NO300686B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater - Google Patents

Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater Download PDF

Info

Publication number: NO300686B1
Authority: NO; Norway
Prior art keywords: acid; mixture; solution; indolizintetrol; compound
Prior art date: 1990-06-04

Application number

NO924670A

Other languages

English (en)

Norwegian (no)

Other versions

NO924670D0 (no

NO924670L (no

Inventor

Paul Sai-Ho Liu

Mohinder Singh Kang

Original Assignee

Merrell Dow Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-06-04

Filing date

1992-12-03

Publication date

1997-07-07

1992-12-03 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1992-12-03 Publication of NO924670D0 publication Critical patent/NO924670D0/no

1992-12-03 Publication of NO924670L publication Critical patent/NO924670L/no

1997-07-07 Publication of NO300686B1 publication Critical patent/NO300686B1/no

Links

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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)

NO924670A 1990-06-04 1992-12-03 Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater NO300686B1 (no)

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 (fr)	1990-06-04	1991-05-08	Derives de 6-amino-octahydro-indolizinetriol

Publications (3)

Publication Number	Publication Date
NO924670D0 NO924670D0 (no)	1992-12-03
NO924670L NO924670L (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 (fr)
EP (1)	EP0532530B1 (fr)
JP (1)	JP3019265B2 (fr)
KR (1)	KR100195421B1 (fr)
AT (1)	ATE155685T1 (fr)
AU (1)	AU641771B2 (fr)
CA (1)	CA2082820C (fr)
DE (1)	DE69126978T2 (fr)
DK (1)	DK0532530T3 (fr)
ES (1)	ES2106080T3 (fr)
FI (1)	FI97226C (fr)
GR (1)	GR3025044T3 (fr)
HU (1)	HU212579B (fr)
NO (1)	NO300686B1 (fr)
WO (1)	WO1991018598A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1995013538A1 (fr) *	1993-11-12	1995-05-18	Operon Technologies, Inc.	Procede d'obtention et de criblage de bibliotheques de composes chimiques complexes
WO1995019359A1 (fr) *	1994-01-12	1995-07-20	Massachusetts Institute Of Technology	Procede de production de composes a base de xanthene ou de cubane et inhibitors de protease
US20070066543A1 (en) *	2003-05-22	2007-03-22	The Hospital For Sick Children	Treatment of tay sachs or sandhoff diseases by enhancing hexosaminidase activity
WO2005072268A2 (fr) *	2004-01-20	2005-08-11	Optimer Pharmaceuticals, Inc.	Traitement des pathologies cartilagineuses degeneratives chez les mammiferes au moyen d'inhibiteurs de la glycosidase
KR100858512B1 (ko)	2007-03-29	2008-09-12	포항공과대학교 산학협력단	헥소스아미니데이즈 활성 저해 방법
CA2732335A1 (fr)	2008-08-01	2010-02-04	Simon Fraser University	Inhibiteurs selectifs des glycosidases et leurs utilisations
RU2609210C2 (ru)	2010-12-23	2017-01-31	Алектос Терапьютикс Инк.	Селективные ингибиторы гликозидазы и их применение
EP2691407B1 (fr)	2011-03-31	2017-02-22	Alectos Therapeutics Inc.	Inhibiteurs sélectifs de glycosidases et leurs utilisations
US9701693B2 (en)	2011-06-27	2017-07-11	Alectos Therapeutics Inc.	Selective glycosidase inhibitors and uses thereof
EP2890676B1 (fr)	2012-08-31	2018-12-05	Alectos Therapeutics Inc.	Inhibiteurs de glycosidases et leurs utilisations
EP2890675A4 (fr)	2012-08-31	2016-01-13	Alectos Therapeutics Inc	Inhibiteurs des glycosidases et leurs utilisations
KR20150079711A (ko)	2012-10-31	2015-07-08	알렉토스 테라퓨틱스 인크.	글리코시다아제 저해제 및 이의 용도

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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 (fr) *	1987-07-02	1993-03-30	Paul S. Liu	Esters et glucosides de castanospermine
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 WO PCT/US1991/003179 patent/WO1991018598A1/fr not_active Ceased
- 1991-05-08 HU HU9203829A patent/HU212579B/hu not_active IP Right Cessation
- 1991-05-08 DE DE69126978T patent/DE69126978T2/de not_active Expired - Lifetime
- 1991-05-08 ES ES91909495T patent/ES2106080T3/es not_active Expired - Lifetime
- 1991-05-08 AT AT91909495T patent/ATE155685T1/de not_active IP Right Cessation
- 1991-05-08 EP EP91909495A patent/EP0532530B1/fr not_active Expired - Lifetime
- 1991-05-08 JP JP3509415A patent/JP3019265B2/ja not_active Expired - Lifetime
- 1991-05-08 CA CA002082820A patent/CA2082820C/fr not_active Expired - Lifetime
- 1991-05-08 DK DK91909495.3T patent/DK0532530T3/da active
- 1991-05-08 KR KR1019920703085A patent/KR100195421B1/ko not_active Expired - Fee Related
- 1991-05-08 AU AU78743/91A patent/AU641771B2/en not_active Ceased
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
AU641771B2 (en)	1993-09-30
NO924670D0 (no)	1992-12-03
NO924670L (no)	1992-12-03
ATE155685T1 (de)	1997-08-15
HU212579B (en)	1996-08-29
FI97226B (fi)	1996-07-31
FI925260L (fi)	1992-11-19
CA2082820A1 (fr)	1991-12-05
HU9203829D0 (en)	1993-03-29
WO1991018598A1 (fr)	1991-12-12
AU7874391A (en)	1991-12-31
DK0532530T3 (da)	1997-08-25
KR930700502A (ko)	1993-03-15
US5079254A (en)	1992-01-07
CA2082820C (fr)	2002-01-22
JPH05507474A (ja)	1993-10-28
FI925260A0 (fi)	1992-11-19
FI97226C (fi)	1996-11-11
DE69126978D1 (de)	1997-08-28
EP0532530B1 (fr)	1997-07-23
GR3025044T3 (en)	1998-01-30
HUT62585A (en)	1993-05-28
EP0532530A4 (en)	1993-05-26
JP3019265B2 (ja)	2000-03-13
EP0532530A1 (fr)	1993-03-24
DE69126978T2 (de)	1997-11-27
KR100195421B1 (ko)	1999-06-15
ES2106080T3 (es)	1997-11-01

Legal Events

Date	Code	Title	Description
2001-01-02	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN NOVEMBER 2000

Publication	Publication Date	Title
EP1026157B1 (fr)	2006-06-21	Procédé de synthèse de l'huperzine A et ses analogues et composés utiles dans cette synthèse
US20010049377A1 (en)	2001-12-06	Glucocortiocoid-selective antiinflammatory agents
NO300686B1 (no)	1997-07-07	Analogifremgangsmåte for fremstilling av terapeutisk aktive 6-aminooktahydroindolizintriolderivater
US6284789B1 (en)	2001-09-04	Formation and composition of new optically active compounds
KR20090106633A (ko)	2009-10-09	ＰＤＥ5 억제제로서 유용한 6-벤질-2,3,4,7-테트라히드로-인돌로[2,3-ｃ]퀴놀린 화합물
US5162335A (en)	1992-11-10	Di- and tetrahydroisoquinoline derivatives
CA2004986A1 (fr)	1990-06-12	Derives de piperidine
EP0680950B1 (fr)	2001-05-23	Derives de propenone
US5017704A (en)	1991-05-21	Fucosidase inhibitor
EP0401800A2 (fr)	1990-12-12	Dérivés acylés d'étoposide
Hu et al.	1992	Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4. beta.-(arylamino)-4'-O-demethylpodophyllotoxins
WO2018086242A1 (fr)	2018-05-17	Complexe de phtalocyanine de silicium à substitution axiale sensible au ph, son procédé de préparation et son application médicale
NO171555B (no)	1992-12-21	Analogifremgangsmaate for fremstilling av nye, terapeutiskaktive, substituerte alkanfenoner
EP0000306B1 (fr)	1980-05-28	Hexahydro benzopyrano (3,2-c) pyridines substituées, leur procédé de préparation et médicament les contenant
NO781051L (no)	1978-09-26	Kinazolinderivater.
US5220016A (en)	1993-06-15	Synthesis of navelbine analogs
US4895854A (en)	1990-01-23	Antitumor alkaloids
US5175297A (en)	1992-12-29	Methyl-quinoline derivatives as mefloquin intermediates and process for preparation thereof
US5153325A (en)	1992-10-06	Fucosidase inhibitor
US4999351A (en)	1991-03-12	7-aryl and heteroaryl ethers of desacetylforskolin
US5096909A (en)	1992-03-17	Fucosidase inhibitor
EP1474390B1 (fr)	2009-07-22	Derives d'indole substitues avec des alcools a longue chaine et medicaments contenant ceux-ci
JP2818976B2 (ja)	1998-10-30	ロイコトリエンｄ４拮抗薬としての二環式カルバメート
US5177207A (en)	1993-01-05	7-aryl and heteroaryl ethers of desacetylforskolin
JP2009537487A (ja)	2009-10-29	抗増殖薬及び血管新生阻害薬としてのボレリジン誘導体