SU1014471A3 - Способ получени производных 3,4,5-тригидроксипиперидина - Google Patents
Способ получени производных 3,4,5-тригидроксипиперидина Download PDFInfo
- Publication number
- SU1014471A3 SU1014471A3 SU813246202A SU3246202A SU1014471A3 SU 1014471 A3 SU1014471 A3 SU 1014471A3 SU 813246202 A SU813246202 A SU 813246202A SU 3246202 A SU3246202 A SU 3246202A SU 1014471 A3 SU1014471 A3 SU 1014471A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- melting point
- yield
- ethyl
- trihydroxypiperidine
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- RMCNETIHECSPMZ-UHFFFAOYSA-N piperidine-3,4,5-triol Chemical class OC1CNCC(O)C1O RMCNETIHECSPMZ-UHFFFAOYSA-N 0.000 title 1
- -1 3,4,5-trihydroxypiperidine compound Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 241000231697 Zelus means Species 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 4
- 150000003053 piperidines Chemical class 0.000 abstract 3
- 235000019728 animal nutrition Nutrition 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- KHANGFJTBIHUNK-UHFFFAOYSA-N 1-hydroxypiperidine-2,2-diol Chemical class ON1CCCCC1(O)O KHANGFJTBIHUNK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 201000005577 familial hyperlipidemia Diseases 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UEFBOQYLXLEJSM-UHFFFAOYSA-N 2-bromoethylsulfanylbenzene Chemical compound BrCCSC1=CC=CC=C1 UEFBOQYLXLEJSM-UHFFFAOYSA-N 0.000 description 1
- WNGRHTGNGQSCTL-UHFFFAOYSA-N 5-bromopentoxybenzene Chemical compound BrCCCCCOC1=CC=CC=C1 WNGRHTGNGQSCTL-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- 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
-
- 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
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Polymers & Plastics (AREA)
- Endocrinology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Emergency Medicine (AREA)
- Food Science & Technology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Rolls And Other Rotary Bodies (AREA)
- Paints Or Removers (AREA)
- Supply Devices, Intensifiers, Converters, And Telemotors (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803007078 DE3007078A1 (de) | 1980-02-26 | 1980-02-26 | Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel sowie in der tierernaehrung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1014471A3 true SU1014471A3 (ru) | 1983-04-23 |
Family
ID=6095540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813246202A SU1014471A3 (ru) | 1980-02-26 | 1981-02-23 | Способ получени производных 3,4,5-тригидроксипиперидина |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4407809A (OSRAM) |
| EP (1) | EP0034784B1 (OSRAM) |
| JP (3) | JPS56133267A (OSRAM) |
| AT (1) | ATE8623T1 (OSRAM) |
| AU (1) | AU538463B2 (OSRAM) |
| CA (1) | CA1160634A (OSRAM) |
| DE (2) | DE3007078A1 (OSRAM) |
| DK (1) | DK153545C (OSRAM) |
| ES (1) | ES8201549A1 (OSRAM) |
| FI (1) | FI75807C (OSRAM) |
| GR (1) | GR73691B (OSRAM) |
| HU (1) | HU183346B (OSRAM) |
| IE (1) | IE51317B1 (OSRAM) |
| IL (1) | IL62198A (OSRAM) |
| NO (1) | NO155804B (OSRAM) |
| PT (1) | PT72507B (OSRAM) |
| SU (1) | SU1014471A3 (OSRAM) |
| ZA (1) | ZA811252B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2702133C2 (ru) * | 2013-09-16 | 2019-10-04 | ЭМЕРГЕНТ ВИРОЛОДЖИ ЭлЭлСи | Производные дезоксинойиримицина и способы их применения |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3737523A1 (de) * | 1987-11-05 | 1989-05-18 | Bayer Ag | Verwendung von substituierten hydroxypiperidinen als antivirale mittel |
| GB8827701D0 (en) * | 1987-12-09 | 1988-12-29 | Nippon Shinyaku Co Ltd | Thrombolytic &c compositions |
| US5192772A (en) * | 1987-12-09 | 1993-03-09 | Nippon Shinyaku Co. Ltd. | Therapeutic agents |
| US4985445A (en) * | 1988-02-12 | 1991-01-15 | Meiji Seika Kaisha, Ltd. | Cancer cell metastasis inhibitors and novel compounds |
| CA2065446A1 (en) * | 1989-09-07 | 1991-03-08 | Yoshiaki Yoshikuni | Antiviral drug |
| US5252587A (en) * | 1990-04-27 | 1993-10-12 | Merrell Dow Pharmaceuticals, Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5536732A (en) * | 1990-04-27 | 1996-07-16 | Merrell Pharmaceuticals Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5258518A (en) * | 1992-04-01 | 1993-11-02 | G. D. Searle & Co. | 2-substituted tertiary carbinol derivatives of deoxynojirimycin |
| US6177447B1 (en) * | 1996-07-15 | 2001-01-23 | Universiteit Van Amsterdam | Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors |
| GB0100889D0 (en) * | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| US7985760B2 (en) * | 2002-07-17 | 2011-07-26 | Actelion Pharmaceuticals Ltd. | Piperidinetriol derivatives as inhibitors of glycosyceramid synthase |
| ES2393919T3 (es) | 2002-07-17 | 2013-01-02 | Actelion Pharmaceuticals Ltd. | Derivados de PIPERIDINETRIOL como inhibidores de GLUCOSILCERAMIDA SINTASA |
| GB0313678D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compounds |
| GB0313677D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
| WO2007140184A2 (en) * | 2006-05-24 | 2007-12-06 | United Therapeutics Corporation | Deoxynojirimycin and d-arabinitol analogs and methods of using |
| WO2010027996A1 (en) * | 2008-09-02 | 2010-03-11 | Institute For Hepatitis And Virus Research | Novel imino sugar derivatives demonstrate potent antiviral activity and reduced toxicity |
| JP2015518896A (ja) * | 2012-06-06 | 2015-07-06 | ユニザー ヴィロロジー，エルエルシー | 新規イミノ糖およびそれらの用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) * | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| GB2020278B (en) * | 1978-05-03 | 1983-02-23 | Nippon Shinyaku Co Ltd | Moranoline dervitives |
| DE2839309A1 (de) * | 1978-09-09 | 1980-03-27 | Bayer Ag | 3,4,5-trihydroxypiperidin-derivate |
| JPS5683409A (en) * | 1979-12-13 | 1981-07-08 | Nippon Shinyaku Co Ltd | Plant growth regulator |
| DE3322006A1 (de) * | 1983-06-18 | 1984-12-20 | Robert Bosch Gmbh, 7000 Stuttgart | Vorrichtung zur steuerung eines induktiven stellgliedes, insbesondere eines vergasers |
-
1980
- 1980-02-26 DE DE19803007078 patent/DE3007078A1/de not_active Withdrawn
-
1981
- 1981-02-05 US US06/231,695 patent/US4407809A/en not_active Expired - Lifetime
- 1981-02-12 NO NO810485A patent/NO155804B/no unknown
- 1981-02-14 AT AT81101056T patent/ATE8623T1/de not_active IP Right Cessation
- 1981-02-14 DE DE8181101056T patent/DE3164944D1/de not_active Expired
- 1981-02-14 EP EP81101056A patent/EP0034784B1/de not_active Expired
- 1981-02-16 PT PT72507A patent/PT72507B/pt not_active IP Right Cessation
- 1981-02-20 AU AU67480/81A patent/AU538463B2/en not_active Ceased
- 1981-02-23 SU SU813246202A patent/SU1014471A3/ru active
- 1981-02-23 IL IL62198A patent/IL62198A/xx not_active IP Right Cessation
- 1981-02-24 GR GR64232A patent/GR73691B/el unknown
- 1981-02-24 CA CA000371582A patent/CA1160634A/en not_active Expired
- 1981-02-24 FI FI810559A patent/FI75807C/fi not_active IP Right Cessation
- 1981-02-25 IE IE391/81A patent/IE51317B1/en not_active IP Right Cessation
- 1981-02-25 ES ES499782A patent/ES8201549A1/es not_active Expired
- 1981-02-25 ZA ZA00811252A patent/ZA811252B/xx unknown
- 1981-02-25 JP JP2556881A patent/JPS56133267A/ja active Granted
- 1981-02-25 DK DK084181A patent/DK153545C/da not_active IP Right Cessation
- 1981-02-26 HU HU81468A patent/HU183346B/hu not_active IP Right Cessation
-
1984
- 1984-12-21 JP JP59268709A patent/JPS60166663A/ja active Pending
- 1984-12-21 JP JP59268708A patent/JPS60166616A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| 1. Вейганд-Хильгетаг Методы эксперимента в органической химии, .М., Хими , 1968, с. . * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2702133C2 (ru) * | 2013-09-16 | 2019-10-04 | ЭМЕРГЕНТ ВИРОЛОДЖИ ЭлЭлСи | Производные дезоксинойиримицина и способы их применения |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56133267A (en) | 1981-10-19 |
| US4407809A (en) | 1983-10-04 |
| NO155804B (no) | 1987-02-23 |
| IE51317B1 (en) | 1986-12-10 |
| CA1160634A (en) | 1984-01-17 |
| PT72507B (en) | 1982-02-05 |
| JPS60166616A (ja) | 1985-08-29 |
| DE3164944D1 (en) | 1984-08-30 |
| ATE8623T1 (de) | 1984-08-15 |
| EP0034784B1 (de) | 1984-07-25 |
| DE3007078A1 (de) | 1981-09-10 |
| HU183346B (en) | 1984-04-28 |
| ES499782A0 (es) | 1981-12-16 |
| IE810391L (en) | 1981-08-26 |
| IL62198A (en) | 1985-03-31 |
| JPS60166663A (ja) | 1985-08-29 |
| AU6748081A (en) | 1981-09-03 |
| JPH0342243B2 (OSRAM) | 1991-06-26 |
| IL62198A0 (en) | 1981-03-31 |
| ZA811252B (en) | 1982-03-31 |
| PT72507A (en) | 1981-03-01 |
| FI75807B (fi) | 1988-04-29 |
| EP0034784A1 (de) | 1981-09-02 |
| FI810559L (fi) | 1981-08-27 |
| DK153545C (da) | 1988-12-05 |
| AU538463B2 (en) | 1984-08-16 |
| GR73691B (OSRAM) | 1984-04-03 |
| DK153545B (da) | 1988-07-25 |
| DK84181A (da) | 1981-08-27 |
| ES8201549A1 (es) | 1981-12-16 |
| JPS6152147B2 (OSRAM) | 1986-11-12 |
| NO810485L (no) | 1981-08-27 |
| FI75807C (fi) | 1988-08-08 |
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