GB1063786A - Improvements in or relating to podophyllum derivatives and their preparation - Google Patents
Improvements in or relating to podophyllum derivatives and their preparationInfo
- Publication number
- GB1063786A GB1063786A GB13120/64A GB1312064A GB1063786A GB 1063786 A GB1063786 A GB 1063786A GB 13120/64 A GB13120/64 A GB 13120/64A GB 1312064 A GB1312064 A GB 1312064A GB 1063786 A GB1063786 A GB 1063786A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen atom
- double bond
- signifies
- splitting
- compound
- 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
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- -1 methylenedioxy ring Chemical group 0.000 abstract 1
- 230000011278 mitosis Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention comprises compounds of formula <FORM:1063786/C2/1> wherein each of R4, R5, R6 and R7 signifies a hydrogen atom, or a methyl group, R1 is a hydrogen atom or a hydroxy group, each of R2 and R3 represents hydrogen or R2 together with R1 or R3 signifies a carbon-carbon bond, with R3 or R1, respectively, signifying a hydrogen atom, and their acetyl derivatives, which are prepared by splitting the methylenedioxy ring of lignanlactones of formula <FORM:1063786/C2/2> where R15 and R17 represent methyl groups, if desired, simultaneously or subsequently converting alkoxy radicals present in the C ring to hydroxy groups, and, if desired, if R1 is H and H in position 2 is in the a -position, splitting off the elements of water to produce a compound with a double bond in the 3,4-position. When acetylating a compound with a 3,4-double bond, and one or more free hydroxy groups to form the acetoxy derivative in the presence of a base, the double bond is displaced from 3,4- to 2,3-position. Various alternative processes are specifically described. Pharmaceutical compositions, which have mitosis inhibiting properties, and which may be administered enterally, parenterally or intranasally, contain as active ingredients compounds of the first general formula above or their acetyl derivatives.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH463163A CH436335A (en) | 1963-04-11 | 1963-04-11 | Process for the production of new Podophyllum compounds |
| CH60064 | 1964-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1063786A true GB1063786A (en) | 1967-03-30 |
Family
ID=25685081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13120/64A Expired GB1063786A (en) | 1963-04-11 | 1964-03-31 | Improvements in or relating to podophyllum derivatives and their preparation |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH436335A (en) |
| ES (1) | ES298471A1 (en) |
| FR (1) | FR3673M (en) |
| GB (1) | GB1063786A (en) |
| NL (1) | NL6403629A (en) |
-
1963
- 1963-04-11 CH CH463163A patent/CH436335A/en unknown
-
1964
- 1964-03-31 GB GB13120/64A patent/GB1063786A/en not_active Expired
- 1964-04-06 NL NL6403629A patent/NL6403629A/xx unknown
- 1964-04-09 ES ES298471A patent/ES298471A1/en not_active Expired
- 1964-07-08 FR FR981141A patent/FR3673M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| NL6403629A (en) | 1964-10-12 |
| ES298471A1 (en) | 1964-09-01 |
| CH436335A (en) | 1967-05-31 |
| FR3673M (en) | 1964-11-08 |
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