CS244692B2 - Production method of benzilphenylosides - Google Patents
Production method of benzilphenylosides Download PDFInfo
- Publication number
- CS244692B2 CS244692B2 CS845568A CS556884A CS244692B2 CS 244692 B2 CS244692 B2 CS 244692B2 CS 845568 A CS845568 A CS 845568A CS 556884 A CS556884 A CS 556884A CS 244692 B2 CS244692 B2 CS 244692B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- compound
- beta
- reducing agent
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- -1 alpha -hydroxybenzylphenyl Chemical group 0.000 claims abstract description 4
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 125000003404 beta-D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
- 239000003638 chemical reducing agent Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000003381 deacetylation reaction Methods 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 230000006196 deacetylation Effects 0.000 claims 1
- KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 claims 1
- 201000005577 familial hyperlipidemia Diseases 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 150000008366 benzophenones Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8311982A FR2549476B1 (fr) | 1983-07-20 | 1983-07-20 | Benzyl-phenyl-osides, procede de preparation et utilisation en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS556884A2 CS556884A2 (en) | 1985-09-17 |
| CS244692B2 true CS244692B2 (en) | 1986-08-14 |
Family
ID=9290966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS845568A CS244692B2 (en) | 1983-07-20 | 1984-07-19 | Production method of benzilphenylosides |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4598068A (de) |
| EP (1) | EP0133103B1 (de) |
| JP (1) | JPS6041691A (de) |
| KR (1) | KR910008109B1 (de) |
| AT (1) | ATE30726T1 (de) |
| CA (1) | CA1226576A (de) |
| CS (1) | CS244692B2 (de) |
| DD (1) | DD224596A5 (de) |
| DE (1) | DE3467349D1 (de) |
| DK (1) | DK164556C (de) |
| ES (1) | ES534528A0 (de) |
| FR (1) | FR2549476B1 (de) |
| GR (1) | GR82068B (de) |
| HU (1) | HU195835B (de) |
| NO (1) | NO157259C (de) |
| PT (1) | PT78938B (de) |
| ZA (1) | ZA845580B (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960758A (en) * | 1987-05-04 | 1990-10-02 | Fournier Innovation Et Synergie | Novel β-D-phenylthioxylosides, their method of preparation and their use as pharmaceuticals |
| FR2614893B1 (fr) * | 1987-05-04 | 1989-12-22 | Fournier Innovation Synergie | Nouveaux b-d-phenyl-thioxylosides, leur procede de preparation et leur application en therapeutique |
| FR2614894B1 (fr) * | 1987-05-06 | 1989-06-16 | Adir | Nouvelles oximes derivees de la tylosine, leur procede de preparation et les compositions pharmaceutiques les contenant |
| US5246961A (en) * | 1988-10-18 | 1993-09-21 | Fournier Industrie Et Sante | β-d-phenylthioxylosides, and their use as therapeutic agents |
| IE63544B1 (en) * | 1988-10-18 | 1995-05-17 | Fournier Ind & Sante | Novel Beta-d-phenylthioxylosides their method of preparation and their use in therapy |
| DE68907857T2 (de) * | 1988-11-03 | 1993-12-23 | Fournier Ind Et Sante Paris | Beta-D-phenylthioxyloside, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel. |
| FR2652353B1 (fr) * | 1989-09-22 | 1994-02-11 | Fournier Industrie Sante | Nouveaux benzopyran-2-one-beta-d-thioxylosides, leur procede de preparation et leur utilisation en therapeutique. |
| CA2024476C (en) * | 1989-09-22 | 1999-10-12 | Soth Samreth | Benzopyranone-.beta.-d-thioxylosides their method of preparation and their use in therapy |
| US6291433B1 (en) | 1999-06-11 | 2001-09-18 | Fournier Industrie Et Sante | Derivatives of α-D-Thioxyloside and their use against atheroma |
| NZ521369A (en) * | 2000-03-17 | 2004-07-30 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives |
| SK287811B6 (sk) * | 2000-09-29 | 2011-10-04 | Kissei Pharmaceutical Co., Ltd | Glukopyranozyloxybenzylbenzénový derivát, farmaceutická kompozícia a ľudský SGLT2-inhibítor tento derivát obsahujúci a použitie tohto derivátu |
| EP1344780A4 (de) * | 2000-11-30 | 2004-01-28 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzolderivate, medizinische zusammensetzungen, die diese verbindungen enthalten, und zwischenprodukte für deren herstellung |
| TWI255817B (en) * | 2001-02-14 | 2006-06-01 | Kissei Pharmaceutical | Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof |
| FR2826368B1 (fr) * | 2001-06-21 | 2004-01-30 | Fournier Lab Sa | Nouveaux derives de [4-(4-cyanobenzoyl)phenyl] glycofuranoside, utilisation en tant que medicamment, procede d'obtention et compositions pharmaceutiques les contenant |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL167151C (nl) * | 1971-04-09 | 1981-11-16 | Acf Chemiefarma Nv | Werkwijze ter bereiding van geneesmiddelen met anti-parasitaire werking op basis van halogeen bevatten- de 2,2'-methyleendifenolderivaten, alsmede werkwijze ter bereiding van deze geneeskrachtige verbindingen. |
| FR2492830A1 (fr) * | 1980-10-29 | 1982-04-30 | Sori Soc Rech Ind | Nouveaux composes appartenant a la famille des benzoyl- et a-hydroxybenzyl-phenyl-osides, leur procede de preparation et leur application en therapeutique |
-
1983
- 1983-07-20 FR FR8311982A patent/FR2549476B1/fr not_active Expired
-
1984
- 1984-07-17 DE DE8484401496T patent/DE3467349D1/de not_active Expired
- 1984-07-17 EP EP84401496A patent/EP0133103B1/de not_active Expired
- 1984-07-17 AT AT84401496T patent/ATE30726T1/de not_active IP Right Cessation
- 1984-07-17 NO NO842916A patent/NO157259C/no unknown
- 1984-07-18 US US06/632,009 patent/US4598068A/en not_active Expired - Fee Related
- 1984-07-18 PT PT78938A patent/PT78938B/pt not_active IP Right Cessation
- 1984-07-18 HU HU842794A patent/HU195835B/hu not_active IP Right Cessation
- 1984-07-19 DD DD84265446A patent/DD224596A5/de not_active IP Right Cessation
- 1984-07-19 DK DK353184A patent/DK164556C/da not_active IP Right Cessation
- 1984-07-19 JP JP59151113A patent/JPS6041691A/ja active Pending
- 1984-07-19 ZA ZA845580A patent/ZA845580B/xx unknown
- 1984-07-19 GR GR75362A patent/GR82068B/el unknown
- 1984-07-19 CA CA000459291A patent/CA1226576A/en not_active Expired
- 1984-07-19 CS CS845568A patent/CS244692B2/cs unknown
- 1984-07-20 ES ES534528A patent/ES534528A0/es active Granted
- 1984-07-20 KR KR1019840004282A patent/KR910008109B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS556884A2 (en) | 1985-09-17 |
| DE3467349D1 (en) | 1987-12-17 |
| PT78938A (fr) | 1984-08-01 |
| PT78938B (fr) | 1986-06-02 |
| DD224596A5 (de) | 1985-07-10 |
| HUT36133A (en) | 1985-08-28 |
| FR2549476B1 (fr) | 1986-04-25 |
| HU195835B (en) | 1988-07-28 |
| ZA845580B (en) | 1985-02-27 |
| KR910008109B1 (ko) | 1991-10-10 |
| DK164556B (da) | 1992-07-13 |
| DK164556C (da) | 1992-12-07 |
| NO157259C (no) | 1988-02-17 |
| ES8505382A1 (es) | 1985-05-16 |
| EP0133103B1 (de) | 1987-11-11 |
| CA1226576A (en) | 1987-09-08 |
| FR2549476A1 (fr) | 1985-01-25 |
| DK353184A (da) | 1985-01-21 |
| US4598068A (en) | 1986-07-01 |
| GR82068B (de) | 1984-12-13 |
| JPS6041691A (ja) | 1985-03-05 |
| ATE30726T1 (de) | 1987-11-15 |
| KR850001227A (ko) | 1985-03-16 |
| ES534528A0 (es) | 1985-05-16 |
| NO842916L (no) | 1985-01-21 |
| NO157259B (no) | 1987-11-09 |
| DK353184D0 (da) | 1984-07-19 |
| EP0133103A1 (de) | 1985-02-13 |
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