CA2621117A1 - Steroids nitrooxyderivatives - Google Patents
Steroids nitrooxyderivatives Download PDFInfo
- Publication number
- CA2621117A1 CA2621117A1 CA002621117A CA2621117A CA2621117A1 CA 2621117 A1 CA2621117 A1 CA 2621117A1 CA 002621117 A CA002621117 A CA 002621117A CA 2621117 A CA2621117 A CA 2621117A CA 2621117 A1 CA2621117 A1 CA 2621117A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- integer
- ono2
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000003431 steroids Chemical class 0.000 title abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 230000000699 topical effect Effects 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 239000012528 membrane Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 122
- 229910004679 ONO2 Inorganic materials 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 239000003246 corticosteroid Substances 0.000 claims description 23
- 229910052731 fluorine Chemical group 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 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 17
- -1 isopropylidenedioxy Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 230000004054 inflammatory process Effects 0.000 claims description 14
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 14
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- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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- 231100000321 erythema Toxicity 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 208000003251 Pruritus Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 150000002828 nitro derivatives Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 7
- 230000003637 steroidlike Effects 0.000 claims description 7
- 206010048768 Dermatosis Diseases 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 208000010247 contact dermatitis Diseases 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000001301 oxygen Chemical group 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
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 6
- 206010012444 Dermatitis diaper Diseases 0.000 claims description 5
- 208000003105 Diaper Rash Diseases 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 5
- 201000010618 Tinea cruris Diseases 0.000 claims description 5
- 208000000260 Warts Diseases 0.000 claims description 5
- 239000006071 cream Substances 0.000 claims description 5
- 230000003628 erosive effect Effects 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- 201000011486 lichen planus Diseases 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 201000010153 skin papilloma Diseases 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 4
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+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 NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- 229940041677 topical spray Drugs 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 16
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 7
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 28
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 10
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- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 10
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- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 description 2
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 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
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 208000024891 symptom Diseases 0.000 description 1
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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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05019155.0 | 2005-09-02 | ||
| EP05019155 | 2005-09-02 | ||
| PCT/EP2006/007746 WO2007025632A2 (en) | 2005-09-02 | 2006-08-04 | Nitrooxy derivatives op glucocorticoids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2621117A1 true CA2621117A1 (en) | 2007-03-08 |
Family
ID=37450883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002621117A Abandoned CA2621117A1 (en) | 2005-09-02 | 2006-08-04 | Steroids nitrooxyderivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US20080221073A1 (enExample) |
| EP (1) | EP1940863B1 (enExample) |
| JP (1) | JP5216589B2 (enExample) |
| KR (1) | KR20080039442A (enExample) |
| 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) |
| TW (1) | TW200801031A (enExample) |
| 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 |
| CN101652380A (zh) | 2007-02-05 | 2010-02-17 | 尼科克斯公司 | 释放一氧化氮的类固醇 |
| 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. |
| EP2318427B1 (en) * | 2008-07-31 | 2013-10-23 | Nicox S.A. | Glucocorticoids attached to nitrate esters via an aromatic linker in position 21 and their use in ophthalmology |
| US20110130375A1 (en) * | 2008-08-05 | 2011-06-02 | Nicox S.A. | New no-releasing steroids for the treatment of retina and macula lutea diseases |
| CA2731477A1 (en) * | 2008-08-05 | 2010-02-11 | Nicox S.A. | New no releasing steroids derivatives |
| US8062653B2 (en) * | 2009-02-18 | 2011-11-22 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
| WO2010096320A2 (en) * | 2009-02-18 | 2010-08-26 | 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. |
| EP3525870B1 (en) * | 2016-10-14 | 2023-05-10 | Van Andel Research Institute | Highly potent glucocorticoids |
| US20230131943A1 (en) | 2020-03-24 | 2023-04-27 | Burnet Micheal W | Anti-infective and anti-viral compounds and compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1201114A (en) | 1980-02-15 | 1986-02-25 | Gordon H. Phillipps | Androstane carbothioates |
| 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. |
| ITMI20020148A1 (it) * | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| 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 |
-
2006
- 2006-08-04 AU AU2006286838A patent/AU2006286838C1/en not_active Ceased
- 2006-08-04 CN CNA2006800405622A patent/CN101300265A/zh active Pending
- 2006-08-04 SG SG201000520-5A patent/SG158916A1/en unknown
- 2006-08-04 CN CN2011100265155A patent/CN102134269A/zh active Pending
- 2006-08-04 WO PCT/EP2006/007746 patent/WO2007025632A2/en not_active Ceased
- 2006-08-04 BR BRPI0614967-7A patent/BRPI0614967A2/pt not_active IP Right Cessation
- 2006-08-04 US US12/065,561 patent/US20080221073A1/en not_active Abandoned
- 2006-08-04 NZ NZ566128A patent/NZ566128A/en not_active IP Right Cessation
- 2006-08-04 JP JP2008528372A patent/JP5216589B2/ja not_active Expired - Fee Related
- 2006-08-04 ES ES06776617T patent/ES2393363T3/es active Active
- 2006-08-04 RU RU2008111076/04A patent/RU2415864C2/ru not_active IP Right Cessation
- 2006-08-04 CA CA002621117A patent/CA2621117A1/en not_active Abandoned
- 2006-08-04 KR KR1020087004591A patent/KR20080039442A/ko not_active Ceased
- 2006-08-04 EP EP06776617A patent/EP1940863B1/en active Active
- 2006-09-01 AR ARP060103835A patent/AR056868A1/es not_active Application Discontinuation
- 2006-09-01 UY UY29779A patent/UY29779A1/es unknown
- 2006-09-01 TW TW095132322A patent/TW200801031A/zh unknown
-
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
-
2009
- 2009-06-26 US US12/492,359 patent/US20090258849A1/en not_active Abandoned
- 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
-
2011
- 2011-08-10 US US13/207,231 patent/US20110294769A1/en not_active Abandoned
- 2011-11-22 IL IL216516A patent/IL216516A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20090264393A1 (en) | 2009-10-22 |
| EP1940863A2 (en) | 2008-07-09 |
| EP1940863B1 (en) | 2012-09-05 |
| JP5216589B2 (ja) | 2013-06-19 |
| ES2393363T3 (es) | 2012-12-20 |
| ZA200801789B (en) | 2008-12-31 |
| SG158916A1 (en) | 2010-02-26 |
| AR056868A1 (es) | 2007-10-31 |
| NZ566128A (en) | 2011-03-31 |
| US20090264394A1 (en) | 2009-10-22 |
| CN101300265A (zh) | 2008-11-05 |
| WO2007025632A2 (en) | 2007-03-08 |
| RU2415864C2 (ru) | 2011-04-10 |
| CN102134269A (zh) | 2011-07-27 |
| US20090258849A1 (en) | 2009-10-15 |
| WO2007025632A3 (en) | 2007-04-19 |
| AU2006286838B2 (en) | 2012-03-29 |
| US20080221073A1 (en) | 2008-09-11 |
| KR20080039442A (ko) | 2008-05-07 |
| JP2009506994A (ja) | 2009-02-19 |
| TW200801031A (en) | 2008-01-01 |
| AU2006286838C1 (en) | 2013-05-02 |
| UY29779A1 (es) | 2006-12-29 |
| IL189337A0 (en) | 2008-06-05 |
| RU2008111076A (ru) | 2009-10-10 |
| BRPI0614967A2 (pt) | 2013-01-01 |
| US20110294769A1 (en) | 2011-12-01 |
| AU2006286838A1 (en) | 2007-03-08 |
| NO20081614L (no) | 2008-05-28 |
| IL216516A0 (en) | 2011-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140805 |