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Index Symbols β-Adrenoreceptor-blocking drugs (–)-Pseudoephedrine 53 403 (-) 3S, 4R-Enantiomer of α-Adrenergic 305 β-Agonist 384 cromakalim 890 α-Adrenergic blocking activity β-Antagonist 391 (-) Bromhexine hydrochloride 390 β-Blockers 364, 882, 889 566 α-Adrenergic Blocking Drugs β (BIC) 827 344 -Halo-arylamines 34 β (DIC) 827 α-Adrenoceptor Blocking Agents -Ketoacidosis 669 (MIC) 827 388, 389 β-Lactam antibiotics 737 (R) and (S) Isomers of ampheta- α β-Lactam inhibitors 751 -Adrenoreceptor antagonists mine 270 388 β-Lactam ring 743 (R)-Amphetamine 270 α-Designation 865 β-Lactamase 748, 750, 758, (S) – (+) Naproxen sodium 52 α-Eucaine 140, 141 759, 762 (Z)-Isomer 514 α-Glucosidase inhibitors β-Lactamase activity 760 β [D-Ala2, D-Leu5] enkephalin 672, 682 -Dimethylcysteine 738 310 α β -Glycosidase as a substrate 683 -Lactam structure 741 1, 3-Diaminoinositol 789 α β -Methylnorepinephrine 354 -Lactamase combinations 751 11-Hydroxy CPZ 846 α β -Prodine 548, 549 -Lactamase producers 751 11β-Hydroxysteroid α-Adrenerging blocking drugs β-Lactamase-producing Gram- dehydrogenase 722 367 negative organisms 758 14C-Labelled substrate 782 α -Lipoproteins 868 β-Lactams 742, 761 16β-Hydroxy-17β-estradiol 705 α -Prodine 548 β-Lipoproteins 868 17-Hydroxy-CPZ 846 α β 1-Adrenoreceptors 388 -Naphthyl salicylate 281 17β-Estradiol 688, 705 α β 1-Agonist 384 -Receptor-blocking pharmaco- 197Hg isotope 443 α logical characteristic 2-Adrenergic receptors 354 2, 3-Diphosphoglycerate (DPG) α features 384 analogues 71 2-Adrenoreceptors 388 α β-Receptors 55, 384 2, 5A Synthetase 857 2-Agonist activity 354 α β-Solamarine 825, 826 2-Deoxystreptamine 789 2-Agonists 391 α β-Substituting groups 687 2-Hydroxy-5-nitrobenzyl chloride 2-Globulin 349 α β-Tubulin 657 618 2-Receptors 388 β1 and β agents 386 2-Hydroxyestrone 705 17α-Hydroxyestrone 705 2 β β-Adrenergic activity 387 1-Partial agonist 398 2-Log-drug 800 β β-Adrenergic agonist 884 2-Adrenergic stimulant 54 2-Methoxyestrone 705 β β-Adrenergic blocking drugs 344 2-Agonist 387 2-Nitroaniline 24, 25 β 2D Display coordinates 67 β-Adrenergic receptor agonists 2-Receptors 387 386 β2-Selective bronchodilator 387 3, 4, 5-Trimethoxybenzaldehyde 643 β-Adrenergic receptors 371 3, 4, 5-trimethoxy benzoid acid 3, 4-Dihydroxyphenylalanine β-Adrenoceptor Blocking Agents 838 (DOPA) 431 391 (–) 3S, 4R Cromakalin 890 3, 4-Dihydroxyphenylethylamine β (–)-Ephedrine 53 -Adrenoreceptor antagonist 889 431 897 898 MEDICINAL CHEMISTRY 3-Bromo-4 (hexylamino)-N- 4-Log drug 799, 800 7-Log combination 800 hexyl-1, 894 4-Phenylpiperidine analogues 8-Naphthalimide 894 3-Diethylamino propyl ester of 3, 322 8-Amino quinoline structural 4, 5-Trimethoxy 838 4′-Hydroxy fenoprofen analogues 632 3-Log drug 799, 800 glucuronide 533 8-Aminoquinoline 637 3-Quinoline carboxylic acid 786 5, 5-Diphenylhydantoin 216 8-Aminoquinoline analogues 623 3, 4-Dihydroxyhexylethylamone 5, 5-Diphenylhydantoin sodium 9-Aminoacridines 632 431 220 99 mTc 889 11β-Hydroxysteroid 5α-Cholestane 689 dehydrogenase 722 A 5-CH3 hydroxylation 518 3-Tubulin 657 5-Ethyl-5-phenylhydantoin 220 A-Type compounds 865 3D Chemical databses 74 5-Fluorodeoxyuridine-5′- Aberrant calcium signalling 219 3D Contour map 73 monophosphate Abnormal synchronous discharg- 3D Database from chemical (FUMP) 816 ing 218 abstracts 74 5-Fluorouracil from uracil 47 Absence seizures 219, 220 3D Database searching methods 5-Fluorouracil 47 Absolute configuration 55 79 5-Hydroxytryptamine 89 Absorption, distribution, metabo- 3D Databases 74 5α-Pregnane 688 lism and excretion (ADME) 3D Isoptential contour map 89 5α-Androst-8-ene 688 22, 90, 91 3D Search 75 5-Substituted hydantoins 216 Acarbose 682 3D Structure 60 5′, 3′-Phosphodiester bond 892 ACE inhibitors 87, 88, 889 3D Structure of macromolecular 5α, 8α-Androstane 689 Acetamido functional moiety targets 66 5α-Androst-8(14)-ene 688 396 3D Structure of macromolecular 5α-DHT 696 Acetaminophen 276, 274, 275, targets 66 297, 300, 298 5α-Dihydrotestosterone 696 3D Transformed ‘world coordi- Acetophentidine 274 5α-Estrane 688 nates’ 67 Acetanilid 299 5α-Reductase 697 3D-Databases 73, 74 Acetanilide 5, 274, 276, 278, 5β-Androstane 688, 689 3D-Databases of ligands 76 279, 298, 585, 656 5β-Pregnane-3α-20α-diol(I) 709 3D-Orientation 50 Acetazolamide 457, 458, 3D-QSAR 88 6-Deoxy-6-demethyltetracycline 459, 461 ′ 776 4, 4 -Diaminodiphenyl sulfone Acetohexamide 673 644 6-Deoxy-6- Acetyl salicylic acid 15, 284 4-Aminoquinoline analogues methylenetetracyclines 776 Acetyl sulphafurazole 597 614, 632 6-Hydroxytryptamine 89 4-Aminoquinoline counterparts 6-Keto-prostaglandin F1α Acetylcholine 10, 16, 16, 623 42, 156, 245, 399, 399, (6-oxo-prostaglandin F1α) 424 4-Aminoquinoline drugs 622 867 Acetylcholine chloride 403, 4-Aminoquinolines 623, 636, 6α-Hydroxytestosterone 696 637 400, 399 6-Mercaptopurine 814 4-Hydroxy cyclophosphamide Acetylcholinesterase 407 7-ACA 754, 755 804 Acetylcystein 566 7-Aminocephalosporanic acid 4-Hydroxyestrone 705 755, 754 Acetylcysteine 568 INDEX 899 Acetylsalicylic acid 15 Adipate 654 AIDS-vaccines 891, 894 Acrylic 218 Adjuvant therapy 541 Al-Mg-antacids 785 Aciclovir 858 Adrenal cortex 718 Albendazole 655, 656, 657 Acid (DNA) 854 Adrenal cortical hormones 686 Albuterol 386, 387 Acidotic diuretics 477 Administered antineoplasmic Alcuronium chloride 227, 232 Acquired immunodeficiency drug 798 Aldol condensation 142, 263 syndrome (AIDS) 890 Adrenoreceptor antagonists 388 Aldophosphamide 804 Acriquine 637 Adrenoceptor blocking agents Aldosterone 471, 472, 718, Acrivastine 509 388 873 ACTH 472 Adrenergic stimulant 54 Aldosterone antagonists 872 Actinomycin C 818 Adreno-receptor blocking drugs Aldosterone titer values 720 Actinomycin D 818 403 Aldosterone inhibitors 471 Action potential 219 Adrenal cortical steroids 718 Algorithm 73 β Adrenal corticoids 730 Activation of 1-receptors 384 Alimemazine 503 Active benzoyl ecognine 129 Adrenal steroids 537 Alkali therapy 598 Active cavity 69 Adrenaline 376 Alkaloids 823, 837 Active conformers 93 Adrenaline 147, Alkylating agents 801 374, 375, 376, 385 Active drug 466, 220 Alkylating antineoplastics 800 Adrenergic 375 Active metabolite 220, 300, Alkylene diols 839 Adrenergic blocking profile 34 367, 480, 507, 583, Allobarbital 179 Adrenergic neuron blockers 375 816, 860 Allopurinol 539, 541, 813 Adrenergic neuron blocking Active metabolite FUMP 816 Allosteric sites 71 agents 431 Active site 69, 73, 76, 83 Aloprostadil 866 Adrenergic receptors 55 Active site for a target molecule Alpha-adrenoceptor 389 69 Adrenocortical steroids Alpha-shape method 69 Active steroids 696 718, 720, 732 Alprostadil 866, 867 Actual receptor mapping 88 Adrenocorticosteroids 830 Alternative drug 761, 775, 790 Acute myocardial infarction 337 Adrenocorticotropic hormone (ACTH) 472 Althiazide 454, 455 Acyclic tertiary amines 821 Adriamycin 827 Altizide 445, 454, 455 Acyclovir 857, 858, 859, 860 Advanced molecular graphics 70 Al-Mg antacids 785 Acyclovir 860 Aedes aegypti mosquito 613 Amantadine 553, 560 Acylamino-propanediol chain Amantadine hydrochloride 556, 771 Age Incidence 795 560, 561, 855 Addison’s disease 696 Agents 386 Amantadinum 855 Adenine 814 Aglycones 710 Amantidine 856 Adenine deaminase 860 Agonists/antagonists 335 AIDS 890, 891, 892, 893, 894 Amantidine hydrochloride Adenocarcinoma strains 818 855, 856 Adenosine 255 AIDS immunoglobulin prepara- tions 893 Amaryllidaceae alkaloids 821 Adenosine triphosphate (ATP) Amaryllidaceae group of alka- 658 AIDS-Immunoglobulins 891, 893 loids 820 Adenylate cyclase stimulants 884 AIDS-related complex (ARC) Amethocaine 164 Adenylate cylase activity 312 891, 892, 893 900 MEDICINAL CHEMISTRY Amethocaine hydrochloride 135 Amodiaquine iminoquinone 622 Analgesic-antipyretic 275 AMI-H-atom abstraction 91 Amoxicillin trihydrate 753 Anhydrotetracycline 774 Amidase enzymes 676 Amorphous zinc-insulin compo- ANS 374 Amidopyrine 288, 289 nent 670 Antagonists 335 Amikacin 761, 785 Amoxicillin 749, 753 Angiotensinogen 349 Amino Acid Antagonists 817, AMPA 219, 268 Anileridine 325 811 Amphetamine 255 Anileridine hydrochloride 322, Aminoacetaldehyde 739 Amphetamine-type hallucino- 325, 326, 338 Aminoacetyl-t-RNA 789 genic drugs 7 Aniline 277, 286 Aminoacrichin 636, 637 Amphetamines 254, 270 Aniline and p-Aminophenol Aminoadipyl side-chain 754 Ampicillin 748, 749, analogues 275 Aminoalcohol 425 753, 756, 770 Aniline-based analgesic-antipy- Aminoalcohol carbamates Ampicillin-resistant strains 758 retic 275 416, 424 Amrinone 883, 884 Anodynes 566 Aminoalcohol esters 409, 423 Amylobarbitone 180 Anopheles mosquito 613 Aminoalcohol ethers 416, 424 Amylocaine 131 Antazoline 497 Aminoalcohols 417, 425 An opioid 308 Antazoline hydrochloride 497, Aminoalkylethers 485, 486, Anabolic activity 696 498, 500 560, 514 Anaesthesia 106 Anthelmintic 654 Aminoamides 425 Anaesthesiophoric moiety Anthelmintics Aminoglycosides 789, 790, 791 129, 155 652, 653, 654, 661 Aminometradine 474 Anaesthetic ether 107 Anthracyclines 819 Aminopenicillin oral prodrug Anaesthetist 247 Anti-muscarinic agents 408 749 Analeptics 256, 260 Anti-psychotics 304 Aminopenicillins 748 Analgesic 305, 579 Anti-UV erythema 301 Aminophenazone 288, 542 Analgesic activity 579 Antiabsence activity 221 Aminophylline 256, Analgesic drugs 297 Antiandrogens 871 258, 259, 269 Antiasthamatics 867 Aminopterin 47 Analgesics 275 Antibacterial activity 754, 791 Aminopyrine 288, 289, 300, Analogues 3 Antibacterial agent 644 542 Analogues of purines 811, 813 Aminosalicylic acid 785 Analogues of pyrimidines Antibiotic 736, 788, 818 Amiodarone 365,
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    Eu^^esP— || | MMMMI 1 1 1 1 1 1|||| 1 1 1||| || J European Patent Office _ _ _ _ _ © Publication number: 0 665 009 A1 Office europeen desj brevets © EUROPEAN PATENT APPLICATION published in accordance with Art. 158(3) EPC © Application number: 93922625.4 © Int. CI.6: A61 K 9/00 @ Date of filing: 13.10.93 © International application number: PCT/JP93/01469 © International publication number: WO 94/08561 (28.04.94 94/10) ® Priority: 14.10.92 JP 303085/92 Koga-gun, Shiga 520-32 (JP) @ Date of publication of application: Inventor: IZUMI, Shougo 02.08.95 Bulletin 95/31 3-94, Nlshltsutsujlgaoka Mlyamadal 1-chome Kameoka-shl, © Designated Contracting States: Kyoto 621 (JP) AT BE CH DE DK ES FR GB GR IE IT LI LU MC Inventor: OKA, Masaakl NL PT SE 18-8-207, Hoshlgaoka 1-chome Hlrakata-shl, © Applicant: NIPPON SHINYAKU COMPANY, Osaka 573 (JP) LIMITED 14, Klssholn Nlshlnosho Monguchlcho Mlnaml-ku © Representative: Vogeser, Werner, Dipl.-lng. et Kyoto-shl al Kyoto 601 (JP) Patent- und Rechtsanwalte Hansmann, Vogeser, Dr. Boecker, © Inventor: NAKAMICHI, Koulchl Alber, Dr. Strych, Lledl 13-16, Kltayamadal 1-chome, Albert-Rosshaupter-Strasse 65 Koselcho D-81369 Munchen (DE) © CRYSTALLINE CONDITION DISLOCATING METHOD. © An object of this invention is to provide a meth- od of the crystalline condition of dislocating cry- \A/ < stalline medicine simply, speedily and homoge- 4 ^ 0 at neously, and, moreover, in large quantities at once. A X. X O O x.X o °o This invention is directed to a method using an x x.x O outlet side melting zonex cooling zone.
  • The Organic Chemistry of Drug Synthesis

    The Organic Chemistry of Drug Synthesis

    The Organic Chemistry of Drug Synthesis VOLUME 2 DANIEL LEDNICER Mead Johnson and Company Evansville, Indiana LESTER A. MITSCHER The University of Kansas School of Pharmacy Department of Medicinal Chemistry Lawrence, Kansas A WILEY-INTERSCIENCE PUBLICATION JOHN WILEY AND SONS, New York • Chichester • Brisbane • Toronto Copyright © 1980 by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. Reproduction or translation of any part of this work beyond that permitted by Sections 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful. Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc. Library of Congress Cataloging in Publication Data: Lednicer, Daniel, 1929- The organic chemistry of drug synthesis. "A Wiley-lnterscience publication." 1. Chemistry, Medical and pharmaceutical. 2. Drugs. 3. Chemistry, Organic. I. Mitscher, Lester A., joint author. II. Title. RS421 .L423 615M 91 76-28387 ISBN 0-471-04392-3 Printed in the United States of America 10 987654321 It is our pleasure again to dedicate a book to our helpmeets: Beryle and Betty. "Has it ever occurred to you that medicinal chemists are just like compulsive gamblers: the next compound will be the real winner." R. L. Clark at the 16th National Medicinal Chemistry Symposium, June, 1978. vii Preface The reception accorded "Organic Chemistry of Drug Synthesis11 seems to us to indicate widespread interest in the organic chemistry involved in the search for new pharmaceutical agents. We are only too aware of the fact that the book deals with a limited segment of the field; the earlier volume cannot be considered either comprehensive or completely up to date.
  • (Ph OH N N Me O YO O YO

    (Ph OH N N Me O YO O YO

    US 20070265293A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0265293 A1 Boyd et al. (43) Pub. Date: Nov. 15, 2007 (54) (S)-N-METHYLNALTREXONE Publication Classification (76) Inventors: Thomas A. Boyd, Grandview, NY (51) Int. Cl. (US); Howard Wagoner, Warwick, NY A6II 3L/4355 (2006.01) (US); Suketu P. Sanghvi, Kendall Park, A6M II/00 (2006.01) NJ (US); Christopher Verbicky, A6M I5/08 (2006.01) Broadalbin, NY (US); Stephen 39t. 35O C Andruski, Clifton Park, NY (US) (2006.01) A6IP 3L/00 (2006.01) Correspondence Address: St. 4. CR WOLF GREENFIELD & SACKS, P.C. (2006.01) 6OO ATLANTIC AVENUE 3G (i. 308: BOSTON, MA 02210-2206 (US) A6IP 33/02 (2006.01) C07D 489/00 (2006.01) (21) Appl. No.: 11/441,452 (52) U.S. Cl. .............. 514/282; 128/200.23; 128/202.17; (22) Filed: May 25, 2006 546/45 Related U.S. Application Data (57) ABSTRACT This invention relates to S-MNTX, methods of producing (60) Provisional application No. 60/684,570, filed on May S-MNTX, pharmaceutical preparations comprising 25, 2005. S-MNTX and methods for their use. O G M Br Br e (pH OH N N Me O YO O YO OH OH R-MNTX S-MNTX Patent Application Publication Nov. 15, 2007 Sheet 1 of 6 US 2007/0265293 A1 Fig. 1 OH OH Me-N Me-N D / O O -----BBr, O O CHCI NMP, 3 AUTOCLAVE, 70'C OMe OH 1 2 Br OH As GE) G As 69 GOH Me-N ION Me-N -lass O SO EXCHANGE O SO OH OH 3 S-MNTX 1 - OXYCODONE 2 - OXYMORPHONE 3 - ODIDE SALT OF S-MNTX Fig.