CA2530662A1 - Benzothiazole-4,7-diones et benzoxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation - Google Patents
Benzothiazole-4,7-diones et benzoxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation Download PDFInfo
- Publication number
- CA2530662A1 CA2530662A1 CA002530662A CA2530662A CA2530662A1 CA 2530662 A1 CA2530662 A1 CA 2530662A1 CA 002530662 A CA002530662 A CA 002530662A CA 2530662 A CA2530662 A CA 2530662A CA 2530662 A1 CA2530662 A1 CA 2530662A1
- Authority
- CA
- Canada
- Prior art keywords
- radical
- dione
- amino
- alkyl
- benzoxazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- KGCQVCRIAZKTIR-UHFFFAOYSA-N 1,3-benzoxazole-4,7-dione Chemical class O=C1C=CC(=O)C2=C1N=CO2 KGCQVCRIAZKTIR-UHFFFAOYSA-N 0.000 title abstract description 19
- BTHOJZRXYXQUTI-UHFFFAOYSA-N 1,3-benzothiazole-4,7-dione Chemical class O=C1C=CC(=O)C2=C1N=CS2 BTHOJZRXYXQUTI-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000003814 drug Substances 0.000 claims abstract description 30
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 27
- 229940079593 drug Drugs 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 13
- WSQGSLIWRYNKOL-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound FC1=CC=CC(Cl)=C1C1=NC(C(C(NCCN2CCCC2)=CC2=O)=O)=C2S1 WSQGSLIWRYNKOL-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 alkoxyalkyl radical Chemical group 0.000 claims description 294
- 150000001875 compounds Chemical class 0.000 claims description 215
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 100
- 150000003254 radicals Chemical class 0.000 claims description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 47
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 11
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 239000003586 protic polar solvent Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000005840 aryl radicals Chemical group 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 10
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- HXWPKDLSQVPQNG-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound C1=CC(F)=CC=C1C1=NC(C(C(NCCN2CCCC2)=CC2=O)=O)=C2S1 HXWPKDLSQVPQNG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- PZTFVEXPTRLXGC-UHFFFAOYSA-N 2-(2,5-dichlorothiophen-3-yl)-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound S1C(Cl)=CC(C=2SC3=C(C(C(NCCN4CCCC4)=CC3=O)=O)N=2)=C1Cl PZTFVEXPTRLXGC-UHFFFAOYSA-N 0.000 claims description 6
- IHZUQXVCAYBGNN-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C1=C(F)C=CC=C1F IHZUQXVCAYBGNN-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- KQOYYIUMAGYDHB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound O=C1C=2OC(C=3C=C4OCOC4=CC=3)=NC=2C(=O)C=C1NCCN1CCCC1 KQOYYIUMAGYDHB-UHFFFAOYSA-N 0.000 claims description 5
- LSOWTSJESCKUMW-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound BrC1=CC=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 LSOWTSJESCKUMW-UHFFFAOYSA-N 0.000 claims description 5
- WCUXJAHSNPROCI-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C1=C(F)C=CC=C1Cl WCUXJAHSNPROCI-UHFFFAOYSA-N 0.000 claims description 5
- VRRWARUFPFGFBO-UHFFFAOYSA-N 2-(3-bromophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound BrC1=CC=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 VRRWARUFPFGFBO-UHFFFAOYSA-N 0.000 claims description 5
- LYJGKODOQGDIRP-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound ClC1=CC(Br)=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 LYJGKODOQGDIRP-UHFFFAOYSA-N 0.000 claims description 5
- XRIJJOYQZVVEMZ-UHFFFAOYSA-N 2-(4-bromophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound C1=CC(Br)=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 XRIJJOYQZVVEMZ-UHFFFAOYSA-N 0.000 claims description 5
- ZFDIRIRYJUNZPD-UHFFFAOYSA-N 2-(4-bromophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC=C(Br)C=C1 ZFDIRIRYJUNZPD-UHFFFAOYSA-N 0.000 claims description 5
- PKGLTQZDWLUGNO-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound C1=CC(F)=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 PKGLTQZDWLUGNO-UHFFFAOYSA-N 0.000 claims description 5
- OQYMDHDGGXMBGS-UHFFFAOYSA-N 6-[2-(dimethylamino)ethylamino]-2-naphthalen-2-yl-1,3-benzothiazole-4,7-dione Chemical compound C1=CC=CC2=CC(C3=NC=4C(=O)C=C(C(C=4S3)=O)NCCN(C)C)=CC=C21 OQYMDHDGGXMBGS-UHFFFAOYSA-N 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- FFVFVGZJVGNKRT-UHFFFAOYSA-N 2-(2,3-difluorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC=CC(F)=C1F FFVFVGZJVGNKRT-UHFFFAOYSA-N 0.000 claims description 4
- UKGGZBHWHUUGEV-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound S1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC(F)=CC=C1F UKGGZBHWHUUGEV-UHFFFAOYSA-N 0.000 claims description 4
- JLGBOGHFCQJXRX-UHFFFAOYSA-N 2-(2-bromophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC=CC=C1Br JLGBOGHFCQJXRX-UHFFFAOYSA-N 0.000 claims description 4
- HRYTTZGDUJKAID-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 HRYTTZGDUJKAID-UHFFFAOYSA-N 0.000 claims description 4
- BSLQGZVKGUQMBQ-UHFFFAOYSA-N 2-(3,5-dibromophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound BrC1=CC(Br)=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 BSLQGZVKGUQMBQ-UHFFFAOYSA-N 0.000 claims description 4
- GKLDSXVHMRSCPR-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound FC1=CC(F)=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 GKLDSXVHMRSCPR-UHFFFAOYSA-N 0.000 claims description 4
- IBKLZXYCWTYVGO-UHFFFAOYSA-N 2-(3-chlorophenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound ClC1=CC=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 IBKLZXYCWTYVGO-UHFFFAOYSA-N 0.000 claims description 4
- AITCDJDKIOTYAS-UHFFFAOYSA-N 2-(4-ethylphenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound C1=CC(CC)=CC=C1C1=NC(C(C=C(NCCN2CCCC2)C2=O)=O)=C2O1 AITCDJDKIOTYAS-UHFFFAOYSA-N 0.000 claims description 4
- SFSIRTJZZTYSNB-UHFFFAOYSA-N 6-(2-pyrrolidin-1-ylethylamino)-2-(3,4,5-trimethoxyphenyl)-1,3-benzoxazole-4,7-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 SFSIRTJZZTYSNB-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 4
- OATJAIRTLJSUJZ-UHFFFAOYSA-N 2-(2,3-difluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2OC=1C1=CC=CC(F)=C1F OATJAIRTLJSUJZ-UHFFFAOYSA-N 0.000 claims description 3
- HYJHRMRZZSOIKS-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2OC=1C1=CC(F)=CC=C1F HYJHRMRZZSOIKS-UHFFFAOYSA-N 0.000 claims description 3
- FOJHTOMZWUIILB-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC(F)=CC=C1F FOJHTOMZWUIILB-UHFFFAOYSA-N 0.000 claims description 3
- GRURYTQEVMHRTP-UHFFFAOYSA-N 2-(2-bromophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2OC=1C1=CC=CC=C1Br GRURYTQEVMHRTP-UHFFFAOYSA-N 0.000 claims description 3
- KTQJFPUZZOHGLN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C(C=C(NCCN(C)C)C2=O)=O)=C2O1 KTQJFPUZZOHGLN-UHFFFAOYSA-N 0.000 claims description 3
- SDTAJQMVBKZMSB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound FC1=CC(F)=CC(C=2OC3=C(C(C(NCCN4CCCC4)=CC3=O)=O)N=2)=C1 SDTAJQMVBKZMSB-UHFFFAOYSA-N 0.000 claims description 3
- PKIQFTUWWDNUBC-UHFFFAOYSA-N 2-(3-bromophenyl)-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound BrC1=CC=CC(C=2OC3=C(C(C(NCCN4CCCC4)=CC3=O)=O)N=2)=C1 PKIQFTUWWDNUBC-UHFFFAOYSA-N 0.000 claims description 3
- VFCQYGURDDJJQU-UHFFFAOYSA-N 2-(3-chlorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC=CC(Cl)=C1 VFCQYGURDDJJQU-UHFFFAOYSA-N 0.000 claims description 3
- KFMAFARKULOIKB-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC=C(Br)C=C1Cl KFMAFARKULOIKB-UHFFFAOYSA-N 0.000 claims description 3
- OVBAJJSRJDQIMS-UHFFFAOYSA-N 2-(4-bromo-3-methylphenyl)-6-(2-pyrrolidin-1-ylethylamino)-1,3-benzoxazole-4,7-dione Chemical compound C1=C(Br)C(C)=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 OVBAJJSRJDQIMS-UHFFFAOYSA-N 0.000 claims description 3
- YCOPQWHJPZMDRT-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1CC1=C(Cl)C=CC=C1Cl YCOPQWHJPZMDRT-UHFFFAOYSA-N 0.000 claims description 3
- TYMFWTFOGORBKI-UHFFFAOYSA-N 5-(2-pyrrolidin-1-ylethylamino)-2-(3,4,5-trifluorophenyl)-1,3-benzoxazole-4,7-dione Chemical compound FC1=C(F)C(F)=CC(C=2OC3=C(C(C(NCCN4CCCC4)=CC3=O)=O)N=2)=C1 TYMFWTFOGORBKI-UHFFFAOYSA-N 0.000 claims description 3
- LPEHETKTJYHXOD-UHFFFAOYSA-N 5-[2-(dimethylamino)ethylamino]-2-(4-fluorophenyl)-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C1=CC=C(F)C=C1 LPEHETKTJYHXOD-UHFFFAOYSA-N 0.000 claims description 3
- KMQZWARFDYVZSX-UHFFFAOYSA-N 6-(2-pyrrolidin-1-ylethylamino)-2-(3,4,5-trifluorophenyl)-1,3-benzoxazole-4,7-dione Chemical compound FC1=C(F)C(F)=CC(C=2OC3=C(C(C=C(NCCN4CCCC4)C3=O)=O)N=2)=C1 KMQZWARFDYVZSX-UHFFFAOYSA-N 0.000 claims description 3
- ULBHEDHPLUXSDQ-UHFFFAOYSA-N 6-[2-(dimethylamino)ethylamino]-2-(3,4,5-trimethoxyphenyl)-1,3-benzoxazole-4,7-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C(C=C(NCCN(C)C)C3=O)=O)N=2)=C1 ULBHEDHPLUXSDQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 3
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 3
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- NIWKJYIFRLQGSC-UHFFFAOYSA-N 2-(2,5-dichlorothiophen-3-yl)-5-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C=1C=C(Cl)SC=1Cl NIWKJYIFRLQGSC-UHFFFAOYSA-N 0.000 claims description 2
- QKTFHHAPASFUJV-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound S1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=C(F)C=CC=C1Cl QKTFHHAPASFUJV-UHFFFAOYSA-N 0.000 claims description 2
- KZEXHFYTUSUMJG-UHFFFAOYSA-N 2-(3,5-dibromophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC(Br)=CC(Br)=C1 KZEXHFYTUSUMJG-UHFFFAOYSA-N 0.000 claims description 2
- YONONEFVGAFJHN-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2OC=1C1=CC(F)=CC(F)=C1 YONONEFVGAFJHN-UHFFFAOYSA-N 0.000 claims description 2
- KKIZXRUACHELEK-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-6-[2-(dimethylamino)ethylamino]-1,3-benzoxazole-4,7-dione Chemical compound O1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2N=C1C1=CC(F)=CC(F)=C1 KKIZXRUACHELEK-UHFFFAOYSA-N 0.000 claims description 2
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Reproductive Health (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Cardiology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0307648A FR2856686A1 (fr) | 2003-06-25 | 2003-06-25 | Benzothiazole-4,7-diones et benzooxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation |
| FR03/07648 | 2003-06-25 | ||
| PCT/FR2004/001578 WO2005000843A2 (fr) | 2003-06-25 | 2004-06-24 | Benzothiazole-4,7-diones et benzoxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2530662A1 true CA2530662A1 (fr) | 2005-01-06 |
Family
ID=33515381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002530662A Abandoned CA2530662A1 (fr) | 2003-06-25 | 2004-06-24 | Benzothiazole-4,7-diones et benzoxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7335674B2 (enExample) |
| EP (1) | EP1641789A2 (enExample) |
| JP (1) | JP2007515383A (enExample) |
| KR (1) | KR20060024814A (enExample) |
| CN (1) | CN1842522A (enExample) |
| AR (1) | AR044929A1 (enExample) |
| AU (1) | AU2004251912A1 (enExample) |
| BR (1) | BRPI0411871A (enExample) |
| CA (1) | CA2530662A1 (enExample) |
| FR (1) | FR2856686A1 (enExample) |
| IL (1) | IL172774A0 (enExample) |
| MX (1) | MXPA06000217A (enExample) |
| NO (1) | NO20060124L (enExample) |
| RU (1) | RU2006101980A (enExample) |
| WO (1) | WO2005000843A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2834289B1 (fr) * | 2001-12-27 | 2004-03-19 | Sod Conseils Rech Applic | Derives de benzothiazole-4,7-diones et benzooxazole-4,7- diones, leur preparation et leurs applications therapeutiques |
| ATE368654T1 (de) * | 2001-12-27 | 2007-08-15 | Sod Conseils Rech Applic | Benzothiazol- und benzoxazol-4,7-dionderivate und ihre verwendung als cdc25-phosphatasen- inhibitoren |
| FR2856688B1 (fr) * | 2003-06-25 | 2008-05-30 | Sod Conseils Rech Applic | PRODUIT COMPRENANT AU MOINS UN INHIBITEUR DE PHOSPHATASE CDc25 EN ASSOCIATION AVEC AU MOINS UN AUTRE AGENT ANTI-CANCEREUX |
| FR2877667B1 (fr) | 2004-11-05 | 2007-03-23 | Sod Conseils Rech Applic | Derives de 4,7-dioxobenzothiazole-2-carboxamides, leur preparation et leurs applications therapeutiques |
| FR2879598B1 (fr) | 2004-12-17 | 2007-03-30 | Sod Conseils Rech Applic | Inhibiteurs de phosphatases cdc25 |
| FR2945532A1 (fr) * | 2009-05-15 | 2010-11-19 | Ipsen Pharma Sas | Derives de tri-amino-pyrimidine comme inhibiteurs de phosphatases cdc25 |
| BR112019007271A2 (pt) * | 2016-10-10 | 2019-09-17 | Dev Ct Biotechnology | compostos de quinoxalina como inibidores do receptor da tirosina quinase do tipo iii |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2825278A1 (fr) * | 2001-05-30 | 2002-12-06 | Sod Conseils Rech Applic | Produit comprenant du mikanolide, du dihydromikanolide ou un analogue de ceux-ci en association avec un autre agent anti-cancereux pour une utilisation therapeutique dans le traitement du cancer |
| ATE368654T1 (de) * | 2001-12-27 | 2007-08-15 | Sod Conseils Rech Applic | Benzothiazol- und benzoxazol-4,7-dionderivate und ihre verwendung als cdc25-phosphatasen- inhibitoren |
-
2003
- 2003-06-25 FR FR0307648A patent/FR2856686A1/fr active Pending
-
2004
- 2004-06-24 AU AU2004251912A patent/AU2004251912A1/en not_active Abandoned
- 2004-06-24 US US10/562,949 patent/US7335674B2/en not_active Expired - Fee Related
- 2004-06-24 CN CNA2004800243949A patent/CN1842522A/zh active Pending
- 2004-06-24 RU RU2006101980/04A patent/RU2006101980A/ru not_active Application Discontinuation
- 2004-06-24 CA CA002530662A patent/CA2530662A1/fr not_active Abandoned
- 2004-06-24 WO PCT/FR2004/001578 patent/WO2005000843A2/fr not_active Ceased
- 2004-06-24 KR KR1020057024694A patent/KR20060024814A/ko not_active Withdrawn
- 2004-06-24 EP EP04767434A patent/EP1641789A2/fr not_active Ceased
- 2004-06-24 MX MXPA06000217A patent/MXPA06000217A/es not_active Application Discontinuation
- 2004-06-24 JP JP2006516315A patent/JP2007515383A/ja not_active Abandoned
- 2004-06-24 BR BRPI0411871-5A patent/BRPI0411871A/pt not_active IP Right Cessation
- 2004-06-25 AR ARP040102256A patent/AR044929A1/es not_active Application Discontinuation
-
2005
- 2005-12-22 IL IL172774A patent/IL172774A0/en unknown
-
2006
- 2006-01-09 NO NO20060124A patent/NO20060124L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006101980A (ru) | 2006-07-27 |
| US20060135573A1 (en) | 2006-06-22 |
| JP2007515383A (ja) | 2007-06-14 |
| WO2005000843A2 (fr) | 2005-01-06 |
| US7335674B2 (en) | 2008-02-26 |
| BRPI0411871A (pt) | 2006-08-08 |
| AU2004251912A1 (en) | 2005-01-06 |
| WO2005000843A3 (fr) | 2005-05-26 |
| NO20060124L (no) | 2006-01-20 |
| IL172774A0 (en) | 2006-04-10 |
| CN1842522A (zh) | 2006-10-04 |
| KR20060024814A (ko) | 2006-03-17 |
| AR044929A1 (es) | 2005-10-12 |
| FR2856686A1 (fr) | 2004-12-31 |
| EP1641789A2 (fr) | 2006-04-05 |
| MXPA06000217A (es) | 2006-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |