DE2117902C3 - Salze des Arabogalactansulfats mit stickstoffhaltigen heterocyclischen Basen, Verfahren zur Herstellung dieser Salze und diese enthaltende Arzneimittel - Google Patents
Salze des Arabogalactansulfats mit stickstoffhaltigen heterocyclischen Basen, Verfahren zur Herstellung dieser Salze und diese enthaltende ArzneimittelInfo
- Publication number
- DE2117902C3 DE2117902C3 DE2117902A DE2117902A DE2117902C3 DE 2117902 C3 DE2117902 C3 DE 2117902C3 DE 2117902 A DE2117902 A DE 2117902A DE 2117902 A DE2117902 A DE 2117902A DE 2117902 C3 DE2117902 C3 DE 2117902C3
- Authority
- DE
- Germany
- Prior art keywords
- salts
- arabogalactan
- sulfate
- nitrogen
- water
- 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
- 150000003839 salts Chemical class 0.000 title claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 14
- 239000003814 drug Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 9
- 229920001282 polysaccharide Polymers 0.000 claims description 8
- 239000005017 polysaccharide Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 claims description 5
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004098 Tetracycline Substances 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 229960001789 papaverine Drugs 0.000 claims description 3
- 229960003910 promethazine Drugs 0.000 claims description 3
- 229960002180 tetracycline Drugs 0.000 claims description 3
- 229930101283 tetracycline Natural products 0.000 claims description 3
- 235000019364 tetracycline Nutrition 0.000 claims description 3
- 150000003522 tetracyclines Chemical class 0.000 claims description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 claims description 2
- 239000002585 base Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- -1 alkaline earth metal salt Chemical class 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical class CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229960003276 erythromycin Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 3
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000021513 Cinchona Nutrition 0.000 description 2
- 241000157855 Cinchona Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOTMYNBWXDUBNX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolin-2-ium;chloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 UOTMYNBWXDUBNX-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229930013397 isoquinoline alkaloid Natural products 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 229960003207 papaverine hydrochloride Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002808 pholcodine Drugs 0.000 description 1
- GPFAJKDEDBRFOS-FKQDBXSBSA-N pholcodine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCCN1CCOCC1 GPFAJKDEDBRFOS-FKQDBXSBSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229960002244 promethazine hydrochloride Drugs 0.000 description 1
- XXPDBLUZJRXNNZ-UHFFFAOYSA-N promethazine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 XXPDBLUZJRXNNZ-UHFFFAOYSA-N 0.000 description 1
- 229930002341 quinoline alkaloid Natural products 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1838770 | 1970-04-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2117902A1 DE2117902A1 (de) | 1971-11-04 |
| DE2117902B2 DE2117902B2 (de) | 1975-01-23 |
| DE2117902C3 true DE2117902C3 (de) | 1975-09-04 |
Family
ID=10111587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2117902A Expired DE2117902C3 (de) | 1970-04-17 | 1971-04-13 | Salze des Arabogalactansulfats mit stickstoffhaltigen heterocyclischen Basen, Verfahren zur Herstellung dieser Salze und diese enthaltende Arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE764677A (enExample) |
| CA (1) | CA946378A (enExample) |
| CH (1) | CH516937A (enExample) |
| DE (1) | DE2117902C3 (enExample) |
| ES (1) | ES389832A1 (enExample) |
| GB (1) | GB1302118A (enExample) |
| NL (1) | NL7105144A (enExample) |
| ZA (1) | ZA712440B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3334595A1 (de) * | 1983-09-24 | 1985-04-18 | B. Braun Melsungen Ag, 3508 Melsungen | Wirkstoffdepot |
| JP4873513B2 (ja) * | 1998-04-27 | 2012-02-08 | ロンザ，インコーポレイティド | アラビノガラクタンの誘導体類及びそれらを含む組成物 |
-
1970
- 1970-04-17 GB GB1838770A patent/GB1302118A/en not_active Expired
-
1971
- 1971-03-23 BE BE764677A patent/BE764677A/xx unknown
- 1971-04-02 ES ES389832A patent/ES389832A1/es not_active Expired
- 1971-04-13 DE DE2117902A patent/DE2117902C3/de not_active Expired
- 1971-04-14 CA CA110,356*7A patent/CA946378A/en not_active Expired
- 1971-04-16 CH CH568071A patent/CH516937A/fr not_active IP Right Cessation
- 1971-04-16 ZA ZA712440A patent/ZA712440B/xx unknown
- 1971-04-16 NL NL7105144A patent/NL7105144A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2117902B2 (de) | 1975-01-23 |
| NL7105144A (enExample) | 1971-10-19 |
| GB1302118A (enExample) | 1973-01-04 |
| BE764677A (fr) | 1971-08-16 |
| CA946378A (en) | 1974-04-30 |
| CH516937A (fr) | 1971-12-31 |
| ZA712440B (en) | 1972-01-26 |
| DE2117902A1 (de) | 1971-11-04 |
| ES389832A1 (es) | 1973-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |