GB1432135A - 21-substituted pregnanes - Google Patents
21-substituted pregnanesInfo
- Publication number
- GB1432135A GB1432135A GB2114572A GB2114572A GB1432135A GB 1432135 A GB1432135 A GB 1432135A GB 2114572 A GB2114572 A GB 2114572A GB 2114572 A GB2114572 A GB 2114572A GB 1432135 A GB1432135 A GB 1432135A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnane
- hydroxy
- dione
- prepared
- acid
- 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
- 150000003128 pregnanes Chemical class 0.000 title abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 8
- -1 21-Substituted-pregnanes Chemical class 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- YUXCNRNSGTZKLR-VKMGZQQJSA-N (3S,5S,8S,9S,10R,13S,14S,17S)-17-(2-bromoacetyl)-3-hydroxy-10,13-dimethyl-3,4,5,6,7,8,9,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-11-one Chemical compound BrCC([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](C=C[C@]4(C)[C@H]3C(C[C@]12C)=O)O)=O YUXCNRNSGTZKLR-VKMGZQQJSA-N 0.000 abstract 1
- FWTPXHBMBKSTCE-RRSMVVDXSA-N (5S,8S,9S,10S,13S,14S,17S)-10,13-dimethyl-17-(2-sulfanylacetyl)-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound SCC([C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)=O FWTPXHBMBKSTCE-RRSMVVDXSA-N 0.000 abstract 1
- CLSXKTLOJDBKJJ-RRSMVVDXSA-N (5s,8s,9s,10s,13s,14s,17s)-17-(2-bromoacetyl)-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CBr)[C@@H]4[C@@H]3CC[C@H]21 CLSXKTLOJDBKJJ-RRSMVVDXSA-N 0.000 abstract 1
- FNYXEXBNSRQOIO-UHFFFAOYSA-N 2-(3,6-dihydro-2H-pyridin-1-yl)ethanethioic S-acid Chemical compound OC(=S)CN1CCC=CC1 FNYXEXBNSRQOIO-UHFFFAOYSA-N 0.000 abstract 1
- DVBSECCFBPJRQL-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyridin-1-yl)acetic acid Chemical compound OC(=O)CN1CCC=CC1 DVBSECCFBPJRQL-UHFFFAOYSA-N 0.000 abstract 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 abstract 1
- BJKQPYFGPCZERI-UHFFFAOYSA-N 2-morpholin-4-ylethanethioic s-acid Chemical compound SC(=O)CN1CCOCC1 BJKQPYFGPCZERI-UHFFFAOYSA-N 0.000 abstract 1
- VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 abstract 1
- GVAFFAFMFXQVQW-UHFFFAOYSA-N 2-piperidin-1-ylethanethioic s-acid Chemical compound OC(=S)CN1CCCCC1 GVAFFAFMFXQVQW-UHFFFAOYSA-N 0.000 abstract 1
- FETGYRQICBIFSX-UACMURHESA-N 2α,3αepoxy-5α-pregnane-11,20-dione Chemical compound C([C@@H]1CC2)[C@@H]3O[C@@H]3C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1=O FETGYRQICBIFSX-UACMURHESA-N 0.000 abstract 1
- KBXXJWDSHUJCMA-UHFFFAOYSA-N 3-(oxan-3-yloxy)oxane Chemical compound C1CCOCC1OC1COCCC1 KBXXJWDSHUJCMA-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- VIWZVFVJPXTXPA-UHFFFAOYSA-N N-(2-Carboxymethyl)-morpholine Chemical compound OC(=O)CN1CCOCC1 VIWZVFVJPXTXPA-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- IKKQTROUYIFNJA-UHFFFAOYSA-O OC(C[S+]1CCOCC1)=S Chemical compound OC(C[S+]1CCOCC1)=S IKKQTROUYIFNJA-UHFFFAOYSA-O 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- SCZQCQBAFVRBKC-UHFFFAOYSA-N [O-]C(C[S+]1CCOCC1)=O Chemical compound [O-]C(C[S+]1CCOCC1)=O SCZQCQBAFVRBKC-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 159000000009 barium salts Chemical class 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 229940106681 chloroacetic acid Drugs 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 239000012038 nucleophile Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- JRPKWTCMSLUTPR-VDVAPIPPSA-N s-[2-[(5s,8s,9s,10s,13s,14s,17s)-10,13-dimethyl-3,11-dioxo-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2-morpholin-4-ylethanethioate Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(CCC(=O)C[C@@H]4CC3)C)C(=O)C[C@@]21C)CSC(=O)CN1CCOCC1 JRPKWTCMSLUTPR-VDVAPIPPSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2114572A GB1432135A (en) | 1972-05-05 | 1972-05-05 | 21-substituted pregnanes |
| BE130750A BE799103A (fr) | 1972-05-05 | 1973-05-04 | Nouveaux steroides de la serie du pregnane |
