KR910009631A - 신규한 n-아실리조스핀고리피드와 그의 유도체 및 그의 제조방법 - Google Patents
신규한 n-아실리조스핀고리피드와 그의 유도체 및 그의 제조방법 Download PDFInfo
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- KR910009631A KR910009631A KR1019890017925A KR890017925A KR910009631A KR 910009631 A KR910009631 A KR 910009631A KR 1019890017925 A KR1019890017925 A KR 1019890017925A KR 890017925 A KR890017925 A KR 890017925A KR 910009631 A KR910009631 A KR 910009631A
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- aliphatic
- derived
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- 238000002360 preparation method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 125000001931 aliphatic group Chemical group 0.000 claims 10
- -1 aliphatic alcohols Chemical class 0.000 claims 9
- VAKIESMDOCVMDV-HNNXBMFYSA-N Spinosine Chemical compound C1C2=CC(O)=C(O)C=C2C[C@@H]2N1CCC1=C2C=C(OC)C(OC)=C1 VAKIESMDOCVMDV-HNNXBMFYSA-N 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001298 alcohols Chemical class 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001174 sulfone group Chemical group 0.000 claims 6
- 150000007513 acids Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 150000002772 monosaccharides Chemical group 0.000 claims 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000004036 acetal group Chemical group 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical group OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 150000004676 glycans Chemical group 0.000 claims 2
- 125000005597 hydrazone group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229920001282 polysaccharide Chemical group 0.000 claims 2
- 239000005017 polysaccharide Chemical group 0.000 claims 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- OTKJDMGTUTTYMP-ZWKOTPCHSA-N sphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO OTKJDMGTUTTYMP-ZWKOTPCHSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 150000003462 sulfoxides Chemical class 0.000 claims 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Chemical group OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims 1
- KLTIMEXKPRJOIS-UHFFFAOYSA-N 2-chloro-1-methyl-2H-pyridine hydroiodide Chemical compound I.CN1C=CC=CC1Cl KLTIMEXKPRJOIS-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical group O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010008748 Chorea Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 claims 1
- 125000003319 D-arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical group OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical group O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005277 alkyl imino group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical group OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 208000012601 choreatic disease Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 235000013681 dietary sucrose Nutrition 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229960002050 hydrofluoric acid Drugs 0.000 claims 1
- 239000008101 lactose Chemical group 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 claims 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/24—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 혈액중에 존재하는 D-스핀고 신과 N-디클로로아세틸스핀고신의 농도가 용혈현상에 미치는 효과를 나타낸 것이다.
Claims (30)
- 다음 일반식(I) 또는 (Ⅱ)을 갖는 N-아실리스핀고리피드와 그의 유도체 및 그의 염.윗 식에서, A는-CH=CH- 이거나 -CH2- 이고, n1은 6 내지 18의 정수이며, n2는 11 내지 15의 정수이고, X는 수소원자이거나, 단당류, 다당류 또는 포스포릴콜리의 잔기이여 R는 -염소, 브롬 및 불소; -자유 히드록 시기 또는 유기산이나 무기산으로 에스테르화된 히드록시기;- 에테르화된 히드록시기;- 저급 지방족 알콜이나 아르지방족(araliphatic)알콜로 부터 유도된 케토, 케탈 및 아세탈기;- 임으로, 저급알킬기 또는 아르알킬기로 치환된 케톡심, 알독심 또는 히드라존기;- 자유 메르캅토기 또는 저급 지방족 산이나 아르지방족산으로 에스테르화 되었거나 저급 지방족 알코이나 아르지방족 알콜로 에테르화된 메르캅토기;- 자유 카르복시기 또는 에스테르화 된 카르복시기;- 자유술폰기 또는 저급 지방족 알콜이나 아르지방족 알콜로 에스테르화 된 술폰기;- 술퍼아미드기 또는 저급 알킬이나 아르알키기 또는 저급알킬렌기로 치환된 술퍼아미드기;- 저급 알킬이나 아르알킬기로 부터 유도된 술폭사이드 또는 술폰기;- 니트릴기;- 자유 아미노기나 치환된 아미노기 및 이러한 아미노기의 4차 암모늄 유도체들로 이루어진 그룹으로 부터 선택된 하나이상의 극성기로 치환되어지고, 탄소수 2 내지 24인 포화 또는 불포화된 지방족 카르복실산으로 부터 유도된 알킬라디칼 및 N-(r-아미노-부티릴)스핀고신, N-(디클로로아세틸)스핀고신, N-(디클로로아세틸) 디히드로스핀고신 또는 N-아실리조스핀고리피드의 혼합물을 제외한 과아크릴화된 히드록시기를 가진 유도체와 금속이나 유기염 기성염 또는 이들의 산첨가염이다.
- 제1항에 있어서, 아실기는 최대 탄소수가 12개인 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항에 있어서, 아실기는 최대 탄소수가 4개인 알킬기와 최대 탄소수가 12개인 산이 측쇄로 된 분쇄를 갖는 산으로 부터 유도된 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항에 있어서, 극성기는 아실라디칼로 치환된 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항에 있어서, 극성기는 지방족, 방향족, 아르지방족, 지환족 또는 헤테로환족계열의 산으로 부터 유도된 에스테르화 된 히드록시기이며 치료학적으로 수용될 수 있는 것들임을 특징으로 하는 N-아실린스핀고리피드.
- 제5항에 있어서, 에스테르기는 최대 탄소수가 8개인 지방족산으로 부터 유도된 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제5항에 있어서, 에스테르기는 하나의 단일 고리형기를 갖는 지방족, 방향족, 아르지방족 또는 헤테로환족 산으로 부터 유도된 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항에 있어서, 극성기는 최대탄소수가 12개인 지방족계열의 알콜이나 임의로 1급 내지 3급의 저급알킬기로 치환된 지방족 부분에서 최대 탄소수가 4이고 한개의 단일 벤젠고리아르지방족 계열의 알콜이나, 지환족 또는 하나의 환상지방족 고리와 최대 탄소수가 14개인 지방족 지환족 계열의 알콜이거나 최대 탄소수가 12개이면서 N.O.S 로 형성된 기로 부터 선택된 헤테로원자를 함유하는 하나의 단일헤테로 환형고리로 된 헤테로 환족계의 알코올로된 에스테르화된 히드록시기 임을 특징으로 하는 N-아실린스핀고리피드.
- 제8항에 있어서, 극성기는 알킬부분에서 최대탄소수가 4인 히드록시, 아미노 및 알콕시기와 알킬부분에서 최대 탄소수가 4인 알킬이미노 또는 디알킬아미노기로 부터 선택된 관능기로 알콜을 치환시킨 에테르화된 히드록시기인 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항에 있어서, N-아실기는 모노, 디 또는 트리-클로로산이가나, 모노, 디 또는 트리-플루오르산으로 부터 유도된 것임을 특징으로 하는 N-아실린스핀고리피드.
- 제1항 내지 제10항중 어느 하나의 항에 있어서, 최대탄소수 6인 지방족산으로 부터 유도된 것을 특징으로 하는 N-아실린스핀고리피드의 과아실화 유도체.
- 제1항 내지 제11항중 어느 하나의 항에 있어서의 N-아실린스핀고리피드는 상기 일반식(I)중에서 X가 D-아라비노오즈, D-크실로오즈, D-리보도즈, L-람노오즈, D-글루코오즈, L-글루코오즈, D-갈락토오즈, D-N-아세틸 글루코스아민, L-N-아세틸 갈락토오즈아민, D-만노오즈, D-프럭토오즈 및 디키톡소오즈로 이루어진 그룹으로 부터 선택된 단당류인 일반식(I)의 화합물에 의하여 형성된 그룹으로 부터 선택된 스핀고리피드를 염기성 스핀고리피드로 갖는 것을 특징으로 하는 N-아실린스핀고리피드.
- 제1항 내지 12항중 어느 하나의 항에 있어서의 N-아실린스핀고리피드는 상기 일반식(I)중에서 X가 사카로오즈, 락토오즈, 셀로비오즈와 말토오즈로 이루어진 그룹으로 부터 선택된 이당류인 일반식(I)의 화합물에 의하여 형성된 그룹으로 부터 선택된 것을 염기성 리소스핀고리피드로 갖는 것을 특징으로 하는 N-아실린스핀고리피드.
- 제1항 내지 제10항중 어느 하나의 항에 있어서의 N-아실리조스핀고리피드는 스핀고신, 디히도로스핀고신, 프시코신, 디히드로스핀고신, 포스포릴클로린-스핀고신, 포스포릴크로린-디히드록시스핀고신 및 피토스핀고신으로 부터 형성된 그룹으로 부터 선택된 것을 염기성 리소스핀고리피드로 갖는 것을 특징으로 하는 N-아실리조스핀고리피드.
- 제1항 내지 제10항중 어느 하나의 항에 있어서의 N-아실리조스핀고리피드는 클로로아세틸스핀고신, 트리클로로아세틸 스핀고신 메르캅토아세틸 스핀고신, 말레리일스핀고신, 12-히드록시스테아로일스핀고신, 2-히드록시부티로일스핀고신, 플루오로아세틸스핀고신, 디플루오로 아세틸스핀고신, 3-아미노프로피오닐스핀고신, 아미노아세틸스핀고신, 트리플루오로아세틸코실스핀고신, 트리클로로피발로일스핀고신, 히드록시아세틸스핀고신, 트리클로로피발로일스핀고신, 시아노아세틸스핀고신, 디에틸아미노아세틸스핀고신, 및 이들의 과아실레이트로 이루어진 그룹으로 부터 선택된 것임을 특징으로 하는 N-아실리조스핀고리피드.
- 분자중에서 적어도 하나의 산작용기를 갖는 N-아실리조스핀고리피드나 그 혼합물의 치료학적 가능한 금속임.
- 제16항에 따른 N-아실리조스핀고리피드의 나트륨, 칼륨, 암모늄, 마그네슘 또는 암모늄염.
- 다음 일반식(I) 또는 (Ⅱ)중 하나의 리조스핀고리피드나 그 혼합물을 아실화 성분중에서 자유관능기를 일시적으로 보호한후, 아실화시켜서 되어짐을 특징으로 하는 N-아실리조스핀고리피드와 그의 염의 제조방법.윗 식에서, A는-CH=CH- 이거나 -CH2- 이고, n1은 6 내지 18의 정수이며, n2는 11 내지 15의 정수이고, X는 수소원자이거나, 단당류, 다당류 또는 포스포릴콜리의 잔기이여 R는 -염소, 브롬 및 불소; -자유 히드록 시기 또는 유기산이나 무기산으로 에스테르화된 히드록시기;- 에테르화된 히드록시기;- 저급 지방족 알콜이나 아르지방족(araliphatic)알콜로 부터 유도된 케토, 케탈 및 아세탈기;- 임으로, 저급알킬기 또는 아르알킬기로 치환된 케톡심, 알독심 또는 히드라존기;- 자유 메르캅토기 또는 저급 지방족 산이나 아르지방족산으로 에스테르화 되었거나 저급 지방족 알코이나 아르지방족 알콜로 에테르화된 메르캅토기;- 자유 카르복시기 또는 에스테르화 된 카르복시기;- 자유술폰기 또는 저급 지방족 알콜이나 아르지방족 알콜로 에스테르화 된 술폰기;- 술퍼아미드기 또는 저급 알킬이나 아르알키기 또는 저급알킬렌기로 치환된 술퍼아미드기;- 저급 알킬이나 아르알킬기로 부터 유도된 술폭사이드 또는 술폰기;- 니트릴기;- 자유 아미노기나 치환된 아미노기 및 이러한 아미노기의 4차 아모늄 유도체들로 이루어진 그룹으로 선택된 하나이상의 극성기로 치환되어지고, 탄소수 2 내지 24인 포화 또는 불포화된 지방족 카르복실산으로 유도된 알킬라디칼 및 N-(r-아미노-부티릴)스핀고신, N-(디클로로아세틸)스핀고신, N-(디클로로아세틸) 디히드로스핀고신 또는 N-아실리조스핀고리피드의 혼합물을 제외한 과아크릴화된 히드록시기를 가진 유도체와 금속이나 유기염 기성염 또는 이들의 산첨가염이다.
- 제18항에 있어서, 출발물지른 산의 반응적인 관능성 유도체와 반응되어짐을 특징으로 하는 제조방법.
- 제18항에 있어서의 방법은 1. 리조스핀고리피드 유도체와 산아지드와의 반응; 2. 리조스핀고리피드 유도체와 아실이미다졸의 반응; 3. 리조스핀고리피드 유도체와 산과 트리플루오로아세트산의 혼합무수물과의 반응; 4. 리조스핀고리피드 유도체와 산의 염화물과의 반응; 5. 카르보디이미드와 1-히드록시벤조트리아졸의 존재하에 리조스핀고리피드 유도체와 산과의 반응; 6. 고온에서 리조스핀고리피드 유도체와 산과의 반응; 7. 고온에서 리조스핀고리피드 유도체와 산의 메틸에스테르와의 반응; 8. 리조스핀고리피드와, 산의 염과 1-메틸-2-클로로피디린 요오드화물이나 그와 유사한 생성물간의 교환에서 유도된 에스테르와의 반응에서 이루어진 그룹으로 부터 선택된 제조방법.
- 제18항에 내지 제20항중 어느 하나의 항에 있어서, 자유 1차 또는 2차 아미노기 또는 카르복시기는 아실화반응시 히드록시기에 일시적으로 보호시켜서 됨을 특징으로 하는 제조방법.
- 제18항 내지 제21항중 어느 하나의 항에 있어서의 방법은 어떠한 단계에서 방해받거나 또는 중간단계에서 시작하게 되고, 그때 나머지단계가 수행되게 됨을 특징으로 하는 제조방법.
- 약제학적으로 제1항 내지 제10항의 화합물을 사용하는 방법.
- 약제학적으로 허용가능한 부형제와 함께 활성성분으로서 제1항 내지 제10항의 화합물을 함유하는 조약제제.
- 신경계통의 병리를 치료하기 위하여 제1항 내지 제10항의 화합물을 치료하는데 사용하는 방법.
- 발작증, 충격증, 무도병 노쇠증, 간질병 심근경색증, 및/또는 협심증의 요법에 제25항인 화합물을 치료하는데 사용하는 방법.
- 제25항에 있어서, 활성성분을 경구투여시, 몸무게 1kg당 0.05 내지 5mg의 양으로 투여하여 치료하는데 사용하는 방법.
- N-디클로아세틸스핀고신, N-디클로아세틸디히드로스핀고신, 또는 N-(r-아미노부티릴)스핀고신을 약제학적으로 사용하는 방법.
- 활성성분으로서 N-디클로아세틸스핀고신, N-디클로아세틸디히드로스핀고신, 또는 N-(r-아미노부티릴)스핀고신을 함유하는 조약제제.
- N-디클로아세틸스핀고신, N-디클로아세틸디히드로스핀고신, 또는 N-(r-아미노부티릴)스핀고신을 치료하는데 사용하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT8848619A IT1235162B (it) | 1988-12-02 | 1988-12-02 | Derivati di lisosfingolipidi |
IT48619A/88 | 1988-12-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR910009631A true KR910009631A (ko) | 1991-06-28 |
Family
ID=11267672
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019890017925A KR910009631A (ko) | 1988-12-02 | 1989-12-02 | 신규한 n-아실리조스핀고리피드와 그의 유도체 및 그의 제조방법 |
Country Status (16)
Country | Link |
---|---|
US (2) | US5519007A (ko) |
EP (1) | EP0373038B1 (ko) |
JP (1) | JP3004297B2 (ko) |
KR (1) | KR910009631A (ko) |
AT (1) | ATE149506T1 (ko) |
AU (1) | AU632771B2 (ko) |
CA (1) | CA2004190A1 (ko) |
DE (1) | DE68927821T2 (ko) |
DK (1) | DK589789A (ko) |
FI (1) | FI895766A0 (ko) |
HU (3) | HU209561B (ko) |
IL (1) | IL92511A0 (ko) |
IT (1) | IT1235162B (ko) |
NO (1) | NO894819L (ko) |
NZ (1) | NZ231590A (ko) |
TW (1) | TW204300B (ko) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1235011B (it) * | 1988-07-26 | 1992-06-16 | Fidia Farmaceutici | Sintesi di derivati di glicosfingolipidi ed in particolare di gangliosidi utilizzabili per la preparazione di immunoadsorbenti ed adsorbenti per affinita' impiegabili per la purificazione di anticorpi e di tossine specifiche, e per uso diagnostico |
US5466675A (en) * | 1992-02-04 | 1995-11-14 | Piljac; Goran | Immunological activity of rhamnolipids |
TW261533B (ko) * | 1992-07-16 | 1995-11-01 | Kirin Brewery | |
FR2711138B1 (fr) * | 1993-10-12 | 1995-11-24 | Oreal | Céramides, leur procédé de préparation et leurs applications en cosmétique et en dermopharmacie. |
DE69433062T2 (de) * | 1993-10-28 | 2004-06-17 | Cosmoferm B.V. | Ceramid i analoge auf basis von phytosphingosine |
US5663151A (en) * | 1994-03-04 | 1997-09-02 | Bristol-Myers Squibb Company | Sulfated α-glycolipid derivatives as cell adhesion inhibitors |
US5651981A (en) * | 1994-03-29 | 1997-07-29 | Northwestern University | Cationic phospholipids for transfection |
DE69514306T2 (de) * | 1994-04-27 | 2000-06-21 | Dsm Nv | Kurzkettige 2-hydroxycarbonsäurederivate von ceramiden |
US6428999B1 (en) | 1994-07-21 | 2002-08-06 | Takara Shuzo Co., Ltd. | Sphingolipid ceramide N-deacylase, methods for producing sphingolipids and sphingolipid derivatives, and spingolipid ceramide N-deacylase gene |
EP0707063B1 (en) * | 1994-07-21 | 1998-06-17 | Takara Shuzo Co. Ltd. | Glycolipid ceramide deacylase |
JP4101320B2 (ja) * | 1996-10-11 | 2008-06-18 | 高砂香料工業株式会社 | 一級アミド誘導体の製造方法 |
JP3485232B2 (ja) * | 1997-01-31 | 2004-01-13 | 高砂香料工業株式会社 | 光学活性化合物及びその製造方法 |
US6063387A (en) * | 1997-04-17 | 2000-05-16 | Elizabeth Arden Co., Division Of Conopco, Inc. | Anhydrous cosmetic composition with ceramides for firming skin |
EP1159256A1 (en) * | 1999-03-09 | 2001-12-05 | Cosmoferm B.V. | Sphingoid base derivatives and uses thereof |
EP1435972B1 (en) | 2001-08-29 | 2016-03-09 | Seneb Biosciences Inc. | Novel synthetic ganglioside derivatives and compositions thereof |
FR2839310A1 (fr) * | 2002-05-03 | 2003-11-07 | Pasteur Institut | Nouveau procede de preparation d' alpha-glycosylceramides, nouveaux derives alpha-glycosylceramide et leurs applications |
ES2325260T3 (es) * | 2003-01-20 | 2009-08-31 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Utilizacion de esfingolipidos para reducir los niveles de triacilglicerol y colesterol en el plasma. |
NL1022443C2 (nl) | 2003-01-20 | 2004-07-22 | Tno | Sphingolipiden voor verbetering van de samenstelling van de darmflora. |
AU2004220087A1 (en) | 2003-03-06 | 2004-09-23 | Seneb Biosciences, Inc. | Methods and compositions for the enzymatic synthesis of gangliosides |
ATE500752T1 (de) * | 2004-03-16 | 2011-03-15 | Tno | Verwendung von sphingolipiden bei der behandlung und vorbeugung von typ-2-diabetes mellitus, insulinresistenz und metabolismussyndrom |
JP2008521888A (ja) | 2004-11-30 | 2008-06-26 | ネーデルランドセ オルガニサティエ フォール トエゲパストナトールヴェテンシャッペリク オンデルゾエク ティエヌオー | 脂肪症の、又は肝毒性及びその後遺症の治療及び予防におけるスフィンゴ脂質 |
EP2410846B1 (en) | 2009-03-25 | 2016-09-07 | Seneb Biosciences, Inc. | Glycolipids as treatment for disease |
WO2018200931A1 (en) * | 2017-04-28 | 2018-11-01 | University Of Virginia Patent Foundation | Compositions and methods for treating cancer |
KR102640816B1 (ko) | 2021-02-17 | 2024-02-23 | 곽영민 | 식별선이 구비된 파이프라인 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1171432B (it) * | 1981-08-03 | 1987-06-10 | Fidia Farmaceutici | Amidi organiche derivate da lipidi azotati utilizzabili come farmaci |
AU546872B2 (en) * | 1982-06-16 | 1985-09-26 | Unilever Plc | Skin treatment compositions containing a fatty acid or ester |
CH679209A5 (en) * | 1983-12-05 | 1992-01-15 | Solco Basel Ag | New neutral glyco-sphingolipid derivs. |
EP0146810A3 (de) * | 1983-12-05 | 1987-05-13 | Solco Basel AG | Verfahren zur Herstellung von Sphingosinderivaten |
