DE2359621C2 - Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure - Google Patents
Antiviral wirksame Alkalimetall- oder Ammoniumsalze der PolyacrylsäureInfo
- Publication number
- DE2359621C2 DE2359621C2 DE19732359621 DE2359621A DE2359621C2 DE 2359621 C2 DE2359621 C2 DE 2359621C2 DE 19732359621 DE19732359621 DE 19732359621 DE 2359621 A DE2359621 A DE 2359621A DE 2359621 C2 DE2359621 C2 DE 2359621C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- molecular weight
- salt
- acid
- poly
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229920002125 Sokalan® Polymers 0.000 title claims description 42
- 239000004584 polyacrylic acid Substances 0.000 title claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 6
- 150000001340 alkali metals Chemical class 0.000 title claims description 4
- 150000003863 ammonium salts Chemical class 0.000 title claims description 3
- 230000000840 anti-viral effect Effects 0.000 title description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 3
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 3
- 239000003443 antiviral agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 229920001585 atactic polymer Polymers 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 15
- 241000700605 Viruses Species 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 9
- 239000000725 suspension Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- -1 hydrocarbon radicals Chemical class 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012062 aqueous buffer Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- HQPSKTOGFFYYKN-UHFFFAOYSA-N CC(C)[Na] Chemical compound CC(C)[Na] HQPSKTOGFFYYKN-UHFFFAOYSA-N 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 241000710188 Encephalomyocarditis virus Species 0.000 description 1
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 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 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000029812 viral genome replication 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
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymerization Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732359621 DE2359621C2 (de) | 1973-11-30 | 1973-11-30 | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure |
| CA214,192A CA1028446A (en) | 1973-11-30 | 1974-11-18 | Antiviral polymer |
| NL7415340A NL180480C (nl) | 1973-11-30 | 1974-11-25 | Werkwijze voor de bereiding van een geneesmiddel. |
| GB5164674A GB1469845A (en) | 1973-11-30 | 1974-11-28 | Antiviral polymer |
| JP13596574A JPS5739245B2 (nl) | 1973-11-30 | 1974-11-28 | |
| BE151063A BE822845A (fr) | 1973-11-30 | 1974-12-02 | Sel d'acide polyacrylique a effet antiviral |
| FR7439373A FR2253530B1 (nl) | 1973-11-30 | 1974-12-02 | |
| US05/757,503 US4150238A (en) | 1973-11-30 | 1977-01-07 | Antiviral polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732359621 DE2359621C2 (de) | 1973-11-30 | 1973-11-30 | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2359621A1 DE2359621A1 (de) | 1975-06-05 |
| DE2359621C2 true DE2359621C2 (de) | 1982-11-18 |
Family
ID=5899471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732359621 Expired DE2359621C2 (de) | 1973-11-30 | 1973-11-30 | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5739245B2 (nl) |
| BE (1) | BE822845A (nl) |
| CA (1) | CA1028446A (nl) |
| DE (1) | DE2359621C2 (nl) |
| FR (1) | FR2253530B1 (nl) |
| GB (1) | GB1469845A (nl) |
| NL (1) | NL180480C (nl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2639669C3 (de) * | 1976-09-03 | 1982-05-06 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung eines Poly(meth)acrylsäureesters mit hoher Isotaxie und enger Molekulargewichtsverteilung |
| FR2857361B1 (fr) | 2003-07-08 | 2005-09-09 | Genfit S A | PREPARATION DE DERIVES DE 1,3-DIPHENYPROP-2-¼n-1-one |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3222339A (en) * | 1962-08-14 | 1965-12-07 | Rohm & Haas | Polymerization process using an organomagnesium compound as catalyst |
| BE794403A (fr) * | 1972-04-05 | 1973-07-23 | Rohm & Haas | Polymeres nouveaux d'acrylates d'alcoyle |
-
1973
- 1973-11-30 DE DE19732359621 patent/DE2359621C2/de not_active Expired
-
1974
- 1974-11-18 CA CA214,192A patent/CA1028446A/en not_active Expired
- 1974-11-25 NL NL7415340A patent/NL180480C/nl not_active IP Right Cessation
- 1974-11-28 GB GB5164674A patent/GB1469845A/en not_active Expired
- 1974-11-28 JP JP13596574A patent/JPS5739245B2/ja not_active Expired
- 1974-12-02 FR FR7439373A patent/FR2253530B1/fr not_active Expired
- 1974-12-02 BE BE151063A patent/BE822845A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2253530B1 (nl) | 1978-06-30 |
| BE822845A (fr) | 1975-06-02 |
| NL180480C (nl) | 1987-03-02 |
| JPS5739245B2 (nl) | 1982-08-20 |
| DE2359621A1 (de) | 1975-06-05 |
| NL7415340A (nl) | 1975-06-03 |
| GB1469845A (en) | 1977-04-06 |
| JPS5087185A (nl) | 1975-07-14 |
| FR2253530A1 (nl) | 1975-07-04 |
| CA1028446A (en) | 1978-03-21 |
| NL180480B (nl) | 1986-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69737232T2 (de) | Ionische polymere als anti-infektiöse mittel | |
| DE746788C (de) | Verfahren zur Herstellung von Polymerisationsprodukten aus Vinylestern | |
| DE1745214A1 (de) | Neue Copolymerisate auf der Basis von Vinylverbindungen und Krotonsaeure,Verfahren zu deren Herstellung und die Copolymerisate enthaltende kosmetische Mittel | |
| DE3045078A1 (de) | Nucleasebestaendiger hydrophiler komplex aus polyriboinosinsaeure, verfahren zu seiner herstellung und verwendung desselben | |
| DE1495656B2 (nl) | ||
| DE832680C (de) | Verfahren zur Polymerisation von Amiden von Saeuren der Acrylsaeurereihen | |
| DE1745565A1 (de) | Verfahren zur Herstellung von Copolymeren aus AEthylen und Vinylestern | |
| DE2253977C2 (de) | Antiviraler Komplex, Verfahren zu seiner Herstellung und diesen Komplex enthaltende Arzneimittel | |
| DE2359621C2 (de) | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure | |
| DE2631780B2 (de) | Sulfonamid-Trimethoprim-Lösungen | |
| DE1032537B (de) | Verfahren zur Herstellung von phosphorhaltigen Polymerisaten | |
| DE953119C (de) | Verfahren zur Herstellung von Vinylchloridpolymeren | |
| DE2262449C3 (de) | Divinyläther-Maleinsäureanhydrid-Copolymerisate | |
| DE2445679C3 (de) | Stimulierung der Immunität | |
| DE68922826T2 (de) | Verwendung einer Zusammensetzung, die organisch gebundenes Germanium enthaltet, zur Herstellung von Arzneimitteln zur Behandlung von AIDS. | |
| DE69407491T2 (de) | Copolymere aus Acetylsalicylat und Vinylalkohol | |
| DE2503442A1 (de) | Antivirale substanzen, verfahren zu ihrer herstellung und diese substanzen enthaltende arzneimittel | |
| DE1214404B (de) | Verfahren zur Herstellung modifizierter Polyvinylalkohole | |
| DE704039C (de) | Verfahren zur Emulsionspolymerisation von Butadienen | |
| DE2911642C2 (de) | Verfahren zur Herstellung von &alpha;,&beta;-ungesättigten N-substituierten Carbonsäureamiden und ihre Verwendung zur Herstellung von Polymerisaten sowie das N-(N',N',2,2 Tetramethyl-3-aminopropyl)-methacrylamid | |
| DE1266502B (de) | Verfahren zur Herstellung hochmolekularer Polymerisate von Vinylalkylaethern | |
| DE936296C (de) | Verfahren zur Herstellung wasserloeslicher, nicht salzbildender Hochpolymerer | |
| DE3026447A1 (de) | Antitumoral wirkende mittel | |
| Mejzlík et al. | Blockierung der endgruppen von polyformaldehyd. II. Acetylierung der endgruppen von polyformaldehyd mit acetanhydrid | |
| DE1595115C (de) | Verfahren zur Herstellung von fluor haltigen Copolymerisaten von Ketonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |