CA1334845C - Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal - Google Patents

Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal

Info

Publication number: CA1334845C
Authority: CA; Canada
Prior art keywords: formula; hydrogen; compound; diene; process according
Prior art date: 1985-04-04
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.): Expired - Lifetime

Application number

CA000589467A

Other languages

English (en)

Inventor

Paul Hakan Andersson

Per Ture Andersson

Bengt Ingemar Axelsson

Bror Arne Thalen

Jan William Trofast

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Draco AB

Original Assignee

Draco AB

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.)

1985-04-04

Filing date

1989-01-27

Publication date

1995-03-21

1985-04-04 Priority claimed from SE8501693A external-priority patent/SE8501693D0/xx

1989-01-27 Application filed by Draco AB filed Critical Draco AB

1989-01-27 Priority to CA000589467A priority Critical patent/CA1334845C/fr

1995-03-21 Application granted granted Critical

1995-03-21 Publication of CA1334845C publication Critical patent/CA1334845C/fr

2012-03-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 31
-1 steroid compound Chemical class 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 12
239000000460 chlorine Chemical group 0.000 claims abstract description 12
229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 11
239000011737 fluorine Chemical group 0.000 claims abstract description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052794 bromium Chemical group 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 22
150000003431 steroids Chemical class 0.000 claims description 22
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 17
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 claims description 10
HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 10
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims description 10
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 10
GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 claims description 10
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 10
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 10
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 9
150000002430 hydrocarbons Chemical group 0.000 claims description 9
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 8
150000001299 aldehydes Chemical class 0.000 claims description 7
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 5
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 5
150000008282 halocarbons Chemical class 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
230000009885 systemic effect Effects 0.000 abstract description 3
239000003377 acid catalyst Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
239000000203 mixture Substances 0.000 description 34
229940073584 methylene chloride Drugs 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000004128 high performance liquid chromatography Methods 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000009472 formulation Methods 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
229960001701 chloroform Drugs 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000003862 glucocorticoid Substances 0.000 description 9
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
229920005654 Sephadex Polymers 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
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 5
230000027455 binding Effects 0.000 description 5
229960003957 dexamethasone Drugs 0.000 description 5
229940057995 liquid paraffin Drugs 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229940083542 sodium Drugs 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
102000003676 Glucocorticoid Receptors Human genes 0.000 description 4
108090000079 Glucocorticoid Receptors Proteins 0.000 description 4
239000012507 Sephadex™ Substances 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000004185 ester group Chemical group 0.000 description 4
229940043075 fluocinolone Drugs 0.000 description 4
FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000012265 solid product Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
229960004436 budesonide Drugs 0.000 description 3
239000000284 extract Substances 0.000 description 3
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000001509 sodium citrate Substances 0.000 description 3
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
229960005294 triamcinolone Drugs 0.000 description 3
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 3
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 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
229910018890 NaMoO4 Inorganic materials 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
239000004147 Sorbitan trioleate Substances 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DBWAFSOUGKJFPC-UHFFFAOYSA-N chloroform;ethanol;heptane Chemical compound CCO.ClC(Cl)Cl.CCCCCCC DBWAFSOUGKJFPC-UHFFFAOYSA-N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000008309 hydrophilic cream Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229940075582 sorbic acid Drugs 0.000 description 2
235000010199 sorbic acid Nutrition 0.000 description 2
239000004334 sorbic acid Substances 0.000 description 2
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230000009870 specific binding Effects 0.000 description 2
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
DPWQJNOCSXEZDU-VRYCVARASA-N (8r,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-17-(2,2,2-trihydroxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)C(O)(O)O)[C@@H]4[C@@H]3CCC2=C1 DPWQJNOCSXEZDU-VRYCVARASA-N 0.000 description 1
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IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 1
RKRZYVQFKUXDEZ-UHFFFAOYSA-N 1-bromoethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Br RKRZYVQFKUXDEZ-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
229940122601 Esterase inhibitor Drugs 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
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Steroid Compounds (AREA)

CA000589467A 1985-04-04 1989-01-27 Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal Expired - Lifetime CA1334845C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000589467A CA1334845C (fr)	1985-04-04	1989-01-27	Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
SE8501693A SE8501693D0 (sv)	1985-04-04	1985-04-04	Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters
SE8501693-9		1985-04-04
CA000505744A CA1333597C (fr)	1985-04-04	1986-04-03	Esters de l'acide 16,17-(substituant acetal)-androstane-17.beta.-carbo xylique
CA000589467A CA1334845C (fr)	1985-04-04	1989-01-27	Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000505744A Division CA1333597C (fr)	1985-04-04	1986-04-03	Esters de l'acide 16,17-(substituant acetal)-androstane-17.beta.-carbo xylique

Publications (1)

Publication Number	Publication Date
CA1334845C true CA1334845C (fr)	1995-03-21

Family

ID=25670953

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000589467A Expired - Lifetime CA1334845C (fr)	1985-04-04	1989-01-27	Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal

Country Status (1)

Country	Link
CA (1)	CA1334845C (fr)

1989
- 1989-01-27 CA CA000589467A patent/CA1334845C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2012-03-21	MKEX	Expiry

Publication	Publication Date	Title
US5939409A (en)	1999-08-17	Processes for the production of anti-inflammatory steroids
EP0054010B1 (fr)	1985-02-20	Dérivés du 4-pregnène, procédé de préparation, composition pour le traitement de conditions inflammatoires
GB2247680A (en)	1992-03-11	Acetals and esters of 16alpha-hydroxyprednisolone and fluocinolone
EP0143764B1 (fr)	1990-06-27	Esters d'androstane-17beta-carboxylique acides, un procédé et produits intermédiaires pour leur préparation, compositions et méthode de traitement de conditions inflammatoires
CA1333597C (fr)	1994-12-20	Esters de l'acide 16,17-(substituant acetal)-androstane-17.beta.-carbo xylique
IE58309B1 (en)	1993-09-08	Novel androstane-17 beta-carboxylic acid esters
CA1334845C (fr)	1995-03-21	Esters d'acide androstane-17.beta.-carboxylique a substitution 16, 17- acetal
HK7197A (en)	1997-01-24	Process for the preparation of intermediates for 11-beta,16-alpha,17-alpha,21-tetrahydroxypregna-3,20-dione 16-alpha,17-alpha-acetals and 21-esters thereof
IE66261B1 (en)	1995-12-27	Preparation of intermediates for 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters
Hong et al.	1994	Synthesis of 6-(methoxycarbonyl) prednisolone and its derivatives as new antiinflammatory steroidal antedrugs
NZ230570A (en)	1990-01-29	The preparation of intermediate 16,17-acetal substituted androstang-17#b#-carboxylic acid esters