GB1346350A - Cardenolides and bufadienolides and a process for the manu facture thereof - Google Patents
Cardenolides and bufadienolides and a process for the manu facture thereofInfo
- Publication number
- GB1346350A GB1346350A GB3475671A GB3475671A GB1346350A GB 1346350 A GB1346350 A GB 1346350A GB 3475671 A GB3475671 A GB 3475671A GB 3475671 A GB3475671 A GB 3475671A GB 1346350 A GB1346350 A GB 1346350A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- compounds
- azido
- epidigoxigenin
- exx
- 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
- 150000001652 bufadienolides Chemical class 0.000 title 1
- 150000001738 cardenolides Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- SHIBSTMRCDJXLN-DYQFMBOASA-N 3-epi-digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-DYQFMBOASA-N 0.000 abstract 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 4
- SHRGTLYZJIVTMQ-HAXYUZPQSA-N (5r,10s,13r,14s,17r)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,4,5,6,7,8,9,11,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,12-dione Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)C2C([C@@]4(C)CCC(=O)C[C@H]4CC2)CC3=O)C)=CC(=O)OC1 SHRGTLYZJIVTMQ-HAXYUZPQSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- QEEBRPGZBVVINN-SIBWXOBNSA-N 5-[(3r,5r,8r,9s,10s,13r,14s,17r)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@@H](O)C[C@H]5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 QEEBRPGZBVVINN-SIBWXOBNSA-N 0.000 abstract 2
- SHIBSTMRCDJXLN-UHFFFAOYSA-N Digoxigenin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)CC2O)(O)C2(C)C1C1=CC(=O)OC1 SHIBSTMRCDJXLN-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 N-(2-acetoxyethyl)acetylamino Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229940089960 chloroacetate Drugs 0.000 abstract 2
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 abstract 2
- SHIBSTMRCDJXLN-KCZCNTNESA-N digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-KCZCNTNESA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- REJBTXQSIQFRRE-UHFFFAOYSA-N odorigenone-B Natural products CC12CCC(C3(CCC(=O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 REJBTXQSIQFRRE-UHFFFAOYSA-N 0.000 abstract 2
- YHPFWEDUGHFFTA-UHFFFAOYSA-N (5alpha,14beta)-14-Hydroxy-3-oxobufa-20,22-dienolide Natural products CC12CCC(C3(CCC(=O)CC3CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 YHPFWEDUGHFFTA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
- XZTUSOXSLKTKJQ-CTZIAKJASA-N 3-[(3r,5r,8r,9s,10s,13r,14s,17r)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 XZTUSOXSLKTKJQ-CTZIAKJASA-N 0.000 abstract 1
- YHPFWEDUGHFFTA-PNERCMSUSA-N 5-[(5r,8r,9s,10s,13r,14s,17r)-14-hydroxy-10,13-dimethyl-3-oxo-2,4,5,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]pyran-2-one Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CCC(=O)C[C@H]5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 YHPFWEDUGHFFTA-PNERCMSUSA-N 0.000 abstract 1
- IWCNCUVTGOMGKG-UHFFFAOYSA-N 5alpha-oleandrigenin Natural products CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 IWCNCUVTGOMGKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- QEEBRPGZBVVINN-UHFFFAOYSA-N Desacetyl-bufotalin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 QEEBRPGZBVVINN-UHFFFAOYSA-N 0.000 abstract 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 abstract 1
- PVAMXWLZJKTXFW-UHFFFAOYSA-N Gitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CC(O)C2C1=CC(=O)OC1 PVAMXWLZJKTXFW-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- XZTUSOXSLKTKJQ-UHFFFAOYSA-N Uzarigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 XZTUSOXSLKTKJQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- QEEBRPGZBVVINN-BMPKRDENSA-N bufalin Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 QEEBRPGZBVVINN-BMPKRDENSA-N 0.000 abstract 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- XZTUSOXSLKTKJQ-CESUGQOBSA-N digitoxigenin Chemical class C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 XZTUSOXSLKTKJQ-CESUGQOBSA-N 0.000 abstract 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 abstract 1
- 229960005156 digoxin Drugs 0.000 abstract 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 abstract 1
- PVAMXWLZJKTXFW-VQMOFDJESA-N gitoxigenin Chemical class C1([C@H]2[C@@H](O)C[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 PVAMXWLZJKTXFW-VQMOFDJESA-N 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IWCNCUVTGOMGKG-YOVVEKLRSA-N oleandrigenin Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C)CC[C@H](O)C[C@H]5CC[C@H]4[C@@]3(O)C[C@@H]2OC(=O)C)=CC(=O)OC1 IWCNCUVTGOMGKG-YOVVEKLRSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1123870A CH551962A (de) | 1970-07-24 | 1970-07-24 | Verfahren zur herstellung von neuen cardenoliden und bufadienoliden. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1346350A true GB1346350A (en) | 1974-02-06 |
Family
ID=4371487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3475671A Expired GB1346350A (en) | 1970-07-24 | 1971-07-23 | Cardenolides and bufadienolides and a process for the manu facture thereof |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007081835A3 (en) * | 2006-01-09 | 2008-08-14 | Btg Int Ltd | Modulators of hypoxia inducible factor-1 and related uses |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415640A1 (fr) * | 1978-01-27 | 1979-08-24 | Nativelle Sa Ets | Derives d'amino-3-cardenolides, procede pour leur preparation, et medicaments les contenant |
| FR2415641A1 (fr) * | 1978-01-27 | 1979-08-24 | Nativelle Sa Ets | Amino-3-cardenolides, procede pour leur preparation, et medicaments les contenant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1365255A (fr) * | 1960-07-05 | 1964-07-03 | Roussel Uclaf | Dérivés du bis-hydroxyméthylène pregnane et procédé de préparation |
-
1970
- 1970-07-24 CH CH1123870A patent/CH551962A/xx not_active IP Right Cessation
-
1971
- 1971-06-16 FI FI711702A patent/FI50632C/fi active
- 1971-06-25 NL NL7108804A patent/NL7108804A/xx unknown
- 1971-06-28 ZA ZA714215A patent/ZA714215B/xx unknown
- 1971-06-28 CA CA116,791A patent/CA959046A/en not_active Expired
- 1971-07-05 IL IL37236A patent/IL37236A/xx unknown
- 1971-07-15 BR BR4492/71A patent/BR7104492D0/pt unknown
- 1971-07-20 IE IE920/71A patent/IE35461B1/xx unknown
- 1971-07-22 FR FR7126843A patent/FR2100951B1/fr not_active Expired
- 1971-07-22 SE SE7109438A patent/SE375778B/xx unknown
- 1971-07-23 DE DE19712137047 patent/DE2137047A1/de active Pending
- 1971-07-23 NO NO2811/71A patent/NO136151C/no unknown
- 1971-07-23 AT AT642171A patent/AT307642B/de not_active IP Right Cessation
- 1971-07-23 GB GB3475671A patent/GB1346350A/en not_active Expired
- 1971-07-23 HU HUHO1398A patent/HU162587B/hu unknown
- 1971-07-23 AT AT1077072A patent/AT322749B/de not_active IP Right Cessation
- 1971-07-23 ES ES393552A patent/ES393552A1/es not_active Expired
- 1971-07-23 AT AT1076972A patent/AT324588B/de not_active IP Right Cessation
- 1971-07-23 BE BE770401A patent/BE770401A/xx unknown
-
1972
- 1972-04-04 AR AR241287A patent/AR192757A1/es active
-
1975
- 1975-01-13 CH CH1123870A patent/CH565202A5/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007081835A3 (en) * | 2006-01-09 | 2008-08-14 | Btg Int Ltd | Modulators of hypoxia inducible factor-1 and related uses |
| GB2453819A (en) * | 2006-01-09 | 2009-04-22 | Btg Int Ltd | Modulators of hypoxia inducible factor-1 and related uses |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 48S | Specification amended (sect. 8/1949) | ||
| 49R | Reference inserted (sect. 9/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |