CH531493A - Verfahren zur Herstellung neuer Steroide der Pregnanreihe - Google Patents
Verfahren zur Herstellung neuer Steroide der PregnanreiheInfo
- Publication number
- CH531493A CH531493A CH860372A CH860372A CH531493A CH 531493 A CH531493 A CH 531493A CH 860372 A CH860372 A CH 860372A CH 860372 A CH860372 A CH 860372A CH 531493 A CH531493 A CH 531493A
- Authority
- CH
- Switzerland
- Prior art keywords
- beta
- pregnene
- acid
- dione
- methylene
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-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
- 125000000468 ketone group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 239000002253 acid Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- ZNCXUFVDFVBRDO-UHFFFAOYSA-N pyridine;sulfuric acid Chemical compound [H+].[O-]S([O-])(=O)=O.C1=CC=[NH+]C=C1 ZNCXUFVDFVBRDO-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH860372A CH531493A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH860372A CH531493A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH1883169A CH525872A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH531493A true CH531493A (de) | 1972-12-15 |
Family
ID=4435537
Family Applications (11)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH859772A CH531485A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH859972A CH531490A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860172A CH531487A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860372A CH531493A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH1883169A CH525872A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860472A CH531494A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860072A CH531491A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860672A CH531486A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860272A CH531492A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH859872A CH529734A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860572A CH531495A (de) | 1969-12-17 | 1970-10-30 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH859772A CH531485A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH859972A CH531490A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860172A CH531487A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1883169A CH525872A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860472A CH531494A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860072A CH531491A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860672A CH531486A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860272A CH531492A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH859872A CH529734A (de) | 1969-12-17 | 1969-12-17 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
| CH860572A CH531495A (de) | 1969-12-17 | 1970-10-30 | Verfahren zur Herstellung neuer Steroide der Pregnanreihe |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4920774B1 (enExample) |
| AT (8) | AT315396B (enExample) |
| BE (1) | BE760392A (enExample) |
| CA (1) | CA955931A (enExample) |
| CH (11) | CH531485A (enExample) |
| DE (1) | DE2061183C3 (enExample) |
| ES (2) | ES386503A1 (enExample) |
| FI (1) | FI47484C (enExample) |
| FR (1) | FR2081369B1 (enExample) |
| GB (1) | GB1276419A (enExample) |
| HU (1) | HU162802B (enExample) |
| IE (1) | IE34816B1 (enExample) |
| IL (1) | IL35790A (enExample) |
| NL (1) | NL7016761A (enExample) |
| NO (1) | NO135528C (enExample) |
| YU (1) | YU34700B (enExample) |
| ZA (1) | ZA708096B (enExample) |
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 (de) * | 1974-11-11 | 1984-08-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11β,17α-Dihydroxy-15α,16α-methylen-1,4-pregnadien-3,20-dion |
| 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 (de) * | 1968-04-22 | 1971-07-15 | Hoffmann La Roche | Verfahren zur Herstellung neuer Pregnene |
-
1969
- 1969-12-17 CH CH859772A patent/CH531485A/de not_active IP Right Cessation
- 1969-12-17 CH CH859972A patent/CH531490A/de not_active IP Right Cessation
- 1969-12-17 CH CH860172A patent/CH531487A/de not_active IP Right Cessation
- 1969-12-17 CH CH860372A patent/CH531493A/de not_active IP Right Cessation
- 1969-12-17 CH CH1883169A patent/CH525872A/de not_active IP Right Cessation
- 1969-12-17 CH CH860472A patent/CH531494A/de not_active IP Right Cessation
- 1969-12-17 CH CH860072A patent/CH531491A/de not_active IP Right Cessation
- 1969-12-17 CH CH860672A patent/CH531486A/de not_active IP Right Cessation
- 1969-12-17 CH CH860272A patent/CH531492A/de not_active IP Right Cessation
- 1969-12-17 CH CH859872A patent/CH529734A/de not_active IP Right Cessation
-
1970
- 1970-10-30 CH CH860572A patent/CH531495A/de not_active IP Right Cessation
- 1970-11-14 IE IE1600/70A patent/IE34816B1/xx unknown
- 1970-11-16 NL NL7016761A patent/NL7016761A/xx unknown
- 1970-11-26 FI FI703190A patent/FI47484C/fi active
- 1970-11-30 ZA ZA708096*A patent/ZA708096B/xx unknown
- 1970-12-02 HU HUHO1335A patent/HU162802B/hu unknown
- 1970-12-04 IL IL35790A patent/IL35790A/xx unknown
- 1970-12-07 YU YU2980/70A patent/YU34700B/xx unknown
- 1970-12-10 CA CA100,261A patent/CA955931A/en not_active Expired
- 1970-12-11 DE DE2061183A patent/DE2061183C3/de not_active Expired
- 1970-12-15 GB GB59497/70A patent/GB1276419A/en not_active Expired
- 1970-12-16 JP JP45111944A patent/JPS4920774B1/ja active Pending
- 1970-12-16 NO NO4845/70A patent/NO135528C/no unknown
- 1970-12-16 AT AT675472A patent/AT315396B/de not_active IP Right Cessation
- 1970-12-16 AT AT675672A patent/AT315397B/de not_active IP Right Cessation
- 1970-12-16 BE BE760392A patent/BE760392A/xx unknown
- 1970-12-16 AT AT675572A patent/AT316773B/de not_active IP Right Cessation
- 1970-12-16 AT AT1130470A patent/AT308292B/de not_active IP Right Cessation
- 1970-12-16 AT AT675172A patent/AT315395B/de not_active IP Right Cessation
- 1970-12-16 AT AT675272A patent/AT316771B/de active
- 1970-12-16 AT AT675372A patent/AT316772B/de not_active IP Right Cessation
- 1970-12-16 FR FR7045351A patent/FR2081369B1/fr not_active Expired
- 1970-12-16 ES ES386503A patent/ES386503A1/es not_active Expired
- 1970-12-16 AT AT675772A patent/AT316774B/de active
-
1972
- 1972-06-10 ES ES403723A patent/ES403723A2/es not_active Expired
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| PL | Patent ceased |