CH542829A - Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens - Google Patents
Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnensInfo
- Publication number
- CH542829A CH542829A CH1289373A CH1289373A CH542829A CH 542829 A CH542829 A CH 542829A CH 1289373 A CH1289373 A CH 1289373A CH 1289373 A CH1289373 A CH 1289373A CH 542829 A CH542829 A CH 542829A
- Authority
- CH
- Switzerland
- Prior art keywords
- alpha
- methyl
- acetoxy
- difluoro
- trioxo
- Prior art date
Links
- 230000035558 fertility Effects 0.000 title claims description 5
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 title 1
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 239000000583 progesterone congener Substances 0.000 claims description 6
- 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 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- QMBJSIBWORFWQT-DFXBJWIESA-N Chlormadinone acetate Chemical compound C1=C(Cl)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 QMBJSIBWORFWQT-DFXBJWIESA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 claims description 2
- 239000004264 Petrolatum Substances 0.000 claims description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 150000003938 benzyl alcohols Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 229960001616 chlormadinone acetate Drugs 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 230000003152 gestagenic effect Effects 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 235000019271 petrolatum Nutrition 0.000 claims description 2
- 229940066842 petrolatum Drugs 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 2
- WKAVAGKRWFGIEA-LANMLWSUSA-N (8s,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene-3,11-dione 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=O WKAVAGKRWFGIEA-LANMLWSUSA-N 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1289373A CH542829A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1291070A CH542831A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens bzw. - 1,4-pregnadiens |
| CH1289373A CH542829A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH542829A true CH542829A (de) | 1973-10-15 |
Family
ID=4387518
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1289373A CH542829A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens |
| CH1289173A CH542833A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens bzw. - 1,4-pregnadiens |
| CH1291070A CH542831A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens bzw. - 1,4-pregnadiens |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1289173A CH542833A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens bzw. - 1,4-pregnadiens |
| CH1291070A CH542831A (de) | 1970-08-28 | 1970-08-28 | Verfahren zur Herstellung des 6a,9a-Difluor-16a-methyl-17a-acetoxy-3,11,20-trioxo- 4-pregnens bzw. - 1,4-pregnadiens |
Country Status (11)
| Country | Link |
|---|---|
| AR (1) | AR196989A1 (enExample) |
| AT (1) | AT312822B (enExample) |
| AU (1) | AU3275071A (enExample) |
| BE (1) | BE771900A (enExample) |
| BR (1) | BR7105636D0 (enExample) |
| CH (3) | CH542829A (enExample) |
| DE (1) | DE2141559A1 (enExample) |
| FR (1) | FR2103585A1 (enExample) |
| HU (1) | HU162767B (enExample) |
| NL (1) | NL7111859A (enExample) |
| SU (1) | SU426363A3 (enExample) |
-
1970
- 1970-08-28 CH CH1289373A patent/CH542829A/de not_active IP Right Cessation
- 1970-08-28 CH CH1289173A patent/CH542833A/de not_active IP Right Cessation
- 1970-08-28 CH CH1291070A patent/CH542831A/de not_active IP Right Cessation
-
1971
- 1971-08-19 DE DE19712141559 patent/DE2141559A1/de active Pending
- 1971-08-26 AU AU32750/71A patent/AU3275071A/en not_active Expired
- 1971-08-27 SU SU1695204A patent/SU426363A3/ru active
- 1971-08-27 NL NL7111859A patent/NL7111859A/xx unknown
- 1971-08-27 BE BE771900A patent/BE771900A/xx unknown
- 1971-08-27 AT AT751971A patent/AT312822B/de not_active IP Right Cessation
- 1971-08-27 FR FR7131153A patent/FR2103585A1/fr active Granted
- 1971-08-27 HU HUCI001152 patent/HU162767B/hu unknown
- 1971-08-27 BR BR563671A patent/BR7105636D0/pt unknown
-
1972
- 1972-05-05 AR AR24184272A patent/AR196989A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7111859A (enExample) | 1972-03-01 |
| AR196989A1 (es) | 1974-03-08 |
| AU3275071A (en) | 1973-03-01 |
| HU162767B (enExample) | 1973-04-28 |
| FR2103585B1 (enExample) | 1974-11-15 |
| BE771900A (fr) | 1972-02-28 |
| SU426363A3 (enExample) | 1974-04-30 |
| DE2141559A1 (de) | 1972-03-02 |
| CH542831A (de) | 1973-10-15 |
| CH542833A (de) | 1973-10-15 |
| FR2103585A1 (en) | 1972-04-14 |
| AT312822B (de) | 1974-01-25 |
| BR7105636D0 (pt) | 1973-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |