ZA200204307B - Novel piperidine and piperazine derivatives. - Google Patents
Novel piperidine and piperazine derivatives. Download PDFInfo
- Publication number
- ZA200204307B ZA200204307B ZA200204307A ZA200204307A ZA200204307B ZA 200204307 B ZA200204307 B ZA 200204307B ZA 200204307 A ZA200204307 A ZA 200204307A ZA 200204307 A ZA200204307 A ZA 200204307A ZA 200204307 B ZA200204307 B ZA 200204307B
- Authority
- ZA
- South Africa
- Prior art keywords
- acetamide
- cis
- methyl
- dimethylpiperazin
- methylphenyl
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title abstract description 8
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 4
- 150000004885 piperazines Chemical class 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 128
- -1 cyano, hydroxyl Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- BPEXTIMJLDWDTL-UHFFFAOYSA-N N-Ac-2-methylaniline Natural products CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- DDLBCGOBBLHYON-HDICACEKSA-N 2-[(3r,5s)-4-(3-acetamidophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=C(NC(C)=O)C=CC=2)C)N1CC(=O)NC1=CC=CC=C1C DDLBCGOBBLHYON-HDICACEKSA-N 0.000 claims description 2
- LYNXVGQDKOZWQR-HDICACEKSA-N 2-[(3r,5s)-4-(3-cyanophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=C(C=CC=2)C#N)C)N1CC(=O)NC1=CC=CC=C1C LYNXVGQDKOZWQR-HDICACEKSA-N 0.000 claims description 2
- RUAMGJAHMMHUOF-HDICACEKSA-N 2-[(3r,5s)-4-(4-acetamidophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)C)N1CC(=O)NC1=CC=CC=C1C RUAMGJAHMMHUOF-HDICACEKSA-N 0.000 claims description 2
- YUALGOXBFMYQDA-IYBDPMFKSA-N 2-[(3s,5r)-4-(benzenesulfonyl)-3,5-dimethylpiperazin-1-yl]-n-(2-chlorophenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC(=O)NC1=CC=CC=C1Cl YUALGOXBFMYQDA-IYBDPMFKSA-N 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- ZFHHZVOEYFTYJC-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-(3-methyl-4-thieno[2,3-d]pyrimidin-4-ylpiperazin-1-yl)acetamide Chemical compound C1CN(C=2C=3C=CSC=3N=CN=2)C(C)CN1CC(=O)NC1=C(C)C=CC=C1C ZFHHZVOEYFTYJC-UHFFFAOYSA-N 0.000 claims description 2
- FFHJZGMGUJQGON-HDICACEKSA-N n-(5-cyano-2-methylphenyl)-2-[(3r,5s)-4-(3-cyanophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=C(C=CC=2)C#N)C)N1CC(=O)NC1=CC(C#N)=CC=C1C FFHJZGMGUJQGON-HDICACEKSA-N 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 239000000126 substance Substances 0.000 claims 9
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 239000002671 adjuvant Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- KDTPTUYEWAOQQO-QGZVFWFLSA-N 2-[(3r)-4-(4-acetamidophenyl)sulfonyl-3-methylpiperazin-1-yl]-n-quinolin-5-ylacetamide Chemical compound C([C@H]1C)N(CC(=O)NC=2C3=CC=CN=C3C=CC=2)CCN1S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 KDTPTUYEWAOQQO-QGZVFWFLSA-N 0.000 claims 1
- MGZLCRZIZJQIQW-QGZVFWFLSA-N 2-[(3r)-4-(4-cyanophenyl)sulfonyl-3-methylpiperazin-1-yl]-n-quinolin-5-ylacetamide Chemical compound C([C@H]1C)N(CC(=O)NC=2C3=CC=CN=C3C=CC=2)CCN1S(=O)(=O)C1=CC=C(C#N)C=C1 MGZLCRZIZJQIQW-QGZVFWFLSA-N 0.000 claims 1
- RRVXEVBHMRKESD-OYRHEFFESA-N 2-[(3r,5s)-3,5-dimethyl-4-quinazolin-4-ylpiperazin-1-yl]-n-(2-methyl-5-piperidin-4-yloxyphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)C=2C3=CC=CC=C3N=CN=2)C)N1CC(=O)NC(C(=CC=1)C)=CC=1OC1CCNCC1 RRVXEVBHMRKESD-OYRHEFFESA-N 0.000 claims 1
- ZITKWSBODJMPDY-CALCHBBNSA-N 2-[(3r,5s)-4-(3-cyanophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-(3-methoxy-2-methylphenyl)acetamide Chemical compound COC1=CC=CC(NC(=O)CN2C[C@@H](C)N([C@@H](C)C2)S(=O)(=O)C=2C=C(C=CC=2)C#N)=C1C ZITKWSBODJMPDY-CALCHBBNSA-N 0.000 claims 1
- NPELZWLNXLDTQR-HDICACEKSA-N 2-[(3r,5s)-4-(4-cyanophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-quinolin-5-ylacetamide Chemical compound N1([C@H](C)CN(CC(=O)NC=2C3=CC=CN=C3C=CC=2)C[C@@H]1C)S(=O)(=O)C1=CC=C(C#N)C=C1 NPELZWLNXLDTQR-HDICACEKSA-N 0.000 claims 1
- MGZLCRZIZJQIQW-KRWDZBQOSA-N 2-[(3s)-4-(4-cyanophenyl)sulfonyl-3-methylpiperazin-1-yl]-n-quinolin-5-ylacetamide Chemical compound C([C@@H]1C)N(CC(=O)NC=2C3=CC=CN=C3C=CC=2)CCN1S(=O)(=O)C1=CC=C(C#N)C=C1 MGZLCRZIZJQIQW-KRWDZBQOSA-N 0.000 claims 1
- MVMFFLSBOXBMFM-IYBDPMFKSA-N 2-[(3s,5r)-3,5-dimethyl-4-thieno[2,3-d]pyrimidin-4-ylpiperazin-1-yl]-n-isoquinolin-5-ylacetamide Chemical compound N1([C@H](C)CN(CC(=O)NC=2C3=CC=NC=C3C=CC=2)C[C@@H]1C)C1=NC=NC2=C1C=CS2 MVMFFLSBOXBMFM-IYBDPMFKSA-N 0.000 claims 1
- XQXZZIBHLLXMOS-UHFFFAOYSA-N 2-[8-(benzenesulfonyl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-n-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1NC(=O)CN1CC(N2S(=O)(=O)C=3C=CC=CC=3)CCC2C1 XQXZZIBHLLXMOS-UHFFFAOYSA-N 0.000 claims 1
- FTADYIJBAKOHCZ-UHFFFAOYSA-N 2-[8-(benzenesulfonyl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-n-(3-fluoro-2-methylphenyl)acetamide Chemical compound CC1=C(F)C=CC=C1NC(=O)CN1CC(N2S(=O)(=O)C=3C=CC=CC=3)CCC2C1 FTADYIJBAKOHCZ-UHFFFAOYSA-N 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- XNDPVBAKLSNBSF-OKILXGFUSA-N n-(2-chlorophenyl)-2-[(3s,5r)-3,5-dimethyl-4-(9-methylpurin-6-yl)piperazin-1-yl]acetamide Chemical compound C([C@@H](N([C@H](C)C1)C=2C=3N=CN(C)C=3N=CN=2)C)N1CC(=O)NC1=CC=CC=C1Cl XNDPVBAKLSNBSF-OKILXGFUSA-N 0.000 claims 1
- OARZXYGWJHWZJT-UHFFFAOYSA-N n-(2-methylphenyl)-2-[8-([1,3]thiazolo[5,4-d]pyrimidin-7-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]acetamide Chemical compound CC1=CC=CC=C1NC(=O)CN1CC(N2C=3C=4N=CSC=4N=CN=3)CCC2C1 OARZXYGWJHWZJT-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 102000002294 Purinergic P2X Receptors Human genes 0.000 description 2
- 108010000836 Purinergic P2X Receptors Proteins 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 210000000612 antigen-presenting cell Anatomy 0.000 description 2
- 210000003630 histaminocyte Anatomy 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 description 1
- AEKHOEGYZSRGRR-CALCHBBNSA-N 2-[(3r,5s)-3,5-dimethyl-4-(3-nitrophenyl)sulfonylpiperazin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C)N1CC(=O)NC1=CC=CC=C1C AEKHOEGYZSRGRR-CALCHBBNSA-N 0.000 description 1
- VMNBDUYVUIJBAP-CALCHBBNSA-N 2-[(3r,5s)-4-(3-aminophenyl)sulfonyl-3,5-dimethylpiperazin-1-yl]-n-(2-methylphenyl)acetamide Chemical compound C([C@@H](N([C@H](C)C1)S(=O)(=O)C=2C=C(N)C=CC=2)C)N1CC(=O)NC1=CC=CC=C1C VMNBDUYVUIJBAP-CALCHBBNSA-N 0.000 description 1
- VFRXDTAXNMFFLD-UHFFFAOYSA-N 2-[8-(3-cyanophenyl)sulfonyl-3,8-diazabicyclo[3.2.1]octan-3-yl]-n-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1NC(=O)CN1CC(N2S(=O)(=O)C=3C=C(C=CC=3)C#N)CCC2C1 VFRXDTAXNMFFLD-UHFFFAOYSA-N 0.000 description 1
- KLFDAGKXARXXMV-UHFFFAOYSA-N 2-[8-[4-(acetamidomethoxy)phenyl]sulfonyl-3,8-diazabicyclo[3.2.1]octan-3-yl]-n-(2-methylphenyl)acetamide Chemical compound C1=CC(OCNC(=O)C)=CC=C1S(=O)(=O)N1C2CCC1CN(CC(=O)NC=1C(=CC=CC=1)C)C2 KLFDAGKXARXXMV-UHFFFAOYSA-N 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108010092694 L-Selectin Proteins 0.000 description 1
- 102000016551 L-selectin Human genes 0.000 description 1
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- 102100037602 P2X purinoceptor 7 Human genes 0.000 description 1
- 101710189965 P2X purinoceptor 7 Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000002798 bone marrow cell Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 210000003584 mesangial cell Anatomy 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000002025 microglial effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- 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
- C07D401/12—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9904738A SE9904738D0 (sv) | 1999-12-22 | 1999-12-22 | Novel compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200204307B true ZA200204307B (en) | 2003-08-29 |
Family
ID=20418266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200204307A ZA200204307B (en) | 1999-12-22 | 2002-05-29 | Novel piperidine and piperazine derivatives. |
Country Status (17)
Country | Link |
---|---|
US (2) | US6969713B2 (no) |
EP (1) | EP1242427B1 (no) |
JP (1) | JP2003518126A (no) |
KR (1) | KR100733548B1 (no) |
CN (1) | CN1330657C (no) |
AT (1) | ATE247123T1 (no) |
AU (1) | AU776592B2 (no) |
BR (1) | BR0016543A (no) |
CA (1) | CA2394095A1 (no) |
DE (1) | DE60004564T2 (no) |
IL (2) | IL150201A0 (no) |
MX (1) | MXPA02006261A (no) |
NO (1) | NO20023037L (no) |
NZ (1) | NZ519498A (no) |
SE (1) | SE9904738D0 (no) |
WO (1) | WO2001046200A1 (no) |
ZA (1) | ZA200204307B (no) |
Families Citing this family (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE9904505D0 (sv) | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
TWI258462B (en) | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
US7456184B2 (en) * | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
US7354923B2 (en) * | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
US7732451B2 (en) * | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
CA2462200A1 (en) * | 2001-08-10 | 2003-02-20 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
US7655658B2 (en) * | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
WO2003022214A2 (en) * | 2001-09-06 | 2003-03-20 | Millennium Pharmaceuticals, Inc. | Piperazine and homopiperazine compounds |
PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
WO2003082855A1 (fr) * | 2002-03-28 | 2003-10-09 | Kyowa Hakko Kogyo Co., Ltd. | Agent anti-inflammatoire |
US7071223B1 (en) * | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
US7727991B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds |
US7968548B2 (en) | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
ATE355273T1 (de) * | 2003-05-12 | 2006-03-15 | Pfizer Prod Inc | Benzamidinhibitoren des p2x7-rezeptors |
GB0324498D0 (en) | 2003-07-21 | 2003-11-26 | Aventis Pharma Inc | Heterocyclic compounds as P2X7 ion channel blockers |
US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
JPWO2005107804A1 (ja) * | 2004-05-06 | 2008-03-21 | 小野薬品工業株式会社 | 呼吸器疾患治療剤 |
BRPI0512781A (pt) * | 2004-06-29 | 2008-04-08 | Pfizer Prod Inc | método para preparação de derivados de 5-{4-(2-hidroxi-propil)-3,5-dioxo-4,5-diidro-3h-[1,2,4]tria zin-2-il}-benzamida através da desproteção dos precursores de protetores de hidroxila |
WO2006003517A1 (en) * | 2004-06-29 | 2006-01-12 | Warner-Lambert Company Llc | Combination therapies utilizing benzamide inhibitors of the p2x7 receptor |
WO2006004880A2 (en) * | 2004-06-30 | 2006-01-12 | Schering Corporation | Substituted n-arylsulfonylheterocyclic amines as gamma-secretase inhibitors |
EP1844792A4 (en) * | 2004-12-14 | 2008-05-21 | Shionogi & Co | THERAPEUTIC AGENT AGAINST OBSTIPATION |
US8153803B2 (en) | 2006-07-18 | 2012-04-10 | The General Hospital Corporation | Compositions and methods for modulating sirtuin activity |
US20080021063A1 (en) * | 2006-07-18 | 2008-01-24 | Kazantsev Aleksey G | Compositions and methods for modulating sirtuin activity |
US7834017B2 (en) | 2006-08-11 | 2010-11-16 | Palatin Technologies, Inc. | Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents |
GB0713602D0 (en) * | 2007-07-12 | 2007-08-22 | Syngenta Participations Ag | Chemical compounds |
JP2011500767A (ja) | 2007-10-26 | 2011-01-06 | グラクソ グループ リミテッド | P2x7モジュレータとしての4−ベンゾイル−1−置換ピペラジン−2−オン誘導体 |
CA2719745C (en) | 2008-03-25 | 2016-07-05 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
ATE541832T1 (de) | 2009-04-14 | 2012-02-15 | Affectis Pharmaceuticals Ag | Neuartige p2x7r-antagonisten und ihre verwendung |
WO2011026241A1 (en) * | 2009-09-04 | 2011-03-10 | Zalicus Pharmaceuticals Ltd. | Substituted heterocyclic derivatives for the treatment of pain and epilepsy |
EP2322149A1 (en) | 2009-11-03 | 2011-05-18 | Universidad del Pais Vasco | Methods and compositions for the treatment of ischemia |
CN102858741A (zh) | 2010-05-14 | 2013-01-02 | 阿费克蒂斯制药股份公司 | 制备p2x7r拮抗剂的新方法 |
WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
GB201114212D0 (en) * | 2011-08-18 | 2011-10-05 | Ucb Pharma Sa | Therapeutic agents |
GB201119401D0 (en) * | 2011-11-10 | 2011-12-21 | Ucb Pharma Sa | Therapeutic agents |
AR090037A1 (es) | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
EP2961403A4 (en) | 2013-03-01 | 2016-11-30 | Zalicus Pharmaceuticals Ltd | HETEROCYCLIC INHIBITORS OF SODIUM CHANNEL |
NZ728915A (en) * | 2014-08-16 | 2018-01-26 | Suven Life Sciences Ltd | Process for large scale production of n-[4-(1- cyclobutyl piperidin-4-yloxy) phenyl]-2-(morpholin-4-yl) acetamide dihydrochloride |
UY36390A (es) * | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen |
EP3215141A4 (en) | 2014-11-05 | 2018-06-06 | Flexus Biosciences, Inc. | Immunoregulatory agents |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3029241A (en) * | 1962-04-10 | Phenylpbperazinylacyl anilines | ||
JPS5849550B2 (ja) * | 1974-02-07 | 1983-11-05 | 住友化学工業株式会社 | シンキナアニリンユウドウタイ ノ セイホウ |
FR2346011A1 (fr) | 1976-02-02 | 1977-10-28 | Orsymonde | Acetanilido-piperazines |
ZA825719B (en) | 1981-09-03 | 1983-06-29 | Recordati Chem Pharm | Alkanoylanilides |
JPH03141258A (ja) * | 1989-10-25 | 1991-06-17 | Kowa Co | 新規なピペラジン誘導体 |
CA2101311A1 (en) | 1992-07-31 | 1994-02-01 | Neelakantan Balasubramanian | Adenosine re-uptake inhibiting derivatives of diphenyl oxazoles, thiazoles and imidazoles |
JP3229693B2 (ja) * | 1993-02-22 | 2001-11-19 | 協和醗酵工業株式会社 | ピペラジン誘導体 |
JP3531169B2 (ja) * | 1996-06-11 | 2004-05-24 | 三菱ウェルファーマ株式会社 | 縮合ヘテロ環化合物およびその医薬用途 |
SE9704544D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
SE9704545D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
WO1999031096A1 (en) * | 1997-12-18 | 1999-06-24 | Shaman Pharmaceuticals, Inc. | Piperazine derivatives useful as hypoglycemic agents |
AU3985699A (en) | 1998-05-19 | 1999-12-06 | Centaur Pharmaceuticals, Inc. | Amide therapeutics for the treatment of inflammatory bowel disease |
HUP0202214A3 (en) * | 1999-04-09 | 2002-12-28 | Astrazeneca Ab | Adamantane derivatives, preparation and use thereof |
SE9901875D0 (sv) * | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
SE9904505D0 (sv) * | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
TWI258462B (en) | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
SE9904652D0 (sv) * | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
-
1999
- 1999-12-22 SE SE9904738A patent/SE9904738D0/xx unknown
-
2000
- 2000-12-18 JP JP2001547110A patent/JP2003518126A/ja active Pending
- 2000-12-18 BR BR0016543-3A patent/BR0016543A/pt not_active Application Discontinuation
- 2000-12-18 AT AT00989102T patent/ATE247123T1/de not_active IP Right Cessation
- 2000-12-18 CN CNB008190453A patent/CN1330657C/zh not_active Expired - Fee Related
- 2000-12-18 AU AU25648/01A patent/AU776592B2/en not_active Ceased
- 2000-12-18 IL IL15020100A patent/IL150201A0/xx active IP Right Grant
- 2000-12-18 CA CA002394095A patent/CA2394095A1/en not_active Abandoned
- 2000-12-18 DE DE60004564T patent/DE60004564T2/de not_active Expired - Fee Related
- 2000-12-18 NZ NZ519498A patent/NZ519498A/en unknown
- 2000-12-18 MX MXPA02006261A patent/MXPA02006261A/es active IP Right Grant
- 2000-12-18 US US10/168,094 patent/US6969713B2/en not_active Expired - Fee Related
- 2000-12-18 KR KR1020027008039A patent/KR100733548B1/ko not_active IP Right Cessation
- 2000-12-18 EP EP00989102A patent/EP1242427B1/en not_active Expired - Lifetime
- 2000-12-18 WO PCT/SE2000/002580 patent/WO2001046200A1/en active IP Right Grant
-
2002
- 2002-05-29 ZA ZA200204307A patent/ZA200204307B/en unknown
- 2002-06-12 IL IL150201A patent/IL150201A/en not_active IP Right Cessation
- 2002-06-21 NO NO20023037A patent/NO20023037L/no not_active Application Discontinuation
-
2005
- 2005-05-10 US US11/125,335 patent/US20050272745A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
MXPA02006261A (es) | 2002-12-05 |
CA2394095A1 (en) | 2001-06-28 |
WO2001046200A8 (en) | 2002-02-28 |
EP1242427B1 (en) | 2003-08-13 |
CN1434827A (zh) | 2003-08-06 |
US20050272745A1 (en) | 2005-12-08 |
US20030013721A1 (en) | 2003-01-16 |
KR20020069221A (ko) | 2002-08-29 |
WO2001046200A1 (en) | 2001-06-28 |
NO20023037D0 (no) | 2002-06-21 |
IL150201A (en) | 2008-06-05 |
DE60004564D1 (de) | 2003-09-18 |
CN1330657C (zh) | 2007-08-08 |
EP1242427A1 (en) | 2002-09-25 |
AU776592B2 (en) | 2004-09-16 |
JP2003518126A (ja) | 2003-06-03 |
DE60004564T2 (de) | 2004-06-24 |
NZ519498A (en) | 2004-02-27 |
BR0016543A (pt) | 2002-09-17 |
SE9904738D0 (sv) | 1999-12-22 |
AU2564801A (en) | 2001-07-03 |
KR100733548B1 (ko) | 2007-06-28 |
ATE247123T1 (de) | 2003-08-15 |
NO20023037L (no) | 2002-08-22 |
IL150201A0 (en) | 2002-12-01 |
US6969713B2 (en) | 2005-11-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200204307B (en) | Novel piperidine and piperazine derivatives. | |
JP2003518126A5 (no) | ||
ES2284617T3 (es) | Compuestos de pirimidina. | |
ES2277841T3 (es) | Derivados de 5-ciano-2-aminopiridina. | |
DE60024854T2 (de) | 4,5-disubstituierte 2-aminopyrimidine | |
ES2208397T3 (es) | Derivados de imidazo (1,2-a) piridina y de pirazolo (2,3-a) piridina. | |
ES2292599T3 (es) | Derivados de pirimidina. | |
ES2155045T3 (es) | Inhibicion de la quinasa raf utilizando ureas heterociclicas sustituidas con arilo y heteroarilo. | |
ES2556946T3 (es) | Pirimidinaminas como moduladores de la angiogénesis | |
ES2260036T3 (es) | Derivados de urea como inhibidores del receptor ccr-3. | |
RU2376309C2 (ru) | Производное тиенопиразола, имеющее ингибирующую фосфодиэстеразу 7 (pde 7) активность | |
CN101006088A (zh) | 作为cxcr3受体调节剂用于预防和治疗炎性和免疫调节性失调和疾病的融合的嘧啶衍生物和其组合物 | |
SK3822002A3 (en) | Quinazoline derivatives, process for the preparation thereof and their use | |
SK3872002A3 (en) | Therapeutic quinazoline derivatives, method for the preparation thereof and pharmaceutical composition comprising same | |
AU2006309013A1 (en) | Bi-aryl meta-pyrimidine inhibitors of kinases | |
PT1268444E (pt) | Pirimidinas 2, 4-di(hetero-) arilamino(-oxi)-5-substituídas como agentes antineoplásicos | |
NO941611L (no) | Nye aminosyrederivater, fremgangsmåte for deres fremstilling og farmasöytiske preparater inneholdende disse forbindelser | |
JP2005508336A5 (no) | ||
CA2675884A1 (en) | Quinoxaline compounds and use thereof | |
SA99200059A (ar) | مركبات إميدازول جديدة مستبدلة | |
ZA200108969B (en) | Quinoline derivatives as inhibitors of MEK enzymes. | |
EA012875B1 (ru) | ПРОИЗВОДНЫЕ ПИРИМИДИНА И ИХ ПРИМЕНЕНИЕ В ТЕРАПИИ В КАЧЕСТВЕ ИНГИБИТОРОВ КИНАЗЫ CSBP/RK/p38 | |
CZ20031013A3 (en) | Bridged piperazine derivatives | |
CA2352045A1 (en) | Substituted benzo[de]isoquinoline-1,3-diones | |
ES2334491T3 (es) | Antagonistas del receptor 5-ht7. |