IL123394A - Use of aminoadamantane compounds in the preparation of drugs for immune regulation - Google Patents

Use of aminoadamantane compounds in the preparation of drugs for immune regulation

Info

Publication number: IL123394A
Authority: IL; Israel
Prior art keywords: neutrophils; formula; activity; adamantane; aminoadamantane
Prior art date: 1995-08-25

Application number

IL12339496A

Other languages

English (en)

Hebrew (he)

Other versions

IL123394A0 (en

Original Assignee

Merz Pharma Gmbh & Co Kgaa

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.)

1995-08-25

Filing date

1996-08-21

Publication date

2004-07-25

1996-08-21 Application filed by Merz Pharma Gmbh & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa

1998-09-24 Publication of IL123394A0 publication Critical patent/IL123394A0/xx

2004-07-25 Publication of IL123394A publication Critical patent/IL123394A/en

Links

239000003814 drug Substances 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 7
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 title abstract description 25
210000000440 neutrophil Anatomy 0.000 claims abstract description 45
230000000694 effects Effects 0.000 claims abstract description 29
-1 aminoadamantane compound Chemical class 0.000 claims abstract description 20
208000030507 AIDS Diseases 0.000 claims abstract description 5
210000002381 plasma Anatomy 0.000 claims abstract description 5
208000003669 immune deficiency disease Diseases 0.000 claims abstract 3
239000012190 activator Substances 0.000 claims description 10
230000001965 increasing effect Effects 0.000 claims description 10
229920000392 Zymosan Polymers 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
230000033228 biological regulation Effects 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 claims description 6
230000004913 activation Effects 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000000338 in vitro Methods 0.000 claims description 4
206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 3
208000016532 chronic granulomatous disease Diseases 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
QJZCXHNEPQJAPJ-UHFFFAOYSA-N 3-ethyl-5,7-dimethyladamantan-1-amine Chemical compound C1C(C2)(C)CC3(C)CC2(N)CC1(CC)C3 QJZCXHNEPQJAPJ-UHFFFAOYSA-N 0.000 claims 1
238000001514 detection method Methods 0.000 claims 1
LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
229960004640 memantine Drugs 0.000 description 11
150000001875 compounds Chemical class 0.000 description 7
230000000638 stimulation Effects 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
239000003642 reactive oxygen metabolite Substances 0.000 description 5
PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000007124 immune defense Effects 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
210000000265 leukocyte Anatomy 0.000 description 4
238000005259 measurement Methods 0.000 description 4
230000019254 respiratory burst Effects 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
102000014384 Type C Phospholipases Human genes 0.000 description 3
108010079194 Type C Phospholipases Proteins 0.000 description 3
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
229960003805 amantadine Drugs 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000001982 diacylglycerols Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
229960002163 hydrogen peroxide Drugs 0.000 description 3
HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
102000003896 Myeloperoxidases Human genes 0.000 description 2
108090000235 Myeloperoxidases Proteins 0.000 description 2
102000004722 NADPH Oxidases Human genes 0.000 description 2
108010002998 NADPH Oxidases Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102000003923 Protein Kinase C Human genes 0.000 description 2
108090000315 Protein Kinase C Proteins 0.000 description 2
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
125000006193 alkinyl group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
101150037263 PIP2 gene Proteins 0.000 description 1
206010057249 Phagocytosis Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
101100262439 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBA2 gene Proteins 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
241000700605 Viruses Species 0.000 description 1
MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
208000038016 acute inflammation Diseases 0.000 description 1
230000006022 acute inflammation Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000078 anti-malarial effect Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
210000004958 brain cell Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
230000005779 cell damage Effects 0.000 description 1
208000037887 cell injury Diseases 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
206010008118 cerebral infarction Diseases 0.000 description 1
208000037976 chronic inflammation Diseases 0.000 description 1
230000006020 chronic inflammation Effects 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000003831 deregulation Effects 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000001723 extracellular space Anatomy 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
208000007345 glycogen storage disease Diseases 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
210000004698 lymphocyte Anatomy 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
239000012528 membrane Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000005445 natural material Substances 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000008782 phagocytosis Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000010837 receptor-mediated endocytosis Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229960000888 rimantadine Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/06—Fungi, e.g. yeasts
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/06—Fungi, e.g. yeasts
- A61K36/062—Ascomycota
- A61K36/064—Saccharomycetales, e.g. baker's yeast
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
- 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
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Natural Medicines & Medicinal Plants (AREA)
Mycology (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Medical Informatics (AREA)
Botany (AREA)
Biotechnology (AREA)
Alternative & Traditional Medicine (AREA)
Tropical Medicine & Parasitology (AREA)
Gastroenterology & Hepatology (AREA)
Communicable Diseases (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Oncology (AREA)
Virology (AREA)
Diabetes (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Investigating Or Analysing Biological Materials (AREA)

IL12339496A 1995-08-25 1996-08-21 Use of aminoadamantane compounds in the preparation of drugs for immune regulation IL123394A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19531342A DE19531342B4 (de)	1995-08-25	1995-08-25	Verwendung von Aminoadamantan-Verbindungen als Immunregulatoren
PCT/EP1996/003678 WO1997007791A1 (en)	1995-08-25	1996-08-21	Use of aminoadamantane compounds as immunoregulators

Publications (2)

Publication Number	Publication Date
IL123394A0 IL123394A0 (en)	1998-09-24
IL123394A true IL123394A (en)	2004-07-25

Family

ID=7770407

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12339496A IL123394A (en)	1995-08-25	1996-08-21	Use of aminoadamantane compounds in the preparation of drugs for immune regulation

Country Status (21)

Country	Link
US (2)	US6172116B1 (de)
EP (2)	EP0845984B1 (de)
JP (1)	JPH11512093A (de)
KR (1)	KR100392986B1 (de)
CN (1)	CN1282452C (de)
AT (1)	ATE234083T1 (de)
AU (1)	AU718219B2 (de)
CA (1)	CA2230159C (de)
CZ (1)	CZ299356B6 (de)
DE (3)	DE19531342B4 (de)
DK (1)	DK0845984T3 (de)
EE (1)	EE04261B1 (de)
ES (1)	ES2193259T3 (de)
GE (1)	GEP19991779B (de)
IL (1)	IL123394A (de)
MX (1)	MX217078B (de)
NO (1)	NO319153B1 (de)
RU (1)	RU2219916C2 (de)
UA (1)	UA57711C2 (de)
WO (1)	WO1997007791A1 (de)
ZA (1)	ZA967137B (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2369997C (en) *	1999-04-28	2009-11-17	Queen's University At Kingston	Compositions and methods for treating amyloidosis
RU2196575C2 (ru) *	1999-07-30	2003-01-20	Научно-исследовательский институт фармакологии РАМН	Вещество, обладающее психостимулирующим и антиастеническим действием
US6444702B1 (en)	2000-02-22	2002-09-03	Neuromolecular, Inc.	Aminoadamantane derivatives as therapeutic agents
RU2226391C2 (ru) *	2002-05-28	2004-04-10	Плотников Владимир Михайлович	Средство для повышения активности нейтрофилов
RU2246482C2 (ru) *	2002-12-25	2005-02-20	ООО "Циклан"	Способ получения гидрохлорида 1-амино-3,5-диметиладамантана
US20070010573A1 (en) *	2003-06-23	2007-01-11	Xianqi Kong	Methods and compositions for treating amyloid-related diseases
US7414076B2 (en) *	2003-06-23	2008-08-19	Neurochem (International) Limited	Methods and compositions for treating amyloid-related diseases
UA79908C2 (en) *	2004-06-24	2007-07-25	Olainfarm Joint Stock Company	Application of polymeric salts 3,5-dimethyl-1-adamantilammonium as immunostimulative and interferonogenous agent
EP1836161B1 (de)	2004-12-22	2016-07-20	BHI Limited Partnership	Verfahren und zusammensetzungen zur behandlung von amyloidassoziierten krankheiten
SI2089417T1 (sl)	2006-10-12	2015-04-30	Bhi Limited Partnership	Metode, spojine, sestavki in vektorji za dostavo 3-amino-1-propansulfonske kisline
TWI511958B (zh) *	2010-08-09	2015-12-11	Shionogi & Co	胺基金剛烷胺基甲酸酯衍生物之製造方法
CN109922796B (zh)	2016-06-23	2023-04-07	考里安有限责任公司	具有亲水和疏水域的粘合剂基质和治疗剂
EP3490544A1 (de)	2016-07-27	2019-06-05	Corium International, Inc.	Transdermale abgabesysteme für memantin
KR102424270B1 (ko)	2016-07-27	2022-07-25	코리움, 인크.	경구 전달과 생물학적으로 동등한 약물동역학을 가진 경피 전달 시스템
JP7071330B2 (ja)	2016-07-27	2022-05-18	コリウム，インコーポレイテッド	炭酸水素ナトリウムのｉｎｓｉｔｕ変換で促進されたアミン薬物の経皮送達
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DE4014672A1 (de) *	1990-05-08	1991-11-14	Werner E G Prof Dr Mueller	Verwendung von adamantan-derivaten zur zytoprotektion von nicht-infizierten und virus-infizierten lymphozyten als auch anderen zelltypen

1995
- 1995-08-25 DE DE19531342A patent/DE19531342B4/de not_active Expired - Fee Related
1996
- 1996-08-21 MX MX9801496A patent/MX217078B/es not_active IP Right Cessation
- 1996-08-21 DE DE69626650T patent/DE69626650T2/de not_active Expired - Fee Related
- 1996-08-21 DE DE2003199029 patent/DE10399029I1/de active Pending
- 1996-08-21 EE EE9800057A patent/EE04261B1/xx not_active IP Right Cessation
- 1996-08-21 CN CNB961973471A patent/CN1282452C/zh not_active Expired - Fee Related
- 1996-08-21 KR KR19980701329A patent/KR100392986B1/ko not_active Expired - Fee Related
- 1996-08-21 UA UA98031521A patent/UA57711C2/uk unknown
- 1996-08-21 EP EP96930065A patent/EP0845984B1/de not_active Expired - Lifetime
- 1996-08-21 US US09/029,335 patent/US6172116B1/en not_active Expired - Fee Related
- 1996-08-21 RU RU98105150/14A patent/RU2219916C2/ru not_active IP Right Cessation
- 1996-08-21 WO PCT/EP1996/003678 patent/WO1997007791A1/en not_active Ceased
- 1996-08-21 EP EP02026914A patent/EP1293201A3/de not_active Withdrawn
- 1996-08-21 GE GEAP19964199A patent/GEP19991779B/en unknown
- 1996-08-21 ES ES96930065T patent/ES2193259T3/es not_active Expired - Lifetime
- 1996-08-21 CA CA002230159A patent/CA2230159C/en not_active Expired - Fee Related
- 1996-08-21 AT AT96930065T patent/ATE234083T1/de not_active IP Right Cessation
- 1996-08-21 IL IL12339496A patent/IL123394A/en not_active IP Right Cessation
- 1996-08-21 CZ CZ0052498A patent/CZ299356B6/cs not_active IP Right Cessation
- 1996-08-21 AU AU69263/96A patent/AU718219B2/en not_active Ceased
- 1996-08-21 DK DK96930065T patent/DK0845984T3/da active
- 1996-08-21 JP JP9509816A patent/JPH11512093A/ja active Pending
- 1996-08-22 ZA ZA967137A patent/ZA967137B/xx unknown
1998
- 1998-02-25 NO NO19980793A patent/NO319153B1/no unknown
2000
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Also Published As

Publication number	Publication date
EP0845984A1 (de)	1998-06-10
NO980793L (no)	1998-02-25
US6255348B1 (en)	2001-07-03
MX9801496A (es)	1998-05-31
JPH11512093A (ja)	1999-10-19
GEP19991779B (en)	1999-10-05
MX217078B (es)	2003-10-22
CA2230159C (en)	2008-02-26
UA57711C2 (uk)	2003-07-15
DK0845984T3 (da)	2003-06-23
EE04261B1 (et)	2004-04-15
EP0845984B1 (de)	2003-03-12
DE19531342B4 (de)	2007-11-29
EE9800057A (et)	1998-08-17
CN1198669A (zh)	1998-11-11
KR100392986B1 (ko)	2003-11-17
ES2193259T3 (es)	2003-11-01
US6172116B1 (en)	2001-01-09
DE19531342A1 (de)	1997-02-27
CA2230159A1 (en)	1997-03-06
CZ52498A3 (cs)	1999-04-14
AU718219B2 (en)	2000-04-13
CN1282452C (zh)	2006-11-01
DE10399029I1 (de)	2004-01-08
IL123394A0 (en)	1998-09-24
ZA967137B (en)	1997-03-12
RU2219916C2 (ru)	2003-12-27
EP1293201A2 (de)	2003-03-19
KR19990044096A (ko)	1999-06-25
EP1293201A3 (de)	2003-05-21
NO319153B1 (no)	2005-06-27
DE69626650T2 (de)	2003-12-18
DE69626650D1 (de)	2003-04-17
AU6926396A (en)	1997-03-19
CZ299356B6 (cs)	2008-07-02
NO980793D0 (no)	1998-02-25
ATE234083T1 (de)	2003-03-15
WO1997007791A1 (en)	1997-03-06

Legal Events

Date	Code	Title
2004-12-15	FF	Patent granted
2005-03-20	KB	Patent renewed
2006-10-04	KB	Patent renewed
2011-04-28	MM9K	Patent not in force due to non-payment of renewal fees

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