CA1113452A - Water-soluble corticoids - Google Patents

Water-soluble corticoids

Info

Publication number: CA1113452A
Authority: CA; Canada
Prior art keywords: alpha; methyl; beta; delta; pregnadien
Prior art date: 1977-04-06
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

Application number

CA300,512A

Other languages

English (en)

French (fr)

Inventor

Ulrich Kerb

Rudolf Wiechert

Joachim-Friedrich Kapp

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.)

Bayer Pharma AG

Original Assignee

Schering AG

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.)

1977-04-06

Filing date

1978-04-05

Publication date

1981-12-01

1978-04-05 Application filed by Schering AG filed Critical Schering AG

1981-12-01 Application granted granted Critical

1981-12-01 Publication of CA1113452A publication Critical patent/CA1113452A/en

Status Expired legal-status Critical Current

Links

229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical group CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims abstract description 8
150000001340 alkali metals Chemical group 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
239000000126 substance Substances 0.000 claims description 19
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
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 claims description 14
229910052708 sodium Inorganic materials 0.000 claims description 14
239000011734 sodium Substances 0.000 claims description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
229940014800 succinic anhydride Drugs 0.000 claims description 9
-1 alkali metal salt Chemical class 0.000 claims description 6
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
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 6
239000012300 argon atmosphere Substances 0.000 claims 6
125000004429 atom Chemical group 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 abstract description 3
206010061216 Infarction Diseases 0.000 abstract description 2
208000005374 Poisoning Diseases 0.000 abstract description 2
208000010378 Pulmonary Embolism Diseases 0.000 abstract description 2
208000006673 asthma Diseases 0.000 abstract description 2
230000000747 cardiac effect Effects 0.000 abstract description 2
230000015556 catabolic process Effects 0.000 abstract description 2
230000002349 favourable effect Effects 0.000 abstract description 2
230000007574 infarction Effects 0.000 abstract description 2
231100000572 poisoning Toxicity 0.000 abstract description 2
230000000607 poisoning effect Effects 0.000 abstract description 2
230000035939 shock Effects 0.000 abstract description 2
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
GUHFLRTWNHWJBS-VLTGGNAYSA-N (8r,9s,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 GUHFLRTWNHWJBS-VLTGGNAYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000005457 ice water Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
229940001593 sodium carbonate Drugs 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
229920002527 Glycogen Polymers 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000004316 dimethyl dicarbonate Substances 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002327 eosinophilic effect Effects 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229940094025 potassium bicarbonate Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
229940093932 potassium hydroxide Drugs 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- C07J5/0007—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 not substituted in position 17 alfa
- C07J5/0023—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 not substituted in position 17 alfa substituted in position 16
- C07J5/003—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes
- C07J5/0038—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 not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group including 16-alkylidene substitutes by an alkyl group

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Medicines Containing Plant Substances (AREA)

CA300,512A 1977-04-06 1978-04-05 Water-soluble corticoids Expired CA1113452A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2715853.8		1977-04-06
DE19772715853 DE2715853A1 (de)	1977-04-06	1977-04-06	Wasserloesliche kortikoide

Publications (1)

Publication Number	Publication Date
CA1113452A true CA1113452A (en)	1981-12-01

Family

ID=6005979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA300,512A Expired CA1113452A (en)	1977-04-06	1978-04-05	Water-soluble corticoids

Country Status (29)

Country	Link
JP (1)	JPS53149963A (cs)
AT (1)	ATA239978A (cs)
AU (1)	AU3481178A (cs)
BE (1)	BE865760A (cs)
BG (1)	BG28578A3 (cs)
CA (1)	CA1113452A (cs)
CH (1)	CH638537A5 (cs)
CS (1)	CS198295B2 (cs)
DD (1)	DD135082A5 (cs)
DE (1)	DE2715853A1 (cs)
DK (1)	DK153378A (cs)
EG (1)	EG13249A (cs)
ES (1)	ES468572A1 (cs)
FI (1)	FI781053A7 (cs)
FR (1)	FR2386557A1 (cs)
GB (1)	GB1602266A (cs)
IE (1)	IE46602B1 (cs)
IL (1)	IL54443A0 (cs)
IT (1)	IT1094296B (cs)
LU (1)	LU79375A1 (cs)
NL (1)	NL7803188A (cs)
NO (1)	NO781200L (cs)
NZ (1)	NZ186745A (cs)
PL (1)	PL114096B1 (cs)
PT (1)	PT67872B (cs)
RO (1)	RO81076A2 (cs)
SE (1)	SE7803837L (cs)
SU (1)	SU668611A3 (cs)
ZA (1)	ZA781977B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4948533A (en) *	1984-03-28	1990-08-14	The Upjohn Company	11a-hydroxy steroid diester

