NO155804B - Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. - Google Patents

Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. Download PDF

Info

Publication number: NO155804B
Authority: NO; Norway
Prior art keywords: melting point; ethyl; alkyl; irimycin; preparation
Prior art date: 1980-02-26

Application number

NO810485A

Other languages

English (en)

Norwegian (no)

Other versions

NO810485L (no

Inventor

Bodo Junge

Juergen Stoltefuss

Lutz Mueller

Hans-Peter Krause

Ruediger Sitt

Original Assignee

Bayer Ag

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.)

1980-02-26

Filing date

1981-02-12

Publication date

1987-02-23

1981-02-12 Application filed by Bayer Ag filed Critical Bayer Ag

1981-08-27 Publication of NO810485L publication Critical patent/NO810485L/no

1987-02-23 Publication of NO155804B publication Critical patent/NO155804B/no

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 8
230000001225 therapeutic effect Effects 0.000 title description 3
RMCNETIHECSPMZ-UHFFFAOYSA-N piperidine-3,4,5-triol Chemical class OC1CNCC(O)C1O RMCNETIHECSPMZ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 22
-1 3,4,5-trihydroxypiperidine compound Chemical class 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
238000005932 reductive alkylation reaction Methods 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 21
150000003053 piperidines Chemical class 0.000 abstract description 4
235000019728 animal nutrition Nutrition 0.000 abstract 1
238000002844 melting Methods 0.000 description 35
230000008018 melting Effects 0.000 description 35
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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 description 3
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000019219 chocolate Nutrition 0.000 description 1
239000004927 clay Substances 0.000 description 1
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
229960001214 clofibrate Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
230000029087 digestion Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000005429 filling process Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
229950006238 nadide Drugs 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940127017 oral antidiabetic Drugs 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000013573 potato product Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Supply Devices, Intensifiers, Converters, And Telemotors (AREA)
Rolls And Other Rotary Bodies (AREA)
Paints Or Removers (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

NO810485A 1980-02-26 1981-02-12 Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. NO155804B (no)

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 (2)

Publication Number	Publication Date
NO810485L NO810485L (no)	1981-08-27
NO155804B true NO155804B (no)	1987-02-23

Family

ID=6095540

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO810485A NO155804B (no)	1980-02-26	1981-02-12	Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.

Country Status (18)

Country	Link
US (1)	US4407809A (th)
EP (1)	EP0034784B1 (th)
JP (3)	JPS56133267A (th)
AT (1)	ATE8623T1 (th)
AU (1)	AU538463B2 (th)
CA (1)	CA1160634A (th)
DE (2)	DE3007078A1 (th)
DK (1)	DK153545C (th)
ES (1)	ES499782A0 (th)
FI (1)	FI75807C (th)
GR (1)	GR73691B (th)
HU (1)	HU183346B (th)
IE (1)	IE51317B1 (th)
IL (1)	IL62198A (th)
NO (1)	NO155804B (th)
PT (1)	PT72507B (th)
SU (1)	SU1014471A3 (th)
ZA (1)	ZA811252B (th)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
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
WO1991003242A1 (en) *	1989-09-07	1991-03-21	Nippon Shinyaku Co., Ltd.	Antiviral drug
US5536732A (en) *	1990-04-27	1996-07-16	Merrell Pharmaceuticals Inc.	N-derivatives of 1-deoxy nojirimycin
US5252587A (en) *	1990-04-27	1993-10-12	Merrell Dow 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
AU2003248960B2 (en)	2002-07-17	2009-06-25	Idorsia Pharmaceuticals Ltd	Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
ES2393331T3 (es) *	2002-07-17	2012-12-20	Actelion Pharmaceuticals Ltd.	Derivados de piperidintriol como inhibidores de la glucosiliceramida 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
CN101489554A (zh) *	2006-05-24	2009-07-22	联合治疗公司	脱氧吉瑞霉素和d-阿拉伯胶素醇类似物及使用方法
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
CA2875975A1 (en) *	2012-06-06	2013-12-12	Unither Virology, Llc	Novel iminosugars and their applications
CA2924026C (en) *	2013-09-16	2021-12-28	Emergent Virology Llc	Deoxynojirimycin derivatives and methods of their using

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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 DE DE8181101056T patent/DE3164944D1/de not_active Expired
- 1981-02-14 EP EP81101056A patent/EP0034784B1/de not_active Expired
- 1981-02-14 AT AT81101056T patent/ATE8623T1/de not_active IP Right Cessation
- 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 IL IL62198A patent/IL62198A/xx not_active IP Right Cessation
- 1981-02-23 SU SU813246202A patent/SU1014471A3/ru active
- 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 ES ES499782A patent/ES499782A0/es active Granted
- 1981-02-25 JP JP2556881A patent/JPS56133267A/ja active Granted
- 1981-02-25 IE IE391/81A patent/IE51317B1/en not_active IP Right Cessation
- 1981-02-25 DK DK084181A patent/DK153545C/da not_active IP Right Cessation
- 1981-02-25 ZA ZA00811252A patent/ZA811252B/xx unknown
- 1981-02-26 HU HU81468A patent/HU183346B/hu not_active IP Right Cessation
1984
- 1984-12-21 JP JP59268708A patent/JPS60166616A/ja active Granted
- 1984-12-21 JP JP59268709A patent/JPS60166663A/ja active Pending

Also Published As

Publication number	Publication date
DK84181A (da)	1981-08-27
SU1014471A3 (ru)	1983-04-23
DE3007078A1 (de)	1981-09-10
ES8201549A1 (es)	1981-12-16
IL62198A0 (en)	1981-03-31
JPS56133267A (en)	1981-10-19
CA1160634A (en)	1984-01-17
JPS6152147B2 (th)	1986-11-12
AU538463B2 (en)	1984-08-16
EP0034784B1 (de)	1984-07-25
DE3164944D1 (en)	1984-08-30
IE51317B1 (en)	1986-12-10
ZA811252B (en)	1982-03-31
JPS60166616A (ja)	1985-08-29
JPH0342243B2 (th)	1991-06-26
PT72507B (en)	1982-02-05
NO810485L (no)	1981-08-27
EP0034784A1 (de)	1981-09-02
IL62198A (en)	1985-03-31
FI75807B (fi)	1988-04-29
DK153545B (da)	1988-07-25
GR73691B (th)	1984-04-03
FI810559L (fi)	1981-08-27
AU6748081A (en)	1981-09-03
FI75807C (fi)	1988-08-08
IE810391L (en)	1981-08-26
DK153545C (da)	1988-12-05
HU183346B (en)	1984-04-28
US4407809A (en)	1983-10-04
ES499782A0 (es)	1981-12-16
ATE8623T1 (de)	1984-08-15
JPS60166663A (ja)	1985-08-29
PT72507A (en)	1981-03-01

Publication	Publication Date	Title
NO154918B (no)	1986-10-06	Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
US4533668A (en)	1985-08-06	Antihyperglycemic moranoline derivatives
US4871747A (en)	1989-10-03	3-Amino-4,5-dihydroxypiperidines, process for their preparation and their use
EP1966193B1 (en)	2010-09-29	New salt and polymorph of dpp-iv inhibitor
CA1088073A (en)	1980-10-21	Hydantoin therapeutic agents
US5276058A (en)	1994-01-04	3,4-dihydroxychalcone derivatives
CA1292000C (en)	1991-11-12	Solid forms of 2-ethoxy-4-[n-(1-(2-piperidino- phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoic acid
KR100388747B1 (ko)	2004-03-30	인돌유도체
EP0749423B1 (en)	2003-06-18	Piperidines and pyrrolidines
PL121663B1 (en)	1982-05-31	Process for preparing novel amides of n2 upwards-arylsulfonyl-l-argininenina
DK155321B (da)	1989-03-28	Analogifremgangsmaade til fremstilling af 3,4,5-trihydroxypiperidinderivater
US4407809A (en)	1983-10-04	N-phenoxy(or thio)hydrocarbon 3,4,5-trihydroxypiperidine derivatives, their use in medicine and in animal nutrition
NO165922B (no)	1991-01-21	Analogifremgangsmaate for fremstilling av terapeutisk aktive estere av hexahydro-8-hydroxy-2,6-methano-2h-kinolizin-3-(4h)-on og beslektede forbindelser.
US4312872A (en)	1982-01-26	1-Alka-2,4-dienyl-2-hydroxymethyl-3,4,5-trihydroxypiperidines as inhibitors of α-glucoside hydrolases
NO151837B (no)	1985-03-04	Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner
AU602083B2 (en)	1990-09-27	Pyrimidine derivatives
AU609146B2 (en)	1991-04-26	Castanospermine esters and glycosides
US5041444A (en)	1991-08-20	Benzoxepin derivatives
CA1153766A (en)	1983-09-13	Thioxo-1h-benz(de)isoquinoline-2(3h)- acetic acid derivatives
NO852778L (no)	1980-12-08	Nye derivater av 3,4,5-trihydroksypiperidin, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel saavel i dyrenaering
US3829434A (en)	1974-08-13	Piperidinesulfonylurea derivatives
EP0121197B1 (en)	1986-11-20	Pyrazolopyridine derivatives, therapeutic compositions comprising same, and process thereof
NO150280B (no)	1984-06-12	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 9-aminopyrido(1,2-a)pyrimidinderivater
US4034095A (en)	1977-07-05	Benzo[5,6]cyclohepta[1,2-c]pyridines
US3583983A (en)	1971-06-08	N-benzenesulfonyl-iso-indole carboxamides