JP2006511552A - Ｃｃｒ５拮抗薬としてのピロリジンおよびアゼチジン化合物 - Google Patents
Ｃｃｒ５拮抗薬としてのピロリジンおよびアゼチジン化合物 Download PDFInfo
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- JP2006511552A JP2006511552A JP2004560830A JP2004560830A JP2006511552A JP 2006511552 A JP2006511552 A JP 2006511552A JP 2004560830 A JP2004560830 A JP 2004560830A JP 2004560830 A JP2004560830 A JP 2004560830A JP 2006511552 A JP2006511552 A JP 2006511552A
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- Prior art keywords
- optionally substituted
- dichlorophenyl
- triazaspiro
- ring
- compound
- Prior art date
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 15
- 239000005557 antagonist Substances 0.000 title claims description 6
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 title description 12
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 title description 12
- 150000001539 azetidines Chemical class 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 31
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- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 133
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 229910052757 nitrogen Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 241000124008 Mammalia Species 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
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- 239000011593 sulfur Chemical group 0.000 claims description 20
- 230000009385 viral infection Effects 0.000 claims description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 19
- 229910052698 phosphorus Inorganic materials 0.000 claims description 19
- 239000011574 phosphorus Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
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- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 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 9
- 206010052779 Transplant rejections Diseases 0.000 claims description 9
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 9
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- 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 9
- 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 7
- 239000002253 acid Substances 0.000 claims description 7
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- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 6
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 6
- 206010035148 Plague Diseases 0.000 claims description 6
- 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 6
- 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 6
- 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 6
- 229960004308 acetylcysteine Drugs 0.000 claims description 6
- 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 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 208000037976 chronic inflammation Diseases 0.000 claims description 6
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound 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 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 6
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 6
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 6
- 229960000311 ritonavir Drugs 0.000 claims description 6
- 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 6
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 6
- 229960002555 zidovudine Drugs 0.000 claims description 6
- HNDXHGWVNQBTNH-UHFFFAOYSA-N 8-[3-[3-(3,4-dichlorophenyl)-1-pentanoylpyrrolidin-3-yl]propyl]-1-[3-(trifluoromethyl)phenyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1N(C(=O)CCCC)CCC1(C=1C=C(Cl)C(Cl)=CC=1)CCCN1CCC2(C(NCN2C=2C=C(C=CC=2)C(F)(F)F)=O)CC1 HNDXHGWVNQBTNH-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 206010003178 Arterial thrombosis Diseases 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 claims description 5
- 208000035473 Communicable disease Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 208000022461 Glomerular disease Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000009608 Papillomavirus Infections Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 230000001363 autoimmune Effects 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
- 201000011510 cancer Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 5
- 201000001981 dermatomyositis Diseases 0.000 claims description 5
- 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 5
- 201000002491 encephalomyelitis Diseases 0.000 claims description 5
- 231100000852 glomerular disease Toxicity 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 208000021145 human papilloma virus infection Diseases 0.000 claims description 5
- 230000008595 infiltration Effects 0.000 claims description 5
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- 208000017169 kidney disease Diseases 0.000 claims description 5
- 210000000265 leukocyte Anatomy 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 230000003589 nefrotoxic effect Effects 0.000 claims description 5
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- 231100000381 nephrotoxic Toxicity 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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- SFVBFGGJQKQUNE-UHFFFAOYSA-N 8-[3-[1-(cyclobutanecarbonyl)-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]propyl]-1-[3-(trifluoromethyl)phenyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound FC(F)(F)C1=CC=CC(N2C3(CCN(CCCC4(CN(CC4)C(=O)C4CCC4)C=4C=C(Cl)C(Cl)=CC=4)CC3)C(=O)NC2)=C1 SFVBFGGJQKQUNE-UHFFFAOYSA-N 0.000 claims description 4
- XHDQHNDEKMSTLH-UHFFFAOYSA-N 8-[3-[3-(3,4-dichlorophenyl)-1-(1,2-oxazole-5-carbonyl)pyrrolidin-3-yl]propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CCCN2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CN(C(=O)C=2ON=CC=2)CC1 XHDQHNDEKMSTLH-UHFFFAOYSA-N 0.000 claims description 4
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- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000002955 immunomodulating agent Substances 0.000 claims description 4
- 229940121354 immunomodulator Drugs 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
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- 125000003003 spiro group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
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- BMLMGCPTLHPWPY-REOHCLBHSA-N (4R)-2-oxo-4-thiazolidinecarboxylic acid Chemical compound OC(=O)[C@@H]1CSC(=O)N1 BMLMGCPTLHPWPY-REOHCLBHSA-N 0.000 claims description 3
- KYRSNWPSSXSNEP-ZRTHHSRSSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one Chemical compound 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 KYRSNWPSSXSNEP-ZRTHHSRSSA-N 0.000 claims description 3
- UXDWYQAXEGVSPS-GFUIURDCSA-N (4s)-6-chloro-4-[(e)-2-cyclopropylethenyl]-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one Chemical compound C(/[C@]1(C2=CC(Cl)=CC=C2NC(=O)N1)C(F)(F)F)=C\C1CC1 UXDWYQAXEGVSPS-GFUIURDCSA-N 0.000 claims description 3
- RBEXWVGCIBHYAD-HTQZYQBOSA-N 1-[(2r,5r)-4-hydroxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C(O)[C@@H](CO)O1 RBEXWVGCIBHYAD-HTQZYQBOSA-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
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims description 3
- SCBFBAWJWLXVHS-UHFFFAOYSA-N 2-amino-9-[4-hydroxy-2-(hydroxymethyl)butyl]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(CC(CO)CCO)C=N2 SCBFBAWJWLXVHS-UHFFFAOYSA-N 0.000 claims description 3
- RBWQFZGAMMYYBQ-UHFFFAOYSA-N 3-acetyl-8-[3-[1-acetyl-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]propyl]-1-(3-methylphenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1N(C(=O)C)CCC1(C=1C=C(Cl)C(Cl)=CC=1)CCCN1CCC2(C(N(C(C)=O)CN2C=2C=C(C)C=CC=2)=O)CC1 RBWQFZGAMMYYBQ-UHFFFAOYSA-N 0.000 claims description 3
- WKVDSZYIGHLONN-RRKCRQDMSA-N 5-chloro-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 WKVDSZYIGHLONN-RRKCRQDMSA-N 0.000 claims description 3
- RXBIVTVHJAPOFO-UHFFFAOYSA-N 8-[2-[1-(benzenesulfonyl)-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]oxyethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(OCCN2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CN(S(=O)(=O)C=2C=CC=CC=2)CC1 RXBIVTVHJAPOFO-UHFFFAOYSA-N 0.000 claims description 3
- UBECTFKELCFEJP-UHFFFAOYSA-N 8-[2-[1-(cyclopentanecarbonyl)-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]oxyethyl]-1-(3-methoxyphenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound COC1=CC=CC(N2C3(CCN(CCOC4(CN(CC4)C(=O)C4CCCC4)C=4C=C(Cl)C(Cl)=CC=4)CC3)C(=O)NC2)=C1 UBECTFKELCFEJP-UHFFFAOYSA-N 0.000 claims description 3
- BDGIQNNCLSFLPH-UHFFFAOYSA-N 8-[2-[1-(cyclopentanecarbonyl)-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]oxyethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(OCCN2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CN(C(=O)C2CCCC2)CC1 BDGIQNNCLSFLPH-UHFFFAOYSA-N 0.000 claims description 3
- SBUICUBXZZDNFD-UHFFFAOYSA-N 8-[2-[1-acetyl-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]oxyethyl]-1-(3-methoxyphenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound COC1=CC=CC(N2C3(CCN(CCOC4(CN(CC4)C(C)=O)C=4C=C(Cl)C(Cl)=CC=4)CC3)C(=O)NC2)=C1 SBUICUBXZZDNFD-UHFFFAOYSA-N 0.000 claims description 3
- DVTGJLGNKBFZNW-UHFFFAOYSA-N 8-[2-[1-acetyl-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]oxyethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1N(C(=O)C)CCC1(C=1C=C(Cl)C(Cl)=CC=1)OCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DVTGJLGNKBFZNW-UHFFFAOYSA-N 0.000 claims description 3
- GHEGZKINMNYSGV-UHFFFAOYSA-N 8-[2-[3-(3,4-dichlorophenyl)-1-(furan-2-carbonyl)pyrrolidin-3-yl]oxyethyl]-1-(3-methoxyphenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound COC1=CC=CC(N2C3(CCN(CCOC4(CN(CC4)C(=O)C=4OC=CC=4)C=4C=C(Cl)C(Cl)=CC=4)CC3)C(=O)NC2)=C1 GHEGZKINMNYSGV-UHFFFAOYSA-N 0.000 claims description 3
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Virology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43337202P | 2002-12-13 | 2002-12-13 | |
| PCT/US2003/039618 WO2004055016A1 (en) | 2002-12-13 | 2003-12-12 | Pyrrolidine and azetidine compounds as ccr5 antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006511552A true JP2006511552A (ja) | 2006-04-06 |
| JP2006511552A5 JP2006511552A5 (enExample) | 2007-01-11 |
Family
ID=32595168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004560830A Pending JP2006511552A (ja) | 2002-12-13 | 2003-12-12 | Ｃｃｒ５拮抗薬としてのピロリジンおよびアゼチジン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7271172B2 (enExample) |
| EP (1) | EP1569933B1 (enExample) |
| JP (1) | JP2006511552A (enExample) |
| AT (1) | ATE402176T1 (enExample) |
| AU (1) | AU2003296992A1 (enExample) |
| DE (1) | DE60322423D1 (enExample) |
| ES (1) | ES2309400T3 (enExample) |
| WO (1) | WO2004055016A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1569647B1 (en) * | 2002-12-13 | 2008-08-20 | Smithkline Beecham Corporation | Cyclohexyl compounds as ccr5 antagonists |
| GB0417801D0 (en) * | 2004-08-10 | 2004-09-15 | Novartis Ag | Organic compounds |
| JP2008517916A (ja) * | 2004-10-22 | 2008-05-29 | メルク エンド カムパニー インコーポレーテッド | Ｃｇｒｐ受容体拮抗薬 |
| WO2007011810A1 (en) * | 2005-07-18 | 2007-01-25 | Merck & Co., Inc. | Spiropiperidine beta-secretase inhibitors for the treatment of alzheimer's disease |
| US20080108586A1 (en) * | 2006-09-06 | 2008-05-08 | Incyte Corporation | Combination therapy for human immunodeficiency virus infection |
| JP2010503714A (ja) | 2006-09-18 | 2010-02-04 | エフ．ホフマン−ラ ロシュ アーゲー | オクタヒドロピロロ［３，４−ｃ］ピロール誘導体、抗ウイルス剤としてのそれらの使用 |
| KR20090101278A (ko) * | 2006-12-22 | 2009-09-24 | 인더스트리얼 리서치 리미티드 | 누클레오시다제 및 포스포릴라제 억제제의 아제티딘 유사체 |
| US8338622B2 (en) | 2008-05-30 | 2012-12-25 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| WO2010018131A1 (en) | 2008-08-11 | 2010-02-18 | Smithkline Beecham Corporation | Purine derivatives for use in the treatment of allergic, inflammatory and infectious diseases |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| CN102176911B (zh) | 2008-08-11 | 2014-12-10 | 葛兰素史密丝克莱恩有限责任公司 | 新的腺嘌呤衍生物 |
| WO2011098451A1 (en) | 2010-02-10 | 2011-08-18 | Glaxosmithkline Llc | Purine derivatives and their pharmaceutical uses |
| CA2786973C (en) | 2010-02-10 | 2018-04-10 | Robert Hermann Gibbon | 6-amino-2-{[(1s)-1-methylbutyl] oxy}-9-[5-(1-piperidinyl)-7,9-dihydro-8h-purin-8-one maleate |
| JO3387B1 (ar) | 2011-12-16 | 2019-03-13 | Glaxosmithkline Llc | مشتقات بيتولين |
| AU2015220888B2 (en) | 2014-02-20 | 2017-05-18 | Glaxosmithkline Intellectual Property (No.2) Limited | Pyrrolo[3,2] pyrimidine derivatives as inducers of human interferon |
| CA2967248A1 (en) | 2014-11-13 | 2016-05-19 | Glaxosmithkline Biologicals Sa | Adenine derivatives which are useful in the treatment of allergic diseases or other inflammatory conditions |
| TW201712012A (zh) | 2015-06-16 | 2017-04-01 | 美國禮來大藥廠 | ２－側氧基－１，３，８－三氮雜螺［４．５］癸－３－基羧酸衍生物 |
| NZ738202A (en) | 2015-12-03 | 2019-07-26 | Glaxosmithkline Ip Dev Ltd | Cyclic purine dinucleotides as modulators of sting |
| SI3440076T1 (sl) | 2016-04-07 | 2022-09-30 | Glaxosmithkline Intellectual Property Development Limited | Heterociklični amidi uporabni kot proteinski modulatorji |
| CN109563081A (zh) | 2016-04-07 | 2019-04-02 | 葛兰素史克知识产权开发有限公司 | 可用作蛋白调节剂的杂环酰胺类 |
| JP2020536106A (ja) | 2017-10-05 | 2020-12-10 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｈｉｖの処置に有用なインターフェロン遺伝子の刺激物質（ｓｔｉｎｇ）の調節物質 |
| WO2019069270A1 (en) | 2017-10-05 | 2019-04-11 | Glaxosmithkline Intellectual Property Development Limited | GENERATOR STIMULATOR MODULATORS (STING) INTERFERON |
| GB201807924D0 (en) | 2018-05-16 | 2018-06-27 | Ctxt Pty Ltd | Compounds |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020232375A1 (en) | 2019-05-16 | 2020-11-19 | Silicon Swat, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| CN114391015A (zh) | 2019-05-16 | 2022-04-22 | 斯汀塞拉股份有限公司 | 苯并[b][1,8]萘啶乙酸衍生物和使用方法 |
| GB201910304D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| GB201910305D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| JP7662644B2 (ja) | 2019-12-18 | 2025-04-15 | シーティーエックスティー・ピーティーワイ・リミテッド | 化合物 |
| US11116737B1 (en) | 2020-04-10 | 2021-09-14 | University Of Georgia Research Foundation, Inc. | Methods of using probenecid for treatment of coronavirus infections |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995028389A1 (en) * | 1994-04-15 | 1995-10-26 | Yamanouchi Pharmaceutical Co., Ltd. | Spiro compound and medicinal composition thereof |
| JPH09500361A (ja) * | 1993-05-06 | 1997-01-14 | メレルダウファーマス−ティカルズ インコーポレイテッド | タキキニン拮抗剤として有用な置換ピロリジン−３−イル−アルキル−ピペリジン類 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5635510A (en) | 1993-05-06 | 1997-06-03 | Merrell Pharmaceuticals Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines |
| US5861417A (en) | 1996-12-19 | 1999-01-19 | Hoechst Marion Roussel, Inc. | Heterocyclic substituted pyrrolidine amide derivatives |
| US7053090B2 (en) * | 2001-03-19 | 2006-05-30 | Ono Pharmaceutical Co., Ltd. | Triazaspiro[5.5]undecane derivatives and drugs containing the same as the active ingredient |
-
2003
- 2003-12-12 AT AT03813415T patent/ATE402176T1/de not_active IP Right Cessation
- 2003-12-12 AU AU2003296992A patent/AU2003296992A1/en not_active Abandoned
- 2003-12-12 JP JP2004560830A patent/JP2006511552A/ja active Pending
- 2003-12-12 WO PCT/US2003/039618 patent/WO2004055016A1/en not_active Ceased
- 2003-12-12 DE DE60322423T patent/DE60322423D1/de not_active Expired - Lifetime
- 2003-12-12 US US10/538,134 patent/US7271172B2/en not_active Expired - Fee Related
- 2003-12-12 ES ES03813415T patent/ES2309400T3/es not_active Expired - Lifetime
- 2003-12-12 EP EP03813415A patent/EP1569933B1/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09500361A (ja) * | 1993-05-06 | 1997-01-14 | メレルダウファーマス−ティカルズ インコーポレイテッド | タキキニン拮抗剤として有用な置換ピロリジン−３−イル−アルキル−ピペリジン類 |
| WO1995028389A1 (en) * | 1994-04-15 | 1995-10-26 | Yamanouchi Pharmaceutical Co., Ltd. | Spiro compound and medicinal composition thereof |
Non-Patent Citations (2)
| Title |
|---|
| ROY J. VAZ, ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 7(22), JPN6010023258, 1997, pages 2825 - 2830, ISSN: 0001605089 * |
| TIMOTHY P. BURKHOLDER, ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6(8), JPN6010023259, 1996, pages 951 - 956, ISSN: 0001605090 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US7271172B2 (en) | 2007-09-18 |
| US20060058284A1 (en) | 2006-03-16 |
| DE60322423D1 (de) | 2008-09-04 |
| ES2309400T3 (es) | 2008-12-16 |
| ATE402176T1 (de) | 2008-08-15 |
| EP1569933B1 (en) | 2008-07-23 |
| AU2003296992A1 (en) | 2004-07-09 |
| EP1569933A1 (en) | 2005-09-07 |
| WO2004055016A1 (en) | 2004-07-01 |
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