HUP0003666A2 - Method for the preparation of citalopram and pharmaceutical compositions containing them - Google Patents
Method for the preparation of citalopram and pharmaceutical compositions containing themInfo
- Publication number
- HUP0003666A2 HUP0003666A2 HU0003666A HUP0003666A HUP0003666A2 HU P0003666 A2 HUP0003666 A2 HU P0003666A2 HU 0003666 A HU0003666 A HU 0003666A HU P0003666 A HUP0003666 A HU P0003666A HU P0003666 A2 HUP0003666 A2 HU P0003666A2
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- citalopram
- preparation
- formula
- pharmaceutical compositions
- Prior art date
Links
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title abstract 2
- 229960001653 citalopram Drugs 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 2
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Preparation of citalopram (1-(3-(dimethylamino)propyl)- 1-(4-fluorophenyl)-1,3-dihydro- 5-isobenzofurancarbonitrile) (I) comprises: (a) reducing a compound of formula (IV); (b) effecting ring closure of the resulting compound of formula (V) to give a compound of formula (VI); then (c) if R1 = CN, using compound (VI) directly in the next step, and if R1 = 1-6C alkyloxycarbonyl or 1-6C alkylaminocarbonyl, converting (VI) to the compound where R1 = CN; and (d) alkylating the resulting compound (VI; R1 = CN) with 3-dimethylaminopropylhalide under basic conditions to give (I), which is isolated as the base or a salt. R1 = CN, 1-6C alkyloxycarbonyl or 1-6C alkylaminocarbonyl. Compounds (V) and (VI), and step (d) are claimed per se.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/DK1997/000511 WO1998019511A2 (en) | 1997-11-10 | 1997-11-10 | Method for the preparation of citalopram |
CNB971825017A CN100338051C (en) | 1997-11-10 | 1997-11-10 | Method for preparation of citalopram |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0003666A2 true HUP0003666A2 (en) | 2002-06-29 |
HUP0003666A3 HUP0003666A3 (en) | 2002-12-28 |
Family
ID=38543967
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0003666A HUP0003666A3 (en) | 1997-11-10 | 1997-11-10 | Method for the preparation of citalopram and pharmaceutical compositions containing them |
Country Status (1)
Country | Link |
---|---|
HU (1) | HUP0003666A3 (en) |
-
1997
- 1997-11-10 HU HU0003666A patent/HUP0003666A3/en unknown
Also Published As
Publication number | Publication date |
---|---|
HUP0003666A3 (en) | 2002-12-28 |
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