| DE2322560A DE2322560A1 (de) | 1972-05-05 | 1973-05-04 | Pregnanderivate und verfahren zu ihrer herstellung |
| JP48050184A JPS4947361A (enrdf_load_stackoverflow) | 1972-05-05 | 1973-05-04 | |
| AU55285/73A AU477138B2 (en) | 1972-05-05 | 1973-05-04 | Anaesthetic pregnanes |
| FR7316111A FR2183794B1 (enrdf_load_stackoverflow) | 1972-05-05 | 1973-05-04 | |
| ZA733036A ZA733036B (en) | 1972-05-05 | 1973-05-04 | Compounds of the pregnane series having anaesthetic activity |
| LU67549A LU67549A1 (enrdf_load_stackoverflow) | 1972-05-05 | 1973-05-04 | |
| NL7306233A NL7306233A (enrdf_load_stackoverflow) | 1972-05-05 | 1973-05-04 | |
| IL42197A IL42197A0 (en) | 1972-05-05 | 1973-05-04 | Anaesthetic steroids |
| ES0414412A ES414412A1 (es) | 1972-05-05 | 1973-05-04 | Procedimiento para la preparacion de esteroides de las series del pregnano o del 19-norpregnano. |
| US05/488,989 US3959260A (en) | 1972-05-05 | 1974-07-16 | Anaesthetic steroids of the pregnane and 19-norpregnane series having a sulfur-containing group at the 21-position |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2114572A GB1432135A (en) | 1972-05-05 | 1972-05-05 | 21-substituted pregnanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1432135A true GB1432135A (en) | 1976-04-14 |
Family
ID=10157962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2114572A Expired GB1432135A (en) | 1972-05-05 | 1972-05-05 | 21-substituted pregnanes |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996040043A3 (en) * | 1995-06-06 | 1997-03-27 | Cocensys Inc | Neuroactive steroids of the androstane and pregnane series |
| US6780853B1 (en) | 1995-06-06 | 2004-08-24 | Euro-Celtique S.A. | Neuroactive steroids of the androstane and pregnane series |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5249509B2 (ja) | 2006-11-10 | 2013-07-31 | 三菱重工業株式会社 | 軌道系交通システムの分岐装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878157A (en) * | 1956-02-29 | 1959-03-17 | Pfizer & Co C | Sulfur containing steroid compositions |
-
1972
- 1972-05-05 GB GB2114572A patent/GB1432135A/en not_active Expired
-
1973
- 1973-05-04 IL IL42197A patent/IL42197A0/xx unknown
- 1973-05-04 ES ES0414412A patent/ES414412A1/es not_active Expired
- 1973-05-04 ZA ZA733036A patent/ZA733036B/xx unknown
- 1973-05-04 BE BE130750A patent/BE799103A/xx unknown
- 1973-05-04 JP JP48050184A patent/JPS4947361A/ja active Pending
- 1973-05-04 AU AU55285/73A patent/AU477138B2/en not_active Expired
- 1973-05-04 FR FR7316111A patent/FR2183794B1/fr not_active Expired
- 1973-05-04 NL NL7306233A patent/NL7306233A/xx unknown
- 1973-05-04 DE DE2322560A patent/DE2322560A1/de active Pending
- 1973-05-04 LU LU67549A patent/LU67549A1/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996040043A3 (en) * | 1995-06-06 | 1997-03-27 | Cocensys Inc | Neuroactive steroids of the androstane and pregnane series |
| US5925630A (en) * | 1995-06-06 | 1999-07-20 | Cocensys, Inc. | Neuroactive steroids of the androstane and pregnane series |
| EP1288220A3 (en) * | 1995-06-06 | 2004-07-21 | Euro-Celtique | Neuroactive 3.alpha.-hydroxy-steroids of the androstane and pregnane series |
| US6780853B1 (en) | 1995-06-06 | 2004-08-24 | Euro-Celtique S.A. | Neuroactive steroids of the androstane and pregnane series |
Also Published As
| Publication number | Publication date |
|---|---|
| ES414412A1 (es) | 1976-02-01 |
| AU477138B2 (en) | 1976-10-14 |
| NL7306233A (enrdf_load_stackoverflow) | 1973-11-07 |
| LU67549A1 (enrdf_load_stackoverflow) | 1973-07-13 |
| BE799103A (fr) | 1973-11-05 |
| ZA733036B (en) | 1974-04-24 |
| IL42197A0 (en) | 1973-07-30 |
| FR2183794A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| DE2322560A1 (de) | 1973-11-15 |
| JPS4947361A (enrdf_load_stackoverflow) | 1974-05-08 |
| AU5528573A (en) | 1974-11-07 |
| FR2183794B1 (enrdf_load_stackoverflow) | 1976-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |