KR850001227A - 벤질 페닐 오사이드 유도체의 제조방법 - Google Patents
벤질 페닐 오사이드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850001227A KR850001227A KR1019840004282A KR840004282A KR850001227A KR 850001227 A KR850001227 A KR 850001227A KR 1019840004282 A KR1019840004282 A KR 1019840004282A KR 840004282 A KR840004282 A KR 840004282A KR 850001227 A KR850001227 A KR 850001227A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- phenyl
- radical
- carbon atoms
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- -1 α- hydroxybenzyl phenyl compound Chemical class 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 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 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- DELQDRUXFQFMQT-XDNAFOTISA-N (2s,3r,4s,5r)-2-[4-[(4-chlorophenyl)methyl]phenoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1OC(C=C1)=CC=C1CC1=CC=C(Cl)C=C1 DELQDRUXFQFMQT-XDNAFOTISA-N 0.000 claims 1
- QSDSZOAFLXTJCE-XDNAFOTISA-N (2s,3r,4s,5r)-2-[4-[(4-nitrophenyl)methyl]phenoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1OC(C=C1)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 QSDSZOAFLXTJCE-XDNAFOTISA-N 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical group CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 1
- 125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 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
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 다음 일반식(II)의 벤조일 페닐 오사이드 또는 α-하이드록시 벤질 페닐 오사이드 화합물을 트리플루오로 아세트산 중에서 NaBH4또는 KBH4의 환원 제로 환원시킴을 특징으로 하여 다음 일반식(I)의 벤질 페닐 오사이드 유도체 및 이의 산부가염(하기 X1,X2,X3,X4,X5및 R의 적어도 하나가 염기성 래디칼을 포함하는 경우)상기 일반식에서,X1,X2,X3,X4및 X5는 같거나 다르며, 각기 수소원자, 할로겐원자, 탄소수 1 내지 4의 알킬그룹, 하나이상의 할로겐 원자로 치환된 탄소수 1 내지 4의 알킬 그룹(특히 CF3그룹), OH그룹, 탄소수 1 내지 4의 알콕시 그룹, 하나이상의 할로겐 원자로 치환된 탄소수 1 내지 4의 알콕시 그룹, 니트로 그룹, NR'R"그룹(여기에서 R' 및 R"는 같거나 다르며, 각기 수소원자, 탄소수 1 내지 4의 알킬 그룹 또는 아세틸 그룹을 나타냄), 메틸 티오그룹, 메틸 설피닐 그룹 또는 메실 그룹을 나타내고, R은 (a)α-L-람노실래디칼, (b) 비-가수분해성 모노사카라이드 래디칼 (c) 2-위치의 탄소원자상의 하이드록실 그룹이 아민 그룹으로 치환된 비-가수분해성 모노사카라이드 래디칼중에서 선택된 오스 래디칼을 나타내고, R그룹의 하이드록실 그룹 및 아민 그룹은 아세틸화 할 수 있으며 Z는 CO 또는 CHOH를 나타낸다.
- 제1항에 있어서, 연속적으로 (i)화합물(II) 및 트리플루오로아세트산으로 이루어진 혼합물로 0℃이하의 온도에서 적어도 0.5시간에 걸쳐 화합물(II)에 대해 과량의 환원제를 도입하고 (ii)첨가를 마치면, 반응이 계속되도록 0내지 20℃의 온도에서 교반하면서 0.5 내지 12시간동안 방치시키는 방법.
- 제1항 또는 제2항에 있어서, X1,X2,X3,X4및 X5가 같거나 다르며, 각기 H, Cl, Br, CH3, CF3, OH, OCH3, NO2, NH2, N(CH3)2, SCH3, SOCH3또는 SO2CH3를 나타내고, R은 α-L-람노실, β-D-글루코실, β-D-크실로실, β-D-갈락토실, α-L-아라비노실 및 β-D-글루코사미닐래시칼중에서 선택된 래디칼을 나타내며, 필요시 OH 및 NH2그룹을 아세틸화할 수 있는 방법.
- 제1항 내지 제3항중 어느 하나에 있어서, R이 β-D-글루코실, β-D-크실로실, β-D-갈락토실, α-L-아라비노실, β-D-글루코사미닐 및 α-L-람노실 래디칼중에서 선택되고, 필요시 하이드록실 및 아민그룹이 아세틸 그룹으로 치환될 수 있는 방법.
- 제1항에 있어서, 다음 화합물을 제조하는 방법.4-(4-니트로벤질)페닐 β-D-크실로피라노사이드, 4-(4-클로로벤질)페닐 β-D-크실로피라노사이드, 3-(4-클로로벤질)페닐 β-D-크실로피라노사이드, 4-(4-메실벤질)페닐 β-D-크실로피라노사이드.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR83-11982 | 1983-07-20 | ||
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 |
---|---|
KR850001227A true KR850001227A (ko) | 1985-03-16 |
KR910008109B1 KR910008109B1 (ko) | 1991-10-10 |
Family
ID=9290966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840004282A KR910008109B1 (ko) | 1983-07-20 | 1984-07-20 | 벤질페닐 오사이드 유도체의 제조방법 |
Country Status (17)
Country | Link |
---|---|
US (1) | US4598068A (ko) |
EP (1) | EP0133103B1 (ko) |
JP (1) | JPS6041691A (ko) |
KR (1) | KR910008109B1 (ko) |
AT (1) | ATE30726T1 (ko) |
CA (1) | CA1226576A (ko) |
CS (1) | CS244692B2 (ko) |
DD (1) | DD224596A5 (ko) |
DE (1) | DE3467349D1 (ko) |
DK (1) | DK164556C (ko) |
ES (1) | ES8505382A1 (ko) |
FR (1) | FR2549476B1 (ko) |
GR (1) | GR82068B (ko) |
HU (1) | HU195835B (ko) |
NO (1) | NO157259C (ko) |
PT (1) | PT78938B (ko) |
ZA (1) | ZA845580B (ko) |
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 |
EP0367671B1 (en) * | 1988-11-03 | 1993-07-28 | Fournier Industrie Et Sante | Novel beta-d-phenylthioxylosides, their method of preparation and their use as pharmaceuticals |
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. |
EP0421829B1 (fr) * | 1989-09-22 | 1994-11-09 | Fournier Industrie Et Sante | Nouveaux benzopyranone-beta-D-thioxylosides, leur procédé de préparation et leur utilisation en thérapeutique |
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 |
CZ303544B6 (cs) * | 2000-09-29 | 2012-11-28 | Kissei Pharmaceutical Co., Ltd. | Glukopyranosyloxybenzylbenzenový derivát a farmaceutická kompozice s jeho obsahem |
CA2429833A1 (en) * | 2000-11-30 | 2002-06-06 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
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 NO NO842916A patent/NO157259C/no unknown
- 1984-07-17 DE DE8484401496T patent/DE3467349D1/de not_active Expired
- 1984-07-17 EP EP84401496A patent/EP0133103B1/fr not_active Expired
- 1984-07-17 AT AT84401496T patent/ATE30726T1/de not_active IP Right Cessation
- 1984-07-18 HU HU842794A patent/HU195835B/hu not_active IP Right Cessation
- 1984-07-18 PT PT78938A patent/PT78938B/pt not_active IP Right Cessation
- 1984-07-18 US US06/632,009 patent/US4598068A/en not_active Expired - Fee Related
- 1984-07-19 CS CS845568A patent/CS244692B2/cs unknown
- 1984-07-19 JP JP59151113A patent/JPS6041691A/ja active Pending
- 1984-07-19 DD DD84265446A patent/DD224596A5/de not_active IP Right Cessation
- 1984-07-19 CA CA000459291A patent/CA1226576A/en not_active Expired
- 1984-07-19 ZA ZA845580A patent/ZA845580B/xx unknown
- 1984-07-19 GR GR75362A patent/GR82068B/el unknown
- 1984-07-19 DK DK353184A patent/DK164556C/da not_active IP Right Cessation
- 1984-07-20 KR KR1019840004282A patent/KR910008109B1/ko not_active IP Right Cessation
- 1984-07-20 ES ES534528A patent/ES8505382A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2549476B1 (fr) | 1986-04-25 |
JPS6041691A (ja) | 1985-03-05 |
HUT36133A (en) | 1985-08-28 |
ES534528A0 (es) | 1985-05-16 |
ATE30726T1 (de) | 1987-11-15 |
PT78938B (fr) | 1986-06-02 |
ZA845580B (en) | 1985-02-27 |
PT78938A (fr) | 1984-08-01 |
DK353184D0 (da) | 1984-07-19 |
NO157259C (no) | 1988-02-17 |
KR910008109B1 (ko) | 1991-10-10 |
GR82068B (ko) | 1984-12-13 |
CS244692B2 (en) | 1986-08-14 |
DK164556C (da) | 1992-12-07 |
NO157259B (no) | 1987-11-09 |
DD224596A5 (de) | 1985-07-10 |
CS556884A2 (en) | 1985-09-17 |
CA1226576A (en) | 1987-09-08 |
US4598068A (en) | 1986-07-01 |
DK164556B (da) | 1992-07-13 |
HU195835B (en) | 1988-07-28 |
FR2549476A1 (fr) | 1985-01-25 |
NO842916L (no) | 1985-01-21 |
EP0133103B1 (fr) | 1987-11-11 |
ES8505382A1 (es) | 1985-05-16 |
DK353184A (da) | 1985-01-21 |
EP0133103A1 (fr) | 1985-02-13 |
DE3467349D1 (en) | 1987-12-17 |
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GRNT | Written decision to grant | ||
LAPS | Lapse due to unpaid annual fee |