BE904614A - Procede de preparation de la diosmine. - Google Patents

Procede de preparation de la diosmine. Download PDF

Info

Publication number: BE904614A
Authority: BE; Belgium
Prior art keywords: diosmin; preparation; pyridine; esperidin; solvent
Prior art date: 1985-05-30

Application number

BE0/216543A

Other languages

English (en)

French (fr)

Inventor

G Vandoni

Original Assignee

Edmond Pharma Srl

Priority date (The priority date 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 date listed.)

1985-05-30

Filing date

1986-04-17

Publication date

1986-08-18

1986-04-17 Application filed by Edmond Pharma Srl filed Critical Edmond Pharma Srl

1986-08-18 Publication of BE904614A publication Critical patent/BE904614A/fr

Links

238000000034 method Methods 0.000 title claims abstract description 24
GZSOSUNBTXMUFQ-YFAPSIMESA-N diosmin Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 GZSOSUNBTXMUFQ-YFAPSIMESA-N 0.000 title claims abstract description 22
229960004352 diosmin Drugs 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims description 8
GZSOSUNBTXMUFQ-NJGQXECBSA-N 5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4cc(O)c(OC)cc4)Oc3c2)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 GZSOSUNBTXMUFQ-NJGQXECBSA-N 0.000 claims abstract description 21
IGBKNLGEMMEWKD-UHFFFAOYSA-N diosmin Natural products COc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 IGBKNLGEMMEWKD-UHFFFAOYSA-N 0.000 claims abstract description 21
VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 claims abstract description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
150000007530 organic bases Chemical class 0.000 claims description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 8
229920005989 resin Polymers 0.000 claims description 8
229920000075 poly(4-vinylpyridine) Polymers 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims 2
239000012442 inert solvent Substances 0.000 claims 1
KKOAVMPFXWZPNS-UHFFFAOYSA-N Esperidin Natural products COc1ccc(cc1O)C2CC(=O)c3c(O)cc(OC4OC(C)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4O)cc3O2 KKOAVMPFXWZPNS-UHFFFAOYSA-N 0.000 abstract description 11
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 10
229910052740 iodine Inorganic materials 0.000 abstract description 10
239000011630 iodine Substances 0.000 abstract description 10
239000003960 organic solvent Substances 0.000 abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
229940071870 hydroiodic acid Drugs 0.000 description 8
239000000203 mixture Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
150000007514 bases Chemical class 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
230000026045 iodination Effects 0.000 description 2
238000006192 iodination reaction Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BE0/216543A 1985-05-30 1986-04-17 Procede de preparation de la diosmine. BE904614A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8520974A IT1191620B (it)	1985-05-30	1985-05-30	Procedimento per la preparazione della diosmina

Publications (1)

Publication Number	Publication Date
BE904614A true BE904614A (fr)	1986-08-18

Family

ID=11174849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/216543A BE904614A (fr)	1985-05-30	1986-04-17	Procede de preparation de la diosmine.

Country Status (3)

Country	Link
BE (1)	BE904614A (it)
ES (1)	ES8706659A1 (it)
IT (1)	IT1191620B (it)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0860443A1 (fr) *	1997-02-21	1998-08-26	Innokem, SARL	Procédé de fabrication industrielle de diosmine à partir de l'hesperidine
FR2760015A1 (fr) *	1997-02-21	1998-08-28	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine
FR2782518A1 (fr) *	1998-08-19	2000-02-25	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine par reaction avec de l'iode et de la pyridine
EP3321273A4 (en) *	2016-08-30	2018-11-14	Chengdu Okay Pharmaceutical Co., Ltd	Preparation method of diosmin
US10287310B2 (en)	2015-02-03	2019-05-14	Interquim, S.A.	Process for the preparation of diosmin

1985
- 1985-05-30 IT IT8520974A patent/IT1191620B/it active
1986
- 1986-04-17 BE BE0/216543A patent/BE904614A/fr not_active IP Right Cessation
- 1986-05-28 ES ES555384A patent/ES8706659A1/es not_active Expired

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0860443A1 (fr) *	1997-02-21	1998-08-26	Innokem, SARL	Procédé de fabrication industrielle de diosmine à partir de l'hesperidine
FR2760015A1 (fr) *	1997-02-21	1998-08-28	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine
FR2760016A1 (fr) *	1997-02-21	1998-08-28	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine
FR2782518A1 (fr) *	1998-08-19	2000-02-25	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine par reaction avec de l'iode et de la pyridine
WO2000011009A3 (fr) *	1998-08-19	2000-06-29	Innokem Sarl	Procede de fabrication industrielle de diosmine a partir de l'hesperidine par reaction avec de l'iode et de la pyridine
US10287310B2 (en)	2015-02-03	2019-05-14	Interquim, S.A.	Process for the preparation of diosmin
US10711025B2 (en)	2015-02-03	2020-07-14	Interquim, S.A.	Process for the preparation of diosmin
EP3321273A4 (en) *	2016-08-30	2018-11-14	Chengdu Okay Pharmaceutical Co., Ltd	Preparation method of diosmin

Also Published As

Publication number	Publication date
ES555384A0 (es)	1987-07-16
IT8520974A0 (it)	1985-05-30
IT1191620B (it)	1988-03-23
ES8706659A1 (es)	1987-07-16

Legal Events

Date

Code

Title

Description

1992-10-31

RE

Patent lapsed

Owner name: EDMOND S.P.R.L.

Effective date: 19920430

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