USRE37979E1 - Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof - Google Patents

Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof Download PDF

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USRE37979E1
USRE37979E1 US08957358 US95735897A USRE37979E US RE37979 E1 USRE37979 E1 US RE37979E1 US 08957358 US08957358 US 08957358 US 95735897 A US95735897 A US 95735897A US RE37979 E USRE37979 E US RE37979E
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halogen
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Tadashi Miyasaka
Hiromichi Tanaka
Erik Desiré DeClercq
Masanori Baba
Richard Thomas Walker
Masaru Ubasawa
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Mitsubishi Chemical Corp
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    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulfur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulfur or nitrogen atoms
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    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulfur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • C07D239/54Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulfur or nitrogen atoms
    • C07D239/60Three or more oxygen or sulfur atoms

Abstract

The disclosure concerns pyrimidine derivatives represented by the following general formulas [I] and [I′] and having antiviral activity, particularly antiretroviral activity such as anti-HIV activity:
Figure USRE037979-20030204-C00001
and pharmaceutical compositions having antiviral activity and comprising the above-described derivative(s) as an active ingredient.

Description

This is a continuation of application Ser. No. 07/590,475 filed on Sep. 28, 1990, now abandoned.

FIELD OF THE INVENTION

The present invention relates to novel 6-substituted acyclopyrimidine derivatives and antiviral agents containing the derivative as the active ingredients.

BACKGROUND OF THE INVENTION

Infectious diseases caused by human acquired immunodeficiency virus (HIV), which is a type of retrovirus, have recently become a serious social problem. A compound of 3′-deoxy-3′-azidothymidine is known as a nucleoside compound used in the clinical treatment for diseases caused by HIV-infection. However, this compound has side-effects since it also exhibits considerable strong toxicity in the host cells.

Although some 2′,3′-dideoxyribonucleosides are known as nucleoside compounds exhibiting an anti-viral activity, it is still necessary to develop a substance possessing a higher activity and lower toxicity to the host cell (Hiroaki Mitsuya, Bodily Defense, Vol. 4, pp.213-223 (1987)).

On the other hand, various acyclonucleoside compounds have been synthesized since Acyclovir (acycloguanosine) was developed as an antiviral substance effective against herpes virus (C. K. Chu and S. J. Culter, J. Heterocyclic Chem., 23, p.289 (1986)). However, no acyclonucleoside compound having a sufficient activity especially against retroviruses has yet been discovered.

We have focussed our attention on 6-substituted acyclopyrimidine nucleoside compounds and have synthesized various novel 6-substituted acyclopyrimidine nucleoside derivatives and screened those compounds to detect effective antiviral agents, especially to the retrovirus, in order to provide antiviral agents exhibiting an effective activity particularly against retroviruses.

Some 6-substituted acyclopyrimidine nucleoside compounds such as 6-fluoro substituted derivatives, 6-alkylamino substituted derivatives (DD-A-232492) and 6-methyl substituted derivatives (C. A. 107, 129717w (1987)) are known; however, the antiviral activity of these compounds has not been described.

As a result of our researches for compounds exhibiting an effective antiviral activity, particularly anti-retroviral activity, we found that specific 6-substituted pyrimidine nucleoside compounds according to the invention satisfy the above demand to achieve the present invention.

SUMMARY OF THE INVENTION

The present invention concerns 6-substituted acyclopyrimidine nucleoside derivatives represented by the following general formula I;

Figure USRE037979-20030204-C00002

wherein R1 represents a hydrogen atom, halogen atom, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, arylcarbonyl, arylcarbonylalkyl, arylthio or aralkyl group;

R2 represents an arylthio, alkylthio, cycloalkylthio, arylsulfinyl, alkylsulfinyl, cycloalkylsulfinyl, alkenyl, alkynyl, aralkyl, arylcarbonyl, arylcarbonylalkyl or aryloxy group, those groups optionally substituted by one or more of substituents selected from a halogen atom, alkyl, halogenated alkyl, alkoxy, hydroxyl, nitro, amino, cyano and acyl groups;

R3 represents a hydrogen atom, methyl, branched alkyl or —CH2—Z—(CH2)n—R5 group where R5 represents a hydrogen atom, halogen atom, hydroxyl, heterocyclic carbonyloxy, formyloxy, alkylcarbonyloxy, cycloalkylcarbonyloxy, aralkylcarbonyloxy, arylcarbonyloxy, azido, alkoxycarbonyloxy, N-alkylcarbamoyloxy, N-arylcarbamoyloxy, alkoxy, aralkyloxy, branched alkyl, cycloalkyl or aryl group, the alkoxycarbonyloxy to aryl groups mentioned above as R5 optionally substituted by one or more substituents selected from a halogen atom, aryl, alkyl, alkoxy and halogenated alkyl groups, Z represents an oxygen, sulfur atom or methylene group, and n represents 0 or an integer of 1 to 5,

R4 represents a hydrogen atom, alkyl or aralkyl group,

X and Y represent an oxygen or sulfur atom independently, provided that when R4 and Z represent a hydrogen atom and oxygen atom respectively R5 does not represent a hydroxyl group, or the following general formula I′;

Figure USRE037979-20030204-C00003

wherein R1, R2, R3 and Y have the same meanings as defined for the formula I above, pharmaceutically acceptable salts thereof and antiviral agents containing the derivative or the salt thereof as an active ingredient.

DETAILED DESCRIPTION OF THE INVENTION

The 6-substituted acyclopyrimidine nucleoside derivatives according to the invention are represented by the general formula I or I′.

The group of R1 represents a hydrogen atom; halogen atom such as chlorine, iodine, bromine and fluorine; alkyl group such as methyl, ethyl, n-propyl, i-propyl and n-butyl; cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; alkenyl group such as vinyl, propenyl, butenyl, phenylvinyl, bromovinyl, cyanovinyl, alkoxycarbonylvinyl and carbamoylvinyl; alkynyl group such as ethynyl, propynyl and phenylethynyl; alkylcarbonyl group such as acetyl, propionyl, and i-butyryl; arylcarbonyl group such as benzoyl and naphthoyl; arylcarbonylalkyl group such as phenacyl; arylthio group such as phenylthio, tolylthio and naphthylthio; or aralkyl group such as benzyl.

The group of R2 represents an arylthio group such as phenylthio and naphthylthio; alkylthio group such as methylthio, ethylthio, propylthio, butylthio and pentylthio; cycloalkylthio group such as cyclopentylthio, cyclohexylthio and cycloheptylthio; arylsulfinyl group such as phenylsulfinyl; alkylsulfinyl group such as methylsulfinyl, ethylsulfinyl and butylsulfinyl; cycloalkylsulfinyl group such as cyclopentylsulfinyl and cyclohexylsulfinyl; alkenyl group such as vinyl, propenyl and phenylvinyl; alkynyl group such as ethynyl, propynyl and phenylethynyl; aralkyl group such as benzyl; arylcarbonyl group such as benzoyl; arylcarbonylalkyl group such as phenacyl; or aryloxy group such as phenoxy, and those groups may be optionally substituted by one or more of substituents selected from a halogen atom such as chlorine, bromine, fluorine and iodine, alkyl group such as methyl, ethyl, propyl, butyl and pentyl, a halogenated alkyl group such as trifluoromethyl, alkoxy group such as methoxy, ethoxy, propoxy and butoxy, hydroxyl group, nitro group, amino group, cyano group and acyl group such as acetyl.

The group of R3 represents a hydrogen atom, methyl group, branched alkyl group such as i-propyl and t-butyl or —CH2—Z—(CH2)n—R5 group where R5 represents a hydrogen atom; halogen atom such as fluorine, chlorine, iodine and bromine; hydroxyl group; heterocyclic carbonyloxy group such as nicotinoyloxy; formyloxy group; optionally branched alkylcarbonyloxy group such as acetoxy, propyonyloxy, n-butyryloxy, i-butyryloxy, valeryloxy, hexanoyloxy, heptanoyloxy and decanoyloxy; cycloalkylcarbonyloxy group such as cyclohexylcarbonyloxy; aralkylcarbonyloxy group such as benzylcarbonyloxy; arylcarbonyloxy group such as benzoyloxy, toluoylcarbonyloxy and naphthoylcarbonyloxy group; azido group; alkoxycarbonyloxy group such as methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, i-propoxycarbonyloxy, n-butoxycarbonyloxy and t-butoxycarbonyloxy group, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; N-alkylcarbamoyloxy group such as N-methylcarbamoyloxy, N-ethylcarbamoyloxy, N-propylcarbamoyloxy, N-butylcarbamoyloxy and N-pentylcarbamoyloxy, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; N-arylcarbamoyloxy group such as N-phenylcarbamoyloxy and N-tolylcarbamoyloxy, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; N-alkylthiocarbamoyloxy group such as N-methytiocarbamoyloxy, N-ethylthiocarbamoyloxy, N-propylthiocarbamoyloxy, N-butylthiocarbamoyloxy and N-pentylthiocarbamoyloxy, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; N-arylthiocarbamoyloxy group such as N-phenylthiocarbamoyloxy and N-tolylthiocarbamoyloxy, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, t-butoxy, n-pentyloxy and n-hexyloxy group, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; branched alkyl group such as i-propyl, i-butyl, sec-butyl, t-butyl, i-heptyl and i-hexyl, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl; or aryl group such as phenyl, optionally substituted by one or more substituents selected from a halogen atom such as fluorine, chlorine, bromine and iodine, aryl group such as phenyl, toluyl and naphthyl, alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl, an alkoxy group such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy and t-butoxy and halogenated alkyl group such as trifluoromethyl, and Z represents an oxygen, sulfur atom or methylene group, and n represents 0 or an integer of 1 to 5,

R4 represents a hydrogen atom; optionally branched alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl and t-butyl; or aralkyl group such as benzyl.

X and Y represent oxygen or sulfur atom independently.

In the above formula I, when R4 and Z represent a hydrogen atom and oxygen atom respectively, R5 does not represent a hydroxyl group.

The preferred compounds according to the invention have R1 of a hydrogen atom, halogen atom, C1 to C5 alkyl group or C2 to C5 alkenyl group, particularly C1 to C5 alkyl group; R2 of C6 to C10 arylthio group, C3 to C10 cycloalkylthio group or C7 to C11 aralkyl group, particularly C6 to C10 arylthio, C3 to C10 cycloalkylthio or C7 to C11 aralkyl group, optionally substituted by one or more substituents selected from a halogen atom, C1 to C5 alkyl, C1 to C5 alkoxy and nitro groups; R3 of a hydrogen atom, methyl or —CH2—Z—(CH2)n—R5 group where R5 represents a hydrogen atom, halogen atom, hydroxyl, heterocyclic carbonyloxy, C2 to C11 alkylcarbonyloxy, C4 to C10 cycloalkylcarbonyloxy, C8 to C12 aralkylcarbonyloxy, C7 to C13 arylcarbonyloxy, C2 to C11 alkoxycarbonyloxy, C8 to C10 aralkyloxycarbonyloxy, C2 to C8 N-alkylcarbamoyloxy, C7 to C13 arylcarbamoyloxy, C2 to C8 alkylthiocarbamoyloxy, C7 to C13 arylthiocarbamoyloxy, C1 to C10 alkoxy, C7 to C13 aralkyloxy, azido, C3 to C5 branched alkyl, C5 to C7 cycloalkyl or C6 to C10 aryl group optionally substituted by one or more substituents selected from a halogen atom, aryl, alkyl, alkoxy and halogenated alkyl groups, Z represents an oxygen, sulfur atom or methylene group, and n represents 0 or an integer of 1 to 5; R4 of a hydrogen atom, C1 to C13 alkyl or C7 to C11 aralkyl group; X of an oxygen or sulfur atom; and Y of an oxygen or sulfur atom; provided that when R4 and Z represent a hydrogen atom and oxygen atom respectively R5 does not represent hydroxyl group,

Examples of the preferred compounds according to the present invention are listed in Table 1 below. t,120

TABLE 1
Figure USRE037979-20030204-C00004
Com- Melting
pound point
No. R1 R2 R3 R4 X Y (° C.)
 1 —CH3
Figure USRE037979-20030204-C00005
Figure USRE037979-20030204-C00006
—H O S 112˜ 113
 2 O 112˜ 113
 3
Figure USRE037979-20030204-C00007
155.5˜ 156.6
 4 S 144˜ 145
 5
Figure USRE037979-20030204-C00008
O 132˜ 133
 6
Figure USRE037979-20030204-C00009
100˜ 115
 7
Figure USRE037979-20030204-C00010
Figure USRE037979-20030204-C00011
120˜ 121
 8
Figure USRE037979-20030204-C00012
107˜ 108
 9
Figure USRE037979-20030204-C00013
9˜102
 10 —CH3
Figure USRE037979-20030204-C00014
Figure USRE037979-20030204-C00015
—H O O 80˜81
 11
Figure USRE037979-20030204-C00016
101˜ 102
 12
Figure USRE037979-20030204-C00017
132˜ 133
 13
Figure USRE037979-20030204-C00018
139˜ 140
 14
Figure USRE037979-20030204-C00019
115˜ 119
 15
Figure USRE037979-20030204-C00020
Figure USRE037979-20030204-C00021
95˜97
 16
Figure USRE037979-20030204-C00022
Figure USRE037979-20030204-C00023
175˜ 176
 17
Figure USRE037979-20030204-C00024
148˜ 150
 18
Figure USRE037979-20030204-C00025
157˜ 159
 19
Figure USRE037979-20030204-C00026
Figure USRE037979-20030204-C00027
107˜ 109
 20
Figure USRE037979-20030204-C00028
102˜ 104
 21 —CH3
Figure USRE037979-20030204-C00029
Figure USRE037979-20030204-C00030
—H O O 74˜80
 22
Figure USRE037979-20030204-C00031
148˜ 150
 23
Figure USRE037979-20030204-C00032
133˜ 134
 24
Figure USRE037979-20030204-C00033
91˜92
 25
Figure USRE037979-20030204-C00034
136˜ 137
 26
Figure USRE037979-20030204-C00035
123˜ 124
 27
Figure USRE037979-20030204-C00036
238˜ 242
 28
Figure USRE037979-20030204-C00037
229˜ 230
 29
Figure USRE037979-20030204-C00038
158˜ 160
 30
Figure USRE037979-20030204-C00039
124˜ 127
 31
Figure USRE037979-20030204-C00040
157˜ 158
 32 —CH3
Figure USRE037979-20030204-C00041
Figure USRE037979-20030204-C00042
—H O O 159˜ 161
 33
Figure USRE037979-20030204-C00043
Figure USRE037979-20030204-C00044
Oil
 34
Figure USRE037979-20030204-C00045
—CH3 74˜75
 35
Figure USRE037979-20030204-C00046
—H
 36
Figure USRE037979-20030204-C00047
 37
Figure USRE037979-20030204-C00048
 38
Figure USRE037979-20030204-C00049
 39
Figure USRE037979-20030204-C00050
 40
Figure USRE037979-20030204-C00051
 41
Figure USRE037979-20030204-C00052
136˜ 138
 42
Figure USRE037979-20030204-C00053
S
 43 —CH3
Figure USRE037979-20030204-C00054
Figure USRE037979-20030204-C00055
—CH3 O S
 44
Figure USRE037979-20030204-C00056
—H
 45
Figure USRE037979-20030204-C00057
 46
Figure USRE037979-20030204-C00058
 47
Figure USRE037979-20030204-C00059
 48
Figure USRE037979-20030204-C00060
 49
Figure USRE037979-20030204-C00061
 50
Figure USRE037979-20030204-C00062
 51
Figure USRE037979-20030204-C00063
 52
Figure USRE037979-20030204-C00064
 53
Figure USRE037979-20030204-C00065
 54 —CH3
Figure USRE037979-20030204-C00066
Figure USRE037979-20030204-C00067
—H O S
 55
Figure USRE037979-20030204-C00068
 56
Figure USRE037979-20030204-C00069
 57
Figure USRE037979-20030204-C00070
 58
Figure USRE037979-20030204-C00071
 59
Figure USRE037979-20030204-C00072
 60
Figure USRE037979-20030204-C00073
 61
Figure USRE037979-20030204-C00074
 62
Figure USRE037979-20030204-C00075
 63
Figure USRE037979-20030204-C00076
 64
Figure USRE037979-20030204-C00077
 65 —CH3
Figure USRE037979-20030204-C00078
Figure USRE037979-20030204-C00079
—H O S
 66
Figure USRE037979-20030204-C00080
O
 67
Figure USRE037979-20030204-C00081
Figure USRE037979-20030204-C00082
 68
Figure USRE037979-20030204-C00083
Figure USRE037979-20030204-C00084
 69
Figure USRE037979-20030204-C00085
—H
 70
Figure USRE037979-20030204-C00086
 71
Figure USRE037979-20030204-C00087
 72
Figure USRE037979-20030204-C00088
 73
Figure USRE037979-20030204-C00089
 74
Figure USRE037979-20030204-C00090
 75
Figure USRE037979-20030204-C00091
 76 —CH3
Figure USRE037979-20030204-C00092
Figure USRE037979-20030204-C00093
—H O O
 77
Figure USRE037979-20030204-C00094
 78
Figure USRE037979-20030204-C00095
 79
Figure USRE037979-20030204-C00096
 80
Figure USRE037979-20030204-C00097
 81
Figure USRE037979-20030204-C00098
 82
Figure USRE037979-20030204-C00099
 83
Figure USRE037979-20030204-C00100
 84
Figure USRE037979-20030204-C00101
 85
Figure USRE037979-20030204-C00102
 86
Figure USRE037979-20030204-C00103
 87 —CH3
Figure USRE037979-20030204-C00104
Figure USRE037979-20030204-C00105
—H O O
 88
Figure USRE037979-20030204-C00106
 89
Figure USRE037979-20030204-C00107
 90
Figure USRE037979-20030204-C00108
 91
Figure USRE037979-20030204-C00109
 92
Figure USRE037979-20030204-C00110
 93
Figure USRE037979-20030204-C00111
 94
Figure USRE037979-20030204-C00112
 95
Figure USRE037979-20030204-C00113
Figure USRE037979-20030204-C00114
 96
Figure USRE037979-20030204-C00115
 97
Figure USRE037979-20030204-C00116
 98 —CH3
Figure USRE037979-20030204-C00117
Figure USRE037979-20030204-C00118
—H O O
 99
Figure USRE037979-20030204-C00119
100
Figure USRE037979-20030204-C00120
101
Figure USRE037979-20030204-C00121
102
Figure USRE037979-20030204-C00122
103
Figure USRE037979-20030204-C00123
104
Figure USRE037979-20030204-C00124
105
Figure USRE037979-20030204-C00125
106
Figure USRE037979-20030204-C00126
107
Figure USRE037979-20030204-C00127
108
Figure USRE037979-20030204-C00128
109 —CH3
Figure USRE037979-20030204-C00129
Figure USRE037979-20030204-C00130
—H O O
110
Figure USRE037979-20030204-C00131
111
Figure USRE037979-20030204-C00132
112
Figure USRE037979-20030204-C00133
113
Figure USRE037979-20030204-C00134
114
Figure USRE037979-20030204-C00135
115
Figure USRE037979-20030204-C00136
116
Figure USRE037979-20030204-C00137
117
Figure USRE037979-20030204-C00138
118
Figure USRE037979-20030204-C00139
119
Figure USRE037979-20030204-C00140
120 —CH3
Figure USRE037979-20030204-C00141
Figure USRE037979-20030204-C00142
—H O O
121
Figure USRE037979-20030204-C00143
122
Figure USRE037979-20030204-C00144
123
Figure USRE037979-20030204-C00145
Figure USRE037979-20030204-C00146
S
124
Figure USRE037979-20030204-C00147
125
Figure USRE037979-20030204-C00148
126
Figure USRE037979-20030204-C00149
127
Figure USRE037979-20030204-C00150
128
Figure USRE037979-20030204-C00151
129
Figure USRE037979-20030204-C00152
130
Figure USRE037979-20030204-C00153
131 —CH3
Figure USRE037979-20030204-C00154
Figure USRE037979-20030204-C00155
—H O S
132
Figure USRE037979-20030204-C00156
133
Figure USRE037979-20030204-C00157
134
Figure USRE037979-20030204-C00158
135
Figure USRE037979-20030204-C00159
136
Figure USRE037979-20030204-C00160
137
Figure USRE037979-20030204-C00161
138
Figure USRE037979-20030204-C00162
139
Figure USRE037979-20030204-C00163
140
Figure USRE037979-20030204-C00164
141
Figure USRE037979-20030204-C00165
142 —CH3
Figure USRE037979-20030204-C00166
Figure USRE037979-20030204-C00167
—H O S
143
Figure USRE037979-20030204-C00168
144
Figure USRE037979-20030204-C00169
145
Figure USRE037979-20030204-C00170
146
Figure USRE037979-20030204-C00171
147
Figure USRE037979-20030204-C00172
148
Figure USRE037979-20030204-C00173
149
Figure USRE037979-20030204-C00174
150
Figure USRE037979-20030204-C00175
Figure USRE037979-20030204-C00176
151
Figure USRE037979-20030204-C00177
152
Figure USRE037979-20030204-C00178
153 —CH3
Figure USRE037979-20030204-C00179
Figure USRE037979-20030204-C00180
—H O S
154
Figure USRE037979-20030204-C00181
155
Figure USRE037979-20030204-C00182
156
Figure USRE037979-20030204-C00183
157
Figure USRE037979-20030204-C00184
158
Figure USRE037979-20030204-C00185
159
Figure USRE037979-20030204-C00186
160
Figure USRE037979-20030204-C00187
161
Figure USRE037979-20030204-C00188
162
Figure USRE037979-20030204-C00189
163
Figure USRE037979-20030204-C00190
Figure USRE037979-20030204-C00191
O
164 —CH3
Figure USRE037979-20030204-C00192
Figure USRE037979-20030204-C00193
—H O O
165
Figure USRE037979-20030204-C00194
166
Figure USRE037979-20030204-C00195
167
Figure USRE037979-20030204-C00196
168
Figure USRE037979-20030204-C00197
169
Figure USRE037979-20030204-C00198
170
Figure USRE037979-20030204-C00199
171
Figure USRE037979-20030204-C00200
172
Figure USRE037979-20030204-C00201
173
Figure USRE037979-20030204-C00202
174
Figure USRE037979-20030204-C00203
175 —CH3
Figure USRE037979-20030204-C00204
Figure USRE037979-20030204-C00205
—H O O
176
Figure USRE037979-20030204-C00206
177
Figure USRE037979-20030204-C00207
178
Figure USRE037979-20030204-C00208
179
Figure USRE037979-20030204-C00209
180
Figure USRE037979-20030204-C00210
181
Figure USRE037979-20030204-C00211
182
Figure USRE037979-20030204-C00212
183
Figure USRE037979-20030204-C00213
Figure USRE037979-20030204-C00214
184
Figure USRE037979-20030204-C00215
185
Figure USRE037979-20030204-C00216
186 —CH3
Figure USRE037979-20030204-C00217
Figure USRE037979-20030204-C00218
—H O O
187
Figure USRE037979-20030204-C00219
188
Figure USRE037979-20030204-C00220
189
Figure USRE037979-20030204-C00221
190
Figure USRE037979-20030204-C00222
191
Figure USRE037979-20030204-C00223
192
Figure USRE037979-20030204-C00224
193
Figure USRE037979-20030204-C00225
194
Figure USRE037979-20030204-C00226
195
Figure USRE037979-20030204-C00227
196
Figure USRE037979-20030204-C00228
197 —CH3
Figure USRE037979-20030204-C00229
Figure USRE037979-20030204-C00230
—H O O
198
Figure USRE037979-20030204-C00231
199
Figure USRE037979-20030204-C00232
200
Figure USRE037979-20030204-C00233
201
Figure USRE037979-20030204-C00234
202
Figure USRE037979-20030204-C00235
Figure USRE037979-20030204-C00236
203
Figure USRE037979-20030204-C00237
204
Figure USRE037979-20030204-C00238
205
Figure USRE037979-20030204-C00239
206
Figure USRE037979-20030204-C00240
207
Figure USRE037979-20030204-C00241
208 —CH3
Figure USRE037979-20030204-C00242
Figure USRE037979-20030204-C00243
—H O O
209
Figure USRE037979-20030204-C00244
210
Figure USRE037979-20030204-C00245
211
Figure USRE037979-20030204-C00246
212
Figure USRE037979-20030204-C00247
213
Figure USRE037979-20030204-C00248
214
Figure USRE037979-20030204-C00249
215
Figure USRE037979-20030204-C00250
216
Figure USRE037979-20030204-C00251
217
Figure USRE037979-20030204-C00252
218
Figure USRE037979-20030204-C00253
219 —CH3
Figure USRE037979-20030204-C00254
Figure USRE037979-20030204-C00255
—H O O
220
Figure USRE037979-20030204-C00256
221
Figure USRE037979-20030204-C00257
222
Figure USRE037979-20030204-C00258
223
Figure USRE037979-20030204-C00259
Figure USRE037979-20030204-C00260
—CH3 S
224
Figure USRE037979-20030204-C00261
Figure USRE037979-20030204-C00262
225
Figure USRE037979-20030204-C00263
—CH3
226
Figure USRE037979-20030204-C00264
227
Figure USRE037979-20030204-C00265
228
Figure USRE037979-20030204-C00266
229
Figure USRE037979-20030204-C00267
Figure USRE037979-20030204-C00268
230 —CH3
Figure USRE037979-20030204-C00269
Figure USRE037979-20030204-C00270
Figure USRE037979-20030204-C00271
O S
231
Figure USRE037979-20030204-C00272
232
Figure USRE037979-20030204-C00273
233
Figure USRE037979-20030204-C00274
234
Figure USRE037979-20030204-C00275
—CH3
235
Figure USRE037979-20030204-C00276
Figure USRE037979-20030204-C00277
236 —C2H5
Figure USRE037979-20030204-C00278
Figure USRE037979-20030204-C00279
—H O
237
Figure USRE037979-20030204-C00280
238
Figure USRE037979-20030204-C00281
239
Figure USRE037979-20030204-C00282
240
Figure USRE037979-20030204-C00283
241 —C2H5
Figure USRE037979-20030204-C00284
Figure USRE037979-20030204-C00285
—H O O
242
Figure USRE037979-20030204-C00286
243
Figure USRE037979-20030204-C00287
244
Figure USRE037979-20030204-C00288
245
Figure USRE037979-20030204-C00289
246
Figure USRE037979-20030204-C00290
247
Figure USRE037979-20030204-C00291
123˜ 125
248
Figure USRE037979-20030204-C00292
249
Figure USRE037979-20030204-C00293
250
Figure USRE037979-20030204-C00294
251
Figure USRE037979-20030204-C00295
252 —C2H5
Figure USRE037979-20030204-C00296
Figure USRE037979-20030204-C00297
—H O O 107˜ 108
253
Figure USRE037979-20030204-C00298
254
Figure USRE037979-20030204-C00299
255
Figure USRE037979-20030204-C00300
256
Figure USRE037979-20030204-C00301
—CH3
257
Figure USRE037979-20030204-C00302
Figure USRE037979-20030204-C00303
258
Figure USRE037979-20030204-C00304
—CH3
259
Figure USRE037979-20030204-C00305
260
Figure USRE037979-20030204-C00306
Figure USRE037979-20030204-C00307
H S
261
Figure USRE037979-20030204-C00308
O
262
Figure USRE037979-20030204-C00309
—CH3 S
263 —C2H5
Figure USRE037979-20030204-C00310
Figure USRE037979-20030204-C00311
—H O S
264
Figure USRE037979-20030204-C00312
265
Figure USRE037979-20030204-C00313
—CH3
266 —CH═CHBr
Figure USRE037979-20030204-C00314
Figure USRE037979-20030204-C00315
H
267
Figure USRE037979-20030204-C00316
O
268
Figure USRE037979-20030204-C00317
269
Figure USRE037979-20030204-C00318
270
Figure USRE037979-20030204-C00319
143˜ 148
271
Figure USRE037979-20030204-C00320
S
272
Figure USRE037979-20030204-C00321
273
Figure USRE037979-20030204-C00322
274 —CH═CHBr
Figure USRE037979-20030204-C00323
Figure USRE037979-20030204-C00324
—H O S
275
Figure USRE037979-20030204-C00325
—CH3
276
Figure USRE037979-20030204-C00326
Figure USRE037979-20030204-C00327
H O
277
Figure USRE037979-20030204-C00328
278 —CH3
Figure USRE037979-20030204-C00329
Figure USRE037979-20030204-C00330
S
279
Figure USRE037979-20030204-C00331
O
280
Figure USRE037979-20030204-C00332
S
281
Figure USRE037979-20030204-C00333
H
282
Figure USRE037979-20030204-C00334
Figure USRE037979-20030204-C00335
O
283
Figure USRE037979-20030204-C00336
284
Figure USRE037979-20030204-C00337
285 —CH3
Figure USRE037979-20030204-C00338
Figure USRE037979-20030204-C00339
—CH3 O O
286
Figure USRE037979-20030204-C00340
Figure USRE037979-20030204-C00341
H
287
Figure USRE037979-20030204-C00342
288
Figure USRE037979-20030204-C00343
Figure USRE037979-20030204-C00344
S
289
Figure USRE037979-20030204-C00345
290
Figure USRE037979-20030204-C00346
—CH3
291
Figure USRE037979-20030204-C00347
Figure USRE037979-20030204-C00348
H
292
Figure USRE037979-20030204-C00349
293
Figure USRE037979-20030204-C00350
294
Figure USRE037979-20030204-C00351
Figure USRE037979-20030204-C00352
O
295
Figure USRE037979-20030204-C00353
296 —CH3
Figure USRE037979-20030204-C00354
Figure USRE037979-20030204-C00355
—H O O
297
Figure USRE037979-20030204-C00356
298
Figure USRE037979-20030204-C00357
S
299
Figure USRE037979-20030204-C00358
300
Figure USRE037979-20030204-C00359
Figure USRE037979-20030204-C00360
301
Figure USRE037979-20030204-C00361
302
Figure USRE037979-20030204-C00362
303
Figure USRE037979-20030204-C00363
304
Figure USRE037979-20030204-C00364
Figure USRE037979-20030204-C00365
O
305
Figure USRE037979-20030204-C00366
306
Figure USRE037979-20030204-C00367
307 —CH3
Figure USRE037979-20030204-C00368
Figure USRE037979-20030204-C00369
—H O O
308
Figure USRE037979-20030204-C00370
309
Figure USRE037979-20030204-C00371
310
Figure USRE037979-20030204-C00372
S
311
Figure USRE037979-20030204-C00373
312
Figure USRE037979-20030204-C00374
Figure USRE037979-20030204-C00375
313
Figure USRE037979-20030204-C00376
314
Figure USRE037979-20030204-C00377
315
Figure USRE037979-20030204-C00378
316
Figure USRE037979-20030204-C00379
317
Figure USRE037979-20030204-C00380
318 —CH3
Figure USRE037979-20030204-C00381
Figure USRE037979-20030204-C00382
—H O S
319
Figure USRE037979-20030204-C00383
320
Figure USRE037979-20030204-C00384
Figure USRE037979-20030204-C00385
321
Figure USRE037979-20030204-C00386
322
Figure USRE037979-20030204-C00387
323
Figure USRE037979-20030204-C00388
324
Figure USRE037979-20030204-C00389
325
Figure USRE037979-20030204-C00390
326
Figure USRE037979-20030204-C00391
327
Figure USRE037979-20030204-C00392
328
Figure USRE037979-20030204-C00393
Figure USRE037979-20030204-C00394
O
329 —CH3
Figure USRE037979-20030204-C00395
Figure USRE037979-20030204-C00396
—H O S
330
Figure USRE037979-20030204-C00397
331
Figure USRE037979-20030204-C00398
332
Figure USRE037979-20030204-C00399
333
Figure USRE037979-20030204-C00400
334
Figure USRE037979-20030204-C00401
335
Figure USRE037979-20030204-C00402
336
Figure USRE037979-20030204-C00403
337
Figure USRE037979-20030204-C00404
338
Figure USRE037979-20030204-C00405
339
Figure USRE037979-20030204-C00406
340 —CH3
Figure USRE037979-20030204-C00407
Figure USRE037979-20030204-C00408
—H O S
341
Figure USRE037979-20030204-C00409
Figure USRE037979-20030204-C00410
342
Figure USRE037979-20030204-C00411
Figure USRE037979-20030204-C00412
343
Figure USRE037979-20030204-C00413
344
Figure USRE037979-20030204-C00414
345
Figure USRE037979-20030204-C00415
346 —C2H5
Figure USRE037979-20030204-C00416
Figure USRE037979-20030204-C00417
347
Figure USRE037979-20030204-C00418
348
Figure USRE037979-20030204-C00419
349
Figure USRE037979-20030204-C00420
350
Figure USRE037979-20030204-C00421
351 —CH═CHBr
Figure USRE037979-20030204-C00422
Figure USRE037979-20030204-C00423
—H O S
352
Figure USRE037979-20030204-C00424
353
Figure USRE037979-20030204-C00425
354
Figure USRE037979-20030204-C00426
355
Figure USRE037979-20030204-C00427
356
Figure USRE037979-20030204-C00428
357 —C2H5
Figure USRE037979-20030204-C00429
Figure USRE037979-20030204-C00430
O 165˜ 166
358
Figure USRE037979-20030204-C00431
S 106˜ 109
359
Figure USRE037979-20030204-C00432
155˜ 156
360
Figure USRE037979-20030204-C00433
Figure USRE037979-20030204-C00434
O 110˜ 112
361
Figure USRE037979-20030204-C00435
156˜ 158
362 —CH3
Figure USRE037979-20030204-C00436
Figure USRE037979-20030204-C00437
—H O O 157˜ 161
363 —C2H5 S 151˜ 153
364
Figure USRE037979-20030204-C00438
158˜ 160
365
Figure USRE037979-20030204-C00439
Figure USRE037979-20030204-C00440
O 159˜ 162
366 S 112˜ 116
367
Figure USRE037979-20030204-C00441
O
368 S
369
Figure USRE037979-20030204-C00442
Figure USRE037979-20030204-C00443
O
370
Figure USRE037979-20030204-C00444
371
Figure USRE037979-20030204-C00445
372 —C2H5
Figure USRE037979-20030204-C00446
Figure USRE037979-20030204-C00447
—H O S 157˜ 160
373
Figure USRE037979-20030204-C00448
374
Figure USRE037979-20030204-C00449
375
Figure USRE037979-20030204-C00450
Figure USRE037979-20030204-C00451
O
376 S
377
Figure USRE037979-20030204-C00452
O
378 S
379 —CH3
Figure USRE037979-20030204-C00453
Figure USRE037979-20030204-C00454
380
Figure USRE037979-20030204-C00455
O
381 S
382 —CH3
Figure USRE037979-20030204-C00456
Figure USRE037979-20030204-C00457
—H O O
383 S
384
Figure USRE037979-20030204-C00458
O
385 S
386
Figure USRE037979-20030204-C00459
O
387 S
388
Figure USRE037979-20030204-C00460
O
389 S
390
Figure USRE037979-20030204-C00461
O
391 S
392
Figure USRE037979-20030204-C00462
Figure USRE037979-20030204-C00463
393
Figure USRE037979-20030204-C00464
Figure USRE037979-20030204-C00465
394
Figure USRE037979-20030204-C00466
395
Figure USRE037979-20030204-C00467
O
396 S
397
Figure USRE037979-20030204-C00468
Figure USRE037979-20030204-C00469
398 O
399
Figure USRE037979-20030204-C00470
Figure USRE037979-20030204-C00471
S
400
Figure USRE037979-20030204-C00472
401
Figure USRE037979-20030204-C00473
Figure USRE037979-20030204-C00474
O
402 S
403
Figure USRE037979-20030204-C00475
O
404 —CH3
Figure USRE037979-20030204-C00476
Figure USRE037979-20030204-C00477
—H O S
405
Figure USRE037979-20030204-C00478
Figure USRE037979-20030204-C00479
406
Figure USRE037979-20030204-C00480
407
Figure USRE037979-20030204-C00481
408
Figure USRE037979-20030204-C00482
O
409 S
410
Figure USRE037979-20030204-C00483
Figure USRE037979-20030204-C00484
O
411
Figure USRE037979-20030204-C00485
S
412
Figure USRE037979-20030204-C00486
413
Figure USRE037979-20030204-C00487
O
414 S
415 —CH3
Figure USRE037979-20030204-C00488
Figure USRE037979-20030204-C00489
—H O S
416
Figure USRE037979-20030204-C00490
417
Figure USRE037979-20030204-C00491
418
Figure USRE037979-20030204-C00492
O
419 S
420
Figure USRE037979-20030204-C00493
Figure USRE037979-20030204-C00494
O
421 S
422 —C2H5 O
423 S
424 —CH3
Figure USRE037979-20030204-C00495
O
425 S
426 —C2H5
Figure USRE037979-20030204-C00496
Figure USRE037979-20030204-C00497
—H O O
427 S
428 —CH3
Figure USRE037979-20030204-C00498
O
429 S
430 —C2H5 O
431
Figure USRE037979-20030204-C00499
S
432 —CH3
Figure USRE037979-20030204-C00500
O
433 S
434 —C2H5 O
435 S
436 —CH3
Figure USRE037979-20030204-C00501
O
437 —CH3
Figure USRE037979-20030204-C00502
Figure USRE037979-20030204-C00503
—H O S
438 —C2H5 O
439 S
440 —CH3
Figure USRE037979-20030204-C00504
O
441 S
442 —C2H5
Figure USRE037979-20030204-C00505
O
443 S
444 —CH3
Figure USRE037979-20030204-C00506
O
445 S
445 —C2H5 O
447 S
448 —C2H5
Figure USRE037979-20030204-C00507
Figure USRE037979-20030204-C00508
—H O S
449
Figure USRE037979-20030204-C00509
O
450 S
451
Figure USRE037979-20030204-C00510
O
452 S
453
Figure USRE037979-20030204-C00511
O
454 S
455
Figure USRE037979-20030204-C00512
O
456 S
457
Figure USRE037979-20030204-C00513
O
458 S
459 —C2H5
Figure USRE037979-20030204-C00514
Figure USRE037979-20030204-C00515
—H S
460
Figure USRE037979-20030204-C00516
O
461 S
462
Figure USRE037979-20030204-C00517
O
463 S
464
Figure USRE037979-20030204-C00518
O
465 S
466
Figure USRE037979-20030204-C00519
O
467 S
468
Figure USRE037979-20030204-C00520
O
469 S
470 —C2H5
Figure USRE037979-20030204-C00521
Figure USRE037979-20030204-C00522
—H O O
471 S
472
Figure USRE037979-20030204-C00523
O 92.5˜95
473 S
474
Figure USRE037979-20030204-C00524
O 160˜ 160.7
475 S
476
Figure USRE037979-20030204-C00525
Figure USRE037979-20030204-C00526
O
477 S
478
Figure USRE037979-20030204-C00527
O
479 S
480
Figure USRE037979-20030204-C00528
O
481 —C2H5
Figure USRE037979-20030204-C00529
Figure USRE037979-20030204-C00530
—H O S
482
Figure USRE037979-20030204-C00531
Figure USRE037979-20030204-C00532
483
Figure USRE037979-20030204-C00533
O
484 S
485 —CH3
Figure USRE037979-20030204-C00534
Figure USRE037979-20030204-C00535
O 118˜ 120
486
Figure USRE037979-20030204-C00536
Figure USRE037979-20030204-C00537
O
487 S
488 —C2H5 O
489 S
490 —CH3
Figure USRE037979-20030204-C00538
O
491 S
492 —C2H5
Figure USRE037979-20030204-C00539
Figure USRE037979-20030204-C00540
—H O O
493 S
494
Figure USRE037979-20030204-C00541
Figure USRE037979-20030204-C00542
Figure USRE037979-20030204-C00543
O
495
Figure USRE037979-20030204-C00544
496
Figure USRE037979-20030204-C00545
112˜ 114
497 S 138˜ 140
498
Figure USRE037979-20030204-C00546
O
499 S
500
Figure USRE037979-20030204-C00547
O
501
Figure USRE037979-20030204-C00548
Figure USRE037979-20030204-C00549
S
502
Figure USRE037979-20030204-C00550
O
503
Figure USRE037979-20030204-C00551
Figure USRE037979-20030204-C00552
Figure USRE037979-20030204-C00553
−H O S
504
Figure USRE037979-20030204-C00554
O
505 S
506
Figure USRE037979-20030204-C00555
O
507 S
508
Figure USRE037979-20030204-C00556
O
509 S
510
Figure USRE037979-20030204-C00557
O
511 S
512
Figure USRE037979-20030204-C00558
Figure USRE037979-20030204-C00559
O 138˜ 141
513 S 165˜ 168
514
Figure USRE037979-20030204-C00560
Figure USRE037979-20030204-C00561
Figure USRE037979-20030204-C00562
—H O O
515 S
516
Figure USRE037979-20030204-C00563
O
517 S
518
Figure USRE037979-20030204-C00564
O
519 S
520
Figure USRE037979-20030204-C00565
O
521 S
522
Figure USRE037979-20030204-C00566
O
523 S
524
Figure USRE037979-20030204-C00567
O
525
Figure USRE037979-20030204-C00568
Figure USRE037979-20030204-C00569
Figure USRE037979-20030204-C00570
—H O S
526
Figure USRE037979-20030204-C00571
Figure USRE037979-20030204-C00572
O
527 S
528
Figure USRE037979-20030204-C00573
O
529 S
530
Figure USRE037979-20030204-C00574
O
531 S
532
Figure USRE037979-20030204-C00575
O
533 S
534
Figure USRE037979-20030204-C00576
O
535 S
536
Figure USRE037979-20030204-C00577
Figure USRE037979-20030204-C00578
Figure USRE037979-20030204-C00579
—H O O
537 S
538
Figure USRE037979-20030204-C00580
O
539 S
540
Figure USRE037979-20030204-C00581
O
541 S
542
Figure USRE037979-20030204-C00582
Figure USRE037979-20030204-C00583
O
543 S
544
Figure USRE037979-20030204-C00584
O
545 S
546
Figure USRE037979-20030204-C00585
O
547
Figure USRE037979-20030204-C00586
Figure USRE037979-20030204-C00587
Figure USRE037979-20030204-C00588
—H O S
548
Figure USRE037979-20030204-C00589
O
549 S
550
Figure USRE037979-20030204-C00590
O
551 S
552
Figure USRE037979-20030204-C00591
O
553 S
554
Figure USRE037979-20030204-C00592
O
555 S
556
Figure USRE037979-20030204-C00593
Figure USRE037979-20030204-C00594
O
557 S
558
Figure USRE037979-20030204-C00595
Figure USRE037979-20030204-C00596
Figure USRE037979-20030204-C00597
—H O O
559 S
560
Figure USRE037979-20030204-C00598
O
561 S
562
Figure USRE037979-20030204-C00599
O
563 S
564
Figure USRE037979-20030204-C00600
O
565 S
566
Figure USRE037979-20030204-C00601
O
567 S
568
Figure USRE037979-20030204-C00602
O
569
Figure USRE037979-20030204-C00603
Figure USRE037979-20030204-C00604
Figure USRE037979-20030204-C00605
—H O S
570
Figure USRE037979-20030204-C00606
Figure USRE037979-20030204-C00607
Figure USRE037979-20030204-C00608
O
571
Figure USRE037979-20030204-C00609
S
572
Figure USRE037979-20030204-C00610
O
573 S
574
Figure USRE037979-20030204-C00611
Figure USRE037979-20030204-C00612
O 94˜97
575 S 123˜ 124
576
Figure USRE037979-20030204-C00613
O
577 S
578
Figure USRE037979-20030204-C00614
O
579 S
580
Figure USRE037979-20030204-C00615
Figure USRE037979-20030204-C00616
Figure USRE037979-20030204-C00617
—H O O
581 S
582
Figure USRE037979-20030204-C00618
O
583 S
584
Figure USRE037979-20030204-C00619
O
585 S
586
Figure USRE037979-20030204-C00620
O
587 S
588
Figure USRE037979-20030204-C00621
O
589 S
590
Figure USRE037979-20030204-C00622
Figure USRE037979-20030204-C00623
O
591
Figure USRE037979-20030204-C00624
Figure USRE037979-20030204-C00625
Figure USRE037979-20030204-C00626
—H O S
592
Figure USRE037979-20030204-C00627
O
593 S
594
Figure USRE037979-20030204-C00628
O
595 S
596
Figure USRE037979-20030204-C00629
O
597 S
598
Figure USRE037979-20030204-C00630
O
599 S
600
Figure USRE037979-20030204-C00631
O
601 S
602
Figure USRE037979-20030204-C00632
Figure USRE037979-20030204-C00633
Figure USRE037979-20030204-C00634
—H O O
603 S
604
Figure USRE037979-20030204-C00635
Figure USRE037979-20030204-C00636
O
605 S
606
Figure USRE037979-20030204-C00637
O
607 S
608
Figure USRE037979-20030204-C00638
O
609 S
610
Figure USRE037979-20030204-C00639
O
611 S
612
Figure USRE037979-20030204-C00640
O
613
Figure USRE037979-20030204-C00641
Figure USRE037979-20030204-C00642
Figure USRE037979-20030204-C00643
—H O S
614
Figure USRE037979-20030204-C00644
O
615 S
616
Figure USRE037979-20030204-C00645
O
617 S
618
Figure USRE037979-20030204-C00646
Figure USRE037979-20030204-C00647
O
619 S
620
Figure USRE037979-20030204-C00648
O
621 S
622
Figure USRE037979-20030204-C00649
O
623 S
624
Figure USRE037979-20030204-C00650
Figure USRE037979-20030204-C00651
Figure USRE037979-20030204-C00652
—H O O
625 S
626
Figure USRE037979-20030204-C00653
O
627 S
628
Figure USRE037979-20030204-C00654
O
629 S
630
Figure USRE037979-20030204-C00655
O
631 S
632
Figure USRE037979-20030204-C00656
Figure USRE037979-20030204-C00657
O
633 S
634
Figure USRE037979-20030204-C00658
O
635
Figure USRE037979-20030204-C00659
Figure USRE037979-20030204-C00660
Figure USRE037979-20030204-C00661
—H O S
636
Figure USRE037979-20030204-C00662
O
637 S
638
Figure USRE037979-20030204-C00663
O
639 S
640
Figure USRE037979-20030204-C00664
O
641 S
642
Figure USRE037979-20030204-C00665
O
643 S
644
Figure USRE037979-20030204-C00666
O
645 S
646 n-C3H7
Figure USRE037979-20030204-C00667
Figure USRE037979-20030204-C00668
—H O O
647
Figure USRE037979-20030204-C00669
Figure USRE037979-20030204-C00670
S
648
Figure USRE037979-20030204-C00671
Figure USRE037979-20030204-C00672
O
649 S
650
Figure USRE037979-20030204-C00673
O
651 S
652
Figure USRE037979-20030204-C00674
O
653 S
654
Figure USRE037979-20030204-C00675
O
655 S
656
Figure USRE037979-20030204-C00676
Figure USRE037979-20030204-C00677
O
657 n-C3H7
Figure USRE037979-20030204-C00678
Figure USRE037979-20030204-C00679
—H O S
658
Figure USRE037979-20030204-C00680
O
659 S
660
Figure USRE037979-20030204-C00681
O
661 S
662
Figure USRE037979-20030204-C00682
O