SU1318169A3 - Способ получени стероидных соединений или их четвертичных аммонийных солей - Google Patents

Способ получени стероидных соединений или их четвертичных аммонийных солей Download PDF

Info

Publication number: SU1318169A3
Authority: SU; USSR - Soviet Union
Prior art keywords: carboxylate; chloromethyl; diene; fluoro; hydroxy
Prior art date: 1980-07-10

Application number

SU813306552A

Other languages

English (en)

Russian (ru)

Inventor

Стивен Бодор Николас

Original Assignee

Оцука Фармасьютикал Ко, Лтд (Фирма)

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.)

1980-07-10

Filing date

1981-07-09

Publication date

1987-06-15

1981-07-09 Application filed by Оцука Фармасьютикал Ко, Лтд (Фирма) filed Critical Оцука Фармасьютикал Ко, Лтд (Фирма)

1987-06-15 Application granted granted Critical

1987-06-15 Publication of SU1318169A3 publication Critical patent/SU1318169A3/ru

Links

-1 steroid compounds Chemical class 0.000 title claims abstract description 9
150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 52
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 88
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 62
210000001541 thymus gland Anatomy 0.000 claims description 25
238000000034 method Methods 0.000 claims description 12
241000700159 Rattus Species 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
206010018691 Granuloma Diseases 0.000 claims description 7
235000009161 Espostoa lanata Nutrition 0.000 claims description 6
240000001624 Espostoa lanata Species 0.000 claims description 6
150000007942 carboxylates Chemical class 0.000 claims description 5
OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 claims description 4
229940070710 valerate Drugs 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 claims description 2
229960001524 hydrocortisone butyrate Drugs 0.000 claims description 2
241001302806 Helogenes Species 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate 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)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims 1
229960004703 clobetasol propionate Drugs 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 claims 1
230000000551 effect on thymus Effects 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
125000004742 propyloxycarbonyl group Chemical group 0.000 claims 1
238000007920 subcutaneous administration Methods 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 8
150000003839 salts Chemical class 0.000 abstract description 7
229910052731 fluorine Inorganic materials 0.000 abstract description 6
239000002904 solvent Substances 0.000 abstract description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 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 abstract 1
238000012360 testing method Methods 0.000 description 24
150000003431 steroids Chemical class 0.000 description 15
230000009885 systemic effect Effects 0.000 description 15
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
206010033546 Pallor Diseases 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
229960000890 hydrocortisone Drugs 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
229940117173 croton oil Drugs 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
206010063560 Excessive granulation tissue Diseases 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000011737 fluorine Chemical group 0.000 description 4
210000001126 granulation tissue Anatomy 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003429 steroid acids Chemical class 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000009471 action Effects 0.000 description 3
SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate 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)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000006187 pill Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
210000004100 adrenal gland Anatomy 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000010171 animal model Methods 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002513 implantation Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
229940074928 isopropyl myristate Drugs 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
238000013222 sprague-dawley male rat Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000003096 thymolvtic effect Effects 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
WOCDNIPNRKMMHO-KIRKNLRZSA-N (8S,9S,10R,13S,14S)-6,10,13-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound CC1C[C@H]2[C@@H]3CCC(C(O)=O)[C@@]3(C)CC[C@@H]2[C@@]2(C)C=CC(=O)C=C12 WOCDNIPNRKMMHO-KIRKNLRZSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
125000006012 2-chloroethoxy group Chemical group 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
208000009129 Ear Neoplasms Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960001102 betamethasone dipropionate Drugs 0.000 description 1
CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate 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)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 1
PRNFLFIICMGARJ-UHFFFAOYSA-N carbonochloridic acid;pyridine Chemical compound OC(Cl)=O.C1=CC=NC=C1 PRNFLFIICMGARJ-UHFFFAOYSA-N 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
238000005562 fading Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000000245 forearm Anatomy 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000033687 granuloma formation Effects 0.000 description 1
UKJFVOWPUXSBOM-UHFFFAOYSA-N hexane;oxolane Chemical compound C1CCOC1.CCCCCC UKJFVOWPUXSBOM-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
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 1
238000005406 washing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 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
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU813306552A 1980-07-10 1981-07-09 Способ получени стероидных соединений или их четвертичных аммонийных солей SU1318169A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16845380A	1980-07-10	1980-07-10

