SU902668A3 - Способ получени производных 9-хлорпреднизолона - Google Patents

Способ получени производных 9-хлорпреднизолона Download PDF

Info

Publication number: SU902668A3
Authority: SU; USSR - Soviet Union
Prior art keywords: dione; chloro; pregnadien; hydroxy; dihydroxy
Prior art date: 1976-10-04

Application number

SU792764204A

Other languages

English (en)

Russian (ru)

Inventor

Анне Клаус

Лаурент Хенри

Хофмайстер Хельмут

Вихерт Рудольф

Вендт Ханс

Фридрих Капп Иоахим

Original Assignee

Шеринг Аг (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.)

1976-10-04

Filing date

1979-05-04

Publication date

1982-01-30

1979-05-04 Application filed by Шеринг Аг (Фирма) filed Critical Шеринг Аг (Фирма)

1982-01-30 Application granted granted Critical

1982-01-30 Publication of SU902668A3 publication Critical patent/SU902668A3/ru

Links

238000000034 method Methods 0.000 title claims description 15
125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 6
150000008065 acid anhydrides Chemical class 0.000 claims description 4
150000001805 chlorine compounds Chemical class 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
230000003993 interaction Effects 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 2
239000001632 sodium acetate Substances 0.000 abstract description 2
235000017281 sodium acetate Nutrition 0.000 abstract description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 abstract 1
BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
-1 1-ethoxy-benzylidenedioxy Chemical group 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
229960002903 benzyl benzoate Drugs 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000005303 weighing Methods 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
SIKHQNIGPLUJDX-ZEQQQVMLSA-N [2-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)CC)[C@@]1(C)CC2 SIKHQNIGPLUJDX-ZEQQQVMLSA-N 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
210000001541 thymus gland Anatomy 0.000 description 2
HDDPEOCLXKUHHO-HUJIQXBTSA-N (8R,9R,10R,13S,14R,17S)-17-acetyl-8-hydroxy-10,13-dimethyl-7,9,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one Chemical compound O[C@@]12[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@@H]2[C@]2(C=CC(C=C2CC1)=O)C)C HDDPEOCLXKUHHO-HUJIQXBTSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
TYNLGDBUJLVSMA-UHFFFAOYSA-N 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid Chemical compound O=C1C2=CC(C(O)=O)=CC(OC(C)=O)=C2C(=O)C2=C1C=CC=C2OC(=O)C TYNLGDBUJLVSMA-UHFFFAOYSA-N 0.000 description 1
WAIJIHDWAKJCBX-BULBTXNYSA-N 9-Fluoroprednisolone Chemical class O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WAIJIHDWAKJCBX-BULBTXNYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BUXDDNQBJRGXTB-DVFHKXEWSA-N CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C(O)[C@]4(C)[C@H]3CC[C@]12C Chemical compound CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C(O)[C@]4(C)[C@H]3CC[C@]12C BUXDDNQBJRGXTB-DVFHKXEWSA-N 0.000 description 1
241001391944 Commicarpus scandens Species 0.000 description 1
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 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
206010012455 Dermatitis exfoliative Diseases 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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 1
241000186359 Mycobacterium Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003470 adrenal cortex hormone Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
229940117173 croton oil Drugs 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
OJAGAAVUZKMVGX-UHFFFAOYSA-N ethyl acetate;pyridine Chemical compound CCOC(C)=O.C1=CC=NC=C1 OJAGAAVUZKMVGX-UHFFFAOYSA-N 0.000 description 1
230000035876 healing Effects 0.000 description 1
DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002973 irritant agent Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000003096 thymolvtic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SU792764204A 1976-10-04 1979-05-04 Способ получени производных 9-хлорпреднизолона SU902668A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2645105A DE2645105C2 (de)	1976-10-04	1976-10-04	Derivate des 9-Chlorprednisolons, Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Präparat

Publications (1)

Publication Number	Publication Date
SU902668A3 true SU902668A3 (ru)	1982-01-30

Family

ID=5989829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU792764204A SU902668A3 (ru)	1976-10-04	1979-05-04	Способ получени производных 9-хлорпреднизолона

Country Status (9)

Country	Link
AU (1)	AU518954B2 (fr)
BE (1)	BE859345A (fr)
CA (1)	CA1100943A (fr)
DD (1)	DD132348A5 (fr)
DE (1)	DE2645105C2 (fr)
ES (3)	ES471733A1 (fr)
PL (1)	PL112152B1 (fr)
SU (1)	SU902668A3 (fr)
ZA (1)	ZA775914B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2932165A1 (de) *	1979-08-06	1981-02-26	Schering Ag	Neue derivate des 9-chlorprednisolons, ihre herstellung und verwendung
DE3227312A1 (de) *	1982-07-19	1984-01-19	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue 6,16-dimethylkortikoide, ihre herstellung und verwendung

1976
- 1976-10-04 DE DE2645105A patent/DE2645105C2/de not_active Expired
1977
- 1977-09-30 PL PL1977214009A patent/PL112152B1/pl unknown
- 1977-10-04 BE BE181431A patent/BE859345A/fr not_active IP Right Cessation
- 1977-10-04 DD DD7700201347A patent/DD132348A5/xx unknown
- 1977-10-04 CA CA288,063A patent/CA1100943A/fr not_active Expired
- 1977-10-04 AU AU29310/77A patent/AU518954B2/en not_active Expired
- 1977-10-04 ZA ZA00775914A patent/ZA775914B/xx unknown
1978
- 1978-07-14 ES ES471733A patent/ES471733A1/es not_active Expired
- 1978-07-14 ES ES471732A patent/ES471732A1/es not_active Expired
- 1978-07-14 ES ES471734A patent/ES471734A1/es not_active Expired
1979
- 1979-05-04 SU SU792764204A patent/SU902668A3/ru active

Also Published As

Publication number	Publication date
DD132348A5 (de)	1978-09-20
DE2645105C2 (de)	1986-03-13
CA1100943A (fr)	1981-05-12
DE2645105A1 (de)	1978-04-06
ZA775914B (en)	1978-05-30
AU518954B2 (en)	1981-10-29
BE859345A (fr)	1978-04-04
PL112152B1 (en)	1980-09-30
ES471733A1 (es)	1979-02-01
ES471732A1 (es)	1979-02-01
ES471734A1 (es)	1979-02-01
AU2931077A (en)	1979-04-12

Publication	Publication Date	Title
FI80888C (fi)	1990-08-10	Foerfarande foer framstaellning av terapeutiskt verkande steroida karboxylsyraestrar.
GB2247680A (en)	1992-03-11	Acetals and esters of 16alpha-hydroxyprednisolone and fluocinolone
US5972922A (en)	1999-10-26	Steroids which inhibit angiogenesis
EP0072547B1 (fr)	1986-03-26	Dérivés de 6-alpha-méthyl prednisolone, leur préparation et leur utilisation
US3529060A (en)	1970-09-15	Betamethasone 17-benzoate and its use as an anti-inflammatory
US4567172A (en)	1986-01-28	6α-Methylprednisolone derivatives
JPH0415239B2 (fr)	1992-03-17
JPS59106500A (ja)	1984-06-20	新規６α―メチルコルチコイド及びその製法
SU902668A3 (ru)	1982-01-30	Способ получени производных 9-хлорпреднизолона
US4243664A (en)	1981-01-06	Novel corticoids
US5082835A (en)	1992-01-21	Novel steroid diols, pharmaceutical compositions containing them and process for preparing same
SU751327A3 (ru)	1980-07-23	Способ получени производных 9-хлорпреднизолона
EP0141684B1 (fr)	1987-09-30	17-oxo-21-thioesters d'hydrocortisone, leur préparation et leurs applications comme médicament
BG60440B2 (bg)	1995-03-31	Нови стероидни производни,фармацевтични състави,които ги съдържат,и метод за получаването им
EP0149222A2 (fr)	1985-07-24	6-Alpha, 16 alpha-diméthylcorticoides
EP0003341A2 (fr)	1979-08-08	Prégnanes substitués en positions 11 et 17, leur préparation et leur utilisation pour la préparation de compositions pharmaceutiques
DE1125422B (de)	1962-03-15	Verfahren zur Herstellung von 6-Fluor-í¸-3-ketosteoriden
JPS6246557B2 (fr)	1987-10-02
KR820002025B1 (ko)	1982-10-25	하이드로 코르티죤 유도체의 제조방법
US3450722A (en)	1969-06-17	Preparation of bisnorcholanic acid derivatives
US3467677A (en)	1969-09-16	17alpha-oxa-d-homo-pregnanes and methods for their manufacture
AT373604B (de)	1984-02-10	Verfahren zur herstellung von neuen derivaten des 9-chlorprednisolons
GB1603281A (en)	1981-11-25	Derivatives of 9-fluoroprednisolone
US3462423A (en)	1969-08-19	Cyano-derivatives of steroids
AP157A (en)	1991-11-15	Novel steroid derivatives.