Voglibose V 2181 Visnodine J By extraction from Ammi visnaga L. (Umbelliferae) and chromatographic purification. Reference(s): US2816 118 (S. B. Penick&Co.; 10.12.1957; prior. 12.11.1953). US 2 980 699 (S. B. Penick & Co.; 18.4.1961; prior. 20.12.1957). Formulation(s): cps. 70 mg Trude Name(s): D: Carduben (Madaus); wfm F: Vibeline (Roger Bellon); J: Visnamine (Chinoin) wfm Voglibose ATC: A10 Use: antidiabetic, antiobesity, a- glucosidase inhibitor RN: 83480-29-9 MF: C,,H,,NO, MW: 267.28 CN: 3,4-dideoxy-4-[[2-hydroxy-l-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-~-epi-inositol 1. Br,. H,O ' 2. NaBH4. H20 1 , HO-H 2. sodium Hoo.~o.~'O borohydride OH NoBHSCN. DMF. 2N HCI OH sodium cyono- borahydride 1,J-dihydroxy- acetone voliolornine (11) I Voglibose I Reference(s): EP 56 194 (Takeda Chem.; appl. 24.12.1984; J-prior. 5.1.1981,6.10.1981). Hori, S. et al.: J. Med. Chem. (JMCMAR) 29, 1038 (1986). EP 260 121 (Takeda Chem.; appl. 9.9.1987; J-prior. 9.9.1986, 5.1 l.l986,6.1.1987). EP240 175 (Takeda Chem.; appl. 5.3.1987; J-prior. 21.5.1986, 5.3.1986,4.3.1987). 2182 V , Voglibose uncoated tablets with improved resistance: EP 610 854 (Takeda Chem.; appl. 7.2.1994; J-prior. 10.2.1993). composition for promoting calcium absorption: EP 364 696 (Takeda Chem.; appl. 21.8.1989; J-prior. 22.8.1988). EP 197 661 (Takeda Chem.; appl. 10.3.1986; J-prior. 11.3.1985). EP 194 794 (Takeda Chem.; appl. 4.3.1986; WO-prior. 8.3.1985, 30.4.1985). combination for obesity treatment: WO 8 605 094 (Takeda Chem.; appl. 8.3.1985; WO-prior. 8.3.1985, 30.4.1985). EP 638 3 17 (Hoffmann-La Roche; appl. 22.7.1 994; CH-prior. 5.8.1993). Formulation(s): tabl. 0.2 rng, 0.3 mg Trade Name(s): J: Basen (Takeda) Glustat (Takeda) Warfarin W 2183 Warfarin ATC: BOlAA03 Use: anticoagulant RN: 81-81-2 MF: C,,H,,O, MW: 308.33 EINECS: 201-377-6 LD,,: 165 mglkg (M, i.v.); 3 mglkg (M, p.0.); 1600 ~gkg (R, p.0.); 3 mdkg (dog, p.4 CN: 4-hydroxy-3-(3-oxo-I-phenylbutyl)-2H-l-benzopyran-2-one sodium salt RN: 129-06-6 MF: C,,H,,Na04 MW: 330.32 EINECS: 204-929-4 LD,,: 160 mgkg (M, i.v.); 374 mglkg (M, p.0.); 25 mgkg (R, i.v.); 8700 ~glkg (R, p.0.); 200 mgkg (dog, i.v.); 200 mglkg (dog, p.0.) pyridine OH 0 4-hydroxy- benzal- coumarin acetone Reference(s): US 2427 578 (Wisconsin Alumni Res. Found.; 1947; prior. 1945). sodium salt: US 2 777 859 (Wisconsin Alumni Res. Found.; 1957; prior. 1953). US 2 765 321 (Wisconsin Alumni Res. Found.; 1956; appl. 1955). US 3 077 481 (Wisconsin Alumni Res. Found.; 12.2.1963; appl. 21.2.1961) Formulation(s): amp. 2 mglml; tabl. 1 mg, 2 mg, 2.5 mg, 3 mg, 4 mg, 5 mg, 6 mg, 7.5 mg, 10 mg (as sodium salt) Trade Name(s): D: Coumadin (Du Pont) GB: Marevan (Goldshield) J: Warfarin (Eisai) F: Coumadine (Du Pont) I: Coumadin Endo (Du Pont) USA: Coumadin (Du Pont) 21 84 X Xamoterol Xamoterol (ICI- 1 1 8587) ATC: COICA; COICX07 Use: cardiac stimulant, P-antagonist RN: 81801-12-9 MF: C,,Hz5N,05 MW: 339.39 CN: (+)-N-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide fumarate RN: 69630-19-9 MF: C,,Hz5N,0S . C4H404 MW: 455.46 (&)-monohydrochloride RN: 112008-18-1 MF: C16Hz5N,05 . HC1 MW: 375.85 (+)-fumarate (2: 1) RN: 90730-93-1 MF: Cl6HZ5N3Ov 1/2C4H404 MW: 794.86 fumarate (2:l) RN: 73210-73-8 MF: ClhHZ5N3O5 . 1/2C4H404 MW: 794.86 EINECS: 277-3 19-9 epichlaro- hydrin NaOH d 0J.N-~~2. KOH H b 1 4-[N-(2-amino- ethyl)corbornoyl]- rnorpholine Reference(s): DOS 2 822 473 (ICI; appl. 23.5.1978; GB-prior. 23.5.1977). US 4 143 140 (ICI; 6.3.1979; GB-prior. 23.5197'7). Barlow, J.J. et al.: J. Med. Chem. (JMCMAR) 24, 315 (1981). Formulation(s): tabl. 200 mg Trade Name(s): GB: Corwin (Zeneca) J: Sepan (Yamanouchi) USA: Corwin (Zeneca) Xantinol nicotinate (Xanthinol-Niacinate) ATC: C04AD02 Use: vasodilator RN: 437-74-1 MF: CI3Hz1N4O4. C6H5N02 MW: 434.45 EINECS: 207-115-7 LD,,: 673 mglkg (M, i.v.); 17350 mglkg (M, p.0.); 690 mglkg (R, i.v.); 14130 mglkg (R, p.0.) CN: 3-pyridinecarboxylic acid compd. with 3,7-dihydro-7-[2-hydroxy-3-[(2- hydroxyethyl)methylamino]propyl]-1,3-dimethyl- lH-purine-2,6-dione (1: 1) Xibenolol X 2185 - 0 1 CH3 epichloro- Z-methylomino- hydrin ethanol +OH +OH COOH QCOOH CH3 CH3 Reference(s): US 2 924 598 (J. A. Wiilfing; 9.2.1960; D-prior. 26.10.1957). xanthinol (I) nicotinic Formulation(s): amp. 300 mg; s. r. cps. 500 mg; s. r tabl. 150 mg, 300 mg, 1000 mg; tabl. 150 mg, 300 mg, 1000 mg Xontinol nicotinate Trade Narne(s): D: Complamin (SmithKline Xantinol-nicotinal retard- GB: Complamex (Gemini); wfm Beecham) ratiopharm (ratiopharm) I: Complamin (Italchimici) Theonikol (rnedpharm) F: Complamine (LatCrna); USA: Complamin (Riker); wfm wfm acid Xibenolol Use: beta blocking agent RN: 30187-90-7 MF: Cl,H2sNOZ MW: 251.37 CN: 1 -[(I ,1-dimethylethyl)amino]-3-(2,3-dimethylphenoxy)-2-propanol 2,3-xylenol (I) epichloro- hydrin (11) tert-butyl- Xibenolol I omine (N) 2186 X Xibornol Reference(s): JP 7 029 294 (Teikoku; appl. 17.8.1968). JP 6 041 623 (Teikoku; appl. 17.8.1968). alternative synthesis: JP 4 033 185 (Teikoku; appl. 5.8.1969). DOS 2 058 532 (Teikoku; appl. 27.1 1.1970; J-prior. 28.1 1.1969, 31.3.1970,21.7.1970, 13.1 1.1970). DOS 2065 365 (Teikoku; appl. 27.11.1970; J-prior. 28.11.1969, 31.3.1970,21.7.1970, 13.11.1970). inedical use: GB 1 422 046 (Teikoku; appl. 19.1.1973). Trade Narne(s): J: Rythminal (Teikoku) Xibornol ATC: JOlXXO2 Use: bronchochemotherapeutic RN: 13741- 18-9 MF: C,8H2,0 MW: 258.41 EINECS: 237-312-3 CN: exo-4,5-dimethyl-2-(1,7,7-trimethylbicyclo[2.2.l]hept-2-yl)phenol (-)-carn~hene (I) 3.4-xylenol anisole SnCI4. 70-80 OC and chromotog. purification ______, Reference(s): a GB 1 206 774 (Mar-Pha; appl. 23.10.1967). b DOS 2 032 170 (Mar-Pha; appl. 30.6.1970; GB-prior. 4.7.1969). p CH3 " H Xibornol allernative process: DOS 2 912 762 (Farmatis; appl. 30.3.1979). Xipamide X 2187 Formulation(s): cps. 250 rng; spray 3 %; susp. 100 mg Trade Name(s): F: Nanbacine (Bellon Groupe I: Bracen (Zyma); wfrn RhBne-Poulenc Rorer) Xibor (Benedetti); wfm Xipamide ATC: C03BA10 Use: diuretic RN: 14293-44-8 MF: C,sH,sCIN20,S MW: 354.81 EINECS: 238-216-4 LD,,: 1810 rngkg (M, p.0.); 1640 mgkg (R, p.0.); >50 rngkg (dog, i.v.); > 1500 rngkg (dog, p.0.) CN: 5-(arninosuIfonyl)-4-chloro-N-(2,6-dirnethylphenyl)-2-hydroxybenzarnide 4-chloro- salicylic acid 5-arninosulfonyl- 4-chlorosalicylic acid (I) PC13 I + - phosphorous trichloride Reference(s): US 3 567 777 (Beiersdorf; 2.3.1971; D-prior. 19.6.1965). DE 1 270 544 (Beiersdorf; appl. 19.6.1965). 2,6-dimethyl- Formulation(s): tabl. 10 rng, 20 mg, 40 rng Xipamide Trade Name(s): D: Aquaphor (Beiersdorf- Neotri (Beiersdorf-Lillyl Lurnitens (Solvay Pharrna) LillyILilly) Lilly)-comb. with GB: Diurexan (ASTA Medica) Durotan (Beiersdorf-Lil1y)- triarnterene I: Aquafor (ASTA Medica comb. with reserpine F: Chronexan (ASTA Medica) AWD) aniline I Xylometazoline ATC: ROlAA07; RO1 ABO6; SOlGA03 Use: vasoconstrictor, rhinological therapeutic RN: 526-36-3 MF: C,,H,N2 MW: 244.38 EINECS: 208-390-6 LD,,: 215 rnglkg (M, p.0.) CN: 2-[[4-(1,l -dirnethylethyl)-2,6-dirnethylphenyl]rnethyl]-4,5-dihydro- 1 H-irnidazole monohydrochloride RN: 1218-35-5 MF: C16H24Nl. HCI MW: 280.84 EINECS: 214-936-4 21 88 X Xvlometazoline 4-tert-butyl-2.6- ethylene- Xylometozoline dimethylbenzyl diomine cyanide Reference(s): US 2 868 802 (Ciba; l3.1.19S9; CH-prior. 10.7.1956). DE 1 049 387 (Ciba; appl. 3.7.1957; CH-prior. 10.7.1956). Formularion(s): drops 0.5 mglml, 1 glml; eye drops 1 mglml; gel 1 mg/g; sol. 0.25 mglml, 0.5 mg/ml, 1 mgtrnl: spray 0.5 mglml, lmglml (as hydrochloride) Trade Name(s): D: Balkis (Dolorgiet) Dorenasin (Rentschler) Gelonasal (Pohl) Imidin (Pharma Wernigerode) Lomupren comp. (Fisons)- comb. rnentopin (Hermes) Nasan (Hexal) Nasengel-ratiopharm (ratiopharm) Nasenspray-ratiopharrn (ratiopharm) Nasentropfen K-ratiopharm (ratiopharm) Ol y nth (Warner-Lambert) Otriven (Novartis) Otriven (CIBA Vision) Pertix Hommel (Hornmel) Rapako (Truw) schnupfen endrine (Asche) stas Nasenspray (Stada) X ylo-COMOD (Ursapharm) Xylo-E (ct-Arzneimittel) GB: Otrivine (Novartis) Otrivine-Antistin (CIBA Vision)-comb. with antazoline Rynacrom compound (RhBne-Poulenc Rorer) I: Neorinoleina (Synthelabo) Otrivin (CIBA Vision) Kespiro (B yk Gulden)- comb. Rinos (Mo1teni)-comb. USA: Otnvm (Geigy); wfm Zafirlukast Z 2 189 Zafirlukast (ICI-2042 19) ATC: R03DCOI Use: antiasthmatic, LTD,-antagonist RN: 107753-78-6 MF: C3,H,,N30,S MW: 575.69 CN: [3-[[2-methoxy-4-[[[(2-methylphenyl)sulfony]amino]carbonyl]phenyI]methyl]- 1 methyl-1 H-indol-5- yllcarbamic acid cyclopentyl ester monohy drate RN: 143052-93-1 MF: C3,H33N30,S . H20 MW: 593.70 calcium salt (2:l) RN: 107753-86-6 MF: C6,H,CaN,O1,S2 MW: 1 189.43 3 Ag20, dioxone H3C-0 H3C-0 -I methyl 3-methoxy- 4-methylbenzoote methyl 4-bromo- methyl-3-methoxy- benzoote methyl 3-methoxy-4- iodo- (5-nitroindol-3-ylmethyl)- methane benzoote (I) methyl 3-methoxy-4- (1 -methyl-5-nitroindol- 3-ylmethyl)benzoote (11) A H,. ~d-c O-N-CH3 , CH,CI, I1 * cyclopentyl chloroformate (111) H3C-0 methyl 4-(5-amino-1 -methyl- indol-3-ylmethy1)-3- methoxybenzoate methyl 4-[S-(cyclopentyloxy- carbonylamino)-1 -methylindol- 3-ylmethyll-3-methoxybenzoate (1V) 4-[S-(cyclopentylaxycarbonyl- amino)-1 -methylindol-3- ylmethyll-3-methoxybenzoic acid (V) 2190 Z Zafirlukast 2-rnethylbekne- sulfonornide (V1) . - H3C- xN\cH3 e HCI N=C=N DMAP 1 -(3-dirnethylarninopropyl)- 3-ethylcorbodiirnide hydrochloride I Zofirlukost Zofirlukost u Vl . SOCb, DMF, CH2C12 CHf NoOH, , w H3C-0 4-(5-nitro-1 -rnethylindol- 3-ylrnethy1)-3-rnethoxy- benzoic acid Vlll + 111 + Zafirlukost I Referencefs): a EP 199 543 (ICI, Zeneca; appl. 16.4.1986; GB-prior. 17.4.1985). crystalline form suitable for inhalation: b EP 490 649 (ICI, Zeneca; 1 1.12.1991 ; GB-prior. 12.12.1990). Matassa, G. et al.: J. Med. Chem. (JMCMAR) 33, 1781 (1990). Formulation(s): tabl. 20 mg Trade Namefs): USA: Accolate (Zeneca) . (111) H3C-0 methyl 4-( 5-amino-1 -methyl- indol-3-ylmethy1 )-3 - methoxybenzoate methyl 4-[ S-(cyclopentyloxy- carbonylamino )-1 -methylindol- 3-ylmethyll-3-methoxybenzoate (1V) 4-[ S-(cyclopentylaxycarbonyl-. 10775 3-8 6-6 MF: C6,H,CaN,O1,S2 MW: 1 189.43 3 Ag20, dioxone H3C-0 H3C-0 -I methyl 3-methoxy- 4-methylbenzoote methyl 4-bromo- methyl-3-methoxy- benzoote methyl 3-methoxy- 4- iodo-. 3-pyridinecarboxylic acid compd. with 3,7-dihydro- 7-[ 2-hydroxy- 3-[ ( 2- hydroxyethyl)methylamino]propyl ]-1 ,3-dimethyl- lH-purine-2,6-dione (1: 1) Xibenolol X 2185 - 0 1 CH3 epichloro-