Supporting information for J. Med. Chem., 1994, 37(5), , DOI: /jm00031a018
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1 Supporting information for J. Med. Chem., 1994, 37(5), , DOI: /jm00031a018 Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at Copyright 1994 American Chemical Society
2 11 WO- (1%%-m Compound homogeneity was determined by analytical reverse phase HPLC using a Dynamax-60A column (5µ; 250 mm 4.6 mm; C18) using eluents A: water, 0.1% TFA, and B: acetonitrile, 0.1% TFA, with gradient elution from 85% A : 15% to 20% A : 80% over 30 min with a flow rate of 1.5 ml/min. The eluent was monitored by UV absorption at 215 nm. Compounds were characterized by NMR using a Varian Unity 300 spectrometer using TMS or solvent as an internal standard. 70
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4 DELAY FILE 1 VIAL 1.05 INJ 1 OF 1 VOL TRAY 14 EQUIL. TIME.00 GRAD..00 CHANNEL A INJECT :03:23 STORED TO BIN # 66??? ER 0 DATA SAVED TO BIN# 66 INPUT OVERRANGE AT RT = FILE 1. METHOD 1. ^ INDEX 58 " ro CH= "A" PS= BIN 0. RUN 58 PEAK# AREA% RT BIN 66 AREA BC / V r --* r 01 * 3
5
6 m. DIALOGl AUTOSAMPLER FILE...PRESS ERASE? (Y OR ) Y <ENTER> TO SKIP TO NEXT QUERY VIAL INJ VOL I J/VIAL CAL INT CAL VIAL FILE LAST VIAL? (0 ) 1.04 SYRINGE RATE? ( 2) END A/S DIALOG FILE 1 VIAL 1.01 INJ 1 OF 1 VOL 1010 TRAY 1 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :09:13 STORED TO BIN # 45 It78???ER 0 DATA SAVED TO BIN # 45
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8 CHANNEL A INJECT :33:33 STORED TO BIN # 103??? DATA SAVED TO BIN # 103 INPUT OVERRANGE AT RT= :33:33 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 127 INDEX 127 BIN 103 PEAK# AREA% RT AREA BC TOTAL
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10 CHANNEL A INJECT :22:49 STORED TO BIN # 34??? DATA SAVED TO BIN # 34 LC CONDITIONS UNIT1 RUN FILE 1 TIME %A %B %C FLOW MAX. PRESS. LIMIT=3500 PSl M1N. PRESS. LIMIT0PSl 3 j* oo INPUT OVERRANGE AT RT= :22:49 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 55 INDEX 28 BIN 34 PEAK# AREA% RT AREA BL AREA BL
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13 ??? DATA SAVED TO BIN # 45 INPUT OVERRANGE AT RT= :17:47 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 63 INDEX 63 BIN 45 PEAK# AREA% RT AREA BC c 3 TOTAL
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15 CHANNEL A INJECT :44: 18 STORED TO BIN # 29??? DATA SAVED TO BIN # 29 INPUT OVERRANGE AT RT= :44:18 CH= "A" PS= 1. FILE 1 METHOD 0. RUN 312 INDEX 312 BIN 29 3 " PEAK# AREA% RT AREA BC c D u in TOTAL
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17 CHANNEL A INJECT :27: 57 STORED TO BIN # 9??? DATA SAVED TO BIN # 9 c/i CO INPUT OVERRANGE AT RT= 8.24 RUN FILE1. METHOD 0. RUN 419 PEAK# AREA% "A" PS= 1. INDEX 419 BIN 9 BIN 9 RT AREA BC TOTAL :27:57 CH=
18
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20 ' W if??? DATA SAVED TO BIN tt 6 3 INPUT OVERRANGE AT RT= Q. cn :49:34 CH= "A" PS= 1. (71 FILE 1. METHOD 0. RUN 772 INDEX 772 BIN 6 PEAK# AREA% RT AREA BC TOTAL c WARNING - MEMORY AT UNPROTECTED CHROMATOGRAMS WILL BE REPLACED
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22
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24 01? FILE 1 VIAL 2.04 INJ 1 OF 1 VOL 1010 TRAY 15 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :52:20 STORED TO BIN # 128??? DATA SAVED TO BIN # 128
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26 . CHANNEL A INJECT 05/03/91 09:18:59 REPLAYED FROM BIN # 48 4^.??? INPUT OVERRANGE AT RT= Q 3 05/03/91 09:18:59 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 205 INDEX 205 BIN 48 PEAK# AREA% RT AREA BC > * r 1 orx OO 1
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30 CHANNEL A INJECT :44:13 STORED TO BIN # 50??? DATA SAVED TO BIN # 50 LC CONDITIONS UNIT 1 RUN FILE 1 TIME XA XB XC FLOW MAX. PRESS. LIMIT = 3500 PSI M1N. PRESS. LIMIT = 0 PSI INPUT OVERRANGE AT RT= Q :44:13 CH= "A" PS= 1 3 FILE 1. METHOD 0. RUN 72 INDEX 45 BIN 50 Q) CO PEAK# AREA% RT AREA BC
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32 pj CHANNEL A INJECT :03: 56 STORED TO BIN tt 100??? DATA SAVED TO BIN # 100 > A INPUT OVERRANGE AT RT= 16.51
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34
35 U1514/62/1 CRUDE DS1.A FAULT 10 CHANNEL A INJECT :05:13 STORED TO BIN # 97??? DATA SAVED TO BIN # 97
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37 CHANNEL A INJECT :55:22 REPLAYED FROM BIN # 46 AZ 1??? INPUT OVERRANGE AT RT= :55:22 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 320 INDEX 320 BIN 46 PEAK# AREA% RT AREA BC
38
39 CHANNEL A INJECT :49:32 REPLAYED FROM BIN # 121??? INPUT OVERRANGE AT RT= :49:32 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 147 INDEX 147 BIN 121 PEAK# AREA%. RT AREA BC TOTAL INK LOW - CHANGE PRINT CARTRIDGE AND PRESS [CTRL-SHIFT-C]
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41 VIAL 4.05 INJ 1 OF 1 VOL 1010 TRAY 12 EQUIL TIME.00 GRAD DELAY.00 CHANNEL A INJECT :01:46 STORED TO BIN # 55??? 3 > < DATA SAVED TO BIN # 55 INPUT OVERRANGE AT RT= FILE 1 METHOD 0. RUN 315 5:01:46 CH= "A" PS= 1. INDEX 315 BIN 55 PEAK# AREA% RT AREA BC A OC"J / rs r\ 4
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43 CHANNEL A INJECT :32:27 STORED TO BIN # 71??? DATA SAVED TO BIN # 71 INPUT OVERRANGE AT RT= :32:27 CH= "A" PS= 1. C FILE 1. METHOD 0. RUN 464 INDEX 464 BIN 71 V PEAK# AREA% RT AREA BC -%l ( (?f,r74 1 fl*
44
45 CHANNEL A INJECT :54:32 STORED TO BIN # 120 AZ1??? DATA SAVED TO BIN # 120 INPUT OVERRANGE AT RT= 2.24 g :54:32 CH= "A" PS= 1. C D FILE 1. METHOD 0. RUN 117 INDEX 117 BIN 120 Q PEAK# AREA% RT AREA BC > " T-*/-. -» / /-«I OO
46
47 END A/S DIALOG FILE 1 VIAL 2.01 INJ 1 OF 1 VOL 1010 TRAY 15 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :39:51 STORED TO BIN # 80??? ER 0 2 DATA SAVED TO BIN # 80. -J ro c INPUT OVERRANGE AT RT= :39:51 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 72 INDEX 72 BIN 80 PEAK# AREA% RT AREA BC 1 n nn ooo / m
48
49 , vi:a- v:v<:3 i "' ' V ! < : :/47856 ;40 '> TOTAL WARNING - MEMORY AT 0. - UNPROTECTED FILE 1 VIAL 3.02 INJ 1 OF 1 VOL 1010 TRAY 9 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :13:22 STORED TO BIN It 119 AZ 1??? DATA SAVED TO BIN # 119 W INPUT OVERRANGE AT RT= 2.24
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51 U1514/81/ AFTER FREEZE-DRYER DS1.A FAULT 10 CHANNEL A INJECT :52:21 STORED TO BIN # 102??? DATA SAVED TO BIN # 102 INPUT OVERRANGE AT RT= 16.94
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53 ??? data saved to bin # 91.g :06:54 ch= "a" ps= 1. c 3 ci file 1. method 0. run 438 index 438 bin 91 (j\ peak# area% rt area bc
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55 ??? DATA SAVED TO BIN # 123 INPUT OVERRANGE AT RT= 2.2 q :42:42 CH= "A" PS= 1. FILE 1. METHOD 0. RUN 467 INDEX 467 BIN 123 PEAK# AREA% RT AREA BC Q
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57 FILE 1 VIAL 4.02 INJ 1 OF 1 VOL 1010 TRAY 12 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :05:51 STORED TO BIN # 57??? 1 DATA SAVED TO BIN # 57 INPUT OVERRANGE AT RT= :05:51 CH= MA" PS= 1. FILE 1 METHOD 0. RUN 317 INDEX 317 BIN 57 PEAK# AREA% RT AREA BC
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59 ??? CHANNEL A INJECT :18:51 STORED TO BIN #82 AZ1 DATA SAVED TO BIN # 82 INPUT OVERRANGE AT RT :18:51 CH= "A" PS= 1. FILE 1 METHOD 0. RUN 80 INDEX 80 BIN 82 PEAK# AREA% RT AREA BC TOTAL WARN 1NG - MEMORY AT UNPROTECTED CHROMATOGRAMS W1ILL BE REPLACED
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61 FILE 1 VIAL 2.02 INJ 1 OF 1 VOL 1010 TRAY 15 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :29:58 STORED TO BIN # 126??? DATA SAVED TO BIN # 126 I PUT OVERRANGE AT RT= 2.29
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63 ??? DATA SAVED TO BIN # 81 INPUT OVERRANGE AT RT :37:40 CH= "A" PS= 1. FILE 1 METHOD 0. RUN 79 INDEX 79 BIN 81 PEAK# AREA% RT AREA BC L TOTAL WARNING - MEMORY AT 5. - UNPROTECTED CHROMATOGRAMS W1ILL BE REPLACED
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65 EQUIL. TIME.00 GRAD. DELAY.00 CHANNEL A INJECT :15:49 STORED TO BIN # 2 AZ 1??? DATA SAVED TO BIN # 7.86 ner 0 INPUT OVERRANGE AT RT= " :15:49 CH= "A" PS= 1. ^ FILE 1. METHOD 0. RUN 253 PEAK# AREA% RT AREA BC TOTAL INDEX 253 BIN 2 00 WARNING - MEMORY AT 0. - UNPROTECTED CHROMATOGRAMS WILL BE REPLACED
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