JPH0555518B2 - - Google Patents

Info

Publication number: JPH0555518B2
Authority: JP; Japan
Prior art keywords: diosmin; complex; sulfur trioxide; aluminum; pyridine
Prior art date: 1987-07-31
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 - Lifetime

Application number

JP88189532A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6463590A (en

Inventor

Oruharesu Benero Aurerio

Mosukeera Pesutaanya Ramon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FUABURIKA ESUPANYOORA DE PUROD

Original Assignee

FUABURIKA ESUPANYOORA DE PUROD

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.)

1987-07-31

Filing date

1988-07-28

Publication date

1993-08-17

1987-07-31 Priority claimed from ES8702270A external-priority patent/ES2004465A6/es

1988-07-28 Application filed by FUABURIKA ESUPANYOORA DE PUROD filed Critical FUABURIKA ESUPANYOORA DE PUROD

1989-03-09 Publication of JPS6463590A publication Critical patent/JPS6463590A/ja

1993-08-17 Publication of JPH0555518B2 publication Critical patent/JPH0555518B2/ja

Status Granted legal-status Critical Current

Links

AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 23
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 claims description 22
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 description 20
229960004352 diosmin Drugs 0.000 claims description 20
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 description 20
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 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
230000001180 sulfating effect Effects 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
NNCOOIBIVIODKO-UHFFFAOYSA-N aluminum;hypochlorous acid Chemical compound [Al].ClO NNCOOIBIVIODKO-UHFFFAOYSA-N 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
APGUSRKQFBWUPZ-UHFFFAOYSA-K disulfooxyalumanyl hydrogen sulfate Chemical compound [Al+3].OS([O-])(=O)=O.OS([O-])(=O)=O.OS([O-])(=O)=O APGUSRKQFBWUPZ-UHFFFAOYSA-K 0.000 claims description 3
230000002496 gastric effect Effects 0.000 claims description 3
239000002904 solvent Substances 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
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
239000003223 protective agent Substances 0.000 claims 1
238000005670 sulfation reaction Methods 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000005270 trialkylamine group Chemical group 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010908 decantation Methods 0.000 description 2
230000000762 glandular Effects 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930003944 flavone Natural products 0.000 description 1
150000002212 flavone derivatives Chemical class 0.000 description 1
235000011949 flavones Nutrition 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000013824 polyphenols Nutrition 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
230000001681 protective effect Effects 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
-1 sulfate alcohols Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP63189532A 1987-07-31 1988-07-28 Novel diosmine derivative and its production Granted JPS6463590A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES8702270A ES2004465A6 (es)	1986-05-09	1987-07-31	Procedimiento de preparcion de un nuevo derivado de diosmina
EP87500053A EP0302155B1 (en)	1986-05-09	1987-07-31	Preparation of a new diosmine derivate

Publications (2)

Publication Number	Publication Date
JPS6463590A JPS6463590A (en)	1989-03-09
JPH0555518B2 true JPH0555518B2 (da)	1993-08-17

Family

ID=26112482

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63189532A Granted JPS6463590A (en)	1987-07-31	1988-07-28	Novel diosmine derivative and its production

Country Status (8)

Country	Link
JP (1)	JPS6463590A (da)
AR (1)	AR247216A1 (da)
AT (1)	AT397504B (da)
AU (1)	AU613386B2 (da)
CA (1)	CA1318317C (da)
FI (1)	FI88924C (da)
GR (1)	GR880100499A (da)
NO (1)	NO171165C (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3730858B2 (ja) *	2000-12-01	2006-01-05	株式会社エヌ・ティ・ティ・ドコモ	メールシステム、サーバ及びメール送受信装置

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR6967M (da) *	1968-01-22	1969-05-19
EP0075626A1 (en) *	1981-09-29	1983-04-06	American Cyanamid Company	Novel rutin nona- and deca(H-)sulfate salts, methods of preparing novel salts, and use of novel salts of complement inhibitors

1988
- 1988-07-19 AT AT0185388A patent/AT397504B/de not_active IP Right Cessation
- 1988-07-26 FI FI883508A patent/FI88924C/fi not_active IP Right Cessation
- 1988-07-28 GR GR880100499A patent/GR880100499A/el unknown
- 1988-07-28 JP JP63189532A patent/JPS6463590A/ja active Granted
- 1988-07-28 CA CA000573330A patent/CA1318317C/en not_active Expired - Fee Related
- 1988-07-29 NO NO883363A patent/NO171165C/no unknown
- 1988-07-29 AR AR88311551A patent/AR247216A1/es active
- 1988-07-29 AU AU20128/88A patent/AU613386B2/en not_active Ceased

Also Published As

Publication number	Publication date
FI883508L (fi)	1989-02-01
FI88924C (fi)	1993-07-26
AU613386B2 (en)	1991-08-01
JPS6463590A (en)	1989-03-09
AR247216A1 (es)	1994-11-30
NO883363L (no)	1989-02-01
ATA185388A (de)	1993-09-15
NO171165B (no)	1992-10-26
NO883363D0 (no)	1988-07-29
FI883508A0 (fi)	1988-07-26
FI88924B (fi)	1993-04-15
CA1318317C (en)	1993-05-25
AU2012888A (en)	1989-02-02
AT397504B (de)	1994-04-25
GR880100499A (el)	1989-04-12
NO171165C (no)	1993-02-03

Publication	Publication Date	Title
Green et al.	1937	Glycofuranosides and Thioglycofuranosides. I. A Method of Preparation and its Application to Galactose and Glucose
EP0302155B1 (en)	1993-10-27	Preparation of a new diosmine derivate
JPS61140599A (ja)	1986-06-27	５’‐メチルチオ‐５’‐デオキシアデノシンと長鎖アルキルスルホン酸との塩
WO2026091351A1 (zh)	2026-05-07	一种水飞蓟宾的衍生物，其制备方法及应用
EP0251039B1 (en)	1991-09-18	Esters of salsalate with guaiacol, for treating phlogistic bronchopneumopathies
CA1318317C (en)	1993-05-25	Preparation of a new diosmine derivative
Wolfrom et al.	1939	Tritylation Experiments in the Sugar Alcohol Series
WO1998056750A1 (en)	1998-12-17	A process for the preparation of diacerein
KR100272646B1 (ko)	2000-11-15	황산화 디오스민 유도체
US2705232A (en)	1955-03-29	Ternorcholanylthiazoles
JPS5890584A (ja)	1983-05-30	新規な抗炎症薬剤
JPS61100593A (ja)	1986-05-19	グリゼオ−ル酸誘導体
JPS6241230B2 (da)	1987-09-02
JP4310820B2 (ja)	2009-08-12	カルバゾクロムスルホン酸誘導体の製法
JPH04500677A (ja)	1992-02-06	モノ―またはポリヒドロキシル化された分子のヒドロキシル化されたサイトを置換することによる新規なジチオカルバミン酸エステルの特殊な合成方法と、この方法によって得られた製品と、その応用
US4073802A (en)	1978-02-14	Process for the preparation and purification of 3-(4-lithiosulfophenoxy)-1,2-propanediol
KR100877134B1 (ko)	2009-01-09	아캄프로세이트 칼슘의 제조방법
JPS60260540A (ja)	1985-12-23	ジフタル酸エステル誘導体及びその製造法，並びにこれを有効成分とする抗潰瘍剤
KR810001154B1 (ko)	1981-09-22	5-설파모일-오르트아닐린산의 제조방법
KR890000173B1 (ko)	1989-03-09	3-부톡시-1-페녹시-2-푸로판올의 제조방법
JPS6155914B2 (da)	1986-11-29
GB2120243A (en)	1983-11-30	Phenolic antioxidant
KR900006216B1 (ko)	1990-08-25	탄닌산 카나마이신과 그 제조방법 및 그 용도와 의약조성물
US858446A (en)	1907-07-02	Organic iodin preparation.
JPH06239903A (ja)	1994-08-30	シクロデキストリン誘導体及びその製造方法