RU2415864C2 - Нитрооксипроизводные стероидов - Google Patents
Нитрооксипроизводные стероидов Download PDFInfo
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- RU2415864C2 RU2415864C2 RU2008111076/04A RU2008111076A RU2415864C2 RU 2415864 C2 RU2415864 C2 RU 2415864C2 RU 2008111076/04 A RU2008111076/04 A RU 2008111076/04A RU 2008111076 A RU2008111076 A RU 2008111076A RU 2415864 C2 RU2415864 C2 RU 2415864C2
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- Russia
- Prior art keywords
- formula
- group
- nitrate
- compounds
- compound
- Prior art date
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- 150000003431 steroids Chemical class 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 69
- -1 nitrooxymethyl Chemical group 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- QIEPWCSVQYUPIY-LEKSSAKUSA-N Delta(1)-progesterone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QIEPWCSVQYUPIY-LEKSSAKUSA-N 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- 239000003246 corticosteroid Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 201000004624 Dermatitis Diseases 0.000 claims description 17
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 208000017520 skin disease Diseases 0.000 claims description 15
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 14
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910002651 NO3 Inorganic materials 0.000 claims description 11
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
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- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 8
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- 125000005843 halogen group Chemical group 0.000 claims description 7
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 6
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 claims description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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- 238000009835 boiling Methods 0.000 claims description 3
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- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000243 solution Substances 0.000 description 36
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 231100000401 skin blanching Toxicity 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
-
- 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
- A61P17/04—Antipruritics
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- A61P17/08—Antiseborrheics
-
- 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
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05019155 | 2005-09-02 | ||
| EP05019155.0 | 2005-09-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008111076A RU2008111076A (ru) | 2009-10-10 |
| RU2415864C2 true RU2415864C2 (ru) | 2011-04-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008111076/04A RU2415864C2 (ru) | 2005-09-02 | 2006-08-04 | Нитрооксипроизводные стероидов |
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| CN (2) | CN101300265A (enExample) |
| AR (1) | AR056868A1 (enExample) |
| AU (1) | AU2006286838C1 (enExample) |
| BR (1) | BRPI0614967A2 (enExample) |
| CA (1) | CA2621117A1 (enExample) |
| ES (1) | ES2393363T3 (enExample) |
| IL (2) | IL189337A0 (enExample) |
| NO (1) | NO20081614L (enExample) |
| NZ (1) | NZ566128A (enExample) |
| RU (1) | RU2415864C2 (enExample) |
| SG (1) | SG158916A1 (enExample) |
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| UY (1) | UY29779A1 (enExample) |
| WO (1) | WO2007025632A2 (enExample) |
| ZA (1) | ZA200801789B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8802726B2 (en) | 2006-02-03 | 2014-08-12 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| MX2009008334A (es) * | 2007-02-05 | 2009-08-12 | Nicox Sa | Esteroides que liberan oxido nitrico. |
| EP1964550A1 (en) * | 2007-03-01 | 2008-09-03 | NicOx S.A. | Glucocorticoid-nitrooxyderivative compositions |
| ES2324007A1 (es) * | 2007-10-25 | 2009-07-28 | Ferrer Internacional, S.A. | Una forma amorfa de un compuesto antiinflamatorio. |
| WO2010012567A1 (en) * | 2008-07-31 | 2010-02-04 | Nicox S.A. | Glucocorticoids attached to nitrate esters via an aromatic linker in position 21 and their use in ophthalmology |
| US20110130376A1 (en) * | 2008-08-05 | 2011-06-02 | Nicox S.A. | New no releasing steroids derivatives |
| CN102186873A (zh) * | 2008-08-05 | 2011-09-14 | 尼科克斯公司 | 用于治疗视网膜和黄斑疾病的新型释放no的甾类化合物 |
| WO2010096320A2 (en) * | 2009-02-18 | 2010-08-26 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
| US8062653B2 (en) * | 2009-02-18 | 2011-11-22 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
| US9022788B2 (en) * | 2009-10-17 | 2015-05-05 | Gregory John Stahler | System and method for cardiac defibrillation response simulation in health training mannequin |
| ES2362894B1 (es) | 2009-11-16 | 2012-05-21 | Ferrer Internacional S.A. | Procedimiento de preparación del �?cido 4-nitro-oxi-metil-benzoico. |
| ES2359708B1 (es) * | 2009-11-16 | 2012-03-30 | Ferrer Internacional S.A. | Procedimiento de preparación de la (11beta,16alfa)-9-fluoro-11-hidroxi-16,17-[1-metil-etilidenebis(oxi)]-21-[1-oxo-[4-(nitrooximetil)benzoxi]]preña-1,4-dien-3,20-diona. |
| US10954265B2 (en) * | 2016-10-14 | 2021-03-23 | Van Andel Research Institute | Structures and mechanism for the design of highly potent glucocorticoids |
| WO2021195126A1 (en) | 2020-03-24 | 2021-09-30 | Burnet Michael W | Anti-infective and anti-viral compounds and compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2003064443A2 (en) * | 2002-01-29 | 2003-08-07 | Nicox S.A. | New corticosteroids |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE887518A (fr) | 1980-02-15 | 1981-08-13 | Glaxo Group Ltd | Cartothioates d'androstanes |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
| IT1311922B1 (it) | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| EP1336602A1 (en) * | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
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2006
- 2006-08-04 KR KR1020087004591A patent/KR20080039442A/ko not_active Ceased
- 2006-08-04 SG SG201000520-5A patent/SG158916A1/en unknown
- 2006-08-04 WO PCT/EP2006/007746 patent/WO2007025632A2/en not_active Ceased
- 2006-08-04 AU AU2006286838A patent/AU2006286838C1/en not_active Ceased
- 2006-08-04 JP JP2008528372A patent/JP5216589B2/ja not_active Expired - Fee Related
- 2006-08-04 ES ES06776617T patent/ES2393363T3/es not_active Expired - Lifetime
- 2006-08-04 BR BRPI0614967-7A patent/BRPI0614967A2/pt not_active IP Right Cessation
- 2006-08-04 NZ NZ566128A patent/NZ566128A/en not_active IP Right Cessation
- 2006-08-04 RU RU2008111076/04A patent/RU2415864C2/ru not_active IP Right Cessation
- 2006-08-04 EP EP06776617A patent/EP1940863B1/en not_active Expired - Lifetime
- 2006-08-04 US US12/065,561 patent/US20080221073A1/en not_active Abandoned
- 2006-08-04 CN CNA2006800405622A patent/CN101300265A/zh active Pending
- 2006-08-04 CA CA002621117A patent/CA2621117A1/en not_active Abandoned
- 2006-08-04 CN CN2011100265155A patent/CN102134269A/zh active Pending
- 2006-09-01 TW TW095132322A patent/TW200801031A/zh unknown
- 2006-09-01 AR ARP060103835A patent/AR056868A1/es not_active Application Discontinuation
- 2006-09-01 UY UY29779A patent/UY29779A1/es unknown
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2008
- 2008-02-07 IL IL189337A patent/IL189337A0/en unknown
- 2008-02-25 ZA ZA200801789A patent/ZA200801789B/xx unknown
- 2008-04-01 NO NO20081614A patent/NO20081614L/no not_active Application Discontinuation
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2009
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- 2009-06-26 US US12/492,337 patent/US20090264393A1/en not_active Abandoned
- 2009-06-26 US US12/492,404 patent/US20090264394A1/en not_active Abandoned
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2011
- 2011-08-10 US US13/207,231 patent/US20110294769A1/en not_active Abandoned
- 2011-11-22 IL IL216516A patent/IL216516A0/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003064443A2 (en) * | 2002-01-29 | 2003-08-07 | Nicox S.A. | New corticosteroids |
Non-Patent Citations (1)
| Title |
|---|
| HAMMER S. Et al // Steroids, v 68, №4 (2003), p.329339. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5216589B2 (ja) | 2013-06-19 |
| US20110294769A1 (en) | 2011-12-01 |
| JP2009506994A (ja) | 2009-02-19 |
| WO2007025632A3 (en) | 2007-04-19 |
| RU2008111076A (ru) | 2009-10-10 |
| CA2621117A1 (en) | 2007-03-08 |
| BRPI0614967A2 (pt) | 2013-01-01 |
| WO2007025632A2 (en) | 2007-03-08 |
| US20090258849A1 (en) | 2009-10-15 |
| US20090264393A1 (en) | 2009-10-22 |
| TW200801031A (en) | 2008-01-01 |
| NO20081614L (no) | 2008-05-28 |
| EP1940863A2 (en) | 2008-07-09 |
| US20080221073A1 (en) | 2008-09-11 |
| CN102134269A (zh) | 2011-07-27 |
| EP1940863B1 (en) | 2012-09-05 |
| NZ566128A (en) | 2011-03-31 |
| AU2006286838B2 (en) | 2012-03-29 |
| CN101300265A (zh) | 2008-11-05 |
| US20090264394A1 (en) | 2009-10-22 |
| IL216516A0 (en) | 2011-12-29 |
| AU2006286838C1 (en) | 2013-05-02 |
| ZA200801789B (en) | 2008-12-31 |
| KR20080039442A (ko) | 2008-05-07 |
| AR056868A1 (es) | 2007-10-31 |
| AU2006286838A1 (en) | 2007-03-08 |
| ES2393363T3 (es) | 2012-12-20 |
| SG158916A1 (en) | 2010-02-26 |
| UY29779A1 (es) | 2006-12-29 |
| IL189337A0 (en) | 2008-06-05 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20140805 |