DD261165A5 (de) * | 1985-08-13 | 1988-10-19 | Solco Basel Ag,Ch | Neues verfahren zur herstellung von sphingosinderivaten |
EP0212400B1 (de) * | 1985-08-13 | 1992-01-02 | Solco Basel AG | Neues Verfahren zur Herstellung von Sphingosinderivaten |
JPH0692349B2 (ja) * | 1986-03-06 | 1994-11-16 | 和光純薬工業株式会社 | 光学活性不飽和アミノアルコール誘導体の新規な製法 |
US4937232A (en) * | 1986-09-15 | 1990-06-26 | Duke University | Inhibition of protein kinase C by long-chain bases |
US4816450A (en) * | 1986-09-15 | 1989-03-28 | Duke University | Inhibition of protein kinase C by long-chain bases |
-
1988
- 1988-12-02 IT IT8848619A patent/IT1235162B/it active
-
1989
- 1989-11-23 DK DK589789A patent/DK589789A/da not_active Application Discontinuation
- 1989-11-29 EP EP89403309A patent/EP0373038B1/en not_active Expired - Lifetime
- 1989-11-29 DE DE68927821T patent/DE68927821T2/de not_active Expired - Fee Related
- 1989-11-29 AT AT89403309T patent/ATE149506T1/de not_active IP Right Cessation
- 1989-11-29 CA CA002004190A patent/CA2004190A1/en not_active Abandoned
- 1989-11-30 AU AU45664/89A patent/AU632771B2/en not_active Ceased
- 1989-11-30 IL IL92511A patent/IL92511A0/xx unknown
- 1989-11-30 NZ NZ231590A patent/NZ231590A/xx unknown
- 1989-12-01 HU HU913514A patent/HU209561B/hu not_active IP Right Cessation
- 1989-12-01 HU HU896336A patent/HU205365B/hu not_active IP Right Cessation
- 1989-12-01 FI FI895766A patent/FI895766A0/fi not_active Application Discontinuation
- 1989-12-01 NO NO89894819A patent/NO894819L/no unknown
- 1989-12-01 TW TW078109297A patent/TW204300B/zh active
- 1989-12-01 HU HU913514A patent/HU913514D0/hu unknown
- 1989-12-02 KR KR1019890017925A patent/KR910009631A/ko not_active Application Discontinuation
- 1989-12-02 JP JP1314136A patent/JP3004297B2/ja not_active Expired - Fee Related
-
1992
- 1992-07-21 US US07/916,257 patent/US5519007A/en not_active Expired - Fee Related
-
1996
- 1996-04-05 US US08/628,344 patent/US5792858A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
NZ231590A (en) | 1992-12-23 |
EP0373038B1 (en) | 1997-03-05 |
CA2004190A1 (en) | 1990-06-02 |
US5519007A (en) | 1996-05-21 |
IL92511A0 (en) | 1990-08-31 |
DE68927821T2 (de) | 1997-09-25 |
AU632771B2 (en) | 1993-01-14 |
IT1235162B (it) | 1992-06-22 |
TW204300B (ko) | 1993-04-21 |
EP0373038A3 (en) | 1992-01-08 |
HU205365B (en) | 1992-04-28 |
JP3004297B2 (ja) | 2000-01-31 |
FI895766A0 (fi) | 1989-12-01 |
NO894819D0 (no) | 1989-12-01 |
DK589789A (da) | 1990-06-03 |
DE68927821D1 (de) | 1997-04-10 |
US5792858A (en) | 1998-08-11 |
HU913514D0 (en) | 1992-01-28 |
ATE149506T1 (de) | 1997-03-15 |
AU4566489A (en) | 1990-06-21 |
NO894819L (no) | 1990-06-05 |
HUT52107A (en) | 1990-06-28 |
DK589789D0 (da) | 1989-11-23 |
HU209561B (en) | 1994-07-28 |
IT8848619A0 (it) | 1988-12-02 |
EP0373038A2 (en) | 1990-06-13 |
JPH02200691A (ja) | 1990-08-08 |
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