GB1452179A - 3-oximes of steroids - Google Patents
3-oximes of steroidsInfo
- Publication number
- GB1452179A GB1452179A GB916974A GB916974A GB1452179A GB 1452179 A GB1452179 A GB 1452179A GB 916974 A GB916974 A GB 916974A GB 916974 A GB916974 A GB 916974A GB 1452179 A GB1452179 A GB 1452179A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- ethisterone
- cycloalkyl
- reaction
- oximes
- 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
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 abstract 4
- 229960000445 ethisterone Drugs 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 238000004440 column chromatography Methods 0.000 abstract 2
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 abstract 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 abstract 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 abstract 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 abstract 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33723673A | 1973-03-01 | 1973-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1452179A true GB1452179A (en) | 1976-10-13 |
Family
ID=23319690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB916974A Expired GB1452179A (en) | 1973-03-01 | 1974-02-28 | 3-oximes of steroids |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5926640B2 (enExample) |
| AT (1) | AT343292B (enExample) |
| CA (1) | CA1034942A (enExample) |
| CH (1) | CH606108A5 (enExample) |
| DE (1) | DE2409648A1 (enExample) |
| FR (1) | FR2219783B1 (enExample) |
| GB (1) | GB1452179A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005000867A1 (en) * | 2003-06-30 | 2005-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | PURE D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS |
| US7576226B2 (en) | 2003-06-30 | 2009-08-18 | Richter Gedeon Vegyeszeti Gyar Rt. | Process of making isomers of norelgestromin and methods using the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2664895B1 (fr) * | 1990-07-20 | 1992-10-30 | Theramex Laboratoire | Nouveaux derives de la 6-methyl 19-nor progesterone, substitues en 3 et leur procede d'obtention. |
| AU3257993A (en) * | 1991-12-22 | 1993-07-28 | Schering Aktiengesellschaft | 3-methylsulphonylhydrazono and 3-oxyimino steroids, a method of preparing them, pharmaceutical preparations containing them and their use in the preparation of drugs |
| JPH0568898U (ja) * | 1992-02-19 | 1993-09-17 | 株式会社明和スクリーン | プルトップ部オープナ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299107A (en) * | 1965-02-12 | 1967-01-17 | Searle & Co | 17-(unsaturated hydrocarbon-substituted)-3-hydroxyimino-5alpha-androstan-17beta-ols,alkyl and acyl derivatives thereof |
| US3686237A (en) * | 1969-12-04 | 1972-08-22 | Ortho Pharma Corp | O-(nitroaryl)oximes of 3-keto steroids |
-
1974
- 1974-02-28 CA CA193,688A patent/CA1034942A/en not_active Expired
- 1974-02-28 AT AT165374A patent/AT343292B/de not_active IP Right Cessation
- 1974-02-28 DE DE19742409648 patent/DE2409648A1/de not_active Withdrawn
- 1974-02-28 GB GB916974A patent/GB1452179A/en not_active Expired
- 1974-02-28 FR FR7406871A patent/FR2219783B1/fr not_active Expired
- 1974-03-01 CH CH294474A patent/CH606108A5/xx not_active IP Right Cessation
- 1974-03-01 JP JP49023481A patent/JPS5926640B2/ja not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005000867A1 (en) * | 2003-06-30 | 2005-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | PURE D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS |
| EA008174B1 (ru) * | 2003-06-30 | 2007-04-27 | Рихтер Гедеон Ведьесети Дьяр Рт. | ЧИСТЫЕ ИЗОМЕРЫ D-(17α)-13-ЭТИЛ-17-ГИДРОКСИ-18,19-ДИНОРПРЕГН-4-ЕН-20-ИН-3-ОН-3Е И 3Z-ОКСИМОВ, СПОСОБ СИНТЕЗА СМЕСИ ИЗОМЕРОВ И ЧИСТЫХ ИЗОМЕРОВ |
| US7576226B2 (en) | 2003-06-30 | 2009-08-18 | Richter Gedeon Vegyeszeti Gyar Rt. | Process of making isomers of norelgestromin and methods using the same |
| US7816546B2 (en) | 2003-06-30 | 2010-10-19 | Richter Gedeon Vegyeszeti Gyar Rt. | Process for the synthesis of high purity d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime |
Also Published As
| Publication number | Publication date |
|---|---|
| CH606108A5 (enExample) | 1978-10-13 |
| AT343292B (de) | 1978-05-26 |
| DE2409648A1 (de) | 1974-09-12 |
| JPS5926640B2 (ja) | 1984-06-29 |
| FR2219783B1 (enExample) | 1977-06-03 |
| FR2219783A1 (enExample) | 1974-09-27 |
| JPS5029550A (enExample) | 1975-03-25 |
| ATA165374A (de) | 1977-09-15 |
| CA1034942A (en) | 1978-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |