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Diese Erfindung betrifft bestimmte substituierte 2-Imidazolinamino indol-Verbindungen. This invention relates to certain substituted 2-Imidazolinamino indole compounds.

Of the compounds was found that they represent alpha-2 agonists Adrenoakzeptor and that they are useful in the treatment of modulated by alpha-2 adrenoceptors disorders. Therapeutische Indikationen von alphaAdrenorezeptor-Agonisten sind please click for source der Literatur diskutiert worden: Therapeutic indications of alpha-2 adrenoceptor agonists have been discussed in the literature: Juni ; US Patent No.

Here compounds that are related to those of the present invention in terms of structure, however, do not provide the activity and specificity, which is desirable when treated by alpha-2 adrenoceptors modulated interference be. The compounds are represented as myotonolytisch and anti-hypertensive agents useful.

Thus, for example, many compounds was observed by those that they are effective nasal decongestant, found that they often have in systemically active doses undesirable side effects such as causing hypertension and Hyposomnie. There is a need for new drugs that provide remedy for nasal congestion without causing these undesirable side effects. It is an object of the invention to provide compounds and compositions which are Dropper für Krampfadern in the treatment of modulated by alpha-2 adrenoceptors disorders.

It is Dropper für Krampfadern object of this invention to provide new compounds which provide a substantial activity in Dropper für Krampfadern or treating nasal congestion, otitis media, and sinusitis, without undesired side effects.

It is also an object of this invention to provide novel compounds for the treatment of eye diseases, such as eye-hypertension, glaucoma, hyperemia, kann werden, verwendet während Schwangerschaft das auf Krampfadern der and uveitis to provide.

It is also an object of this invention to provide novel compounds for the treatment of gastrointestinal disorders to provide such as diarrhea, irritable bowel syndrome, hyperchlorhydria hyperacidity and peptic ulcer ulcer is available. It is also an object of this invention to provide novel compounds for the treatment Dropper für Krampfadern migraine available. This invention relates to compounds of claim 1.

Dropper für Krampfadern described herein means "alkanyl" means a saturated hydrocarbon with a straight or branched chain, unsubstituted or substituted. As described herein, means "alkenyl" means a hydrocarbon substituent with one double bond, straight or branched chain, unsubstituted or substituted. As described herein means "alkylthio" means a substituent having the structure QA, wherein Q is alkanyl Dropper für Krampfadern alkenyl.

As described herein means "alkoxy" means a substituent having the structure QO- where Q is alkanyl or alkenyl. As described herein means "alkylamino" means a substituent having the structure Q-NH- where Q is alkanyl or alkenyl. Septemberdie hierin durch Bezugnahme aufgenommen ist. Bevorzugte anionische Salze beinhalten Halogenide, Sulfonate, Carboxylate, Phosphate und dergleichen.

A "pharmaceutically acceptable salt" is an at any acidic. Eg, carboxyl group Dropper für Krampfadern cationic salt, or at any basic. Eg, amino group anionic salt formed. Preferred cationic salts include the alkali metal salts such as sodium and potassiumalkaline earth metal such as magnesium and calcium and organic salts. Preferred anionic salts include halides, sulfonates, carboxylates, phosphates, and the like. For example, can a chiral tartaric acid salt prepared from the compounds Dropper für Krampfadern the invention, this definition includes such chiral salts.

The compounds of the invention are sufficiently basic to form acid-addition salts. The compounds are useful both in the free base form and the form of acid-addition salts, and Dropper für Krampfadern forms are within the scope of the invention. The acid-addition salts Dropper für Krampfadern in some cases the more convenient form for use.

In practice, the use of the salt form already comes right to the use of the base form of the drug. Acids used to prepare Dropper für Krampfadern salts preferably include those which produce, when combined with the free Dropper für Krampfadern form, medically acceptable salts. These salts have anions that relatively safe with respect to in medicinal doses of the salts of Dropper für Krampfadern animal organism, such as, for example a mammal, such that the free base inherent advantageous properties not be made by any of the anions of the acid attributable to side effects to naught.

Include examples of suitable acid addition salts include, Dropper für Krampfadern are not Dropper für Krampfadern to, hydrochloride, hydrobromide, hydroiodide, sulfate, bisulfate, acetate, trifluoroacetate, nitrate, maleate, citrate, fumarate, format, stearate, succinate, Mallat, malonate, adipate, glutarate, lactatepropionate, Butrat, tartrate, methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate, dodecyl sulfate, cyclohexanesulfamate, and the like.

However, other suitable, medically acceptable salts within the scope of the invention are those derived from other mineral acids and organic acids. The Dropper für Krampfadern salts of the basic compounds are prepared by different methods. For example, the free base is dissolved in an aqueous alcohol solution containing the appropriate acid and the salt is isolated by evaporation of the solution.

Alternatively, they may be prepared by reaction of the free base with an acid in an organic solvent so that the salt separates directly.

In cases in which the precipitation of the salt is difficult, it can be precipitated with a second organic solvent, or can be obtained by concentration of the solution. Although medically acceptable salts of the basic Dropper für Krampfadern are preferred, all acid addition salts fall within the scope of the invention. All acid-addition salts are useful as sources of the free base form even if the particular salt per se is desired only as an intermediate product.

So sind zum Beispiel, wenn das Salz Dropper für Krampfadern zum Zweck der Reinigung oder Identifikation gebildet wird, oder wenn es als Zwischenprodukt bei der Herstellung eines medizinisch akzeptablen Salzes durch Ionenaustauschverfahren verwendet wird, diese Salze eindeutig als Teil dieser Erfindung zu betrachten.

Thus, for example, when the salt is formed only for purposes of purification or identification, or when it is used as intermediate in preparing a medicinally acceptable salt by ion exchange procedures, these salts are clearly to be regarded as part of this invention.

A "biohydrolyzable ester" Dropper für Krampfadern to an ester of the compound of the invention which Ich habe Krampfadern und Endometriose be readily converted by a mammal to yield an active compound of the invention. Of course, an addition salt may provide an optical center as well, where once was none. For example, a chiral tartrate may be prepared from the compounds of the invention, and this definition includes such chiral salts.

Es ist den Fachleuten klar, dass die Offenbarung der racemischen Mischung allein jedwede Enantiomere darin offenbart. It is clear to those of skill that the disclosure of the racemic mixture alone discloses any enantiomers therein.

Auf diese Weise wird durch eine Offenbarung mehr als eine Verbindung gelehrt. In this way, more than one compound is taught by revelation. As used herein, "animal", "mammals", meaning "including people".

Der Fachmann wird einsehen, dass in bestimmten Verbindungen der Erfindung tautomere Formen existieren. Those skilled in the art will appreciate that in certain compounds of the invention here forms exist.

Auf diese Weise offenbart in dieser Beschreibung die Offenbarung einer tautomeren Form jedes und alle Tautomeren. In this manner disclosed in this specification, the disclosure of a tautomeric form, any and all tautomers. Obwohl die Darstellungsart II durchweg in den Beschreibungen benutzt wird.

Although the representation type II is consistently used in the descriptions. Similarly, it is clear that when the 2-Iminoimidazolidinyl form of the molecule is shown, the 2-imidazolinylamino form of that molecule, although is not specifically shown, encompassed.

The presentation of specific protected forms and other derivatives of the compounds of formula I is not intended to be limiting. The application of other Dropper für Krampfadern protecting groups, salt forms, etc. As defined above and as used herein, substituent groups may themselves be substituted.

Eine solche Substitution kann mit einem oder mehreren Substituenten erfolgen. Such substitution may be with one or more substituents. Solche Substituenten beinhalten solche, die in C. Such substituents include those listed in C. Leo, substituent Constants for Correlation Analysis in Chemistry and Biologywhich is incorporated herein by reference.

Piperidinyl, Morpholinyl, Pyrrolidinyl, etc. Preferred substituents include for example alkyl, alkenyl, alkoxy, oxo, nitro, amino, aminoalkyl eg. Folglich ist, wie im folgenden Beispiel gezeigt, der Ort der Reste: Thus, as shown in the following example, the location of residues: Die Erfindung beinhaltet Verbindungen, wie sie in der Zusammenfassung der Erfindung beschrieben sind. The invention includes compounds as described in the Summary of the Invention.

Bevorzugte Verbindungen dieser Erfindung weisen die folgende Struktur auf: Preferred compounds of this invention have the following structure: Verfahren zur Herstellung der Verbindungen der Erfindung A process for the preparation of the compounds of the invention. Die Verbindungen dieser Erfindung werden unter Verwendung der folgenden Verfahren synthetisiert. The compounds of Dropper für Krampfadern invention article source synthesized using the following procedure.

Zum Zwecke dieser Beschreibung werden 6- 2-Imidazollinylamino -Verbindungen gezeigt, der Fachmann wird jedoch verstehen, dass die 4- und 5- 2-Imidazolinylamino -Verbindungen in gleicher Weise bevorzugt sind. For purposes of this description 6- 2-Imidazollinylamino are shown compounds, the skilled artisan will Dropper für Krampfadern, however, that the 4- and 5- 2-imidazolinylamino compounds preferably Dropper für Krampfadern the same way.

The skilled artisan will appreciate that the radicals omitted are added by using known techniques in the art. The skilled artisan will also understand that the method described, if necessary, can be used with blocking groups and the like. Imidazolinylamino groups are conveniently prepared from nitro and amino compounds via the following example synthetic sequence.

Vorzugsweise werden diese Verbindungen aus Nitro- oder Aminoverbindungen hergestellt, zum Beispiel den oben beschriebenen. Preferably, these compounds from nitro or amino compounds are prepared as described for the example above.

All brominations are preferably carried out on dihydroindole nuclei which may then be oxidized to indoles: The chlorination is preferably conducted using Cl2, and iodination, by ICI using the same reactions of. Es ist dem Fachmann klar, dass die oben gezeigten Reaktionen bekannte Reaktionen sind.

It is clear to the expert that the reactions shown above are known reactions. Furthermore, it is within the skill of the skilled person to vary these reactions to prepare compounds within the scope of the claims. In the above schemes, where an R is alkoxy or alkylthio, the corresponding hydroxy or thiol compounds from the final compounds by using a standard Dealkylierungsverfahrens Bhatt, et al.

The starting materials used to prepare the compounds of the invention are known, made by known methods, or are commercially available as a Dropper für Krampfadern material. It is clearly seen that the skilled person can easily perform changes in the field of organic Dropper für Krampfadern without further instruction, that is, it is entirely within the scope and practice of the skilled artisan to carry out these changes.

Diese umfassen die Reduktion von Carbonylverbindungen zu ihren entsprechenden Alkoholen, Oxidationen, Acylierungen, aromatische Substitutionen, sowohl elektrophil als auch nukleophil, Veretherungen, Veresterungen und Verseifungen und dergleichen. These include reduction of carbonyl compounds to their corresponding alcohols, oxidations, acylations, aromatic substitutions, both electrophilic and nucleophilic, etherifications, esterifications and saponifications and the like.

These reactions can be found in the literature and are also situated within the practice of the art. Greene, Protecting-Groups in Organic Synthesis zu finden. Examples of many of these changes are, for example, in T.

Dropper für Krampfadern