EP0000190A1 - Solutions with a local anesthetic effect. - Google Patents
Solutions with a local anesthetic effect. Download PDFInfo
- Publication number
- EP0000190A1 EP0000190A1 EP78100230A EP78100230A EP0000190A1 EP 0000190 A1 EP0000190 A1 EP 0000190A1 EP 78100230 A EP78100230 A EP 78100230A EP 78100230 A EP78100230 A EP 78100230A EP 0000190 A1 EP0000190 A1 EP 0000190A1
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- EP
- European Patent Office
- Prior art keywords
- amino
- dibromo
- trans
- hydroxycyclohexyl
- solutions
- 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.)
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Classifications
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- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Definitions
- solutions which, if appropriate, in combination with a fluorescent dye such as fluorescein 2-amino-3,5-dibromo-N- (trans-4-hydroxy-cyclohexyl) benzylamine or its physiologically tolerable acid addition salts with inorganic and organic acids, have an excellent short-term local anesthetic effect, as required for short-term eye examinations or in the case of short-term diagnostic or minor therapeutic manipulations on mucous membranes.
- the duration of action is at most 20 - 25 minutes.
- solutions according to the invention are obtained by dissolving 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine or its; physiologically compatible acid addition salts with inorganic and organic acids in a suitable aqueous carrier in a concentration of 0.5-4%, but preferably 1.0-2.5%, optionally with the addition of a fluorescent dye such as fluorescein.
- the locally anesthetically effective solutions according to the invention have, for example as eye drops, a local anesthetic effect, as is particularly the case for short-term eye examinations, e.g. when tonometry is desired. Tonometry, especially applanation tonometry, is used to measure intraocular pressure, especially when glaucoma patients are being checked.
- the commercially available local anesthetics for short-term eye examinations have a duration of action that is too long, which means that the effect has not yet subsided when the patient comes back on the street and thus the possibility of undetected penetration of dust and other foreign bodies between the eyelids and The cornea is exposed, which causes injuries to the corneal epithelium.
- allergic reactions must be expected (see therapy week 26, 8640-8643 (1976)).
- the locally anesthetically effective solutions according to the invention are suitable as short-term mucosal anesthetics, as are desired for the area of the mouth or throat.
- the annoyance of the patient associated with a longer-acting local anesthetic namely taste impairment, furry feeling or difficulty swallowing, is eliminated by switching off the swallowing reflex mechanism
- the table below contains the test results found:
- the new locally anesthetically effective solutions (NA 872) according to the invention thus have a shorter local anesthetic effect than the comparison solution, and also a lower side effect on the epithelium.
- the effect shown above could be confirmed using the Aesthe-siometer according to Cochet and Bonnet on the human eye with drip or, when used as a spray application, with the help of the pump-metering valve on the mouth or throat mucosa.
- the local anesthetic effect occurs within 30 to 60 seconds, the duration of action was 15 to 30 minutes, or with the application of a second % NA 872 solution by means of 3-8 strokes of the pump-metering valve on the oral or pharynx mucosa of humans, slight anesthesia could be demonstrated in 6 test subjects; the duration of action was 15 to 25 minutes.
- Citric acid, active substance, Na 2 HPO 4 x 2H 2 0 and sodium chloride (solution I) are dissolved in half the water with gentle heating and stirring.
- alkyl-benzyl-dimethylammonium chloride and methyl cellulose are dissolved with ice cooling and stirring and left to swell overnight (solution II).
- Solutions I and II are combined and filtered through a membrane filter.
- citric acid In half of the water, citric acid, active substance and Na 2 HPO 4 x 2H 2 0 are dissolved in succession with gentle heating and stirring (solution I).
- Sorbitol, polyvinyl alcohol and alkylbenzyldimethylammonium chloride are dissolved in the other half of the water at 90 ° C. with stirring, then the mixture is cooled to room temperature and left to swell overnight (solution II).
- Solutions I and II are combined and filtered through a membrane filter.
- Boric acid is dissolved in water at 60 ° C. After cooling to room temperature, borax, active substance and alkylbenzyldimethylammonium chloride are added in succession. After swelling over night is filtered through a membrane filter.
- Solution I is prepared analogously to Example 1.
- Sorbitol, methyl cellulose and phenyl Hg borate are dissolved in the other half of the water with ice cooling and stirring and left to swell overnight (solution II). Solutions I and II are combined and filtered through a membrane filter.
- the solution is carried out in the order of citric acid, active substance Na 2 HPO 4 , sodium chloride and alkyl-benzyl-dimethylammonium chloride in water. It is then filtered with a membrane filter.
- the substances are dissolved in the following order in the larger amount of water: active substance, citric acid, Na 2 HPO 4 , alkyl-benzyl-dimethylammonium chloride, sorbitol and glycerin. Then it is filtered.
- the solution is carried out in the following order in the main amount of water: citric acid, active substance, Na 2 HPO 4 , alkyl-benzyl-dimethylammonium chloride, sodium chloride and propylene glycol. Then it is filled with water and pressure filtered.
- Active substance, sorbitan trioleate, isopropyl myristate are ground together in a part of propellant gas 11 in a ball mill. This concentrate is transferred to a cold filling system, cooled to -40 ° C and filled with the rest of the propellant gas mixture and filled into suitable aerosol cans, immediately provided with a suitable metering valve and sealed.
Abstract
Description
Die Verbindung 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclohexyl- benzylamin (NA-872) und deren Säureadditionssalze werden crystals in der Belgischen Patentschrift 698 244 beschrieben, hierbei werden als pharmakologische Eigenschaften neben einer Beeinflussung der peripheren Atmungsfunktion insbesondere die antipyretische, hustenstillende und sekretölytische Wirkung genannt.The compound 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexylbenzylamine (NA-872) and its acid addition salts are described in crystals in Belgian patent specification 698 244, which are described as pharmacological properties in addition to influencing the peripheral Respiratory function in particular called the antipyretic, antitussive and secretory effects.
Ferner ist aus der Belgischen Patentschrift 827 466 die Antiulcus-Wirkung von 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclo- hexyl)-benzylamin und dessen Säureadditionssalzen bekannt.Furthermore, the antiulcus effect of 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine and its acid addition salts is known from Belgian patent 827 466.
überraschenderweise wurde nun gefunden, daß Lösungen, die gege- 'benenfalls in Kombination mit einem Fluoreszensfarbstoff wie Fluorescein 2-Amino-3,5-dibrom-N-(trans-4-hydroxy-cyclohexyl)-benzylamin oder dessen physiologisch verträgliche Säureadditionssalze mit anorganischen und organischen Säuren enthalten, eine vorzügliche kurzfristige lokalanästhetische Wirkung aufweisen, wie sie für kurzfristige Augenuntersuchungen oder bei kurz andauernden diagnostischen oder kleineren therapeutischen Manipulationen an Schleimhäuten erforderlich ist. Die Wirkungsdauer beträgt hierbei längstens 20 - 25 Minuten.Surprisingly, it has now been found that solutions which, if appropriate, in combination with a fluorescent dye such as fluorescein 2-amino-3,5-dibromo-N- (trans-4-hydroxy-cyclohexyl) benzylamine or its physiologically tolerable acid addition salts with inorganic and organic acids, have an excellent short-term local anesthetic effect, as required for short-term eye examinations or in the case of short-term diagnostic or minor therapeutic manipulations on mucous membranes. The duration of action is at most 20 - 25 minutes.
Die erfindungsgemäßen Lösungen erhält man durch Lösen von 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclohexyl)-benzylamin oder dessen ; physiologisch verträglichen Säureadditionssalzen mit anorganischen und organischen Säuren in einem geeigneten wässrigen Träger in einer Konzentration von 0,5 - 4 %, vorzugsweise jedoch 1,0 - 2,5 %gegebenenfalls unter Hinzufügung eines Fluoreszensfarbstoffes wie Fluorescein.The solutions according to the invention are obtained by dissolving 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine or its; physiologically compatible acid addition salts with inorganic and organic acids in a suitable aqueous carrier in a concentration of 0.5-4%, but preferably 1.0-2.5%, optionally with the addition of a fluorescent dye such as fluorescein.
Die erfindungsgemäßen lokalanästhetisch wirksamen Lösungen weisen beispielsweise als Augentropfen eine lokalanästhetische Wirkung auf, wie sie insbesondere für kurzfristige Augenuntersuchungen, z.B. bei der Tonometrie erwünscht ist. Die Tonometrie, besonders die Applanationstonometrie, dient der Messung des intraokularen Druckes, insbesondere bei der laufenden Kontrolle von Glaukom-Patienten. Die im Handel befindlichen Lokalanästhetika für kurzfristige Augenuntersuchungen weisen eine zu lange Wirkungsdauer auf, was dazu führt, daß die Wirkung noch nicht abgeklungen ist, wenn der Patient wieder auf die Straße kommt und damit der Möglichkeit eines unbemerkten Eindringens von Staub und anderen Fremdkörpern zwischen Lidern und Hornhaut ausgesetzt ist, wodurch Verletzungen des Hornhaut-Fpithels hervorgerufen werden, außerdem muß wegen der beim Glaukom-Patienten häufigen Anwendung beim Einsatz der bisher gebräuchlichen Lokalanästhetika mit allergischen Reaktionen gerechnet werden (siehe Therapiewoche 26, 8640 - 8643 (1976)).The locally anesthetically effective solutions according to the invention have, for example as eye drops, a local anesthetic effect, as is particularly the case for short-term eye examinations, e.g. when tonometry is desired. Tonometry, especially applanation tonometry, is used to measure intraocular pressure, especially when glaucoma patients are being checked. The commercially available local anesthetics for short-term eye examinations have a duration of action that is too long, which means that the effect has not yet subsided when the patient comes back on the street and thus the possibility of undetected penetration of dust and other foreign bodies between the eyelids and The cornea is exposed, which causes injuries to the corneal epithelium. In addition, due to the frequent use in glaucoma patients with the use of the local anesthetics that were previously used, allergic reactions must be expected (see therapy week 26, 8640-8643 (1976)).
Ferner sind die erfindungsgemäßen lokalanästhetisch wirksamen Lösungen als kurzfristig wirkende Schleimhaut-Anästhetika, wie sie für den Bereich des Mundes oder des Rachens erwünscht sind, geeignet. Bei ihrer Anwendung entfällt die mit einem länger wirkende Lokalanästhetikum einhergehende Belästigung des Patienten, nämlich die Geschmacksbeeinträchtigung, das pelzige Gefühl oder die Schluckbeschwerden durch Ausschalten des Schluckreflex-MechanismusFurthermore, the locally anesthetically effective solutions according to the invention are suitable as short-term mucosal anesthetics, as are desired for the area of the mouth or throat. When used, the annoyance of the patient associated with a longer-acting local anesthetic, namely taste impairment, furry feeling or difficulty swallowing, is eliminated by switching off the swallowing reflex mechanism
Die überlegene kurzfristige lokalanästhetische Wirkung der neuen Lösungen wurde im Vergleich zu Proxymetacain (0,5%ige 2-Diäthyl- aminoäthyl-3-amino-4-propoxybenzoesäure-hydrochlorid-Lösung = Chibro® -Kerakain) am Kaninchen wie folgt geprüft:
- Den Versuchstieren, die nach Spaltlampen-Untersuchung keine Schädigung des Cornea-Epithels zeigten und klinisch keine konjunktivale Entzündung aufwiesen, wurden jeweils 2 Tropfen der entsprechenden Augentropfen appliziert. Die Sensibilität der zentralen Cornea ist eine Minute nach Applikation durch Berührungsreiz, das gesamte Hornhautepithel und die Sensibilität 5, 10, 15 und 30 Minuten nach Applikation beurteilt worden. Der Untersuchen. der die Sensibilität und den Hornhaut-Epithel-Status beurteilte, war hierbei nicht darüber informiert, welches Auge jeden Tieres mit Chibro® -Kerakain behandelt war.
- The test animals, which showed no damage to the corneal epithelium after slit lamp examination and showed no clinical conjunctivitis, were each given 2 drops of the corresponding eye drops. The sensitivity of the central cornea is one minute after application by touch stimulus, the entire corneal epithelium and sensitivity were assessed 5, 10, 15 and 30 minutes after application. The Examine. who assessed sensitivity and corneal epithelium status was not informed which eye of each animal was treated with Chibro® kerakain.
Die nachfolgende Tabelle enthält die aufgefundenen Versuchsergebnisse:
Die oben aufgezeigte Wirkung konnte unter Heranziehung des Aesthe-siometers nach Cochet und Bonnet am menschlichen Auge mit Tropf- bzw. bei der Anwendung als Spray-Applikation mit Hilfe des Pump-Dosier-Ventils an der Mund- bzw. Rachenschleimhaut bestätigt werden. Bei einer Konzentration von 0,5 bis 1 % NA 872 und der Appli kation von 1 bis 2 Tropfen pro Auge tritt die lokalanästhetische Wirkung innerhalb von 30 bis 60 Sekunden ein, die Wirkungsdauer betrug 15 bis 30 Minuten, bzw. bei der Applikation einer 2%igen NA 872-Lösung mittels 3-8 Hüben des Pump-Dosier-Ventils an der Mund- bzw. Rachenschleimhaut des Menschens konnte an 6 Probanden eine leichte Anästhesie nachgewiesen werden, die Wirkungsdauer betrug 15 bis 25 Minuten.The effect shown above could be confirmed using the Aesthe-siometer according to Cochet and Bonnet on the human eye with drip or, when used as a spray application, with the help of the pump-metering valve on the mouth or throat mucosa. With a concentration of 0.5 to 1% NA 872 and the application of 1 to 2 drops per eye, the local anesthetic effect occurs within 30 to 60 seconds, the duration of action was 15 to 30 minutes, or with the application of a second % NA 872 solution by means of 3-8 strokes of the pump-metering valve on the oral or pharynx mucosa of humans, slight anesthesia could be demonstrated in 6 test subjects; the duration of action was 15 to 25 minutes.
Ergänzend sei hier erwähnt, daß die Substanz 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclohexyl)-benzylamin und dessen physiologisch verträgliche Säureadditionssalze mit anorganischen und organischen Säuren eine geringe akute Toxizität aufweist, beispielsweise als Hydrochlorid eine LD50 von 2 720 mg/kg p.o. an der Maus.In addition, it should be mentioned here that the substance 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine and its physiologically compatible acid addition salts with inorganic and organic acids have a low acute toxicity, for example as an LD hydrochloride 50 of 2,720 mg / kg po on the mouse.
Die nachfolgenden Beispiele sollen die Erfindung näher erläutern:The following examples are intended to explain the invention in more detail:
Zusammensetzung:
In der Hälfte des Wassers werden unter schwachem Erwärmen und Rühren Citronensäure, Wirksubstanz, Na2HPO4 x 2H20 und Natriumchlorid gelöst (Lösung I).Citric acid, active substance, Na 2 HPO 4 x 2H 2 0 and sodium chloride (solution I) are dissolved in half the water with gentle heating and stirring.
In der anderen Hälfte des Wassers werden unter Eiskühlung und Rühren Alkyl-benzyl-dimethylammoniumchlorid und Methylcellulose gelöst und über Nacht quellen gelassen (Lösung II).In the other half of the water, alkyl-benzyl-dimethylammonium chloride and methyl cellulose are dissolved with ice cooling and stirring and left to swell overnight (solution II).
Lösung I und II werden vereinigt und durch ein Membranfilter fil- triert.Solutions I and II are combined and filtered through a membrane filter.
Augentropfen mit 2 % 2-Amino- 3,5-dibrom-N-(trans-4-hydroxycyclo- hexyl)-benzylamin-hydrochloridEye drops with 2% 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine hydrochloride
Zusammensetzung:
In der Hälfte des Wassers werden unter schwachem Erwärmen und Rühren Citronensäure, Wirksubstanz und Na2HPO4 x 2H20 nacheinande gelöst (Lösung I).In half of the water, citric acid, active substance and Na 2 HPO 4 x 2H 2 0 are dissolved in succession with gentle heating and stirring (solution I).
In der anderen Hälfte des Wassers werden bei 90°C und unter Rühr Sorbit, Polyvinylalkohol und Alkyl-benzyl-dimethylammoniumchlorid gelöst, anschließend wird auf Raumtemperatur abgekühlt und über Nacht quellen gelassen (Lösung II).Sorbitol, polyvinyl alcohol and alkylbenzyldimethylammonium chloride are dissolved in the other half of the water at 90 ° C. with stirring, then the mixture is cooled to room temperature and left to swell overnight (solution II).
Lösung I und II werden vereinigt und durch ein Membranfilter filtriert.Solutions I and II are combined and filtered through a membrane filter.
Augentropfen mit 0,5 % 2-Amino-3,5-dibrom-N-(trans-4-hydroxy- cyclohexyl)-benzylamin-hydrochloridEye drops with 0.5% 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine hydrochloride
Zusammensetzung:
Borsäure wird in Wasser bei 60°C gelöst. Nach dem Abkühlen auf Raumtemperatur gibt man hierzu nacheinander Borax, Wirksubstanz und Alkyl-benzyl-dimethylammoniumchlorid. Nach Quellen über Nach wird über ein Membranfilter filtriert.Boric acid is dissolved in water at 60 ° C. After cooling to room temperature, borax, active substance and alkylbenzyldimethylammonium chloride are added in succession. After swelling over night is filtered through a membrane filter.
Augentropfen mit 1,0 % 2-Amino-3,5-dibrom-N-(trans-4-hydroxy- cyclohexyl-benzylamin-hydrochloridEye drops with 1.0% 2-amino-3,5-dibromo-N- (trans-4-hydroxy-cyclohexyl-benzylamine hydrochloride
Zusammensetzung:
analog Beispiel 1.analogous to example 1.
Zusammensetzung:
Lösung I wird analog Beispiel 1 hergestellt.Solution I is prepared analogously to Example 1.
In der anderen Hälfte des Wassers werden unter Eiskühlung und Rühren Sorbit, Methylcellulose und Phenyl-Hg-borat gelöst und über Nacht quellen gelassen (Lösung II). Lösung I und II werden vereinigt und durch ein Membranfilter filtriert.Sorbitol, methyl cellulose and phenyl Hg borate are dissolved in the other half of the water with ice cooling and stirring and left to swell overnight (solution II). Solutions I and II are combined and filtered through a membrane filter.
Zusammensetzung:
Die Lösung erfolgt in der Reihenfolge Zitronensäure, Wirksubstanz Na2HPO4, Natriumchlorid und Alkyl-benzyl-dimethylammoniumchlorid in Wasser. Anschließend wird mit einem Membranfilter filtriert.The solution is carried out in the order of citric acid, active substance Na 2 HPO 4 , sodium chloride and alkyl-benzyl-dimethylammonium chloride in water. It is then filtered with a membrane filter.
Zusammensetzung:
Die Substanzen werden in folgender Reihenfolge in der größeren Menge Wasser gelöst: Wirksubstanz, Zitronensäure, Na2HPO4, Alkyl-benzyl-dimethylammoniumchlorid, Sorbit und Glycerin. Anschließend wird filtriert.The substances are dissolved in the following order in the larger amount of water: active substance, citric acid, Na 2 HPO 4 , alkyl-benzyl-dimethylammonium chloride, sorbitol and glycerin. Then it is filtered.
Lösung für Pumpdosierventilspray mit 0,5 - 2,0 % 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclohexyl)-benzylaminSolution for pump metering valve spray with 0.5 - 2.0% 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine
Zus ammensetzung:
Die Lösung wird in folgender Reihenfolge in der Hauptmenge Wasser durchgeführt: Zitronensäure, Wirksubstanz, Na2HPO4, Alkyl-benzyl-dimethylammoniumchlorid, Natriumchlorid und Propylenglykol. Danach wird mit Wasser aufgefüllt und druckfiltriert.The solution is carried out in the following order in the main amount of water: citric acid, active substance, Na 2 HPO 4 , alkyl-benzyl-dimethylammonium chloride, sodium chloride and propylene glycol. Then it is filled with water and pressure filtered.
Dosier-Aerosol auf Treibgasbasis mit 0,5 - 2,0 % 2-Amino-3,5-dibrom-N-(trans-4-hydroxycyclohexyl)-benzylaminDosing aerosol based on propellant gas with 0.5 - 2.0% 2-amino-3,5-dibromo-N- (trans-4-hydroxycyclohexyl) benzylamine
Zusammensetzung:
Wirksubstanz, Sorbitantrioleat, Isopropylmyristat werden zusammen in einem Teil Treibgas 11 in der Kugelmühle gemahlen. Dieses Konzentrat wird in eine Kaltfüllanlage überführt, auf -40°C abgekühlt und mit dem Rest Treibgasgemisch aufgefüllt und in geeignete Aerosoldosen abgefüllt, sofort mit einem geeigneten Dosierventil versehen und verschlossen.Active substance, sorbitan trioleate, isopropyl myristate are ground together in a part of propellant gas 11 in a ball mill. This concentrate is transferred to a cold filling system, cooled to -40 ° C and filled with the rest of the propellant gas mixture and filled into suitable aerosol cans, immediately provided with a suitable metering valve and sealed.
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2729786 | 1977-07-01 | ||
| DE19772729786 DE2729786A1 (en) | 1977-07-01 | 1977-07-01 | LOCAL ANESTHETICALLY EFFECTIVE SOLUTIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0000190A1 true EP0000190A1 (en) | 1979-01-10 |
Family
ID=6012934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100230A Withdrawn EP0000190A1 (en) | 1977-07-01 | 1978-06-23 | Solutions with a local anesthetic effect. |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0000190A1 (en) |
| DE (1) | DE2729786A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101240119B (en) * | 1994-12-15 | 2011-05-11 | 卡伯特公司 | Carbon black reacted with diazonium salts and products |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3485756D1 (en) * | 1983-09-17 | 1992-07-09 | Thomae Gmbh Dr K | ANTIADHAESIVE PROPHYLACTICA AND MEDICINAL PRODUCTS CONTAINING A SECRETOLYTICALLY EFFECTIVE BENZYLAMINE DERIVATIVE. |
| DE3731528A1 (en) * | 1987-09-18 | 1989-04-13 | Krewel Werke Gmbh | Use of trans-4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol for the local treatment of disorders of the eye |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1113760A (en) * | 1966-12-16 | 1968-05-15 | Barnes Hind Lab Inc | Ophthalmic composition |
-
1977
- 1977-07-01 DE DE19772729786 patent/DE2729786A1/en not_active Withdrawn
-
1978
- 1978-06-23 EP EP78100230A patent/EP0000190A1/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1113760A (en) * | 1966-12-16 | 1968-05-15 | Barnes Hind Lab Inc | Ophthalmic composition |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, 54, 9106 bcd (1960) zitiert "Farmaco" (Pavia) Ed. sci. 14, 440-64 (1959) * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101240119B (en) * | 1994-12-15 | 2011-05-11 | 卡伯特公司 | Carbon black reacted with diazonium salts and products |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2729786A1 (en) | 1979-01-18 |
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| 18W | Application withdrawn |
Withdrawal date: 19850320 |
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| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: RENOVANZ, HANS-DIETRICH, DR. Inventor name: PAPENDICK, UWE, DR. Inventor name: VON SEEFELD, HEIDE ANGELA, DR. Inventor name: PUESCHMANN, SIGFRID, DR. Inventor name: KECK, JOHANNES, DIPL.-CHEM., DR. |