ZA200207112B - New CCR5 modulators: benzimidazoles or benzotriazoles. - Google Patents
New CCR5 modulators: benzimidazoles or benzotriazoles. Download PDFInfo
- Publication number
- ZA200207112B ZA200207112B ZA200207112A ZA200207112A ZA200207112B ZA 200207112 B ZA200207112 B ZA 200207112B ZA 200207112 A ZA200207112 A ZA 200207112A ZA 200207112 A ZA200207112 A ZA 200207112A ZA 200207112 B ZA200207112 B ZA 200207112B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- phenyl
- heteroaryl
- formula
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- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 title claims 2
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 title claims 2
- 150000001556 benzimidazoles Chemical class 0.000 title description 2
- 150000001565 benzotriazoles Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 151
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000001072 heteroaryl group Chemical group 0.000 claims description 89
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- -1 nitro, hydroxy Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 238000004519 manufacturing process Methods 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 102000004274 CCR5 Receptors Human genes 0.000 claims 2
- 108010017088 CCR5 Receptors Proteins 0.000 claims 2
- 206010063094 Cerebral malaria Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 102000019034 Chemokines Human genes 0.000 description 4
- 108010012236 Chemokines Proteins 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 102100033668 Cartilage matrix protein Human genes 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 102000000012 Chemokine CCL8 Human genes 0.000 description 2
- 108010055204 Chemokine CCL8 Proteins 0.000 description 2
- 102000009571 Macrophage Inflammatory Proteins Human genes 0.000 description 2
- 108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
- 101150019010 CCR3 gene Proteins 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006041 cell recruitment Effects 0.000 description 1
- 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical group C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
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- A61P31/18—Antivirals for RNA viruses for HIV
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0005642.4A GB0005642D0 (en) | 2000-03-10 | 2000-03-10 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207112B true ZA200207112B (en) | 2003-12-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207112A ZA200207112B (en) | 2000-03-10 | 2002-09-04 | New CCR5 modulators: benzimidazoles or benzotriazoles. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6989393B2 (ko) |
| EP (1) | EP1265870A1 (ko) |
| JP (1) | JP2003525928A (ko) |
| KR (1) | KR20020080479A (ko) |
| CN (1) | CN1416421A (ko) |
| AU (1) | AU2001244899A1 (ko) |
| BR (1) | BR0109109A (ko) |
| CA (1) | CA2401524A1 (ko) |
| GB (1) | GB0005642D0 (ko) |
| IL (1) | IL151381A0 (ko) |
| MX (1) | MXPA02008656A (ko) |
| NO (1) | NO20024310L (ko) |
| NZ (1) | NZ521113A (ko) |
| WO (1) | WO2001066525A1 (ko) |
| ZA (1) | ZA200207112B (ko) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| GB2359078A (en) * | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| GB2359551A (en) * | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| SE0102716D0 (sv) * | 2001-08-14 | 2001-08-14 | Astrazeneca Ab | Novel compounds |
| US7244744B2 (en) * | 2001-11-01 | 2007-07-17 | Icagen, Inc. | Piperidines |
| US7812035B2 (en) * | 2001-12-11 | 2010-10-12 | Sepracor Inc. | 4-substituted piperidines, and methods of use thereof |
| GB0221828D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| DE60336576D1 (de) | 2002-10-30 | 2011-05-12 | Merck Sharp & Dohme | Hemmer der akt aktivität |
| AU2004233827B2 (en) | 2003-04-24 | 2009-05-28 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| SE0301369D0 (sv) * | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| EP1496058A1 (en) * | 2003-07-09 | 2005-01-12 | Boehringer Ingelheim Pharma GmbH & Co.KG | Novel N-(heterobicycloalkanes)-substituted Indoles or heteroderivatives thereof |
| US7157471B2 (en) | 2003-08-25 | 2007-01-02 | Boehringer Ingelheim International Gmbh | Haloalkyl- and piperidine-substituted benzimidazole-derivatives |
| CA2536787C (en) * | 2003-08-25 | 2012-02-21 | Boehringer Ingelheim International Gmbh | Haloalkyl- and piperidine-substituted benzimidazole-derivatives |
| WO2005037827A1 (en) | 2003-10-16 | 2005-04-28 | Smithkline Beecham Corporation | Process for preparing benzimidazole thiophenes |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| TW200610761A (en) * | 2004-04-23 | 2006-04-01 | Astrazeneca Ab | Chemical compounds |
| US7723360B2 (en) * | 2004-08-06 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Alkyl-and piperidine-substituted benzimidazole derivatives |
| ES2338590T3 (es) * | 2005-09-06 | 2010-05-10 | Glaxosmithkline Llc | Procedimiento regioselectivo de preparacion de benzoimidazoltiofenos. |
| JP2009515826A (ja) | 2005-10-19 | 2009-04-16 | エフ．ホフマン−ラ ロシュ アーゲー | フェニル−アセトアミドｎｎｒｔ阻害剤 |
| RU2469032C2 (ru) | 2006-12-13 | 2012-12-10 | Ф.Хоффманн-Ля Рош Аг | Производные 2-(пиперидин-4-ил)-4-фенокси- или фениламинопиримидина в качестве ненуклеозидных ингибиторов обратной транскриптазы |
| GB0625523D0 (en) * | 2006-12-21 | 2007-01-31 | Ge Healthcare Ltd | In vivo imaging agents |
| BRPI0815327A2 (pt) * | 2007-08-31 | 2015-12-15 | Purdue Pharma Lp | "compostos de piperidina do tipo quinoxalina substituída e os usos destes" |
| WO2011079087A1 (en) * | 2009-12-23 | 2011-06-30 | Glaxo Group Limited | Enac blockers |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| US11452541B2 (en) | 2016-12-22 | 2022-09-27 | Scientia Vascular, Inc. | Intravascular device having a selectively deflectable tip |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3318900A (en) * | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| EG12406A (en) * | 1976-08-12 | 1979-03-31 | Janssen Pharmaceutica Nv | Process for preparing of novel n-aryl-n-(1-l-4-piperidinyl)-arylacetamides |
| FR2421899A1 (fr) * | 1978-01-16 | 1979-11-02 | Roussel Uclaf | Nouveaux derives du tetrahydropyridinyl-indole et leurs sels, le procede de preparation et l'application a titre de medicaments de ces nouveaux produits |
| US4410528A (en) * | 1980-05-16 | 1983-10-18 | Kyowa Hakko Kogyo Co., Ltd. | Hypotensive piperidine derivatives |
| US5521197A (en) * | 1994-12-01 | 1996-05-28 | Eli Lilly And Company | 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and 3-<1-alkylenearyl>-4-piperidinyl-1h-indoles: new 5-HT1F agonists |
| EP0898568B1 (en) | 1996-04-19 | 2006-10-04 | Neurosearch A/S | 1-(4-piperidyl)-benzimidazoles having neurotrophic activity |
| WO1999004794A1 (en) | 1997-07-25 | 1999-02-04 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| AR013669A1 (es) * | 1997-10-07 | 2001-01-10 | Smithkline Beecham Corp | Compuestos y metodos |
| DK1049689T3 (da) | 1998-01-19 | 2002-07-22 | Pfizer | 4-(2-keto-1-benzimidazolinyl)piperidinderivater som ORL1-receptoragonister |
| US6407121B1 (en) * | 1998-03-19 | 2002-06-18 | Nihon Nohyaku Co., Ltd. | Arylpiperidine derivatives and use thereof |
| MA26659A1 (fr) * | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| PE20001420A1 (es) | 1998-12-23 | 2000-12-18 | Pfizer | Moduladores de ccr5 |
| US6248755B1 (en) * | 1999-04-06 | 2001-06-19 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| WO2000076514A1 (en) | 1999-06-11 | 2000-12-21 | Merck & Co., Inc. | Cyclopentyl modulators of chemokine receptor activity |
| US6340681B1 (en) | 1999-07-16 | 2002-01-22 | Pfizer Inc | 2-benzimidazolylamine compounds as ORL-1-receptor agonists |
| AR025884A1 (es) * | 1999-10-01 | 2002-12-18 | Takeda Pharmaceutical | Compuestos de amina ciclica, su produccion y su uso |
| ES2249237T3 (es) | 2000-01-05 | 2006-04-01 | Pfizer Inc. | Compuestos de bencimidazol como antagonistas del receptor orl1. |
| AU4274401A (en) * | 2000-03-24 | 2001-10-03 | Meiji Seika Kaisha | Diphenylalkylamine derivatives useful as opioid delta receptor agonists |
-
2000
- 2000-03-10 GB GBGB0005642.4A patent/GB0005642D0/en not_active Ceased
-
2001
- 2001-03-06 CN CN01806376A patent/CN1416421A/zh active Pending
- 2001-03-06 JP JP2001565342A patent/JP2003525928A/ja active Pending
- 2001-03-06 WO PCT/SE2001/000470 patent/WO2001066525A1/en not_active Application Discontinuation
- 2001-03-06 BR BR0109109-3A patent/BR0109109A/pt not_active IP Right Cessation
- 2001-03-06 NZ NZ521113A patent/NZ521113A/en unknown
- 2001-03-06 MX MXPA02008656A patent/MXPA02008656A/es unknown
- 2001-03-06 EP EP01918028A patent/EP1265870A1/en not_active Withdrawn
- 2001-03-06 US US10/220,915 patent/US6989393B2/en not_active Expired - Fee Related
- 2001-03-06 IL IL15138101A patent/IL151381A0/xx unknown
- 2001-03-06 KR KR1020027011797A patent/KR20020080479A/ko not_active Application Discontinuation
- 2001-03-06 AU AU2001244899A patent/AU2001244899A1/en not_active Abandoned
- 2001-03-06 CA CA002401524A patent/CA2401524A1/en not_active Abandoned
-
2002
- 2002-09-04 ZA ZA200207112A patent/ZA200207112B/en unknown
- 2002-09-09 NO NO20024310A patent/NO20024310L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20024310D0 (no) | 2002-09-09 |
| MXPA02008656A (es) | 2003-02-24 |
| US20030119869A1 (en) | 2003-06-26 |
| GB0005642D0 (en) | 2000-05-03 |
| NZ521113A (en) | 2004-05-28 |
| KR20020080479A (ko) | 2002-10-23 |
| BR0109109A (pt) | 2003-06-03 |
| AU2001244899A1 (en) | 2001-09-17 |
| IL151381A0 (en) | 2003-04-10 |
| CA2401524A1 (en) | 2001-09-13 |
| CN1416421A (zh) | 2003-05-07 |
| US6989393B2 (en) | 2006-01-24 |
| JP2003525928A (ja) | 2003-09-02 |
| EP1265870A1 (en) | 2002-12-18 |
| NO20024310L (no) | 2002-10-25 |
| WO2001066525A1 (en) | 2001-09-13 |
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