Droperidol D 721 isolation. 95-1 20 OC I Zab. sativa. Cannabis indica. Cannobis ruderalis heference(s): a Handrick, G.R. et al.: Tetrahedron Lett. (TELEAY) 1979, 681. b US 4 116 979 (Sheehan Inst. for Research; 26.9.1978; appl. 7.2.1977; pnor. 28.11.1975, 24.6.1975) US 4381 399 (Aerojet; 26.4.1983; appl. 21.12.1981). c US 4 279 824 (L. 0. McKinney; 21.7.1981; appl. 1.1 1.1979). alternative methods: US 3 734 930 (US Dep. of Health; 22.5.1973; appl. 22.9.1971) Straight, R. et al.: Biochem. Med. (BIMDA2) 8,341 (1973). Ribi, E. et al.: Prep. Biochem. (PRBCBQ) 3, 209 (1973). review: Mechoulam, R. et al.: Chem. Rev. (Washington, D. C.) (CHREAY) 76, 75 (1976). Formulation(s): cps. 2.5 mg, 5 mg, 10 mg Trade Name(s): USA: Marinol (Roxane) Droperidol (Dehydrobenzperidol) ATC: NOlAXOl; NOSAD08 Use: neuroleptic, anesthetic (neuroleptanesthesia) RN: 548-73-2 MF: C2,H2,FN302 MW: 379.44 EINECS: 208-957-8 LD,,: 20 mgkg (M, i.v.); 30 mgkg (R, i.v.); 750 mglkg (R, p.0.) CN: 1-[1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-dihydro-2H-ben~imidazo1-2-one ethyl 1 -benzyl- 4-0x0-piperidine- 3-carboxylote a-phenylene- diarnine 140 OC, xylene - H,, Pd-C b 1 722 D Dropropizine 1 -(1.2.3.6-tetra- 4-chlora-4'-fluaro- hydro-4-pyridyl). butyraphenane 2-benzimidazolinane (I) Droperidol I GB 989 755 (Janssen; appl. 24.12.1962; USA-prior. 22.12.1961). US 3 141 823 (Janssen; 21.7.1964; appl. 4.9.1962). US 3 161 645 (Janssen; 15.12.1964; appl. 18.12.1962). Formulatinn(s): amp. 2.5 mglml, 5 mg12 ml, 12.5 mg15 ml, 25 mg1lO ml; tabl. 10 mg; vial 5 mgl2 ml, 12.5 mg15 ml, 25 mg/lO ml Trade Name(s): D: Dehydrobenzperidol GB: Droleptan (Janssen-Cilag) USA: Droperidol (Astra) (Janssen-Cilag) I: Leptofen (Carlo Erba)- Inapsine (Janssen; Thalamonal (Janssen- comb. McNeil)'; wfm Cilag)-comb. Sintodian (Carlo Erba) Innovar (Janssen); wfm F: Droleptan (Janssen-Cilag) J: Droleptan (Sankyo) Dropropizine ATC: R05DB 19 Use: antitussive RN: 17692-3 1-8 MF: C,,H,,,N,O, MW: 236.32 EINECS: 241-683-7 LD,,,: 200 mglkg (R, i.v.); 750 mglkg (R, p.0.) CN: 3-(4-phenyl- l -piperazinyl)- 1,2-propanediol 0 1-phenyl- glycide Dropropizine piperazine Referenceis): DE 1 178 435 (H. Morren; appl. 13.3.1962; B-prior. 16.3.1961,21.2.1962) Fornzulution(s): syrup I5 mg, 57 mg Trade Name(s): D: Dehydrobenzperidol I: Elisir Terpina Ribexen Espet. (Formenti)- (Janssen-Cilag) (Schiapparelli Salute). comb. Thalamonal (Janssen- comb. Tiocalmina (0ttolenghi)- Ci1ag)-comb. with fentanyl Guaiacalcium Complex comb. hydrogen citrate (Celsius)-comb. Tussamag (Zil1iken)-comb, F: Catabex (Darcy)-comb. Ribex (Formenti) 722 D Dropropizine 1 -(1.2.3.6-tetro- 4-chloro-4'-fluora- Droperidol hydro-4-pyridy1)- butyrophenone 2-benzimidozolinone (I) Reference(s): GB 989 755 (Janssen; appl. 24.12.1962; USA-prior. 22.12.1961). US 3 141 823 (Janssen; 21.7.1964; appl. 4.9.1962). US 3 161 645 (Janssen; 15.12.1964; appl. 18.12.1962). Formulation(s): amp. 2.5 mg/ml, 5 mg/2 ml, 12.5 mg/5 ml, 25 mg/lO ml; tabl. 10 mg; vial 5 mg/2 ml, 12.5 mgI5 ml, 25 mg/lO ml Trade Name(s): D: Dehydrobenzperidol GB: Droleptan (Janssen-Cilag) USA: Droperidol (Astra) (Janssen-Cilag) 1: Leptofen (Carlo Erba)- Inapsine (Janssen, Thalamonal (Janssen- comb. McNeil)'; wfm Cilag)-comb. Sintodian (Carlo Erba) Innovar (Janssen); wfm F: Droleptan (Janssen-Cilag) J: Droleptan (Sankyo) Dropropizine ATC: R05DB19 Use: antitussive RN: 17692-3 1-8 MF: C,,H2,,N,02 MW: 236.32 EINECS: 241-683-7 LD,,,: 200 mglkg (R, i.v.); 750 mg/kg (R, p.0.) CN: 3-(4-phenyl-l -piperazinyl)-1.2-propanediol 1 -phenyl- piperozine glycide I Dropropizine I Reference(s): DE 1 178 435 (H. Morren; appl. 13.3.1962; B-prior. 16.3.1961, 21.2.1962). Formulation(s): syrup 15 mg, 57 mg Trade Name(s): D: Dehydrobenzperidol I: Elisir Terpina Ribexen Espet. (Formenti)- (Janssen-Cilag) (Schiapparelli Salute)- comb. Thalamonal (Janssen- comb. Tiocalmina (0ttolenghi)- Ci1ag)-comb. with fentanyl Guaiacalcium Complex comb. hydrogen citrate (Celsius)-comb. Tussamag (Zi1liken)-comb. F: Catabex (Darcy)-comb. Ribex (Formenti) 724 D Dyclonine 3-ethoxycorbonyl- 2-phenoxycdrbonyl- Droxicam 4-hydroxy-2-methyl- aminopyridine 2H- 1.2-benzothiozine 1,l -dioxide (cf. piroxicom synthesis) Reference(s): EP 99 770 (Provesan, Esteve; appl. 8.6.1983; F-prior. 15.6.1982). US 4 563 452 (Provesan, Esteve; 7.1.1986; appl. 8.6.1983; F-prior. 15.6.1982). alternative synthesis: EP 242 289 (Provesan; appl. 13.4.1987; F-prior. 15.4.1986). EP 412 014 (Esteve; appl. 2.8.1990; F-prior. 4.8.1989). Formulation(s): cps. 20 mg Trade Name(s): 1: Dobenam (Angelini) Droxar (Upjohn) D yclonine ATC: NOlBX02 Use: local anesthetic (only topic) RN: 586-60-7 MF: C,,H,,NO, MW: 289.42 CN: 1-(4-butoxypheny1)-3-(1-piperidiny1)- 1-propanone hydrochloride RN: 536-43-6 MF: CluH27N02. HCI MW: 325.88 EINECS: 208-633-6 LD,,,: 20 mglkg (M, i.v.); 9500 ~glkg (dog, i.v.) Reference(s): US 2 771 391 (Allied Laboratories; 1956; prior. 1953). US 2 868 689 (Allied Laboratories; 1959; appl. 1956). 4'-butoxyacetophenone piperidine paroform- Formulation(s): sol. 0.5 %, 1 % Dyclonine Trade Name(s): J: Epicain Ace (S. S. Pharm.)- Epirocain (Eisai) USA: Dyclone (Astra; as comb. hydrochloride) aldehyde ATC: G03DBOI Use: progestogen RN: 152-62-5 MF: C,,H,,O, MW: 312.45 EINECS: 205-806-8 LD,: >7200 mglkg (M, p.0.); A600 mglkg (R, p.0.) CN: (9P,lOa)-pregna-4,6-diene-3,20-dione chloronil, tert-butonol ntmprogesterone Dydrogesterone (from lum~steml~) i 9 1 Reference(s): US3 198 792 (North Amencan Phllips; 3.8.1965; prior. 8.4.1959, 12.6.1962). 1 Westerhof, P.; Reerink, E H.: Recl. Trav. Chim. Pays-Bas (RTCPA3) 79, 771 (1960) (also startlng matend). t alternative synthesis: j Rappoldt, M.P.; Westerhof, P.: Recl. Trav Chlm Pays-Bas (RTCPA3) 80.43 (1961). P Formulation(s): tabl. 10 mg I - Tmde Name(s): 1 D: Duphaston (Solvay $ Arzneimittel) f R Duphaston (Solvay Femapak 40 (Sohay)- J: Duphaston (Daiichi) comb. USA: Duphaston (Philips Femoston 1/10 (Solvay)- Roxane); wfm Pharma) comb. B: Duphaston (Solvay) I: Dufaston (UCM) Gynorest (Mead Johnson wfm 4 726 E Ebastine Ebastine ATC: DO4AA; R06AA; R06AX22 Use: antihistaminic RN: 90729-43-4 MF: CJ2H3,N02 MW: 469.67 LD,,,: 500 mglkg (M, i.v.); >4 glkg (M, p.0.); >4 glkg (R, p.0.); >I60 mglkg (dog, p.0.) CN: 1 -[4-(1,l -dimethylethyl)phenyl]-4-[4-(diphenylmethoxy) 1 -piperidinyl]- 1-butanone 4-tert-butyl-w-chloro- 4-hydroxypiperidine 1 -[3-(4-tert-butylbenzoyl)- butyrophenone (I) propyll-4-hydroxypiperidine -([I) 3. 1 ______, 1. ethyl chloroformate diphenylmethyl bromide diphenylpyraline Ebastine Reference(s): EP 134 124 (Fordonal; appl. 2.8.1984; GB-prior. 5.8.1983). US 4 550 116 (Fordonal; 29.10.1985; appl. 24.7.1984; GB-prior. 5.8.1983). Formulafion(s): sol. I0 mgllO ml; tabl. 5 mg, 10 mg Trade Name(s): J: Ebastel (Dainippon-Meji Seika) Ebrotidine (Fl-3542) ATC: A02B09 Use: gastric antisecretory, H,-receptor antagonist, gastroprotective RN: 100981-43-9 MF: C,,H,,BrN,O,S, MW: 477.43 CN: [N(E)]-N-[[[2-[[[2-[(Aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]ethyl]amino]-methylene]-4 bromobenzenesulfonamide Ecabet sodium E 727 b 4-brornabenzene- triethyl ~ulfanarnide orthoforrnate ! I j b, + Fr c NH2 ! [4-[[(2-arninoethyl)thio]- Ebrot~d~ne I methyl]-2-thiazolyll- $ 6, guonidine (11) (cf famatidine synthesis) E 1-ornidinath~ourea 1,3-dichloro- acetane Reference(s): EP 159 012 (Ferrer Internacional; appl. 16.4.1985; E-prior. 18.4.1984). % Anglada, L.; Marquez, M.; Sacr~stan, A.; Ortiz, J.A.: Eur. J. Med. Chem. (EJMCA5) 23 (I), 97 (1988). Anglada, L.; Raga, M.; Marquez, M.; Sacristan, A.; Castello, J.M.; Ortiz, J.A.: Arzneim Forsch. (ARZNAD) 47 (4a), 431 (1997). + new bromobenzenesulphonamide derivatives - used as histamine receptor antagonists to inhiblt acid secretion: WO 9 614 306 (Ferrer Int.; WO-pr~or. 4.1 1.1994). synthesis of [4-[[(2-aminoethyl)thio]methyl]-2-thiazolyl]guanidine: DE 2 817 078 (ICI; appl. 19.4.1978; GB-prior. 20.4.1977). Roman, E.; Galceran, M.T.; Anglada, L.; Albet, C.: J. Pharm. Sci. (JPMSAE) 83 (2), 252 (1994) Trade Name(s): ES: Ebrocit (Ferrer; Labs. Robert; 1997) Ecabet sodium (TA-2711) Use: ulcer therapeutic RN: 86408-72-2 MF: C2,,H2,Na0,S MW: 402.49 LD,,: >2 glkg (R, p.0.) CN: [1R-(la,4a~,10aa)]-l,2,3,4,4a,9,10,l0a-octahydro-l,4a-dimethyl-7-(l-methylethyl)-6-sulfo- 1 - phenanthrenecarboxylic acid monosodium salt free acid , RN: 33159-27-2 MF: C2,,H,,0SS MW: 380.51 728 E Econazole abietic acid dehydroobietic acid Ecobet sodium Reference(s): Fieser, L.F. et al.: J. Am. Chem. Soc. (JACSAT) 60,263 1 (1938). Wada, H. el al.: Chem. Pharm. Bull. (CPBTAL) 33 (4), 1472 (1985). EP 78 152 (Tanabe Seiyaku; appl. 21.10.1982; GB-prior. 22.10.1981, 29.6.1982). oral preparations: JP 07 165 572 (Tanabe Seiyaku; appl. 9.12.1993; J-prior. 9.12.1993). Formulation(s): gran. 66.7 % Trade Nume(s): J: Gastrom (Tanabe Seiyaku- Nippon; Boehringer Ing.) Econazole ATC: DO IAC03; GOlAFO5 Use: fungicide, antifungal RN: 27220-47-9 MF: ClnHljC13N20 MW: 381.69 EINECS: 248-341-6 CN: 1 -[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]- lH-imidazole mononitrate RN: 24169-02-6 MF: CInHISC13N20 HNO, MW: 444.70 EINECS: 246-053-5 LD,,: 38 mglkg (M,i.v.); 463 mglkg (M, p.0.); 50 mglkg (R, i.v.); 668 mglkg (R, p.0.); > 160 mg/kg (dog, p.0.) ? 1. NaH . 1. sodium hydride 2. 4-chlorobenzyl chloride 1 -(2.4-dichloropheny1)- 2-(1 H-irnidazol- l -yl)eihanol (cf. rniconozole synthesis) Econazole I Reference(s): DAS 1 940 388 (Janssen; appl. 8.8.1969; USA-prior. 19.8.1968). US 3 717 655 (Janssen; 20.2.1973; prior. 19.8.1968). Godefroi, E.F. et al.: J. Med. Chern. (JMCMAR) 12,784 (1969). Form~darion(s): cream 1 g1100 g; lotion 1 g1100 g; pastes I0 mg; powder 1 g/100 g; sol. 1 @I00 g; spray 1 gI100 g (as nitrate) Ecothiopate iodide E 729 Trade Name(s): D: Epi Pevaryl (Janssen-Cilag) Gyno-Pevaryl (Janssen- Cilag) F: Dermazol (Bailleul) FongCryl (L'Arguenon) Gyno-PCvaryl (Janssen- Cilag; 1976) I: Pevaryl (Janssen-Cilag; 1976) Pevisone (Janssen-Ci1ag)- comb. GB: Econacort (Bristol-Myers Squibb)-comb. Ecothiopate iodide (Echothiopate iodide) Ecostatin (Bristol-Myers Squibb) Gyno Pevaryl (Janssen- Cilag) Pevaryl (Janssen-Cilag; 1978) Amicel (Salus) Chemionazolo (Brocchieri) Dermazol (CT) Eco Mi (Geymonat) Ecodergin (Von Boch) Ecorex (Tosi-Novara) Ifenec (Italfarmaco) Micofugal (Biopharma) Micogin (Crosara) Micos (AGIPS) Micosten (Bergamon) Pargin (Gibipharma) Pevaryl (Cilag; 1978) Pevisone (Ci1ag)-comb. Skilar (Bonomelli Farm.) Skilar (Italchemie) J: Palavale (Otsuka; 1981) USA: Spectazole (Ortho Dermatological; 1983) ATC: SOlEB03 Use: cholinesterase inhibitor RN: 513-10-0 MF: C9H231N03PS MW: 383.23 EINECS: 208-1 52-1 LD,,: 5100 ~glkg (M, p.0.); 174 ~glkg (R, p.0.) CN: 2-[(diethoxyphosphinyl)thio]-N,N,N-trimethylethanaminium iodide U' 0 ~~3 methyl7 H~c-' iodide diethyl 2-dimethylamina- phospho- ethyl mercoptan chloddate Ecothiopate iodide Reference(s): US 2 91 1 430 (Campbell Pharmaceuticals; 3.1 1.1959; prior. 15.1.1958). Formulation(s): eye drops 1.25 mglml Trade Name(s). D: Ophtorenin (Winzer); wfrn GB: Phospoline Jodide (Ayerst); USA: Echodide (Alcon); wfrn Phospholinjodid wfm Phospholine Jodide Augentropfen (Winzer); I: Phospholine Jodide (Ayerst); wfm wfm (Chinoin); wfm F: Phospholine Iodide J: Phospholin Jodide (Promedica) (Tobishi) Edetic acid ATC: V03~~03 (Acide edetique; Acidum edeticum; Tetracemin) Use: antidote, chelating agent RN: 60-00-4 MF: Cl,Hl,N20, MW: 292.24 EINECS: 200-449-4 LD,: 28.5 mglkg (M, i.v.); 30 mglkg (M, p.0.) CN: N,llr-1,2-ethanediylbis[N-(carboxymethyl)glycine] disodium salt RN: 139-33-3 MF: C,,H,,N,Na20, MW: 336.21 EINECS: 205-358-3 730 E Edetic acid disodiurn salt dihydrate RN: 6781 -92-6 MF: C1,H,,N2Na2O, . 2H20 MW: 372.24 calcium disodium salt RN: 62-33-9 MF: Cl,,H12CaN2Na,0, MW: 374.27 EINECS. 200-529-9 calcium disodium salt hydrate RN: 2341 1-34-9 MF: C,,H,,CaN,Na,O, . xH20 MW: unspecified dipotassium salt RN: 2001-94-7 MF: C,,,Hl4K,N20, MW: 368.42 EINECS: 217-895-0 dipotassium salt monohydrate RN: 58 167-76-3 MF. C1,,HI4K,N2O, . H,O MW: 386.44 dipotassium salt dihydrate RN: 25 102- 12-9 MF: C,,H14K2N20, . 2H20 MW. 404.45 tetrasodium salt RN: 64-02-8 MF: C,,H12N2Na40, MW: 380.17 EINECS: 200-573-9 LD,,,: 330 mglkg (M, i.p.) triwdium salt RN: 150-38-9 MF: CI,H13N2Na,0, MW: 358.19 EINECS: 205-758-8 LD,,,: 2150 mgkg (M, p 0.); 2150 mgkg (R, p.0.) iron(II1) sodium salt RN 15708-41-5 MF: CloH,2FeN2Na0, MW: 367.05 EINECS: 239-802-2 LD,,,: 5 g/kg (M, p.0.); 5 gfkg (R, p.0.) diarnine (I) I 1 1. 60-110 OC 2. HCI ar HZSO+ H2N~NH2 + 0=cn2 + NaCN - ethylene- (I1) f CN I + n + HCN -4 NCfiN~NvCN (COOH HOOCfiN-N-COOH LOOH Edetic acid ethylenediarnine- tetraacetonitrile Refcnr~ce(s j: Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 8, 198. a DOS 2 150 994 (BASF; appl. 13.10.1971). DOS 1 493 480 (BASF; appl. 30.4.1965). DOS 2 049 223 (BASF; appl. 7.10.1970). b DRP 694 780 (I.G. Farben; appl. 1937). Formulation(s): inj. sol. 200 mglml (as calcium disodium salt) Trade Name(s j: D: Calcium Vitis (Neopharma) Duracare (Pharm- F: Calci tetracCn~ate disodique Complete all-in-one- Allergan)-comb. (L' Arguenon) Liisung (Pharm-Allergan)- Oxysept (Pharm-Allergan)- Chelatran (L'Arguenon) comb. comb. KClocyanor (L'Arguenon; as cobalt salt) . 1-[ 1-[ 4-( 4-fluorophenyl )-4 -oxobutyl ]-1 ,2,3,6-tetrahydro-4-pyridinyl ]-1 ,3-dihydro-2H-ben~imidazo 1-2 -one ethyl 1 -benzyl- 4-0 x0-piperidine- 3-carboxylote a-phenylene- diarnine 140 OC, xylene - H,, Pd-C b 1 722 D Dropropizine 1 -( 1.2.3.6-tetra-. -dimethylethyl)phenyl ]-4 -[ 4-( diphenylmethoxy) 1 -piperidinyl ]- 1-butanone 4-tert-butyl-w-chloro- 4-hydroxypiperidine 1 -[ 3-( 4-tert-butylbenzoyl )- butyrophenone (I) propyll-4-hydroxypiperidine -( [I) 3. 1 ______,. RN: 54 8-7 3-2 MF: C2,H2,FN302 MW: 379.44 EINECS: 20 8-9 5 7-8 LD,,: 20 mgkg (M, i.v.); 30 mgkg (R, i.v.); 750 mglkg (R, p.0.) CN: 1-[ 1-[ 4-( 4-fluorophenyl )-4 -oxobutyl ]-1 ,2,3,6-tetrahydro-4-pyridinyl ]-1 ,3-dihydro-2H-ben~imidazo 1-2 -one