I Perlapine P 1601 I PH "(c2H5)3v H,c&Ac,. a:> , DCC, m Tos-OH b V 1 - hydroxy- benzotriozole Reference(s): Vincent, M. et al.: Tetrahedron Lett. (TELEAY) 23, 1677 (1982). US 4 508 729 (ADIR). EP 49 658 (ADIR; appl. 29.9.1981 ; F-prior. 2.10.1980,7.4.1981). 1. Hz. Pd-C industrial process: US 4914 214 (ADIR; 3.4.1990; F-prior. 17.9.1987). 0 CH O CH3 2. H~N+CH, CH3 - (v) Formulation(s): tabl. 2 mg, 4 mg, 8 mg C"3 H~N+CH~ H CH3 CH3 Perindopril erburnine Trade Name(s): D: Coversum Cor (Servier) I: Coversyl (Servier) USA: Aceon (RhBne-Poulenc F: Coversyl (Servier) Procaptan (Stroder) Rorer) GB: Coversyl (Servier) Perlapine ATC: N05C Use: hypnotic RN: 1977-11-3 MF: C,,H,,N, MW. 291.40 LD,,: 61 mglkg (M, i.v.); 270 mglkg (M, p.0.); 60 mglkg (R, i.v.1; 660 mglkg (R, p.0.) CN: 6-(4-methyl- 1 -piperazinyl)- 1 IH-dibcnz[b,e]azepine AICI3. toluene, 1.2-dichlorobenzene +I I1 $ 0 2-orninodiphenyl- phosgene 2-isocyanotodi- methane phenylmethane 1602 P Perphenazine POCI,, ____, CI 1 -methyl- piperazine 6-0x0-5,6-dihydro-1 1 H- 6-chloro- 11 H-di- Perlopine dibenz[b.e]azepine (I) benz[b,e]azepine Referencels): US 3 389 139 (Dr. A. Wander; 18.6.1968; prior. 10.6.1964; 2.6.1966). Fort~zularion(s): tabl. 2.5 mg Trade Nanze(s): J: Hypnodin (Takeda) Perphenazine ATC: N05AB03 Use: neuroleptic, anti-emetic RN: 58-39-9 MF: C2,H2,C1N10S MW: 403.98 EINECS: 200-381-5 LD,,: 19 mgkg (M, i.v.); 120 mglkg (M, p.0.); 34 mgkg (R, i.v.); 318 mgkg (R, p.0.); 5 1 mgkg (dog, i.v.) CN: 4-[3-(2-chloro- 1 OH-phenothiazin- 10- yl)propyl]- 1 -piperazineethanol 2-chlorophenothiazine I -brama-3- chloropropana Referencefs): US 2 838 507 (Searle; 1958; appl. 1957; prior. 1955). 1 -(2-hydroxyethy1)- carbama~e derivatives: US 2 860 138 (Schering Corp.; 1958; appl. 1956). Perphenozine acetate: IJS 2 766 235 (J. W. Cusic; 1956; appl. 1956). piperazine Formulation(s): amp. 76 mglml; drops 4 rng/ml; inj. flask 1000 mg; tabl. 2 mg, 4 mg, 8mg, 16 mg Peruvosidc P 1603 Trade Name(s): D: Decentan (Merck) I: Mutabon (Schering- USA: Etrafon (Schering)-comb. F: Trilifan Retard (Schering- Plough) with amitryptiline Plough) Trilafon (Schering-Plough) Triavil (Merck Sharp & GB: Fentazin (Goldshield) J: Trilafon (Schering- Dohme)-comb with Triptafen (Goldshield)- Shionogi) amitryptiline comb. Triomin (Yamanouchi) Trilafon (Schering) Peruvoside ATC: COlAX02 Use: cardiac glycoside RN: 1182-87-2 MF: C,,,H,O, MW: 548.67 EINECS: 214-659-9 LD,,,: 145 pglkg (cat, i.v.) CN: (3~,5~)-3-[(6-deo~y-3-O-methyl-a-~-glucopyranosyl)oxy]-14-hydroxy-l9-oxocard-20(22)-enolide thevetin A (crude extract from Thevetia neriifalia Juss.) enzyrnotic hydroly&, 45-55 OC r - glucose 0-CH, Peruvoside From the seeds of Thevetia peruviana. DE 1 959 039 (Merck Patent GmbH; appl. 25.11.1969). Ullmmns Encykl. Tcch. Chern., 3. Aufl Vol. 8,239. Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 12, 617. starting material: Bloch et al.: Helv. Chim. Acta (HCACAV) 43,652 (1960). Formulation(s): drg. 0.3 mg; drops 0.3 mgltnl Trade Name(s): D: Encordin (Merck); wfm Nerial (Simes); wfm Pcrusid (Malesci); wfm 1: Largitor (Inverni della Perusid (Dietopharma); Beffa); wfm wfm Pethidine (Meperidine) ATC: N02AB02 Use: analgesic, antispasmodic RN: 57-42-1 MF: C15H21N02 MW: 247.34 EINECS: 200-329-1 LD,,,: 34.7 mglkg (M, i.v.); 200 mgtkg (M, p.0.); 22.5 mglkg (R, i.v.); 162 mglkg (R, p.0.) CN: 1-methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester 1 1604 P Phanquinone hydrochloride RN: 50-13-5 MF: CI,H,,N02.HCI MW: 283.80 EINECS: 200-013-3 LD,,,: 32 rnglkg (M, i.v.); 178 mg/kg (M, p.0.); 30 rnglkg (R, i.v.); 170 m>k& (R, p.o.); 68 rnglkg (dog, i.v.) y3 7'43 CI sodium arnide benzyl N,N-bis(2-chloro- 4-cyono-1 -methyl- cyanide ethyl)-N-methyl- 4-phenylpiperidine arnine 1 Pethidine I Reference(s): US 2 I67 35 1 (Winthrop; 1939; D-prior. 1937) DE 679 281 (I. G. Farben; appl. 1937). Formulation(s): drops 50 mglml; suppos. 100 mg; syrup 50 mg15 ml; tabl. 50 mg, 100 mg; vial 20 ml(100 mglml), 30 rnl (50 mglml) (as hydrochloride) Trade Name(s): D: Dolantin (Hoechst) GB: Parnergan PI00 USA: Demerol (Sanofi) F: Dolosal (Specia) (Martindale)-comb. Mepergan (Wyeth-Ayerst)- J: Neonlochin (Surnitomo) comb. Phanquinone (Phanchinonum; Phanquone) ATC: POIAX04 Use: arnoebicide, bactericide RN: 84-12-8 MF: C,,H,N20, MW: 210.19 EINECS: 201-516-0 LD,,,: 4 mglkg (M, p.0.); 5 mglkg (R, p.0.) CN: 4,7-phenanthroline-5,6-dione . 2,5-diominoonisole glycerin 5-methoxy-4.7- phenonthroline Reference(.r): GB 688 802 (Ciba; appl. 1951 ; CH-prior. 1950). Druey, J. et al.: Helv. Chirn. Acta (HCACAV) 33, 1080 (1950). Druey, J.: Angew. Chem. (ANCEAD) 72,677 (1960). For~nulation(s): drg. 10 rng, 20 mg; drops 0.3 mglml Trade Name(s): D: Mexaform plus/S (Ciba)- comb.; wfm Mexase (Ciba)-comb.; wfm Phcnacaine P 1605 F: Entobex (Ciba); wfm Mexase (Ciba)-comb.; wfm J: Mexaform forte (Ciba- Mexaform (Ciba)-comb.; I: Entobex (Ciba); wfm Geigy-Takeda)-comb. wfm Mexase (Ciba)-comb.; wfm Phenacaine (Fenacaine) RN: 101-93-9 MF: C,,H2,N,02 MW: 298.39 CN: N,N-bis(4-ethoxypheny1)ethanimidamide ATC: NOlB Use: local anesthetic Reference(s): DRP 79 868 (E. Tauber, appl. 1894); also further methods. phenacetin Trade Namefs): USA: Holocaine (Lilly); wfrn Phenacaine Phenacemide (9. v.1 ATC: N03AX07 Use: antiepileptic RN: 63-98-9 MF: C9HloN202 MW: 178.19 EINECS: 200-570-2 LD,,: 987 mglkg (M, p.0.); 1600 mgkg (R, p.0.) CN: N-(aminocarbonyl)benzeneacetamide Referencefs): Spielman, M.A. et al.: J. Am. Chem. Soc. (JACSAT) 70,4189 (1948). phenylacetyl ureo Formulation(s): tabl. 500 mg Phenocemide Trade Name(s): F: Epiclase (Roger Bellon); USA: Phenurone (Abbott); wfrn wfrn chloride 3 1606 P Phenacetin Phenacetin (Acetophenetidin) ATC: N02BE03 Use: analgesic, antipyretic RN: 62-44-2 MF: CI,H,3N0, MW: 179.22 EINECS: 200-533-0 LD,,,: 866 mglkg (M, p.0.); 3600 mgkg (R, p.0.) CN: N-(4-cthoxyphenyl)acetamide NoOH DO-CH3 H JPd-C or Roney-Ni + 1 O2N OzN 4- nitrophenol chloro- 4-nitrophenetole ethane Referencefs): Ullmanns Encykl. Tech. Chem., 3. Aufl., Vol. 13,296. Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 7,543. p-phenetidine (I) ocetic anhydride Formulation(s): f. c. tabl. 50 mg Phenacetin Trade Name(s): D: numerous combination Ciclergol(1TA)-comb.; Thomapir~na N @her)- preparations; wfm wfm comb.; wfm F: Polipirine (Lehning) Neuroxin (Edmond)-comb.; J: numerous generic I: Cachets Lia (Arnaldi)- wfrn preparations comb.; wfm Novamon (Farge)-comb., USA: numerous combination % Pm preparations; wfm Phenaglycodol ATC: N05C Use: psychosedative, tranquilizer RN: 79-93-6 MF: CI,H15C10, MW: 214.69 EINECS: 201-235-3 LD,,,: 254 mglkg (M, i.v.); 5 14 mgkg (M, p.0.); 832 mglkg (R, p.0.) CN: 2-(4-chloropheny1)-3-methyl-2,3-butanediol 4-chlorophenyl- 2-methyl-3-0x0- Phenoglycodol magnesium bromide 2-bulanol Rrference(s): US 2 8 12 363 (Eli Lilly; 1957; prior. 1953). DE 1 038 024 (Eli Lilly; appl. 1956). Phenazocine P 1607 Trade Namds): I: Felixyn (Radiumfarma); USA: Ultran (Lilly); wfm wfm Phenazocine ATC: N02AD02 Use: analgesic RN: 127-35-5 MF: C,,H,,NO MW: 321.46 EINECS: 204-835-3 LDS,: 20 mgkg (M, i.v.); 90 mgkg (R, p.0.) CN: 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(2-phenylethyl)-2,6-methano-3-benzazocin-8-01 hydrobromide RN: 1239-04-9 MF: C,,H,,NO . HBr MW: 402.38 E1NECS: 214-982-5 LD,,: I 1 mglkg (M, i.v.) 5.9-dimethyl-2'- hydroxybenzo-6- morphen (cf. pentazocine synthesis) LiAIH, 1 b lithium alanate phenylacetyl 5.9-dimethyl-2'-hydroxy-2- chloride phenylacetylbenzo-6-morphen (1) Phenazocine 3.4-dimethyl- 2-phenylethyl pyridine bromide a "c+m.gcl H3cn+ . I1 H3C 4-methoxybenzyl- Br- magnesium chloride 3.4-dimethyl-1 -phen- ethylpyridinium bromide 2-(4-methoxybenzy1)-3.4- dimethyl- 1 -phenethyl- 1.2.5.6-tetrahydropyridine 1608 P Phenazopyridine I Reference(s): US 2 959 594 (Smith Kline & French; 8.1 1.1960; prior. 