Sciences and Techn.; appl.. Sciences and Techn.; appl.. Sciences and Techn.; appl.. Sciences and Techn.; appl.. Sciences and Techn.; appl.. Sciences and Techn.; appl.. fornesylocetic oci
Trang 1Galliumnitrate G 951
Use: hypocalcemic agent against cancer- related hypercalcemia
RN: 13494-90-1 MF: GaN,O, MW: 255.74 EINECS: 236-815-5
LD,,,: 55 mgkg (M, i.v.1; 4360 m g k g (M, p.0.); 600 mglkg (M, s.c.);
46 mgkg (R, i.v.)
CN: gallium nitratc
Go + HNO, G O ( N O ~ ) ~
Gallium nitrate
i
Reference(s):
Duprk, A.: C R Hebd Seances Acad Sci (COREAF) 86,721 (1878)
medicai use as Izypocalcemic agent:
EP 109 564 (Sloan Kettering Inst.; appl 2 1 IO.l983; USA-prior 22.10.1982)
US 4 529 593 (Sloan Kettering Inst.; 16.7.1985; prior 20.6.1984, 22.10.1982)
medical use as antitumor e f i c t enhancer:
JP 1 104 016 (Taishitsu Kenkyukai; appl 31.7.1987)
Fonnulatiorz(s): vial 500 mg
Trade Name(s):
USA: Ganite (SoloPak)
Use: coronary vasodilator, verapamil analog
RN: 16662-47-8 MF: C,,H,,N,O, MW: 484.64
CN: a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propylj-3,4,5-trimethoxy-a-(l-
methy1ethyl)benzeneacetonitrile
hydrochloride
RN: 16662-46-7 MF: C2,H,N,0S HCI MW: 521.10
3,4.5-trimethoxy- 2-chloro- 2-(3.4.5-trimethoxypheny1)-
phenylocetonitrile propane 3-methylbutyronitrile (1)
oxyphenyl)ethyl]- chloropropone
methylomine
Trang 2952 G Gamolenic acid
NaNH2
sodium
arnide
Reference( s):
Galloparnil I
DE 1 154 810 (Knoll; appl 28.4.1961)
DE 1 158 083 (Knoll; appl 19.12.1962)
DE 2 059 985 (Knoll; prior 5.12.1970)
Trade Natne(s):
D: Gallopamil (ct-
Arzneimittel)
Procorum retard (Knoll; I: Algocor (Ravizza)
Use: treatment of eczema RN: 506-26-3 MF: C,,H3,O2 MW: 278.44
CN: (Z,Z,Z)-6,9,12-octadecatrienoic acid
potassium salt
RN: 106868-38-6 MF: C,,H2,K02 MW: 316.53
sodium salt
RN: 86761-55-9 MF: C,,H2,Na02 MW: 300.42
ri Garnolenic a c ~ d
a From fermentation of Mortierella
b From fermentation of mucor
c Extration and isolation from natural sources (seeds of black currant, evening primrose, borage)
Trang 3Gamolenic acid G 953
Referencefs):
a JP59 130 191 (Agency of Ind Sciences and Techn.; appl 12.1.1983)
JP 60 168 391 (Agency of Ind Sciences and Techn.; appl 9.2.1984)
JP 63 112 536 (Agency of Ind Sciences and Techn.; appl 30.10.1986)
WO 8 604 354 (Agency of Ind Sciences and Techn.; appl 13.12.1985; J-prior 22.1.1985,21.2.1985)
EP 155 420 (Agency of Ind Sciences and Techn.; appl 25.9.1984; J-prior 9.2.1984, 5.6.1984)
EP253 556 (Suntory; appl 7.7.1987; J-prior 8.7.1986)
EP 276 982 (Suntory; appl 26.1.1988; J-prior 27.1.1987)
US 4857 329 (Agency of Ind Sciences and Techn.; 15.8.1989; appl 1.8.1986; J-prior 19.8.1985)
Suzuki, 0.: Proc World Conf Biotechnol Fats Oils Ind (56NIAQ) 1987, p.110-116, Ed T H Applewhite
b JP 1 132 371 (Itochu Seito; appl 18.11.1987)
EP 269 351 (Lion Corp.; appl 17.1 1.1987; J-prior 26.1 1.1986)
Fukuda, H.; Morikawa, H.: Appl Microbiol Biotechnol (AMBIDG) 27, 15 (1987); Bioreact Biotransform., [Pap Int Conf.] (56GJAS), p 386, Ed G W Moody, P.B Baker (Elsevier, London, 1987)
Aggelis G et a].: Oleagineux (OLEAAF) 43,3 11 (1988)
Hansson, L et al.: Appl Microbiol Biotechnol (AMBIDG) 31, 223 (1989)
alternative fermentation processes:
EP 153 134 (Efamol; appl 12.2.1985; GB-prior 21.2.1984)
GB 2 163 424 (Nisshin Oil Mills; appl 22.7.1985; J-prior 31.7.1984)
JP 1 199 588 (Nitto Chem.; appl 2.6.1988; prior 27.10.1987)
JP 63 240 791 (Kanegafuchi; appl 27.3.1987)
JP 62 210 995 (Nisshin Flour Milling; 12.3.1986)
JP 62 232 379 (Nisshin Oil Mills; appl 2.4.1986)
JP49 013 988 (A Watanabe et al.; appl 10.1.1969)
JP 47 022 280 (Ono; appl 13.8.1969)
c DOS 3 542 932 (HVG Barth, Raiser Co; appl 4.12.1985)
EP 271 747 (Nestle; appl 25.1 1.1987; CH-prior 17.12.1986)
EP 178 442 (Nestle; appl 4.9.1985; CH-prior 10.10.1984)
FR 1 603 383 (Ono; appl 3.10.1968)
US 4 703 060 (Nestec S.A.; 27.10.1987; appl 14.10.1983; prior 6.4.1983)
JP 1051 496 (Nippon Oils and Fats; appl 21.8.1987)
JP63 216 845 (Agency of Ind Sciences and Techn.; appl 5.3.1987)
Traitler, H et al.: J Am Oil Chem Soc (JAOCA7) 65, 755 (1988)
Wille, H.; Traitler, H.: Fett Wiss Techno] (FWTEEG) 90,476 (1988)
combination with calcium:
EP 261 814 (Efamol; appl 28.8.1987; GB-prior 10.9.1986)
modeling of androgen action in men:
EP 309 086 (Efamol; appl 9.8.1988; GB-prior 7.9.1987)
prevention of side effects of non-steroidal anti-injlatnmatories:
EP 195 570 (Efamol; appl 7.3.1986; GB-prior 19.3.1985)
treatment of premenstrual syndrome:
US 4415 554 (Efamol; 15.1 1.1983; appl 10.6.1981; GB-prior 23.1.1978,7.2.1978, 19.4.1978, 17.8.1978, 24.10.1978, 19.1.1979, 30.10.1979)
ZA 8 604 779 (Efamol; appl 27.6.1986; GB-prior 4.7.1985)
treatment of complications of diabetes mellitus:
EP218 460 (Efamol; appl 1.10.1986; GB-prior 2.10.1985)
treatment of skin disorders:
US 4 444 755 (Efamol; 24.4.1984; appl 10.6.1981; prior 19.1.1979, 30.10.1979)
EP 173 478 (Efamol; appl 5.8.1985; GB-prior 15.8.1984)
treatment of prostatornegaly:
JP61 207 330 (Efamol; appl 6.3.1986; GB-prior 8.3.1985)
treatment of endometriosis:
EP 222 483 (Efamol; appl 1 lo 1986; GB-prior 2.10.1985)
Trang 49 5 4 G Ganciclovir
treatmenr of amnesia:
EP 296 751 (Efamol; appl 15.6.1988; GB-prior 24.6.1987)
treatment of allergic rhinitis and asthma:
JP 61 087 621 (Nisshin Oil Mills; appl 5.10.1984)
skin improving composition:
EP 334 507 (Efamol; appl 7.3.1989; GB-prior 22.3.1988)
pharmaceutical and dietary composition:
EP 3 407 (Verronmay; appl 20.1 1979; GB-prior 23.1.1978)
EP 4 770 (Verronmay; appl 10.4.1979; GB-prior 11.4.1978)
EP 19 423 (Efamol; appl 8.5.1980; GB-prior 18.5.1979)
US 4 273 763 (Efamol; 16.6.1981; GB-prior 23.1.1978)
Trade Name(s):
D: Epogam (Beiersdorf; 1990) Epogam (Searle)
GB: Efamast (Searle) I: Epogam (Whitehall)
Ganciclovir
(Biolf-62; BW-759U; D H P G ; 2'-NOG)
ATC: SO1AD09 Use: antiviral nucleoside for treatment of
cytomegalovirus infections in AIDS patients
RN: 82410-32-0 MF: CYHl3N5O4 MW: 255.23
LD,,: 1 glkg (M, i.p.); 900 mglkg (M, i.v.); >2 g/kg (M, p.0.);
>I50 mglkg (dog, i.v.); >I glkg (dog, p.0.)
CN: 2-amino-l,9-dihydro-9-[[2-hydroxy-l-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one
monosodium salt
RN: 107910-75-8 MF: CyH,,N5Na04 MW: 277.22
'NaOH 2 KO a CH3
, I
1 paraformaldehyde epichloro- benzyl
hydrin alcohol
1.3-di-0-benzylglycerol 2 potossium acetate
3L a I' 'kCH3 I p-toluene- ' 2 " "
0 sulfonic acid '-0
1.3-di-0-benzyl-2-0- ~ ~ 9 - d i a c e t ~ l
(acetoxymethyi)glycerol (1) guanine
Trang 5Gefarnate G 955
0
1 (N1i4)2S04, HMDS
0 2 H, Pd-C
Reference(s):
EP 85 424 (Syntex; appl 3 1.1.1983; USA-prior 1.2.1982,22.12.1982)
EP49 072 (Syntex; appl 15.9.1981 ; USA-prior 16.9.1980)
US4423 050 (Syntex; 27.12.1983; prior 24.5.1982, 21.5.1981)
US 4 355 032 (Syntex; 14.6.1983; appl 21.5.1981)
Martin, J.C et al.: J Med Chem (JMCMAR) 26,759 (1983)
Ogilvie, K.K et al.: Can J Chem (CJCHAG) 60, 3005 (1982)
Ashton, W.A.: Biochem Biophys Res Commun (BBRCA9) 108, 1716 (1982)
anhydrous crystalline form:
US 4 642 346 (Syntex; 10.2.1987; appl 24.6.1985)
combination with interferon:
EP 109 234 (BioLogicals; appl 3.1 1.1983; USA-prior 4.1 1.1982)
alternative synthesis:
McGee, D.P et al.: Synth Commun (SYNCAV) 18, 1651 (1988)
ES 548 093 (Inke S.A.; appl 22.10.1985)
ES 549 248 (M.J Verde Casanova; appl 25.1 1.1985)
WO 8 302 723 (BioLogicals; appl 12.2.1982)
Boryski, J.; Golankiewicz, B.: Synthesis (SYNTBF) 1999 (4), 625
Review:
Gao, H.; Mitra, A.K.: Synthesis (SYNTBF) 2000 (3), 329
Trade Name(s):
D: Cymeven ( ~ o c h e ) GB: Cymevene (Roche) USA: Cytovene (Rochc)
F: CymCvan (Roche) I: Cymavene (Recardati) Cy tovene (Roche)
Virgan (ThCa) J: Denosine (Syntex)
Use: peptic ulcer therapeutic, antispasmodic
RN: 51-77-4 MF: C2,Hu02 MW: 400.65 EINECS: 200-121-0
LD5,,: 2821 m g k g (M, i.v.); >8 glkg (M, p.0.);
2040 m g k g (R i.v.); >9 glkg (R, p.0.)
CN: (E,E,E)-5,9,13-trimethyl-4,8,12-tetradecatrienoic acid 3,7-dimethyl-2,6-ocladienyl estcr
Trang 6956 G Gemcitahine
Reference(s):
BE 617 994 (1st de Angeli; appl 23.5.1962; GB-prior 24.5.1961)
fornesylocetic ocid gerar~iol
Gefornate
Trade Name(s):
GB: Gefarnil (Crookes); wfm
I: Famesil (AGIPS); wfrn
Farnisol (Firma); wfrn
Gefarnaxl-forte (De
Angc1i)-comb.; wfrn
Gefarnil (De Angeli); wfrn
Gefarnil Compositum (De
Ange1i)-comb.; wfrn
Gefarol (Iti); wfrn
Nolesil (Geymonat); wfrn
Ulco (Elea); wfrn
Ulcofarrn (Ausonia); wfrn Ulcofarm (Iton); wfrn Ulcotrofina (Ripari-Gero);
wfrn Vagogernil (Benvegna);
wfrn J: Alsanate (Dainippon) Dixnalate (San-a) Eszyme Dental (SS Seiyaku)
Gefalon (Sawai)
Gefanil (Sumitorno) Gefulcer (Ohta) Ketonil (Mohan) Matorozin (Kanto-Isei) Poly 1 (Teikoku) Salanil (Sato) Terpanil (Kakenyaku) Zackal (SS Seiyaku) Zenowal (Daigo-Takeda)
Gemcitabine
(dFdC; LY- 18801 1)
RN: 95058-81-4 MF: C,H,,F,N,O, MW: 263.20
CN: 2'deoxy-2',2'-difluorocytidine
monohydrochloride
RN: 1221 1 1-03-9 MF: C9H,IF2N30, HCI MW: 299.66
ATC: LOIBCO5 Use: antiviral, antineoplastic
(R)-2,3-0-iso- ethyl brorno-
propylidene- difluoroacetate
glyceraldehyde
Trang 7-+
terl-butyldimethylsilyl
trifluoromethonesulfonote,
2,6-dimethylpyridine
H 3 C p A 1 7 c H 3
CH, H CH, toluene
diisobutyloluminum hydride
f N(c,H,), CH&IZ
I I
0
CH3 CH3
msthane-
sulfonyl
chloride (V)
H~cKN'>H, 3 HPLc
YI + t; H3c\ ,CH3 1 trimethylsilyl
b
' , ' t r i f h o r o m e h o n e s u ~ f o n ~ (MU)
CH3
N-acetyl-N.0-bis-
(trirnethylsily1)-
cytosine (Vn)
Gerncitabine
u
, dcl , pyr~dine, lut~dine, 0 OC
2 H 3 C ~ A 1 7 C H 3 CH3 H CH, Br2, H20, DOC 3 V
HO 1 benzoyl chloride
OH F 2 diisobutylolumlnum chloride
Z-deoxy-2.2-
difluoro-0-
ribopyranose
Trang 8958 G Gentamicin
1 VIII 1.2-dichloroethane, 84 OC
2 NH3 CH30H
3 crystollizotion and separation
in isopropanol/HZO
Yo F
Reference(s):
a Hertel, L.W et al.: J Org Chem (JOCEAH) 53 (1 I), 2406 (1988)
EP 122 707 (Eli Lilly & Co.; appl 6.3.1984; USA-prior 10.3.1983,4.12.1984,4.6.1987)
EP 184 365 (Eli Lilly & Co.; appl 25.1 1.1985; USA-prior 10.10.1985, 4.12.1984, 3.3.1988)
b US 4 954 623 (Eli Lilly & Co.; appl 13.11.1989; USA-prior 13.1 1.1989, 20.3.1989)
c EP 306 190 (Eli Lilly & Co.; appl 22.8.1988; USA-prior 28.8.1987)
EP 577 303 (Eli Lilly & Co.; appl 21.6.1993; USA-prior 7.4.1993, 22.6.1992, 30.5.1995)
Trude Name(s):
D: Gemzar (Lilly) GB: Gemzar (Lilly; as USA: Gemzar (Lilly; as
hydrochloride)
Gentamicin
(Gentamycin)
ATC: D06AX07; JOlGB03; SO1 AAl I ;
S03AA06 Use: antibiotic RN: 1403-66-3 MF: unspecified MW: unspecified EINECS: 215-765-8
LD,,,: 43.5 mglkg (M, i.v.); 10 glkg (M, p.0.);
70 mglkg (R, i.v.); 6600 mglkg (R, p.0.);
184 mglkg (dog, i.v.)
CN: gentamicin
suIfate
RN: 1405-41 -0 MF: H2S04 x unspecified MW: unspecified EINECS: 21 5-778-9
LD,,,: 47 mglkg (M, i.v.); >11.269 glkg (M, pa.);
96 mglkg (R, i.v.); >5 glkg (R, p.0.)
H3C-NH
N H 2
Gentornicin
Gentarnicin C1 R1: - C H 3 ; RZ: -CH, Gentamicin CZ R1: -CH, ; R ~ : -H Gentornicin C,, ~ 1 -H : ; RZ: -H
From fermentation solutions of Micrornonospora purpurea; Micromonospora echinospora
Trang 9Gentisic a c i d G 959
Rejerence(s):
US 3 091 572 (Schering Corp.; 28.5.1963; prior 16.7.1962)
US 3 136 704 (Schering Corp.; 9.6.1964; prior 5.12.1962)
Weinstein, M.J et al.: Antimicrob Agents Chemother (AACHAX), 1 (1963)
Trade Name(s):
Dispagent (CIBA Vision)
duragentamicin 40180160
(durachzmie)
Gencin (curasan)
Genta (ct-Arzneimittel)
Gentamicin POS
(Ursapharm)
Gentamytrcx (Mann)
Gent-Ophtal (Winzer)
Ophtagram (Chauvin
ankerpharm)
Refobacin (Merck)
Sulmycin (Essex Pharma)
numerous combination
preparations
Gentabilles (Schering-
Plough)
GB:
I
Gentalline (Schering- Plough)
Gentamicine Chauvin (Chauvin)
Gentasone (Schering- Plough)-comb
Palacos (Schering-Plough) Cidomycin (Hoechst) Garamycin (Schering- Plough)
Genticin (Roche) Gentisone C (Roche)- comb
Lugacin (Lagap) Minims gentamicin (Chauvin)
Citrizan Antibiotic0 (ID1)- comb
Diprogenta (Sca)-comb Farmomicin (Farmigea)- comb
Genall'a (1ntes)-comb Genatrop (1ntes)-comb Gentalyn (Schering- Plough)
Gentamen (Pierrel) Gentibioptal (Farmila) Genticol (Siti) Ribomicm (Farmigea) Septopal (Bracco) combination preparations J: Gentacin (Shionogi) USA: Garamycin (Schering) GentaPair (Pharmafair) G-my ticin (Pedinol)
Gentisic acid
(Acide gentisique)
ATC: M01; NO2 Use: anli-inf ammatory, analgesic
RN: 490-79-9 MF: C,H,O, MW: 154.12 EINECS: 207-718-5
LDSo: 374 mgkg (M, i.v.); 4500 mg/kg (M, p.0.)
CN: 2,5-dihydroxybenzoic acid
monosodium salt
RN: 4955-90-2 MF: C,H,NaO, MW: 176.10 EINECS: 225-598-2
LDs,,: 3735 m g k g (M, i.p.); 3900 mg/kg (M, s.c.1
K2C03, 35 bar,
hydro-
winone
Gentisic acid
u
Reference(s):
US 2 547 241 (Monsanto; 1951; appl 1950)
US 2 588 336 (Monsanto; 1952; appl 1950)
US 2 608 579 (Monsanto; 1952; appl 1949)
US 2 816 137 (Eastman Kodak; 1957; appl 1954)
Trang 10960 G Gestodene
Trade Narne(s):
D : Gentisinamid (Herbrand)- Prigenta (Reis)-comb.; Rheumadrag (Schuck)
Gestodene
(SHB 331)
ATC: G03AB; G03AA Use: progestogen, oral contraceptive RN: 60282-87-3 MF: C,,H,,O, MW: 310.44 EINECS: 262-145-8
CN: (17a)-13-ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one
1 HCI CH30H HzO
2 fementative hydroxylation with Penicillium roistrickii (ATCC 10490)
b
H,C
H3C triethyl ortho-
formote
p-toluene-
H 3 C sulfonic acid
H3C 2.2-dimethyl- 1 5a-hydroxy-3.3-(2,2-dimethyl-trirnethylenedioxy)-
1.3-propanediol 13-ethyl-5(5(tO))-gonsn- 17-one (mixture) (11)
1 (CH,CO),O
2 BrMg-CECH
3 (COOH)2
2 ethynylrnagnesiurn bromide (111)
3 oxalic acid
I Gestodene
1 CISi(CH3),
2.111
11
1 trirnethyl-
silyl chloride