MXPA02012596A - Derivados de benzotiazol. - Google Patents
Derivados de benzotiazol.Info
- Publication number
- MXPA02012596A MXPA02012596A MXPA02012596A MXPA02012596A MXPA02012596A MX PA02012596 A MXPA02012596 A MX PA02012596A MX PA02012596 A MXPA02012596 A MX PA02012596A MX PA02012596 A MXPA02012596 A MX PA02012596A MX PA02012596 A MXPA02012596 A MX PA02012596A
- Authority
- MX
- Mexico
- Prior art keywords
- methoxy
- benzothiazol
- methyl
- benzamide
- phenyl
- Prior art date
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 554
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 18
- 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 14
- -1 2, 3-dihydro-lH-indolyl Chemical group 0.000 claims description 300
- 125000000217 alkyl group Chemical group 0.000 claims description 157
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 130
- 238000000034 method Methods 0.000 claims description 109
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 31
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 27
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 22
- VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- KUZPSPIMIBWVAW-UHFFFAOYSA-N 4-methoxy-7-phenyl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C1=CC=CC=C1 KUZPSPIMIBWVAW-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- KYPGODAIYIMXKT-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KYPGODAIYIMXKT-UHFFFAOYSA-N 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- UFFMEJQEKDEIJH-UHFFFAOYSA-N 4-methoxy-7-(5-methylthiophen-2-yl)-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C1=CC=C(C)S1 UFFMEJQEKDEIJH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 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 6
- 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 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- CEKSPMMCISUSTR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroquinoline Chemical compound C1CCC2CCCNC2=C1 CEKSPMMCISUSTR-UHFFFAOYSA-N 0.000 claims description 5
- BWALCOILYZRIII-UHFFFAOYSA-N 4-(2-methoxyethoxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(COCCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 BWALCOILYZRIII-UHFFFAOYSA-N 0.000 claims description 5
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- YYPCSESDMWDOFG-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=NC=2C(OC)=CC=C1N1CCOCC1 YYPCSESDMWDOFG-UHFFFAOYSA-N 0.000 claims description 5
- JYDYGXJAYSGYLW-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 JYDYGXJAYSGYLW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- CXIQCNVCWNPHKF-UHFFFAOYSA-N 2-[[ethyl(2-methoxyethyl)amino]methyl]-N-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C(C)N(CCOC)CC1=C(C(=O)NC=2SC3=C(N=2)C(=CC=C3N2CCOCC2)OC)C=CC=C1 CXIQCNVCWNPHKF-UHFFFAOYSA-N 0.000 claims description 4
- YTOSWUCZMFQXPJ-UHFFFAOYSA-N 4-(aminomethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 YTOSWUCZMFQXPJ-UHFFFAOYSA-N 0.000 claims description 4
- PBKWNISRGRRYNU-UHFFFAOYSA-N 4-(methoxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(COC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 PBKWNISRGRRYNU-UHFFFAOYSA-N 0.000 claims description 4
- MEUOPNIKWUHUCN-QFIPXVFZSA-N 4-[[(3s)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4C[C@H](CC4)N(C)C)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 MEUOPNIKWUHUCN-QFIPXVFZSA-N 0.000 claims description 4
- MKKPOTULIHKQAY-UHFFFAOYSA-N 4-chloro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methyl-3-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCCC4)C(Cl)=CC=3)C)=NC=2C(OC)=CC=C1N1CCOCC1 MKKPOTULIHKQAY-UHFFFAOYSA-N 0.000 claims description 4
- CGJSHTWSNBHKOB-UHFFFAOYSA-N 4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 CGJSHTWSNBHKOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
- BRCDUYGLCKTGBB-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCN(C)CC4)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 BRCDUYGLCKTGBB-UHFFFAOYSA-N 0.000 claims description 4
- KEJUVOFMRNLHJQ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KEJUVOFMRNLHJQ-UHFFFAOYSA-N 0.000 claims description 4
- GGPJGAFHQGWMQZ-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=CN=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 GGPJGAFHQGWMQZ-UHFFFAOYSA-N 0.000 claims description 4
- DGVSPGPQRYCAOD-UHFFFAOYSA-N n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)-2-methyl-4-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCCC3)C)=NC=2C(OC)=CC=C1C1=CC=CS1 DGVSPGPQRYCAOD-UHFFFAOYSA-N 0.000 claims description 4
- LODRHLUBEKIPME-UHFFFAOYSA-N n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C1=CC=CS1 LODRHLUBEKIPME-UHFFFAOYSA-N 0.000 claims description 4
- NZBIKEZYGQOFQF-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methyl-4-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCCC3)C)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 NZBIKEZYGQOFQF-UHFFFAOYSA-N 0.000 claims description 4
- PAQSHTQSRJVUNK-UHFFFAOYSA-N n-[4-methoxy-7-(5-methylthiophen-2-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C1=CC=C(C)S1 PAQSHTQSRJVUNK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- XICAMVNHDMHQHG-UHFFFAOYSA-N thiomorpholine-4-carboxylic acid Chemical compound OC(=O)N1CCSCC1 XICAMVNHDMHQHG-UHFFFAOYSA-N 0.000 claims description 4
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 3
- LHRIKPIZVNNGRU-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-2-methylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCNCCC3)C)=NC=2C(OC)=CC=C1C1=CC=CC=C1 LHRIKPIZVNNGRU-UHFFFAOYSA-N 0.000 claims description 3
- QWMBZRZDPAXYTF-UHFFFAOYSA-N 4-(hydroxymethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CO)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 QWMBZRZDPAXYTF-UHFFFAOYSA-N 0.000 claims description 3
- OOGKLPSYQCECGD-UHFFFAOYSA-N 4-[(2-ethoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CNCCOCC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 OOGKLPSYQCECGD-UHFFFAOYSA-N 0.000 claims description 3
- IGKOAYSPGWNDKE-UHFFFAOYSA-N 4-[(2-hydroxyethylamino)methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CNCCO)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 IGKOAYSPGWNDKE-UHFFFAOYSA-N 0.000 claims description 3
- KRVYMJBQDLNWEL-UHFFFAOYSA-N 4-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CNCCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(C=3C=CC=CC=3)=C2S1 KRVYMJBQDLNWEL-UHFFFAOYSA-N 0.000 claims description 3
- NBQUZAZEWMNNFG-UHFFFAOYSA-N 4-chloro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-(methylaminomethyl)benzamide Chemical compound C1=C(Cl)C(CNC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 NBQUZAZEWMNNFG-UHFFFAOYSA-N 0.000 claims description 3
- XFNHDSINBXOVKV-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 XFNHDSINBXOVKV-UHFFFAOYSA-N 0.000 claims description 3
- JQKBYRBSVQPASR-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CS1 JQKBYRBSVQPASR-UHFFFAOYSA-N 0.000 claims description 3
- HUDJEBHKLCEUPL-UHFFFAOYSA-N 4-methoxy-7-(2-piperidin-1-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C(N=1)=CSC=1N1CCCCC1 HUDJEBHKLCEUPL-UHFFFAOYSA-N 0.000 claims description 3
- GHLPFMFBOAKGMD-UHFFFAOYSA-N 4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1N1CCCCC1 GHLPFMFBOAKGMD-UHFFFAOYSA-N 0.000 claims description 3
- BEJVLWOGKNSBCK-UHFFFAOYSA-N 4-methoxy-7-pyridin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1C1=CC=NC=C1 BEJVLWOGKNSBCK-UHFFFAOYSA-N 0.000 claims description 3
- SLFFYIOTDHJEQL-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)C=2C=NC(=CC2)C Chemical compound COC1=CC=C(C2=C1N=C(S2)C2N(CCOC2)C(=O)N)C=2N=C(SC2)C=2C=NC(=CC2)C SLFFYIOTDHJEQL-UHFFFAOYSA-N 0.000 claims description 3
- MWUUSBWKKMKSDN-UHFFFAOYSA-N methyl n-[[4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]phenyl]methyl]-n-methylcarbamate Chemical compound C1=CC(CN(C)C(=O)OC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 MWUUSBWKKMKSDN-UHFFFAOYSA-N 0.000 claims description 3
- GJAAOLKLYVTDTK-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methyl-3-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCCC4)C=CC=3)C)=NC=2C(OC)=CC=C1N1CCOCC1 GJAAOLKLYVTDTK-UHFFFAOYSA-N 0.000 claims description 3
- KLUQUYACYZVTAO-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KLUQUYACYZVTAO-UHFFFAOYSA-N 0.000 claims description 3
- URPRNFSLUZCUOJ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-(methylaminomethyl)benzamide Chemical compound CNCC1=CC=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 URPRNFSLUZCUOJ-UHFFFAOYSA-N 0.000 claims description 3
- VEHWZDFLDCERBM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(methylaminomethyl)benzamide Chemical compound C1=CC(CNC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 VEHWZDFLDCERBM-UHFFFAOYSA-N 0.000 claims description 3
- ZWNDFSJRYITZEO-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-[(2-methylimidazol-1-yl)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4C(=NC=C4)C)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 ZWNDFSJRYITZEO-UHFFFAOYSA-N 0.000 claims description 3
- OCUSKKKYPLDSAK-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-4-[(2-methylsulfanylethylamino)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CNCCSC)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 OCUSKKKYPLDSAK-UHFFFAOYSA-N 0.000 claims description 3
- GXNDDKYHSLGFMK-UHFFFAOYSA-N n-(4-methoxy-7-pyridin-3-yl-1,3-benzothiazol-2-yl)-5-methylthiophene-2-carboxamide Chemical compound C1=2SC(NC(=O)C=3SC(C)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CN=C1 GXNDDKYHSLGFMK-UHFFFAOYSA-N 0.000 claims description 3
- UHUICRMEVKTTGT-UHFFFAOYSA-N n-(4-methoxy-7-thiomorpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCSCC1 UHUICRMEVKTTGT-UHFFFAOYSA-N 0.000 claims description 3
- XILGMURDLOXRDG-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyrrolidin-1-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(C)N=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1N1CCCC1 XILGMURDLOXRDG-UHFFFAOYSA-N 0.000 claims description 3
- VFPNTXSBUIMXPE-UHFFFAOYSA-N 3-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound COCCNCC1=CC=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 VFPNTXSBUIMXPE-UHFFFAOYSA-N 0.000 claims description 2
- RRKKFQFQAIWSGK-UHFFFAOYSA-N 4-(ethylaminomethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CNCC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 RRKKFQFQAIWSGK-UHFFFAOYSA-N 0.000 claims description 2
- JDIPCXLCIPCFMU-UHFFFAOYSA-N 4-[2-(dimethylamino)ethylsulfanylmethyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CSCCN(C)C)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 JDIPCXLCIPCFMU-UHFFFAOYSA-N 0.000 claims description 2
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
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- UMDIVWIGYWZOJA-UHFFFAOYSA-N methyl 3-(carbamothioylamino)-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(NC(N)=S)=C1 UMDIVWIGYWZOJA-UHFFFAOYSA-N 0.000 description 1
- MCEBXXSZFFMJLM-UHFFFAOYSA-N methyl 3-amino-4-bromo-2-nitrobenzoate Chemical group COC(=O)C1=CC=C(Br)C(N)=C1[N+]([O-])=O MCEBXXSZFFMJLM-UHFFFAOYSA-N 0.000 description 1
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- SNVRPWGUVYOWAG-UHFFFAOYSA-N methyl 4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCN1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 SNVRPWGUVYOWAG-UHFFFAOYSA-N 0.000 description 1
- JHDQHPJHLHKZDL-UHFFFAOYSA-N methyl 4-chloro-4-oxobut-2-enoate Chemical compound COC(=O)C=CC(Cl)=O JHDQHPJHLHKZDL-UHFFFAOYSA-N 0.000 description 1
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- BKVVBRXEIAOOOU-UHFFFAOYSA-N methyl n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1N1CCOCC1 BKVVBRXEIAOOOU-UHFFFAOYSA-N 0.000 description 1
- KBPRJKWKRZGCOO-UHFFFAOYSA-N methyl n-(4-methoxy-7-prop-1-enyl-1,3-benzothiazol-2-yl)carbamate Chemical compound C1=CC(C=CC)=C2SC(NC(=O)OC)=NC2=C1OC KBPRJKWKRZGCOO-UHFFFAOYSA-N 0.000 description 1
- FRZZQXKKFPIPKM-UHFFFAOYSA-N methyl n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CC=CS1 FRZZQXKKFPIPKM-UHFFFAOYSA-N 0.000 description 1
- MSQFGWVFPPNBDG-UHFFFAOYSA-N methyl n-(7-acetyl-4-methoxy-1,3-benzothiazol-2-yl)carbamate Chemical compound C1=CC(C(C)=O)=C2SC(NC(=O)OC)=NC2=C1OC MSQFGWVFPPNBDG-UHFFFAOYSA-N 0.000 description 1
- PZGRDMGGOKHRIT-UHFFFAOYSA-N methyl n-(7-ethenyl-4-methoxy-1,3-benzothiazol-2-yl)carbamate Chemical compound C1=CC(C=C)=C2SC(NC(=O)OC)=NC2=C1OC PZGRDMGGOKHRIT-UHFFFAOYSA-N 0.000 description 1
- BXYXRKBQJWQFKK-UHFFFAOYSA-N methyl n-[4-methoxy-7-(2-methyl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CSC(C)=N1 BXYXRKBQJWQFKK-UHFFFAOYSA-N 0.000 description 1
- DMQVPEOYYNTYJZ-UHFFFAOYSA-N methyl n-[4-methoxy-7-(2-methylpyridin-4-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CC=NC(C)=C1 DMQVPEOYYNTYJZ-UHFFFAOYSA-N 0.000 description 1
- IKVLWQHTQYUROK-UHFFFAOYSA-N methyl n-[4-methoxy-7-(2-piperidin-1-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C(N=1)=CSC=1N1CCCCC1 IKVLWQHTQYUROK-UHFFFAOYSA-N 0.000 description 1
- IXJKOMXDIYYZAE-UHFFFAOYSA-N methyl n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C(N=1)=CSC=1C1=CC=CC=N1 IXJKOMXDIYYZAE-UHFFFAOYSA-N 0.000 description 1
- INLDMMHJJDCULJ-UHFFFAOYSA-N methyl n-[4-methoxy-7-(2-pyrrolidin-1-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C(N=1)=CSC=1N1CCCC1 INLDMMHJJDCULJ-UHFFFAOYSA-N 0.000 description 1
- PXQSICGYKDFAML-UHFFFAOYSA-N methyl n-[4-methoxy-7-(5-methylthiophen-2-yl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CC=C(C)S1 PXQSICGYKDFAML-UHFFFAOYSA-N 0.000 description 1
- MXGTTWDYQZLGEI-UHFFFAOYSA-N methyl n-[4-methoxy-7-[2-(tritylamino)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C(N=1)=CSC=1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MXGTTWDYQZLGEI-UHFFFAOYSA-N 0.000 description 1
- ODMJLRDMJSWVLN-UHFFFAOYSA-N methyl n-[7-(2,5-dimethyl-1,3-thiazol-4-yl)-4-methoxy-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C=1N=C(C)SC=1C ODMJLRDMJSWVLN-UHFFFAOYSA-N 0.000 description 1
- CMOZCOOONUNZFI-UHFFFAOYSA-N methyl n-[7-(2-amino-1,3-thiazol-4-yl)-4-methoxy-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CSC(N)=N1 CMOZCOOONUNZFI-UHFFFAOYSA-N 0.000 description 1
- CVKQPPZDHXMDQO-UHFFFAOYSA-N methyl n-[7-(2-amino-1h-imidazol-5-yl)-4-methoxy-1,3-benzothiazol-2-yl]carbamate Chemical compound C=12SC(NC(=O)OC)=NC2=C(OC)C=CC=1C1=CNC(N)=N1 CVKQPPZDHXMDQO-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- DJQOGYTZMZEXJN-UHFFFAOYSA-N pyrrolidine-1-carbothioamide Chemical compound NC(=S)N1CCCC1 DJQOGYTZMZEXJN-UHFFFAOYSA-N 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical class OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- LUKQTNVNMALRMG-UHFFFAOYSA-N tert-butyl 4-carbonochloridoylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(Cl)=O)CC1 LUKQTNVNMALRMG-UHFFFAOYSA-N 0.000 description 1
- UMOZLQVSOVNSCA-UHFFFAOYSA-N tert-butyl n-(diaminomethylidene)carbamate Chemical compound CC(C)(C)OC(=O)NC(N)=N UMOZLQVSOVNSCA-UHFFFAOYSA-N 0.000 description 1
- VHYXAWLOJGIJPC-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNCC1 VHYXAWLOJGIJPC-UHFFFAOYSA-N 0.000 description 1
- FZQBAINUENUNKK-UHFFFAOYSA-N tert-butyl n-[[1-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]piperidin-4-yl]methyl]carbamate Chemical compound C1=2SC(NC(=O)N3CCC(CNC(=O)OC(C)(C)C)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 FZQBAINUENUNKK-UHFFFAOYSA-N 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
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- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
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- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ADIMXRAVQWIAQG-UHFFFAOYSA-N trimethyl(thiophen-3-yl)stannane Chemical compound C[Sn](C)(C)C=1C=CSC=1 ADIMXRAVQWIAQG-UHFFFAOYSA-N 0.000 description 1
- KQNRAJPEEFHXHR-UHFFFAOYSA-N trimethyl-(2-methylpyridin-4-yl)stannane Chemical compound CC1=CC([Sn](C)(C)C)=CC=N1 KQNRAJPEEFHXHR-UHFFFAOYSA-N 0.000 description 1
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- DOFNIDPLSQZBSU-UHFFFAOYSA-N tritylthiourea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NC(=S)N)C1=CC=CC=C1 DOFNIDPLSQZBSU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D277/82—Nitrogen atoms
-
- 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
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-
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- 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
- C07D417/14—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 three or more hetero rings
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- Engineering & Computer Science (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00113219 | 2000-06-21 | ||
| PCT/EP2001/006506 WO2001097786A2 (en) | 2000-06-21 | 2001-06-08 | Benzothiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02012596A true MXPA02012596A (es) | 2003-04-10 |
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ID=8169041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02012596A MXPA02012596A (es) | 2000-06-21 | 2001-06-08 | Derivados de benzotiazol. |
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Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2251419C2 (ru) * | 2000-06-21 | 2005-05-10 | Ф. Хоффманн-Ля Рош Аг | Производные бензотиазола |
| US6599901B1 (en) * | 2001-11-19 | 2003-07-29 | Hoffman-La Roche Inc. | Pyridone substituted benzothiazole derivatives |
| US6620811B2 (en) * | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
| MXPA04004982A (es) * | 2001-11-27 | 2004-08-11 | Hoffmann La Roche | Derivados de benzotiazol. |
| US6624163B2 (en) | 2001-11-29 | 2003-09-23 | Hoffman-La Roche Inc. | Benzothiazole derivatives |
| US6727247B2 (en) * | 2001-12-10 | 2004-04-27 | Hoffman-La Roche Inc. | Substituted benzothiazole amide derivatives |
| US6734179B2 (en) | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| EP1456196B1 (en) * | 2001-12-12 | 2009-01-07 | F. Hoffmann-La Roche Ag | Benzothiophenes as adenosine receptor modulators |
| US6713499B2 (en) * | 2001-12-12 | 2004-03-30 | Hoffman-La Roche Inc. | 7-Amino-benzothiazole derivatives |
| ES2716404T3 (es) | 2002-01-28 | 2019-06-12 | Kyowa Hakko Kogyo Kk | Antagonistas de receptores A2A para su uso en el tratamiento de trastornos del movimiento |
| DK1522314T3 (da) | 2002-06-26 | 2014-05-26 | Ono Pharmaceutical Co | Midler for sygdomme forårsaget af vaskulær sammentrækning eller udvidelse |
| US6958420B2 (en) * | 2002-07-19 | 2005-10-25 | Board Of Trustees Of Michigan State University | Synthesis of aminoarylboronic esters and substituted anilines from arenes via catalytic C-H activation/borylation/amination and uses thereof |
| US7338956B2 (en) | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| CN1738797A (zh) | 2002-11-19 | 2006-02-22 | 阿基里昂药品公司 | 取代的芳基硫脲和相关的化合物,病毒复制的抑制剂 |
| AR056615A1 (es) * | 2002-12-27 | 2007-10-17 | Kyowa Hakko Kogyo Kk | Un metodo de tratamiento de trastornos de la conducta |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| CN100406446C (zh) | 2003-01-13 | 2008-07-30 | 弗·哈夫曼-拉罗切有限公司 | 苯并唑衍生物及其作为腺苷受体配体的用途 |
| US6872833B2 (en) | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| WO2004101558A1 (en) * | 2003-05-13 | 2004-11-25 | F. Hoffmann-La Roche Ag | 2-imidazo-benzothiazoles as adenosine receptor ligands |
| ATE389652T1 (de) | 2003-05-19 | 2008-04-15 | Hoffmann La Roche | Benzothiazol-derivate als liganden des adenosinrezeptors |
| EP1628662B1 (en) * | 2003-05-21 | 2007-02-14 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives and use thereof in the treatment of diseases related to the adenosine a2a receptor |
| RU2348629C2 (ru) * | 2003-05-30 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг | Производные бензотиазола и их применение при лечении заболеваний, связанных с аденозиновыми a2a-рецепторами |
| BRPI0411699A (pt) * | 2003-06-20 | 2006-08-29 | Hoffmannn La Roche Ag F | compostos para uso como substáncia terapeuticamente ativa; método para o tratamento e/ou profilaxia de doenças que estão associadas à modulação de receptores cb1 e uso destes compostos |
| BRPI0412502A (pt) * | 2003-07-10 | 2006-09-19 | Achillion Pharmaceuticals Inc | derivados de ariltiouréia substituìda úteis como inibidores de replicação viral |
| ES2327684T3 (es) | 2003-07-24 | 2009-11-02 | Euro-Celtique S.A. | Compuestos heteroaril-tetrahidropiridilo utiles para el tratamiento o la prevencion del dolor. |
| EP1659881B1 (en) | 2003-08-06 | 2019-04-03 | Senomyx Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| WO2005028484A1 (en) | 2003-09-19 | 2005-03-31 | F. Hoffmann-La Roche Ag | Thiazolopyridine derivatives as adenosine receptor ligands |
| TW200600492A (en) * | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| AU2005247567B2 (en) * | 2004-05-24 | 2010-09-02 | F. Hoffmann-La Roche Ag | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide |
| KR100834179B1 (ko) * | 2004-05-24 | 2008-05-30 | 에프. 호프만-라 로슈 아게 | 4-하이드록시-4-메틸-피페리딘-1-카복실산(4-메톡시-7-모폴린-4-일-벤조티아졸-2-일)-아마이드 |
| AU2005263500B2 (en) | 2004-07-22 | 2011-02-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| RU2381227C2 (ru) * | 2004-07-22 | 2010-02-10 | Ф. Хоффманн-Ля Рош Аг | Замещенные бензотиазолы |
| SE0401970D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Novel compounds |
| EP1812392B1 (en) | 2004-11-05 | 2008-07-09 | F.Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| PT1863818E (pt) | 2005-03-23 | 2010-04-09 | Hoffmann La Roche | Derivados de acetilenil-pirazolo-pirimidina como antagonistas de mglur2 |
| TWI370820B (en) | 2005-04-27 | 2012-08-21 | Takeda Pharmaceutical | Fused heterocyclic compounds |
| ATE463495T1 (de) | 2005-09-27 | 2010-04-15 | Hoffmann La Roche | Oxadiazolylpyrazolopyrimidine als mglur2- antagonisten |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| EP1991528A2 (en) * | 2006-01-18 | 2008-11-19 | Siena Biotech S.p.A. | Modulators of alpha7 nicotinic acetylcholine receptors and therapeutic uses thereof |
| DK3235811T3 (en) | 2006-04-21 | 2018-11-12 | Senomyx Inc | PROCEDURE FOR THE PREPARATION OF OXALAMIDS |
| US7429589B2 (en) | 2006-04-27 | 2008-09-30 | Hoffmann-La Roche Inc. | Mono-nitration of aromatic compounds via nitrate salts |
| KR101077295B1 (ko) * | 2006-05-18 | 2011-10-26 | 에프. 호프만-라 로슈 아게 | 아데노신 ａ2ｂ 수용체 길항물질로서의 티아졸로-피라미딘/피리딘 우레아 유도체 |
| US8481544B2 (en) | 2006-06-22 | 2013-07-09 | Biota Europe Limited | Antibacterial compositions |
| GB0612428D0 (en) * | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
| WO2008077809A1 (en) * | 2006-12-22 | 2008-07-03 | F. Hoffmann-La Roche Ag | Process for the manufacture of 7-oxa-bicyclo derivatives |
| JP5606075B2 (ja) * | 2007-02-14 | 2014-10-15 | ビーエーエスエフ ソシエタス・ヨーロピア | エレクトロルミネッセンス金属錯体 |
| EP2142529B1 (en) * | 2007-04-27 | 2013-12-25 | Purdue Pharma LP | Trpv1 antagonists and uses thereof |
| MX2010000938A (es) * | 2007-07-23 | 2010-07-01 | Synosia Therapeutics Inc | Uso de (4-metoxi-7-morfolin-4-il-benzotiazol-2-il)-amida del ácido 4-hidroxi-4-metil-piperidin-1-carboxílico para el tratamiento del trastorno por estrés postraumático. |
| US7913765B2 (en) * | 2007-10-19 | 2011-03-29 | Baker Hughes Incorporated | Water absorbing or dissolving materials used as an in-flow control device and method of use |
| GB0724342D0 (en) | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| JO3101B1 (ar) | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
| KR101064258B1 (ko) * | 2008-12-29 | 2011-09-14 | 한국과학기술연구원 | 벤조아릴우레이도 화합물, 및 이를 함유하는 퇴행성 뇌질환예방 또는 치료용 조성물 |
| US8168785B2 (en) | 2009-06-17 | 2012-05-01 | Biotie Therapies, Inc. | Benzothiazole derivatives |
| WO2010150927A1 (en) * | 2009-06-25 | 2010-12-29 | Sk Holdings Co., Ltd. | Pharmaceutical composition for prevention and treatment of cancer diseases comprising benzamide derivatives |
| RU2455293C2 (ru) * | 2010-09-15 | 2012-07-10 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО ПГФА Росздрава) | N-(2-бензотиазолил)амид 3-бром-2,4-диоксо-4-(4-метоксифенил)бутановой кислоты, обладающий гипогликемической активностью |
| RU2448100C1 (ru) * | 2010-09-24 | 2012-04-20 | Татьяна Николаевна Иванова | Производные 2-аминобензотиазола, обладающие противогипоксической активностью, и способ их использования |
| US9000154B2 (en) * | 2010-10-19 | 2015-04-07 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| RS55701B1 (sr) | 2011-06-22 | 2017-07-31 | Purdue Pharma Lp | Trpv1 antagonisti koji uključuju dihidroksi supstituent i njihove upotrebe |
| TWI571466B (zh) * | 2011-10-14 | 2017-02-21 | 艾伯維有限公司 | 用於治療癌症及免疫與自體免疫疾病之細胞凋亡誘發劑 |
| CN103772376B (zh) * | 2012-10-24 | 2017-01-11 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| CA2957785C (en) | 2014-08-11 | 2023-01-03 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| CA2970819A1 (en) * | 2014-12-31 | 2016-07-07 | Angion Biomedica Corp. | Methods and agents for treating disease |
| WO2017066225A1 (en) * | 2015-10-14 | 2017-04-20 | Texas Tech University System | Pharmacoperones of the v2 receptor |
| ES2978159T3 (es) * | 2016-09-16 | 2024-09-06 | Hsf Pharmaceuticals | Inhibidores de factores de choque térmico (HSF) y usos de los mismos |
| WO2019025099A1 (en) * | 2017-08-01 | 2019-02-07 | Merck Patent Gmbh | THIAZOLOPYRIDINE DERIVATIVES AS ADENOSINE RECEPTOR ANTAGONISTS |
| WO2019062803A1 (zh) * | 2017-09-28 | 2019-04-04 | 基石药业 | 作为a2a受体抑制剂的并环类衍生物 |
| AR117844A1 (es) * | 2019-01-22 | 2021-09-01 | Merck Patent Gmbh | Derivados de tiazolopiridina como antagonistas del receptor de adenosina |
| DE102019110904B4 (de) * | 2019-04-26 | 2022-01-20 | Helmholtz-Zentrum Dresden - Rossendorf E. V. | N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-acetamid-Derivate und deren Verwendung |
| KR102796857B1 (ko) * | 2019-10-08 | 2025-04-15 | 현대자동차주식회사 | 냉각장치와 냉각시스템 및 냉각시스템의 제어방법 |
| CA3162227A1 (en) | 2019-12-16 | 2021-06-24 | David Scott Grierson | Antiviral compounds, compositions and methods of use |
| WO2021247921A1 (en) * | 2020-06-03 | 2021-12-09 | Yumanity Therapeutics, Inc. | Benzothiazole compounds and uses thereof |
| WO2022164135A1 (ko) * | 2021-01-29 | 2022-08-04 | 한국화학연구원 | 벤조티아졸 및 벤즈이미다졸 유도체, 약제학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH505543A (de) * | 1968-11-01 | 1971-04-15 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel |
| GB1318291A (en) * | 1970-04-15 | 1973-05-23 | Shell Int Research | Carboxamide derivatives and fungicidal compositions containing them |
| NL7109150A (enExample) * | 1970-07-06 | 1972-01-10 | ||
| JPS5516147B2 (enExample) * | 1971-12-24 | 1980-04-30 | ||
| US4028374A (en) * | 1975-11-03 | 1977-06-07 | Morton-Norwich Products, Inc. | Antibacterial thiocyanatobenzothiazoles |
| DE2656468A1 (de) * | 1976-12-14 | 1978-06-15 | Boehringer Mannheim Gmbh | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
| US4471957A (en) * | 1979-12-03 | 1984-09-18 | Baltimore Therapeutic Equipment Company | Method and apparatus for rehabilitation of damaged limbs |
| CA1153867A (en) | 1980-05-16 | 1983-09-20 | Michael A. M. Boersma | Process for the preparation of crystalline silicates, crystalline silicates so prepared and process for carrying out catalytic reactions |
| KR930005004B1 (ko) * | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
| FI91859C (fi) | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| EP0300688A1 (en) * | 1987-07-21 | 1989-01-25 | FISONS plc | Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them |
| US5348519A (en) * | 1988-02-04 | 1994-09-20 | Loredan Biomedical, Inc. | Exercise and diagnostic apparatus and method |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| JPH0667923B2 (ja) | 1989-05-11 | 1994-08-31 | 東洋紡績株式会社 | 新規なベンゾチアゾール誘導体 |
| WO1990015801A1 (en) * | 1989-06-22 | 1990-12-27 | Pfizer Inc. | Substituted sulfonamides and related compounds in the treatment of asthma, arthritis and related diseases |
| EP0427963B1 (de) | 1989-11-10 | 1994-03-30 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Verfahren zur Herstellung reiner, unsymmetrisch disubstituierter Harnstoffe |
| US5142910A (en) * | 1990-06-27 | 1992-09-01 | Occupational Orthopaedic Systems, Inc. | Dynamic physiological function testing apparatus and method |
| ES2082232T3 (es) * | 1990-10-15 | 1996-03-16 | Pfizer | Derivados de pirrolidina diona. |
| US5275045A (en) * | 1991-03-07 | 1994-01-04 | Isotechnologies, Inc. | Apparatus and method for use in assessing the lifting capability of a human subject |
| JP2599665B2 (ja) * | 1991-05-01 | 1997-04-09 | 大塚製薬株式会社 | ピラジン誘導体 |
| JP2759228B2 (ja) * | 1992-05-21 | 1998-05-28 | 株式会社大塚製薬工場 | ホスホン酸ジエステル誘導体 |
| US5312107A (en) * | 1993-05-13 | 1994-05-17 | Kordun, Ltd. | Golf club swing training and exercise device |
| JPH0725858A (ja) * | 1993-07-13 | 1995-01-27 | Otsuka Pharmaceut Co Ltd | ピペラジン誘導体 |
| JPH0940646A (ja) * | 1995-07-27 | 1997-02-10 | Yamanouchi Pharmaceut Co Ltd | ベンゼン縮合環誘導体又はその塩 |
| FR2753970B1 (fr) * | 1996-10-01 | 1998-10-30 | Synthelabo | Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique |
| JPH11130761A (ja) * | 1997-10-24 | 1999-05-18 | Otsuka Pharmaceut Co Ltd | ベンゾチアゾール誘導体 |
| NZ503491A (en) * | 1997-11-10 | 2002-08-28 | Bristol Myers Squibb Co | 2-substituted amino-1,3-benzothiazole derivatives useful as protein tyrosine kinase inhibitors |
| AU1924099A (en) * | 1997-12-18 | 1999-07-05 | Lyonnaise Industrielle Pharmaceutique (Lipha) | Piperazine derivatives useful as hypoglycemic agents |
| CA2318969A1 (en) * | 1998-01-23 | 1999-07-29 | Mikhail F. Gordeev | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| CN1325397A (zh) | 1998-09-30 | 2001-12-05 | 纽罗根公司 | 2－哌嗪烷基氨基苯并吡咯衍生物∶多巴胺受体亚型特异配体 |
| UA71587C2 (uk) * | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| ATE240316T1 (de) * | 1998-12-23 | 2003-05-15 | Lilly Co Eli | Heteroaromatische amide als inhibitoren von faktor xa |
| IL133680A0 (en) * | 1999-09-10 | 2001-04-30 | Can Fite Technologies Ltd | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
| EP1237862A1 (en) * | 1999-12-17 | 2002-09-11 | Versicor, Inc. | Succinate compounds, compositions and methods of use and preparation |
| RU2251419C2 (ru) * | 2000-06-21 | 2005-05-10 | Ф. Хоффманн-Ля Рош Аг | Производные бензотиазола |
| US6620811B2 (en) * | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
| US6727247B2 (en) * | 2001-12-10 | 2004-04-27 | Hoffman-La Roche Inc. | Substituted benzothiazole amide derivatives |
-
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