GB2435825A - Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake - Google Patents

Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake Download PDF

Info

Publication number
GB2435825A
GB2435825A GB0604775A GB0604775A GB2435825A GB 2435825 A GB2435825 A GB 2435825A GB 0604775 A GB0604775 A GB 0604775A GB 0604775 A GB0604775 A GB 0604775A GB 2435825 A GB2435825 A GB 2435825A
Authority
GB
United Kingdom
Prior art keywords
benzimidazole
ethyl
dioxide
group
butyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
GB0604775A
Other versions
GB0604775D0 (en
Inventor
Helmut Heinrich Buschmann
Jordi-Ramon Quintana Ruiz
Jordi Corbera Arjona
Xavier Codony Soler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Esteve Pharmaceuticals SA
Original Assignee
Laboratorios del Dr Esteve SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratorios del Dr Esteve SA filed Critical Laboratorios del Dr Esteve SA
Priority to GB0604775A priority Critical patent/GB2435825A/en
Publication of GB0604775D0 publication Critical patent/GB0604775D0/en
Publication of GB2435825A publication Critical patent/GB2435825A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—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
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
    • 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
    • A61K31/42—Oxazoles
    • 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
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/433—Thidiazoles
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/549—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 having two or more nitrogen atoms in the same ring, e.g. hydrochlorothiazide
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Substituted benzimidazole sulphonamides of formula I [wherein: <DL TSIZE=14> <DT>Z<1-4><DD>are N or optionally substituted C (as defined herein), provided that no more than one of <DT>Z<1-4><DD>is N; <DT>R<1>, R<2> and R<3><DD>are H or a substituent (as defined herein), or R<1> and R<2> together form a linkage -X-, or R<2> and R<3> together form a linkage -(CH2)n-(Y)m-CHR<10>- (in which case R<1> and R<10> together may optionally be -CH2-); <DT>-X-<DD>is -(CHR<8>)n-(CHR<9>)m- or -CR<8>=CR<9>-; <DT>R<8> and R<9><DD>are H,C1-5-alkyl, aryl or heteroaryl; <DT>n<DD>is 1-4; <DT>m<DD>is 0-1; <DT>-Y-<DD>is -CH2-O-CH2- or -CH2-NR<11>-CH2-; <DT>R<10><DD>is H -COO-alkyl, -CH2-OH or -CH2-Cl; and <DT>R<11><DD>is H or alkyl optionally substituted by hydroxy] </DL> are useful in the prophylaxis or treatment of disorders or diseases that are at least partially mediated via 5-HT6 receptors, such as those related to food intake, eg regulation of appetite and body weight, obesity, bulimia, anorexia, cachexia, type II diabetes (non insulin dependent diabetes). They may also be used in a range of therapeutic applications as detailed in claims 22-24, such as strokes, seizures, cognitive enhancement, and drug addiction or withdrawal.

