NO330531B1 - Pyrimidylsulfonamidderivater som kemokinreseptormodulatorer, og fremgangsmate fremstilling derav. - Google Patents
Pyrimidylsulfonamidderivater som kemokinreseptormodulatorer, og fremgangsmate fremstilling derav. Download PDFInfo
- Publication number
- NO330531B1 NO330531B1 NO20051042A NO20051042A NO330531B1 NO 330531 B1 NO330531 B1 NO 330531B1 NO 20051042 A NO20051042 A NO 20051042A NO 20051042 A NO20051042 A NO 20051042A NO 330531 B1 NO330531 B1 NO 330531B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- compound
- hydroxy
- pyrimidin
- yield
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 97
- 102000009410 Chemokine receptor Human genes 0.000 title claims description 8
- 108050000299 Chemokine receptor Proteins 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 6
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 385
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 150000002148 esters Chemical class 0.000 claims abstract description 49
- 238000001727 in vivo Methods 0.000 claims abstract description 35
- 239000012453 solvate Substances 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 33
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- 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 11
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 11
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 9
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 9
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 9
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 9
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 9
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 7
- -1 -NR<5>R<6> Chemical group 0.000 claims description 132
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 63
- 239000002904 solvent Substances 0.000 claims description 60
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
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- 201000010099 disease Diseases 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000002393 azetidinyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229940124530 sulfonamide Drugs 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- DLXZKQCNTIPINT-SNVBAGLBSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-(dimethylsulfamoylamino)-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidine Chemical compound OC[C@@H](C)NC1=CC(NS(=O)(=O)N(C)C)=NC(SCC=2C(=C(Cl)C=CC=2)F)=N1 DLXZKQCNTIPINT-SNVBAGLBSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- KSNXUQRPDJFHTM-LLVKDONJSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 KSNXUQRPDJFHTM-LLVKDONJSA-N 0.000 claims description 2
- CWSXHDBZSCOEHO-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]morpholine-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCOCC1 CWSXHDBZSCOEHO-GFCCVEGCSA-N 0.000 claims description 2
- ZYCHLELHVSMDDI-CYBMUJFWSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]piperidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCCCC1 ZYCHLELHVSMDDI-CYBMUJFWSA-N 0.000 claims description 2
- PXRZFKNGQMUYCZ-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]pyrrolidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCCC1 PXRZFKNGQMUYCZ-GFCCVEGCSA-N 0.000 claims description 2
- RGVHAQJTGULLAX-LLVKDONJSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(Cl)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 RGVHAQJTGULLAX-LLVKDONJSA-N 0.000 claims description 2
- RWIPDXJLNZVYPR-SNVBAGLBSA-N n-[6-[[(2r)-1-hydroxypropan-2-yl]amino]-2-[(2,3,4-trifluorophenyl)methylsulfanyl]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C(F)=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 RWIPDXJLNZVYPR-SNVBAGLBSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 claims 1
- SNCCUTVKNBUBRR-SECBINFHSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]methanesulfonamide Chemical compound OC[C@@H](C)NC1=CC(NS(C)(=O)=O)=NC(SCC=2C(=C(Cl)C=CC=2)F)=N1 SNCCUTVKNBUBRR-SECBINFHSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 298
- 238000004949 mass spectrometry Methods 0.000 description 212
- 239000000047 product Substances 0.000 description 208
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
- 238000005481 NMR spectroscopy Methods 0.000 description 69
- 238000003756 stirring Methods 0.000 description 64
- 239000000203 mixture Substances 0.000 description 60
- 238000004440 column chromatography Methods 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 46
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 43
- 239000012267 brine Substances 0.000 description 43
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
- 238000004007 reversed phase HPLC Methods 0.000 description 42
- 239000000543 intermediate Substances 0.000 description 41
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 39
- 239000000908 ammonium hydroxide Substances 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 36
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 31
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
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- 239000008346 aqueous phase Substances 0.000 description 26
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- 239000012312 sodium hydride Substances 0.000 description 23
- 229910000104 sodium hydride Inorganic materials 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 16
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- 239000013058 crude material Substances 0.000 description 15
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 15
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 10
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB0217431.6A GB0217431D0 (en) | 2002-07-27 | 2002-07-27 | Novel compounds |
PCT/GB2003/003175 WO2004011443A1 (en) | 2002-07-27 | 2003-07-23 | Pyrimidyl sulphone amide derivatives as chemokine receptor modulators |
Publications (2)
Publication Number | Publication Date |
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NO20051042L NO20051042L (no) | 2005-03-31 |
NO330531B1 true NO330531B1 (no) | 2011-05-09 |
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Family Applications (1)
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NO20051042A NO330531B1 (no) | 2002-07-27 | 2005-02-25 | Pyrimidylsulfonamidderivater som kemokinreseptormodulatorer, og fremgangsmate fremstilling derav. |
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US (2) | US7582644B2 (ja) |
EP (1) | EP1527051B1 (ja) |
JP (1) | JP4619782B2 (ja) |
KR (2) | KR101074626B1 (ja) |
CN (1) | CN100345829C (ja) |
AR (1) | AR040700A1 (ja) |
AU (1) | AU2003281684B2 (ja) |
BR (1) | BR0312967A (ja) |
CA (1) | CA2493785C (ja) |
CO (1) | CO5680479A2 (ja) |
EG (1) | EG25893A (ja) |
ES (1) | ES2392965T3 (ja) |
GB (1) | GB0217431D0 (ja) |
HK (1) | HK1076465A1 (ja) |
IL (1) | IL166290A0 (ja) |
IS (1) | IS7697A (ja) |
MX (1) | MXPA05000960A (ja) |
MY (1) | MY139561A (ja) |
NO (1) | NO330531B1 (ja) |
NZ (1) | NZ537914A (ja) |
PL (1) | PL375400A1 (ja) |
RU (1) | RU2342366C2 (ja) |
TW (1) | TWI340038B (ja) |
UA (1) | UA80283C2 (ja) |
WO (1) | WO2004011443A1 (ja) |
ZA (1) | ZA200500791B (ja) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0217431D0 (en) * | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
DE60318219T2 (de) | 2002-08-24 | 2009-01-15 | Astrazeneca Ab | PYRIMIDINDERIVATE ALS MODULATOREN DER AKTIVITuT VON CHEMOKINREZEPTOREN |
GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
EP1809624B1 (en) | 2004-08-28 | 2013-11-20 | AstraZeneca AB | Pyrimidine sulphonamide derivatives as chemokine receptor modulators |
US20060178388A1 (en) | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
WO2006124744A1 (en) * | 2005-05-16 | 2006-11-23 | Vertex Pharmaceuticals Incorporated | Bicyclic derivatives as modulators of ion channels |
GB0526255D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
US20090176785A1 (en) * | 2007-11-16 | 2009-07-09 | Abbott Laboratories | Method of treating arthritis |
US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
HUE035029T2 (en) | 2008-05-21 | 2018-03-28 | Ariad Pharma Inc | Kinase inhibitor phosphorus derivatives |
WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
BRPI0915908A2 (pt) * | 2008-07-16 | 2018-07-10 | Astrazeneca Ab | derivado de pirimidil sulfonamida e seu uso para o tratamento de doenças mediadas por quimiocina |
EP2516416A1 (en) | 2009-12-23 | 2012-10-31 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
US20130259830A1 (en) | 2010-07-12 | 2013-10-03 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
US20130216552A1 (en) | 2010-07-12 | 2013-08-22 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
MY167869A (en) | 2010-07-13 | 2018-09-26 | Astrazeneca Ab | New Crystalline forms of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-{[(1R, 2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]-1-azetidinesulfonamide |
JP5999177B2 (ja) | 2011-05-04 | 2016-09-28 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Egfr発動性がんの細胞増殖阻害用化合物 |
MY180039A (en) | 2011-07-12 | 2020-11-20 | Astrazeneca Ab | N- (6- ( (2r,3s) -3,4-dihydroxybutan-2-yloxy) -2- (4 - fluorobenzylthio) pyrimidin- 4 - yl) -3- methylazetidine- 1 - sulfonamide as chemokine receptor modulator |
AU2013204563B2 (en) | 2012-05-05 | 2016-05-19 | Takeda Pharmaceutical Company Limited | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
US9890158B2 (en) | 2015-10-09 | 2018-02-13 | Abbvie S.Á.R.L. | N-sulfonylated pyrazolo[3,4-b]pyridin-6-carboxamides and method of use |
AU2017231832B2 (en) | 2016-03-11 | 2021-11-11 | Ardea Biosciences, Inc. | CXCR-2 inhibitors for treating crystal arthropathy disorders |
GB201807898D0 (en) * | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2540356A (en) | 1949-03-12 | 1951-02-06 | Sharp & Dohme Inc | Sulfonamide derivatives |
GB866843A (en) | 1958-12-08 | 1961-05-03 | Ici Ltd | Sulphonamidopyrimidines |
NL279406A (ja) | 1961-06-16 | |||
NL127990C (ja) | 1962-12-29 | |||
US3457278A (en) | 1964-10-15 | 1969-07-22 | Geigy Chem Corp | Cyclopropyl-4-sulfanilamido-pyrimidines |
US3452018A (en) | 1966-08-29 | 1969-06-24 | American Home Prod | 1 - (2 - substituted - 6 - arylsulfonamidopyrimidin - 4 - yl)pyridinium hydroxide inner salts |
US3673184A (en) * | 1970-09-02 | 1972-06-27 | Dainippon Pharmaceutical Co | Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives |
JPS61118372A (ja) | 1984-11-12 | 1986-06-05 | Nippon Mektron Ltd | 新規ピリミジン誘導体およびその製造法 |
JPH03197467A (ja) | 1989-12-26 | 1991-08-28 | Nippon Kayaku Co Ltd | ピリミジノン誘導体その製法及びそれを有効成分とする殺虫・殺ダニ剤 |
EP0522038A4 (en) | 1990-03-30 | 1993-05-26 | Merck & Co. Inc. | Substituted pyrimidines, pyrimidinones and pyridopyrimidines |
GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
KR19990082463A (ko) | 1996-02-13 | 1999-11-25 | 돈 리사 로얄 | 혈관 내피 성장 인자 억제제로서의 퀴나졸린유도체 |
CN1116286C (zh) | 1996-03-05 | 2003-07-30 | 曾尼卡有限公司 | 4-苯胺基喹唑啉衍生物 |
GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
EA200000840A1 (ru) | 1998-02-17 | 2001-02-26 | Туларик, Инк. | Антивирусные производные пиримидина |
SE9802729D0 (sv) * | 1998-08-13 | 1998-08-13 | Astra Pharma Prod | Novel Compounds |
GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
AU5108000A (en) | 1999-06-10 | 2001-01-02 | Yamanouchi Pharmaceutical Co., Ltd. | Novel nitrogen-contaiing heterocyclic derivatives or salts thereof |
SE9903544D0 (sv) | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
ATE255584T1 (de) | 2000-02-11 | 2003-12-15 | Astrazeneca Ab | Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität |
IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
CN1255391C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管破坏剂的colchinol衍生物 |
PL359181A1 (en) | 2000-07-07 | 2004-08-23 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
KR100835770B1 (ko) | 2000-09-25 | 2008-06-09 | 액테리온 파마슈티칼 리미티드 | 엔도텔린 길항 활성을 갖는 아릴알칸-설폰아마이드 |
AU2002258400A1 (en) | 2001-02-16 | 2002-08-28 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
TWI328007B (en) | 2002-01-16 | 2010-08-01 | Astrazeneca Ab | Novel compounds |
GB0217431D0 (en) | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
DE60318219T2 (de) | 2002-08-24 | 2009-01-15 | Astrazeneca Ab | PYRIMIDINDERIVATE ALS MODULATOREN DER AKTIVITuT VON CHEMOKINREZEPTOREN |
EP1809624B1 (en) | 2004-08-28 | 2013-11-20 | AstraZeneca AB | Pyrimidine sulphonamide derivatives as chemokine receptor modulators |
-
2002
- 2002-07-27 GB GBGB0217431.6A patent/GB0217431D0/en not_active Ceased
-
2003
- 2003-07-23 AU AU2003281684A patent/AU2003281684B2/en not_active Ceased
- 2003-07-23 UA UAA200500513A patent/UA80283C2/uk unknown
- 2003-07-23 WO PCT/GB2003/003175 patent/WO2004011443A1/en active Application Filing
- 2003-07-23 KR KR1020057001454A patent/KR101074626B1/ko not_active IP Right Cessation
- 2003-07-23 EP EP03740844A patent/EP1527051B1/en not_active Expired - Lifetime
- 2003-07-23 CA CA2493785A patent/CA2493785C/en not_active Expired - Fee Related
- 2003-07-23 BR BR0312967-5A patent/BR0312967A/pt not_active IP Right Cessation
- 2003-07-23 PL PL03375400A patent/PL375400A1/xx not_active Application Discontinuation
- 2003-07-23 JP JP2004523926A patent/JP4619782B2/ja not_active Expired - Fee Related
- 2003-07-23 CN CNB038221497A patent/CN100345829C/zh not_active Expired - Fee Related
- 2003-07-23 RU RU2005101406/04A patent/RU2342366C2/ru not_active IP Right Cessation
- 2003-07-23 NZ NZ537914A patent/NZ537914A/en not_active IP Right Cessation
- 2003-07-23 KR KR1020117006101A patent/KR20110033313A/ko not_active Application Discontinuation
- 2003-07-23 US US10/522,871 patent/US7582644B2/en not_active Expired - Fee Related
- 2003-07-23 MX MXPA05000960A patent/MXPA05000960A/es active IP Right Grant
- 2003-07-23 ES ES03740844T patent/ES2392965T3/es not_active Expired - Lifetime
- 2003-07-25 AR AR20030102688A patent/AR040700A1/es unknown
- 2003-07-25 TW TW092120405A patent/TWI340038B/zh not_active IP Right Cessation
- 2003-07-25 MY MYPI20032818A patent/MY139561A/en unknown
- 2003-07-28 EG EG2003070726A patent/EG25893A/xx active
-
2005
- 2005-01-13 IL IL16629005A patent/IL166290A0/xx unknown
- 2005-01-24 CO CO05005309A patent/CO5680479A2/es not_active Application Discontinuation
- 2005-01-26 ZA ZA200500791A patent/ZA200500791B/en unknown
- 2005-02-17 IS IS7697A patent/IS7697A/is unknown
- 2005-02-25 NO NO20051042A patent/NO330531B1/no not_active IP Right Cessation
- 2005-09-27 HK HK05108513.6A patent/HK1076465A1/xx not_active IP Right Cessation
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2009
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