Alibendol A 6 1 16-dehydroprogesterone 16u, 17a-dihydroxy- progesterone (I) I , acetophenone 1 Algestone acetophenide I Reference(s): DE 1 125 423 (Oh Mathieson; appl. 1959; USA-prior. 1958). Fried, J. et al.: Chem. Ind. (London) (CHINAG) 1961,465. alternative synthesis; US 3 008 958 (Olin Mathieson; 1961; prior. 1961). synthesis of intermediates: US 2 727 909 (Searle; 1955; prior. 1954). US 3 165 541 (Olin Mathieson; 12.1.1965; prior. 20.5.1963). Cooley, G. eta].: J. Chem. Soc. (JCSOA9) 1955,4373. Inhoffen, H.H. et al.: Chem. Ber. (CHBEAM) 87,593 (1954). Hydorn, A.E. et al.: Steroids (STEDAM) 3,493 (1964). injection solution: US 3 164 520 (Olin Mathieson; 5.1.1965; prior. 29.10.1962). medical me as contraceptive: GB 1 060 632 (Oh Mathieson; appl. 16.8.1963; USA-prior. ll.ll.1962). Formulation(s): cream 2 % Trade Name(s): I: Neolutin Depos. (Medici) Alibendol ATC: ClOA; A03 Use: antispasmodic, choleretic, cholekinetic RN: 26750-81-2 MF: C,,H,,NO, MW: 251.28 EINECS: 247-960-9 LD,: >3000 mglkg (M, p.0.); >2000 mgkg (M, s.c.) CN: 2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(2-propenyl)benzamide 2-hydroxy -3- methoxy- benzaldehyde - ethyl P-hydroxy- 3-methoxybenzoate 62 A Alimemazine 0 0-CH, /,,&h3 + H2NmOH * H,C' ethyl 5-ollyl-2- ethonolamine Alibendol hydroxy-3-methoxy- benzoate (I) Reference(s): DE 1 768 615 (Roussel-Uclaf; appl. 1968; F-prior. 1967). Clemence, F. et al.: Chim. Ther. (CHTPBA) 5, 188 (1970). Formulation(s): tabl. 100 mg Trade Name(s): F: Cebera (Irex) Alimemazine (Trimeprazine) ATC: R06ADO1 Use: antihistaminic, psychosedative RN: 84-96-8 MF: C,,H,,N,S MW: 298.45 EINECS: 201-577-3 LD,,: 33 mgkg (M, i.v.); 300 mglkg (M, p.0.); 35 mgkg (R, i.v.); 210 mglkg (R, p.0.) CN: N,N,P-trimethyl-lOH-phenothiazine-10-propanamine tartrate (2:l) RN: 4330-99-8 MF: C,,H2,N2S. 1/2C4H606 MW: 746.99 EINECS: 224-368-9 LD,,: 33 mgkg (M, i.v.); 300 mglkg (M, p.0.); 35 mgkg (R, i.v.); 210 mglkg (R, p.0.) H CH CH, + clA'.CH3 sodium omide Reference(s): US 2 837 518 (RhGne-Poulenc; 1958; F-prior. 1954). DE 1 034 639 (RhGne-Poulenc; appl. 1955; GB-prior. 1954 and 1955). phenothiozine 3-dimethylomino- Formulation(s): drops 40 mg; tabl. 2.5 mg, 5 mg (as tartrate) Alimemozine Trade Name(s): D: Repeltin (Bayer) GB: Vallergan (RhGne-Poulenc F: Theralhne (Evans Medical) Rorer; as tartrate) ThCralene Pectoral (Evans I: in comb. with prednisolone Medical)-comb. J: Alimezine (Daiichi) 2-methylpropyl chloride Alizapride A 63 Alizapride ATC: A03FA05; A04AD Use: antl-emetic, neuroleptic RN: 59338-93-1 MF: C,,H,,N,O, MW: 315.38 EINECS: 261-710-6 LDw: 92.7 mglkg (M, i.v.) CN: 6-mcthoxy-N-[[I-(2-propenyl)-2-pyrrolidinyl]methyl]-1H-benzotriazole-5-carboxamide I: FH3 HODC I1 H3C' II H3C 0 0 p-amino- dimethyl methyl 4-amino- salicylic acid sulfoie 2-methoxybenzoote (9. v.1 NONO*, HCI sodium 0 nitrite aminomethyl- methyl 4.5-diomino- methyl 6-mthox- p~rra1idi.e I Uizopride 1 . 2-methoxybenzoate (I) benzotriozale-5- corboxylote Reference(s): DE 2 500 919 (Delagrange; appl. 11.1.1975). US 4 039 672 (Delagrange; 2.8.1977; D-priol. 1 1.1.1975). synthesis of methyl 4-amino-2-methoxybenzoate: DOS 1966 212 (Yamanouchi; appl. 29.12.1969; J-prior. 2.12.1968, 9.12.1968,4.4.1969). Formulation(s): amp. 50 mg/2 ml; drinking amp. 360 mg; suppos. 50 mg; tabl. 50 mg Trade Name(s): D: Vergentan (Synthelabo) I: Limican (Synthelabo) F: Plitican (S ynthelabo) Nausilen (Baldacci) Allantoin ATC: Use: RN: 97-59-6 MF: C4H,N403 MW: 158.12 EINECS: 202-592-8 CN: (2,5-dioxo-4-imidazolidiny1)urea D03; DO5 wound remedy, antipsoriatic, adstringent, web stimulant, keratolytic, antacid RN: 13 17-25-5 MF: C4H,A1,CIN40, MW: 3 14.55 EINECS: 215-262-3 LD,,,: 28 gkg (MA p.o.1 CN: chloro[(2,5-dioxo-4-imidazolidinyl)uretato]tetrahydroxyaluminum 64 A Aldioxa Aldioxa RN: 5579-81 -7 MF: C4H,A1N,0s MW: 218.1 1 EINECS: 226-964-4 LD,,: >8 glkg (M, p.0.) CN: [(2,.5-dioxo-4-imidazolidinyl)ureato]dihydroxyaluminum urea glyoxylic acid Alcloxo I I Aldioxo Reference(s): DOS 1 939 924 (BASF; appl. 6.8.1969). from glyoxal viu "in situr'-glyoxylic acid: DOS 2 7 14 938 (Akad. d. Wiss. der DDR; appl. 2.4.1977; DDR-prior. 29 10.1976). from chloral hydrate via "in situV-glyoxylic acid: DOS 2 717 698 (Akad. d. Wiss. der DDR; appl. 21.4.1977; DDR-prior. 29.10.1976). by oxidation of uric acid with PbO, or H202 or potassium permanganate: Org. Synth. (ORSYAT) 13 1 (1933). by oxidation of glycoluril widz H20,: Biltz, H.; Schiemann, G.: J. Prakt. Chem. (JPCEAO) 113,92 (1926). US 2 802 01 1 (Carbogen Corp.; 19.57; appl. 19.56). by condensation of glyoxylic acid esters or glyoxylic acid acetul esters with urea: US 2 1.58 098 (Merck & Co.; 1939; appl. 1937). Formulation(s): cream 0.2 %; ointment 2 %; powder 0.5 %; tabl. 100 mg Trade Name(s): D: more than 70 combination preparations allantoin Brand- und Wundgel (Eu Rho Arznei)-comb. Contractubex Gel (Merz & Co.)-comb. Ellsurex (Ga1derma)-comb. Essaven (Nattermann)- comb. HAEMO-Exhirud (Sanofi Winthrop)-comb. Hydro Cordes (Block Drug Company; Ichthyo1)-comb. Lipo Cordes (Block Drug Company)-comb. Psoralon (Herma1)-comb. Psoriasis-Salbe M (Balneopharm) Ulcurilen (Spitzner)-comb alcloxa Ansudor (Basotherm)- comb. aldioxa Ansudor (Basotherm)- comb. Dexa-Mederma Akne (Merz & Co.)-comb. GB: Elmedal (Thiemann)-comb. Mederima (Merz & Co.)- comb. ZeaSorb Puder (Stiefe1)- comb. alcloxa Ulfon (Lafon)-comb. aldioxa Ulfon (Lafon)-comb. allantoin Actinac (Hoechst)-comb. with chloramphenicol and hydrocortisone Allobarbital A 65 Alphosyl (Stafford-Miller)- comb. Aphosyl HC (Stafford- Miller)-comb. with hydrocortisone Dermalex (Sanofi Winthrop)-comb. with squalene and hexachlorophane 1: allantoin Alphosyle (Po1i)-comb. Antiacne Samil (Sami1)- comb. Apsor pomata (ID1 Farrnaceutici)-comb. J: aldioxa Aldioxa (Isei) Chlokale (Sawai) USA: allantoin Alphosyl (Reed & Camrick)-comb.; wfrn Bahnex (Maxsi1)-comb.; wfrn Cervex (Medics)-comb.; wfrn Cutemol Creme (Summers); wfrn Herpecin-L (Campbell) comb.; wfm Sufamal (Milex)-comb.; wfm Vagilia (Lemmon)-comb.; wfrn Allobarbital (Allobarbitone) ATC: N05CA21 Use: hypnotic, sedative RN: 52-43-7 MF: CIOHl,N,O, MW: 208.22 EINECS: 200-140-4 LD,,: 21 8 mglkg (M, i.v.) CN: 5,5-di-2-propenyl-2,4,6(1H,3H,SH)-pyrimidinetrione ally1 bramide borbituric 1 Allobarbital 1 acid Reference(s): DRP 268 158 (Ciba; appl. 1911). DRP 526 854 (Hoffmann-La Roche; appl. 1930). Formulation(s): tabl. 30 mg, 100 mg, 300 mg Trade Name(s): D: Toximer (Merck1e)-comb.; F: Spasmo-Cibalgine (Ciba)- I: Allobarb (Tariff. wfm comb.; wfm Integrative) USA: Diadol (Durst); wfrn Allopurinol ATC: M04AAO1 Use: uricosuric agent RN: 315-30-0 MF: C,H,N,O MW: 136.1 1 EINECS: 206-250-9 L&: >l glkg (M, p.0.) CN: 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 66 . A Allopurinol ethyl cyanoacetate triethy ortho- ethyl ethoxymethylene- forrnate cyonoacetaie (I) ethyl 5-amino- pyrazole-4-carboxylate H2N-NH2 H2N-CHO I hydrazine ' b forrnornide 0 Allopurinol u H 0 cyanoaceiarnide forrnamidine hydrochloride 3-amino-2-cyano- acrylarnide (11) H,N-NH2 H,N-CHO 11 hydrozine formamide 0 Reference(s): a US 2 868 803 (Ciba; 13.1.1959; CH-prior. 10.2.1956). US 3 624 205 (Burroughs Wellcome; 30.1 1.197 1; USA-prior. 25.4.1967). b DAS 1 720 024 (Wellcome Found; appl: 12.7.1967; GB-prior. 14.7.1966). similar process: DAS 1 904 894 (Wellcome Found; appl. 3 1.1.1969; GB-prior. 2.2.1968). US 4 146 713 (Burroughs Wellcome; 27.3.1979; GB-prior. 2.2.1968). alrernative syntheses: US 3 474 098 (Burroughs Wellcome; 21.10.1969; prior. 29.3.1956). DAS 2 224 382 (Henning Berlin; appl. 18.5.1972). DE 1 118 221 (Wellcomc Found; appl. 4.8.1956; GB-prior. 10.8.1955). DAS 1 814 082 (Wellcome Found; appl. 11.12.1968). DAS 1 950 075 (Henning Berlin; appl. 3.10.1969). DOS 2 018 345 (Delmar Chemicals; appl. 16.4.1970; GB-prior. 17.4.1969). cornbirzation with benzbromarone: GB 1 493 237 (Henning Berlin; appl. 11.5.1976; D-prior. 10.12.1975) Formulation(s): tahl. 100 mg, 200 mg, 300 mg Trade Nu~ne(s): D: ~110-300-Tablinen (ct- Allomaron (Nattermann). Arzneimittel) comb. Allo-Puren 1001-300 (Isis Puren) ~leminol (gepepharm) Allylestrenol A 67 Cellidrin (Henning) dura A1 300 (durachemie) Foligan (Henning Berlin) Remid 1001-300 (TAD) Suspend01 (Merckle) Uribenz 300 (R.A.N.) Uripurinol 1001300 (Azupharma) Urosin (Boehringer Mannh.) Zyloric (Glaxo Wellcome; 1966) combination preparations F: Zy loric (Glaxo Wellcome; 1968) GB: Zyloric (Glaxo Wellcome; J: 1966) USA: 1: Allopuri (Formulario Naz.) Allurit (RBS Pharma) Allurit (Rh8ne-Poulenc Rorer) Uricemil (KT) Uricodue (IF[)-comb. Zyloric (Wellcome; 1969) Zyloric (Tanabe; 1969) Zyloprim (Glaxo Wellcome; 1966) Allylestrenol (Allyloestrenol) ATC: G03DCOI Use: progestogen RN: 432-60-0 MF: C,,H,,O MW: 300.49 EINECS: 207-082-9 LD,,: >640 mglkg (M, p.0.) CN: (17P)-17-(2-propenyl)estr-4-en-17-ol nandrolone ethane- (q.v.) 1,2-dithial EirtJ9+,CH2 A allylmagnesium bromide 17P-hydroxy- 4-estrene (I) 17-0x0-4- estrene / Allylestrenol Referencefs): GB 841 41 1 (Organon; appl. 2.4.1958; NL-prior. 10.4.1957). alternative syntheses: GB 875 549 (Organon; appl. 31 .l2.1959; NL-prior. 13.1.19.59). US 2 878 267 (Organon; appl. 16.4.1958; NL-prior. 1 S.1957). Formulation(s): tabl. 5 mg Trade Name(s): D: Gestanon (Organon); wfm 1: Gestanon (Organon Italia) GB: Gestanin (Organon); wfm J: Gestanon (Sankyo) Alminoprofen ATC: MOlAE16 Use: non-steroidal anti-inflammatory, analgesic RN: 39718-89-3 MF: C,,Hl,NO, MW: 219.28 EINECS: 254-604-6 LD,,: 2400 mglkg (M, p.0.) CN: a-methyl-4-[(2-methyl-2-propenyl)amino]benzeneacetic acid 68 A Almitrine 1. HCI YH3 CH3 2.HO-CH3 UCooH + 0=CH2 + COOH , I O2N HN\ CH3 4-nitrobenzene- form- dimethyl- acetic ocid oldehyde omine Hp. Pd-C 2. NoOH fl\CH3- &0\cH3 T= H3cvN 02N / 0 Hzt4 chloride (1) I Alminoprofen Referenceis): Dumaitre, B. et al.: Eur. J. Med. Chem. (EJMCAS) 14, 207 (1979). alternative synthesis: FR 2 289 180 (Lab. Bouchara; appl. 17.5.1971). Formulation(s): tabl. I50 mg, 300 mg Trade Name(s): F: Minalfkne (Bouchara) J: Minalfen (Fujirebio) Almitrine ATC: R07AB07 Use: analeptic, respiratory stimulant RN: 27469-53-0 MF: C,,H,,F,N, MW: 477.56 EINECS: 248-475-5 CN: 6-[4-[bis(4-fluorophenyl)methyl]-l-piperazinyl]-N,l\r-di-2-propenyl-1,3,5-triazine-2,4-diamine 1 -[bis(4-fluoropheny1)- cyonuric methyllpiperozine chloride 2-[4-[bis(4-1luorophenyl)- methyl]-1 -piperozinyl]- 4.6-dichloro-1 .3,5-triozine (I) H2N4~H2 . NoOH I b ollylomine F N yN HNd'~~, Alrnitrine Aloxiprin A 69 Reference(s): FR 2 019 646 (Science Union; appl. 22.9.1969; GB-prior. 2.10.1968). DOS 1 947 332 (Science Union; appl. 18.9.1969; GB-prior. 2.10.1968). US 3 647 794 (Science Union; 7.3.1972; GB-prior. 2.10.1968). GB 1 256 51 3 (Science Union; appl. 2.10.1968; valid from 30.9.1969). Formulation(s): f. c. tabl. 50 mg; vial 15 mg/5 ml; tabl. 50 mg Trade Narne(s): D: Vectarion (Servier; 1984) F: Duxil (Therval Mtdical; Vectarion (EuthCrapie; 1979)-comb. 1983) Aloxiprin ATC: BOIACIS; N02BA02 Use: analgesic RN: 9014-67-9 MF: unspecified MW: unspecificd CN: aloxiprin polymeric condensotion product of aluminum oxide and ocetylsolicylic acid aluminum isoprapylate acetylsalicylic ocid Aloxiprin (q. v-1 Reference(s): Cummings, A.J. et al.: J. Pharm. Pharmacol. (JPPMAB) 15, 56 (1963). Forrnulation(s): tabl. 400 mg, 450 mg, 600 mg Trade Name(s): GB: Palaprin (Nicholas); wfm Palaprin forte (Nicholas); wfm Alphaprodine (Alfaprodina) ATC: N02AB Use: analgesic RN: 77-20-3 MF: C,,H,,NO, MW: 261.37 EINECS: 201-011-5 CN: cis-1,3-dimethyl-4-phenyl-4-piperidinol propanoate (ester) hydrochloride RN: 561-78-4 MF: C,,H2,NO2. HCI MW: 297.83 LD,,,: 32 mgkg (M, i.v.); 25 mgkg (R, i.v.); 90 mglkg (R, p.0.); 36.2 mgkg (dog, i.v.) 70 A Alpidem bromo- phenyllithium benzene H SO 11 +. H~C/)~OY'CH~ L+ 0 0 HSC propionic anhydride Alphaprodine I Reference(s): US 2 498 433 (Hoffmann-La Roche; 19.50; prior. 1946) starting material: I ,3-dimethyl-4-piperidone: Howton: J. Org. Chem. (JOCEAH) 10,277 (1945) Formulation(s): amp. 4 %, 6 % Trade Name(s): USA: Nisentil (Roche); wfm Alpidem ATC: N05B Use: anxiolytic, o,-agonist RN: 82626-01 -5 MF: C2,Hz3CI2N3O MW: 404.34 CN: 6-chloro-2-(4-chlorophenyl)-N,~propylimidazo[l,2-a]pyridine-3-acetamide 2-omino-5- 4'-chloro-2-brorno- 6-chloro-2-(4-chloro- chloropyridine acetophenone phenyl)imidazo[l,2-a]- pyridine 2. NaCN cI~~l 3. HCI. CH3COOH - COOH H,C-N, . RN: 8262 6-0 1 -5 MF: C2,Hz3CI2N3O MW: 404.34 CN: 6-chloro- 2-( 4-chlorophenyl)-N,~propylimidazo[l,2-a]pyridine-3-acetamide 2-omino- 5- 4'-chloro-2-brorno- 6-chloro- 2-( 4-chloro- chloropyridine. ATC: R07AB 07 Use: analeptic, respiratory stimulant RN: 274 6 9-5 3-0 MF: C,,H,,F,N, MW: 477 .56 EINECS: 24 8-4 7 5-5 CN: 6-[ 4-[ bis(4-fluorophenyl)methyl]-l-piperazinyl]-N,l -di-2-propenyl-1,3,5-triazine-2,4-diamine. EINECS: 24 7- 9 6 0-9 LD,: >3000 mglkg (M, p.0.); >2000 mgkg (M, s.c.) CN: 2-hydroxy-N-(2-hydroxyethyl )-3 -methoxy- 5-( 2-propenyl)benzamide 2-hydroxy -3 - methoxy- benzaldehyde - ethyl P-hydroxy-