ES2291539T3 - Antagonistas vii del receptor ccr3. - Google Patents
Antagonistas vii del receptor ccr3. Download PDFInfo
- Publication number
- ES2291539T3 ES2291539T3 ES02803781T ES02803781T ES2291539T3 ES 2291539 T3 ES2291539 T3 ES 2291539T3 ES 02803781 T ES02803781 T ES 02803781T ES 02803781 T ES02803781 T ES 02803781T ES 2291539 T3 ES2291539 T3 ES 2291539T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- compound
- formula
- cycloalkyl
- hydrogen
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
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- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 title claims description 21
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 title claims description 21
- 239000005557 antagonist Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002252 acyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- -1 C 1 -C 6 aryl-alkyl Chemical group 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 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 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- PYNGHJRZUVXEJW-IAGOWNOFSA-N (1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentan-1-amine Chemical compound N[C@@H]1CCC[C@H]1N1CCC(CC=2C=CC(Cl)=CC=2)CC1 PYNGHJRZUVXEJW-IAGOWNOFSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- NGJFTTUFSAZOMS-DHIUTWEWSA-N 1-[(1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentyl]-3-cyclohexylurea Chemical compound C1=CC(Cl)=CC=C1CC1CCN([C@H]2[C@@H](CCC2)NC(=O)NC2CCCCC2)CC1 NGJFTTUFSAZOMS-DHIUTWEWSA-N 0.000 claims description 4
- LQNAGGWPLKQCEK-WOJBJXKFSA-N 1-[(1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)N[C@@H]1CCC[C@H]1N1CCC(CC=2C=CC(Cl)=CC=2)CC1 LQNAGGWPLKQCEK-WOJBJXKFSA-N 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000005354 acylalkyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- MLOZBBSHHJOKIK-NHCUHLMSSA-N 1-butyl-3-[(1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentyl]urea Chemical compound CCCCNC(=O)N[C@@H]1CCC[C@H]1N1CCC(CC=2C=CC(Cl)=CC=2)CC1 MLOZBBSHHJOKIK-NHCUHLMSSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 239000000460 chlorine Substances 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 238000004587 chromatography analysis Methods 0.000 description 25
- 101710139422 Eotaxin Proteins 0.000 description 22
- 102100023688 Eotaxin Human genes 0.000 description 22
- 210000003979 eosinophil Anatomy 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000035605 chemotaxis Effects 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000002502 liposome Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- VPESQEWIPDEGSY-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1CC1CCNCC1 VPESQEWIPDEGSY-UHFFFAOYSA-N 0.000 description 8
- 102100032367 C-C motif chemokine 5 Human genes 0.000 description 8
- 102100032366 C-C motif chemokine 7 Human genes 0.000 description 8
- 101710155834 C-C motif chemokine 7 Proteins 0.000 description 8
- 108010055166 Chemokine CCL5 Proteins 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 230000001404 mediated effect Effects 0.000 description 8
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- 241000699670 Mus sp. Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 108010058846 Ovalbumin Proteins 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 229940092253 ovalbumin Drugs 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 108010017316 CCR3 Receptors Proteins 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- CHYODESHQQQYFD-IAGOWNOFSA-N (1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentan-1-ol Chemical compound O[C@@H]1CCC[C@H]1N1CCC(CC=2C=CC(Cl)=CC=2)CC1 CHYODESHQQQYFD-IAGOWNOFSA-N 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33481901P | 2001-11-30 | 2001-11-30 | |
| US334819P | 2001-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2291539T3 true ES2291539T3 (es) | 2008-03-01 |
Family
ID=23308965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02803781T Expired - Lifetime ES2291539T3 (es) | 2001-11-30 | 2002-11-20 | Antagonistas vii del receptor ccr3. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7019007B2 (OSRAM) |
| EP (1) | EP1453804B1 (OSRAM) |
| JP (1) | JP2005518364A (OSRAM) |
| KR (1) | KR100579352B1 (OSRAM) |
| CN (1) | CN1296356C (OSRAM) |
| AR (1) | AR037586A1 (OSRAM) |
| AT (1) | ATE370932T1 (OSRAM) |
| AU (1) | AU2002356694A1 (OSRAM) |
| BR (1) | BR0214611A (OSRAM) |
| CA (1) | CA2468402A1 (OSRAM) |
| DE (1) | DE60222015T2 (OSRAM) |
| ES (1) | ES2291539T3 (OSRAM) |
| MX (1) | MXPA04004980A (OSRAM) |
| PL (1) | PL373275A1 (OSRAM) |
| RU (1) | RU2004120065A (OSRAM) |
| WO (1) | WO2003045917A2 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR034257A1 (es) * | 2000-06-30 | 2004-02-18 | Du Pont Pharm Co | Compuesto ureido, composicion farmaceutica que lo comprende y metodo para modular la actividad del receptor de quimiocinas |
| US7491737B2 (en) * | 2002-10-30 | 2009-02-17 | Merck & Co., Inc. | Heterarylpiperidine modulators of chemokine receptor activity |
| EP2415760A3 (en) * | 2003-02-20 | 2012-02-22 | Encysive Pharmaceuticals, Inc. | CCR-9 antagonists |
| IN2006CH00378A (en) | 2003-06-30 | 2007-05-11 | Sumitomo Chemical Co | Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst |
| US7541468B2 (en) * | 2004-06-10 | 2009-06-02 | Bristol-Myers Squibb Company | Process of preparing N-ureidoalkyl-piperidines |
| ES2624845T3 (es) * | 2010-09-29 | 2017-07-17 | Intervet International B.V. | Compuestos de N-heteroarilo con unidad de puente cíclico para el tratamiento de enfermedades parasitarias |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB953005A (en) * | 1961-02-24 | 1964-03-18 | Soc Ind Fab Antibiotiques Sifa | Substituted n-phenylethyl-n-phenyl-piperazines |
| US5051423A (en) | 1988-07-13 | 1991-09-24 | Schering Ag | Derivatized alkanolamines as cardiovascular agents |
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| JPH0592921A (ja) * | 1991-05-17 | 1993-04-16 | Yamanouchi Pharmaceut Co Ltd | シクロヘキシルアルキルアミド および 該化合物を有効成分とするタキキニン抑制剤 |
| ZA9610745B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| GB9601724D0 (en) * | 1996-01-29 | 1996-03-27 | Merck Sharp & Dohme | Therapeutic agents |
| DE69829875T2 (de) * | 1997-10-14 | 2006-03-09 | Mitsubishi Pharma Corp. | Piperazin-verbindungen und ihre medizinische verwendung |
| WO2000035451A1 (en) | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US6486180B1 (en) | 1998-12-18 | 2002-11-26 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CA2347770A1 (en) * | 1998-12-18 | 2000-06-22 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| EP1156807A4 (en) | 1998-12-18 | 2002-04-03 | Du Pont Pharm Co | N-UREIDOALKYL-PIPERIDINES FOR USE AS MODULATORS OF THE ACTIVITY OF CHIMIOKIN RECEPTORS |
| US6331541B1 (en) * | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| EP1140087A4 (en) | 1998-12-18 | 2002-04-03 | Du Pont Pharm Co | N-UREIDOALKYL-PIPERIDINES FOR USE AS MODULATORS OF THE ACTIVITY OF CHIMIOKIN RECEPTORS |
| WO2001007427A1 (en) * | 1999-07-28 | 2001-02-01 | Daiichi Radioisotope Laboratories, Ltd. | Vesamicol piperazine derivatives and drugs containing the same |
| GB0012240D0 (en) * | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
-
2002
- 2002-11-20 DE DE60222015T patent/DE60222015T2/de not_active Expired - Fee Related
- 2002-11-20 PL PL02373275A patent/PL373275A1/xx not_active Application Discontinuation
- 2002-11-20 BR BR0214611-8A patent/BR0214611A/pt not_active IP Right Cessation
- 2002-11-20 KR KR1020047008306A patent/KR100579352B1/ko not_active Expired - Fee Related
- 2002-11-20 CA CA002468402A patent/CA2468402A1/en not_active Abandoned
- 2002-11-20 JP JP2003547369A patent/JP2005518364A/ja active Pending
- 2002-11-20 MX MXPA04004980A patent/MXPA04004980A/es not_active Application Discontinuation
- 2002-11-20 CN CNB028239768A patent/CN1296356C/zh not_active Expired - Fee Related
- 2002-11-20 AU AU2002356694A patent/AU2002356694A1/en not_active Abandoned
- 2002-11-20 ES ES02803781T patent/ES2291539T3/es not_active Expired - Lifetime
- 2002-11-20 AT AT02803781T patent/ATE370932T1/de not_active IP Right Cessation
- 2002-11-20 EP EP02803781A patent/EP1453804B1/en not_active Expired - Lifetime
- 2002-11-20 RU RU2004120065/04A patent/RU2004120065A/ru not_active Application Discontinuation
- 2002-11-20 WO PCT/EP2002/012997 patent/WO2003045917A2/en not_active Ceased
- 2002-11-27 US US10/306,820 patent/US7019007B2/en not_active Expired - Fee Related
- 2002-11-28 AR ARP020104583A patent/AR037586A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040062663A (ko) | 2004-07-07 |
| WO2003045917A2 (en) | 2003-06-05 |
| US20030153578A1 (en) | 2003-08-14 |
| CN1296356C (zh) | 2007-01-24 |
| WO2003045917A3 (en) | 2003-10-09 |
| PL373275A1 (en) | 2005-08-22 |
| AR037586A1 (es) | 2004-11-17 |
| CN1599721A (zh) | 2005-03-23 |
| US7019007B2 (en) | 2006-03-28 |
| DE60222015T2 (de) | 2008-06-05 |
| ATE370932T1 (de) | 2007-09-15 |
| DE60222015D1 (de) | 2007-10-04 |
| RU2004120065A (ru) | 2005-05-27 |
| AU2002356694A1 (en) | 2003-06-10 |
| BR0214611A (pt) | 2004-09-14 |
| MXPA04004980A (es) | 2004-08-11 |
| KR100579352B1 (ko) | 2006-05-12 |
| JP2005518364A (ja) | 2005-06-23 |
| EP1453804A2 (en) | 2004-09-08 |
| CA2468402A1 (en) | 2003-06-05 |
| EP1453804B1 (en) | 2007-08-22 |
| WO2003045917B1 (en) | 2003-12-04 |
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