-17

1999-01-12 Application filed by Sentor Pharmaceuticals Inc filed Critical Sentor Pharmaceuticals Inc

2004-05-17 Publication of UA66401C2 publication Critical patent/UA66401C2/uk

Links

-1 aryl nitrone compounds Chemical class 0.000 title claims abstract description 84
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 42
150000001875 compounds Chemical class 0.000 claims abstract description 146
230000004054 inflammatory process Effects 0.000 claims abstract description 21
206010061218 Inflammation Diseases 0.000 claims abstract description 19
241000124008 Mammalia Species 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims description 108
125000000753 cycloalkyl group Chemical group 0.000 claims description 82
125000000547 substituted alkyl group Chemical group 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 47
238000000034 method Methods 0.000 claims description 45
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 44
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 44
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
125000000392 cycloalkenyl group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 22
125000003118 aryl group Chemical group 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 22
125000002947 alkylene group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000005017 substituted alkenyl group Chemical group 0.000 claims description 15
125000005156 substituted alkylene group Chemical group 0.000 claims description 15
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
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
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 11
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 11
125000004426 substituted alkynyl group Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
238000012876 topography Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 55
206010003246 arthritis Diseases 0.000 abstract description 12
239000003153 chemical reaction reagent Substances 0.000 abstract description 10
239000003814 drug Substances 0.000 abstract description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 51
230000015572 biosynthetic process Effects 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
239000007787 solid Substances 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 33
238000003786 synthesis reaction Methods 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
239000003921 oil Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
238000004611 spectroscopical analysis Methods 0.000 description 19
125000001424 substituent group Chemical group 0.000 description 19
238000004809 thin layer chromatography Methods 0.000 description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
108010037462 Cyclooxygenase 2 Proteins 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 14
210000002683 foot Anatomy 0.000 description 14
239000007858 starting material Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 14
125000003545 alkoxy group Chemical group 0.000 description 13
238000002474 experimental method Methods 0.000 description 13
125000005309 thioalkoxy group Chemical group 0.000 description 13
DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
108010037464 Cyclooxygenase 1 Proteins 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
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 12
239000000047 product Substances 0.000 description 12
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 11
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 11
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 11
241000700159 Rattus Species 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
239000000126 substance Substances 0.000 description 11
238000004435 EPR spectroscopy Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
229930194542 Keto Natural products 0.000 description 10
125000004423 acyloxy group Chemical group 0.000 description 10
238000011156 evaluation Methods 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
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 10
230000004968 inflammatory condition Effects 0.000 description 10
125000000468 ketone group Chemical group 0.000 description 10
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 10
238000011282 treatment Methods 0.000 description 10
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 9
108090000790 Enzymes Proteins 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
125000004442 acylamino group Chemical group 0.000 description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
125000004104 aryloxy group Chemical group 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 8
230000002035 prolonged effect Effects 0.000 description 8
150000003180 prostaglandins Chemical class 0.000 description 8
125000005415 substituted alkoxy group Chemical group 0.000 description 8
238000012360 testing method Methods 0.000 description 8
125000005296 thioaryloxy group Chemical group 0.000 description 8
150000003573 thiols Chemical class 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002671 adjuvant Substances 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
235000010418 carrageenan Nutrition 0.000 description 7
239000000679 carrageenan Substances 0.000 description 7
229920001525 carrageenan Polymers 0.000 description 7
229940113118 carrageenan Drugs 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
125000005323 thioketone group Chemical group 0.000 description 7
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
229940114079 arachidonic acid Drugs 0.000 description 6
235000021342 arachidonic acid Nutrition 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 6
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
206010030113 Oedema Diseases 0.000 description 5
125000005129 aryl carbonyl group Chemical group 0.000 description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 5
150000002443 hydroxylamines Chemical class 0.000 description 5
229960000905 indomethacin Drugs 0.000 description 5
230000006698 induction Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
XWESXZZECGOXDQ-UHFFFAOYSA-N n-tert-butylhydroxylamine Chemical compound CC(C)(C)NO XWESXZZECGOXDQ-UHFFFAOYSA-N 0.000 description 5
229940094443 oxytocics prostaglandins Drugs 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
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CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
125000004001 thioalkyl group Chemical group 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
102000008186 Collagen Human genes 0.000 description 4
108010035532 Collagen Proteins 0.000 description 4
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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239000004480 active ingredient Substances 0.000 description 4
125000006598 aminocarbonylamino group Chemical group 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000002156 mixing Methods 0.000 description 4
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HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000012748 slip agent Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
239000001962 taste-modifying agent Substances 0.000 description 1
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 description 1
210000002435 tendon Anatomy 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
150000003595 thromboxanes Chemical class 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
238000011269 treatment regimen Methods 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
201000010653 vesiculitis Diseases 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
239000003871 white petrolatum Substances 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 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)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (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)

