DE2756713A1 - 5-hydroxycytidylsaeure enthaltende copolymere, verfahren zu deren herstellung sowie dieselben enthaltende pharmazeutische praeparate - Google Patents
5-hydroxycytidylsaeure enthaltende copolymere, verfahren zu deren herstellung sowie dieselben enthaltende pharmazeutische praeparateInfo
- Publication number
- DE2756713A1 DE2756713A1 DE19772756713 DE2756713A DE2756713A1 DE 2756713 A1 DE2756713 A1 DE 2756713A1 DE 19772756713 DE19772756713 DE 19772756713 DE 2756713 A DE2756713 A DE 2756713A DE 2756713 A1 DE2756713 A1 DE 2756713A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- poly
- copolymer
- component
- mol
- 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.)
- Withdrawn
Links
- 229920001577 copolymer Polymers 0.000 title claims description 58
- 239000002253 acid Substances 0.000 title claims description 48
- 238000000034 method Methods 0.000 title claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229930183912 Cytidylic acid Natural products 0.000 claims description 11
- IERHLVCPSMICTF-UHFFFAOYSA-N cytidine monophosphate Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(COP(O)(O)=O)O1 IERHLVCPSMICTF-UHFFFAOYSA-N 0.000 claims description 11
- IERHLVCPSMICTF-XVFCMESISA-N cytidine 5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-XVFCMESISA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000005893 bromination reaction Methods 0.000 claims description 8
- 230000031709 bromination Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000000862 absorption spectrum Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 20
- 208000015181 infectious disease Diseases 0.000 description 18
- 108091033319 polynucleotide Proteins 0.000 description 13
- 239000002157 polynucleotide Substances 0.000 description 13
- 102000040430 polynucleotide Human genes 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000000840 anti-viral effect Effects 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000000502 dialysis Methods 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 108091036414 Polyinosinic:polycytidylic acid Proteins 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 241000710772 Yellow fever virus Species 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000010257 thawing Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 229940051021 yellow-fever virus Drugs 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 108020002230 Pancreatic Ribonuclease Proteins 0.000 description 2
- 102000005891 Pancreatic ribonuclease Human genes 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 1
- IDIOXQQTCONHED-UHFFFAOYSA-N 4-hydroxy-2-piperazin-1-ylbutane-2-sulfonic acid Chemical compound OCCC(C)(S(O)(=O)=O)N1CCNCC1 IDIOXQQTCONHED-UHFFFAOYSA-N 0.000 description 1
- 241000722946 Acanthocybium solandri Species 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 1
- 241000710188 Encephalomyocarditis virus Species 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000656145 Thyrsites atun Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011176 biofiber Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB53822/76A GB1545099A (en) | 1976-12-23 | 1976-12-23 | Poly-5-hydroxycytidylic acid copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2756713A1 true DE2756713A1 (de) | 1978-07-13 |
Family
ID=10469095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772756713 Withdrawn DE2756713A1 (de) | 1976-12-23 | 1977-12-20 | 5-hydroxycytidylsaeure enthaltende copolymere, verfahren zu deren herstellung sowie dieselben enthaltende pharmazeutische praeparate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4151350A (enExample) |
| JP (1) | JPS53111400A (enExample) |
| CA (1) | CA1094056A (enExample) |
| DE (1) | DE2756713A1 (enExample) |
| FR (1) | FR2375254A1 (enExample) |
| GB (1) | GB1545099A (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435571A (en) * | 1973-04-02 | 1976-05-12 | Searle & Co | Polynucleotides |
| JPS518295A (en) * | 1974-07-12 | 1976-01-23 | Kojin Kk | 55 hidorokishi 2*2** saikuroshichijin mataha sonoennoseizohoho |
-
1976
- 1976-12-23 GB GB53822/76A patent/GB1545099A/en not_active Expired
-
1977
- 1977-12-05 US US05/857,851 patent/US4151350A/en not_active Expired - Lifetime
- 1977-12-06 CA CA292,512A patent/CA1094056A/en not_active Expired
- 1977-12-20 DE DE19772756713 patent/DE2756713A1/de not_active Withdrawn
- 1977-12-22 JP JP15500977A patent/JPS53111400A/ja active Pending
- 1977-12-23 FR FR7739093A patent/FR2375254A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2375254B1 (enExample) | 1981-01-16 |
| FR2375254A1 (fr) | 1978-07-21 |
| JPS53111400A (en) | 1978-09-28 |
| US4151350A (en) | 1979-04-24 |
| CA1094056A (en) | 1981-01-20 |
| GB1545099A (en) | 1979-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69005394T2 (de) | Zusammensetzungen welche komplexe von hyaluronsäure enthalten und verfahren zu deren herstellung. | |
| DE2515600C2 (de) | Verwendung einer wäßrigen Lösung eines Block-Copolymeren aus Äthylenoxyd und Propylenoxyd als Reinigungslösung für Wunden | |
| DE69310122T2 (de) | Zahnpastezusammensetzung | |
| DE69327642T2 (de) | Verfahren zur behandlung von viralen infectionen | |
| DE68902860T2 (de) | Verfahren zur verhuetung der aids-uebertragung durch blutuebertragung. | |
| DE19549421C2 (de) | Pharmazeutische Zubereitung zur Behandlung akuter Rhinitiden | |
| DE2051745A1 (de) | Von Nucleinsäuren stammende Arznei mittel und Verfahren zu ihrer Herstellung | |
| DE2514536A1 (de) | Verfahren zur reaktivierung von interferon | |
| DE68904264T2 (de) | Fragmente und fraktionen von heparin mit wirkung gegen hiv. | |
| DE2435746C2 (enExample) | ||
| DE69300492T2 (de) | Orale Zusammensetzung. | |
| DE2208787B2 (de) | Mittel zur Behandlung von Herpes-Virusinfektionen | |
| DE19541919C2 (de) | Pharmazeutische Zubereitung zur Behandlung akuter Rhinitiden | |
| DE2751454A1 (de) | Steuerung und umkehr der immunologischen alterung | |
| DE3832401C2 (enExample) | ||
| DE2756713A1 (de) | 5-hydroxycytidylsaeure enthaltende copolymere, verfahren zu deren herstellung sowie dieselben enthaltende pharmazeutische praeparate | |
| DE69308762T2 (de) | Behandlung des Muskulschwunds | |
| DE69624558T2 (de) | Inhibitor der eindickung der intravaskulären membran | |
| DE1617659C3 (de) | Interferonbildendes Arzneimittel und dessen Verwendung | |
| EP1443921B1 (de) | Herstellung reiner stereoisomere von tricyclo-[5.2.1.0(2.6) ]-dec-9-yl-xanthogenat sowie deren verwendung als arzneimittel | |
| DE69527205T2 (de) | Arzneimittel gegen endotoxinschock und dadurch ausgelöstes multiples organversagen | |
| FR2677650B1 (fr) | Retinouides substitues par un cycle dithiane et leur utilisation, procede de preparation desdits composes, compositions cosmetique et pharmaceutique les contenant et utilisation therapeutique de cette derniere. | |
| DE2225548C3 (de) | Intravenös verträglicher Impfstoff gegen Staupe- und Hepatite contagiosa canis | |
| DE3520325C2 (enExample) | ||
| DE2415812A1 (de) | Poly(5-hydroxycytidylsaeuren) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |