CN1926138A

CN1926138A - Substituted imidazo ring systems and methods

Info

Publication number: CN1926138A
Application number: CN 200480040954
Authority: CN
Inventors: 拉里·R·克莱普斯基; 小约瑟夫·F·德拉里亚; 丹尼尔·E·达菲; 马修·R·拉德默; 戴维·T·阿莫斯
Original assignee: 3M Innovative Properties Co
Current assignee: 3M Innovative Properties Co
Priority date: 2003-11-25
Filing date: 2004-11-24
Publication date: 2007-03-07
Also published as: ZA200605216B; CN1905874A

Abstract

Imidazo ring systems substituted at the 1-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

Description

The imidazo ring systems and the method that replace

The cross reference of related application

The application requires the right of priority of U.S. Provisional Application of submitting on November 25th, 2,003 60/524961 and the U.S. Provisional Application of submitting on June 16th, 2,004 60/580139, and the full content that is incorporated herein these two applications as a reference.

Background

In 50 generations of 20th century, 1H-imidazo [4,5-c] quinoline ring system is developed, and discloses synthetic 1-(6-methoxyl group-8-quinolyl)-2-methyl isophthalic acid H-imidazo [4, the 5-c] quinoline that may be used as antimalarial drug.Subsequently, report 1H-imidazo [4,5-c] quinoline synthetic of various replacements.For example, synthesized compound 1-[2-(4-piperidyl) ethyl that may be used as spasmolytic and cardiovascular drug]-1H-imidazo [4,5-c] quinoline.In addition, reported also [4,5-c] quinoline of several 2-oxo-imidazoles.

The derivative that some 1H-imidazo [4,5-c] quinoline 4-amine and 1-thereof and 2-replace found can be used as antiviral drug, bronchodilator and immunomodulator afterwards.Subsequently, the 1H-imidazo [4 that has synthesized some replacement, 5-c] pyridine-4-amine, quinoline-4-amine, tetrahydroquinoline-4-amine, naphthyridines-4-amine, with Tetrahydronaphthyridderivates-4-amine compound and thiazole Bing that some is similar with oxazole and compound, and find that they can be used as immune response modifier (IRM), this makes them can be used for treating various diseases.

Like this imidazoquinoline ring system and other ring systems are continued to become interested, and continue to need and to regulate immunoreactive compound by the biosynthesizing of the inducing cell factor or other mechanism.

General introduction

The invention provides a class and be used for the biosynthetic novel cpd of induced animal cytokine.This compound has following formula (I):

Wherein: Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-; With

Wherein: X, R _A, R _B, R ₂, R _1-1, Q, and R _1-3By following defined.

Because the compound of formula I-1 has the biosynthetic ability of the inducing cell factor (for example, inducing the synthetic of at least a cytokine), and has the immunoreactive ability of adjusting when being administered to animal, therefore is used as immune response modifier (IRM).This makes this compound can be used for treating various illnesss, and as virus disease and tumour, these illnesss are all in response to these variations in the immune response.

In another aspect, the invention provides the pharmaceutical composition of the compound of the formula I-1 that contains significant quantity, and by the compound of the formula I-1 of significant quantity is obeyed to animal, come cytokine biosynthesizing in the induced animal, the method for neoplastic disease in viral infection and/or the treatment animal in the treatment animal.

In addition, the invention provides the compound of synthesis type I-1 and be used for the method for the intermediate of synthetic these compounds.

Herein, " a kind of (a) ", " a kind of (an) ", " this (the) ", " at least a " reach " one or more " and are used interchangeably.

Term in specification sheets and claims " comprises " and variant is not a limited significance.

General introduction is not intended to illustrate each disclosed embodiment of the present invention or each embodiment above of the present invention.Following specification sheets has more particularly been illustrated these exemplary.In several places of the application, a series of examples also provide directive function, can use by various array modes.In each example, the content of listing only is representational, should not be interpreted as limiting content.

The invention exemplary describes in detail

The invention provides the compound of following formula (I-1):

Wherein: Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-; With

The more specific compound of formula (I-2, I-3, and I-4), represent different center ring structures:

Wherein: Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-; And the more specific compound of following formula (Ia, Ib, Id, and Ie):

Wherein: X, R, R _a, R _A, R _B, R _A', R _B', R ₂, R ₃, R _1-1, Q, R _1-3And n is by following defined; With the acceptable salt of its medicine.

The present invention also provides the compound of following formula (II, III, and IV):

Wherein: Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

Wherein: X, R, R ₂, R _1-1, R _1-6, Q, R _1-3And n is by following defined; With the acceptable salt of its medicine.

The compound or the acceptable salt of its medicine of following formula (I-1) are provided in one embodiment:

Wherein:

X is an alkylidene group, chooses wantonly to be inserted with one or more-O-group;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

By the alkyl that one or more substituting groups replace, aryl, alkylidene group-aryl, heteroaryl, or alkylidene group-heteroaryl, described substituting group is selected from:

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

By the alkyl that one or more substituting groups replace, aryl, alkylidene group-aryl, heteroaryl, or alkylidene group-heteroaryl, this substituting group is selected from:

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Or R _1-3Group can be joined together to form and comprise saturated or undersaturated 5-, 6-, or the ring system of 7-unit ring;

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

X ' is selected from alkylidene group, alkylene group, and alkynylene, arylidene, and inferior heteroaryl, alkylidene group wherein, alkylene group and alkynylene be optional to be inserted with arylidene or inferior heteroaryl or with its end-blocking with optionally be inserted with one or more-O-group;

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₄Be selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl heteroarylidene, alkyl wherein, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, the heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl heteroarylidene can be unsubstituted, perhaps can be replaced by one or more substituting group, this substituting group is independently selected from alkyl, alkoxyl group, hydroxyalkyl, haloalkyl, halogenated alkoxy, halogen, nitro, hydroxyl, sulfydryl, cyano group, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroaryl alkylene oxide group, heterocyclic radical, amino, alkylamino, dialkylamino, (dialkylamino) alkylene oxide group, and at alkyl, be oxo under alkenyl and the alkynyl situation;

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₈Be selected from hydrogen, alkyl, alkoxyl group alkylidene group, and aryl alkylene;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

Q ' is selected from key ,-C (R ₆)-,-C (R ₆)-C (R ₆)-,-S (O) ₂-and-S (O) ₂-N (R ₈)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7;

R _AAnd R _BEach is independently selected from:

Hydrogen,

Halogen,

Alkyl,

Alkenyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂；

Or R _AAnd R _BForm fused aromatic rings unsubstituted or that replaced by one or more R groups together, or unsubstituted or by one or more R _aGroup replaced condenses 5～7 yuan of saturated rings;

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

-N(R ₉) ₂；

R _aBe selected from:

Halogen,

Hydroxyl,

Alkyl,

Alkenyl,

Haloalkyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂。

The compound or the acceptable salt of its medicine of following formula (I-2) are provided in one embodiment:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

-N(R ₉) ₂；

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₄Be selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl heteroarylidene, alkyl wherein, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, the heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl heteroarylidene can be unsubstituted, perhaps can be replaced by one or more substituting group, this substituting group is independently selected from alkyl, alkoxyl group, hydroxyalkyl, haloalkyl, halogenated alkoxy, halogen, nitro, hydroxyl, sulfydryl, cyano group, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, the heteroaryl alkylene oxide group, heterocyclic radical, amino, alkylamino, dialkylamino, (dialkylamino) alkylene oxide group, and at alkyl, alkenyl is an oxo under alkynyl and the heterocyclic radical situation;

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-,-N (R ₈)-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7.

The compound or the acceptable salt of its medicine of following formula (I-3) are provided in another embodiment:

Wherein:

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7;

R _A' and R _B' each is independently selected from:

Hydrogen,

Halogen,

Alkyl,

Alkenyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂。

The compound or the acceptable salt of its medicine of following formula (I-4) are provided in another embodiment:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R _aBe selected from:

Halogen,

Hydroxyl,

Alkyl,

Alkenyl,

Haloalkyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂；

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7.

The compound or the acceptable salt of its medicine of following formula (Ia) are provided in another embodiment:

Wherein:

N is 0～4 integer;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl,

-N (CH ₃) (OCH ₃) and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

N (R ₉) ₂With

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

By alkyl or alkenyl that one or more substituting groups replace, this substituting group is selected from:

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

The compound or the acceptable salt of its medicine of following formula (Ib) are provided in another embodiment:

Wherein:

X is an alkylidene group;

N is 0～4 integer;

R _1-1Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

In another embodiment, the invention provides the compound or the acceptable salt of its medicine of formula (Id):

Wherein:

N is 0～4 integer;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

The compound or the acceptable salt of its medicine of following formula (Ie) are provided in another embodiment:

Wherein:

N is 0～4 integer;

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

The compound or the acceptable salt of its medicine of following formula (II) are provided in another embodiment:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N(R ₉) ₂；

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

The compound or the acceptable salt of its medicine of following formula (III) are provided in another embodiment:

Wherein:

N is the integer of O～4;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-6Be alkyl or R _1-6Group can be joined together to form the ring system that comprises saturated 5-or 6-unit ring;

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

N (R ₉) ₂With

R ₉Be selected from hydrogen and alkyl.

The compound or the acceptable salt of its medicine of following formula (IV) are provided in another embodiment:

Wherein:

X is an alkylidene group;

N is 0～4 integer;

R _1-1Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂With

R ₉Be selected from hydrogen and alkyl.

Herein, term " alkyl ", " alkenyl ", " alkynyl " and prefix " alkane-" comprise straight chain and branched group and cyclic group, i.e. cycloalkyl and cycloalkenyl group.Unless refer else, these groups contain 1～20 carbon atom, and wherein alkenyl contains 2～20 carbon atoms, and alkynyl contains 2～20 carbon atoms.In certain embodiments, these groups are always total up to 10 carbon atoms, up to 8 carbon atoms, and up to 6 carbon atoms, or up to 4 carbon atoms.Cyclic group can be monocycle or polycyclic, preferably has 3-10 ring carbon atom.Exemplary cyclic group comprises cyclopropyl, the cyclopropyl methyl, and cyclopentyl, cyclohexyl, adamantyl replaces and unsubstituted bornyl, norcamphyl and norbornene.

Unless refer else, " alkylidene group (alkylene) ", " alkylene group (alkenylene) " and " alkynylene (alkynylene) " are " alkyl " of above-mentioned definition, the bivalent form of " alkenyl " and " alkynyl ".When " alkylidene group ", " alkylene group " and " alkynylene " uses term " alkylidene group ", " alkylene group ", " alkynylene " when being substituted respectively.For example, aryl alkylene comprises the alkylene moiety that links to each other with aryl.

Term " haloalkyl " comprises and comprises fully-fluorinated group by the alkyl that is replaced by one or more halogen atoms.For other groups that comprise prefix " halo-" also is like this.The example that is fit to haloalkyl is a chloromethyl, trifluoromethyl etc.

Herein, term " aryl " comprises carbocyclic ring aromatic nucleus or ring system.The aryl example comprises phenyl, naphthyl, xenyl, fluorenyl and indenyl.

Unless refer else, term " heteroatoms " refers to atom O, S, or N.

Term " heteroaryl " comprises and contains at least one ring hetero atom (for example, O, S, aromatic nucleus N) or ring system.Suitable heteroaryl comprises furyl, thienyl, pyridyl, quinolyl, isoquinolyl, indyl, pseudoindoyl, triazolyl, pyrryl, tetrazyl, imidazolyl, pyrazolyl oxazolyl, thiazolyl, benzofuryl, benzo thiophenyl, carbazyl, benzoxazolyl, pyrimidyl, benzimidazolyl-, quinoxalinyl, benzothiazolyl, phthalazinyl ， isoxazolyl, isothiazolyl, purine radicals, quinazolyl, pyrazinyl, 1-pyridine oxide base, pyridazinyl, triazinyl, tetrazine Ji ， oxadiazole base, thiadiazolyl group etc.

Term " heterocyclic radical " comprise contain at least one ring hetero atom (for example, O, S, N) non-aromatic ring or ring system, all that comprise above-mentioned heteroaryl are saturated and undersaturated derivatives of part fully.Exemplary heterocyclic group comprises pyrrolidyl, tetrahydrofuran base, morpholinyl, thio-morpholinyl, piperidyl, piperazinyl, thiazolinyl, imidazolinyl, the isothiazoline base, THP trtrahydropyranyl, quinuclidinyl, homopiperidinyl (nitrogen Zhuo Ji), high piperazinyl (phenodiazine Zhuo Ji), 1, the 3-dioxolanyl, acridyl, dihydro-isoquinoline-(1H)-and Ji, octahydro isoquinoline 99.9-(1H)-Ji, dihydroquinoline-(2H)-Ji, the octahydro quinoline-(2H)-and Ji, dihydro-1H-imidazolyl etc.When " heterocyclic radical " when containing nitrogen-atoms, the tie point of heterocyclic radical can be a nitrogen-atoms.

Term " arylidene (arylene) ", " inferior heteroaryl (heteroarylene) ' ' and " inferior heterocyclic radical (heterocyclylene) " being above-mentioned definition " aryl ", " heteroaryl " and " heterocyclic radical " bivalent form.When " arylidene ", " inferior heteroaryl " and " inferior heterocyclic radical " uses term " arylidene " when being substituted respectively, " inferior heteroaryl " and " inferior heterocyclic radical ".For example, alkyl arylene comprises the arylidene part that links to each other with alkyl.

When in any formula, when group (or substituting group or variant) occurred more than one time, whether each group (or substituting group or variant) was selected independently, no matter specified.For example, for formula-N (R ₃) ₂, select each R independently ₃In another example, when existing more than a R _1-3The time, and each R _1-3All contain one or more R _1-4, select each R so independently _1-3, also select each R independently _1-4

Any medicine that the present invention includes compound of the present invention can be accepted form, comprises isomer (for example, diastereomer and enantiomer), salt, solvate, polymorphic etc.Especially, if compound is optically active, the present invention specifically comprises the racemic mixture of the enantiomer and the enantiomer of each compound so.Should be appreciated that no matter whether spell out (, spelling out " salt " although sometimes), term " compound " comprises any or the form of ownership in these forms.

Will be understood by those skilled in the art that for described any compound following variable in any embodiment (for example, Z, X, Y, Y ', R _A, R _B, R ₂, R _1-1, Q, R _1-3, n etc.) in each can change combination with any one or a plurality of other in any embodiment, and relevant with above-mentioned any formula.Every kind of combination of variant also is embodiment of the present invention.

For some embodiment, A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-.

For some embodiment, Q is-O-or-S-.For some embodiment, Q is-O-.

For some embodiment, Q ' is selected from key ,-C (R ₆)-,-C (R ₆)-C (R ₆)-,-S (O) ₂-and-S (O) ₂-N (R ₈)-.

For some embodiment, V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-.

For some embodiment, X is an alkylidene group, chooses wantonly to be inserted with one or more-O-group.For some embodiment, X is C _1-6Alkylidene group or-(CH ₂) _2-4-O-(CH ₂) _1-3-.For some embodiment, X is an alkylidene group.For some embodiment, X is selected from-(CH ₂) _1-6-,-CH ₂-C (CH ₃) ₂-,-(CH ₂) ₂-O-CH ₂-,-(CH ₂) ₃-O-CH ₂-and-CH ₂-C (CH ₃) ₂-CH ₂-.For some embodiment, X is selected from-CH ₂-,-(CH ₂) ₂-,-(CH ₂) ₃-,-(CH ₂) ₄-,-(CH ₂) ₅-,-(CH ₂) ₆-,-CH ₂C (CH ₃) ₂-,-CH ₂C (CH ₃) ₂CH ₂-and-(CH ₂) ₂OCH ₂-.

For some embodiment, X ' is selected from alkylidene group, alkylene group, alkynylene, arylidene, and inferior heteroaryl, wherein alkylidene group, alkylene group and alkynylene be optional to be inserted with arylidene or inferior heteroaryl or with its end-blocking with optionally be inserted with one or more-O-group.

For some embodiment, Y is-O-or-S (O) _0-2-.

For some embodiment, Y ' is selected from-S (O) _0-2-,-S (O) ₂-N (R ₈)-,-C (R ₆)-,-C (R ₆)-O-,-O-C (R ₆)-,-O-C (O)-O-,-N (R ₈)-Q '-,-C (R ₆)-N (R ₈)-,-O-C (R ₆)-N (R ₈)-,-C (R ₆)-N (OR ₉)-,

For some embodiment, Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂For some embodiment, Z is-C (O)-.For some embodiment, Z is-C (O) O-.For some embodiment, Z is-C (Q-R _1-3) ₂-.

For some embodiment, R is selected from fluorine, alkyl, alkoxyl group, haloalkyl and-N (R ₉) ₂In some of these embodiments, R ₉Be selected from hydrogen and alkyl.

For some embodiment, R _AAnd R _BEach is independently selected from: hydrogen, halogen, alkyl, alkenyl, alkoxyl group, alkyl sulfide and-N (R ₉) ₂For some embodiment, R _AAnd R _BEach is independently selected from hydrogen and alkyl.For some embodiment, R _AAnd R _BIt all is methyl.

For some selectable embodiment, R _AAnd R _BForm fused aromatic rings unsubstituted or that replaced by one or more R groups.

For some selectable embodiment, R _AAnd R _BFormation condenses 5～7 yuan of saturated rings, and it is unsubstituted or by one or more R _aGroup replaces.

For some embodiment, R _aBe selected from halogen, hydroxyl, alkyl, alkenyl, haloalkyl, alkoxyl group, alkyl sulfide and-N (R ₉) ₂

For some embodiment, R _A' and R _B' each is independently selected from: hydrogen, halogen, alkyl, alkenyl, alkoxyl group, alkyl sulfide and-N (R ₉) ₂For some embodiment, R _AAnd R _BBe independently selected from hydrogen and alkyl.For some embodiment, R _A' and R _B' all be methyl.

For some embodiment, R _1-1Be selected from hydrogen, alkyl, aryl, alkylidene group-aryl, heteroaryl, alkylidene group-heteroaryl and the alkyl that is replaced by one or more substituting groups, aryl, alkylidene group-aryl, heteroaryl, or alkylidene group-heteroaryl, described substituting group is selected from halogen, cyano group, nitro, alkoxyl group, dialkylamino, alkyl sulfide, haloalkyl, halogenated alkoxy, alkyl ,-NH-SO ₂-R _1-4,-NH-C (O)-R _1-4,-NH-C (O)-NH ₂,-NH-C (O)-NH-R _1-4And-N ₃

For some embodiment, R _1-1Be selected from aryl, alkyl and-N (CH ₃) OCH ₃For some embodiment, R _1-1Be selected from aryl, alkyl, and hydrogen.For some embodiment, R _1-1Be selected from alkyl and aryl.For some embodiment, R _1-1Be selected from methyl, ethyl, n-propyl, sec.-propyl, cyclopropyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, phenyl, 4-chloro-phenyl-and 2,4 dichloro benzene base.

For some embodiment, R _1-3Be selected from alkyl, aryl, alkylidene group-aryl, heteroaryl, alkylidene group-heteroaryl and the alkyl that is replaced by one or more substituting groups, aryl, alkylidene group-aryl, heteroaryl, or alkylidene group-heteroaryl, described substituting group is selected from halogen, cyano group, nitro, alkoxyl group, dialkylamino, alkyl sulfide, haloalkyl, halogenated alkoxy, alkyl ,-NH-SO ₂-R _1-4,-NH-C (O)-R _1-4,-NH-C (O)-NH ₂,-NH-C (O)-NH-R _1-4And-N ₃For some embodiment, R _1-3Group can be joined together to form ring system.This ring system comprises 5-, 6-, or 7-unit ring.Will be understood by those skilled in the art that the size and the composition that do not limit ring system, as long as they do not destroy the immunomodulator activity (that is, it is non-interferential) of compound.Usually, this is meant 5-, 6-, or 7-unit ring is unsubstituted, or optional one or two saturated or unsaturated 5-that all condenses into, 6-, or 7-unit ring, or by one or more aryl that are selected from, heteroaryl, halogen, haloalkyl, the substituting group of the aryl of alkylidene group-O-alkyl and replacement replaces.For some embodiment, R _1-3Be alkyl, or R _1-3Group is connected to form 5-unit ring.

For some embodiment, R _1-4Be selected from alkyl, aryl, alkylidene group-aryl, heteroaryl, alkylidene group-heteroaryl and the alkyl that is replaced by one or more substituting groups, aryl, alkylidene group-aryl, heteroaryl, or alkylidene group-heteroaryl, described substituting group is selected from halogen, cyano group, nitro, alkoxyl group, dialkylamino, alkyl sulfide, haloalkyl, halogenated alkoxy, alkyl and-N ₃

For some embodiment, R _1-6Be alkyl or R _1-6Group can be joined together to form the ring system that comprises saturated 5-or 6-unit ring.

For some embodiment, R ₂Be selected from hydrogen, alkyl, alkenyl, aryl, heteroaryl, heterocyclic radical, alkylidene group-Y-alkyl, alkylidene group-Y-alkenyl, alkylidene group-Y-aryl and the alkyl or the alkenyl that are replaced by one or more substituting groups, described substituting group is selected from hydroxyl, halogen ,-N (R ₃) ₂,-C (O)-C _1-10Alkyl ,-C (O)-O-C _1-10Alkyl ,-N (R ₃)-C (O)-C _1-10Alkyl ,-N ₃, aryl, heteroaryl, heterocyclic radical ,-C (O)-aryl and-C (O)-heteroaryl.In some of these embodiments, Y is-O-or-S (O) _0-2-; And R ₃Be selected from hydrogen, C _1-10Alkyl, and C _2-10Alkenyl.

For some embodiment, R ₂Be selected from hydrogen, alkyl, hydroxyalkyl, and alkoxyalkyl.For some embodiment, R ₂Be selected from hydrogen, alkyl, and alkoxyalkyl.For some embodiment, R ₂Be selected from hydrogen, hydroxymethyl, methyl, ethyl, n-propyl, normal-butyl, ethoxyl methyl and 2-methoxy ethyl.

For some embodiment, the embodiment of formula I-1 especially, R ₂Be selected from :-R ₄,-X '-R ₄,-X '-Y '-R ₄And-X '-R ₅

For some embodiment, R ₃Be selected from hydrogen, C _1-10Alkyl, and C _2-10Alkenyl.

For some embodiment, R ₄Be selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl inferior heteroaryl, alkyl wherein, alkenyl, alkynyl, aryl, aryl alkylene, aryloxy alkylidene group, alkyl arylene, heteroaryl, the heteroaryl alkylidene group, heteroaryloxy alkylidene group and alkyl inferior heteroaryl can be unsubstituted, perhaps can be replaced by one or more substituting group, this substituting group is independently selected from alkyl, alkoxyl group, hydroxyalkyl, haloalkyl, halogenated alkoxy, halogen, nitro, hydroxyl, sulfydryl, cyano group, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroaryl alkylene oxide group, heterocyclic radical, amino, alkylamino, dialkylamino, (dialkylamino) alkylene oxide group, and at alkyl, be oxo under alkenyl and the alkynyl situation.

For some embodiment, R ₄It is unsubstituted or the alkyl of hydroxyl or alkoxyl group replacement.

For some embodiment, R ₅Be selected from

For some embodiment, R ₆Be selected from=O and=S.

For some embodiment, R ₇Be C _2-7Alkylidene group.

For some embodiment, R ₈Be selected from hydrogen, alkyl, alkoxyl group alkylidene group, and aryl alkylene.For some embodiment, R ₈Be H or CH ₃

For some embodiment, R ₉Be selected from hydrogen and alkyl.

For some embodiment, R ₁₀Be C _3-8Alkylidene group.

For some embodiment, a and b are 1～6 integer independently, and condition is a+b≤7.

For some embodiment, n is 0～4 integer.For some embodiment, n is 0.

For some embodiment, the embodiment of formula (I-1) especially: if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃); If Z is-C (O) O-, R so _1-1Not hydrogen; If with Z be-C (O) O-, X does not comprise-the O-group so.

For some embodiment, the embodiment of formula (I-2) especially: if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃); If Z is-C (O) O-, R so _1-1Not hydrogen; If with Z be-C (O) O-, X does not comprise-the O-group so.

For some embodiment, the embodiment of formula (I-3) especially: if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃); If Z is-C (O) O-, R so _1-1Not hydrogen; If with Z be-C (O) O-, X does not comprise-the O-group so.

For some embodiment, the embodiment of formula (I-4) especially: if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃); If Z is-C (O) O-, R so _1-1Not hydrogen; If with Z be-C (O) O-, X does not comprise-the O-group so.

For some embodiment, the embodiment of formula (II) especially: if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃); If Z is-C (O) O-, R so _1-1Not hydrogen; If with Z be-C (O) O-, X does not comprise-the O-group so.

For some embodiment, Z is-C (O)-, and preferably, R _1-1Be selected from aryl, alkyl and-N (CH ₃) OCH ₃For some other embodiment, R _1-1Be selected from methyl, ethyl, n-propyl, sec.-propyl, cyclopropyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, phenyl, 4-chloro-phenyl-and 2,4 dichloro benzene base.

For some embodiment, Z is-C (O) O-, and preferably, R _1-1Be selected from alkyl and aryl.

For some embodiment, Z is-C (Q-R _1-3) ₂-, and preferably, R _1-1Be selected from alkyl, aryl, and hydrogen.For some of these embodiments, Q is-O-.

For some embodiment, Z is-C (Q-R _1-3) ₂-, and preferably, by connecting R _1-3The 5-that group forms, 6-, or 7-unit ring optional with one or two saturated or undersaturated 5-, 6-, or 7-unit ring condenses, or by one or more aryl that are selected from, heteroaryl, halogen, haloalkyl, the substituting group of alkylidene group-O-alkyl and the aryl that replaces replaces.For some of these embodiments, R _1-3Be alkyl, or R _{The 1-3 base}Group is connected to form 5-unit ring.

The preparation compound

Compound of the present invention can according to shown in path of preparing, R wherein _1-1, R _1-3, R _1-6, R ₂, R, Q, X and n are by as defined above, except R _1-1Be not-N (CH ₃) (OCH ₃).At reaction scheme 1a, 1b, 2b, in 4 and 6, R is not a hydroxyl, R _1-1Not hydrogen, and R _1-1And R ₂Do not contain those skilled in the art and think that Grignard reagent is had reactive substituting group.These substituting groups for example comprise, ketone, ester, hydroxyl, and the group of cyano group (that is nitrile) and containing-NH-.

The ketone of the present invention of formula Ia can be derived from a path of preparing two routes of alcohol intermediate from ketone groups, shown in reaction scheme 1a and 1b.Optional, ketone of the present invention can be derived from the path of preparing of ketal or acetal intermediates from ketone groups, shown in reaction scheme 2a and 2b.In another selectable embodiment, they can be derived from the path of preparing of ester intermediate from ketone groups, shown in reaction scheme 4.

The ketal of the present invention of formula XXI or acetal can wherein also have been listed the preparation of formula III compound by the path of preparing shown in the reaction scheme 2a.The ketal of the present invention of formula Id or acetal also can be by the path of preparing shown in the reaction scheme 3.

The ester of formula Ib of the present invention can begin to prepare by the compound of reaction scheme 5 from formula XXV, and the preparation of formula XXV compound is shown in reaction scheme 4.

The Weinreb acid amides of formula Ie of the present invention can be derived from the path of preparing of ester intermediate from acid amides, shown in reaction scheme 4.

Reaction scheme 1a

In the step (1) of reaction scheme 1a, in the presence of triethylamine, in suitable solvent such as methylene dichloride, with the 4-chloro-3-nitroquinoline of amino alcohol processing formula VI, wherein the amino alcohol general formula is H ₂N-X-CH ₂-OH, X is by defined herein.Formula H ₂N-X-CH ₂The multiple amino alcohol of-OH is commercial available; Other the known method of can using easily prepares.The 4-chloro-3-nitroquinoline of multiple formula VI is known, maybe can use the preparation of known synthetic method, referring to for example, and United States Patent (USP) 4,689,338; 5,175,296; 5,367,076; With 5,389,640; Yin Shu document wherein.

In the step (2) of reaction scheme 1, can make the generation compound of the reduction-type VII that ins all sorts of ways, with the quinoline-3 that formula VIII is provided, 4-diamines.Use heterogeneous hydrogenation catalyst such as platinum charcoal to react by hydrogenation.By in suitable solvent such as toluene or ethanol, in the Parr device, carrying out hydrogenation easily.Reaction can be carried out at ambient temperature, uses the ordinary method separated product.

Optional, can use single-phase or two-phase SODIUM HYDROSULPHITE sodium reduction carries out step (2).Use Park, K.K.; Oh, C.H.; And Joung, W.K.; Tetrahedron Lett., 1993,34, the described condition of 7445-7446, at ambient temperature, in the presence of salt of wormwood and ethyl purpurine dibromide, in the mixture of methylene dichloride and water, can react easily by the compound that V-Brite B is added to formula VII.Use the ordinary method separated product.

In the step (3) of reaction scheme 1a, with the quinoline-3 of carboxylic acid equivalent processing formula VIII, the 4-diamines is with 1H-imidazo [4, the 5-c] quinoline that formula IX is provided.The carboxylic acid equivalent that is fit to comprises formula R ₂C (O-alkyl) ₃Ortho ester, formula R ₂C (O-alkyl) ₂(O-C (O)-alkyl) 1,1-dialkoxy alkyl chain alkanoic acid ester and formula R ₂The acyl chlorides of C (O) Cl.According to R ₂The required substituting group decision carboxylic acid equivalent of position.For example, triethyl orthoformate can provide R ₂The compound and the original acid methyl ester that are hydrogen can provide R ₂It is the compound of butyl.By the carboxylic acid equivalent being added to the quinoline-3 of the formula VIII in being fit to solvent such as toluene or dimethylbenzene, in the 4-diamines, can react easily.Optional, can add catalysis pyridine hydrochloride or tosic acid pyridinium salt.Reaction needed is carried out under sufficiently high temperature, to remove alcohol or the water that forms in reaction.Easily, can use the Dean-Stark water trap to collect volatile matter.

Optional, can be in step (2) before with the alcohol groups on the compound of the pure protecting group protection VII that is fit to, and remove protecting group before in step (4).The protecting group that is fit to comprises t-butyldimethylsilyl, and can use ordinary method to introduce and remove.

In the step (4) of reaction scheme 1a, use ordinary method, for example, the Swern condition is with 1H-imidazo [4, the 5-c] quinoline of aldehyde-replacement of 1H-imidazo [4,5-c] the quinoline oxidation accepted way of doing sth X of alcohol-replacement of formula IX.By compound with formula IX, be that triethylamine is added in oxalyl chloride and the mixture of dimethyl sulfoxide (DMSO) in being fit to solvent such as methylene dichloride then, can carry out the Swern oxidation easily.Reaction can be carried out under as-78 ℃ being lower than envrionment temperature, uses the ordinary method separated product.

In the step (5) of reaction scheme 1a, handle 1H-imidazo [4, the 5-c] quinoline of aldehyde-replacement of formula X with Grignard reagent.Grignard reagent is formula R _1-1Mg halogenide is used to form the compound of formula XI.Several in these reagent are commercial available; Other the known synthetic method of can using prepares.In being fit to solvent such as tetrahydrofuran (THF), grignard reagent solution is added in the solution of compound of formula X, can reacts easily.Reaction can be carried out at ambient temperature, uses the ordinary method separated product.

In the step (6) of reaction scheme 1a, use the ketone of ordinary method with 1H-imidazo [4,5-c] the quinoline oxidation accepted way of doing sth XII of alcohol-replacement of formula XI.Can react easily under the described Swern condition of step (4) below.

In the step (7) of reaction scheme 1a, use can form 1H-imidazo [4, the 5-c] quinoline of ketone-replacement of the conventional oxidant oxidation-type XII of N-oxide compound, so that the N-oxide compound of formula XIII to be provided.In the solution of compound in solvent such as chloroform or methylene dichloride that at ambient temperature the 3-chloro peroxide acid is added to formula XII, can react easily.

In the step (8) of reaction scheme 1a, the N-oxide compound of ammonification formula XIII is with 1H-imidazo [4, the 5-c] quinoline-4-amine of ketone-replacement that formula Ia is provided.Step (8) comprises by changing into ester, the N-oxide compound that ester and ammoniation agent is reacted activate formula XIII.The activator that is fit to comprises alkyl-or aryl sulfonyl chloride such as benzene sulfonyl chloride, methane sulfonyl chloride, or Tosyl chloride.The ammoniation agent that is fit to comprises ammoniacal liquor (for example ammonium hydroxide form) and ammonium salt (for example, volatile salt, bicarbonate of ammonia, ammonium phosphate).In the solution of N-oxide compound in being fit to solvent such as methylene dichloride or chloroform that ammonium hydroxide is added to formula XIII, add Tosyl chloride then, can react easily.Reaction can be carried out at ambient temperature.Can use ordinary method from reaction mixture, to separate 1H-imidazo [4, the 5-c] quinoline-4-amine or the acceptable salt of its medicine of ketone-replacement of the formula Ia that generates.

Reaction scheme 1a

Reaction scheme 1b

In reaction scheme 1b, react extremely similar, but order is different to reaction scheme 1a.In the step (1) of reaction scheme 1b,, handle the 4-chloro-3-nitroquinoline of formula VI with amino alcohol by the step (1) of reaction scheme 1a.In step (2), by the step (4) of reaction scheme 1a, use the formula VII compound of ordinary method oxidation generation, form the aldehyde of formula XIV.In step (3), by the step (5) of reaction scheme 1, handle the aldehyde of the formula XIV that generates with Grignard reagent, form the compound of formula XV.In step (4), by the step (6) of reaction scheme la, the compound of the compound formation formula XVI of oxidation-type XV.In step (5), by the step (2) of reaction scheme 1a, the quinoline-3 of ketone-replacement of the compound formation formula XVII of reduction-type XVI, 4-diamines.In step (6), by the step (3) of reaction scheme 1a, use for example quinoline-3 of ortho ester cyclisation formula XVII, the 4-diamines forms 1H-imidazo [4, the 5-c] quinoline of ketone-replacement of formula XII.In step (7),, become the H-oxide compound to form the compound of formula XIII the compound oxidation of formula XII by the step (7) of reaction scheme 1a.In step (8), by the step (8) of reaction scheme 1a, the N-oxide compound of ammonification formula XIII, with 1H-imidazo [4, the 5-c] quinoline-4-amine of ketone-replacement that formula Ia is provided.

Reaction scheme 1b

Reaction scheme 2a

The ketone of the present invention of formula Ia and the ketal of the present invention of formula XXI and acetal can prepare according to reaction scheme 2a.In the step (1) of reaction scheme 2a, in the presence of the triethylamine in suitable solvent such as chloroform or methylene dichloride, 4-chloro-3-nitroquinoline and the formula H of formula VI ₂N-X-C (R _1-1) (O-R _1-6) ₂Compound reaction, as the amino ketal of this formula, wherein R _1-1Be methyl, R _1-6It is ethylidene.Formula H ₂N-X-C (R _1-1) (O)-R _1-6) ₂Compound can obtain from commercial, or use ordinary method easily synthetic.For example, referring to people such as C.J.Stewart, J.Liebigs Ann.der Chem., 1978, the open WO 01/51486 of 57-65 and PCT.

Formula H ₂NCH ₂C (CH ₃) ₂CH ₂C (O-R _1-6) ₂CH ₃Ketal can prepare according to reference method, by making the reaction of Nitromethane 99Min. and mesityl oxide, the ketone that generates is changed into ketal, and nitroreduction is become amine.

In the step (2) of reaction scheme 2a, the formula XVIII compound that the reduction that ins all sorts of ways is generated is with the ketal that forms formula III-or the quinoline-3 of acetal-replacement, 4-diamines.Can be by described reduction of reaction scheme 1a step (2).

In the step (3) of reaction scheme 2a, handle the quinoline-3 of formula III with the carboxylic acid equivalent, the 4-diamines is with the ketal that forms formula XIX-or 1H-imidazo [4, the 5-c] quinoline of acetal-replacement.Reaction can be undertaken by reaction scheme 1a step (3) is described.

In the step (4) of reaction scheme 2a, can use the described method of reaction scheme 1a step (7) 1H-imidazo [4, the 5-c] quinoline of formula XIX to be transformed the N-oxide compound of accepted way of doing sth XX.In step (5), by the compound (for example, ketal) (subclass of formula Id compound) of reaction scheme 1a step (8) with the N-oxide compound ammonification accepted way of doing sth XXI of formula XX.Use ordinary method separated product or the acceptable salt of its medicine.

In step (6), can the compound of formula XXI be transformed the ketone of accepted way of doing sth Ia by acid catalyzed hydrolysis.By the strong acid example hydrochloric acid being added in the ketal of formula XXI, can react easily.Reaction can be carried out in suitable solvent such as water at ambient temperature.Use ordinary method separated product or the acceptable salt of its medicine.

Reaction scheme 2a

Reaction scheme 2b

The compound of formula Ia also can prepare according to reaction scheme 2b.In the step (1) of reaction scheme 2b, (it is the subclass of formula XIX, wherein R to the acetal of formula XIX-b _1-1Be hydrogen) acid catalyzed hydrolysis takes place, so that the aldehyde of formula X to be provided.Reaction can be undertaken by reaction scheme 2a step (6).

In the step (2) of reaction scheme 2b, the aldehyde of formula X and formula R _1-1The halid Grignard reagent reaction of Mg.Reaction can be undertaken by reaction scheme 1a step (5), so that the alcohol of formula XI to be provided.

In step (3)～(5) of reaction scheme 2b, use 1H-imidazo [4, the 5c] quinoline of ordinary method with ketone-replacement of the pure oxidation accepted way of doing sth XII of formula XI, transform the N-oxide compound of accepted way of doing sth XIII again.The compound of the XIII of ammonification formula then is with 1H-imidazo [4, the 5-c] quinoline-4-amine of ketone-replacement that formula Ia is provided.The step of reaction scheme 2b (3), (4) and (5) can be by the step (6) of reaction scheme 1a, and carry out (7) and (8).

Reaction scheme 2b

Reaction scheme 3

Ketal of the present invention and acetal can be according to reaction scheme 3 preparations.The step of reaction scheme 3 (1) comprises ketone or aldehyde and the formula H-Q-R that makes formula XII _1-3Or H-Q-R _1-3The compound reaction of-Q-H transforms ketal or the acetal of accepted way of doing sth XIX.By in the presence of acid catalyst, use formula H-Q-R _1-3The compound of-Q-H or two equivalent formula H-Q-R _1-3Ketone or the aldehyde of compound treatment formula XII, can react.The condition of this reaction is known for those skilled in the art.Referring to, for example, Greene, T.W.; Wuts, P.G.M.Protective Groups in OrganicSynthesis; John Wiley ﹠amp; Sons, Inc.:New York, 2 ^NdEd, 199l, p.178.

In the step (2) of reaction scheme 3, with 1H-imidazo [4,5-c] quinoline-5N-oxide compound of the compound oxidation accepted way of doing sth XXIII of formula XXII, the 1H-imidazo of the Id of an ammonification accepted way of doing sth then [4,5-c] quinoline-4-amine.The step of reaction scheme 3 (2) and (3) can be undertaken by step (7) and (8) of reaction scheme 1a.Use ordinary method separated product or the acceptable salt of its medicine.

Optional, can be by the ketal of the described reaction of reaction scheme 3 steps (1) with the ketone conversion accepted way of doing sth Id of formula Ia.

Reaction scheme 3

Reaction scheme 4

The compound of formula Ia and formula Ie can be according to reaction scheme 4 preparations.In the step (1) of reaction scheme 4,4-chloro-3-nitroquinoline and the formula H of formula VI ₂N-X-C (O) (O-R _1-1The compound of)-HCl reacts, and forms the compound of formula XXIV.In the presence of the triethylamine in suitable solvent such as methylene dichloride, can react easily.Formula H ₂N-X-C (O) (O-R _1-1The compound of)-HCl can obtain from commerce, or uses ordinary method easily synthetic.For example, R wherein _1-1Be that ethyl and X are that the amino ester of propylidene or inferior dodecyl can be synthetic according to following process: people such as C.Temple, J.Med.Chem., 1988,31,697-700.

In the step (2) and (3) of reaction scheme 4, with the quinoline-3 of the compound of formula XXIV reduction formation formula IV, the 4-diamines with the cyclisation of carboxylic acid equivalent, forms 1H-imidazo [4, the 5-c] quinoline of formula XXV.The step of reaction scheme 4 (2) and (3) can be undertaken by step (2) and (3) of reaction scheme 1a.

In step (4), the ester group of 1H-imidazo [4, the 5-c] quinoline of formula XXV is changed into the Weinreb acid amides, with 1H-imidazo [4, the 5-c] quinoline that XXVI is provided.Conversion is performed as follows: form carboxylic acid by the alkali catalyzed hydrolysis ester, use ordinary method to change into acyl chlorides and use N, the O-dimethyl hydroxylamine hydrochloride is handled the Weinreb acid amides that acyl chlorides forms formula XXVI.In 1H-imidazo [4, the 5-c] quinoline that sodium hydroxide is added to the ester-replacement that is fit to the formula XXV in solvent such as the ethanol, can carry out the hydrolysis of base catalysis easily.Reaction can be carried out at ambient temperature, uses the ordinary method separated product.Can carry out the conversion of carboxylic acid easily by oxalyl chloride being added in the solution of carboxylic acid in being fit to solvent such as methylene dichloride to acyl chlorides.Reaction can be carried out carrying out under as 0 ℃ being lower than envrionment temperature.In suitable solvent such as methylene dichloride, use N then, O-dimethyl hydroxylamine hydrochloride, the acyl chlorides that generates with the triethylamine processing then.Reaction can be carried out at ambient temperature, uses the product of ordinary method separate type XXVI.

Optional, to use from trimethyl aluminium and N, the aurin tricarboxylic acid that the O-dimethyl hydroxylamine hydrochloride makes is handled 1H-imidazo [4, the 5-c] quinoline of ester-replacement of formula XXV, can carry out step (4) in a step.By 1H-imidazo [4 with ester-replacement of formula XXV, 5-c] solution of quinoline in being fit to solvent such as methylene dichloride is added to trimethyl aluminium and N, in the pre-reaction mixture of O-dimethyl hydroxylamine hydrochloride in being fit to solvent such as methylene dichloride, can react easily.Reaction heating at high temperature then, for example, the reflux temperature of solvent.Use the ordinary method separated product.

In the step (5) and (6) of reaction scheme 4,1H-imidazo [4, the 5-c] quinoline of formula XXVI is transformed the N-oxide compound of accepted way of doing sth XXVII, ammonification is with 1H-imidazo [4,5-c] quinoline-4-amine that formula Ie is provided.The step of reaction scheme 4 (5) and (6) can be undertaken by step (7) and (8) of reaction scheme 1a.Use ordinary method separated product or the acceptable salt of its medicine.

Can use reaction scheme 4 steps (7), the optional route shown in (8) and (9) obtains the compound of formula Ia.In step (7), use formula R _1-1The halid Grignard reagent of Mg is handled the Weinreb acid amides of formula XXVI, forms the ketone of formula XII.Grignard reaction can be undertaken by reaction scheme 1a step (5).In step (8), press the N-oxide compound of the step (7) of reaction scheme 1a with 1H-imidazo [4,5-c] the quinoline oxidation accepted way of doing sth XIII of ketone-replacement of formula XII.In step (9), by the H-oxide compound of reaction scheme 1a step (8) ammonification formula XIII, with 1H-imidazo [4, the 5-c] quinoline-4-amine of ketone-replacement that formula Ia is provided.

Reaction scheme 4

Reaction scheme 5

In reaction scheme 5, will transform the compound of accepted way of doing sth Ib by 1H-imidazo [4, the 5-c] quinoline of the formula XXV of reaction scheme 5 steps (1)～(3) preparations.In step (1), by the step (7) of reaction scheme 1a 1H-imidazo [4, the 5-c] quinoline of formula XXV is oxidized to the N-oxide compound, form the compound of formula XXVIII.In step (2), by the N-oxide compound of reaction scheme 1a step (8) ammonification formula XXVIII, with 1H-imidazo [4, the 5-c] quinoline-4-amine of ester-replacement that formula Ib is provided.Use ordinary method separated product or the acceptable salt of its medicine.

Reaction scheme 5

Reaction scheme 6

The ketone of formula I-3b can be according to reaction scheme 6 preparation, wherein R _1-1, R ₂, R _A', R _B' and X by as defined above, Ph is a phenyl.In the step (1) of reaction scheme 6,2 of formula XXX, 4-two chloro-3-nitropyridines and formula H ₂The amino ester of N-X-C (O)-O-alkyl or the reaction of its hydrochloride are to form the 2-chloro-3-nitropyridine of formula XXXI.In the presence of alkali such as triethylamine, at inert solvent such as N, in the dinethylformamide (DMF), by with formula H ₂2 of the amino ester of N-X-C (O)-O-alkyl-HCl and formula XXX, 4-two chloro-3-nitropyridines mix, and can react easily.Reaction can be carried out at ambient temperature, uses ordinary method separated product from reaction mixture.2 of multiple formula XXX, 4-two chloro-3-nitropyridines are known, and can use known synthetic method easily to prepare.(referring to, for example, people such as Dellaria, United States Patent (USP) 6,525,064 and wherein the citation document).

In the step (2) of reaction scheme 6, the 2-chloro-3-nitropyridine of formula XXXI and an alkali metal azide reaction are to provide 8-nitro tetrazolo [1,5-a] pyridine-7-amine of formula XXXII.In being fit to solvent as acetonitrile/water in, preferred 90/10 acetonitrile/water, in the presence of Cerium II Chloride III, preferred Cerium II Chloride III heptahydrate, the compound by making formula XXXI and an alkali metal azide for example sodiumazide mix, and react.Optional, by heating, for example, under reflux temperature, react.Optional, the compound by making formula XXXI and an alkali metal azide for example sodiumazide mix in suitable solvent such as DMF, and are heated to for example about 50-60 ℃, react, and choose wantonly in the presence of ammonium chloride.Use ordinary method separated product from reaction mixture.

In the step (3) of reaction scheme 6,8-nitro tetrazolo [1,5-a] pyridine-7-amine of reduction-type XXXVI is with tetrazolo [1, the 5-a] pyridine-7 that formula XXXIII is provided, 8-diamines.Use conventional heterogeneous hydrogenation catalyst such as palladium charcoal or platinum charcoal to reduce by hydrogenation.By in suitable solvent such as acetonitrile or ethyl acetate, on the Parr device, reacting easily.Can use ordinary method separated product from reaction mixture.Optional, can be by the described use of reaction scheme 1a step (2) single-phase or two-phase SODIUM HYDROSULPHITE sodium reduction reduce.

In the step (4) of reaction scheme 6, the tetrazolo of formula XXXIII [1,5-a] pyridine-7,8-diamines and the reaction of carboxylic acid equivalent are with 7H-imidazo [4,5-c] tetrazolo [1, the 5-a] pyridine that formula XXXIV is provided.Reaction can be undertaken by the step (3) of reaction scheme 1a, can use ordinary method separated product from reaction mixture.

In the step (5) of reaction scheme 6, the ester group of the 7H-imidazo of formula XXXIV [4,5-c] tetrazolo [1,5-a] pyridine changes into the Weinreb acid amides, with 7H-imidazo [4,5-c] tetrazolo [1, the 5-a] pyridine that formula XXXV is provided.Can transform by reaction scheme 4 steps (4), can use ordinary method separated product from reaction mixture.

In the step (6) of reaction scheme 6, use formula R _1-1The halid Grignard reagent of Mg is handled the Weinreb acid amides of formula XXXV, forms the ketone of formula XXXVI.Can carry out grignard reaction by the step (5) of reaction scheme 1a, can use ordinary method separated product from reaction mixture.

In the step (7) of reaction scheme 6, the 7H-imidazo [4 of formula XXXVI, 5-c] tetrazolo [1,5-α] the N-triphenylphosphinyl intermediate of pyridine and triphenylphosphine reaction formation formula XXXVII, can be in suitable solvent such as toluene or 1, in the 2-dichlorobenzene, under nitrogen, for example under reflux temperature, heat, carry out reaction with triphenylphosphine.Can use ordinary method separated product from reaction mixture.

In the step (8) of reaction scheme 6, the N-triphenylphosphinyl intermediate of hydrolyzing type XXXVII, IH-imidazo [4, the 5-c] pyridine-4-amine that replaces with the ketone that formula I-3b is provided.Can use the known common method of those skilled in the art to be hydrolyzed, for example, can in low-grade alkane alcohol, heat and carry out by in the presence of acid.Use ordinary method separated product from reaction mixture, obtain compound or the acceptable salt of its medicine of formula I-3b.

The ester of formula I-3 (Z is-C (O) O-) can be by omitting step (5) and (6) preparation.

The Weinreb acid amides of formula I-3 (Z is-C (O)-and R _1-1Be-N (CH ₃) (OCH ₃)) can use of the ester preparation of the method for step (5) from formula I-3.

Reaction scheme 6

Reaction scheme 7

The ketone of formula I-4b can prepare according to reaction scheme 7, wherein R _bBe alkyl, alkoxyl group, or-N (R ₉) ₂, R _2b, R _1-1bAnd X _bBe R defined above ₂, R _1-1With the subclass of X, do not comprise that those skilled in the art think under the acid hydrogenation conditions of described reaction, to be easy to those substituting groups of reductive.These easy reductive groups comprise for example alkenyl, alkynyl and aryl and the group that has nitro substituent.

In the step (1) of reaction scheme 7, the 1H-imidazo of formula XIb [4,5-c] quinoline transforms 1H-imidazo [4,5-c] quinoline-4-amine of accepted way of doing sth XXXVIIIb.Can transform by step (7) and (8) of reaction scheme 1a, can use ordinary method separated product from reaction mixture.

In the step (2) of reaction scheme 7, the 1H-imidazo of formula XXXVIIIb [4,5-c] quinoline-4-amine is reduced 6,7,8 of accepted way of doing sth XXXIXb, 9-tetrahydrochysene-1H-imidazo [4,5-c] quinoline-4-amine.By under the heterogeneous hydrogenation condition, platinum (IV) oxide compound is added to formula XXXVIIIb compound in the solution of trifluoroacetic acid, and reaction is under the hydrogen pressure, can react easily.Can on the Parr device, react at ambient temperature.Can use ordinary method separated product from reaction mixture.

In the step (3) of reaction scheme 7,6,7,8 of alcohol-replacement of formula XXXIXb, 6,7,8 of ketone-replacement of 9-tetrahydrochysene-1H-imidazo [4,5-c] quinoline-oxidized accepted way of doing sth I-4b of 4-amine, 9-tetrahydrochysene-1H-imidazo [4,5-c] quinoline-4-amine.Can carry out oxidation by reaction scheme 1a step (4).Use ordinary method separated product or the acceptable salt of its medicine.

Reaction scheme 7

Also can use the variant of synthetic route shown in the reaction scheme 1～7 to prepare compound of the present invention, this is obvious for those skilled in the art.For example, the method that can use reaction scheme (3) step (1) changes into ketal with the ketone of formula Ia, I-3b and I-4b.Also can use the synthetic route shown in the following embodiment to prepare compound of the present invention.

Pharmaceutical composition and biological activity

Pharmaceutical composition of the present invention contains above-claimed cpd of the present invention or the salt and the medicine acceptable carrier for the treatment of significant quantity.

Term " treatment significant quantity " and " significant quantity " are meant that the amount of compound or salt is enough to cause treatment or preventive effect, as cytokine induction, and immunomodulatory, anti-tumor activity, and/or antiviral property activity.Although being used for the active compound of pharmaceutical composition of the present invention or the accurate amount of salt can change according to the known factor of those skilled in the art, physics and chemical property as compound or salt, the performance of carrier and dosage regimen, but what can expect is, composition of the present invention should contain the activeconstituents of capacity, with with about 100 nanogram/kilograms (ng/kg)～about 50 mg/kg (mg/kg), compound or the salt of preferred about 10 microgram/kilograms (μ m/kg)～about 5mg/kg offer the patient.Can use various dosage forms, as tablet, cough drop, capsule, parenteral administration, syrup, creme, ointment, spray, skin patch, film subsides etc.

In treatment plan, compound of the present invention or salt can be by the administrations of single therapy medicine, compound perhaps of the present invention or salt can with another kind of compound or with other active drug administrations, comprise other immune response modifier, antiviral property, microbiotic, antibody, albumen, peptide, oligonucleotide etc.

In the experiment of carrying out according to following test, compound of the present invention or salt show the preparation that can induce some cytokine.These results show that compound or salt can be used as immune response modifier, can regulate immune response in many ways, thereby make them can be used for treating various illnesss.

Can generally include interferon-' alpha ' (IFN-α) and/or tumor necrosis factor-alpha (TNF-α) and some interleukin (IL) by giving the cytokine that compound of the present invention or salt induces its preparation.Can induce its biosynthetic cytokine to comprise IFN-α by compound of the present invention or salt, TNF-α, IL-1, IL-6, IL-10 and IL-12 and various other cytokines.At other on, the cytokine of these and other can suppress virus and produce and growth of tumour cell, thereby makes compound or salt can be used for treating virus disease and neoplastic disease.Therefore, the invention provides the biosynthetic method of cytokine in the induced animal, comprise the The compounds of this invention of significant quantity or salt or composition are given to animal.Give compound or salt or composition and may suffer from following disease with the biosynthetic animal of the inducing cell factor, for example virus disease or neoplastic disease give described compound or salt therapeutic treatment can be provided.Optional, can before animal suffers from described disease, described compound or salt be given to animal, thereby prophylactic treatment can be provided for clothes compound or salt.

Compound of the present invention or salt also can influence other aspects of innate immunity reaction except the ability of preparation with inducing cell factor.For example, because the effect of cytokine induction can stimulate natural killer cell activity.Compound or salt also can activated macrophages, stimulate the secretion of oxynitride then and prepare extra cytokine.In addition, compound or salt can cause lymphocytic propagation of B-and differentiation.

The posteriori immune response of compound of the present invention or salt pair is also influential.For example, but through giving compound or salt indirect induction T auxiliary type 1 (T _H1) preparation of cytokine IFN-γ, and suppress T auxiliary type 2 (T _H2) cytokine IL-4, the preparation of IL-5 and IL-13.

No matter be that compound or salt or composition can give separately, or give with one or more activeconstituentss for the prevention of disease or therapeutic treatment with for influence for the congenital or acquired immunity, for example, vaccine adjuvant.When giving with other compositions, compound or salt and other compositions or composition can give separately; Give together, but respectively in solution for example; Or give together, and be connected to each other, covalently bound or (b) the non-covalent connection as (a), for example, in soliquid.

The condition of described herein compound or salt can be used for treatment, includes but not limited to:

(a) virus disease, for example, the disease of suffering from because of following viral communication: adenovirus, simplexvirus (for example, HSV-I, HSV-II, CMV, or VZV), poxvirus is (for example, vaccinia subgroup virus, as smallpox or cowpox, or molluscum contagiosum), picornavirus (for example, rhinovirus or enterovirus), orthomyxovirus is (for example, influenza virus), paramyxovirus (for example, parainfluenza virus, parotitis, Measles virus and respiratory syncytial virus (RSV)), coronavirus is (for example, SARS), papovavirus (for example, mastoid process tumor virus, as cause Genital warts, common wart, or those of plantar wart), hepadnavirus (for example, hepatitis B virus), flavivirus (for example, hepatitis C virus or dengue fever virus), or retrovirus (for example, slow virus such as HIV);

(b) bacteriosis, for example, the disease of suffering from because of following bacterial infection, for example, Escherichia (Escherichia), enterobacteria (Enterobacter), sramanaization bacterium (Salmonella), staphylococcus (Staphylococcus), Shigellae (Shigella), listeria spp (Listeria), gas bacillus (Aerobacter), breathe out bit bacterium (Helicobacter), Klebsiella (Klebsiella), Bacillus proteus (Proteus), pseudomonas (Pseudomonas), suis (Streptococcus), chlamydozoan (Chlamydia), mycoplasma (Mycoplasma), streptococcus pneumoniae (Pneumococcus), Neisser bacterium (Neisseria), clostridium (Clostridium), bacillus (Bacillus), coryneform bacteria (Corynebacterium), mycobacterium (Mycobacterium), Campylobacter (Campylobacter), vibrios (Vibrio), Serratia (Serratia), Providence (Providencia), pigment bacterium (Chromobacterium), brucella (Brucella), Yersinia (Yersinia), influenzae (Haemophilus), or Bo Erdeshi bacillus (Bordetella);

(c) other communicable diseases, as the chlamydozoan disease, fungal disease (includes but not limited to moniliosis, aspergillosis, histoplasmosis, crypotococcal), or management of parasitic diseases (includes but not limited to malaria, pneumocystis carinii pneumonia, leishmaniasis, cryptosporidiosis, toxoplasmosis and trypanosome are infected);

(d) neoplastic disease, as above skin and flesh tumorigenesis, cervical cell pathology, actinic keratosis, rodent cancer, squamous cell carcinoma, renal cell carcinoma, Kaposi sarcoma, melanoma, leukemia (includes but not limited to myelomatosis, chronic lymphocytic leukemia, multiple myeloma, non_hodgkin lymphoma, cutaneous T cell lymphoma, B cell lymphoma and hairy cell leukemia and other cancers);

(e) T _HThe disease of 2-mediation, the heredity anaphylactic disease, as atopic dermatitis or eczema, eosinophilia, asthma, transformation reactions, allergic rhinitis and Ommen syndromes;

(f) some autoimmune disorders, as the whole body lupus erythematosus, primary thrombocyte hyperplasia disease, multiple sclerosis, discoid lupus erythematosus, alopecia areata; With

(g) restore relevant disease with wound, as the inhibition (for example, strengthening wound healing (comprising chronic trauma)) of keloid formation and its alloytype scar.

In addition, compound of the present invention or salt can be with causing body fluid and/or cell-mediated immunoreactive any material as vaccine adjuvant, for example, and challenge virus, bacterium, or parasitics immunogen; Nonactive viral, come from tumour, protozoic, come from organic, fungoid, or bacillary immunogen, toxoid, toxin; From antigen; Polysaccharide; Albumen; Glucoprotein; Peptide; Cell vaccine; Dna vaccination; From body homology type vaccine; Recombinant protein etc.; As the adjuvant of following disease, for example, BCG, cholera, pestilence, typhoid fever, hepatitis A, hepatitis B, hepatitis C, influenza A, influenza B, parainfluenza, poliomyelitis, rabies, measles, parotitis, rubella, yellow jack, tetanus, diphtheria, b type haemophilus influenza infects, pulmonary tuberculosis, meningococcus property disease and pneumovax, adenovirus, HIV, varicella, cytomegalovirus, singapore hemorrhagic fever, the cat leukemia, fowl plague, HSV-1 and HSV-2, swine fever, Japanese encephalitis, respiratory syncytial virus, rotavirus, papillomavirus, yellow jack and Alzheimer disease.

Compound of the present invention or salt accommodate the individuality in immune function depression especially.For example, the opportunistic that compound or salt can be used for treating after cell-mediated immunity is suppressed infects and tumour, for example the transplant patient, among cancer patient and the HIV patient.

Therefore, one or more above-mentioned diseases or go up the class disease, for example virus disease or neoplastic disease, The compounds of this invention or salt that can be by will treat significant quantity or give and obey the animal (suffering from this disease) for the treatment of needs to animal.

Biosynthetic compound of the inducing cell factor or salt amount are meant effectively is enough to cause that one or more cell types are (as monocyte, scavenger cell, dendritic cell and B-cell) (for example produce a certain amount of one or more cytokines, IFN-α, TNF-α, IL-1, IL-6, IL-10 and IL-12) amount, the cytokine of generation is with respect to background level raise (by inducing).Accurately measure according to factors vary as known in the art, but the about 100ng/kg of projected dose～about 50mg/kg, preferred about 10 μ g/kg～about 5mg/kg.The present invention also provides in the treatment animal method of neoplastic disease in the viral infectious method and treatment animal, comprises the The compounds of this invention of significant quantity or salt or composition are obeyed to animal.Treat effectively or suppress viral infectious amount and be meant the amount of comparing one or more reductions in viral infection (as viral infringement), virus quantity, virus production speed and the mortality ratio with not subject control animal.The accurate amount of effective treatment is according to factors vary as known in the art, but the about 100ng/kg of projected dose～about 50mg/kg, preferred about 10 μ g/kg～about 5mg/kg.The compound or the salt amount for the treatment of neoplastic disease effectively are meant the amount that causes that tumour size or tumour focal length (tumor foci) size reduce.Equally, accurately measure according to factors vary as known in the art, but the about 100ng/kg of projected dose～about 50mg/kg, preferred about 10 μ g/kg～about 5mg/kg.

Embodiment

Objects and advantages of the present invention are further illustrated by following embodiment, but described in these embodiments certain material and consumption thereof, other conditions and details should not be interpreted as limiting inadequately the present invention.

Embodiment 1

4-(4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone

Step 1:

To 4-chloro-3-nitroquinoline (100.0g, 479mmol) and triethylamine (72.8g, 719mmol) drip in the stirring the mixture in methylene dichloride (700mL) 4-amino-1-butanols (42.7g, 479mmol).After adding, water (500mL) is added to makes product precipitation in the reaction mixture.Add more water (2L), mixture stirs and spends the night, and filters.Use dried over sodium sulfate organic solution, concentrating under reduced pressure is with the product merging of filtering separation, to provide 4-(3-nitroquinoline-4-base is amino) fourth-1-alcohol (113g), the glassy yellow solid.

Step 2:

To 4-(3-nitroquinoline-4-base amino) fourth-1-alcohol (70.0g, 268mmol) and triethylamine (54.2g, 536mmol) add in the stirred solution in chloroform (900mL) tert-butyldimethylsilyl chloride (TBDMSCl, 60.6g, 402mmol).3.5 after hour, add again triethylamine (19.0g, 188mmol) and TBDMSCl (20.2g, 134mmol), mixture stirs and to spend the night.Add again TBDMSCl (4.0g, 27mmol) after, thin-layer chromatography (TLC) judges that reaction finishes.Add chloroform (900mL), mixture is used the 0.10N hydrochloric acid soln in succession, saturated sodium bicarbonate aqueous solution and salt water washing, every kind of 360mL; Use dried over sodium sulfate; Filter; Evaporating solvent obtains the mixture (117g, about 65:35mol:mol) altogether of [4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl] (3-nitro-quinolyl-4) amine and tertiary butyl dimethyl-silicon alkanol, is not further purified when next step uses.

Step 3:

[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl] (3-nitro-quinolyl-4) amine of above-mentioned steps and the mixture of tertiary butyl dimethyl-silicon alkanol (110g) are dissolved in the toluene (880mL), and place the Parr hydrogenation vessel together with 5% platinum carbon catalyst (3.0g).Container is forced into 50psi (3.4 * 10 ⁵Pa) hydrogen shook on the Parr device 1.5 hours, and adding extra hydrogen once in a while is 50psi (3.4 * 10 to keep-up pressure ⁵Pa).After 3 hours, reaction mixture filters and concentrating under reduced pressure with the CELITE filtering medium, so that N to be provided ⁴-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl] quinoline-3, the 4-diamines, dark oil is not further purified and is directly used in next step.

Step 4:

With N ⁴-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl] quinoline-3,4-diamines (62.9g, 182mmol) and original acid methyl ester (45.2g, 278mmol) vlil in toluene (200mL) is 2 hours, concentrating under reduced pressure is to provide 2-butyl-1-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl]-1H-imidazo [4,5-c] quinoline, oil is not further purified and is directly used in next step.

Step 5:

2-butyl-1-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl with abovementioned steps]-1H-imidazo [4,5-c] quinoline and tetrabutyl ammonium fluoride (142mL, 1M solution in the tetrahydrofuran (THF)) be dissolved in tetrahydrofuran (THF) (THF) (400mL), stirred 1 hour, concentrating under reduced pressure is to provide 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) fourth-1-alcohol (20.0g), behind the silica gel chromatography (with 10% methanol-eluted fractions in the methylene dichloride), obtain the light brown solid.

Step 6:

(101mmol) solution in methylene dichloride (130mL) cools off in dry ice/acetone batch for DMSO, 7.88g, and stirs with dimethyl sulfoxide (DMSO).(9.40g 74mmol), drips 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) fourth-1-alcohol (20.0g, 67.3mmol) solution in methylene dichloride (320mL) then to drip oxalyl chloride.After 5 minutes, (20.42g, 202mmol), mixture rises to room temperature to add triethylamine.After adding chloroform (500mL), mixture is used saturated ammonium chloride solution (200mL) and saturated sodium bicarbonate aqueous solution (200mL) washing in succession, uses dried over sodium sulfate, filters, and is condensed into dark solid.Solid forms slurry in ether, up to obtaining thin solid.Filtration product, drying is to provide 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) butyraldehyde (17.9g), the light brown solid.

Step 7:

(8.0g 27.1mmol) drips the solution of phenyl-magnesium-bromide (27.08mL, 1M solution is among the THF) in the stirred solution in anhydrous THF (270mL) to 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) butyraldehyde.After 30 minutes, solution with ethyl acetate dilution (300mL), separates each layer with saturated ammonium chloride (100mL) quencher.Organic solution is used saturated sodium bicarbonate aqueous solution (100mL) and salt solution (100mL) washing in succession, uses dried over sodium sulfate, filters, and is condensed into light orange oil.Silica gel chromatography (with 5% methanol-eluted fractions in the methylene dichloride) provides 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-alcohol (4.3g), light orange, viscous solid.

Step 8:

(1.35g, 17.3mmol) solution in methylene dichloride (22mL) cools off in dry ice/acetone batch, and stirs with DMSO.(1.61g 12.7mmol), drips 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-alcohol (4.3g, 11.5mmol) solution in methylene dichloride (55mL) then to drip oxalyl chloride.After 5 minutes, (3.49g, 34.5mmol), mixture rises to room temperature to add triethylamine.After adding chloroform (300mL), mixture is used saturated ammonium chloride solution (100mL) and saturated sodium bicarbonate aqueous solution (100mL) washing in succession, use dried over sodium sulfate, filter, with concentrated, so that 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone (4.15g), white solid to be provided.

Step 9:

In several minutes, in batches to 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone (4.15g, 11.2mmol) add 3-chloro peroxide acid (m-CPBA in the stirred solution in chloroform (56mL), about 77% is pure, 2.75g, 12.3mmol).After 1 hour, TLC judgement reaction is not finished, so add m-CPBA (1.0g) again.Stir after 30 minutes, mixture dilutes (200mL) with chloroform, use saturated sodium bicarbonate aqueous solution (2 * 100mL) and salt solution (100mL) washing in succession, use dried over sodium sulfate, filter, concentrate, so that 4-to be provided (2-butyl-5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone, dark oil is not further purified and is directly used in next step.

Step 10:

In several minutes, the 4-of the abovementioned steps in methylene dichloride (49mL) (2-butyl-5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl)-add in the vigorous stirring mixture of 1-phenyl fourth-1-ketone and ammonium hydroxide (16mL) Tosyl chloride (2.34g, 12.3mmol).After 15 minutes, with chloroform (200mL) and saturated sodium bicarbonate aqueous solution (100mL) diluted reaction mixture.Separate each layer, organic phase is washed with saturated sodium bicarbonate aqueous solution (100mL).With chloroform (50mL) strip aqueous.Merge organism, use dried over sodium sulfate, filter, be condensed into the deep yellow solid.The deep yellow solid forms slurry in ether, filter, and forms tenderly white look solid.Solid N, dinethylformamide (DMF) and water recrystallization are to provide 4-(4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone, white cotton-shaped solid, mp 178-180 ℃.

MS(APCI)m/z 387(M+H) ⁺；

Analyze: calculated value: C ₂₄H ₂₆N ₄O:C, 74.58; H, 6.78; N, 14.50.Observed value: C, 74.45; H, 6.77; N, 14.47.

Embodiment 2

5-(4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone

By the preparation embodiment 1 described step 1-6 that carries out.

Step 7:

Utilize the general method described in embodiment 1 step 7 to make 4-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) butyraldehyde (8.5g, 28.8mmol) and methyl-magnesium-bromide (20.6mL, 1.4M solution among toluene/THF, 28.8mmol), so that 5-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) to be provided penta-2-alcohol (3.54g), behind the silica gel chromatography (with 5% methanol-eluted fractions in the methylene dichloride), get white solid.

Step 8:

Utilize the general method described in embodiment 1 step 8, with DMSO (1.33g, 17.1mmol), oxalyl chloride (1.59g, 12.5mmol), and triethylamine (3.45g, 34.1mmol) oxidation 5-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-alcohol (3.54g, 11.4mmol), to provide 5-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone (2.15g), dark solid.

Step 9 and 10:

Use the general method described in embodiment 1 step 9 and 10, by with m-CPBA (1.71g, 7.64mmol) reaction, ammonification 5-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone (2.15g, 6.95mmol), so that 5-to be provided (2-butyl-5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone, then with Tosyl chloride (1.46g, 7.64mmol) and solution of ammonium hydroxide (10mL) reaction, so that 5-to be provided (4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone, white solid, mp 173-176 ℃.

MS(APCI)m/z 325(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₄N ₄O:C, 70.34; H, 7.46; N, 17.27.Observed value: C, 70.24; H, 7.37; N, 17.25.

Embodiment 3

4-(4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone

By the preparation embodiment 1 described step 1-3 that carries out.

Step 4:

With N ⁴-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl] quinoline-3,4-diamines (101g, 293mmol) and triethyl orthoformate (43.4g, 293mmol) mixture heating up in toluene (200mL) refluxed 2 hours, concentrating under reduced pressure then, so that 1-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl to be provided]-1H-imidazo [4,5-c] quinoline, oil is not further purified and is directly used in next step.

Step 5:

1-[4-(tertiary butyl dimethyl-silicon alcoxyl base) butyl with abovementioned steps]-1H-imidazo [4,5-c] quinoline (46.0g, 129mmol) and tetrabutyl ammonium fluoride (142mL, 1M solution among the THF) be dissolved among the THF (400mL), and stirred concentrating under reduced pressure 1 hour, so that 4-to be provided (1H-imidazo [4,5-c] quinoline-1-yl) fourth-1-alcohol (20.0g), behind the silica gel chromatography (with 10% methanol-eluted fractions in the methylene dichloride), get the light brown solid.

Step 6:

Utilize the general method described in embodiment 1 step 6, with DMSO (48.6g, 620mmol), oxalyl chloride (58.0g, 456mmol), and triethylamine (126g, 1.25mol) oxidation 4-(1H-imidazo [4,5-c] quinoline-1-yl) fourth-1-alcohol (20.0g, 82.9mmol), so that 4-to be provided (1H-imidazo [4,5-c] quinoline-1-yl) butyraldehyde (10.0g), behind the silica gel chromatography (with 10% methanol-eluted fractions in the methylene dichloride), use the trifluoroacetic acid (0.10g in THF (50mL) and water (20mL) mixture then, 1mmol) simple process gets light orange oil.

Step 7:

Utilize the general method described in embodiment 1 step 7, make 4-(1H-imidazo [4,5-c] quinoline-1-yl) butyraldehyde (7.94g, 33.2mmol) (33.2mL, 1M solution among the THF 33.2mmol) react with phenyl-magnesium-bromide, so that 4-to be provided (1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-alcohol (7.2g), white solid is not further purified and is directly used in next step.

Step 8:

Use the general method described in embodiment 1 step 6, and usefulness DMSO (2.70g, 34.0mmol), oxalyl chloride (3.20g, 25.0mmol), and triethylamine (6.90g, 68.1mmol) oxidation 4-(1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-alcohol) (7.2g, 22.7mmol), so that 4-(1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone (4.08g) to be provided, behind the silica gel chromatography (with 10% methanol-eluted fractions in the methylene dichloride), get light yellow solid.

Step 9:

Use the general method described in embodiment 1 step 9 and 10, by with m-CPBA (3.20g, 14.2mmol) reaction, ammonification 4-(1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone (4.08g, 12.9mmol), so that 4-to be provided (5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone, then with Tosyl chloride (2.71g, 14.2mmol) and solution of ammonium hydroxide (22mL) reaction, so that 4-to be provided (4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl fourth-1-ketone), white needles body, mp 209-211 ℃.

MS(APCI)m/z 331(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₁₈N ₄O:C, 72.71; H, 5.49; N, 16.96.Observed value: C, 72.60; H, 5.39; N, 16.98.

Embodiment 4

6-(4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone

Step 1:

In 10 minutes, in batches to 4-chloro-3-nitroquinoline (50.0g, 240mmol) and triethylamine (36.4g, 360mmo1) add in the stirring the mixture in methylene dichloride (370mL) 6-amino-1-hexanol (28.1g, 240mmol).Mixture heating up refluxed 35 minutes, and cooling is with chloroform dilution (300mL).Solution is water (200mL) in succession, saturated sodium bicarbonate aqueous solution (200mL), and salt solution (200mL) washing; Use dried over sodium sulfate; Filter; Be condensed into the glassy yellow solid, 6-(3-nitroquinoline-4-base is amino) is own-1-alcohol (68.3g), is not further purified to be directly used in next step.

Step 2:

Use the general method described in embodiment 1 step 6, with DMSO (4.05g, 51.8mmol), oxalyl chloride (4.83g, 38.0mmol), and triethylamine (10.5g, the 104mmol) alcohol of oxidation step 1,6-(3-nitro-quinolyl-4 amino) oneself-1-alcohol (10.0g, 34.6mmol), so that 6-(3-nitroquinoline-4-base amino) to be provided hexanal (9.9g), the glassy yellow solid is not further purified and is directly used in next step.

Step 3:

Use the general method described in embodiment 1 step 7, make 6-(3-nitroquinoline-4-base is amino) hexanal (9.9g, 34.5mmol) and phenyl-magnesium-bromide (36.2mL, 1M solution among the THF, 36.2mmol), with provide 6-(3-nitroquinoline-4-base amino)-1-phenyl oneself-1-alcohol (4.4g), silica gel chromatography is (with ethyl acetate and hexane wash-out, 1: 1, volume: volume), get the glassy yellow solid.

Step 4:

Use the general method described in embodiment 1 step 6, with DMSO (1.28g, 16.4mmol), oxalyl chloride (1.53g, 12.0mmol), and triethylamine (3.32g, 32.8mmol) oxidation 6-(3-nitroquinoline-4-base amino)-1-phenyl oneself-1-alcohol (4.0g, 11mmol), with provide 6-(3-nitroquinoline-4-base is amino)-1-phenyl oneself-1-ketone (2.27g), after re-crystallizing in ethyl acetate, get the light orange crystal.

Step 5:

With 6-(3-nitroquinoline-4-base amino)-1-phenyl oneself-1-ketone (2.27g, 6.25mmol) and the mixture of 5% platinum carbon catalyst (0.50g) in toluene (60mL) on the Parr wobbler at 50psi (3.4 * 10 ⁵Pa) hydrogenation is 3 hours under.Filter with the CELITE filtering medium, concentrating under reduced pressure, obtain 6-(3-quinolylamine-4-base is amino)-1-phenyl oneself-1-ketone (2.09g), deep yellow oil is not further purified and is directly used in next step.

Step 6:

Use the Dean-Stark water trap, with 6-(3-quinolylamine-4-base amino)-1-phenyl oneself-1-ketone (2.09g, 6.25mmol) and original acid methyl ester (1.52g, 9.37mmol) vlil in toluene (50mL) 2 hours, concentrating under reduced pressure then, with provide 6-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone (2.19g), scarlet oil is not further purified and is directly used in next step.

Step 7 and 8:

Use the general method described in embodiment 1 step 9 and 10, by with m-CPBA (1.35g, 6.03mmol) reaction, ammonification 6-(2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-the 1-phenyl oneself-1-ketone (2.19g, 5.48mmol), so that 6-to be provided (2-butyl-5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl)-the 1-phenyl oneself-1-ketone, then with Tosyl chloride (1.15g, 6.03mmol) and solution of ammonium hydroxide (9mL) reaction, with provide 6-(4-amino-2-butyl-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone (0.50g), silica gel chromatography (with 10% methanol-eluted fractions in the methylene dichloride) and with behind the ethyl alcohol recrystallization, get white solid, mp 149-151 ℃.

MS(APCI)m/z 415(M+H) ⁺；

Analyze: calculated value: C ₂₆H ₃₀N ₄O:C, 75.33; H, 7.29; N, 13.52.Observed value: C, 75.14; H, 7.13; N, 13.48.

Embodiment 5

6-(4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone

Step 1:

Use the general method described in embodiment 4 steps 6, use the Dean-Stark water trap, with 6-(3-quinolylamine-4-base is amino)-1-phenyl own-1-ketone (2.76g, 8.25mmol), trimethyl orthoformate (1.5g, 9.9mmol), and pyridine hydrochloride (95mg, 0.83mmol) vlil in toluene (26mL) 2 hours, concentrating under reduced pressure, with provide 6-(1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone, dark oil is not further purified and is directly used in next step.

Step 2:

Use the general method described in embodiment 1 step 9 and 10, by with m-CPBA (1.44g, 6.41mmol) reaction, ammonification 6-(1H-imidazo [4,5-c] quinoline-1-yl)-the 1-phenyl oneself-1-ketone (2.0g, 5.8mmol), so that 6-to be provided (5-oxidation-1H-imidazo [4,5-c] quinoline-1-yl)-the 1-phenyl oneself-1-ketone, then with Tosyl chloride (1.22g, 6.41mmol) and solution of ammonium hydroxide (10mL) reaction, with provide 6-(4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl oneself-1-ketone (0.29g), silica gel chromatography (with 5% methanol-eluted fractions in the methylene dichloride) and with behind the ethylene dichloride recrystallization, get white solid, mp 163-165 ℃.

MS(APCI)m/z 359(M+H) ⁺；

Analyze: calculated value: C ₂₂H ₂₂N ₄O:C, 73.72; H, 6.19; N, 15.63.Observed value: C, 73.66; H, 5.88; N, 15.55.

Embodiment 6

2-methyl isophthalic acid-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine

Step 1:

Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (45.0g, 216mmol), 3-(2-methyl-[1,3] propyl group amine (37.0g dioxolane-2-yl), 255mmol, press PCT and announce WO 01/51486 described preparation) and triethylamine (37.0g, 366mmol) in methylene dichloride, reacted 15 hours, so that [3-(2-methyl-[1 to be provided, 3] propyl group dioxolane-2-yl)]-(3-nitroquinoline-4-yl) amine (44.1g), with getting yellow solid behind the toluene/hexane mixtures recrystallization.

Step 2:

Product with abovementioned steps, [3-(2-methyl-[1,3] propyl group dioxolane-2 base)] (3-nitro-quinolyl-4) amine (29.5g, 93.0mmol) and V-Brite B (67.0g, about 85% is pure), and salt of wormwood (51.4g, 372mmol), (0.37g, 1mmol) solution in the mixture of methylene dichloride and water (every kind of 375mL) stirred 15 hours together with ethyl purpurine dibromide.Separate each layer, organic phase is used saturated sodium bicarbonate aqueous solution and water (every kind of 250mL) washing in succession, uses the salt of wormwood drying, filters, and concentrating under reduced pressure is to provide N ⁴-[3-(2-methyl-[1,3] dioxolane-2-yl)-propyl group] quinoline-3,4-diamines (26.0g), dark solid is not further purified and is directly used in next step.

Step 3:

Use the Dean-Stark water trap, with N ⁴-[3-(2-methyl-[1,3] propyl group dioxolane-2-yl)] quinoline-3,4-diamines (6.20g, 21.6mmol), triethly orthoacetate (3.10g, 25.8mmol) and tosic acid pyridinium salt (0.18g, 0.71mmol) vlil in toluene (250mL) 2 hours, periodically remove distillment, in reaction mixture, add fresh toluene.Decompression concentrated solution, residue is dissolved in the methylene dichloride (150mL), use saturated sodium bicarbonate aqueous solution and water (every kind of 100mL) washing in succession, use the salt of wormwood drying, filter, concentrating under reduced pressure, so that 2-methyl isophthalic acid-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline (6.70g) to be provided, dark oil is not further purified and is directly used in next step.

Step 4:

Utilize the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (9.4g), ammonification 2-methyl isophthalic acid-[3-(2-methyl-[1,3] propyl group dioxolane-2-yl)]-1H-imidazo [4,5-c] quinoline (6.70g, 21.5mmol), so that 2-methyl isophthalic acid-[3-(2-methyl-[1 to be provided, 3] dioxolane-2-yl)-propyl group]-5-oxidation-1H-imidazo [4,5c] quinoline, then with Tosyl chloride (7.20g, 37.8mmol) and solution of ammonium hydroxide (100mL) reaction, so that 2-methyl isophthalic acid-[3-(2-methyl-[1 to be provided, 3] propyl group dioxolane-2-yl)]-1H-imidazo [4,5-c] quinoline-4-amine (3.9g), with getting white solid, mp 193-195 ℃ behind the toluene recrystallization.

MS(APCI)m/z 327(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O ₂: C, 66.24; H, 6.79; N, 17.17.Observed value: C, 66.07; H, 6.58; N, 16.91.

Prepare embodiment 7,8 by top embodiment 6 described general methods, 9 and 10, ortho ester below wherein using or acyl chlorides replace the triethly orthoacetate in the synthesis step 3.

Embodiment 7

2-ethyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine

Utilize the triethyl orthopropionate of embodiment 6 steps 3, preparation 2-ethyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine, mp195-196.5 ℃.

MS(APCI)m/z 341(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₄N ₄O ₂: C, 67.04; H, 7.11; N, 16.46.Observed value: C, 66.77; H, 7.20; N, 16.41.

Embodiment 8

1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine

Utilize the former butyric acid trimethyl of embodiment 6 steps 3, preparation 1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine, mp 184-186 ℃.

MS(APCI)m/z＝355(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₆N ₄O ₂: C, 67.77; H, 7.39; N, 15.81.Observed value: C, 67.55; H, 7.45; N, 15.74.

Embodiment 9

2-butyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine

Utilize the original acid methyl ester of embodiment 6 steps 3, preparation 2-butyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine, mp 169-171.5 ℃.

MS(APCI)m/z＝369(M+H) ⁺；

Analyze: calculated value: C ₂₁H ₂₈N ₄O ₂0.9 H ₂O:C, 68.17; H, 7.67; N, 15.14.Observed value: C, 67.84; H, 7.69; N, 14.99.

Embodiment 10

2-ethoxyl methyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine

Utilize triethly orthoacetate and tosic acid pyridinium salt in oxyethyl group Acetyl Chloride 98Min. (1.1 equivalent) and triethylamine (1.1 equivalent) replacement embodiment 6 steps 3, preparation 2-ethoxyl methyl-1-[3-(2-methyl-[1,3] propyl group dioxolane-2-yl)]-1H-imidazo [4,5-c] quinoline-4-amine, mp150-152 ℃.

MS(APCI)m/z 371(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₆N ₄O ₃: C, 64.84; H, 7.07; N, 15.12.Observed value: C, 64.65; H, 7.13; N, 15.01.

Embodiment 11

5-(4-amino-2-methyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone

With concentrated hydrochloric acid (3mL) be added to 2-methyl isophthalic acid-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine (1.0g, 2.7mmol) in, mixture stirs several minutes, up to all substances all in solution.Add entry (5mL), solution at room temperature stirred 1 hour.After adding methylene dichloride (75mL) and water (25mL), solution is adjusted to alkalescence by slow adding salt of wormwood (10.0g).Separate each layer, organic layer is used the salt of wormwood drying with saturated sodium bicarbonate aqueous solution washing (25mL), filters, and concentrating under reduced pressure is to provide 5-(4-amino-2-methyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone, mp 194-196 ℃.

MS(APCI)m/z 283(M+H) ⁺；

Analyze: calculated value: C ₁₆H ₁₈N ₄O0.44 H ₂O:C, 66.20; H, 6.56; N, 19.30.Observed value: C, 66.23; H, 6.52; N, 19.35.

By top embodiment 11 described general methods, by the corresponding ketal of acid-catalyzed hydrolysis, preparation embodiment 12,13,14.

Embodiment 12

5-(4-amino-2-ethyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone

With 2-ethyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine is hydrolyzed into 5-(the amino 2-ethyl of 4--1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone, mp 206-208 ℃.

MS(APCI)m/z＝297(M+H) ⁺；

Analyze: calculated value: C ₁₇H ₂₀N ₄O:C, 68.90; H, 6.80; N, 18.9.Observed value C, 68.66; H, 6.84; N, 18.62.

Embodiment 13

5-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone

With 1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine is hydrolyzed into 5-(4-amino-2-propyl group-1H-imidazo [4,5c] quinoline-1-yl) penta-2-ketone, mp 176-177 ℃.

MS(APCI)m/z＝311(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O0.0125 CH ₂Cl ₂: C, 69.46; H, 7.13; N, 17.99.Observed value C, 69.12; H, 7.15; N, 17.71.

Embodiment 14

5-(4-amino-2-ethoxyl methyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone

With 2-ethoxyl methyl-1-[3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine is hydrolyzed into 5-(4-amino-2-ethoxyl methyl-1H-imidazo [4,5-c] quinoline-1-yl) penta-2-ketone, mp 173-175 ℃.

MS(APCI)m/z 327(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O ₂: C, 66.24; H, 6.79; N, 17.17.Observed value: C, 66.05; H, 6.94; N, 16.89.

Embodiment 15

7-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-2-ketone

Step 1:

By C.Temple, Jr., R.D.Elliott and J.A.Montgomery, J.Med.Chem., 1988,31, the described general method of 697-700, from 6-aminocaprolc acid, thionyl chloride and ethanol preparation 6-aminocaprolc acid carbethoxy hydrochloride.Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (41.7g, 200mmol), 6-aminocaprolc acid carbethoxy hydrochloride (46.9g, 240mmol) and triethylamine (50.6g, 500mmol) in methylene dichloride, reacted 15 hours, to provide 6-(3-nitroquinoline-4-base is amino) ethyl hexanoate (60.6g), yellow solid.

Step 2:

In the Parr hydrogenation vessel, add 6-(3-nitroquinoline-4-base amino) ethyl hexanoate (14.4g, 43.2mmol), 10% palladium carbon catalyst (1.0g), and ethanol (250mL); Place on the Parr wobbler; System is forced into 40psi (2.7 * 10 ⁵Pa) hydrogen.Shook 15 hours, reaction mixture filters with the CELITE filtering medium, concentrating under reduced pressure, and so that 6-(3-quinolylamine-4-base is amino) to be provided ethyl hexanoate, dark oil (9.8g) is not further purified and is directly used in next step.This step repeats several times, for later step is supplied raw materials.

Step 3:

Use the Dean-Stark water trap, with 6-(3-quinolylamine-4-base is amino) ethyl hexanoate (34.3g, 114mmol), former butyric acid trimethyl (19.5g, 131mmol) and the tosic acid pyridinium salt (1.0g, 4.0mmol) vlil in toluene (250mL) is 5 hours, periodically remove distillment, in reaction mixture, add new toluene.Decompression concentrated solution, residue is dissolved in the methylene dichloride (150mL), use saturated sodium bicarbonate aqueous solution and water (every kind of 100mL) washing in succession, use the salt of wormwood drying, filter concentrating under reduced pressure, so that 6-to be provided (2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl hexanoate (36.0g), dark oil is not further purified and is directly used in next step.

Step 4:

(39.0g 110mmol) adds sodium hydroxide (5.73g, 143mmol) solution in water (100mL) in the solution in ethanol (100mL) to 6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl hexanoate.Stir under the room temperature and spend the night, volatile matter is removed in decompression, and residue is dissolved in the water (200mL), and the solution washed with dichloromethane (3 * 75mL), be acidified to about pH 6.(3 * 75mL), the merging organic fraction is used dried over mgso to aqueous mixture with dichloromethane extraction, filter, concentrating under reduced pressure is to provide 6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) caproic acid (31.0g), solid is not further purified and is directly used in next step.

Step 5:

30 minutes introversive place ice bath 6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) caproic acid (31.0g, 95.3mmol) drip in the solution in methylene dichloride (200mL) oxalyl chloride (21.9g, 172mmol).Reaction mixture at room temperature stirred 1 hour, concentrating under reduced pressure then, with methylene dichloride (400mL) and N, the O-dimethyl hydroxylamine hydrochloride (18.6g 190mmol) is added in the residue, drip then triethylamine (38.5g, 380mmol).At room temperature stir and spend the night, reaction mixture is used saturated sodium bicarbonate aqueous solution and salt solution (every kind of 100mL) washing in succession, use the salt of wormwood drying, filter, concentrating under reduced pressure is to provide N-methoxyl group-N-methyl-6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) hexanamide (28.0g), dark oil is not further purified and is directly used in next step.

Step 6:

To the methoxyl group of the N-in ice bath-N-methyl-6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) hexanamide (22.0g, 59.7mmol) drip methyl-magnesium-bromide (40mL, the 3M solution in the ether, solution 120mmol) in the solution in chloroform (20mL) and THF (200mL).After 1 hour, (120mmol), reaction mixture at room temperature stirred 1 hour for 40mL, the 3M solution in the ether, added 10% hydrochloric acid soln (about 10mL) quencher then to add methyl-magnesium-bromide again.Concentrating under reduced pressure mixture, residue are dissolved in the methylene dichloride (200mL), and solution is used saturated sodium bicarbonate aqueous solution and salt solution (every kind of 100mL) washing in succession, uses the salt of wormwood drying, filters.Decompression concentrated solution, purifying on silica gel chromatography (with 3% methanol-eluted fractions in the methylene dichloride), so that 7-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-2-ketone (12.6g) to be provided, oil is not further purified and is directly used in next step.

Step 7:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (8.0g), ammonification 7-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-2-ketone (5.0g, 15.5mmol), so that 7-(5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-2-ketone to be provided, then with Tosyl chloride (4.42g, 23.2mmol) and solution of ammonium hydroxide (50mL) reaction, with provide 7-(, 4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-2-ketone), use acetonitrile, the mixture recrystallization of ethyl acetate and hexane, get white solid, mp 161-163 ℃.

MS(APCI)m/z＝339(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₆N ₄O:C, 70.98; H, 7.74; N, 16.55.Observed value C, 70.62; H, 7.91; N, 16.37.

Embodiment 16

12-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl dodecane-1-keto hydrochloride

Step 1:

By C.Temple, Jr., R.D.Elliott and J.A.Montgomery, J.Med.Chem., 1988,31, the described general method of 697-700, from the amino lauric acid of 12-, the amino lauric acid carbethoxy hydrochloride of thionyl chloride and ethanol preparation 12-.Utilize the general method described in embodiment 15 steps 1, make 4-chloro-3-nitroquinoline (15.5g, 74.4mmol), the amino lauric acid carbethoxy hydrochloride of 12-(25.0g, 89.3mmol), and triethylamine (18.8g, 186mmol) in methylene dichloride, reacted 15 hours, so that 12-(3-nitroquinoline-4-base amino) to be provided lauric acid ethyl ester (30.0g), yellow solid is not further purified and is directly used in next step.

Step 2:

General method described in embodiment 15 steps 2, reduction 12-(3-nitroquinoline-4-base is amino) lauric acid ethyl ester (30.0g, 77.0mmol), so that 12-(3-quinolylamine-4-base is amino) to be provided lauric acid ethyl ester (30.4g), solid is not further purified and is directly used in next step.

Step 3:

Use the general method described in embodiment 15 steps 3, by with former butyric acid trimethyl (13.4g, 90.6mmol) reaction, cyclisation 12-(3-quinolylamine-4-base is amino) lauric acid ethyl ester (30.4g, 78.8mmol), so that 12-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided lauric acid ethyl ester (32.1g), solid does not advance-goes on foot purifying and is directly used in next step.

Step 4 and 5:

Use the general method described in embodiment 15 steps 4, so that 12-to be provided (2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) lauric acid (33.6g), convert it into N-methoxyl group-N-methyl isophthalic acid 2-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) dodecane acid amides (36.8g) by the general method described in embodiment 15 steps 5.

Step 6:

Use the general method described in embodiment 15 steps 6, make N-methoxyl group-N-methyl isophthalic acid 2-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) dodecane acid amides (6.0g, 13.3mmol) and phenyl-magnesium-bromide (26.5mmol, 26.5mL 1M solution, among the THF), so that 1-phenyl-12-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided dodecane-1-ketone (6.0g).

Step 7:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (8.18g), ammonification 1-phenyl-12-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) dodecane-1-ketone (6.0g, 12.8mmol), so that 12-(5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl dodecane-1-ketone to be provided, then with Tosyl chloride (3.65g, 19.2mmol) and solution of ammonium hydroxide (40mL) reaction.Product is dissolved in the mixture of ethanol and ether, adds hydrochloric acid soln (1 equivalent, 1.0M solution is in the ether).Form precipitation, removal of solvent under reduced pressure.The solid that generates is with the mixture recrystallization with Virahol and hexane, so that 12-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-1-phenyl dodecane-1-keto hydrochloride, white solid, mp 195-196 ℃ to be provided.

MS(APCI)m/z＝485(M+H) ⁺；

Analyze: calculated value: C ₃₁H ₄₀N ₄O1.20 HCl0.17H ₂O:C, 70.05; H, 7.87; N, 10.52.Observed value C, 69.97; H, 7.70; N, 10.46.

Embodiment 17

1-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-6-methyl heptan-4-ketone

Step 1:

Utilize the general method described in embodiment 15 steps 1, make 4-chloro-3-nitroquinoline (49.6g, 238mmol), 4-aminobutyric acid carbethoxy hydrochloride (43.8g, 262mmol), and triethylamine (36.1g, 357mmol) in methylene dichloride, reacted 15 hours, so that 4-(3-nitroquinoline-4-base amino) to be provided ethyl butyrate (63.8g), yellow solid is not further purified and is directly used in next step.

Step 2:

Use the general method described in embodiment 6 steps 2, reduction 4-(3-nitroquinoline-4-base is amino) butyric acid ethyl ester (37.0g, 122mmol), so that 4-(3-quinolylamine-4-base is amino) to be provided ethyl butyrate (24.9g), dark oil is not further purified and is directly used in next step.

Step 3:

Use the general method described in embodiment 15 steps 3, by with former butyric acid trimethyl (10.4g, 70.2mmol) reaction, cyclisation ethyl 4-(3-quinolylamine-4-base is amino) butyric ester (18.0g, 65.9mmol), so that 4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided ethyl butyrate (14.2g), obtain solid behind the silica gel chromatography (with 5% methanol-eluted fractions in the methylene dichloride).

Step 4:

Under 0 ℃, (160mmol) drips of solution in is added to N for 80mL, 2M solution, and (15.6g is 160mmol) in the stirred suspension in methylene dichloride (150mL) for the O-dimethyl hydroxylamine hydrochloride at toluene with trimethyl aluminium.After 15 minutes, take out reaction flask from ice bath, solution at room temperature stirred 15 minutes.In ice bath, cool off flask then, drip 4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl butyrate (34.7g, 107mmol) solution in methylene dichloride (100mL) fast.After 15 minutes, remove ice bath, vlil makes gas evolution.After 20 hours, slowly add 10% solution (15mL) of hydrochloric acid in water, add saturated sodium bicarbonate aqueous solution (50mL) then.Separate each layer, aqueous mixture dichloromethane extraction (2 * 50mL).Merge organic solution, use in succession 5% aqueous sodium hydroxide solution (2 * 50mL) and saturated sodium bicarbonate aqueous solution (1 * 50mL) washing, use the salt of wormwood drying, filter, concentrating under reduced pressure is to provide N-methoxyl group-N-methyl-4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide (35.9g), dark oil is not further purified and is directly used in next step.

Step 5:

In the several minutes, to N-methoxyl group-N-methyl-4-(the 2-propyl group-1H-imidazo [4 in dry ice/isopropanol is bathed, 5-c] quinoline-1-yl) butyramide (4.80g, 14.1mmol) add isobutyl-chlorination magnesium (28mL in the stirred solution in THF (100mL), 2M solution in the ether, solution 56mmol).Add when finishing, remove reaction flask from cooling bath, mixture at room temperature stirred 4 hours.Slowly add 10% aqueous hydrochloric acid (3mL), add saturated sodium bicarbonate aqueous solution (15mL) and methylene dichloride (100mL) then.Separate each layer, (1 * 75mL), the merging organism is used the salt of wormwood drying to water, filters concentrating under reduced pressure with dichloromethane extraction.Behind the silica gel chromatography (with 5% methanol-eluted fractions in the methylene dichloride), obtain buttery 6-methyl isophthalic acid-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-4-ketone (2.40g).

Step 6:

Utilize the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (3.9g), ammonification 6-methyl isophthalic acid-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) heptan-4-ketone (2.40g, 7.10mmol), so that 6-methyl isophthalic acid-(5-oxo-2-propyl group-1H-imidazo [4 to be provided, 5-c] quinoline-1-yl) heptan-4-ketone, then with Tosyl chloride (2.0g, 10.5mmol) and solution of ammonium hydroxide (75mL) reaction, so that 1-to be provided (4-amino-2-propyl group-1H-imidazo [4,5c] quinoline-1-yl)-6-methyl heptan-4-ketone, behind the methanol aqueous solution recrystallization, get the brown crystal, mp 136-138 ℃.

MS(APCI)m/z 353(M+H) ⁺；

Analyze: calculated value: C ₂₁H ₂₈N ₄O:C, 71.56; H, 8.01; N, 15.90.Observed value: C, 71.33; H, 8.09; N, 15.69.

Embodiment 18

1-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) last of the ten Heavenly stems-4-ketone

Step 1～4:

Utilize the general method described in embodiment 17 steps 1～4 to prepare N-methoxyl group-N-methyl-4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide.

Step 5:

Utilize the general method described in embodiment 17 steps 5, make N-methoxyl group-N-methyl-4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide (6.10g, 17.9mmol) (13.5mL, 2M solution in the ether 27mmol) react with the n-hexyl magnesium bromide, so that 1-to be provided (2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) last of the ten Heavenly stems-4-ketone (6.10g), yellow oil is not further purified and is directly used in next step.

Step 6:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (8.50g), ammonification 1-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) last of the ten Heavenly stems-4-ketone (6.10g, 17.2mmol), so that 1-to be provided (5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) last of the ten Heavenly stems-4-ketone, then with Tosyl chloride (4.90g, 25.8mmol) and solution of ammonium hydroxide (100mL) reaction, so that 1-to be provided (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) last of the ten Heavenly stems-4-ketone), behind the methanol aqueous solution recrystallization, get white solid, mp 111-113 ℃.

MS(APCI)m/z 381(M+H) ⁺；

Analyze: calculated value: C ₂₃H ₃₂N ₄O:C, 72.59; H, 8.48; N, 14.72.Observed value: C, 72.53; H, 8.59; N, 14.63.

Embodiment 19

6-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methyl hexanamide

Step 1～5:

Utilize the method described in embodiment 15 steps 1～5 to prepare N-methoxyl group-N-methyl-6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) hexanamide.

Step 6:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (6.13g), ammonification N-methoxyl group-N-methyl-6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) hexanamide (4.01g, 10.9mmol), so that N-methoxyl group-N-methyl-6-to be provided (5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) hexanamide, then with Tosyl chloride (2.53g, 13.3mmol) and solution of ammonium hydroxide (40mL) reaction, so that 6-to be provided (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methyl hexanamide), behind the mixture recrystallization with ethyl acetate and hexane, get white solid, mp 134-135 ℃.

MS(APCI)m/z＝384(M+H) ⁺；

Analyze: calculated value: C ₂₁H ₂₉N ₅O ₂0.023 C ₄H ₈O ₂: C, 65.71; H, 7.63; N, 18.17.Observed value C, 65.44; H, 7.77; N, 17.88.

Embodiment 20

4-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methylbutyryl amine

Step 1～4:

Use the method for embodiment 17 steps 1～4 to prepare N methoxyl group-N-methyl-4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide.

Step 5:

Utilize the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (9.50g), ammonification N-methoxyl group-N methyl-4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide (7.4g, 21.7mmol), so that N-methoxyl group-N-methyl-4-to be provided (5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) butyramide, then with Tosyl chloride (7.20g, 37.8mmol) and solution of ammonium hydroxide (200mL) reaction, so that 4-to be provided (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methyl-butyramide, behind the methanol aqueous solution recrystallization, get white crystal, mp 163-165 ℃.

MS(APCI)m/z 356(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₅N ₅O ₂: C, 64.20; H, 7.09; N, 19.70.Observed value: C, 64.10; H, 6.91; N, 19.57.

Embodiment 21

12-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methyl dodecanoyl amine hydrochlorate

Step 1～5:

Use the method for embodiment 16 steps 1～5 to prepare N methoxyl group-N-methyl isophthalic acid 2-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) dodecane acid amides.

Step 6:

Use embodiment 1 step 9 and 10 and embodiment 16 steps 7 described in general method, by reacting with m-CPBA (6.13g), ammonification N-methoxyl group-N-methyl isophthalic acid 2-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) dodecane acid amides (4.01g, 8.86mmol), so that N-methoxyl group-N-methyl isophthalic acid 2-to be provided (5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) the dodecane acid amides, then with Tosyl chloride (2.53g, 13.3mmol) and solution of ammonium hydroxide (40mL) reaction, so that 2-to be provided (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methyl dodecanoyl amine hydrochlorate, behind Virahol recrystallization hydrochloride, get white solid, mp 156-158 ℃.

MS(APCI)m/z＝468(M+H) ⁺；

Analyze: calculated value: C ₂₇H ₄₁N ₅O ₂1.20 HCl:C, 63.41; H, 8.31; N, 13.69.Observed value C, 63.44; H, 8.24; N, 13.74.

Embodiment 22

1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-methyl isophthalic acid H-imidazo [4,5-c] quinoline-4-amine

Step 1:

(36.3g, 0.59mol), (53.0g, 0.54mol) and 1, (DBU, 1.5g, mixture 10mmol) at room temperature left standstill 14 days 5-diazabicyclo [5.4.0] undecane 7-alkene mesityl oxide with Nitromethane 99Min..Add methylene dichloride (150mL), (the salt of wormwood drying is used in 3 * 35mL) washings to solution, filters with 10% hydrochloric acid soln.4, the dichloromethane solution of 4-dimethyl-5-nitro penta-2-ketone is directly used in next step, is not further purified.

Step 2:

In dry ice/isopropanol is bathed, cooling 1, two (the trimethyl silyl oxygen base) ethane (26.5g of 2-, 128mmol) the stirred solution in methylene dichloride (50mL), and adding trimethyl silyl trifluoromethayl sulfonic acid ester (2.2g, 1.0mmol), add 4 of abovementioned steps then, the dichloromethane solution of 4-dimethyl-5-nitro penta-2-ketone (50mL, 19.0g, 119mmol).After 30 minutes, remove cooling bath, solution rises to room temperature.Solution filters with salt of wormwood, concentrating under reduced pressure, and so that 2-(2,2-dimethyl-3-nitro propyl group)-2-methyl-[1,3] dioxolane (23.5g) to be provided, dark oil is not further purified and is directly used in next step.

Step 3:

In the Parr hydrogenation vessel, add 2-(2,2-dimethyl-3-nitro propyl group)-2-methyl-[1,3] dioxolane (23.1g, 113mmol), 5% platinum carbon catalyst (3.0g) and ethanol (250mL); Place on the Parr wobbler; System is forced into 50psi (3.4 * 10 ⁵Pa) hydrogen.After shaking 24 hours, reaction mixture filters with the CELITE filtering medium, concentrating under reduced pressure, and providing 2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group amine (19.8g), oil is not further purified and is directly used in next step.

Step 4:

Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (21.8g, 104mmol), 2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group amine (19.8g, 114mmol) and triethylamine (15.2g, 150mmol) in methylene dichloride, reacted 75 hours, so that [2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-(3-nitroquinoline-4-yl) amine (35.9g) to be provided, yellow solid is not further purified and is directly used in next step.

Step 5:

General method reduction [2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-(3-nitroquinoline-4-yl) amine described in use embodiment 6 steps 2 (35.9g, 104mmol), so that N to be provided ⁴-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group] quinoline-3,4-diamines (25.2g), dark oil is not further purified and is directly used in next step.

Step 6:

Use the general method described in embodiment 6 steps 3, by (3.6g 30mmol) reacts cyclisation N with trimethyl orthoacetate ⁴-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group] quinoline-3,4-diamines (8.0g, 25.4mmol), to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-methyl isophthalic acid H-imidazo [4,5-c] quinoline (5.80g), behind the silica gel chromatography (, containing the solution of ammonium hydroxide of the 5mL that has an appointment in every liter of eluent) with 7% methanol solution wash-out in the methylene dichloride, solid.

Step 7:

Utilize the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (7.5g), ammonification 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-methyl isophthalic acid H-imidazo [4,5-c] quinoline (5.80g, 17.1mmol), to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-methyl-5-oxidation-1H-imidazo [4,5-c] quinoline, then with Tosyl chloride (5.7g, 30mmol) and solution of ammonium hydroxide (150mL) reaction, so that 1-[2 to be provided, 2-dimethyl-3-(2-methyl-[1,3] propyl group dioxolane-2-yl)]-2 methyl isophthalic acid H-imidazo [4,5-c] quinoline-4-amine, use acetonitrile, methyl alcohol, behind the mixture recrystallization of water, the light brown solid, mp 209-211 ℃.

MS(APCI)m/z 355(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₆N ₄O ₂: C, 67.77; H, 7.39; N, 15.81.Observed value: C, 67.68; H, 7.62; N, 15.87.

Embodiment 23

1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine

Step 1-5 is identical with embodiment 22.

Step 6:

Utilize the general method described in embodiment 22 steps 6, by (4.4g 30mmol) reacts cyclisation N with former butyric acid trimethyl ⁴-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group] quinoline-3,4-diamines (9.1g, 28.9mmol), to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline (3.10g), behind the silica gel chromatography (, containing the solution of ammonium hydroxide of the 5mL that has an appointment in every liter of eluent), obtain solid with 7% methanol solution wash-out in the methylene dichloride.

Step 7:

Utilize the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (3.70g), ammonification 1-[2,2-dimethyl-3-(2-methyl-[1,3] propyl group dioxolane-2-yl)]-2-propyl group-1H-imidazo [4,5-c] and quinoline (3.10g, 8.44mmol), so that 1-[2 to be provided, 2-dimethyl-3-(2-methyl-[1,3] propyl group dioxolane-2-yl)]-5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline, then with Tosyl chloride (2.80g, 14.7mmol) and solution of ammonium hydroxide (100mL) reaction, to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine, behind the methanol aqueous solution recrystallization, get the white needles body, mp 186-188 ℃.

MS(APCI)m/z 383(M+H) ⁺；

Analyze: calculated value: C ₂₂H ₃₀N ₄O ₂: C, 69.08; H, 7.91; N, 14.65.Observed value: C, 69.03; H, 8.15; N, 14.60.

Embodiment 24

5-(4-amino-2-methyl-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone

Use embodiment 11 described general methods, with aqueous hydrochloric acid hydrolysis 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-methyl isophthalic acid H-imidazo [4,5-c] quinoline-4-amine, so that 5-to be provided (4-amino-2-methyl-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone is behind the acetonitrile solution recrystallization, get the light brown solid, mp 223-225 ℃.

MS(APCI)m/z 311(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O:C, 69.65; H, 7.14; N, 18.05.Observed value: C, 69.64; H, 7.42; N, 18.04.

Embodiment 25

5-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone

Use embodiment 11 described general methods, with aqueous hydrochloric acid hydrolysis 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine, so that 5-to be provided (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone is behind the acetonitrile solution recrystallization, get the light brown solid, mp 178-180 ℃.

MS(APCI)m/z 339(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₆N ₄O:C, 70.97; H, 7.74; N, 16.55.Observed value: C, 70.80; H, 7.89; N, 16.66.

Embodiment 26

3-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl propionate

Step 1:

Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (45.3g, 217mmol), β alanine carbethoxy hydrochloride (40.0g, 240mmol), and triethylamine (54.8g, 542mmol) in methylene dichloride the reaction 15 hours, to provide 3-(3-nitroquinoline-4-base is amino) ethyl propionate (62.0g), yellow solid.

Step 2:

Use the general method described in embodiment 6 steps 2, reduction 3-(3-nitroquinoline-4-base is amino) ethyl propionate, so that 3-(3-quinolylamine-4-base is amino) to be provided ethyl propionate (40.2g), dark oil is not further purified and is directly used in next step.

Step 3:

Utilize the general method described in embodiment 15 steps 3, by with former butyric acid trimethyl (7.22g, 48.7mmol) reaction, cyclisation 3-(3-quinolylamine-4-base is amino) ethyl propionate (11.0g, 42.4mmol), so that 3-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided ethyl propionate (10.6g), dark oil is not further purified and is directly used in next step.

Step 4:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (4.63g), ammonification 3-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl propionate (3.30g, 10.6mmol), so that 3-to be provided (5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) the propionic acid ethyl ester, then with Tosyl chloride (3.53g, 18.6mmol) and solution of ammonium hydroxide (50mL) reaction, so that 3-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided ethyl propionate, after white solid is used the methanol aqueous solution recrystallization, mp 156-157 ℃.

MS(APCI)m/z＝327(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O ₂: C, 66.24; H, 6.79; N, 17.16.Observed value C, 65.98; H, 6.96; N, 17.29.

Embodiment 27

4-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl butyrate

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (14.1g), ammonification 4-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl butyrate (8.20g, 25.2mmol, obtain from the step 3 of embodiment 17), so that 4-(5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided the butyric acid ethyl ester, then with Tosyl chloride (8.40g, 44.1mmol) and solution of ammonium hydroxide (150mL) reaction, so that 4-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided ethyl butyrate, behind the methanol aqueous solution recrystallization, get white solid, mp 154-156 ℃.

MS(APCI)m/z＝341(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₄N ₄O ₂: C, 67.04; H, 7.11; N, 16.46.Observed value: C, 66.68; H, 6.87; N, 16.51.

Embodiment 28

6-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl hexanoate

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (13.1g), ammonification 6-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) ethyl hexanoate (6.30g, 17.8mmol, obtain from embodiment 15 steps 3), so that 6-(5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided the caproic acid ethyl ester, then with Tosyl chloride (4.58g, 24.0mmol) and solution of ammonium hydroxide (60mL) reaction, so that 6-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) to be provided ethyl hexanoate, behind the methanol aqueous solution recrystallization, get the brown solid, mp 112-113 ℃.

MS(APCI)m/z＝369(M+H) ⁺；

Analyze: calculated value: C ₂₁H ₂₈N ₄O ₂1.0 H ₂O:C, 67.77; H, 7.69; N, 15.05.Observed value: C, 67.39; H, 7.73; N, 14.79.

Embodiment 29

1-(2,2-diethoxy ethyl)-2-propyl group-1H-imidazo [4,5-c] quinoline 4-amine

Step 1:

Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (20.9g, 100mmol), the aminoacetaldehyde diethyl acetal (14.4g, 110mmol), and triethylamine (12.6g, 125mmol) in methylene dichloride, reacted 15 hours, so that (2,2-diethoxy ethyl)-(3-nitroquinoline-4-yl) amine (29.7g), yellow solid to be provided.

Step 2:

General method reduction (2,2-diethoxy ethyl)-(3-nitroquinoline-4-yl) amine described in embodiment 6 steps 2 is to provide N ⁴-(2,2-diethoxy ethyl) quinoline-3,4-diamines (26.5g), dark oil is not further purified and is directly used in next step.

Step 3:

Utilize the general method described in embodiment 15 steps 3, by (15.9g 107mmol) reacts cyclisation N with former butyric acid trimethyl ⁴-(2,2-diethoxy ethyl) quinoline-3, (26.5g, 96.2mmol), so that 1-(2,2-diethoxy ethyl)-2-propyl group-1H-imidazo [4,5-c] quinoline (25.4g) to be provided, dark oil is not further purified and is directly used in next step the 4-diamines.

Step 4:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (6.0g), ammonification 1-(2,2-diethoxy ethyl)-2-propyl group-1H-imidazo [4,5-c] and quinoline (4.50g, 13.7mmol), so that 1-(2 to be provided, 2-diethoxy ethyl)-5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline, then with Tosyl chloride (4.60g, 24.1mmol) and solution of ammonium hydroxide (130mL) reaction, so that 1-(2 to be provided, 2-diethoxy ethyl)-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine, behind the methanol aqueous solution recrystallization, get white solid, mp 148-150 ℃.

MS(APCI)m/z＝343(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₆N ₄O ₂: C, 66.64; H, 7.65; N, 16.36.Observed value: C, 66.62; H, 7.80; N, 16.43

Embodiment 30

1-(3,3-diethoxy propyl group)-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine

Step 1:

Utilize the general method described in embodiment 1 step 1, make 4-chloro-3-nitroquinoline (20.3g, 97.1mmol), 1-amino-3, and the 3-di ethyl propyl ether (25.0g, 116mmol) and triethylamine (33.8g, 333mmol) in methylene dichloride, reacted 15 hours, so that (3,3-diethoxy propyl group)-(3-nitroquinoline-4-yl) amine (30.5g), yellow solid to be provided.

Step 2:

Use general method reduction (3,3-diethoxy propyl group)-(3-nitroquinoline-4-yl) amine described in embodiment 6 steps 2, so that N to be provided ⁴-(3,3-diethoxy propyl group) quinoline-3,4-diamines (20.7g), dark oil is not further purified and is directly used in next step.

Step 3:

Use the general method described in embodiment 15 steps 3, by (13.2g 89.4mmol) reacts cyclisation N with former butyric acid trimethyl ⁴-(3,3-diethoxy propyl group) quinoline-3, (20.7g, 71.5mmol), so that 1-(3,3-diethoxy propyl group)-2-propyl group-1H-imidazo [4,5-c] quinoline (22.3g) to be provided, dark oil is not further purified and is directly used in next step the 4-diamines.

Step 4:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (5.3g), ammonification 1-(3,3-diethoxy propyl group)-2-propyl group-1H-imidazo [4,5-c] and quinoline (4.50g, 13.2mmol), so that 1-(3 to be provided, 3-diethoxy propyl group)-5-oxo-2-propyl group-1H-imidazo [4,5-c] quinoline, then with Tosyl chloride (4.89g, 25.7mmol) and solution of ammonium hydroxide (40mL) reaction, so that 1-(3 to be provided, 3-diethoxy propyl group)-2-propyl group-1H-imidazo [4,5-c] quinoline-4-amine, behind recrystallization methyl alcohol, get the grey needles, mp 148-150 ℃.

MS(APCI)m/z＝357(M+H) ⁺；

Analyze: calculated value: C ₂₀H ₂₈N ₄O ₂: C, 67.39; H, 7.92; N, 15.72.Observed value: C, 67.24; H, 8.05; N, 15.70.

Embodiment 31

1-[2,2-dimethyl-3-(2-methyl [1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine

Step 1-5 is identical with embodiment 22.

Step 6:

Use the general method described in embodiment 22 steps 6, by (3.3g 10mmol) reacts cyclisation N with trimethyl orthoformate ⁴-[2,2-dimethyl-3-(2-methyl-[1,3] propyl group dioxolane-2-yl)] quinoline-3, the 4-diamines (8.1g, 25.7mmol), so that 1-[2 to be provided, 2-dimethyl-3-(2-methyl [1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline (8.8g), oil is not further purified and is directly used in next step.

Step 7:

Use the general method described in embodiment 1 step 9 and 10, by reacting with m-CPBA (11.8g), ammonification 1-[2,2-dimethyl-3-(2-methyl [1,3] dioxolane-2-yl) propyl group]-1H imidazo [4,5-c] quinoline (8.8g, 27mmol), to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-5-oxidation-1H imidazo [4,5-c] quinoline, then with Tosyl chloride (9.1g, 48mmol) and solution of ammonium hydroxide (100mL) reaction, so that 1-[2 to be provided, 2-dimethyl-3-(2-methyl [1,3] propyl group dioxolane-2-yl)]-1H-imidazo [4,5-c] quinoline-4 amine, silica gel chromatography (, with 7% methanol solution wash-out in the methylene dichloride, the solution of ammonium hydroxide that contains the 5mL that has an appointment in every liter of eluent) with behind the methanol aqueous solution recrystallization, the light brown solid, mp 153-155 ℃.

MS(APCI)m/z 341(M+H) ⁺；

Analyze: calculated value: C ₁₉H ₂₄N ₄O ₂: C, 67.04; H, 7.11; N, 16.46.Observed value: C, 66.76; H, 7.39; N, 16.41.

Embodiment 32

5-(4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone

Use embodiment 11 described general methods, with aqueous hydrochloric acid hydrolysis 1-[2,2-dimethyl-3-(2-methyl-[1,3] dioxolane-2-yl) propyl group]-1H-imidazo [4,5-c] quinoline-4-amine, so that 5-to be provided (4-amino-1H-imidazo [4,5-c] quinoline-1-yl)-4,4-dimethyl-penten-2-ketone is behind the methanol aqueous solution recrystallization, get light yellow solid, mp 214-216 ℃.

MS(APCI)m/z 297(M+H) ⁺；

Analyze: calculated value: C ₁₈H ₂₂N ₄O:C, 68.89; H, 6.80; N, 18.90.Observed value: C, 68.91; H, 6.85:N, 19.12.

Embodiment 33

5-(4-amino-6,7-dimethyl-2-propyl group-1H-imidazo [4,5-c] pyridine-1-yl) penta-2-ketone

Step 1:

Under 0 ℃, at N, dinethylformamide (675mL) (DMF) in, grind 2,4-two chloro-5,6-dimethyl-3-nitropyridine (135.0g, 0.488mol) and 4-aminobutyric acid carbethoxy hydrochloride (114.0g, 0.683mol).(272.6mL 1.95mol), produces brown slurry to add triethylamine.After 15 minutes, reaction mixture rises to envrionment temperature, and reaction is stirred and spent the night. ¹The reaction of H NMR analysis revealed is not finished.(102.2mL, 0.73mol) (35.28g, 0.159mol) solution in DMF (200mL) is added in the reaction mixture, restir 24 hours with 4-aminobutyric acid carbethoxy hydrochloride with the triethylamine of additional quantity.Half reaction mixture is added to and separates in the flask, adds deionized water (3L) in each flask, restir 1 hour.Filter and collect the precipitation that generates in each flask, drying under reduced pressure.The crude product re-crystallizing in ethyl acetate is filtered and is obtained 86.20g 4-[(2-chloro-5,6-dimethyl-3-nitropyridine-4-yl) amino] ethyl butyrate, yellow granular solids.

Step 2:

Acetonitrile at 9: 1: in water (1012mL) mixture, grind 4-[(2-chloro-5,6-dimethyl-3-nitropyridine-4-yl) amino] ethyl butyrate (86.2g, 0.276mol), sodiumazide (35.49g, 0.552mol), with the Cerium II Chloride heptahydrate (50.86g, 0.138mol).Stirred reaction mixture, reflux 18 hours.Filtering reaction, the concentrating under reduced pressure yellow filtrate obtains the 90.94g crude product.Use 360mL ethyl acetate abrasive substance down at 95 ℃, filter.Filtrate produces light yellow crystal at ambient temperature, to provide 64.3g 4-[(5,6-dimethyl-8-nitro tetrazolo [1,5-a] pyridine-7-yl) amino] ethyl butyrate, yellow solid.

Step 3:

With 4-[(5,6-dimethyl-8-nitro tetrazolo [1,5-a] pyridine-7-yl) amino] (64.3g 0.198mol) mixes with acetonitrile (2L) ethyl butyrate, adds catalytic 10% palladium charcoal.Mixture places hydrogenator last 72 hour, filters with one deck CELITE filtration adjuvant.Concentrating under reduced pressure filtrate obtains 58.2g 4-[(8 amino-5,6-dimethyl tetrazolo [1,5-a] pyridine-7-yl) amino] ethyl butyrate.

Step 4:

In succession with pyridine hydrochloride (8.57g, 74mmol) with former butanic acid trimethylammonium ester (34.6mL, 217mmol) be added to the 4-[(8-amino-5 that in toluene (1165mL), grinds, 6-dimethyl tetrazolo [1,5-a] pyridine-7-yl) amino] ethyl butyrate (58.2g, 198mmol), and reflux 0.5 hour.The reaction mixture concentrating under reduced pressure distributes between methylene dichloride and saturated aqueous sodium carbonate.Separate organic layer, concentrating under reduced pressure, 52.99g 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) ethyl butyrate solid is used re-crystallizing in ethyl acetate, is not further purified.

Step 5:

(52.99g 0.153mol) forms slurry in ethanol (550mL), handled 0.5 hour with 50% sodium hydroxide solution with 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) ethyl butyrate.The concentrating under reduced pressure reaction keeps spending the night, and is dissolved in (250mL) in the water.PH regulator to 5 filters the white precipitate that generates.Residue uses methyl alcohol (1L) to grind at ambient temperature, and concentrating under reduced pressure so that 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) to be provided butyric acid, is not further purified during use.

Step 6:

With 5 N, dinethylformamide (DMF) is added to 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) butyric acid, and (36.22g is 113.8mmol) and in the methylene dichloride (725mL).(29.8mL 341.3mmol) is added drop-wise in the reaction mixture with oxalyl chloride.After 10 minutes, the concentrating under reduced pressure reaction mixture is to provide 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) butyryl chloride.

Step 7:

(38.39g 114mmol), is cooled to 0 ℃ to butyryl chloride to grind 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) with chloroform (768mL).In succession with N, the O-dimethyl hydroxylamine hydrochloride (16.68g, 171mmol) and triethylamine (47.7mL, 342mmol drip) be added in the reaction mixture, stirred 0.5 hour.After adding saturated sodium bicarbonate aqueous solution (400mL), reaction mixture restir 10 minutes.Separate organic phase, use dried over sodium sulfate, concentrating under reduced pressure is to provide 40.01g 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl)-N-methoxyl group-N-methylbutyryl amine, yellow oil.

Step 8:

Under 0 ℃ slowly with methyl magnesium iodide (5.5mL, 41.5mmol) slowly be added drop-wise to 4-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl)-(10.0g is 27.7mmol) and in the grinding mixture of tetrahydrofuran (THF) (125mL) for N-methoxyl group-N-methylbutyryl amine.Reaction rises to envrionment temperature, after stirring is spent the night, ¹H NMR shows that reaction do not finish.After initial the adding, at the 18th and 21.75 hour, the methyl magnesium iodide of adding additional quantity (5.5mL, 41.5mmol).(3.6mL 27mmol), reacted 1 hour more finally to add the methyl magnesium iodide at the 23rd hour after initial the adding.Add 1N aqueous hydrochloric acid (35mL), produce Huang-orange slurry, the concentrating under reduced pressure mixture.Residue is dissolved in the methylene dichloride (200mL), with saturated sodium bicarbonate aqueous solution washing (100mL), uses dried over sodium sulfate, concentrating under reduced pressure, with provide 8.15g 5-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) penta-2-ketone, be not further purified.

Step 9:

With triphenylphosphine (13.5g, 51.5mmol) be added to 5-(5,6-dimethyl-8-propyl group-1H-imidazo [4,5-c] tetrazolo [1,5-a] pyridine-7-yl) (8.15g is 25.8mmol) with 1 for penta-2-ketone, in the mixture of 2-dichlorobenzene (163mL), be heated to 133 ℃ and kept 13.5 hours.Temperature of reaction rose to 140 ℃ in 1.5 hours.(3.39g 12.9mmol), reacted reheat 1 hour to add triphenylphosphine again.The dark-brown solution that obtains is cooled to envrionment temperature, concentrating under reduced pressure.The residue that obtains is dissolved in the methyl alcohol (150mL), adds 1N aqueous hydrochloric acid (75mL) and produces slurry.Be reflected at 40 ℃ and stir down hour, filtering mixt, concentrating under reduced pressure is dissolved in (100mL) in the methylene dichloride, with the washing of washing 1N aqueous hydrochloric acid.With saturated sodium bicarbonate aqueous solution and 50% sodium hydroxide solution water layer is adjusted to pH 14, product extracts into chloroform (250mL).Use the dried over sodium sulfate organic layer, concentrating under reduced pressure produces 4.61g brown solid material.Material acetonitrile recrystallization obtains the isolated material of 2.53g.Part material (1.22g) on the efficient fast chromatographic instrument of BIOTAGE HORIZON by the column chromatography purifying (with the chloroform/methanol/ammonium hydroxide (80/18/2) of 0: 100～40: 60 ratios: the chloroform wash-out), so that 0.81g 5-to be provided (4-amino-6,7-dimethyl-2-propyl group-1H-imidazo [4,5-c] pyridine-1-yl) penta-2-ketone, white powder, mp 148.5-149.5 ℃.

¹H NMR(300MHz，DMSO-d ₆)65.58(s，2H)，4.16(t，8.1Hz，2H)，2.77(t，8.1Hz，2H)，2.58(t，2H)，2.37(s，3H)，2.30(s，3H)，2.10(s，3H)，1.80(m，J＝7.5Hz，4H)，1.00(t，J＝7.5Hz，3H)；

MS(APCI)289(M+H) ⁺；

Analyze: C ₂₀H ₂₆N ₆O ₂: calculated value: C, 66.64; H, 8.39; N, 19.43.Observed value: C, 66.40; H, 8.63; N, 1944.

Embodiment 34

4-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] ethyl butyrate

Step 1:

At room temperature with oxyethyl group Acetyl Chloride 98Min. (7.00g, 57.1mmol) drips of solution in methylene dichloride (10mL) is added to 4-(3-quinolylamine-4-base is amino) ethyl butyrate and (press that embodiment 17 step 1-2 prepare, 12.5g, 45.7mmol) in the stirred solution in methylene dichloride (100mL).1.5 after hour, the concentrating under reduced pressure reaction mixture, so that solid to be provided, to wherein add ethanol (100mL) and triethylamine (17.4mL, 125mmol).Solution was at room temperature placed 5 days, and reflux is 2 hours then.Decompression concentrated solution.Residue distributes between methylene dichloride (150mL) and water (50mL).The salt of wormwood drying is used in organic layer water (50mL) and saturated sodium bicarbonate aqueous solution (50mL) washing, filters, concentrating under reduced pressure obtains 15.4g 4-[2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] ethyl butyrate, brown oil, water is further purified when next step uses.

Step 2:

Under 0 ℃ to 4-[2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] ethyl butyrate (and 15.4g, 45.1mmol) in the stirred solution in methylene dichloride (150mL) gradation add mCPBA (about 77% is pure, 19.7g, 87.9mmol).Reaction mixture at room temperature stirred 1.5 hours, added dense ammonium hydroxide (50mL).Gradation is added to Tosyl chloride in the mixture, stirs 1 hour, filters.Filtrate is transferred to separating funnel, adds saturated sodium bicarbonate aqueous solution (50mL), separates each layer.Water layer dichloromethane extraction (2 * 50mL).Merge organic layer, with 5% aqueous sodium hydroxide washes wash (2 * 75mL), use the salt of wormwood drying, filter, concentrating under reduced pressure obtains brown solid, formation slurry in ethyl acetate (50mL), filtration.Concentrating under reduced pressure filtrate, solid ethanol/water recrystallization four times are dissolved in the methylene dichloride (100mL) then.(2 * 50mL) washings, concentrating under reduced pressure obtains solid to solution, uses ethanol/water recrystallization three times with saturated sodium bicarbonate aqueous solution.Crystal is dry in 70 ℃ of vacuum ovens, so that 4-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl to be provided] ethyl butyrate, pale yellow crystals, mp129-131 ℃.

MS(APCI)m/z 357(M+H+)；

Analyze: calculated value: C ₁₉H ₂₄N ₄O ₃: C, 64.03; H, 6.79; N, 15.72.Observed value: C, 63.76; H, 6.89; N, 15.49.

Embodiment 35

4-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl]-N-methoxyl group-N-methylbutyryl amine

Step 1:

(2M, 35mL 70mmol) are added to N, and (6.81g is 69.9mmol) in the suspension that stirs in methylene dichloride (100mL) for the O-dimethyl hydroxylamine hydrochloride with the solution of trimethyl aluminium in toluene under 0 ℃.Reaction mixture stirred 15 minutes at 0 ℃, at room temperature 15 minutes then, had been cooled to 0 ℃ then.Add 4-[2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] solution of ethyl butyrate (press embodiment 34 steps 1 prepare) in methylene dichloride (50mL).After 15 minutes, reaction mixture rises to room temperature, reflux 2 days.Reaction mixture is cooled to room temperature, adds methylene dichloride (150mL).Slowly add methyl alcohol (10mL) and 10% aqueous hydrochloric acid (10mL).In mixture, add saturated sodium bicarbonate aqueous solution.Mixture is transferred to separating funnel, separates each layer.The water layer dichloromethane extraction.Merge organic layer,, use the salt of wormwood drying with the saturated sodium bicarbonate aqueous solution washing, filtration, concentrating under reduced pressure obtains 13.9g oil, not purifiedly is used for next step.

Step 2:

Material (13.9g) according to the described general condition treatment step 1 of embodiment 34 steps 2.Crude product forms slurry in ethyl acetate, filter.Concentrated filtrate with purification by flash chromatography (silica gel, with 7% methanol-eluted fractions in the methylene dichloride, solution contains the dense ammonium hydroxide of 0.4 volume %), so that oil to be provided, grinds with ethyl acetate.Form solid, filtering separation is used twice in methanol recrystallization.Crystal is dried overnight in 70 ℃ of vacuum ovens, so that 1.59g 4-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl to be provided]-N-methoxyl group-N-methylbutyryl amine, light yellow solid, mp 163-165 ℃.

MS(APCI)m/z 372(M+H+)；

Analyze: calculated value: C ₁₉H ₂₅N ₅O ₃: C, 61.44; H, 6.78; N, 18.85.Observed value: C, 61.48; H, 6.82; N, 18.68.

Embodiment 36

5-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methylpent acid amides

Step 1:

With salt of wormwood (66.23g, 0.479mol), triethylamine (167mL, 1.20mol) and 5-aminovaleric acid carbethoxy hydrochloride (104g, (100g is 0.470mol) and in the mixture of chloroform (1L) 0.575mol) to be added to 4-chloro-3-nitroquinoline.Reaction mixture at room temperature stirred 4 hours, added entry (200mL).Mixture is transferred to separating funnel, separates each layer.Organic layer is used dried over mgso with saturated sodium bicarbonate aqueous solution and salt water washing, filters, and concentrating under reduced pressure is to provide 151g 5-[(3-nitroquinoline-4-yl) amino] Valeric acid ethylester.

Step 2:

Utilize the general method reduction 5-[(3-nitroquinoline-4-yl described in embodiment 6 steps 2) amino] Valeric acid ethylester (151g, 0.476mol), obtain the thick 5-[(3-quinolylamine of 131.5g-4-yl) amino] Valeric acid ethylester, be not further purified when in next step, using.

Step 3:

Utilize the general method described in embodiment 6 steps 3, make thick 5-[(3-quinolylamine-4-yl) amino] Valeric acid ethylester (26.3g, 91.5mmol) change into the thick 5-of 28g (2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) Valeric acid ethylester, use former butyric acid trimethyl to replace triethly orthoacetate.

Step 4:

(2.23g, 55.9mmol) solution in water (100mL) is added to 5-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) Valeric acid ethylester (14.6g is 43.0mmol) in the solution in ethanol (100mL) with sodium hydroxide.Reaction mixture at room temperature stirs and spends the night, and ethanol is removed in decompression.Remaining aqueous solution washed with dichloromethane is adjusted to pH 5 with 10% aqueous hydrochloric acid.Water layer dichloromethane extraction (2x).Merge the organic layer of back, use dried over mgso, filter, concentrate, obtain 11.5g 5-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) valeric acid, yellow solid.

Step 5

At room temperature (2.62mL, (5.21g is 16.7mmol) in the solution in methylene dichloride (50mL) 30.1mmol) to be added to 5-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) valeric acid with oxalyl chloride.Reaction was stirred 1 hour, and volatile matter is removed in decompression.(50mL) is added in the residue with methylene dichloride, adds N then, and the O-dimethyl hydroxylamine hydrochloride (3.26g, 33.5mmol) and N, dinethylformamide (2mL).Reaction mixture at room temperature stirs and spends the night concentrating under reduced pressure.Residue dilutes with methylene dichloride and solution of ammonium hydroxide.Mixture is transferred to separating funnel, separates each layer.Organic layer is used dried over mgso with saturated sodium bicarbonate aqueous solution and salt water washing, filters, concentrating under reduced pressure is to provide the thick N-methoxyl group of 5.5g-N-methyl-5-(2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl) valeramide, brown oil is not further purified when using in next step.

Step 6:

Material according to the described process treatment step 5 of embodiment 34 steps 2.Come reaction mixture by using separating funnel to separate each layer.Organic layer is used dried over mgso with saturated sodium bicarbonate aqueous solution and salt water washing, filters concentrating under reduced pressure.With flash chromatography (silica gel is with 10% methanol-eluted fractions in the methylene dichloride) the thick 5-of purifying (4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methylpent acid amides, so that solid to be provided.Acetone is added in the solid supersound process mixture.The filtering separation solid, dry in 80 ℃ of vacuum ovens, so that 5-(4-amino-2-propyl group-1H-imidazo [4,5-c] quinoline-1-yl)-N-methoxyl group-N-methylpent acid amides, brown needles, mp 150-151 ℃ to be provided.

MS(APCI)m/z 370.1(M+H+)；

Analyze: calculated value: C ₂₀H ₂₇N ₅O ₂0.15 H ₂O:C, 64.51; H, 7.40; N, 18.81.Observed value: C, 64.16; H, 7.40; N, 18-81.

Embodiment 37

1-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] fourth-2-ketone

Step 1:

Use I.L.Lysenko and O.G.Kulinkovich, Russ.J.Org.Chem., 37, the method described in the pp.1238-1243 (2001) prepares 1-(amino methyl) ring propyl alcohol.With 4-chloro-3-nitroquinoline (7.28g, 34.9mmol) drips of solution in methylene dichloride (30mL) is added to 1-(amino methyl) ring propyl alcohol (36.7mmol) and triethylamine (6.30mL is 45.4mmol) in 0 ℃ of stirred suspension in methylene dichloride (120mL).Mixture at room temperature stirred 3 days, concentrating under reduced pressure.Residue is suspended in the water (150mL), stirs 3 hours.The filtering separation solid, water (50mL) washing, dry in 75 ℃ of vacuum ovens, so that 8.99g 1-{[(3-nitroquinoline-4-yl to be provided) amino] and methyl ring propyl alcohol, yellow solid.

Step 2:

With 1-{[(3-nitroquinoline 4-yl) amino] methyl) and the ring propyl alcohol (4.00g, 15.4mmol) and the mixture of 5% platinum charcoal (400mg) in ethyl acetate (80mL) and methyl alcohol (8mL) on the Parr device at 35psi (2.4 * 10 ⁵Pa) room temperature hydrogenation 3 hours under the hydrogen pressure.With CELITE filtering medium filtering mixt, with 10% methanol/ethyl acetate rinsing.Filtrate is condensed into orange oil, is directly used in next step.

Step 3:

With the material dissolves of step 2 in methylene dichloride (70mL).Solution is cooled to 0 ℃, and dropping oxyethyl group Acetyl Chloride 98Min. (1.7mL, 16.9mmol).Reaction mixture stirred removal of solvent under reduced pressure 1 hour at 0 ℃.Residue is directly used in next step.

Step 4:

The material dissolves of step 3 in ethanol (70mL), add the 2M aqueous sodium hydroxide solution (15mL, 30.8mmol).Reaction mixture heated 1 hour down at 60 ℃, at room temperature stirred and spent the night.Volatile matter is removed in decompression, adds methylene dichloride (70mL) and water (50mL) in the residue that obtains.With 1M HCl mixture is adjusted to pH 7.Separate each layer, water layer dichloromethane extraction (25mL).Merge organic layer, use dried over mgso, filter, concentrate, so that the thick 1-[2-of 4.23g (ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl to be provided] fourth-2-ketone, the brown solid.

Step 5:

At room temperature with mCPBA (2.11g 8.57mmol) is added to 1-[2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl] (1.96g is 6.59mmol) in the solution in chloroform (30mL) for fourth-2-ketone.Reaction mixture stirred 1 hour, was cooled to 0 ℃ then.Add dense ammonium hydroxide (10mL) and Tosyl chloride (1.38g, 7.25mmol).Mixture stirred 1 hour at 0 ℃, filtered.Filtrate is diluted with methylene dichloride (50mL) and saturated sodium bicarbonate aqueous solution (50mL).Separate each layer, water layer dichloromethane extraction (25mL).Merge organic layer, use dried over mgso, filter, concentrate, obtain brown solid.Solid on the efficient flash chromatography of HORIZON (HPFC) instrument purifying (from Biotage, Inc, Charlottesville, Virginia, USA obtains) (silica gel is with comprising 80%CHCl in the chloroform ₃, 18%MeOH and 2% dense NH ₄The 0-35% solution gradient wash-out of OH (CMA)), so that the brown solid to be provided, with chloroform/hexane recrystallization.The filtering separation crystal, dry in 80 ℃ of vacuum ovens, so that 0.718g 1-[4-amino-2-(ethoxyl methyl)-1H-imidazo [4,5-c] quinoline-1-yl to be provided] fourth-2-ketone, lightpink needles, mp 187-188 ℃.

MS(APCI)m/z 313(M+H) ⁺；

Analyze: calculated value: C ₁₇H ₂₀N ₄O ₂: C, 65.37; H, 6.45; N, 17.94.Observed value: C, 65.22; H, 6.19; N, 17.71.

Exemplary compounds

Some exemplary compounds is included in some described in the foregoing description, has following formula following formula (I-2a, I-4a, and I-3a), X wherein, R ₂, and R _1-1Define as following table.In following table, for ring system, a kind of concrete compound of each row representative.

R ₂	X	R _1-1
R ₂	X	R _1-1	H (hydrogen)	-CH ₂-	Methyl
H	-CH ₂-	Ethyl	H (hydrogen)	-CH ₂-	Methyl
H	-CH ₂-	Ethyl	H	-CH ₂-	N-propyl
H	-CH ₂-	Sec.-propyl	H	-CH ₂-	N-propyl
H	-CH ₂-	Sec.-propyl	H	-CH ₂-	Cyclopropyl
H	-CH ₂-	Normal-butyl	H	-CH ₂-	Cyclopropyl
H	-CH ₂-	Normal-butyl	H	-CH ₂-	Sec-butyl
H	-CH ₂-	Isobutyl-	H	-CH ₂-	Sec-butyl
H	-CH ₂-	Isobutyl-	H	-CH ₂-	The tertiary butyl
H	-CH ₂-	N-pentyl	H	-CH ₂-	The tertiary butyl
H	-CH ₂-	N-pentyl	H	-CH ₂-	Cyclopentyl
H	-CH ₂-	N-hexyl	H	-CH ₂-	Cyclopentyl
H	-CH ₂-	N-hexyl	H	-CH ₂-	Cyclohexyl
H	-CH ₂-	Phenyl	H	-CH ₂-	Cyclohexyl
H	-CH ₂-	Phenyl	H	-CH ₂-	The 4-chloro-phenyl-

H	-CH ₂-	The 2,4 dichloro benzene base
H	-CH ₂-	The 2,4 dichloro benzene base	H	-(CH ₂) ₂-	Methyl
H	-(CH ₂) ₂-	Ethyl	H	-(CH ₂) ₂-	Methyl
H	-(CH ₂) ₂-	Ethyl	H	-(CH ₂) ₂-	N-propyl
H	-(CH ₂) ₂-	Sec.-propyl	H	-(CH ₂) ₂-	N-propyl
H	-(CH ₂) ₂-	Sec.-propyl	H	-(CH ₂) ₂-	Cyclopropyl
H	-(CH ₂) ₂-	Normal-butyl	H	-(CH ₂) ₂-	Cyclopropyl
H	-(CH ₂) ₂-	Normal-butyl	H	-(CH ₂) ₂-	Sec-butyl
H	-(CH ₂) ₂-	Isobutyl-	H	-(CH ₂) ₂-	Sec-butyl
H	-(CH ₂) ₂-	Isobutyl-	H	-(CH ₂) ₂-	The tertiary butyl
H	-(CH ₂) ₂-	N-pentyl	H	-(CH ₂) ₂-	The tertiary butyl
H	-(CH ₂) ₂-	N-pentyl	H	-(CH ₂) ₂-	Cyclopentyl
H	-(CH ₂) ₂-	N-hexyl	H	-(CH ₂) ₂-	Cyclopentyl
H	-(CH ₂) ₂-	N-hexyl	H	-(CH ₂) ₂-	Cyclohexyl
H	-(CH ₂) ₂-	Phenyl	H	-(CH ₂) ₂-	Cyclohexyl
H	-(CH ₂) ₂-	Phenyl	H	-(CH ₂) ₂-	The 4-chloro-phenyl-
H	-(CH ₂) ₂-	The 2,4 dichloro benzene base	H	-(CH ₂) ₂-	The 4-chloro-phenyl-
H	-(CH ₂) ₂-	The 2,4 dichloro benzene base	H	-(CH ₂) ₃-	Methyl
H	-(CH ₂) ₃-	Ethyl	H	-(CH ₂) ₃-	Methyl
H	-(CH ₂) ₃-	Ethyl	H	-(CH ₂) ₃-	N-propyl
H	-(CH ₂) ₃-	Sec.-propyl	H	-(CH ₂) ₃-	N-propyl
H	-(CH ₂) ₃-	Sec.-propyl	H	-(CH ₂) ₃-	Cyclopropyl
H	-(CH ₂) ₃-	Normal-butyl	H	-(CH ₂) ₃-	Cyclopropyl
H	-(CH ₂) ₃-	Normal-butyl	H	-(CH ₂) ₃-	Sec-butyl
H	-(CH ₂) ₃-	Isobutyl-	H	-(CH ₂) ₃-	Sec-butyl
H	-(CH ₂) ₃-	Isobutyl-	H	-(CH ₂) ₃-	The tertiary butyl
H	-(CH ₂) ₃-	N-pentyl	H	-(CH ₂) ₃-	The tertiary butyl
H	-(CH ₂) ₃-	N-pentyl	H	-(CH ₂) ₃-	Cyclopentyl
H	-(CH ₂) ₃-	N-hexyl	H	-(CH ₂) ₃-	Cyclopentyl
H	-(CH ₂) ₃-	N-hexyl	H	-(CH ₂) ₃-	Cyclohexyl
H	-(CH ₂) ₃-	Phenyl	H	-(CH ₂) ₃-	Cyclohexyl
H	-(CH ₂) ₃-	Phenyl	H	-(CH ₂) ₃-	The 4-chloro-phenyl-
H	-(CH ₂) ₃-	The 2,4 dichloro benzene base	H	-(CH ₂) ₃-	The 4-chloro-phenyl-
H	-(CH ₂) ₃-	The 2,4 dichloro benzene base	H	-(CH ₂) ₄-	Methyl
H	-(CH ₂) ₄-	Ethyl	H	-(CH ₂) ₄-	Methyl
H	-(CH ₂) ₄-	Ethyl	H	-(CH ₂) ₄-	N-propyl
H	-(CH ₂) ₄-	Sec.-propyl	H	-(CH ₂) ₄-	N-propyl
H	-(CH ₂) ₄-	Sec.-propyl	H	-(CH ₂) ₄-	Cyclopropyl
H	-(CH ₂) ₄-	Normal-butyl	H	-(CH ₂) ₄-	Cyclopropyl

H	-(CH ₂) ₄-	Sec-butyl
H	-(CH ₂) ₄-	Sec-butyl	H	-(CH ₂) ₄-	Isobutyl-
H	-(CH ₂) ₄-	The tertiary butyl	H	-(CH ₂) ₄-	Isobutyl-
H	-(CH ₂) ₄-	The tertiary butyl	H	-(CH ₂) ₄-	N-pentyl
H	-(CH ₂) ₄-	Cyclopentyl	H	-(CH ₂) ₄-	N-pentyl
H	-(CH ₂) ₄-	Cyclopentyl	H	-(CH ₂) ₄-	N-hexyl
H	-(CH ₂) ₄-	Cyclohexyl	H	-(CH ₂) ₄-	N-hexyl
H	-(CH ₂) ₄-	Cyclohexyl	H	-(CH ₂) ₄-	Phenyl
H	-(CH ₂) ₄-	The 4-chloro-phenyl-	H	-(CH ₂) ₄-	Phenyl
H	-(CH ₂) ₄-	The 4-chloro-phenyl-	H	-(CH ₂) ₄-	The 2,4 dichloro benzene base
H	-(CH ₂) ₅-	Methyl	H	-(CH ₂) ₄-	The 2,4 dichloro benzene base
H	-(CH ₂) ₅-	Methyl	H	-(CH ₂) ₅-	Ethyl
H	-(CH ₂) ₅-	N-propyl	H	-(CH ₂) ₅-	Ethyl
H	-(CH ₂) ₅-	N-propyl	H	-(CH ₂) ₅-	Sec.-propyl
H	-(CH ₂) ₅-	Cyclopropyl	H	-(CH ₂) ₅-	Sec.-propyl
H	-(CH ₂) ₅-	Cyclopropyl	H	-(CH ₂) ₅-	Normal-butyl
H	-(CH ₂) ₅-	Sec-butyl	H	-(CH ₂) ₅-	Normal-butyl
H	-(CH ₂) ₅-	Sec-butyl	H	-(CH ₂) ₅-	Isobutyl-
H	-(CH ₂) ₅-	The tertiary butyl	H	-(CH ₂) ₅-	Isobutyl-
H	-(CH ₂) ₅-	The tertiary butyl	H	-(CH ₂) ₅-	N-pentyl
H	-(CH ₂) ₅-	Cyclopentyl	H	-(CH ₂) ₅-	N-pentyl
H	-(CH ₂) ₅-	Cyclopentyl	H	-(CH ₂) ₅-	N-hexyl
H	-(CH ₂) ₅-	Cyclohexyl	H	-(CH ₂) ₅-	N-hexyl
H	-(CH ₂) ₅-	Cyclohexyl	H	-(CH ₂) ₅-	Phenyl
H	-(CH ₂) ₅-	The 4-chloro-phenyl-	H	-(CH ₂) ₅-	Phenyl
H	-(CH ₂) ₅-	The 4-chloro-phenyl-	H	-(CH ₂) ₅-	The 2,4 dichloro benzene base
H	-(CH ₂) ₆-	Methyl	H	-(CH ₂) ₅-	The 2,4 dichloro benzene base
H	-(CH ₂) ₆-	Methyl	H	-(CH ₂) ₆-	Ethyl
H	-(CH ₂) ₆-	N-propyl	H	-(CH ₂) ₆-	Ethyl
H	-(CH ₂) ₆-	N-propyl	H	-(CH ₂) ₆-	Sec.-propyl
H	-(CH ₂) ₆-	Cyclopropyl	H	-(CH ₂) ₆-	Sec.-propyl
H	-(CH ₂) ₆-	Cyclopropyl	H	-(CH ₂) ₆-	Normal-butyl
H	-(CH ₂) ₆-	Sec-butyl	H	-(CH ₂) ₆-	Normal-butyl
H	-(CH ₂) ₆-	Sec-butyl	H	-(CH ₂) ₆-	Isobutyl-
H	-(CH ₂) ₆-	The tertiary butyl	H	-(CH ₂) ₆-	Isobutyl-
H	-(CH ₂) ₆-	The tertiary butyl	H	-(CH ₂) ₆-	N-pentyl
H	-(CH ₂) ₆-	Cyclopentyl	H	-(CH ₂) ₆-	N-pentyl
H	-(CH ₂) ₆-	Cyclopentyl	H	-(CH ₂) ₆-	N-hexyl
H	-(CH ₂) ₆-	Cyclohexyl	H	-(CH ₂) ₆-	N-hexyl

H	-(CH ₂) ₆-	Phenyl
H	-(CH ₂) ₆-	Phenyl	H	-(CH ₂) ₆-	The 4-chloro-phenyl-
H	-(CH ₂) ₆-	The 2,4 dichloro benzene base	H	-(CH ₂) ₆-	The 4-chloro-phenyl-
H	-(CH ₂) ₆-	The 2,4 dichloro benzene base	H	-CH ₂C(CH ₃) ₂-	Methyl
H	-CH ₂C(CH ₃) ₂-	Ethyl	H	-CH ₂C(CH ₃) ₂-	Methyl
H	-CH ₂C(CH ₃) ₂-	Ethyl	H	-CH ₂C(CH ₃) ₂-	N-propyl
H	-CH ₂C(CH ₃) ₂-	Sec.-propyl	H	-CH ₂C(CH ₃) ₂-	N-propyl
H	-CH ₂C(CH ₃) ₂-	Sec.-propyl	H	-CH ₂C(CH ₃) ₂-	Cyclopropyl
H	-CH ₂C(CH ₃) ₂-	Normal-butyl	H	-CH ₂C(CH ₃) ₂-	Cyclopropyl
H	-CH ₂C(CH ₃) ₂-	Normal-butyl	H	-CH ₂C(CH ₃) ₂-	Sec-butyl
H	-CH ₂C(CH ₃) ₂-	Isobutyl-	H	-CH ₂C(CH ₃) ₂-	Sec-butyl
H	-CH ₂C(CH ₃) ₂-	Isobutyl-	H	-CH ₂C(CH ₃) ₂-	The tertiary butyl
H	-CH ₂C(CH ₃) ₂-	N-pentyl	H	-CH ₂C(CH ₃) ₂-	The tertiary butyl
H	-CH ₂C(CH ₃) ₂-	N-pentyl	H	-CH ₂C(CH ₃) ₂-	Cyclopentyl
H	-CH ₂C(CH ₃) ₂-	N-hexyl	H	-CH ₂C(CH ₃) ₂-	Cyclopentyl
H	-CH ₂C(CH ₃) ₂-	N-hexyl	H	-CH ₂C(CH ₃) ₂-	Cyclohexyl
H	-CH ₂C(CH ₃) ₂-	Phenyl	H	-CH ₂C(CH ₃) ₂-	Cyclohexyl
H	-CH ₂C(CH ₃) ₂-	Phenyl	H	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
H	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	H	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
H	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	H	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	H	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	H	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	H	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	H	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
H	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	H	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
H	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
H	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
H	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	H	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
H	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	H	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-
H	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base	H	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-
H	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base	H	-(CH ₂) ₂OCH ₂-	Methyl
H	-(CH ₂) ₂OCH ₂-	Ethyl	H	-(CH ₂) ₂OCH ₂-	Methyl
H	-(CH ₂) ₂OCH ₂-	Ethyl	H	-(CH ₂) ₂OCH ₂-	N-propyl
H	-(CH ₂) ₂OCH ₂-	Sec.-propyl	H	-(CH ₂) ₂OCH ₂-	N-propyl

H	-(CH ₂) ₂OCH ₂-	Cyclopropyl
H	-(CH ₂) ₂OCH ₂-	Cyclopropyl	H	-(CH ₂) ₂OCH ₂-	Normal-butyl
H	-(CH ₂) ₂OCH ₂-	Sec-butyl	H	-(CH ₂) ₂OCH ₂-	Normal-butyl
H	-(CH ₂) ₂OCH ₂-	Sec-butyl	H	-(CH ₂) ₂OCH ₂-	Isobutyl-
H	-(CH ₂) ₂OCH ₂-	The tertiary butyl	H	-(CH ₂) ₂OCH ₂-	Isobutyl-
H	-(CH ₂) ₂OCH ₂-	The tertiary butyl	H	-(CH ₂) ₂OCH ₂-	N-pentyl
H	-(CH ₂) ₂OCH ₂-	Cyclopentyl	H	-(CH ₂) ₂OCH ₂-	N-pentyl
H	-(CH ₂) ₂OCH ₂-	Cyclopentyl	H	-(CH ₂) ₂OCH ₂-	N-hexyl
H	-(CH ₂) ₂OCH ₂-	Cyclohexyl	H	-(CH ₂) ₂OCH ₂-	N-hexyl
H	-(CH ₂) ₂OCH ₂-	Cyclohexyl	H	-(CH ₂) ₂OCH ₂-	Phenyl
H	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	H	-(CH ₂) ₂OCH ₂-	Phenyl
H	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	H	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
H	-(CH ₂) ₃OCH ₂-	Methyl	H	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
H	-(CH ₂) ₃OCH ₂-	Methyl	H	-(CH ₂) ₃OCH ₂-	Ethyl
H	-(CH ₂) ₃OCH ₂-	N-propyl	H	-(CH ₂) ₃OCH ₂-	Ethyl
H	-(CH ₂) ₃OCH ₂-	N-propyl	H	-(CH ₂) ₃OCH ₂-	Sec.-propyl
H	-(CH ₂) ₃OCH ₂-	Cyclopropyl	H	-(CH ₂) ₃OCH ₂-	Sec.-propyl
H	-(CH ₂) ₃OCH ₂-	Cyclopropyl	H	-(CH ₂) ₃OCH ₂-	Normal-butyl
H	-(CH ₂) ₃OCH ₂-	Sec-butyl	H	-(CH ₂) ₃OCH ₂-	Normal-butyl
H	-(CH ₂) ₃OCH ₂-	Sec-butyl	H	-(CH ₂) ₃OCH ₂-	Isobutyl-
H	-(CH ₂) ₃OCH ₂-	The tertiary butyl	H	-(CH ₂) ₃OCH ₂-	Isobutyl-
H	-(CH ₂) ₃OCH ₂-	The tertiary butyl	H	-(CH ₂) ₃OCH ₂-	N-pentyl
H	-(CH ₂) ₃OCH ₂-	Cyclopentyl	H	-(CH ₂) ₃OCH ₂-	N-pentyl
H	-(CH ₂) ₃OCH ₂-	Cyclopentyl	H	-(CH ₂) ₃OCH ₂-	N-hexyl
H	-(CH ₂) ₃OCH ₂-	Cyclohexyl	H	-(CH ₂) ₃OCH ₂-	N-hexyl
H	-(CH ₂) ₃OCH ₂-	Cyclohexyl	H	-(CH ₂) ₃OCH ₂-	Phenyl
H	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	H	-(CH ₂) ₃OCH ₂-	Phenyl
H	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	H	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂OH	-CH ₂-	Methyl	H	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂OH	-CH ₂-	Methyl	-CH ₂OH	-CH ₂-	Ethyl
-CH ₂OH	-CH ₂-	N-propyl	-CH ₂OH	-CH ₂-	Ethyl
-CH ₂OH	-CH ₂-	N-propyl	-CH ₂OH	-CH ₂-	Sec.-propyl
-CH ₂OH	-CH ₂-	Cyclopropyl	-CH ₂OH	-CH ₂-	Sec.-propyl
-CH ₂OH	-CH ₂-	Cyclopropyl	-CH ₂OH	-CH ₂-	Normal-butyl
-CH ₂OH	-CH ₂-	Sec-butyl	-CH ₂OH	-CH ₂-	Normal-butyl
-CH ₂OH	-CH ₂-	Sec-butyl	-CH ₂OH	-CH ₂-	Isobutyl-
-CH ₂OH	-CH ₂-	The tertiary butyl	-CH ₂OH	-CH ₂-	Isobutyl-
-CH ₂OH	-CH ₂-	The tertiary butyl	-CH ₂OH	-CH ₂-	N-pentyl
-CH ₂OH	-CH ₂-	Cyclopentyl	-CH ₂OH	-CH ₂-	N-pentyl

-CH ₂OH	-CH ₂-	N-hexyl
-CH ₂OH	-CH ₂-	N-hexyl	-CH ₂OH	-CH ₂-	Cyclohexyl
-CH ₂OH	-CH ₂-	Phenyl	-CH ₂OH	-CH ₂-	Cyclohexyl
-CH ₂OH	-CH ₂-	Phenyl	-CH ₂OH	-CH ₂-	The 4-chloro-phenyl-
-CH ₂OH	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-CH ₂-	The 4-chloro-phenyl-
-CH ₂OH	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₂-	Methyl
-CH ₂OH	-(CH ₂) ₂-	Ethyl	-CH ₂OH	-(CH ₂) ₂-	Methyl
-CH ₂OH	-(CH ₂) ₂-	Ethyl	-CH ₂OH	-(CH ₂) ₂-	N-propyl
-CH ₂OH	-(CH ₂) ₂-	Sec.-propyl	-CH ₂OH	-(CH ₂) ₂-	N-propyl
-CH ₂OH	-(CH ₂) ₂-	Sec.-propyl	-CH ₂OH	-(CH ₂) ₂-	Cyclopropyl
-CH ₂OH	-(CH ₂) ₂-	Normal-butyl	-CH ₂OH	-(CH ₂) ₂-	Cyclopropyl
-CH ₂OH	-(CH ₂) ₂-	Normal-butyl	-CH ₂OH	-(CH ₂) ₂-	Sec-butyl
-CH ₂OH	-(CH ₂) ₂-	Isobutyl-	-CH ₂OH	-(CH ₂) ₂-	Sec-butyl
-CH ₂OH	-(CH ₂) ₂-	Isobutyl-	-CH ₂OH	-(CH ₂) ₂-	The tertiary butyl
-CH ₂OH	-(CH ₂) ₂-	N-pentyl	-CH ₂OH	-(CH ₂) ₂-	The tertiary butyl
-CH ₂OH	-(CH ₂) ₂-	N-pentyl	-CH ₂OH	-(CH ₂) ₂-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₂-	N-hexyl	-CH ₂OH	-(CH ₂) ₂-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₂-	N-hexyl	-CH ₂OH	-(CH ₂) ₂-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₂-	Phenyl	-CH ₂OH	-(CH ₂) ₂-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₂-	Phenyl	-CH ₂OH	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₃-	Methyl
-CH ₂OH	-(CH ₂) ₃-	Ethyl	-CH ₂OH	-(CH ₂) ₃-	Methyl
-CH ₂OH	-(CH ₂) ₃-	Ethyl	-CH ₂OH	-(CH ₂) ₃-	N-propyl
-CH ₂OH	-(CH ₂) ₃-	Sec.-propyl	-CH ₂OH	-(CH ₂) ₃-	N-propyl
-CH ₂OH	-(CH ₂) ₃-	Sec.-propyl	-CH ₂OH	-(CH ₂) ₃-	Cyclopropyl
-CH ₂OH	-(CH ₂) ₃-	Normal-butyl	-CH ₂OH	-(CH ₂) ₃-	Cyclopropyl
-CH ₂OH	-(CH ₂) ₃-	Normal-butyl	-CH ₂OH	-(CH ₂) ₃-	Sec-butyl
-CH ₂OH	-(CH ₂) ₃-	Isobutyl-	-CH ₂OH	-(CH ₂) ₃-	Sec-butyl
-CH ₂OH	-(CH ₂) ₃-	Isobutyl-	-CH ₂OH	-(CH ₂) ₃-	The tertiary butyl
-CH ₂OH	-(CH ₂) ₃-	N-pentyl	-CH ₂OH	-(CH ₂) ₃-	The tertiary butyl
-CH ₂OH	-(CH ₂) ₃-	N-pentyl	-CH ₂OH	-(CH ₂) ₃-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₃-	N-hexyl	-CH ₂OH	-(CH ₂) ₃-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₃-	N-hexyl	-CH ₂OH	-(CH ₂) ₃-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₃-	Phenyl	-CH ₂OH	-(CH ₂) ₃-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₃-	Phenyl	-CH ₂OH	-(CH ₂) ₃-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₃-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₃-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₃-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₄-	Methyl
-CH ₂OH	-(CH ₂) ₄-	Ethyl	-CH ₂OH	-(CH ₂) ₄-	Methyl

-CH ₂OH	-(CH ₂) ₄-	N-propyl
-CH ₂OH	-(CH ₂) ₄-	N-propyl	-CH ₂OH	-(CH ₂) ₄-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₄-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₄-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₄-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₄-	Normal-butyl
-CH ₂OH	-(CH ₂) ₄-	Sec-butyl	-CH ₂OH	-(CH ₂) ₄-	Normal-butyl
-CH ₂OH	-(CH ₂) ₄-	Sec-butyl	-CH ₂OH	-(CH ₂) ₄-	Isobutyl-
-CH ₂OH	-(CH ₂) ₄-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₄-	Isobutyl-
-CH ₂OH	-(CH ₂) ₄-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₄-	N-pentyl
-CH ₂OH	-(CH ₂) ₄-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₄-	N-pentyl
-CH ₂OH	-(CH ₂) ₄-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₄-	N-hexyl
-CH ₂OH	-(CH ₂) ₄-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₄-	N-hexyl
-CH ₂OH	-(CH ₂) ₄-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₄-	Phenyl
-CH ₂OH	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₄-	Phenyl
-CH ₂OH	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₅-	Methyl	-CH ₂OH	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₅-	Methyl	-CH ₂OH	-(CH ₂) ₅-	Ethyl
-CH ₂OH	-(CH ₂) ₅-	N-propyl	-CH ₂OH	-(CH ₂) ₅-	Ethyl
-CH ₂OH	-(CH ₂) ₅-	N-propyl	-CH ₂OH	-(CH ₂) ₅-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₅-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₅-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₅-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₅-	Normal-butyl
-CH ₂OH	-(CH ₂) ₅-	Sec-butyl	-CH ₂OH	-(CH ₂) ₅-	Normal-butyl
-CH ₂OH	-(CH ₂) ₅-	Sec-butyl	-CH ₂OH	-(CH ₂) ₅-	Isobutyl-
-CH ₂OH	-(CH ₂) ₅-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₅-	Isobutyl-
-CH ₂OH	-(CH ₂) ₅-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₅-	N-pentyl
-CH ₂OH	-(CH ₂) ₅-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₅-	N-pentyl
-CH ₂OH	-(CH ₂) ₅-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₅-	N-hexyl
-CH ₂OH	-(CH ₂) ₅-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₅-	N-hexyl
-CH ₂OH	-(CH ₂) ₅-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₅-	Phenyl
-CH ₂OH	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₅-	Phenyl
-CH ₂OH	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₆-	Methyl	-CH ₂OH	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₆-	Methyl	-CH ₂OH	-(CH ₂) ₆-	Ethyl
-CH ₂OH	-(CH ₂) ₆-	N-propyl	-CH ₂OH	-(CH ₂) ₆-	Ethyl
-CH ₂OH	-(CH ₂) ₆-	N-propyl	-CH ₂OH	-(CH ₂) ₆-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₆-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₆-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₆-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₆-	Normal-butyl
-CH ₂OH	-(CH ₂) ₆-	Sec-butyl	-CH ₂OH	-(CH ₂) ₆-	Normal-butyl
-CH ₂OH	-(CH ₂) ₆-	Sec-butyl	-CH ₂OH	-(CH ₂) ₆-	Isobutyl-
-CH ₂OH	-(CH ₂) ₆-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₆-	Isobutyl-

-CH ₂OH	-(CH ₂) ₆-	N-pentyl
-CH ₂OH	-(CH ₂) ₆-	N-pentyl	-CH ₂OH	-(CH ₂) ₆-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₆-	N-hexyl	-CH ₂OH	-(CH ₂) ₆-	Cyclopentyl
-CH ₂OH	-(CH ₂) ₆-	N-hexyl	-CH ₂OH	-(CH ₂) ₆-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₆-	Phenyl	-CH ₂OH	-(CH ₂) ₆-	Cyclohexyl
-CH ₂OH	-(CH ₂) ₆-	Phenyl	-CH ₂OH	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂OH	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂OH	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂OH	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂OH	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂OH	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂OH	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂OH	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-
-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base	-CH ₂OH	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-

-CH ₂OH	-(CH ₂) ₂OCH ₂-	Methyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂OH	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂OH	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂OH	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂OH	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂OH	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂OH	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₂OH	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₂OH	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₃(methyl)	-CH ₂-	Methyl	-CH ₂OH	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₃(methyl)	-CH ₂-	Methyl	-CH ₃	-CH ₂-	Ethyl
-CH ₃	-CH ₂-	N-propyl	-CH ₃	-CH ₂-	Ethyl
-CH ₃	-CH ₂-	N-propyl	-CH ₃	-CH ₂-	Sec.-propyl
-CH ₃	-CH ₂-	Cyclopropyl	-CH ₃	-CH ₂-	Sec.-propyl
-CH ₃	-CH ₂-	Cyclopropyl	-CH ₃	-CH ₂-	Normal-butyl
-CH ₃	-CH ₂-	Sec-butyl	-CH ₃	-CH ₂-	Normal-butyl

-CH ₃	-CH ₂-	Isobutyl-
-CH ₃	-CH ₂-	Isobutyl-	-CH ₃	-CH ₂-	The tertiary butyl
-CH ₃	-CH ₂-	N-pentyl	-CH ₃	-CH ₂-	The tertiary butyl
-CH ₃	-CH ₂-	N-pentyl	-CH ₃	-CH ₂-	Cyclopentyl
-CH ₃	-CH ₂-	N-hexyl	-CH ₃	-CH ₂-	Cyclopentyl
-CH ₃	-CH ₂-	N-hexyl	-CH ₃	-CH ₂-	Cyclohexyl
-CH ₃	-CH ₂-	Phenyl	-CH ₃	-CH ₂-	Cyclohexyl
-CH ₃	-CH ₂-	Phenyl	-CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₃	-(CH ₂) ₂-	Methyl
-CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₃	-(CH ₂) ₂-	Methyl
-CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₃	-(CH ₂) ₃-	Methyl
-CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₃	-(CH ₂) ₃-	Methyl
-CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₃	-(CH ₂) ₃-	The tertiary butyl
-CH ₃	-(CH ₂) ₃-	N-pentyl	-CH ₃	-(CH ₂) ₃-	The tertiary butyl
-CH ₃	-(CH ₂) ₃-	N-pentyl	-CH ₃	-(CH ₂) ₃-	Cyclopentyl
-CH ₃	-(CH ₂) ₃-	N-hexyl	-CH ₃	-(CH ₂) ₃-	Cyclopentyl
-CH ₃	-(CH ₂) ₃-	N-hexyl	-CH ₃	-(CH ₂) ₃-	Cyclohexyl
-CH ₃	-(CH ₂) ₃-	Phenyl	-CH ₃	-(CH ₂) ₃-	Cyclohexyl

-CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-
-CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₄-	Methyl	-CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₄-	Methyl	-CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₅-	Methyl	-CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₅-	Methyl	-CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₆-	Methyl	-CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₆-	Methyl	-CH ₃	-(CH ₂) ₆-	Ethyl
-CH ₃	-(CH ₂) ₆-	N-propyl	-CH ₃	-(CH ₂) ₆-	Ethyl
-CH ₃	-(CH ₂) ₆-	N-propyl	-CH ₃	-(CH ₂) ₆-	Sec.-propyl
-CH ₃	-(CH ₂) ₆-	Cyclopropyl	-CH ₃	-(CH ₂) ₆-	Sec.-propyl

-CH ₃	-(CH ₂) ₆-	Normal-butyl
-CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl

-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃(ethyl)	-CH ₂-	Methyl	-CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃(ethyl)	-CH ₂-	Methyl	-CH ₂CH ₃	-CH ₂-	Ethyl
-CH ₂CH ₃	-CH ₂-	N-propyl	-CH ₂CH ₃	-CH ₂-	Ethyl

-CH ₂CH ₃	-CH ₂-	Sec.-propyl
-CH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl
-CH ₂CH ₃	-(CH ₂) ₃-	N-pentyl	-CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl

-CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl
-CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₆-	Methyl	-CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base

-CH ₂CH ₃	-(CH ₂) ₆-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl

-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl

-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃(n-propyl)	-CH ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂CH ₂CH ₃(n-propyl)	-CH ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂CH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂CH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂CH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl

-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Uncle's normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Uncle's normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Uncle's normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Uncle's normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl

-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl

-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl

-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃(normal-butyl)	-CH ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃(normal-butyl)	-CH ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Methyl

-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-

-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-

-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl

-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂CH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃(ethoxyl methyl)	-CH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂OCH ₂CH ₃(ethoxyl methyl)	-CH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-CH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-CH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-CH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-CH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-CH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-CH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Cyclohexyl

-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-propyl

-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Methyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Methyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Ethyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Ethyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Methyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Ethyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-propyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl

-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	Phenyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Ethyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Methyl

-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-propyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	Phenyl
-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃(2-methoxy ethyl)	-CH ₂-	Methyl	-CH ₂OCH ₂CH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃(2-methoxy ethyl)	-CH ₂-	Methyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-CH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-CH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Methyl	-CH ₂CH ₂OCH ₃	-CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Isobutyl-

-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂～	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂～	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	Phenyl

-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₄-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₅-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₆-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Methyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Ethyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-propyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Normal-butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclopropyl

-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Methyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 4-chloro-phenyl-	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂OCH ₃	-CH ₂C(CH ₃) ₂CH ₂-	The 2,4 dichloro benzene base
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Methyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Ethyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Sec.-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Cyclopropyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Normal-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Sec-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Isobutyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The tertiary butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-pentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Cyclopentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Cyclohexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	N-hexyl

-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Phenyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₂OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Methyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Ethyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-propyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Sec.-propyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclopropyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Normal-butyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Sec-butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Isobutyl-	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	The tertiary butyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-pentyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclopentyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	N-hexyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Cyclohexyl
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	Phenyl	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-
-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	The 2,4 dichloro benzene base	-CH ₂CH ₂OCH ₃	-(CH ₂) ₃OCH ₂-	The 4-chloro-phenyl-

Cytokine induction in people's cell

When using following method to test, but find the compound inducing cell factor of the present invention biosynthesizing.

Vitro human hemocyte system is used to the analysis of cells factor and induces.Press people such as testing Testerman at " Cytokine Induction by the Immunomodulators Imiquimod andS-27609 ", Journal of Leukocyte Biology, 58,365-372 (September nineteen ninety-five) is described, activity is based on the measurement to Interferon, rabbit and tumour necrosis factor (α) (being respectively IFN and TNF), and they are secreted in the substratum.

The substratum preparation of hemocyte

By venipuncture with healthy people contributor's whole blood collection in EDTA vacuum blood-collecting tube.Use HISTOPAQUE-1077 from whole blood, to isolate peripheral blood mononuclear cell (PBMC) by density gradient centrifugation.With Dulbecco phosphate-buffered salt (DPBS) or Hank balanced salt solution (HBSS) with hemodilution to 1: 1.Collect the PBMC layer, wash 2 times with DPBS or HBSS, and with 4 * 10 ⁶Cell/mL is resuspended in the RPMI perfect medium.PBMC suspension is added to (Costar, Cambridge, MA or Becton Dickinson Labware in the flat sterilization tissue culturing plate of 48 holes, Lincoln Park, NJ), wherein contain isopyknic RPMI perfect medium, contain test compounds in the described substratum.

Compound

With compound dissolution in dimethyl sulfoxide (DMSO) (DMSO).For being added in the culture hole, DMSO concentration is no more than 1% ultimate density.Compound is usually at the scope build-in test of concentration 30-0.014 μ M.

Cultivate

Test compounds solution is added to 60 μ M in first hole of containing the RPMI perfect medium, and serial dilution is 3 times in each hole., then isopyknic PBMC suspension is added in each hole, test compounds concentration is transferred to required scope (30-0.014 μ M).The ultimate density of PBMC suspension is 2 * 10 ⁶Cell/mL.Each plate covers with the sterilization plastic cover, the gentle mixing, is cultivating in 5% carbon dioxide atmosphere 18～24 hours under 37 ℃ then.

Separate

After the cultivation, each plate under 4 ℃ with 1000rpm (about 200 * g) centrifugal 10 minutes.Remove not celliferous culture supernatant with sterilization polypropylene suction pipe, and transfer in the sterilization polypropylene tube.Sample remains on-30～-70 ℃, up to analysis.By the elisa assay sample, pass through ELISA or IGEN analytic sample for Interferon, rabbit (α) for tumour necrosis factor (α).

By elisa assay Interferon, rabbit (α) and tumour necrosis factor (α)

Use is from PBL Biomedical Laboratories, and many species of people test kit that New Brunswick, NJ obtain is measured Interferon, rabbit (α) concentration by ELISA.The result represents with pg/mL.

Use is from Biosource International, and the ELISA kit measurement tumour necrosis factor (α) that Camarillo, CA obtain is concentration (TNF).Optional, can pass through ORIGEN M-series immune analysis determination TNF concentration, and at IGEN International, Gaithersburg, reading on the IGEN M-8 analyzer of MD.Immunoassay uses from Biosource International, and people TNF grabber that Camarillo, CA obtain and detection antibody are right.The result represents with pg/mL.

Yin Shu patent, patent document and publication seem each all Individual existence with its full content as a reference herein.Those skilled in the art can make various modifications and variations to the present invention without departing from the spirit and scope of the present invention.Should be appreciated that the present invention should not be interpreted as being limited inadequately by these exemplary as herein described and embodiment, these embodiment and embodiment are only represented the embodiment in the scope of the invention, and the present invention is only limited by following claims.

Claims

1. the compound of a formula (I-1) or the acceptable salt of its medicine:

Wherein:

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7;

R _AAnd R _BEach is independently selected from:

Hydrogen,

Halogen,

Alkyl,

Alkenyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂；

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

-N(R ₉) ₂；

R _aBe selected from:

Halogen,

Hydroxyl,

Alkyl,

Alkenyl,

Haloalkyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂。

2. the compound of a formula (I-2) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Or R _1-3Group can be joined together to form and comprise saturated or undersaturated 5-, 6-, or

The ring system of 7-unit ring;

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

-N(R ₉) ₂；

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) _0-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7.

3. the compound of a formula (I-3) or the acceptable salt of its medicine:

Wherein:

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) _0-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) ₀-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7;

R _A' and R _B' each is independently selected from:

Hydrogen,

Halogen,

Alkyl,

Alkenyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂。

4. the compound of a formula (I-4) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃With

R _aBe selected from:

Halogen,

Hydroxyl,

Alkyl,

Alkenyl,

Haloalkyl,

Alkoxyl group,

Alkyl sulfide and

-N(R ₉) ₂；

R ₂Be selected from:

-R ₄，

-X′-R ₄，

-X '-Y '-R ₄And

-X′-R ₅；

Y ' is selected from:

-S(O) ₀-2-，

-S(O) ₂-N(R ₈)-，

-C(R ₆)-，

-C(R ₆)-O-，

-O-C(R ₆)-，

-O-C(O)-O-，

-N(R ₈)-Q′-，

-C(R ₆)-N(R ₈)-，

-O-C(R ₆)-N(R ₈)-，

-C(R ₆)-N(OR ₉)-，

R ₅Be selected from

R ₆Be selected from=O and=S;

R ₇Be C _2-7Alkylidene group;

R ₉Be selected from hydrogen and alkyl;

R ₁₀Be C _3-8Alkylidene group;

A is selected from-O-,-C (O)-and ,-S (O) ₀-2-,-CH ₂-and-N (R ₄)-;

V is selected from-C (R ₆)-,-O-C (R ₆)-and-S (O) ₂-;

A and b are 1～6 integer independently, and condition is a+b≤7.

5. the compound of a formula (Ia) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl,

-N (CH ₃) (OCH ₃) and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Haloalkyl,

Alkoxyl group and

N (R ₉) ₂With

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

6. the compound of a formula (Ib) or the acceptable salt of its medicine:

Wherein:

X is an alkylidene group;

N is 0～4 integer;

R _1-1Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Oxygen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

7. the compound of a formula (Id) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

8. the compound of a formula (Ie) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂And

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

9. compound as claimed in claim 3 or salt, wherein R _A' and R _B' be independently selected from hydrogen and alkyl.

10. compound as claimed in claim 9 or salt, wherein R _A' and R _B' all be methyl.

11. as each described compound or salt in claim 2 or 4～8, wherein n is 0.

12. as claim 1～4,9, or 10 or quote each described compound or salt in the claim 11 of one of claim 2 or 4, wherein Z be-C (O)-.

13. as claim 1～4,9, or 10 or quote each described compound or salt in the claim 11 of one of claim 2 or 4, wherein Z is-C (O) O-.

14. as claim 1～4,9, or 10 or quote each described compound or salt in the claim 11 of one of claim 2 or 4, wherein Z is-C (Q-R _1-3) ₂-.

15. compound as claimed in claim 14 or salt, wherein R _1-3Be alkyl, or R _1-3Group is connected to form 5-unit ring.

16. compound as claimed in claim 14 or salt, wherein R _1-35-, 6-, or 7-unit ring is optional condenses into one or two saturated or unsaturated 5-, 6-, or 7-unit ring, or by one or more aryl that are selected from, heteroaryl, halogen, haloalkyl, the substituting group of alkylidene group-O-alkyl and the aryl that replaces replaces.

17. as claim 1～4,9, or 10, or quote the claim 11 of one of claim 2,4 or 7, or each described compound or salt in the claim 14～16, wherein each Q is-O-.

18. as claim 1～5,9, or 10, or quote the claim 11 of one of claim 2,4 or 5, or each described compound or salt, wherein R in the claim 12 _1-1Be selected from aryl, alkyl and-N (CH ₃) OCH ₃

19. as claim 1～5, one of 7,9, or 10, or quote claim 2,4,5 or 7 claim 11, or claim 12, or each described compound or salt, wherein R in the claim 14～17 _1-1Be selected from alkyl, aryl, and hydrogen.

20. as claim 1～5, one of 7～10, or quote claim 2,4,5,7 or 8 claim 11, or claim 12, or each described compound or salt in the claim 14～19, wherein X is C _1-6Alkylidene group or-(CH ₂) _2-4-O-(CH ₂) _1-3-.

21. compound as claimed in claim 20 or salt, wherein X is selected from-(CH ₂) _1-6-,-CH ₂-C (CH ₃) ₂-,-(CH ₂) ₂-O-CH ₂-,-(CH ₂) ₃-O-CH ₂-and-CH ₂-C (CH ₃) ₂-CH ₂-.

22. as claim 1～7,9 or 10; Or quote the claim 11 of one of claim 2 or 4～7; Or claim 12～19; Or quote claim 1～5,7,9,10, or quote claim 2,4,5, or one of 7 claim 11, or the claim 20 of one of claim 14～19; Or quote claim 1～5,7,9,10, or quote claim 2,4,5, or one of 7 claim 11, or each described compound or salt, wherein R in the claim 21 of one of claim 14～19 _1-1Be selected from alkyl and aryl.

23. compound as claimed in claim 22 or salt, wherein R _1-1Be selected from methyl, ethyl, n-propyl, sec.-propyl, cyclopropyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, phenyl, 4-chloro-phenyl-and 2,4 dichloro benzene base.

24. as each described compound or salt, wherein R in the claim 1～23 ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from hydrogen, C _1-10Alkyl, and C _2-10Alkenyl.

25. as each described compound or salt, wherein R in the claim 1～24 ₂Be selected from hydrogen, alkyl, hydroxyalkyl, and alkoxyalkyl.

26. compound as claimed in claim 25 or salt, wherein R ₂Be selected from hydrogen, hydroxymethyl, methyl, ethyl, n-propyl, normal-butyl, ethoxyl methyl and 2-methoxy ethyl.

27. as each described compound or salt in the claim 1～26, wherein X is C _1-6Alkylidene group.

28. compound as claimed in claim 27 or salt, wherein X is selected from-(CH ₂) _1-6-,-CH ₂-C (CH ₃) ₂-and-CH ₂-C (CH ₃) ₂-CH ₂-.

29. a pharmaceutical composition, comprise the treatment significant quantity as each described compound or salt and medicine acceptable carrier in the claim 1～28.

30. the biosynthetic method of cytokine in the induced animal, comprise significant quantity to clothes as each described compound or salt in the claim 1～28 to as described in animal.

31. a method for the treatment of virus disease in the animal that needs treatment, comprise to clothes treatment significant quantity as each described compound or salt in the claim 1～28 to described animal.

32. a method for the treatment of neoplastic disease in the animal that needs treatment, comprise treat significant quantity as each described compound or salt in the claim 1～28 to described animal.

33. the compound of a formula (II) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

Z is-C (O)-,-C (O) O-, or-C (Q-R _1-3) ₂-;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

Condition be if Z be-C (O)-, R so _1-1Also can be-N (CH ₃) (OCH ₃);

Further condition is if Z is-C (O) O-, R so _1-1Not hydrogen;

Further condition is that X does not comprise-the O-group so if Z is-C (O) O-;

Q is O or S;

R _1-3Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N(R ₉) ₂；

R ₂Be selected from:

Hydrogen,

Alkyl,

Alkenyl,

Aryl,

Heteroaryl,

Heterocyclic radical,

Alkylidene group-Y-alkyl,

Alkylidene group-Y-alkenyl,

Alkylidene group-Y-aryl and

Hydroxyl,

Halogen,

-N(R ₃) ₂，

-C (O)-C _1-10Alkyl,

-C (O)-O-C _1-10Alkyl,

-N (R ₃)-C (O)-C _1-10Alkyl,

-N ₃，

Aryl,

Heteroaryl,

Heterocyclic radical,

-C (O)-aryl and

-C (O)-heteroaryl;

Wherein:

Y is-O-or-S (O) _0-2-; With

R ₃Be selected from:

Hydrogen,

C _1-10Alkyl and

C _2-10Alkenyl and

R ₉Be selected from hydrogen and alkyl.

34. the compound of a formula (III) or the acceptable salt of its medicine:

Wherein:

N is 0～4 integer;

R _1-1Be selected from:

Hydrogen,

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl,

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

N (R ₉) ₂With

R ₉Be selected from hydrogen and alkyl.

35. the compound of a formula (IV) or the acceptable salt of its medicine:

Wherein:

X is an alkylidene group;

N is 0～4 integer;

R _1-1Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl,

-NH-SO ₂-R _1-4，

-NH-C(O)-R _1-4，

-NH-C(O)-NH ₂，

-NH-C (O)-NH-R _1-4And

-N ₃；

R _1-4Be selected from:

Alkyl,

Aryl,

Alkylidene group-aryl,

Heteroaryl,

Alkylidene group-heteroaryl and

Halogen,

Cyano group,

Nitro,

Alkoxyl group,

Dialkylamino,

Alkyl sulfide,

Haloalkyl,

Halogenated alkoxy,

Alkyl and

-N ₃；

R is selected from:

Fluorine,

Alkyl,

Alkoxyl group,

Haloalkyl and

-N (R ₉) ₂With

R ₉Be selected from hydrogen and alkyl.