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1169444B (de) *	1961-02-22	1964-05-06	Schering Ag	Verfahren zur Herstellung von ?-16ª-Methylsteroiden
YU34304B (en) *	1968-08-17	1979-04-30	Schering Ag	Process for preparing corticoid-21-mono-phosphates
DK290774A (cs) *	1973-06-08	1975-02-03	Schering Ag

1977
- 1977-04-06 DE DE19772715853 patent/DE2715853A1/de not_active Withdrawn
1978
- 1978-03-21 NZ NZ186745A patent/NZ186745A/xx unknown
- 1978-03-23 NL NL7803188A patent/NL7803188A/xx not_active Application Discontinuation
- 1978-03-29 DD DD78204456A patent/DD135082A5/xx unknown
- 1978-03-30 SU SU782595445A patent/SU668611A3/ru active
- 1978-03-31 BG BG039252A patent/BG28578A3/xx unknown
- 1978-04-03 CH CH357378A patent/CH638537A5/de not_active IP Right Cessation
- 1978-04-04 IL IL54443A patent/IL54443A0/xx unknown
- 1978-04-04 RO RO7893718A patent/RO81076A2/ro unknown
- 1978-04-04 LU LU79375A patent/LU79375A1/de unknown
- 1978-04-04 PL PL1978205800A patent/PL114096B1/pl unknown
- 1978-04-05 AT AT0239978A patent/ATA239978A/de not_active Application Discontinuation
- 1978-04-05 EG EG239/78A patent/EG13249A/xx active
- 1978-04-05 CA CA300,512A patent/CA1113452A/en not_active Expired
- 1978-04-05 IT IT21995/78A patent/IT1094296B/it active
- 1978-04-05 NO NO781200A patent/NO781200L/no unknown
- 1978-04-05 PT PT67872A patent/PT67872B/pt unknown
- 1978-04-05 IE IE672/78A patent/IE46602B1/en unknown
- 1978-04-05 SE SE7803837A patent/SE7803837L/xx unknown
- 1978-04-05 AU AU34811/78A patent/AU3481178A/en active Pending
- 1978-04-05 ES ES468572A patent/ES468572A1/es not_active Expired
- 1978-04-06 DK DK153378A patent/DK153378A/da not_active IP Right Cessation
- 1978-04-06 FI FI781053A patent/FI781053A7/fi not_active Application Discontinuation
- 1978-04-06 CS CS782252A patent/CS198295B2/cs unknown
- 1978-04-06 JP JP4077278A patent/JPS53149963A/ja active Pending
- 1978-04-06 BE BE186622A patent/BE865760A/xx not_active IP Right Cessation
- 1978-04-06 FR FR7810202A patent/FR2386557A1/fr active Granted
- 1978-04-06 GB GB13527/78A patent/GB1602266A/en not_active Expired
- 1978-04-06 ZA ZA00781977A patent/ZA781977B/xx unknown