UA2001064521A 1998-12-02 1999-01-12 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same UA66401C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11054198P	1998-12-02	1998-12-02
PCT/US1999/028479 WO2000032567A1 (en)	1998-12-02	1999-12-01	3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same

Publications (1)

Publication Number	Publication Date
UA66401C2 true UA66401C2 (en)	2004-05-17

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ID=22333591

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001064521A UA66401C2 (en)	1998-12-02	1999-01-12	3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same

Country Status (21)

Country	Link
US (1)	US6342523B1 (is)
EP (1)	EP1135367A1 (is)
JP (1)	JP2002531435A (is)
KR (1)	KR20010087407A (is)
CN (1)	CN1334800A (is)
AU (1)	AU773343B2 (is)
BR (1)	BR9915886A (is)
CA (1)	CA2353402A1 (is)
CZ (1)	CZ20011830A3 (is)
EA (1)	EA004931B1 (is)
HK (1)	HK1044147A1 (is)
HU (1)	HUP0104576A3 (is)
IL (1)	IL143506A0 (is)
IS (1)	IS5958A (is)
NO (1)	NO20012727L (is)
NZ (1)	NZ512032A (is)
PL (1)	PL349916A1 (is)
SK (1)	SK7502001A3 (is)
UA (1)	UA66401C2 (is)
WO (1)	WO2000032567A1 (is)
ZA (1)	ZA200104378B (is)

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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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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
US9156862B2 (en)	2011-11-01	2015-10-13	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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1999
- 1999-01-12 UA UA2001064521A patent/UA66401C2/uk unknown
- 1999-12-01 BR BR9915886-8A patent/BR9915886A/pt not_active IP Right Cessation
- 1999-12-01 IL IL14350699A patent/IL143506A0/xx unknown
- 1999-12-01 JP JP2000585209A patent/JP2002531435A/ja not_active Withdrawn
- 1999-12-01 HU HU0104576A patent/HUP0104576A3/hu unknown
- 1999-12-01 CZ CZ20011830A patent/CZ20011830A3/cs unknown
- 1999-12-01 SK SK750-2001A patent/SK7502001A3/sk unknown
- 1999-12-01 AU AU19298/00A patent/AU773343B2/en not_active Ceased
- 1999-12-01 PL PL99349916A patent/PL349916A1/xx unknown
- 1999-12-01 CA CA002353402A patent/CA2353402A1/en not_active Abandoned
- 1999-12-01 KR KR1020017006908A patent/KR20010087407A/ko not_active Ceased
- 1999-12-01 HK HK02105710.6A patent/HK1044147A1/zh unknown
- 1999-12-01 NZ NZ512032A patent/NZ512032A/xx unknown
- 1999-12-01 CN CN99815924A patent/CN1334800A/zh active Pending
- 1999-12-01 EP EP99962967A patent/EP1135367A1/en not_active Withdrawn
- 1999-12-01 WO PCT/US1999/028479 patent/WO2000032567A1/en not_active Ceased
- 1999-12-01 EA EA200100607A patent/EA004931B1/ru not_active IP Right Cessation
- 1999-12-01 US US09/452,529 patent/US6342523B1/en not_active Expired - Fee Related
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

Also Published As

Publication number	Publication date
EP1135367A1 (en)	2001-09-26
CA2353402A1 (en)	2000-06-08
IL143506A0 (en)	2002-04-21
CZ20011830A3 (cs)	2001-10-17
HK1044147A1 (zh)	2002-10-11
NO20012727L (no)	2001-07-26
PL349916A1 (en)	2002-10-07
AU773343B2 (en)	2004-05-20
CN1334800A (zh)	2002-02-06
HUP0104576A2 (hu)	2002-05-29
WO2000032567A1 (en)	2000-06-08
ZA200104378B (en)	2002-08-28
NZ512032A (en)	2004-02-27
IS5958A (is)	2001-05-31
NO20012727D0 (no)	2001-06-01
EA200100607A1 (ru)	2001-12-24
AU1929800A (en)	2000-06-19
SK7502001A3 (en)	2002-02-05
US6342523B1 (en)	2002-01-29
KR20010087407A (ko)	2001-09-15
HUP0104576A3 (en)	2002-11-28
EA004931B1 (ru)	2004-10-28
BR9915886A (pt)	2001-08-21
JP2002531435A (ja)	2002-09-24

Publication	Publication Date	Title
UA66401C2 (en)	2004-05-17	3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same
CN102020563A (zh)	2011-04-20	新的姜黄素类似物及其用途
US6835754B2 (en)	2004-12-28	Use of aryl nitrone compounds in methods for treating neuropathic pain
US6083989A (en)	2000-07-04	Aryl nitrone therapeutics for the treatment of inflammatory bowel disease
US5972977A (en)	1999-10-26	Ophthalmic pharmaceutical compositions comprising a nitrone compound and methods for treating ocular inflammation using such compositions
US6730700B2 (en)	2004-05-04	3,4,5,-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same
US6197826B1 (en)	2001-03-06	α-(2-hydroxyphenyl) nitrone compounds, pharmaceutical compositions containing the same and methods for treating inflammation
JP3157846B2 (ja)	2001-04-16	カテコール誘導体、その生理学的に許容しうる塩を有効成分としてなる脂質過酸化により引き起こされる組織損傷の予防または治療剤
US20020128256A1 (en)	2002-09-12	Methods for the treatment or prevention of inflammatory diseases characterized by abnormal cell proliferation
EP1077694A1 (en)	2001-02-28	Aryl nitrone therapeutics for the treatment of inflammatory bowel disease
CA2311129A1 (en)	1999-06-03	Use of substituted diphenyl indanone, indane and indole compounds for the treatment or prevention of sickle cell disease, inflammatory diseases characterized by abnormal cell proliferation, diarrhea and scours
US20040142983A1 (en)	2004-07-22	Nitrone compounds, pharmaceutical compositions containing the same and methods for treating inflammation and neuropathic pain
MXPA01005555A (en)	2002-05-09	3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same
CA1243671A (en)	1988-10-25	2-adamantanone oxime carbamate derivatives
US3899488A (en)	1975-08-12	2H-indazolone compound
EP0706995A1 (fr)	1996-04-17	Utilisation de dérivés de déhydroalanines pour protéger la peau, les muqueuses et/ou les cheveux du stress oxydant, compositions cosmétiques ou dermatologiques les contenant et composés nouveaux utilisés
JPH04211676A (ja)	1992-08-03	新規化合物並びにそれを含有する血管拡張剤及び皮膚外用剤
WO2006125276A1 (en)	2006-11-30	Phenylalkanol compounds
JPH0138085B2 (is)	1989-08-11
BE718270A (is)	1969-01-20
AU2003264308A1 (en)	2004-01-08	Aryl nitrone therapeutics for the treatment of inflammatory bowel disease
HK1032357A1 (en)	2001-07-20	Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation
HK1032357B (en)	2005-01-21	Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation