- Glipizide G 971 Glipizide ATC: A 108807 Use: antidiabetic 29094-61-9 MF: C21H27N50,S MW: 445.54 EINECS: 249-427-6 >3 g/kg (M, i.p.); 1200 mgkg (R, i.p.) N-[2-[4-[[[(cyclohexylamino)carbonyl]ami1io]sulfonyl]phenyI]ethyl]-5-methylpyrazinecarboxamide 2. 4-(2-arninoethy1)- 5-methylpyrozinc- benzenesulfonomide (1) 2-carboxylic acid Referencefs): DAS 2 012 138 (Carlo Erba; appl. l4.Y.1970; I-prior. 26.3.1969, 18.6.1969). US 3 669 966 (Carlo Erba; 13.6.1972; I-prior. 26.3.1969, 18.6.1969). Ambrogli, V. et al.: Arzneim-Forsch. (ARZNAD) 21, 200 (1 97 1). NaOH preparation of5-methylpyrazinc-2-carboxylic acid from 2,s-dimethylpyrazine via oxidutiort: Stoehr: J. Prakt. Chem. (JPCEAO) (2), 51, 464 (1895). Stoehr: J. Prakt. Chem. (JPCEAO) (2), 47, 480 (1 893). Kiener, A,: Angew. Chem. (ANCEAD) 104 (6), 748 (1992). Goldberg, Yu.; Shymanska, M.: Org. Prep. Proced. Int. (OPPIAK) 23 (2), 188 (1991). cyclohexyl electrochemical preparation of 5-methylpyrazine-2-carboxylic acid: Borsotti, G.P.; Foh, M.; Gatti, N.: Synthesis (SYNTBF) 1990 (3), 207. Feldman, D. et al.: Chem. Heterocycl. Compd. (N. Y.) (CHCCAL) 31 (l), 80 (1995). GI:pizide Formulation(s): tabl. 2.5 mg, 5 mg, 10 mg isocyanate Trade Name(s): D: Glibenese (Pfizer; 1977.) Osidia cp B lib ~nodifike I: Minidiab (Carlo Erba; F: GliEn6se (Pfizer; 1974) (CC) (Pfizer) 1972) Minidiab (Pharmacia & GB: Glibenese (Pfizer; 1975) USA: Glucotrol (Pfizer; 1984) Upjohn; 1974) Minodiab (Pharmacia & Upjohn; 1975) Gliquidone ATC: AlOBBO8 Use: antidiabetic RN: 33342-05-1 MF: C,,H,,N,O,S MW: 527.64 EINECS: 251-463-2 LD,,: 234 mdkg (M, i.v.); >2glkg (M, p.0.) CN: N-~(cyclohexylan1ino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1 H)- 972 G Glisoxepide I. HNO, 2. Hz, Roney-Ni 3. NoNO2 4. oq. H,SO, 5. H,c-O\ S $' 1. NaOH oQ \,+H, , H3c,0y$f~3 2. H2S04 , , 0 H,C CH, 7-methaxy-2,4,4- trimethyl- 1.2.3.4- tetrahydroiso- quinoline- 1.3-dione 4.4-dirnethyi-7- 4-(2-orninoethy1)- metnoxyisochrornon- benzenesulfonamide 1.3-dione (I) I1 + cyclahexyl- potassium isocyanate tert-butylate Gliquidone Reference(s): DAS 2 000 339 (Thomae; appl. 5.1.1970). DOS 2 01 1 126 (Thomae; appl. 10.3.1970). US 3 708 486 (Boehringer Ing.; 2.1.1973; D-prior. 5.1.1970 and 17.4.1969). Formulation(s): tabl. 30 mg Trade Name(s): D: Clurcnorm (Yamanouchi) GB: Glurenorm (Sanofi I: Glurenor (Guidotti) Winthrop) Glisoxepide ATC: AlOBBll Use: antidiabetic RN: 25046-79- 1 MF: C20H27N505S MW: 449.53 EINECS: 246-579-5 LD,,,: 283 mglkg (M, i.v.); >10 gkg (M, p.0.); 196 mglkg (R, i.v.); >10 g/kg (R, p.0.); >2 glkg (dog, p.0.) CN: N-[2-[4-[[[[(hexahydro-lH-azepin-l-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethy1]-5-methyl-3- isoxazolecarboxamide !" Glucametacin G 973 1 S0CI2 0 OYOOH +I "3C 2. 4-(2-ominoethy1)- H3C methyl benzenesulfonom~de chloroformote 5-rncthylisoxozolc- 3-corboxylic acid H3C (1) I -ominohem- Glisoxepida hydroozepine L Rejerence(s): DE 1 670 952 (Bayer; appl. 25.11.1967). US 3 668 215 (Bayer; 6.6.1972; D-prior. 25.11.1967). Plbmpe, H. et al.: Arzneirn Forsch. (ARZNAD) 24, 363 (1974). Formulntion(s): tabl. 4 mg Trade Namels): D: Pro-Diaban (Bayer Vital) I: Glucoben (Farrnadcs); wfm Glucametacin ATC: A02A Use: anti-inflammatory RN: 52443-21 -7 MF: C25H2,C1N20~ MW: 5 18.95 EINECS: 257-923-9 CN: 2-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyI]arnino]-2-deoxy-~-glucose indornetacin (9. v.) 1 -(4-chlorobenzoyl)-2- methyl-5-methoxyindol- 3-acetyl chloride (I) n-D-glucosarnine hydrochloride Glucornetocin Referencefs): DOS 2 223 051 (SIR; appl. 12.5.1972; I-prior. 9.5.1972). Formulation(s): cps. 70 mg, 140 mg Trade Name(s): I: Teorema (Farmades); wfm Teoremac (Sir); wfm D-Ghcosamine ATC: MOlAXOS (Chi tosamine) Use: antirheumatic, antiarthritic RN: 3416-24-8 MF: C,H,,NO, MW: 179.17 EINECS: 222-31 1-2 CN: 2-amino-2-deoxy-D-glucose hydrochIoride RN: 66-84-2 MF: ChH,,NOs . HCI MW: 215.63 EINECS: 200-638-1 sulfate (2:l) RN: 14999-43-0 MF: ChHl,NO,. 1/2H,04S MW: 456.42 EINECS: 239-088-2 hydriodide RN: 14999-44-1 MF: C6H13N05. HI MW: 307.08 EINECS: 239-089-8 Unit of chitin, mucoproteins and mucopolysaccharids, obtained by hydrolysis with HCI. Referencefs): Ledderhose, G.: Z. Physiol. Chem. (ZPCHAS) 2, 213 (1878). preparation of glucosarnine salts: GB 1 056 33 1 (Rotta Research; appl. 15.1.1964; I-prior. 18.1.1963), stable complex from glucosamine sulfate and NaCI: GB 2 101 585 (Rotta Research; appl. 26.4.1982; I-prior. 30.4.1981). combinarion of glucosamine sulfate and hydriodide for therapy of rheumatoid arthritis and osteoarthritis: US 3 683 076 (L. Rovati; 8.8.1972; I-prior. 26.10.1968). Glutethimide G 975 Formulation(s): drg. 200 mg, 250 mg (as sulfate); vial 400 mg (as sulfate) Trade Nameis): D: Dona-200 S (Opfermann) I: Dona (Rottapharm; as sulfate) Glutethimide ATC: NOSCEOI Use: hypnotic, sedative RN: 77-21-4 MF: C13H,5N0, MW: 217.27 EINECS: 201-012-0 LD,,: 360 mglkg (M, p.0.); 600 mgkg (R, p.0.); 500 mglkg (dog, p.0.) CN: 3-ethyl-3-phenyl-2,6-piperidinedione methyl 2-phenyl- ocrylate butyronitrile Glutethimide I Reference(s): US 2 673 205 (Ciba; 1954; CH-prior. 195 1). DE 9.50 193 (Ciba; appl. 1952; CH-prior. 195 1). Formulation(s): cps.; tabl. 250 mg, 500 mg Trade Nameis): D: Doriden (Ciba); wfm I: Doriden (Ciba); wfm USA: Doriden (USV); wfm F: DoridCne (Ciba): wfm J: Doriden (Ciba-Geigy- generic GB: Doriden (Ciba); wfm Takeda) Glybuzole (Desagl y buzole) ATC: V03AH Use: antidiabetic RN: 1492-02-0 MF: CI2HI5N3O2S2 MW: 297.40 EINECS: 216-081-2 LD,,,: 193 mglkg(M,i.v.); 550 mg/kg(M,p.o.); 500 mglkg (R, p.0.) CN: N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]benzenesulfonamide benzene- 2-omino-5-tert- sulfonyl butyl- 1,3,4- chloride thiadiozole Glybuzole Referenceis): GB 822 947 (Smith & Nephew; appl. 1957; valid from 1958). FR-M 3 389 (RhGne-Poulenc; appl. 27.1.1964). 976 G Glyconiaxide Forndation(s): 250 mg (oral) Trade Name(s): J: Gludiase (Kyowa Hakko) Glyconiazide (Gluconiazide) ATC: J04A Usc: tuberculostatic RN: 3691-74-5 MF: Cl,H13N30, MW: 295.25 EINECS: 223-005-1 LD,,,: 641 mglkg (M, i.v.); 748 mgkg (M, p.0.); 1763 mgkg (R, i.v.); 6423 mgkg (R, p.0.) CN: glucuronic acid y-lactone 1 -[(4-pyridinylcarbonyI)hydrazone] Reference(s): US 2 940 899 (Univ. of California; 14.6.1960; prior. 28.9.1953). Sah, P.P.T.: J. Am. Chem. Soc. (JACSAT) 75,2512 (1953). isoniozid D-qlucuronoloctone Formulation(s): (oral) 0.01 5 g/kg Glyconiozide Trade Narne(s): D: Gluronazid (Hormon- Isozidoron 444 I: Glucazide (Stholl); wfm Chemie); wfm (Saarstickstoffl-comb.; J: Hy dronsan (Chugai) - wfm (9. v.) Glycopyrronium bromide (Glycopyrrolate) ATC: A03AB02 Use: anticholinergic, antispasmodic RN: 596-51 -0 MF: C,,H,,BrN03 MW: 398.34 EINECS: 209-887-0 LD,,,: 15 mgikg (M, i.v.); 570 mgikg (M, p.0.); 709 mgkg (R, p.0.) CN: 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide HC + OH b I '0 J-hydroxy- 0 1 -methyl- pyrrolidine methyl phenyl- cyclopenty\- methyl glyoxylate magnesium a-cyclopentyl- bromide mandelote Glymidine G 977 (1) ( Glycopyrroniurn bromide Reference(s): US 2 956 062 (A. H. Robins; 11.10.1960; prior. 26.2.1959) Formulation(s): amp. 0.2 mgfml, 500 pglml Trade Nanie(s): D: Robinul (Brenner-Efeka) GB: Robinul (Anpharm) F: Adcryl (Martinet); wfm J: Robinul (Kaken) USA: Robinul (Robins) Glyrnidine (Glycodiazin) ATC: AlOBCOl Use: antidiabetic RN: 339-44-6 MF: C13H15N304S MW: 309.35 EINECS: 206-426-5 LD,,: 3100mgkg (R, p.0.) CN: N-[5-(2-methoxyethoxy)-2-pyrimidinyl]benzenesulfonamide sodium salt RN: 3459-20-9 MF: Cl3Hl4N3NaO,S MW: 331.33 EINECS: 222-399-2 LD,,: 3100 mgkg (R, p.0.) dimethyl- 1 ,I .2-tris(2-rnethoxyethoxy)- farmamide ethane Reference (s): US 3 275 635 (Schering AG; 27.9.1966; D-prior. lR.10.1960, 22.2.1961,23.2.1961). DAS 1 445 142 (Schering AG; appl. 22.2.1961). DAS 1 445 146 (Schering AG; appl. 9.9.1961; addition to DAS 1 445 142). Gutsche, K. et al.: Arzneim Forsch. (ARZNAD) 14, 373 (1964). benzenesulfonyl- Formulation(s): tabl. 0.5 g, 1 g (as sodium salt) Glyrnidine Trade Name(s): D: Redul (Bayer-Schering); wfm guanidine 978 G Granisetron Redul plus (Bayer- F: Glyconormal (Bayer- I: Glycanol (Bayer); wfm Schering)-comb, with Pharma); wfm Gondafon (Schering); wfm buformin; wfm Gondafon (SEPPS); wfm J: Lycanol (Bayer-Yoshitomi) Redul28 (Schering); wfrn GB: Gondafon (Schering Chemicals); wfrn Granisetron (BRL-43694) ATC: A04AA02 Use: anti-emetic, 5-HT,-antagonist RN: 109889-09-0 MF: C,,H2,N40 MW: 312.42 CN: endo-l-methyl-N-(9-methyl-9-azabicyclo[3.3.l]non-3-yl)-1H-indazole-3-carboxamide monohydrochloride RN: 107007-99-8 MF: C,,H,,N,O. HCI MW: 348.88 LD,,,: 17 mgkg (M, i.v.); 350 mglkg (M, p.0.); 14 mglkg (R, i.v.); 350 mgkg (R, p.0.) COOH COC IH chloride indarole-3- methyl carboxylic acid iodide 1 -methyl- indazole-3- carboxylic acid Reference(s): EP 200 444 (Beecham; appl. 21.4.1986; GB-prior. 27.4.1985, 21.10.1985). Bermudez, J. et al.: Bioorg. Med. Chem. Lett. (BMCLE8) 4 (20), 2376 (1994). 1 -methyl- endo-9-methyl- alternurive synthesis: WO 9 730 049 (SmithKline Beecham; appl. 11.2.1992; GB-prior. 13.2.1996). Granisetron synthrsis of 1-methylindazole-3-carboxylic acid: EP 323 105 (Beecham; appl. 19.12.1988; GB-prior. 22.12.1987). Bermudez, J. et a].: J. Med. Chem. (JMCMAR) 33, 1924 (1990). indazole-3- 9-azobicyclo[3.3.1]- carbonyl chloride (I) nanan-3-amine (granatanearnine) synthesis of granataneamine: Jones, G.; Stanger, J.: J. Chem. Soc. C (JSOOAX) 1969,901. medic~tl use for freutment of CNS und cognitive disorders: EP 223 385 (Beecham; appl. 7.10.1986; GB-prior. 21.10.1985). EP 279 990 (Glaxo; appl. 16.12.1987; GB-prior. 17.1 2.1986, 25.3.1987). Grepafloxacin G 979 , . medical use for treatment of withdrawal syndrome: EP278 161 (Glaxo; appl. 20.1 1.1987; GB-prior. 21.11.1986, 25.3.1987). EP 279 114 (Glaxo; appl. 20.11 .I 987; GB-prior. 21.11.1986,25.3.1987). medical use for treatment of visceral pain: EP 279 512 (Beecham; appl. 18.1.1988; GB-prior. 19.1.1987). US 4 845 092 (Beecham; 4.7.1989; appl. 19.1.1988; GB-prior. 19.1.1987). medical use for treatment of cough and bronchoconstriction: EP 340 270 (Beecham; appl. 14.1 1.1988; GB-prior. 14.1 1.1987). medical use for treatment of myocardial instability: WO 9 109 593 (Beecham; appl. 20.12.1990; GB-prior. 