Tuaminoheptane T 2 14 1 Tyson L-Tryptophan U.S.P. (Tyson); wfm lhaminoheptane ATC: ROIAAI I; ROIABO~ (Heptylamine) Use: sympathomimetic, vasoconstrictor RN: 123-82-0 MF: C7HI,N MW: 115.22 EINECS: 204-655-5 LD,,,: 60 mglkg (M, i.p.); 1 15 mglkg (M, s.c.); 130 mgkg (R, s.c.) CN: 2-heptanamine sulfate (2:l) RN: 641 1-75-2 MF: C,H17N. 112H204S MW: 328.52 EINECS: 229-1 13-5 LD,,: 16.3 mdkg (M, i.v.); 47.3 mglkg (R, i.v.) NHJ. H? Raney-Ni H3C omyl methyl ketone Referencefs): Norton, D.G. et al.: J. Org. Chem. (JOCEAH) 19, 1054 (1954). Formulation(s): nasal spray 50 mgIl0 ml Trade Namefs): D: Rinofluimucil-S F: Rhinofluimucil (Zambon)- Rinofluimucil (Zambon (1npharzam)-comb. comb. 1talia)-comb. I: Otomicetina (Deca)-comb. lhbocurarine chloride ATC: ~03~~02 Use: muscle relaxant RN: 6989-98-6 MF: C37H41CIN206. HC1. 5H20 MW: 771.73 LD,,: 130 pglkg (M, i.v.); 150 mglkg (M, p.0.) CN: 7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraranium chloride hydrochloride pentahydrate anhydrous RN: 57-94-3 MF: C37H41CIN206 . HCl MW: 681.66 EINECS: 200-356-9 LD,,,: 97 ~glkg (M, i.v.); 33 mdkg (M, p.0.); 66 pdkg (R, i.v.); 28 mgkg (R, p.0.) 2142 T Tulohuterol Tubocurarine chloride By extraction from Chondrodendron tomentosum (Ampi Huasca) and purification via the picrate. Reference(s): US 2 409 241 (Squibb; 1946; prior. 1944). US 2 600 539 (Parke Davis; 1952; appl. 1947). Everett, A J. et al.: J. Chem. Soc. D (CCJDAO) 1970, 1020. Codding, P.W.; James, M.N.G.: J. Chem. Soc. D (CCJDAO) 1972, 1. Fonnulation(s): amp. 3 mglml Trade Name(s): D: Curarin Asta (ASTA), wfrn GB: Jexm (Duncan, Flockhart); Tubarine (Wellcome); wfm Curarin HAF (Ethicon); wfm J: Amelizol (Yoshitomi) wfm Tubarm (Calm~c); wfm USA: Tubocurarine Chloride F: D-Tubocurarine Abbott I. Curarln (Schenng), wfm (Lilly) (Abbott); wfm Intocortnn T (Squibb); wfm ATC: R03AC11; R03CCI I Use: bronchodilator RN: 41570-61-0 MF: C,,H,,CINO MW: 227.74 CN: 2-chloro-a-[[(I ,I-dimethylethyl)amino]methyl]benzenemcthanol 1. H~N~C~~ H,C CH3 dcH3 3 dcHo 2.N0'3H4 ' c1 1. tert-butylornine , CI H3C 2'-chloro- 2. sodium 2-chloro- Tulobuterol phenyl- borohydride acetophenone glyoxol Reference(s): DOS 2 244 737 (Hokuriku; appl. 12.9.1972; J-prior. 13.9.1971). Forrnulation(s): sol. 1 mg/5 ml; syrup 1 mg15 ml; tabl. 2 mg (as hydrochloride) Trade Nutne(s): D: Atenos (UCB; 1985) GB: Respacal (UCB) Hokunalin (Hokuriku) Brelomax (Abbott; 1985) J: Berachin (Tokyo Tanabe) Tybamate T 2143 Tybamate ATC: M03 Use: tranquilizer, skeletal muscle relaxant RN: 4268-36-4 MF: C13HzN204 MW: 274.36 EINECS: 224-254-9 LDS,,: 254 mglkg (M, i.v.); 800 mglkg (M, p.0.); 1040 mgkg (R, p.0.) CN: butylcarbamic acid 2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester 2-methyl-2-propyl- diethyl 1.3-proponediol carbonate (cf. meprobamate synthesis) 5-methyl-5-propyl- 1,3-dioxan-2-one (I) 0 AI[OCH(CHJ)~I~ 1 + n2~~cti3 -+ ROAN-CHI H3C OH H ethyl corbomote butylomine Tybornote liq. NH3 I + H3C kNH2 butyl isocyanate 0 Reference(s): US 2 937 119 (Carter Products; 17.5.1960; prior. 11.6.1959). illfenlafive synfhesis: DE 1 196 638 (Orgamol; appl. 27.2.1962; CH-prior. 2.3.1961). Trude Name(s): USA: Solacen (Wallace); wfm Tybatran (Robins); wfm Tyloxapol ATC: ROSCAO1 Use: tenside, rnucolytic agent RN: 25301-02-4 MF: [C,,H,,O . C,H40 . CH,O]x MW: unspecified CN: formaldehyde polymer with oxirane and 4-(1,1,3,3-tetramethylbutyl)phenol 4-(1,1,3.3-tetra- form- methylbuty1)- aldehyde ~henol ethylene oxide 1 I: ~~-(cH2-o-cn2)m-cn2-oti Tyloxapol Reference(s): US 2 454 541 (Rohm & Haas; 1948; appl. 1944). Formulation(s): eye drops 2.5 mglrnl, 10 mglrnl; intratracheal susp. 8 mgIl0 ml; sol. 0.25 mg/ml, 1.25 mgfml; vial 0.25 mg/ml Trade Name(s): D: Complete (Pharrn- Tacholiquin (bene- CB: Alevaire (Winthrop); wfm Allergan)-comb. Arzneimitte1)-comb. J: Alevaire (Nippon Shoji) Enoclen (Alcon)-comb. F: Contact01 (Merck Sharp & USA: Exosurf Neonatal (Glaxo Exosurf (Glaxo Wellcome)- Dohme-Chibret)-comb.; Wellcome)-comb. comb. wfm Use: non-essential proteinogenic amno acid (for infusion solution) RN: 60-18-4 MF: C,H,,NO, MW: 181.19 EINECS: 200-460-4 LD,,,: >I450 mg/kg (M, i.p.) CN: L-tyrosine Preparation by acidic proteine hydrolysis (e. g. of keratines) with following fractionated crystallization (obtained in commonly with 1 cystine). Heferencers): Ullrnann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A2, 74. Formulation(s): sol. 2.5 %, 3 %, 3.5 %,4.5 %, 6 %, 10 YO, 15 %; tahl. 30 mg Trade Name(s): D: numerous combination I: Alfa Kappa (Farma- IS1 F/2/st (1SI)-comb. preparations Biagini)-comb. USA: Catemine (Tyson)-comb. 2 146 U Ubidecarenone Ubidecarenone ATC: ~01~~09 (Coenzym Q; Ubiquinone- 10) Use: cardiovascular agent, antihypertensive RN: 303-98-0 MF: C,,H,O, MW: 863.37 EINECS: 206-147-9 CN: 2-(3,7,11 ,I 5,l9,23,27,3l,3~,39-decamethyl-2,6,lO,l4,l8,22,26,3O,34,3S-tetracontadecaenyl)-5,6- Ubidecarenone From culture of Sporidiobolus johnsonii (ATCC 20490), Sporidiobolus ruinenii (ATCC-20489), Oosporidium nzargaritiferum (ATCC 10676), Rhodotorula muciladinosa (AHM 3946), Xanthomonas stewartii (Pasteur-No. 1035 and 1036). Referencefs): US 4 070 244 (Takeda; 24.1.1978; J-prior. 27.2.1976). DOS 2 740 614 (Kanegafuchi; appl. 9.9.1977; J-prior. 14.9.1976). DOS 2 834 952 (Lab. Bellon; appl. 10.8.1978; GB-prior. 17.8.1977). synthesis from 2-methyl-4,5,6-trimethoxyphenol and decaprenol: US 3 068 295 (Merck & Co.; 11.12.1962; appl. 3.9.1958). US 3 896 153 (Eisai; 22.7.1975; J-prior. 6.4.1973). US 4 062 879 (Eisai; 13.12.1977; J-prior. 29.9.1975). medical use as antihypertensive: US 3 808 330 (Eisai; 30.4.1974; J-prior. 13.7.1972). medical use for improvement of hearing: US 4 073 883 (Eisai; 14.2.1978; J-prior. 5.3.1976). medical use as gerontotherapeutic: US 4 156 718 (The New England Institute; 29.5.1979; prior. 19.1 1.1976, 12.12.1977). Formulation(s): amp. 50 mg; cps. 50 mg; drg. 50 mg; tab]. 10 mg, 25 mg, 50 mg, 60 mg, 200 mg Trade Name(s): I: Caomet (Astra Farmaceutici) Coedieci (Mitim) Decafar (Lafare) Decorenone (Italfarmaco) Dymion (Pulitzer) luvacor (Scharper) Miodene (Bioprogress) J: Miotyn (Ibirn) Inokiten (Nippon Yakuhin) Mitocor (Zambon Italia) Neuquinon (Eisai) Roburis (Ripari-Gero) Yubekinon (Hishiyama) Ubifactor (Sancarlo) USA: Coenzyme QlO (Vitaline) Ubimaior (Master Pharma) Co-Q- 10 (Tyson) Ubiten (Zilliken) Co-Q 10 (Carlson) generics Heartcin (Ohta) Ulobetasol propionate U 21 47 I Ulobetasol propionate ATC: D07A Use: topical corticosteroid RN: 66852-54-8 MF: C2,H,,C1F2O5 MW: 484.97 LDS,: >I5 mllkg (R, p.0.) CN: (6a,11 P, 16P)-21 -chloro-6,9-difluoro-ll-hydroxy-l6-methyl-l7-(1-oxopropoxy)pregna- 1,4-diene-3,20- dione halobetasol RN: 98651-66-2 MF: C2,H,C1F2O4 MW: 428.90 1. CHJSO2Cl, pyridine & H3 2. CH,CONH-Br, ticlo., Me H CH3 2. N-bromoacetamide H H 0 / H ortholormote 21-chlaro-9P. 1 la-epoxy- 166-methyl-1 7-propio- nyloxypreqn-4-enc- 3.20-dime CI0,F 11 + perchloryl fluoride 03\. benzoquinone I Ulobetasol propionote 1 Rej'erence(s): CH 631 185 (Ciba-Geigy; appl. 1.1.1978). DE 2 743 069 (Ciba-Geigy; appl. 24.9.1977; LUX-prior. 29.9.1976). BE 849 268 (Ciba-Geigy; appl. 28.9.1977; LUX-prior. 29.9.1976). GB 1 537 130 (Ciba-Geigy; appl. 27.9.1977; LUX-prior. 29.9.1976). synthesis of 21-chloro- 11 P-hydroxy- 16P-methyl- 17-propionyloxy pregn-4-ene-3,20-dione: GB 898 293 (Upjohn; appl. 14.3.1960; USA-prior. 18.3.1959). Formulation(s): cream 0.05 %; ointment 0.05 % 2 148 U Undccylenic acid Tra& Name(s): USA: Ultravate (Westwood- Squibb) Undecylenic acid (I 0-Undecensaure; Undecenoic acid) ATC: DOlAEO4 Use: antifungal RN: 112-38-9 MF: C,,H,,O, MW: 184.28 EINECS: 203-965-8 LD,,,: 81 50 mgtkg (M, p.0.); 2500 mglkg (R, p.o.1 CN: 1 0-undecenoic acid Reference (s): Krafft, F.: Ber. Dtsch. Chem. Ges. (BDCGAS) 10,2034 (1877). Perkins, G.A.; Cruz, A.O.: J. Am. Chem. Soc. (JACSAT) 49, 1070 (1927). ricinolic acid side product Fonnrrlation(s): cream 43 mg; liquid 30 mg; ointment 43 mg; powder 53 mg; soap 1 g; sol. 0.1 dl00 g Undecylenic acid Trade Na~ne(s): D: Skinman soft (Hent~el) Micofoot Zeta (Zeta)- USA: Breezee Mist Foot Powder GB: Ceanel (Quinodcrm)-comb. comb. (Pedino1)-comb. I: Foot Zeta (Zeta)-comb. J: Andecin (Fuji Seiaku) (also from castor oil) 1 Unoprostone isopropyl (UF-02 1 ) ATC: G02AD Use: ocular antihypertensive, antiglaucoma, prostaglandin derivative RN: 120373-24-2 MF: C,,H,05 MW. 424.62 CN: [1R-[la(Z),-2~,3a,5a]]-7-[3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl~-5-heptenoic acid I-methylethyl ester unoprostone RN: 120373-36-6 MF: CuH3,0, MW: 382.54 Unoprostone isopropyl U 2 149 (-)-Corey lactone (cf. dinaprost) y3 . a:) , CH&N I CH, Unaprostone isopropyl ~ko, R.; Kuno, S.; Miwa, N.; Takase, M.: 7th Int. Conf. Prostagland. Relat. Compound (May 28-June 1, Florence) 1990,28. EP 289 349 (Kabushiki Kaisha Keno Seiyaku Oyo Kenkyusho; appl. 2.1 1.1988; J-prior. 30.4.1987, 18.9.1987, 29.12.1987,30.4.1987, 17.9.1987). EP 308 135 (Kabushiki Kaisha Keno Seiyaku Oyo Kenkyusho; appl. 8.9.1988; J-prior. 18.9.1987; 29.12.1987). preparation of prostaglandin inter~nediates: EP 532 218 (R-Tech Keno Ltd; appl. 2.9.1992; J-prior. 3.9.1991). use of unoprostone isopropyl: EP 308 135 (Kabushiki Kaisha Keno Seiyaku Oyo Kenkyusho; appl. 22.3.1989; J-prior. 18.9.1988, 29.12.1 987). EP 561 073 (R-Tech Keno; appl. 22.9.1993; J-prior. 19.3.1992). EP 501 678 (Keno Seiyaku Oyo Kenkyujo; appl. 2.9.1992; J-prior. 1.3.1991). EP458 589 (Kabushiki Kaisha Keno Seiyaku Oyo Kenkyusho; appl. 27.11.1991; 22.5.1990). pharmaceutical compositions: CA 2 065 889 (R-Tech Keno; appl. 3.4.1993; J-prior. 2.10.1991). EP 330 51 1 (Kabushiki Kaisha Keno Seiyaku Oyo Kenkyusho; appl. 30.8.1989; J-prior. 26.2.1989). EP 668 076 (R-Tech Keno; appl. 15.3.1994; J-prior. 26.8.1992; EP-prior. 16.2.1994; CA-prior. 17.2.1994; USA- prior. 25.2.1994). 2150 U Uramustine Formulation(s): eye drops 6 mg/5 rnl Trade Narne(s): J: Rescula (UenoIFujisawa) Uramustine (Chlorethaminacil; Uracil-Mustard) ATC: LO1 Use: antineoplastic RN: 66-75-1 MF: C,H,,CI,N,O, MW: 252.10 EINECS: 200-63 1-3 LDS,,: 3550 Fg/kg (R, p.0.) CN: 5-[bis(2-chloroethyl)arnino]-2,4(1 H,3H)-pyrirnidinedionc 5-amino- ethylene uracil oxide Reference(s): US 2 969 364 (Upjohn; 24.1.1961; appl. 26.12.1957). Form~ulution(s): cps. 1 rng Trade Name(s); GB: Uracil Mustard (Upjohn); USA: Uracil Mustard (Upjohn); wfrn wfm Urapidil ATC: C02CA06 Use: antihypertensive RN: 34661 -75-1 ME C2(,H2yN,0, MW: 387.48 EINECS: 252-130-4 LDv,: 203 mglkg (M, i.v.); 508 rnglkg (M, p.0.); 140 mglkg (R, 1.v.); 520 mglkg (R, p.0.); 357 mglkg (dog, p.0.) CN: 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]amino]-l,3-dirnethyl-2,4(1H,3H)-pyrirnidinedione hydrochloride RN: 64887-14-5 MF: C,o112yN503 . HCI MW: 423.95 fumarate RN: 10241 1-1 1-0 MF: C,,H2,N503 . xC4H,0, MW: unspecified 1,3-dimethyl- 6-chloro-1.3- borblturic acid dmethyluracil 1.3-dimethyl-6-(3- hydroxypropylamino)- uracil (I) . RN: 6685 2-5 4-8 MF: C2,H,,C1F2O5 MW: 484.97 LDS,: >I5 mllkg (R, p.0.) CN: (6a,11 P, 16P )-2 1 -chloro-6,9-difluoro-ll-hydroxy-l6-methyl-l 7-( 1-oxopropoxy)pregna- 1,4-diene-3,2 0- dione halobetasol. 2-[ [(aminocarbonyl)oxy]methyl ]-2 -methylpentyl ester 2-methyl-2-propyl- diethyl 1.3-proponediol carbonate (cf. meprobamate synthesis) 5-methyl-5-propyl- 1,3-dioxan-2-one (I) 0 AI[OCH(CHJ)~I~ 1 + n2~~cti3 -+ ROAN-CHI H3C. polymer with oxirane and 4-( 1,1,3,3-tetramethylbutyl)phenol 4-( 1,1,3.3-tetra- form- methylbuty1 )- aldehyde ~henol ethylene oxide 1 I: ~ ~-( cH2-o-cn2)m-cn2-oti Tyloxapol Reference(s):