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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| AR046078A1 (es) | 2003-08-06 | 2005-11-23 | Senomyx Inc | Nuevos sabores, modificadores de sabores, sustancias gustativas, mejoradores de gusto, sustancias gustativas y/o mejoradoras del gusto umani o dulce y uso de los mismos. |
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| BRPI0706610A2 (pt) * | 2006-01-18 | 2011-04-05 | Siena Biotech Spa | moduladores de receptores alfa 7 nicotìnico acetilcolina e usos terapêuticos destes |
| WO2007124152A2 (en) | 2006-04-21 | 2007-11-01 | Senomyx, Inc. | Comestible compositions comprising high potency savory flavorants, and processes for producing them |
| US7429589B2 (en) | 2006-04-27 | 2008-09-30 | Hoffmann-La Roche Inc. | Mono-nitration of aromatic compounds via nitrate salts |
| EP2027132B1 (en) * | 2006-05-18 | 2010-09-15 | F. Hoffmann-La Roche AG | Thiazolo-pyramidine / pyridine urea derivatives as adenosine a2b receptor antagonists |
| GB0612428D0 (en) | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
| US8481544B2 (en) | 2006-06-22 | 2013-07-09 | Biota Europe Limited | Antibacterial compositions |
| WO2008077809A1 (en) * | 2006-12-22 | 2008-07-03 | F. Hoffmann-La Roche Ag | Process for the manufacture of 7-oxa-bicyclo derivatives |
| KR101516441B1 (ko) * | 2007-02-14 | 2015-05-07 | 바스프 에스이 | 전계발광 금속 착물 |
| UY31050A1 (es) * | 2007-04-27 | 2008-07-03 | Shionogi & Co | Antagonistas de trpv1 y usos de los mismos |
| AU2008279169A1 (en) * | 2007-07-23 | 2009-01-29 | Biotie Therapies, Inc | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide for the treatment of post-traumatic stress disorder |
| 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 |
| JP5769326B2 (ja) * | 2010-10-19 | 2015-08-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Rhoキナーゼ阻害薬 |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| MY185061A (en) | 2011-06-22 | 2021-04-30 | Shionogi & Co | Trpv1 antagonists including dihydroxy substituent and uses thereof |
| 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 |
| CN112961149A (zh) | 2014-08-11 | 2021-06-15 | 安吉恩生物医药公司 | 细胞色素p450抑制剂及其用途 |
| CN107531631B (zh) * | 2014-12-31 | 2021-09-03 | 安吉昂生物医药公司 | 用于治疗疾病的方法和药剂 |
| WO2017066225A1 (en) * | 2015-10-14 | 2017-04-20 | Texas Tech University System | Pharmacoperones of the v2 receptor |
| US11597708B2 (en) | 2016-09-16 | 2023-03-07 | Hsf Pharmaceuticals Sa | Inhibitors of heat shock factors and uses thereof |
| US11186592B2 (en) * | 2017-08-01 | 2021-11-30 | 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 |
| CN115151536A (zh) * | 2019-12-16 | 2022-10-04 | 不列颠哥伦比亚大学 | 抗病毒化合物、组合物及使用方法 |
| WO2021247921A1 (en) * | 2020-06-03 | 2021-12-09 | Yumanity Therapeutics, Inc. | Benzothiazole compounds and uses thereof |
| CN116829542A (zh) * | 2021-01-29 | 2023-09-29 | 韩国化学研究院 | 苯并噻唑及苯并咪唑衍生物、药学上可接受的盐、其制备方法以及包含其作为活性成分的药物组合物 |
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 (cs) * | 1970-07-06 | 1972-01-10 | ||
| JPS5516147B2 (cs) * | 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 |
| ATE103589T1 (de) | 1989-11-10 | 1994-04-15 | Agrolinz Agrarchemikalien | 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 |
| DE69116162T2 (de) * | 1990-10-15 | 1996-05-02 | Pfizer | Pyrrolidin-dionderivate |
| US5275045A (en) * | 1991-03-07 | 1994-01-04 | Isotechnologies, Inc. | Apparatus and method for use in assessing the lifting capability of a human subject |
| CN1038586C (zh) * | 1991-05-01 | 1998-06-03 | 大制药株式会社 | 吡嗪衍生物的制备方法 |
| PT604657E (pt) * | 1992-05-21 | 2000-04-28 | Otsuka Pharma Co Ltd | Derivado de diester fosfonico |
| 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 |
| CN1290165A (zh) * | 1997-11-10 | 2001-04-04 | 布里斯托尔-迈尔斯斯奎布公司 | 苯并噻唑蛋白酪氨酸激酶抑制剂 |
| WO1999031096A1 (en) * | 1997-12-18 | 1999-06-24 | Shaman Pharmaceuticals, Inc. | Piperazine derivatives useful as hypoglycemic agents |
| AU764184B2 (en) * | 1998-01-23 | 2003-08-14 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| CA2345944A1 (en) | 1998-09-30 | 2000-04-06 | Neurogen Corporation | 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands |
| UA71587C2 (uk) * | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| ES2196917T3 (es) * | 1998-12-23 | 2003-12-16 | Lilly Co Eli | Amidas heteroaromaticas como inhibidores del factor xa`. |
| IL133680A0 (en) * | 1999-09-10 | 2001-04-30 | Can Fite Technologies Ltd | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
| WO2001044179A1 (en) * | 1999-12-17 | 2001-06-21 | Versicor, Inc. | Novel succinate compounds, compositions and methods of use and preparation |
| HRP20020962A2 (en) * | 2000-06-21 | 2005-02-28 | F. Hoffmann - La Roche Ag | Benzothiazole derivatives |
| 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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