Description

<p>Use of substituted benzimidazole sulfonamide compounds for the
treatment of food related disorders The present invention relates to the use of subsituted benzimidazole sulfonamide compounds of general formula I, R1 4 / 0 R2</p>
<p> IT N I,</p>
<p>for the prophylaxis and/or treatment of disorders or diseases that are at least partially mediated via 5-HT6 receptors.</p>
<p>The superfamily of serotonin receptors (5-HT) includes 7 classes (5-HT1-5-HT7) encompassing 14 human subclasses [D. Hoyer, et al., Neuropharmacology, 1997, 36, 419]. The 5-HT6 receptor is the latest serotonin receptor identified by molecular cloning both in rats [F.J. Monsma et al., Mol. Pharmacol., 1993, 43, 320; M. Ruat et al., Biochem. Biophys. Res. Commun., 1993, 193, 268] and in humans [R. Kohen, et al., J. Neurochem., 1996, 66, 47].</p>
<p>Recently, it has been shown that the 5-HT6 receptor plays a role in food ingestion [Neuropharmacology, 41, 2001, 210-219].</p>
<p>Food ingestion disorders, particularly obesity, are a serious, fast growing threat to the health of humans of all age groups, since they increase the risk of developing other serious, even life-threatening diseases such as diabetes or coronary diseases as well.</p>
<p>Therefore an object of the present invention was to provide compounds that can be used for the prophylaxis and/or treatment of disorders or diseases related to 5-HT6 receptors such as food intake related disorders.</p>
<p>S * . S..</p>
<p>* S * S S S S * :: ;. :. :.</p>
<p>Surprisingly, it has been found that the substituted benzimidazole sulfonamide compounds of general formula I given below show good to excellent affinity to 5-HT6-receptors. These compounds are therefore particularly suitable for the prophylaxis and/or treatment of disorders or diseases related to 5-HT6-receptors such as food intake related disorders like obesity.</p>
<p>Thus, in one of its aspects the present invention relates to the use of at least one substituted benzimidazole sulfonamide compound of general formula I, R1 4 I 0 R2 b-S-N' wherein Z1 represents a nitrogen atom or a carbon atom bonded to another radical R4 (C-R4); z2 represents a nitrogen atom or a carbon atom bonded to another radical R5 (C-R5); z3 represents a nitrogen atom or a carbon atom bonded to another radical R6 (C-R6); z4 represents a nitrogen atom or a carbon atom bonded to another radical R7 (C-R7); with the restriction that only one of the groups Z', Z2, Z3 or Z4 can represent a nitrogen atom; R1 and R2, independently of one another, in each case represent a hydrogen atom; a linear or branched alkyl radical which may optionally be substituted with substituents selected from the group consisting of aryl, cyctoalkyl radical which may be condensed with a mono-or bicyclic ring system, -C(=O)-alkyl, -C(=0)-aryl and -C(=O)-heteroaryl; * S S S *SS * S S S * S * S * . I * *fl S * *. e * S I * S * S S * S S. * 555 SIe S a cycloalkyl radical which may be condensed with a mono-or bicyclic ring system; -C(=O)-O-alkyl; -C(=O)-alkyl or -NO2; or alternatively R1 and R2 together form a linkage represented by a group X; R3 represents a hydrogen atom; a linear or branched alkyl radical which may optionally be substituted with substituents selected from the group consisting of-OH, -NH2, -NH-alkyl, -N(alkyl)(alkyl), -S-alkyl, -S(=O)-alkyl, -S(=O)2-alkyl, halogen, -CN, -NH[(CH2)1,2, 3 or 4 aryl], -N[alkyl][(CH2)1,2,30r4-aryl], piperazinyl, piperidinyl, morpholinyl, aryl, heteroaryl, -C(=O)-O-alkyl, -S-aryl, -S(=O)-aryl, -S(=O)2-aryl, -S-heteroaryl, -S(=O)-heteroaryl, -S(=O)2-heteroaryl, -S-(CH2)1, 2, 3 or4-aryl, -S(0)-(CH2)1, 2,3 0r4-aryl, -S(O)2-(CH2)i, 2, 3 or4aryl, S(CH2)1, 2,3 or4heteroatyl, -S(=O)-(CH2)1, 2, 30r4-heteroaryl and -S(0)2-(CH2)1, 2, 3or4heteroatyl, an aryl radical; a heteroaryl radical; a cycloalkyl radical which may be condensed with a mono-or bicyclic ring system and/or may be bridged by linear or branched alkylene; or -C(=O)-alkyl; X represents (CHR8)n(CHR9)m or -CR8=CR9; or alternatively R2 and R3 together form a linkage represented by a group -(CH2)-YmCHR10 Y represents -CH2-O-CH2-or -CH2-NR11 -CH2-; n represents 1, 2, 3 or 4; m represents 0 or 1; R4 and R7, independently of one another, in each case represent a hydrogen atom; a halogen atom; -NO2; -NH2; -NH-(alkyl); -N(alkyl)(alkyl) or -NH-C(=O)-alkyl; * S S * S*S * * S S S * * S * S S * *fl * S S. S S...) . S * . . S S S S *5 * 555 *S* S R5 and R6, independently of one another, in each case represent a hydrogen atom; a halogen atom; -NO2; -NH2, a C1..5-alkyl radical; -CF3; -0-alkyl; -0- aryl; -SH; -S-alkyl; -S(=O)-alkyl; -S(=O)2-alkyl, -N=C=S, -C(=O)-alkyl; -C(=O)-aryl; -NH-C(=O)-alkyl; -CN; -C(=O)-OH; -C(=O)-NH2; -C(=O)-O-alkyl or -S(=0)2-NH2; R8 and R9, independently of one another, in each case represent a hydrogen atom; a C,..5-alkyl radical; an aryl radical or a heteroaryl radical; R1 represents a hydrogen atom; -C(=O)-0-alkyl; a radical -CH2OH; a radical -CH2CI or a methylene radical (-CH2-); or alternatively R1 together with R1 form a linkage, in case R1 represents a methylene radical (-CH2-) and R1 itself represents a linkage; and R11 represents a hydrogen atom or an alkyl radical which may optionally be wherein aryl represents a phenyl group, a naphthyl group or a substituted phenyl or heteroaryl represents an aromatic 5-to 14-membered heterocyclic group in which the heteroatom or heteroatoms of the ring is/are selected from the group consisting of 0 and N and the heterocyclic group can be substituted; alkyl, if not defined otherwise, represents a C1..10 alkyl radical; cycloalkyl represents a C3.16 cycloalkyl radical which can be substituted and which may contain at least on heteroatom in the ring which is selected from the group consisting of 0 and N; * S S * *SS * * S S * * S I * * S * * * *. * a.4. S S S * I S S S *. S **I *S* S the mono-or bicyclic ring system can be substituted and the rings of the aforementioned mono-or bicyclic ring system are in each case independently of one another 5-, 6-or 7-membe red and may in each case independently of one another optionally contain 1, 2 or 3 heteroatom(s) independently selected from the group consisting of 0 and N; alkylene represents a C1.. 5 alkylene group which can be substituted; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof; for the manufacture of a medicament for the prophylaxis and/or treatment of a disorder or disease related to food intake.</p>
<p>If one or more of the residues R1 to R11 represents or comprises an aryl or heteroaryl radical, which may be substituted, unless defined otherwise, preferably said aryl or heteroaryl radical may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of C1-perf1uoraIkyl, -C1-alkyI substituted with one or more methoxy and/or ethoxy groups, -C1-alkyl, -C1-alkyl substituted with one or more hydroxy groups, -C1-alkyl substituted with one or more chlorine atoms, -O-C1-alkyl, -O-C1-alkyl substituted with one or more methoxy and/or ethoxy groups, -S-C1..6-alkyl, -C(=O)-OH, -C(=O)-O-C1-alkyl, -O-C(=O)-C1- alkyl, F, CI, Br, I, -CN, -OCF3, -O-C2F5, -O-C3F7, -O-C4F9, -SCF3, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=O)-C1-alkyl, -N(C1..6-alkyl)-C(=O)-C1..6-alkyl, -NO2, -CHO, -C(=O)-C1-aIkyl, -C(=O)-C1-perfluoroalkyl, -C(=S)-NH-Cj..6-alkyl, -CF2H, -CFH2, C(O)NRARB, C(=O)NHNRcRD, -S(=O)-C1-alkyl, -S(=O)2-Ci..6-alkyl, -S(=O)2-phenyl, -(Ci..5-alkylene)-S-Ci..6-alkyl, -(C1..5-alkylene)-S(=O)-C1..6-alkyl, -(C1..5- alkylene)-S(=O)2-C1-alkyl, NRERF, -(Ci..5-alkylene)-N RERF, -S(=O)-NH2, -S(=O)2-N H-C1-alkyl, -S(=O)2-NH-phenyl, -NH-S(=O)2-Ci-alkyI, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl; * * . S..</p>
<p>* S S S S S * * S * . S S. S S 1* . S S * S S * S S* S *** S*S S whereby in each case the cyclic moieties cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl can optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of F, Cl, Br, I, -OH, -CE3, -CN, -NO2, -C1..6-alkyl, -0-C1..6-alkyl, -0-CF3 and -S-CF3 and whereby RA, RB, RE and RF, independently of one another, represent hydrogen or -C1..</p>
<p>6-alkyl or RA and RB in each case together with the bridging nitrogen atom form a radical selected from the group consisting of pyrrolidinyl, imidazolidinyl, piperazinyl, piperidinyl, morpholinyl, azepanyl and diazepanyl which may be at least mono-substituted with one or more identical or different C1..6 alkyl radicals and whereby Rc and RD, independently of one another, represent hydrogen, -C1..6- alkyl, -C(=0)-0-C1-alkyl, C3..8-cycloalkyl, -(C1..5-alkylene)-C8-cycloalkyl, -(C1..6-alkylene)-O-C1..6-alkyl or -C1..6-alkyl substituted with one or more hydroxy groups or Rc and R in each case together with the bridging nitrogen atom form a radical selected from the group consisting of pyrrolidinyl, imidazolidinyl, piperazinyl, piperidinyl, morpholinyl, azepanyl and diazepanyl which may be at least mono-substituted with one or more substituents independently selected from the group consisting -C1..6-alkyl, -C(=O)-C1-alkyl, -C(=O)-O-C1.6-alkyl, -C(=O)-NH-C1.6-alkyl, -C(=S)-NH-C1..6-alkyl, oxo (=0), -C1-alkyl substituted with one or more hydroxy groups, -(C1-alkylene)-0-C1-alkyl and -C(=0)-NH2.</p>
<p>More preferably said aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of-CF3, - C2F5, -C3E7, -C4F9, -CH2CI, -CHCI2, -C2H4CI, methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH, -O-CH2-O-CH3, -O-CH2-CH2-0-CH3, -O-CH2-O-C2H5, -C(OCH3)(C2H5)2, -C(OCH3)(CH3)2, -O-CH3, -0-C2H5, -O-CH2-CH2-CH3, -0-CH(CH3)2, -0-CH2-CH2-CH2-CH3, -0-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, -C(=0)-OH, -C(=0)-0-CH3, -C(=0)-0-C2H5, - C(=0)-0-C3H7, -C(=0)-0-C(CH3)3, -0-C(=O)-CH3, -0-C(=0)-C2H5, -0-C(=0)- CH(CH3)2, .-0-C(=0)-CH2-CH2-CH3, -0-C(=0)-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -0-C2F5, -0-C3E7, -0-C4F9, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=0)-CH3, * S S * * s * S S S *j4 S S S * S 5 * * S *S 5 5 5 5 S * S S S S S * S* S 555 **S S -NH-C(=O)-C2H5, -NH-C(=O)-C(CH3)3, -NO2, -CHO, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-C(CH3)3, -C(=O)-CF3, -C(=O)-C2F5, -C(=O)-C3F7, -C(=S)-NH-CH3, -C(=S)-NH- C2H5, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH- C3H7, -C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -C(=O)-NH-NH-CH3, -C(=O)-NH-NH-C2H5, - C(=O)-NH-NH2, -C(=O)-NH-N(CH3)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, -S(=O)2-C3H7, .-S(=O)2-phenyl, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2, -N(C2H5)2, -CH2-N(CH3)2, -(CH2)-morpholinyl, -(CH2)-piperidinyl, -(CH2)- piperazinyl, -(CH2)-N(C2H5)2, -CH2-N(C3H7)2, -CH2-N(C4H9)2, -CH2-N(CH3)(C2H5), -S(=O)N H2, -S(=O)2-N H-CH3, -S(=O)2-N H-phenyl, -N H-S(=O)2-CH3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl, whereby said thiophenyl radical can be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl.</p>
<p>Even more preferably said aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3, -O-C2H5, -NO2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
<p>Preferred aryl radicals which are optionally at least mono-substituted are phenyl and naphthyl (1-and 2-naphthyl).</p>
<p>Preferably the heteroatoms which are present as ring members in the heteroaryl radical may, unless defined otherwise, independently be selected from the group consisting of nitrogen and oxygen. More preferably a heteroaryl radical is 5-to 14-membered and may comprise 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of nitrogen and oxygen.</p>
<p>Preferred heteroaryl radicals which are unsubstituted or at least mono-substituted are pyridinyl, furyl (furanyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxadiazolyl, triazolyl, pyridazinyl, indolyl, isoindolyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, benzo[b]fu ranyl, benzo[b]thiophenyl, [2,1,3]-benzoxadiazolyl, [1,2,3]-benzoxadiazolyl, benzoxazolyl, benzisoxazolyl, 2H-chromenyl, pyranyl, indazolyl and quinazolinyl.</p>
<p>* ,. . * *ia * a a * * a * a * a.7 a *i. * a * * S S S a a as. a.. a If one or more of the residues R1 to R11 represents or comprises an optionally at least one heteroatom as a ring member containing C316 cycloalkyl radical, which may be substituted, unless defined otherwise, preferably said cycloalkyl radical may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), Ci..6-perfluoralkyl, -C1..6-alkyl, -C,6-alkyl substituted with one or more hydroxy groups, -C1-alkyI substituted with one or more chlorine atoms, -C1..6-alkyl substituted with one or more methoxy and/or ethoxy groups, -0-C1..6-alkyl, -O-C1..6-alkyl substituted with one or more methoxy and/or ethoxy groups, -S-C1..6-alkyl, -C(=0)-OH, -C(=O)-O-C1-aIkyl, -O-C(0)-C1.6-alkyl, F, Cl, Br, I, -CN, -OCF3, -O-C2F5, -O-C3F7, -O-C4F9, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=O)-C1..6-alkyl, -N(C1..6-alkyl)-C(=O)-C1..6-alkyl, -NO2, -CHO, -C(0)-C1..</p>
<p>6-alkyl, -C(=0)-C1-perfluoroaIkyI, -C(=S)-NH-C1..6-alkyl, -CF2H, -CFH2, -C(0)- NRARB, C(=O)NHNRcRt), -S(=0)-C,..6-alkyl, -S(=O)2-C1.6-alkyl, -S(=O)2-phenyl, - (C15-alkylene)-S-C1..6-alkyl, -(C1..5-alkyIene)-S(O)-C16-aIkyI, -(Cl..5-alkylene)-S(0)2- C1..6-alkyl, NRERF, (Ci..5alkylene)NRERF, -S(=O)-NH2, -S(=0)2-NH-C1-alkyI, -S(=0)2-N H-phenyl, -NH-S(=0)2-Cj-aIkyI, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl; whereby in each case the cyclic moieties cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl can optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of F, Cl, Br, I, -OH, -CF3, -CN, -NO2, -C1..6-alkyl, -0-C1.6-alkyl, -0-CF3 and -S-CF3 and whereby RA, RB, RE and RF, independently of one another, represent hydrogen or -C1.</p>
<p>6-alkyl or RA and RB in each case together with the bridging nitrogen atom form a radical selected from the group consisting of pyrrolidinyl, imidazolidinyl, piperazinyl, piperidinyl, morpholinyl, azepanyl and diazepanyl which may be at least mono-substituted with one or more identical or different C1 alkyl radicals and whereby Rc and RD, independently of one another, represent hydrogen, -C1..6- alkyl, -C(=O)-O-C1-aIkyI, C33-cycloalkyl, -(C1..5-alkylene)-C3..8-cycloalkyl, -(C1..6-alkylene)-O-Ci..6-alkyl or -C1..6-alkyl substituted with one or more hydroxy groups or * * *4 I * 4 * a * * S I a 4* 4.' . ap. SI. I Rc arid RD in each case together with the bridging nitrogen atom form a radical selected from the group consisting of pyrrolidinyl, imidazolidinyl, piperazinyl, piperidinyl, morpholinyl, azepanyl and diazepanyl which may be at least mono-substituted with one or more substituents independently selected from the group consisting -C1..6-alkyl, -C(=O)-Ci-alkyI, -C(=O)-O-Ci-alkyl, -C(=O)-NH-C1-alkyl, -C(=S)-NH-C1..6-alkyl, oxo (=0), -C1-alkyl substituted with one or more hydroxy groups, -(C1..6-aIkyIene)-O-Cl6-alkyl and -C(0)-NH2.</p>
<p>More preferably said cycloalkyl radical may optionally be substituted with 1, 2, 3, 4 or substituent(s) independently selected from the group consisting of oxo (0), thioxo (=S), -CF3, -C2F5, -C3F7, -C4F9, -CH2CI, -CHCI2, -C2H4CI, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -CH2-OH, -CH2-CH2- OH, -CH2-CH2-CH2-OH, -O-CH2-O-CH3, -O-CH2-CH2-O-CH3, -O-CH2-O-C2H5, -C(OCH3)(C2H5)2, -C(OCH3)(CH3)2, -0-CH3, -0-C2H5, -0-CH2-CH2-CH3, -0-CH(CH3)2, -0-CH2-CH2-CH2-CH3, -0-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, -C(=0)-OH, -C(=O)-0-CH3, -C(=0)-0-C2H5, - C(=0)-0-C3H7, -C(=0)-0-C(CH3)3, -0-C(=O)-CH3, -0-C(=0)-C2H5, -O-C(=0)- CH(CH3)2, -0-C(0)-CH2-CH2-CH3, -0-C(0)-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -0-C2F5, -0-C3F7, -0-C4F9, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -NH-C(=O)-C(CH3)3, -NO2, -CHO, -C(=O)-CH3, -C(=0)-C2H5, - C(=O)-C(CH3)3, -C(=O)-CF3, -C(=0)-C2F5, -C(=O)-C3F7, -C(=S)-NH-CH3, -C(=S)-NH- C2H5, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=0)-NH- C3H7, -C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -C(=O)-NH-NH-CH3, -C(=O)-NH-NH-C2H5, -C(=0)-NH-NH2, -C(=O)-NH-N(CH3)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-C3H7, -S(0)2-CH3, -S(=0)2-C2H5, -S(0)2-C3H7, -S(=0)2-phenyl, -NH2, -N H-CH3, -N H-C2H5, -N(CH3)2, -N(C2H5)2, -CH2-N(CH3)2, -(CH2)-morpholinyl, -(CH2)-piperidinyl, -(CH2)- piperazinyl, -(CH2)-N(C2H5)2, -CH2-N(C3H7)2, -CH2-N(C4H9)2, -CH2-N(CH3)(C2H5), -S(=O)-N H2, -S(=O)2-NH-CH3, -S(=O)2-NH-phenyl, -N H-S(0)2-CH3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl, whereby said thiophenyl radical can be substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl. * S *</p>
<p>( , a A. a * i S _, 1 5 1 S I a * S * a Sal I Even more preferably said cycloalkyl radical is unsubstituted or may be substituted with oxo (=0).</p>
<p>If one or more of the residues R1 to R11 represents or comprises a C3..16 cycloalkyl radical which contains one or more heteroatoms as ring members, unless defined otherwise, each of these heteroatoms may preferably be selected from the group consisting of nitrogen and oxygen. More preferably a C3..16 cycloalkyl radical may optionally contain 1, 2, 3 or 4 heteroatom(s) independently selected from the group consisting of nitrogen and oxygen as ring members.</p>
<p>Suitable optionally at least one heteroatom as ring member containing cycloalkyl radicals may preferably be selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, aziridinyl, azetidinyl, imidazolidinyl, pyrazolidinyl, tetrahydrofuranyl, azepanyl, diazepany, azocanyl, tetrahydropyranyl, [1,3]-oxazinanyl, hexahydropyrimidinyl, oxazolidinyl, (1,3)-dioxanyl, (1,4)-dioxanyl and (1,3)-dioxolanyl.</p>
<p>Suitable optionally at least one heteroatom as ring member containing C3..16 cycloalkyl radicals which are condensed with an unsubstituted or at least mono-substituted mono-or bicyclic ring system may preferably be selected from the group consisting of indolinyl, dihydrobenzo[d]imidazOlyl, isoindolinyl, decahydronaphthyl, (1,2,3,4)-tetrahydroquinolinyl, (1,2,3,4)-tetrahydroisoquinoliflyl and (1,2,3,4)-tetrahydronaphthyl.</p>
<p>Suitable C3..16 cycloalkyl radicals which are bridged by at least one unsubstituted or at least mono-substituted linear or branched alkylene group may preferably be selected from the group consisting of adamantyl, bicyclo[2.2.1]heptyl and bicyclo[3.1.1]heptyl.</p>
<p>A mono-or bicyclic ring system according to the present invention -if not defined otherwise -means a mono-or bicyclic hydrocarbon ring system that may be saturated, unsaturated or aromatic. Each of its different rings may show a different degree of saturation, i.e. they may be saturated, unsaturated or aromatic. Optionally * * * S *s * S..</p>
<p>.: : : *.io * . S S S * . S. * ** . S S..</p>
<p>each of the rings of the mono-or bicyclic ring system may contain one or more, preferably 1, 2 or 3, heteroatom(s) as ring member(s), which may be identical or different and which can preferably be selected from the group consisting of nitrogen and oxygen. The rings of the mono-or bicyclic ring system are preferably 5-, 6-or 7-membered.</p>
<p>The term "condensed" according to the present invention means that a ring or ring system is attached to another ring or ring system, whereby the terms "annulated" or "annelated" are also used by those skilled in the art to designate this kind of attachment.</p>
<p>If one or more of the residues R1 to R11 comprises a mono-or bicyclic ring system, which may be substituted, unless defined otherwise, preferably said mono-or bicyclic ring system may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of oxo (=0), thioxo (=S), -CE3, - C2F5, -C3F7, -C4F9, -CH2CI, -CHCI2, -C2H4CI, methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH, -O-CH2-O-CH3, -O-CH2-CH2-O-CH3, -O-CH2-O-C2H5, -C(OCH3)(C2H5)2, -C(OCH3)(CH3)2, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-CH2-CH2-CH2-CH3, -O-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, -C(=0)-OH, -C(=0)-O-CH3, -C(=0)-0-C2H5, - C(=0)-O-C3H7, -C(=0)-0-C(CH3)3, -0-C(=0)-CH3, -0-C(=0)-C2H5, -0-C(=0)- CH(CH3)2, -0-C(=0)-CH2-CH2-CH3, -0-C(=0)-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -0-C2E5, -0-C3F7, -0-C4E9, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -NH-C(=O)-C(CH3)3, -NO2, -CHO, -C(=O)-CH3, -C(=0)-C2H5, - C(=0)-C(CH3)3, -C(=O)-CF3, -C(=O)-C2E5, -C(=0)-C3E7, -C(=S)-NH-CH3, -C(=S)-NH- C2H5, -CF2H, -CEH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH- C3H7, -C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -C(=O)-NH-NH-CH3, -C(=O)-NH-NH-C2H5, -C(=O)-NH-NH2, -C(=O)-NH-N(CH3)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=0)-C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, -S(=O)-C3H7, -S(=0)2-phenyl, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2, -N(C2H5)2, -CH2-N(CH3)2, -(CH2)-morpholinyl, -(CH2)-piperidinyl, -(CH2)- piperazinyl, -(CH2)-N(C2H5)2, -CH2-N(C3H7)2, -CH2-N(C4H9)2, -CH2-N(CH3)(C2H5), -S(=0)-NH2, -S(=0)2-N H-CH3, -S(=O)2-NH-phenyl, -NH-S(=O)2-CH3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, * S *** ** S *5* : : : *11 * 5.</p>
<p>* S * * S S * 555 5 5 S 5*S S phenoxy and benzyl, whereby said thiophenyl radical can be substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl.</p>
<p>If one or more of the residues R1 to R11 represents or comprises a linear or branched C11o alkyl radical or a linear or branched C1.5-alkylene group, which may be substituted, unless defined otherwise, preferably said C110 alkyl radical or said Ci.5 alkylene group may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of-OH, -NH2, -NH-alkyl, -N(alkyl)(alkyl), -S-alkyl, -S(=O)-alkyl, -S(=O)2-alkyl, halogen, -CN, -NH[(CH2)i, 2, 3 or4 aryl], -N[alkyl][(CH2)l,2,3or4-aryl], piperazinyl, piperidinyl, morpholinyl, aryl, heteroaryl, -C(0)-alkyl, -C(O)-aryl, -C(0)-heteroaryl, -C(=O)-O-atkyl, -S-aryl, -S(=O)-aryl, -S(=O)2-aryl, -S-heteroaryl, -S(=O)-heteroaryl, -S(=O)2-heteroaryl, -S-(CH2)i 2,3 or 4 aryl, -S(0)-(CH2)i, 2, 3 or 4-aryl, S(0)2(CH2)1, 2, 3 or 4-aryl, -S-(CH2)i, 2, 3 or 4-heteroaryl, S(0)(CH2)i, 2,3or4-heteroal and -S(0)2-(CH2)1, 2,3or4-heteroal; whereby the aforementioned aryl and heteroaryl groups may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) selected from the group consisting of -CF3, -C2F5, -C3F7, -C4F9, -CH2CI, -CHCI2, -C2H4CI, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -CH2-OH, -CH2-CH2-OH, -CH2-CH2- CH2-OH, -O-CH2-O-CH3, -O-CH2-CH2-O-CH3, -O-CH2-O-C2H5, -C(OCH3)(C2H5)2, - C(OCH3)(CH3)2, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-CH2-CH2-CH2- CH3, -O-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2- CH3, -S-C(CH3)3, -C(=O)-OH, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-C3H7, - C(=O)-O-C(CH3)3, -O-C(=O)-CH3, -O-C(=O)-C2H5, -O-C(=O)-CH(CH3)2, -O-C(=O)- CH2-CH2-CH3, -O-C(0)-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -O-C2F5, -O-C3F7, -0- C4F9, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -SO3H, -NH-C(=O)-CH3, -NH-C(=O)-C2H5, -NH-C(=O)-C(CH3)3, -NO2, -CHO, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-C(CH3)3, -C(=O)- CF3, -C(=O)-C2F5, -C(=O)-C3F7, -C(=S)-NH-CH3, -C(=S)-NH-C2H5, -CF2H, -CFH2, - C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH-C3H7, -C(=O)-N(CH3)2, - C(=O)-N(C2H5)2, -C(=O)-NH-NH-CH3, -C(=O)-NH-NH-C2H5, -C(=O)-NH-NH2, -C(=O)- NH-N(CH3)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, - S(0)2-C3H7, -S(=O)2-phenyl, -N H2, -NH-CH3, -N H-C2H5, -N(CH3)2, -N(C2H5)2, -CH2-N(CH3)2, -(CH2)-morpholinyl, -(CH2)-piperidinyl, -(CH2)-piperazinyl, -(CH2)-N(C2H5)2,</p>
<p>S</p>
<p>* * * S * S 555 $ 5 5 5 * 5 5 0* S * * 0 * * * S S * S S. * *** * . . ** * -CH2-N(C3H7)2, -CH2-N(C4H9)2, -CH2-N(CH3)(C2H5), -S(=O)-NH2, -S(=O)2-NH-CH3, -S(=O)2-N H-phenyl, -N H-S(=O)2-CH3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, phenyl, thiophenyl, phenoxy and benzyl, whereby said thiophenyl radical can be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl and n-propyl.</p>
<p>More preferably said C1..10 alkyl or said C1..5-alkylene group may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of Cl, Br, F, I, -OH, -CN, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2, -N(C2H5)2, - N(CH3)(C2H5), piperazinyl, piperidinyl, morpholinyl, -S-CH3, -S-C2H5, -S-CH(CH3)2, -S-C(CH3)3, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-CH(CH3)2, -S(=O)-C(CH3)3, -C(=O)- CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-C(CH3)3, -C(=O)-aryl, -C(=O)-heteroaryl, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, aryl and heteroaryl; wherein aryl represents a phenyl radical or a naphthyl radical and heteroaryl represents a radical selected from the group consisting of pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, indolyl and isoindolyl, and wherein the aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -CE3, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -0- CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-CH2-CH2-CH2-CH3, -O-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -NO2, -CHO, -C(0)- CH3, -C(=O)-C2H5, -C(=O)-C(CH3)3, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH-C3H7, -C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -S(=O)-CH3, - S(=O)-C2H5, -S(=O)-C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, -S(=O)2-C3H7, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2 and -N(C2H5)2.</p>
<p>Suitable C1..10 alkyl radicals are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2- octyl, 3-octyl, 4-octyl, 2-(6-methyl)-heptyl, 2-(5-methyl)-heptyl, 2-(5-methyl)-hexyl, 2- (4-methyl)-hexyl, 2-(7-methyl)-octyl, 2-(6-methyl)-octyl, n-nonyl and n-decyl.</p>
<p>S</p>
<p>* S S S S 555 : : : * * S S 5 5 5 * *.. :.. .</p>
<p>--</p>
<p>Suitable C1..5-alkylene groups include -(CH2)-, -CH(CH3), -C(CH3)2-, -(CH2)2-, - (CH2)3-,-(CH2)4-and -(CH2)5-.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R1 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3- pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl; a radical selected from the group consisting of-CH2-C(0)-CH3, -CH2-C(0)-C2H5, - CH2-C(=O)-CH2-CH2-CH3, -CH2-C(=O)-CH(CH3)2, -CH2-C(=O)-C(CH3)3, -CH2-CH2- C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2-CH2-C(=O)-CH2-CH2-CH3, -CH2-CH2- C(=O)-CH(CH3)2, -CH2-CH2-C(=O)-C(CH3)3, -CH2-CH2-CH2-C(0)-CH3, -CH2-CH2- CH2-C(=O)-C2H5, -CH2-CH2-CH2-C(=O)-CH2-CH2-CH3, -CH2-CH2-CH2-C(=O)-CH(CH3)2 and -CH2-CH2-CH2-C(=O)-C(CH3)3, a radical selected from the group consisting of -CH2-aryl, -CH2-CH2-aryl, -CH2-CH2- CH2-aryl, -CH(CH3)-CH2-aryl, -CH(C2H5)-CH2-aryl, -CH2-CH(CH3)-aryl, -CH2- CH(C2H5)-aryl, -CH2-CH2-CH2-CH2-aryl, -CH2-C(=O)-aryl, -CH2-CH2-C(=O)-aryl, -CH2-CH2-CH2-C(=O)-aryl, -CH(CH3)-CH2-C(=O)-aryl, -CH(C2H5)-CH2-C(0)-aryl, - CH2-CH(CH3)-C(0)-aryl, -CH2-CH(C2H5)-C(=O)-aryl, -CH2-CH2-CH2-CH2-C(0)-aryl, -CH2-C(=O)-heteroaryl, CH2-CH2-C(=O)-heteroaryl, -CH2-CH2-CH2-C(=O)-heteroaryl, CH(CH3)-CH2-C(=O)-heteroaryl, -CH(C2H5)-C H2-C(=O)-heteroaryl, -CH2CH(CH3)-C(=O)-heteroaryl, -CH2-CH(C2H5)-C(=O)-heteroaryl and -CH2-CH2-CH2-CH2-C(=O)-heteroaryl; wherein aryl represents a phenyl radical or a naphthyl radical and heteroaryl represents a radical selected from the group consisting of pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, indolyl and isoindolyl, and wherein the aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -C F3, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -0- CH3, -O-C2H5, -O-CH2-CH2-CH3, -O-CH(CH3)2, -O-CH2-CH2-CH2-CH3, -O-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -NO2, -CHO, -C(=O)-* S * S S S 5 * S 555 * S S S S * . . 14 * * S S * . * *.* :.. .* CH3, -C(=O)-C2H5, -C(=O)-C(CH3)3, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, - C(=O)-NH-C2H5, -C(=O)-NH-C3H7, -C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -S(=O)-CH3, - S(=O)-C2H5, -S(=O)-C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, -S(=O)2-C3H7, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2 and -N(C2H5)2, a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of-C(=O)-O-CH3, -C(0)-O-C2H5, - C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-C(CH3)3, -C(=O)-O-CH2-CH2- CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; and Z1, Z2, Z3, Z4, m, n and R2 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R2 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3- pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3octyl and 4-octyl; or a radical selected from the group consisting of -C(=O)-O-CH3, -C(=O)-O-C2H5, - C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-C(CH3)3, -C(=O)-O-CH2-CH2- CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; and Z1, Z2, Z3, Z4, m, n, R1 and R3 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>* S S S 5 * S..</p>
<p> :.155..S * *.. :.. a Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R1 and R2 together form a linkage represented by a group X, wherein X represents -(CHR8)-, -(CHR8)-(CHR9)-, -(CHR8)-(CHR8)-, - (CHR8)-(CH R8)-(CH R6)-, -(CH R8)-(CH R8)-(CH R8)-(CH R8)-or -CR8=CR9-; and Z1, Z2, Z3, Z4, m, n and R3 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Also preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R3 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3- pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of Cl, Br, F, I, -OH, -CN, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2, -N(C2H5)2, -N(CH3)(C2H5), -NH-CH2-CH2- aryl, -N(CH3)-CH2-CH2-aryl, piperazinyl, piperidinyl, morpholinyl, -S-CH3, -S-C2H5, -S-CH(CH3)2, -S-C(CH3)3, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-CH(CH3)2, -S(=O)-C(CH3)3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-C(CH3)3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, aryl and heteroaryl; an aryl radical; a heteroaryl radical: a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, imidazolidinyl, azepanyl, diazepanyl, azocanyl, adamantyl, bicyclo[2.2.1]heptyl and bicyclo[3. 1.1]heptyl, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, iso-butyl, tert-butyl, oxo (=0) and thioxo (=S); * * * * S a * * S S..</p>
<p>S S * S * . . ID S * S * * S I * S * S.. * or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, -C(0)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; whereby aryl represents a phenyl radical or a naphthyl radical and heteroaryl represents a radical selected from the group consisting of pyridinyl, furyl (furanyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, indolyl and isoindolyl, and whereby the aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -CF3, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -O-CH3, -O-C2H5, -O-CH2-CH2-CH3, -0- CH(CH3)2, -O-CH2-CH2-CH2-CH3, -O-C(CH3)3, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S- CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -NO2, -CHO, -C(=O)-CH3, -C(=O)-C2H5, -C(O)-C(CH3)3, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH-C3H7, - C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)-C3H7, -S(=O)2- CH3, -S(=O)2-C2H5, -S(=O)2-C3H7, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2 and -N(C2H5)2; and Z1, Z2, Z3, Z4, m, n, R1, R2 and R4 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>More preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R3 represents a hydrogen atom; a radical selected from the group consisting of-CH3, -CH2-CH3, -CH(CH3)2, -CH2- CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, -CH2-CH2-CH2-CN, -CH2-CH2-CH2- CH2-CN, -CH2-Cl, -CH2-CH2-Cl, -CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-Cl, -CH2-CH2- CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-CH2-Cl, -CH2-N(C2H5)2, -CH2-CH2- N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-N(CH3)2, -CH2-CH2- N(CH3)2, -CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-p p * a a a * * * * 17 * a * * a a * * * a. * p * * as. * CH2-N(CH3)2, -c H2-CH2-CH2-C H2-CH2-CH2-N(CH3)2, -CH2-NH-(C2H5), -CH2-CH2-N H- (C2H5), -c H2-CH2-CH2-N H-(C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2- N H-(C2H5), -CH2-CH2-CH2-CH2-CH2-N H-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-NH- (C2H5), -CH2-CH2-S(=O)2-CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(=O)2CH2-CH3, -CH2-CH2-S(=O)2-CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(=O)2-CH3, CH2-CH2-S(=O)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2-S(=O)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2-S(=O)-CH3, -CH2-CH2-CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-SCH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CH2-NH2, -CH2-CH2-NH2, -CH2-CH2-CH2NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH(CH3)-CH2-CH2N(C2H5)2, -CH(CH3)-CH2-CH2-CH2-N(C2H5)2, -CH(CH3)-CH2-N(CH3)2, .-CH(CH3)-CH2-CH2-N(CH3)2, -c H(CH3)-CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2-OH, -CH2-CH2- CH2-OH; -CH2-C(0)-O-CH3, -CH2-C(0)-O-CH2-CH3, -CH2-C(0)-O-C(CH3)3, -CH2- CH2-C(=O)-O-CH3, -CH2-CH2-C(=O)-O-CH2-CH3, -CH2-CH2-C(=O)-O-C(CH3)3, - CH[C(=O)-CH2-CH3]-CH2-CH2-C(0)-CH2-CH3, -CH[C(=O)-CH3]-CH2-CH2-C(0)- CH3, -CH2-morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2- pyridinyl, -CH2-CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl, a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl; or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(cH3)2, -C(=O)-CH2-CH2-CH3, -c(=o)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; and Z1, Z2, Z3, Z4, m, n, R1, R2 and R4 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, I i * IQ * SI * * *IJ S I. S I I. ** S ( *55 p preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Also preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R2 and R3 together form a linkage represented by a group -CH2-CH2-O-CH2-CHR10-, -CH2-CH2-CH2-CH R10-, -CH2-CH2-CH2-CH2-CHR10-or -CH2-CH2-NR11-CH2-CHR10-; and Z1, Z2, Z3, Z4, m, n, R1 and R4 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R4 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(0)-CH3 or -NH-C(=O)-C2H5; and Z1, Z2, Z3, Z4, m, n, R1 to R3 and R5 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R5 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and Z1, Z2, Z3, Z4, m, n, R1 to R4 and R6 to R11 have any of the above defined meanings, optionally in form of one of its stereolsomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, a*. *-.</p>
<p>-.; : : . 19. I z II *</p>
<p>preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Also preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R6 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(0)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and Z1, Z2, Z3, Z4, m, n, R1 to R5 and R7 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomerS, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R7 represents a hydrogen atom; F; Cl; Br or -NO2; and Z1, Z2, Z3, Z4, m, n, R1 to R6 and R8 to R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R8 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and Z1, Z2, Z3, Z4, m, n, R1 to R7, R9, R1 and R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, :: : 20.</p>
<p>* *. :. : E i preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Also preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R9 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and Z1, Z2, Z3, Z4, m, n, R1 to R8, R1 and R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R1 represents a hydrogen atom; -C(=O)-O-CH3; -C(O)-O-C2H5; -CH2-OH; -CH2-Cl or -CH2-; and Z1, Z2, Z3, Z4, m, n, R1 to R9 and R11 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Also preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein R11 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH; and Z1, Z2, Z3, Z4, m, n and R1 to R1 have any of the above defined meanings, optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>:: :: .*. 21 * More preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I, wherein Z1 represents a nitrogen atom or a carbon atom bonded to another radical R4 (C-R4); z2 represents a nitrogen atom or a carbon atom bonded to another radical R5 (C-R5); Z3 represents a nitrogen atom or a carbon atom bonded to another radical R6 (C-R6); z4 represents a nitrogen atom or a carbon atom bonded to another radical R7 (C-R7); with the restriction that only one of the groups Z1, Z2, Z3 or Z4 can represent a nitrogen atom; R1 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of -CH2-C(=O)-CH3, -CH2-C(=O)- C2H5, -CH2-CH2-C(0)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2-C(=O)-phenyl, -CH2-C(=O)-pyridinyl, -CH2-CH2-C(=O)-phenyl and -CH2-CH2-C(=O)-pyrid inyl; R2 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3- pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl; or a radical selected from the group consisting of -C(=O)-O-CH3, -C(=O)-O-C2H5, - C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)-O-C(CH3)3, -C(=O)-O-CH2-CH2- CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; or alternatively R1 and R2 together form a linkage represented by a group X, wherein X represents -(CH R8)-, -(CHR8)-(CH R9)-, -(CH R8)-(CH R8)-, -(CH R8)-(CH R8)-(CH R8)-, :: 22 * -(CH R8)-(CH R8)-(CH R8)-(CH R8)-or -CR8=CR9-; R3 represents a hydrogen atom; a radical selected from the group consisting of -CH3, -CH2-CH3, -CH(CH3)2, -CH2- CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, -CH2-CH2-CH2-CN, -CH2-CH2-CH2- CH2-CN, -CH2-Cl, -CH2-CH2-Cl, -CH2-CH2-CH2-Cl, -cH2-CH2-CH2-QH2-Cl, -CH2-CH2- CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-CH2-Cl, -CH2-N(C2H5)2, -CH2-CH2- N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-N (CH3)2, -CH2-CH2- N(CH3)2, -CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2- CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-CH2-N (CH3)2, -CH2-N H-(C2H5), -CH2-CH2-N H- (C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2- NH-(C2H5), -CH2-CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-N H- (C2H5), -CH2-CH2-S(=O)2-CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(0)2- CH2-CH3, -CH2-CH2-S(0)2-CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(0)2-CH3, -CH2-CH2-S(=O)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2-S(0)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2-S(=O)-CH3, -CH2-CH2-CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CH2-N H2, -CH2-CH2-N H2, -CH2-CH2-CH2-NH2, -CH2-CH2-CH2- CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-N(C2H5)2, -CH (CH3)-CH2- CH2-CH2-N(C2H5)2, -CH(CH3)-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH; -CH2-C(0)-OCH3, -CH2-C(=O)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2-C(=O)-O-CH3, CH2-CH2-C(0)-O-CH2-CH3, -CH2-CH2-C(=O)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]CH2-CH2-C(0)-CH2-CH3, -CH[C(0)-CH3J-CH2-CH2-C(0)-CH3, -CH2-morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br;</p>
<p>S 23 *</p>
<p>*. * S a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl or a radical selected from the group consisting of -C(0)-CH3, -C(0)-C2H5, -C(0)-CH(cH3)2: -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and c(=o)-cH2-cl-I2-cH2-cI-I3; or alternatively R2 and R3 together form a linkage represented by a group -CH2-CH2- O-CH2-CHR10-, -CH2-CH2-CH2-CHR10-, -CH2-CH2-CH2-CH2-CHR10 or -CH2-CH2-NR11-CH2-CHR10-; R4 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(0)-CH3 or -NH-C(=O)-C2H5; R5 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(0)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or-C(0)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7 represents a hydrogen atom; F; Cl; Br or -NO2; R8 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with I, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; : 24 a * * * a * _* * R9 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R1 represents a hydrogen atom; -C(0)-O-CH3; -C(=O)-O-C2H5; -CH2-OH; -CH2-CI or -CH2-; or alternatively R1 together with R1 form a linkage, in case R1 represents a methylene radical (-CH2-) and R1 itself represents a linkage; and R11 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>More particularly preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula Ia, R1 z4a 0 ; z' N> L KR3a Ia wherein zia represents a nitrogen atom or a carbon atom bonded to another radical R4a (c-R43); z2a represents a nitrogen atom or a carbon atom bonded to another radical</p>
<p>S</p>
<p>: : : : 25 s *</p>
<p>S</p>
<p>S. * .. .1 R5a (C_R5a); z3a represents a nitrogen atom or a carbon atom bonded to another radical R6a (CR6a) z4a represents a nitrogen atom or a carbon atom bonded to another radical R7a (c.R7a) with the restriction that only one of the groups Zia, z2a, z3a or z4a can represent a nitrogen atom; R represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; a 2oxo-2,3-dihydrobenzo[dJimidazOl-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of -CH2-C(=O)-CH3, -CH2-C(0)- C2H5, -CH2-CH2-C(0)-CH3, -CH2-CH2-C(0)-C2H5, -CH2-C(0)-phenyl, -CH2-C(=O)-pyrid inyl, -CH2-CH2-C(=O)-phenyl and -CH2-CH2-C(=O)-pyridinyl; R2a represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyt and n-pentyl; or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, -C(=O)- CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; R3 represents a hydrogen atom; a radical selected from the group consisting of -CH3, -CH2-CH3, -CH(CH3)2, -CH2- CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, -CH2-CH2-CH2-CN, -CH2-CH2-CH2- CH2-CN, -CH2-Cl, -CH2-CH2-Cl, -CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-Cl, -CH2-CH2- CH2-CH2-CH2-Cl, -CH2-CH2-GH2-CH2-CH2-CH2-Cl, -CH2-N(C2H5)2, -CH2-CH2-N(C2H5)2, -CH2-.CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, CH2CH2CH2 CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-C H2-CH2-CH2-N(C2H5)2, -CH2-N(CH3)2, -CH2-CH2- N(CH3)2, -CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2- CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-NH-(C2H5), -CH2-CH2-NH- (C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2- :: *. *. 26 *. : : * a a I a CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-S(=O)2-CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(=O)2-CH2-CH3, -CH2-CH2-S(=O)2- CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(=O)2-CH3, -CH2-CH2-S(=O)-CH2-CH3, - CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2-S(=O)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2- S(=O)-CH3, -CFI2-CH2-CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, - CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, - CH2-NH2, -CH2-CH2-NH2, -CH2-CH2-CH2-NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)- CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-CH2-N(C2H5)2, -CH(CH3)-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH; -CH2-C(0)-O-CH3, -CH2-C(=O)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2-C(=O)-O-CH3, -CH2-CH2-C(=O)-O-CH2-CH3, -CH2-CH2-C(0)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2-C(=O)-CH2-CH3, -c H[C(=O)-CH3]-CH2-CH2-C&0)-CH3, -CH2-morpholinyl, -CH2-CH2- morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; aradical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl, or a radical selected from the group consisting of -C(=O)-CH3, -C(0)-C2H5, -C(=O)-CH(CH3)2, -C(0)-CH2-CH2-CH3, -C(0)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; R4a represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5a represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; :: * .. 27 *. : : * . I 4 I -_. a -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R63 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2- CH2-CH3; -CE3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or-C(0)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and R7a represents a hydrogen atom; F; Cl; Br or -NO2; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>More particularly preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula lb, D3b Xb,, Z41' / Z3b Z2b 1b N lb wherein Zb represents a nitrogen atom or a carbon atom bonded to another radical R4b (C_R4b); Z2b represents a nitrogen atom or a carbon atom bonded to another radical R5b (CR5b); Z3b represents a nitrogen atom or a carbon atom bonded to another radical :: . *. 28 *0 * * 0</p>
<p>I I</p>
<p>*0 S * R61' (CR6b); Z4b represents a nitrogen atom or a carbon atom bonded to another radical R7b (CR7b); with the restriction that only one of the groups Z2b, Z3b or Z4b can represent a nitrogen atom; Xb represents -(CH R8b), (CHR8b)(CHR9b), -(CH R8b)(CH RBb), -(CH R8b)(CH R8 (CHR8b), -(CH R8b)(C H R8b)(CH R8b)(C HR81')-or _CRBb=CR9b; R3t represents a hydrogen atom; a radical selected from the group consisting of -CH3, -CH2-CH3, -CH(CH3)2, -CH2- CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, -CH2-CH2-CH2-CN, -CH2-CH2-CH2- CH2-CN, -CH2-Cl, -CH2-CH2-Cl, -CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-Cl, -CH2-CH2- CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-CH2-CI, -CH2-N(C2H5)2, -CH2-C H2- N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-N (CH3)2, -CH2-CH2- N(CH3)2, CH2-CH2-CH2-N(CH3)2 -CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2- CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-NH-(C2H5), -CH2-CH2-N H- (C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2- CH2-CH2-N H-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-N H-(C2H5), -CH2-CH2-S(0)2- CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(0)2-CH2-CH3, -CH2-CH2-S(0)2- CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(0)2-CH3, -CH2-CH2-S(0)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2-S(0)-CH2-CH3, -CH2-CH2-S(0)-CH3, -CH2-S(=O)-CH3, -CH2-CH2-CH2-S(0)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CH2-NH2, -CH2-CH2-N H2, -CH2-CH2-CH2-NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-CH2-N(C2H5)2, - CH(CH3)-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH; -CH2-C(0)-O-CH3, -CH2-C(=O)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2-C(0)-O-CH3, -CH2-CH2-C(=O)-O-CH2-CH3, -CH2-CH2-C(0)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2-C(=O)-CH2-CH3, -CH[C(0)-CH3]-CH2-CH2-C(0)-CH3, -CH2-morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2- :: :: : 29 * * * : * * N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with 1 012 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl, or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, -C(0)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; R4b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CE3; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1 012 substituent(s) independently selected from the group consisting of F, CI, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2- CH2-CH3; -CF3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or-C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7' represents a hydrogen atom; F; Cl; Br or -NO2; RBb represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, CI, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; : *. 30 : : : * S a * a and R9b represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomerS, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>More particularly preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula Ic, R ROc 4c I 2c S-N yC Z1c N ( 2)nc Ic wherein Z1c represents a nitrogen atom or a carbon atom bonded to another radical R4c (CR4c); Z2c represents a nitrogen atom or a carbon atom bonded to another radical R5c (CR5c); z3c represents a nitrogen atom or a carbon atom bonded to another radical R6c (CR6c); z4c represents a nitrogen atom or a carbon atom bonded to another radical R7c (CR7c); with the restriction that only one of the groups Z, Z2c, Z3c or Z4 can represent a nitrogen atom; :: :: . 31.</p>
<p>Rc represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of -CH2-C(=O)-CH3, -CH2-C(0)- C2H5, -CH2-CH2-C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2-C(=O)-phenyl, -CH2-C(=O)-pyridinyl, -CH2-CH2-C(=O)-phenyl and -CH2-CH2-C(=O)-pyrid inyl; yC represents -CH2-O-CH2-or -CH2-NR11 c..cH2...; nc represents 1, 2, 3 or 4; mc represents 0 or 1; R4c represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5c represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6c represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2- CH2-CH3; -CE3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7c represents a hydrogen atom; F; Cl; Br or -NO2; RbOC represents a hydrogen atom; -C(=O)-O-CH3; -C(=O)-O-C2H5; -CH2-OH; -CH2-Cl or -CH2-; * * * * a a * * * * I..</p>
<p>a. * * a * * * a * * a ** 1 and RuG represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>More particularly preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula Id, d md 4d / \ ,(CH)</p>
<p>N 2d Z1d N Id</p>
<p>wherein Z represents a nitrogen atom or a carbon atom bonded to another radical R4d (C_R4d); Z2d represents a nitrogen atom or a carbon atom bonded to another radical R5c (CR5d); Z3d represents a nitrogen atom or a carbon atom bonded to another radical R6d (CR6d); Z4d represents a nitrogen atom or a carbon atom bonded to another radical R7d (CR7d); with the restriction that only one of the groups Zd, Z2d, Z3d or Z4d can represent a nitrogen atom; yd represents -CH2-O-CH2-or -CH2-NR1 ldCH2; :: *: ::: nd represents 1,2, 3 or4; md represents 0 or 1; R4d represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5d represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CE3; -0-phenyl or.-C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6d represents a hydrogen atom; F; CI; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2- CH2-CH3; -CE3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(0)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7d represents a hydrogen atom; F; Cl; Br or -NO2; and R'w represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>Even more particularly preferred is the use of at least one substituted benzimidazole sulfonamide compound selected from the group consisting of is. .* . 34 * a * * a S a. S a [1] 5-Benzoyl-N-ethyl-1 Hbenzimidazole-2-SUlfOflamide [2] N-Methyl-I Hbenzimidazole-2SUlfOflam1de [3] N-(2-Pyridyl)-I Hbenzimidazole-2-SUlfOflamide [4] N-2-[(4-MorpholinoethYl)]-I Hbenzimidazole-2-SUlfOflamide [5] N-(4-Aminobutyl)-I Hbenzimidazole-2-SUlfOflamide [6] N-[3-(4-MorpholiflOPrOPYl)1-I Hbenzimidazole-2-SUlfOflamide [7] 5-Chloro-N-ethyl-I HbenzimidazoIe-2-SUlfOflam1de [8] 5-Phenoxy-N-ethyl-I Hbenzimidazole-2-SUlfOflamide [9] N[2(3,4-DimethoxyPheflYlethYl)1-l HbenzimidazoIe-2-SUIfOflam1de [101 N, N-Diethyl-I Hbenzimidazole-2-SUlfOflamide [11] N-Butyl-I Hbenzimidazole-2SUlfOflamide [12] NEthyl4,7dichlOrO5,6-dimethyI-1 HbenzimidaZOle-2-SUlfOflamide [13] N(4-Chloropheflyl)-I Hbenzimidazole-2-SUlfOflamide [141 5ChloroN(4-chlorOpheflyI)-I HbenzimidaZOle-2-SUlfOflamide [15] 5Chloro-N-(4-diethYlamiflO-I -methylbutyl)-I Hbenzimidazole-2- SUlfOflamide [17] 4-Chloro-5,6-dimethyl-N-ethyl-I Hbenzimidazole-2-SUlfOflam1de [18] 4-Nitro-1 Hbenzimidazole-2-SUlfOflamide [19] N-Ethyl-4-nitro-I HbenzimidazOle-2-SUlfOflam1de [20] N-(4-D,ethylamino-l -methylbutyl)-I Hbenzimidazole-2-SUlfOflamide [21] N-Cyanomethyl-I HbenzimidazoIe-2-SUlfOflamide [22] N-Cyclohexyl-1 Hbenzimidazole-2-SUlfOflamide [23] N-(1 -Naphthyl)-1 Hbenzimidazote-2-SUlfOflam1de [24] N-Ethyl-5-trifl uoromethyl-I H-benzimidazole-2-SU Ifonamide [25] N-(1 -Adamantyl)-1 Hbenzimidazole-2-SUlfOnamide [26] 2(SulfonyI-2-hYdrOXYmethYl-1 -piperidinyl)-I H-benzimidazole [27] N(4MethoxybenZyl)-I Hbenzimidazoe-2-SUlfOflamide [28] N(5Methyl-3-iSOXaZOlyl)-I HbenzimidazoIe-2-SUlfOflam1de [29] N-(2-Pyridylmethyl)-I Hbenzimidazole-2-SUlfOflamide [301 N-[2-(2-Pyridylethyl)]-l Hbenzimidazole-2-SUlfOflamIde [311 5Benzoyl-N-(4-diethYlamiflO-1 -methylbutyl)-1 Hbenzimidazole-2-SUlfOflam1de [32] 5-Nitro-I Hbenzimidazole-2-SUtfOflamide [33] N-Ethyl-5-nitro-I Hbenzimidazole-2-SUlfOflamide [341 N[2(4MorpholinOethYl)]-5-flitrOI Hbenzimidazole-2-SUlfOflam1de [35] N, N-Diethyl-5-flitrO-1 HbenzimidazoIe-2-SUlfOflam1de :s: .. 35. $ .</p>
<p>I SI</p>
<p>[36] N-[3-(4-Morpholinopropyl)]-5-flitrO-1 H-benzimidazole-2-su Ifonamide [37] N-Butyl-4-nitro-1 H-benzimidazole-2-sulfOflamide [38] N-(2-Hydroxy-1 -ethyl)-4-nitro-1 H-benzimidazole-2-sulfOflamide [39] N-Carboxyethylmethyl-4-flitrO-1 H-benzimidazole-2-sulfoflamide [40] N-Ethyl-N,4-dinitro-1 H-benzimidazole-2-sulfoflamide [411 N-[2-(4-Morpholinoethyl)]-4-flitrO-1 H-benzimidazole-2-sulfonamide [42] N-Acetyl-N-ethyl-4-nitro-1 H-benzimidazole-2-sulfOflamide [43] N-Acetyl-4-nitro-1 H-benzimidazole-2-sulfonamide [44] 2-[S u lfonyl-4-(2-hyd roxy-I -ethyl)piperazinyl]-4-n itro-1 H-benzimid azole [45] N-(4-Fluorophenyl)-4-n itro-1 H-benzimidazole-2-sulfoflamide [46] 2[Sulfonyl-2-(carboxymethyl)PYrrOlidiflYl]-4-flitrO-I H-benzimidazole [47] N-Methyl-4-nitro-I H-benzimidazole-2-sulfonamide [48] N-Propyl-4-nitro-I H-benzimidazole-2-sulfOflamide [49] N-lsopropyl-4-nitro-I H-benzimidazole-2-sulfonamide [50] N-Ethylthioethyl-4-nitro-1 H-benzimidazole-2-sulfonamide [51] N-Ethylsulfonylethyl-4-flitrO-1 H-benzimidazole-2-sulfOflamide [52] N-[3-(2-Oxo-hexamethylefleimiflYl)]-4-flitrO-l H-benzimidazole-2-sUlfOflamide [53] N-El -[1, 3-Bis(carboxyethyl)propyl]]-4-flitrO-1 H-benzimidazole-2-sulfonamide [54] 2-[Sulfonyl-4-methylpiperaziflylj-l H-benzimidazole [55] 5-Chloro-N-cyclohexyl-l H-benzimidazole-2-sulfonamide [56] N-(2-Diethylamino-I -ethyl)-l H-benzimidazole-2-sulfoflamide [57] N-Ethyl-I H-imidazo[4,5-b]pyridine-2-sulfonamide [58] N-Butyl-1 H-imidazo[4,5-b]pyridine-2-SUlfOflamide [59] N-Butyl-l H-imidazo[4,5-c]pyridifle-2-SUlfOflamide [60] 1, N-Diethyl-l H-benzimidazole-2-sulfOflamide [61] 1, N, N-Triethyl-l H-benzimidazole-2-sulfOflamide [62] 1, N-Dimethyl-N-ethyl-I H-benzimidazole-2-sulfOflamide [63] 1 -Benzoylmethyl-N-ethyl-1 H-benzimidazole-2-sulfOflamide [64] I-Acetylmethyl-N-ethyl-I H-benzimidazole-2-SUlfOflamide [65] N-Ethyl-I -(2-pyridylcarbonylmethYl)1 H-benzimidazole-2-sulfoflamide [66] 5-Ch loro-N-(4-diethylamiflO-1 -methylbutyl)-I -ethyl-I H-benzimidazole-2-sulfonamide [67] 6Chloro-N-(4-diethylamiflO-I -methylbutyl)-1 -ethyl-I H-benzimidazole-2-sulfonamide * * 36 * I * * * * I I</p>
<p>I I I</p>
<p>dl -* [68] 1, N-Diethyl-4-nitro-1 H-benzimidazol-2-sulfoflamide [69] 1,N, N-Triethyl-6-nitro-1 H-benzimidazole-2-sulfonamide [70] 1, N, N-Triethyl-5-nitro-1 H-benzimidazole-2-sulfoflamide [71] 5-Chloro-1, N-diethyl-N-(4-diethylamiflO-1 -methylbutyl)-1 H-benzimidazole-2-sulfonamide [72] 6-Chloro-1, N-diethyl-N-(4-diethylamino-1 -methylbutyl)-1 H-benzimidaZole-2-sulfonamide [73] 1, N, N-Triethyl-4-nitro-1 H-benzimidazole-2-sulfonamide [74] 1, N, N-Triethyl-7-nitro-1 H-benzimidazole-2-sulfonamide [75] 1, N-Diethyl-5, N-dinitro-1 H-benzimidazole-2-sulfoflamide [76] 1, N-Diethyl-6, N-dinitro-1 H-benzimidazole-2-sulfOflamide [77] 1, N-Diethyl-5-nitro-I H-benzimidazole-2-SulfOflamide [78] 1, N-Diethyl-6-nitro-I H-benzimidazole-2-sulfOflamide [79] 5-Amino-I H-benzimidazole-2-sulfonamide [80] 4-Amino-I H-benzimidazole-2-sulfoflamide [81] 4-Amino-N-(carboxyethylfllethyl)-1 H-benzimidazole-2-sulfOnamide [82] 4-Amino-N-ethyl-I H-benzimidazole-2-sulfOnamide [83] 4-Acetylamino-N-ethyl-I H-benzimidazole-2-sUlfOflamide [84] 3,4-Dihydro-2H-2-ethyl-[I,2,5]-thiadiazino[5,6-a]-beflZimidaZOle-I, I-dioxide [85] 3,4-Dihydro-2H-[1,2, 5]-thiadiazino[5,6-a]beflZimidaZOle-1,I-dioxide [86] 3,4-Dihydro-2H-2-methyl-[1,2,5]-thiadiazino[5,6-a]-benzimidazole-I, I-dioxide [87] 3,4,5-Trihydro-2H-2-methyl-[I,2,6]-thiadiazepino[6,7-a]-benzimidazole-1, I -dioxide [88] 3,4,5-Trihydro-2H-2-ethyl-[I,2,6]-thiadiazepino[6,7-aJ-benZimidaZole-I, I -dioxide [89] 3,4,5,6-Tetrahydro-2H-2-ethyl-EI,2,7]-thiadiazino-[7,8-a]benzimidazole-I, 1-dioxide [90] 3,4Dihydro2H[3(4-mOrpholiflOP1OPyl)]-EI,2,5]-thiadiazino(5 6-a]benzimidazole-I,1-dioxide [91] 3,4,5-Trihydro-2H-[2-(4-morpholinoethYl)]-[I,2,6]-thiadiazepino[6,7-a] benzimidazole-I,I-dioxide [92] 3,4-Dihydro-2H-2-ethyl-8-phenOXY-[I,2,5]-thiadiazino-[5,6-a] benzimidazole-1,1-dioxide [93] 3,4-Dihydro-2H-2-ethyl-7-phefloXY-[I,2,5]-thiadiazino-[5,6-a] beflZimidaZOle-* .S S $11 :: ) ;: ;: 1,1-dioxide [94] 8-Chloro-3,4-dihydro-2H-2-ethyl-7-phenoxy-[1,2, 5]thiad iazino-5,6-a]benzimidazole-1,1-dioxide [95] 7-Chloro-3,4-dihydro-2H-2-ethyl-7-phenOxy-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [96] 3,4,5-Trihydro-2H-[1,2,6]-thiadiazepino[6,7-a]benzimidazole-1,1-dioxide [97] 3,4-Dihydro-2 H-2-[2-(3,4-dimethoxyphenylethyl)]-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [98] 2 H-2-Butyl-3,4-Dihyd ro-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1,1-dioxide [99] 6,9-Dichloro-3,4-dihydro-7,8-dimethyl-2H-2-ethyl-[1,2,5]-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [100] 8-Chloro-3,4-dihydro-2H-2-(4-diethylamiflO-1 -methylbutyl)-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [101] 7-Chloro-3,4-dihydro-2H-2-(4-diethylamiflO-1 -methylbutyl)-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [102] 2H-2-(4-Chlorophenyl)-3,4-dihydro-[1,2,5]-thiadiazino-[5,6-a] benzimidazole- 1,1-dioxide [103] 3,4-Dihydro-2H-2-(5-methyl-3-isoxazoIyI)-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [104] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-1, 1-dioxide [105] 3,4-Dihydro-2H-2-ethyl-9-nitro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [106] 3,4-Dihydro-2 H-2-ethyl-6-n itro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [107] 3-Hydro-2H-2-methyl-6-nitro-[1,2,4]-thiadiazolo[4,5-a]-benzimidazole-1, 1-dioxide [108] 2H-2-Cyclohexyl-3,4-dihydro-[1,2,5]-thiadiazino[5,6-a]-benzimidazole-1,1 -dioxide [109] 3,4-Dihydro-2H-2-( I -naphthyl)-[1,2, 5]-thiadiazino-[5,6-ajbenzimidazole-1,1 -dioxide [110] 3,4-Dihydro-2 H-2-ethyl-7-trifluoromethyl-[1,2,5]-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [111] 3,4-Dihydro-2H-2-ethyl-8-trifluoromethyl-[1,2,5]-th iadiazino[5,6-* . S S * I S S S S S S S S S S. I S. S * I S S S S S * I S I 555 55I I albenzimidaZOle-1, I -dioxide [1121 2H-2-(1 AdamantyI)-3,4-dihYdr01l,2,5]thiadiazinO15,6a]beflZ1m1daz0l, 1-dioxide [113] 7-Benzoyl-3,4dihydro-2H-2-ethYI-11,2, 51-thiadiaziflO-[5,6-albenzimidaZOle-1, 1-dioxide 1114] 8BenzoyI3,4dihYdrO-2H2"ethY[l,2,5]-thiadiazino-[5,6-a]benzimidaZOle-l, 1-dioxide [1151 3,4Dihydro2H-2-(4-methOXYbeflZYf' ,2, 5]thiadiazino[5,6a]beflZimidaZ0 1,1-dioxide [116] 3,4-Dihyd ro2H-2-(2-pyridYlmethYI)1l,2 1,1-dioxide [117] 3,4Dihydro2H-2-[2-(2-PYfldYIethYI)1[l,2, 5]-thiadiazino[5,6-a]benzimidaZOle- 1,1-dioxide [118] 8ChIoro3,4dihydrO-2H2CYC10FYI1l,2,5]thiadiazino15,6a]beflZimidaZ0 1,1-dioxide [1191 7-Chloro-3,4dihydro-2H-2-CYCIOheXYI1l,2, 5]-th iadiazino[5,6-a]benzimidaZOe- 1,1-dioxide [120] 2-(2-DiethylamiflO-1 ethyI)-3,4-dihydro-2H-[1,2, 5]-thiadiaZiflO[5,6-a]benzimidaZole-1,1-dioxide [121] 8-Chloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-aJ-benzimidaZOle-1, 1-dioxide [122] 7-Chloro-3,4-dihyd ro-2H-[1,2,5]thiadiazino[5,6-a]-beflZimidaz0i,1-dioxide [123] 7,8DichIoro3,4-dihYdrO-2H[1,2,5]thiadiazino[5,6a1-beflZimidaZ0te, 1-dioxide 1124] ,2,5]-thiadiazino[5,6-a]benzimidaZOle-1,1-dioxide [125] 3,4DihydrO-2H-2-ethYI7flitr0f' ,2,5]-thiadiaZiflO-[5,6-a]benzimidaZole-1, 1-dioxide [1261 3,4DihydrO-2H-2-ethYI-8-flitr0[l,2,5]thiadiazino[5,6-a1beflZimidaZ0Ie, 1-dioxide [127] 3,4DihydrO2H-2-methYI-7-flitr0[l,2,5]thiadiazinO[5,6-a]beflZimidaZ0I, 1-dioxide [1281 3,4Dihydro2H-2-methYl-8-fl1tr0[I,2,5]-thiadiazino-[5,6-albenzimidaZole-1, 1-dioxide [129] 3,4,5TrihydrO-2H-2-ethYI-8-flitr0[l,2,6]thiadiazePiflO[6,7a]beflZimidaz0 * I * I S S I S * ** S 0 0 0 * I. S S * 00 * *.* * :.. . 1,1-dioxide [130] 3,4,5Trihydro-2H-2-ethYI-9-flitr0-[1,2,6]thiadiazepino[6,7a] beflZimidaZ0Ie 1,1-dioxide [1311 2H-2-Butyl-3,4-dihydro-7-nitrO-[1,2,5]-thiad iazino-[5,6-a]benzimidaZOle-1, 1-dioxide [132] 2H-2-Butyl-3,4-d ihydro-8-nitro-[1,2,5]thiadiazino[5,6-a]beflZimidaZ0tel, 1-dioxide [133] 3,4Dihydro2H8nitrO-2-[2-(2-PYr1dYIethYI)F[l,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [134] 3,4-Dihyd ro2H7nitro-2-[2-(2-PYridYIethYI)H 1,2,5]-thiadiaziflo[5,6-a]benzimidazole-1,1-dioxide [135] 3,4-Dihyd ro-2H-8-nitro-(2-pyridYlmethYl)[l,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [136] 3,4-Dihydro-2 H-7-nitro-(2-pyridylmethYl)-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [137] 3,4,5,6TetrahydrO-2H-2-ethYI-9-fl1tr01l,2,7]-thiadiazozinO[7,8-a] benzimidazole-1,1-dioxide [138] 3,4,5,6-Tetrahydro-2H-2-ethYl-1 0-nitro-[1,2,7]-thiadiazozino[7,8-a]benzimidazOle-1,1-dioxide [139] ,2,5]-thiadiazino[5,6-a]benzimidazOle-1,1-dioxide 1140] 3,2, 5]-thiadiazino[5,6-a]benzimidaZOle-1,1-dioxide [1411 2H-2-(4-DiethylamiflO-1 methyIbutyI)-3,4-dihydrO-7-flitr01l,2,5]-thiadiazino[5,6-a] benzimidazOle-1,1-dioxide [142] 2H-2-(4-Diethylamiflo-1 methyIbutyI)-3,4-dihydrO-8-flitr0[l,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [143] 3,4-Dihydro-2H-7-flitrO-[1,2,5]-thiadiazino[5,6-a]-benzimidazOle-1, 1-dioxide [144] 3,4-Dihydro-2H-8-flitrO-[1,2, 5]thiadiazino[5,6-a1-beflZimidaZ0Iel,1-dioxide [145] 2H-2-( 1 AdamantyI)-3,4-dihydrO-7-flitr01l,2,5J-thiadiazino[5,6-a]berizimidazole-1, 1-dioxide [146] 2H-2-(1 AdamantyI)-3,4-dihYdrO-8-fl1tr01l,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [147] 7-Amino-3,4-dihydro-2H-2-ethYl-[1,2,5]-thiadiazino-[5,6-a]benzimidaZOle-1, 1- ** *. . a.: ;. 40: * S as, I..</p>
<p>dioxide [1481 3,4-Dihyd ro-2H-2-ethyl-7-isothiocyanatO-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [149] 7-Acetylamino-3,4-dihydro-2H-2-ethyl-[1,2, 5]-thiad iazino[5,6-a]benzimidazote- 1,1-dioxide [150] 2-Carboxyethylmethyl-8-chIorO-3,4-dihydro-2H-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [151] 2-Carboxyethylmethyl-7-chloro-3,4-dihyd ro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [152] 8-Chloro-2-(6-chloro-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [153] 7-Chloro-2-(6-ch Ioro-1 -hexyl)-3,4-dihydro-2H-[ 1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [154] 8-Chloro-2-(2-chloro-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazote-1,1dioxide [155] 7-Ch Ioro-2-(2-chloro-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [156] 2-(3-Chloro-1 -propyl)-3,4-dihydro-2H-7-nitro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [157] 8-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [158] 7-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [159] 2-{3-(N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]]-prOpylamiflO}-3,4-dihyd ro- 2H-7-nitro-[1,2,5]-thiadiazino-[5,6-a]benzimidaZOle-1,1-dioxide [160] 8-Chloro-2-(6-diethytamino-1 -hexyl)-3,4-dihyd ro-2H-[1,2,5]-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [161] 7-Chloro-2-(6-diethylamiflO-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [162] 8-Chloro-2-cyanomethyl-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [163] 7-Chloro-2-cyanomethyl-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [164] 8-Chloro-2-(2-d iethylamino-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6- !: : :: 41 : albenzimidazole-1,1-dioxide [165] 7-Chloro-2-(2-diethylamiflO-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [1661 7-Chloro-2-(6-ethylamino-1 -hexyl)-3,4-dihyd ro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [167] 7-Chloro-2-(2-pyridyl)-3,4-dihYdrO-2H-[1,2,5]-thiadiazino[5,6-a Jbenzimidazole-I,1-dioxide [168] 3,4-Dihydro-2H-2-ethyl-3-methYl-[1,2,5]-thiadiazino[5,6-albenzimidazole-1, 1-dioxide [169] 3,4-Dihyd ro-2H-2-ethyl-3-methyl-7-flitrO-[1,2, 5]-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [170] 3,4-Dihyd ro-2H-2-ethyl-3-methyl-8-flitro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [1711 2H-2-Butyl-3,4-d ihydropyrido[3',2':4,5]imidaZo[1,2-e]-[1,2, 5]-thiadiazine-1, 1-dioxide [172] 2-Butyl-3,4-dihydro-2H-pyrido[3' ,4':4,5]imidazo[1,2-e]-[1,2,5]-thiadiazine-1, 1-dioxide [173] 1,2,3,4,13, 1 4-Hexahydropyrido[1,2':2,3]-[1,2,5]-thiadiazino[5,6-a]benzimidazole-6, 6-dioxide [174] 1,2,3,4,13,1 4-Hexahydro-9-nitropyridO[1,2':2,3]-[1,2,5]-thiadiazino[5,6-a] benzimidazole-6,6-diOXide [175] 1,2,3,4,13,1 4-Hexahydro-1 O-nitropyrido[1,2':2,3]-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-6, 6-diOXide [176] 2H-2-Ethyl-[1,2, 5]-thiadiazino[5,6-a]beflZimidaZOle-1,1-dioxide [177] 2H-2-Ethyl-3-methyl-[1,2,5]-thiadiazino[5,6-a]-beflZimidaZOle-1,1-dioxide [178] 2H-2-Ethyl-3-phenyl-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1,1-dioxide [1791 2H-2-Ethyl-7-nitro-3-(4-flitroPheflYl)-[1,2, 5]-thiadiazino-[5,6-a]benzimidaZOle- 1,1-dioxide; [180] N-ethyl-I -((2-oxo-2,3-dihydrobenzo[d]imidaZOl-1 -yl)methyl)-1 H-benzo[d]imidazole-2-SUlfOflamide and [1811 1,2,3,4,13,1 4-Hexahydro-9, I 0-dinitropyrido[1,2':2,31-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-6, 6-diOxide optionally in form of one of its stereoisomers, preferably enantiomers or *. a'. .*. a. val * a a A') * * S. * S * T. * * * . : . 5 diasteromers, a racemate or in form of a mixture of at least two of its stereolsomers, preferably eriantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
<p>In another aspect the present invention relates to the use of at least one substituted benzimidazole sulfonamide compound of general formula I, Ia, lb, Ic or Id given above, in the following text referred to as compound of general formula I, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the manufacture of a medicament suitable for 5-HT6-receptor regulation, preferably for the prophylaxis and/or treatment of a disorder or a disease that is least partially mediated via 5-HT6-receptors.</p>
<p>In another aspect the present invention relates to the use of at least one substituted benzimidazole sulfonamide compound of general formula I given above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the manufacture of a medicament for the regulation of appetite; for the maintenance, increase or reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus); for the prophylaxis and/or treatment of stroke; seizures; migraine; head trauma; epilepsy; irritable colon syndrome; irritable bowel syndrome; disorders of the central nervous system; anxiety; panic attacks; depression; bipolar disorders; obsessive compulsory disorder; cognitive disorders; cognitive dysfunction associated with psychiatric diseases; memory disorders; memory loss; senile dementia; mood disorders; sleep disorders; psychosis; neurodegenerative disorders, preferably selected from the group consisting of Morbus Alzheimer, Morbus Parkinson, Morbus Huntington and Multiple Sclerosis; schizophrenia; chronic intermittent hypoxia; convulsions; or hyperactivity disorder (ADHD, attentiondeficit/hyperactivity disorder) or for the * S * * . -S * * a S * S I S. S a * 43. * a S P S S * SS S *** SoS S improvement of cognition (cognitive enhancement) and/or for the improvement of cognitive memory (cognitive memory enhancement).</p>
<p>More preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I as defined above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomerS, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the preparation of a medicament for the regulation of appetite; for the maintenance, increase or reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus).</p>
<p>Most preferred is the use of at least one substituted benzimidazole sulfonamide compound of general formula I as defined above, optionally in form of one of their stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two stereoisomers, preferably enantiomers and/or diastereomerS, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof, for the preparation of a medicament for the prophylaxis and/or treatment of obesity.</p>
<p>The inventively obtained medicament may be in any form suitable for the application to patients and can be produced by standard procedures known to those skilled in the art. The composition of the medicament may vary depending on the route of administration.</p>
<p>Such medicaments may be produced according to standard procedures known to those skilled in the art, e.g. from the tables of contents from,,Pharmaceutics: the Science of Dosage Forms", Second Edition, Aulton, M.E. (Ed.) Churchill Livingstone, Edinburgh (2002); ,,Encyclopedia of Pharmaceutical Technology", Second Edition, Swarbrick, J. and Boylan J.C. (Eds.), Marcel Dekker, Inc. New York (2002); ,,Modern Pharmaceutics", Fourth Edition, Banker G.S. and Rhodes C.T. (Eds.) Marcel Dekker, Inc. New York 2002 and,,The Theory and Practice of Industrial Pharmacy", Lachman L., Lieberman H. and Kanig J. (Eds.), Lea & Febiger, Philadelphia (1986). The a'. *. *.</p>
<p>:: :. :.</p>
<p>-</p>
<p>respective descriptions are incorporated by reference and form part of the present</p>
<p>disclosure.</p>
<p>The medicament obtained according to the present invention may, for example, be administered parentally in combination with conventional injectable liquid carriers, such as water or suitable alcohols. Conventional pharmaceutical excipients for injection, such as stabilizing agents, solubilizing agents, and buffers, may be included in such injectable compositions. These medicaments may for example be injected intramuscularly, intraperitoneally, or intravenously. The medicament obtained according to the present invention may also be administered topically, e.g. by means of a transdermal therapeutic system (US), or via a suppository.</p>
<p>In a preferred embodiment of the present invention, the medicament is suitable for oral administration.</p>
<p>Suitable oral administration forms include tablets, dragees, capsules, syrups, gels, juices (oil-or water-based), chewing gums, sprays, aqueous or oily suspensions, or dry powdered forms, preferably in a sachet, suitable for reconstitution with water or other suitable liquid medium before use.</p>
<p>Other suitable oral administration forms are multiparticulate formulations, preferably microtablets, microparticles, nanoparticles, pellets or granules, optionally compressed into a tablet, filled into a capsule or suspended in a suitable liquid.</p>
<p>Suitable liquids are known to those skilled in the art.</p>
<p>The inventively obtained medicament may also comprise at least one substituted benzimidazole sulfonamide compound of general formula I given above at least partially in sustained-release form. By incorporating one or more of the substituted benzimidazole sulfonamide compounds of general formula I given above at least partially or completely into a sustained-release form it is possible to extend the duration of their effect, allowing for the beneficial effects of such a sustained release form, e.g. the maintenance of optimal therapeutical plasma or tissue concentrations.</p>
<p>* . * S *I* * At * I * I I * I * * S. S * * I S S * I S S I -II S S.. S Suitable sustained-release forms as well as materials and methods for their preparation are known to those skilled in the art, e.g. from the tables of contents from Modified-Release Drug Delivery Technology", Rathbone, M.J. Hadgraft, J. and Roberts, M.S. (Eds.), Marcel Dekker, Inc., New York (2002); ,,Handbook of Pharmaceutical Controlled Release Technology", Wise, D.L. (Ed.), Marcel Dekker, Inc. New York, (2000);"Controlled Drug Delivery", Vol. I, Basic Concepts, Bruck, S.D.</p>
<p>(Ed.), CRC Press Inc., Boca Raton (1983) and from Takada, K. and Yoshikawa, H., Oral Drug delivery", Encyclopedia of Controlled Drug Delivery, Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 2, 728-742; Fix, J., ,,OraI drug delivery, small intestine and colon", Encylopedia of Controlled Drug Delivery, Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 2, 698-728. The respective descriptions are incorporated by reference and are part of the present</p>
<p>disclosure.</p>
<p>If the medicament obtained according to the present invention comprises at least one of the substituted benzimidazole sulfonamide compounds of general formula I at least partially in a sustained-release form, said sustained release may preferably be achieved by the application of at least one coating or provision of a matrix comprising at least one sustained-release material.</p>
<p>The sustained-release material is preferably based on an optionally modified, water-insoluble, natural, semisynthetic or synthetic polymer, or a natural, semisynthetic or synthetic wax or fat or fatty alcohol or fatty acid, or on a mixture of at least two of these afore mentioned components.</p>
<p>The water-insoluble polymers used to produce a sustained-release material are preferably based on an acrylic resin, which is preferably selected from the group of poly(meth)acrylateS, particularly preferably poly(Ci4alkyl (meth)acrylates, poly(C14dialkylamiflO(C14)alkyl (meth)acrylates and/or copolymers or mixtures thereof, and very particularly preferably copolymers of ethyl acrylate and methyl methacrylate with a monomer molar ratio of 2:1 (Eudragit NE3OD ), copolymers of ethyl acrylate, methyl methacrylate and trimethylammoniUm ethyl methacrylate-chloride with a monomer molar ratio of 1:2:0.1 (Eudragit RS ), copolymers of ethyl acrylate, methyl methacrylate and trimethylammonium ethyl methacrylate-chloride * * S S 4.5 :. 46: with a monomer molar ratio of 1:2:0.2 (Eudragit RL ), or a mixture of at least two of the above-mentioned copolymers. These coating materials are commercially available as 30 wt.% aqueous latex dispersions, i.e. as Eudragit RS3OD , Eudragit NE3OD or Eudragit RL3OD , and may also be used as such for coating purposes.</p>
<p>In another embodiment, the sustained-release material is based on water-insoluble cellulose derivatives, preferably alkyl celluloses, particularly preferably ethyl cellulose, or cellulose esters, e.g. cellulose acetate. Aqueous ethyl cellulose dispersions are commercially available, for example, under the trademarks Aquacoat or Surelease .</p>
<p>As natural, semisynthetic or synthetic waxes, fats or fatty alcohols, the sustained-release material may be based on carnauba wax, beeswax, glycerol monostearate, glycerol monobehenate, glycerol ditripalmitostearate, microcrystalline wax, cetyl alcohol, cetylstearyl alcohol or a mixture of at least two of these components.</p>
<p>The afore mentioned polymers of the sustained-release material may also comprise a conventional, physiologically acceptable plasticizer in amounts known to those skilled in the art.</p>
<p>Examples of suitable plasticizers are lipophilic diesters of a C6-C4o aliphatic or aromatic dicarboxylic acid and a C1-C8 aliphatic alcohol, e.g. dibutyl phthalate, diethyl phthalate, dibutyl sebacate or diethyl sebacate, hydrophilic or lipophilic citric acid esters, e.g. triethyl citrate, tributyl citrate, acetyltributyl citrate or acetyltriethyl citrate, polyethylene glycols, propylene glycol, glycerol esters, e.g. triacetin, Myvacet (acetylated mono-and diglycerides, C23H4405 to C25H4707), medium-chain triglycerides (Miglyol ), oleic acid or mixtures of at least two of said plasticizers.</p>
<p>Aqueous dispersions of Eudragit RS and optionally Eudragit RL preferably contain triethyl citrate. The sustained-release material may comprise one or more plasticisers in amounts of, for example, 5 to 50 wt. % based on the amount of polymer(s) used.</p>
<p>The sustained-release material may also contain other conventional auxiliary substances known to those skilled in the art, e.g. lubricants, coloured pigments or surfactants.</p>
<p>S. S..</p>
<p>:: ) :. :.</p>
<p>The medicament obtained according to the present invention may also have at least one enteric coating which dissolves as a function of pH. Because of this coating, the medicament can pass through the stomach undissolved and the compounds of general formula I are only released in the intestinal tract. The enteric coating preferably dissolves at a pH of between 5 and 7.5.</p>
<p>The enteric coating may be based on any enteric material known to those skilled in the art, e.g. on methacrylic acid/methyl methacrylate copolymers with a monomer molar ratio of 1:1 (Eudragit L ), methacrylic acid/methyl methacrylate copolymers with a monomer molar ratio of 1:2 (Eudragit S ), methacrylic acid/ethyl acrylate copolymers with a monomer molar ratio of 1:1 (Eudragit L3OD-55 ), methacrylic acid/methyl acrylate/methyl methacrylate copolymers with a monomer molar ratio of 7:3:1 (Eudragit FS ), shellac, hydroxypropyl methyl cellulose acetate-succiflateS, cellulose acetate-phthalates or a mixture of at least two of these components, which can optionally also be used in combination with the above-mentioned water-insoluble poly(meth)acrYlates, preferably in combination with Eudragit NE3OD and/or Eudragit RL and/or Eudragit RS .</p>
<p>The coatings of the medicament of the present invention may be applied by the conventional processes known to those skilled in the art, e.g. from Johnson, J.L., Pharmaceutical tablet coating", Coatings Technology Handbook (Second Edition), Satas, D. and Tracton, A.A. (Eds), Marcel Dekker, Inc. New York, (2001), 863-866; Carstensen, T., ,,Coating Tablets in Advanced Pharmaceutical Solids", Swarbrick, J. (Ed.), Marcel Dekker, Inc. New York (2001), 455-468; Leopold, C.S., ,,Coated dosage forms for colon-specific drug delivery", Pharmaceutical Science & Technology Today, 2(5), 197-204 (1999), Rhodes, C.T. and Porter, S.C., Coatings, in Encyclopedia of Controlled Drug Delivery. Mathiowitz, E. (Ed.), John Wiley & Sons, Inc., New York (1999), Vol. 1, 299-311. The respective descriptions are incorporated by reference</p>
<p>and are part of the disclosure.</p>
<p>In another embodiment, the medicament obtained according to the present invention may contain one or more of the substituted benzimidazole sulfonamide compounds of general formula I not only in sustained-release form, but also in non-retarded form. * * S S 555</p>
<p>* S * S S * : : : . 48 *. *5 * S S * S S I * * S.. 555 5 By combination with the immediately released form, a high initial dose can be achieved for the rapid onset of the beneficial effect. The slow release from the sustained release form then prevents the beneficial effect from diminishing.</p>
<p>Preferred is the administration of the benzimidazole sulfonamide compound at a dosage of 0.1 -50 mg/kg/day, more preferred 0.15-10 mg/kg/day, even more preferred 0.2-5 mg/kg/day Preferably the medicament is designed for once daily, twice daily, or three times daily administration. More preferably the medicament is designed for once daily or twice daily administration, most preferably for once daily administration.</p>
<p>The inventively used substituted benzimidazole sulfonamide compounds can be prepared as outlined in "BenzimidazolesulfonamideS and their application as drugs", Constansas, J. F., Corominas, J. P., Pinol, A. C., US 4933338 and "Benzimidazolesulfonamides and Imidazopyridinesulfonamides and their application as drugs", Constansas, J. F., Corominas, J. P., Pinol, A. C., US 4943570. The respective description is hereby incorporated by reference and forms part of the disclosure.</p>
<p>The inventively used substituted benzimidazole sulfonamide compounds may, for example, be obtained by the following process, according to which at least one compound of general formula II, R1 z4 o II, * , * * *.* : * * * * :* 49: ** S. S *** eu *</p>
<p>F</p>
<p>wherein Z", Z2, Z3, Z4 and R1 have the meaning given above, is reacted with at least one compound of general formula HNR2R3, wherein R2 and R3 have the meaning given above, in at least one reaction medium, preferably in a reaction medium selected from the group consisting of water, acetone, methanol, ethanol, isopropanol and n-butanol, in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of potassium carbonate, potassium hydroxide, sodium carbonate and sodium hydroxide, to yield a compound of general formula I, R1 N 0 R2 r II / z2 ------_ // N R3 wherein Z1, Z2, Z3, Z4, R1, R2 and R3 have the meaning given above, which is optionally isolated and/or optionally purified.</p>
<p>The inventively used substituted benzimidazole sulfonamide compounds of general formula lb may, for example, be obtained by the following process, according to which at least one compound of general formula Ia, R1 z4a 0 z3a _-\ II /</p>
<p>II I</p>
<p>Z2 L7 II \3 zla N 0 Ia, wherein za, z2a, z3a, z4a and R3 have the meaning given above and both and R2a represent hydrogen, is reacted with at least one compound of general formula Al _(CHR8b)A2, Al -(CH R8b)(CHR9b)A2, Al (CHR8b)(CH RBb)A2, Al (CHR8b) (CH R8b)(CH R8b)A2, Al (CHR8b)(CH R8b)(CH RBb)(CHR8b)A2 and/or Al -CR8b=CR9bA2, wherein R81' and R9b have the meaning given above and Al and A2, independently of one another, each represent a leaving group, preferably a leaving group selected from the group consisting of chlorine, bromine and iodine, S 5. *..</p>
<p>* S a. * * S S : : : 50. * a a. * * , , S SS* *5. S in at least one reaction medium, preferably in a reaction medium selected from the group consisting of dimethylsulfoxide, ethanol, methanol, isopropanol, n-butanol, acetone, acetonitrile, ether, tetrahydrofurane and dioxane, in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, pyridine, triethylamine and diisopropylethylamine, to yield a compound of general formula Ib, R3b Xb V 4b / 3b -N I Z \-S Z2b 1b N Ib, wherein Z, Z2b, Z3b, Z4b, Xb and R3b have the meaning given above, which is optionally isolated and/or optionally Pu rifled.</p>
<p>The inventively used substituted benzimidazole sulfonamide compounds of general formula Id may, for example, be obtained by the following process, according to which at least one compound of general formula Ic, R1' R'Oc z3c \ II z2c SN /Ymc Z1c N 0 ( 2)nc Ic, wherein Z1, Z2c, Z3c, Z4, n, C and m have the meaning given above, R represents hydrogen and Roc represents -CH2-OH; is reacted with at least one dehydrating compound, preferably at least one dehydrating compound selected from the group consisting of polyphosphoric acid and thionyl chloride, preferably in a reaction medium selected from the group consisting of dimethylsulfoxide, ethanol, * e a*. **. * I..</p>
<p>* a a. a a. * * * . .</p>
<p>S S S</p>
<p>S S S S</p>
<p>S., 55. 5 methanol, isopropanol, n-butanol, acetone, acetonitrile, ether, tetrahydrofurane and dioxane, in the presence of at least one base, preferably in the presence of at least one base selected from the group consisting of potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, pyridine, triethylamine and diisopropylethylamifle, to yield a compound of general formula Id, yd __7' \md Z4d1 / \ ,.(CH)</p>
<p>-N N</p>
<p>Z1d N o Id, wherein Zd, Z2d, Z3d, Z4d, d m" and yd have the meaning given above, which is optionally isolated and/or optionally purified.</p>
<p>During the processes described above the protection of sensitive groups or of reagents may be necessary and/or desirable. The introduction of conventional protective groups as well as their removal may be performed by methods well-known to those skilled in the art.</p>
<p>If the substituted benzimidazole sulfonamide compounds of general formula I themselves are obtained in form of a mixture of stereoisomers, particularly enantiomers or diastereomers, said mixtures may be separated by standard procedures known to those skilled in the art, e.g. chromatographic methods or fractionalised crystallisation with chiral reagents.</p>
<p>Salts of the inventively used benzimidazole sulfonamide compounds of general formula I and stereoisomerS thereof, may be obtained by a process, wherein at least one compound of general formula I having at least one basic group is reacted with at least one inorganic and/or organic acid, preferably in the presence of a suitable reaction medium. Suitable reaction media include, for example, any of the ones given above. Suitable inorganic acids include hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, suitable organic acids are e. g. citric acid, ** . . . : 52 *. .* ** * *. :,.</p>
<p>maleic acid, fumaric acid, tartaric acid, or derivatives thereof, p-toluenesulfonic acid, methanesu Ifonic acid or camphersulfonic acid.</p>
<p>Salts of the inventively used substituted benzimidazole sulfonamide compounds of general formula I or stereoisomers thereof may also be prepared by a method, wherein at least one compound of general formula I having at least one acidic group is reacted with one or more suitable bases, preferably in the presence of a suitable reaction medium. Suitable bases are e. g. hydroxides, carbonates or alkoxides, which include suitable cations, derived e. g. from alkaline metals, alkaline earth metals or organic cations, e. g. [NHR4..], wherein n is 0, 1, 2, 3 or 4 and R represents a branched or unbranched C1-alkyl-radical. Suitable reaction media are, for example, any of the ones given above.</p>
<p>The term "solvate" according to this invention is to be understood as meaning any form of the substituted benzimidazole sulfonamide compounds of general formula I in which they have attached to it via non-covalent binding another molecule (most likely a polar solvent) especially including hydrates and alcoholats, e.g. methanolat.</p>
<p>Solvates, preferably hydrates, of the inventively used substituted benzimidazole sulfonamide compounds of general formula I, of corresponding stereoisomers, or of corresponding salts thereof may also be obtained by standard procedures known to those skilled in the art.</p>
<p>Those skilled in the art understand that the term substituted benzimidazole sulfonamide compounds as used herein is to be understood as encompassing derivatives such as ethers, esters and complexes of these compounds as well. The term "derivatives" as used in this application is defined here as meaning a chemical compound having undergone a chemical derivation starting from an acting (active) compound to change (ameliorate for pharmaceutical use) any of its physicochemical properties, especially a so-called prodrug, e. g. their esters and ethers. Examples of well known methods of producing a prodrug of a given acting compound are known to those skilled in the art and can be found e. g. in Krogsgaard-Larsen et al., Textbook of Drugdesign and Discovery, Taylor & Francis (April 2002). The respective description is hereby incorporated by reference and forms part of the disclosure.</p>
<p>0 0 *0s * * I * I a : : : 53 I. ** * I I I S 1 0* 0*5</p>
<p>-</p>
<p>The purification and isolation of the inventively used substituted benzimidazole sulfonamide compounds of general formula (I), of a corresponding stereoisomer, or salt, or solvate or any intermediate thereof may, if required, be carried out by conventional methods known to those skilled in the art, e. g. chromatographic methods or recrystallization.</p>
<p>* * * d * I I J * *ru * * * I I * * a * I... * a a a a. j * * * I.. a Pharmacological Methods: I) BINDING TO SEROTONIN RECEPTOR 5-HT6 Cell membranes of HEK-293 cells expressing the 5HT6-human recombinant receptor were supplied by Receptor Biology. In said membranes the receptor concentration is 2.18 pmol/mg protein and the protein concentration is 9.17 mg/mI. The experimental protocol follows the method of B. L. Roth et al. [B. L. Roth, S. C. Craigo, M. S. Choudhary, A. Uluer, F. J. Monsma, Y. Shen, H. Y. Meltzer, D. R. Sibley: Binding of Typical and Atypical Antipsychotic Agents to 5-Hydroxytryptamine-6 and Hydroxytryptamine-7 Receptors. The Journal of Pharmacology and Experimental Therapeutics, 1994, 268, 14031 with the following slight changes. The respective part of the literature description is hereby incorporated by reference and forms part of the</p>
<p>disclosure.</p>
<p>The commercial membrane is diluted (1:40 dilution) with the binding buffer: 50 mM Tris-HCI, 10mM MgCl2,0.5 mM EDTA (pH 7.4). The radioligand used is [3H]-LSD at a concentration of 2.7 nM with a final volume of 200 p1. Incubation is initiated by adding 100 p1 of membrane suspension, ( 22.9 pg membrane protein), and is prolonged for 60 minutes at a temperature of 37 C. The incubation is ended by fast filtration in a Brandel Cell Harvester through fiber glass filters made by Schleicher & Schuell GF 3362 pretreated with a solution of polyethylenimine at 0.5 %. The filters are washed three times with three milliliters of buffer Tris-HCI 50 mM pH 7.4. The filters are transferred to flasks and 5 ml of Ecoscint H liquid scintillation cocktail are added to each flask. The flasks are allowed to reach equilibrium for several hours before counting with a Wallac Winspectral 1414 scintillation counter. Non-specific binding is determined in the presence of 100 pM of serotonin. Tests were made in triplicate. The inhibition constants (K1, nM) were calculated by non-linear regression analysis using the program EBDA/LIGAND described in Munson and Rodbard, Analytical Biochemistry, 1980, 107, 220, the respective part of which is hereby incorporated by reference and forms part of the disclosure.</p>
<p>* * * * rn : : : * 5 * S * * S I ** :_. *_ II.) FOOD INTAKE MEASUREMENT (BEHAVIOURAL MODEL): Male W rats (200-270 g) obtained from Harlan, S.A. are used. The animals are acclimatized to the animal facility for at least 5 days before they are subjected to any treatment. During this period the animals are housed (in groups of five) in translucid cages and provided with food and water ad libitum. At least 24 hours before the treatment starts, the animals are adapted to single-housing conditions.</p>
<p>The acute effect of the substituted benzimidazole sulfonamide compounds according to the present invention in fasted rats is then determined as follows: The rats were fasted for 23 hours in their single homecages. After this period, the rats are orally or intraperitoneally dosed with a composition comprising a substituted benzimidazole sulfonamide compound or a corresponding composition (vehicle) without said substituted benzimidazole sulfonamide compound. Immediately afterwards, the rat is left with preweighed food and cumulative food intake is measured after 1, 2, 4 and 6 hours.</p>
<p>Said method of measuring food intake is also described in the literature publications of Kask et al., European Journal of Pharmacology 414 (2001), 215-224 and Turnbull et al., Diabetes, Vol. 51, August 2002. The respective parts of the descriptions are hereby incorporated by reference and form part of the disclosure.</p>
<p>The present invention is illustrated below with the aid of examples. These illustrations are given solely by way of example and do not limit the general spirit of the present invention.</p>
<p>:: :: *. :: S * S *S S * *** :_. 4_s</p>
<p>Examples</p>
<p>Example 1: 5-Benzoyl-N-ethyl-1 Hbenzimidazole-2-SUlfOflamide Chlorine is bubbled for one hour into a suspension of 50.9 g (0.2 mol) of 2-mercapto- 5-benzoyl-1 H-benzimidazole in 1200 ml of 20% aqueous acetic acid in such a way that the temperature does not exceed 7 C. The acid chloride obtained is filtered off, washed with cold water and immediately added in small portions to 200 ml of 17% aqueous ethylamine cooled to 5 C beforehand. The mixture is stirred until it reaches room temperature, and stirring is then continued for 1 hour. The solution is adjusted to pH 5 with hydrochloric acid and the product is filtered off and washed with water.</p>
<p>Recrystallization from ethyl acetate gives 51.3 g (78%) of 5-benzoyl-N-ethyl-1 H-benzimidazole-2-SulfOflamide melting at 250-253 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 6 1,09 (t,3H); 3,14 (quint.,2H); 7,70(m,7H); 8,04 (s,1 H); 8,41 (t,1 H); 13,86 (b,1 H) Example 60: 1,N-Diethyl-1 HbenzimidazoIe-2-SUlfOflamide 46.8 g (0.3 mol) of ethyl iodide are added to a suspension of 67.5 g (0.3 mol) of N-ethyl-I Hbenzimidazole-2-SulfOflaflhide and 47.7 g (0.45 mol) of sodium carbonate in 450 ml of acetone and 20 ml of water. The mixture is left under reflux for 20 hours, the acetone is evaporated off, 200 ml of water are added and the product is extracted with methylene chloride. The organic layer is dried and evaporated. The residue is recrystallized from an ethanol/water mixture (2:1) to give 56.8 g (75%) of 1,N-diethyl-1Hbenzimidazole-2-SUlfOnaflhide melting at 135-139 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 6 1,14 (t,3H); 1,40 (t,3H); 3,23 (q,2H); 4,58 (q,2H); 7,37 (m,2H); 7,76 (m,2H); 8,61 (s,IH) Example 69: 1,N,N-Triethyl-6-flitrO-1 HbenzimidazOle-2-SUlfOflamide 2.6 g (0.11 mol) of sodium hydride are added to a solution of 29.8 g (0.1 mol) of 6-nitro-1,N-diethyl-1 Hbenzimidazole-2-5UIfOflamide in 100 ml of dimethylformamide.</p>
<p>The solution is stirred for one hour at4O C, 10.8 g (0.1 mol) of ethyl bromide are added and the mixture is stirred for 12 hours at 50 C. It is poured into water and the * * * * S S S *** * * * S 57 * I. I S * I a * * * S * S IS * ** :._ *_* product is filtered off and washed with water. The precipitate is recrystallized from ethanol to give 25.6 g (78%) of 6-nitro-1,N,N-triethyl-1 H-benzimidazole-2-sulfonamide melting at 90- 91 C.</p>
<p>1,22 (t,6H); 1,44 (t,3H); 3,50 (q,4H); 4,69 (q,2H); 7,92 (d,IH); 8,14 (d,IH); 8,74 (s,IH) Example 84: 3,4-Dihydro-2H-2-ethyl-[1,2,5]thiadiazino(5,6-aJ-benzimidaZOIe-1,1 -dioxide 4 g of tetrabutylammonium bisulfate, 45 g (0.24 mol) of I,2-dibromoethane and 138 g (I mol) of finely powdered potassium carbonate are added to a solution of 45 g (0.2 mol) of N-ethyl-I H-benzimidazole-2-sulfonamide in 400 ml of dimethylsulfoxide. The mixture is stirred for 12 hours at room temperature and poured into a water/ice mixture. The precipitate obtained is filtered off and washed with water to give 44.5 g (88%) of 3,4-dihydro-2H-2-ethyl-[I,2, 5]-thiadiazino[5,6-a]benzimidazole-1,I-dioxide melting at 176-1 78 CC.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 6 1,30 (t,3H); 3,36 (q,2H); 4,20 (t,2H); 4,45 (t,2H); 7,34-7,90 (m,4H) Example 101: 7-Ch Ioro-3,4-dihyd ro-2H-2-(4-diethylamino-1 -methylbutyl)-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1 -dioxide A solution of 1.5 g (0.022 mol) of sodium nitrite in 5 ml of water is added dropwise to a solution of 7.58 g (0.02 mol) of 7amino3,4dihydro-2H-2-(4-diethylamiflO-1-methylbutyl)-[1,2,5]-thiadiazino[5,6-a]benzimidazole-I,1-dioxide in 50 ml of I 2N hydrochloric acid, the temperature being kept between -5. C. and 0 C. When the addition is complete, the mixture is stirred for 15 minutes at the same temperature and the whole of it is poured into a solution of 4.4 g (0.044 mol) of cuprous chloride in ml of concentrated hydrochloric acid, cooled to 00 C beforehand, the mixture being added in several portions over a period of 5 minutes, taking care to avoid excessive effervescence. When the addition is complete, the mixture is left to warm up to room temperature, with continued stirring, and then heated to a temperature of CC. It is left to cool to room temperature and 100 ml of water are added. The product is filtered off, washed with water and dried to give 2.5 g (31%) of 7-chloro-* * * * * S CflS * * S S S Q S * S. S S S S S S * S S *S S *** :.. *_* 3,4-dihydro-2H-2-(4-d iethylamino-1 -methylbutyl)-[1,2, 5]-thiadiazino[5,6-a]benzimidazole 1,1-dioxide melting at 150-1 52 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 60,86 (t,6H); 1,19 (d,3H); 1,39 (m,4H); 2,34 (m,6H); 3,42 (m,IH); 4,10 (t,2H); 4,34 (t,2H); 7,39 (dd,IH); 7,81 (d,IH); 7,83 (d,IH) Preparation of example 125: 3,4-Dihydro-2H-2-ethyl-7-fl itro-[1,2,5]-thiadiazino- [5,6-a]benzimidazole-1,1-dioxide and example 126: 3,4-Dihydro-2H-2-ethYl-8-nitro-[1,2,5J-thiadiazino-(5,6-a] beflzimidaZOle-1,1-dioxide A cold solution consisting of 45 ml of concentrated sulfuric acid and 55 ml of 65% nitric acid is added dropwise to a solution of 100.4 g (0.4 mol) of 3,4-dihydro-2H-2-ethyl-[1,2,5]-thiadiazino[5,6-a]beflZimidaZOte-1, 1-dioxide in 500 ml of concentrated sulfuric acid at 5 C. When the addition is complete, the mixture is stirred for 2 hours at room temperature and poured onto ice and the product is filtered off and washed with water and ethanol to give 110.1 g (93%) of a mixture of two isomers. Fractional recrystallization from nitromethane gives 51.3 g of 3,4-dihydro-2H-2-ethyl-7-flitrO-[1,2,5]-thiadiazino[5,6-a]benzimidaZOle-1, 1-dioxide melting at 255 C. and 47.8 g of 3,4-dihydro-2H-2-ethyl-8-nitrO-[1,2,51thiadiazino[5,6-a]benZimidaZOle-1, 1-dioxide melting at 208 C. Example 125: 1H-NMR (100 MHz, DMSO-d6): 6 1,25 (t,3H); 3,38 (q,2H); 4,23 (t,2H); 4,58 (t,2H); 8,02 (d,IH); 8,25 (dd,IH); 8,74 (d,IH) Example 126: 1H-NMR (100 MHz, DMSO-d6): 6 1,27 (t,3H); 3,40 (q,2H); 4,23 (t,2H); 4,54 (t,2H); 7,88 (d,IH); 8,31 (dd,IH); 8,67 (d,IH) Example 131: 2H-2-Butyl-3,4-d ihydro-7-nitro-[1,2,5]-thiad iazino-[5,6-a]benzimidazole-1,1 -dioxide 2.6 g (0.11 mol) of sodium hydroxide are added to a solution of 26.8 g (0.1 mol) of 3,4-dihydro-2H-7-nitro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide in 200 ml of dimethylformamide. The solution is stirred for one hour at room temperature and 13.6 g (0.1 mol) of butyl bromide are then added. Stirring is continued for a further 3 hours at 40 C., the mixture is poured into water and the product is filtered off and washed with water. The precipitate is recrystallized from acetonitrile to give 29.2 g !: ;: (90%) of 2H-2-butyl-3,4-dihydrO-7-flitrO-E1,2,5]-thiadiazino[5,6-a]benzimidaZOle-1, 1-dioxide melting at 195-1 97 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 0,93 (t,3H); 1,51 (m,4H); 3,36 (t,2H); 4,24 (t,2H); 4,61 (t,2H); 8,07 (d,IH); 8,20 (dd,IH); 8,65 (d,IH) Example 147: 7Amino3,4-dihydrO-2H-2-ethYI.L1,2,5]-thiadiazino-L5,6-ajbenzimidazole-1,1 -dioxide A solution of 5.9 g (0.02 mol) of 3,4dihydro-2H-2-ethYl-7-nitrO-E1,2,5]-thiadiazinO[5,6-a]benzimidazole-1, 1-dioxide in 200 ml of methanol, containing 0.2 g of 10% palladium-on-charcoal, is hydrogenated at room temperature for 12 hours at a pressure of 60 psi. The mixture is filtered and the methanol is concentrated to give 4.6 g (87%) of 7amino-3,4-dihydrO-2H-2-ethYl-[l,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-diOXide melting at 232-234 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 1,22 (t,3H); 3,29 (q,2H); 4,16 (m,4H); 5,36 (b,2H); 6,58 (d,IH); 6,75 (dd,IH); 7,45 (d,IH) Example 148: ,2,5]-thiadiazinoE5,6-a]benzimidazOle-1,1 -dioxide A solution of 4.5 g (0.017 mol) of 7amino-3,4-dihydrO-2H-2-ethYl-[l,2,5]-thiadiazino[5,6a]beflZimidaZole1, 1di0xide in 100 ml of 4N hydrochloric acid is added, with stirring, to a solution of 2 ml (0.02 mol) of thiophosgene in 100 ml of chloroform. The mixture is stirred at room temperature until the orange color of the organic layer has disappeared (about 6 hours), and the latter is separated off by decantation, washed with water, dried over sodium sulfate and evaporated to dryness. The residue is recrystallized from an acetone/water mixture (9:1) to give 3.0 g (49%) of 3,4-dihyd ro2H2ethyl-7-isOthiocyaflatO1l,2,5]-thiadiazino[5 6-a]benzimidazole-1,1-dioXide melting at 218-225 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 1,25 (t,3H); 3,36 (q,2H); 4,19 (t,2H); 4,41 (t,21); 7,39 (dd,IH); 7,84 (d,IH, J = 2 Hz); 7,84 (d,IH, J = 8,6 Hz) * * * S S *** * 1 * 6u. * S. S S * * . S * * * I S * *.* :__ * Example 149: 7AcetylaminO-3,4-dihydrO-2H-2ethYlLl,2,5]-thiadiaziflOE5,6-a] benzimidazole-1,1 -dioxide 1.6 g (0.02 mol) of acetyl chloride are added slowly to a solution of 5.3 g (0.02 mol) of 7amino-3,4-dihydro-2H-2-ethYl-I1,2,5]thiadiazino[5,6-a]benZimidaz0le.I, l-dioxide in ml of pyridine cooled in a water/ice bath. When the addition is complete, the mixture is stirred for 2 hours at room temperature and poured onto ice. The product is filtered off, washed with water and dried to give 4.2 g (68%) of 7-acetylamiflo-34- dihydro-2H-2-ethyl-[1,2, 5]thiadiazino[5,6-a]benZimidaZOle-l,1-dioxide melting at 245-248 C.</p>
<p>1H-NMR (100 MHz, DMSO-d6): 61,24 (t,3H); 2,10 (s,3H); 3,34 (q,2H); 4,16 (t,2H); 4,36 (t,2H); 7,37 (d,IH); 7,70 (d,IH); 8,10 (s,IH); 10,06 (s,IH) Example 173: 1,2,3,4,1 3,14HexahydropyridO(1',2'2,3]-[l,2,5]-thiadiazino(5,6-a]benzimidazole-6, 6-d ioxide 2.95 g (0.01 mol) of 2-(su Ifonyl-2-hydroxymethYl-1 -piperidinyl)-1 H-benzimidazole are refluxed for 1 hour in 20 ml of thionyl chloride. The mixture is evaporated to dryness and the residue is recrystallized from an ethanol/ethyl acetate mixture (1:1)to give 2.0 g (73%) of 1,2,3,4,13,1 4-hexahydropyridOEl,2':2,3]-[1,2,5]-thiadiazino[5,6-a]benzimidazole-6, 6-diOXide melting at 246-248 C.</p>
<p>1H-NMR (1 00 MHz, DMSO-d6): 6 1,82 (m,6H); 3,02 (m,IH); 4,39 (m,2H); 4,71 (d,2H); 7,31-7,88 (m,4H) Example 178: 2H-2-Ethyl-3-pheflYl-[1,2,51thiadiazino[5,6a]beflZimidaZ0le.l,1 -dioxide A mixture of 13.7 g (0.04 mol) of 1benzoylmethylNethYl-1H-benZimidaZ0le2 sulfonamide and 230 g of polyphosphoric acid is stirred at 125 C for 4 hours. The resulting solution is poured onto ice and the product is filtered off and washed with water, then with an aqueous solution of sodium bicarbonate and again with water to give 8.7 g (67%) of 2H-2-ethyl-3-pheflYl-[1,2,5]-thiadiazino[5,6-a]benzimidaZOle-1, 1-dioxide melting at 15 C.</p>
<p>S</p>
<p>!: 61: ; 1H-NMR (100 MHz, DMSO-d6): 6 0,75 (t,3H); 3,55 (q,2H); 7,53 (m,5H); 7,83 (m,3H); 8,21 (d,IH); 8,51 (s,IH) The examples in table 1 are prepared according to the methods and examples given above.</p>
<p>Table I.</p>
<p>[2] N-Methyl-I H-benzimidazole-2-sulfonamide [3] N-(2-Pyridyl)-1 H-benzimidazole-2-sulfonamide [4] N-2-[(4-Morpholinoethyl)]-I H-benzimidazole-2-sulfonamide [5] N-(4-Aminobutyl)-1 H-benzimidazole-2-sulfonamide [6] N-[3-(4-Morpholinopropyl)]-1 H-benzimidazole-2-sulfonamide [7] 5-Ch loro-N-ethyl-I H-benzimidazole-2-sulfonamide [8] 5-Phenoxy-N-ethyl-I H-benzimidazole-2-sulfoflamide [9] N-[2-(3,4-Dimethoxyphenylethyl)]-1 H-benzimidazole-2-sulfOflamide [10] N, N-Diethyl-I H-benzimidazole-2-sulfonamide [11] N-Butyl-1 H-benzimidazole-2sulfonamide [12] N-Ethyl-4,7-dichloro-5,6-difllethYl-1 H-benzimidazole-2-sulfoflamide [13] N-(4-Chlorophenyl)-I H-benzimidazole-2-sulfOflamide [14] 5-Chloro-N-(4-chloropheflyl)-1 H-benzimidazole-2-sulfOflamide [15] 5-Chloro-N-(4-diethylamiflO-I -methylbutyl)-I H-benzimidazole-2-sulfoflamide [17] 4-Ch Ioro-5,6-dimethyl-N-ethyl-1 H-benzimidazole-2-sulfOflamide [18] 4-Nitro-1 H-benzimidazole-2-sulfOflamide [19] N-Ethyl-4-nitro-I H-benzimidazole-2-sulfOflamide [20] N-(4-Diethylamino-1 -methylbutyl)-1 H-benzimidazole-2-su Ifonamide [21] N-Cyanomethyl-I H-benzimidazole-2-sulfonamide [22] N-Cyclohexyl-1 H-benzimidazole-2-sulfOflamide [23] N-(I -Naphthyl)-I H-benzimidazole-2-sulfoflamide [24] N-Ethyl-5-trifluoromethyl-I H-benzimidazole-2-sulfonamide [25] N-(I -Adamantyl)-1 H-benzimidazole-2-sulfonamide [26] 2-(Sulfonyl-2-hydroxymethyl-1 -piperidinyl)-1 H-benzimidazole [27] N-(4-Methoxybenzyl)-1 H-benzimidazole-2-sulfOflamide [28] N-(5-Methyl-3-isoxazolyl)-1 H-benzimidazole-2-sulfoflamide * . .., :: 6Z;: :.</p>
<p>[29] N-(2-Pyridylmethyl)-1 H-benzimidazole-2-sulfonamide [30] N-[2-(2-Pyridylethyl)]-1 H-benzimidazole-2-sulfonamide [311 5-Benzoyl-N-(4-d iethylamino-I -methylbutyl)-1 H-benzimidazole-2-sulfonamide [32] 5-Nitro-1 H-benzimidazole-2-su Ifonamide [33] N-Ethyl-5-n itro-1 H-benzimidazole-2-sulfonamide [34] N-[2-(4-Morpholinoethyl)]-5-n itro-1 H-benzimidazole-2-sulfonamide [35] , N-Diethyl-5-n itro-1 H-benzimidazole-2-sulfonamide [36] N-[3-(4-Morpholinopropyl)]-5-nitro-1 H-benzimidazole-2-sulfonamide [37] N-Butyl-4-n itro-1 H-benzimidazole-2-su Ifonamide [38] N-(2-Hydroxy-1 -ethyl)-4-n itro-1 H-benzimidazole-2-sulfonamide [39] N-Carboxyethylmethyl-4-nitro-1 H-benzimidazole-2-sulfonamide [40] N-Ethyl-N,4-dinitro-1 H-benzimidazole-2-sulfonamide [41] N-[2-(4-Morpholinoethyl)]-4-nitro-1 H-benzimidazole-2-sulfonamide [42] N-Acetyl-N-ethyl-4-nitro-1 H-benzimidazole-2-su Ifonamide [43] N-Acetyl-4-n itro-1 H-benzimidazole-2-sulfonamide [44] 2-[Sulfonyl-4-(2-hydroxy-1 -ethyl)piperazinyl]-4-nitro-1 H-benzimidazole [45] N-(4-Fluorophenyl)-4-nitro-1 H-benzimidazole-2-sulfonamide [46] 2-[Sulfonyl-2-(carboxymethyl)pyrrolidinyll-4-nitrO-I H-benzimidazole [47] N-Methyl-4-nitro-1 H-benzimidazole-2-su Ifonamide [48] N-Propyl-4-nitro-1 H-benzimidazole-2-sulfonamide [49] N-lsopropyl-4-nitro-1 H-benzimidazole-2-sulfonamide [50] N-Ethylthioethyl-4-nitro-1 H-benzimidazole-2-sulfonamide [51] N-Ethylsulfonylethyl-4-n itro-1 H-benzimidazole-2-sulfonamide [52] N-[3-(2-Oxo-hexamethyleneiminyl)]-4-n itro-1 H-benzimidazole-2-sulfonamide [53] N-[1 -[1, 3-Bis(carboxyethyl)propyl]]-4-nitro-1 H-benzimidazole-2-sulfonamide [54] 2-[Sulfonyl-4-methylpiperazinyl]-1 H-benzimidazole [55] 5-Chloro-N-cyclohexyl-I H-benzimidazole-2-sulfonamide [56] N-(2-Diethylamino-I -ethyl)-I H-benzimidazole-2-sulfonamide [57] N-EthylI H-imidazo[4,5-b]pyridine-2-sulfonamide [58] N-Butyl-I H-imidazo[4,5-b]pyridine-2-sulfoflamide [59] N-Butyl-1 H-imidazo[4,5-c]pyridine-2-sulfonamide [611 1, N, N-Triethyl-I H-benzimidazole-2-su Ifonamide * * * S I *flfl * . *1* * S * *O.). * * S. 5 * * -a S S S * . S S. S *** S S [62] 1,N-Dimethyl-N-ethyl-1 H-benzimidazole-2-sulfonamide [63] 1 -Benzoylmethyl-N-ethyl-1 H-benzimidazole-2-sulfonamide [64] 1 -Acetylmethyl-N-ethyl-I H-benzimidazole-2-sulfonam ide [65] N-Ethyl-I -(2-pyridylcarbonylmethyl)I H-benzimidazole-2-sulfonam ide [66] 5-Ch loro-N-(4-d iethylam mo-I -methylbutyl)-1-ethyl-I H-benzimidazole-2-sulfonamide [67] 6-Chloro-N-(4-diethylamino-I -methylbutyl)-1 -ethyl-I H-benzimidazole-2-sulfonamide [68] 1, N-Diethyl-4-nitro-I H-benzimidazol-2-su Ifonam ide [70] 1, N, N-Triethyl-5-nitro-I H-benzimidazole-2-sulfonam ide [71] 5-Chloro-I, N-diethyl-N-(4-diethylamino-1 -methylbutyl)-1 H-benzimidazole-2-sulfonamide [72] 6-Chloro-1, N-diethyl-N-(4-d iethylamino-I -methylbutyl)-1 H-benzimidazole-2-sulfonamide [73] 1, N, N-Triethyl-4-nitro-I H-benzimidazole-2-sulfonamide [74] 1, N, N-Triethyl-7-nitro-1 H-benzimidazole-2-sulfonamide [75] 1, N-Diethyl-5, N-dinitro-1 H-benzimidazole-2-sulfonamide [76] 1, N-Diethyl-6, N-dinitro1 H-benzimidazole-2-sulfonamide [77] 1, N-Diethyl-5-n itro-I H-benzimidazole-2-sulforiamide [78] 1, N-Diethyl-6-n itro-I H-benzimidazole-2-sulfonamide [79] 5-Amino-I H-benzim idazole-2-su Ifonamide [80] 4-Amino-I H-benzimidazole-2-sulfonamide [81] 4-Amino-N-(carboxyethylmethyl)-I H-benzim idazole-2-sulfonamide [821 4-Amino-N-ethyl-I H-benzimidazole-2-sulfonamide [83] 4-Acetylam mo-N-ethyl-I H-benzimidazole-2-sulfonamide [85] 3,4-Dihydro-2H-[I,2, 5]-thiadiazino[5,6-a]benzimidazole-I,I-dioxide [86] 3,4-Dihydro-2H-2-methyl-[I,2,5]-thiadiazino[5,6-a]-benzimidazole-I, I-dioxide [87] 3,4,5-Trihydro-2H-2-methyl-[I,2,6]-thiadiazepino[6,7-a]-benzimidazole-I, 1-dioxide [88] 3,4,5-Trihydro-2 H-2-ethyl-[ 1,2,6J-thiad iazepino[6,7-a]-benzimidazole-1,1 -dioxide [89] 3,4,5,6-Tetrahyd ro-2H-2-ethyl-[ 1,2,7]-thiad iazi no-[7,8-a]benzimidazole-l, 1-dioxide * . S S S S * * S.: : . S S * * S. S ** :.. *_* [90] 3,4-Dihydro-2H-[3-(4-morpholinopropyl)]-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [91] 3,4,5-Trihydro-2H-[2-(4-morpholinoethyl)1-[1,2,6]-thiadiazepino[6, 7-ajbenzimidazole-1, 1-dioxide [92] 3,4-Dihyd ro-2H-2-ethyl-8-phenoxy-[1,2, 5]-thiad iazino-[5,6-ajbenzimidazole- 1, 1-dioxide [93] 3,4-Dihyd ro-2H-2-ethyl-7-phenoxy-[1,2, 51-thiad iazino-[5,6-a]benzim idazole- 1,1-dioxide [94] 8-Chloro-3,4-d ihyd ro-2H-2-ethyl-7-phenoxy-[ 1,2, 5]thiad iazino-5,6-a]benzimidazole-1,1-dioxide [95] 7-Chloro-3,4-d ihyd ro-2H-2-ethyl-7-phenoxy-[1,2, 5]-thiad iazino[5,6-a]benzimidazole-1, 1-dioxide [96] 3,4,5-Trihydro-2H-[1,2,61-thiadiazepino[6,7-a]benzimidazole-1, 1-dioxide [97] 3,4-Dihydro-2H-2-[2-(3,4-d imethoxyphenylethyl)]-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [98] 2H-2-Butyl-3,4-Dihydro-[1,2,5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [99] 6, 9-Dichloro-3,4-d ihyd ro-7, 8-d imethyl-2H-2-ethyl-[1,2, 5J-thiad iazino[5,6-a]benzimidazole-1, 1-dioxide [100] 8-Chloro-3,4-d ihydro-2H-2-(4-d iethylamino-1 -methylbutyl)-[1,2, 51-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [102] 2H-2-(4-Chlorophenyl)-3,4-dihydro-[1,2,5]-thiadiazino-[5, 6-ajbenzimidazole- 1,1-dioxide [103] 3,4-Dihyd ro-2 H-2-(5-methyl-3-isoxazolyl)-[1,2, 5]-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [104] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [105] 3,4-Dihydro-2H-2-ethyl-9-nitro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [1061 3,4-Dihyd ro-2H-2-ethyl-6-nitro-[ 1,2, 5]-th iadiazino-[5,6-a]benzim idazole-1,1 -dioxide [107] 3-Hyd ro-2H-2-methyl-6-nitro-[ 1,2,4]-thiad iazolo[4, 5-a]-benzim idazole-1,1 -dioxide [108] 2H-2-Cyclohexyl-3,4-d ihyd ro-[ 1,2, 5]-thiad iazino[5,6-a]-benzim idazole-1,1 -dioxide * S * S S S * * S *S* * * S * * S S. S 65. * * I * S a. e:.. *.* [109] 3,4-Dihydro-2H-2-( I -naphthyl)-[1,2, 5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [110] 3,4-Dihydro-2H-2-ethyl-7-trifluoromethyl-[ 1,2, 5]-th iad iazino[5,6-ajbenzimidazole-1,1-dioxide [111] 3,4-Dihydro-2H-2-ethyl-8-trifluoromethyl-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [112] 2H-2-(1 -Adamantyl)-3,4-dihydro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [113] 7-Benzoyl-3,4-d ihyd ro-2 H-2-ethyl-[1, 2, 5]-thiadiazino-[5,6-a]benzimidazole- 1,1-dioxide [114] 8-Benzoyl-3,4-d ihyd ro-2 H-2-ethyl-[ 1,2, 5]-thiadiazino-[5, 6-ajbenzimidazole-1,1-dioxide [115] 3,4-Dihyd ro-2H-2-(4-methoxybenzyl)-[ 1,2, 5]-th iad iazino-[5,6-a]benzimidazole-1,1-dioxide [116] 3,4-Dihyd ro-2H-2-(2-pyridylmethyl)-[ 1,2, 5]-thiad iazino-[5,6-a]benzimidazole-1,1-dioxide [117] 3,4-Dihyd ro-2H-2-[2-(2-pyridylethyl)]-[ 1,2, 5]-thiad iazino[5, 6-a]benzimidazole1,1-dioxide [118] 8-Chloro-3,4-d ihydro-2H-2-cyclohexyl-[1,2, 5]-th iad iazino-[5,6-a]benzimidazole-1,1-dioxide [119] 7-Chloro-3,4-dihydro-2H-2-cyclohexyl-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [120] 2-(2-Diethylamino-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [121] 8-Chloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [122] 7-Chloro-3,4-dihydro-2H-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1,1-dioxide [123] 7,8-Dichloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [124] 2-Butyl-7, 8-d ich Ioro-3,4-d ihyd ro-2H-9-nitro-[1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [127] 3,4-Dihyd ro-2H-2-methyl-7-nitro-[ 1,2, 5]-thiad iazino-[5,6-aJbenzimidazole-1, 1-dioxide [128] 3,4-Dihydro-2H-2-methyl-8-nitro-[1,2,5]-thiadiazino-[5,6-a] benzimidazole-1, 1-dioxide i.</p>
<p>[129] 3,4,5-Trihydro-2H-2-ethyl-8-nitro-[1,2,6]-thiadiazepino-[6,7-a] benzimidazole- 1,1-dioxide [130] 3,4,5-Trihyd ro-2 H-2-ethyl-9-nitro-[1,2,6]-thiadiazepino-[6, 7-a]benzim idazole-1,1dioxide [132] 2H-2-Butyl-3,4-dihydro-8-nitro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [133] 3,4-Dihyd ro-2H-8-n itro-2-[2-(2-pyridylethyl)]-[1,2, 5]-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [1341 3,4-Dihyd ro-2H-7-nitro-2-[2-(2-pyridylethyl)]-[ 1,2,5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [135] 3,4-Dihyd ro-2H-8-n itro-(2-pyridylmethyl)-[1, 2, 5J-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [136] 3,4-Dihyd ro-2 H-7-nitro-(2-pyridylmethyl)-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-1, 1-dioxide [137] 3,4, 5,6-Tetrahyd ro-2H-2-ethyl-9-n itro-[ 1,2,7]-thiad iazozino[7, 8-a]benzimidazole-1,1-dioxide [138] 3,4,5,6-Tetrahydro-2H-2-ethyl-I 0-nitro-[1,2,7]-thiad iazozi no[7, 8-a]benzimidazole-1,1-dioxide [139] 3,4-Dihydro-2H-2-[3-(4-morpholinopropyl)]-7-nitro-[1,2,5]-thiadiazino[5, 6-a]benzimidazole-1,1-dioxide [140] 3,4-Dihyd ro-2H-2-[3-(4-morpholinopropyl)]-8-nitro-[1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [141] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-7-nitro-[1,2,5J-thiadiazino[5, 6-ajbenzimidazole-1,1-dioxide [142] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-d ihydro-8-n itro-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [143] 3,4-Dihydro-2H-7-nitro-[1,2,5J-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [144] 3,4-Dihydro-2H-8-nitro-[1,2, 5]-thiadiazino[5,6-aJ-benzimidazole-1,1-dioxide [145] 2H-2-( I -Adamantyl)-3,4-d ihyd ro-7-nitro-[1,2, 5]-thiadiazino[5, 6-a]benzimidazole-1,1-dioxide [146] 2H-2-(1 -Adamantyl)-3,4-dihydro-8-nitro-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-1, 1-dioxide [150] 2-Carboxyethylmethyl-8-chloro-3,4-d ihyd ro-2H-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide 44 *1 I las *: ; : [151] 2-Carboxyethylmethyl-7-chloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [152] 8-Chloro-2-(6-chloro-1 -hexyl)-3,4-dihydro-2H-[ I,2,5]-thiad iazino[5,6-a]benzimidazole-1, [153] 7-Chloro-2-(6-chloro-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, [154] 8-Ch Ioro-2-(2-chloro-1 -ethyl)-3,4-d ihyd ro-2 H-[1,2, 5]-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [155] 7-Chloro-2-(2-chloro-1 -ethyl)-3,4-dihydro-2H-[1,2 15]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [156] 2-(3-Chloro-I -propyl)-3,4-dihydro-2H-7-nitro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, [157] 8-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5]-thiad iazino[5,6-ajbenzimidazole-1,1-dioxide [158] 7-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [159] 2-{3-[N-methyl-N-[2-(3,4-d imethoxyphenyl)ethyl]J-propylamino}-3,4-d ihyd ro-2H-7-nitro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1,1-dioxide [160] 8-Chloro-2-(6-diethylamino-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [161] 7-Chloro-2-(6-diethylamino-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-albenzimidazole-1,1dioxide [162] 8-Chloro-2-cyanomethyl-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1, 1-dioxide [163] 7-Chloro-2-cyanomethyl-3,4-d ihyd ro-2H[ I,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [164] 8-Chloro-2-(2-diethylamino-1 -ethyl)-3,4-dihyd ro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [165] 7-Chloro-2-(2-diethylamino-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-1,1dioxide [166] 7-Chloro-2-(6-ethylamino-I -hexyl)-3,4-d ihydro-2H-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [167] 7-Chloro-2-(2-pyridyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a ]benzimidazole-1,1-dioxide s s_ 4 aa : : 8 a -a -$ * . I a [168] 3,4-Dihydro-2H-2-ethyl-3-methyl-[1,2, 51-thiad iazino[5,6-a]benzimidazole-1, 1-dioxide [169] 3,4-Dihyd ro-2 H-2-ethyl-3-methyl-7-n itro-[ 1,2, 5]-th lad iazino[5,6-a]benzimidazole-1,1-dioxide [170] 3,4-Dihyd ro-2H-2-ethyl-3-methyl-8-n itro-[1,2, 5]-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [171] 2H-2-Butyl-3,4-dihydropyrido[3',2':4,5]imidazo[1,2-e]-[1,2, 5]-thiadiazine-1, 1-dioxide [172] 2-Butyl-3,4-dihydro-2H-pyrido[3',4':4,5]imidazo[1,2-eJ-[1,2, 5]-thiadiazine-1, 1-dioxide [174] 1,2,3,4,13,1 4-Hexahydro-9-nitropyrido[1,2':2,3]-[1,2,5J-thiadiazino[5,6-a]benzim idazole-6,6-d ioxide [175] 1,2,3,4,1 3,14-Hexahydro-1 0-nitropyrido[1,2':2,3]-[1,2,5]-thiadiazino[5,6-a]benzim idazole-6,6-dioxide [176] 2H-2-Ethyl-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [177] 2H-2-Ethyl-3-methyl-[ 1,2, 5]-th iadiazino[5,6-a]-benzimidazole-1,1-dioxide [179] 2 H-2-Ethyl-7-nitro-3-(4-nitrophenyl)-[1,2, 5]-th iad iazino-[5,6-a]benzimidazole- 1,1-dioxide; [180] N-ethyl-I -((2-oxo-2, 3-d ihyd robenzo[djimidazol-1 -yl)methyl)-I H-benzo[d]imidazole-2-sulfonamide and [1811 1,2,3,4,13,14-Hexahydro-9,10-dinitropyrido[1',2':2,3]-[1,2,5]-thiadiazino [5,6-ajbenzim idazole-6,6-d ioxide C a S I 151 * S * S * I I I * S S p S * S W * * * S S I I * * * * I 1St IS. S Pharmacological data: The binding of the substituted benzimidazole sulfonamide compounds of general formula I to the 5-HT6 receptor was determined as described above.</p>
<p>The binding results for some of these compounds are given in the following</p>
<p>table:</p>
<p>Compound according Compound Binding to 5-HT6 to example number receptor [%] 171 E-3894 67.2 E-3893 60.1 E-1862 56.2 181 E-3896 62 * * S * * S S S * S S S S S 7( S * 4 * S * * S S S S S 5 *5 S *SS *sS. Jo'</p>

Claims (1)

  1. <p>Claims: Use of at least one substituted benzimidazolesulfonamide of
    general formula I, R1 N R2 TIE >--N'</p>
    <p>N R I,</p>
    <p>wherein Z1 represents a nitrogen atom or a carbon atom bonded to another radical R4 (C-R4); z2 represents a nitrogen atom or a carbon atom bonded to another radical R5 (C-R5); z3 represents a nitrogen atom or a carbon atom bonded to another radical R6 (C-R6); z4 represents a nitrogen atom or a carbon atom bonded to another radical R7 (C-R7); with the restriction that only one of the groups Z1, Z2, Z3 or Z4 can represent a nitrogen atom; R1 and R2, independently of one another, in each case represent a hydrogen atom; a linear or branched alkyl radical which may optionally be substituted with substituents selected from the group consisting of aryl, cycloalkyl radical which S * * . s.</p>
    <p>* * * S S S S S :: 71 * :. :.</p>
    <p>I</p>
    <p>may be condensed with a mono-or bicyclic ring system, -C(=O)-alkyl, -C(0)-aryl and -C(=O)-heteroaryl; a cycloalkyl radical which may be condensed with a mono-or bicyclic ring system; -C(=O)-O-alkyl; -C(=O)-alkyl or -NO2; or alternatively R' and R2 together form a linkage represented by a group X; R3 represents a hydrogen atom; a linear or branched alkyl radical which may optionally be substituted with substituents selected from the group consisting of-OH, -NH2, -NH-alkyl, -N(alkyl)(alkyl), -S-alkyl, -S(=O)-alkyl, -S(=O)2-alkyl, halogen, -CN, -NH[(CH2)i, 2, 3or4a1'Yl], -N[alkyl][(CH2)1, 2, 3or4-aryl], piperazinyl, piperidinyl, morpholinyl, aryl, heteroaryl, -C(=O)-O-alkyl, -S-aryl, -S(=O)-aryl, -S(0)2-aryl, -S- heteroaryl, -S(=O)-heteroaryl, -S(=O)2-heteroaryl, -S-(CH2)i,2,3or4-aryl, - 2,3 or4arYl, -S(=O)2-(CH2)i, 2,3 or4-aryl, -S-(CH2)i, 2,3 or4 heteroaryl, -S(0)-(CH2)i, 2,3or4heteroal and -S(=O)2-(CH2)i,2, 3 Q-heteroaryl; an aryl radical; a heteroaryl radical; a cycloalkyl radical which may be condensed with a mono-or bicyclic ring system and/or may be bridged by linear or branched alkylene; or -C(=O)-alkyl; X represents -(CHR8)n-(CHR9)m-or -CR8=CR9; or alternatively R2 and R3 together form a linkage represented by a group -(CH2)nYnrCHR -, Y represents -CH2-O-CH2-or -CH2-NR-CH2-; n represents 1, 2, 3 or 4; m represents 0 or 1;</p>
    <p>S S</p>
    <p>0 S * * S S * :: ::72. :. :.</p>
    <p>R4 and R7, independently of one another, in each case represent a hydrogen atom; a halogen atom; -NO2; -NH2; -NH-(alkyl); -N(alkyl)(alkyl) or -NH-C(0)-alkyl; R5 and R6, independently of one another, in each case represent a hydrogen atom; a halogen atom; -NO2; -NH2, a C1..5-alkyl radical; -CF3; -0-alkyl; -0-aryl; -SH; -S-alkyl; -S(=O)-alkyl; -S(=O)2-alkyl, -N=C=S, -CO)-alkyl; -C(0)-aryl; -NH-C(=O)-alkyl; -CN; -C(=O)-OH; -C(=O)-NH2; -C(=O)-O-alkyl or -S(=O)2-NH2; R8 and R9, independently of one another, in each case represent a hydrogen atom; a C1..5-alkyl radical; an aryl radical or a heteroaryl radical; R1 represents a hydrogen atom; -C(=O)-O-alkyl; a radical -CH2OH; a radical -CH2CI or a methylene radical (-CH2-); or alternatively R1 together with R1 form a linkage, in case R1 represents a methylene radical (-CH2-) and R1 itself represents a linkage; and R11 represents a hydrogen atom or an alkyl radical which may optionally wherein aryl represents a phenyl group, a naphthyl group or a substituted phenyl or heteroaryl represents an aromatic 5-to 14-membered heterocyclic group in which the heteroatom or heteroatoms of the ring is/are selected from the group consisting of 0 and N and the heterocyclic group can be substituted; alkyl, if not defined otherwise, represents a C1..10 alkyl radical; 4 a. ...</p>
    <p>:: :. :. :.</p>
    <p>cycloalkyl represents a C cycloalkyl radical which can be substituted and which may contain at least on heteroatom in the ring which is selected from the group consisting of 0 and N; the mono-or bicyclic ring system can be substituted and the rings of the aforementioned mono- or bicyclic ring system are in each case independently of one another 5-, 6-or 7-membered and may in each case independently of one another optionally contain 1, 2 or 3 heteroatom(s) independently selected from the group consisting of 0 and N; alkylene represents a C1.5 alkylene group which can be substituted; optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereolsomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof; for the manufacture of a med icament for the prophylaxis and/or treatment of a disorder or disease related to food intake.</p>
    <p>2. Use according to claim 1, characterized in that R1 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl; a radical selected from the group consisting of -CH2-C(=0)-CH3, -C H2- C(=O)-C2H5, -CH2-C(=0)-CH2-CH2-CH3, -CH2-C(=0)-CH(CH3)2, -CH2- C(=O)-C(CH3)3, -CH2-CH2-C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2- CH2-C(=O)-C H2-CH2-CH3, -C H2-C H2-C(=O)-CH (CH3)2, -CH2-C H2-S S 5 0 :: : :* :: C(=O)-C(CH3)3, -CH2-CH2-CH2-C(0)-CH3, -CH2-CH2-CH2-C(0)-C2H5, -CH2-CH2-CH2-C(=O)-CH2-CH2-CH3, -CH2-CH2-CH2-C(=O)-CH(CH3)2 and -CH2-CH2-CH2-C(0)-C(CH3)3, a radical selected from the group consisting of -CH2-aryl, -CH2-CH2- aryl, -CH2-CH2-CH2-aryl, -CH(CH3)-CH2-aryl, -CH(C2H5)-CH2-aryl, -CH2-CH(CH3)-aryl, -CH2-CH(C2H5)-aryl, -CH2-CH2-CH2-CH2-aryl, -CH2C(=O)-aryl, -CH2-CH2-C(=O)-aryl, -CH2-CH2-CH2-C(0)-aryl, -CH(CH3)-CH2-C(=O)-aryl, -CH(C2H5)-CH2-C(=O)-aryl, -CH2-CH(CH3)-C(0)-aryl, -CH2-CH(C2H5)-C(=O)-aryl, -CH2-CH2-CH2-CH2-C(=O)-aryl, -CH2-C(=O)-heteroaryl, -CH2-C H2-C(=O)-heteroaryl, -CH2-CH2-CH2-C(0)-heteroaryl, -CH (C H3)-C H2-C(=O)-heteroaryl, -CH(C2H5)-C H2-C (0)-heteroaryl, -CH2-C H(C H3)-C(=O)-heteroaryl, -CH2-C H (C2H5)-C(0)-heteroaryl and -CH2-CH2-CH2-CH2-C(=O)-heteroaryl; wherein aryl represents a phenyl radical or a naphthyl radical and heteroaryl represents a radical selected from the group consisting of pyridinyl, furyl (furanyl), thienyl (thiophenyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxad iazolyl, triazolyl, pyridazinyl, pyrimid inyl, indolyl and isoindolyl, and wherein the aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or 5 substituent(s) independently selected from the group consisting of -CF3, methyl, ethyl, n-propyl, isopropyl, n- butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, n-hexyl, -O-CH3, -O-C2H5, - O-CH2-CH2-CH3, -O-CH(CH3)2, -O-CH2-CH2-CH2-CH3, -O-C(CH3)3, -S- CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH3)2, -S-CH2-CH2-CH2-CH3, -S-C(CH3)3, F, Cl, Br, I, -CN, -OCF3, -SCF3, -SCF2H, -SCFH2, -OH, -SH, -NO2, -CHO, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-C(CH3)3, -CF2H, -CFH2, -C(=O)-NH2, -C(=O)-NH-CH3, -C(=O)-NH-C2H5, -C(=O)-NH-C3H7, - C(=O)-N(CH3)2, -C(=O)-N(C2H5)2, -S(=O)-CH3, -S(=O)-C2H5, -S(=O)- C3H7, -S(=O)2-CH3, -S(=O)2-C2H5, -S(=O)2-C3H7, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2 and -N(C2H5)2, a 2-oxo-2,3-dihydrobenzo[d]imidazol-1yl radical, which may be bonded via a -(CH2)-group, * S. *I.</p>
    <p>e I I I * * * I a * I * * *. * .75 I * I * I * * S S S I. I S*. *SS a or a radical selected from the group consisting of -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)- O-C(CH3)3, -C(=O)-O-CH2-CH2-CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, - C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2.</p>
    <p>3. Use according to claim I or 2, characterized in that R2 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl; or a radical selected from the group consisting of -C(=O)-O-CH3, - C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)- O-C(CH3)3, -C(=O)-O-CH2-CH2-CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2.</p>
    <p>4. Use according to one or more of claims I to 3, characterized in that R1 and R2 together form a linkage represented by a group X, wherein X represents -(CH R8)-, -(C H R8)-(CH R9)-, -(CH R8)-(C H R8)-, -(CH R8)-(CH R8)- (CHR8)-, -(CHR8)-(CHR8)-(CHR8)-(CHR8)-or -CR8=CR9-.</p>
    <p>5. Use according to one or more of claims 1 to 4, characterized in that R3 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, S S. 0.S * S * * * * . :: 76:. :.</p>
    <p>ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2- pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3- octyl and 4-octyl, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of Cl, Br, F, I, -OH, -CN, -NH2, -NH-CH3, -NH-C2H5, -N(CH3)2, -N(C2H5)2, -N(CH3)(C2H5), -NH-CH2-CH2-aryl, -N(CH3)-CH2-CH2-aryl, piperazinyl, piperidinyl, morpholinyl, -S-CH3, -S-C2H5, -S-CH(CH3)2, -S-C(CH3)3, -S(0)- CH3, -S(=O)-C2H5, -S(=O)-CH(CH3)2, -S(=O)-C(CH3)3, -C(=O)-CH3, -C(=O)- C2H5, -C(=O)-CH(CH3)2, -C(=O)-C(CH3)3, -C(=O)-O-CH3, -C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-C(CH3)3, aryl and heteroaryl; an aryl radical; a heteroaryl radical; a radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, pyrrolid inyl, piperid inyl, piperazinyl, morpholiriyl, imidazolidinyl, azepanyl, diazepanyl, azocanyl, adamantyl, bicyclo[2.2.1]heptyl and bicyclo[3.1.1]heptyl, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, iso-butyl, tert-butyl, oxo (=0) and thioxo (=S); or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, - C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(0)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; whereby aryl represents a phenyl radical or a naphthyl radical and heteroaryl represents a radical selected from the group consisting of pyridinyl, furyl (furanyl), pyrrolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, oxadiazolyl, triazolyl, pyridazinyl, pyrimidinyl, indolyl and isoindolyl, and whereby the aryl and heteroaryl radicals may optionally be substituted with 1, 2, 3, 4 or5 substituent(s) independently selected from the group consisting of-CF3, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, * S S V * a a * * * * S * * S S S S SS * c'7 * S S * * b a a * VS S Is. S.. S</p>
    <p>U -</p>
    <p>n-hexyl, -0-CH3, -0-C2H5, -0-CH2-CH2-CH3, -0-CH(CH, -0-CHrCHrCHr CH3, -0-C(CHs)a, -S-CH3, -S-C2H5, -S-CH2-CH2-CH3, -S-CH(CH, -S-CH2- CH2-CHrCH3, -S-C(CH, F, Cl, Br, I, -CN, -OCF3, -SCF3, -SCF2H, -SCFH2, - OH, -SH, 4402, -CHO, -C(=0)-CH3, -C(=0)-C2H5, -C(=0)-C(CFM3, -CF2H, - CFH2, -C(=O)-NH2, -C(=0)-NH-CH3, -C(=0)-NH-C2H5, -C(=0)-NH-C3HT, - C(=0)-N(CH, -C(=0)-N(C2H.)2, S(:O)CHa, -S&0)-C2Hs, $(0)C3Hi, -S(C)rCH3, -S(=0)2-C2H5, -S(=0)rC3H7, -NH2, -NH-CH3, -NH-C2H5, 41(CH and C2H.</p>
    <p>6. Useaccordingtoclakn5,characterizedinthat R3 represents a hydrogen atom; a radical selected from the group consisting of-CH3, -CH2-CH3, -CH(CHO, - CH2-CH2-CH2-CH3, -C(CH, -CH2-CN, -CH2-CH2-CN, -CHrCH2-CHrCN, -CHrCH2-CHrCHrCN, -CHrCI, -CHrCHa-Cl, -CHrCH2-CHrCI, CHrCHr CH2-CH2-Cl, -CH2-CHrCHrCHrCHrCI, -CHrCHrCHrCHrCHrCHrCI, -CHrN(C2He), CH2-CHrN(C2He, CH2-CHrCHrN(C2H02, CHrCHrCHr CHrN(C2Hs), CHrCHrCHrCHrCHrN(C2H)a, CHrCHrCHrCH2-CHr CHrN(C2H.)z -CH2-N(CFW2, -CH2-CH2-N(CHt CH2-CH3-CHrN(CHa)z -CH2-CHrCH2-CHrN(CHt CHrCHrCHrCHrCHrN(CHM, CHrCHrCHr CHrCHrCHrN(CHO, -CH2-NH-(C2H), CHrCHrNH-(C2HO, CKrCHrCHr NH-(C2H5), -CH2-CH2-CHrNH-(C2HS), CHrCHrCHrCHrNH-(C2HO, -CHr CHrCH2-CHrCHrNH-(CtIe), CHrCHrCHrCHrCHrCHrNH(CzHO, CH2-CH2-S(0)rCHrCHa, CHrS(0)rCHrCH& CHrCHrCHaS(0)r CH2-CH3, CHrCHz-S&0)rCFb, CHrS(0)rCH3, CHrCHrCHrS(0)r CH3, CH2-CH -S("O)-CHrCHa, CH2S(0)CHrCH3, CHrCHrCHa-S(0> CHrCI"b, H2-CH2-S(0)-CEb, -CH2-S(=0)-CH3, -CH2-CH2-CH2-S(0)-CH3, CHrCHrSCHrCH& -CHrS-CHrCH& -CHrCHVCHrSCHrCH3, -CHr CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CHrNH2, CHrCHrNH2, - CHa-CHrCHa-NH2, -CHrCHrCH2-CHrNH2, CH(CHS)-CHrN(C2Hè, - CH(CEb)-CHrCHZ-N(C2H02, CH(CFb)-CHrCHrCHrN(C2HO)2, -CH(CH3)- CHrN(CH)z CH(CH3)-CH2-CHrN(CHO2, CH(CHO-CHrCHrCHrN(CHO, - C14-OH, -CH2-CHrOH, -CHrCH2-CHrOH; -CHrC(C)-0-CH3, -CH2-C(C)- * S S S 555 * S S S S S S S</p>
    <p>S S S S S S S</p>
    <p>*S *fl S S S SSqu S S SS S. S 555 *sS S O-CH2-CH3, -CH2-C(=O)-O-C(C H3)3, -CH2-C H2-C(=O)-O-CH3, -CH2-C H2- C(=O)-O-CH2-CH3, -CH2-CH2-C(=O)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2-C(=O)-CH2-CH3, -CH[C(=O)-CH3J-CH2-CH2-C(=O)-CH3, -CH2-morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2- pyridinyl, -CH2-CH2-pyridinyl, -CH2-CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl; or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)-C2H5, - C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3.</p>
    <p>7. Use according to one or more of claims 1 to 6, characterized in that R2 and R3 together form a linkage represented by a group -CH2-CH2-O-CH2-CHR10-, -CH2-CH2-CH2-CHR10-, -CH2-CH2-CH2-CH2-CHR10-or -CH2-CH2-NR11-CH2-CHR10-.</p>
    <p>8. Use according to one or more of claims I to 7, characterized in that * * * * *0I * * * * * S S S S S * * * S. S 7Q * S I * S S * e 0 ** . S.. **S * R4 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(0)-CH3 or -NH-C(=O)-C2H5.</p>
    <p>9. Use according to one or more of claims I to 8, characterized in that R5 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
    <p>10. Use according to one or more of claims I to 9, characterized in that R6 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2- CH2-CH3; -CF3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
    <p>11. Use according to one or more of claims I to 10, characterized in that R7 represents a hydrogen atom; F; Cl; Br or -NO2.</p>
    <p>12. Use according to one or more of claims I to 11, characterized in that R8 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
    <p>13. Use according to one or more of claims I to 12, characterized in that R9 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or3 substituent(s) * S * a a..</p>
    <p>* a a a a S a a * S I I * * I 4. S Sfl * a * * S I I S I S. * *55 *S* S independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
    <p>14. Use according to one or more of claims I to 13, characterized in that R1 represents a hydrogen atom; -C(=O)-O-CH3; -C(=O)-O-C2H5; -CH2-OH; -CH2-Cl or -C H2-.</p>
    <p>15. Use according to one or more of claims I to 14, characterized in that R11 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or-CH2-CH2-OH.</p>
    <p>16. Use according to one or more of claims 1 to 15, characterized in that Z1 represents a nitrogen atom or a carbon atom bonded to another radical R4 (C-R4); z2 represents a nitrogen atom or a carbon atom bonded to another radical R5 (C-R5); z3 represents a nitrogen atom or a carbon atom bonded to another radical R6 (C-R6); z4 represents a nitrogen atom or a carbon atom bonded to another radical R7 (C-R7); with the restriction that only one of the groups Z1, Z2, Z3 or Z4 can represent a nitrogen atom; R1 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; * * * * *** * * * * * * * * * I I S I S S ** S S S * S S S S S * 5 55. S*S S a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of -CH2-C(=O)-CH3, - CH2-C(=O)-C2H5, -CH2-CH2-C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2- C(=O)-phenyl, -CH2-C(=O)-pyridinyl, -CH2--CH2-C(=O)-phenyl and -CH2-CH2-C(0)-pyrid i nyl; R2 represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, n-octyl, 2-octyl, 3-octyl and 4-octyl; or a radical selected from the group consisting of-C(=O)-O-CH3, - C(=O)-O-C2H5, -C(=O)-O-CH(CH3)2, -C(=O)-O-CH2-CH2-CH3, -C(=O)- O-C(CH3)3, -C(=O)-O-CH2-CH2-CH2-CH3, -C(=O)-CH3, -C(=O)-C2H5, - C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; or alternatively R1 and R2 together form a linkage represented by a group X, wherein X represents -(CHR8)-, -(CHR8)-(CHR9)-, -(CHR8)-(CHR6)-, -(CHR8)- (CHR8)-(CH R8)-, -(CH R8)-(CHR8)-(CH R8)-(CH R8)-or -CR8=CR9-; R3 represents a hydrogen atom; a radical selected from the group consisting of -CH3, -CH2-CH3, - CH(CH3)2, -CH2-CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, - CH2-CH2-CH2-CN, -CH2-CH2-CH2-CH2-CN, -CH2-Cl, -CH2-CH2-Cl, - CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-CH2-Cl, -CH2-N(C2H5)2, -CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-</p>
    <p>S S SS</p>
    <p>* S I S * I I I * I S S I S I S. *) * S S S I S * * S. S *5 III L. --N(CH3)2, -CH2-CH2-N(CH3)2, -CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-NH-(C2H5), -CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-NH(C2H5), -CH2-CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-CH2CH2-NH-(C2H5), -CH2-CH2-S(=O)2-CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(=O)2-CH2-CH3, -CH2-CH2-S(=O)2-CH3, -CH2-S(=O)2- CH3, -CH2-CH2-CH2-S(=O)2-CH3, -CH2-CH2-S(=O)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2-S(=O)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2-S(=O)-CH3, -CH2-CH2-CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, - CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S- CH3, -CH2-CH2-CH2-S-CH3, -CH2-NH2, -CH2-CH2-NH2, -CH2-CH2-CH2- NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH (CH3)-CH2- CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-CH2-N(C2H5)2, -CH(CH3)-CH2- N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-CH2- N(CH3)2, -CH2-OH, -CH2-CH2-OH, -CH2-CH2-CH2-OH; -CH2-C(=O)-O- CH3, -CH2-C(=O)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2- C(=O)-O-CH3, -CH2-CH2-C(=O)-O-CH2-CH3, -CH2-CH2-C(=O)-O- C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2-C(=O)-CH2-CH3, -CH[C(=O)- CH3]-CH2-CH2-C(=O)-CH3, -CH2-morpholinyl, -CH2-CH2-morpholinyl, - CH2-CH2-CH2-morpholinyl, -c H2-pyrid inyl, -c H2-CH2-pyrid inyl, -c H2-CH2-pyridinyl, -CH2-phenyl, -CH2-CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with 1 or 2 substituent(s) independently selected from the group consisting of F, CI, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; * I * a a a A S * * A 5 0 a S as * -a -A A S A 5*0 0*5 a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl; or a radical selected from the group consisting of -C(0)-CH3, -C(O)- C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; or alternatively R2 and R3 together form a linkage represented by a group -CH2-CH2-O-CH2-CHR1 O, -CH2-CH2-CH2-CHR1 O, .-CH2-CH2-CH2-CH2-CH R1 or -CH2-CH2-NR1 1-CH2-CHR10-; R4 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6 represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7 represents a hydrogen atom; F; Cl; Br or -NO2; R8 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with I, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; 0) S I SI.</p>
    <p>IS S S SI S</p>
    <p>S I I S I</p>
    <p>S IA S S S</p>
    <p>S.cw*t. . SI I ISa 0*5 I R9 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R1 represents a hydrogen atom; -C(=O)-O-CH3; -C(0)-O-C2H5; -CH2-OH; -CH2-Cl or -C H2-; or alternatively R1 together with R1 form a linkage, in case R1 represents a methylene radical (-CH2-) and R1 itself represents a linkage; and R11 represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or-CH2-CH2-OH.</p>
    <p>16. Use of at least one substituted benzimidazolesulfonamide according to one or more of claims I to 15 of general formula Ia, R1 4a / ô 2a NR3a Ia wherein za represents a nitrogen atom or a carbon atom bonded to another radical R4a (cR4a); z2a represents a nitrogen atom or a carbon atom bonded to another radical R5a (c_R5a); z3a represents a nitrogen atom or a carbon atom bonded to another radical :: 85 *: :: S. * *** *..</p>
    <p>R6a (c-R) z4a represents a nitrogen atom or a carbon atom bonded to another radical R7a (c-R7 with the restriction that only one of the groups zia, z2a, z3a or Z4a can represent a nitrogen atom; R1a represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of-CH2-C(=O)-CH3, - CH2-C(=O)-C2H5, -CH2-CH2-C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2- C(=O)-phenyl, -CH2-C(=O)-pyridinyl, -CH2--CH2-C(=O)-phenyl and -CH2-CH2-C(=O)-pyrid inyl; R2a represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and n-pentyl; or a radical selected from the group consisting of -C(=O)-CH3, -C(=O)- C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3, -C(=O)-CH2-CH2-CH2-CH3 and -NO2; R3a represents a hydrogen atom; a. *. *, . Pt.</p>
    <p>:: ;:. 86:. :.</p>
    <p>a radical selected from the group consisting of -CH3, -CH2-CH3, -CH(CH3)2, -CH2-CH2-CH2-CH3, -C(CH3)3, -CH2-CN, -CH2-CH2-CN, -CH2-CH2-CH2-CN, -CH2-CH2-CH2-CH2-CN, -CH2-Cl, -CH2-CH2-CI, - CH2-CH2-C H2-Cl, -CH2-CH2-CH2-CH2-Cl, -CH2-CH2-CH2-CH2-CH2-CI, -CH2-CH2-CH2-CH2-CH2-CH2-Cl, -CH2-N(C2H5)2, -CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2N(CH3)2, -CH2-CH2-N(CH3)2, -CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2CH2-CH2-N(CH3)2, -CH2-NH-(C2H5), -CH2-CH2-NH-(C2H5), -CH2-CH2CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2S(=O)2-CH2-CH3, -CH2-S(=O)2-CH2-CH3, -CH2-CH2-CH2-S(=O)2-CH2- CH3, -CH2-CH2-S(=O)2-CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(=O)2- CH3, -CH2-CH2-S(=O)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2- S(=O)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2-S(=O)-CH3, -CH2-CH2- CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CH2-NH2, -CH2-CH2-NH2, -CH2-CH2-CH2-NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-CH2-N(C2H5)2, -CH(CH3)-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2- OH, -CH2-CH2-CH2-OH; -CH2-C(=O)-O-CH3, -CH2-C(0)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2-C(=O)-O-CH3, -CH2-CH2-C(=O)-O- CH2-CH3, -CH2-CH2-C(=O)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2- C(=O)-CH2-CH3, -CH[C(=O)-CH3]-CH2-CH2-C(=O)-CH3, -CH2- morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2- pyrid inyl, -c H2-C H2-pyrid inyl, -c H2C H2-pyrid inyl, -CH2-phenyl, -CH2- CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; S * S a * I..</p>
    <p>:: ) 87:. :.</p>
    <p>a radical selected from the group consisting of phenyl and naphthyl which may be substituted with 1 or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl; or a radical selected from the group consisting of -C(=O)-CH3, -C(O)- C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(0)-CH2-CH2-CH2-CH3; R4a represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5a represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6a represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and R7a represents a hydrogen atom; F; Cl; Br or -NO2.</p>
    <p>!: 88 17. Use of at least one substituted benzimidazolesulfonamideaccording to one or more of claims 1 to 15 of general formula Ib, 3b Xb,R 4b / : lb wherein Z represents a nitrogen atom or a carbon atom bonded to another radical R4b (C_R4b); Z2b represents a nitrogen atom or a carbon atom bonded to another radical R5b (CR5b); Z3b represents a nitrogen atom or a carbon atom bonded to another radical R6b Z4b represents a nitrogen atom or a carbon atom bonded to another radical R7b (CRTb); with the restriction that only one of the groups Zw, Z2b, Z3b or Z4b can represent a nitrogen atom; Xb represents -(CH R8b), -(CH R8b)(C H R9b), -(CH R8b)(CH R8b), -(C H R8b)_ (CH R8b)(CH R8b), -(C H R8b)(CH R8b)(C H R8b)(CH RBb) or _CR8b=C R9b; R3b represents a hydrogen atom; a radical selected from the group consisting of -CH3, -CH2-CH3, - CH(CH3)2, -CH-CIj2-CHCH3, -c(çH, -CH2-CN, -CH2-CH2-CN, - :: : 89:. :.</p>
    <p>CH2-CH2-CH2-CN, -CH2-CH2-CH2-CH2-CN, -CH2-CI, -CH2-CH2-CI, -CH2-CH2-CH2-CI, -CH2-CH2-CH2-CH2-CI, -CH2-CH2-CH2-CH2-CH2-CI, -CH2-CH2-CH2-CH2-CH2-CH2-CI, -CH2-N(C2H5)2, -CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2-CH2-CH2-CH2-CH2-CH2-N(C2H5)2, -CH2N(CH3)2, -CH2-CH2-N(CH3)2, CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2- CH2-N(CH3)2, -CH2-CH2-CH2-CH2-CH2-N(CH3)2, -CH2-CH2-CH2-CH2- CH2-CH2-N(C H3)2, -CH2-NH-(C2H5), -CH2-CH2-NH-(C2H5), -CH2-CH2- CH2-NH-(C2H5), -CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2-CH2-CH2- CH2-.NH-(C2H5), -CH2-CH2-CH2-CH2-CH2-CH2-NH-(C2H5), -CH2-CH2- S(=O)2-CH2-C H3, -c H2-S(=O)2-C H2-C H3, -CH2-CH2-C H2-S(=O)2-CH2- CH3, -CH2-CH2-S(=O)2-CH3, -CH2-S(=O)2-CH3, -CH2-CH2-CH2-S(=O)2- CH3, -CH2-CH2-S(=O)-CH2-CH3, -CH2-S(=O)-CH2-CH3, -CH2-CH2-CH2- S(=O)-CH2-CH3, -CH2-CH2-S(=O)-CH3, -CH2-S(=O)-CH3, -CH2-CH2- CH2-S(=O)-CH3, -CH2-CH2-S-CH2-CH3, -CH2-S-CH2-CH3, -CH2-CH2-CH2-S-CH2-CH3, -CH2-CH2-S-CH3, -CH2-S-CH3, -CH2-CH2-CH2-S-CH3, -CH2-NH2, -CH2-CH2-NH2, -CH2-CH2-CH2-NH2, -CH2-CH2-CH2-CH2-NH2, -CH(CH3)-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-N(C2H5)2, -CH (CH3)-CH2-CH2-CH2-N(C2H5)2, -CH(CH3)-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-N(CH3)2, -CH (CH3)-CH2-CH2-CH2-N(CH3)2, -CH2-OH, -CH2-CH2OH, -CH2-CH2-CH2-OH; -CH2-C(=O)-O-CH3, -CH2-C(=O)-O-CH2-CH3, -CH2-C(=O)-O-C(CH3)3, -CH2-CH2-C(=O)-O-CH3, -CH2-CH2-C(=O)-O- CH2-CH3, -CH2-CH2-C(=O)-O-C(CH3)3, -CH[C(=O)-CH2-CH3]-CH2-CH2- C(=O)-CH2-CH3, -CH[C(=O)-CH3]-CH2-CH2-C(=O)-CH3, -CH2- morpholinyl, -CH2-CH2-morpholinyl, -CH2-CH2-CH2-morpholinyl, -CH2- pyridinyl, -CH2-C H2-pyrid inyl, -c H2-CH2-pyrid inyl, -CH2-phenyl, -c H2- CH2-phenyl, -CH2-CH2-CH2-phenyl, -CH2-CH2-CH2-N(CH3)-CH2-CH2-phenyl, whereby the phenyl radical in each case may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, -O-CH3 and -O-C2H5; a radical selected from the group consisting of phenyl and naphthyl which may be substituted with 1 or 2 substituent(s) independently selected from the group consisting of F, Cl and Br; *. .*. .*. S..</p>
    <p>* a * * * . ::: . 90 * *5 * S.. a.. a' a radical selected from the group consisting of pyridinyl and isoxazolyl which may be substituted with I or 2 substituent(s) independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; a radical selected from the group consisting of cyclopentyl, cyclohexyl, adamantyl and azepan-2-on-yl; or a radical selected from the group consisting of -C(=O)-CH3, -C(0)- C2H5, -C(=O)-CH(CH3)2, -C(=O)-CH2-CH2-CH3, -C(=O)-C(CH3)3 and -C(=O)-CH2-CH2-CH2-CH3; R4b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(0)-CH3 or -NH-C(=O)-C2H5; R5b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1 or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6b represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CE3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7b represents a hydrogen atom; F; Cl; Br or -NO2; R8b represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; *. .*. St. S. *S* :: ;:. 91:. :: and R9b represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-CH2-CH3 or a phenyl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of -NO2; F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.</p>
    <p>18. Use of at least one substituted benzimidazolesulfonamide according to one or more of claims I to 15 of general formula Ic, R1 R10 z3c II 2c SN /YCmc Z1c N ( 2)nc Ic wherein Z1c represents a nitrogen atom or a carbon atom bonded to another radical R4c (CR4c); z2c represents a nitrogen atom or a carbon atom bonded to another radical R5c (C_R5c); Z represents a nitrogen atom or a carbon atom bonded to another radical R6c (CR6c); z4c represents a nitrogen atom or a carbon atom bonded to another radical R7c (C_R7c); with the restriction that only one of the groups Z1, Z2c, Z3c or Z4 can represent a nitrogen atom; *S. .*. S * :: :: 92:. :.</p>
    <p>R represents a hydrogen atom; an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; a 2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl radical, which may be bonded via a -(CH2)-group, or a radical selected from the group consisting of -CH2-C(0)-CH3, - CH2-C(=O)-C2H5, -CH2-CH2-C(=O)-CH3, -CH2-CH2-C(=O)-C2H5, -CH2- C(=O)-phenyl, -CH2-C(=O)-pyridinyl, -CH2--CH2-C(=O)-phenyl and -CH2-CH2-C(0)-pyridinyl; Yc represents -CH2-O-CH2-or -CH2-NR-CH2-; nc represents 1, 2, 3 or 4; mc represents 0 or 1; R4c represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R5c represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6c represents a hydrogen atom; F; CI; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(=O)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, CI, * * . SI.</p>
    <p>* * . S I * 5 S * 5 8 * 5 5 5 *. . * I 8 8 * * * I. . S S. * *.. I Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7c represents a hydrogen atom; F; Cl; Br or -NO2; RiOc represents a hydrogen atom; -C(=O)-O-CH3; -C(=O)-O-C2H5; -CH2-OH; -CH2-Cl or -CH2-. and</p>
    <p>Rlc represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH.</p>
    <p>19. Use of at least one substituted benzimidazolesulfonamide according to one or more of claims I to 15 of general formula Id, d md 74d / \ (CH)n</p>
    <p>N N :: Z1d N Id</p>
    <p>wherein Zd represents a nitrogen atom or a carbon atom bonded to another radical R4d (CR4d); Z2d represents a nitrogen atom or a carbon atom bonded to another radical R5d (CR5d); Z3d represents a nitrogen atom or a carbon atom bonded to another radical R (CR6d); Z4d represents a nitrogen atom or a carbon atom bonded to another radical S S. S..</p>
    <p>* S * 4 * S * . :: ;:. ;:. :.</p>
    <p>R7d (C_R7d); with the restriction that only one of the groups Z, Z2d, Z3d or Z4d can represent a nitrogen atom; Y' represents -CH2-O-CH2-or -CH2-NR-CH2-; nd represents 1,2,3 or4; md represents 0 or 1; R4d represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -N(CH3)2; -N(C2H5)2; -NH-C(=O)-CH3 or -NH-C(=O)-C2H5; R represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH2; -CH2-CH2-CH3; -CF3; -0-phenyl or -C(=O)-phenyl; which may be substituted with I or 2 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R6d represents a hydrogen atom; F; Cl; Br; -NO2; -NH2; -CH3; -CH2-CH3; -CH2-CH2-CH3; -CF3; -NH-C(0)-CH3; -NH-C(=O)-C2H5; -N=C=S; -0-phenyl or -C(=O)-phenyl; which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; R7d represents a hydrogen atom; F; Cl; Br or -NO2; and R1 td represents a hydrogen atom; -CH3; -CH2-CH3; -CH2-OH or -CH2-CH2-OH.</p>
    <p>* * . .** * * * * * * * * * * , I * flg I I S. I S * Q) . . I I I S I S * 1*1 *II I 20. Use of at least one substituted benzimidazolesulfonamide according to one or more of claims I to 19 selected from the group consisting of [1] 5-Benzoyl-N-ethyl-I H-benzimidazole-2-sulfonamide [2] N-Methyl-I H-benzimidazole-2-sulfonam ide [3] N-(2-Pyridyl)-I H-benzimidazole-2-sulfonamide [4J N-2-[(4-Morpholinoethyl)J-I H-benzimidazole-2-sulfonamide [5] N-(4-Aminobutyl)-I H-benzimidazole-2-sulfonamide [6] N-[3-(4-Morpholinopropyl)]-1 H-benzimidazole-2-su Ifonamide [7] 5-Chloro-N-ethyl-I H-benzimidazole-2-sulfonamide [8] 5-Phenoxy-N-ethyl-I H-benzim idazole-2-su Ifonam ide [9] N-[2-(3,4-Dimethoxyphenylethyl)]-1 H-benzimidazole-2-sulfonamide [101, N-Diethyl-I H-benzimidazole-2-sulfonamide [11] N-Butyl-IH-benzimidazole-2-sulfonamide [12] N-Ethyl-4,7-dichloro-5,
    6-dimethyl-I H-benzimidazole-2-sulfonamide [13] N-(4-Chlorophenyl)-I H-benzimidazole-2-sulfonamide [14] 5-Chloro-N-(4-chlorophenyl)-I H-benzimidazole-2-sulfonamide [15] 5-Chloro-N-(4-d iethylamino-I -methylbutyl)-1 H-benzimidazole-2-sulfonamide : 96: :.</p>
    <p>[17] 4-Chloro-5,6-d imethyl-N-ethyl-1 H-benzimidazole-2-sulfonamide [18] 4-Nitro-1 H-benzimidazole-2- sulfonamide [19] N-Ethyl-4-nitro-1 H-benzimidazole-2-sulfonamide [20] N-(4-Diethylamino-1 -methylbutyl)-1 H-benzimidazole-2-sulfonamide [211 N-Cyanomethyl-1 H-benzimidazole-2-sulfonamide [22] N-Cyclohexyl-1 H-benzimidazole-2-sulfonamide [23] N-(1 -Naphthyl)-1 H-benzimidazole-2-sulfonamide [241 N-Ethyl-5-trifluoromethyl-1 H-benzimidazole-2-sulfonam ide [25] N-(1 -Adamantyl)-1 H-benzimidazole-2-sulfonamide [261 2-(Sulfonyl-2-hydroxymethyl-1 -piperid inyl)-1 H-benzimidazole [27] N-(4-Methoxybenzyl)-1 H-benzimidazole-2-sulfonamide [28] N-(5-Methyl-3-isoxazolyl)-1 H-benzimidazole-2-sulfonamide [29] N-(2-Pyridylmethyl)-1 H-benzimidazole-2-sulfonamide [30] N-[2-(2-Pyridylethyl)]-I H-benzimidazole-2-sulfonam ide [31] 5-Benzoyl-N-(4-d iethylamino-1 -methylbutyl)-I H-benzimidazole-2-sulfonamide [32] 5-Nitro-1 H-benzimidazole-2-sulfonamide [33] N-Ethyl-5-nitro-1 H-benzimidazole-2-sulfonamide * a. a ass * a a a a a * S * I a a a a a : : : . 97 * a. * a.. *.. p [34] N-[2-(4-Morpholinoethyl)]-5-nitro-I H-benzim idazole-2-su Ifonamide [35] N, N-Diethyl-5-n itro-1 H-benzim idazole-2-sulfonamide [36] N-[3-(4-Morpholinopropyl)]-5-nitro-I H-benzim idazole-2-sulfonamide [37] N-Butyl-4-nitro-1 H-benzimidazole-2sulfonamide [38] N-(2-Hyd roxy-I -ethyl)-4-nitro-1 H-benzim idazole-2-su Ifonamide [39] N-Carboxyethylmethyl-4-nitro-1 H-benzim idazole-2-sulfonam ide [40] N-Ethyl-N,4-dinitro-1 H-benzimidazole-2-sulfonamide [41] N-[2-(4-Morpholinoethyl)]-4-n itro-I H-benzimidazole-2-su Ifonam ide [42] N-Acetyi-N-ethyl-4-nitro-1 H-benzim idazole-2-sulfonamide [43] N-Acetyl-4-n itro-I H-benzim idazole-2-su Ifonam ide [44] 2-[Sulfonyl-4-(2-hydroxy-1 -ethyl)piperazinylj-4-nitro-1 H-benzimidazole [45] N-(4-Fiuorophenyl)-4-nitro-1 H-benzimidazole-2-sulfonamide [46] 2-[Sulfonyl-2-(carboxymethyl)pyrrolid inyl]-4-n itro-I H-benzimidazole [47] N-Methyl-4-nitro-1 H-benzim idazole-2-sulfonam ide [48] N-Propyl-4-nitro-I H-benzimidazole-2-su Ifonamide [49] N-Isopropyl-4-n itro-1 H-benzimidazole-2-sulfonam ide [50] N-Ethylthioethyl-4-nitro-1 H-benzim idazole-2-sulfonamide S $ S S $ * * * S a a a * S S S. S a * flQ a S S S S a U * * aSS a.. * [51] N-Ethylsu lfonylethyl-4-nitro-I H-benzim idazole-2-sulfonam ide [52] N-[3-(2-Oxo-hexamethyleneim inyl)]-4-nitro-I H-benzimidazole-2-sulfonamide [53] N-[1 -[I, 3-Bis(carboxyethyl)propyl]]-4-nitro-I H-benzim idazole-2-sulfonamide [54J 2-[Sulfonyl-4-methylpiperazinyl]-1 H-benzimidazole [55] 5-Ch loro-N-cyclohexyl-I H-benzimidazole-2-su Ifonamide [56] N-(2-Diethylam mo-1-ethyl)-I H-benzim idazole-2-sulfonam ide [57] N-Ethyl-I H-im idazo[4, 5-b]pyridine-2-sulfonam ide [58] N-Butyl-I H-imidazo[4,5-b]pyridine-2-sulfonamide [59] N-Butyl-I H-imidazo[4,5-cjpyridine-2-sulfonamide [601 1,N-Diethyl-1 H-benzimidazole-2-sulfonamide [61] 1, N, N-Triethyl-I H-benzimidazole-2-sulfonamide [62] 1, N-Dimethyl-N-ethyl-1 H-benzim idazole-2-su Ifonamide [63] 1 -Benzoylmethyl-N-ethyl-I H-benzim idazole-2-sulfonamide [64] 1 -Acetylmethyl-N-ethyl-I H-benzimidazole-2-sulfonamide [65] N-Ethyl-I -(2-pyridylcarbonylmethyl)-I H-benzimidazole-2-su Ifonam ide [66] 5-Ch loro-N-(4-d iethylamino-I -methylbutyl)-1 -ethyl-I H-benzim idazole-2-* . .1 * I * I * 4 I</p>
    <p>I S S</p>
    <p>SI S S a flfl -I * S S a 44 4 III I*p S sulfonamide [67] 6-C hloro-N-(4-diethylam mo-I -methylbutyl)-1-ethyl-I H-benzim idazole-2-sulfonamide [68] 1, N-Diethyl-4-n itro-I H-benzim idazol-2-sulfonamide [69] 1,, N-Triethyl-6-nitro-I H-benzim idazole-2-sulfonamide [70] 1,, N-Triethyl-5-nitro-I H-benzim idazole-2-sulfonam ide [71] 5-Ch loro-I, N-d iethyl-N-(4-d iethylam mo-i -methylbutyl)-1 H-benzimidazole-2-sulfonamjde [72] 6-Chloro-1, N-d iethyl-N-(4-d iethylamino-1 -methylbutyl)-I H-benzimidazole-2sulfonamjcje [73] 1, N, N-Triethyl-4-nitro-I H-benzimidazole-2-su Ifonamide [74] I, N, N-Triethyl-7-nitro-I H-benzimidazole-2-su Ifonamide [75] 1, N-Diethyl-5, N-dinitro-1 H-benzimidazole-2-sulfonamide [76] 1, N-Diethyl-6, N-dinitro- l H-benzimidazole-2-sulfonamide [77] 1, N-Diethyl-5-n itro-I H-benzimidazole-2-su Ifonamide [78] 1, N-Diethyl-6-nitro-I H-benzimidazole-2-su Ifonam ide [79] 5-Amino-I H-benzimidazole-2-su Ifonamide [80] 4-Amino-l H-benzimidazole-2-sulfonamide [811 4-Amino-N-(carboxyethylmethyl)-I H-benzimidazole-2-sulfonamide S $ . a_I S a I I $ $ 1 d I I I a a aI I00 I S a I I *</p>
    <p>I III III I</p>
    <p>[82] 4-Amino-N-ethyl-I H-benzimidazole-2-sulfonamide [83] 4-Acetylamino-N-ethyl-1 H-benzimidazole-2-sulfonamide [84] 3,4-Dihydro-2H-2-ethyl-[I,2, 5]-thiadiazino[5,6-a]-benzimidazole-I, I -dioxide [85] 3,4-Dihydro-2H-[I,2,5]-thiadiazino[5,6-a]benzimidazole-I,I-dioxide [86] 3,4-Dihydro-2H-2-methyl-[I,2, 5]-thiadiazino[5,6-a]-benzimidazole-I, I -dioxide [87] 3,4, 5-Trihyd ro-2H-2-methyl-[I, 2,6]-thiadiazepino[6,7-a]-benzimidazole- 1,1-dioxide [88] 3,4,5-Trihyd ro-2H-2-ethyl-[1,2, 6]-th iad iazepino[6,7-aJ-benzimidazole- 1,1-dioxide [89] 3,4,5,6-Tetrahyd ro-2H-2-ethyl-[ 1,2,7]-th iad iazino-[7, 8-a]benzim idazole- 1,1-dioxide [90] 3,4-Dihydro-2H-[3-(4-morpholinopropyl)]-[1,2,5J-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [91] 3,4,5-Trihydro-2H-[2-(4-morpholinoethyl)]-[1,2,6]-thiadiazepino[6,7-a] benzimidazole-1,1-dioxide [92] 3,4-Dihyd ro-2H-2-ethyl-8-phenoxy-[1,2, 5]-th iad iazino-[5, 6-a]benzimidazole-1,1-dioxide [93] 3,4-Dihydro-2 H-2-ethyl-7-phenoxy-[ 1,2, 5]-th iad iazino-[5,6-ajbenzimidazole-1,1-dioxide S * * S S S * * . *S* * S S 01 S * * * S * S * * S S * S * t * S.. :.. *.</p>
    <p>[94] 8-Ch Ioro-3,4-d ihyd ro-2H-2-ethyl-7-phenoxy-[ 1,2, 5]th iad iazino-5,6-a]benzimidazole-1,1-dioxide [95] 7-Chloro-3,4-dihydro-2H-2-ethyl-7-phenoxy-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [96] 3,4,5-Trihydro-2H-[1,2,6]-thiadiazepino[6,7-a]benzimidazole-1,1-dioxide [97] 3,4-Dihydro-2 H-2-[2-(3,4-d imethoxyphenylethyl)]-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [98] 2H-2-Butyl-3,4-Dihydro-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [99] 6,9-Dichloro-3,4-dihydro-7,8-dimethyl-2H-2-ethyl-[1,2,5]-thiadiazino[5, 6-a]benzimidazole-1,1-dioxide [100] 8-Ch Ioro-3,4-d ihyd ro-2H-2-(4-diethylamino-1 -methylbutyl)-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [101] 7-Ch Ioro-3,4-d ihydro-2H-2-(4-d iethylamino-1 -methylbutyl)-[1,2, 5]-thiadiazino[5,6-a]benzimidazole-1, I -dioxide [102] 2H-2-(4-Chlorophenyl)-3,4-dihydro-[1,2,5]-thiadiazino-[5,6-a] benzimidazole-1,1-dioxide [103] 3,4-Dihyd ro-2 H-2-(5-methyi-3-isoxazolyl)-[ 1,2, 51-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [104] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [105] 3,4-Dihyd ro-2 H-2-ethyl-9-nitro-[1, 2, 5]-th iad iazino-[5,6-a]benzim idazole- 1,1-dioxide S * :: i02:.' : 5 [106] 3,4-Dihyd ro-2 H-2-ethyl-6-n itro-[ 1,2, 51-th iadiazino-[5,6-a]benzimidazole- 1,1-dioxide [107] 3-Hyd ro-2H-2-methyl-6-nitro-[1,2,4]-th iad iazolo[4,5-a]-benzimidazole-1,1-dioxide [108] 2 H-2-Cyclohexyl-3,4-d ihyd ro-[ 1,2, 5]-th iad iazino[5,6-a]-benzim idazole- 1,1-dioxide [109] 3,4-Dihydro-2H-2-(1 -naphthyl)-[1,2,5]-thiadiazino-[5,6-a]benzimidazole1,1-dioxide [110] 3,4-Dihydro-2H-2-ethyl-7-trifluoromethyl-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [111] 3,4-Dihyd ro-2H-2-ethyI-8-trifluoromethy-[1, 2, 5]-thiad iazino[5, 6-a]benzimidazole-1,1-dioxide [112] 2H-2-(1 -Adamantyl)-3,4-dihydro-[1,2,5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide [113] 7-Benzoyl-3,4-d ihydro-2H-2-ethyl-[1,2, 5]-thiadiazino-[5,6-a]benzimidazole-1,1-dioxide [114] 8-Benzoyl-3,4-d ihyd ro-2H-2-ethyl-[ 1,2, 5]-thiad iazino-[5, 6-a]benzimidazole-1,1-dioxide [115] 3,4-Dihydro-2H-2-(4-methoxybenzyl)-[1,2,51-thiadiazino-[5,6-a] benzimidazole-1,1-dioxide [116] 3,4-Dihydro-2H-2-(2-pyridylmethyl)-[1,2,51-thiadiazino-[5,6-a] benzimidazole-1,1-dioxide * I * * I * * * * * * ..n, * I ** * vJ * S * * S S S * S * *.. :.. SS [117] 3,4-Dihydro-2H-2-[2-(2-pyridylethyl)]-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [118] 8-Chloro-3,4-dihydro-2H-2-cyclohexyl-[1,2,5]-thiadiazino-[5,6-a] benzimidazole-1,1-dioxide [119] 7-Chloro-3,4-d ihydro-2H-2-cyclohexyl-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [120] 2-(2-Diethylamino-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [121] 8-Chloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-aJ-benzimidazole-1, 1-dioxide [122] 7-Chloro-3,4-dihydro-2H-[1,2,5J-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [123] 7, 8-Dichloro-3,4-d ihydro-2H-[1,2,5]-thiadiazino[5,
    6-aJ-benzimidazole- 1,1-dioxide [124] 2-Butyl-7,8-dichloro-3,4-dihydro-2H-9-nitro-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [125] 3,4-Dihyd ro-2H-2-ethyl-7-nitro-[1,2, 5]-thiad iazino-[5,6-a]benzimidazole- 1,1-dioxide [126] 3,4-Dihyd ro-2 H-2-ethyl-8-n itro-[ I,2,5]-thiadiazino-[5,6-a]benzim idazole- 1,1dioxide [127] 3,4-Dihydro-2H-2-methyl-7-nitro-[1,2,5]-thiadiazino-[5, 6-ajbenzimidazole-1,1-dioxide [128] 3,4-Dihyd ro-2H-2-methyl-8-nitro-[1, 2, 5]-thiad iazino-[5,6-</p>
    <p>S S</p>
    <p>* . S * * * S : : t04 * S * ** * S S S * S * *.S:.. , a]benzimidazole-1,1-dioxide [1291 3,4,5-Trihydro-2H-2-ethyl-8-nitro-[1,2,6]-thiadiazepino-[6,7-a] benzimidazole-1, 1-dioxide [130] 3,4, 5-Trihydro-2 H-2-ethyl-9-nitro-[ 1,2,61-thiadiazepino-[6,7-a]benzimidazole-1,1-dioxide [131] 2H-2-B utyl-3,4-d ihyd ro-7-n itro-[1, 2,5]-thiad iazino-[5,6-a]benzim idazole-1,1-dioxide [132] 2 H-2-Butyl-3,4-d ihyd ro-8-n itro-[1,2, 5]-thiad iazino-[5,6-a]benzim idazole- 1,1-dioxide [133] 3,4-Dihyd ro-2H-8-nitro-2-[2-(2-pyridylethyl)J-[ 1,2,5J-th iadiazino[5,6-a]benzimidazole-1,1-dioxide [134] 3,4-Dihyd ro-2H-7-n itro-2-[2-(2-pyridylethyl)]-[ 1,2, 5]-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [135] 3,4-Dihyd ro-2H-8-n itro-(2-pyridylmethyl)-[1,2, 5J-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [136] 3,4-Dihydro-2H-7-nitro-(2-pyridylmethyl)-[ I,2,5]-thiad iazino[5,6-a]benzimidazole-1,
    1-dioxide [137] 3,4,5,6-Tetrahydro-2H-2-ethyl-9-nitro-[ 1,2,7]-thiad iazozino[7, 8-a]benzimidazole-1,1-dioxide [138] 3,4,5,6-Tetrahydro-2H-2-ethyl-1 0-nitro-[1,2,7]-thiadiazozino[7,8-a]benzimidazole-1,1-dioxide [139] 3,4-Dihyd ro-2H-2-[3-(4-morpholinopropyl)J-7-nitro-[ 1,2,5]-thiadiazino[5,6-a]benzimidazole-1, I -dioxide e. **. .* . " :. .
    </p>..CLME: <p>* * :.. *.* [140] 3,4-Dihydro-2H-2-[3-(4-morpholinopropyl)]-8-n itro-[ 1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [141] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-7-nitro-[1,2, 5]-thiadiazino[5,6-ajbenzimidazole-1,1-dioxide [142] 2H-2-(4-Diethylamino-1 -methylbutyl)-3,4-dihydro-8-nitro-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [143] 3,4-Dihydro-2H-7-nitro-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [144] 3,4-Dihydro-2H-8-nitro-[1,2, 5J-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [145] 2H-2-(1 -Adamantyl)-3,4-dihydro-7-nitro-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1, 1-dioxide [1461 2H-2-( I -Adamantyl)-3,4-d ihydro-8-nitro-[ 1,2, 5]-th iad iazino[5,6-a]benzimidazole-1,1-dioxide [147] 7-Amino-3,4-d ihyd ro-2H-2-ethyl-[1, 2, 5J-th iad iazino-[5,6-a]benzimidazole-1,1-dioxide [148] 3,4-Dihyd ro-2H-2-ethyl-7-isoth iocyanato-[1,2,5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [1491 7-Acetylamino-3,4-dihydro-2H-2-ethyl-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [150] 2-Carboxyethylmethyl-8-chloro-3,4-d ihydro-2H-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide</p>
    <p>S</p>
    <p>:: 16 *: ::: a. * *.. :.. * [151] 2-Carboxyethylmethyl-7-chloro-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a] benzimidazole-1,1-dioxide [152] 8-Chloro-2-(6-chioro-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [153] 7-Chloro-2-(6-chloro-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [154] 8-Chloro-2-(2-chloro-I -ethyl)-3,4-d ihyd ro-2 H-[1,2, 5]-th lad iazino[5,6-a]benzimidazole-1,1-dioxide [155] 7-Chloro-2-(2-chloro-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [156] 2-(3-Ch loro-I -propyl)-3,4-d ihydro-2H-7-nitro-[1,2, 5]-thiad iazino[5,6-a]benzimidazole-1, 1-dioxide [157] 8-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-ajbenzimidazole-1,1dioxide [158] 7-Chloro-2-(4-cyano-1 -butyl)-3,4-dihydro-2H-[1,2,5J-thiadiazino[5,6-a]benzimidazole-1,
    1-dioxide [159] 2-{3-[N-methyl-N-[2-(3,4-d imethoxyphenyl)ethylj]-propylamino}-3,4-d ihyd ro-2 H-7-nitro-[1,2, 5]-thiad iazino-[5,6-a]benzim idazole-1,1-dioxide [160] 8-Chloro-2-(6-diethylamino-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [161] 7-Chloro-2-(6-diethylamino-1 -hexyl)-3,4-dihydro-2H-[1,2,5J-thiadiazino[5,6-ajbenzimidazole-1,1dioxide [162] 8-Chloro-2-cyanomethyl-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-</p>
    <p>S</p>
    <p> I:. : ! a]benzimidazole-l,1-dioxide [163] 7-Chloro-2-cyanomethyl-3,4-dihydro-2H-[1,2,5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [164] 8-Chloro-2-(2-diethylamino-1 -ethyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,i [165] 7-Ch Ioro-2-(2-diethylam mo-I -ethyl)-3,4-d ihyd ro-2 H-El,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [1661 7-Chloro-2-(6-ethylamino-1 -hexyl)-3,4-dihydro-2H-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1dioxide [167] 7-Chloro-2-(2-pyridyl)-3,4-d ihydro-2 H-[1,2, 5]-th iad iazino[5,6- a Jbenzimidazole-1,1-dioxide [168] 3,4-Dihydro-2H-2-ethyl-3-methyl-[1,2, 5J-thiadiazmno[5,6-a]benzimidazole-1, 1-dioxide [169] 3,4-Dihyd ro-2H-2-ethyl-3-methyl-7-n itro-[ 1,2, 5]-thiad iazino[5,6-a]benzimidazole-1,1-dioxide [170] 3,4-Dihyd ro-2H-2-ethyl-3-methyl-8-nitro-[1,2, 5]-thiad iazino[5, 6-a]benzimidazole-1,1-dioxide [171] 2H-2-Butyl-3,
    4-dihydropyrido[3',2':4,5]imidazo[1,2-e]-[1,2,5] -thiadiazine-1,1-dioxide [1721 2-Butyl-3,4-dihydro-2H-pyrido[3',4':4,5]imidazo[1,2-el-[l,2,5] -thiadiazine-1,1-dioxide [173] 1,2,3,4,1 3,14-Hexahydropyrido[1,2':2,3]-[1,2,5]-thiadiazino[5,6-a]benzimidazole-6, 6-dioxide * * **. **. * S..</p>
    <p>: :18 * * S S * * S S *5 * * * . S 5 S *** S</p>
    <p>E</p>
    <p>[174] 1,2,3,4,13, 14-Hexahydro-9-nitropyrido[I,2':2,3]-[1,2,5]-thiadiazino[5,6-a] benzimidazole-6,6-d ioxide [175] 1,2,3,4,1 3,14-Hexahydro-1 0-nitropyrido[1,2':2,3]-[1,2,5]-thiadiazino[5,6-a]benzimidazole-6, 6-dioxide [176] 2H-2-Ethyl-[1,2,5]-thiadiazino[5,6-a]benzimidazole-1,1-dioxide [177] 2H-2-Ethyl-3-methyl-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1, 1dioxide [178] 2H-2-Ethyl-3-phenyl-[1,2, 5]-thiadiazino[5,6-a]-benzimidazole-1, 1-dioxide [179] 2H-2-Ethyl-7-nitro-3-(4-nitrophenyl)-[1,2, 5]-thiadiazino-[5,6-a]benzimidazole-1, 1-dioxide; [180] N-ethyl-I -((2-oxo-2,3-dihydrobenzo[d]imidazol-I -yl)methyl)-I H-benzo[djimidazole-2-sulfonamide and [181] I,2,3,4,13,14-Hexahydro-9,I0-dinitropyrido[I',2':2,3]-[I,2,5]-thiadiazino [5,6-a]benzimidazole-6,6-dioxide optionally in form of one of its stereoisomers, preferably enantiomers or diasteromers, a racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers, in any mixing ratio, or a physiologically acceptable salt thereof, or a corresponding solvate thereof.</p>
    <p>21. Use of at least one substituted benzimidazolesulfonamide of general formula I, Ia, Ib, Ic or Id according to one or more of claims I to 20 for the manufacture of a medicament for the regulation of appetite; for the maintenance, increase or</p>
    <p>S</p>
    <p> . S * * * . .: :109 ** a 4 S S S " :.. *.</p>
    <p>reduction of body weight; or for the prophylaxis and/or treatment of obesity, bulimia, anorexia, cachexia or type II diabetes (non insulin dependent diabetes mellitus), more preferably for the prophylaxis and/or treatment of obesity.</p>
    <p>22. Use of at least one substituted benzimidazolesulfonamide of general formula I, Ia, lb, Ic or Id according to one or more of claims I to 20 for the manufacture of a medicament for the prophylaxis and/or treatment of stroke; seizures; migraine; head trauma; epilepsy; irritable colon syndrome; irritable bowel syndrome; disorders of the central nervous system; anxiety; panic attacks; depression; bipolar disorders; obsessive compulsory disorder; cognitive disorders; cognitive dysfunction associated with psychiatric diseases; memory disorders; memory loss; senile dementia; mood disorders; sleep disorders; psychosis; neurodegenerative disorders, preferably selected from the group consisting of Morbus Alzheimer, Morbus Parkinson, Morbus Huntington and Multiple Sclerosis; schizophrenia; chronic intermittent hypoxia; convulsions; or hyperactivity disorder (ADH D, attention deficit/hyperactivity disorder).</p>
    <p>23. Use of at least one substituted benzimidazolesulfonamide of general formula I; Ia, Ib, Ic or Id according to one or more of claims I to 20 for the manufacture of a medicament for the improvement of cognition (cognitive enhancement) and/or for the improvement of cognitive memory (cognitive memory enhancement).</p>
    <p>24. Use of at least one substituted benzimidazolesulfonamide of general formula I; Ia, Ib, Ic or Id according to one or more of claims I to 20 for the manufacture of a medicament for the prophylaxis and/or treatment of drug addiction and/or withdrawal, preferably for the prophylaxis and/or treatment of addiction and/or withdrawal related to one or more of drugs selected from the group consisting of benzodiazepines, natural, semisynthetic or synthetic opioids like cocaine, ethanol and/or nicotine.</p>
    <p> a a * ;I10. a a a. * -*P</p>
GB0604775A 2006-03-09 2006-03-09 Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake Withdrawn GB2435825A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB0604775A GB2435825A (en) 2006-03-09 2006-03-09 Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB0604775A GB2435825A (en) 2006-03-09 2006-03-09 Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake

Publications (2)

Publication Number Publication Date
GB0604775D0 GB0604775D0 (en) 2006-04-19
GB2435825A true GB2435825A (en) 2007-09-12

Family

ID=36241299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0604775A Withdrawn GB2435825A (en) 2006-03-09 2006-03-09 Benzimidazole-2- & pyrido[d]imidazole-2- sulphonamide derivatives for treatment of disorders mediated via 5-HT6 receptors, eg those related to food intake

Country Status (1)

Country Link
GB (1) GB2435825A (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0355827A2 (en) * 1988-08-24 1990-02-28 Mochida Pharmaceutical Co., Ltd. Hydantoin derivatives
WO2005014589A1 (en) * 2003-07-30 2005-02-17 Laboratorios Del Dr. Esteve S.A. Benzoxazinone-derived sulfonamide compounds, their preparation and use as medicaments

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0355827A2 (en) * 1988-08-24 1990-02-28 Mochida Pharmaceutical Co., Ltd. Hydantoin derivatives
WO2005014589A1 (en) * 2003-07-30 2005-02-17 Laboratorios Del Dr. Esteve S.A. Benzoxazinone-derived sulfonamide compounds, their preparation and use as medicaments

Also Published As

Publication number Publication date
GB0604775D0 (en) 2006-04-19

Similar Documents

Publication Publication Date Title
CA2596636C (en) Heterocyclyl substituted phenyl methanones as inhibitors of the glycine transporter 1
ES2350460T3 (en) DERIVATIVES OF 3-AZA-BICICLO [3.1.0] HEXANO.
CA2610042C (en) 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses
ES2371514T3 (en) 3-AZA-BICYCLE COMPOUNDS [3.3.0] OCTANO.
BRPI0720876A2 (en) 2-AZA-BICYCLE DERIVATIVE COMPOUNDS [3.1.0] HEXAN AND USES OF THESE.
AU2005315914A1 (en) Bi- and tricyclic substituted phenyl methanones as glycine transporter I (GlyT-1) inhibitors for the treatment of Alzheimer&#39;s disease
CA2589695A1 (en) Thiazolopyridinone derivates as mch receptor antagonists
AU2007217040A1 (en) Compounds having 5-HT6 receptor affinity
KR101800607B1 (en) 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives
EP2235014A2 (en) Bicyclic derivatives of azabicyclic carboxamides, preparation thereof and therapeutic use thereof
WO2007028460A1 (en) TETRAHYDRO-β-CARBOLIN-SULFONAMIDE DERIVATIVES AS 5-HT6 LIGANDS
WO2010004507A1 (en) Thiazolidine compounds as orexin receptor antagonists
MX2007001541A (en) Substituted indole compounds, their preparation and use in medicaments.
ES2327847T3 (en) DERIVATIVES OF 5-INDOLILSULFONAMIDS, THEIR PREPARATION AND THEIR USE AS MODULATORS OF 5-HT-6.
NZ545301A (en) Indole-6-sulfonamide derivatives, their preparation and their use as 5-ht-6 modulators
WO2012114252A1 (en) Novel indole and pyrrolopyridine amides
WO2010002802A1 (en) Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity
KR0145706B1 (en) Antipsychotic 3-piperazinyl benzazole benzisoxozole and benzisothiazole derivatives
AU2004237420B2 (en) Use of sulphonamide derivatives for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion
WO2006051410A1 (en) Azabenzoxazoles for the treatment of cns disorders
JP3980054B2 (en) Antipsychotic 4- (1H-indolyl-1-yl) -1-substituted piperidine derivatives
EP1947085A1 (en) Substituted indole sulfonamide compounds, their preparation and use as medicaments
CN100518736C (en) Indol-4 sulfonamide derivatives, their preparation and their use 5-ht-6 as modulators
GB2435827A (en) Use of substituted piperazine compounds for the treatment of food related disorders
KR20230015404A (en) Competitive and non-competitive inhibitors of the muscarinic acetylcholine receptor M5

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)