CA1262894A - 13 .alpha.-ALKYL-17 .beta.-(3-ACYLOXYPROPYL)-GONANES - Google Patents
13 .alpha.-ALKYL-17 .beta.-(3-ACYLOXYPROPYL)-GONANESInfo
- Publication number
- CA1262894A CA1262894A CA000497807A CA497807A CA1262894A CA 1262894 A CA1262894 A CA 1262894A CA 000497807 A CA000497807 A CA 000497807A CA 497807 A CA497807 A CA 497807A CA 1262894 A CA1262894 A CA 1262894A
- Authority
- CA
- Canada
- Prior art keywords
- beta
- process according
- hydroxy
- methyl
- gonadiene
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- -1 acyl radical Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000035558 fertility Effects 0.000 abstract description 2
- 230000000380 anti-gestagenic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000000203 mixture Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- GVGLGOZIDCSQPN-UHFFFAOYSA-N (9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl) acetate Chemical compound C12C=CC(OC(C)=O)C3OC4=C5C32CCN(C)C1CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 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 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003418 antiprogestin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000003152 gestagenic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3446661.4 | 1984-12-18 | ||
| DE19843446661 DE3446661A1 (de) | 1984-12-18 | 1984-12-18 | Neue 13(alpha)-alkyl-17(beta)-(3-acyloxypropyl)-gonane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1262894A true CA1262894A (en) | 1989-11-14 |
Family
ID=6253403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000497807A Expired CA1262894A (en) | 1984-12-18 | 1985-12-17 | 13 .alpha.-ALKYL-17 .beta.-(3-ACYLOXYPROPYL)-GONANES |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4434488A1 (de) * | 1994-09-14 | 1996-03-21 | Schering Ag | Steroidester und -amide, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| DE3461090D1 (en) * | 1983-02-18 | 1986-12-04 | Schering Ag | 11-beta-aryl-estradienes, process for their preparation and pharmaceutical compositions containing them |
| ES533260A0 (es) * | 1983-06-15 | 1985-02-01 | Schering Ag | Procedimiento para la preparacion de 13a-alquilgonanos |
-
1984
- 1984-12-18 DE DE19843446661 patent/DE3446661A1/de not_active Withdrawn
-
1985
- 1985-12-03 FI FI854788A patent/FI83089C/fi not_active IP Right Cessation
- 1985-12-05 NZ NZ214449A patent/NZ214449A/xx unknown
- 1985-12-13 DE DE8585115925T patent/DE3572670D1/de not_active Expired
- 1985-12-13 AT AT85115925T patent/ATE45957T1/de not_active IP Right Cessation
- 1985-12-13 EP EP85115925A patent/EP0186834B1/de not_active Expired
- 1985-12-16 GR GR853017A patent/GR853017B/el unknown
- 1985-12-16 ES ES549998A patent/ES8701194A1/es not_active Expired
- 1985-12-16 DD DD85284398A patent/DD242231A5/de not_active IP Right Cessation
- 1985-12-16 IE IE316985A patent/IE58147B1/en not_active IP Right Cessation
- 1985-12-17 CA CA000497807A patent/CA1262894A/en not_active Expired
- 1985-12-17 JP JP60282175A patent/JPH0662665B2/ja not_active Expired - Lifetime
- 1985-12-17 NO NO855090A patent/NO163014C/no unknown
- 1985-12-17 PT PT81690A patent/PT81690B/pt not_active IP Right Cessation
- 1985-12-17 DK DK587585A patent/DK166502B1/da not_active IP Right Cessation
- 1985-12-17 HU HU854813A patent/HU193357B/hu not_active IP Right Cessation
- 1985-12-18 AU AU51436/85A patent/AU580646B2/en not_active Ceased
- 1985-12-18 ZA ZA859666A patent/ZA859666B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI83089B (fi) | 1991-02-15 |
| HU193357B (en) | 1987-09-28 |
| PT81690A (de) | 1986-01-01 |
| JPS61145197A (ja) | 1986-07-02 |
| NO163014C (no) | 1990-03-21 |
| NO855090L (no) | 1986-06-19 |
| NO163014B (no) | 1989-12-11 |
| EP0186834A2 (de) | 1986-07-09 |
| HUT40138A (en) | 1986-11-28 |
| ES549998A0 (es) | 1986-12-01 |
| JPH0662665B2 (ja) | 1994-08-17 |
| GR853017B (enrdf_load_stackoverflow) | 1986-04-15 |
| DE3446661A1 (de) | 1986-06-19 |
| DD242231A5 (de) | 1987-01-21 |
| FI854788L (fi) | 1986-06-19 |
| EP0186834A3 (en) | 1986-11-26 |
| ES8701194A1 (es) | 1986-12-01 |
| IE853169L (en) | 1986-06-18 |
| IE58147B1 (en) | 1993-07-14 |
| ZA859666B (en) | 1986-08-27 |
| FI854788A0 (fi) | 1985-12-03 |
| DK587585A (da) | 1986-06-19 |
| DE3572670D1 (de) | 1989-10-05 |
| FI83089C (fi) | 1991-05-27 |
| DK587585D0 (da) | 1985-12-17 |
| EP0186834B1 (de) | 1989-08-30 |
| DK166502B1 (da) | 1993-06-01 |
| PT81690B (pt) | 1988-02-17 |
| NZ214449A (en) | 1989-01-06 |
| ATE45957T1 (de) | 1989-09-15 |
| AU5143685A (en) | 1986-06-26 |
| AU580646B2 (en) | 1989-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |