NO300686B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater Download PDFInfo
- Publication number
- NO300686B1 NO300686B1 NO924670A NO924670A NO300686B1 NO 300686 B1 NO300686 B1 NO 300686B1 NO 924670 A NO924670 A NO 924670A NO 924670 A NO924670 A NO 924670A NO 300686 B1 NO300686 B1 NO 300686B1
- Authority
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- Norway
- Prior art keywords
- acid
- mixture
- solution
- indolizintetrol
- compound
- Prior art date
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000004709 cell invasion Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007911 effervescent powder Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000036212 malign transformation Effects 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- KNWQLFOXPQZGPX-UHFFFAOYSA-N methanesulfonyl fluoride Chemical compound CS(F)(=O)=O KNWQLFOXPQZGPX-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000006548 oncogenic transformation Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/532,522 US5079254A (en) | 1990-06-04 | 1990-06-04 | Derivatives of 6-aminooctahydroindolizinetriol |
| PCT/US1991/003179 WO1991018598A1 (en) | 1990-06-04 | 1991-05-08 | Derivatives of 6-aminooctahydroindolizinetriol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924670L NO924670L (no) | 1992-12-03 |
| NO924670D0 NO924670D0 (no) | 1992-12-03 |
| NO300686B1 true NO300686B1 (no) | 1997-07-07 |
Family
ID=24122149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924670A NO300686B1 (no) | 1990-06-04 | 1992-12-03 | Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5079254A (fi) |
| EP (1) | EP0532530B1 (fi) |
| JP (1) | JP3019265B2 (fi) |
| KR (1) | KR100195421B1 (fi) |
| AT (1) | ATE155685T1 (fi) |
| AU (1) | AU641771B2 (fi) |
| CA (1) | CA2082820C (fi) |
| DE (1) | DE69126978T2 (fi) |
| DK (1) | DK0532530T3 (fi) |
| ES (1) | ES2106080T3 (fi) |
| FI (1) | FI97226C (fi) |
| GR (1) | GR3025044T3 (fi) |
| HU (1) | HU212579B (fi) |
| NO (1) | NO300686B1 (fi) |
| WO (1) | WO1991018598A1 (fi) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995013538A1 (en) * | 1993-11-12 | 1995-05-18 | Operon Technologies, Inc. | Methods of producing and screening complex chemical libraries |
| AU1562895A (en) * | 1994-01-12 | 1995-08-01 | Massachusetts Institute Of Technology | Process for making xanthene or cubane based compounds, and protease inhibitors |
| EP1633356A1 (en) * | 2003-05-22 | 2006-03-15 | The Hospital for Sick Children | Treatment of tay sachs or sandhoff diseases by enhancing hexosaminidase activity |
| US20070197471A1 (en) * | 2004-01-20 | 2007-08-23 | Optimer Pharmaceuticals, Inc. | Treatment of degenerative cartilage conditions in a mammal with Glycosidasc Inhibitors |
| KR100858512B1 (ko) | 2007-03-29 | 2008-09-12 | 포항공과대학교 산학협력단 | 헥소스아미니데이즈 활성 저해 방법 |
| CA2732335A1 (en) * | 2008-08-01 | 2010-02-04 | Simon Fraser University | Selective glycosidase inhibitors and uses thereof |
| WO2012083435A1 (en) | 2010-12-23 | 2012-06-28 | Alectos Therapeutics, Inc. | Selective glycosidase inhibitors and uses thereof |
| EP2691407B1 (en) | 2011-03-31 | 2017-02-22 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2013000086A1 (en) | 2011-06-27 | 2013-01-03 | Alectos Therapeutics Inc. | Selective glycosidase inhibitors and uses thereof |
| WO2014032185A1 (en) | 2012-08-31 | 2014-03-06 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
| EP2890675A4 (en) | 2012-08-31 | 2016-01-13 | Alectos Therapeutics Inc | GLYCOSIDASE INHIBITORS AND USES THEREOF |
| WO2014067003A1 (en) | 2012-10-31 | 2014-05-08 | Alectos Therapeutics Inc. | Glycosidase inhibitors and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5973519A (ja) * | 1982-09-17 | 1984-04-25 | Fujisawa Pharmaceut Co Ltd | スワインソニンの製造法およびそれを含む免疫調整剤 |
| GB8429810D0 (en) * | 1984-11-26 | 1985-01-03 | Fujisawa Pharmaceutical Co | Indolizidine derivatives |
| JPS61277685A (ja) * | 1985-05-31 | 1986-12-08 | Fujisawa Pharmaceut Co Ltd | 新規インドリジジン誘導体、その製造法およびそれを含有する組成物 |
| DE3620645A1 (de) * | 1985-12-20 | 1987-07-02 | Bayer Ag | 3-amino-4,5-dihydroxypiperidine, verfahren zu ihrer herstellung und ihre verwendung |
| CA1315276C (en) * | 1987-07-02 | 1993-03-30 | Paul S. Liu | Castanospermine esters and glycosides |
| JPH01129182A (ja) * | 1987-11-16 | 1989-05-22 | Tokyo Keiki Co Ltd | 波動伝搬時間測定装置 |
| JPH01277685A (ja) * | 1988-04-28 | 1989-11-08 | Hitachi Ltd | ピストンポンプ |
-
1990
- 1990-06-04 US US07/532,522 patent/US5079254A/en not_active Expired - Lifetime
-
1991
- 1991-05-08 KR KR1019920703085A patent/KR100195421B1/ko not_active IP Right Cessation
- 1991-05-08 DE DE69126978T patent/DE69126978T2/de not_active Expired - Lifetime
- 1991-05-08 DK DK91909495.3T patent/DK0532530T3/da active
- 1991-05-08 WO PCT/US1991/003179 patent/WO1991018598A1/en active IP Right Grant
- 1991-05-08 AU AU78743/91A patent/AU641771B2/en not_active Ceased
- 1991-05-08 AT AT91909495T patent/ATE155685T1/de not_active IP Right Cessation
- 1991-05-08 ES ES91909495T patent/ES2106080T3/es not_active Expired - Lifetime
- 1991-05-08 JP JP3509415A patent/JP3019265B2/ja not_active Expired - Lifetime
- 1991-05-08 HU HU9203829A patent/HU212579B/hu not_active IP Right Cessation
- 1991-05-08 EP EP91909495A patent/EP0532530B1/en not_active Expired - Lifetime
- 1991-05-08 CA CA002082820A patent/CA2082820C/en not_active Expired - Lifetime
-
1992
- 1992-11-19 FI FI925260A patent/FI97226C/fi not_active IP Right Cessation
- 1992-12-03 NO NO924670A patent/NO300686B1/no not_active IP Right Cessation
-
1997
- 1997-10-15 GR GR970402690T patent/GR3025044T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI925260A (fi) | 1992-11-19 |
| HU9203829D0 (en) | 1993-03-29 |
| FI925260A0 (fi) | 1992-11-19 |
| JP3019265B2 (ja) | 2000-03-13 |
| DK0532530T3 (da) | 1997-08-25 |
| AU7874391A (en) | 1991-12-31 |
| DE69126978T2 (de) | 1997-11-27 |
| GR3025044T3 (en) | 1998-01-30 |
| CA2082820A1 (en) | 1991-12-05 |
| FI97226C (fi) | 1996-11-11 |
| NO924670L (no) | 1992-12-03 |
| KR100195421B1 (ko) | 1999-06-15 |
| EP0532530A4 (en) | 1993-05-26 |
| EP0532530B1 (en) | 1997-07-23 |
| JPH05507474A (ja) | 1993-10-28 |
| DE69126978D1 (de) | 1997-08-28 |
| ES2106080T3 (es) | 1997-11-01 |
| HU212579B (en) | 1996-08-29 |
| WO1991018598A1 (en) | 1991-12-12 |
| EP0532530A1 (en) | 1993-03-24 |
| AU641771B2 (en) | 1993-09-30 |
| HUT62585A (en) | 1993-05-28 |
| US5079254A (en) | 1992-01-07 |
| FI97226B (fi) | 1996-07-31 |
| NO924670D0 (no) | 1992-12-03 |
| ATE155685T1 (de) | 1997-08-15 |
| CA2082820C (en) | 2002-01-22 |
| KR930700502A (ko) | 1993-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN NOVEMBER 2000 |