WO1993018767A1 - Use of sydnonimines to treat erectile dysfunction - Google Patents

Use of sydnonimines to treat erectile dysfunction Download PDF

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Publication number
WO1993018767A1
WO1993018767A1 PCT/EP1993/000546 EP9300546W WO9318767A1 WO 1993018767 A1 WO1993018767 A1 WO 1993018767A1 EP 9300546 W EP9300546 W EP 9300546W WO 9318767 A1 WO9318767 A1 WO 9318767A1
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WIPO (PCT)
Prior art keywords
sydnonimine
methyl
carbonyl
dimethyl
amino
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PCT/EP1993/000546
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German (de)
French (fr)
Inventor
Karl Schönafinger
Eckard Kujath
Christian Stief
Original Assignee
Cassella Aktiengesellschaft
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Priority claimed from DE19924209462 external-priority patent/DE4209462A1/en
Priority claimed from DE19924213338 external-priority patent/DE4213338A1/en
Application filed by Cassella Aktiengesellschaft filed Critical Cassella Aktiengesellschaft
Publication of WO1993018767A1 publication Critical patent/WO1993018767A1/en

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame

Definitions

  • the present invention relates to the use of svdnonimines and pharmacologically acceptable salts thereof for the treatment of erectile dysfunctions.
  • vasoactive substances such as yohimbine, phenoxybenzamine, terbutaline, Bethanechol, levodopa, verapamil or theophylline has proven unsuccessful.
  • vasoactive substances such as yohimbine, phenoxybenzamine, terbutaline, Bethanechol, levodopa, verapamil or theophylline has proven unsuccessful.
  • prosthetic implants or revascular An intracavernous injection of papaverine (Virag, Lancet, 2, 938, 1982), the ⁇ -receptor blocker phenoxybenzamine (Brindley, Br. J. Psychiatr., 143, 332, 1983) and a combination of papaverine and the - ⁇ -receptor blocker phentolamine (Stief, Urologe A, 25, 63, 1986) as successful.
  • the latter therapy method can be carried out independently by the patient and is also referred to as erectile tissue auto-injection therapy (SKAT).
  • acetylcholine is associated with strong systemic side effects in the case of a short-term erection and the injection of prostaglandin E ⁇ is rejected by the patients because of excessive pain.
  • the object of the invention was therefore the development and manufacture of medicaments for the treatment of neurogenic, arterial, neurotransmitter-related, myopathic, venous or psychogenic erectile dysfunctions without the side effects mentioned. Surprisingly, it has now been found that this problem can be solved by Sydnonimine.
  • Sydnonimines are compounds whose pharmacology has been known for a long time (Chemistry in our time, 13th year, page 51 (1984)), and besides the vasodilating effects, the antithrombotic effects are also described (J. Cardiovasc. Pharmacol. 1989 , 14 (Suppl. 11), page 129). Sydnonimines to the cardiovascular-Sys ⁇ tems are used as a means of preventing a nd treatment of diseases and as such commercially.
  • the present invention thus relates to the use of sydnonimines of the general formula I.
  • R is an amino group of the formula
  • R ' is hydrogen, halogen, alkyl, cycloalkyl, arylalkyl,
  • alkyl alkenyl, cycloalkyl, bicycloalkyl, tricycloalkyl, alkyl-X-alkyl, arylalkyl, which also by
  • Alkyl or halogen can be substituted, hydroxyalkyl, a heterocyclic ring bound via an alkylene chain or a radical
  • R represents hydrogen or one of the meanings of R has 4 ;
  • R 6 represents alkyl
  • R 7 aryl, by 1 to 3 halogen atoms and / or 1 to 3 alkyl radicals and / or 1 to 3 alkoxy radicals and / or 1 or 2 nitro groups mono-, di- or tri-substituted aryl radical, arylalkenyl, tricycloalkyl, bicycloalkoxy, tricycloalkoxy , Aryloxy, alkoxycarbonyl, pyridyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl,
  • X is NR 4 , NS0 2 R 8 , NC0 2 alkyl, S (0) n , 0, (CH 2 ) m or a simple bond; n is 0, 1 or 2; m is 1, 2 or 3; and o R denotes alkyl, aryl, alkylaryl, haloaryl or dialkyl-a ino, where the aryl groups can also be substituted by alkyl or halogen, for the treatment of erectile dysfunctions, where X cannot be 0 if R 2 and R 3 are hydrogen .
  • Alkyl residues and alkenyl residues can be straight-chain or branched and preferably have 1 to 6 C atoms, particularly preferably 1 to 4 C atoms. This also applies if they are in connection with other groups, e.g. B. as alkoxy, arylalkyl, etc. are present.
  • alkyl radicals are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl and tert-butyl.
  • Cycloalkyl preferably has 5 to 7 carbon atoms and particularly preferably denotes cyclopentyl and cyclohexyl.
  • Bicycloalkyl preferably has 7 to 14 carbon atoms. Tricycloalkyl preferably has 7 to 16 carbon atoms.
  • Halogen preferably means fluorine, chlorine, bromine or iodine.
  • Aryl preferably has 6 to 10 carbon atoms and particularly preferably means ⁇ - or ⁇ -naphthyl or phenyl.
  • Arylalkyl is preferably benzyl and phenylethyl.
  • Aryl-O-alkyl is preferably phenoxymethyl and phenoxyethyl. The same applies to aryl-S-alkyl.
  • aryl radicals which stand for R can be mono-, di- or tri-substituted, although only a maximum of 2 nitro groups, such as 2-methyl-4,6-dinitrophenyl and 2-chloro-6-, can be present even when trisubstituted. methyl-4-nitrophenyl.
  • Halogen substituents for the aryl radicals are, for example Chlorine and bromine atoms in loading
  • Preferred radicals R are piperidino, pyrrolidino, dimethylamino, diethylamino, diisopropylamino, tert.butylmethylamino, tert.butylethylamino, tert.butylpropylamino, ter .butylbutylamino, tert.butyl-hydroxyethylamino, dibenzylamino, 2-carboxy-pyrrolidino, 2-carboxy-piperidino, 4-carboxypiperidino, dicyclohexylamino, N-methylpiperazino, 2,2-dimethylpiperidino, 3,3-dimethyl-morpholino, 3,3-dimethylthiomorpholino, 3,3-dimethyl-
  • Preferred radicals R 2 are hydrogen, methyl, ethyl, propyl, isopropyl and butyl, with hydrogen being particularly preferred.
  • Preferred radicals R 3 are hydrogen, formyl, acetyl,
  • Propionyl, butyryl, isobutyryl, pivaloyl, benzoyl, anisoyl, hydrogen is particularly preferred.
  • N N'-dicarboxy-3,3'-diphenyl-4,4'-bisydnonimine
  • N N'-dicarboxy-3,3'-dimethyl-4,4'-bisydnonimine
  • N-Benzoyl-3 - (((2-carboxy-3- (hydroxymethyl) -8-oxo-5-thia-1-azabicyclo (4.2.0) oct-2-en-7-yl) carbamoyl) methyl) - syd ⁇ nonimin acetate; 3 - (((2-Carboxy-3- (hydroxymethyl) -8-oxo-5-thia-l-azabicyclo (4.2.0) oct-2-en-7-yl) carbamoyl) methyl) -N- (methylcarbamoyl) -sydnonimine acetate; 3-sec-octyl-sydnonimine;
  • N-carboxy-3- (p-chlorophenyl) sydnonimine methyl ester N-carboxy-3- ⁇ -tolyl-sydnonimine methyl ester;
  • Pharmacologically acceptable salts of the sydnonimines of the general formula I are in particular acid addition salts with inorganic or organic acids.
  • Suitable acids are, for example, hydrogen chloride, hydrogen bromide, naphthalenedisulfonic acids, in particular naphthalene disulfonic acid (1,5), phosphoric, nitric, sulfuric, oxalic, milk, wine, vinegar, salicylic, benzoic , Ants, propion, pivaline, diethyl vinegar, malon, amber, pimelin, fumar, malein, apple, sulfamine, phenylpropion, glucon, ascorbin, isonicotine, Methane sulfonic, p-toluenesulfonic, citric or adipic acid.
  • the hydrochlorides are particularly preferred.
  • Sydnonimine in a pharmaceutical preparation.
  • parenteral and topical forms of application such as lotions, creams, solutions, gels, sprays, elastic liquid plasters, transdermal systems or coatings for condoms in question.
  • Parenteral administration is preferred, since it is the safest form of using a targeted amount of active ingredient directly without further adulteration by other factors.
  • Preparations for parenteral administration contain 0.1 to 5 mg, preferably 0.1 to 2 mg of sydnonimine of the general formula I per dose unit and can be given in separate
  • Dosage unit forms such as B. ampoules or vials. Solutions of the active ingredient are preferably used, preferably aqueous solutions and above all isotonic solutions, but also suspensions. These injection forms can be made available as a ready-to-use preparation or only directly before use by mixing the active compound, eg. B. the lyophilizate, optionally with other solid carriers, with the desired solvent or suspending agent. For topical forms of application, a higher active substance concentration than that mentioned for parenteral preparations is of course indicated.
  • Parenteral and topical forms can be sterilized and / or optionally contain auxiliaries such as preservatives, stabilizers, wetting agents, penetrants, emulsifiers, spreading agents, solubilizers, salts for regulating the osmotic pressure or for buffering and / or viscosity regulators.
  • auxiliaries such as preservatives, stabilizers, wetting agents, penetrants, emulsifiers, spreading agents, solubilizers, salts for regulating the osmotic pressure or for buffering and / or viscosity regulators.
  • Such additives are e.g. B. tartrate and citrate buffers, ethanol, complexing agents (such as ethylenediamine-tetraacetic acid and its non-toxic salts).
  • High-molecular polymers such as liquid polyethylene oxide, carboxymethyl- cellulosic, polyvinylpyrrolidones, dextrans or gelatin.
  • Solid carriers are e.g. B. starch, lactose, mannitol, methyl cellulose, talc, highly disperse silicas, higher molecular weight fatty acids (such as stearic acid), gelatin, agar, calcium phosphate, magnesium stearate, animal and vegetable fats, solid high molecular weight polymers, such as polyethylene glycol.
  • Oily suspensions for parenteral or topical applications can be vegetable synthetic or semisynthetic oils such as liquid fatty acid esters with 8 to 22 carbon atoms in the fatty acid chains, e.g. B. palmitic, lauric, tridecyl, margarine, stearic, araquinic, myristic, behenic, pentadecyl, linoleic, elaidic, brasidic, erucic or oleic acid, with a-bis trivalent alcohols with 1 to 6 carbon atoms, such as, for example, methanol, ethanol, propanol, butanol, pentanol or their isomers, glycol or glycerol, have been esterified.
  • vegetable synthetic or semisynthetic oils such as liquid fatty acid esters with 8 to 22 carbon atoms in the fatty acid chains, e.g. B. palmitic, lauric, tridecyl, margarine, ste
  • Such fatty acid esters are, for example, commercially available miglyols, isopropyl myristate, isopropyl palmitate, isopropyl stearate, PEG 6-capric acid, cypryl / capric acid esters of saturated fatty alcohols, polyoxyethylene glycerol trioleates, ethyl oleate, wax-like fatty acid esters such as artificial duck fatty acid, ethyl ester fatty acid, coconut oil fatty acid, coconut oil ester, isol fatty acid ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isopropyl fatty acid ethy
  • silicone oils of various viscosities or fatty alcohols such as isotidexyl alcohol, 2-octyldodecanol, cetylstearyl alcohol or oleyl alcohol, fatty acids such as oleic acid.
  • Vegetable oils such as castor oil, almond oil, olive oil, sesame oil, cottonseed oil, peanut oil or soybean oil can also be used.
  • the substances mentioned also have the properties of a spreading agent, ie there is a particularly good distribution on the skin.
  • Suitable solvents, gel formers and solubilizers are water or water-miscible solvents. Are suitable for. B.
  • alcohols such as ethanol or isopropyl alcohol, benzyl alcohol, 2-0ctyl-dodecanol, polyethylene glycols, phthalates, adipates, propylene glycol, glycerol, di- or tripropylene glycol, waxes, methyl cellosolve, cellosolve, ester, morpholines, dioxane, dimethyl sulfoxide, dimethylformamide, Tetrahydrofuran, cyclohexanone etc.
  • alcohols such as ethanol or isopropyl alcohol, benzyl alcohol, 2-0ctyl-dodecanol, polyethylene glycols, phthalates, adipates, propylene glycol, glycerol, di- or tripropylene glycol, waxes, methyl cellosolve, cellosolve, ester, morpholines, dioxane, dimethyl sulfoxide, dimethylformamide, Tetrahydrofuran,
  • Cellulose ethers which dissolve or swell both in water and in organic solvents and which form a type of film after drying, such as, for example, hydroxypropyl cellulose, methyl cellulose, ethyl cellulose or soluble starches, can be used as film formers.
  • Ionic macromolecules in particular are used here, such as sodium carboxymethyl cellulose, polyacrylic acid, polymethacrylic acid and its salts, sodium amylopectin semiglycolate, alginic acid or propylene glycol alginate as sodium salt, gum arabic, xanthan gum, guar gum or carrageenan.
  • auxiliaries that can be used are: glycerol, paraffin of different viscosities, triethanolamine, collagen, allantoin, novantisol acid, perfume oils.
  • surfactants such as, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, di-Na-N-lauryl- ⁇ -iminodipropionate, polyoxyethylated castor oil or sorbitan monooleate, sorbitan monostearate, cetylal - alcohol, lecithin, glycerol monostearate, polyoxyethylene stearate, alkylphenol polyglycol ether, cetyltrimethylammonium chloride or mono- / dialkylpolyglycol ether-orthophosphoric acid-monoethanolamine salts.
  • surfactants such as, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, di-Na-N-lauryl- ⁇ -iminodipropionate, polyoxyethylated castor oil or sorbitan monooleate, sorbitan monostearate, cetylal - alcohol,
  • Stabilizers such as montmorillonites or colloidal silicas for stabilizing emulsions or for preventing the breakdown of active substances such as antioxidants, for example tocopherols or butylhydroxyanisole, or preservatives such as p-hydroxybenzoic acid esters can also be used to prepare the ge ⁇ desired formulations may be required.
  • Formulations preferably organic solvents which are well tolerated by the skin, such as ethanol, methylpyrrolidone, polyethylene glycol, oleyl alcohol, octanol, linoleic acid, triacetine, propylene glycol, glycerol, solketal or dimethyl sulfoxide.
  • organic solvents such as ethanol, methylpyrrolidone, polyethylene glycol, oleyl alcohol, octanol, linoleic acid, triacetine, propylene glycol, glycerol, solketal or dimethyl sulfoxide.
  • Compounds such as quinolines, for example 8-hydroxyquinoline or quinoline yellow, are suitable as photostabilizers; suitable food colors; Flavanoids such as B. hesperidin, hesperidin-methylchalcon, hesperidin phosphate, hesperitin, quercetin, quercitrin, rutin, rutin sulfate, naringenin, camphor oil, kaempferol 7,4'-dimethyl ether, morin, apigetrin, luteolin and its 7-glycoside, or Troxerutin. They are added in a quantity ratio of 0.001: 1 to 50: 1, preferably 0.1: 1 to 20: 1.
  • the preparation, filling and sealing of the preparations is carried out under the usual antimicrobial and aseptic conditions.
  • packaging is also possible in separate dose units to facilitate handling, here too, as in parenteral forms, if necessary for reasons of stability, by separate packaging of the active substances or their combinations as lyophilisate, if appropriate with solid carriers, and the necessary solvents etc.
  • the sydnonimines of the general formula I are used in combination with one or more synergistically active substances.
  • synergistic substances are, for example, adenosine, vitamins, e.g. B. Vitamin A or H, prostaglandins, e.g. B. E ⁇ , peptides such. B.
  • Citricone gene related peptides CGRP
  • calcium antagonists such as nifedipine, verapamil, diltiaze, gallopamil, niludipine, nimodipine, nicardipine, prenylamine, fendiline, terodiline, nisaldipine, nitrendipine or perhexiline, for example ⁇ -receptor blockers Phentolamine methanesulfonate, phenoxybenzamine or minoxidil, smooth muscle relaxants such as papaverine, trinitroglycerin, sodium nitroprusside or S-nitroso-N-acetylpenicillamine.
  • Particularly advantageous and also an object of the present invention is a disposable medicament package containing in sterile packaging a disposable syringe with a parenteral preparation of a sydnonimine of the general formula I, optionally in combination with a synergistically active substance; with disinfectant provided sterile swabs as well as usage information.
  • the disposable pre-filled syringes mentioned are preferably of the ultrafine type, as are used, for example, in insulin therapy. Syringes of the type of auto-injectors that are even easier to handle are also preferred.
  • the pre-filled syringes are preferably made in opaque form, since this adds photostabilizers to the parenteral ones
  • Preparations are unnecessary. However, they can also be designed in such a way that the active ingredient and associated injection solvent are only mixed directly before the injection. This can e.g. B. happen in two-container ampoules or syringes. As a result, any photostabilizer additive that may be required can also be omitted.
  • the sterile swabs for disinfection contain the usual skin disinfectants such as ethanol. However, they can also contain erection-promoting agents in a topically applicable form to increase or prolong the action.

Abstract

The present invention concerns the use of sydnonimines of general formula (I) as disclosed in the main claim, as well as pharmacologically non-toxic salts thereof, for treating erectile dysfunction.

Description

Verwendung von Svdnoniminen zur Behandlung erektiler DvsfunktionenUse of svdnonimines to treat erectile functions
Die vorliegende Erfindung betri ft die Verwendung von Svdnoniminen sowie pharmakologisch verträgliche Salze davon zur Behandlung erektiler Dysfunktionen.The present invention relates to the use of svdnonimines and pharmacologically acceptable salts thereof for the treatment of erectile dysfunctions.
Etwa 5 % der Männer im 40. Lebensjahr und 20 % im 60. Lebensjahr leiden an einer erektilen Dysfunktion. Diese Störungen bedürfen einer medizinischen Behandlung, da insbesondere Patienten mit chronischer erektiler Dysfunk¬ tion in Ihrer Sexualität und Persönlichkeit verunsichert und als krank anzusehen sind.About 5% of men in their 40s and 20% in their 60s suffer from erectile dysfunction. These disorders require medical treatment, since patients with chronic erectile dysfunction in particular are unsettled in their sexuality and personality and can be regarded as sick.
Zur Behandlung von bis in die siebziger Jahre überwiegend auf psychische Ursachen zurückgeführten PotenzStörungen wurden neben psychotherapeutischen Maßnahmen Testosterone oder Aphrodisiaka von umstrittenem Wert eingesetzt. Erst durch die Erforschung der Physiologie des Erektionsab- laufs wurde festgestellt, daß bei mehr als 60 % der Pa- • tienten organische Ursachen die ErektionsStörung bewir¬ ken, wobei autonome Efferenzen aus dem parasympathischen Anteil des Sakralmarkes, Neurotransmitter, Dilatation der Penisarterien, Relaxation der cavernösen Räume und Kon- striktion der Venen eine Rolle spielen. In über 70 % der Fälle sind vaskuläre Faktoren ursächlich beteiligt, wie pathologische arterielle Blutversorgungen oder abnorm gesteigerter venöser Abfluß aus den kavernosen Räumen. Neurogene Störungen sind zu etwa 20 % beteiligt.In addition to psychotherapeutic measures, testosterones or aphrodisiacs of controversial value were used to treat erectile dysfunction, which was mainly attributed to psychological causes until the 1970s. It was only through research into the physiology of the erection process that it was found that in more than 60% of the patients • organic causes cause the erection disorder, with autonomous efferences from the parasympathetic portion of the sacral marrow, neurotransmitters, dilation of the penile arteries, relaxation of the cavernous spaces and constriction of the veins play a role. In more than 70% of cases, vascular factors are causally involved, such as pathological arterial blood supplies or abnormally increased venous drainage from the cavernous spaces. About 20% of neurogenic disorders are involved.
Die orale Therapie dieser organisch bedingten Dysfunktio- nen mit vasoaktiven Substanzen wie Yohimbin, Phenoxy- benzamin, Terbutalin, Bethanechol, Levodopa, Verapamil oder Theophyllin erwies sich als erfolglos. Neben der Anwendung von Prothesenimplantationen oder Revaskulari- sierungsoperationen erwies sich eine intrakavernöse In¬ jektion von Papaverin (Virag, Lancet, 2, 938, 1982), dem α-Rezeptorenblocker Phenoxybenzamin (Brindley, Br. J. Psychiatr., 143, 332, 1983) und eine Kombination von Papaverin und dem- α-Rezeptorenblocker Phentolamin (Stief, Urologe A, 25, 63, 1986) als erfolgreich. Letztere Thera¬ piemethode läßt sich vom Patienten selbständig durchfüh¬ ren und wird auch als Schwellkörper-Autoinjektionsthera¬ pie (SKAT) bezeichnet.Oral therapy for these organic dysfunctions with vasoactive substances such as yohimbine, phenoxybenzamine, terbutaline, Bethanechol, levodopa, verapamil or theophylline has proven unsuccessful. In addition to the use of prosthetic implants or revascular An intracavernous injection of papaverine (Virag, Lancet, 2, 938, 1982), the α-receptor blocker phenoxybenzamine (Brindley, Br. J. Psychiatr., 143, 332, 1983) and a combination of papaverine and the - α-receptor blocker phentolamine (Stief, Urologe A, 25, 63, 1986) as successful. The latter therapy method can be carried out independently by the patient and is also referred to as erectile tissue auto-injection therapy (SKAT).
Nachteilig erwiesen sich jedoch eine teilweise uner¬ wünscht verlängerte Erektion mit der Gefahr des Priapis- mus bei der Verwendung von Papaverin, unerwünschte Schmerzhaf igkeit bei der Anwendung von Phenoxybenzamin sowie eine mögliche Cancerogenität dieser Verbindung.However, a partially undesirably prolonged erection with the risk of priapism when using papaverine, undesirable painfulness when using phenoxybenzamine and a possible carcinogenicity of this compound proved to be disadvantageous.
Im Tierexperiment (Cynomolgus) wurden zudem bei 1 - 2 Intracavernös-Injektionen Papaverin wöchentlich über 12 Monate ausgedehnte Fibroisierungen weiter Teile des Schwellkörpers festgestellt, was beim Menschen zu äußerst negativen Langzeitergebnissen führen würde, da bei einer Fibroisierung des corpus cavernosum keine Erektion mehr erfolgen kann.In animal experiments (cynomolgus), 1 to 2 intra-cavernous papaverine injections were carried out over a period of 12 months, and extensive fibroisings of large parts of the erectile tissue were found, which would lead to extremely negative long-term results in humans, since an erection could no longer occur if the corpus cavernosum was fibroized.
Die Anwendung von Acetylcholin ist bei nur kurzzeitiger Erektion mit starken systemischen Nebenwirkungen verbun¬ den und die Injektion von Prostaglandin E^ wird von den Patienten wegen zu großer Schmerzhaftigkeit abgelehnt.The use of acetylcholine is associated with strong systemic side effects in the case of a short-term erection and the injection of prostaglandin E ^ is rejected by the patients because of excessive pain.
Aufgabe der Erfindung war daher die Entwicklung und Her¬ stellung von Arzneimitteln zur Behandlung von neurogenen, arteriellen, neurotransmitterbedingten, myopathischen, venösen oder psychogenen erektilen Dysfunktionen ohne die genannten Nebenwirkungen. Überraschenderweise wurde nun gefunden, daß diese Aufgabe durch Sydnonimine gelöst werden kann.The object of the invention was therefore the development and manufacture of medicaments for the treatment of neurogenic, arterial, neurotransmitter-related, myopathic, venous or psychogenic erectile dysfunctions without the side effects mentioned. Surprisingly, it has now been found that this problem can be solved by Sydnonimine.
Sydnonimine sind Verbindungen, deren Pharmakologie schon lange bekannt ist (Chemie in unserer Zeit, 13, Jahrgang, Seite 51 (1984)), wobei neben der vasodilatierenden ins¬ besondere auch die antithrombotisehen Wirkungen beschrie¬ ben sind (J. Cardiovasc. Pharmacol. 1989, 14 (Suppl. 11), Seite 129). Sydnonimine können als Mittel zur Vorbeugung und Behandlung von Erkrankungen des Herz-Kreislauf-Sys¬ tems eingesetzt werden und sind als solche im Handel.Sydnonimines are compounds whose pharmacology has been known for a long time (Chemistry in our time, 13th year, page 51 (1984)), and besides the vasodilating effects, the antithrombotic effects are also described (J. Cardiovasc. Pharmacol. 1989 , 14 (Suppl. 11), page 129). Sydnonimines to the cardiovascular-Sys¬ tems are used as a means of preventing a nd treatment of diseases and as such commercially.
Die vorliegende Erfindung betrifft somit die Verwendung von Sydnoniminen der allgemeinen Formel IThe present invention thus relates to the use of sydnonimines of the general formula I.
Figure imgf000005_0001
Figure imgf000005_0001
oder eines phar akologisch verträglichen Salzes davon, wobei R eine Aminogruppe der Formel or a pharmaceutically acceptable salt thereof, wherein R is an amino group of the formula
Figure imgf000006_0001
Figure imgf000006_0001
bedeutet;means;
R' Wasserstoff, Halogen, Alkyl, Cycloalkyl, Arylalkyl,R 'is hydrogen, halogen, alkyl, cycloalkyl, arylalkyl,
Aryl-O-Alkyl, Aryl-S-Alkyl, Alkoxyalkyl, Alkylthio- alkyl oder Alkenylthioalkyl bedeutet;Aryl-O-alkyl, aryl-S-alkyl, alkoxyalkyl, alkylthioalkyl or alkenylthioalkyl;
R- Wasserstoff -NO, die Gruppe -S02R oder die GruppeR- hydrogen -NO, the group -S0 2 R or the group
-COR7 bedeutet;-COR 7 ;
Ε Alkyl, Alkenyl, Cycloalkyl, Bicycloalkyl, Tricyclo- alkyl, Alkyl-X-Alkyl, Arylalkyl, das auch durchΕ alkyl, alkenyl, cycloalkyl, bicycloalkyl, tricycloalkyl, alkyl-X-alkyl, arylalkyl, which also by
Alkyl oder Halogen substituiert sein kann, Hydroxy- alkyl, einen über eine Alkylenkette gebundenen hete- rocyclischen Ring oder einen RestAlkyl or halogen can be substituted, hydroxyalkyl, a heterocyclic ring bound via an alkylene chain or a radical
SS
bedeutet;means;
R- Wasserstoff bedeutet oder eine der Bedeutungen von R4 hat;R represents hydrogen or one of the meanings of R has 4 ;
R6 Alkyl bedeutet;R 6 represents alkyl;
R7 Aryl, durch 1 bis 3 Halogenatome und/oder 1 bis 3 Alkylreste und/oder 1 bis 3 Alkoxyreste und/oder 1 oder 2 Nitrogruppen mono-, di- oder trisubstituier- ten Arylrest, Arylalkenyl, Tricycloalkyl, Bicyclo- alkoxy, Tricycloalkoxy, Aryloxy, Alkoxycarbonyl, Pyridyl, Pyrrolyl, Imidazolyl, Pyrazolyl, Pyrazinyl,R 7 aryl, by 1 to 3 halogen atoms and / or 1 to 3 alkyl radicals and / or 1 to 3 alkoxy radicals and / or 1 or 2 nitro groups mono-, di- or tri-substituted aryl radical, arylalkenyl, tricycloalkyl, bicycloalkoxy, tricycloalkoxy , Aryloxy, alkoxycarbonyl, pyridyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl,
Pyrimidinyl, Pyridazinyl oder OR bedeutet oder eine der Bedeutungen von R2 hat;Represents pyrimidinyl, pyridazinyl or OR or has one of the meanings of R 2 ;
X NR4, NS02R8, NC02Alkyl, S(0)n, 0, (CH2)m oder eine einfache Bindung bedeutet; n 0, 1 oder 2 ist; m 1, 2 oder 3 ist; und o R Alkyl, Aryl, Alkylaryl, Halogenaryl oder Dialkyl- a ino bedeutet, wobei die Arylgruppen auch durch Alkyl oder Halogen substituiert sein können, zur Behandlung erektiler Dysfunktionen, wobei X nicht für 0 stehen kann, wenn R2 und R3 Wasserstoff bedeuten.X is NR 4 , NS0 2 R 8 , NC0 2 alkyl, S (0) n , 0, (CH 2 ) m or a simple bond; n is 0, 1 or 2; m is 1, 2 or 3; and o R denotes alkyl, aryl, alkylaryl, haloaryl or dialkyl-a ino, where the aryl groups can also be substituted by alkyl or halogen, for the treatment of erectile dysfunctions, where X cannot be 0 if R 2 and R 3 are hydrogen .
Alkylreste und Alkenylreste können geradkettig oder ver¬ zweigt sein und haben bevorzugt 1 bis 6 C-Atome, beson¬ ders bevorzugt 1 - 4 C-Atome. Dies gilt auch, wenn sie in Verbindung mit anderen Gruppen, z. B. als Alkoxy, Arylal- kyl usw. vorliegen.Alkyl residues and alkenyl residues can be straight-chain or branched and preferably have 1 to 6 C atoms, particularly preferably 1 to 4 C atoms. This also applies if they are in connection with other groups, e.g. B. as alkoxy, arylalkyl, etc. are present.
Beispiele für Alkylreste sind Methyl, Ethyl, Propyl, Iso- propyl, Butyl, sek.-Butyl und tert.-Butyl.Examples of alkyl radicals are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl and tert-butyl.
Cycloalkyl hat bevorzugt 5 bis 7 C-Atome und bedeutet be¬ sonders bevorzugt Cyclopentyl und Cyclohexyl.Cycloalkyl preferably has 5 to 7 carbon atoms and particularly preferably denotes cyclopentyl and cyclohexyl.
Bicycloalkyl hat bevorzugt 7 bis 14 C-Atome. Tricyclo¬ alkyl hat bevorzugt 7 bis 16 C-Atome. Halogen bedeutet bevorzugt Fluor, Chlor, Brom oder Iod. Aryl hat bevorzugt 6 bis 10 C-Atome und bedeutet beson¬ ders bevorzugt α- oder ß-Naphthyl oder Phenyl. Arylalkyl ist bevorzugt Benzyl und Phenylethyl. Aryl-O-alkyl ist bevorzugt Phenoxymethyl und Phenoxy- ethyl. Entsprechendes gilt für Aryl-S-alkyl.Bicycloalkyl preferably has 7 to 14 carbon atoms. Tricycloalkyl preferably has 7 to 16 carbon atoms. Halogen preferably means fluorine, chlorine, bromine or iodine. Aryl preferably has 6 to 10 carbon atoms and particularly preferably means α- or β-naphthyl or phenyl. Arylalkyl is preferably benzyl and phenylethyl. Aryl-O-alkyl is preferably phenoxymethyl and phenoxyethyl. The same applies to aryl-S-alkyl.
Die für R stehenden Arylreste können mono-, di- oder trisubstituiert sein, wobei jedoch auch bei einer Trisub stitution nur maximal 2 Nitrogruppen vorhanden sein kön¬ nen, wie beispielsweise 2-Methyl-4,6-dinitrophenyl und 2-Chlor-6-methyl-4-nitrophenyl. Als Halogensubstituenten für die Arylreste kommen z.B. Chlor und Bromatome in Be-The aryl radicals which stand for R can be mono-, di- or tri-substituted, although only a maximum of 2 nitro groups, such as 2-methyl-4,6-dinitrophenyl and 2-chloro-6-, can be present even when trisubstituted. methyl-4-nitrophenyl. Halogen substituents for the aryl radicals are, for example Chlorine and bromine atoms in loading
•7 tracht. Als für R stehende Arylreste sind insbesondere zu nennen: Methylphenyl (= Toj.yl), Nitrophenyl und Chlo- rophenyl, insbesondere 4-Nitrophenyl und 4-Chlorophenyl. • 7 costume. Aryl radicals which stand for R include, in particular: methylphenyl (= Toj.yl), nitrophenyl and chlorophenyl, in particular 4-nitrophenyl and 4-chlorophenyl.
Bevorzugte Reste R sind Piperidino, Pyrrolidino, Di- methylamino, Diethylamino, Diisopropylamino, tert.Butyl- methylamino, tert.Butyl-ethylamino, tert.butyl-propyl- amino, ter .butylbutylamino, tert.Butyl-hydroxyethyl- amino, Dibenzylamino, 2-Carboxy-pyrrolidino, 2-Carboxy- piperidino, 4-Carboxypiperidino, Dicyclohexylamino , N-Methylpiperazino, 2,2-Dimethylpiperidino, 3.3-Dimethyl- morpholino, 3.3-Dimethylthiomorpholino, 3.3-Dimethyl-Preferred radicals R are piperidino, pyrrolidino, dimethylamino, diethylamino, diisopropylamino, tert.butylmethylamino, tert.butylethylamino, tert.butylpropylamino, ter .butylbutylamino, tert.butyl-hydroxyethylamino, dibenzylamino, 2-carboxy-pyrrolidino, 2-carboxy-piperidino, 4-carboxypiperidino, dicyclohexylamino, N-methylpiperazino, 2,2-dimethylpiperidino, 3,3-dimethyl-morpholino, 3,3-dimethylthiomorpholino, 3,3-dimethyl-
1.1-dioxo-thiomorpholino, 3.3-Dimethyl-l-oxo-thiomorpho- lino, cis-2.6-Dimethylpiperidino, 2.2.6.6-Tetramethyl- piperidino, 2.2-Dimethyl-N-methylsulfonyl-piperazino, 2.2-Dimethyl-N-tosyl-piperazino, 2.2-Dimethyl-pyrrolidi- no, 2.2-Dimethyl-N-dimethylaminosulfonyl-piperazino,1.1-dioxo-thiomorpholino, 3.3-dimethyl-l-oxo-thiomorpholino, cis-2.6-dimethylpiperidino, 2.2.6.6-tetramethyl-piperidino, 2.2-dimethyl-N-methylsulfonyl-piperazino, 2.2-dimethyl-N-tosyl- piperazino, 2,2-dimethyl-pyrrolidino, 2,2-dimethyl-N-dimethylaminosulfonyl-piperazino,
Ethylamino, (2-Hydroxyethyl)-amino und Cyclohexylamino. Bevorzugte Reste R2 sind Wasserstoff, Methyl, Ethyl, Propyl, Isopropyl und Butyl, wobei Wasserstoff besonders bevorzugt ist. Bevorzugte Reste R3 sind Wasserstoff, Formyl, Acetyl,Ethylamino, (2-hydroxyethyl) amino and cyclohexylamino. Preferred radicals R 2 are hydrogen, methyl, ethyl, propyl, isopropyl and butyl, with hydrogen being particularly preferred. Preferred radicals R 3 are hydrogen, formyl, acetyl,
Propionyl, Butyryl, Isobutyryl, Pivaloyl, Benzoyl, Aniso- yl, besonders bevorzugt ist Wasserstoff.Propionyl, butyryl, isobutyryl, pivaloyl, benzoyl, anisoyl, hydrogen is particularly preferred.
Als Beispiele für die erfindungsgemäße Verwendbarkeit sind die folgenden Verbindungen genannt:The following compounds are mentioned as examples of the usability according to the invention:
3-(2,6-Dimethyl-l-piperidinyl)-sydnonimin;3- (2,6-dimethyl-1-piperidinyl) sydnonimine;
N-( (Butoxyacetyl)oxy)-3-(3,3-dimethyl-4-thiomorpholinyl)- sydnonimin; N-(Butoxycarbonyl)-3-(3,3-dimethyl-4-thiomorpholinyl)- sydnonimin;N- ((butoxyacetyl) oxy) -3- (3,3-dimethyl-4-thiomorpholinyl) sydnonimine; N- (butoxycarbonyl) -3- (3,3-dimethyl-4-thiomorpholinyl) sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-N-( ethoxycarbonyl)- sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) -N- (ethoxycarbonyl) sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-N-(ethoxycarbonyl)- sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) -N- (ethoxycarbonyl) sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-N-(4-methoxybenzoyl)- sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) -N- (4-methoxybenzoyl) sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) sydnonimine;
N-(Cyclohexylcarbonyl)-3-(3,3-dimethyl-4-thiomorpholi- ny1)-sydnonimin;N- (cyclohexylcarbonyl) -3- (3,3-dimethyl-4-thiomorpholine-1) -sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-N-(4-methoxybenzoyl)- sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) -N- (4-methoxybenzoyl) sydnonimine;
3-(3,3-Dimethyl-4-thiomorpholinyl)-N-(ethoxycarbonyl)- sydnonimin; 3-(3,3-Dimethyl-4-thiomorpholinyl)-sydnonimin;3- (3,3-dimethyl-4-thiomorpholinyl) -N- (ethoxycarbonyl) sydnonimine; 3- (3,3-dimethyl-4-thiomorpholinyl) sydnonimine;
N-Benzoy1-3-(2,6-dimethy1-1-piperidinyl)-4-(2-pheny1- ethyl)-sydnonimin;N-Benzoy1-3- (2,6-dimethy1-1-piperidinyl) -4- (2-pheny1-ethyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-(2-phenylethyl)-sydnon¬ imin; 3-(2,6-Dimethyl-l-piperidinyl)-N-(ethoxycarbonyl)-4-3- (2,6-dimethyl-1-piperidinyl) -4- (2-phenylethyl) -sydnon¬ imine; 3- (2,6-dimethyl-l-piperidinyl) -N- (ethoxycarbonyl) -4-
(phenylmethyl)-sydnonimi ;(phenylmethyl) sydnonimi;
3-(2,6-Dimethyl-l-piperidinyl)-4-(phenylmethyl)-sydnon¬ imin;3- (2,6-dimethyl-l-piperidinyl) -4- (phenylmethyl) -sydnon¬ imine;
3-(2,6-Dimethyl-l-piperidinyl)-4-(1-methylethyl)-sydnon- imin; N-Benzoyl-3- ( 2 , 6-dimethyl-l-piperidinyl ) -4-hexyl-sydnon- i in;3- (2,6-dimethyl-1-piperidinyl) -4- (1-methylethyl) -sydnone imine; N-benzoyl-3- (2,6-dimethyl-l-piperidinyl) -4-hexyl-sydnon-i in;
3-(2,6-Dimethyl-l-piperidinyl)-4-hexyl-sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -4-hexyl-sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-N-(ethoxycarbonyl)-4- methyl-sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -N- (ethoxycarbonyl) -4-methyl-sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-methyl-sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -4-methyl-sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-N-(4-methoxybenzoyl)- sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -N- (4-methoxybenzoyl) sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-(phenoxymethyl)-sydnon- imin;3- (2,6-dimethyl-l-piperidinyl) -4- (phenoxymethyl) -sydnone imine;
3-(2,6-Dimethyl-l-piperidinyl)-4-( (( henylmethyl)thio)- raethyl)-sydnonimin;3- (2,6-dimethyl-1-piperidinyl) -4- (((henylmethyl) thio) raethyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-N-(ethoxycarbonyl)-4-3- (2,6-dimethyl-l-piperidinyl) -N- (ethoxycarbonyl) -4-
((phenylmethoxy)methyl)-sydnonimin; 3-(2,6-Dimethyl-l-piperidinyl)-4-( (phenylmethoxy)methyl)- sydnonimin;((phenylmethoxy) methyl) -sydnonimine; 3- (2,6-dimethyl-l-piperidinyl) -4- ((phenylmethoxy) methyl) sydnonimine;
4-(l-Methyl-2-( (phenylmethyl)thio)ethyl)-3-(4-morpholi¬ no)-sydnonimin;4- (l-methyl-2- ((phenylmethyl) thio) ethyl) -3- (4-morpholino-no) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-N-(4-methoxybenzoyl)-4- (((phenylmethyl)thio)methyl)-sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -N- (4-methoxybenzoyl) -4- (((phenylmethyl) thio) methyl) -sydnonimine;
N-Benzoyl-3-(2,6-dimethyl-l-piperidinyl)-4-(( (phenyl¬ methyl)thio)methyl)-sydnonimin;N-benzoyl-3- (2,6-dimethyl-l-piperidinyl) -4 - (((phenyl¬ methyl) thio) methyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)tetra-N-(ethoxycarbonyl)-4-3- (2,6-dimethyl-l-piperidinyl) tetra-N- (ethoxycarbonyl) -4-
(( (phenylmethyl)thio)methyl)-sydnonimin; 3-(2,6-Dimethyl-1-piperidinyl)-4-( ((phenylmethyl)thio)- methyl)-sydnonimi ;(((phenylmethyl) thio) methyl) -sydnonimine; 3- (2,6-dimethyl-1-piperidinyl) -4- (((phenylmethyl) thio) methyl) -sydnonimi;
3-(4-Morpholinyl)-4-(((phenylmethyl)thio)methyl)-sydnon¬ imin;3- (4-morpholinyl) -4 - (((phenylmethyl) thio) methyl) -sydnon¬ imine;
N-Benzoyl-3-(2,6-dimethyl-l-piperidinyl)-4-( (phenylthio)- methyl)-sydnonimin;N-benzoyl-3- (2,6-dimethyl-l-piperidinyl) -4- ((phenylthio) methyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-((phenylthio)methyl)- sydnonimine;3- (2,6-dimethyl-l-piperidinyl) -4 - ((phenylthio) methyl) sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-( (2-propenylthio)- methyl)-sydnonimin; N-Benzoyl-3-(2,6-dimethyl-l-piperidinyl)-4-( (ethylthio)- methyl)-sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -4- ((2-propenylthio) methyl) -sydnonimine; N-benzoyl-3- (2,6-dimethyl-l-piperidinyl) -4- ((ethylthio) - methyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-N-(ethoxycarbonyl)-4-3- (2,6-dimethyl-l-piperidinyl) -N- (ethoxycarbonyl) -4-
( (ethyl hio)methyl)-sydnonimin;((ethyl hio) methyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-4-( (ethyl hio)methyl)- sydnonimin;3- (2,6-dimethyl-l-piperidinyl) -4- ((ethyl hio) methyl) sydnonimine;
3-(Cyclohexyl(1,1-dimethylethyl)amino)-sydnonimin;3- (cyclohexyl (1,1-dimethylethyl) amino) -sydnonimine;
3-(Tricyclo(3.3.1.13,7)dec-l-ylamino)-sydnonimin;3- (tricyclo (3.3.1.13,7) dec-l-ylamino) -sydnonimine;
N-(Ethoxycarbonyl)-3-((2-hydroxycyclohexyl)amino)-sydnon¬ imin; N-(4-Chlorbenzoyl)-3-((2-hydroxycyclohexyl)amino)-sydnon¬ imin;N- (ethoxycarbonyl) -3 - ((2-hydroxycyclohexyl) amino) -sydnon¬ imine; N- (4-chlorobenzoyl) -3 - ((2-hydroxycyclohexyl) amino) -sydnon¬ imine;
N-(Cyclohexylcarbonyl)-3-((2-hydroxycyclohexyl)amino)- sydnonimin;N- (cyclohexylcarbonyl) -3 - ((2-hydroxycyclohexyl) amino) sydnonimine;
N-Benzoyl-3-((2-hydroxycyclohexyl)amino)-sydnonimin; 3-( (2-Hydroxycyclohexyl)amino)-sydnonimin;N-benzoyl-3 - ((2-hydroxycyclohexyl) amino) -sydnonimine; 3- ((2-Hydroxycyclohexyl) amino) -sydnonimine;
3-(Cyclohexylamino)-sydnonimin;3- (cyclohexylamino) -sydnonimine;
N-(Ethoxycarbonyl)-3-(ethylamino)-sydnonimin;N- (ethoxycarbonyl) -3- (ethylamino) -sydnonimine;
3-(Ethylamino)-sydnonimin;3- (ethylamino) -sydnonimine;
3-( (2-Hydroxyethyl)amino)-sydnonimin; 3-(2,2-Dimethyl-l-pyrrolidinyl)-sydnonimin;3- ((2-Hydroxyethyl) amino) -sydnonimine; 3- (2,2-dimethyl-l-pyrrolidinyl) sydnonimine;
3-(2,2-Dimethyl-4-(1-methylethyl)-1-piperazinyl)-N-(2- methyl-1-oxopropyl)-sydnonimin;3- (2,2-dimethyl-4- (1-methylethyl) -1-piperazinyl) -N- (2-methyl-1-oxopropyl) sydnonimine;
N-(Cyclohexylcarbonyl)-3-(2,2-dimethyl-4-morpholinyl)- sydnonimin; 3-(2,2-Dimethyl-l-piperidinyl)-N-(ethoxycarbonyl)-sydnon¬ imin;N- (cyclohexylcarbonyl) -3- (2,2-dimethyl-4-morpholinyl) sydnonimine; 3- (2,2-dimethyl-l-piperidinyl) -N- (ethoxycarbonyl) -sydnon¬ imine;
N-Acetyl-3-(2,2-dimethyl-l-piperidinyl)-sydnonimin;N-acetyl-3- (2,2-dimethyl-l-piperidinyl) sydnonimine;
3-(4-Chlorbenzoyl)-sydnonimin;3- (4-chlorobenzoyl) -sydnonimine;
3-(2,2-Dimethyl-4-(1-methylethyl)-1-piperazinyl)-sydnon- imin;3- (2,2-dimethyl-4- (1-methylethyl) -1-piperazinyl) sydnone imine;
3-(2,2-Dimethyl-l-piperidinyl)-sydnonimin;3- (2,2-dimethyl-l-piperidinyl) -sydnonimine;
3-(3,3-Dimethyl-4-morpholinyl)-sydnonimin;3- (3,3-dimethyl-4-morpholinyl) -sydnonimine;
3-( (2-(bis(1-Methylethyl)amino)ethyl) (1,1-dimethylethyl)- amino)-N-(2,2-dimethyl-l-oxopropyl)-sydnonimin; N-Acetyl-3-( (2-(dimethylamino)ethyl) (1,1-dimethylethyl)- amino)-sydnonimi ;3- ((2- (bis (1-methylethyl) amino) ethyl) (1,1-dimethylethyl) amino) -N- (2,2-dimethyl-l-oxopropyl) sydnonimine; N-acetyl-3- ((2- (dimethylamino) ethyl) (1,1-dimethylethyl) - amino) -sydnonimi;
N-(Cyclohexylcarbonyl)-3-( (1,1-dimethylethyl) (2-(1- methylethoxy)ethyl)amino)-sydnonimin;N- (cyclohexylcarbonyl) -3- ((1,1-dimethylethyl) (2- (1-methylethoxy) ethyl) amino) -sydnonimine;
N-Benzoyl-3-((1,1-dimethylethyl) (2-methoxyethyl)amino)- sydnonimin; ; .N-benzoyl-3 - ((1,1-dimethylethyl) (2-methoxyethyl) amino) sydnonimine; ; .
3-( (1,1-Dirnethylethyl) (2-(4-morpholinyl)ethyl)amino)- sydnonimin;3- ((1,1-dirnethylethyl) (2- (4-morpholinyl) ethyl) amino) sydnonimine;
3-((2-(bis(1-Methylethyl)amino)ethyl) (1,1-dimethylethyl)- amino)-sydnonimin; 3-((2-(Dimethylamino)ethyl) (1,1-dimethylethyl)amino)- sydnonimin;3 - ((2- (bis (1-Methylethyl) amino) ethyl) (1,1-dimethylethyl) amino) -sydnonimine; 3 - ((2- (dimethylamino) ethyl) (1,1-dimethylethyl) amino) sydnonimine;
3-( (1,1-Dimethylethyl) (2-(1-methylethoxy)ethyl)amino)- sydnonimin;3- ((1,1-dimethylethyl) (2- (1-methylethoxy) ethyl) amino) sydnonimine;
3-((1,1-Dimethylethyl) (2-methoxyethyl)amino)-sydnonimin; 3-((l,l-Dimethylethyl)(2-hydroxyethy1)amino)-N-(ethoxy¬ carbonyl)-sydnonimin;3 - ((1,1-dimethylethyl) (2-methoxyethyl) amino) -sydnonimine; 3 - ((l, l-dimethylethyl) (2-hydroxyethy1) amino) -N- (ethoxycarbonyl) -sydnonimine;
3-((1,1-Dimethylethyl)(2-hydroxyethyl)amino)-sydnonimin;3 - ((1,1-dimethylethyl) (2-hydroxyethyl) amino) -sydnonimine;
3-( -Ethoxyphenyl)-sydnonimin;3- (-ethoxyphenyl) -sydnonimine;
3-(2,6-Dimethyl-l-piperidinyl)-sydnonimin; -(Ethoxycarbonyl)-3-(2,2,6,6-tetramethyl-l-piperidinyl)- sydnonimin; —3- (2,6-dimethyl-1-piperidinyl) sydnonimine; - (Ethoxycarbonyl) -3- (2,2,6,6-tetramethyl-l-piperidinyl) sydnonimine; -
3-(2,2,6,6-Tetramethyl-1-piperidinyl)-sydnonimin;3- (2,2,6,6-tetramethyl-1-piperidinyl) sydnonimine;
4-Benzoyl-3-((phenylmethyl) mino)-sydnonimin;4-benzoyl-3 - ((phenylmethyl) mino) -sydnonimine;
N-(Ethoxycarbonyl)-3-(4-morpho1iny1)-sydnonimi ; 3-(4-(Ethoxycarbonyl)-1-piperazinyl)-sydnonimin;N- (ethoxycarbonyl) -3- (4-morpholiny1) -sydnonimi; 3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnonimine;
N-((2-Propenylthio)acetyl)-3-(1-pyrrolidinyl)-sydnonimin;N - ((2-propenylthio) acetyl) -3- (1-pyrrolidinyl) -sydnonimine;
3-(1-Piperidinyl)-N-( (2-propenylthio)acetyl)-sydnonimin;3- (1-piperidinyl) -N- ((2-propenylthio) acetyl) -sydnonimine;
3-(Dimethylamino)-N-( (2-propenylthio)acetyl)-sydnonimin;3- (dimethylamino) -N- ((2-propenylthio) acetyl) -sydnonimine;
3-(Methyl(tetrahydro-3-thienyl)amino)-N-((2-propenyl- thio)acetyl)-sydnonimin;3- (methyl (tetrahydro-3-thienyl) amino) -N - ((2-propenyl-thio) acetyl) -sydnonimine;
N-( (2-Propenylthio)acetyl)-3-(4-thiomorpholinyl)-sydnon¬ imin;N- ((2-propenylthio) acetyl) -3- (4-thiomorpholinyl) -sydnon¬ imine;
3-(4-((Dimethylamino)sulfonyl)-1-piperazinyl)-N-((2-pro- penylthio)acetyl)-sydnonimin; 3-(4-(Methylsulfonyl)-1-piperazinyl)-N-.((2-propenylthio)- acetyl)-sydnonimi ;3- (4 - ((Dimethylamino) sulfonyl) -1-piperazinyl) -N - ((2-propenylthio) acetyl) -sydnonimine; 3- (4- (Methylsulfonyl) -1-piperazinyl) -N -. ((2-propenylthio) - acetyl) sydnonimi;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-((2-propenylthio)- acetyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -N - ((2-propenylthio) acetyl) -sydnonimine;
3-(4-Morpholinyl)-N-( (2-propenylthio)acetyl)-sydnonimin; 3-Methyl-4-(1-methylethyl)-sydnonimin;3- (4-morpholinyl) -N- ((2-propenylthio) acetyl) -sydnonimine; 3-methyl-4- (1-methylethyl) sydnonimine;
N~( ( (4-((2-(Diethylamino)ethoxy)carbonyl)phenyl)amino)- carbonyl)-3-(l-methyl-2-phenylethyl)-sydnonimin; N ~ ((( 4 - (( 2 - (diethylamino) ethoxy) carbonyl) phenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine;
N-(((4-Aminophenyl)amino)carbonyl)-3-(1-methyl-2-phenyl- ethyl)-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-( (phenylamino)carbonyl)- sydnonimin;N - (((4-aminophenyl) amino) carbonyl) -3- (1-methyl-2-phenyl-ethyl) -dydnonimine; 3- (1-methyl-2-phenylethyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-( ( (4-sulfophenyl)amino)- carbon l)-sydnonimin;3- (l-methyl-2-phenylethyl) -N- (((4-sulfophenyl) amino) carbon 1) -sydnonimine;
N-(((4-Chlor-3-hydroxyphenyl)amino)carbonyl)-3-(1-methyl- 2-phenylethyl)-sydnonimin;N - (((4-chloro-3-hydroxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-(((4-nitrophenyl)amino)- carbonyl)-sydnonimin;3- (l-methyl-2-phenylethyl) -N - (((4-nitrophenyl) amino) carbonyl) -sydnonimine;
N-(( (3-Chlor-4-methylphenyl)amino)carbonyl)-3-(1-methyl-N - (((3-chloro-4-methylphenyl) amino) carbonyl) -3- (1-methyl-
2-phenylethyl)-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-(((2,4,6-trimethylphenyl)- amino)-carbonyl)-sydnonimin; - _2-phenylethyl) sydnonimine; 3- (1-methyl-2-phenylethyl) -N - (((2,4,6-trimethylphenyl) amino) carbonyl) -sydnonimine; - _
N-(((2,6-Dimethylphenyl)amino)carbonyl)-3-(l-methyl-2- phenylethyl)-sydnonimin;N - (((2,6-dimethylphenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine;
N-(((2-Methylphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl- ethyl)-sydnonimin;N - (((2-methylphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -sydnonimine;
N-l,3,2-Dioxaphospholan-2-yl-3-(1-methyl-2-phenylethyl)- sydnonimin;N-1,2,3-dioxaphospholan-2-yl-3- (1-methyl-2-phenylethyl) sydnonimine;
4-(4-Chlorphenyl)-3-(2,3-dihydro-l ,5-dimethyl-3-oxo-2- phenyl-lH-pyrazol-4-yl)-sydnonimin; 4-(2-Chlorphenyl)-3-(2,3-dihydro-l,5-dimethyl-3-oxo-2- pheny1-1 H-pyrazo1-4-y1)-sydnonimin;4- (4-chlorophenyl) -3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -sydnonimine; 4- (2-chlorophenyl) -3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-pheny1-1 H-pyrazo1-4-y1) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(1-methylethyl)-sydnonimin;3- (2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (1-methylethyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(2-phenylethenyl)-sydnonimin; 3- ( 2 , 3-Dihydro-l , 5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(2-furanyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (2-phenylethenyl) sydnonimine; 3- (2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (2-furanyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-3-( -methoxyphenyl)-sydnonimin; 3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-ρyrazol-4- yl)-4-(4-nitrophenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -3- (-methoxyphenyl) -sydnonimine; 3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-ρyrazol-4-yl) -4- (4-nitrophenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(3-nitrophenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (3-nitrophenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(4-(dimethylamino)phenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (4- (dimethylamino) phenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-( -hydroxy-3-methoxyphenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (-hydroxy-3-methoxyphenyl) -sydnonimine;
4-(3,5-Dibrom-2-hydroxyphenyl)-3-(2,3-dihydro-l,5-di- methyl-3-oxo-2-phenyl-lH-pyrazol-4-yl)-sydnonimin; 4-(3-Brom-2-hydroxyphenyl)-3-(2,3-dihydro-l,5-dimethyl-4- (3,5-dibromo-2-hydroxyphenyl) -3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4-yl) -sydnonimine; 4- (3-bromo-2-hydroxyphenyl) -3- (2,3-dihydro-l, 5-dimethyl-
3-oxo-2-phenyl-lH-pyrazol-4-yl)-sydnonimin;3-oxo-2-phenyl-1H-pyrazol-4-yl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(4-hydroxyphenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (4-hydroxyphenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(3-hydroxyphenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (3-hydroxyphenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-(2-hydroxyphenyl)-sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4- (2-hydroxyphenyl) -sydnonimine;
3-(2,3-Dihydro-l,5-dimethyl-3-oxo-2-phenyl-lH-pyrazol-4- yl)-4-phenyl-sydnonimin; N-(Dichlorphosphinothioyl)-3-(l-methyl-2-phenylethyl)- sydnonimin;3- (2,3-dihydro-l, 5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl) -4-phenyl-sydnonimine; N- (dichlorophosphinothioyl) -3- (l-methyl-2-phenylethyl) sydnonimine;
3-(Methyl(tetrahydro-3-thienyl)amino)-sydnonimin;3- (methyl (tetrahydro-3-thienyl) amino) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-((2,6,6,7,7-penta- methylbicyclo(3.1.1)hept-3-yl)carbonyl)-sydnonimin; N-(3-Chlorbenzoyl)-3-(4-morpholinyl)-sydnonimin;3- (4- (Ethoxycarbonyl) -1-piperazinyl) -N - ((2,6,6,7,7-penta-methylbicyclo (3.1.1) hept-3-yl) carbonyl) -sydnonimine; N- (3-chlorobenzoyl) -3- (4-morpholinyl) -sydnonimine;
N-((Cyclohexyloxy)carbonyl)-3-(4-morpholinyl)-sydnonimin;N - ((Cyclohexyloxy) carbonyl) -3- (4-morpholinyl) -sydnonimine;
N-Acetyl-3-(methyl(tetrahydro-3-thienyl)amino)-sydnon¬ imin;N-acetyl-3- (methyl (tetrahydro-3-thienyl) amino) -sydnon¬ imine;
N-Acetyl-3-(bis(2-hydroxyethyl)amino)-sydnonimin; 3-(bis(2-Hydroxyethyl)amino)-N-( (phenylmethoxy)carbo- ny1)-sydnonimin;N-acetyl-3- (bis (2-hydroxyethyl) amino) -sydnonimine; 3- (bis (2-hydroxyethyl) amino) -N- ((phenylmethoxy) carbo- ny1) -sydnonimine;
3-(Dimethylamino)-N-(( (5-methyl-2-(1-methylethyl)cyclo- hexyl)-oxy)carbonyl)-sydnonimin;3- (dimethylamino) -N - (((5-methyl-2- (1-methylethyl) cyclohexyl) oxy) carbonyl) -sydnonimine;
N-(3-Methyl-l-oxopentyl)-3-(1-piperidinyl)-sydnonimin; 3-(Dimethylamino)-N—(•(2-methylbutoxy)carbonyl)-sydnon¬ imin;N- (3-methyl-l-oxopentyl) -3- (1-piperidinyl) -sydnonimine; 3- (dimethylamino) -N— ( • (2-methylbutoxy) carbonyl) -sydnon¬ imine;
N-( ( (5-Methyl-2-(1-methylethyl)cyclohexyl)oxy)carbonyl)-N- (((5-methyl-2- (1-methylethyl) cyclohexyl) oxy) carbonyl) -
3-(1-piperidinyl)-sydnonimin-;3- (1-piperidinyl) -sydnonimine-;
3-(Methyl(tetrahydro-3-thienyl) mino)-N-(((1,7,7-tri- methylbicyclo(2.2.1)hept-2-yl)oxy)carbonyl)-sydnonimin;3- (methyl (tetrahydro-3-thienyl) mino) -N - (((1,7,7-tri-methylbicyclo (2.2.1) hept-2-yl) oxy) carbonyl) -sydnonimine;
N-(2-Methoxy-l-oxopropyl)-3-(4-morpholinyl)-sydnonimin;N- (2-methoxy-l-oxopropyl) -3- (4-morpholinyl) -sydnonimine;
N-( (Acetyloxy)phenylacetyl)-3-(4-(ethoxycarbonyl)-1-pipe- razinyl)-sydnonimin;N- ((acetyloxy) phenylacetyl) -3- (4- (ethoxycarbonyl) -1-pipe-razinyl) -sydnonimine;
N-( (Acetyloxy)phenylacetyl)-3-(4-morpholinyl)-sydnonimin; N-(2-Methoxy-l-oxopropyl)-3-(4-(methylsulfonyl)-1-pipera- zinyl)-sydnonimin;N- ((acetyloxy) phenylacetyl) -3- (4-morpholinyl) -sydnonimine; N- (2-methoxy-l-oxopropyl) -3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(2-methoxy-l-oxo- propyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- (2-methoxy-l-oxo-propyl) -sydnonimine;
N-( ( (2,2-Dimethyl-l,3-dioxolan-4-yl)methoxy)carbonyl)-3- (4-(ethoxycarbonyl)-1-piperazinyl)-sydnonimin;N- (((2,2-Dimethyl-1,3-dioxolan-4-yl) methoxy) carbonyl) -3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(((1,7,7-tri- ethylbicyc lo(2.2.1)hept-2-yl)oxy)carbonyl)-sydnonimin;3- (4- (Ethoxycarbonyl) -1-piperazinyl) -N - ((((1,7,7-tri-ethylbicyclo (2.2.1) hept-2-yl) oxy) carbonyl) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(((2,6,6-tri- methyl-bicyclo(3.1.1)hept-3-yl)oxy)carbonyl)-sydnonimin; 3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-( ( (5-methyl-2-(1- methylethyl)cyclohexyl)oxy)carbonyl)-sydnonimin;3- (4- (Ethoxycarbonyl) -1-piperazinyl) -N - (((2,6,6-trimethyl-bicyclo (3.1.1) hept-3-yl) oxy) carbonyl) -sydnonimine; 3- (4- (Ethoxycarbonyl) -1-piperazinyl) -N- (((5-methyl-2- (1-methylethyl) cyclohexyl) oxy) carbonyl) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-( (2-ethoxy-l- methyl-2-oxoethoxy)carbonyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- ((2-ethoxy-l-methyl-2-oxoethoxy) carbonyl) -sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-( (2-methylbutoxy)- carbonyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- ((2-methylbutoxy) carbonyl) -sydnonimine;
3-(4-Morpholinyl)-N-(((2,6,6-trimethylbicyclo(3.1.1)- hept-3-y1)ox )carbonyl)-sydnonimin;3- (4-Morpholinyl) -N - (((2,6,6-trimethylbicyclo (3.1.1) - hept-3-y1) ox) carbonyl) -sydnonimine;
3-(4-Morpholinyl)-N-(((1,7,7-trimethylbicyclo(2.2.1)- hept-2-yl)oxy)carbonyl)-sydnonimin; N-( ( (5-Methyl-2-(l-methylethyl)cyclohexyl)oxy)carbonyl)- 3_(4-morpholinyl)-sydnonimin;3- (4-morpholinyl) -N - ((((1,7,7-trimethylbicyclo (2.2.1) - hept-2-yl) oxy) carbonyl) -sydnonimine; N- (((5-methyl-2- (l-methylethyl) cyclohexyl) oxy) carbonyl) - 3_ (4-morpholinyl) -sydnonimine;
N-((2-Ethoxy-l-methyl-2-oxoethoxy)carbonyl)-3-(4-morpho- linyl)-sydnonimin;N - ((2-ethoxy-l-methyl-2-oxoethoxy) carbonyl) -3- (4-morpholinoyl) -sydnonimine;
N-( (2-Methylbutoxy)carbonyl)-3-(4-morpholinyl)-sydnon- i in;N- ((2-methylbutoxy) carbonyl) -3- (4-morpholinyl) -sydnone-i in;
3-(4-(Methylsulfonyl)-1-piperazinyl)-N-(((2,6,6-trime- thylbicyclo(3.1.1)hept-3-yl)oxy)carbonyl)-sydnonimin;3- (4- (Methylsulfonyl) -1-piperazinyl) -N - (((2,6,6-trimethylbicyclo (3.1.1) hept-3-yl) oxy) carbonyl) -sydnonimine;
N-(((5-Methyl-2-(1-methylethyl)cyclohexyl)oxy)carbonyl)-N - (((5-methyl-2- (1-methylethyl) cyclohexyl) oxy) carbonyl) -
3-(4-(methylsulfonyl)-1-piperazinyl)-sydnonimin; N-(((2,2-Dimethyl-l,3-dioxolan-4-yl)methoxy)carbonyl)-3-3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine; N - (((2,2-dimethyl-1,3-dioxolan-4-yl) methoxy) carbonyl) -3-
(4-morpholinyl)-sydnonimi ;(4-morpholinyl) -sydnonimi;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(2-methoxy-l-oxo- propyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- (2-methoxy-l-oxo-propyl) -sydnonimine;
N-((2-Methylbutoxy)carbonyl)-3-(4-(methylsulfonyl)-1-pi- perazinyl)-sydnonimin;N - ((2-methylbutoxy) carbonyl) -3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine;
3-(bis(2-Hydroxyethyl)amino)-N-(ethoxycarbonyl)-sydnon¬ imin;3- (bis (2-hydroxyethyl) amino) -N- (ethoxycarbonyl) -sydnon¬ imine;
N-Methyl-3-phenyl-sydnonimin;N-methyl-3-phenyl-sydnonimine;
N-( -Methyl-l,3,2-dioxaphosphorinan-2-yl)-3-(1-methyl-2- phenylethyl)-sydnonimin;N- (-Methyl-l, 3,2-dioxaphosphorinan-2-yl) -3- (1-methyl-2-phenylethyl) -sydnonimine;
4-(3-Nitrophenyl)-3-(phenylmethyl)-sydnonimin;4- (3-nitrophenyl) -3- (phenylmethyl) -sydnonimine;
4-(4-(bis(2-Chlorethyl) mino)phenyl)-3-phenyl-sydnonimin;4- (4- (bis (2-chloroethyl) mino) phenyl) -3-phenyl-sydnonimine;
3-(4-((Diethylamino)sulfonyl)phenyl)-sydnonimin;3- (4 - ((Diethylamino) sulfonyl) phenyl) -sydnonimine;
3-(4-(1-Pyrrolidinylsulfonyl)phenyl)-sydnonimin; 3-(4-(1-Piperidinylsulfonyl)phenyl)-sydnonimin;3- (4- (1-pyrrolidinylsulfonyl) phenyl) -sydnonimine; 3- (4- (1-piperidinylsulfonyl) phenyl) -sydnonimine;
3-(4-(4-Morpholinylsulfonyl) henyl)-sydnonimin;3- (4- (4-morpholinylsulfonyl) henyl) -sydnonimine;
3-( -((Ethylphenylamino)sulfonyl)phenyl)-sydnonimin;3- (- ((Ethylphenylamino) sulfonyl) phenyl) -sydnonimine;
3-(4-((Methylphenylamino)sulfonyl)phenyl)-sydnonimin;3- (4 - ((Methylphenylamino) sulfonyl) phenyl) -sydnonimine;
3-(3-0xa-9-azabicyclo(3.3.1)non-9-yl)-sydnonimin; 3-(3-0xa-8-azabicyclo(3.2.1)oct-8-yl)-sydnonimin;3- (3-0xa-9-azabicyclo (3.3.1) non-9-yl) -sydnonimine; 3- (3-0xa-8-azabicyclo (3.2.1) oct-8-yl) -sydnonimine;
3-(2-((3-Pyridinylcarbonyl)amino)ethyl)-sydnonimin;3- (2 - ((3-Pyridinylcarbonyl) amino) ethyl) -sydnonimine;
N-(Ethoxycarbonyl)-3-(3-oxa-9-azabicyclo(3.3.1)non-9- yl)-sydnonimin;N- (ethoxycarbonyl) -3- (3-oxa-9-azabicyclo (3.3.1) non-9-yl) -sydnonimine;
N-(Ethoxycarbonyl)-3-(3-oxa-8-azabicyclo(3.2.1)oct-8- yl)-sydnonimin; 3-(4-Thiomorpholinyl)-sydnonimin;N- (ethoxycarbonyl) -3- (3-oxa-8-azabicyclo (3.2.1) oct-8-yl) -sydnonimine; 3- (4-thiomorpholinyl) -sydnonimine;
3-(2-Hydroxy-2-phenylethyl)-N-( (phenylamino)carbonyl)- sydnonimin;3- (2-hydroxy-2-phenylethyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-(2-(((Diethylamino)acetyl)oxy)-2-phenylethyl)-N-( (phe- nylamino)carbonyl)-sydnonimin;3- (2 - (((diethylamino) acetyl) oxy) -2-phenylethyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-(2-( (Chloracetyl)oxy)-2-phenylethyl)-N-( (phenylamino)- carbonyl)-sydnonimin;3- (2- ((Chloroacetyl) oxy) -2-phenylethyl) -N- ((phenylamino) carbonyl) -sydnonimine;
3-(2-Hydroxy-2-(3-hydroxyphenyl)ethyl)-sydnonimin;3- (2-hydroxy-2- (3-hydroxyphenyl) ethyl) -sydnonimine;
N-(4-(Chlormethyl)tetrahydro-7,7-dimethyl-4H-(1,3)dioxo- lo(4,5)furo(3,2-d)-1,3,2-dioxaphosphoran-2-yl)-3-(1- methyl-2-phenylethyl)-sydnonimin;N- (4- (chloromethyl) tetrahydro-7,7-dimethyl-4H- (1,3) dioxolo (4,5) furo (3,2-d) -1,3,2-dioxaphosphorane-2- yl) -3- (1-methyl-2-phenylethyl) -sydnonimine;
N-(Diethoxyphosphinyl)-3-(1-methyl-2-phenylethyl)-sydnon¬ imin;N- (diethoxyphosphinyl) -3- (1-methyl-2-phenylethyl) -sydnon¬ imine;
N-(Dipropoxyphosphinyl)-3-(1-methyl-2-phenylethyl)-syd- nonimin;N- (dipropoxyphosphinyl) -3- (1-methyl-2-phenylethyl) -syd-nonimin;
N-l,3,2-Benzodioxaphosphol-2-yl-3-(1-methyl-2-phenyl¬ ethyl)-sydnonimin;N-1,2,3-benzodioxaphosphol-2-yl-3- (1-methyl-2-phenylethyl) -sydnonimine;
N-(5,5-Dimethyl-l,3,2-dioxaphosphorinan-2-yl)-3-(1-me- thyl-2-phenylethyl)-sydnonimin; N-(4-Methyl-l,3,2-dioxaphosphorinan-2-yl)-3-(l-methyl-2- phenylethyl)-sydnonimin;N- (5,5-dimethyl-l, 3,2-dioxaphosphorinan-2-yl) -3- (1-methyl-2-phenylethyl) sydnonimine; N- (4-methyl-l, 3,2-dioxaphosphorinan-2-yl) -3- (l-methyl-2-phenylethyl) sydnonimine;
N-(Ethoxycarbonyl)-3-(4-(5-oxo-5-phenylpentyl)-1-pipera- ziny1)-sydnonimine;N- (ethoxycarbonyl) -3- (4- (5-oxo-5-phenylpentyl) -1-piperaziny1) -sydnonimine;
N-Benzoyl-3-(4-(4-benzoyl-6-methylheptyl)-1-piperazinyl)- sydnonimin;N-benzoyl-3- (4- (4-benzoyl-6-methylheptyl) -1-piperazinyl) sydnonimine;
N-(Ethoxycarbonyl)-3-(4-(9-oxo-9-phenylnonyl)-1-piperazi- nyl)-sydnonimin;N- (ethoxycarbonyl) -3- (4- (9-oxo-9-phenylnonyl) -1-piperazinyl) sydnonimine;
N-(Ethoxycarbonyl)-3-(4-(2-oxo-2-phenylethyl)-1-piperazi- nyl)-sydnonimin; N-Benzoyl-3-(4-(2-oxo-2-phenylethyl)-1-piperazinyl)-syd¬ nonimin;N- (ethoxycarbonyl) -3- (4- (2-oxo-2-phenylethyl) -1-piperazinyl) sydnonimine; N-benzoyl-3- (4- (2-oxo-2-phenylethyl) -1-piperazinyl) -syd nonimin;
N-Acetyl-3-(4-(2-oxo-2-phenylethyl)-1-piperazinyl)-syd¬ nonimin;N-acetyl-3- (4- (2-oxo-2-phenylethyl) -1-piperazinyl) hydroxydimine;
3-(4-(4-Benzoyl-6-methylheptyl)-1-piperazinyl)-sydnon- imin; 3-(4-(9-0xo-9-phenylnonyl)-1-piperazinyl)-sydnonimin; 3-(4-(7-0xo-7-phenylheptyl)-1-piperazinyl)-sydnonimin; 3-(4-(6-0xo-6-phenylhexyl)-1-piperazinyl)-sydnonimin; 3-(4-(4-0xo-4-phenylbutyl)-1-piperazinyl)-sydnonimin; 3-Methyl-N-(trimethylsilyl)-sydnonimin;3- (4- (4-Benzoyl-6-methylheptyl) -1-piperazinyl) sydnone imine; 3- (4- (9-0xo-9-phenylnonyl) -1-piperazinyl) sydnonimine; 3- (4- (7-0xo-7-phenylheptyl) -1-piperazinyl) sydnonimine; 3- (4- (6-0xo-6-phenylhexyl) -1-piperazinyl) sydnonimine; 3- (4- (4-0xo-4-phenylbutyl) -1-piperazinyl) sydnonimine; 3-methyl-N- (trimethylsilyl) -sydnonimine;
3-(1-(Hydroxymethyl)-2-phenylethyl)-sydnonimin; 3-(1-(hydroxymethyl)-2-phenylethyl)-N-( phenylamino)car¬ bonyl)-sydnonimin; N-((( -Chlorphenyl)amino)carbonyl)-3-(1-(hydroxymethyl)- 2-phenylethyl)-sydnonimin;3- (1- (hydroxymethyl) -2-phenylethyl) sydnonimine; 3- (1- (hydroxymethyl) -2-phenylethyl) -N- (phenylamino) carbonyl) -sydnonimine; N - (((chlorophenyl) amino) carbonyl) -3- (1- (hydroxymethyl) -2-phenylethyl) -sydnonimine;
3-(Methyl(phenylmethyl)amino)-N-((phenylamino)carbonyl)- sydnonimin;3- (methyl (phenylmethyl) amino) -N - ((phenylamino) carbonyl) sydnonimine;
3-(4-(Ethoxycarbonyl.)phenyl)-4-(2-methylpropyl)-sydnon¬ imin; 3-(4-(Ethoxycarbonyl)phenyl)-4-(2-furanylmethyl)-sydnon¬ imin;3- (4- (Ethoxycarbonyl.) Phenyl) -4- (2-methylpropyl) -sydnon¬ imine; 3- (4- (ethoxycarbonyl) phenyl) -4- (2-furanylmethyl) -sydnon¬ imine;
3-(4-(Ethoxycarbonyl)phenyl)-4-( -methoxyphenyl)-sydnon¬ imin; 3-( -(Ethoxycarbonyl)phenyl)-4-(3-phenyl-2-propenyl)- sydnonimin;3- (4- (ethoxycarbonyl) phenyl) -4- (-methoxyphenyl) -sydnon¬ imine; 3- (- (Ethoxycarbonyl) phenyl) -4- (3-phenyl-2-propenyl) sydnonimine;
3-(4-(Ethoxycarbonyl)phenyl)-4-(4-hydroxy-3-methoxyphe- nyl)-sydnonimi ;3- (4- (ethoxycarbonyl) phenyl) -4- (4-hydroxy-3-methoxyphenyl) sydnonimi;
4-(3,5-Dibrom-2-hydroxyphenyl)-3-(4-(ethoxycarbonyl)phe¬ nyl)-sydnonimin; 4-(3-Brom-2-hydroxyphenyl)-3-(4-(ethoxycarbonyl)phenyl)- sydnonimin;4- (3,5-dibromo-2-hydroxyphenyl) -3- (4- (ethoxycarbonyl) phenyl) -sydnonimine; 4- (3-bromo-2-hydroxyphenyl) -3- (4- (ethoxycarbonyl) phenyl) sydnonimine;
3-(4-(Ethoxycarbonyl)phenyl)-4-(4-hydroxyphenyl)-sydnon¬ imin; 3-(4-(Ethoxycarbonyl)phenyl)-4-(3-hydroxyphenyl)-sydnon- imin;3- (4- (ethoxycarbonyl) phenyl) -4- (4-hydroxyphenyl) -sydnon¬ imine; 3- (4- (ethoxycarbonyl) phenyl) -4- (3-hydroxyphenyl) sydnone imine;
3-(4-(Ethoxycarbonyl)phenyl)-4-(2-hydroxyphenyl)-sydnon¬ imin;3- (4- (ethoxycarbonyl) phenyl) -4- (2-hydroxyphenyl) -sydnon¬ imine;
3-(4-(Ethoxycarbonyl)phenyl)-4-phenyl-sydnonimin; N-( -Methyl-l,3,2-dioxaphosphorinan-2-yl)-3-(l-methyl-2- phenylethyl)-sydnonimin; 3-(4-(5-0xo-5-phenylpentyl)-1-piperazinyl)-sydnonimin; N-(Methoxyacetyl)-3-(methyl(tetrahydro-3-thienyl)amino)- sydnonimin; N-Acetyl-3-(4-(ethoxycarbonyl)-1-piperazinyl)-sydnonimin; N-(4-Methoxybenzoyl)-3-(methyl(tetrahydro-3-thienyl)ami¬ no)-sydnonimin;3- (4- (ethoxycarbonyl) phenyl) -4-phenyl-sydnonimine; N- (-Methyl-l, 3,2-dioxaphosphorinan-2-yl) -3- (l-methyl-2-phenylethyl) -sydnonimine; 3- (4- (5-0xo-5-phenylpentyl) -1-piperazinyl) sydnonimine; N- (methoxyacetyl) -3- (methyl (tetrahydro-3-thienyl) amino) sydnonimine; N-acetyl-3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnonimine; N- (4-methoxybenzoyl) -3- (methyl (tetrahydro-3-thienyl) amino) -nonnimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-({2-,6,6-trimethyl- bicyclo(3.1.1)hept-3-yl)carbonyl)-sydnonimin; 3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(tricyclo- (3.3.1.13,7)dec-l-ylcarbonyl)-sydnonimin;3- (4- (Ethoxycarbonyl) -1-piperazinyl) -N - ({2-, 6,6-trimethyl-bicyclo (3.1.1) hept-3-yl) carbonyl) -sydnonimine; 3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- (tricyclo- (3.3.1.13,7) dec-l-ylcarbonyl) -sydnonimine;
N-(2,2-Dimethyl-l-oxopropyl)-3-(4-(ethoxycarbonyl)-1-pi- perazinyl)-sydnonimin;N- (2,2-dimethyl-l-oxopropyl) -3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnonimine;
N-(4-Chlorbenzoyl)-3-(4-(ethoxycarbonyl)-1-piperazinyl)- sydnonimin; 3-(4-(Ethoxycarbonyl)-1-piperazinyl)-N-(ethoxyoxoacetyl)- sydnonimin;N- (4-chlorobenzoyl) -3- (4- (ethoxycarbonyl) -1-piperazinyl) sydnonimine; 3- (4- (ethoxycarbonyl) -1-piperazinyl) -N- (ethoxyoxoacetyl) sydnonimine;
N-Benzoyl-3-(4-(ethoxycarbonyl)-1-piperazinyl)-sydnon¬ imin; N-(Cyclohexylcarbonyl)-3-(4-(ethoxycarbonyl)-1-piperazi- nyl)-sydnonimin;N-benzoyl-3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnon¬ imine; N- (cyclohexylcarbonyl) -3- (4- (ethoxycarbonyl) -1-piperazinyl) sydnonimine;
N-(Ethoxycarbonyl)-3-(4-(ethoxycarbonyl)-1-piperazinyl)- sydnonimin;N- (ethoxycarbonyl) -3- (4- (ethoxycarbonyl) -1-piperazinyl) sydnonimine;
N-(4-Methylbenzoyl)-3-(methyl(tetrahydro-3-thienyl)ami¬ no)-sydnonimin; N-(Cyclohexylcarbonyl)-3-(methyl(tetrahydro-3-thienyl)- amino)-sydnonimin;N- (4-methylbenzoyl) -3- (methyl (tetrahydro-3-thienyl) amino) -nydnonimine; N- (cyclohexylcarbonyl) -3- (methyl (tetrahydro-3-thienyl) amino) -sydnonimine;
3-(Methyl(tetrahydro-3-thienyl)amino)-N-(4-nitrobenzoyl)- sydnonimin; N-Benzoyl-3-(methyl(tetrahydro-3-thienyl)amino)-sydnon- imin;3- (methyl (tetrahydro-3-thienyl) amino) -N- (4-nitrobenzoyl) sydnonimine; N-benzoyl-3- (methyl (tetrahydro-3-thienyl) amino) -sydnonimine;
N-(Ethoxycarbonyl)-3-(methyl(tetrahydro-3-thienyl)amino)- sydnonimin;N- (ethoxycarbonyl) -3- (methyl (tetrahydro-3-thienyl) amino) sydnonimine;
3-(4-(Ethoxycarbonyl)-1-piperazinyl)-sydnonimin; 3-(Methyl(tetrahydro-3-thienyl)amino)-sydnonimin; N-( ( (4-Chlorphenyl)amino)carbonyl)-3-(2-hydroxy-2-phenyl- ethyl)-sydnonimin;3- (4- (ethoxycarbonyl) -1-piperazinyl) -sydnonimine; 3- (methyl (tetrahydro-3-thienyl) amino) -sydnonimine; N- (((4-chlorophenyl) amino) carbonyl) -3- (2-hydroxy-2-phenyl- ethyl) -sydnonimine;
3-(2-(( -Morpholinylacetyl)oxy)-2-phenylethyl)-N-((phe¬ nylamino)carbonyl)-sydnonimin;3- (2 - ((-Morpholinylacetyl) oxy) -2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
3-(2-((Chloracetyl)oxy)-2-phenylethyl)-N-( (phenylamino)- carbonyl)-sydnonimin;3- (2 - ((chloroacetyl) oxy) -2-phenylethyl) -N- ((phenylamino) - carbonyl) -sydnonimine;
N-( ( (4-Chlorphenyl)amino)carbonyl)-3-(2-(((diethylamino)- acetyl)oxy)-2-phenylethyl)-sydnonimin; .N- ((((4-chlorophenyl) amino) carbonyl) -3- (2 - (((diethylamino) acetyl) oxy) -2-phenylethyl) sydnonimine; .
N-( ((4-Chlorphenyl)amino)carbonyl)-3-(2-(( (diethylamino)- acetyl)oxy)-2-phenylethyl)-sydnonimin; 3-(2-(((4-Methyl-l-piperazinyl)acetyl)oxy)-2-phenyl- ethyl)N-( (phenylamino)carbonyl)-sydnonimin;N- ((((4-chlorophenyl) amino) carbonyl) -3- (2 - (((diethylamino) acetyl) oxy) -2-phenylethyl) sydnonimine; 3- (2 - (((4-methyl-l-piperazinyl) acetyl) oxy) -2-phenylethyl) N- ((phenylamino) carbonyl) -sydnonimine;
3-(2-((Chloracetyl)oxy)-2-phenylethyl)-N-(((4-chlorphe- nyl)amino)carbonyl)-sydnonimin;3- (2 - ((chloroacetyl) oxy) -2-phenylethyl) -N - (((4-chlorophenyl) amino) carbonyl) -sydnonimine;
3-(2-(((Diethylamino)acetyl)oxy)-2-phenylethyl)-N-((phe- nylamino)carbonyl)-sydnonimin;3- (2 - (((diethylamino) acetyl) oxy) -2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
3-(2-(((4-Methyl-l-piperazinyl) cetyl)oxy)-2-phenyl- ethyl)-N-((phenylamino)carbonyl)-sydnonimin;3- (2 - (((4-Methyl-1-piperazinyl) cetyl) oxy) -2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
N-(((4-Chlorphenyl)amino)carbonyl)-3-(2-phenyl-2-((tri- methylsilyl)ox )ethyl)-sydnonimin; 3-(2-(Acetyloxy)-2-phenylethyl)-N-(( (4-chlorphenyl)ami¬ no)carbonyl)-sydnonimin;N - (((4-chlorophenyl) amino) carbonyl) -3- (2-phenyl-2 - ((trimethylsilyl) ox) ethyl) -sydnonimine; 3- (2- (acetyloxy) -2-phenylethyl) -N - (((4-chlorophenyl) amino) carbonyl) -sydnonimine;
3-(2-(Dimethylamino)-2-phenylethyl)-sydnonimin;3- (2- (dimethylamino) -2-phenylethyl) -sydnonimine;
N-(4-Methyl-l,3,2-dioxaphosphorinan-2-yl)-3-(1-methyl-l- phenylethyl)-sydnonimin; N-l,3,2-Benzodioxaphosphol-2-yl-3-(1-methyl-l-phenyl- ethyl)-sydnonimin;N- (4-methyl-l, 3,2-dioxaphosphorinan-2-yl) -3- (1-methyl-l-phenylethyl) sydnonimine; N-l, 3,2-benzodioxaphosphol-2-yl-3- (1-methyl-l-phenyl-ethyl) -dydnonimine;
3-(1-( (( -Morpholinylacetyl)oxy)methyl)-2-phenylethyl)-3- (1- (((-Morpholinylacetyl) oxy) methyl) -2-phenylethyl) -
N-((phenylamino)carbonyl)-sydnonimin;N - ((phenylamino) carbonyl) -sydnonimine;
3-(1-((((4-Methyl-l-piperazinyl)acetyl)oxy)methyl) -2- phenyleth yl)-N-((phenylamino)carbonyl)-sydnonimin;3- (1 - ((((4-methyl-1-piperazinyl) acetyl) oxy) methyl) -2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
N-((( -Chlorphenyl)amino)carbonyl)-3-(1-(((4-morpholinyl- acetyl)oxy)methyl)-2-phenylethyl)-sydnonimin;N - (((-chlorophenyl) amino) carbonyl) -3- (1 - (((4-morpholinylacetyl) oxy) methyl) -2-phenylethyl) -sydnonimine;
3-(1-(((Chloracetyl)oxy)methyl)-2-phenylethyl)-N-((phe¬ nylamino)carbonyl)-sydnonimin; 3-(1-(Hydroxymethyl)-2-phenylethyl)-N-( (phenylamino)car- bony1)-sydnonimin;3- (1 - (((chloroacetyl) oxy) methyl) -2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine; 3- (1- (hydroxymethyl) -2-phenylethyl) -N- ((phenylamino) car- bony1) -sydnonimin;
N-( ( (4-Chlorphenyl)amino)carbonyl)-3-(1-(hydroxymethyl)-N- (((4-chlorophenyl) amino) carbonyl) -3- (1- (hydroxymethyl) -
2-phenylethyl)-sydnonimin;2-phenylethyl) sydnonimine;
3-(1-( (Acetyloxy)methyl)-2-phenylethyl)-N-( ( (4-chlorphe- nyl)amino)carbonyl)-sydnonimin;3- (1- ((acetyloxy) methyl) -2-phenylethyl) -N- (((4-chlorophenyl) amino) carbonyl) -sydnonimine;
N-(((4-(Methoxycarbonyl)phenyl)amino)carbonyl)-3-(1-me- thyl-2-phenylethyl)-sydnonimin;N - (((4- (methoxycarbonyl) phenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-( ( (4-Carboxyphenyl)amino)carbonyl)-3-(l-methyl-2-phe- nylethyl)-sydnonimin; N-( (Dimethylamino)carbonyl)-3-(1-methyl-2-phenylethyl)- sydnonimin;N- (((4-carboxyphenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) sydnonimine; N- ((dimethylamino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-( ( (4-Chlorphenyl)amino)carbonyl)-3-(2-(Dimethylamino)-N- (((4-chlorophenyl) amino) carbonyl) -3- (2- (dimethylamino) -
2-phenylethyl)-sydnonimin;2-phenylethyl) sydnonimine;
3-(2-(Dimethylamino)-2-phenylethyl)-N-((phenylamino)car- bonyl)-sydnonimin;3- (2- (dimethylamino) -2-phenylethyl) -N - ((phenylamino) carbonyl) sydnonimine;
3,3'-Methylenebis-sydnonimin;3,3'-methylenebis-sydnonimine;
3-(2-Hydroxy-1-methyl-2-phenylethyl)-sydnonimin;3- (2-hydroxy-1-methyl-2-phenylethyl) sydnonimine;
N-( ((4-Chlorphenyl)amino)carbonyl)-3-(2-hydroxy-2-phenyl- propyl)-sydnonimin; o 3-(l-Methyl-2-phenylethyl)-N-( ( (phenylmethyl)amino)carbo¬ nyl)-sydnonimin;N- (((4-chlorophenyl) amino) carbonyl) -3- (2-hydroxy-2-phenylpropyl) sydnonimine; o 3- (l-methyl-2-phenylethyl) -N- (((phenylmethyl) amino) carbonyl) -sydnonimine;
N~(( ((4-(Methoxycarbonyl)phenyl)methyl)amino)carbonyl)- N ~ ((((4- (methoxycarbonyl) phenyl) methyl) amino) carbonyl) -
3-(l-methyl-2-phenylethyl)-sydnonimin;3- (l-methyl-2-phenylethyl) -sydnonimine;
N_( ( ( ( -Carboxyphenyl)methyl)amino)carbonyl)-3-(1-methyl- 5 2-phenylethyl)-sydnonimin; N_ ((((-carboxyphenyl) methyl) amino) carbonyl) -3- (1-methyl- 5 2-phenylethyl) -sydnonimine;
N_( ( ( (4~(Ethoxycarbonyl)phenyl)methyl)amino)carbonyl)-3- N_ (((( 4 ~ (ethoxycarbonyl) phenyl) methyl) amino) carbonyl) -3-
(l-methyl-2-phenylethyl)-sydnonimin;(l-methyl-2-phenylethyl) sydnonimine;
N-( ( (2-Hydroxyphenyl)amino)carbonyl)-3-(1-methyl-2-phe¬ nylethyl)-sydnonimin; 0 N"( ( (2-Carboxyphenyl)amino)carbonyl)-3-(1-methyl-2-phe¬ nylethyl)-sydnonimin;N- (((2-hydroxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine; 0 N "(((2-carboxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-(((3-Carboxyphenyl)amino)carbonyl)-3-(1-methyl-2-phe¬ nylethyl)-sydnonimin;N - (((3-carboxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-( ( (4-(Methoxycarbonyl)phenyl)amino)carbonyl)-3-(1-me- 5 thyl-2-phenylethyl)-sydnonimin; N-((( -Carboxyphenyl)amino)carbonyl)-3-(l-methyl-2-phe- nylethyl)-sydnor -min;N- (((4- (methoxycarbonyl) phenyl) amino) carbonyl) -3- (1-me-5-thyl-2-phenylethyl) -sydnonimine; N - (((-carboxyphenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -nydnor -min;
N-((( -(Ethoxycarbonyl)phenyl)amino)carbonyl)-3-(1-me¬ thyl-2-phenylethyl)-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-((phenylamino)carbonyl)-syd¬ nonimin;N - (((((ethoxycarbonyl) phenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -dydnonimine; 3- (1-methyl-2-phenylethyl) -N - ((phenylamino) carbonyl) -syd¬ nonimin;
N-(Cyclohexylcarbonyl)-3-(4-(methylsulfonyl)-1-piperazi- nyl)-sydnonimi ; N-Formyl-3-( -thiomorpholinyl)-sydnonimin; 3-(4-( (Dimethylamino)sulfonyl)-1-piperazinyl)-sydnonimin; 3-(4-(( -Methylphenyl)sulfonyl)-1-piperazinyl)-sydnon¬ imin;N- (cyclohexylcarbonyl) -3- (4- (methylsulfonyl) -1-piperazinyl) sydnonimi; N-formyl-3- (-thiomorpholinyl) -sydnonimine; 3- (4- ((Dimethylamino) sulfonyl) -1-piperazinyl) -sydnonimine; 3- (4 - ((Methylphenyl) sulfonyl) -1-piperazinyl) -sydnon¬ imine;
3-(4-(Methylsulfonyl)-1-piperazinyl)-sydnonimin; 3-(4-Thiomorpholinyl)-sydnonimin; 4-Brom-N-(ethoxycarbonyl)-3-(4-thiomorpholinyl)-sydnon¬ imin;3- (4- (methylsulfonyl) -1-piperazinyl) sydnonimine; 3- (4-thiomorpholinyl) -sydnonimine; 4-bromo-N- (ethoxycarbonyl) -3- (4-thiomorpholinyl) -sydnon¬ imine;
4-Brom-N-(ethoxycarbonyl)-3-(4-(methylsulfonyl)-1-pipera- zinyl)-sydnonimin; N-nitroso-3-(4-thiomorpholinyl)-sydnonimin; N-((4-Methylphenyl)sulfonyl)-3-(4-thiomorpholinyl)-syd¬ nonimin;4-bromo-N- (ethoxycarbonyl) -3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine; N-nitroso-3- (4-thiomorpholinyl) sydnonimine; N - ((4-methylphenyl) sulfonyl) -3- (4-thiomorpholinyl) -syd nonimin;
N-((4-Methylphenyl)sulfonyl)-3-(4-(methylsulfonyl)-1-pi- perazinyl)-sydnonimin; N-(Butoxyacetyl)-3-(4-((4-methylphenyl)sulfonyl)-1-pipe- razinyl)-sydnonimin;N - ((4-methylphenyl) sulfonyl) -3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine; N- (butoxyacetyl) -3- (4 - ((4-methylphenyl) sulfonyl) -1-pipe-razinyl) -sydnonimine;
3-(4-((4-Methylphenyl)sulfonyl)-1-piperazinyl)-N-(phenyl- acetyl)-sydnonimin;3- (4 - ((4-Methylphenyl) sulfonyl) -1-piperazinyl) -N- (phenyl-acetyl) -sydnonimine;
N-Benzoyl-3-(4-((dimethylamino)sulfonyl)-1-piper zinyl)- sydnonimin; N-(Ethoxyoxoacetyl)-3-(4-(methylsulfonyl)-1-piperazinyl)- sydnonimin;N-benzoyl-3- (4 - ((dimethylamino) sulfonyl) -1-piperzinyl) sydnonimine; N- (ethoxyoxoacetyl) -3- (4- (methylsulfonyl) -1-piperazinyl) sydnonimine;
N-(2, -Dichlorbenzoyl)-3-(4-((dimethylamino)sulfonyl)-1- piperazinyl)-sydnonimin; N-(3-Pyridinylcarbonyl)-3-(4-thiomorpholinyl)-sydnonimin; 3-(4-(Methylsulfonyl)-1-piperazinyl)-N-(3-pyridinylcar- bonyl)-sydnonimin;N- (2, -Dichlorobenzoyl) -3- (4 - ((dimethylamino) sulfonyl) -1-piperazinyl) -sydnonimine; N- (3-pyridinylcarbonyl) -3- (4-thiomorpholinyl) -sydnonimine; 3- (4- (methylsulfonyl) -1-piperazinyl) -N- (3-pyridinylcar- bonyl) -sydnonimine;
3-(4-( (Dimethylamino)sulfonyl)-1-piperazinyl)-N-(ethoxy¬ carbonyl)-sydnonimin;3- (4- ((Dimethylamino) sulfonyl) -1-piperazinyl) -N- (ethoxycarbonyl) -sydnonimine;
N-(3,3-Dimethyl-l-oxobutyl)-3-(4-thiomorpholinyl)-sydno- nimin;N- (3,3-dimethyl-l-oxobutyl) -3- (4-thiomorpholinyl) -dynnimine;
N-(Ethoxyoxoacetyl)-3-(4-thiomorpholinyl)-sydnonimin;N- (ethoxyoxoacetyl) -3- (4-thiomorpholinyl) -sydnonimine;
N-(Ethoxycarbonyl)-3-(4-(methylsulfonyl)-1-piper zinyl)- sydnonimin;N- (ethoxycarbonyl) -3- (4- (methylsulfonyl) -1-piperzinyl) sydnonimine;
3-(4-Thiomorpholinyl)-N-(3,4,5-trimethoxybenzoyl)-sydnon- imin;3- (4-thiomorpholinyl) -N- (3,4,5-trimethoxybenzoyl) -sydnone imine;
N-(2,2-Dimethyl-l-oxopropyl)-3-(4-thiomorpholinyl)-syd¬ nonimin;N- (2,2-dimethyl-l-oxopropyl) -3- (4-thiomorpholinyl) -syd nonimin;
3-(4-((4-Methylphenyl)sulfonyl)-1-piperazinyl)-N-(phen- oxyacetyl)-sydnonimin; N-(Ethoxycarbonyl)-3-(4-( (4-methylphenyl)sulfonyl)-1- piperazin yl)-sydnonimin;3- (4 - ((4-Methylphenyl) sulfonyl) -1-piperazinyl) -N- (phenoxyacetyl) -sydnonimine; N- (ethoxycarbonyl) -3- (4- ((4-methylphenyl) sulfonyl) -1- piperazin yl) -sydnonimine;
N-Benzoyl-3-(4-thiomorpholinyl)-sydnonimin;N-benzoyl-3- (4-thiomorpholinyl) sydnonimine;
3-(4-((Dimethylamino)sulfonyl)-1-piperazinyl)-N-(1-oxo-3- (4 - ((Dimethylamino) sulfonyl) -1-piperazinyl) -N- (1-oxo-
3-phenyl-2-propenyl)-sydnonimin; N-(Phenoxycarbonyl)-3-(4-thiomorpholinyl)-sydnonimin;3-phenyl-2-propenyl) -sydnonimine; N- (phenoxycarbonyl) -3- (4-thiomorpholinyl) -sydnonimine;
N-(4-Chlorbenzoyl)-3-(4-thiomorpholinyl)-sydnonimin;N- (4-chlorobenzoyl) -3- (4-thiomorpholinyl) -sydnonimine;
N-(Ethoxycarbonyl)-3-(4-thiomorpholinyl)-sydnonimin;N- (ethoxycarbonyl) -3- (4-thiomorpholinyl) -sydnonimine;
N-(Cyclohexylcarbonyl)-3-(4-thiomorpholinyl)-sydnonimin;N- (cyclohexylcarbonyl) -3- (4-thiomorpholinyl) -sydnonimine;
N-Benzoyl-3-(4-(methylsulfonyl)-1-piperazinyl)-sydnon- imin;N-benzoyl-3- (4- (methylsulfonyl) -1-piperazinyl) sydnone imine;
N-(2,2-Dimethyl-l-oxopropyl)-3-(4-(methylsulfonyl)-1- piperazinyl)-sydnonimin;N- (2,2-dimethyl-l-oxopropyl) -3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine;
3-(4-((Dimethylamino)sulfonyl)-1-piperazinyl)-N-(1-oxo- propyl)-sydnonimin; N-Acetyl-3-(4-(methylsulfonyl)-1-piperazinyl)-sydnonimin;3- (4 - ((Dimethylamino) sulfonyl) -1-piperazinyl) -N- (1-oxo-propyl) -sydnonimine; N-acetyl-3- (4- (methylsulfonyl) -1-piperazinyl) -sydnonimine;
N-Acetyl-3-(4-( (dimethylamino)sulfonyl)-1-piperazinyl)- sydnonimin;N-acetyl-3- (4- ((dimethylamino) sulfonyl) -1-piperazinyl) sydnonimine;
N-(Methoxyacetyl)-3-(4-thiomorpholinyl)-sydnonimin; N-Acetyl-3-(4-thiomorpholinyl)-sydnonimin; N-( ( (4-Chlorpheny1)amino)carbonyl)-3-(2-hydroxy-2-phenyl- ethyl ) - sydnonimin ;N- (methoxyacetyl) -3- (4-thiomorpholinyl) -sydnonimine; N-acetyl-3- (4-thiomorpholinyl) -sydnonimine; N- (((4-chloropheny1) amino) carbonyl) -3- (2-hydroxy-2-phenyl- ethyl) - sydnonimine;
N-( ( (4-Acetylphenyl)amino )carbohyl ) -3-(2-hydroxy-2-phe- nylethyl)-sydnonimin;N- (((4-acetylphenyl) amino) carbohyl) -3- (2-hydroxy-2-phenylethyl) sydnonimine;
3-(2-Hydroxy-2-phenylethyl)-N-( ((4-nitrophenyl)amino)- carbonyl)-sydnonimin;3- (2-Hydroxy-2-phenylethyl) -N- (((4-nitrophenyl) amino) carbonyl) -sydnonimine;
N-(((3,4-Dichlorphenyl)amino)carbonyl)-3-(2-hydroxy-2- phenylethyl)-sydnonimin;N - (((3,4-dichlorophenyl) amino) carbonyl) -3- (2-hydroxy-2-phenylethyl) -sydnonimine;
N-(((4-Fluorphenyl)amino)carbonyl)-3-(2-hydroxy-2-phenyl¬ ethyl)-sydnonimin; N-(( (4-Chlorphenyl)amino)carbonyl)-3-(2-hydroxy-1-methyl-N - (((4-fluorophenyl) amino) carbonyl) -3- (2-hydroxy-2-phenylethyl) -sydnonimine; N - (((4-chlorophenyl) amino) carbonyl) -3- (2-hydroxy-1-methyl-
2-phenylethyl)-sydnonimin;2-phenylethyl) sydnonimine;
3-(2-Hydroxy-l-methyl-2-phenylethyl)-N-((phenylamino)car¬ bonyl)-sydnonimin;3- (2-hydroxy-l-methyl-2-phenylethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
3-(2-Hydroxy-2-phenylethyl)-N-( (phenylamino)carbonyl)- sydnonimin;3- (2-hydroxy-2-phenylethyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-(2-Hydroxy-2-phenylethyl)-sydnonimin;3- (2-hydroxy-2-phenylethyl) -sydnonimine;
N-(((4-Chlorphenyl)amino)carbonyl)-3-(2-hydroxy-2-phenyl- propyl)-sydnonimin;N - (((4-chlorophenyl) amino) carbonyl) -3- (2-hydroxy-2-phenylpropyl) sydnonimine;
3-(2-hydroxy-2-phenylpropyl)-N-( (phenylamino)carbonyl)- sydnonimin;3- (2-hydroxy-2-phenylpropyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-(2-Hydroxy-2-phenylethyl)-N-((phenylamino)carbonyl)- sydnonimin;3- (2-hydroxy-2-phenylethyl) -N - ((phenylamino) carbonyl) - sydnonimine;
N-(((4-Methylphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl¬ ethyl)-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-(( (3-(trifluormethyl)phenyl) amino)carbonyl)-sydnonimin;N - (((4-methylphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -sydnonimine; 3- (1-methyl-2-phenylethyl) -N - (((3- (trifluoromethyl) phenyl) amino) carbonyl) -sydnonimine;
N-(((3,4-Dichlorphenyl)amino)carbonyl)-3-(1-methyl-2-phe¬ nylethyl)-sydnonimin;N - (((3,4-dichlorophenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-( ((4-Chlorphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl- ethyl)-sydnonimin;N- (((4-chlorophenyl) amino) carbonyl) -3- (1-methyl-2-phenyl-ethyl) -dydnonimine;
N-Acetyl-3-(1-methyl-2-phenylethyl)-sydnonimin;N-acetyl-3- (1-methyl-2-phenylethyl) sydnonimine;
N-((( -Chlorphenyl)amino)carbonyl)-3-(2-phenylethyl)- sydnonimin;N - (((chlorophenyl) amino) carbonyl) -3- (2-phenylethyl) sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-((phenylamino)carbonyl)- sydnonimin; 1 3-(1-Methyl-1-phenylethyl)-N-(( henylamino)carbonyl)- sydnonimin;3- (l-methyl-2-phenylethyl) -N - ((phenylamino) carbonyl) sydnonimine; 1 3- (1-methyl-1-phenylethyl) -N - ((henylamino) carbonyl) sydnonimine;
3-(2-Hydroxy-1-methyl-2-phenylethyl)-N-( (phenylamino)- carbonyl)-sydnonimin; 5 3-(2-Hydroxy-1-methyl-2-phenylethyl)-N-( ( (4-hydroxyphe¬ nyl)amino)carbonyl)-sydnonimin;3- (2-hydroxy-1-methyl-2-phenylethyl) -N- ((phenylamino) carbonyl) -sydnonimine; 5 3- (2-Hydroxy-1-methyl-2-phenylethyl) -N- (((4-hydroxyphenyl) amino) carbonyl) -sydnonimine;
N-( ( (4-Hydroxyphenyl)amino)carbonyl)-3-.(1-methyl-2-phe¬ nylethyl)-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-( (phenylamino)carbonyl)- o sydnonimin; N-((Cyclohexylamino)carbonyl)-3-(l-methyl-2- phenylethyl)-sydnonimin;N- (((4-Hydroxyphenyl) amino) carbonyl) -3 -. (1-methyl-2-phenylethyl) -sydnonimine; 3- (1-methyl-2-phenylethyl) -N- ((phenylamino) carbonyl) - o sydnonimine; N - ((Cyclohexylamino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine;
3-(1-Methyl-2-phenylethyl)-N-( (phenylamino)acetyl)-syd¬ nonimin; N-( (Methylamino)acetyl)-N-(1-methyl-2-phenylethyl)-syd- 5 nonimin;3- (1-methyl-2-phenylethyl) -N- ((phenylamino) acetyl) -syd¬ nonimin; N- ((methylamino) acetyl) -N- (1-methyl-2-phenylethyl) -syd- 5 nonimin;
N-(2-Amino-l-oxopropyl)-N-(1-methyl-2-phenylethyl)-syd¬ nonimin;N- (2-amino-1-oxopropyl) -N- (1-methyl-2-phenylethyl) -syd¬ nonimin;
N-(Aminoacetyl)-3-(1-methyl-2-phenylethyl)-sydnonimin; N-( ( (1-Carboxypentyl)amino)carbonyl)-3-(1-methyl-2-phe- o nylethyl)-sydnonimin;N- (aminoacetyl) -3- (1-methyl-2-phenylethyl) -sydnonimine; N- (((1-carboxypentyl) amino) carbonyl) -3- (1-methyl-2-phe-nylethyl) -sydnonimine;
N-(( (l-Carboxy-3-methylbutyl)amino)carbonyl)-3-(1-methyl- 2-phenylethyl)-sydnonimin;N - (((l-carboxy-3-methylbutyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-(2-( ( (1,1-Dimethylethoxy)carbonyl)amino)-3-(lH-indol-3- yl)-1-oxopropyl)-3-(1-methyl-2-phenylethyl)-sydnonimin; 5 N~( ( (Carboxymethyl)amino)carbonyl)-3-(1-methyl-2-phenyl¬ ethyl)-sydnonimin;N- (2- (((1,1-dimethylethoxy) carbonyl) amino) -3- (1H-indol-3-yl) -1-oxopropyl) -3- (1-methyl-2-phenylethyl) -sydnonimine; 5 N ~ (((carboxymethyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -sydnonimine;
N-( ( ( (Carboxyphenyl) ethyl)amino)carbonyl)-3-(l-methyl-2- phenylethyl)-sydnonimin; N-( ( (Carboxyphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl- 0 ethyl)-sydnonimin;N- ((((carboxyphenyl) ethyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine; N- (((carboxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenyl-0ethyl) -sydnonimine;
N-Acety1-3-cyclohexy1-4-methyl-sydnonimin;N-acety1-3-cyclohexy1-4-methyl-sydnonimine;
3-Cyclohexyl-4-methyl-sydnonimi ;3-cyclohexyl-4-methyl-sydnonimi;
4-Brom-3-methyl-N-( (methylamino)carbonyl)-sydnonimin;4-bromo-3-methyl-N- ((methylamino) carbonyl) -sydnonimine;
N-Acetyl-3-cyclohexyl-4-methyl-sydnonimin; 5 N-Acetyl-3-cyclohexyl-sydnσnimin; 3-(l-Methyl-2-phenylethyl)-N-(( (3-(trifluormethyl)phe¬ nyl)amino)carbonyl)-sydnonimin;N-acetyl-3-cyclohexyl-4-methyl-sydnonimine; 5 N-acetyl-3-cyclohexyl-sydnσnimin; 3- (l-methyl-2-phenylethyl) -N - (((3- (trifluoromethyl) phenyl) amino) carbonyl) -sydnonimine;
N-(((3,4-Dichlorphenyl)amino)carbonyl)-3-(1-methyl-2- phenylethyl)-sydnonimin; N-(((4-Chlorphenyl)amino)carbonyl)-3-(l-methyl-2-phenyl- ethyl)-sydnonimin;N - (((3,4-dichlorophenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -sydnonimine; N - (((4-chlorophenyl) amino) carbonyl) -3- (l-methyl-2-phenyl-ethyl) -dydnonimine;
N-Acetyl-3-(l-methyl-2-phenylethyl)-sydnonimin;N-acetyl-3- (l-methyl-2-phenylethyl) sydnonimine;
N-(((4-Methylphenyl)amino)carbonyl)-3-(l-methyl-2-phenyl- ethyl)-sydnonimin 3-(2-Phenylethyl)-N-(( (3-(trifluormethyl)phenyl)amino)- carbonyl)-sydnonimin;N - (((4-methylphenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine 3- (2-phenylethyl) -N - (((3- (trifluoromethyl) phenyl) amino ) - carbonyl) -sydnonimine;
N-(((3,4-Dichlorphenyl)amino)carbonyl)-3-(2-phenylethyl)- sydnonimin;N - (((3,4-dichlorophenyl) amino) carbonyl) -3- (2-phenylethyl) sydnonimine;
N-(Chlor(dimethyliminio)methyl)-3-(1-methyl-2-phenyl- ethyl)-sydnonimin;N- (chloro (dimethyliminio) methyl) -3- (1-methyl-2-phenyl-ethyl) -dydnonimine;
N-( (Dimethylamino)carbonyl)-3-(1-methyl-2-phenylethyl)- sydnonimin;N- ((dimethylamino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-((Dimethylamino)(phenylimino)methyl)-3-(l-methyl-2- phenylethyl)-sydnonimin; N-( (Dimethylamino) ((phenylmethyl)imino)methyl)-3-(1-me¬ thyl-2-phenylethyl)-sydnonimin;N - ((dimethylamino) (phenylimino) methyl) -3- (l-methyl-2-phenylethyl) -sydnonimine; N- ((dimethylamino) ((phenylmethyl) imino) methyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-((Dimethylamino)iminomethyl)-3-(l-methyl-2-phenyl- ethyl)-sydnonimin;N - ((dimethylamino) iminomethyl) -3- (l-methyl-2-phenyl-ethyl) -sydnonimine;
3-Tricyclo(3.3.1.13,7)dec-1-yl-sydnonimin; 3-Cyclohexyl-N-(( (3,4-dichlorphenyl)amino)carbonyl)-syd¬ nonimin;3-tricyclo (3.3.1.13.7) dec-1-yl-sydnonimine; 3-cyclohexyl-N - (((3,4-dichlorophenyl) amino) carbonyl) -syd¬ nonimin;
N-(Cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnonimin;N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnonimine;
N-((Phenylamino)carbonyl)-3-(tricyclo(3.3.1.13,7)dec-1- ylmethyl)-sydnonimin; N-( (Phenylamino)carbonyl)-3-tricyclo(3.3.1.13,7)dec-l- yl-sydnonimin;N - ((phenylamino) carbonyl) -3- (tricyclo (3.3.1.13,7) dec-1-ylmethyl) -sydnonimine; N- ((phenylamino) carbonyl) -3-tricyclo (3.3.1.13.7) dec-1-yl-sydnonimine;
3-Cyclohexyl-N-((phenylamino)carbonyl)-sydnonimin;3-cyclohexyl-N - ((phenylamino) carbonyl) -sydnonimine;
N-((Methylamino)carbonyl)-3-(1-methyl-2-phenylethyl)-syd¬ nonimin; 3-Methyl-N-( (methylamino)carbonyl)-sydnonimin; N-(((4-Ethoxyphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl- ethyl)-sydnonimin;N - ((methylamino) carbonyl) -3- (1-methyl-2-phenylethyl) -syd nonimin; 3-methyl-N- ((methylamino) carbonyl) -sydnonimine; N - (((4-ethoxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenyl-ethyl) -dydnonimine;
3-(Tricyclo(3.3.1.13,7)dec-l-ylmethyl)-sydnonimin;3- (tricyclo (3.3.1.13,7) dec-l-ylmethyl) -sydnonimine;
N-( ( (4-Methoxyphenyl)amino)carbonyl)-3-(1-methyl-2-phe- nylethyl)-sydnonimin;N- (((4-methoxyphenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
N-Acetyl-3-(1-methylethyl)-sydnonimin;N-acetyl-3- (1-methylethyl) -sydnonimine;
N-Acetyl-3-ethyl-sydnonimin;N-acetyl-3-ethyl-sydnonimine;
N-Acetyl-3-methyl-sydnonimin;N-acetyl-3-methyl-sydnonimine;
N-Acetyl-3-propyl-sydnonimin; 4-(4-Methoxyphenyl)-3-(phenylmethyl)-sydnonimin;N-acetyl-3-propyl-sydnonimine; 4- (4-methoxyphenyl) -3- (phenylmethyl) sydnonimine;
4-(4-Methylphenyl)-3-(phenylmethyl)-sydnonimin;4- (4-methylphenyl) -3- (phenylmethyl) -sydnonimine;
4-(4-Hydroxyphenyl)-3-(phenylmethyl)-sydnonimin;4- (4-hydroxyphenyl) -3- (phenylmethyl) sydnonimine;
4-(2-Hydroxyphenyl)-3-(phenylmethyl)-sydnonimin;4- (2-hydroxyphenyl) -3- (phenylmethyl) sydnonimine;
4-(3,4-Dimethoxyphenyl)-3-( henylmethyl)-sydnonimin; 3-(2,2,2-Trinitroethyl)-sydnonimin;4- (3,4-dimethoxyphenyl) -3- (henylmethyl) sydnonimine; 3- (2,2,2-trinitroethyl) sydnonimine;
3-(4-Ethoxyphenyl)-4-(4-methylphenyl)-sydnonimin;3- (4-ethoxyphenyl) -4- (4-methylphenyl) sydnonimine;
3-(3-Ethoxyphenyl)-4-(4-methylphenyl)-sydnonimin;3- (3-ethoxyphenyl) -4- (4-methylphenyl) sydnonimine;
3-(2-Ethoxyphenyl)-4-(4-methylphenyl)-sydnonimin;3- (2-ethoxyphenyl) -4- (4-methylphenyl) sydnonimine;
3-(4-Methoxyphenyl)-4-(4-methylphenyl)-sydnonimin; 3-(3-Methoxyphenyl)-4-(4-methylphenyl)-sydnonimin;3- (4-methoxyphenyl) -4- (4-methylphenyl) sydnonimine; 3- (3-methoxyphenyl) -4- (4-methylphenyl) sydnonimine;
3-(2-Methoxyphenyl)-4-(4-methylphenyl)-sydnonimin;3- (2-methoxyphenyl) -4- (4-methylphenyl) sydnonimine;
3,4-bis(4-Methylphenyl)-sydnonimin;3,4-bis (4-methylphenyl) hydnonimine;
3-(3-Methylphenyl)-4-(4-methylphenyl)-sydnonimin;3- (3-methylphenyl) -4- (4-methylphenyl) sydnonimine;
3-(2-Methylphenyl)-4-(4-methylphenyl)-sydnonimin; 4-(4-Methylphenyl)-3-phenyl-sydnonimin;3- (2-methylphenyl) -4- (4-methylphenyl) sydnonimine; 4- (4-methylphenyl) -3-phenyl-sydnonimine;
3-(3-Ethoxy-3-oxo-l-phenylpropyl)-sydnonimin;3- (3-ethoxy-3-oxo-l-phenylpropyl) sydnonimine;
3-(2-(4-Aminophenyl)ethyl)-N-( (phenylamino)carbonyl)-syd¬ nonimin;3- (2- (4-aminophenyl) ethyl) -N- ((phenylamino) carbonyl) -syd¬ nonimin;
3-(2-(4-Nitrophenyl)ethyl)-N-( (phenylamino)carbonyl)-syd- nonimin;3- (2- (4-nitrophenyl) ethyl) -N- ((phenylamino) carbonyl) -syd nonimin;
3-(l-Methyl-2-(4-nitrophenyl)ethyl)-N-((phenylamino)car¬ bonyl)-sydnonimin;3- (l-methyl-2- (4-nitrophenyl) ethyl) -N - ((phenylamino) carbonyl) -sydnonimine;
N-((Phenylamino)carbonyl)-3-(2-phenylethyl)-sydnonimin;N - ((phenylamino) carbonyl) -3- (2-phenylethyl) -sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-( (phenylamino)carbonyl)-syd- nonimin; 3-(2-(4-Nitrophenyl)ethyl)-sydnonimin;3- (l-methyl-2-phenylethyl) -N- ((phenylamino) carbonyl) -syd nonimin; 3- (2- (4-nitrophenyl) ethyl) -sydnonimine;
3-(l-Methyl-2-(4-nitrophenyl)ethyl)-sydnonimin;3- (l-methyl-2- (4-nitrophenyl) ethyl) -sydnonimine;
3-(2-(4-Aminophenyl)ethyl)-N-( ( henylamino)carbonyl)-syd¬ nonimin; N-( ((4-Brompheny1)amino)carbonyl)-3-methyl-sydnonimin;3- (2- (4-aminophenyl) ethyl) -N- ((henylamino) carbonyl) -syd nonimin; N- (((4-bromopheny1) amino) carbonyl) -3-methyl-sydnonimine;
N-(((4-Bromphenyl)amino)carbonyl)-3-(l-methyl-2-phenyl- ethyl)-sydnonimin;N - (((4-bromophenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine;
4-Brom-N-((methylamino)carbonyl)-3-(l-methyl-2-phenyl- ethyl)-sydnonimin; N-(((2,4-Dinitrophenyl)amino)carbonyl)-3-methyl-sydnon- imin;4-bromo-N - ((methylamino) carbonyl) -3- (l-methyl-2-phenyl-ethyl) -sydnonimine; N - (((2,4-dinitrophenyl) amino) carbonyl) -3-methyl-sydnonimine;
N-((Methylamino)carbonyl)-3-(1-methyl-2-(4-nitrophenyl)- ethyl)-sydnonimin;N - ((methylamino) carbonyl) -3- (1-methyl-2- (4-nitrophenyl) ethyl) -sydnonimine;
N-( ((2, -dinitrophenyl)amino)carbonyl)-3-(l-methyl-2-(4- nitrophenyl)ethyl)-sydnonimin;N- (((2, -dinitrophenyl) amino) carbonyl) -3- (l-methyl-2- (4-nitrophenyl) ethyl) -sydnonimine;
4-Brom-N-(((2,4-dibromphenyl)amino)carbonyl)-3-(1-methyl-4-bromo-N - (((2,4-dibromophenyl) amino) carbonyl) -3- (1-methyl-
2-phenylethyl)-sydnonimin;2-phenylethyl) sydnonimine;
4-Brom-N-(((4-bromphenyl)amino)carbonyl)-3-methyl-sydnon- imin; 4-Brom-N-(((4-bromphenyl)amino)carbonyl)-3-(l-methyl-2- phenylethyl)-sydnonimin;4-bromo-N - (((4-bromophenyl) amino) carbonyl) -3-methyl-sydnonimine; 4-bromo-N - (((4-bromophenyl) amino) carbonyl) -3- (l-methyl-2-phenylethyl) -sydnonimine;
N-(((4-Bromphenyl)amino)carbonyl)-3-methyl-sydnonimin;N - (((4-bromophenyl) amino) carbonyl) -3-methyl-sydnonimine;
N-(((4-Bromphenyl)amino)carbonyl)-3-(1-methyl-2-phenyl¬ ethyl)-sydnonimin; 4-Brom-N-((methylamino)carbonyl)-3-(1-methyl-2-phenyl¬ ethyl)-sydnonimin;N - (((4-bromophenyl) amino) carbonyl) -3- (1-methyl-2-phenylethyl) -sydnonimine; 4-bromo-N - ((methylamino) carbonyl) -3- (1-methyl-2-phenyl¬ ethyl) -sydnonimine;
3-Methyl-N-((phenylamino)carbonyl)-sydnonimin;3-methyl-N - ((phenylamino) carbonyl) -sydnonimine;
N-((Methylamino)carbonyl)-3-(l-methyl-2-phenylethyl)-syd¬ nonimin; 3-(7-Methoxy-7-oxoheptyl)-sydnonimin;N - ((methylamino) carbonyl) -3- (l-methyl-2-phenylethyl) -syd nonimin; 3- (7-methoxy-7-oxoheptyl) sydnonimine;
3-(4-(Carboxymethyl)phenyl)-sydnonimin;3- (4- (carboxymethyl) phenyl) -sydnonimine;
3-(3-Ethoxy-3-oxo-2-phenylpropyl)-sydnonimin;3- (3-ethoxy-3-oxo-2-phenylpropyl) sydnonimine;
3-(2-Ethoxy-2-oxo-l-(phenylmethyl)ethyl)-sydnonimin;3- (2-ethoxy-2-oxo-l- (phenylmethyl) ethyl) -sydnonimine;
3-(2-Ethoxy-l-methyl-2-oxoethyl)-sydnonimin; 3-(6-Methoxy-6-oxohexyl)-sydnonimin; 3-(4-Ethoxy-4-oxobutyl)-sydnonimin; 3-(2-Carboxyethyl)-sydnonimin; 4-Brom-3-(1-piperidinyl)-sydnonimin;3- (2-ethoxy-l-methyl-2-oxoethyl) sydnonimine; 3- (6-methoxy-6-oxohexyl) sydnonimine; 3- (4-ethoxy-4-oxobutyl) sydnonimine; 3- (2-carboxyethyl) sydnonimine; 4-bromo-3- (1-piperidinyl) -sydnonimine;
4-Chlor-N-(ethoxycarbonyl)-3-(1-piperidinyl)-sydnonimin; 4-Chlor-3-(dimethylamino)-N-(3-pyridinylcarbonyl)-sydnon¬ imin;4-chloro-N- (ethoxycarbonyl) -3- (1-piperidinyl) -sydnonimine; 4-chloro-3- (dimethylamino) -N- (3-pyridinylcarbonyl) -sydnon¬ imine;
4-Chlor-3-(4-morpholinyl)-sydnonimin;4-chloro-3- (4-morpholinyl) -sydnonimine;
4-Chlor-N-(cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnon¬ imin; 4-Brom-N-(ethoxycarbonyl)-3-(1-piperidinyl)-sydnonimin; N-(Ethoxycarbonyl)-3-(1-piperidinyl)-sydnonimin; N-Acetyl-3-(hexahydro-lH-azepin-l-yl)-sydnonimin; 4-Brom-3-(hexahydro-lH-azepin-1-yl)-sydnonimin; 4-Brom-3-(dimethylamino)-N-(3-pyridinylcarbonyl)-sydnon- imin;4-chloro-N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnon¬ imine; 4-bromo-N- (ethoxycarbonyl) -3- (1-piperidinyl) -sydnonimine; N- (ethoxycarbonyl) -3- (1-piperidinyl) -sydnonimine; N-acetyl-3- (hexahydro-lH-azepin-l-yl) -sydnonimine; 4-bromo-3- (hexahydro-1H-azepin-1-yl) -sydnonimine; 4-bromo-3- (dimethylamino) -N- (3-pyridinylcarbonyl) -sydnonimine;
3-(Dimethylamino)-N-(3-pyridinylcarbonyl)-sydnonimin; 4-Brom-3-(4-morpholinyl)-sydnonimin;3- (dimethylamino) -N- (3-pyridinylcarbonyl) -sydnonimine; 4-bromo-3- (4-morpholinyl) -sydnonimine;
4-Brom-N-(cyclohexylcarbonyl)-3-( -morpholinyl)-sydnon¬ imin; N-(Cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnonimin; 4-Brom-3-(dimethylamino)-sydnonimin; N-Acetyl-3-(dimethylamino)-sydnonimin;4-bromo-N- (cyclohexylcarbonyl) -3- (-morpholinyl) -sydnon¬ imine; N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnonimine; 4-bromo-3- (dimethylamino) -sydnonimine; N-acetyl-3- (dimethylamino) -sydnonimine;
4-Methyl-3-(4-(2-(nitrooxy)ethyl)-1-piperazinyl)-sydnon¬ imin; N-(Ethoxycarbonyl)-3-(4-(2-(nitrooxy)ethyl)-1-piperazi- nyl)-sydnonimin;4-methyl-3- (4- (2- (nitrooxy) ethyl) -1-piperazinyl) -sydnon¬ imine; N- (ethoxycarbonyl) -3- (4- (2- (nitrooxy) ethyl) -1-piperazinyl) sydnonimine;
N-(2-Ethoxy-2-oxoethyl)-4-methyl-3-(4-(2-(nitrooxy)- ethyl)-1-piperazinyl)-sydnonimin; - N-Nitro-3-(3,3,3-trinitropropyl)-sydnonimin; N-Nitroso-3-(3,3,3-trinitropropyl)-sydnonimin; 3-(3,3,3-Trinitropropyl)-sydnonimine;N- (2-ethoxy-2-oxoethyl) -4-methyl-3- (4- (2- (nitrooxy) ethyl) -1-piperazinyl) sydnonimine; - N-nitro-3- (3,3,3-trinitropropyl) -sydnonimine; N-nitroso-3- (3,3,3-trinitropropyl) sydnonimine; 3- (3,3,3-trinitropropyl) -sydnonimine;
3,3'-(3,3-Dinitro-l,5-pentanediyl)bis(N-nitroso)-sydnon¬ imin; N-Acetyl-1-butyl-sydnonimin; 1-( (4-Carboxyphenyl)methyl)-N-( (phenylamino)carbonyl)- sydnonimin;3,3 '- (3,3-dinitro-l, 5-pentanediyl) bis (N-nitroso) -sydnon¬ imine; N-acetyl-1-butyl-sydnonimine; 1- ((4-Carboxyphenyl) methyl) -N- ((phenylamino) carbonyl) - sydnonimin;
N-Benzoyl-1-(6-carboxypentyl)-sydnonimin;N-benzoyl-1- (6-carboxypentyl) -sydnonimine;
N-Benzoyl-1-(6-carboxyhexyl)-sydnonimin;N-benzoyl-1- (6-carboxyhexyl) -sydnonimine;
1-(5-Carboxypentyl)-N-((phenylamino)carbonyl)-sydnonimin; N-(Aminocarbonyl)-1-(5-carboxypentyl)-sydnonimin;1- (5-carboxypentyl) -N - ((phenylamino) carbonyl) -sydnonimine; N- (aminocarbonyl) -1- (5-carboxypentyl) -sydnonimine;
N-Benzoyl-1-(5-carboxypentyl)-sydnonimin;N-benzoyl-1- (5-carboxypentyl) -sydnonimine;
N-Benzoyl-1-(5-carboxyhexyl)-sydnonimin; •N-benzoyl-1- (5-carboxyhexyl) -sydnonimine; •
N-Acetyl-1-(5-carboxypentyl)-sydnonimin;N-acetyl-1- (5-carboxypentyl) -sydnonimine;
N-Acetyl-1-(5-carboxyhexyl)-sydnonimin; 1-(6-Carboxyhexyl)-sydnonimin;N-acetyl-1- (5-carboxyhexyl) -sydnonimine; 1- (6-carboxyhexyl) -sydnonimine;
3-(4-Carboxybutyl)-sydnonimin;3- (4-carboxybutyl) -sydnonimine;
1-((4-Carboxyphenyl)methyl)-sydnonimin;1 - ((4-carboxyphenyl) methyl) -sydnonimine;
3-(6-Carboxyhexyl)-sydnonimin;3- (6-carboxyhexyl) -sydnonimine;
3-(4-Carboxybutyl)-sydnonimin; 4-(2-Methoxy-2-oxoethyl)-N-( (methylamino)carbonyl)-3- phenyl-sydnonimin;3- (4-carboxybutyl) -sydnonimine; 4- (2-methoxy-2-oxoethyl) -N- ((methylamino) carbonyl) -3-phenyl-sydnonimine;
3-(2-Carboxy-1-piperidinyl)-N-nitroso-sydnonimin;3- (2-carboxy-1-piperidinyl) -N-nitroso-sydnonimine;
N-Benzoyl-3-(dibutylamino)-sydnonimin;N-benzoyl-3- (dibutylamino) -sydnonimine;
N-Benzoyl-3-(2-carboxy-l-piperidinyl)-sydnonimin; N-Benzoyl-3-(diethylamino)-sydnonimin;N-benzoyl-3- (2-carboxy-l-piperidinyl) sydnonimine; N-benzoyl-3- (diethylamino) -sydnonimine;
Sydnonimin;Sydnonimin;
4-Brom-3-(4-methyl-1-piperazinyl)-N-(phenoxycarbonyl)- sydnonimin;4-bromo-3- (4-methyl-1-piperazinyl) -N- (phenoxycarbonyl) sydnonimine;
4-Chlor-N-(ethoxycarbonyl)-3-(4-morpholinyl)-sydnonimin; 3-Octyl-sydnonimin;4-chloro-N- (ethoxycarbonyl) -3- (4-morpholinyl) -sydnonimine; 3-octyl-sydnonimine;
4-(4-Methoxyphenyl)-3-(1-methyl-2-phenylethyl)-sydnon¬ imin;4- (4-methoxyphenyl) -3- (1-methyl-2-phenylethyl) -sydnon¬ imine;
4-( (Diethylamino)methyl)-3-(1-methyl-2-phenylethyl)-syd¬ nonimin; 3-(4-Ethoxyphenyl)-sydnonimin;4- ((diethylamino) methyl) -3- (1-methyl-2-phenylethyl) -syd¬ nonimin; 3- (4-ethoxyphenyl) -sydnonimine;
N-Acetyl-3-(1-piperidinyl)-sydnonimin; 4-Methyl-3-(1-piperidinyl)-sydnonimin; 3-(2-Carboxyethyl)-sydnonimin; 3-(Methyl-2-propenylamino)-sydnonimin; 3-(Aminocarbonyl)-sydnonimin; N-Benzoyl-3,4-diphenyl-sydnonimin;N-acetyl-3- (1-piperidinyl) -sydnonimine; 4-methyl-3- (1-piperidinyl) sydnonimine; 3- (2-carboxyethyl) sydnonimine; 3- (methyl-2-propenylamino) -sydnonimine; 3- (aminocarbonyl) sydnonimine; N-benzoyl-3,4-diphenyl-sydnonimine;
3-(4-(4,4-bis(4-Fluorphenyl)butyl•)-1-piperazinyl)-N-(1- oxopropyl)-sydnonimin;3- (4- (4,4-bis (4-fluorophenyl) butyl •) -1-piperazinyl) -N- (1-oxopropyl) sydnonimine;
3-(4-(2-Methoxyphenyl)-1-piperazinyl)-N-(3,4,5-trimeth- oxybenzoyl)-sydnonimin;3- (4- (2-methoxyphenyl) -1-piperazinyl) -N- (3,4,5-trimethoxybenzoyl) -sydnonimine;
3-(4-(Diphenylmethyl)-1-piperazinyl)-N-(1-oxopropyl)- sydnonimin;3- (4- (diphenylmethyl) -1-piperazinyl) -N- (1-oxopropyl) sydnonimine;
N-(1,3-Benzodioxol-5-ylcarbonyl)-3-(4-(2-methoxyphenyl)-N- (1,3-benzodioxol-5-ylcarbonyl) -3- (4- (2-methoxyphenyl) -
1-piperazinyl)-sydnonimin; 3-(4-(2-Pyrimidinyl)-1-piperazinyl)-N-(3,4,5-trimethoxy- benzoyl)-sydnonimin;1-piperazinyl) -sydnonimine; 3- (4- (2-pyrimidinyl) -1-piperazinyl) -N- (3,4,5-trimethoxybenzoyl) sydnonimine;
3-(4-(2-Methoxyphenyl)-1-piperazinyl)-N-( (phenylamino)- carbonyl)-sydnonimin;3- (4- (2-methoxyphenyl) -1-piperazinyl) -N- ((phenylamino) carbonyl) -sydnonimine;
N-(l-Oxopropyl)-3-( (4-(2,3,4-trimethoxyphenyl)methyl)-1- piperazinyl)-sydnonimin;N- (l-oxopropyl) -3- ((4- (2,3,4-trimethoxyphenyl) methyl) -1-piperazinyl) -sydnonimine;
3-(4-(Diphenylmethyl)-1-piperazinyl)-sydnonimin;3- (4- (Diphenylmethyl) -1-piperazinyl) -sydnonimine;
N-(2,2-Dimethyl-l-oxopropyl)-3-(4-(2-methoxyphenyl)-1- piperazinyl)-sydnonimin;N- (2,2-dimethyl-l-oxopropyl) -3- (4- (2-methoxyphenyl) -1-piperazinyl) -sydnonimine;
3-(2-(4-((2,3,4-Trimethoxyphenyl)methyl)-1-piperazinyl)- ethylsydnonimin;3- (2- (4 - ((2,3,4-Trimethoxyphenyl) methyl) -1-piperazinyl) ethylsydnonimine;
N-(1,3-Benzodioxol-5-ylcarbonyl)-3-(4-(2-pyrimidinyl)-1- piperazinyl)-sydnonimin;N- (1,3-benzodioxol-5-ylcarbonyl) -3- (4- (2-pyrimidinyl) -1-piperazinyl) -sydnonimine;
3-(4-((2,3-Dihydro-l,4-benzodioxin-2-yl)methyl)-1-pipera- zinyl)-N-(1-oxopropyl)-sydnonimin; 3-(4-(2-Methoxyphenyl)-1-piperazinyl)-(1-oxopropyl)-syd¬ nonimin;3- (4 - ((2,3-Dihydro-l, 4-benzodioxin-2-yl) methyl) -1-piperazinyl) -N- (1-oxopropyl) -sydnonimine; 3- (4- (2-methoxyphenyl) -1-piperazinyl) - (1-oxopropyl) -syd nonimin;
3-(2-(4-(1,3-Benzodioxol-5-ylmethyl)-1-piperazinyl)- ethyl)-sydnonimin;3- (2- (4- (1,3-Benzodioxol-5-ylmethyl) -1-piperazinyl) ethyl) -sydnonimine;
3-(4-( (2,3,4-Trimethoxyphenyl)methyl)-1-piperazinyl)-syd- nonimin;3- (4- ((2,3,4-Trimethoxyphenyl) methyl) -1-piperazinyl) -syd nonimin;
N-( (Phenylamino)carbonyl)-3-(4-(2-pyrimidinyl)-1-pipera- zinyl)-sydnonimin;N- ((phenylamino) carbonyl) -3- (4- (2-pyrimidinyl) -1-piperazinyl) -sydnonimine;
3-(4-(2-Methoxyphenyl)-1-piperazinyl)-(1-oxybutyl)-syd¬ nonimin; N-(l-Oxopropyl)-3-(4-(2-pyridinyl)-1-piperazinyl)-sydnon- imin;3- (4- (2-methoxyphenyl) -1-piperazinyl) - (1-oxybutyl) -syd nonimin; N- (l-oxopropyl) -3- (4- (2-pyridinyl) -1-piperazinyl) -sydnon- imin;
N-(l-Oxobutyl)-3-(4-(2-pyrimidinyl)-1-piperazinyl)-syd¬ nonimin;N- (l-oxobutyl) -3- (4- (2-pyrimidinyl) -1-piperazinyl) -syd¬ nonimin;
3-(4-((2,3-Dihydro-l,4-benzodioxin-2-yl)methyl)-1-pipera- zinyl)-sydnonimin;3- (4 - ((2,3-Dihydro-l, 4-benzodioxin-2-yl) methyl) -1-piperazinyl) -sydnonimine;
3-(2-(4-(2-Methoxyphenyl)-1-piperazinyl)ethyl)-sydnon¬ imin;3- (2- (4- (2-methoxyphenyl) -1-piperazinyl) ethyl) -sydnon¬ imine;
N-(2,2-Dimethyl-l-oxopropyl)-3-(4-(2-pyrimidinyl)-1-pipe- razinyl)-sydnonimin; 3-(4-(1,3-Benzodioxol-5-yl)-1-piperazinyl)-N-(1-oxopro- pyl)-sydnonimin;N- (2,2-dimethyl-l-oxopropyl) -3- (4- (2-pyrimidinyl) -1-pipe-razinyl) -sydnonimine; 3- (4- (1,3-Benzodioxol-5-yl) -1-piperazinyl) -N- (1-oxopropyl) sydnonimine;
3-(4-(1,3-Benzodioxol-5-ylmethyl)-1-piperazinyl)-sydnon¬ imin; 3-(2-(4-(2-Pyridinyl)-1-piperazinyl)ethyl)-sydnonimin; N-(l-Oxopropyl)-3-(4-(2-pyrimidinyl)-1-piperazinyl)-syd¬ nonimin;3- (4- (1,3-Benzodioxol-5-ylmethyl) -1-piperazinyl) -sydnon¬ imine; 3- (2- (4- (2-pyridinyl) -1-piperazinyl) ethyl) -sydnonimine; N- (l-oxopropyl) -3- (4- (2-pyrimidinyl) -1-piperazinyl) -syd nonimin;
3-(4-(2-Methoxyphenyl)-1-piperazinyl)-sydnonimin; 3-(2-(4-(2-pyrimidinyl)-1-piperazinyl)ethyl)-sydnonimin; 3-(4-(2-Pyridinyl)-1-piperazinyl)-sydnonimin; 3-(4-(2-Pyrimidinyl)-1-piperazinyl)-sydnonimin; 3-Phenyl-N-(trichloracetyl)-sydnonimin; 3-(2-(3,4-Dimethoxyphenyl)ethyl)-sydnonimin; 3-(2-(4-Methoxyphenyl)ethyl)-sydnonimin; 3-(2-(4-Hydroxyphenyl)ethyl)-sydnonimin; 3-(2-(4-Hydroxyphenyl) ethyl)-sydnonimin; N-Benzoyl-3-(2-phenylethyl)-sydnonimin; 3-(3-Phenylpropyl)-N-(2,3, -trimethoxybenzoyl)-sydnon¬ imin; 3-(2-Phenylethyl)-N-(2,3,4-trimethoxybenzoyl)-sydnonimin; 3-(2-(3,4-Dimethoxyphenyl)ethyl)-N-( (phenylamino)carbo¬ nyl)-sydnonimin;3- (4- (2-methoxyphenyl) -1-piperazinyl) sydnonimine; 3- (2- (4- (2-pyrimidinyl) -1-piperazinyl) ethyl) -sydnonimine; 3- (4- (2-pyridinyl) -1-piperazinyl) sydnonimine; 3- (4- (2-pyrimidinyl) -1-piperazinyl) sydnonimine; 3-phenyl-N- (trichloroacetyl) -sydnonimine; 3- (2- (3,4-dimethoxyphenyl) ethyl) -sydnonimine; 3- (2- (4-methoxyphenyl) ethyl) -sydnonimine; 3- (2- (4-Hydroxyphenyl) ethyl) -sydnonimine; 3- (2- (4-Hydroxyphenyl) ethyl) -sydnonimine; N-benzoyl-3- (2-phenylethyl) -sydnonimine; 3- (3-phenylpropyl) -N- (2,3, -trimethoxybenzoyl) -sydnon¬ imine; 3- (2-phenylethyl) -N- (2,3,4-trimethoxybenzoyl) sydnonimine; 3- (2- (3,4-dimethoxyphenyl) ethyl) -N- ((phenylamino) carbonyl) -sydnonimine;
N-Acetyl-3-(2-(3,4-dimethoxyphenyl)ethyl)-sydnonimi ; 4-Phenyl-3-(2-phenylethyl)-sydnonimin; 4-Methyl-3-(2-phenylethyl)-sydnonimin; 3-(2-Ethoxy-2-oxoethyl)-N-(1-oxopropyl)-sydnonimin; N-Acetyl-3-(2-ethoxy-2—oxoethyl)-sydnonimin;N-acetyl-3- (2- (3,4-dimethoxyphenyl) ethyl) -sydnonimi; 4-phenyl-3- (2-phenylethyl) -sydnonimine; 4-methyl-3- (2-phenylethyl) -sydnonimine; 3- (2-ethoxy-2-oxoethyl) -N- (1-oxopropyl) -sydnonimine; N-acetyl-3- (2-ethoxy-2-oxoethyl) sydnonimine;
3-(2-Phenyl-l-(phenylmethyl)ethyl)-sydnonimin;3- (2-phenyl-1- (phenylmethyl) ethyl) -sydnonimine;
N,N'-Diformyl-3,3'-dimethyl-4,4'-bisydnonimin;N, N'-diformyl-3,3'-dimethyl-4,4'-bisydnonimine;
N,N'-Dicarboxy-3,3'-diphenyl-4,4'-bisydnonimin; N,N'-Dicarboxy-3,3'-dimethyl-4,4'-bisydnonimin;N, N'-dicarboxy-3,3'-diphenyl-4,4'-bisydnonimine; N, N'-dicarboxy-3,3'-dimethyl-4,4'-bisydnonimine;
N,N'-Dibenzoyl-3,3'-dimethyl-4,4'-bisydnonimin;N, N'-dibenzoyl-3,3'-dimethyl-4,4'-bisydnonimine;
3-(5-Carboxypentyl)-sydnonimin;3- (5-carboxypentyl) -sydnonimine;
3-(5-Carboxypentyl)-4-methyl-sydnonimin;3- (5-carboxypentyl) -4-methyl-sydnonimine;
3-(5-Carboxypentyl)-N-nitroso-sydnonimin; 3-(1-Methyl-2-phenylethyl)-N-( (phenylamino)carbonyl)- sydnonimin;3- (5-carboxypentyl) -N-nitroso-sydnonimine; 3- (1-methyl-2-phenylethyl) -N- ((phenylamino) carbonyl) sydnonimine;
3-Acetoxy-4-propyl-sydnonimin;3-acetoxy-4-propyl-sydnonimine;
3-Acetoxy-N-methyl-4-propyl-sydnonimin;3-acetoxy-N-methyl-4-propyl-sydnonimine;
N-(Phenylcarbamoyl)-3-( (phenylcarbamoyl)oxy)-4-propyl- sydnonimin;N- (phenylcarbamoyl) -3- ((phenylcarbamoyl) oxy) -4-propylsydnonimine;
3-( (Phenylcarbamoyl)oxy)-4-propy1-sydnonimin;3- ((Phenylcarbamoyl) oxy) -4-propy1-sydnonimine;
3-Acetoxy-N-acetyl-4-propyl-sydnonimin;3-acetoxy-N-acetyl-4-propyl-sydnonimine;
4-(Carboxymethyl)-N-(methylcarbamoyl)-3-phenyl-sydnon- imin-ethylester; 3-(m-( (Cyanomethyl)nitrosamino)phenyl)-sydnonimin;Ethyl 4- (carboxymethyl) -N- (methylcarbamoyl) -3-phenyl-sydnonimine; 3- (m- ((Cyanomethyl) nitrosamino) phenyl) -sydnonimine;
3-Benzyl-4-(m-nitrophenyl)-sydnonimin;3-benzyl-4- (m-nitrophenyl) -sydnonimine;
3,3'-p-Phenylenedisydnonimin;3,3'-p-phenylenedisydnonimine;
3,3'-(1,2-Ethanediyl)bis-sydnonimin;3,3 '- (1,2-ethanediyl) bis-sydnonimine;
3-Morpholino-N-(3,4,5-trimethoxybenzoyl)-sydnonimin; 3-(Dibenzylamino)-4-methyl-sydnonimin;3-morpholino-N- (3,4,5-trimethoxybenzoyl) sydnonimine; 3- (dibenzylamino) -4-methyl-sydnonimine;
3-(Dimethylamino)-4-methyl-sydnonimin;3- (dimethylamino) -4-methyl-sydnonimine;
N-Benzoyl-3-(2-methyl-1-piperidinyl)-sydnonimin;N-benzoyl-3- (2-methyl-1-piperidinyl) sydnonimine;
N-Benzoyl-3-(1-piperidinyl)-sydnonimin;N-benzoyl-3- (1-piperidinyl) -sydnonimine;
3-(Dimethylamino)-N-nitroso-sydnonimin; 3-(Dimethylamino)-N-(ethoxycarbonyl)-sydnonimin;3- (dimethylamino) -N-nitroso-sydnonimine; 3- (dimethylamino) -N- (ethoxycarbonyl) -sydnonimine;
N-Carboxy-3-morpholino-sydnonimin-3,3,5-trimethylcyclo- hexyl-ester;N-carboxy-3-morpholino-sydnonimine-3,3,5-trimethylcyclohexyl ester;
N-Carboxy-3-morpholino-sydnonimin-2-(p-tolylsulfonyl)- ethyl-ester; N-Carboxy-3-morpholino-sydnonimin-ethylester; 1 N-(Ethoxycarbonyl)-3-(4-morpholinyl)-sydnonimin;N-carboxy-3-morpholinosydnonimine-2- (p-tolylsulfonyl) ethyl ester; N-carboxy-3-morpholino-sydnonimine ethyl ester; 1 N- (ethoxycarbonyl) -3- (4-morpholinyl) -sydnonimine;
N-(N-Carboxyalanyl)-3-morpholino"-sydnonimin-benzylester;N- (N-carboxyalanyl) -3-morpholino " -sydnonimine-benzyl ester;
3-(4-Morpholinyl)-N-(phenoxyacetyl)-sydnonimin;3- (4-morpholinyl) -N- (phenoxyacetyl) -sydnonimine;
N-Acetyl-3-(4-morpholinyl)-sydnonimin; 5 3-(Carboxymethyl)-4-phenyl-sydnonimin ethylester;N-acetyl-3- (4-morpholinyl) -sydnonimine; 5 3- (carboxymethyl) -4-phenyl-sydnonimine ethyl ester;
N-Acetyl-3-butyl-4-phenyl-sydnonimin;N-acetyl-3-butyl-4-phenyl-sydnonimine;
N-Acetyl-3-phenyl-sydnonimin;N-acetyl-3-phenyl-sydnonimine;
N-Acetyl-3-benzyl-sydnonimin;N-acetyl-3-benzyl-sydnonimine;
3-Benzyl-4-phenyl-sydnonimin; o 3-Phenyl-sydnonimin;3-benzyl-4-phenyl-sydnonimine; o 3-phenyl-sydnonimine;
3-Benzyl-sydnonimin;3-benzyl-sydnonimine;
3-(((2-Carboxy-3,3-dimethyl-7-oxo-4-thia-l-azabicyclo-3 - (((2-carboxy-3,3-dimethyl-7-oxo-4-thia-l-azabicyclo-
(3.2.0)hept-6-yl)carbamoyl)methyl)-N-( (o-chlorphenyl)- carbamoyl)-sydnonimin; 5 N-Acetyl-3-(carbamoylmethyl)-sydnonimin;(3.2.0) hept-6-yl) carbamoyl) methyl) -N- ((o-chlorophenyl) carbamoyl) -sydnonimine; 5 N-acetyl-3- (carbamoylmethyl) -sydnonimine;
4-(Carbamoylmethyl)-3-methyl-N-(phenylcarbamoyl)-sydnon¬ imin;4- (carbamoylmethyl) -3-methyl-N- (phenylcarbamoyl) -sydnon¬ imine;
4-(Carboxymethyl)-3-methyl-N-(phenylcarbamoyl)-sydnon- imin-ethylester; 0 N-(Benzylcarbamoyl)-3-(carboxymethyl)-sydnonimin-ethyl- ester;4- (carboxymethyl) -3-methyl-N- (phenylcarbamoyl) -sydnone imine ethyl ester; 0 N- (benzylcarbamoyl) -3- (carboxymethyl) -sydnonimine-ethyl ester;
3-(Carboxymethyl)-N-(methylcarbamoyl)-4-phenyl-sydnon- imin-ethylester;3- (carboxymethyl) -N- (methylcarbamoyl) -4-phenyl-sydnonimine ethyl ester;
3-(α-Methylphenethyl)-sydnonimin; 5 3 ,3'-(3,3-Dinitro-l,5-pentanediyl)bis-sydnonimin;3- (α-methylphenethyl) -sydnonimine; 5 3, 3 '- (3,3-Dinitro-l, 5-pentanediyl) bis-sydnonimine;
N-Benzoyl-3-(carboxymethyl)-sydnonimin-ethylester;N-benzoyl-3- (carboxymethyl) -sydnonimine ethyl ester;
3-Isopropyl-4-phenyl-sydnonimin;3-isopropyl-4-phenyl-sydnonimine;
N-Benzoyl-3-(carbamoylmethyl)-4-phenyl-sydnonimin;N-benzoyl-3- (carbamoylmethyl) -4-phenyl-sydnonimine;
3-(Carbamoylmethyl)-4-phenyl-N-(phenylthiocarbamoyl)- o sydnonimin;3- (carbamoylmethyl) -4-phenyl-N- (phenylthiocarbamoyl) - o-sydnonimine;
3-(α-Carbamoyl-p-tolyl)-N-(methylcarbamoyl)-sydnonimin; N-(Benzylcarbamoyl)-3-(carbamoylmethyl)-sydnonimin;3- (α-carbamoyl-p-tolyl) -N- (methylcarbamoyl) -sydnonimine; N- (benzylcarbamoyl) -3- (carbamoylmethyl) -sydnonimine;
4-(Carbamoylmethyl)-3-methyl-N-(methylcarbamoyl)-sydnon¬ imin; 5 3-( ((2-Hydroxyethyl)carbamoyl)methyl)-4-phenyl-N-(phenyl- carbamoyl)-sydnonimin;.4- (carbamoylmethyl) -3-methyl-N- (methylcarbamoyl) -sydnon¬ imine; 5 3- (((2-Hydroxyethyl) carbamoyl) methyl) -4-phenyl-N- (phenyl- carbamoyl) -sydnonimine ;.
3-(Carbamoylmethyl)-N-( (o-chlorphenyl)carbamoyl)-sydnon¬ imin;3- (carbamoylmethyl) -N- ((o-chlorophenyl) carbamoyl) -sydnon¬ imine;
3-(Carbamoylmethyl)-4-methyl-N-(phenylthiocarbamoyl)-syd- nonimin;3- (carbamoylmethyl) -4-methyl-N- (phenylthiocarbamoyl) -syd-nonimin;
3-(Carbamoylmethyl)-4-phenyl-N-(phenylcarbamoyl)-sydnon¬ imin;3- (carbamoylmethyl) -4-phenyl-N- (phenylcarbamoyl) -sydnon¬ imine;
3-(Carbamoylmethyl)-N-(methylcarbamoyl)-4-phenyl-sydnon- imin; 3-(oj-Carboxy-p-tolyl)-N-((o-chlorphenyl)carbamoyl)-syd- nonimin-ethylester;3- (carbamoylmethyl) -N- (methylcarbamoyl) -4-phenyl-sydnonimine; 3- (oj-carboxy-p-tolyl) -N - ((o-chlorophenyl) carbamoyl) -syd-nonimin ethyl ester;
3-(α-Carboxy-p-tolyl)-N-(methylcarbamoyl)-sydnonimin- ethylester;3- (α-carboxy-p-tolyl) -N- (methylcarbamoyl) -sydnonimine ethyl ester;
3-(o-Carboxyphenyl)-N-(methylcarbamoyl)-sydnonimin; 3-Benzyl-4-(carboxymethyl)-N-(methylcarbamoyl)-sydnon- imin-ethylester;3- (o-carboxyphenyl) -N- (methylcarbamoyl) -sydnonimine; 3-benzyl-4- (carboxymethyl) -N- (methylcarbamoyl) -sydnon-imine ethyl ester;
4-(2-Ethoxy-2-oxoethyl)-3-methyl-N-( (methylamino)carbo¬ nyl)-sydnonimin;4- (2-ethoxy-2-oxoethyl) -3-methyl-N- ((methylamino) carbonyl) -sydnonimine;
3-(Carboxymethyl)-4-methyl-N-(phenylthiocarbamoyl)-syd- nonimin-ethylester;3- (carboxymethyl) -4-methyl-N- (phenylthiocarbamoyl) -syd-nonimin ethyl ester;
3-(Carboxymethyl)-4-phenyl-N-(phenylthiocarbamoyl)-syd- nonimin-ethylester;3- (carboxymethyl) -4-phenyl-N- (phenylthiocarbamoyl) -syd-nonimin ethyl ester;
3-(Carboxymethyl)-4-phenyl-N-(phenylcarbamoyl)-sydnon- i in-ethylester; 3-(Carboxymethyl)-N-(methylcarbamoyl)-sydnonimin-ethyl- ester;3- (carboxymethyl) -4-phenyl-N- (phenylcarbamoyl) -sydnone-i in ethyl ester; 3- (carboxymethyl) -N- (methylcarbamoyl) -sydnonimine-ethyl ester;
3-(Carboxymethyl)-N-( (o-chlorphenyl)carbamoyl)-sydnon- imin-ethylester;3- (carboxymethyl) -N- ((o-chlorophenyl) carbamoyl) -sydnonimine ethyl ester;
N-Benzoyl-3-(carboxymethyl)-4-phenyl-sydnonimin-ethyl- ester;N-benzoyl-3- (carboxymethyl) -4-phenyl-sydnonimine-ethyl ester;
N-Benzoyl-3-(carboxymethyl)-sydnonimin;N-benzoyl-3- (carboxymethyl) -sydnonimine;
3-(Carboxymethyl)-sydnonimin;3- (carboxymethyl) -sydnonimine;
4-(Carboxymethyl)-3-methyl-N-(phenylcarbamoyl)-sydnon¬ imin; 3-(α-Carboxy-p-tolyl)-N-( (o-chlorphenyl)carbamoyl)-syd- nonimin;4- (carboxymethyl) -3-methyl-N- (phenylcarbamoyl) -sydnon¬ imine; 3- (α-carboxy-p-tolyl) -N- ((o-chlorophenyl) carbamoyl) -syd- nonimin;
3-(α-Carboxy-p-tolyl)-N-(methylcarbamoyl)-sydnonimin; 4-(Carboxymethyl)-3-methyl-N-(methylcarbamoyl)-sydnon¬ imin; N-(Benzylcarbamoyl)-3-(carboxymethyl)-sydnonimin;3- (α-carboxy-p-tolyl) -N- (methylcarbamoyl) -sydnonimine; 4- (carboxymethyl) -3-methyl-N- (methylcarbamoyl) -sydnon¬ imine; N- (benzylcarbamoyl) -3- (carboxymethyl) -sydnonimine;
3-(Carboxymethyl)-4-phenyl-N-(phenylthiocarbamoyl)-syd¬ nonimin;3- (carboxymethyl) -4-phenyl-N- (phenylthiocarbamoyl) -syd¬ nonimin;
3-(Carboxymethyl)-4-phenyl-N-(phenylcarbamoyl)-sydnon¬ imin; 3-(Carboxymethyl)-N-((o-chlorphenyl)carbamoyl)-sydnon¬ imin;3- (carboxymethyl) -4-phenyl-N- (phenylcarbamoyl) -sydnon¬ imine; 3- (carboxymethyl) -N - ((o-chlorophenyl) carbamoyl) -sydnon¬ imine;
3-(α-Carboxy-p-tolyl)-sydnonimin-ethylester; 3-(o-Carboxyphenyl)-sydnonimin; 3-Benzyl-4-(carboxymethyl)-sydnonimin-ethylester; 4-(Carboxymethyl)-3-methyl-sydnonimin-ethylester; 3-(2-Ethoxy-2-oxoethyl)-sydnonimin; 3-(Methoxyphenyl)-sydnonimin; N-Acetyl-3-cyclohexyl-sydnonimin; N-Formyl-3-morpholino-sydnonimin; 3-Cyclohexyl-4-isopropyl-sydnonimin; 4-Methyl-3-morpholino-sydnonimin; 4-Methyl-3-(l-methyl-2-phenylethyl)-sydnonimin; 3-(3-Piperidinopropyl)-sydnonimin; 3-(3-(Dimethylamino)propyl)-sydnonimin; 3-(2-(Diethylamino)ethyl)-sydnonimin; 3-(2-(Dimethylamino)ethyl)-sydnonimin; 3-Cyclohexyl-4-methyl-sydnonimin;3- (α-carboxy-p-tolyl) -sydnonimine ethyl ester; 3- (o-carboxyphenyl) -sydnonimine; 3-benzyl-4- (carboxymethyl) -sydnonimine ethyl ester; 4- (carboxymethyl) -3-methyl-sydnonimine ethyl ester; 3- (2-ethoxy-2-oxoethyl) sydnonimine; 3- (methoxyphenyl) -sydnonimine; N-acetyl-3-cyclohexyl-sydnonimine; N-formyl-3-morpholinosydnonimine; 3-cyclohexyl-4-isopropyl-sydnonimine; 4-methyl-3-morpholinosydnonimine; 4-methyl-3- (l-methyl-2-phenylethyl) sydnonimine; 3- (3-piperidinopropyl) -sydnonimine; 3- (3- (Dimethylamino) propyl) -sydnonimine; 3- (2- (diethylamino) ethyl) -sydnonimine; 3- (2- (dimethylamino) ethyl) -sydnonimine; 3-cyclohexyl-4-methyl-sydnonimine;
4-Brom-N-carboxy-3-morpholino-sydnonimin phenylester; N-Carboxy-3-(dimethylamino)-sydnonimin benzylester; 4-Brom-N-(methoxycarbonyl)-3-(methyl(1-phenylethyl)ami¬ no)-sydnonimin;4-bromo-N-carboxy-3-morpholinosydnonimine phenyl ester; N-carboxy-3- (dimethylamino) -sydnonimine benzyl ester; 4-bromo-N- (methoxycarbonyl) -3- (methyl (1-phenylethyl) ami¬ no) -sydnonimine;
N-Carboxy-4-chlor-3-(dimethylamino)-sydnonimin-allyl- ester; N-Carboxy-3-(dimethylamino)-sydnonimin-allylester; N-Carboxy-3-(methyl(α-methylbenzyl)amino)-sydnonimin- methylester;N-carboxy-4-chloro-3- (dimethylamino) -sydnonimine allyl ester; N-carboxy-3- (dimethylamino) -sydnonimine allyl ester; N-carboxy-3- (methyl (α-methylbenzyl) amino) -sydnonimine- methyl ester;
4-Brom-N-(butoxycarbonyl)-3-(hexahydro-lH-azepin-1-yl)- sydnonimin;4-bromo-N- (butoxycarbonyl) -3- (hexahydro-1H-azepin-1-yl) sydnonimine;
N-Carboxy-3-(hexahydro-lH-azepin-1-yl)-sydnonimin-butyl- ester;N-carboxy-3- (hexahydro-1H-azepin-1-yl) -sydnonimine-butyl ester;
4-Brom-N-carboxy-3-(4-methyl-l-piperazinyl)-sydnonimin- phenylester;4-bromo-N-carboxy-3- (4-methyl-l-piperazinyl) -sydnonimine-phenyl ester;
N-Carboxy-3-(4-methyl-1-piperazinyl)-sydnoniminphenyl- ester; N-Carboxy-4-chlor-3-(dimethylamino)-sydnoniminbenzyl¬ ester;N-carboxy-3- (4-methyl-1-piperazinyl) -sydnoniminphenyl ester; N-carboxy-4-chloro-3- (dimethylamino) -sydnonimine benzyl ester;
4-Brom-N-carboxy-3-(dimethylamino)-sydnoniminbenzylester;4-bromo-N-carboxy-3- (dimethylamino) -sydnonimine benzyl ester;
N-(Ethoxycarbonyl)-4-iodo-3-(4-morpholinyl)-sydnonimin;N- (ethoxycarbonyl) -4-iodo-3- (4-morpholinyl) -sydnonimine;
4-Brom-N-carboxy-3-morpholino-sydnonimin ethylester; 4-Brom-N-(ethoxycarbonyl)-3-(4-morpholinyl)-sydnonimin;4-bromo-N-carboxy-3-morpholinosydnonimine ethyl ester; 4-bromo-N- (ethoxycarbonyl) -3- (4-morpholinyl) -sydnonimine;
N-Carboxy-4-chlor-3-morpholino-sydnonimin ethylester;N-carboxy-4-chloro-3-morpholinosydnonimine ethyl ester;
N-Acetyl-4-brom-3-(methyl(α-methylbenzyl)amino)-sydnon¬ imin;N-acetyl-4-bromo-3- (methyl (α-methylbenzyl) amino) -sydnon¬ imine;
N-Acetyl-4-brom-3-(3,4-dihydro-2(IH)-isoquinolyl)-sydnon- imin;N-acetyl-4-bromo-3- (3,4-dihydro-2 (IH) -isoquinolyl) -sydnone imine;
3-(Methylpiperonylamino)-sydnonimin;3- (methylpiperonylamino) -sydnonimine;
3-Acetyl-N-morpholino-sydnonimin;3-acetyl-N-morpholinosydnonimine;
N-nitroso-3-(1-piρeridinyl)-sydnonimin;N-nitroso-3- (1-piρeridinyl) -sydnonimine;
3-(4-Morpholinyl)-N-( (phenylamino)carbonyl)-sydnonimin; 3-(4-Methyl-1-piperazinyl)-N-nitroso-sydnonimin;3- (4-morpholinyl) -N- ((phenylamino) carbonyl) -sydnonimine; 3- (4-methyl-1-piperazinyl) -N-nitroso-sydnonimine;
3-(bis(Phenylmethyl)amino)-4-methyl-N-nitroso-sydnonimin;3- (bis (phenylmethyl) amino) -4-methyl-N-nitrososydnonimine;
3,3'-(1,4-piperazinediyl)bis(N-nitroso-sydnonimin) ;3,3 '- (1,4-piperazinediyl) bis (N-nitroso-sydnonimine);
3-(2-Methyl-1-piperidinyl)-N-nitroso-sydnonimin;3- (2-methyl-1-piperidinyl) -N-nitroso-sydnonimine;
N-Nitroso-3-(1-pyrrolidinyl)-sydnonimin; 3-(Dibutylamino)-N-nitroso-sydnonimin;N-nitroso-3- (1-pyrrolidinyl) -sydnonimine; 3- (dibutylamino) -N-nitroso-sydnonimine;
N-( (4-(Acetylamino)phenyl)sulfonyl)-3-(4-morpholinyl)- sydnonimin;N- ((4- (acetylamino) phenyl) sulfonyl) -3- (4-morpholinyl) sydnonimine;
3-(4-Morpholinyl)-N-(3-pyridinylcarbonyl)-sydnonimin;3- (4-morpholinyl) -N- (3-pyridinylcarbonyl) -sydnonimine;
3-(4-Morpholinyl)-N-(l-oxo-2-( ( (phenylmethoxy)carbonyl)- amino)propyl)-sydnonimin; N-(1,3-dioxobutyl)-3-(-4-morpholinyl)-sydnonimin; N-Benzoyl-3-(dimethylamino)-4-methyl-sydnonimin; 3-(4-Morpholinyl)-N-( (phenylmethoxy)carbonyl)-sydnonimin; N-Benzoyl-3-(dimethylamino)-sydnonimin; 3-(4-Morpholinyl)-N-(l-oxo-3-phenyl-2-propenyl)-sydnon¬ imin;3- (4-morpholinyl) -N- (l-oxo-2- (((phenylmethoxy) carbonyl) amino) propyl) -sydnonimine; N- (1,3-dioxobutyl) -3 - (- 4-morpholinyl) -sydnonimine; N-benzoyl-3- (dimethylamino) -4-methyl-sydnonimine; 3- (4-morpholinyl) -N- ((phenylmethoxy) carbonyl) -sydnonimine; N-benzoyl-3- (dimethylamino) -sydnonimine; 3- (4-morpholinyl) -N- (l-oxo-3-phenyl-2-propenyl) -sydnon¬ imine;
3-(4-Morpholinyl)-N-(l-oxo-3-phenylpropyl)-sydnonimin; 3-(4-Morpholinyl)-N-(1-oxopropyl)-sydnonimin; 3-( -Morpholinyl)-N-(trichloracetyl)-sydnonimin; N-(dichloracetyl)-3-(4-morpholinyl)-sydnonimin; N-(Chloracetyl)-3-( -morpholinyl)-sydnonimi ; N-Formyl-3-(4-morpholinyl)-sydnonimin; 3-( -Morpholinyl)-N-(trifluoracetyl)-sydnonimin; 3-(4-Morpholinyl)-N-nitroso-sydnonimin; 3-(4-Morpholinyl)-N-( (phenylamino)carbonyl)-sydnonimin;3- (4-morpholinyl) -N- (l-oxo-3-phenylpropyl) sydnonimine; 3- (4-morpholinyl) -N- (1-oxopropyl) -sydnonimine; 3- (-Morpholinyl) -N- (trichloroacetyl) -sydnonimine; N- (dichloroacetyl) -3- (4-morpholinyl) -sydnonimine; N- (chloroacetyl) -3- (-morpholinyl) -sydnonimi; N-formyl-3- (4-morpholinyl) -sydnonimine; 3- (-morpholinyl) -N- (trifluoroacetyl) -sydnonimine; 3- (4-morpholinyl) -N-nitroso-sydnonimine; 3- (4-morpholinyl) -N- ((phenylamino) carbonyl) -sydnonimine;
N-((4-Chlorphenyl)sulfonyl)-3-(4-morρholinyl)-sydnonimin; N-Benzoyl-3-(4-morpholinyl)-sydnonimin;N - ((4-chlorophenyl) sulfonyl) -3- (4-morρholinyl) -sydnonimine; N-benzoyl-3- (4-morpholinyl) -sydnonimine;
3-(((2-Carboxy-3-(hydroxymethyl)-8-oxo-5-thia-l-azabicyc- lo(4.2 ,0)oct-2-en-7-yl)carbamoyl)methyl)-N-((o-chlor- phenyl)carbamoyl)-sydnoniminacetat;3 - (((2-Carboxy-3- (hydroxymethyl) -8-oxo-5-thia-l-azabicyclo (4.2, 0) oct-2-en-7-yl) carbamoyl) methyl) -N- ((o-chlorophenyl) carbamoyl) -sydnonimine acetate;
N-Benzoyl-3-(((2-carboxy-3-(hydroxymethyl)-8-oxo-5-thia- 1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)methyl)-syd¬ noniminacetat; 3-(((2-Carboxy-3-(hydroxymethyl)-8-oxo-5-thia-l-azabicyc- lo(4.2.0)oct-2-en-7-yl)carbamoyl)methyl)-N-(methylcarb¬ amoyl)-sydnoniminacetat; 3-sec-0ctyl-sydnonimin;N-Benzoyl-3 - (((2-carboxy-3- (hydroxymethyl) -8-oxo-5-thia-1-azabicyclo (4.2.0) oct-2-en-7-yl) carbamoyl) methyl) - syd¬ nonimin acetate; 3 - (((2-Carboxy-3- (hydroxymethyl) -8-oxo-5-thia-l-azabicyclo (4.2.0) oct-2-en-7-yl) carbamoyl) methyl) -N- (methylcarbamoyl) -sydnonimine acetate; 3-sec-octyl-sydnonimine;
4-Chlor-3-(dimethylamino)-N-nicotinoyl-sydnonimin; 4-Chlor-N-(cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnon- imin;4-chloro-3- (dimethylamino) -N-nicotinoyl-sydnonimine; 4-chloro-N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnon imine;
4-Brom-N-(2-chlorbenzoyl)-3-(methyl(phenylmethyl)amino)- sydnonimin;4-bromo-N- (2-chlorobenzoyl) -3- (methyl (phenylmethyl) amino) sydnonimine;
N-Acetyl-4-brom-3-(3,4-dihydro-2(IH)-isoquinolinyl)-syd¬ nonimin; N-Acetyl-4-brom-3-(1-piperidinyl)-sydnonimin; N-(Cyclohexylcarbonyl).-4-iodo-3-(4-morpholinyl)-sydnon¬ imin;N-acetyl-4-bromo-3- (3,4-dihydro-2 (IH) -isoquinolinyl) -syd¬ nonimin; N-acetyl-4-bromo-3- (1-piperidinyl) -sydnonimine; N- (Cyclohexylcarbonyl) .- 4-iodo-3- (4-morpholinyl) -sydnon¬ imine;
4-Chlor-N-(ethoxycarbonyl)-3-(1-piperidinyl)-sydnonimin;4-chloro-N- (ethoxycarbonyl) -3- (1-piperidinyl) -sydnonimine;
N-Acetyl-4-chlor-3-(hexahydro-lH-azepin-1-yl)-sydnonimin; 4-Chlor-3-(4-morpholinyl)-sydnonimin;N-acetyl-4-chloro-3- (hexahydro-lH-azepin-1-yl) -sydnonimine; 4-chloro-3- (4-morpholinyl) -sydnonimine;
4-Brom-N-(ethoxycarbonyl)-3-(1-piperidinyl)-sydnonimin;4-bromo-N- (ethoxycarbonyl) -3- (1-piperidinyl) -sydnonimine;
N-Benzoyl-4-brom-3-(dimethylamino)-sydnonimin;N-benzoyl-4-bromo-3- (dimethylamino) -sydnonimine;
4-Brom-3-(hexahydro-lH-azepin-1-yl)-sydnonimin;4-bromo-3- (hexahydro-1H-azepin-1-yl) -sydnonimine;
N-Acetyl-4-brom-3-(methyl(1-phenylethyl)amino)-sydnon- imin;N-acetyl-4-bromo-3- (methyl (1-phenylethyl) amino) -sydnonimine;
4-Brom-3-(dimethylamino)-N-(3-pyridinylcarbonyl)-sydnon¬ imin;4-bromo-3- (dimethylamino) -N- (3-pyridinylcarbonyl) -sydnon¬ imine;
4-Brom-3-(4-morpholinyl)-sydnonimin;4-bromo-3- (4-morpholinyl) -sydnonimine;
4-Brom-N-(cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnon- imin;4-bromo-N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnone imine;
N-Acetyl-3-(3,4-dihydro-2(IH)-isoquinolyl)-sydnonimin;N-acetyl-3- (3,4-dihydro-2 (IH) isoquinolyl) sydnonimine;
4-Brom-3-(1-piperidinyl)-sydnonimin;4-bromo-3- (1-piperidinyl) -sydnonimine;
4-Brom-3-(dimethylamino)-sydnonimin;4-bromo-3- (dimethylamino) -sydnonimine;
3-Piperidino-4-propyl-sydnonimin; 3-Amino-sydnonimin;3-piperidino-4-propyl-sydnonimine; 3-amino-sydnonimine;
N-(Cyclohexylcarbonyl)-3-(4-morpholinyl)-sydnonimin;N- (cyclohexylcarbonyl) -3- (4-morpholinyl) -sydnonimine;
3-(Allylmethylamino)-sydnonimin;3- (allylmethylamino) -sydnonimine;
N-(2-Chlorbenzoyl)-3-(hexahydro-lH-azepin-1-yl)-sydnon¬ imin; 3-(di-2-Propenylamino)-4-methyl-N-( (5-nitro-2-thienyl)- carbonyl)-sydnonimin;N- (2-chlorobenzoyl) -3- (hexahydro-lH-azepin-1-yl) -sydnon¬ imine; 3- (di-2-propenylamino) -4-methyl-N- ((5-nitro-2-thienyl) carbonyl) -sydnonimine;
N-(2-Chlorbenzoyl)-3-(methyl(phenylmethyl)amino)-sydnon¬ imin;N- (2-chlorobenzoyl) -3- (methyl (phenylmethyl) amino) -sydnon¬ imine;
N-(Cyclohexylcarbonyl)-3-(methyl(phenylmethyl)amino)-syd- nonimin;N- (cyclohexylcarbonyl) -3- (methyl (phenylmethyl) amino) -syd-nonimin;
N-(Cyclohexylcarbonyl)-3-(3 ,4-dihydro-2(IH)-isoquinoli- nyl)-sydnonimin;N- (cyclohexylcarbonyl) -3- (3,4-dihydro-2 (IH) -isoquinolinyl) sydnonimine;
N-(o-Chlorbenzoyl)-3-(3,4-dihydro-2(IH)-isoquinolyl)- sydnonimin; N-(2-Methylbenzoyl)-3-(4-morpholinyl)-sydnonimin; N-(2-Chlorbenzoyl)-3-(-4-morpholinyl)-sydnonimin;N- (o-chlorobenzoyl) -3- (3,4-dihydro-2 (IH) isoquinolyl) sydnonimine; N- (2-methylbenzoyl) -3- (4-morpholinyl) -sydnonimine; N- (2-chlorobenzoyl) -3 - (- 4-morpholinyl) -sydnonimine;
N-Acetyl-3-(hexahydro-lH-azepin-1-yl)-sydnonimin;N-acetyl-3- (hexahydro-1H-azepin-1-yl) -sydnonimine;
N-(Cyclohexylcarbonyl)-3-(hexahydro-lH-azepin-1-yl)-syd¬ nonimin; 3-(Hexahydro-lH-azepin-1-yl)-N-(2-methylbenzoyl)-sydnon¬ imin;N- (cyclohexylcarbonyl) -3- (hexahydro-lH-azepin-1-yl) -syd nonimin; 3- (hexahydro-1H-azepin-1-yl) -N- (2-methylbenzoyl) -sydnon imine;
3-(Dimethylamino)-N-(5-nitro-2-furoyl)-sydnonimin;3- (dimethylamino) -N- (5-nitro-2-furoyl) -sydnonimine;
3-(Dimethylamino)-N-((5-nitro-2-thienyl)carbonyl)-sydnon¬ imin; 3-(Methyl(2-pyridylmethyl)amino)-sydnonimin;3- (dimethylamino) -N - ((5-nitro-2-thienyl) carbonyl) -sydnon¬ imine; 3- (methyl (2-pyridylmethyl) amino) -sydnonimine;
N-(Ethoxycarbonyl)-3-(4-morpholinyl)-sydnonimin;N- (ethoxycarbonyl) -3- (4-morpholinyl) -sydnonimine;
3-(Diallylamino)-4-ethyl-sydnonimin;3- (diallylamino) -4-ethyl-sydnonimine;
3-(Diallylamino)-4-methyl-sydnonimin;3- (diallylamino) -4-methyl-sydnonimine;
3-(Diallylamino)-4-phenethyl-sydnonimin; 3-(Methyl(2-propynyl)amino)-sydnonimin;3- (diallylamino) -4-phenethyl-sydnonimine; 3- (methyl (2-propynyl) amino) -sydnonimine;
3-(Methyl(phenylmethyl)amino)-sydnonimin;3- (methyl (phenylmethyl) amino) -sydnonimine;
3-(Diallylamino)-sydnonimin;3- (diallylamino) -sydnonimine;
N-(Cyclopropylcarbonyl)-3-(dimethylamino)-sydnonimin;N- (cyclopropylcarbonyl) -3- (dimethylamino) -sydnonimine;
N-Carboxy-3-(dimethylamino)-sydnonimin ethylester; 3-(Diethylamino)-sydnonimin;N-carboxy-3- (dimethylamino) -sydnonimine ethyl ester; 3- (diethylamino) -sydnonimine;
3-((p-Chlorbenzyl) ropylamino)-sydnonimin;3 - ((p-chlorobenzyl) ropylamino) -sydnonimine;
3-(Methylphenethylamino)-sydnonimin;3- (methylphenethylamino) -sydnonimine;
3-(Methyl(piperidinomethyl)amino)-sydnonimin;3- (methyl (piperidinomethyl) amino) -sydnonimine;
3-(Methyl(α-methylbenzyl)amino)-sydnonimin; 3-(2-Phenylpiperidino)-sydnonimin;3- (methyl (α-methylbenzyl) amino) -sydnonimine; 3- (2-phenylpiperidino) sydnonimine;
3-(bis(Phenylmethyl)amino)-sydnonimin;3- (bis (phenylmethyl) amino) -sydnonimine;
3-(Hexahydro-lH-azepin-1-yl)-sydnonimin;3- (hexahydro-lH-azepin-1-yl) -sydnonimine;
3-(4-Methyl-l-piperazinyl)-sydnonimin;3- (4-methyl-l-piperazinyl) sydnonimine;
3-(3,4-Dihydro-2(IH)-isoquinolinyl)-sydnonimin; N-Acetyl-3-(dimethylamino)-sydnonimin;3- (3,4-dihydro-2 (IH) isoquinolinyl) sydnonimine; N-acetyl-3- (dimethylamino) -sydnonimine;
3-(Dimethylamino)-N-(3,3-dimethylbutyryl)-sydnonimin;3- (dimethylamino) -N- (3,3-dimethylbutyryl) -sydnonimine;
3-(Dimethylamino)-N-nicotinoyl-sydnonimin;3- (dimethylamino) -N-nicotinoyl-sydnonimine;
N-(Cyclohexylcarbonyl)-3-(dimethylamino)-sydnonimin;N- (cyclohexylcarbonyl) -3- (dimethylamino) -sydnonimine;
3-(Dimethylamino)-N-o-toluoyl-sydnonimin; N-(p-Chlorbenzoyl)-3-(dimethylamino)-sydnonimin; N-(o-Chlorbenzoyl)-3-(dimethylamino)-sydnonimin;3- (dimethylamino) -no-toluoyl-sydnonimine; N- (p-chlorobenzoyl) -3- (dimethylamino) -sydnonimine; N- (o-chlorobenzoyl) -3- (dimethylamino) -sydnonimine;
N-Benzoyl-3-(dimethylamino)-sydnonimin;N-benzoyl-3- (dimethylamino) -sydnonimine;
N-Acetyl-3-(4-acetylhexahydro-lH-l,4-diazepin-l-yl)-syd¬ nonimin; N-Acetyl-3-piperidino-sydnonimin;N-acetyl-3- (4-acetylhexahydro-lH-l, 4-diazepin-l-yl) -syd nonimin; N-acetyl-3-piperidinosydnonimine;
N-Carboxy-3-(diallylamino)-4-ethyl-sydnonimin ethylester;N-carboxy-3- (diallylamino) -4-ethyl-sydnonimine ethyl ester;
N-Carboxy-3-piperidino-sydnonimin ethylester;N-carboxy-3-piperidinosydnonimine ethyl ester;
3-(Dimethylamino)-N-hydrocinnamoyl-sydnonimin;3- (dimethylamino) -N-hydrocinnamoyl-sydnonimine;
3-(Methyl(α-methylbenzyl)amino)-N-nicotinoyl-sydnonimin; N-Benzoyl-3-(hexahydro-lH-azepin-1-yl)-sydnonimin;3- (methyl (α-methylbenzyl) amino) -N-nicotinoyl-sydnonimine; N-benzoyl-3- (hexahydro-1H-azepin-1-yl) -sydnonimine;
N-Acetyl-3-(diallylamino)-sydnonimin;N-acetyl-3- (diallylamino) -sydnonimine;
3-(Dimethylamino)-N-(5-nitro-2-furoyl)-sydnonimin;3- (dimethylamino) -N- (5-nitro-2-furoyl) -sydnonimine;
3-(4-Benzyl-3-phenyl-1-piperazinyl)-sydnonimin;3- (4-benzyl-3-phenyl-1-piperazinyl) sydnonimine;
3-(4-Benzyl-l-piperazinyl)-4-methyl-sydnonimin; 3-(4-Benzyl-l-piperazinyl)-sydnonimin;3- (4-benzyl-l-piperazinyl) -4-methyl-sydnonimine; 3- (4-benzyl-l-piperazinyl) sydnonimine;
3-(4-Methyl-l-piperazinyl)-sydnonimin;3- (4-methyl-l-piperazinyl) sydnonimine;
3-(4-(p-Chlorphenyl)-1-piperazinyl)-sydnonimin;3- (4- (p-chlorophenyl) -1-piperazinyl) sydnonimine;
3-(2-Phenoxyethyl)-sydnonimin;3- (2-phenoxyethyl) sydnonimine;
3-(2-Hydroxyethyl)-sydnonimin; 3-(l-Methyl-2-phenylethyl)-sydnonimin;3- (2-hydroxyethyl) sydnonimine; 3- (l-methyl-2-phenylethyl) -sydnonimine;
3-Phenethyl-sydnonimin;3-phenethyl-sydnonimine;
3-(α-Methylbenzyl)-sydnonimin;3- (α-methylbenzyl) -sydnonimine;
3-(2-Methylpropyl)-sydnonimin;3- (2-methylpropyl) sydnonimine;
4-Ethyl-3-(2-methylpropyl)-N-nitroso-sydnonimin; 3-(3-Chlorphenyl)-N-nitroso-sydnonimin;4-ethyl-3- (2-methylpropyl) -N-nitroso-sydnonimine; 3- (3-chlorophenyl) -N-nitroso-sydnonimine;
3-(2-hydroxyethyl)-sydnoniminacetat;3- (2-hydroxyethyl) sydnonimine acetate;
3-(3-Carboxypropyl)-sydnonimin;3- (3-carboxypropyl) -sydnonimine;
3-Methyl-4-nonyl-sydnonimin;3-methyl-4-nonyl-sydnonimine;
3-(2,2-Diphenylethyl)-N-((phenylamino)carbonyl)-sydnon- imin;3- (2,2-diphenylethyl) -N - ((phenylamino) carbonyl) -sydnone imine;
3-(2,2-Diphenylethyl)-N-nitroso-sydnonimin;3- (2,2-diphenylethyl) -N-nitroso-sydnonimine;
N-(methoxycarbonyl)-3-phenyl-sydnonimin;N- (methoxycarbonyl) -3-phenyl-sydnonimine;
3-Benzyl-5-(carboxyamino)-1,2 ,3-oxadiazoliumhydroxid- methylester; 3-Butyl-N-(methoxycarbonyl)-sydnonimin; N-Benzoyl-3-butyl-sydnonimin;3-benzyl-5- (carboxyamino) -1,2,3-oxadiazolium hydroxide methyl ester; 3-butyl-N- (methoxycarbonyl) -sydnonimine; N-benzoyl-3-butyl-sydnonimine;
N-Acetyl-3-butyl-sydnonimin;N-acetyl-3-butyl-sydnonimine;
N-Acetyl-3-(1-methylethyl)-sydnonimin;N-acetyl-3- (1-methylethyl) -sydnonimine;
3-sec-Butyl-sydnonimin; 3-(1-Methylhepty1)-sydnonimin;3-sec-butyl-sydnonimine; 3- (1-methylhepty1) -sydnonimine;
3-m-Tolyl-sydnonimin;3-m-tolyl-sydnonimine;
3-(2-Phenylethyl)-sydnonimin;3- (2-phenylethyl) -sydnonimine;
3-(1-Methylpropyl)-sydnonimin;3- (1-methylpropyl) -sydnonimine;
3-(1-Methyl-2,2-diphenylethyl)-sydnonimin; 3-(2,2-Diphenylethyl)-sydnonimin;3- (1-methyl-2,2-diphenylethyl) sydnonimine; 3- (2,2-diphenylethyl) -sydnonimine;
3-(2-Hydroxy-1-methyl-2-phenylethyl)-sydnonimin;3- (2-hydroxy-1-methyl-2-phenylethyl) sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-nitroso-4-phenyl-sydnonimin;3- (l-methyl-2-phenylethyl) -N-nitroso-4-phenyl-sydnonimine;
3-Cyclohexyl-4-((diethylamino)methyl)-N-nitroso-sydnon¬ imin; 3-(1-Methylethyl)-N-nitroso-sydnonimin;3-cyclohexyl-4 - ((diethylamino) methyl) -N-nitroso-sydnon¬ imine; 3- (1-methylethyl) -N-nitrososydnonimine;
3-Ethyl-N-nitroso-sydnonimin;3-ethyl-N-nitroso-sydnonimine;
3-Methyl-N-nitroso-sydnonimin;3-methyl-N-nitroso-sydnonimine;
3-(α-Methylphenethyl)-sydnonimin;3- (α-methylphenethyl) -sydnonimine;
3-(p-Ethoxyphenyl)-N-nitroso-sydnonimin; 3-(p-Ethoxyphenyl)-sydnonimin;3- (p-ethoxyphenyl) -N-nitroso-sydnonimine; 3- (p-ethoxyphenyl) -sydnonimine;
3-(l-Methyl-2-phenylethyl)-N-nitroso-4-(1-piperidinyl- methyl)-sydnonimin;3- (l-methyl-2-phenylethyl) -N-nitroso-4- (1-piperidinyl-methyl) -sydnonimine;
4-((Dimethylamino)methyl)-3-(l-methyl-2-phenylethyl)-N- nitroso-sydnonimin; N-Benzoyl-3-(α-methylphenethyl)-4-(piperidinomethyl)-sydn onimin;4 - ((dimethylamino) methyl) -3- (l-methyl-2-phenylethyl) -N-nitrososydnonimine; N-benzoyl-3- (α-methylphenethyl) -4- (piperidinomethyl) sydn onimine;
N-Benzoyl-3-cyclohexyl-4-((diethylamino)methyl)-sydnon¬ imin; 4-((Diethylamino)methyl)-3-(α-methylphenethyl)-sydnon- imin;N-benzoyl-3-cyclohexyl-4 - ((diethylamino) methyl) -sydnon¬ imine; 4 - ((diethylamino) methyl) -3- (α-methylphenethyl) -sydnone imine;
4-( (Dimethylamino)methyl)-3-(α-methylphenethyl)-sydnon¬ imin;4- ((dimethylamino) methyl) -3- (α-methylphenethyl) -sydnon¬ imine;
4-( (Diethylamino)methyl)-3-isopropyl-sydnonimin; 3-Cyclohexyl-4-( (diethylamino)methyl)-sydnonimi ; 3-Cyclohexyl-4-(nitromethyl)-N-nitroso-sydnonimin; 4-(Nitromethyl)-N-nitroso-3-(phenylmethyl)-sydnonimin;4- ((diethylamino) methyl) -3-isopropyl-sydnonimine; 3-cyclohexyl-4- ((diethylamino) methyl) -sydnonimi; 3-cyclohexyl-4- (nitromethyl) -N-nitroso-sydnonimine; 4- (nitromethyl) -N-nitroso-3- (phenylmethyl) -sydnonimine;
3-Cyclohexyl-4-(nitromethyl)-N-nitroso-sydnonimin;3-cyclohexyl-4- (nitromethyl) -N-nitroso-sydnonimine;
3-(1-Methylethyl)-4-(nitromethyl)-N-nitroso-sydnonimin;3- (1-methylethyl) -4- (nitromethyl) -N-nitroso-sydnonimine;
4-(Chlormethyl)-3-isobutyl-sydnonimin; 3-Benzyl-4-(chlormethyl)-sydnonimin;4- (chloromethyl) -3-isobutyl-sydnonimine; 3-benzyl-4- (chloromethyl) -sydnonimine;
3-( -Methylphenethyl)-N-(phenylthiocarbamoyl)-sydnonimin;3- (-Methylphenethyl) -N- (phenylthiocarbamoyl) -sydnonimine;
N-( (m-Chlorphenyl)carbamoyl)-3-(α-methylphenethyl)-syd¬ nonimin;N- ((m-chlorophenyl) carbamoyl) -3- (α-methylphenethyl) -syd nonimin;
3-(2-(Diethylamino)ethyl)-N-(phenylcarbamoyl)-sydnonimin; N-( (Phenylamino)carbonyl)-3-(2-phenylethyl)-sydnonimin;3- (2- (diethylamino) ethyl) -N- (phenylcarbamoyl) -sydnonimine; N- ((phenylamino) carbonyl) -3- (2-phenylethyl) -sydnonimine;
3-(α-Methylbenzyl)-N-(phenylcarbamoyl)-sydnonimin;3- (α-methylbenzyl) -N- (phenylcarbamoyl) -sydnonimine;
3-Benzyl-N-(phenylcarbamoyl)-sydnonimin;3-benzyl-N- (phenylcarbamoyl) -sydnonimine;
N-(Aminocarbonyl)-3-(1-methyl-2-phenylethyl)-sydnonimin;N- (aminocarbonyl) -3- (1-methyl-2-phenylethyl) sydnonimine;
3-(α-Methylphenethyl)-N-nicotinoyl-sydnonimin; 3-(α-Methylphenethyl)-N-(phenylacetyl)-sydnonimin;3- (α-methylphenethyl) -N-nicotinoyl-sydnonimine; 3- (α-methylphenethyl) -N- (phenylacetyl) -sydnonimine;
3-Phenethyl-N-(phenylacetyl)-sydnonimin;3-phenethyl-N- (phenylacetyl) -sydnonimine;
N-Carboxy-3-(α-methylphenethyl)-sydnonimin methylester;N-carboxy-3- (α-methylphenethyl) -sydnonimine methyl ester;
N-Carboxy-3-phenethyl-sydnonimin methylester;N-carboxy-3-phenethyl-sydnonimine methyl ester;
N-Carboxy-3-methyl-sydnonimin methylester; 4-(p-Methoxyphenyl)-3-(α-methylphenethyl)-sydnonimin;N-carboxy-3-methyl-sydnonimine methyl ester; 4- (p-methoxyphenyl) -3- (α-methylphenethyl) sydnonimine;
3-(l-Methyl-2-phenylethyl)-4-phenyl-sydnonimin;3- (l-methyl-2-phenylethyl) -4-phenyl-sydnonimine;
3-(2-Hydroxy-1-methyl-2-phenylethyl)-sydnonimin;3- (2-hydroxy-1-methyl-2-phenylethyl) sydnonimine;
3-(2-Phenoxyethyl)-sydnonimin;3- (2-phenoxyethyl) sydnonimine;
3,3'-(1,2-Ethanediyl)bis(N-nitroso-)sydnonimin; 4-Methyl-N-nitroso-3-(phenylmethyl)-sydnonimin;3,3 '- (1,2-ethanediyl) bis (N-nitroso) sydnonimine; 4-methyl-N-nitroso-3- (phenylmethyl) -sydnonimine;
4-Brom-N-nitroso-3-phenyl-sydnonimin;4-bromo-N-nitroso-3-phenyl-sydnonimine;
3-(4-Chlorphenyl)-N-nitroso-sydnonimin;3- (4-chlorophenyl) -N-nitroso-sydnonimine;
3-(4-Ethoxyphenyl)-N-nitroso-sydnonimin;3- (4-ethoxyphenyl) -N-nitroso-sydnonimine;
3-(4-Methoxyphenyl)-N-nitroso-sydnonimin; N-Nitroso-3-phenyl-sydnonimin;3- (4-methoxyphenyl) -N-nitroso-sydnonimine; N-nitroso-3-phenyl-sydnonimine;
3-Cyclohexyl-N-nitroso-sydnonimin;3-cyclohexyl-N-nitroso-sydnonimine;
N-Nitroso-3-(phenylmethyl)-sydnonimin;N-nitroso-3- (phenylmethyl) -sydnonimine;
N-Nitroso-3-(2-phenylethyl)-sydnonimin;N-nitroso-3- (2-phenylethyl) -sydnonimine;
3-(1-Methyl-2-phenylethyl)-N-nitroso-sydnonimin; 3-Cycloheptyl-sydnonimin; 3-Cyclopentyl-sydnonimin;3- (1-methyl-2-phenylethyl) -N-nitrososydnonimine; 3-cycloheptyl-sydnonimine; 3-cyclopentyl-sydnonimine;
3-(Allylmethylamino)-sydnonimin; •3- (allylmethylamino) -sydnonimine; •
3,3'-(1,4-piperazinediyl)disydnonimin;3,3 '- (1,4-piperazinediyl) disydnonimine;
4-Methyl-3-(1-piperidinyl)-sydnonimin; 3-(Dibutylamino)-sydnonimin;4-methyl-3- (1-piperidinyl) sydnonimine; 3- (dibutylamino) -sydnonimine;
3-(2-Methyl-l-piperidinyl)-sydnonimin;3- (2-methyl-l-piperidinyl) sydnonimine;
3-(Dimethylamino)-sydnonimin; 3-(1-Pyrrolidinyl)-sydnonimin; 3-(1-Piperidinyl)-sydnonimin; 3-(p-Fluorphenyl)-sydnonimin;3- (dimethylamino) -sydnonimine; 3- (1-pyrrolidinyl) -sydnonimine; 3- (1-piperidinyl) -sydnonimine; 3- (p-fluorophenyl) -sydnonimine;
3-(m-Fluorphenyl)-sydnonimin;3- (m-fluorophenyl) -sydnonimine;
4-Methyl-3-piperonyl-sydnonimin; N-Carbamoyl-3-phenyl-sydnonimin; N-Benzoyl-4-brom-3-(2-methylpropyl)-sydnonimin; N-(Ethoxycarbonyl)-3,4-diphenyl-sydnonimin; N-Acetyl-3,4-diphenyl-sydnonimin; 3-p-Tolyl-sydnonimin;4-methyl-3-piperonyl-sydnonimine; N-carbamoyl-3-phenyl-sydnonimine; N-benzoyl-4-bromo-3- (2-methylpropyl) sydnonimine; N- (ethoxycarbonyl) -3,4-diphenyl-sydnonimine; N-acetyl-3,4-diphenyl-sydnonimine; 3-p-tolyl-sydnonimine;
4-(4-(1-Methylethyl)phenyl)-N-nitroso-3-(phenylmethyl)- sydnonimin; 3-(l-Methyl-2-phenylethyl)-N-(phenylsulfonyl)-sydnonimin; 4-(3-Nitrophenyl)-N-nitroso-3-(phenylmethyl)-sydnonimin; 4-(Chlormethyl)-3-isopropyl-sydnonimin; 3-Benzyl-4-(p-(dimethylamino)phenyl)-sydnonimin; 3-1sopropyl-4-methyl-sydnonimin; 3-(1-Methylethyl)-sydnonimin;4- (4- (1-methylethyl) phenyl) -N-nitroso-3- (phenylmethyl) sydnonimine; 3- (l-methyl-2-phenylethyl) -N- (phenylsulfonyl) -sydnonimine; 4- (3-nitrophenyl) -N-nitroso-3- (phenylmethyl) -sydnonimine; 4- (chloromethyl) -3-isopropyl-sydnonimine; 3-benzyl-4- (p- (dimethylamino) phenyl) -sydnonimine; 3-1sopropyl-4-methyl-sydnonimine; 3- (1-methylethyl) -sydnonimine;
4-Brom-3-(α-methylphenethyl)-N-(phenylsulfonyl)-sydnon¬ imin;4-bromo-3- (α-methylphenethyl) -N- (phenylsulfonyl) -sydnon¬ imine;
N-Nitroso-4-phenyl-3-(phenylmethyl)-sydnonimin; 3-Benzyl-4-(4-hydroxy-3-methoxyphenyl)-sydnonimin; 3-Benzyl-4-p-cumenyl-sydnonimin;N-nitroso-4-phenyl-3- (phenylmethyl) -sydnonimine; 3-benzyl-4- (4-hydroxy-3-methoxyphenyl) sydnonimine; 3-benzyl-4-p-cumenyl-sydnonimine;
4-(4-Methoxyphenyl)-N-nitroso-3-(phenylmethyl)-sydnon¬ imin;4- (4-methoxyphenyl) -N-nitroso-3- (phenylmethyl) -sydnon¬ imine;
4-(4-(Dimethylamino)phenyl)-N-nitroso-3-(phenylmethyl)- sydnonimin; 3-Benzyl-4-(m-nitrophenyl)-sydnonimin; 4-(3-Nitrophenyl)-3-(phenylmethyl)-sydnonimin;4- (4- (dimethylamino) phenyl) -N-nitroso-3- (phenylmethyl) sydnonimine; 3-benzyl-4- (m-nitrophenyl) -sydnonimine; 4- (3-nitrophenyl) -3- (phenylmethyl) -sydnonimine;
3-Benzyl-4-(4-hydroxy-3-methoxyphenyl)-sydnonimin;3-benzyl-4- (4-hydroxy-3-methoxyphenyl) sydnonimine;
4-(4-Methoxyphenyl)-N-nitroso-3-(phenylmethyl)-sydnon¬ imin; N-Acetyl-3-benzyl-4-phenyl-sydnonimin;4- (4-methoxyphenyl) -N-nitroso-3- (phenylmethyl) -sydnon¬ imine; N-acetyl-3-benzyl-4-phenyl-sydnonimine;
N-Benzoyl-3-benzyl-4-phenyl-sydnonimin;N-benzoyl-3-benzyl-4-phenyl-sydnonimine;
3-(1,3-Benzodioxol-5-ylmethyl)-sydnonimin;3- (1,3-benzodioxol-5-ylmethyl) -sydnonimine;
N-(N-Acetylsulfanilyl)-3-piperonyl-sydnonimin;N- (N-acetylsulfanilyl) -3-piperonyl-sydnonimine;
3,4-Diphenyl-sydnonimin; 3-Isopropyl-4-methyl-sydnonimin;3,4-diphenyl-sydnonimine; 3-isopropyl-4-methyl-sydnonimine;
3-(2-Chlorethyl)-sydnonimin;3- (2-chloroethyl) sydnonimine;
3-(1-Methylethyl)-sydnonimin;3- (1-methylethyl) -sydnonimine;
4-(Chlormethyl)-3-isopropyl-sydnonimin;4- (chloromethyl) -3-isopropyl-sydnonimine;
3-Cyclohexyl-sydnonimin; 3-Methyl-sydnonimin;3-cyclohexyl-sydnonimine; 3-methyl-sydnonimine;
3-Ethyl-sydnonimin;3-ethyl-sydnonimine;
3-Butyl-sydnonimin;3-butyl-sydnonimine;
4-Methyl-3-(α-methylphenethyl)-sydnonimin;4-methyl-3- (α-methylphenethyl) sydnonimine;
3,4-Diphenyl-sydnonimin; -Methyl-3-phenyl-sydnonimin;3,4-diphenyl-sydnonimine; -Methyl-3-phenyl-sydnonimine;
3-(2-Carboxyethyl)-sydnonimin;3- (2-carboxyethyl) sydnonimine;
4-Phenyl-3-p-tolyl-sydnonimin;4-phenyl-3-p-tolylsydnonimine;
3-(o-Methoxyphenyl)-sydnonimin;3- (o-methoxyphenyl) -sydnonimine;
3-(1-Methyl-2-phenylethyl)-sydnonimin; 3-(2-Methylpropyl)-sydnonimin;3- (1-methyl-2-phenylethyl) sydnonimine; 3- (2-methylpropyl) sydnonimine;
3-(2-Hydroxyethyl)-sydnonimin;3- (2-hydroxyethyl) sydnonimine;
3-(3-Methoxy-3-oxopropyl)-sydnonimin;3- (3-methoxy-3-oxopropyl) -sydnonimine;
N-Benzoyl-3-(2-methylpropyl)-sydnonimin; -N-benzoyl-3- (2-methylpropyl) sydnonimine; -
N-Benzoyl-4-methyl-3-(phenylmethyl)-sydnonimin; N-(Dichlorphosphinyl)-3-(1-methylethyl)-sydnonimin;N-benzoyl-4-methyl-3- (phenylmethyl) sydnonimine; N- (dichlorophosphinyl) -3- (1-methylethyl) -sydnonimine;
N-(Dichlorphosphinyl)-4-methyl-3-phenyl-sydnonimin;N- (dichlorophosphinyl) -4-methyl-3-phenyl-sydnonimine;
3-(1-Phenylethyl)-sydnonimin;3- (1-phenylethyl) -sydnonimine;
4-Phenyl-3-(phenylmethyl)-sydnonimin;4-phenyl-3- (phenylmethyl) -sydnonimine;
4-Methyl-3-(phenylmethyl)-sydnonimin; 3-( (4-Chlorphenyl)methyl)-sydnonimin; 3-(Phenylmet yl)-sydnonimin;4-methyl-3- (phenylmethyl) -sydnonimine; 3- ((4-chlorophenyl) methyl) -sydnonimine; 3- (phenylmet yl) -sydnonimine;
N-Carboxy-3-( -ethoxyphenyl)-sydnonimin methylester;N-carboxy-3- (-ethoxyphenyl) -sydnonimine methyl ester;
N-Carboxy-3-(p-methoxyphenyl)-sydnonimin methylester;N-carboxy-3- (p-methoxyphenyl) -sydnonimine methyl ester;
N-Carboxy-3-(p-chlorphenyl)-sydnonimin methylester; N-Carboxy-3-ρ-tolyl-sydnonimin methylester;N-carboxy-3- (p-chlorophenyl) sydnonimine methyl ester; N-carboxy-3-ρ-tolyl-sydnonimine methyl ester;
N-Carboxy-3-(m-chlorphenyl)-sydnonimin methylester; sowie deren pharmakologisch verträglichen Salze.N-carboxy-3- (m-chlorophenyl) -sydnonimine methyl ester; and their pharmacologically acceptable salts.
Pharmakologisch annehmbare Salze der Sydnonimine der all- gemeinen Formel I sind insbesondere Säureadditionssalze mit anorganischen oder organischen Säuren. Geeignete Säuren sind beispielsweise Chlorwasserstoff, Bromwasser¬ stoff, Naphthalindisulfonsäuren, insbesondere Naphtha- lin-disulfonsäure(l,5), Phosphor-, Salpeter-, Schwefel-, Oxal-, Milch-, Wein-, Essig-, Salicyl-, Benzoe-, Amei¬ sen-, Propion-, Pivalin-, Diethylessig-, Malon-, Bern¬ stein-, Pimelin-, Fumar-, Malein-, Apfel-, Sulfamin-, Phenylpropion-, Glucon-, Ascorbin-, Isonicotin-, Methan¬ sulfon-, p-Toluolsulfon-, Zitronen- oder Adipinsäure. Besonders bevorzugt sind die Hydrochloride.Pharmacologically acceptable salts of the sydnonimines of the general formula I are in particular acid addition salts with inorganic or organic acids. Suitable acids are, for example, hydrogen chloride, hydrogen bromide, naphthalenedisulfonic acids, in particular naphthalene disulfonic acid (1,5), phosphoric, nitric, sulfuric, oxalic, milk, wine, vinegar, salicylic, benzoic , Ants, propion, pivaline, diethyl vinegar, malon, amber, pimelin, fumar, malein, apple, sulfamine, phenylpropion, glucon, ascorbin, isonicotine, Methane sulfonic, p-toluenesulfonic, citric or adipic acid. The hydrochlorides are particularly preferred.
Die Herstellung der anspruchsgemäßen Sydnonimine sowie ihrer pharmakologisch verträglichen Salze ist bekannt und beispielsweise in DE-OS-1620501; DE-OS-1670127; DE-OS-1695897; EP-A-23343; EP-A-59356; EP-A-76952; EP-A-210474; EP-A-276710; EP-A-312773; EP-A-324408; EP-A-346684; EP-A-346694; EP-A-367036; EP-A-406659 und EP-A-406661 beschrieben.The preparation of the claimed Sydnonimine and their pharmacologically acceptable salts is known and for example in DE-OS-1620501; DE-OS-1670127; DE-OS-1695897; EP-A-23343; EP-A-59356; EP-A-76952; EP-A-210474; EP-A-276710; EP-A-312773; EP-A-324408; EP-A-346684; EP-A-346694; EP-A-367036; EP-A-406659 and EP-A-406661.
Es ist normalerweise zweckmäßig, die anspruchsgemäßenIt is usually convenient to do the demanding ones
Sydnonimine in einer pharmazeutischen Zubereitung zu ver¬ abreichen. Dabei kommen insbesondere parenterale und topische Applikationsformen wie beispielsweise Lotionen, Cremes, Lösungen, Gele, Sprays, elastische Flüssig-Pflas- ter, transdermale Systeme oder Beschichtungen für Kondome in Frage .To administer Sydnonimine in a pharmaceutical preparation. In particular, there are parenteral and topical forms of application such as lotions, creams, solutions, gels, sprays, elastic liquid plasters, transdermal systems or coatings for condoms in question.
Bevorzugt ist eine parenterale Applikation, da sie die sicherste Form ist, eine gezielte Wirkstoffmenge direkt ohne weitere Verfälschung durch andere Faktoren gezielt einzusetzen.Parenteral administration is preferred, since it is the safest form of using a targeted amount of active ingredient directly without further adulteration by other factors.
Zubereitungen zur parenteralen Applikation enthalten 0,1 bis 5 mg, bevorzugt 0,1 bis 2 mg Sydnonimin der allgemei- nen Formel I pro Dosiseinheit und können in separatenPreparations for parenteral administration contain 0.1 to 5 mg, preferably 0.1 to 2 mg of sydnonimine of the general formula I per dose unit and can be given in separate
Dosiseinheitsformen wie z. B. Ampullen oder Vials vorlie¬ gen. Vorzugsweise werden Lösungen des Wirkstoffes verwen¬ det, bevorzugt wässrige Lösungen und vor allem isotoni¬ sche Lösungen, aber auch Suspensionen. Diese Injektions- formen können als Fertigpräparat zur Verfügung gestellt werden oder erst direkt vor der Anwendung durch Mischen der wirksamen Verbindung, z. B. des Lyophilisats, gegebe¬ nenfalls mit weiteren festen Trägerstoffen, mit dem ge¬ wünschten Lösungs- oder Suspensionsmittel zubereitet wer- den. Für topische Applikationsformen ist selbstverständ¬ lich eine höhere Wirkstoffkonzentration als die für parenterale Zubereitungen genannte angezeigt.Dosage unit forms such as B. ampoules or vials. Solutions of the active ingredient are preferably used, preferably aqueous solutions and above all isotonic solutions, but also suspensions. These injection forms can be made available as a ready-to-use preparation or only directly before use by mixing the active compound, eg. B. the lyophilizate, optionally with other solid carriers, with the desired solvent or suspending agent. For topical forms of application, a higher active substance concentration than that mentioned for parenteral preparations is of course indicated.
Parenterale wie topische Formen können sterilisiert sein und/oder gegebenenfalls Hilfsstoffe wie Konservierungs¬ mittel, Stabilisatoren, Netzmittel, Penetrationsmittel, Emulgatoren, Spreitmittel, Lösungsvermittler, Salze zur Regelung des osmotischen Drucks oder zur Pufferung und/oder Viskositätsregulatoren enthalten.Parenteral and topical forms can be sterilized and / or optionally contain auxiliaries such as preservatives, stabilizers, wetting agents, penetrants, emulsifiers, spreading agents, solubilizers, salts for regulating the osmotic pressure or for buffering and / or viscosity regulators.
Derartige Zusätze sind z. B. Tartrat- und Citrat-Puffer, Ethanol, Komplexbildner (wie Ethylendiamin-tetraessig- säure und deren nicht-toxische Salze). Zur Regelung der Viskosität kommen hochmolekulare Polymere in Frage wie beispielsweise flüssiges Polyethylenoxid, Carboxymethyl- cellulosen, Polyvinylpyrrolidone, Dextrane oder Gelatine. Feste Trägerstoffe sind z. B. Stärke, Lactose, Mannit, Methylcellulose, Talkum, hochdisperse Kieselsäuren, höhermolekulare Fettsäuren (wie Stearinsäure), Gelatine, Agar-Agar, Calciumphosphat, Magnesiumstearat, tierische und pflanzliche Fette, feste hochmolekulare Polymere, wie Polyethylenglykol.Such additives are e.g. B. tartrate and citrate buffers, ethanol, complexing agents (such as ethylenediamine-tetraacetic acid and its non-toxic salts). High-molecular polymers such as liquid polyethylene oxide, carboxymethyl- cellulosic, polyvinylpyrrolidones, dextrans or gelatin. Solid carriers are e.g. B. starch, lactose, mannitol, methyl cellulose, talc, highly disperse silicas, higher molecular weight fatty acids (such as stearic acid), gelatin, agar, calcium phosphate, magnesium stearate, animal and vegetable fats, solid high molecular weight polymers, such as polyethylene glycol.
Ölige Suspensionen für parenterale oder topische Anwen- düngen können vegetabile synthetische oder semisyntheti¬ sche Öle wie beispielsweise flüssige Fettsäureester mit jeweils 8 bis 22 C-Atomen in den Fettsäureketten, z. B. Palmitin-, Laurin-, Tridecyl-, Margarin-, Stearin-, Ara- chin-, Myristin-, Behen-, Pentadecyl-, Linol-, Elaidin-, Brasidin-, Eruca- oder Ölsäure, die mit ein-bis dreiwer¬ tigen Alkoholen mit 1 bis 6 C-Atomen wie beispielsweise Methanol, Ethanol, Propanol, Butanol, Pentanol oder deren Isomere, Glycol oder Glycerol verestert sein. Derartige Fettsäureester sind beispielsweise handelsübliche Miglyo- le, Isopropylmyristat, Isopropylpalmitat, Isopropylstea- rat, PEG 6-Caprinsäure, Cypryl/Caprinsäureester von ge¬ sättigten Fettalkoholen, Polyoxyethylenglyceroltrioleate, Ethyloleat, wachsartige Fettsäureester wie künstliches Entenbürzeldrüsenfett, Kokosfettsäure-isopropylester, Olsäureoleylester, Olsäuredecylester, Milchsäureethyl- ester, Dibuthylphthalat, Adipinsäurediisopropylester, Polol-Fettsäureester u. a. Ebenso geeignet sind Silikon¬ öle verschiedener Viskosität oder Fettalkohole wie Iso- tridexylalkohol, 2-Octyldodecanol, Cetylstearyl-Alkohol oder Oleylalkohol, Fettsäuren wie beispielsweise Ölsäure. Weiterhin können vegetabile Öle wie Rizinusöl, Mandelöl, Olivenöl, Sesamöl, Baumwollsaatöl, Erdnußöl oder Soja- bohnenöl Verwendung finden. Die genannten Stoffe haben zudem die Eigenschaften eines Spreitmittels, d. h. es erfolgt eine besonders gute Verteilung auf der Haut. Als Lösungsmittel, Gelbildner und- Lösungsvermittler kom¬ men in Frage Wasser oder mit Wasser mischbare Lösungsmit¬ tel. Geeignet sind z. B. Alkohole wie beispielsweise Ethanol oder Isopropylalkohol, Benzylalkohol, 2-0ctyl- dodecanol, Polyethylenglykole, Phthalate, Adipate, Pro- pylenglykol, Glycerin, Di- oder Tripropylenglykol, Wachse, Methylcellosolve, Cellosolve, Ester, Morpholine, Dioxan, Dimethylsulfoxid, Dimethylformamid, Tetrahydro- furan, Cyclohexanon etc.Oily suspensions for parenteral or topical applications can be vegetable synthetic or semisynthetic oils such as liquid fatty acid esters with 8 to 22 carbon atoms in the fatty acid chains, e.g. B. palmitic, lauric, tridecyl, margarine, stearic, araquinic, myristic, behenic, pentadecyl, linoleic, elaidic, brasidic, erucic or oleic acid, with a-bis trivalent alcohols with 1 to 6 carbon atoms, such as, for example, methanol, ethanol, propanol, butanol, pentanol or their isomers, glycol or glycerol, have been esterified. Such fatty acid esters are, for example, commercially available miglyols, isopropyl myristate, isopropyl palmitate, isopropyl stearate, PEG 6-capric acid, cypryl / capric acid esters of saturated fatty alcohols, polyoxyethylene glycerol trioleates, ethyl oleate, wax-like fatty acid esters such as artificial duck fatty acid, ethyl ester fatty acid, coconut oil fatty acid, coconut oil ester, isol fatty acid ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isol fatty acid ethyl ester, isopropyl fatty acid ethyl ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester, isol fatty acid ester; esters, dibuthyl phthalate, diisopropyl adipate, polol fatty acid esters, etc. Likewise suitable are silicone oils of various viscosities or fatty alcohols such as isotidexyl alcohol, 2-octyldodecanol, cetylstearyl alcohol or oleyl alcohol, fatty acids such as oleic acid. Vegetable oils such as castor oil, almond oil, olive oil, sesame oil, cottonseed oil, peanut oil or soybean oil can also be used. The substances mentioned also have the properties of a spreading agent, ie there is a particularly good distribution on the skin. Suitable solvents, gel formers and solubilizers are water or water-miscible solvents. Are suitable for. B. alcohols such as ethanol or isopropyl alcohol, benzyl alcohol, 2-0ctyl-dodecanol, polyethylene glycols, phthalates, adipates, propylene glycol, glycerol, di- or tripropylene glycol, waxes, methyl cellosolve, cellosolve, ester, morpholines, dioxane, dimethyl sulfoxide, dimethylformamide, Tetrahydrofuran, cyclohexanone etc.
Als Filmbildner können Celluloseether verwendet werden, die sich sowohl in Wasser als auch in organischen Lö¬ sungsmitteln lösen bzw. anquellen können und nach dem Trocknen eine Art Film bilden, wie beispielsweise Hydro- xypropylcellulose, Methylcellulose, Ethylcellulose oder lösliche Stärken.Cellulose ethers which dissolve or swell both in water and in organic solvents and which form a type of film after drying, such as, for example, hydroxypropyl cellulose, methyl cellulose, ethyl cellulose or soluble starches, can be used as film formers.
Mischformen zwischen Gel- und Filmbildnern sind durchaus ebenfalls möglich. Hier kommen vor allem ionische Makro¬ moleküle zur Anwendung, wie beispielsweise Natriumcar- boxymethylcellulose, Polyacrylsäure, Polymethacrylsäure und deren Salze, Natriumamylopektinsemiglykolat, Algin- säure oder Propylenglykol-Alginat als Natriumsalz, Gummi arabicum, Xanthan-Gummi, Guar-Gummi oder Carrageenan.Mixed forms between gel and film formers are also quite possible. Ionic macromolecules in particular are used here, such as sodium carboxymethyl cellulose, polyacrylic acid, polymethacrylic acid and its salts, sodium amylopectin semiglycolate, alginic acid or propylene glycol alginate as sodium salt, gum arabic, xanthan gum, guar gum or carrageenan.
Als weitere Formulierungshilfsmittel können eingesetzt werden: Glycerin, Paraffin unterschiedlicher Viskosität, Triethanolamin, Collagen, Allantoin, Novantisolsäure, Parfümöle.Further formulation auxiliaries that can be used are: glycerol, paraffin of different viscosities, triethanolamine, collagen, allantoin, novantisol acid, perfume oils.
Auch die Verwendung von Tensiden, Emulgatoren oder Netz¬ mitteln kann zur Formulierung notwendig sein, wie z.B. von Na-Laurylsulfat, Fettalkoholethersulfaten, Di-Na-N- lauryl-ß-iminodipropionat, polyoxyethyliertes Rizinusöl oder Sorbitan-Monooleat, Sorbitan-Monostearat, Cetylal- kohol, Lecithin, Glycerinmonostearat, Polyoxyethylenstea- rat, Alkylphenolpolyglykolether, Cetyltrimethylammonium- chlorid oder Mono-/Dialkylpolyglykolether-orthophosphor- säure-monoethanolaminsalze.The use of surfactants, emulsifiers or wetting agents may also be necessary for the formulation, such as, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, di-Na-N-lauryl-β-iminodipropionate, polyoxyethylated castor oil or sorbitan monooleate, sorbitan monostearate, cetylal - alcohol, lecithin, glycerol monostearate, polyoxyethylene stearate, alkylphenol polyglycol ether, cetyltrimethylammonium chloride or mono- / dialkylpolyglycol ether-orthophosphoric acid-monoethanolamine salts.
Stabilisatoren wie Montmorillonite oder kolloidale Kie¬ selsäuren zur Stabilisierung von Emulsionen oder zur Ver¬ hinderung des Abbaus der aktiven Substanzen wie Antioxi- dantien, beispielsweise Tocopherole oder Butylhydroxy- anisol, oder Konservierungsmittel, wie p-Hydroxybenzoe- säureester, können ebenfalls zur Zubereitung der ge¬ wünschten Formulierungen gegebenenfalls erforderlich sein.Stabilizers such as montmorillonites or colloidal silicas for stabilizing emulsions or for preventing the breakdown of active substances such as antioxidants, for example tocopherols or butylhydroxyanisole, or preservatives such as p-hydroxybenzoic acid esters can also be used to prepare the ge ¬ desired formulations may be required.
Zur Förderung der Penetration enthalten transdermaleTo promote penetration contain transdermal
Formulierungen vorzugsweise organische, gut hautverträg¬ liche Lösungsmittel wie Ethanol, Methylpyrrolidon, Poly- ethylenglykol, Oleylalkohol, Octanol, Linolsäure, Tri- acetin, Propylenglykol, Glycerin, Solketal oder Dimethyl- sulfoxid.Formulations preferably organic solvents which are well tolerated by the skin, such as ethanol, methylpyrrolidone, polyethylene glycol, oleyl alcohol, octanol, linoleic acid, triacetine, propylene glycol, glycerol, solketal or dimethyl sulfoxide.
Infolge der Lichtempfindlichkeit der Sydnonimine der allgemeinen Formel I ist es angezeigt, den Darreichungs¬ formen Photostabilisatoren zuzusetzen oder sie in ent- sprechend lich schützenden Verpackungen bereitzustellen, wie beispielsweise in lichtundurchlässigen Einmai-Fertig¬ spritzen.As a result of the light sensitivity of the sydnonimines of the general formula I, it is appropriate to add photostabilizers to the dosage forms or to provide them in correspondingly protective packaging, such as in opaque one-time pre-filled syringes.
Als Photostabilisatoren kommen Verbindungen in Frage wie Chinoline, z.B. 8-Hydroxychinolin oder Chinolingelb; geeignete Lebensmittelfarbstoffe; Flavanoide wie z. B. Hesperidin, Hesperidin-methylchalcon, Hesperidinphosphat, Hesperitin, Quercetin, Quercitrin, Rutin, Rutinsulfat, Naringenin, Kampferöl, Kämpferol-7,4'-dimethylether, Morin, Apigetrin, Luteolin und sein 7-Glycosid, oder Troxerutin. Sie werden im Mengenverhältnis 0,001 : 1 bis 50 : 1, vorzugsweise 0,1 : 1 bis 20 : 1 zugesetzt.Compounds such as quinolines, for example 8-hydroxyquinoline or quinoline yellow, are suitable as photostabilizers; suitable food colors; Flavanoids such as B. hesperidin, hesperidin-methylchalcon, hesperidin phosphate, hesperitin, quercetin, quercitrin, rutin, rutin sulfate, naringenin, camphor oil, kaempferol 7,4'-dimethyl ether, morin, apigetrin, luteolin and its 7-glycoside, or Troxerutin. They are added in a quantity ratio of 0.001: 1 to 50: 1, preferably 0.1: 1 to 20: 1.
Die Herstellung, Abfüllung und die Verschließung der Prä- parate erfolgt unter den üblichen antimikrobiellen und aseptischen Bedingungen. Auch für topischen beziehungs¬ weise transdermalen Einsatz erfolgt eine Abpackung mög¬ lichst in separaten Dosiseinheiten zur Erleichterung der Handhabung, auch hier wie bei parenteralen Formen gegebe- nenfalls aus Stabilitätsgründen durch separate Abpackung der Wirkstoffe beziehungsweise deren Kombinationen als Lyophilisat, gegebenenfalls mit festen Trägerstoffen, und den erforderlichen Lösungsmitteln etc.The preparation, filling and sealing of the preparations is carried out under the usual antimicrobial and aseptic conditions. For topical or transdermal use, packaging is also possible in separate dose units to facilitate handling, here too, as in parenteral forms, if necessary for reasons of stability, by separate packaging of the active substances or their combinations as lyophilisate, if appropriate with solid carriers, and the necessary solvents etc.
In einer besonderen Ausführungsform der Erfindung werden die Sydnonimine der allgemeinen Formel I in Kombination mit einem oder mehreren synergistisch wirkenden Substan¬ zen verwendet. Solche synergistisch wirdenden Substanzen sind beispielsweise Adenosin, Vitamine, z. B. Vitamin A oder H, Prostaglandine, z. B. E^, Peptide wie z. B. Cal- citonine gene related peptides (CGRP)_, Calcium-Antago- nisten wie Nifedipin, Verapamil, Diltiaze , Gallopamil, Niludipin, Nimodipin, Nicardipin, Prenylamin, Fendilin, Terodilin, Nisaldipin, Nitrendipin oder Perhexilin, α-Rezeptorenblocker, beispielsweise Phentolaminmethan- sulfonat, Phenoxybenzamin oder Minoxidil, Relaxantien der glatten Muskulatur wie Papaverin, Trinitroglycerin, Natriumnitroprussid oder S-nitroso-N-acetylpenicillamin.In a particular embodiment of the invention, the sydnonimines of the general formula I are used in combination with one or more synergistically active substances. Such synergistic substances are, for example, adenosine, vitamins, e.g. B. Vitamin A or H, prostaglandins, e.g. B. E ^, peptides such. B. Citricone gene related peptides (CGRP) _, calcium antagonists such as nifedipine, verapamil, diltiaze, gallopamil, niludipine, nimodipine, nicardipine, prenylamine, fendiline, terodiline, nisaldipine, nitrendipine or perhexiline, for example α-receptor blockers Phentolamine methanesulfonate, phenoxybenzamine or minoxidil, smooth muscle relaxants such as papaverine, trinitroglycerin, sodium nitroprusside or S-nitroso-N-acetylpenicillamine.
Besonders vorteilhaft und ebenfalls Gegenstand vorliegen¬ der Erfindung ist eine Einmal-Arzneimittelpackung enthal¬ tend in steriler Abpackung eine Einmalspritze mit einer parenteralen Zubereitung eines Sydnonimins der allgemei¬ nen Formel I, gegebenenfalls in Kombination mit einer synergistisch wirkenden Substanz; mit Desinfektionsmit- teln versehene sterile Tupfer sowie Benutzungsinformatio¬ nen.Particularly advantageous and also an object of the present invention is a disposable medicament package containing in sterile packaging a disposable syringe with a parenteral preparation of a sydnonimine of the general formula I, optionally in combination with a synergistically active substance; with disinfectant provided sterile swabs as well as usage information.
Die genannten Einmal-Fertigspritzen sind vorzugsweise vom Typ Ultrafein, wie sie beispielsweise in der Insulinthe¬ rapie zur Anwendung kommen. Bevorzugt sind auch Spritzen in der Art von Autoinjektoren, die noch einfacher in ihrer Handhabung sind. Die Fertigspritzen sind bevorzugt in lichtundurchlässiger Form ausgeführt, da sich dadurch der Zusatz von Photostabilisatoren zu den parenteralenThe disposable pre-filled syringes mentioned are preferably of the ultrafine type, as are used, for example, in insulin therapy. Syringes of the type of auto-injectors that are even easier to handle are also preferred. The pre-filled syringes are preferably made in opaque form, since this adds photostabilizers to the parenteral ones
Zubereitungen erübrigt. Sie können jedoch auch so ausge¬ bildet sein, daß Wirkstoff und zugehöriges Injektions¬ lösungsmittel erst direkt vor der Injektion gemischt werden. Dies kann z. B. in Zwei-Behältnis-Ampullen bzw. -Spritzen geschehen. Dadurch kann sich ein gegebenenfalls erforderlicher Photostabilisatorzusatz ebenfalls erübri¬ gen.Preparations are unnecessary. However, they can also be designed in such a way that the active ingredient and associated injection solvent are only mixed directly before the injection. This can e.g. B. happen in two-container ampoules or syringes. As a result, any photostabilizer additive that may be required can also be omitted.
Die sterilen Tupfer zur Desinfektion enthalten die übli- chen Mittel zur Haut-Desinfektion wie beispielsweise Ethanol. Sie können jedoch auch noch zusätzlich erek- tionsfördernde Mittel in einer topisch applizierbaren Form zur Steigerung bzw. Verlängerung der Wirkung enthal¬ ten.The sterile swabs for disinfection contain the usual skin disinfectants such as ethanol. However, they can also contain erection-promoting agents in a topically applicable form to increase or prolong the action.
Beispiel 1example 1
Zur Herstellung einer Injektionslösung werden 500 mg 3-(3.3-Dimethyl-thiomorpholino)-sydnonimin-hydrochlorid und 750 mg NaCl in destilliertem Wasser gelöst, mit IN Salzsäure auf pH 4,0 eingestellt, mit destilliertem Was¬ ser auf 100 ml aufgefüllt und in 0,5 ml Ampullen abge¬ packt..To prepare a solution for injection, 500 mg of 3- (3,3-dimethyl-thiomorpholino) -sydnonimine hydrochloride and 750 mg of NaCl are dissolved in distilled water, adjusted to pH 4.0 with 1N hydrochloric acid, made up to 100 ml with distilled water and in 0.5 ml ampoules packaged.
In gleicher Weise lassen sich für die Herstellung wei- terer Injektionslösungen die folgenden Sydnonimine ver- 1 wenden :In the same way, the following Sydnonimine can be used for the production of further injection solutions. 1 turn:
2. 300 mg 3-Dibenzylamino-sydnonimin-hydrochlorid2. 300 mg of 3-dibenzylamino-sydnonimine hydrochloride
3. 400 mg 3-(cis-2.5-Dimethyl-pyrrolidino)-sydnonimin- hydrochlorid3. 400 mg of 3- (cis-2,5-dimethyl-pyrrolidino) -sydnonimine hydrochloride
5 4. 600 mg 3-(3.3-Dimethyl-l.l-dioxo-thiomorpholino)-syd- nonimin-hydrochlorid5 4. 600 mg of 3- (3,3-dimethyl-l. L-dioxo-thiomorpholino) -syd-nonimin hydrochloride
5. 500 mg 3-(2.2-Dimethylpiperidino)-sydnonimin-hydro- chlorid5. 500 mg of 3- (2,2-dimethylpiperidino) -sydnonimine hydrochloride
6. 400 mg 3-(3.3-Dimethyl-morpholino)-sydnonimin-hydro- o chlorid6. 400 mg of 3- (3,3-dimethyl-morpholino) -sydnonimine hydrochloride
7. 500 mg 3-(tert.Butyl-methylamino)-sydnonimin-hydro- chlorid7. 500 mg of 3- (tert-butyl-methylamino) -sydnonimine hydrochloride
8. 300 mg 3-(Dicyclohexylamino)-sydnonimin-hydrochlorid8. 300 mg of 3- (dicyclohexylamino) -sydnonimine hydrochloride
9. 400 mg 3-Diisopropylamino-sydnonimin-hydrochlorid 5 10. 500 mg 3-(tert.Butyl-ethyl-amino)-sydnonimin-hydro- chlorid9. 400 mg of 3-diisopropylamino-sydnonimine hydrochloride 5 10. 500 mg of 3- (tert-butyl-ethyl-amino) -sydnonimine hydrochloride
11. 550 mg 3-(tert.Butyl-propyl-amino)-sydnonimin-hydro- chlorid11. 550 mg of 3- (tert-butyl-propyl-amino) -sydnonimine hydrochloride
12. 550 mg 3-(tert.Butyl-butyl-amino)-sydnonimin-hydro- 0 chlorid12. 550 mg of 3- (tert-butyl-butyl-amino) -sydnonimine hydro-0 chloride
13. 300 mg 3-(tert.Butyl-hydroxyethyl-amino)-sydnonimin- hydrochlorid13. 300 mg of 3- (tert-butyl-hydroxyethyl-amino) -sydnonimine hydrochloride
14. 750 mg 3-(cis-2.6-Dimethyl-piperidino)-sydnonimin- hydrochlorid 5 15. 750 mg 3-(2.2.6.6-Tetramethyl-piperidino)-sydnon- imin-hydrochlorid14. 750 mg of 3- (cis-2,6-dimethyl-piperidino) -sydnonimine hydrochloride 5 15. 750 mg of 3- (2.2.6.6-tetramethyl-piperidino) -sydnonimine hydrochloride
16. 400 mg 3-(N-Methyl-piperazino)-sydnonimin-hydrochlo- rid16. 400 mg of 3- (N-methyl-piperazino) -sydnonimine hydrochloride
17. 700 mg 3-(2-Carboxy-pyrrolidino)-sydnonimin-hydro- o chlorid17. 700 mg of 3- (2-carboxypyrrolidino) sydnonimine hydrochloride
18. 700 mg 3-(2-Carboxy-piperidino)-sydnonimin-hydro- chlorid.18. 700 mg of 3- (2-carboxy-piperidino) -sydnonimine hydrochloride.
19. 400 mg 3-(l.l-Dioxo-thiomorpholino)-sydnonimin-hydro- chlorid 5 20. 400 mg 3-(2.2-Dimethyl-4-methylsulfonyl-piperazino)- sydnonimin-hydrochlorid19. 400 mg of 3- (ll-dioxothiomorpholino) -sydnonimine hydrochloride 5 20. 400 mg of 3- (2,2-dimethyl-4-methylsulfonyl-piperazino) - sydnonimine hydrochloride
21. 500 mg 3-(2.2-Dimethyl-4-tosyl-piperazino)-sydnon¬ imin-hydrochlorid21. 500 mg of 3- (2,2-dimethyl-4-tosyl-piperazino) -sydnon¬ imine hydrochloride
22. 250 mg 3-Ethylamino-sydnonimin-hydrochlorid 23. 500 mg 3-(2-Hydroxy-ethylamino)-sydnonimin-hydro¬ chlorid22. 250 mg of 3-ethylamino-sydnonimine hydrochloride 23. 500 mg of 3- (2-hydroxy-ethylamino) -sydnonimine hydrochloride
24. 250 mg 3-Methylamino-sydnonimin-hydrochlorid24. 250 mg of 3-methylamino-sydnonimine hydrochloride
25. 350 mg 3-Cyclohexylamino-sydnonimin-hydrochlorid25. 350 mg of 3-cyclohexylamino-sydnonimine hydrochloride
26. 400 mg 3-Piperidino-4-methyl-sydnonimin-hydrochlorid 27. 500 mg 3-Dimethylamino-4-ethyl-sydnonimin-hydrochlo- rid26. 400 mg of 3-piperidino-4-methyl-sydnonimine hydrochloride 27. 500 mg of 3-dimethylamino-4-ethyl-sydnonimine hydrochloride
28. 500 mg 3-Diisopropylamino-4-isopropyl-sydnonimin- hydrochlorid28. 500 mg of 3-diisopropylamino-4-isopropyl-sydnonimine hydrochloride
29. 600 mg N-Formyl-3-(2.2-dimethyl-thiomorpholino)-syd- nonimin29. 600 mg of N-formyl-3- (2,2-dimethyl-thiomorpholino) -syd-nonimin
30. 750 mg N- cetyl-3-diethylamino-sydnonimin30. 750 mg of N-cetyl-3-diethylamino-sydnonimine
31. 800 mg N-Propionyl-3-(3.3-dimethyl-thiomorpholino)- sydnonimin31. 800 mg of N-propionyl-3- (3,3-dimethylthiomorpholino) sydnonimine
32. 950 mg N-Ethoxycarbonyl-3-(2.2-dimethyl-4-isopropyl- o piperazino)-sydnonimin32.950 mg of N-ethoxycarbonyl-3- (2,2-dimethyl-4-isopropyl-o piperazino) -sydnonimine
33. 1,5 g N-p-Anisoyl-3-(cis-2.6-dimethyl-piperidino)- sydnonimin33. 1.5 g N-p-anisoyl-3- (cis-2,6-dimethyl-piperidino) sydnonimine
34. 1,0 g N-Pivaloyl-3-(2.2-dimethyl-l-oxo-thio- morpholino)-sydnonimin 5 35. 350 mg 3-(4-Ethoxycarbonyl-piperazino)-sydnonimin- hydrochlorid34.1.0 g of N-pivaloyl-3- (2,2-dimethyl-l-oxo-thio-morpholino) -sydnonimine 5 35. 350 mg of 3- (4-ethoxycarbonyl-piperazino) -sydnonimine hydrochloride
00
5 5

Claims

P A T E N T A N S P R Ü C H E PATENT CLAIMS
1. Verwendung von Sydnoniminen der allgemeinen Formel I1. Use of sydnonimines of the general formula I
Figure imgf000055_0001
Figure imgf000055_0001
oder eines pharmakologisch verträglichen Salzes davon, wobei R eine Aminogruppe der Formelor a pharmacologically acceptable salt thereof, wherein R is an amino group of the formula
~ j~ j
Figure imgf000055_0002
Figure imgf000055_0002
bedeutet ;means;
R Wasserstoff, Halogen, Alkyl, Cycloalkyl, Arylalkyl, Aryl-O-Alkyl, Aryl-S-Alkyl, Alkoxyalkyl, Alkylthio- alkyl oder Alkenylthioalkyl bedeutet;R represents hydrogen, halogen, alkyl, cycloalkyl, arylalkyl, aryl-O-alkyl, aryl-S-alkyl, alkoxyalkyl, alkylthioalkyl or alkenylthioalkyl;
R3 Wasserstoff -NO, die Gruppe -S02R oder die GruppeR 3 is hydrogen -NO, the group -S0 2 R or the group
-COR7 bedeutet;-COR 7 ;
R Alkyl, Alkenyl, Cycloalkyl, Bicycloalkyl, Tricyclo- alkyl, Alkyl-X-Alkyl, Arylalkyl, das auch durchR alkyl, alkenyl, cycloalkyl, bicycloalkyl, tricyclo- alkyl, alkyl-X-alkyl, arylalkyl, which also by
Alkyl oder Halogen substituiert sein kann, Hydroxy- alkyl, einen über eine Alkylenkette gebundenen hete- rocyclischen Ring oder einen RestAlkyl or halogen can be substituted, hydroxyalkyl, a heterocyclic ring bound via an alkylene chain or a radical
Figure imgf000056_0001
Figure imgf000056_0001
00
bedeutet;means;
R5 Wasserstoff bedeutet oder eine der Bedeutungen vonR 5 represents hydrogen or one of the meanings of
R4 hat; R6 Alkyl bedeutet;R has 4 ; R 6 represents alkyl;
R Aryl, durch 1 bis 3 Halogenatome und/oder 1 bis 3 Alkylreste und/oder 1 bis 3 Alkoxyreste und/oder 1 oder 2 Nitrogruppen mono-, di- oder trisubstituier- ten Arylrest, Arylalkenyl, Tricycloalkyl, Bicyclo- alkoxy, Tricycloalkoxy, Aryloxy, Alkoxycarbonyl, Pyridyl, Pyrrolyl, Imidazolyl, Pyrazolyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl oder OR bedeutet oder eine der Bedeutungen von R2 hat; X NR4, NS02R8, NC02Alkyl, S(0)n, 0, (CH2)m oder eine einfache Bindung bedeutet; n 0, 1 oder 2 ist; m 1, 2 oder 3 ist; und pR aryl, by 1 to 3 halogen atoms and / or 1 to 3 alkyl radicals and / or 1 to 3 alkoxy radicals and / or 1 or 2 nitro groups mono-, di- or tri-substituted aryl radical, arylalkenyl, tricycloalkyl, bicycloalkoxy, tricycloalkoxy, Means aryloxy, alkoxycarbonyl, pyridyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl or OR or has one of the meanings of R 2 ; X is NR 4 , NS0 2 R 8 , NC0 2 alkyl, S (0) n , 0, (CH 2 ) m or a simple bond; n is 0, 1 or 2; m is 1, 2 or 3; and p
R° Alkyl, Aryl, Alkylaryl, Halogenaryl oder Dialkyl- amino bedeutet, wobei die Arylgruppen auch durch Alkyl oder Halogen substituiert sein können, zur Behandlung erektiler Dysfunktionen, wobei X nicht für 0 stehen kann, wenn R2 und R3 Wasserstoff bedeuten.R ° denotes alkyl, aryl, alkylaryl, haloaryl or dialkylamino, where the aryl groups can also be substituted by alkyl or halogen, for the treatment of erectile dysfunctions, where X cannot stand for 0 if R 2 and R 3 signify hydrogen.
2. Verwendung gemäß Anspruch 1, dadurch gekennzeichnet, daß R1 Piperidino, Pyrrolidino, Dimethylamino, Diethyl- amino, Diisopropylamino, tert.Butyl-methylamino, tert.- Butyl-ethylamino, tert.butyl-propylamino, tert.butylbu- tylamino, tert.Butyl-hydroxyethylamino, Dibenzylamino, 2-Carboxy-pyrrolidino, 2-Carboxy-piperidino, 4-Carboxypi- peridino, Dicyclohexylamino, N-Methylpiperazino, 2,2-Di- methylpiperidino, 3.3-Dimethylmorpholino, 3.3-Dimethyl- thiomorpholino, 3.3-Dimethyl-l.1-dioxo-thiomorpholino, 3.3-Dimethyl-l-oxo-thiomorpholino, cis-2.6-Dimethylpipe- ridino, 2.2.6.6-Tetramethylpiperidino, 2.2-Dimethyl-N- methylsulfonyl-piperazino, 2.2-Dimethyl-N-tosyl-pipera- zino, 2.2-Dimethyl-pyrrolidino, 2.2-Dirnethyl-N-dimethyl- aminosulfonyl-piperazino, Ethylamino, (2-Hydroxyethyl)- amino oder Cyclohexylamino bedeutet.2. Use according to claim 1, characterized in that R 1 piperidino, pyrrolidino, dimethylamino, diethyl amino, diisopropylamino, tert.butylmethylamino, tert.butylethylamino, tert.butylpropylamino, tert.butylbutylamino, tert.butyl-hydroxyethylamino, dibenzylamino, 2-carboxy-pyrrolidino, 2-carboxy-piperidino, 4 -Carboxypi- peridino, dicyclohexylamino, N-methylpiperazino, 2,2-dimethylpiperidino, 3,3-dimethylmorpholino, 3,3-dimethyl-thiomorpholino, 3,3-dimethyl-1,1-dioxothiomorpholino, 3,3-dimethyl-1-oxo-thiomorpholino , cis-2,6-dimethylpiperidino, 2.2.6.6-tetramethylpiperidino, 2.2-dimethyl-N-methylsulfonyl-piperazino, 2.2-dimethyl-N-tosyl-piperazino, 2.2-dimethyl-pyrrolidino, 2.2-dirnethyl-N-dimethyl - aminosulfonyl-piperazino, ethylamino, (2-hydroxyethyl) - amino or cyclohexylamino.
3. Verwendung gemäß Anspruch 1 und/oder 2, dadurch ge- kennzeichnet, daß RΛ Wasserstoff bedeutet.3. Use according to claim 1 and / or 2, characterized in that R Λ is hydrogen.
4. Verwendung gemäß einem oder mehreren der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß RJ Wasserstoff bedeu- tet-4. Use according to one or more of claims 1 to 3, characterized in that R J is hydrogen tet importance -
5. Verwendung gemäß einem oder mehreren der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß das Sydnonimin der allgemeinen Formel I in Kombination mit einem oder mehreren synergistisch wirkenden Substanzen eingesetzt wird.5. Use according to one or more of claims 1 to 4, characterized in that the sydnonimine of the general formula I is used in combination with one or more synergistically active substances.
6. Verwendung gemäß Anspruch 5, dadurch gekennzeichnet, daß die synergistisch wirkende Substanz ein Adenosin, Vitamin, Peptid, Calcium-Antagonist, α-Rezeptorenblocker oder Relaxans der glatten Muskulatur ist.6. Use according to claim 5, characterized in that the synergistic substance is an adenosine, vitamin, peptide, calcium antagonist, α-receptor blocker or relaxant of the smooth muscles.
7. Einmal-Arzneimittelpackung enthaltend in steriler Ab¬ packung eine Einmalspritze mit einer parenteralen Zubereitung eines Sydnonimins der allgemeinen Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4, gegebenenfalls in7. Disposable medicament pack containing a disposable syringe with a parenteral preparation in sterile packaging of a sydnonimine of the general formula I according to one or more of claims 1 to 4, optionally in
Kombination mit einer synergistisch wirkenden Substanz gemäß Anspruch 5 und/oder 6; mit Desinfektionsmitteln versehene sterile Tupfer sowieCombination with a synergistic substance according to claim 5 and / or 6; sterile swabs provided with disinfectants and
BenutzungsInformationen. Usage information.
PCT/EP1993/000546 1992-03-24 1993-03-10 Use of sydnonimines to treat erectile dysfunction WO1993018767A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19924209462 DE4209462A1 (en) 1992-03-24 1992-03-24 Treatment of impotence
DEP4209462.3 1992-03-24
DEP4213338.6 1992-04-23
DE19924213338 DE4213338A1 (en) 1992-04-23 1992-04-23 Treatment of impotence

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WO1994018966A1 (en) * 1993-02-26 1994-09-01 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Transdermal therapeutic system with active substances which represent sources of nitrogen oxide
GB2339533A (en) * 1998-07-14 2000-02-02 James Martin Biggs Topical pharmaceutical preparations
WO2014145126A3 (en) * 2013-03-15 2014-12-18 Melior Discovery, Inc. Methods of treating dyskinesia and related disorders

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DE1695897A1 (en) * 1966-07-04 1972-02-03 Takeda Chemical Industries Ltd N-acyl-sydnonimine derivatives
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DE1695897A1 (en) * 1966-07-04 1972-02-03 Takeda Chemical Industries Ltd N-acyl-sydnonimine derivatives
DE1670127A1 (en) * 1966-08-09 1970-12-03 Boehringer Sohn Ingelheim Process for the preparation of new substituted 3-amino-sydnonimines
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994018966A1 (en) * 1993-02-26 1994-09-01 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Transdermal therapeutic system with active substances which represent sources of nitrogen oxide
GB2339533A (en) * 1998-07-14 2000-02-02 James Martin Biggs Topical pharmaceutical preparations
WO2014145126A3 (en) * 2013-03-15 2014-12-18 Melior Discovery, Inc. Methods of treating dyskinesia and related disorders
US9051312B2 (en) 2013-03-15 2015-06-09 Melior Discovery, Inc. Methods of treating dyskinesia and related disorders
CN105209445A (en) * 2013-03-15 2015-12-30 梅利奥尔探索公司 Methods of treating dyskinesia and related disorders
US9402830B2 (en) 2013-03-15 2016-08-02 Melior Discovery, Inc. Methods of treating dyskinesia and related disorders
US10188651B2 (en) 2013-03-15 2019-01-29 Melior Pharmaceuticals Ii, Llc Methods of treating sleep disorders
EA032064B1 (en) * 2013-03-15 2019-04-30 Мелиор Фармасьютикалз Ii, Ллс Method of treating levodopa-induced dyskinesia using sydnocarb
US11351169B2 (en) 2013-03-15 2022-06-07 Melior Pharmaceuticals Ii, Llc Methods of treating dyskinesia and related disorders

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