ZA200600769B - Sulfonamide substituted imidazoquinolines - Google Patents

Sulfonamide substituted imidazoquinolines Download PDF

Info

Publication number: ZA200600769B
Authority: ZA; South Africa
Prior art keywords: imidazo; quinolin; compound; formula; amino
Prior art date: 2003-06-27

Application number

ZA200600769A

Other languages

English (en)

Inventor

George W Griesgraber

Original Assignee

3M Innovative Properties Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-06-27

Filing date

2006-01-26

Publication date

2007-05-30

2006-01-26 Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co

2007-05-30 Publication of ZA200600769B publication Critical patent/ZA200600769B/en

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RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 8
229940124530 sulfonamide Drugs 0.000 title description 7
125000000565 sulfonamide group Chemical group 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 83
150000003839 salts Chemical class 0.000 claims description 25
108090000695 Cytokines Proteins 0.000 claims description 24
102000004127 Cytokines Human genes 0.000 claims description 24
241001465754 Metazoa Species 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
230000015572 biosynthetic process Effects 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
230000001939 inductive effect Effects 0.000 claims description 9
230000003612 virological effect Effects 0.000 claims description 9
230000001613 neoplastic effect Effects 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
229910052739 hydrogen Inorganic materials 0.000 description 31
229910052757 nitrogen Inorganic materials 0.000 description 30
239000007787 solid Substances 0.000 description 26
229910052799 carbon Inorganic materials 0.000 description 25
238000007429 general method Methods 0.000 description 21
125000000217 alkyl group Chemical group 0.000 description 20
239000000243 solution Substances 0.000 description 19
239000000463 material Substances 0.000 description 17
125000000623 heterocyclic group Chemical group 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
125000001072 heteroaryl group Chemical group 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000007796 conventional method Methods 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
239000001257 hydrogen Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
-1 1,1-dioxidoisothiazolidin-2-yl Chemical group 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
150000001204 N-oxides Chemical class 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
230000028993 immune response Effects 0.000 description 7
GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
125000004103 aminoalkyl group Chemical group 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
150000003456 sulfonamides Chemical group 0.000 description 6
HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 4
YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical class C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000006698 induction Effects 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
238000010189 synthetic method Methods 0.000 description 4
230000009385 viral infection Effects 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
XYYKPSXKBVBMHJ-UHFFFAOYSA-N 3-(2-butylimidazo[4,5-c]quinolin-1-yl)propan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=CN=C21 XYYKPSXKBVBMHJ-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
229940124669 imidazoquinoline Drugs 0.000 description 3
239000010410 layer Substances 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
KCQWOAPKZGATTP-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 KCQWOAPKZGATTP-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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239000002904 solvent Substances 0.000 description 3
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SKPRPEJLFKCOAB-UHFFFAOYSA-N 3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C=NC2=C1 SKPRPEJLFKCOAB-UHFFFAOYSA-N 0.000 description 2
LTPVCZQGBDHLMG-UHFFFAOYSA-N 4-(2-ethylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCN)C3=CN=C21 LTPVCZQGBDHLMG-UHFFFAOYSA-N 0.000 description 2
BHBQPNUVSWIHOD-UHFFFAOYSA-N 4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCN)C3=CN=C21 BHBQPNUVSWIHOD-UHFFFAOYSA-N 0.000 description 2
HKHKLZGFYFCZFA-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN)C3=CN=C21 HKHKLZGFYFCZFA-UHFFFAOYSA-N 0.000 description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 2
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WMJJJJKGVPSSSN-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 WMJJJJKGVPSSSN-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
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Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
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Communicable Diseases (AREA)
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ZA200600769A 2003-06-27 2006-01-26 Sulfonamide substituted imidazoquinolines ZA200600769B (en)

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US48320003P	2003-06-27	2003-06-27

Publications (1)

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ZA200600769B true ZA200600769B (en)	2007-05-30

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ZA200600769A ZA200600769B (en)	2003-06-27	2006-01-26	Sulfonamide substituted imidazoquinolines

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EP (1)	EP1638566A4 (fr)
JP (1)	JP2007521280A (fr)
KR (1)	KR20060035637A (fr)
CN (1)	CN1812789B (fr)
AR (2)	AR044923A1 (fr)
AU (1)	AU2004253929A1 (fr)
BR (1)	BRPI0411916A (fr)
CA (1)	CA2529322A1 (fr)
IL (1)	IL172427A0 (fr)
MX (1)	MXPA06000144A (fr)
MY (1)	MY157827A (fr)
NZ (1)	NZ544330A (fr)
RU (1)	RU2374246C2 (fr)
TW (2)	TW200514784A (fr)
WO (2)	WO2005003065A2 (fr)
ZA (1)	ZA200600769B (fr)

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JP2008530113A (ja)	2005-02-11	2008-08-07	コーリーファーマシューティカルグループ，インコーポレイテッド	オキシムおよびヒドロキシラミン置換イミダゾ［４，５−ｃ］環化合物および方法
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JP2008538550A (ja)	2005-04-01	2008-10-30	コーリーファーマシューティカルグループ，インコーポレイテッド	ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物
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2004
- 2004-06-24 MY MYPI20042461A patent/MY157827A/en unknown
- 2004-06-25 JP JP2006517711A patent/JP2007521280A/ja active Pending
- 2004-06-25 AU AU2004253929A patent/AU2004253929A1/en not_active Abandoned
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Ceased
- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/fr not_active Ceased
- 2004-06-25 NZ NZ544330A patent/NZ544330A/en unknown
- 2004-06-25 CA CA002529322A patent/CA2529322A1/fr not_active Abandoned
- 2004-06-25 AR ARP040102248A patent/AR044923A1/es unknown
- 2004-06-25 EP EP04756208A patent/EP1638566A4/fr not_active Withdrawn
- 2004-06-25 TW TW093118635A patent/TW200514784A/zh unknown
- 2004-06-25 AR ARP040102247A patent/AR044922A1/es unknown
- 2004-06-25 TW TW093118636A patent/TW200511992A/zh unknown
- 2004-06-25 BR BRPI0411916-9A patent/BRPI0411916A/pt not_active IP Right Cessation
- 2004-06-25 CN CN2004800181459A patent/CN1812789B/zh not_active Expired - Fee Related
- 2004-06-25 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 MX MXPA06000144A patent/MXPA06000144A/es unknown
- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/fr not_active Ceased
2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
2006
- 2006-01-26 ZA ZA200600769A patent/ZA200600769B/en unknown

Also Published As

Publication number	Publication date
WO2005003064A3 (fr)	2005-03-31
CN1812789A (zh)	2006-08-02
TW200511992A (en)	2005-04-01
MY157827A (en)	2016-07-29
IL172427A0 (en)	2006-04-10
EP1638566A4 (fr)	2009-03-25
WO2005003064A2 (fr)	2005-01-13
AU2004253929A1 (en)	2005-01-13
MXPA06000144A (es)	2006-04-07
AR044922A1 (es)	2005-10-12
RU2005138915A (ru)	2006-06-27
AR044923A1 (es)	2005-10-12
TW200514784A (en)	2005-05-01
NZ544330A (en)	2009-06-26
CA2529322A1 (fr)	2005-01-13
CN1812789B (zh)	2010-07-14
WO2005003065A2 (fr)	2005-01-13
KR20060035637A (ko)	2006-04-26
WO2005003065A3 (fr)	2005-03-10
BRPI0411916A (pt)	2006-08-15
JP2007521280A (ja)	2007-08-02
EP1638566A2 (fr)	2006-03-29
RU2374246C2 (ru)	2009-11-27

Publication	Publication Date	Title
ZA200600769B (en)	2007-05-30	Sulfonamide substituted imidazoquinolines
US6677349B1 (en)	2004-01-13	Sulfonamide and sulfamide substituted imidazoquinolines
KR100781428B1 (ko)	2007-12-03	술폰아미드 및 술파미드 치환된 이미다조퀴놀린
AU773113B2 (en)	2004-05-20	Amide substituted imidazoquinolines
AU2002230618B2 (en)	2006-11-02	Heterocyclic ether substituted imidazoquinolines
US6969722B2 (en)	2005-11-29	Amide substituted imidazopyridines
NZ515968A (en)	2003-10-31	Urea substituted imidazoquinolines
EP1642580B1 (fr)	2009-08-19	Sulfonamides d' imidazoquinoline
HK1088836A (en)	2006-11-17	Sulfonamide substituted imidazoquinolines
HK1086762B (en)	2010-04-30	Sulfonamide substituted imidazoquinolines