ZA200209730B - Benzothiazole derivatives. - Google Patents
Benzothiazole derivatives. Download PDFInfo
- Publication number
- ZA200209730B ZA200209730B ZA200209730A ZA200209730A ZA200209730B ZA 200209730 B ZA200209730 B ZA 200209730B ZA 200209730 A ZA200209730 A ZA 200209730A ZA 200209730 A ZA200209730 A ZA 200209730A ZA 200209730 B ZA200209730 B ZA 200209730B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- benzothiazol
- methyl
- benzamide
- lower alkyl
- 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 description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- -1 2,3-dihydro-1H-indolyl Chemical group 0.000 claims description 63
- 125000003545 alkoxy group Chemical group 0.000 claims description 63
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 27
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 25
- 229960005305 adenosine Drugs 0.000 claims description 25
- 102000005962 receptors Human genes 0.000 claims description 21
- 108020003175 receptors Proteins 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 102000009346 Adenosine receptors Human genes 0.000 claims description 17
- 108050000203 Adenosine receptors Proteins 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 13
- 125000005605 benzo group Chemical group 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 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
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 7
- 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
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- CEKSPMMCISUSTR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroquinoline Chemical compound C1CCC2CCCNC2=C1 CEKSPMMCISUSTR-UHFFFAOYSA-N 0.000 claims description 4
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 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
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- JIZKFFXGUANXJD-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-oxopiperidine-1-carboxamide Chemical compound C1=2SC(NC(=O)N3CCC(=O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 JIZKFFXGUANXJD-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
- UXKAILIUQKAFKX-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-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=CC=C1 UXKAILIUQKAFKX-UHFFFAOYSA-N 0.000 claims description 4
- PWQWBWNXTAKBFJ-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)morpholine-4-carboxamide Chemical compound C1=2SC(NC(=O)N3CCOCC3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 PWQWBWNXTAKBFJ-UHFFFAOYSA-N 0.000 claims description 4
- GCOUHNUYAZPKTC-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)thiomorpholine-4-carboxamide Chemical compound C1=2SC(NC(=O)N3CCSCC3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 GCOUHNUYAZPKTC-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- KJQLKXGPBVTCPP-UHFFFAOYSA-N n-[4-methoxy-7-[2-(6-methylpyridin-3-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=C(C)N=C1 KJQLKXGPBVTCPP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- SKXVYZIWQHIZQQ-UHFFFAOYSA-N tert-butyl 4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]piperidine-1-carboxylate Chemical compound C1=2SC(NC(=O)C3CCN(CC3)C(=O)OC(C)(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 SKXVYZIWQHIZQQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- QEHJOXFNOQYDIG-UHFFFAOYSA-N 4-[(4-hydroxypiperidin-1-yl)methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCC(O)CC4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 QEHJOXFNOQYDIG-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UEUGIJULIDQKSX-UHFFFAOYSA-N 4-[[2-methoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 UEUGIJULIDQKSX-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
- 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 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
- 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
- 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 3
- 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 3
- YDOMZIFLAYDCAW-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-5-methylfuran-2-carboxamide Chemical compound C1=2SC(NC(=O)C=3OC(C)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 YDOMZIFLAYDCAW-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- 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 3
- 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 3
- FZYJSKAMSGKAAR-UHFFFAOYSA-N n-[4-methoxy-7-(2-methylpyridin-4-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=NC(C)=C1 FZYJSKAMSGKAAR-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- WSXJICSDYKOLLR-UHFFFAOYSA-N n-[4-methoxy-7-[2-(6-methylpyridin-3-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]morpholine-4-carboxamide Chemical compound C1=2SC(NC(=O)N3CCOCC3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=C(C)N=C1 WSXJICSDYKOLLR-UHFFFAOYSA-N 0.000 claims description 3
- 229940037201 oris Drugs 0.000 claims description 3
- HKQONCAOBFVGKI-UHFFFAOYSA-N 1-acetyl-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)piperidine-4-carboxamide Chemical compound C1=2SC(NC(=O)C3CCN(CC3)C(C)=O)=NC=2C(OC)=CC=C1N1CCOCC1 HKQONCAOBFVGKI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
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EP00113219 | 2000-06-21 |
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ZA200209730A ZA200209730B (en) | 2000-06-21 | 2002-11-29 | Benzothiazole derivatives. |
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US (8) | US6521754B2 (fr) |
EP (2) | EP1797878A3 (fr) |
JP (1) | JP3886897B2 (fr) |
KR (2) | KR100526487B1 (fr) |
CN (1) | CN1234358C (fr) |
AR (1) | AR031244A1 (fr) |
AT (1) | ATE385794T1 (fr) |
AU (2) | AU2001281817B2 (fr) |
BR (1) | BR0112395A (fr) |
CA (1) | CA2413086C (fr) |
CY (1) | CY1107401T1 (fr) |
CZ (1) | CZ2003182A3 (fr) |
DE (1) | DE60132777T2 (fr) |
DK (1) | DK1303272T3 (fr) |
EC (1) | ECSP024399A (fr) |
ES (1) | ES2299504T3 (fr) |
HK (1) | HK1058148A1 (fr) |
HR (1) | HRP20020962A2 (fr) |
HU (1) | HUP0301315A3 (fr) |
IL (2) | IL153278A0 (fr) |
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MX (1) | MXPA02012596A (fr) |
MY (1) | MY138352A (fr) |
NO (2) | NO324635B1 (fr) |
NZ (1) | NZ522928A (fr) |
PE (1) | PE20020104A1 (fr) |
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PT (1) | PT1303272E (fr) |
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SI (1) | SI1303272T1 (fr) |
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WO (1) | WO2001097786A2 (fr) |
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AR056615A1 (es) * | 2002-12-27 | 2007-10-17 | Kyowa Hakko Kogyo Kk | Un metodo de tratamiento de trastornos de la conducta |
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AU2004238508B2 (en) * | 2003-05-13 | 2009-11-19 | F. Hoffmann-La Roche Ag | Imidazo-benzothiazoles |
PL1636223T3 (pl) * | 2003-05-19 | 2008-07-31 | Hoffmann La Roche | Pochodne benzotiazolu jako ligandy receptora adenozynowego |
WO2004103367A1 (fr) * | 2003-05-21 | 2004-12-02 | F. Hoffmann-La Roche Ag | Derives du benzothiazole et leur utilisation dans le traitement de maladies liees au recepteur a2a de l'adenosine |
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JP2007523868A (ja) * | 2003-07-10 | 2007-08-23 | アキリオン ファーマシューティカルズ,インコーポレーテッド | ウイルス複製の阻害薬として有用な置換アリールチオウレア誘導体類 |
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SG145745A1 (en) | 2003-08-06 | 2008-09-29 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
WO2005028484A1 (fr) | 2003-09-19 | 2005-03-31 | F. Hoffmann-La Roche Ag | Derives de thiazolopyridine en tant que ligands du recepteur d'adenosine |
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