KR20060100409A - 케모킨 수용체 억제제로서 유용한 비피페리디닐 유도체 - Google Patents
케모킨 수용체 억제제로서 유용한 비피페리디닐 유도체 Download PDFInfo
- Publication number
- KR20060100409A KR20060100409A KR1020067008532A KR20067008532A KR20060100409A KR 20060100409 A KR20060100409 A KR 20060100409A KR 1020067008532 A KR1020067008532 A KR 1020067008532A KR 20067008532 A KR20067008532 A KR 20067008532A KR 20060100409 A KR20060100409 A KR 20060100409A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- aryl
- compound
- group
- heterocyclyl
- 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.)
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- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 102000009410 Chemokine receptor Human genes 0.000 title description 5
- 108050000299 Chemokine receptor Proteins 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 239000003443 antiviral agent Substances 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 55
- -1 -OS (O 2 ) CF 3 Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims description 18
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 230000010076 replication Effects 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 8
- 108010032976 Enfuvirtide Proteins 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229960002656 didanosine Drugs 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 8
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims description 7
- 229960002062 enfuvirtide Drugs 0.000 claims description 7
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 7
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 7
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 7
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 6
- 229960000311 ritonavir Drugs 0.000 claims description 6
- 229960001852 saquinavir Drugs 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229960002555 zidovudine Drugs 0.000 claims description 6
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 5
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 5
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 claims description 5
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 5
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 5
- 229960001203 stavudine Drugs 0.000 claims description 5
- 238000007920 subcutaneous administration Methods 0.000 claims description 5
- 108010065805 Interleukin-12 Proteins 0.000 claims description 4
- 108010002350 Interleukin-2 Proteins 0.000 claims description 4
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- YQXCVAGCMNFUMQ-UHFFFAOYSA-N capravirine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)N=C(COC(N)=O)N1CC1=CC=NC=C1 YQXCVAGCMNFUMQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229960001936 indinavir Drugs 0.000 claims description 4
- 229960000689 nevirapine Drugs 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
- 229960000523 zalcitabine Drugs 0.000 claims description 4
- HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 claims description 3
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 3
- ATCRIOJPQXDFNY-ZETCQYMHSA-N 6-chloro-2-(1-furo[2,3-c]pyridin-5-yl-ethylsulfanyl)-pyrimidin-4-ylamine Chemical compound S([C@@H](C)C=1N=CC=2OC=CC=2C=1)C1=NC(N)=CC(Cl)=N1 ATCRIOJPQXDFNY-ZETCQYMHSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229960004748 abacavir Drugs 0.000 claims description 3
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- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 3
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine mesylate Natural products CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 3
- MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- GWFOVSGRNGAGDL-FSDSQADBSA-N 2-amino-9-[(1r,2r,3s)-2,3-bis(hydroxymethyl)cyclobutyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1C[C@H](CO)[C@H]1CO GWFOVSGRNGAGDL-FSDSQADBSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims description 2
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
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- 235000010290 biphenyl Nutrition 0.000 claims description 2
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
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- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US51695403P | 2003-11-03 | 2003-11-03 | |
| US60/516,954 | 2003-11-03 |
Publications (1)
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|---|---|
| KR20060100409A true KR20060100409A (ko) | 2006-09-20 |
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Country Status (14)
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| US (1) | US7652142B2 (https=) |
| EP (1) | EP1687295B1 (https=) |
| JP (2) | JP4757802B2 (https=) |
| KR (1) | KR20060100409A (https=) |
| CN (2) | CN1898231B (https=) |
| AR (1) | AR046923A1 (https=) |
| AT (1) | ATE520683T1 (https=) |
| AU (1) | AU2004285051A1 (https=) |
| CA (1) | CA2544377A1 (https=) |
| IL (1) | IL175331A0 (https=) |
| PE (1) | PE20050574A1 (https=) |
| TW (1) | TW200528445A (https=) |
| WO (1) | WO2005042517A2 (https=) |
| ZA (1) | ZA200603479B (https=) |
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| BRPI0509803A (pt) | 2004-04-13 | 2007-09-18 | Incyte Corp | derivados de piperazinilpiperidina como antagonistas de receptor de quimiocina |
| US20080108586A1 (en) * | 2006-09-06 | 2008-05-08 | Incyte Corporation | Combination therapy for human immunodeficiency virus infection |
| US8119661B2 (en) | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| WO2015091420A1 (de) * | 2013-12-19 | 2015-06-25 | Bayer Pharma Aktiengesellschaft | Substituierte bipiperidinyl-derivate als adrenrezeptor alpha 2c antagonisten |
| SG11201604949XA (en) | 2013-12-19 | 2016-07-28 | Bayer Pharma AG | Substituted piperidinyl-tetrahydroquinolines |
| AP2016009276A0 (en) | 2013-12-19 | 2016-06-30 | Bayer Pharma AG | Substituted piperidinyl-tetrahydroquinolines and their use as alpha-2c adrenoreceptor antagonists |
| CN106029648A (zh) | 2013-12-19 | 2016-10-12 | 拜耳制药股份公司 | 作为肾上腺素能受体α2C拮抗剂的取代的联哌啶基衍生物 |
| CN105456273A (zh) * | 2014-09-02 | 2016-04-06 | 杭州雷索药业有限公司 | 奈韦拉平在制备抗炎药物中的应用 |
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| US5368854A (en) | 1992-08-20 | 1994-11-29 | Schering Corporation | Use of IL-10 to treat inflammatory bowel disease |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| US5952349A (en) * | 1996-07-10 | 1999-09-14 | Schering Corporation | Muscarinic antagonists for treating memory loss |
| US5977138A (en) * | 1996-08-15 | 1999-11-02 | Schering Corporation | Ether muscarinic antagonists |
| US6391865B1 (en) * | 1999-05-04 | 2002-05-21 | Schering Corporation | Piperazine derivatives useful as CCR5 antagonists |
| CA2371583C (en) | 1999-05-04 | 2005-09-13 | Schering Corporation | Piperazine derivatives useful as ccr5 antagonists |
| US6387930B1 (en) * | 1999-05-04 | 2002-05-14 | Schering Corporation | Piperidine derivatives useful as CCR5 antagonists |
| PL364560A1 (en) * | 2001-03-29 | 2004-12-13 | Schering Corporation | Ccr5 antagonists useful for treating aids |
| GB0108876D0 (en) * | 2001-04-09 | 2001-05-30 | Novartis Ag | Organic Compounds |
| AR036366A1 (es) * | 2001-08-29 | 2004-09-01 | Schering Corp | Derivados de piperidina utiles como antagonistas de ccr5, composiciones farmaceuticas, el uso de dichos derivados para la fabricación de un medicamento y un kit |
| FR2835909B1 (fr) | 2002-02-12 | 2004-07-16 | Valeo Thermique Moteur Sa | Boite collectrice pour echangeur de chaleur, notamment pour un vehicule automobile |
-
2004
- 2004-11-01 CN CN2004800382299A patent/CN1898231B/zh not_active Expired - Fee Related
- 2004-11-01 CA CA002544377A patent/CA2544377A1/en not_active Abandoned
- 2004-11-01 JP JP2006538391A patent/JP4757802B2/ja not_active Expired - Fee Related
- 2004-11-01 WO PCT/US2004/036273 patent/WO2005042517A2/en not_active Ceased
- 2004-11-01 AT AT04800524T patent/ATE520683T1/de not_active IP Right Cessation
- 2004-11-01 AU AU2004285051A patent/AU2004285051A1/en not_active Abandoned
- 2004-11-01 EP EP04800524A patent/EP1687295B1/en not_active Expired - Lifetime
- 2004-11-01 US US10/979,075 patent/US7652142B2/en not_active Expired - Fee Related
- 2004-11-01 KR KR1020067008532A patent/KR20060100409A/ko not_active Withdrawn
- 2004-11-01 CN CN201010003780A patent/CN101798299A/zh active Pending
- 2004-11-02 AR ARP040104031A patent/AR046923A1/es not_active Application Discontinuation
- 2004-11-02 TW TW093133368A patent/TW200528445A/zh unknown
- 2004-11-02 PE PE2004001061A patent/PE20050574A1/es not_active Application Discontinuation
-
2006
- 2006-04-30 IL IL175331A patent/IL175331A0/en unknown
- 2006-05-02 ZA ZA200603479A patent/ZA200603479B/en unknown
-
2007
- 2007-10-11 JP JP2007265958A patent/JP2008031180A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7652142B2 (en) | 2010-01-26 |
| EP1687295B1 (en) | 2011-08-17 |
| PE20050574A1 (es) | 2005-10-08 |
| CN1898231A (zh) | 2007-01-17 |
| WO2005042517A3 (en) | 2005-07-28 |
| ATE520683T1 (de) | 2011-09-15 |
| TW200528445A (en) | 2005-09-01 |
| EP1687295A2 (en) | 2006-08-09 |
| JP2008031180A (ja) | 2008-02-14 |
| US20060025441A1 (en) | 2006-02-02 |
| WO2005042517A2 (en) | 2005-05-12 |
| AU2004285051A1 (en) | 2005-05-12 |
| JP2007510653A (ja) | 2007-04-26 |
| AR046923A1 (es) | 2006-01-04 |
| IL175331A0 (en) | 2006-09-05 |
| ZA200603479B (en) | 2007-09-26 |
| CN1898231B (zh) | 2010-10-27 |
| JP4757802B2 (ja) | 2011-08-24 |
| CA2544377A1 (en) | 2005-05-12 |
| CN101798299A (zh) | 2010-08-11 |
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| PA0105 | International application |
Patent event date: 20060502 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
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