Publications (1)

Publication Number	Publication Date
SU1318169A3 true SU1318169A3 (ru)	1987-06-15

Family

ID=22611544

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU813306552A SU1318169A3 (ru)	1980-07-10	1981-07-09	Способ получени стероидных соединений или их четвертичных аммонийных солей

Country Status (4)

Country	Link
JP (1)	JPS5745200A (da)
BE (1)	BE889563A (da)
SU (1)	SU1318169A3 (da)
ZA (1)	ZA814440B (da)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4607028A (en) *	1983-08-18	1986-08-19	Ciba-Geigy Corporation	Novel carboxylic acid esters
IL78144A0 (en) *	1985-04-04	1986-07-31	Draco Ab	Novel androstane-17beta-carboxylic acid esters
SE8501693D0 (sv) *	1985-04-04	1985-04-04	Draco Ab	Novel 16,17-acetalsubstituted androstane-17beta-carboxylic acid esters
DE19947235A1 (de) *	1999-09-30	2001-04-05	Asta Medica Ag	Neue Kombination von Loteprednol und beta¶2¶-Adrenorezeptor-Agonisten
GB0019172D0 (en)	2000-08-05	2000-09-27	Glaxo Group Ltd	Novel compounds
WO2002012266A1 (en)	2000-08-05	2002-02-14	Glaxo Group Limited	17.beta.-carbothioate 17.alpha.-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents
US6777399B2 (en)	2000-08-05	2004-08-17	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6858596B2 (en)	2000-08-05	2005-02-22	Smithkline Beecham Corporation	Formulation containing anti-inflammatory androstane derivative
PT1383786E (pt) *	2001-04-30	2008-12-30	Glaxo Group Ltd	Derivados anti-inflamatórios de éster 17.beta-carbotioato de androstano com um grupo éster ciclíco na posição 17.alfa
GB2389530B (en)	2002-06-14	2007-01-10	Cipla Ltd	Pharmaceutical compositions
WO2005000317A1 (en) *	2003-06-19	2005-01-06	Bodor Nicholas S	Enhancement of activity and/or duration of action of soft anti-inflammatory steroids for topical or other local application
GB0523251D0 (en) *	2005-11-15	2005-12-21	Glaxo Group Ltd	Novel compounds
AR059216A1 (es) *	2006-01-27	2008-03-19	Sun Pharmaceutical Ind Ltd	11b-hidroxiandrosta-4-eno-3-onas
US7687484B2 (en) *	2006-05-25	2010-03-30	Bodor Nicholas S	Transporter enhanced corticosteroid activity
EP3638249A1 (en)	2017-06-13	2020-04-22	Bodor Laboratories, Inc.	Potent soft anti-inflammatory corticosteroid compounds and uses thereof

1981
- 1981-06-30 ZA ZA814440A patent/ZA814440B/xx unknown
- 1981-07-09 SU SU813306552A patent/SU1318169A3/ru active
- 1981-07-09 BE BE2/59253A patent/BE889563A/fr not_active IP Right Cessation
- 1981-07-10 JP JP56108755A patent/JPS5745200A/ja active Granted

Also Published As

Publication number	Publication date
ZA814440B (en)	1982-10-27
BE889563A (fr)	1981-11-03
JPS5745200A (en)	1982-03-13
JPS6411037B2 (da)	1989-02-23

Publication	Publication Date	Title
SU1318169A3 (ru)	1987-06-15	Способ получени стероидных соединений или их четвертичных аммонийных солей
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JPS6119640B2 (da)	1986-05-17
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