CH531494A - Antiinflammatory pregnene-diones - Google Patents
Antiinflammatory pregnene-dionesInfo
- Publication number
- CH531494A CH531494A CH860472A CH860472A CH531494A CH 531494 A CH531494 A CH 531494A CH 860472 A CH860472 A CH 860472A CH 860472 A CH860472 A CH 860472A CH 531494 A CH531494 A CH 531494A
- Authority
- CH
- Switzerland
- Prior art keywords
- beta
- sep
- pregnene
- acid
- methylene
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 5
- 150000003431 steroids Chemical class 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical group C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000005805 hydroxylation reaction Methods 0.000 abstract 2
- 230000002906 microbiologic effect Effects 0.000 abstract 2
- QYLWKJIGHRLVNZ-WHYACLPYSA-N (8R,9S,10S,13S,14S)-10,13-dimethyl-17-(2,2,2-trihydroxyacetyl)-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one Chemical class OC(C(C1=CC[C@H]2[C@@H]3CCC4CC(CC[C@]4(C)[C@H]3CC[C@]12C)=O)=O)(O)O QYLWKJIGHRLVNZ-WHYACLPYSA-N 0.000 abstract 1
- 241001312183 Coniothyrium Species 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01D—MEASURING NOT SPECIALLY ADAPTED FOR A SPECIFIC VARIABLE; ARRANGEMENTS FOR MEASURING TWO OR MORE VARIABLES NOT COVERED IN A SINGLE OTHER SUBCLASS; TARIFF METERING APPARATUS; MEASURING OR TESTING NOT OTHERWISE PROVIDED FOR
- G01D9/00—Recording measured values
- G01D9/28—Producing one or more recordings, each recording being of the values of two or more different variables
- G01D9/30—Producing one or more recordings, each recording being of the values of two or more different variables there being a separate recording element for each variable, e.g. multiple-pen recorder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01D—MEASURING NOT SPECIALLY ADAPTED FOR A SPECIFIC VARIABLE; ARRANGEMENTS FOR MEASURING TWO OR MORE VARIABLES NOT COVERED IN A SINGLE OTHER SUBCLASS; TARIFF METERING APPARATUS; MEASURING OR TESTING NOT OTHERWISE PROVIDED FOR
- G01D18/00—Testing or calibrating apparatus or arrangements provided for in groups G01D1/00 - G01D15/00
-
- G—PHYSICS
- G07—CHECKING-DEVICES
- G07C—TIME OR ATTENDANCE REGISTERS; REGISTERING OR INDICATING THE WORKING OF MACHINES; GENERATING RANDOM NUMBERS; VOTING OR LOTTERY APPARATUS; ARRANGEMENTS, SYSTEMS OR APPARATUS FOR CHECKING NOT PROVIDED FOR ELSEWHERE
- G07C3/00—Registering or indicating the condition or the working of machines or other apparatus, other than vehicles
- G07C3/08—Registering or indicating the production of the machine either with or without registering working or idle time
- G07C3/12—Registering or indicating the production of the machine either with or without registering working or idle time in graphical form
-
- G—PHYSICS
- G08—SIGNALLING
- G08G—TRAFFIC CONTROL SYSTEMS
- G08G1/00—Traffic control systems for road vehicles
- G08G1/01—Detecting movement of traffic to be counted or controlled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Trihydroxypregnene-3,20-diones (I) and especially 11 beta, 17 alpha, 21-trihydroxy-15, 16 beta-methylene-pregnene (4)-(and pregna-1,4-diene)-3,20-dione, for use as anti-inflammatories. R6 and R9 independently are H, halogen, R17, R21 independently are OH or O-acyl; Z is CO or beta-CH2OH. Preparation of (I) and 1,2-dehydro-deriv. by numerous methods e.g. (a) microbiological 11-hydroxylation of (I) (Z=CH2); (b) 1,2-dehydrogenation of a cmpd. (I); (c) adding HOCl or HOBr to the 9,11-double bond a cmpd. (I) or its, 1,2-dehydro-derivs. (Z = HC). In an example 11 beta, 17 alpha-21-trihydroxy-15,16 beta-methylene-pregnene (4)-3,20-dione, m.p. 219-221 degrees is obtained by microbiological hydroxylation of 17 alpha, 21-dihydroxy-15,16 beta-methylene-pregnene (4)-3,20-dione using Coniothyrium hellebori as organism.
Description
Verfahren zur Herstellung neuer Steroide der Pregnanreihe
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Steroide der Formel
EMI1.1
in der R6 und Rg unabhängig voneinander Wasserstoff, Fluor, Chlor oder Brom, R17 Hydroxy oder Acyloxy und R Acyloxy bedeuten bzw. deren 1,2-Dehydroderivate.
Eine Acyloxygruppe enthält vorzugsweise den Rest einer gesättigten oder ungesättigten aliphatischen oder cycloaliphatischen, einer araliphatischen oder aromatischen Carbonsäure mit bis zu 20, vorzugsweise bis zu 12 C-Atomen. Beispiele solcher Säuren sind Ameisensäure, Essigsäure, Pivalinsäure, Propionsäure, Buttersäure, Capronsäure, Önanthsäure, folsäure, Palmitinsäure, Stearinsäure, Bernsteinsäure, Malonsäure, Fumarsäure, Zintronensäure, Cyclohexylpropionsäure, Phenylessigsäure und Benzoesäure.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man die ll-Hydroxygruppe eines Steroids der Formel Beispiel
2,0 g 2 1-Acetoxy-1 iss, 17-dihydroxy-15ss, 16ss-methylen- pregn-4-en-3,20-dion wurden in 200 ml Aceton gelöst, auf
EMI1.2
in der R6, Rg, R17 und R21 die obige Bedeutung haben, oder des entsprechenden 1,2-Dehydroderivats zur Ketogruppe oxydiert.
Zur Herstellung der Ausgangsstoffe kann auf die belgische Patentschrift Nr. 760 392 verwiesen werden.
Die erfindungsgemäss erhältlichen Steroide sind endocrin, insbesondere antiinflammatorisch, wirksam. Sie können als Heilmittel in Form pharmazeutischer Präparate Verwendung finden, welche sie in Mischung mit einem für die enterale, perkutane oder parenterale Applikation geeigneten pharmazeutischen, organischen oder anorganischen inerten Trägermaterial enthalten. Die pharmazeutischen Präparate können in fester Form, in halbfester oder in flüssiger Form vorliegen.
Gegebenenfalls enthalten sie Hilfsstoffe, wie Konservierungs-, Stabilisierungs-, Netz- oder Emulgiermittel, Salze zur Ver änderung des osmotischen Druckes oder Puffer. Sie können auch noch andere therapeutisch wertvolle Stoffe enthalten. 0 abgekühlt und innert 5 Min. mit 1,7 ml 8n CrO3 in 2n H2S04 (Jones-Reagens) und 20 ml Aceton versetzt. Es wurde noch 10 Min. bei 0 gerührt, dann mit 4 ml Methanol versetzt und schliesslich das Reaktionsgemisch auf Eiswasser gegossen. Durch Extraktion mit Methylenchlorid extrahierte man 2,0 g Substanz, die auf der 50fachen Menge Silicagel chromatographiert wurde.
Mit Methylenchlorid-Aceton 9:1 eluierte man reines 21 -Acetoxy-17-hydroxy-15ss, 16ss-methy len-pregn-4-en-3,1 1,20-trion, Schmelzpunkt 259-261 .
Process for the production of new steroids of the Pregnan range
The invention relates to a process for the preparation of new steroids of the formula
EMI1.1
in which R6 and Rg are independently hydrogen, fluorine, chlorine or bromine, R17 is hydroxy or acyloxy and R is acyloxy or their 1,2-dehydro derivatives.
An acyloxy group preferably contains the residue of a saturated or unsaturated aliphatic or cycloaliphatic, an araliphatic or aromatic carboxylic acid having up to 20, preferably up to 12, carbon atoms. Examples of such acids are formic acid, acetic acid, pivalic acid, propionic acid, butyric acid, caproic acid, enanthic acid, folic acid, palmitic acid, stearic acid, succinic acid, malonic acid, fumaric acid, tintronic acid, cyclohexylpropionic acid, phenylacetic acid and benzoic acid.
The process according to the invention is characterized in that the II-hydroxy group of a steroid of the formula Example
2.0 g of 2 1-acetoxy-1iss, 17-dihydroxy-15ss, 16ss-methylenepreg-4-en-3,20-dione were dissolved in 200 ml of acetone
EMI1.2
in which R6, Rg, R17 and R21 have the above meaning, or the corresponding 1,2-dehydro derivative is oxidized to the keto group.
For the preparation of the starting materials, reference can be made to Belgian patent specification No. 760 392.
The steroids obtainable according to the invention are endocrine, in particular anti-inflammatory, effective. They can be used as remedies in the form of pharmaceutical preparations which they contain as a mixture with a pharmaceutical, organic or inorganic inert carrier material suitable for enteral, percutaneous or parenteral administration. The pharmaceutical preparations can be in solid, semi-solid or liquid form.
They may contain auxiliaries such as preservatives, stabilizers, wetting agents or emulsifiers, salts for changing the osmotic pressure or buffers. They can also contain other therapeutically valuable substances. 0 and 1.7 ml of 8N CrO3 in 2N H2S04 (Jones reagent) and 20 ml of acetone were added within 5 minutes. The mixture was stirred at 0 for a further 10 minutes, then 4 ml of methanol were added and the reaction mixture was finally poured onto ice water. Extraction with methylene chloride was used to extract 2.0 g of substance, which was chromatographed on 50 times the amount of silica gel.
Pure 21-acetoxy-17-hydroxy-15ss, 16ss-methylene-pregn-4-en-3,1 1,20-trione, melting point 259-261, was eluted with methylene chloride-acetone 9: 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH860472A CH531494A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH860472A CH531494A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH1883169A CH525872A (en) | 1969-12-17 | 1969-12-17 | Process for the production of new steroids of the Pregnan range |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH531494A true CH531494A (en) | 1972-12-15 |
Family
ID=4435537
Family Applications (11)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH859872A CH529734A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH859772A CH531485A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860172A CH531487A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH859972A CH531490A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH1883169A CH525872A (en) | 1969-12-17 | 1969-12-17 | Process for the production of new steroids of the Pregnan range |
| CH860672A CH531486A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860072A CH531491A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860472A CH531494A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860272A CH531492A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860372A CH531493A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860572A CH531495A (en) | 1969-12-17 | 1970-10-30 | Antiinflammatory pregnene-diones |
Family Applications Before (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH859872A CH529734A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH859772A CH531485A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860172A CH531487A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH859972A CH531490A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH1883169A CH525872A (en) | 1969-12-17 | 1969-12-17 | Process for the production of new steroids of the Pregnan range |
| CH860672A CH531486A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860072A CH531491A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH860272A CH531492A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860372A CH531493A (en) | 1969-12-17 | 1969-12-17 | Antiinflammatory pregnene-diones |
| CH860572A CH531495A (en) | 1969-12-17 | 1970-10-30 | Antiinflammatory pregnene-diones |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4920774B1 (en) |
| AT (8) | AT316771B (en) |
| BE (1) | BE760392A (en) |
| CA (1) | CA955931A (en) |
| CH (11) | CH529734A (en) |
| DE (1) | DE2061183C3 (en) |
| ES (2) | ES386503A1 (en) |
| FI (1) | FI47484C (en) |
| FR (1) | FR2081369B1 (en) |
| GB (1) | GB1276419A (en) |
| HU (1) | HU162802B (en) |
| IE (1) | IE34816B1 (en) |
| IL (1) | IL35790A (en) |
| NL (1) | NL7016761A (en) |
| NO (1) | NO135528C (en) |
| YU (1) | YU34700B (en) |
| ZA (1) | ZA708096B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2740344A (en) * | 1951-12-05 | 1956-04-03 | Messrs Lumoprint Zindler K G | Device for treating directly exposed photopapers |
| DE2453823C2 (en) * | 1974-11-11 | 1984-08-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11β, 17α-dihydroxy-15α, 16α-methylene-1,4-pregnadiene-3,20-dione |
| JPS56109115A (en) * | 1980-12-05 | 1981-08-29 | Fukui Kikai Kk | Controlling method for feeder for strip material |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438975A (en) * | 1966-07-01 | 1969-04-15 | Syntex Corp | 15alpha,16alpha-methylene pregnanes and 19-nor-pregnanes |
| CH510002A (en) * | 1968-04-22 | 1971-07-15 | Hoffmann La Roche | Hormone active steroids |
-
1969
- 1969-12-17 CH CH859872A patent/CH529734A/en not_active IP Right Cessation
- 1969-12-17 CH CH859772A patent/CH531485A/en not_active IP Right Cessation
- 1969-12-17 CH CH860172A patent/CH531487A/en not_active IP Right Cessation
- 1969-12-17 CH CH859972A patent/CH531490A/en not_active IP Right Cessation
- 1969-12-17 CH CH1883169A patent/CH525872A/en not_active IP Right Cessation
- 1969-12-17 CH CH860672A patent/CH531486A/en not_active IP Right Cessation
- 1969-12-17 CH CH860072A patent/CH531491A/en not_active IP Right Cessation
- 1969-12-17 CH CH860472A patent/CH531494A/en not_active IP Right Cessation
- 1969-12-17 CH CH860272A patent/CH531492A/en not_active IP Right Cessation
- 1969-12-17 CH CH860372A patent/CH531493A/en not_active IP Right Cessation
-
1970
- 1970-10-30 CH CH860572A patent/CH531495A/en not_active IP Right Cessation
- 1970-11-14 IE IE1600/70A patent/IE34816B1/en unknown
- 1970-11-16 NL NL7016761A patent/NL7016761A/xx unknown
- 1970-11-26 FI FI703190A patent/FI47484C/en active
- 1970-11-30 ZA ZA708096*A patent/ZA708096B/en unknown
- 1970-12-02 HU HUHO1335A patent/HU162802B/hu unknown
- 1970-12-04 IL IL35790A patent/IL35790A/en unknown
- 1970-12-07 YU YU2980/70A patent/YU34700B/en unknown
- 1970-12-10 CA CA100,261A patent/CA955931A/en not_active Expired
- 1970-12-11 DE DE2061183A patent/DE2061183C3/en not_active Expired
- 1970-12-15 GB GB59497/70A patent/GB1276419A/en not_active Expired
- 1970-12-16 AT AT675272A patent/AT316771B/en active
- 1970-12-16 AT AT675372A patent/AT316772B/en not_active IP Right Cessation
- 1970-12-16 AT AT675772A patent/AT316774B/en active
- 1970-12-16 ES ES386503A patent/ES386503A1/en not_active Expired
- 1970-12-16 JP JP45111944A patent/JPS4920774B1/ja active Pending
- 1970-12-16 AT AT675572A patent/AT316773B/en not_active IP Right Cessation
- 1970-12-16 AT AT1130470A patent/AT308292B/en not_active IP Right Cessation
- 1970-12-16 AT AT675672A patent/AT315397B/en not_active IP Right Cessation
- 1970-12-16 BE BE760392A patent/BE760392A/en unknown
- 1970-12-16 NO NO4845/70A patent/NO135528C/no unknown
- 1970-12-16 AT AT675472A patent/AT315396B/en not_active IP Right Cessation
- 1970-12-16 AT AT675172A patent/AT315395B/en not_active IP Right Cessation
- 1970-12-16 FR FR7045351A patent/FR2081369B1/fr not_active Expired
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1972
- 1972-06-10 ES ES403723A patent/ES403723A2/en not_active Expired
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| Date | Code | Title | Description |
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| PL | Patent ceased |