Synthesis of Essential Drugs

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1 -., f Synthesis of Essential Drugs R.vS. Vardanyan V.J. Hruby Dt pml»u nl nt Chcini\lr\ IMH> I I ~m\cr\it\ I /m. / M;\ <>! \nroiui I in son. I S\ HiiEVIER Amsterdam - Boston - Heidelberg - London - New York - Oxford Paris - San Diego - San Francisco - Singapore - Sydney - Tokyo

2 Preface vii 1 General Anesthetics Inhalation anesthetics Noninhalation anesthetics 4 2 Local Anesthetics Local Anesthetics of the Aminoether Series Local Anesthetics of the Aminoamide Series Topical Anesthetics 17 3 Analgesics Opioid Analgesics Agonists Mixed agonists/antagonists Opioid antagonists Nonsteroid Anti-Inflammatory Drugs and Anti-Fever Analgesics Salicylic acid derivatives Pyrazolonees p-aminophenol derivatives Anthranylic acid derivatives Propionic acid derivatives Acetic acid derivatives Indolyl/indeneacetic acids Oxicames 51 4 Soporific Agents (Hypnotics and Sedative Drugs) Barbiturates Long-acting barbiturates Intermediate-acting barbiturates Short-action barbiturates Ultrashort-action barbiturates Benzodiazepines Other Hypnotics and Sedative Drugs 65 5 Anxiolytics (Tranquilizers) Benzodiazepines Anxiolytic of Nonbenzodiazepine Structures 78

3 6 Antipsychotics (Neuroleptics) 6.1 Phenothiazine derivatives Thioxanthene derivatives Butyrophenone derivatives Dihydroindolone derivatives Dibenzoxazepine and dibenzdiazepine derivatives Diphenylbutylpiperidine derivatives Other neuroleptics Lithium derivatives Antidepressants Tricyclic Antidepressants Tertiary amines representatives of tricyclic antidepressants Secondary amines representatives of tricyclic antidepressants Monoaminooxidase Inhibitors Second-Generation Antidepressants (Atypical Antidepressants) Amphetamines and other CNS Stimulators Central Nervous System Stimulants Psychomotor Stimulants Methylxanthines Amphetamines, methylphenidate, and pemoline Respiratory Stimulants or Analeptics Appetite Suppressants or Anorectics Antiepileptic Drugs Hydantoin Derivatives Barbiturates Succinimides Valproic Acid Carbamazepine Benzodiazepines Acetazolamide Oxazolidines Antiparkinsonian Drugs Drugs Affecting the Dopaminergic Systems of the Brain Anticholinergic Drugs (Central Cholinoblockers) 138 VI Adrenergic (Sympathomimetic) Drugs Direct-Acting Agonists Drugs stimulating a- and /3-adrenoreceptors 146

4 Drugs stimulating predominantly ^-adrenoreceptors Drugs stimulating predominantly a-adrenoreceptors Antiedema sympathomimetics Indirect-Acting Agonists Agonists of Mixed Action Adrenoblocking Drugs J3-Adrenoblockers a-adrenoblockers Long-lasting noncompetitive antagonists Nonselective, reversible competitive adrenoblockers Reversible, competitive a,-selective adrenoblockers Ergot alkaloids (alkaloids of ergot) Selective 0,-adrenoblockers Adrenergic Neuron Blockers Cholinomimetics Direct-Acting Cholinomimetics Choline esters Natural muscarinic alkaloids Natural nicotinic alkaloids Indirect-Acting Cholinomimetics Reversible cholinesterase inhibitors Carbamates Quaternary amines Irreversible cholinesterase inhibitors Other organophosphorous cholinesterase inhibitors Anticholinergic Drugs Antimuscarinic Drugs Alkaloids Anticholinergics of the quaternary amine series Antiparkinsonian drugs of the quaternary amine series Antispasmodics of the tertiary series Mydriatics of the tertiary amine series Ganglioblocking Substances Muscle Relaxants Neuromuscular Junction Blocking Agents Antidepolarizing neuromuscular junction blockers Depolarizing neuromuscular blockers Direct-Acting Muscle Relaxants Centrally Acting Muscle Relaxants 215

5 16 Antihistamine Drugs H, Antihistamine Drugs Aminoalkyl esters Ethylenediamines Alkylamines Piperazines Phenothiazines Piperidines H, Receptor Antagonists Cardiotonic Drugs Cardiac Glycosides Other Positive Inotropic Drugs Antiarrhythmic Drugs Group I Drugs Subgroup IA Subgroup IB Subgroup IC Group II Drugs Group III Drugs Group IV Drugs Antianginal Drugs Nitrates and Nitrites js-adrenoblockers Calcium channel blockers Other drugs Hypolipidemic Agents Bile acid sequesters Drugs that inhibit cholesterol synthesis Other drugs Diuretics Osmotic Diuretics Carbonic anhydrase Activity Suppressing Diuretics Thiazide Diuretics Drugs related to thiazide diuretics Loop Diuretics Potassium Sparing Diuretics 288

6 22 Antihypertensive Drugs Diuretics Thiazide diuretics Thiazide-related drugs Potassium sparing diuretics /3-adrenoblockers Centrally acting adrenergic drugs (sympatholytics) Peripherally acting sympatholytics (a-adrenoblockers) Reversible competitive «-selective adrenoblockers Adrenergic neuron blockers Calcium channel blockers Myotropic hypotensive drugs Angiotensin-converting enzyme inhibitors Calcium channel activators Drugs for Treating Respiratory System Illnesses Antiedema, Vasoconstricting Drugs Anticough and Expectorant Agents Narcotic anticough drugs Non-narcotic anticough drugs Expectorant drugs Bronchodilators (Broncholytics) Methylxanthines Anticholinergic drugs Inhibitors of allergy mediator release Corticosteroids Adrenergic drugs (/J : -receptor agonists, sympathominietics) Anticoagulants, Antiaggregants, Thrombolytics, and Hemostatics Anticoagulants Direct-acting coagulants or parenteral anticoagulants Direct-acting coagulants, or enteral anticoagulants Antiaggregants Fibrinolytics (Thrombolytics) Hemostatics (Procoagulants) Systemic hemostatics Local procoagulants Thyroid Hormone and Antithyroid Drugs Drugs for Treating Hypothyroidism }}H 25.2 Drugs for Treating Hyperthyroidism Insulin and Synthetic Hypoglycemic Agents Insulin Synthetic Hypoglycemic Drugs 344

7 27 Corticosteroids Glucocorticoids Mineralocorticoids Female Sex Hormones Estrogens Antiestrogens Progestins Male Sex Hormones and Anabolic Steroids Androgens Androgen Antagonists Anabolics Antineoplastics Antimetabolites Folic acid antagonists Purine derivatives Pyrimidine derivatives Alkylating agents Nitro-containing mustard derivatives Ethylenimine derivatives Alkyl sulfonates Nitrosoureas Antibiotics Dactinomycines Bleomycins Anthracyclines Compounds isolated from plants Epipodophyllotoxins Hormonal drugs Androgens Estrogens Progestins Corticosteroids Nonhormonal drugs Other antineoplastic drugs Immunopharmacological Drugs Immunostimulants Immunodepressants Glucocorticoids Cytotoxic drugs 422

8 32 Antibiotics Beta-Lactam Antibiotics Penicillins Cephalosporins Penems and carbapenems Monobactams Macrolide Antibiotics Tetracyclines Aminoglycosides Lincosamides Chloramphenicol Other Antibiotics Antimicrobial Drugs Sulfonamide Drugs and Trimethoprim Diaminopyrimidines (trimethoprim. pyrimethamine. and trimethoprim-sulfamethoxazole) Quinolones Nitrofuranes Antimycobacterial Drugs Antituberculosis Drugs Drugs of the first group Drugs of the second group Drugs for Treating Leprosy Antifungal Drugs Polyene Antifungal Drugs Imidazoles (Triazoles) Allylamines Others Antiviral Drugs Drugs for Treating Protozoan Infections Antimalarial Drugs Drugs effective against the erythrocvte stage of plasmodia infection Drugs effective against the hepatic (exoerythrocyte) stage of plasmodia infection 570

9 Drugs effective against hepatic and erythrocyte forms of plasmodia infection Drugs for Treating Amebiasis Drugs for Treating Leishmaniasis Drugs for Treating Trypanosomiasis Drugs for Treating Other Protozoan Infections Antihelmintic Drugs 583 Index 595

Table of Contents. 1. General Anesthetics. 1.1 Inhaled Anestethics 1.2 Noninhaled Anesthetics. 2. Local Anesthetics

Table of Contents. 1. General Anesthetics. 1.1 Inhaled Anestethics 1.2 Noninhaled Anesthetics. 2. Local Anesthetics Table of Contents 1. General Anesthetics 1.1 Inhaled Anestethics 1.2 Noninhaled Anesthetics 2. Local Anesthetics 2.1. Local Anesthetics of the Aminoether Series 2.2. Local Anesthetics of the Aminoamide