CH496683A - Verfahren zur Herstellung neuer D-Homosteroide - Google Patents
Verfahren zur Herstellung neuer D-HomosteroideInfo
- Publication number
- CH496683A CH496683A CH1754866A CH1754866A CH496683A CH 496683 A CH496683 A CH 496683A CH 1754866 A CH1754866 A CH 1754866A CH 1754866 A CH1754866 A CH 1754866A CH 496683 A CH496683 A CH 496683A
- Authority
- CH
- Switzerland
- Prior art keywords
- dione
- homo
- methylene
- methyl
- androstadien
- Prior art date
Links
- 150000000795 D-homosteroids Chemical class 0.000 title claims abstract description 11
- 230000002280 anti-androgenic effect Effects 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 32
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 26
- 230000008018 melting Effects 0.000 claims description 24
- 238000002844 melting Methods 0.000 claims description 24
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 claims description 23
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 20
- 229960000583 acetic acid Drugs 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000012362 glacial acetic acid Substances 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000001419 dependent effect Effects 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 9
- 235000011152 sodium sulphate Nutrition 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000008707 rearrangement Effects 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 5
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- -1 1,2a-methylene Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims description 4
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 238000001256 steam distillation Methods 0.000 claims description 2
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 2
- 206010000496 acne Diseases 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 201000004240 prostatic hypertrophy Diseases 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 12
- 229960001712 testosterone propionate Drugs 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 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 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 206010020880 Hypertrophy Diseases 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 201000001514 prostate carcinoma Diseases 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- YOPAQWXLWNIFHM-UHFFFAOYSA-N 2-methylpropan-2-ol;hydrochloride Chemical compound Cl.CC(C)(C)O YOPAQWXLWNIFHM-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010036018 Pollakiuria Diseases 0.000 description 1
- 206010046555 Urinary retention Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 206010029446 nocturia Diseases 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960005353 testolactone Drugs 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC038160 | 1965-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496683A true CH496683A (de) | 1970-09-30 |
Family
ID=7434589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1754866A CH496683A (de) | 1965-12-11 | 1966-12-08 | Verfahren zur Herstellung neuer D-Homosteroide |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3492338A (en, 2012) |
| JP (1) | JPS4930833B1 (en, 2012) |
| AT (1) | AT277480B (en, 2012) |
| BE (1) | BE690965A (en, 2012) |
| BR (1) | BR6685240D0 (en, 2012) |
| CH (1) | CH496683A (en, 2012) |
| DE (1) | DE1493183C3 (en, 2012) |
| DK (1) | DK117894B (en, 2012) |
| FR (2) | FR1517823A (en, 2012) |
| GB (1) | GB1148117A (en, 2012) |
| NL (1) | NL152868B (en, 2012) |
| SE (1) | SE328571B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH601351A5 (en, 2012) * | 1973-09-26 | 1978-07-14 | Hoffmann La Roche | |
| DE2349022A1 (de) * | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| DE2349023A1 (de) * | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| US3984476A (en) * | 1974-10-18 | 1976-10-05 | Andor Furst | D-homo-19-norsteroids |
| US4155918A (en) * | 1976-10-28 | 1979-05-22 | Hoffmann-La Roche Inc. | Novel D-homosteroids |
| DE3115995A1 (de) * | 1981-04-13 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | D-homo-4,17-androstadien-3-on, verfahren zu seiner herstellung und diese verbindung enthaltende pharmazeutische praeparate |
| WO2003068229A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150184A (en) * | 1962-11-23 | 1964-09-22 | Parke Davis & Co | 17alpha-amino-d-homoandrost-4-ene-3, 17-dione compounds |
| US3264345A (en) * | 1962-11-23 | 1966-08-02 | Parke Davis & Co | 17alpha-amino-17beta-methyl-d-homoandrost-5-ene-3beta, 17alpha-diol derivatives and salts thereof |
-
1965
- 1965-12-11 DE DE1493183A patent/DE1493183C3/de not_active Expired
-
1966
- 1966-11-23 DK DK607066AA patent/DK117894B/da unknown
- 1966-11-28 AT AT1099566A patent/AT277480B/de not_active IP Right Cessation
- 1966-12-06 GB GB54552/66A patent/GB1148117A/en not_active Expired
- 1966-12-08 CH CH1754866A patent/CH496683A/de not_active IP Right Cessation
- 1966-12-08 US US600028A patent/US3492338A/en not_active Expired - Lifetime
- 1966-12-09 NL NL666617313A patent/NL152868B/xx not_active IP Right Cessation
- 1966-12-09 SE SE16920/66A patent/SE328571B/xx unknown
- 1966-12-09 BR BR185240/66A patent/BR6685240D0/pt unknown
- 1966-12-09 BE BE690965D patent/BE690965A/xx unknown
- 1966-12-12 FR FR87024A patent/FR1517823A/fr not_active Expired
- 1966-12-12 JP JP41081431A patent/JPS4930833B1/ja active Pending
-
1967
- 1967-03-09 FR FR98085A patent/FR6124M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT277480B (de) | 1969-12-29 |
| DE1493183B2 (de) | 1974-08-22 |
| NL6617313A (en, 2012) | 1967-06-12 |
| DK117894B (da) | 1970-06-15 |
| NL152868B (nl) | 1977-04-15 |
| FR1517823A (fr) | 1968-03-22 |
| DE1493183C3 (de) | 1975-04-10 |
| GB1148117A (en) | 1969-04-10 |
| BR6685240D0 (pt) | 1973-12-04 |
| DE1493183A1 (de) | 1969-06-04 |
| FR6124M (en, 2012) | 1968-06-17 |
| BE690965A (en, 2012) | 1967-06-09 |
| SE328571B (en, 2012) | 1970-09-21 |
| US3492338A (en) | 1970-01-27 |
| JPS4930833B1 (en, 2012) | 1974-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH496683A (de) | Verfahren zur Herstellung neuer D-Homosteroide | |
| DE1618065B2 (de) | 21-oxo-23-desoxo-cardenolide, verfahren zu deren herstellung und daraus hergestellte arzneimittel | |
| DE1947221A1 (de) | 3-Aza-19-hydroxy-3,19-cyclo-A-homosteroide und ein Verfahren zu deren Herstellung | |
| AT274260B (de) | Verfahren zur Herstellung von neuen 21-Fluor-Δ<4,6>-pregnadienen | |
| DE1668685C3 (de) | 17-Hydroxy- und 17-Acyloxy-6 beta, 7 beta-epoxy-1 alpha, 2 alpha-methylen-4-pregnen-3,20-dione, Verfahren zu deren Herstellung sowie diese enthaltende Mittel | |
| CH553759A (de) | Verfahren zur herstellung von neuen 4-chlor-1,2(alpha)-methylen-(delta)4,6-pregnadien-17(alpha)-ol-3,20-dion oder dessen 17estern. | |
| AT274256B (de) | Verfahren zur Herstellung von 3-Oxo-4,9,11-triensteroiden | |
| AT241705B (de) | Verfahren zur Herstellung von neuen, ungesättigten Halogensteroiden | |
| AT292210B (de) | Verfahren zur Herstellung von neuen in 2-Stellung durch Chlor substituierten Steroiden der Pregnanreihe | |
| DE1668690C3 (de) | Verfahren zur Herstellung von N-substituierten 4-Aminosteroiden der Androstan-Pregnan- und Cholestanreihe | |
| DE825686C (de) | Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane | |
| DE1668689C3 (de) | N-substltuierte 4-Amlno-l alpha, 2 alpha-Methylen-deita hoch 4,6 -Pregnane | |
| AT233180B (de) | Verfahren zur Herstellung von 17α-Hydroxy-16-methylenpregn-4-en-3, 20-dion und dessen Acylierungsprodukten | |
| AT267088B (de) | Verfahren zur Herstellung neuer 1,2α-Methylen-19-nor-testosterone | |
| AT258487B (de) | Verfahren zur Herstellung von neuen 6 α -Methyl-16-fluormethylen-steroiden | |
| AT233184B (de) | Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden | |
| DE1493174C (de) | 6-Chlor-l,2 alpha; 16,17 alphabismethylen- Delta hoch 4,6- pregnadien-3,20-dion, diese Verbindung enthaltendes Arzneimittel und Verfahren zur Herstellung von 1,2 alpha; 16,17 alpha-Bismethylen- Delta hoch 4,6-pregnadienen | |
| AT275751B (de) | Verfahren zur Herstellung von neuen 16-Methylen-19-nor-progesteron-derivaten | |
| DE893790C (de) | Verfahren zur Herstellung von A9,11-12-Ketocyclopentanopoly-hydrophenanthrenen | |
| AT239967B (de) | Verfahren zur Herstellung von 18,20-Oxidosteroiden | |
| AT218181B (de) | Verfahren zur Herstellung von neuen Laktonen der Steroidreihe | |
| AT235477B (de) | Verfahren zur Herstellung von neuen, mit einem Isoxazolring kondensierten Steroidverbindungen | |
| AT228410B (de) | Verfahren zur Herstellung neuer 6-Methyl-3-oxo-4, 6-dien-steroide | |
| CH515227A (de) | Verfahren zur Herstellung von 21-Fluor- 4,6-pregnadienen | |
| DE1934105A1 (de) | Neue heterocyclische Steriode und ihr Herstellungsverfahren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |