KR830007485A - 벤조일-및 α-히드록시벤질-페닐-옥시드족에 속하는 신규 화합물의 제조방법 - Google Patents
벤조일-및 α-히드록시벤질-페닐-옥시드족에 속하는 신규 화합물의 제조방법 Download PDFInfo
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- KR830007485A KR830007485A KR1019810004143A KR810004143A KR830007485A KR 830007485 A KR830007485 A KR 830007485A KR 1019810004143 A KR1019810004143 A KR 1019810004143A KR 810004143 A KR810004143 A KR 810004143A KR 830007485 A KR830007485 A KR 830007485A
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- 238000000034 method Methods 0.000 title claims 6
- 150000001875 compounds Chemical class 0.000 title claims 5
- KXIOYXDMVGZJLZ-UHFFFAOYSA-N [2-[2-[hydroxy(phenyl)methyl]phenoxy]phenyl]-phenylmethanol Chemical group C=1C=CC=C(OC=2C(=CC=CC=2)C(O)C=2C=CC=CC=2)C=1C(O)C1=CC=CC=C1 KXIOYXDMVGZJLZ-UHFFFAOYSA-N 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- -1 isothiocyano group Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000010287 polarization Effects 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910010082 LiAlH Inorganic materials 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000005947 deacylation reaction Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 238000010575 fractional recrystallization Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
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- 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 하기 구조식(Ⅱ)의 페닐-페놀 유도체 1몰에 대해,(ⅰ) 할로아실로오즈 및 아실로오즈로 구성된 군에서 선택한 하나의 당유도체 1.1-1.2몰을 불활성 용매중에서 반응시키고,(ⅱ) 필요에 따라 탈-아실화 반응시킴을 특징으로 하는, 하기 구조식(Ⅰ)의, 벤조일-및 α-히드록시벤질-페닐-옥시드 족에 속하는 신규화합물 및 그의 이성체의 제조방법.여기서,Z는＞CO 또는＞COOH를 나타내고 :X2,X3,X4및 X5는 동일 또는 상이하며, 각각 수소원자, 할로겐원자, 탄소원자 1-4인 알킬기, 한개 이상의 할로겐 원자로 치환된 탄소원자 1-4인 알킬기, OH 기, 탄소원자 1-4인 알콕시기, 1개 이상의 할로겐원자로 치환된 탄소원자 1-4인 알콕시기, 니트로기, 시아노기, 티오시아노기, 이소티오시아노기 및 NR'R"기(여기서, R' 또는 R"는 동일 또는 상이하고, 각각 수소원자 또는 탄소원자 1-4인 알킬기임)를 나타내고, X1은 수소원자, 할로겐원자, 탄소원자 1-4를 갖는 알킬기, 한개 이상의 할로겐 원자로 치환이 된 탄소원자 1-4를 갖는 알킬기, OH기, 탄소원자 1-4인 알콕시기, 한개 이상의 할로겐 원자로 치환된 탄소원자 1-4인 알콕시기, 니트로기, 시아노기, 티오시아노기, 이소티오시아노기, NR'R"기(여기서 R' 및 R"는 동일 또는 상이하며, 각각 수소원자 또는 탄소원자 1-4인 알킬기를 나타냄), -NH-CS-O-CH3기 또는 -O-C(CH3)2CO2-R' '' 기(여기서, R''는 탄소원자 1-4인 알킬기, 바람직하기는 이소프로필기)를 나타내며: R은 치환이 가능한 당(ose) 라디칼을 나타낸다.(여기서, Z,X1,X2,X3,X4및 X5는 상기에서 정의한 바와 같고, A는 수소 또는, 바람직하기는 나트륨, 칼륨을 나타냄).
- 제 1 항에 있어서, 상기(ⅰ)의 단계에서, 1몰의 페닐-페놀 유도체(Ⅱ)를 (여기서, A는 나트륨 또는 칼륨), 극성 또는 비극성 용매(특히, 디메틸포름아미드, 디옥산, 테트라히드로푸란, 메탄올, 에탄올, 아세토니트릴, 니트로메탄, 디메틸술폭시드 및, 특히 DMF-CH2CI2, DMF-CHCl3, DMF-ClCH2Cl 혼합물과 같은, 이것과 1개의 기타 물질과의 또는 할로알칸류와의 혼합물) 중에서 택한 불활성 용매중에서, 1.1-1.2 몰의 하기식(Ⅲ) 의 할로아실로오즈와 반응시킴을 특징으로 하는 방법.Hal-R0(Ⅲ)(여기서, Hal은 플루오르, 염소, 브롬 및 요오드이고, 최적 수득량을 얻기 위해서는 염소 또는, 브롬이 적당하고, R0는 아실화한 당 라디칼 R을 나타낸다.)
- 제 2 항에 있어서, 화합물(Ⅱ)와 화합물(Ⅲ)과의 반응은, 0℃ 내지 반응 매질의 환류온도 사이의 온도에서, 10-40분 동안 행하는 것이 효과 있음을 특징으로 하는 방법.
- 제 1 항에 있어서, (ⅱ) 단계의 탈-아실화 반응은, 금속 알코올레이트의 존재하 탄소 1-4의 저급알코올 내에서 아실화 유도체를 가열 환류시켜서 수행하며, 바람직한 저급 알코올은 메탄올이고, 바람직한 금속 알코올레이트는 마그네슘 메틸레이트, 또는 나트륨메틸레이트임을 특징으로 하는 방법.
- Z가 CO일 때의 구조식(Ⅰ) 화합물로부터, Z가 CHOH일 때의 구조식(Ⅰ)의 유도체를 제조하는 방법에 있어서, Z가 CO일 때의 구조식(Ⅰ)의 유도체를, 불활성 용매 중에서, 특히 LiAlH4및 KBH4에서 취한 환원제를 이용하여, 0°-50℃ 범위의 온도에서 환원 반응시킴을 특징으로 하는 방법.
- Z가 CHOH일 때, 구조식(Ⅰ)의 부분 일체 이성 질체의 혼합물을 분별 재결정에 의하여 분리해내는 방법에 있어서,a) 부분 입체 이성체 혼합물을 (1 : 1)v/v 메탄올-물 혼합물에 용해시키고서, 일정 편광세기까지 재결정을 실시한 후, 우선성 부분 입체 이성체를 얻은 다음,b) a)단계의 재결정에서 얻은 여액을 (1 : 2)v/v 메탄올-물 혼합물로 처리하고 나서, 일정 편광세기까지재결정하여, 좌선성 부분 입체 이성체를 얻는 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR80-23133 | 1980-10-29 | ||
| FR8023133A FR2492830A1 (fr) | 1980-10-29 | 1980-10-29 | Nouveaux composes appartenant a la famille des benzoyl- et a-hydroxybenzyl-phenyl-osides, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007485A true KR830007485A (ko) | 1983-10-21 |
| KR870001926B1 KR870001926B1 (ko) | 1987-10-22 |
Family
ID=9247461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004143A KR870001926B1 (ko) | 1980-10-29 | 1981-10-29 | 벤조일-및 α-히드록시벤질-페닐-오사이드족에 속하는 신규화합물의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4432973A (ko) |
| EP (1) | EP0051023B1 (ko) |
| JP (1) | JPS57102899A (ko) |
| KR (1) | KR870001926B1 (ko) |
| AT (1) | ATE7701T1 (ko) |
| CA (1) | CA1181745A (ko) |
| CS (1) | CS224629B2 (ko) |
| DD (1) | DD202157A5 (ko) |
| DE (1) | DE3163912D1 (ko) |
| ES (1) | ES506660A0 (ko) |
| FR (1) | FR2492830A1 (ko) |
| GR (1) | GR75759B (ko) |
| HU (1) | HU191341B (ko) |
| ZA (1) | ZA817314B (ko) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549476B1 (fr) * | 1983-07-20 | 1986-04-25 | Rech Ind | Benzyl-phenyl-osides, procede de preparation et utilisation en therapeutique |
| JPS63215688A (ja) * | 1987-03-04 | 1988-09-08 | Jujo Paper Co Ltd | フェノ−ル配糖体の製造法 |
| 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 |
| 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 |
| 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 |
| IE63544B1 (en) * | 1988-10-18 | 1995-05-17 | Fournier Ind & Sante | Novel Beta-d-phenylthioxylosides their method of preparation and their use in therapy |
| ATE113956T1 (de) * | 1989-09-22 | 1994-11-15 | Fournier Ind & Sante | Benzopyranon-beta-d-thioxyloside, verfahren zu ihrer herstellung und ihre therapeutische verwendung. |
| 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. |
| ID26806A (id) * | 1998-06-24 | 2001-02-08 | Fournier Induatrie Et Sante | SENYAWA BARU YANG BERASAL DARI a-D-SILOSA, METODA PEMBUATAN DAN PENGGUNAAN TERAPINYA |
| US6525094B1 (en) | 1999-06-01 | 2003-02-25 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylether derivatives |
| EP1185232A1 (en) | 1999-06-01 | 2002-03-13 | University Of Texas Southwestern Medical Center | Method of treating hair loss using sulfonyl thyromimetic compounds |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| US6291433B1 (en) | 1999-06-11 | 2001-09-18 | Fournier Industrie Et Sante | Derivatives of α-D-Thioxyloside and their use against atheroma |
| FR2802929B1 (fr) * | 1999-12-23 | 2003-06-06 | Fournier Ind & Sante | Benzophenone alpha-d-glycopyranosides, preparation et utilisation en therapeutique |
| FR2802930B1 (fr) * | 1999-12-23 | 2003-10-10 | Fournier Ind & Sante | Benzophenone glycopyranosides, preparation et utilisation en therapeutique |
| US6586434B2 (en) * | 2000-03-10 | 2003-07-01 | G.D. Searle, Llc | Method for the preparation of tetrahydrobenzothiepines |
| FR2826367B1 (fr) * | 2001-06-21 | 2004-01-30 | Fournier Lab Sa | Nouveaux derives de [4-(4-cyanobenzoyl)phenyl] glycopyranoside, utilisation en tant que medicamment, procede d'obtention et compositions pharmaceutiques les contenant |
| 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 |
| FR2860234B1 (fr) | 2003-09-25 | 2005-12-23 | Fournier Lab Sa | Nouveaux derives 666 du thioxylose |
| WO2005077382A1 (ja) * | 2004-02-17 | 2005-08-25 | National Institute Of Advanced Industrial Science And Technology | プリオン増殖抑制剤 |
| EP1911738A4 (en) * | 2005-07-29 | 2009-12-16 | Takeda Pharmaceutical | PHENOXYALKANSÄUREVERBINDUNG |
| FR2903698B1 (fr) | 2006-07-13 | 2009-01-30 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose. |
| FR2906247B1 (fr) * | 2006-09-27 | 2008-12-26 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose |
| FR2906248B1 (fr) | 2006-09-27 | 2008-12-26 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2218569A (en) * | 1939-09-13 | 1940-10-22 | Dow Chemical Co | Glycosides of pentose ethers |
| US2798079A (en) * | 1953-12-29 | 1957-07-02 | Universal Oil Prod Co | Condensation of aromatic hydrocarbon derivatives with carbohydrates and related materials |
| US3152115A (en) * | 1960-11-17 | 1964-10-06 | Geigy Chem Corp | New aryl glucosaminides |
| US3356674A (en) * | 1961-07-07 | 1967-12-05 | Rikagaku Kenkyusho | 3-c-hydroxymethyl-3, 5-didesoxy-l-lyxofuranose and its derivatives, and a process for the production thereof |
| US3496196A (en) * | 1965-10-02 | 1970-02-17 | Tanabe Pharm Co Ltd | 4,6-diazido-4,6-dideoxy-myo-inositol tetraacylates |
| FR2141532B1 (ko) * | 1971-06-14 | 1974-08-23 | Anvar | |
| US3960835A (en) * | 1974-01-18 | 1976-06-01 | Commercial Solvents Corporation | Zearaline glycoside compounds |
| US4175123A (en) * | 1976-12-23 | 1979-11-20 | Bayer Aktiengesellschaft | Amino-sugar derivatives, process for their preparation and pharmaceutical composition thereof |
-
1980
- 1980-10-29 FR FR8023133A patent/FR2492830A1/fr active Granted
-
1981
- 1981-10-21 DE DE8181401654T patent/DE3163912D1/de not_active Expired
- 1981-10-21 AT AT81401654T patent/ATE7701T1/de not_active IP Right Cessation
- 1981-10-21 EP EP81401654A patent/EP0051023B1/fr not_active Expired
- 1981-10-22 US US06/314,032 patent/US4432973A/en not_active Expired - Fee Related
- 1981-10-22 ZA ZA817314A patent/ZA817314B/xx unknown
- 1981-10-23 GR GR66343A patent/GR75759B/el unknown
- 1981-10-28 ES ES506660A patent/ES506660A0/es active Granted
- 1981-10-28 HU HU813167A patent/HU191341B/hu not_active IP Right Cessation
- 1981-10-29 KR KR1019810004143A patent/KR870001926B1/ko active
- 1981-10-29 JP JP56172183A patent/JPS57102899A/ja active Granted
- 1981-10-29 CS CS817961A patent/CS224629B2/cs unknown
- 1981-10-29 CA CA000389050A patent/CA1181745A/en not_active Expired
- 1981-10-29 DD DD81234458A patent/DD202157A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES8302019A1 (es) | 1983-01-01 |
| JPS57102899A (en) | 1982-06-26 |
| HU191341B (en) | 1987-02-27 |
| US4432973A (en) | 1984-02-21 |
| GR75759B (ko) | 1984-08-02 |
| ATE7701T1 (de) | 1984-06-15 |
| CA1181745A (en) | 1985-01-29 |
| CS224629B2 (en) | 1984-01-16 |
| DD202157A5 (de) | 1983-08-31 |
| FR2492830B1 (ko) | 1983-10-07 |
| KR870001926B1 (ko) | 1987-10-22 |
| EP0051023A1 (fr) | 1982-05-05 |
| EP0051023B1 (fr) | 1984-05-30 |
| ES506660A0 (es) | 1983-01-01 |
| ZA817314B (en) | 1982-10-27 |
| JPH024235B2 (ko) | 1990-01-26 |
| FR2492830A1 (fr) | 1982-04-30 |
| DE3163912D1 (en) | 1984-07-05 |
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