SK280286B6 - Analógy 15-deoxyspergualínu, spôsob ich prípravy, - Google Patents
Analógy 15-deoxyspergualínu, spôsob ich prípravy, Download PDFInfo
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- SK280286B6 SK280286B6 SK1357-93A SK135793A SK280286B6 SK 280286 B6 SK280286 B6 SK 280286B6 SK 135793 A SK135793 A SK 135793A SK 280286 B6 SK280286 B6 SK 280286B6
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- 238000002360 preparation method Methods 0.000 title claims abstract description 121
- BLUYEPLOXLPVCJ-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxyethyl]-7-(diaminomethylideneamino)heptanamide Chemical class NCCCNCCCCNC[C@H](O)NC(=O)CCCCCCNC(N)=N BLUYEPLOXLPVCJ-INIZCTEOSA-N 0.000 title claims description 13
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- IDINUJSAMVOPCM-UHFFFAOYSA-N 15-Deoxyspergualin Natural products NCCCNCCCCNC(=O)C(O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-UHFFFAOYSA-N 0.000 description 11
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- 239000003480 eluent Substances 0.000 description 7
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- 230000001506 immunosuppresive effect Effects 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
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- ZRLWXDLSHZCAJM-UHFFFAOYSA-N CC(C)(C)OC(=O)NCCCN(C(=O)OC(C)(C)C)CCCCNC(=O)C(C(O)=O)OCC1=CC=CC=C1 Chemical compound CC(C)(C)OC(=O)NCCCN(C(=O)OC(C)(C)C)CCCCNC(=O)C(C(O)=O)OCC1=CC=CC=C1 ZRLWXDLSHZCAJM-UHFFFAOYSA-N 0.000 description 1
- GKMOQHOMYCPCAF-UHFFFAOYSA-N CC(C)(OC(=O)N(CCCNC(=O)O)CCCCNC(C(C(=O)O)OCC1=CC=CC=C1)=O)C Chemical compound CC(C)(OC(=O)N(CCCNC(=O)O)CCCCNC(C(C(=O)O)OCC1=CC=CC=C1)=O)C GKMOQHOMYCPCAF-UHFFFAOYSA-N 0.000 description 1
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- 108090000695 Cytokines Proteins 0.000 description 1
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- MLXXIHQTUZBJMN-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCCCNCCCCNC(=O)NCC(=O)NCCCCCCCCNC=NN Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCCCNCCCCNC(=O)NCC(=O)NCCCCCCCCNC=NN MLXXIHQTUZBJMN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- PVWDTQFPZHXLQK-UHFFFAOYSA-N [N'-(6-aminohexyl)-N-carboxycarbamimidoyl]carbamic acid Chemical compound NCCCCCCN=C(NC(O)=O)NC(O)=O PVWDTQFPZHXLQK-UHFFFAOYSA-N 0.000 description 1
- BMSCIYHZTFSYAB-UHFFFAOYSA-N [N'-[6-[[2-(carboxyamino)acetyl]amino]hexyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamic acid Chemical compound CC(C)(OC(=O)NC(=NC(=O)O)NCCCCCCNC(CNC(=O)O)=O)C BMSCIYHZTFSYAB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229940043239 cytotoxic antineoplastic drug Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229960002706 gusperimus Drugs 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001031 immunopharmacological effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000001325 log-rank test Methods 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
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- REXQYHKFINRJMM-UHFFFAOYSA-N methyl 2-phenoxycarbonyloxyacetate Chemical compound COC(=O)COC(=O)OC1=CC=CC=C1 REXQYHKFINRJMM-UHFFFAOYSA-N 0.000 description 1
- IDINUJSAMVOPCM-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC(=O)[C@H](O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-INIZCTEOSA-N 0.000 description 1
- ICODKJXEVZVARX-UHFFFAOYSA-N n-[4-(3-aminopropylamino)butyl]-2-fluoro-n'-[6-(hydrazinylmethylideneamino)hexyl]propanediamide Chemical compound NCCCNCCCCNC(=O)C(F)C(=O)NCCCCCCN=CNN ICODKJXEVZVARX-UHFFFAOYSA-N 0.000 description 1
- YBBSLKGEDYCUHT-UHFFFAOYSA-N n-[4-(3-aminopropylamino)butyl]-n'-[6-(hydrazinylmethylideneamino)hexyl]-2-methoxypropanediamide Chemical compound NCCCNCCCCNC(=O)C(OC)C(=O)NCCCCCCN=CNN YBBSLKGEDYCUHT-UHFFFAOYSA-N 0.000 description 1
- SYAQFGWASNXZHL-UHFFFAOYSA-N n-amino-n'-[6-[[1-[4-(3-aminopropylamino)butylamino]-2-hydroxypropyl]amino]hexyl]methanimidamide Chemical compound NCCCNCCCCNC(C(O)C)NCCCCCCN=CNN SYAQFGWASNXZHL-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000004988 splenocyte Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- FQPCRESDVNTGEN-UHFFFAOYSA-N tert-butyl n-[n'-(8-aminooctyl)-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(NC(=O)OC(C)(C)C)=NCCCCCCCCN FQPCRESDVNTGEN-UHFFFAOYSA-N 0.000 description 1
- WOXKZRRFJUMOJE-UHFFFAOYSA-N tert-butyl n-[n'-[6-[(2-aminoacetyl)amino]hexyl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)NCCCCCCNC(=O)CN WOXKZRRFJUMOJE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- 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
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Soil Conditioners And Soil-Stabilizing Materials (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9214517A FR2698628B1 (fr) | 1992-12-02 | 1992-12-02 | Analogues de 15-déoxyspergualine, leur procédé de préparation et leur utilisation en thérapeutique. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK135793A3 SK135793A3 (en) | 1994-06-08 |
| SK280286B6 true SK280286B6 (sk) | 1999-11-08 |
Family
ID=9436147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1357-93A SK280286B6 (sk) | 1992-12-02 | 1993-12-02 | Analógy 15-deoxyspergualínu, spôsob ich prípravy, |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5476870A (enExample) |
| EP (1) | EP0600762B1 (enExample) |
| JP (1) | JP2945261B2 (enExample) |
| KR (1) | KR100187328B1 (enExample) |
| CN (1) | CN1045431C (enExample) |
| AT (1) | ATE140215T1 (enExample) |
| AU (1) | AU664124B2 (enExample) |
| CA (1) | CA2110437C (enExample) |
| CZ (1) | CZ284958B6 (enExample) |
| DE (1) | DE69303583T2 (enExample) |
| DK (1) | DK0600762T3 (enExample) |
| ES (1) | ES2092263T3 (enExample) |
| FI (1) | FI112211B (enExample) |
| FR (1) | FR2698628B1 (enExample) |
| GR (1) | GR3021269T3 (enExample) |
| HU (1) | HU218908B (enExample) |
| NO (1) | NO180483C (enExample) |
| NZ (1) | NZ250330A (enExample) |
| RU (1) | RU2114823C1 (enExample) |
| SK (1) | SK280286B6 (enExample) |
| TW (1) | TW311132B (enExample) |
| UA (1) | UA39920C2 (enExample) |
| ZA (1) | ZA938821B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09511765A (ja) * | 1995-02-10 | 1997-11-25 | フルニエ・アンデュストリ・エ・サンテ | １５−デオキシスペルグアリン類似体、その治療用途及びその調製方法 |
| FR2734263B1 (fr) * | 1995-05-17 | 1997-06-20 | Fournier Ind & Sante | Analogues de la 15-deoxyspergualine, leur procede de preparation et leur utilisation en therapeutique |
| ES2139465T3 (es) * | 1996-12-20 | 2000-02-01 | Sueddeutsche Kalkstickstoff | Piruvatos de creatina y procedimiento para su preparacion. |
| DE19728436A1 (de) * | 1997-07-03 | 1999-01-07 | Niels Franke | Niedrigdosierte 15-Desoxyspergualin-Präparate |
| HK1043801A1 (zh) * | 1998-08-28 | 2002-09-27 | 格莱风科学公司 | 精确长度的聚酰胺链、其制备方法和其与蛋白质的缀合物 |
| DE19923961A1 (de) * | 1999-05-25 | 2000-11-30 | Euro Nippon Kayaku Gmbh | Verwendung von 15-Deoxyspergualin zur Behandlung von hyperreaktiven entzündlichen Erkrankungen und Autoimmunerkrankungen |
| CA2565633C (en) * | 2004-05-05 | 2016-04-26 | Atugen Ag | Lipids, lipid complexes and use thereof |
| WO2006069782A2 (en) | 2004-12-27 | 2006-07-06 | Silence Therapeutics Ag. | Lipid complexes coated with peg and their use |
| WO2010074591A1 (ru) | 2008-12-24 | 2010-07-01 | Закрытое Акционерное Общество "Beptekc" | Амиды креатина, способ их получения, средство, обладающее нейропротекторным действием |
| RU2428414C2 (ru) | 2009-11-03 | 2011-09-10 | Закрытое Акционерное Общество "Вертекс" | Способ получения амидов креатина |
| JP5878172B2 (ja) * | 2010-07-29 | 2016-03-08 | ラボラトワール フルニエ エスアーエス | 炎症性眼疾患の治療／予防用化合物 |
| FR2963238B1 (fr) * | 2010-07-29 | 2012-12-28 | Fournier Lab Sa | Derives de 15-desoxyspergualine pour le traitement et/ou la prevention des maladies inflammatoires oculaires |
| KR101695730B1 (ko) | 2015-03-10 | 2017-01-12 | 하경훈 | 마늘꼭지 절단기의 절단장치 |
| FR3050455B1 (fr) * | 2016-04-26 | 2019-06-14 | Temisis | Derives amides des acides polycafeoylquiniques, procede de preparation et utilisations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5942356A (ja) * | 1982-09-02 | 1984-03-08 | Microbial Chem Res Found | スパガリン関連化合物およびその製造法 |
| DE3770680D1 (de) * | 1986-04-04 | 1991-07-18 | Microbial Chem Res Found | Spergualinaehnliche verbindungen und ihr herstellungsverfahren. |
| US5061787A (en) * | 1988-06-24 | 1991-10-29 | Nippon Kayaku Kabushiki Kaisha | Novel spergualin-related compounds and compositions |
-
1992
- 1992-12-02 FR FR9214517A patent/FR2698628B1/fr not_active Expired - Fee Related
-
1993
- 1993-11-17 AT AT93402795T patent/ATE140215T1/de not_active IP Right Cessation
- 1993-11-17 ES ES93402795T patent/ES2092263T3/es not_active Expired - Lifetime
- 1993-11-17 DE DE69303583T patent/DE69303583T2/de not_active Expired - Fee Related
- 1993-11-17 DK DK93402795.4T patent/DK0600762T3/da active
- 1993-11-17 EP EP93402795A patent/EP0600762B1/fr not_active Expired - Lifetime
- 1993-11-19 TW TW082109707A patent/TW311132B/zh active
- 1993-11-24 AU AU51883/93A patent/AU664124B2/en not_active Ceased
- 1993-11-25 ZA ZA938821A patent/ZA938821B/xx unknown
- 1993-11-29 FI FI935318A patent/FI112211B/fi not_active IP Right Cessation
- 1993-11-30 KR KR1019930025761A patent/KR100187328B1/ko not_active Expired - Fee Related
- 1993-11-30 NZ NZ250330A patent/NZ250330A/en unknown
- 1993-11-30 NO NO934338A patent/NO180483C/no not_active IP Right Cessation
- 1993-12-01 HU HU9303406A patent/HU218908B/hu not_active IP Right Cessation
- 1993-12-01 CA CA002110437A patent/CA2110437C/en not_active Expired - Fee Related
- 1993-12-01 RU RU93053038A patent/RU2114823C1/ru not_active IP Right Cessation
- 1993-12-01 UA UA93003726A patent/UA39920C2/uk unknown
- 1993-12-02 JP JP5342673A patent/JP2945261B2/ja not_active Expired - Fee Related
- 1993-12-02 US US08/161,773 patent/US5476870A/en not_active Expired - Fee Related
- 1993-12-02 CZ CZ932622A patent/CZ284958B6/cs not_active IP Right Cessation
- 1993-12-02 CN CN93121647A patent/CN1045431C/zh not_active Expired - Fee Related
- 1993-12-02 SK SK1357-93A patent/SK280286B6/sk unknown
-
1996
- 1996-10-04 GR GR960402621T patent/GR3021269T3/el unknown
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