GB1374079A - Analogues of proscillaridin - Google Patents
Analogues of proscillaridinInfo
- Publication number
- GB1374079A GB1374079A GB5972671A GB5972671A GB1374079A GB 1374079 A GB1374079 A GB 1374079A GB 5972671 A GB5972671 A GB 5972671A GB 5972671 A GB5972671 A GB 5972671A GB 1374079 A GB1374079 A GB 1374079A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- alkyl
- proscillaridin
- acetyl
- dec
- 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
- MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical class O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- -1 C 3-8 cyeloalkyl Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229930190098 proscillaridin Natural products 0.000 abstract 1
- 229960003584 proscillaridin Drugs 0.000 abstract 1
- MYEJFUXQJGHEQK-UHFFFAOYSA-N proscillaridin A Natural products OC1C(O)C(O)C(C)OC1OC1C=C2CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C)CC1 MYEJFUXQJGHEQK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1374079 Proscillaridin esters BOEHRINGER INGELHEIM GmbH 22 Dec 1971 [23 Dec 1970] 59726/71 Heading C2U The invention comprises compounds of formula wherein R 1 is the group R 2 is C 1-4 haloalkyl, (cycloalkyl)-C 1-4 alkyl, C 2-4 alkyl, C 3-8 cyeloalkyl, aryl, haloaryl, aralkyl; ar-haloaralkyl, or, when R 3 is other than H or acetyl, R 2 may be methyl; R 3 is H, C 1-3 alkyl, acetyl, heteroaroyl (e.g. thenoyl) or -COR<SP>1</SP> 2 where R<SP>1</SP> 2 is as defined for R 2 , the groups R 2 and R<SP>1</SP> 2 being the same or different. Preparation of compounds I is by selective hydrolysis of compounds of formula (wherein R 4 is C 1-4 alkyl), e.g. using aqueous acid. Preparation of compounds IVa is by reaction of proscillaridin with R 2 -C(OR 4 ) 3 , followed when required by alkylation or acylation of the 41-hydroxy group. Compounds I are said to be cardioactive, and may be made up with carriers into pharmaceutical compositions for oral, rectal and parenteral administration. Reference has been directed by the Comptroller to Specifications 1,286,232 and 1,266,251.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2063406A DE2063406C3 (en) | 1970-12-23 | 1970-12-23 | Acyl derivatives of proscillaridin A, process for their preparation and preparations containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1374079A true GB1374079A (en) | 1974-11-13 |
Family
ID=5791955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5972671A Expired GB1374079A (en) | 1970-12-23 | 1971-12-22 | Analogues of proscillaridin |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5741480B1 (en) |
| AT (1) | AT312815B (en) |
| AU (1) | AU469336B2 (en) |
| BE (1) | BE777164A (en) |
| BG (1) | BG20580A3 (en) |
| CA (1) | CA939664A (en) |
| CH (1) | CH593302A5 (en) |
| CS (1) | CS166041B2 (en) |
| DD (1) | DD95231A5 (en) |
| DE (1) | DE2063406C3 (en) |
| DK (1) | DK129654B (en) |
| ES (1) | ES398208A1 (en) |
| FI (1) | FI50248C (en) |
| FR (1) | FR2119045B1 (en) |
| GB (1) | GB1374079A (en) |
| HU (1) | HU162742B (en) |
| IE (1) | IE36110B1 (en) |
| IL (1) | IL38430A (en) |
| NL (1) | NL7117645A (en) |
| NO (1) | NO136671C (en) |
| PL (1) | PL83079B1 (en) |
| RO (1) | RO59396A (en) |
| SE (1) | SE380812B (en) |
| SU (1) | SU420173A3 (en) |
| YU (1) | YU35150B (en) |
| ZA (1) | ZA718589B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2427976C2 (en) * | 1974-06-10 | 1985-12-12 | Knoll Ag, 6700 Ludwigshafen | Proscillaridin ethers, processes for their preparation and pharmaceuticals containing them |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33975B (en) * | 1969-01-09 | 1978-09-08 | Knol Ag Chemische Fabriken | Process for preparing bufatrienolide-rhamnoside-acylates |
| DE1910207C3 (en) * | 1969-02-28 | 1978-04-13 | Knoll Ag, 6700 Ludwigshafen | Process for their manufacture |
| RO60624A (en) * | 1970-03-05 | 1976-07-15 | ||
| JPS512471A (en) * | 1974-06-25 | 1976-01-10 | Yasushi Maeda | SHOOTORINGUTOKOIRUNO TORITSUKEHO |
| JPS526988A (en) * | 1975-07-04 | 1977-01-19 | Sumitomo Electric Ind Ltd | Insulated wire |
-
1970
- 1970-12-23 DE DE2063406A patent/DE2063406C3/en not_active Expired
-
1971
- 1971-12-18 BG BG19278A patent/BG20580A3/xx unknown
- 1971-12-20 JP JP46103559A patent/JPS5741480B1/ja active Pending
- 1971-12-20 CH CH1859471A patent/CH593302A5/xx not_active IP Right Cessation
- 1971-12-21 HU HUBO1338A patent/HU162742B/hu unknown
- 1971-12-21 SU SU1728032A patent/SU420173A3/en active
- 1971-12-21 ES ES398208A patent/ES398208A1/en not_active Expired
- 1971-12-22 GB GB5972671A patent/GB1374079A/en not_active Expired
- 1971-12-22 YU YU3224/71A patent/YU35150B/en unknown
- 1971-12-22 RO RO69152A patent/RO59396A/ro unknown
- 1971-12-22 ZA ZA718589A patent/ZA718589B/en unknown
- 1971-12-22 IL IL38430A patent/IL38430A/en unknown
- 1971-12-22 SE SE7116530A patent/SE380812B/en unknown
- 1971-12-22 AT AT1103471A patent/AT312815B/en not_active IP Right Cessation
- 1971-12-22 PL PL1971152413A patent/PL83079B1/pl unknown
- 1971-12-22 AU AU37197/71A patent/AU469336B2/en not_active Expired
- 1971-12-22 CA CA130,806A patent/CA939664A/en not_active Expired
- 1971-12-22 CS CS8920A patent/CS166041B2/cs unknown
- 1971-12-22 DK DK628671AA patent/DK129654B/en not_active IP Right Cessation
- 1971-12-22 DD DD159823A patent/DD95231A5/xx unknown
- 1971-12-22 NO NO4779/71A patent/NO136671C/en unknown
- 1971-12-22 BE BE777164A patent/BE777164A/en unknown
- 1971-12-22 FI FI713661A patent/FI50248C/en active
- 1971-12-22 NL NL7117645A patent/NL7117645A/xx not_active Application Discontinuation
- 1971-12-23 FR FR7146346A patent/FR2119045B1/fr not_active Expired
- 1971-12-23 IE IE1638/71A patent/IE36110B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI50248C (en) | 1976-01-12 |
| DE2063406A1 (en) | 1972-09-21 |
| CH593302A5 (en) | 1977-11-30 |
| BE777164A (en) | 1972-06-22 |
| RO59396A (en) | 1976-05-15 |
| IE36110B1 (en) | 1976-08-18 |
| IE36110L (en) | 1972-06-23 |
| DK129654B (en) | 1974-11-04 |
| PL83079B1 (en) | 1975-12-31 |
| HU162742B (en) | 1973-04-28 |
| SE380812B (en) | 1975-11-17 |
| FR2119045A1 (en) | 1972-08-04 |
| YU35150B (en) | 1980-09-25 |
| AT312815B (en) | 1974-01-25 |
| DE2063406B2 (en) | 1977-08-25 |
| ZA718589B (en) | 1973-08-29 |
| JPS5741480B1 (en) | 1982-09-03 |
| AU469336B2 (en) | 1973-06-28 |
| YU322471A (en) | 1980-03-15 |
| AU3719771A (en) | 1973-06-28 |
| DK129654C (en) | 1975-04-01 |
| ES398208A1 (en) | 1974-08-16 |
| FR2119045B1 (en) | 1975-10-10 |
| CS166041B2 (en) | 1976-01-29 |
| DE2063406C3 (en) | 1978-05-03 |
| NL7117645A (en) | 1972-06-27 |
| DD95231A5 (en) | 1973-01-20 |
| NO136671C (en) | 1977-10-19 |
| SU420173A3 (en) | 1974-03-15 |
| CA939664A (en) | 1974-01-08 |
| IL38430A (en) | 1975-05-22 |
| BG20580A3 (en) | 1975-12-05 |
| FI50248B (en) | 1975-09-30 |
| NO136671B (en) | 1977-07-11 |
| IL38430A0 (en) | 1972-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |