SK280286B6 - Analógy 15-deoxyspergualínu, spôsob ich prípravy, - Google Patents

Analógy 15-deoxyspergualínu, spôsob ich prípravy, Download PDF

Info

Publication number: SK280286B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; group; och; amino
Prior art date: 1992-12-02

Application number

SK1357-93A

Other languages

English (en)

Slovak (sk)

Other versions

SK135793A3 (en

Inventor

Patrice Renaut

Luc Lebreton

Patrick Dutartre

Philippe Derrepas

Soth Samreth

Original Assignee

Fournier Industrie Et Sante

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.)

1992-12-02

Filing date

1993-12-02

Publication date

1999-11-08

1993-12-02 Application filed by Fournier Industrie Et Sante filed Critical Fournier Industrie Et Sante

1994-06-08 Publication of SK135793A3 publication Critical patent/SK135793A3/sk

1999-11-08 Publication of SK280286B6 publication Critical patent/SK280286B6/sk

Links

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
238000000034 method Methods 0.000 title abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 120
150000003839 salts Chemical class 0.000 claims abstract description 33
-1 alkyl chloroformate Chemical compound 0.000 claims description 72
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 28
239000002585 base Substances 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 17
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 3
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208000023275 Autoimmune disease Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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
SGBRMIGZCHMUBD-UHFFFAOYSA-N CCCCNCCCNCC(=O)OC(C)(C)C Chemical compound CCCCNCCCNCC(=O)OC(C)(C)C SGBRMIGZCHMUBD-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
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)
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)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

SK1357-93A 1992-12-02 1993-12-02 Analógy 15-deoxyspergualínu, spôsob ich prípravy, SK280286B6 (sk)

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 (24)

Country	Link
US (1)	US5476870A (zh)
EP (1)	EP0600762B1 (zh)
JP (1)	JP2945261B2 (zh)
KR (1)	KR100187328B1 (zh)
CN (1)	CN1045431C (zh)
AT (1)	ATE140215T1 (zh)
AU (1)	AU664124B2 (zh)
CA (1)	CA2110437C (zh)
CZ (1)	CZ284958B6 (zh)
DE (1)	DE69303583T2 (zh)
DK (1)	DK0600762T3 (zh)
ES (1)	ES2092263T3 (zh)
FI (1)	FI112211B (zh)
FR (1)	FR2698628B1 (zh)
GR (1)	GR3021269T3 (zh)
HK (1)	HK1000467A1 (zh)
HU (1)	HU218908B (zh)
NO (1)	NO180483C (zh)
NZ (1)	NZ250330A (zh)
RU (1)	RU2114823C1 (zh)
SK (1)	SK280286B6 (zh)
TW (1)	TW311132B (zh)
UA (1)	UA39920C2 (zh)
ZA (1)	ZA938821B (zh)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE172189T1 (de) *	1995-02-10	1998-10-15	Fournier Ind & Sante	15-deoxyspergualin-analoge verbindungen, ihre verwendung als therapeutika und verfahren zu ihrer herstellung
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
DE19728436A1 (de) *	1997-07-03	1999-01-07	Niels Franke	Niedrigdosierte 15-Desoxyspergualin-Präparate
KR20010085742A (ko) *	1998-08-28	2001-09-07	추후제출	정밀한 길이의 폴리아미드 사슬, 그 제조방법 및 단백질결합체의 제조방법
DE19923961A1 (de) *	1999-05-25	2000-11-30	Euro Nippon Kayaku Gmbh	Verwendung von 15-Deoxyspergualin zur Behandlung von hyperreaktiven entzündlichen Erkrankungen und Autoimmunerkrankungen
HUE036916T2 (hu)	2004-05-05	2018-08-28	Silence Therapeutics Gmbh	Lipidek, lipid komplexek és ezek alkalmazása
CN101287497B (zh)	2004-12-27	2013-03-06	赛伦斯治疗公司	涂层脂质复合体和它们的用途
EP2269980A4 (de)	2008-12-24	2011-05-18	Vertex Closed Joint Stock Company	Creatinamide, verfahren zu ihrer herstellung und wirkstoff zur ausführung einer neuroprotektiven aktion
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)

* Cited by examiner, † Cited by third party
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
ES2039213T3 (es) *	1986-04-04	1993-09-16	Microbial Chemistry Research Foundation	Procedimiento para producir nuevos compuestos relacionados con espergualina.
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 EP EP93402795A patent/EP0600762B1/fr not_active Expired - Lifetime
- 1993-11-17 DE DE69303583T patent/DE69303583T2/de not_active Expired - Fee Related
- 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 DK DK93402795.4T patent/DK0600762T3/da active
- 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 UA UA93003726A patent/UA39920C2/uk unknown
- 1993-12-01 RU RU93053038A patent/RU2114823C1/ru 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
- 1993-12-02 CZ CZ932622A patent/CZ284958B6/cs not_active IP Right Cessation
- 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
1996
- 1996-10-04 GR GR960402621T patent/GR3021269T3/el unknown
1997
- 1997-11-04 HK HK97102083A patent/HK1000467A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA938821B (en)	1994-06-30
GR3021269T3 (en)	1997-01-31
RU2114823C1 (ru)	1998-07-10
NO934338L (no)	1994-06-03
JPH06293728A (ja)	1994-10-21
TW311132B (zh)	1997-07-21
HK1000467A1 (en)	1998-03-27
CZ262293A3 (en)	1994-06-15
DK0600762T3 (da)	1996-11-11
NO180483B (no)	1997-01-20
ES2092263T3 (es)	1996-11-16
FI935318L (fi)	1994-06-03
FI935318A0 (fi)	1993-11-29
EP0600762A1 (fr)	1994-06-08
CN1045431C (zh)	1999-10-06
CN1095709A (zh)	1994-11-30
KR940014435A (ko)	1994-07-18
DE69303583D1 (de)	1996-08-14
EP0600762B1 (fr)	1996-07-10
SK135793A3 (en)	1994-06-08
FR2698628A1 (fr)	1994-06-03
AU664124B2 (en)	1995-11-02
HUT65782A (en)	1994-07-28
NO180483C (no)	1997-04-30
DE69303583T2 (de)	1996-11-21
CA2110437C (en)	1999-04-13
KR100187328B1 (ko)	1999-05-15
AU5188393A (en)	1994-06-16
CA2110437A1 (en)	1994-06-03
JP2945261B2 (ja)	1999-09-06
NZ250330A (en)	1995-06-27
HU218908B (hu)	2000-12-28
NO934338D0 (no)	1993-11-30
HU9303406D0 (en)	1994-03-28
UA39920C2 (uk)	2001-07-16
ATE140215T1 (de)	1996-07-15
US5476870A (en)	1995-12-19
CZ284958B6 (cs)	1999-04-14
FR2698628B1 (fr)	1995-02-17
FI112211B (fi)	2003-11-14

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EP0885186B1 (en)	2003-03-26	Amino acid derivatives, pharmaceutical compositions containing these compounds and processes for preparing them
SK280286B6 (sk)	1999-11-08	Analógy 15-deoxyspergualínu, spôsob ich prípravy,
CA2434124A1 (fr)	2002-07-11	Derives de la n(phenylsulfonyl)glycine et leur utilisation en therapeutique
PL211429B1 (pl)	2012-05-31	Zastosowanie medyczne omega-aminoalkiloamidów kwasów R-2-arylo-propionowych oraz nowa klasa omega -R-2-aminoalkiloamidów kwasów R-2-arylo-propionowych i sposób ich wytwarzania
US5637613A (en)	1997-06-10	15-deoxyspergualin analogs, their method of preparation and their use in therapeutics
US5733928A (en)	1998-03-31	15-deoxyspergualin analogs, their method of preparation and their use in therapeutics
US5137917A (en)	1992-08-11	Spergualin-related compound and use thereof
NZ743308B (en)	2020-01-28	Meta-azacyclic amino benzoic acid derivatives as pan integrin antagonists