DE1913042C3 - Neue Tetrahalogenpregnene, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel sowie A> (1 D-Zwischenprodukte - Google Patents
Neue Tetrahalogenpregnene, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel sowie A> (1 D-ZwischenprodukteInfo
- Publication number
- DE1913042C3 DE1913042C3 DE19691913042 DE1913042A DE1913042C3 DE 1913042 C3 DE1913042 C3 DE 1913042C3 DE 19691913042 DE19691913042 DE 19691913042 DE 1913042 A DE1913042 A DE 1913042A DE 1913042 C3 DE1913042 C3 DE 1913042C3
- Authority
- DE
- Germany
- Prior art keywords
- dione
- methyl
- halogen
- new
- pregnadiene
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 3
- 229940079593 drug Drugs 0.000 title description 2
- 239000000543 intermediate Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 description 19
- 150000002367 halogens Chemical class 0.000 description 17
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- -1 chlorine or Bromine Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- FDJABJJEKWDNQO-UHFFFAOYSA-N pentane;propan-2-one Chemical compound CC(C)=O.CCCCC FDJABJJEKWDNQO-UHFFFAOYSA-N 0.000 description 5
- 150000003431 steroids Chemical class 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 206010047139 Vasoconstriction Diseases 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 230000025033 vasoconstriction Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 206010020565 Hyperaemia Diseases 0.000 description 2
- 201000009053 Neurodermatitis Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000037311 normal skin Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VZRAKVPDZIQRGT-WZBAXQLOSA-N (8r,9s,10s,13r,14s,17r)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C=C)[C@@H]4[C@@H]3CCC21 VZRAKVPDZIQRGT-WZBAXQLOSA-N 0.000 description 1
- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
- 229920002527 Glycogen Polymers 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
- 206010061218 Inflammation Diseases 0.000 description 1
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000008350 Pruritus Vulvae Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 102000057288 Tryptophan 2,3-dioxygenases Human genes 0.000 description 1
- 108700016257 Tryptophan 2,3-dioxygenases Proteins 0.000 description 1
- 206010056530 Vulvovaginal pruritus Diseases 0.000 description 1
- 208000026816 acute arthritis Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 230000001890 gluconeogenic effect Effects 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940020414 potassium triiodide Drugs 0.000 description 1
- 150000003130 pregnenes Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/573—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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691913042 DE1913042C3 (de) | 1969-03-11 | 1969-03-11 | Neue Tetrahalogenpregnene, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel sowie A> (1 D-Zwischenprodukte |
| FI700521A FI46952C (fi) | 1969-03-11 | 1970-02-26 | Menetelmä 6alfa-fluori-9alfa,11beta,21-trihalogeeni-1,4-pregnadieeni-3 ,20-dioni-johdannaisten valmistamiseksi |
| PL13925070A PL78935B1 (enExample) | 1969-03-11 | 1970-03-07 | |
| DK115070AA DK120235B (da) | 1969-03-11 | 1970-03-09 | Analogifremgangsmåde til fremstilling af 9α, 11β-disubstituerede 6α-fluor-16α-methyl-21-halogen-4-pregnen-3,20-dionderivater. |
| IL34053A IL34053A (en) | 1969-03-11 | 1970-03-10 | 6alpha,9alpha,11beta,21-tetrahalo steroids of the pregnane series |
| BR217348/70A BR7017348D0 (pt) | 1969-03-11 | 1970-03-10 | Processo para a obtencao de novos 21-halogenos esteroides |
| JP45020417A JPS4810790B1 (enExample) | 1969-03-11 | 1970-03-10 | |
| SE315670A SE360858B (enExample) | 1969-03-11 | 1970-03-10 | |
| IE313/70A IE34052B1 (en) | 1969-03-11 | 1970-03-10 | New 21-halogeno-steroids |
| NO829/70A NO131028C (enExample) | 1969-03-11 | 1970-03-10 | |
| CH364070A CH539624A (de) | 1969-03-11 | 1970-03-11 | Verfahren zur Herstellung von neuen 21-Halogensteroiden |
| BE747210D BE747210A (fr) | 1969-03-11 | 1970-03-11 | Nouveaux 21-halogenosteroides, leur preparation et leur utilisation |
| CH811873A CH539625A (de) | 1969-03-11 | 1970-03-11 | Verfahren zur Herstellung von neuen 21-Halogensteroiden |
| NLAANVRAGE7003505,A NL168521C (nl) | 1969-03-11 | 1970-03-11 | Werkwijze ter bereiding van steroide-derivaten, werkwijze ter bereiding van een farmaceutisch preparaat, alsmede gevormd preparaat. |
| AT229370A AT301769B (de) | 1969-03-11 | 1970-03-11 | Verfahren zur Herstellung von neuen 21-Halogensteroiden |
| GB1167370A GB1308673A (en) | 1969-03-11 | 1970-03-11 | 21-halogeno-steroids |
| FR707008702A FR2034820B1 (enExample) | 1969-03-11 | 1970-03-11 | |
| ES377388A ES377388A1 (es) | 1969-03-11 | 1970-03-11 | Procedimiento para la preparacion de 21-halogenoesteroides. |
| CH811973A CH539626A (de) | 1969-03-11 | 1970-03-11 | Verfahren zur Herstellung von neuen 21-Halogensteroiden |
| RO6271570A RO61998A (enExample) | 1969-03-11 | 1970-03-11 | |
| US00023117A US3718671A (en) | 1969-03-11 | 1970-03-11 | 21-halogen steroids |
| CH1795472A CH540898A (de) | 1969-03-11 | 1970-03-11 | Verfahren zur Herstellung neuer 21-Halogensteroide |
| FI350972A FI47483C (fi) | 1969-03-11 | 1972-12-11 | Menetelmä valmistaa 6alfa-fluori-9alfa-21-dihalogeeni-11beta-hydroksi- 16-metyyli-1,4-pregnadieeni 3,20-dioneja |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691913042 DE1913042C3 (de) | 1969-03-11 | 1969-03-11 | Neue Tetrahalogenpregnene, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel sowie A> (1 D-Zwischenprodukte |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1913042A1 DE1913042A1 (de) | 1970-10-01 |
| DE1913042B2 DE1913042B2 (de) | 1977-11-03 |
| DE1913042C3 true DE1913042C3 (de) | 1978-06-22 |
Family
ID=5728167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691913042 Expired DE1913042C3 (de) | 1969-03-11 | 1969-03-11 | Neue Tetrahalogenpregnene, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel sowie A> (1 D-Zwischenprodukte |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE1913042C3 (enExample) |
| FI (1) | FI47483C (enExample) |
| PL (1) | PL78935B1 (enExample) |
| RO (1) | RO61998A (enExample) |
| SE (1) | SE360858B (enExample) |
-
1969
- 1969-03-11 DE DE19691913042 patent/DE1913042C3/de not_active Expired
-
1970
- 1970-03-07 PL PL13925070A patent/PL78935B1/pl unknown
- 1970-03-10 SE SE315670A patent/SE360858B/xx unknown
- 1970-03-11 RO RO6271570A patent/RO61998A/ro unknown
-
1972
- 1972-12-11 FI FI350972A patent/FI47483C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| SE360858B (enExample) | 1973-10-08 |
| RO61998A (enExample) | 1977-08-15 |
| FI47483B (enExample) | 1973-08-31 |
| PL78935B1 (enExample) | 1975-06-30 |
| FI47483C (fi) | 1973-12-10 |
| DE1913042B2 (de) | 1977-11-03 |
| DE1913042A1 (de) | 1970-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8320 | Willingness to grant licences declared (paragraph 23) | ||
| 8339 | Ceased/non-payment of the annual fee |