DE2117902B2 - Salts of arabogalactan sulfate with nitrogen-containing heterocyclic bases, processes for the preparation of these salts and medicaments containing them - Google Patents
Salts of arabogalactan sulfate with nitrogen-containing heterocyclic bases, processes for the preparation of these salts and medicaments containing themInfo
- Publication number
- DE2117902B2 DE2117902B2 DE2117902A DE2117902A DE2117902B2 DE 2117902 B2 DE2117902 B2 DE 2117902B2 DE 2117902 A DE2117902 A DE 2117902A DE 2117902 A DE2117902 A DE 2117902A DE 2117902 B2 DE2117902 B2 DE 2117902B2
- Authority
- DE
- Germany
- Prior art keywords
- salts
- sulfate
- arabogalactan
- water
- nitrogen
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000004098 Tetracycline Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 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 4
- 229960002180 tetracycline Drugs 0.000 claims description 4
- 229930101283 tetracycline Natural products 0.000 claims description 4
- 235000019364 tetracycline Nutrition 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000003522 tetracyclines Chemical class 0.000 claims description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001789 papaverine Drugs 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 241000218652 Larix Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- ZQVMTYNYYKCYRF-UHFFFAOYSA-N diazanium hydron trisulfate Chemical compound [H+].[H+].[H+].[H+].[NH4+].[NH4+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZQVMTYNYYKCYRF-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound 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 description 9
- 229920001282 polysaccharide Polymers 0.000 description 7
- 239000005017 polysaccharide Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- -1 polysaccharide sulfates Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
- 229960003276 erythromycin Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229930013930 alkaloid Natural products 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
- 150000004676 glycans Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229960003910 promethazine Drugs 0.000 description 2
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound 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 1
- 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
- 206010011224 Cough Diseases 0.000 description 1
- 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 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 241001233037 catfish Species 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
- 125000004122 cyclic group Chemical group 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
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960003207 papaverine hydrochloride Drugs 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
- 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 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)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
heterocyclischen Basen. Da die Salze in Wasser as praktisch unlöslich sind, wird bei oraler Verabreichung der aktive Wirkstoff in Form der Base imheterocyclic bases. Since the salts are practically insoluble in water, they are used orally the active ingredient in the form of the base im
Aus der französischen Patentschrift 2 013 170 sind Darm allmählich freigesetzt, was zu der verlängerten schwerlösliche Verbindungen von Chinarindenalka- Wirkungsdauer führt.From French patent specification 2 013 170 intestines are gradually released, resulting in the elongated sparingly soluble compounds of cinchona alkali duration of action leads.
leiden bekanntgeworden. Es handelt sich hierbei um Der Gehalt des in den erfindungsgemäßen Salzensuffering has become known. This is the content of the salts according to the invention
Salze bestimmter Chinarindenalkaloide mit bestimm- 30 enthaltenen Wirkstoffs richtet sich nach dem Gehalt
ten Polysaccharidsulfaten. Auf Grund dieser Erkennt- der — SO3H-Gruppen des Arabogalactansulfats.
nisse stellte sich die Aufgabe, schwerlösliche Ver- Die erfindungsgemäßen Salze wirken entsprechendSalts of certain cinchona bark alkaloids with certain active ingredients depends on the content of polysaccharide sulfates. On the basis of this knowledge - SO 3 H groups of the arabogalactan sulfate.
Nisse set the task of producing poorly soluble compounds. The salts according to the invention act accordingly
bindungen anderer, in der Therapie eingesetzter stick- der enthaltenen Base z. B. als Spasmolytika, Antistoffhaltiger
heterocyclischer Basen mit Polysaccharid- histiminica oder Antibiotika.
Sulfaten herzustellen. Die Übertragung der hei 35 Die Beispiele erläutern die Erfindung.
Chinolin-Alkaloiden gewonnenen Erkenntnisse ließbonds of other, in the therapy used stick- the base contained z. B. as spasmolytics, anti-substance-containing heterocyclic bases with polysaccharide histiminica or antibiotics.
Making sulfates. The transfer of the hot 35 The examples illustrate the invention.
Quinoline alkaloids
sich nun nicht ohne weiteres auf Isochinolin-Alkaloide Beispiel 1does not automatically refer to isoquinoline alkaloids Example 1
übertragen, denn die mit Polysaccharidsulfaten und „ . . . . . . . ., ,transferred because those with polysaccharide sulfates and “. . . . . . . .,,
z. B. Codein oder Pholcodin hergestellten Salze sind Papavennsalz des Arabogalactansulfatsz. Salts prepared for example codeine or pholcodine are papavenn's salt of arabogalactan sulfate
sehr leicht wasserlöslich. 40 Eine Lösung von 53 g des Calciumsalzes des Arabo-very easily soluble in water. 40 A solution of 53 g of the calcium salt of arabo
Andererseits war aus der britischen Patentschrift galactansulfats in 200 ml entsalztem Wasser wird
1183 403 bekannt, Polysaccharidsulfate, bei denen langsam unter kräftigem Rühren mit einer Lösung
iich der Polysaccharide vom Carageen ableitet, von 55 g Papaverin-hydrochlorid in 2500 ml entmit
Opiumalkaloiden umzusetzen, wobei man eine salztem Wasser versetzt. Der ausgefallene Niederharzartige
Masse erhält, die zerkleinert und gesiebt 45 schlag wird abzentrifugiert, mit Wasser gewaschen
wird. Das erhaltene Produkt, das nach der britischen und erneut zentrifugiert. Der gewaschene Nieder-Patentschrift
als Arzneimittel gegen Husten eingesetzt schlag wird bei 500C unter vermindertem Druck gewerden
kann, stellt nur ein Gemisch von unbestimmten trocknet. Die getrocknete Verbindung hat einen
Verbindungen dar, denn es ist nirgends in der Patenii- Papaveringeh^lt von 61 %.
schrift angegeben, daß man irgendeine bestimmte 50On the other hand, from the British patent specification galactan sulphate in 200 ml of deionized water is known 1183 403, polysaccharide sulphates, in which the polysaccharides from carageenan slowly derive from 55 g of papaverine hydrochloride in 2500 ml with vigorous stirring with a solution, whereby one added salted water. The precipitated low resin-like mass is obtained, which is crushed and sieved 45 blows, centrifuged off, washed with water. The product obtained after the British and centrifuged again. The washed down patent specification used as a medicament against cough blow is at 50 0 C under reduced pressure can be, only represents a mixture of indefinite dries. The dried compound has a compound, for it is nowhere in the patenii papave content of 61%.
Scripture stated that one should have any particular 50th
Verbindung aus diesem Gemisch isoliert hat. Beispiel 2Has isolated compound from this mixture. Example 2
Die vorliegender Erfindung zugrunde liegende Auf- .. . , . . . . „The structure on which the present invention is based. ,. . . . "
labe, schwerlösliche Sake anderer Alkaloide oder Narcotmsalz des ArabogalactansulfatsLabe, sparingly soluble sake of other alkaloids or narcotic salt of arabogalactan sulfate
Seterocyclischer Basen mit Polysaccharidsulfaten her- Eine Lösung von 50 g des Calciumsalzes des Arabo-Seterocyclic bases with polysaccharide sulfates - a solution of 50 g of the calcium salt of arabo
Zustellen, ließ sich in überraschender Weise dadurch 55 galactansulfats in 200 ml entsalztem Wasser wird lösen, daß man ein bestimmtes Polysaccharidsulfat mit unter Rühren mit einer Lösung von 70 g Narcotinbestimmten stickstoffhaltigen heterocyclischen Basen hydrochlorid in 1000 ml entsalztem Wasser versetzt. IW Der auägefäüefle Niederschlag wifd fiiit Wasser ge· It was surprisingly possible to dissolve 55 galactan sulfate in 200 ml of deionized water by adding a certain polysaccharide sulfate with nitrogen-containing heterocyclic base hydrochloride in 1000 ml of deionized water while stirring with a solution of 70 g of narcotine. IW The abundance of precipitation wifd fiiit water
h rifi d bi 5ÖeC ih rifi d bi 5Ö e C i
Gegenstand der Erfindung sind seait Salze de» waschen, zentrifugiert und bei 5ÖeC unter vermin' Afäbogalaetaasulfats mit den stickstoffhaltigen hetero- ίο dertem Druck getrocknet. Die getrocknete Verbin· cyclischen Basen Papaverin, Nareotin» Promethazin, dung hat einen Nareotingehalt von 65%. Tetracyclin und Erythromycin.The invention relates to salts wash seait de ", centrifuged and dried at 5 NC e C under vermin 'Afäbogalaetaasulfats with the nitrogen-containing hetero- ίο dertem pressure. The dried compound · cyclic bases papaverine, nareotine »promethazine, dung has a nareotine content of 65%. Tetracycline and erythromycin.
durch gekennzeichnet ist, daß »an in an sich be· ss Prometnaztosate des Arabogalactansulfats kannter Welse eine wfißrige Lösung eine» Alkali» Eine Lösung von 50 g des Calciuniiälzes des Arabo* öder firdat&alisalzes des Artbogalactansulfats mil! galatansulfats in 200 ml entsalztem Wasser wird lang* einer wäßrigen Lösung eiaes Salzes der stickstoff· sam unter starken Rühren mit einer Lösune ven A11 is characterized by that "in itself be · s s Prometnaztosate of Arabogalactansulfats known per catfish a solution wfißrige an" alkaline "A solution of 50 g of Calciuniiälzes of Arabo * barren firdat & alisalzes of Artbogalactansulfats mil! Galatan sulfate in 200 ml of demineralized water is mixed with an aqueous solution of a salt of nitrogen with vigorous stirring with a solution A11
FrQmethazH>nydrochiarid In 200 ml entsalztem Wasser versetzt. Der ausgefallene Niederschlag wird ab- »ntrifugiert, mit Wasser gewaschen und erneut zentrifugiert Per gewaschene Niederschlag wird bei SO0C unter verroindertem Druck getrocknet. Die getrocknete Verbindung bat einen Promethazingebalt von 58%.FrQmethazH> nydrochiarid Add 200 ml of deionized water. The deposited precipitate is filtered off, washed with water and centrifuged again. The washed precipitate is dried at SO 0 C under reduced pressure. The dried compound had a promethazine content of 58%.
Beispiel 4
Tetracyclinsalz des ArabogalactansulfatsExample 4
Tetracycline salt of arabogalactan sulfate
Eine Lösung von 60 g des Calciumsalzes dts Arabogalactansulfats in 200 ml Wasser wird unter Rühren mit einer Lösung von 75 g Tetracyclin-hydrochlorid in 1000 ml entsalztem Wasser versetzt. Der ausgefallene Niederschlag wird mit Wasser gewaschen, zentrifugiert und bei 50"C unter vermindertem Druck getrocknet. Die getrocknete Verbindung bat einen Tetracyclingebalt von 53%. A solution of 60 g of the calcium salt dts arabogalactan sulfate in 200 ml of water is mixed with a solution of 75 g of tetracycline hydrochloride in 1000 ml of deionized water while stirring. The deposited precipitate is washed with water, centrifuged and dried at 50 ° C. under reduced pressure. The dried compound had a tetracycline content of 53%.
22,5 g Erythromycin in 20 ml entsalztem Wasser werden mit soviel 1 η-Salzsäure versetzt, daß das22.5 g of erythromycin in 20 ml of deionized water are mixed with so much 1 η hydrochloric acid that the
ίο Erythromycin als Hydrochlorid in Lösung geht. Diese Lösung wird zu einer Lösung von 10 g des Calciumsalzes des Arabogalactansulfats in 20 ml Wasser gegeben. Der ausgefallene hellbraune Niederschlag ν ird abzentrifugiert und anschließend unter vermindertemίο Erythromycin goes into solution as the hydrochloride. These The solution is added to a solution of 10 g of the calcium salt of arabogalactan sulfate in 20 ml of water. The resulting light brown precipitate is centrifuged off and then under reduced pressure
is Druck bei 60° C getrocknet. Die Verbindung hat einen Erythromycingehalt von 74%,is print dried at 60 ° C. The connection has one Erythromycin content of 74%,
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1838770 | 1970-04-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2117902A1 DE2117902A1 (en) | 1971-11-04 |
| DE2117902B2 true DE2117902B2 (en) | 1975-01-23 |
| DE2117902C3 DE2117902C3 (en) | 1975-09-04 |
Family
ID=10111587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2117902A Expired DE2117902C3 (en) | 1970-04-17 | 1971-04-13 | Salts of arabogalactan sulfate with nitrogen-containing heterocyclic bases, processes for the preparation of these salts and medicaments containing them |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE764677A (en) |
| CA (1) | CA946378A (en) |
| CH (1) | CH516937A (en) |
| DE (1) | DE2117902C3 (en) |
| ES (1) | ES389832A1 (en) |
| GB (1) | GB1302118A (en) |
| NL (1) | NL7105144A (en) |
| ZA (1) | ZA712440B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3334595A1 (en) * | 1983-09-24 | 1985-04-18 | B. Braun Melsungen Ag, 3508 Melsungen | ACTIVE SUBSTANCE DEPOSIT |
| WO1999055736A2 (en) * | 1998-04-27 | 1999-11-04 | Larex, Inc. | Derivatives of arabinogalactan and compositions including the same |
-
1970
- 1970-04-17 GB GB1838770A patent/GB1302118A/en not_active Expired
-
1971
- 1971-03-23 BE BE764677A patent/BE764677A/en unknown
- 1971-04-02 ES ES389832A patent/ES389832A1/en not_active Expired
- 1971-04-13 DE DE2117902A patent/DE2117902C3/en not_active Expired
- 1971-04-14 CA CA110,356*7A patent/CA946378A/en not_active Expired
- 1971-04-16 NL NL7105144A patent/NL7105144A/xx unknown
- 1971-04-16 CH CH568071A patent/CH516937A/en not_active IP Right Cessation
- 1971-04-16 ZA ZA712440A patent/ZA712440B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7105144A (en) | 1971-10-19 |
| CA946378A (en) | 1974-04-30 |
| DE2117902C3 (en) | 1975-09-04 |
| BE764677A (en) | 1971-08-16 |
| GB1302118A (en) | 1973-01-04 |
| ES389832A1 (en) | 1973-06-01 |
| ZA712440B (en) | 1972-01-26 |
| DE2117902A1 (en) | 1971-11-04 |
| CH516937A (en) | 1971-12-31 |
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