FI84833B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-glykosylamider n-glykosylkarbamider och n -glykosylkarbamater. - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-glykosylamider n-glykosylkarbamider och n -glykosylkarbamater. Download PDFInfo
- Publication number
- FI84833B FI84833B FI862619A FI862619A FI84833B FI 84833 B FI84833 B FI 84833B FI 862619 A FI862619 A FI 862619A FI 862619 A FI862619 A FI 862619A FI 84833 B FI84833 B FI 84833B
- Authority
- FI
- Finland
- Prior art keywords
- deoxy
- glucopyranosyl
- acid amide
- formula
- octadecyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (17)
1. Förfarande för framställning av nya terapeutiskt användbara N-glykosylamider, N-glykosylkarbamider och
5 N-glykosylkarbamater med formeln I 103 84833 R5-0-CH2 y O CO-X-R2 R4-0-{ \-N ^ (I) 10 \r* r3-o nh CO-CH-N-R8 1 7 ' 9 R7 R9 15 väri R1 betecknar en mättad eller enkelt eller mängdubbelt omät-tad alkylrest med 10 - 20 kolatomer; X är -CH2-, -O- eller -NH-; R2 betecknar väte eller en mättad eller enkelt eller mäng-20 dubbelt omättad alkylrest med 10 - 20 kolatomer; R3, R4 och R5 betecknar oberoende av varandra väte eller acyl -C0-R6, varvid R6 betecknar en alkylrest med högst 10 kolatomer; R7 betecknar väte, C^-C^-alkyl, hydroximetyl, 1-hydroxietyl, 25 merkaptometyl, 2-(metyltio)etyl, 3-aminopropyl, 3-ureido- propyl, 3-guanidylpropyl, 4-aminobutyl, karboximetyl, kar-bamoylmetyl, 2-karboxietyl, 2-karbamoyletyl, bensyl, 4-hydroxibensyl, 3-indolylmetyl eller 4-imidazolylmetyl; R8 betecknar väte eller metyl och 30 R9 betecknar väte, metyl, acetyl, bensoyl, trikloracetyl, trifluoracetyl, metoxikarbonyl, t-butyloxikarbonyl eller bensyloxikarbonyl, och R® och R9 kan tillsammans beteckna resten -CH2-CH2-CH2-; även i L- eller R-form eller eventuellt i form av 35 ett inre farmaceutiskt godtagbart sait, k ä n n e - 104 84833 t e c k n a t därav, att ett 2-amino-2-desoxiglykopyrano-sidderivat med formeln II HO-CH2 5 "'y—0 (II) HO -( )- OH HO^-^NH-R10 vari R10 betecknar en aminoskyddsgrupp känd frän peptider-10 nas syntetik och eventuellt selektivt avspjälkbar, i ett första reaktionssteg bringas att reagera med aminer med formeln III HjN-R1 (HI) 15 varl R1 betecknar en mättad eller enkelt eller mängdubbelt omät-tad alkylrest med 10 - 20 kolatomer, till glykosaminer med formeln IV 20 HO-CH2 HO-( }- NH-R1 (IV) H0^ ^ NH-R10 25 och därefter bringas glykosaminerna med formeln IV att reagera med a) lämpliga karboxylsyrederivat med formeln V 30 Rn-CO-CH2-R2 (V) vari R2 betecknar väte eller en mättad eller enkelt eller mäng-dubbelt omättad alkylrest med 10 - 20 kolatomer, och 35 R11 betecknar halogen eller en rest -0-C0-R2 eller -0-C0-0-(C^Cs)-alkyl; li 105 84 8 33 eller b) en halogenmyrsyreester med formeln VII R12-C0-0-R2 (VII) 5 vari R12 betecknar halogen, och R2 betecknar samma som ovan; eller 10 c) ett isocyanat med formeln VIII R2-NC0 (VIII) vari
15 R2 betecknar samma som ovan; de erhällna glykosamiderna VI (X = -CH2-), glykosyl-karbamaterna VI (X = -0-) eller glykosylkarbamiderna VI (X -NH-) renas antingen kromatografiskt eller förestras vid sockerresternas hydroxylgrupper, kristalliseras och 20 därefter förtvälas; frän de erhällna föreningarna med formeln VI H0-CH2 "^>—0 CO-X-R2 • 25 HO -( )- N ^ (VI) /“X ^R2 HO NH-R10 vari symbolerna R1, R2, X och R10 betecknar samma som ovan, 30 avspjälkes skyddsgruppen -R10 för att erhälla förenigarna med formeln X HO-CH2 ^ —0 CO-X-R2 HO-( )- (X) 35 y-^ R1 HO NH2 106 84833 föreningarna med formeln X bringas att reagera med aminosyrederivat med formeln XI H02C-CH-N-R14 (XI)
5 R7 R8 väri R7 betecknar sama som ovan; R8 betecknar väte eller alkyl och 10 R14 betecknar en i samband med peptidsynteser vanligen an- vänd skyddsgrupp som kan avspjälkas selektivt, varvid en peptidförening erhälls; tili föreningar med formeln XII
15 H0-CH2 — O CO-X-R2 HO -^ )-N ^ (XII) HO NH-CO-CH-N-R14
20 R7 R8 den erhällna föreningen med formeln VII renas kro-matografiskt och bringas därefter att reagera genom av-spjälkning av gruppen -R14, varvid amid-, uretan- eller 25 karbamidfunktionen erhälls, tili föreningen med formeln I, eller först förestras sockerhydroxylgrupperna, kristalliseras, förtvälas och därefter avspjälkes resten -R14, varvid amid-, uretan- eller karbamidfunktionen er-hälls, för framställning av föreningar med formeln I. 30 2. Förfarande enligt patentkravet 1 för framställ- ninga av föreningar med formeln I, känneteck-n a t därav, att en förening med formeln XIII li 107 848 33 ho-ch2 —0 HO-( )- OH (XIII) HO ^ NH-CO-CH-N-R14 R7 R8 5 väri symbolerna R7, R8 och R9 betecknar samma som i patent-kravet 1, bringas att reagera med föreningen med formeln III 10 H^-R1 (III) väri R1 betecknar en mättad eller enkelt eller mängdubbelt omät-tad alkylrest med 10 - 20 kolatomer, 15 tili en förening med formeln XIV H0-CH2 ^ HO--( >-NH-R1 (XIV)
20 HO C NH-CO-CH-N-R14 i i R7 R8 väri symbolerna R1, R7, R8 och R14 betecknar samma som ovan eller i patentkravet 1, 25 föreningarna med formeln XIV bringas att reagera a) med lämpliga karboxylsyrederivat med formeln V R11-CO-CH2-R2 (V) 30 väri R2 betecknar väte eller en mättad eller enkelt eller mäng-dubbelt omättad alkylrest med 10 - 20 kolatomer och R11 betecknar halogen eller en rest -0-C0-R2 eller -0-C0-0-(C^Cj)-alkyl; 35 eller b) med en halogenmyrsyreester med formeln VII 108 8 4 8 3 3 R1!-C0-0-R! (VII) väri
5 R12 betecknar halogen, och R2 betecknar sanuna som ovan, eller c) med ett isocyanat med formeln VIII 10 R2-NC0 (VIII) vari R2 betecknar sanuna som ovan, och de sälunda erhällna föreningarna med formeln
15 XII H0-CH2 ---0 CO-X-R2 HO-V. ^-N·^ (XII) 20 )-C R1 HO NH-CO-CH-N-R14 R7 R8 väri symbolerna R1, R2, X, R7, R8 och R14 betecknar sanuna som 25 ovan, bringas att reagera pä sä sätt som beskrivet i pa-tentkravet 1 till föreningar med formeln I.
3. Förening med formeln
30 H0-CH2 ^ y' 0 CO-X-R2 HO ^ )- N (XII) X \ Rl HO NH-CO-CH-N-R14 ‘ 7 ' B
35. R vari 109 8 4 8 3 3 symbolerna R1, R2, R7 och X betecknar samma som i patentkra-vet 1, R8 betecknar väte eller metyl, och R14 betecknar en i samband med peptidsynteser vanligen an-5 vänd skyddsgrupp som kan avspjälkas selektivt, varvid en peptidförening erhälls.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853521994 DE3521994A1 (de) | 1985-06-20 | 1985-06-20 | N-(2-aminoacylamido-2-desoxy-hexosyl)-amide-, -carbamate und -harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE3521994 | 1985-06-20 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI862619A0 FI862619A0 (fi) | 1986-06-18 |
| FI862619A FI862619A (fi) | 1986-12-21 |
| FI84833B true FI84833B (fi) | 1991-10-15 |
| FI84833C FI84833C (sv) | 1992-01-27 |
Family
ID=6273684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI862619A FI84833C (sv) | 1985-06-20 | 1986-06-18 | Förfarande för framställning av nya terapeutiskt användbara N-glykosyl amider, N-glykosylkarbamider och N-glykosylkarbamater |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4855283A (sv) |
| EP (1) | EP0206037B1 (sv) |
| JP (1) | JPH07116207B2 (sv) |
| KR (1) | KR930011281B1 (sv) |
| CN (1) | CN86104185A (sv) |
| AT (1) | ATE71631T1 (sv) |
| AU (1) | AU564222B2 (sv) |
| CA (1) | CA1289952C (sv) |
| CS (1) | CS270209B2 (sv) |
| DE (2) | DE3521994A1 (sv) |
| DK (1) | DK287886A (sv) |
| ES (2) | ES8801769A1 (sv) |
| FI (1) | FI84833C (sv) |
| GR (1) | GR861574B (sv) |
| HU (1) | HU206123B (sv) |
| IE (1) | IE58918B1 (sv) |
| IL (1) | IL79126A (sv) |
| NO (1) | NO166002C (sv) |
| PH (1) | PH26775A (sv) |
| PT (1) | PT82796B (sv) |
| ZA (1) | ZA864571B (sv) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3812681A1 (de) * | 1988-04-16 | 1989-11-02 | Bayer Ag | Substituierte n-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US5977336A (en) * | 1993-03-16 | 1999-11-02 | St. Louis University | High molecular weight surface proteins of non-typeable haemophilus |
| WO1995006654A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | Glycosylamide von 2-aminoacylamino-2-desoxy-zuckern |
| AU705998B2 (en) * | 1993-11-08 | 1999-06-03 | Connaught Laboratories Limited | Haemophilus transferrin receptor genes |
| US6361779B1 (en) | 1993-11-08 | 2002-03-26 | Aventis Pasteur Limited | Transferrin receptor genes |
| US6764682B1 (en) * | 1994-06-16 | 2004-07-20 | Aventis Pasteur Limited | Adjuvant compositions containing more than one adjuvant |
| US6335018B1 (en) | 1995-05-01 | 2002-01-01 | Aventis Pasteur Limited | High molecular weight major outer membrane protein of moraxella |
| US6440425B1 (en) | 1995-05-01 | 2002-08-27 | Aventis Pasteur Limited | High molecular weight major outer membrane protein of moraxella |
| EP1234580A1 (en) | 1995-05-04 | 2002-08-28 | Aventis Pasteur Limited | Acellular Pertussis Vaccines and Methods of Preparation Thereof |
| US5827654A (en) * | 1995-05-08 | 1998-10-27 | University Of Toronto | Basal body rod protein genes of campylobacter |
| US6251405B1 (en) | 1995-06-07 | 2001-06-26 | Connaught Laboratories, Inc. | Immunological combination compositions and methods |
| US5780606A (en) * | 1995-06-07 | 1998-07-14 | Connaught Laboratories Limited | Neisseria meningitidis capsular polysaccharide conjugates |
| US6290971B1 (en) * | 1995-06-15 | 2001-09-18 | Aventis Pasteur Limited | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
| US6048539A (en) * | 1995-11-02 | 2000-04-11 | Connaught Laboratories Limited | Lactoferrin receptor protein |
| FR2746643B1 (fr) * | 1996-04-01 | 1998-06-12 | Techni Pharma | Nouvelles compositions laxatives et leur procede de fabrication |
| TR199802783T2 (xx) | 1996-07-02 | 1999-03-22 | Connaught Laboratories Limited | �ok de�erli DTP polyo a��lar. |
| US6042820A (en) | 1996-12-20 | 2000-03-28 | Connaught Laboratories Limited | Biodegradable copolymer containing α-hydroxy acid and α-amino acid units |
| FR2762788B1 (fr) * | 1997-04-30 | 2000-10-06 | Pasteur Merieux Serums Vacc | Composition vaccinale anti-helicobacter pour usage par voie systemique sous-diaphragmatique |
| FR2762787B1 (fr) * | 1997-04-30 | 2000-10-06 | Pasteur Merieux Serums Vacc | Composition vaccinale anti-helicobacter comprenant un adjuvant de type th1 |
| WO1998048836A1 (fr) * | 1997-04-30 | 1998-11-05 | Merieux Oravax | Composition vaccinale anti-helicobacter comprenant un adjuvant de type th1 |
| US5977337A (en) | 1997-06-03 | 1999-11-02 | Connaught Laboratories Limited | Lactoferrin receptor genes of Moraxella |
| US7459524B1 (en) * | 1997-10-02 | 2008-12-02 | Emergent Product Development Gaithersburg Inc. | Chlamydia protein, sequence and uses thereof |
| US6335182B1 (en) | 1999-03-16 | 2002-01-01 | Aventis Pasteur Limited | Recombinant Haemophilus influenzae adhesin proteins |
| US7785609B1 (en) | 1999-03-16 | 2010-08-31 | Sanofi Pasteur Limited | Recombinant Haemophilus influenzae adhesin proteins |
| US7241449B1 (en) | 1999-04-12 | 2007-07-10 | Aventis Pasteur Limited | Transferrin receptor genes of moraxella |
| EP1808180A3 (en) | 1999-10-22 | 2010-12-22 | Sanofi Pasteur Limited | Modified GP 100 and uses thereof |
| GB0000891D0 (en) * | 2000-01-14 | 2000-03-08 | Allergy Therapeutics Ltd | Formulation |
| US7851212B2 (en) | 2000-05-10 | 2010-12-14 | Sanofi Pasteur Limited | Immunogenic polypeptides encoded by MAGE minigenes and uses thereof |
| AUPS143402A0 (en) * | 2002-03-28 | 2002-05-09 | Alchemia Pty Ltd | Anomeric derivatives of monosaccharides |
| US8506959B2 (en) | 2002-11-01 | 2013-08-13 | Neotope Biosciences Limited | Prevention and treatment of synucleinopathic and amyloidogenic disease |
| WO2008103472A2 (en) | 2007-02-23 | 2008-08-28 | Elan Pharmaceuticals, Inc. | Prevention and treatment of synucleinopathic and amyloidogenic disease |
| TW200509968A (en) | 2002-11-01 | 2005-03-16 | Elan Pharm Inc | Prevention and treatment of synucleinopathic disease |
| ATE480258T1 (de) * | 2002-11-26 | 2010-09-15 | Eurocine Vaccines Ab | Neue adjuvant auf der basis von aminen |
| US7358331B2 (en) | 2003-05-19 | 2008-04-15 | Elan Pharmaceuticals, Inc. | Truncated fragments of alpha-synuclein in Lewy body disease |
| JP4820291B2 (ja) | 2003-05-19 | 2011-11-24 | エラン ファーマシューティカルズ，インコーポレイテッド | レヴィー小体病におけるαシヌクレインの切断断片 |
| MX2007001679A (es) | 2004-08-09 | 2007-05-23 | Elan Pharm Inc | Prevencion y tratamiento de la enfermedad sinucleinopatica y amiloidogenica. |
| UA90569C2 (ru) * | 2006-01-26 | 2010-05-11 | Пфайзер Продактс Инк. | Композиция гликолипидного адьюванта (варианты) и способ ее получения |
| EP2481423A1 (en) | 2006-01-26 | 2012-08-01 | Pfizer Products Inc. | Novel glycolipid adjuvant compositions |
| EP3067066B1 (en) | 2007-02-23 | 2019-03-27 | Prothena Biosciences Limited | Prevention and treatment of synucleinopathic and amyloidogenic disease |
| GB2450088A (en) * | 2007-06-11 | 2008-12-17 | Diosamine Dev Corp | Optionally modified monosaccharides with imine/iminium or glycosidic amine/ammonium group for use in modifying the level of cytokines & in therapy |
| JO3076B1 (ar) | 2007-10-17 | 2017-03-15 | Janssen Alzheimer Immunotherap | نظم العلاج المناعي المعتمد على حالة apoe |
| US8791243B2 (en) | 2007-12-28 | 2014-07-29 | Onclave Therapeutics Limited | Treatment and prophylaxis of amyloidosis |
| EP2196196A1 (en) | 2008-12-10 | 2010-06-16 | Medipol S.A. | Compound, medicament, vaccine composition and nanocapsules |
| GB201000196D0 (en) * | 2010-01-07 | 2010-02-24 | Galvez Julian M | Novel combination |
| KR102085465B1 (ko) | 2010-05-14 | 2020-03-05 | 박스알타 인코퍼레이티드 | 키메라 ｏｓｐａ 유전자, 단백질 및 이의 사용 방법 |
| JP2015524802A (ja) | 2012-07-27 | 2015-08-27 | バクスター・インターナショナル・インコーポレイテッドＢａｘｔｅｒ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃｏｒｐ０Ｒａｔｅｄ | キメラｏｓｐａ分子を含む組成物およびその使用方法 |
| CN104628802B (zh) * | 2013-11-07 | 2017-01-18 | 北大方正集团有限公司 | 从发酵液中提取并纯化尼莫克汀的方法 |
| US11191832B2 (en) | 2013-11-19 | 2021-12-07 | Prothena Biosciences Limited | Monitoring immunotherapy of Lewy body disease from constipation symptoms |
| EP3028711A1 (en) * | 2014-12-05 | 2016-06-08 | Gubra ApS | Molecular building blocks capable of assembling carbohydrate derivatives, fatty acid residues and peptides |
| MX2018000879A (es) * | 2015-07-20 | 2018-05-15 | Zoetis Services Llc | Composiciones de adyuvante liposomal. |
| US10456459B2 (en) * | 2015-07-20 | 2019-10-29 | Zoetis Services Llc | Liposomal adjuvant compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213650A1 (de) * | 1982-04-14 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
| DE3344257A1 (de) * | 1983-12-07 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Substituierte o-acyl-glycosylamide, verfahren zu iherer herstellung sowie ihre verwendung |
-
1985
- 1985-06-20 DE DE19853521994 patent/DE3521994A1/de not_active Withdrawn
-
1986
- 1986-06-03 NO NO862199A patent/NO166002C/no unknown
- 1986-06-05 DE DE8686107665T patent/DE3683410D1/de not_active Expired - Lifetime
- 1986-06-05 EP EP86107665A patent/EP0206037B1/de not_active Expired - Lifetime
- 1986-06-05 AT AT86107665T patent/ATE71631T1/de not_active IP Right Cessation
- 1986-06-16 US US06/874,983 patent/US4855283A/en not_active Expired - Lifetime
- 1986-06-17 IL IL79126A patent/IL79126A/xx not_active IP Right Cessation
- 1986-06-18 PH PH33904A patent/PH26775A/en unknown
- 1986-06-18 CS CS864513A patent/CS270209B2/cs unknown
- 1986-06-18 FI FI862619A patent/FI84833C/sv not_active IP Right Cessation
- 1986-06-18 CA CA000511894A patent/CA1289952C/en not_active Expired - Lifetime
- 1986-06-18 JP JP61140434A patent/JPH07116207B2/ja not_active Expired - Lifetime
- 1986-06-18 AU AU58979/86A patent/AU564222B2/en not_active Expired
- 1986-06-18 GR GR861574A patent/GR861574B/el unknown
- 1986-06-19 PT PT82796A patent/PT82796B/pt not_active IP Right Cessation
- 1986-06-19 HU HU862584A patent/HU206123B/hu unknown
- 1986-06-19 ES ES556287A patent/ES8801769A1/es not_active Expired
- 1986-06-19 KR KR8604878A patent/KR930011281B1/ko not_active IP Right Cessation
- 1986-06-19 ZA ZA864571A patent/ZA864571B/xx unknown
- 1986-06-19 IE IE163686A patent/IE58918B1/en not_active IP Right Cessation
- 1986-06-19 DK DK287886A patent/DK287886A/da not_active Application Discontinuation
- 1986-06-20 CN CN198686104185A patent/CN86104185A/zh active Pending
-
1987
- 1987-09-15 ES ES557729A patent/ES8900231A1/es not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI84833B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-glykosylamider n-glykosylkarbamider och n -glykosylkarbamater. | |
| CN106573962B (zh) | 新颖的聚糖共轭物及其用途 | |
| Toyokuni et al. | Synthetic carbohydrate vaccines: synthesis and immunogenicity of Tn antigen conjugates | |
| US4446128A (en) | Antigen derivatives and processes for their preparation | |
| IE51058B1 (en) | Tetrapeptides and pentapeptides,their preparation and compositions containing them | |
| FI72733C (sv) | Förfarande för framställning av farmakologiskt verkande glukosderivat samt mellanprodukter använda vid förfarandet. | |
| US4461761A (en) | Oligomers of compounds of the muramyl-peptide type and medicaments containing them | |
| NO151201B (no) | Fremgangsmaate for fremstilling av terapeutisk virksomme antigenderivater. | |
| AU2014289342B2 (en) | Synthetic vaccines against Streptococcus pneumoniae type 1 | |
| EP3389643B1 (en) | Novel muramyl peptide derivative compound, synthesis and uses thereof | |
| EP3387005B1 (en) | Novel muramyl peptide derivative compound, synthesis and uses thereof | |
| CA1321993C (en) | Substituted n-glycosylamides, process for their preparation, and their use as medicaments | |
| US4693998A (en) | Novel compounds of the muramyl peptide | |
| KR910008107B1 (ko) | 무라밀디펩타이드 활성 에스테르 유도체의 제조방법 | |
| CA1262015A (en) | Acylated sugar derivatives, processes for their manufacture, and their use | |
| US4473554A (en) | Bestatin-related compounds as immunopotentiator | |
| EP0173960B1 (en) | Muramylpeptide active ester derivatives | |
| GB1584791A (en) | Muromyl peptide immunological adjuvants | |
| JP2934905B2 (ja) | 新規リポペプタイド及び抗腫瘍剤 | |
| US4574058A (en) | Antigen derivatives and processes for their preparation | |
| KR830002059B1 (ko) | 멀아밀-펲타이드형태인 신규 화합물의 제조방법 | |
| AU649242B2 (en) | Amino acids, peptides or derivatives thereof coupled to fats | |
| Dmitriev et al. | Glycopeptidolipids—a new class of artificial antigens with carbohydrate determinants. Synthesis of artificial antigen with type-specific oligosaccharide hapten from Neisseria meningitidis group B | |
| Wu | Modulators of Toll-like Receptors-4 and-2 | |
| IE49617B1 (en) | Novel compounds of the muramyl-peptide type and medicaments containing them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BAYER AKTIENGESELLSCHAFT |