GB928302A - í¸-pregnene compounds - Google Patents
í¸-pregnene compoundsInfo
- Publication number
- GB928302A GB928302A GB43100/61A GB4310061A GB928302A GB 928302 A GB928302 A GB 928302A GB 43100/61 A GB43100/61 A GB 43100/61A GB 4310061 A GB4310061 A GB 4310061A GB 928302 A GB928302 A GB 928302A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- compound
- converted
- methyl
- fluoro
- 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- 238000005805 hydroxylation reaction Methods 0.000 abstract 5
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 229960003387 progesterone Drugs 0.000 abstract 4
- 239000000186 progesterone Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000033444 hydroxylation Effects 0.000 abstract 2
- 238000005907 ketalization reaction Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000002906 microbiologic effect Effects 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- XJLMUIQBTIJCCF-HOQLVIGXSA-N (5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-fluoro-5-hydroxy-10,13,17-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O[C@]12[C@@H](C[C@H]3[C@@H]4CC[C@](C(C)=O)([C@]4(CC[C@@H]3[C@]2(CCC(C1)=O)C)C)C)F XJLMUIQBTIJCCF-HOQLVIGXSA-N 0.000 abstract 1
- XDBMXBFXAJDAFZ-PTANFLNVSA-N (6S,8S,10R,13S,14S,17R)-17-acetyl-6-fluoro-17-hydroxy-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound F[C@H]1C[C@H]2[C@@H]3CC[C@](C(C)=O)([C@]3(CC=C2[C@]2(CCC(C=C12)=O)C)C)O XDBMXBFXAJDAFZ-PTANFLNVSA-N 0.000 abstract 1
- GTALSHVNMQEIEP-UVKGIPGASA-N (6S,8S,10R,13S,14S,17S)-6-fluoro-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound F[C@H]1C[C@H]2[C@@H]3CC[C@H](C(CO)=O)[C@]3(CC=C2[C@]2(CCC(C=C12)=O)C)C GTALSHVNMQEIEP-UVKGIPGASA-N 0.000 abstract 1
- OZGVKJIJRKQNFY-ISBFPKGDSA-N (6s,8s,10r,13s,14s,17r)-6-fluoro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 OZGVKJIJRKQNFY-ISBFPKGDSA-N 0.000 abstract 1
- QMVWLHSWQWZGAO-VDBJYJQWSA-N (8S,10S,13S,14S,17S)-17-(2-bromoacetyl)-10,13-dimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical class BrCC([C@H]1CC[C@H]2[C@@H]3CCC4=CC(C=C[C@]4(C)C3=CC[C@]12C)=O)=O QMVWLHSWQWZGAO-VDBJYJQWSA-N 0.000 abstract 1
- FCXQAQJAIVLTRM-CIKMDYANSA-N (8S,9S,10R,13S,14S,16R,17R)-17-acetyl-5,6-dichloro-17-hydroxy-10,13,16-trimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound ClC12C(C[C@H]3[C@@H]4C[C@H]([C@](C(C)=O)([C@]4(CC[C@@H]3[C@]2(CCC(C1)=O)C)C)O)C)Cl FCXQAQJAIVLTRM-CIKMDYANSA-N 0.000 abstract 1
- SKTGSARUDQVCMC-VDBJYJQWSA-N (8s,10s,13s,14s,17s)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 SKTGSARUDQVCMC-VDBJYJQWSA-N 0.000 abstract 1
- VHKHTCFYSOVMNK-TVWVXWENSA-N 1-[(3S,8R,9S,10R,13S,14S,17R)-17-chloro-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound Cl[C@]1(C(C)=O)CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O VHKHTCFYSOVMNK-TVWVXWENSA-N 0.000 abstract 1
- AUWGBTUZQWKWRS-WISGCMSASA-N 1-[(3S,8S,9S,10R,13S,14S,16R,17S)-16-ethyl-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]([C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)CC AUWGBTUZQWKWRS-WISGCMSASA-N 0.000 abstract 1
- GOQQFXWEQLDTDF-BCPNQWLMSA-N 1-[(3S,8S,9S,10R,13S,14S,16R,17S)-5,6-dichloro-3-hydroxy-10,13,16-trimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound O[C@@H]1CC2(C(C[C@H]3[C@@H]4C[C@H]([C@H](C(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C)C)Cl)Cl GOQQFXWEQLDTDF-BCPNQWLMSA-N 0.000 abstract 1
- XXSFRYVGIQYVIQ-RDTLVLTASA-N 1-[(3s,8s,9s,10r,13s,14s,16r,17s)-3-hydroxy-10,13,16-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(C)=O)[C@@]1(C)CC2 XXSFRYVGIQYVIQ-RDTLVLTASA-N 0.000 abstract 1
- YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 abstract 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 abstract 1
- 241000134727 Agromyces mediolanus Species 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- DSQVKHUTJHFJPO-VDBJYJQWSA-N C[C@]12CC=C3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO Chemical compound C[C@]12CC=C3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO DSQVKHUTJHFJPO-VDBJYJQWSA-N 0.000 abstract 1
- 241000223211 Curvularia lunata Species 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 abstract 1
- 241000235546 Rhizopus stolonifer Species 0.000 abstract 1
- DQHKOPGHSPUDFM-ABVATSDPSA-N [(3S,8R,9S,10R,13S,14S)-17-(1-acetyloxyethylidene)-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CCC(=C(C)OC(C)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C DQHKOPGHSPUDFM-ABVATSDPSA-N 0.000 abstract 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229960001067 hydrocortisone acetate Drugs 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US743492A US2894963A (en) | 1958-06-20 | 1958-06-20 | 9,11-dihalogeno-4-pregnenes and 1,4-pregnadienes |
| CA775651 | 1959-05-30 | ||
| GB20033/59A GB928301A (en) | 1958-06-20 | 1959-06-11 | 9, 11-dihalogeno steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB928302A true GB928302A (en) | 1963-06-12 |
Family
ID=25673299
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20033/59A Expired GB928301A (en) | 1958-06-20 | 1959-06-11 | 9, 11-dihalogeno steroids |
| GB43100/61A Expired GB928302A (en) | 1958-06-20 | 1959-06-11 | í¸-pregnene compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20033/59A Expired GB928301A (en) | 1958-06-20 | 1959-06-11 | 9, 11-dihalogeno steroids |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE579900A (xx) |
| CH (1) | CH386415A (xx) |
| DK (1) | DK118874B (xx) |
| ES (1) | ES250249A1 (xx) |
| FR (1) | FR564M (xx) |
| GB (2) | GB928301A (xx) |
| NL (1) | NL106036C (xx) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8207151B2 (en) | 2008-05-28 | 2012-06-26 | Validus Biopharma Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9198921B2 (en) | 2010-04-05 | 2015-12-01 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397213A (en) * | 1966-01-12 | 1968-08-13 | Squibb & Sons Inc | 12 methyl-9, 11-dihaloprogesterones |
| FR2342738A1 (fr) * | 1976-03-02 | 1977-09-30 | Roussel Uclaf | Nouveaux derives halogenes de la serie du 16a-methyl pregnane |
-
1959
- 1959-06-11 GB GB20033/59A patent/GB928301A/en not_active Expired
- 1959-06-11 GB GB43100/61A patent/GB928302A/en not_active Expired
- 1959-06-18 CH CH7465759A patent/CH386415A/fr unknown
- 1959-06-18 NL NL240357A patent/NL106036C/xx active
- 1959-06-19 ES ES0250249A patent/ES250249A1/es not_active Expired
- 1959-06-19 DK DK220659AA patent/DK118874B/da unknown
- 1959-06-20 BE BE579900A patent/BE579900A/fr unknown
-
1960
- 1960-08-30 FR FR837195A patent/FR564M/fr active Active
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10857161B2 (en) | 2008-05-28 | 2020-12-08 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US8334279B2 (en) | 2008-05-28 | 2012-12-18 | Validus Genetics | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US8673887B2 (en) | 2008-05-28 | 2014-03-18 | Reveragen Biopharma, Inc | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US8207151B2 (en) | 2008-05-28 | 2012-06-26 | Validus Biopharma Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9434758B2 (en) | 2008-05-28 | 2016-09-06 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US9649320B2 (en) | 2008-05-28 | 2017-05-16 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US11833159B2 (en) | 2008-05-28 | 2023-12-05 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US10206933B2 (en) | 2008-05-28 | 2019-02-19 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kB for treatment of disease |
| US9198921B2 (en) | 2010-04-05 | 2015-12-01 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10000525B2 (en) | 2010-04-05 | 2018-06-19 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κB for treatment of disease |
| US10799514B2 (en) | 2015-06-29 | 2020-10-13 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-kappa beta for treatment of disease |
| US11690853B2 (en) | 2015-06-29 | 2023-07-04 | Reveragen Biopharma, Inc. | Non-hormonal steroid modulators of NF-κβ for treatment of disease |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
| US11471471B2 (en) | 2019-03-07 | 2022-10-18 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CH386415A (fr) | 1965-01-15 |
| GB928301A (en) | 1963-06-12 |
| DK118874B (da) | 1970-10-19 |
| BE579900A (fr) | 1959-10-16 |
| FR564M (xx) | 1961-06-05 |
| NL106036C (xx) | 1963-09-16 |
| ES250249A1 (es) | 1960-01-16 |
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