AU2002356694A1 - Ccr-3 receptor antagonists vii - Google Patents
Ccr-3 receptor antagonists vii Download PDFInfo
- Publication number
- AU2002356694A1 AU2002356694A1 AU2002356694A AU2002356694A AU2002356694A1 AU 2002356694 A1 AU2002356694 A1 AU 2002356694A1 AU 2002356694 A AU2002356694 A AU 2002356694A AU 2002356694 A AU2002356694 A AU 2002356694A AU 2002356694 A1 AU2002356694 A1 AU 2002356694A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkylamino
- compound
- hydrogen
- cycloalkyl
- 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.)
- Abandoned
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- 102000004499 CCR3 Receptors Human genes 0.000 title claims description 12
- 108010017316 CCR3 Receptors Proteins 0.000 title claims description 12
- 239000002464 receptor antagonist Substances 0.000 title claims description 6
- 229940044551 receptor antagonist Drugs 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 166
- -1 C-6 alkoxycarbonyl Chemical group 0.000 claims description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- 208000006673 asthma Diseases 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910020008 S(O) Inorganic materials 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 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 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 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 3
- 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 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- KTRSSEQFRCXBDB-NHCUHLMSSA-N ethyl 3-[[(1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentyl]carbamoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)N[C@@H]1CCC[C@H]1N1CCC(CC=2C=CC(Cl)=CC=2)CC1 KTRSSEQFRCXBDB-NHCUHLMSSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000003745 diagnosis Methods 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- VROURLLLOBVPRF-DHIUTWEWSA-N n-[(1r,2r)-2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]cyclopentyl]cyclohexanecarboxamide Chemical compound C1=CC(Cl)=CC=C1CC1CCN([C@H]2[C@@H](CCC2)NC(=O)C2CCCCC2)CC1 VROURLLLOBVPRF-DHIUTWEWSA-N 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- DYBJEOJIXAWVBR-UHFFFAOYSA-N n-[2-(4-benzylpiperazin-1-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1N1CCN(CC=2C=CC=CC=2)CC1 DYBJEOJIXAWVBR-UHFFFAOYSA-N 0.000 claims 2
- JTSYZEMBBZSXBR-UHFFFAOYSA-N n-[2-[4-[2-(3,4-dimethoxyphenyl)ethyl]piperazin-1-yl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCN1CCN(C=2C(=CC=CC=2)NC(C)=O)CC1 JTSYZEMBBZSXBR-UHFFFAOYSA-N 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl 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
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- AZQAWLNVPPPDRY-UHFFFAOYSA-N n-[2-(4-benzylpiperazin-1-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1N1CCN(CC=2C=CC=CC=2)CC1 AZQAWLNVPPPDRY-UHFFFAOYSA-N 0.000 claims 1
- ZOTGCIAILZRDNJ-UHFFFAOYSA-N n-[[4-[[4-(2-acetamido-4-fluorophenyl)piperazin-1-yl]methyl]phenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1CN1CCN(C=2C(=CC(F)=CC=2)NC(C)=O)CC1 ZOTGCIAILZRDNJ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
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- 239000000047 product Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
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- VPESQEWIPDEGSY-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1CC1CCNCC1 VPESQEWIPDEGSY-UHFFFAOYSA-N 0.000 description 12
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- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 201000009732 pulmonary eosinophilia Diseases 0.000 description 1
- 125000003226 pyrazolyl 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
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Chemical group 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- FEXIDQDEGTVERB-UHFFFAOYSA-N tert-butyl 4-[(4-chlorophenyl)methylidene]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1=CC1=CC=C(Cl)C=C1 FEXIDQDEGTVERB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
- 239000003981 vehicle Substances 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
- 238000005303 weighing Methods 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33481901P | 2001-11-30 | 2001-11-30 | |
| US60/334,819 | 2001-11-30 | ||
| PCT/EP2002/012997 WO2003045917A2 (en) | 2001-11-30 | 2002-11-20 | Ccr-3 receptor antagonists vii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2002356694A1 true AU2002356694A1 (en) | 2003-06-10 |
Family
ID=23308965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002356694A Abandoned AU2002356694A1 (en) | 2001-11-30 | 2002-11-20 | Ccr-3 receptor antagonists vii |
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 |
|---|---|---|---|---|
| CA2413245A1 (en) * | 2000-06-30 | 2002-01-10 | Bristol-Myers Squibb Pharma Company | N-ureidoheterocycloaklyl-piperidines as modulators of chemokine receptor activity |
| WO2004041777A2 (en) * | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Heteroarylpiperidine modulators of chemokine receptor activity |
| CA2515780C (en) * | 2003-02-20 | 2012-12-11 | Encysive Pharmaceuticals Inc. | Phenylenediamine urotensin-ii receptor antagonists and ccr-9 antagonists |
| EP1640361B9 (en) * | 2003-06-30 | 2015-11-04 | Sumitomo Chemical Company, Limited | Asymmetric urea compounds and process for producing asymmetric compounds by asymmetric conjugate addition reaction using the same as catalyst |
| US7541468B2 (en) * | 2004-06-10 | 2009-06-02 | Bristol-Myers Squibb Company | Process of preparing N-ureidoalkyl-piperidines |
| BR112013006953A2 (pt) * | 2010-09-29 | 2016-07-26 | Intervet Int Bv | composto, composições farmacêutica e anti-helmíntica, uso de um composto, kit, e, método de tratamento de uma doença |
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 |
| ES2237850T3 (es) * | 1997-10-14 | 2005-08-01 | Mitsubishi Pharma Corporation | Compuestos de piperazina y su uso medicinal. |
| US6331541B1 (en) * | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CA2350730A1 (en) | 1998-12-18 | 2000-06-22 | George V. Delucca | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| AU3126700A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| AU770042B2 (en) * | 1998-12-18 | 2004-02-12 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| DE69926919D1 (de) | 1998-12-18 | 2005-09-29 | Bristol Myers Squibb Pharma Co | N-ureidoalkylpiperidine als modulatoren der aktivität der chemokinrezeptoren |
| WO2000035449A1 (en) | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| 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 CA CA002468402A patent/CA2468402A1/en not_active Abandoned
- 2002-11-20 MX MXPA04004980A patent/MXPA04004980A/es not_active Application Discontinuation
- 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 AU AU2002356694A patent/AU2002356694A1/en not_active Abandoned
- 2002-11-20 DE DE60222015T patent/DE60222015T2/de not_active Expired - Fee Related
- 2002-11-20 RU RU2004120065/04A patent/RU2004120065A/ru not_active Application Discontinuation
- 2002-11-20 JP JP2003547369A patent/JP2005518364A/ja active Pending
- 2002-11-20 BR BR0214611-8A patent/BR0214611A/pt not_active IP Right Cessation
- 2002-11-20 WO PCT/EP2002/012997 patent/WO2003045917A2/en not_active Ceased
- 2002-11-20 CN CNB028239768A patent/CN1296356C/zh not_active Expired - Fee Related
- 2002-11-20 EP EP02803781A patent/EP1453804B1/en not_active Expired - Lifetime
- 2002-11-20 KR KR1020047008306A patent/KR100579352B1/ko not_active Expired - Fee Related
- 2002-11-20 PL PL02373275A patent/PL373275A1/xx not_active Application Discontinuation
- 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 |
|---|---|
| CN1296356C (zh) | 2007-01-24 |
| PL373275A1 (en) | 2005-08-22 |
| US7019007B2 (en) | 2006-03-28 |
| JP2005518364A (ja) | 2005-06-23 |
| DE60222015D1 (de) | 2007-10-04 |
| MXPA04004980A (es) | 2004-08-11 |
| RU2004120065A (ru) | 2005-05-27 |
| CN1599721A (zh) | 2005-03-23 |
| US20030153578A1 (en) | 2003-08-14 |
| AR037586A1 (es) | 2004-11-17 |
| ATE370932T1 (de) | 2007-09-15 |
| EP1453804B1 (en) | 2007-08-22 |
| EP1453804A2 (en) | 2004-09-08 |
| CA2468402A1 (en) | 2003-06-05 |
| WO2003045917A3 (en) | 2003-10-09 |
| KR100579352B1 (ko) | 2006-05-12 |
| BR0214611A (pt) | 2004-09-14 |
| KR20040062663A (ko) | 2004-07-07 |
| WO2003045917A2 (en) | 2003-06-05 |
| ES2291539T3 (es) | 2008-03-01 |
| DE60222015T2 (de) | 2008-06-05 |
| WO2003045917B1 (en) | 2003-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |