CH620455A5 - Process for the preparation of D-homosteroids - Google Patents

Process for the preparation of D-homosteroids Download PDF

Info

Publication number: CH620455A5
Authority: CH; Switzerland
Prior art keywords: formula; homosteroid; oxo; hydroxy; carboxylic acid
Prior art date: 1975-04-03

Application number

CH422475A

Other languages

German (de)

English (en)

Inventor

Leo Dr Alig

Andor Dr Fuerst

Marcel Dr Mueller

Ulrich Dr Kerb

Rudolf Prof Dr Wiechert

Klaus Dr Kieslich

Robert Dr Nickolson

Original Assignee

Hoffmann La Roche

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.)

1975-04-03

Filing date

1975-04-03

Publication date

1980-11-28

1975-04-03 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-04-03 Priority to CH422475A priority Critical patent/CH620455A5/de

1976-02-27 Priority to SE7602849A priority patent/SE427276B/xx

1976-03-01 Priority to IL49124A priority patent/IL49124A/xx

1976-03-29 Priority to NZ180233A priority patent/NZ180233A/xx

1976-03-29 Priority to US05/671,381 priority patent/US4029692A/en

1976-03-30 Priority to IE668/76A priority patent/IE43708B1/en

1976-03-31 Priority to FR7609301A priority patent/FR2305976A1/fr

1976-03-31 Priority to DK156076AA priority patent/DK138545B/da

1976-04-01 Priority to JP51035234A priority patent/JPS6050800B2/ja

1976-04-01 Priority to SU762339139A priority patent/SU689621A3/ru

1976-04-01 Priority to DE2614079A priority patent/DE2614079C2/de

1976-04-01 Priority to AU12565/76A priority patent/AU498557B2/en

1976-04-01 Priority to ZA761970A priority patent/ZA761970B/xx

1976-04-01 Priority to CA249,355A priority patent/CA1049496A/fr

1976-04-01 Priority to MC761188A priority patent/MC1106A1/fr

1976-04-01 Priority to GR50451A priority patent/GR60443B/el

1976-04-02 Priority to DD192182A priority patent/DD124881A5/xx

1976-04-02 Priority to PT64966A priority patent/PT64966B/pt

1976-04-02 Priority to FI760897A priority patent/FI55037C/fi

1976-04-02 Priority to PH18287A priority patent/PH13267A/en

1976-04-02 Priority to BE165816A priority patent/BE840346A/fr

1976-04-02 Priority to NL7603461A priority patent/NL7603461A/xx

1976-04-02 Priority to HU76HO00001891A priority patent/HU172961B/hu

1976-04-02 Priority to GB13437/76A priority patent/GB1520562A/en

1976-04-02 Priority to AR262766A priority patent/AR217802A1/es

1976-04-02 Priority to NO761151A priority patent/NO143665C/no

1976-04-02 Priority to ES446623A priority patent/ES446623A1/es

1976-04-02 Priority to LU74694A priority patent/LU74694A1/xx

1976-04-02 Priority to AT239476A priority patent/AT357701B/de

1979-03-27 Priority to CH282879A priority patent/CH620456A5/de

1980-11-28 Publication of CH620455A5 publication Critical patent/CH620455A5/de

Links

150000000795 D-homosteroids Chemical class 0.000 title claims abstract description 40
238000000034 method Methods 0.000 title claims description 46
238000002360 preparation method Methods 0.000 title claims description 21
229910052801 chlorine Inorganic materials 0.000 claims abstract description 27
239000000460 chlorine Substances 0.000 claims abstract description 27
229910052731 fluorine Inorganic materials 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000011737 fluorine Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 4
239000007858 starting material Substances 0.000 claims description 16
-1 steroid carboxylic acid derivatives Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000012025 fluorinating agent Substances 0.000 claims description 5
239000012320 chlorinating reagent Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000468 ketone group Chemical group 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 3
230000032050 esterification Effects 0.000 abstract description 4
238000005886 esterification reaction Methods 0.000 abstract description 4
230000002124 endocrine Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
206010030113 Oedema Diseases 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
239000008188 pellet Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010047139 Vasoconstriction Diseases 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000025033 vasoconstriction Effects 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
240000001307 Myosotis scorpioides Species 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000004281 calcium formate Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000002683 foot Anatomy 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 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
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
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 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
FGRJGEWVJCCOJJ-UHFFFAOYSA-N 2,2-dimethylaziridine Chemical compound CC1(C)CN1 FGRJGEWVJCCOJJ-UHFFFAOYSA-N 0.000 description 1
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZCJSVRGPHXBSM-UHFFFAOYSA-N 8-chloro-[1,3]dioxolo[4,5-g]quinazoline Chemical compound C1=C2C(Cl)=NC=NC2=CC2=C1OCO2 RZCJSVRGPHXBSM-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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244000067632 Aglaonema simplex Species 0.000 description 1
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241000186063 Arthrobacter Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
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108010010803 Gelatin Proteins 0.000 description 1
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241000193386 Lysinibacillus sphaericus Species 0.000 description 1
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241000011719 Nomada opaca Species 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
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241000589516 Pseudomonas Species 0.000 description 1
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229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000000872 buffer Substances 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229940117173 croton oil Drugs 0.000 description 1
HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
239000004316 dimethyl dicarbonate Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000598 endocrine disruptor Substances 0.000 description 1
231100000049 endocrine disruptor Toxicity 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000000544 hyperemic effect Effects 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
BIZCJSDBWZTASZ-UHFFFAOYSA-N iodine pentoxide Inorganic materials O=I(=O)OI(=O)=O BIZCJSDBWZTASZ-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 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
229940039696 lactobacillus Drugs 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
238000011694 lewis rat Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002395 mineralocorticoid Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000004309 nisin Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 1
235000019271 petrolatum Nutrition 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
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
231100001038 reduction in thymus weight Toxicity 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

CH422475A 1975-04-03 1975-04-03 Process for the preparation of D-homosteroids CH620455A5 (en)

Priority Applications (30)

Application Number	Priority Date	Filing Date	Title
CH422475A CH620455A5 (en)	1975-04-03	1975-04-03	Process for the preparation of D-homosteroids
SE7602849A SE427276B (sv)	1975-04-03	1976-02-27	Forfarande for framstellning av d-homosteroider
IL49124A IL49124A (en)	1975-04-03	1976-03-01	D-homoandrosta-17a -carboxylic acids esters thereof their manufacture and pharmaceutical compositions containing them
NZ180233A NZ180233A (en)	1975-04-03	1976-03-29	11-substituted-17a -hydroxy-3-oxo-d-homo-androst-a-ene-17a -carboxylic acids
US05/671,381 US4029692A (en)	1975-04-03	1976-03-29	Steroid carboxylic acids and derivatives
IE668/76A IE43708B1 (en)	1975-04-03	1976-03-30	D-homosteroid carboxylic acids and derivatives thereof
FR7609301A FR2305976A1 (fr)	1975-04-03	1976-03-31	D-homosteroides et procede pour leur preparation
DK156076AA DK138545B (da)	1975-04-03	1976-03-31	Analogifremgangsmåde til fremstilling af 17a alfa-hydroxy-3-oxo-D-homoandrost-4-en-17a beta-carboxylsyrederivater.
JP51035234A JPS6050800B2 (ja)	1975-04-03	1976-04-01	ステロイドカルボン酸及びその誘導体
SU762339139A SU689621A3 (ru)	1975-04-03	1976-04-01	Способ получени -гомостероидов
DE2614079A DE2614079C2 (de)	1975-04-03	1976-04-01	D-Homosteroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
AU12565/76A AU498557B2 (en)	1975-04-03	1976-04-01	D-homosteroids & pharmaceutical compositions
ZA761970A ZA761970B (en)	1975-04-03	1976-04-01	D-homosteroids and process for the preparation thereof
CA249,355A CA1049496A (fr)	1975-04-03	1976-04-01	D-homosteroides et procede de preparation
MC761188A MC1106A1 (fr)	1975-04-03	1976-04-01	D-homostéroides et procédé pour leur préparation
GR50451A GR60443B (en)	1975-04-03	1976-04-01	D-homosteroids and process for their preparation
DD192182A DD124881A5 (fr)	1975-04-03	1976-04-02
PT64966A PT64966B (en)	1975-04-03	1976-04-02	Process for the preparation of d-homosteroids
FI760897A FI55037C (fi)	1975-04-03	1976-04-02	Foerfarande foer framstaellning av d-homosteroider med endokrin verkan
PH18287A PH13267A (en)	1975-04-03	1976-04-02	D*honoandrostant-117oc-carboxylic acid derivatives
BE165816A BE840346A (fr)	1975-04-03	1976-04-02	D-homosteroides et procede pour leur preparation
NL7603461A NL7603461A (nl)	1975-04-03	1976-04-02	D-homosteroiden en werkwijze voor de bereiding daarvan.
HU76HO00001891A HU172961B (hu)	1975-04-03	1976-04-02	Sposob poluchenija d-gomo-steroidov
GB13437/76A GB1520562A (en)	1975-04-03	1976-04-02	D-homosteroid carboxylic acids and derivatives thereof
AR262766A AR217802A1 (es)	1975-04-03	1976-04-02	Procedimiento para la preparacion de derivados de acido 3-oxo-d-homoandrost-4-eno-17a beta-carboxilico
NO761151A NO143665C (no)	1975-04-03	1976-04-02	Analogifremgangsmaate ved fremstilling av farmasoeytisk virksomme d-homosteroider
ES446623A ES446623A1 (es)	1975-04-03	1976-04-02	Un procedimiento para la preparacion de d-homoesteroides.
LU74694A LU74694A1 (fr)	1975-04-03	1976-04-02
AT239476A AT357701B (de)	1975-04-03	1976-04-02	Verfahren zur herstellung von neuen d-homo- steroiden
CH282879A CH620456A5 (en)	1975-04-03	1979-03-27	Process for the preparation of D-homosteroids

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH422475A CH620455A5 (en)	1975-04-03	1975-04-03	Process for the preparation of D-homosteroids

Publications (1)

Publication Number	Publication Date
CH620455A5 true CH620455A5 (en)	1980-11-28

Family

ID=4272112

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH422475A CH620455A5 (en)	1975-04-03	1975-04-03	Process for the preparation of D-homosteroids
CH282879A CH620456A5 (en)	1975-04-03	1979-03-27	Process for the preparation of D-homosteroids

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH282879A CH620456A5 (en)	1975-04-03	1979-03-27	Process for the preparation of D-homosteroids

Country Status (5)

Country	Link
AT (1)	AT357701B (fr)
BE (1)	BE840346A (fr)
CH (2)	CH620455A5 (fr)
SU (1)	SU689621A3 (fr)
ZA (1)	ZA761970B (fr)

1975
- 1975-04-03 CH CH422475A patent/CH620455A5/de not_active IP Right Cessation
1976
- 1976-04-01 ZA ZA761970A patent/ZA761970B/xx unknown
- 1976-04-01 SU SU762339139A patent/SU689621A3/ru active
- 1976-04-02 AT AT239476A patent/AT357701B/de not_active IP Right Cessation
- 1976-04-02 BE BE165816A patent/BE840346A/fr not_active IP Right Cessation
1979
- 1979-03-27 CH CH282879A patent/CH620456A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH620456A5 (en)	1980-11-28
ATA239476A (de)	1979-12-15
SU689621A3 (ru)	1979-09-30
AT357701B (de)	1980-07-25
ZA761970B (en)	1977-03-30
BE840346A (fr)	1976-10-04

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0072546B1 (fr)	1985-10-09	Dérivés d'hydrocortisone, leur préparation et leur utilisation
DE3243482A1 (de)	1984-05-24	Neue 6(alpha)-methylkortikoide, ihre herstellung und verwendung
AT363202B (de)	1981-07-27	Verfahren zur herstellung von neuen mehrfach halogenierten steroiden
DE1181705B (de)	1964-11-19	Verfahren zur Herstellung von 16ß-niedrig-Alkylcortisonen, -hydrocortisonen, -prednisonen und -prednisolonen sowie von deren 9 alpha-Halogenderivaten und 21-Estern
CH620455A5 (en)	1980-11-28	Process for the preparation of D-homosteroids
EP0003341B1 (fr)	1984-06-27	Prégnanes substitués en positions 11 et 17, leur préparation et leur utilisation pour la préparation de compositions pharmaceutiques
DE2614079C2 (de)	1985-07-11	D-Homosteroide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0013959B1 (fr)	1982-07-07	D-homo stéroides, procédés pour leur préparation et médicaments contenant ces D-homo stéroides
CH498106A (de)	1970-10-31	Verfahren zur Herstellung von Steroidderivaten
EP0005758B1 (fr)	1983-05-18	Procédé de synthèse de la chaîne latérale hydroxy acétylique de stéroides prégnaniques, 21-hydroxy-20-oxo-17alpha prégnanes et préparations pharmaceutiques les contenant
DE2064859C3 (de)	1980-05-22	Neue 6 a -Fluor-16 a , 18dimethyl-l,4-pregnadien-3,20-dion Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
CH637407A5 (de)	1983-07-29	Verfahren zur herstellung neuer kortikoide.
AT361645B (de)	1981-03-25	Verfahren zur herstellung von neuen d-homosteroiden
CH620457A5 (en)	1980-11-28	Process for the preparation of D-homosteroids
DE1793270A1 (de)	1972-02-17	16alpha,17alpha-Methylensteroidverbindungen und Verfahren zu ihrer Herstellung
DE2433178A1 (de)	1975-01-30	In 21-stellung alkylierte steroide der pregnanreihe
AT253142B (de)	1967-03-28	Verfahren zur Herstellung von neuen schwefelhaltigen Androstanderivaten
CH629829A5 (en)	1982-05-14	Process for the preparation of D-homosteroids
AT265537B (de)	1968-10-10	Verfahren zur Herstellung von neuen 9β,10α-Steroiden
DE1593209C3 (de)	1976-03-04	Verfahren zur 17 alpha-Alkylierung von 20-Ketosteroiden der Pregnanreihe und 17alpha-Alkylsteroide der Pregnanreihe
AT363204B (de)	1981-07-27	Verfahren zur herstellung von mehrfach halogenierten steroiden
CH631185A5 (en)	1982-07-30	Multiply halogenated steroids
CH617709A5 (fr)	1980-06-13
CH616950A5 (en)	1980-04-30	Process for the preparation of D-homosteroids.
DE1113453B (de)	1961-09-07	Verfahren zur Herstellung von Substitutionsprodukten von Reichsteins-Substanz-S bzw.von deren 21-Acylaten