Patent US7932406B2 successfully refreshed from Google Patents.
US7932406B2
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for preparing 4β-amino-4′-demethyl-4-desoxypodophyllotoxin
Assignee: Pierre Fabre Medicament SA
•
Filing: 2006-07-19
•
Granted: 2011-04-26
•
Expires: 2026-07-19
Abstract
Abstract The invention relates to a method for synthesizing 4.beta.-amino-4′-demethyl-4-desoxypodophyllotoxin of formula (1), characterized by comprising the following successive steps: a) reacting, in a pure weak acid or in a mixture consisting of acid, water and of organic solvent, without another solvent, at a temperature higher than the ambient temperature, thiourea with 4.beta.-halogenoacetamido-4′-demethyl-4-desoxypodophyllotoxin, and; b) recovering the 4.beta.-amino-4′-demethyl-4-desoxypodophyllotoxin.
Inventors
- 👤 Yves Guminski
- 👤 Martial Grousseaud
- 👤 Thierry Imbert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:00
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
81 words
A method for synthesising a halogenohydrate of 4β-amino-4′-demethyl-4-desoxypodophyllotoxin of formula 1 in which X represents a halogen atom selected from the group consisting of chlorine, bromine and iodine; comprising the following stages: reaction, in a pure weak acid, without another solvent, at a temperature greater than ambient temperature of thiourea with 4β-halogenoacetamino-4′-demethyl-4-desoxypodophyllotoxin of formula 3 in which X represents a halogen atom selected from the group composed of chlorine, bromine and iodine, advantageously chlorine; and recovery of the halogenohydrate of 4β-amino-4′-demethyl-4-desoxypodophyllotoxin.
Claim 2
Independent Claim
81 words
A method for synthesising a halogenohydrate of 4β-amino-4′-demethyl-4-desoxypodophyllotoxin of formula 1 in which X represents a halogen atom selected from the group consisting of chlorine, bromine and iodine; comprising the following stages: reaction, in a pure weak acid, without another solvent, at a temperature greater than ambient temperature of thiourea with 4β-halogenoacetamino-4′-demethyl-4-desoxypodophyllotoxin of formula 3 in which X represents a halogen atom selected from the group composed of chlorine, bromine and iodine, advantageously chlorine; and recovery of the halogenohydrate of 4β-amino-4′-demethyl-4-desoxypodophyllotoxin.
Claim 3
Dependent Claim
36 words
The method as claimed in claim 1 , wherein the pure weak acid is a carboxylic acid of formula 5 R—COOH, in which R represents hydrogen or an alkyl radical in C 1 -C 2 .
Claim 4
Dependent Claim
16 words
The method as claimed in claim 2 , wherein the pure weak acid is acetic acid.
Claim 5
Dependent Claim
25 words
The method as claimed in claim 1 , wherein during stage a) the reaction medium is heated to a temperature between 60 and 100° C.
Claim 6
Dependent Claim
27 words
The method as claimed in claim 1 , wherein during stage a) 4β-halogenoacetamido-4′-demethyl-4-desoxypodophyllotoxin is placed in contact with the pure weak acid prior to addition of thiourea.
Claim 7
Dependent Claim
21 words
The method as claimed in claim 1 , wherein the reaction time of stage a) is between 1 and 3 hours.
Claim 8
Dependent Claim
21 words
The method as claimed in claim 1 , wherein the molar ratio between 4β-halogenoacetamido-4′-demethyl-4-desoxypodophyllotoxin and thiourea is between 0.5 and 1.
Claim 9
Dependent Claim
54 words
The method as claimed in claim 1 , wherein the 4β-halogenoacetamido-4′-demethyl-4-desoxypodophyllotoxin of formula 3 is obtained by reaction of 4′-demethylpipodophyllotoxin of formula 2 with a halogenoacetonitrile of formula 6X—CH 2 —C≡N, in which X represents a halogen atom selected from the group composed of the chlorine, the bromine and the iodine, in acid medium.
Claim 10
Dependent Claim
12 words
The method as claimed in claim 1 , wherein X is chlorine.
References Cited (Backward Citations)
FR2869035A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2014-04-25 | 2014-10-25 | 2015-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2018-04-25 | 2018-10-25 | 2019-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2022-04-25 | 2022-10-25 | 2023-04-26 | $7700.00 | Window Closed / Lapsed |