21.12.1989). Formulation(s): amp. 1 mg, 3 mg; tabl. 1 mg (as hydrochloride) Trade Narne(s): D: Kevatril (Bristol-Myers GB: Kytril (SmithKline SquibbISmithKline Beecham) J: Beecham) I: Broncosedina (Farma>- F: Kytril (SmithKline comb. USA: Beecham; 199 1) Kytril (SmithKline Beecham) Grepafloxacin (OPC- 17 1 16) Sedobex (Ecobi)-comb. Kytril (SmithKline Beecham) Kytril (SmithKline Beecham) ATC: JOlMAll Use: antibacterial (gyrase inhibitor) RN: 119914-60-2 MF: CIYH,,FNO3 MW: 331.39 CN: l-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-l-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (?)-form RN: 146863-02-7 MF: C,,H,,FNO, MW: 33 1.39 (t)-monohydrochloride RN: 161967-81-3 MF: CIyH,,FNO3 . HCI MW: 367.85 LD,,,: 69.2 mglkg (M, i.v.); 3900 mglkg (M, p.0.); 152 mglkg (R, i.v.); 3029 mg/kg.(R, p.0.) 1. S0Cl2 2.H3CvOn0,CH3 0 0 Mg, C2H50H, toluene, 60 'C 2. diethyl rnalonote F OvCH3 CH3 Fm-cH3 CH3 0 0 2-methyl-3.4.6- diethyl (2-methyl- trifluorobenroic acid 3,4,6-trifluorobenzoyl)- rnalonate (I) 980 G Grepafloxacin \/ . C2H50H, 0 OC 1 - 2. ocetic anhydride cyclopropylomine triethoxyrnethane CH~O 6; ethyl 2-(2-methyl- 3.4.6-trifluorobenzayl)- 3-etho~yacr~late ethyl 2-(2-methyl- 3.4.6-trifluorobenzoy1)- 3-cyclopropylamino- acrylate (11) ethyl 1 -cyclopropyl- 6.7-difluoro-5-methyl- 1,4-dihydro-4-0x0- quinaline-3-carboxylote (In) 2-methyl- piperaline 1. NoOH. C2H50H 2. HCI Iv- F H3ChNm CH,O COOH Grepafloxacin Reference(s): EP 287 951 (Otsuka Pharrn.; appl. 14.4.1988; J-prior. 16.4.1987). EP 364 943 (Otsuka Pharrn.; appl. 17.10.1989; J-prior. 20.10.1988). melt-extruded polymeric material: JP 08 280 790 (Otsuka Pharrn.; appl. 17.4.1995). use as,fungicide: JP 07 149 647 (Daiichi Seiyaku; appl. 8.9.1994; USA-prior. 8.9.1993). Formulation(s): f. c. tabl. 400 rng, 600 rng (as hydrochloride) Trccdc Ntrrrre(s); D: Vaxar (Glaxo Wellcornel J: Lungaskin (Otsuka; as USA: Raxar (Glaxo Wellcome; Cascan); wfm hydrochloride); wfrn 1997); wfrn . Use: anti-inflammatory RN: 5244 3-2 1 -7 MF: C25H2,C1N20~ MW: 5 18.95 EINECS: 25 7-9 2 3-9 CN: 2-[ [[ 1-( 4-chlorobenzoyl )-5 -methoxy-2-methyl-1H-indol-3-yl]acetyI]arnino ]-2 -deoxy-~-glucose indornetacin. Granisetron (BRL-43694) ATC: A04AA02 Use: anti-emetic, 5-HT,-antagonist RN: 1 0988 9-0 9-0 MF: C,,H2,N40 MW: 312.42 CN: endo-l-methyl-N-(9-methyl-9-azabicyclo[3.3.l]non-3-yl )-1 H-indazole-3-carboxamide. 331.39 CN: l-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl- 7-( 3-methyl-l-piperazinyl )-4 -oxo-3-quinolinecarboxylic acid (?)-form RN: 14686 3-0 2-7 MF: C,,H,,FNO, MW: 33 1.39 (t)-monohydrochloride