Also Published As

Publication number	Publication date
CH638537A5 (en)	1983-09-30
SE7803837L (sv)	1978-10-07
DK153378A (da)	1978-10-07
PL114096B1 (en)	1981-01-31
EG13249A (en)	1980-12-31
IT7821995A0 (it)	1978-04-05
CS198295B2 (en)	1980-05-30
BG28578A3 (bg)	1980-05-15
RO81076B1 (ro)	1983-01-30
SU668611A3 (ru)	1979-06-15
ATA239978A (de)	1981-06-15
IL54443A0 (en)	1978-07-31
IE46602B1 (en)	1983-07-27
FR2386557B1 (cs)	1980-02-01
PL205800A1 (pl)	1979-01-29
BE865760A (fr)	1978-10-06
FR2386557A1 (fr)	1978-11-03
JPS53149963A (en)	1978-12-27
DD135082A5 (de)	1979-04-11
ZA781977B (en)	1979-03-28
NL7803188A (nl)	1978-10-10
NO781200L (no)	1978-10-09
GB1602266A (en)	1981-11-11
DE2715853A1 (de)	1978-10-19
AU3481178A (en)	1979-10-11
ES468572A1 (es)	1978-12-01
NZ186745A (en)	1980-10-24
RO81076A2 (ro)	1983-02-01
IT1094296B (it)	1985-07-26
IE780672L (en)	1978-10-06
FI781053A7 (fi)	1978-10-07
LU79375A1 (de)	1978-07-13
PT67872A (fr)	1978-05-01
PT67872B (fr)	1979-11-14

Legal Events

Date	Code	Title	Description
1998-12-01	MKEX	Expiry

Publication	Publication Date	Title
JPS59191000A (ja)	1984-10-29	コルチコステロイドのスルホネ−ト含有エステルプロドラツグ
US3318926A (en)	1967-05-09	7alpha-methyl-16alpha-hydroxy-estrones
AP518A (en)	1996-08-23	Spirostanyl glycosidal crystalline monohydrate.
CA1113452A (en)	1981-12-01	Water-soluble corticoids
EP0072546B1 (de)	1985-10-09	Neue Hydrocortison-Derivate, ihre Herstellung und Verwendung
JPS5813600A (ja)	1983-01-26	２β，１６β−ジ−アミノ５α−アンドロスタン類の新規なモノ−及びビス第四級アンモニウム誘導体及びこれらを含有する医薬製剤
US2732383A (en)	1956-01-24	Pregnadeenes and method of preparing
US3966778A (en)	1976-06-29	Production of 21-phosphate corticords having unprotected hydroxyl radicals at least at the 17α- and 21-position
US3705150A (en)	1972-12-05	Process for the preparation of 21-deoxy - 21-n-(n'-methylpiperazinyl)-prednisolone and salts thereof
EP0000471A1 (de)	1979-02-07	Neue Kortikoide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0005758B1 (de)	1983-05-18	Verfahren zum Aufbau der Hydroxyacetyl-Seitenkette von Steroiden des Pregnan-Typs, neue 21-Hydroxy-20-oxo-17alpha-pregnan-Verbindungen und pharmazeutische Präparate enthaltend dieselben
JPH026360B2 (cs)	1990-02-08
DE2431292A1 (de)	1976-01-15	Neue carbazol-derivate
CA1146534A (en)	1983-05-17	Hydrocortisone esters, pharmaceutical formulations containing these and processes for their preparation
CA1114364A (en)	1981-12-15	D-homosteroides
US3254100A (en)	1966-05-31	Hydrocortisone 21-(lower alkane) sulfonate
CH637407A5 (de)	1983-07-29	Verfahren zur herstellung neuer kortikoide.
JPS5817480B2 (ja)	1983-04-07	コルチコステロイド２１− エステルユウドウタイノセイゾウホウ
US3366653A (en)	1968-01-30	Method of preparing steroids
US3236840A (en)	1966-02-22	Cortisone 21-mesylate and intermediates in the preparation thereof
US2901397A (en)	1959-08-25	11-oxygenated 9alpha-21-difluoro-1,4 pregnadiene steroidal compositions
CH514560A (de)	1971-10-31	Verfahren zur Herstellung von 17x-Cyanäthinylsteroiden
US3464980A (en)	1969-09-02	16alpha,17alpha,21-cyclic orthoesters of steroids
US3018295A (en)	1962-01-23	21-methylene steroid compounds
AT275059B (de)	1969-10-10	Vefahren zur Herstellung von neuen 17α-Cyanäthinylsteroiden