22.9.1958). May, E.L. et al.: J. Org. Chem. (JOCEAH) 22, 1366, 1369 (1957); 24, 294, 1435 (1959); 25,984 (1960). Formulation(s): tabl. 5 mg (as hydrobromide) Trade Name(s): GB: Narphen (Napp) USA: Primadol (Smith Kline & French); wfrn Phenazop yridine ATC: G04BX06 Use: chemotherapeutic, antiseptic RN: 94-78-0 MF: C,,H,,N, MW: 213.24 EINECS: 202-363-2 LD,,: 580 mglkg (M, p.0.) CN: 3-(pheny1azo)-2,6-pyridinediaminc monohy drochloride RN: 136-40-3 MF: C,,HllNs . HCl MW: 249.71 EINECS: 205-243-8 LD,,: 180 mglkg (M, i.v.); 472 mglkg (R, p.0.) benzenediazonium 2.6-diamina- chloride pyridine Phenozopyridine I Reference(s): DRP 515 781 (Boehringer; 1927). US 1 680 108, US 1 680 109, US 1 680 110, US 1 680 11 1 (Pyridium Corp.; 1928). Chichibabin, A.F.; Zeide, O.A.: Zh. Russ. Fiz Khim. 0-va (ZRKOAC) 46, 1216 (1914). Shreve, R.N. et al.: J. Am. Chcm. Soc. (JACSAT) 65,2241 (1943). Formulation(s): cps. 50 mg (as hydrochloride) in comb.; f. c. tahl. 50 mg; tabl. 100 mg, 200 mg (as hydrochloride) Trade Name(s1: D: Urospasmon (Heumann)- GB: Pyridium (Parkc Davis); J: Fenason (Kanto) comb. wfm Uriscptin (Nissin) F: Azocline (Bristo1)-comb.; Pyridium (Warner); wfm Uropyridin (Eisai) wfm Uromide (Consolidated)- USA: Pyridium (Warner Chilcott) Pyridium (Servier); wfm comb.; wfm Urobiotic (Pfizer)-comb. Phendimetrazine ATC: A08AA49 Use: appetite depressant, psychostimulant RN: 634-03-7 MF: C,,H,,NO MW: 191.27 EINECS: 211-204-6 CN: (2s-trans)-3,4-dimethyl-2-phenylmorpholine Phenelzine P 1609 hydrochloride RN: 7635-51-0 MF: C,,HI7NO . HCI MW: 227.74 EINECS: 231-566-9 LD,,: 92 mgkg (M, i.v.); 340 mg/kg (M, p.0.); 455 mg/kg (R, p.o.) tartrate (1:l) RN: 50-58-8 MF: C12HL7N0 . C4H606 MW: 341.36 EINECS: 200-051-0 LD,,: 210 mg/kg (M, i.p.) H0b'xcH3 , Ho,,op Z-methylornino- q (3"' formic ethanol acid I CH3 C"3 propiophcnonc a-bromopropio- phenone Reference($): US 2 997 469 (Boehringer Ing.; 22.8.1961; D-prior. 13.3.1958). parnoate: FR 1461 407 (Sobio; appl. 9.6.1965). Formulalion(s): cps. 105 mg; tabl. 35 mg (as tartrate) Trade Name(s): F: Fringanor (Sobio); wfm USA: Bontril (Camrick) Prelu-2 (Roxane) I: Plegine (Wyeth-Lederle) Plegine (Wyeth-Ayerst) Phenelzine ATC: N06AF03 Use: antidepressant, MAO-inhibitor RN: 51-71-8 MF: C,H,,N, MW: 136.20 ElNECS: 200-117-9 LD,,: 130 rngtkg (M, p.0.) CN: (2-pheny1ethyl)hydrazine dihydrogen sulfate . RN: 156-51-4 MF: C,H,,N,. H2S04 MW: 234.28 EINECS: 205-856-0 LD,,: 157 rnglkg (M, i.v.); 156 mglkg (M, p.0.); 210 mg/kg (R, p.0.) dihydrochloride RN: 16904-30-6 MF: C,H,,N,. 2HCl MW: 209.12 LD,,,: 100 rnglkg (M, i.p.) 2-phenylethyl hydrazinc bromide Reference(s): US 3 000 903 (Lakeside Labs.; 19.9.1961; appl. 15.9.1959; prior. 23.8.1956). 16 10 P Pheneticillin Fortn~tlation(s): tabl. 15 nlg (as dihydrogen sulfate) Trade Name(s): F: Nardelzine (Substantia); GB: Nardil (Parke Davis) USA: Nardil (Parke Davis) wfm I: Nardil (Vister); wfm Pheneticillin (Phenethicillin) ATC: JOlCE05 Use: antibiotic RN: 147-55-7 MF: C,,H2,,N205S MW: 364.42 EINECS: 205-691-4 LD,,: 52.25 rnglkg (M, intracerebral) CN: [2S-(2a,5a,6~)]-3,3-dimethyl-7-oxo-6-[(1 -oxo-2-phenoxypropyl)amino]-4-thia- 1 - azabicyclo[3.2.0]heptane-2-carboxylic acid monopotassium salt RN: 132-93-4 MF: C,,Hj9KN205S MW: 402.51 EINECS: 205-084-4 LD,,: 3 12 mglkg (M, i.v.); >2 glkg (M, p.0.); >I03 mglkg (dog, i.v.) COOH a-co-o-cH,-w(cH,),. N(c2H5), triethyl- isobutyl ester amine CH3 Reference(s): GB 877 120 (Beecharn; appl. 10.5.1960; USA-prior. 25.5.1959,22.10.1959). GB 958 478 (Beecham; appl. 28.2.1963; USA-prior. 13.3.1962). GB 899 199 (Pfizer; appl. 7.1.1960; USA-prior. 28.9.1959). GB 904 576 (Bayer; appl. 24.1 1.1960; D-prior. 4.12.1959). DE 1 143 817 (Beecharn; appl. 25.5.1960; USA-prior. 25.5.1959). DE 1 159 449 (Griinenthal; appl. 22.3.1961). DE 1 159 454 (Pfizer; appl. 18.3.1961; USA-prior. 24.6.1960). 2-phenoxypropionic 6-arninopenicillanic actd acid f+ormmlation(s): tabl. 135 mg (as monopotassium salt) Pheneticillin J Trade Nume(s): D: Palliopen (Merck)-comb.; I: Altocillin (Caber); wfm J: Maxipen (Taito Pfizer) wfm Metilpen (Boniscontro & Syncillin (Banyu) Pen-200 (Pfizer); wfm Gazzone); wfm Synthepen (Mciji) F: Peniplus (Fumouze); wfm Penicilloral (Terapeutico USA: Maxipen (Pfizer); wfm Synthecilline (Bristol); M.R.); wfm Syncillin (Bristol); wfm wfm Penorale (Lusofarmaco); GB: Broxil (Beecham); wfm wfm Pheneturide ATC: N03AX13 Use: antiepileptic RN: 90-49-3 MF: CllH14N202 MW: 206.25 EINECS: 201-998-2 LD,,,: 9 10 mglkg (M, p.0.); >2063 mglkg (R, p.0.) CN: N-(aminocarbony1)-a-ethylbcnzeneacetamide . RN: 14 7-5 5-7 MF: C,,H2,,N205S MW: 364.42 EINECS: 20 5-6 9 1-4 LD,,: 52.25 rnglkg (M, intracerebral) CN: [2S-(2a,5a,6~) ]-3 ,3-dimethyl-7-oxo- 6-[ (1 -oxo-2-phenoxypropyl)amino ]-4 -thia- 1 - azabicyclo[3.2.0]heptane-2-carboxylic. C,,,H,O, MW: 548.67 EINECS: 21 4-6 5 9-9 LD,,,: 145 pglkg (cat, i.v.) CN: (3~,5~ )-3 -[ (6-deo~y-3-O-methyl-a-~-glucopyranosyl)oxy ]-1 4-hydroxy-l9-oxocard-20(22)-enolide thevetin A (crude extract. 12 7-3 5-5 MF: C,,H,,NO MW: 321.46 EINECS: 20 4-8 3 5-3 LDS,: 20 mgkg (M, i.v.); 90 mgkg (R, p.0.) CN: 1,2,3,4,5,6-hexahydro-6,11-dimethyl- 3-( 2-phenylethyl )-2 ,6-methano-3-benzazocin- 8-0 1