Prednylidene P 1701 Reference(s): Gardi, R. et al.: Gazz. Chim. Ital. (GCITA9) 93,431 (1963). prednisolone 17-valerote (I) prednisolone 17-valerate: DE 1 214 677 (Francesco Vismara; appl. 1.6.1962; I-prior. 24.6.1961). US 3 147 249 (Francesco Vismara; 1.9.1964; I-prior. 13.6.1961). cf. hydrocortisone butyrate, betametasone valerate Prednivol acetate Trade Narne(s): I: Acepreval (Parke Davis- Vister); wfm Prednylidene ATC: H02AB11 Use: glucocorticoid RN: 599-33-7 MF: C,,H,,O, MW: 372.46 EINECS: 209-964-9 LD,: 7450 mgkg (M, p.0.) CN: (I 1~)-11,17,21-trihydroxy-l6-methylenepregna-l,4-diene-3,20-dione H202. OH- Curvulorio lunoto OH (Wokker) Boodijn 1702 P Prednylidene diethylaminoacetate Bocilllus sphoericus or Corynebocterium simplex 16-methylenehydrocortisone (ID) Prednylidene Reference (s): DE 1 134 074 (E. Merck AG; appl. 3 1.1 .l959). Mannhardt, H.J. et a].: Tetrahedron Lett. (TELEAY) 1960, 21. Taub, D. et al.: J. Org. Chem. (JOCEAH) 25,2258 (1960). alternative synthesis: US 3 068 226 (Merck & Co.; 1962; prior. 1961, 1959). Formulation(s): tabl. 6 mg, 24 mg, 60 mg Trade Name(s): D: Decortilen (Merck) I: Dacortilen Merck (Bracco); F: DCcortilbne (Farmex); wfm wfm Prednylidene diethylaminoacetate ATC: ~02~~11 LJse: glucocorticoid RN: 6890-42-2 MF: C,,H,,NO, MW: 485.62 CN: N,N-diethylglycine (1 1 P)- 1 l,l7-dihydroxy- 16-methylene-3,20-dioxopregna- 1,4-dien-21-yl ester hydrochloride RN: 22887-42-9 MF: C,,H,,NO,. HCI MW: 522.08 EINECS: 245-299-0 prednylidene (4. v.) diethylominoacetic Prednylidene diethylom~noocetote onhydride Reference(s): DE 1 134 074 (E. Merck AG; appl. 3 1.1.1959). combination with quinoline derivatives: BE 829 197 (Grosjean; appl. 16.5.1975). Formulation(s): amp. 30 mglml, 60 mg/ml Trade Name(s): D: Decortilen sol. (Merck) Pregnenolone P 1703 Pregnenolone ATC: L02BA Use: glucocorticoid RN: 145-13-1 MF: C2,H32O2 MW: 316.49 EINECS: 205-647-4 CN: (3P)-3-hydroxypregn-5-en-20-one succinate RN: 4598-67-8 MF: C2,H,,05 MW: 416.56 EINECS: 225-001-5 acetate RN: 1778-02-5 MF: C2,H,,0, MW: 358.52 EINECS: 217-212-6 diosgenin acetic anhydride (1) chrorniurn(V1) oxide )rCH3 0 CH3 1. Hz. Pd 2. hydrolysis dehydropregnenolone ocetate (11) Pregnenolone Reference(s): Ehrhart-Ruschig, 111,341. Ullmanns Encykl. Tech. Chern., 3. Aufl., Vol. 8,664, and there cited literature. alternative syntheses: Ullmanns Encykl. Tech. Chern., 3. Aufl., Vol. 8,660. Formulation(s): cream 0.5 % (as acetate) Trade Name(s): F: Fadiarnone Crkrne (Sauba; USA: Formula 405 (Doak; as Panzalone (Doak; as as acetate)-comb.; wfrn succinate); wfrn succinate); wfrn Prenolon (Schering); wfrn Prenalterol ATC: COlCA13 Use: cardiotonic RN: 57526-81-5 MF: C,,H,,NO, MW: 225.29 EINECS: 260-791-5 CN: (S)-4-[2-hydroxy-3-[(1-rnethylethyl)arnino]propoxy]phenol 1704 P Prenalterol hydrochloride RN: 61 260-05-7 MF: C,,HI9NO3 . HCI MW: 261.75 O NaOH isopropylomine (n) OH 0 H hydroquinone epichloro- CH3 (W monobenzyl hydrin ether (1) OH rocernate resolution with (+)-di-toluoyltartoric acid C"3 Prenalterol p-toluenesulfonyl chloride (V) C"3 5.6-onhydro-1.2-0- isopropylidene-a-D- glucofuranose (VI) pyridine CH3COOH vt + 1 + + VII Prenvlamine P 1705 1. NolO,. CHSOH, CH,COOH 2. NOW+, CHSOH 1. sodium periodate "$ 2. sodium borohydride ' OH (W OH I -(4-benzyloxypheny1)- 2(S),3-dihydroxypropone (VIE) 1. V, pyridine 2. 11, $H50H 3. Hz, Pd-C Vm Reference(s): DOS 2 503 75 1 (Ciba-Geigy; appl. 30.1.1975; CH-prior. 8.2.1974) racemate: NL-appl. 7 501 785 (Hassle; appl. 14.2.1974). US 4 080 471 (Hassle; 21.3.1978; prior. 25.6.1976). synthesis of 5,6-anhydro- 1 ,2-0-isopropylidene-a-D-glucofuranose: Ohle, H.; Dickhbser, E.: Chem. Ber. (CHBEAM) 58, 2593 (1925). Ohle, H.; Vargha, L. v.: Chem. Ber. (CHBEAM) 61, 1203 (1 928); 62, 2435 (1 929) Schmidt, D. Th.: Methods Carbohydr. Chem. (MCACAI) 2, 326 (1963). Horton, D.; Tsai, J.: Methods Carbohydr. Chem. (MCACAI) 8, 177 (1980). Formulation(s): amp. 5 mg (as hydrochloride) Trade Name(s): GB: Hyprenan (Astra); wfm Varbian (Ciba Labs); wfrn I: Varbian (Ciba-Geigy); wfrn Prenylamine ATC: COIDX02 Use: coronary vasodilator RN: 390-64-7 MF: CZ4Hz7N MW: 329.49 EINECS: 206-869-4 LD,,: 250 mglkg (M, i.v.); 11 mglkg (R, i.v.); 250 mglkg (R, p.0.) CN: N-(l-rnethyl-2-phenylethyl)-y-phenylbenzenepropanamine lactate (1:l) RN: 69-43-2 MF: C2,HZ7N . C,H,O, MW: 419.57 EINECS: 200-705-5 LD,,,: 250 mglkg (M, p.0.); 1 glkg (R, p.o.1; 680 mglkg (dog, p.0.) giuconate (1: 1) RN: 21 156-48-9 MF: C2,HZ7N . C,HI2O7 MW: 525.64 LD,,: 14 mgkg (M, i.v.); I l mglkg (R, i.v.) 1706 l' Pridinol phenylocetone 3.3-diphenyl- propylamine ReJerencr(s): DB 1 111 642 (Hoechst; appl. 7.5.1958). DE 1 100 031 (Hoechst; appl. 7.5.1958). Formulution(s): drg. 15 mg, 30 mg, 60 mg; tabl. 4 mg, 15 mg, 30 mg, 60 mg (as lactate) Trade Nume(s): D: Daxauten (Kcttclhack- I: Angiovigor (Violani- J: Crepasin (Hoei) Riker); wfm Farmavigor); wfm Epocol (Teisan-Nagase) Daxauten (Woelm); wfm Angorsan (Isola-Ibi); wfm Herzcon (Sana) Segontin (Albert-Roussel); Carditin-Same (Savoma); Lactarnine (Daisan) wfm wfm NP 30 (Sanken) Segontin (Hoechst); wfm Eucardion (Vita); wfm . Onlemin (Ono) Segontin-Digoxin (Albert- Incoran (ITA); wfm Prectolact (Showa Rousse1)-comb.; wfm Irrorin (Alfa Farm.) Yakuhin) Segontin-Digoxin Reocorin (Parmochimica Prenylamine Lactate (Hoechst)-comb.; wfm Ital.); wfm (Towa) F: Cltmodril (Hoechst)- Segontin (Hoechst); wfm Roinin (Mohan) comb.; wfm Wasangor (IR); wfm Segontin (Hoechst) Segontine (Hoechst); wfm Wasangor (Wassermann); GB: Synadrin (Hoechst); wfm wfm Pridinol ATC: M03BX03 Use: anticholinergic, antiparkinsonian RN: 51 1-45-5 MF: C2,HZ5NO - MW: 295.43 EINECS: 208-128-0 LD,,: 100 mglkg (M, i.p.); 193 mglkg (M, s.c.) CN: a,a-diphenyl- 1 -pipcridinepropanol