Pharmaceutical Substances Syntheses, Patents, Applications - Part 166 ppsx

Piperazine P 1651 Formulation(s): amp. 1 g/10 ml, 2 gl20 ml; vial 1 g, 1.5 g, 2 g, 3 g, 4 g (as sodium salt) Trade Name(s): D: Pipril (Ledcrlc; 1980) Tazocin (Wyeth)-comb. J: Pentcillin (Sankyo; 1980) F: PipCrilline (Wyeth-Lederle) I: Avocin (Wyeth-Lederle; USA: Pipracil (Lederle; 1982) Tazocilline (Wyeth- 1982) Zasyn (Lederle) Lederle) Eril (Savio IBN) GB: Pipril (Wyeth-Lederle; Tazocil (Wyeth-Leder1e)- 1982) comb. Piperazine ATC: P02CBOl Use: anthelmintic RN: 110-85-0 MF: C4Hl,,N2 MW: 86.14 EINECS: 203-808-3 LD,,: 11 80 mgkg (M, i.v.); 600 mgkg (M, p.0.); 1340 mgkg (R, i.v.); 1900 mgkg (R, p.0.) CN: piperazine hexahydrate RN: 142-63-2 MF: C4H,,N2. 6H20 MW: 194.23 LD,,: 11.2 &kg (M, p.0.) dihydrochloride RN: 142-64-3 MF: C4Hl,N2 .2HCl MW: 159.06 EINECS: 205-55 1-2 LD,,,: 4900 mgkg (R, p.0.) phosphate RN: 195 1-97-9 MF: C4Hl,N2 . xH,04P MW: unspecified EINECS: 2 17-775-8 LD,: 20 &kg (M, p.0.) tartrate (1:l) RN: 133-36-8 MF: C4HloN2 . C4H,06 MW: 236.22 EINECS: 205-104-1 citrate (3:2) RN: 144-29-6 MF: C6H80, . 3/2C4HloN2 MW: 642.66 EINECS: 205-622-8 LD,,: 8500 mglkg (M, p.0.); 1 1200 mg/kg (R, p.0.) citrate (3:2) hydrate RN: 41372-10-5 MF: C6H80, . 3/2C4Hl,N2. xH20 MW: unspecified edetate calcium (1:l) - RN: 12002-30-1 MF: C10H14CaN20, . C4HloN, MW: 416.44 edetate calcium (1:l) dihydrate RN: 50322-15-1 MF: C,,H14CaN20c C4H,,N2. 2H20 MW: 452.47 adipate (1:l) RN: 142-88-1 MF: C,H,,O, . C4H,,N2 MW: 232.28 EINECS: 205-569-0 LD,,): 8 gkg (M, p.0.); 7900 mgkg (R, p.0.) Reference(s): Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 7,385. NH3. 150-220 T. 100-250 bar H,N-O~ b ethanolamine Fomulation(s): tabl. 10 mg H (:I H Piperazine Trade Name(s): D: Girheulit (Pfliiger)-comb. GR: Pripsen (Seton)-comb. USA: Antepar (Burroughs F: Carudol (Boehringer Ing.) I: Citropiperazina (RhGne- Wellcome); wfm Vermifuge Sorin (Sorin- Poulenc Pharma) Maxim) J: Bexin (Tanabe) Piperidolate ATC: A03AA30 Use: anticholinergic, antispasmodic RN: 82-98-4 MF: C2,H2,N0, MW: 323.44 EINECS: 201-449-7 LD,,: 75 mgkg (M, i.v.); 100 mglkg (R, i.v.) CN: a-phenylbenzeneacetic acid I-ethyl-3-piperidinyl ester hydrochloride RN: 129-77-1 MF: Cz1Hz5NO2. HCl MW: 359.90 EINECS: 204-964-5 LD,,: 26 mgkg (M, i.v.); 1040 mglkg (M, p.0.); 19 mgkg (R, i.v.); 35 mgkg (dog, i.v.) furfurol ethylamine N-ethyl-N-(tetrahydra- furfuryl)amine 1-ethyl-3-hydroxy- piperidine (1) Referencefs): US 2 918 407 (LakesideLabs.; 22.12.1959; appl. 8.4.1957; prior. 18.8.1950). Biel, J.H. et al.: J. Am. Chem. Soc. (JACSAT) 74, 1485 (1952). diphenylacetyl Formulation(s): tabl. 50 mg (as hydrochloride) Piperidolate Trade Name(s): D: Dactil (Med-Fabrik); wfrn I: Dactil (Roger Bellon); wfm USA: Dactil (Merrell-National); F: Dactil (Roger Bellon); wfm Dactilase (RBS Pharma)- wfm Dactilase (Roger Bellon)- comb.; wfm Dactilase (Merrell- comb.; wfm J: Cactiran (Kyorin) National); wfm GB: Dactil (MCP. Dactil OB (Kissei) Pharmaceuticals); wfm Edelel (Mochida) chloride Piperocaine ATC: NOlBC Use: local anesthetic RN: 136-82-3 MF: C,,H2,N02 MW: 261.37 EINECS: 205-262-1 CN: (+)-2-methyl-I-piperidinepropanol benzoate (ester) hydrochloride RN: 2456 1- 10-2 MF: C,,H2,N02 . HC1 MW: 297.83 LD,,: 18.2 mgkg (M, i.v.); 20 mglkg (R, i.v.) piperidine benzoyl 3-chloro- 3-chloropropyl chloride propanol benzoate Reference(s): US 1 784 903 (S. M. McElvain; 1930; prior. 1927). Trade Name(s): USA: Metycaine (Lilly); wfm s"-8 Piperocoine Piperylone ATC: NO2BB Use: analgesic RN: 2531-04-6 MF: C,,HZ3N3O MW: 285.39 EINECS: 219-788-4 CN: 4-ethyl-l,2-dihydro-2-(l-methyl-4-piperidiny1)-5-phenyl-3H-pyrazol-3-one benzoyl- 1 -methyl-4- hydrozine piperidone butyrote 4-hydrozina-1 -methyl- piperidine dihydrochloride Piperylone I US 2 903 460 (Sandoz; 8.9.1959; CH-prior. 7.4.1956). Ebnother, A. et al.: Helv. Chim. Acta (HCACAV) 42, 1201 (1959). Trade Name(s): D: Pelerol (Sandoz)-comb.; wfm 1654 P Pipobroman Pipobroman RN: 54-91-1 MF: C,,H16Br,N202 MW: 356.06 LD,,,: 382 mglkg (M, p.0.); 220 mgkg (R, pa.) CN: 1,4-bis(3-bromo-1-oxopropy1)piperazine ATC: LOlAXO2 Use: antineoplastic OpBr C I H 3-bromopropionyl piperozine Pipobromon chloride Reference(s): DE 1 138 78 1 (Abbott; appl. 10.10.1960; USA-prior. 11.7.1960). Formulation(s): tabl. 10 mg, 25 mg Trade Namefs): D: Vercyte (Abbott); wfm I: Vercite 25 (Abbott) USA: Vercyte (Abbott); wfm F: Vercyte (Abbott) J: Amedel (Marupi) Pipotiazine ATC: N05AC04 Use: neuroleptic RN: 39860-99-6 MF: C,H3,N30,S, MW: 475.68 EINECS: 254-659-6 CN: 10-[3-[4-(2-hydroxyethyl)-l-piperidinyl]propyl]-N,N-dimethyl-lOH-phenothiazine-2-sulfonamide palmitate RN: 37517-26-3 MF: C,,H,,N-,O,S, MW: 714.09 phenothiozine oxy)propyl chloride 4-(2-hydroxyethy1)- Pipotiazine piperidine Pipoxolan P 1655 Referencefs): DE 1 117 584 (RhBne-Poulenc; appl. 1958; F-prior. 1957). Fonnulationfs): amp. 10 mgl2 ml, 100 mgl4 ml, 25 mgll ml; drops 4 % (as palmitate); tabl. 10 mg Trade Narnefs): F: Piportil (RhBne-Poulenc Piportil LA (RhBne-Poulenc GB: Piportil Depot (1HC; as Rorer Specia) Rorer Specia; as palmitate) palmitate) Pipoxolan ATC: A03AA Use: antispasmodic RN: 23744-24-3 MF: CzzHz5N0, MW: 351.45 CN: 5,5-diphenyl-2-[2-(1-piperidinyl)ethyl]-1,3-dioxolan-4-one hydrochloride RN: 18174-58-8 MF: CzZHz5NO3. HC1 MW: 387.91 LD,,: 35 mgkg (M, i.v.); 700 mgkg (M, p.0.); 60 mgkg (R, i.v.); 1500 mgkg (R, p.0.) 3-chloropropion- piperidine 3-piperidinopropion- aldehyde diethyl aldehyde diethyl acetol ocetol (I) benzilic acid Pipoxolon Reference (s): GB 1 109 959 (Rowa-Wagner; appl. 3.10.1966; A-prior. 5.10.1965). Formulation(s): tabl. 10 mg Trade Narnefs): D: Rowapraxin (Rowa- Wagner) Pipradrol ATC: N06BX15 Use: central stimulant RN: 467-60-7 MF: Cl8H2,NO MW: 267.37 EINECS: 207-394-5 LD,: 74 mgkg (M, p.0.); 30 mgkg (R, i.v.); 180 mgkg (R, p.0.) CN: a,a-diphenyl-2-piperidinemethanol 1656 P Piprinhydrinate hydrochloride RN: 71-78-3 MF: C,,H,,NO. HCI MW. 303.83 EINECS: 200-764-7 LD,,: 20 mgkg (M, i.v.); 120 mgkg (M, p.0.); 30 mgkg (R, i.v.); 180 mgkg (R, p.0.) 0 &" + Mg W5Br , [ 6"'" ] A I ethyl benzophenone bromide 2-bromo- 2-pyridylrnoqnesium py ridine bromide o.a-diphenyl-2- pyridinemethonol (I) Reference(s): Tilford, C.H. et al.: J. Am. Chem. Soc. (JACSAT) 70,4001 (1948). US 2 624 739 (Merrell; 1953; appl. 1949). Formulation(s): drg. 1 mg (as hydrochloride) Trade Name(s): D: Vitazell G forte (Tosse)- I: Detaril (Isom); wfm comb.; wfm Piprinhydrinate ATC: R06 Use: antihistaminic, anti-emetic, antirhinitic RN: 606-90-6 MF: C,,H2,N0 . C7H7C1N402 MW: 496.01 EINECS: 210- 128-0 LD,,: 75 mgkg (M, i.v.); 275 mgkg (M, p.0.) CN: 8-chloro-3,7-dihydro- 1,3-dimethyl- 1 H-purine-2,6-dione compd. with 4-(dipheny1methoxy)-1- methylpiperidine (1: 1) DE 934 890 (Promonta; appl. 1951). y3 7H3 CH3 CH3 diphenyl- 8-chlorotheophylline pyroline Piprinhydrinote Piproxen P 1657 Formulation(s): drg. 1 mg; syrup 0.5 mg in comb. with paracetamol, ethenzamide Trade Name(s): D: Kolton (Byk Gulden)- J: Agiell (Sanwa) comb. Plokon (Nippon Shinyaku) Piproxen (Naproxen piperazine) ATC: MOlAE Use: non-steroidal anti-inflammatory RN: 70981-66-7 MF: C,,Hl4O3. 1/2C4H,JV2 MW: 546.66 EINECS: 275-083-1 CN: (S)-6-methoxy-a-methyl-2-naphthaleneacetic acid, compd. with piperazine (2: 1) I Piproxen I Reference(s): ES 474 535 (Centro Inv. Farm.; appl. 16.3.1979). EP 308 739 (Coop. Farm. Soc.; appl. 9.9.1989; I-prior. 22.9.1987). Formulation(s): suppos. 600 mg; tabl. 300 mg Trade Name(s): I: Alganil (Ibis); wfm Piprozolin ATC: AOSAXOI Use: choleretic RN: 17243-64-0 MF: C14H22N20,S MW: 298.41 EINECS: 241-280-6 LD,,: 1310 mgkg (M, p.0.); . 3256 mgkg (R, p.0.) CN: [3-ethyl-4-oxo-5-(l-piperidinyl)-2-thiazolidinylidene]acetic acid ethyl ester ethyl l-oxothiozolidin- 2-ylideneacetate (cf. etozolin synthesis) H3C7 F) Sm0-CH3 Br2, CHCI, 0-;-0 S-N 0 , I o '-CH, o k~, diethyl sulfate CNH -+ piperidine I Piprozolin I 1658 P Piracetam Refermce(s): DOS 2 414 345 (Godecke; appl. 25.3.1974). Formulatinn(s): drg. 100 mg Trade Nume(s): D: Probilin (Godecke); wfm I: Probilin (Parke Davis); Secrebil (Isnardi); wfm wfm Piracetam ATC: N06BX03 Use: cerebrostimulant RN: 749 1-74-9 MF: C,H,,N,O, MW: 142.16 EINECS: 23 1-3 12-7 LD,,: 9200 mgkg (M, i.v.); 2g/kg(M, p.0.) CN: 2-0x0- 1-pyrrolidineacetamide 1. NOH 0 ti 2. clJo-cH3 NH3. CH30H . PNH~ . 1. sodium hydride e0 2. ethyl chloroocetote 2-pyrrolidone (I) I 1. sodium hydride 2. chloroocetomide Reference(s): US 3 459 738 (UCB; 5.8.1969; GB-prior. 6.8.1964). DAS 1 620 608 (UCB; appl. 4.8.1965; GB-prior. 6.8.1964). alternative synlhesis (from N-(4-chlorobutyry1)glycinamide): DAS 2 759 297 (Pliva; appl. 14.1.1977; YU-prior. 14.1.1976, 11.8.1976). DOS 2 701 450 (Pliva; appl. 14.1.1977; YU-prior. 14.1 .l976, 11.8.1976). platelet aggregation inhibitory activity: DOS 2 746 761 (UCB; appl. 18.10.1977; GB-prior. 19.10.1976). US 4 115 579 (UCB; 19.9.1978; GB-prior. 19.10.1976). Formulation(s): amp. 1 g/5 ml; sol. 333 mg, 41 6.25 mg; cps. 400 mg, 1200 mg; drinking amp. 1 g; f. c. tabl. 800 mg, 1200 mg; gran. 1200 mg, 1600 mg; tabl. 400 mg, 1200 mg Trade Name(s): D: Avigilen (Brenner-Efeka) Normabrain (Hoechst; F: Axonyl (Parke Davis) Cerebroforte (Azuchemie) 1974) Gabacet (Synthklabo) Cerepar (Merckle) Pinacetrop (Holsten) Geram (Vedim) Cuxahrain (TAD) Sinapsan (Rodleben; Nootropyl (UCB; 1972) Encetrop (Kytta-Siegfried) Vedim) GB: Nootropil (UCB) Nootrop (UCB; 1974) generics I: Cerebropan (Nuovo ISM) Pirarubicin P 1659 Clevian (Aesculapius) Nootropil (UCB) Psycoton (Esseti) Flavis (Pulitzer) Norzetam (Vedim Pharma) Pirarubicin (Theprubicin ; THP-ADM) ATC: LOIDB08 Use: antitumor anthracycline antibiotic RN: 72496-41-4 MF: C,,H,,NO,, MW: 627.64 LD,,: 27.8 mglkg (M, i.v.) CN: [8S-[8a,10a(S*)]]-10-[[3-amino-2.3,6-trideoxy-4-0-(tetrahydr0-2H-pyran-2-yl)-a-~-1~~0- hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11 -trihydroxy-8-(hydroxyacety1)-I -methoxy-5,12- naphthacenedione monohydrochloride RN: 95343-20-7 MF: C32H37NO12 . HCI MW: 664.10 LD,,: 14 mgkg (M, i.v.); 420 mglkg (M, p.0.); 18.1 mglkg (R, i.v.); >1.013 g/kg (R, p.0.) OH 0 3cx0* 2. K2C03, H20, CHJOH b OH 0 0, 0 CH3 1. 3,4-dihydro-2H-pyran, HO p-toluenesulfonic acid NH2 Reference(s): EP 14 853 (Zaidan Hojin Biseibutsu Kagaku; appl. 23.1.1980; J-prior. 3.2.1979,31.8.1979). US 4 303 785 (Zaidan Hojin Biseibutsu Kagaku; 1.12.1981 ; J-prior. 5.8.1978, 3.2.1979,31.8.1979). Umezawa, H. et al.: J. Antibiot. (JANTAJ) 32, 1082 (1979). OH 0 HO~ cH3 14-0-ocetyldoxorubicin alternative synthesis: EP 228 546 (Zaidan Hojin Biseibutsu Kagaku; appl. 14.11.1 986; J-prior. 16.1 1.1985). Pirarubicin Formulation(s): amp. 10 mg, 20 mg, 50 mg (as hydrochloride) Trade Name(s): F: ThCpn~bicine (RhBne- J: Pinorubicin (Nippon Therarubicin (Meiji Seika; Poulenc Rorer; 1990) Kay aku/Sanraku; 1988) 1988) Pirbuterol ATC: RO3ACO8; R03CC07 Use: bronchodilator RN: 38677-81-5 MF: C,,HzON,O, MW: 240.30 CN: a~[[(l,l-dimethylethyl)amino]methyl]-3-hydroxy-2,h-pyridinedimethanol dihydrochloride RN: 38029-10-6 MF: C,2H20N203 .2HC1 MW: 313.23 EINECS: 253-751-3 monoacetate RN: 65652-44-0 MF: C,2H20N203. C2H402 MW: 300.36 EINECS: 265-862-4 1660 P Pirbuterol @ 1. HCHO 'u Mn02 A HOTOH aoH I. formaldehyde ' 07 mangones? I 2. benzyl bromide dioxide 3-hydroxy- pyridine 5-benzyloxy-6-(hydroxy- methy1)pyridine-Z- carboxaldehyde (I) tert-butyl- isocyanide HCI diboroner I Pirbuterol nitro- methane tert-butyl bromide Reference(s): US 3 700 681 (Pfizer; 24.10.1972; prior. 16.2.1971). US 3 763 173 (Pfizer; 2.10.1973; pior. 25.5.1972, 16.2.1971). US 3 772 314 (Pfizer; 13.1 1.1973; prior. 24.10.1972,25.5.1972, 16.2.1971). US 3 786 160 (Pfizer; 15.1.1974; prior. 25.5.1972, 24.10.1972, 16.2.1971). DOS 2 204 195 (Pfizer; appl. 29.1.1972; USA-prior. 16.2.1971). alfernafive syntheses: EP 58 069 (Pfizer; appl. 8.2.1982; USA-prior. 9.2.1981). US 3 948 919 (Pfizer; 6.4.1976: prior. 9.10.1974; 26.12.1973). US 4 031 108 (Pfizer; 21.6.1977; prior. 14.7.1976,22.9.1975,9.10.1974, 26.12.1973). . 253 1-0 4-6 MF: C,,HZ3N3O MW: 285.39 EINECS: 21 9-7 8 8-4 CN: 4-ethyl-l,2-dihydro- 2-( l-methyl-4-piperidiny1 )-5 -phenyl-3H-pyrazol-3-one benzoyl- 1 -methyl- 4- hydrozine piperidone butyrote 4-hydrozina-1. [8S-[8a,10a(S*)] ]-1 0-[ [3-amino-2.3,6-trideoxy- 4-0 -( tetrahydr 0-2 H-pyran-2-yl)-a- ~-1 ~~ 0- hexopyranosyl]oxy ]-7 ,8,9,10-tetrahydro-6,8,11 -trihydroxy- 8-( hydroxyacety1)-I -methoxy-5,1 2- naphthacenedione monohydrochloride RN: 9534 3-2 0-7 MF: C32H37NO12. RN: 3986 0-9 9-6 MF: C,H3,N30,S, MW: 475.68 EINECS: 25 4-6 5 9-6 CN: 1 0-[ 3-[ 4-( 2-hydroxyethyl)-l-piperidinyl]propyl]-N,N-dimethyl-lOH-phenothiazine-2-sulfonamide palmitate RN: 3751 7-2 6-3 MF: