MXPA01013004A - Antagonistas del receptor de interleucina-8. - Google Patents

Antagonistas del receptor de interleucina-8.

Info

Publication number: MXPA01013004A
Authority: MX; Mexico
Prior art keywords: urea; hydroxy; bromophenyl; alkyl; phenyl
Prior art date: 1999-06-16

Application number

MXPA01013004A

Other languages

English (en)

Spanish (es)

Inventor

Katherine L Widdowson

Original Assignee

Smithkline Beecham Corp

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.)

1999-06-16

Filing date

2000-06-15

Publication date

2002-07-30

2000-06-15 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2002-07-30 Publication of MXPA01013004A publication Critical patent/MXPA01013004A/es

Links

102000010681 interleukin-8 receptors Human genes 0.000 title description 6
108010038415 interleukin-8 receptors Proteins 0.000 title description 5
239000002464 receptor antagonist Substances 0.000 title 1
229940044551 receptor antagonist Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 189
102000019034 Chemokines Human genes 0.000 claims abstract description 36
108010012236 Chemokines Proteins 0.000 claims abstract description 36
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
201000010099 disease Diseases 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 26
230000001404 mediated effect Effects 0.000 claims abstract description 18
102000012740 beta Adrenergic Receptors Human genes 0.000 claims abstract description 11
108010079452 beta Adrenergic Receptors Proteins 0.000 claims abstract description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 208
-1 C1-10 alkyl halogen Chemical class 0.000 claims description 146
239000004202 carbamide Substances 0.000 claims description 111
125000000217 alkyl group Chemical group 0.000 claims description 108
229910052739 hydrogen Inorganic materials 0.000 claims description 106
239000001257 hydrogen Substances 0.000 claims description 94
125000000623 heterocyclic group Chemical group 0.000 claims description 81
229910052736 halogen Inorganic materials 0.000 claims description 71
125000001072 heteroaryl group Chemical group 0.000 claims description 60
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 54
125000003710 aryl alkyl group Chemical group 0.000 claims description 46
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 37
125000003118 aryl group Chemical group 0.000 claims description 33
125000003107 substituted aryl group Chemical group 0.000 claims description 29
125000003342 alkenyl group Chemical group 0.000 claims description 25
125000005018 aryl alkenyl group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
150000001540 azides Chemical class 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 17
229910052717 sulfur Chemical group 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
239000011593 sulfur Chemical group 0.000 claims description 14
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 12
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
229940124530 sulfonamide Drugs 0.000 claims description 8
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
150000003456 sulfonamides Chemical class 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
UUDFKBXAWIEQJG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-nitrophenyl)urea Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1NC(=O)NC1=CC=CC=C1Br UUDFKBXAWIEQJG-UHFFFAOYSA-N 0.000 claims description 6
XJGIXEVHERZBQV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxyphenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC=C1Br XJGIXEVHERZBQV-UHFFFAOYSA-N 0.000 claims description 6
108010018976 Interleukin-8A Receptors Proteins 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
GZOMTDYQJHIAGF-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-5-nitrophenyl)urea Chemical compound OC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC1=CC=CC(Cl)=C1Cl GZOMTDYQJHIAGF-UHFFFAOYSA-N 0.000 claims description 4
PEBCQTKZVQCXJP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3,4-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC=C1Br PEBCQTKZVQCXJP-UHFFFAOYSA-N 0.000 claims description 4
VIKJECVSALYBJB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-cyano-2-hydroxyphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1Br VIKJECVSALYBJB-UHFFFAOYSA-N 0.000 claims description 4
JFLMWUAMXJXUAG-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1Cl JFLMWUAMXJXUAG-UHFFFAOYSA-N 0.000 claims description 4
KNPLCJZGNRGZAN-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O KNPLCJZGNRGZAN-UHFFFAOYSA-N 0.000 claims description 4
UZWXETXUKFOJFK-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O UZWXETXUKFOJFK-UHFFFAOYSA-N 0.000 claims description 4
MHEWCJHSRKVNIF-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenoxyphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 MHEWCJHSRKVNIF-UHFFFAOYSA-N 0.000 claims description 4
PXEWTGQJHBTLOG-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1O PXEWTGQJHBTLOG-UHFFFAOYSA-N 0.000 claims description 4
UROHGCKFAXVYKN-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 UROHGCKFAXVYKN-UHFFFAOYSA-N 0.000 claims description 4
GTJXCKKJNGSTCK-UHFFFAOYSA-N 1-(3-chloro-2-methoxyphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound COC1=C(Cl)C=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O GTJXCKKJNGSTCK-UHFFFAOYSA-N 0.000 claims description 4
IAIFWAOFGOIHNN-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl IAIFWAOFGOIHNN-UHFFFAOYSA-N 0.000 claims description 4
DQRKQLTUZBFHPB-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl DQRKQLTUZBFHPB-UHFFFAOYSA-N 0.000 claims description 4
ZHFMJOHHDQGOTA-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O ZHFMJOHHDQGOTA-UHFFFAOYSA-N 0.000 claims description 4
WXLBSLQDYGMCGF-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O WXLBSLQDYGMCGF-UHFFFAOYSA-N 0.000 claims description 4
YZAZGBOPFBFDAC-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 YZAZGBOPFBFDAC-UHFFFAOYSA-N 0.000 claims description 4
241000700605 Viruses Species 0.000 claims description 4
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 3
CBPGTUOXTFTWTE-UHFFFAOYSA-N 1-(1,3-benzodioxol-4-yl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC2=C1OCO2 CBPGTUOXTFTWTE-UHFFFAOYSA-N 0.000 claims description 3
WTBSKJMUSCALAE-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl WTBSKJMUSCALAE-UHFFFAOYSA-N 0.000 claims description 3
DNYOWRQDSNGAQQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxy-4-methylphenyl)urea Chemical compound OC1=C(C#N)C(C)=CC=C1NC(=O)NC1=CC=CC=C1Br DNYOWRQDSNGAQQ-UHFFFAOYSA-N 0.000 claims description 3
MPSVIJAQCVNHHQ-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 MPSVIJAQCVNHHQ-UHFFFAOYSA-N 0.000 claims description 3
BNWWISXBCWURFH-UHFFFAOYSA-N 3-[(2-bromophenyl)carbamoylamino]-2-hydroxy-n-phenylbenzamide Chemical compound C1=CC=C(C(=O)NC=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br BNWWISXBCWURFH-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
241000723346 Cinnamomum camphora Species 0.000 claims description 3
208000001132 Osteoporosis Diseases 0.000 claims description 3
230000033115 angiogenesis Effects 0.000 claims description 3
229960000846 camphor Drugs 0.000 claims description 3
229930008380 camphor Natural products 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
208000007565 gingivitis Diseases 0.000 claims description 3
210000003958 hematopoietic stem cell Anatomy 0.000 claims description 3
201000004792 malaria Diseases 0.000 claims description 3
230000000241 respiratory effect Effects 0.000 claims description 3
150000003573 thiols Chemical group 0.000 claims description 3
MQBZVUNNWUIPMK-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1Br MQBZVUNNWUIPMK-UHFFFAOYSA-N 0.000 claims description 2
241000711557 Hepacivirus Species 0.000 claims description 2
241000700721 Hepatitis B virus Species 0.000 claims description 2
SBDNCFMDGBKCIR-UHFFFAOYSA-N OC1=C(C=CC(=C1)[N+](=O)[O-])N(C(=O)N)C1=C(C=CC=C1)I Chemical compound OC1=C(C=CC(=C1)[N+](=O)[O-])N(C(=O)N)C1=C(C=CC=C1)I SBDNCFMDGBKCIR-UHFFFAOYSA-N 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
208000006454 hepatitis Diseases 0.000 claims description 2
231100000283 hepatitis Toxicity 0.000 claims description 2
208000002672 hepatitis B Diseases 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
125000005000 thioaryl group Chemical group 0.000 claims description 2
241001529453 unidentified herpesvirus Species 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
QIGMVYSPXPXCPN-UHFFFAOYSA-N (2-bromophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1Br QIGMVYSPXPXCPN-UHFFFAOYSA-N 0.000 claims 1
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238000000034 method Methods 0.000 abstract description 136
108090001007 Interleukin-8 Proteins 0.000 abstract description 64
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238000002360 preparation method Methods 0.000 description 238
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238000007429 general method Methods 0.000 description 140
238000005481 NMR spectroscopy Methods 0.000 description 131
238000002451 electron ionisation mass spectrometry Methods 0.000 description 118
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238000001556 precipitation Methods 0.000 description 111
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239000007787 solid Substances 0.000 description 96
239000011541 reaction mixture Substances 0.000 description 91
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
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230000015572 biosynthetic process Effects 0.000 description 79
238000003786 synthesis reaction Methods 0.000 description 79
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XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 57
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Classifications

- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
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Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Diabetes (AREA)
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Urology & Nephrology (AREA)
Biotechnology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Cardiology (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Quinoline Compounds (AREA)

MXPA01013004A 1999-06-16 2000-06-15 Antagonistas del receptor de interleucina-8. MXPA01013004A (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13967599P	1999-06-16	1999-06-16
PCT/US2000/016499 WO2000076495A1 (en)	1999-06-16	2000-06-15	Il-8 receptor antagonists

Publications (1)

Publication Number	Publication Date
MXPA01013004A true MXPA01013004A (es)	2002-07-30

Family

ID=22487790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
MXPA01013004A MXPA01013004A (es)	1999-06-16	2000-06-15	Antagonistas del receptor de interleucina-8.

Country Status (20)

Country	Link
EP (1)	EP1185261A4 (ja)
JP (1)	JP2003501459A (ja)
KR (1)	KR20020010709A (ja)
CN (1)	CN1355697A (ja)
AR (1)	AR030391A1 (ja)
AU (1)	AU766083B2 (ja)
BR (1)	BR0010802A (ja)
CA (1)	CA2377341A1 (ja)
CO (1)	CO5200760A1 (ja)
CZ (1)	CZ20014471A3 (ja)
HK (1)	HK1044483A1 (ja)
HU (1)	HUP0201571A3 (ja)
IL (1)	IL145761A0 (ja)
MX (1)	MXPA01013004A (ja)
NO (1)	NO20016053D0 (ja)
NZ (1)	NZ514695A (ja)
PL (1)	PL352232A1 (ja)
TR (1)	TR200103680T2 (ja)
WO (1)	WO2000076495A1 (ja)
ZA (1)	ZA200109479B (ja)

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US7521479B2 (en) *	2001-04-16	2009-04-21	Panacea Pharmaceuticals, Inc.	Methods of treating prion disease in mammals
GB0201882D0 (en) *	2002-01-28	2002-03-13	Novartis Ag	Organic compounds
US20060058395A1 (en) *	2002-08-01	2006-03-16	Neurosearch A/S	Compounds useful for the treatment of diseases responsive to antiangiogenetic therapy
US7550499B2 (en)	2004-05-12	2009-06-23	Bristol-Myers Squibb Company	Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
AU2005245399A1 (en) *	2004-05-12	2005-12-01	Schering Corporation	CXCR1 and CXCR2 chemokine antagonists
TW200600492A (en)	2004-05-18	2006-01-01	Achillion Pharmaceuticals Inc	Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
JP2008517930A (ja)	2004-10-21	2008-05-29	トランステックファーマ，インコーポレイテッド	ＧａｌＲ１のアゴニストとしてのビススルホンアミド化合物、組成物、及び使用法
EP1954696B1 (en)	2005-01-19	2011-02-23	Bristol-Myers Squibb Company	2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders
WO2006089871A2 (en) *	2005-02-23	2006-08-31	Neurosearch A/S	Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias
US7714002B2 (en)	2005-06-27	2010-05-11	Bristol-Myers Squibb Company	Carbocycle and heterocycle antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
WO2007002584A1 (en)	2005-06-27	2007-01-04	Bristol-Myers Squibb Company	Linear urea mimics antagonists of p2y1 receptor useful in the treatment of thrombotic conditions
ES2352796T3 (es)	2005-06-27	2011-02-23	Bristol-Myers Squibb Company	Antagonistas cíclicos unidos a c del receptor p2y1 útiles en el tratamiento de afecciones trombóticas.
EP1896466B1 (en)	2005-06-27	2011-04-13	Bristol-Myers Squibb Company	N-linked heterocyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions
US7960569B2 (en)	2006-10-17	2011-06-14	Bristol-Myers Squibb Company	Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
JP2008184403A (ja) *	2007-01-29	2008-08-14	Japan Health Science Foundation	新規ｃ型肝炎ウイルス阻害剤
KR100982661B1 (ko) *	2008-04-22	2010-09-17	전남대학교산학협력단	플라스멥신 ⅱ 활성을 저해하는 화합물을 유효성분으로함유하는 말라리아 예방 및 치료를 위한 약학 조성물 및이를 이용한 말라리아 치료방법
KR100970940B1 (ko) *	2010-05-03	2010-07-20	전남대학교산학협력단	플라스멥신 ⅱ 활성을 저해하는 화합물을 유효성분으로 함유하는 말라리아 예방 및 치료를 위한 약학 조성물 및 이를 이용한 말라리아 치료방법
US10093617B1 (en) *	2015-10-30	2018-10-09	Sumitomo Chemical Company, Limited	Method for producing 2-amino-4-substituted phenol

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Publication number	Priority date	Publication date	Assignee	Title
ZA921120B (en) *	1991-02-19	1993-01-27	Smithkline Beecham Corp	Cytokine inhibitors
JPH11503110A (ja) *	1995-02-17	1999-03-23	スミスクライン・ビーチャム・コーポレイション	Ｉｌ−８受容体拮抗剤
WO2000016768A1 (en) *	1998-09-18	2000-03-30	Smithkline Beecham Corporation	Cxcr2 inhibitors and pmn adhesion and t-cell chemotaxis

2000
- 2000-06-13 CO CO00043844A patent/CO5200760A1/es not_active Application Discontinuation
- 2000-06-14 AR ARP000102923A patent/AR030391A1/es not_active Application Discontinuation
- 2000-06-15 IL IL14576100A patent/IL145761A0/xx unknown
- 2000-06-15 PL PL00352232A patent/PL352232A1/xx not_active Application Discontinuation
- 2000-06-15 NZ NZ514695A patent/NZ514695A/en unknown
- 2000-06-15 CA CA002377341A patent/CA2377341A1/en not_active Abandoned
- 2000-06-15 JP JP2001502828A patent/JP2003501459A/ja not_active Withdrawn
- 2000-06-15 HU HU0201571A patent/HUP0201571A3/hu unknown
- 2000-06-15 WO PCT/US2000/016499 patent/WO2000076495A1/en not_active Application Discontinuation
- 2000-06-15 CN CN00809045A patent/CN1355697A/zh active Pending
- 2000-06-15 AU AU57413/00A patent/AU766083B2/en not_active Ceased
- 2000-06-15 TR TR2001/03680T patent/TR200103680T2/xx unknown
- 2000-06-15 EP EP00942843A patent/EP1185261A4/en not_active Withdrawn
- 2000-06-15 CZ CZ20014471A patent/CZ20014471A3/cs unknown
- 2000-06-15 KR KR1020017016142A patent/KR20020010709A/ko not_active Application Discontinuation
- 2000-06-15 BR BR0010802-2A patent/BR0010802A/pt not_active IP Right Cessation
- 2000-06-15 MX MXPA01013004A patent/MXPA01013004A/es unknown
2001
- 2001-11-16 ZA ZA200109479A patent/ZA200109479B/en unknown
- 2001-12-11 NO NO20016053A patent/NO20016053D0/no not_active Application Discontinuation
2002
- 2002-08-22 HK HK02106188.7A patent/HK1044483A1/zh unknown

Also Published As

Publication number	Publication date
CO5200760A1 (es)	2002-09-27
PL352232A1 (en)	2003-08-11
CZ20014471A3 (cs)	2002-08-14
BR0010802A (pt)	2002-02-19
TR200103680T2 (tr)	2002-07-22
KR20020010709A (ko)	2002-02-04
JP2003501459A (ja)	2003-01-14
AU5741300A (en)	2001-01-02
HK1044483A1 (zh)	2002-10-25
CN1355697A (zh)	2002-06-26
HUP0201571A2 (en)	2002-08-28
IL145761A0 (en)	2002-07-25
CA2377341A1 (en)	2000-12-21
NZ514695A (en)	2004-05-28
NO20016053L (no)	2001-12-11
WO2000076495A1 (en)	2000-12-21
NO20016053D0 (no)	2001-12-11
EP1185261A1 (en)	2002-03-13
HUP0201571A3 (en)	2002-11-28
EP1185261A4 (en)	2004-02-25
AR030391A1 (es)	2003-08-20
AU766083B2 (en)	2003-10-09
ZA200109479B (en)	2002-11-18

Publication	Publication Date	Title
US6180675B1 (en)	2001-01-30	IL-8 receptor antagonists
US6262113B1 (en)	2001-07-17	IL-8 receptor antagonists
US6005008A (en)	1999-12-21	IL-8 receptor antagonists
US5780483A (en)	1998-07-14	IL-8 receptor antagonists
US6211373B1 (en)	2001-04-03	Phenyl urea antagonists of the IL-8 receptor
US6271261B1 (en)	2001-08-07	IL-8 receptor antagonists
AU726858B2 (en)	2000-11-23	IL-8 receptor antagonists
MXPA01013004A (es)	2002-07-30	Antagonistas del receptor de interleucina-8.
AU3409197A (en)	1998-01-14	Il-8 receptor antagonists
EP0907362A1 (en)	1999-04-14	Il-8 receptor antagonists
AU729893B2 (en)	2001-02-15	IL-8 receptor antagonists
MXPA01013005A (es)	2002-07-02	Antagonistas de receptor de interleucina-8.
EP0915653A1 (en)	1999-05-19	Il-8 receptor antagonists
IL141121A (en)	2004-09-27	Process for preparing cyano-phenol derivatives
CA2432662A1 (en)	1997-08-21	Il-8 receptor antagonists
WO2000073282A1 (en)	2000-12-07	Il-8 receptor antagonists
CZ256998A3 (cs)	1999-02-17	Antagonista IL-8 receptoru
CA2377397A1 (en)	2000-12-21	Il-8 receptor antagonists
WO2000076508A1 (en)	2000-12-21	Il-8 receptor antagonists
NZ500441A (en)	2001-04-27	Preparation of benzo-2-triazole substituted compounds for use in treating chemokine mediated diseases