hydrochloride RN: 968-58-1 MF: C,H,,NO. HCI MW: 331.89 EINECS: 213-529-9 LD,,,: 25 mglkg (M, i.v.1; 33 mgkg (R, i.v.) mesylate RN: 6856-31-1 MF: C,,,H,,NO . CH,03S MW: 391.53 EINECS: 229-953-2 phenylmogncsium ethyl 3-plperldino- bromide (1) propionate acetophenone poroform- piperidine 3-piperidino- oldehyde propiophenone Reference(s): DE 875 660 (Hoechst; appl. 1941). Formulation(s): amp. 2 mglml; drg. 5 mg (as hydrochloride); tabl. 4 mg (as mesylate) Trade Name(s): D: Lyseen-Hommel (Hommel) Ly seen (Novartis) Mitanoline (Toyo Pharmar) Parks 12 (Hommel) J: Hikicenon (Tatsumi) Trilax (Toyo Seiyaku F: Parks-12 (Laroze); wfm Konlax (Nippon Shinyaku) Kasei) I: Algolisina (Celsius)-comb. Loxeen (Maruko-Tobishi) Prilocaine ATC: NOlBB04 Use: local anesthetic RN: 721-50-6 MF: C,,H2,N20 MW: 220.32 EINECS: 21 1-957-0 LD,,: 59.9 mglkg (M, i.v.) CN: N-(2-methylpheny1)-2-(propy1amino)propanamide monohydrochloride RN: 1786-81-8 MF: C,3H20N20. HCI MW: 256.78 EINECS: 217-244-0 LD,,: 55 mgkg (M, i.v.); 56.6 mglkg (R, i.v.) Reference(s): GB 839 943 (Astra; appl. 6.6.1958; S-prior. 26.6.1957). Lofgren, N.; Tegner, C.: Acta Chem. Scand. (ACHSE7) 14,486,490 (1960). o-toluidine 2-bromopropionyl Formulation(s): cream 25 mglg in comb. with lidocaine; plaster 25 mg; vial 5 mglml, 10 mg/ml, 20 mglml, 30 mglml Prilocoine Trade Name(s): D: EMLA Creme (Astra)- Emlapatch (Astra) Emla (Astra Farmaceutici). comb. with lidocaine GB: Citanest (Astra) comb. Xylonest (Astra) EMLA (Astra)-comb. J: Citanest (Astra-Fujisawa) Xylonest (Astra)-comb. I: Citanest 3 % Octapressin USA: Emla (Astra) F: Emla (Astra)-comb. (Astra Farmaceutici)-comb. bromide 1708 P Primaperone Primaperone ATC: COlD Use: vasodilator, antihypotensive RN: 1219-35-8 MF: CIsH2,FNO MW: 249.33 EINECS: 214-941-1 CN: 1 -(4-fluoropheny1)-4-(]-piperidyl)- 1 -butanone hydrochloride RN: 15847-48-0 MF: C,,H2,FN0. HC1 MW: 285.79 4-chloro-4'-fluora- piperidine butyrophenone Primoperone Refprence(s): FR 1 301 863 (Science Union; appl. 29.6.1961). FR 1 459 M (Science Union; appl. 18.8.1961; prior. 29.6.1961). Trade Name(s): F: Diviator (Servier)-comb.; wfm Primaquine (Primachin) ATC: POlBAO3 Use: antimalarial RN: 90-34-6 MF: CISHllN30 MW: 259.35 EINECS: 201-987-2 LD,,,: 15.9 mg/kg (M, i.v.1; 100 mglkg (M, p.0.) CN: 1V-(6-methox~-8-~uinolin~l)-1,4-pen~anediamine phosphate (1:2) RN: 63-45-6 MF: CIH2,N30 . 2H304P MW: 455.34 EINECS: 200-560-8 LD,,,: 68 mgkg (M, p.0.); 177 mglkg (R, p.0.) H2SO4 Fa, HCI H C '-0 oH (Skra~~ synthesis) 4-rnethoxy-2- glycerol 6-rnethoxy- 8-amino- nitroaniline 8-nitra- 6-rnethoxy- quinoline quinaline (I) 'a 0 H2N-NHZ 1 4-brorno-1 -phthol- irnidapentone H C '0 '0 I Primaquine I Primidone P 1709 Reference(s): Elderfield, R.C. et al.: J. Am. Chem. Soc. (JACSAT) 68, 1524 (1946). Elderfield, R.C. et al.: J. Am. Chem. Soc. (JACSAT) 77,4816 (1955). Fomtulation(s): tabl. 15 mg Trade Name(s): D: Primaquine Bayer (Bayer); GB: Primaquine Phosphate USA: Primaquine Phosphate wfm (ICI); wfm (Sanofi); wfm I: Primachina fosfato (IN) Prirnidone (Primaclone) ATC: N03AA03 Use: antiepileptic, anticonvulsant RN: 125-33-7 MF: C,,H,,N,O, MW: 218.26 EINECS: 204-737-0 LDSo: 280 mdkg (M, p.0.); I500 mglkg (R, p.0.) CN: 5-ethyldihydro-5-phenyl-4,6(1H,5fl-pyrimidinedione ethylphenyl- forrnarnide rnalandiamide Prirnidone Reference(s): US 2 578 847 (ICI; 195 I; GB-prior. 1949). DE 843 413 (ICI; appl. 1950; GB-prior. 1949). Formulation(sJ: susp. 250 mg/5 ml; syrup 125 mg/5 ml; tabl. 250 mg Trade Name(s): D: Liskatin (Desitin) F: Mysoline (Zeneca) J: My soline (Dainippon; Mylepsinum (Zeneca) GB: Mysoline (Zeneca) Marupi) ResimatiI (Sanofi I: Mysoline (SIT) Primron (Fujinaga) Winthrop) USA: Mysoline (Wyeth-Ayerst) Probenecid ATC: M04ABOI Use: uricosuric agent RN: 57-66-9 MF: C, 3HI,N0,S MW: 285.36 EINECS: 200-344-3 LD,,: 1666 mglkg (M, p.0.); 1600 mgkg (R, p.0.) CN: 4-[(dipropylamino)suIfonyl]benzoic acid 1710 P Probucol H H~c++~-'YH~ o=s=o o=s=o CI dipropylamine 4-corboxybenzene- Probenecid sulfonyl chloride Reference(s): US 2 608 507 (Sharp & Dohme; 1952; prior. 1949). Formularion(s): tabl. 500 mg Trade Name(s): D: Probenecid (Weimer) Colbenemid (Merck Sharp USA: Benemid (Merck Sharp & F: BCnCmide (ThCraplix); & Dohme)-comb.; wfm Dohme) wfm I: Probcnecid (IFI) Col BENEMID (Merck Prototapen (Bristo1)-comb.; J: Benecid (Kaken) Sharp & Dohme)-comb. w fm Probenemid (Merck- with colchidine GB: Benemid (Merck Sharp & Banyu) Dohme) Probucol ATC: CIOAXO2 Use: antiarteriosclerotic (cholesterol depressant and antihyperlipidemic) RN: 23288-49-5 MF: C,,H,,O,S, M W: 5 16.86 EINECS: 245-560-9 LDSo: >5 glkg (M, p.0.); 25 glkg (R, p.0.) CN: 4.4'-[(I -methylethylidene)bis(thio)]bis[2,6-bis(1 ,I -dimethylethyl)phenol] Referc.nce(s): US 3 576 883 (Consol. Coal; 27.4.1971; prior. 3.6.1969). US 3 862 332 (Dow; 21.1.1975; prior. 11.5.1967, 19.1 1.1969). DE 1 767 443 (Dow; appl. 10.5.1968; USA-prior. 11.5.1967). DE 1 768 334 (Consol. Coal; prior. 2.5.1968). 2.6-di-tert-butyl- starting material: 1JS 3 129 262 (Consolidation Coal Comp.; 14.4.1964; appl. 8.10.1962). Probucol Furmulation(s): tabl. 250 mg, 500 mg 4-mercaptophenol . &apos ;-0 oH (Skra~~ synthesis) 4-rnethoxy- 2- glycerol 6-rnethoxy- 8-amino- nitroaniline 8-nitra- 6-rnethoxy- quinoline quinaline (I) 'a 0 H2N-NHZ 1 4-brorno-1 -phthol- irnidapentone. RN: 14 5-1 3-1 MF: C2,H32O2 MW: 316.49 EINECS: 20 5-6 4 7-4 CN: (3P )-3 -hydroxypregn-5-en-20-one succinate RN: 459 8-6 7-8 MF: C2,H,,05 MW: 416.56 EINECS: 22 5-0 0 1-5 acetate RN: 177 8-0 2-5 MF: C2,H,,0,. glucocorticoid RN: 689 0-4 2-2 MF: C,,H,,NO, MW: 485.62 CN: N,N-diethylglycine (1 1 P )- 1 l,l7-dihydroxy- 16-methylene-3,20-dioxopregna- 1,4-dien-21-yl ester hydrochloride RN: 2288 7-4 2-9 MF: C,,H,,NO,.