JP2003503488A5 - - Google Patents
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- Publication number
- JP2003503488A5 JP2003503488A5 JP2001507819A JP2001507819A JP2003503488A5 JP 2003503488 A5 JP2003503488 A5 JP 2003503488A5 JP 2001507819 A JP2001507819 A JP 2001507819A JP 2001507819 A JP2001507819 A JP 2001507819A JP 2003503488 A5 JP2003503488 A5 JP 2003503488A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- piperazinyl
- chloro
- benzamide
- oxoethoxy
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 description 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000012453 solvate Substances 0.000 description 13
- -1 2-amino-2-oxoethoxy Chemical group 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 206010039083 rhinitis Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 208000030507 AIDS Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- VZFADCKFFSRCCK-UHFFFAOYSA-N 2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 VZFADCKFFSRCCK-UHFFFAOYSA-N 0.000 description 3
- CDVKHECUVHJVDE-UHFFFAOYSA-N 4-chloro-n-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethyl]-2-[2-(1-hydroxypropan-2-ylamino)-2-oxoethoxy]benzamide Chemical compound OCC(C)NC(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 CDVKHECUVHJVDE-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 206010025135 lupus erythematosus Diseases 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 201000008283 Atrophic Rhinitis Diseases 0.000 description 2
- 0 CC1(C)CN(*C(*)*)CCN(CCN(*)C(C2=CC=CC(C)(CCO*C3OC3*)C=C2)=O)C1 Chemical compound CC1(C)CN(*C(*)*)CCN(CCN(*)C(C2=CC=CC(C)(CCO*C3OC3*)C=C2)=O)C1 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039088 Rhinitis atrophic Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- HMVVXQUMJHPGMH-UHFFFAOYSA-N 1-[2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 HMVVXQUMJHPGMH-UHFFFAOYSA-N 0.000 description 1
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 description 1
- OJJKMGBNZWBKMT-UHFFFAOYSA-N 2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetic acid;hydrochloride Chemical compound Cl.OC(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 OJJKMGBNZWBKMT-UHFFFAOYSA-N 0.000 description 1
- MXSGLNZJFMYFKR-UHFFFAOYSA-N 2-[[2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 MXSGLNZJFMYFKR-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- POBRWJKFEQDGKH-UHFFFAOYSA-N 4-chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acid Chemical compound CN(C)C(=O)COC1=CC(Cl)=CC=C1C(O)=O POBRWJKFEQDGKH-UHFFFAOYSA-N 0.000 description 1
- LRKQKBKMOVRRKM-UHFFFAOYSA-N 4-chloro-n-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethyl]-2-[2-(dimethylamino)-2-oxoethoxy]-n-methylbenzamide Chemical compound CN(C)C(=O)COC1=CC(Cl)=CC=C1C(=O)N(C)CCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 LRKQKBKMOVRRKM-UHFFFAOYSA-N 0.000 description 1
- DETLBALLVUKOLF-UHFFFAOYSA-N 4-chloro-n-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethyl]-2-hydroxybenzamide Chemical compound OC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 DETLBALLVUKOLF-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 208000035939 Alveolitis allergic Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- 206010016228 Fasciitis Diseases 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 206010024227 Lepromatous leprosy Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 208000036284 Rhinitis seasonal Diseases 0.000 description 1
- 208000009359 Sezary Syndrome Diseases 0.000 description 1
- 208000021388 Sezary disease Diseases 0.000 description 1
- 206010043561 Thrombocytopenic purpura Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 201000009151 chronic rhinitis Diseases 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- UUSQWLHRIZOHTN-UHFFFAOYSA-N ethyl 1-[2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 UUSQWLHRIZOHTN-UHFFFAOYSA-N 0.000 description 1
- CISDNFRBNOPCQA-UHFFFAOYSA-N ethyl 1-[2-[5-chloro-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethylcarbamoyl]phenoxy]acetyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)COC1=CC(Cl)=CC=C1C(=O)NCCN1CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 CISDNFRBNOPCQA-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 208000022195 farmer lung disease Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9902551A SE9902551D0 (sv) | 1999-07-02 | 1999-07-02 | Novel compounds |
| SE9902551-2 | 1999-07-02 | ||
| PCT/GB2000/002470 WO2001002381A1 (en) | 1999-07-02 | 2000-06-27 | Piperazine derivatives as modulators of chemokine receptor activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003503488A JP2003503488A (ja) | 2003-01-28 |
| JP2003503488A5 true JP2003503488A5 (enExample) | 2007-07-19 |
Family
ID=20416365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001507819A Withdrawn JP2003503488A (ja) | 1999-07-02 | 2000-06-27 | ケモカインレセプター活性の調節剤としてのピペラジン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6562825B1 (enExample) |
| EP (1) | EP1196404B1 (enExample) |
| JP (1) | JP2003503488A (enExample) |
| AT (1) | ATE384708T1 (enExample) |
| AU (1) | AU5692500A (enExample) |
| DE (1) | DE60037888T2 (enExample) |
| ES (1) | ES2298149T3 (enExample) |
| SE (1) | SE9902551D0 (enExample) |
| WO (1) | WO2001002381A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1604982A1 (en) | 2001-07-02 | 2005-12-14 | AstraZeneca AB | Intermediates for the preparation of piperidine derivatives useful as modulators of chemokine receptor activity |
| GB0120461D0 (en) * | 2001-08-22 | 2001-10-17 | Astrazeneca Ab | Novel compounds |
| GB0122503D0 (en) | 2001-09-18 | 2001-11-07 | Astrazeneca Ab | Chemical compounds |
| TW200303304A (en) * | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| SE0200843D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0200844D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
| SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| JP2009501793A (ja) | 2005-07-21 | 2009-01-22 | アストラゼネカ・アクチエボラーグ | 新規ピペリジン誘導体 |
| US9551033B2 (en) | 2007-06-08 | 2017-01-24 | Genentech, Inc. | Gene expression markers of tumor resistance to HER2 inhibitor treatment |
| EP2215065B1 (en) * | 2007-10-19 | 2012-07-11 | Boehringer Ingelheim International GmbH | Ccr10 antagonists |
| WO2011139636A1 (en) * | 2010-05-03 | 2011-11-10 | Philadelphia Health & Education Corporation | Small molecule inhibitors of functions of the hiv-1 matrix protein |
| CN103012318B (zh) * | 2012-11-25 | 2014-12-10 | 大理学院 | 氟苄基取代哌嗪类化合物及其制备和医药用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2027897A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la difenilmetilpiperacina. |
| IL125658A0 (en) * | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
-
1999
- 1999-07-02 SE SE9902551A patent/SE9902551D0/xx unknown
-
2000
- 2000-06-27 AT AT00942220T patent/ATE384708T1/de not_active IP Right Cessation
- 2000-06-27 JP JP2001507819A patent/JP2003503488A/ja not_active Withdrawn
- 2000-06-27 AU AU56925/00A patent/AU5692500A/en not_active Abandoned
- 2000-06-27 ES ES00942220T patent/ES2298149T3/es not_active Expired - Lifetime
- 2000-06-27 EP EP00942220A patent/EP1196404B1/en not_active Expired - Lifetime
- 2000-06-27 WO PCT/GB2000/002470 patent/WO2001002381A1/en not_active Ceased
- 2000-06-27 DE DE60037888T patent/DE60037888T2/de not_active Expired - Lifetime
- 2000-06-27 US US09/640,398 patent/US6562825B1/en not_active Expired - Fee Related
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