HU198733B - Process for producing salts of n-acetylneuraminic acid and pharmaceutical compositions comprising same - Google Patents
Process for producing salts of n-acetylneuraminic acid and pharmaceutical compositions comprising same Download PDFInfo
- Publication number
- HU198733B HU198733B HU883140A HU314085A HU198733B HU 198733 B HU198733 B HU 198733B HU 883140 A HU883140 A HU 883140A HU 314085 A HU314085 A HU 314085A HU 198733 B HU198733 B HU 198733B
- Authority
- HU
- Hungary
- Prior art keywords
- acid
- acetyl
- sputum
- salt
- acetylneuraminic acid
- Prior art date
Links
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 title claims description 38
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 7
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 title abstract description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 abstract description 24
- 208000024794 sputum Diseases 0.000 abstract description 24
- 210000003802 sputum Anatomy 0.000 abstract description 24
- 230000003419 expectorant effect Effects 0.000 abstract description 14
- 239000003172 expectorant agent Substances 0.000 abstract description 13
- 230000001886 ciliary effect Effects 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 17
- 210000004877 mucosa Anatomy 0.000 description 11
- 230000001133 acceleration Effects 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 210000004081 cilia Anatomy 0.000 description 9
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 8
- 229960004373 acetylcholine Drugs 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- -1 amine compound Chemical class 0.000 description 8
- 159000000007 calcium salts Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 230000032258 transport Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MVHOXPMVPRDZIH-CBSHMQKXSA-M sodium N-[(3S,4R,5R,6S,7R)-1-carboxy-3,5,6,7,8-pentahydroxy-1-oxooctan-4-yl]ethanimidate Chemical compound [Na+].CC(=O)N[C@H]([C@@H](O)CC(=O)C([O-])=O)[C@@H](O)[C@H](O)[C@H](O)CO MVHOXPMVPRDZIH-CBSHMQKXSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000004209 hair Anatomy 0.000 description 4
- 210000003254 palate Anatomy 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000003047 N-acetyl group Chemical group 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 229960001231 choline Drugs 0.000 description 3
- 239000007799 cork Substances 0.000 description 3
- 239000008263 liquid aerosol Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000420 mucociliary effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 2
- 241000269350 Anura Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000223782 Ciliophora Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000012812 general test Methods 0.000 description 2
- 210000002768 hair cell Anatomy 0.000 description 2
- 210000003780 hair follicle Anatomy 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 2
- 210000004988 splenocyte Anatomy 0.000 description 2
- 229960000195 terbutaline Drugs 0.000 description 2
- ZGARTFOIAZCVKF-SGBOKBNOSA-N (4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid;sodium Chemical compound [Na].CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ZGARTFOIAZCVKF-SGBOKBNOSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 206010006448 Bronchiolitis Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- JUGOREOARAHOCO-UHFFFAOYSA-M acetylcholine chloride Chemical compound [Cl-].CC(=O)OCC[N+](C)(C)C JUGOREOARAHOCO-UHFFFAOYSA-M 0.000 description 1
- 229960004266 acetylcholine chloride Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000000442 hair follicle cell Anatomy 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000003612 virological effect Effects 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
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59189950A JPS6168418A (ja) | 1984-09-11 | 1984-09-11 | 去痰薬 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU198733B true HU198733B (en) | 1989-11-28 |
Family
ID=16249907
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU883140A HU198733B (en) | 1984-09-11 | 1985-09-10 | Process for producing salts of n-acetylneuraminic acid and pharmaceutical compositions comprising same |
| HU853417A HU197515B (en) | 1984-09-11 | 1985-09-10 | Process for production of medical compositions with expectorating effect containing n-acetil neuramin acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU853417A HU197515B (en) | 1984-09-11 | 1985-09-10 | Process for production of medical compositions with expectorating effect containing n-acetil neuramin acid |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4698332A (OSRAM) |
| EP (2) | EP0429430B1 (OSRAM) |
| JP (1) | JPS6168418A (OSRAM) |
| KR (1) | KR880001234B1 (OSRAM) |
| CN (1) | CN85108388B (OSRAM) |
| AT (2) | ATE111738T1 (OSRAM) |
| AU (1) | AU582584B2 (OSRAM) |
| CA (1) | CA1246452A (OSRAM) |
| DE (2) | DE3587587T2 (OSRAM) |
| DK (1) | DK165046C (OSRAM) |
| ES (1) | ES8606323A1 (OSRAM) |
| FI (1) | FI83963C (OSRAM) |
| HU (2) | HU198733B (OSRAM) |
| ZA (1) | ZA856905B (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61289037A (ja) * | 1985-06-14 | 1986-12-19 | Mect Corp | 新規去痰薬 |
| GB8519416D0 (en) * | 1985-08-01 | 1985-09-04 | Unilever Plc | Oligosaccharides |
| JP2573594B2 (ja) * | 1987-03-06 | 1997-01-22 | メクト株式会社 | Ｎーアセチルー３ーフルオローノイラミン酸誘導体およびその製造方法 |
| US5843445A (en) * | 1987-06-24 | 1998-12-01 | Autoimmune, Inc. | Method of treating rheumatoid arthritis with type II collagen |
| JP2517293B2 (ja) * | 1987-06-25 | 1996-07-24 | メクト株式会社 | 細胞、組織修復剤 |
| US5393742A (en) * | 1990-08-30 | 1995-02-28 | Mect Corporation | Preparation for treating renal disease |
| US5514665A (en) * | 1993-12-30 | 1996-05-07 | University Of British Columbia | Method of preventing or reducing the risk of infection by bacterial pathogens utilizing simple and conjugated dextrans |
| AUPM411494A0 (en) * | 1994-02-25 | 1994-03-24 | Central Sydney Area Health Service | Method and device for the provocation of upper or lower airway narrowing and/or the induction of sputum |
| US5856446A (en) * | 1995-07-07 | 1999-01-05 | Autoimmune Inc. | Method of treating rheumatoid arthritis with low dose type II collagen |
| AUPQ275799A0 (en) * | 1999-09-10 | 1999-10-07 | Luminis Pty Limited | Recombinant bacterium expressing an oligosaccharide receptor mimic |
| JP4005115B1 (ja) | 2007-02-08 | 2007-11-07 | 日本臓器製薬株式会社 | 疼痛疾患治療剤 |
| WO2012009474A1 (en) | 2010-07-13 | 2012-01-19 | Ultragenyx Pharmaceutical Inc. | Method and formulations for treating sialic acid deficiencies |
| US9241896B2 (en) * | 2008-12-19 | 2016-01-26 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| UA110325C2 (en) | 2009-07-03 | 2015-12-25 | Australian Biomedical Company Pty Ltd | Medicinal carbohydrates for treating respiratory conditions |
| CA2849114C (en) | 2011-10-24 | 2020-12-15 | Ultragenyx Pharmaceutical Inc. | Sialic acid analogs |
| CN113101294A (zh) | 2013-03-15 | 2021-07-13 | 杭州惠瑞生物医药有限公司 | 感染相关疾病或病症的生物治疗产品 |
| CN105101971A (zh) | 2013-03-15 | 2015-11-25 | 王慧茹 | 用于传染性或炎症性疾病或病症的组合物和产品 |
| SG11201700697YA (en) | 2014-07-30 | 2017-02-27 | Kyowa Hakko Bio Co Ltd | Crystal of alkali metal n-acetylneuraminate anhydrate, and process for producing same |
| ES2777838T3 (es) * | 2015-01-28 | 2020-08-06 | Kyowa Hakko Bio Co Ltd | Cristal de anhidrato de N-acetilneuraminato de amonio y procedimiento para producir el mismo |
| WO2017048817A1 (en) | 2015-09-14 | 2017-03-23 | Ultragenyx Pharmaceutical Inc. | Crystal forms of sialic acid or salt or solvate thereof |
| CN109771316B (zh) * | 2018-12-29 | 2022-02-25 | 中国科学院合肥物质科学研究院 | 一种提高n-乙酰神经氨酸水溶液稳定性的方法及其应用 |
| CN110606864B (zh) * | 2019-10-08 | 2023-10-10 | 中国科学院合肥物质科学研究院 | 一种n-乙酰神经氨酸钙盐晶体及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199116B (it) * | 1984-07-03 | 1988-12-30 | Fidia Farmaceutici | Derivati di gangliosidi |
| IT1177863B (it) * | 1984-07-03 | 1987-08-26 | Fidia Farmaceutici | Una miscela gangliosidica come agente terapeutico capare di eliminare il dolore nele neuropatie periferiche |
| IT1182209B (it) * | 1985-02-18 | 1987-09-30 | Fidia Farmaceutici | Uso terapeutico del monosialoganglioside gm1 e dei suoi derivati in gravi patologie di infarti cerebrali |
-
1984
- 1984-09-11 JP JP59189950A patent/JPS6168418A/ja active Granted
-
1985
- 1985-09-06 US US06/773,036 patent/US4698332A/en not_active Expired - Fee Related
- 1985-09-10 AU AU47199/85A patent/AU582584B2/en not_active Ceased
- 1985-09-10 DE DE91100080T patent/DE3587587T2/de not_active Expired - Fee Related
- 1985-09-10 AT AT85111414T patent/ATE111738T1/de not_active IP Right Cessation
- 1985-09-10 HU HU883140A patent/HU198733B/hu unknown
- 1985-09-10 AT AT91100080T patent/ATE94396T1/de not_active IP Right Cessation
- 1985-09-10 DE DE3587928T patent/DE3587928T2/de not_active Expired - Fee Related
- 1985-09-10 CA CA000490308A patent/CA1246452A/en not_active Expired
- 1985-09-10 EP EP91100080A patent/EP0429430B1/en not_active Expired - Lifetime
- 1985-09-10 ES ES546840A patent/ES8606323A1/es not_active Expired
- 1985-09-10 FI FI853456A patent/FI83963C/fi not_active IP Right Cessation
- 1985-09-10 KR KR1019850006606A patent/KR880001234B1/ko not_active Expired
- 1985-09-10 ZA ZA856905A patent/ZA856905B/xx unknown
- 1985-09-10 EP EP85111414A patent/EP0177783B1/en not_active Expired - Lifetime
- 1985-09-10 HU HU853417A patent/HU197515B/hu not_active IP Right Cessation
- 1985-09-11 DK DK413785A patent/DK165046C/da not_active IP Right Cessation
- 1985-11-15 CN CN85108388A patent/CN85108388B/zh not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4719985A (en) | 1986-03-20 |
| CN85108388A (zh) | 1987-06-03 |
| CN85108388B (zh) | 1988-08-24 |
| KR860002525A (ko) | 1986-04-26 |
| US4698332A (en) | 1987-10-06 |
| DK165046C (da) | 1993-02-22 |
| EP0177783A2 (en) | 1986-04-16 |
| JPS6168418A (ja) | 1986-04-08 |
| FI853456L (fi) | 1986-03-12 |
| EP0429430A2 (en) | 1991-05-29 |
| EP0429430B1 (en) | 1993-09-15 |
| ES546840A0 (es) | 1986-04-16 |
| JPS6328411B2 (OSRAM) | 1988-06-08 |
| HU197515B (en) | 1989-04-28 |
| HUT40804A (en) | 1987-02-27 |
| FI83963C (fi) | 1991-09-25 |
| EP0177783B1 (en) | 1994-09-21 |
| FI83963B (fi) | 1991-06-14 |
| ES8606323A1 (es) | 1986-04-16 |
| CA1246452A (en) | 1988-12-13 |
| DK165046B (da) | 1992-10-05 |
| FI853456A0 (fi) | 1985-09-10 |
| ATE94396T1 (de) | 1993-10-15 |
| DE3587928T2 (de) | 1995-01-26 |
| AU582584B2 (en) | 1989-04-06 |
| ATE111738T1 (de) | 1994-10-15 |
| DK413785A (da) | 1986-03-12 |
| EP0177783A3 (en) | 1989-02-22 |
| DE3587587D1 (de) | 1993-10-21 |
| EP0429430A3 (en) | 1991-10-23 |
| ZA856905B (en) | 1986-06-25 |
| DE3587587T2 (de) | 1994-03-31 |
| DE3587928D1 (de) | 1994-10-27 |
| KR880001234B1 (ko) | 1988-07-12 |
| DK413785D0 (da) | 1985-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |