ZA200207069B - Aryl substituted pyridines, pyrimidines, pyrazines and triazines and the use thereof. - Google Patents
Aryl substituted pyridines, pyrimidines, pyrazines and triazines and the use thereof. Download PDFInfo
- Publication number
- ZA200207069B ZA200207069B ZA200207069A ZA200207069A ZA200207069B ZA 200207069 B ZA200207069 B ZA 200207069B ZA 200207069 A ZA200207069 A ZA 200207069A ZA 200207069 A ZA200207069 A ZA 200207069A ZA 200207069 B ZA200207069 B ZA 200207069B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- group
- amino
- alkyl
- hydrogen
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims description 35
- 150000003216 pyrazines Chemical class 0.000 title description 12
- 150000003222 pyridines Chemical class 0.000 title description 11
- 150000003230 pyrimidines Chemical class 0.000 title description 11
- 150000003918 triazines Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 132
- -1 2-imidazolinyl Chemical group 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000003342 alkenyl group Chemical group 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
- 125000003282 alkyl amino group Chemical group 0.000 claims description 30
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 229940002612 prodrug Drugs 0.000 claims description 23
- 239000000651 prodrug Substances 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 21
- 208000002193 Pain Diseases 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 19
- 150000001356 alkyl thiols Chemical class 0.000 claims description 18
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 13
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004442 acylamino group Chemical group 0.000 claims description 12
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
- 150000003573 thiols Chemical class 0.000 claims description 12
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 11
- 230000036407 pain Effects 0.000 claims description 11
- MKRVOXRLAFVYCF-UHFFFAOYSA-N C(#N)NN([N+](=O)[O-])O Chemical compound C(#N)NN([N+](=O)[O-])O MKRVOXRLAFVYCF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 108010052164 Sodium Channels Proteins 0.000 claims description 9
- 102000018674 Sodium Channels Human genes 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 208000000094 Chronic Pain Diseases 0.000 claims description 7
- 208000009205 Tinnitus Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000028867 ischemia Diseases 0.000 claims description 7
- 231100000886 tinnitus Toxicity 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 230000036461 convulsion Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000000626 neurodegenerative effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- QMVBNJRNXHVTRL-UHFFFAOYSA-N 6-(dimethylamino)-n,n-dimethyl-2-(4-phenoxyphenyl)pyrimidine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(N(C)C)=NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 QMVBNJRNXHVTRL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 2
- ATMZLYHEQVWQRN-UHFFFAOYSA-N 2-[4-(4-chloro-2-fluorophenoxy)phenyl]-n-methylpyrimidine-4-carboxamide Chemical compound CNC(=O)C1=CC=NC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 ATMZLYHEQVWQRN-UHFFFAOYSA-N 0.000 claims description 2
- PIJRDAGFQBHTSY-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-6-methylpyridine Chemical compound CC1=CC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 PIJRDAGFQBHTSY-UHFFFAOYSA-N 0.000 claims description 2
- KXCKPPJTZRZWNG-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 KXCKPPJTZRZWNG-UHFFFAOYSA-N 0.000 claims description 2
- RYFIRHQXJRDOOI-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenoxy)phenyl]pyrimidin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 RYFIRHQXJRDOOI-UHFFFAOYSA-N 0.000 claims description 2
- DPALLLMMVFJSQV-UHFFFAOYSA-N 2-methyl-4-[4-(4-nitrophenoxy)phenyl]-1,3,5-triazine Chemical compound CC1=NC=NC(C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 DPALLLMMVFJSQV-UHFFFAOYSA-N 0.000 claims description 2
- LLHYGTSULGYMFT-UHFFFAOYSA-N 2-methyl-6-(4-phenoxyphenyl)pyridine Chemical compound CC1=CC=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 LLHYGTSULGYMFT-UHFFFAOYSA-N 0.000 claims description 2
- PLRKONMTZWEDAQ-UHFFFAOYSA-N 3,5-diamino-6-(4-phenoxyphenyl)pyrazine-2-carboxamide Chemical compound N1=C(N)C(C(=O)N)=NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1N PLRKONMTZWEDAQ-UHFFFAOYSA-N 0.000 claims description 2
- RVAGMEJJTRXKLJ-UHFFFAOYSA-N 4-[3-fluoro-4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=C(F)C(OC=3C=CC(F)=CC=3)=CC=2)=N1 RVAGMEJJTRXKLJ-UHFFFAOYSA-N 0.000 claims description 2
- WOPOSJSIRYNYJB-UHFFFAOYSA-N 4-[4-(4-chloro-2-fluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 WOPOSJSIRYNYJB-UHFFFAOYSA-N 0.000 claims description 2
- NIPYMEJEJIJBBQ-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)phenyl]-2-(1h-pyrazol-5-yl)pyrimidine Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=C(N=CC=2)C2=NNC=C2)C=C1 NIPYMEJEJIJBBQ-UHFFFAOYSA-N 0.000 claims description 2
- VRJVILHZJJQKKH-UHFFFAOYSA-N 4-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 VRJVILHZJJQKKH-UHFFFAOYSA-N 0.000 claims description 2
- HJEYZPBTKCSSQP-UHFFFAOYSA-N 6-(4-butylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(CCCC)=CC=C1C1=CC=CC(C(N)=O)=N1 HJEYZPBTKCSSQP-UHFFFAOYSA-N 0.000 claims description 2
- VKOJOHPYKSVBJH-UHFFFAOYSA-N 6-(4-methoxyphenyl)pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(C(N)=O)=N1 VKOJOHPYKSVBJH-UHFFFAOYSA-N 0.000 claims description 2
- XEKGGPAHQNVZMO-UHFFFAOYSA-N 6-(4-phenoxyphenyl)pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 XEKGGPAHQNVZMO-UHFFFAOYSA-N 0.000 claims description 2
- XHSVLAXDUYLSRW-UHFFFAOYSA-N 6-(4-phenoxyphenyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 XHSVLAXDUYLSRW-UHFFFAOYSA-N 0.000 claims description 2
- IMVMSRQXEUOIAI-UHFFFAOYSA-N 6-(4-propylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC(C(N)=O)=N1 IMVMSRQXEUOIAI-UHFFFAOYSA-N 0.000 claims description 2
- HRFMUXRVAOOKPB-UHFFFAOYSA-N 6-(4-tert-butylphenyl)pyridine-2-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C(N)=O)=N1 HRFMUXRVAOOKPB-UHFFFAOYSA-N 0.000 claims description 2
- LBJHVJOCNFEDQG-UHFFFAOYSA-N 6-[4-(2,4-difluorophenoxy)phenyl]pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)F)=CC=2)=N1 LBJHVJOCNFEDQG-UHFFFAOYSA-N 0.000 claims description 2
- AOMWTDFUWKTRKL-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-n-(2-piperidin-1-ylethyl)pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=C(C=CC=2)C(=O)NCCN2CCCCC2)C=C1 AOMWTDFUWKTRKL-UHFFFAOYSA-N 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- WHCCLTLUZWUDHL-UHFFFAOYSA-N n-methyl-6-(4-phenoxyphenyl)pyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 WHCCLTLUZWUDHL-UHFFFAOYSA-N 0.000 claims description 2
- LXMYTVZYLYWCNY-UHFFFAOYSA-N n-tert-butyl-4-[4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound CC(C)(C)NC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 LXMYTVZYLYWCNY-UHFFFAOYSA-N 0.000 claims description 2
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 2
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 2
- IIZXKJKYBKWGNW-UHFFFAOYSA-M sodium;4-[4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 IIZXKJKYBKWGNW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims 4
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 4
- TVELBYZQRWPJQR-UHFFFAOYSA-N 2-[4-(4-chloro-2-fluorophenoxy)phenyl]pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 TVELBYZQRWPJQR-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- 238000002690 local anesthesia Methods 0.000 claims 2
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims 2
- XFDYSANXRMIAEK-UHFFFAOYSA-N 1-[4-[4-(4-fluorophenoxy)phenyl]pyrimidin-2-yl]ethanone Chemical compound CC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 XFDYSANXRMIAEK-UHFFFAOYSA-N 0.000 claims 1
- WIUJAEYEOGDJOM-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)-4-[4-(4-fluorophenoxy)phenyl]pyrimidine Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=C(N=CC=2)C=2NCCN=2)C=C1 WIUJAEYEOGDJOM-UHFFFAOYSA-N 0.000 claims 1
- NHWPKKKCQZITLB-UHFFFAOYSA-N 2-[3-fluoro-4-(4-fluorophenoxy)phenyl]pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2C=C(F)C(OC=3C=CC(F)=CC=3)=CC=2)=N1 NHWPKKKCQZITLB-UHFFFAOYSA-N 0.000 claims 1
- VYTMYDJWGZCWGL-UHFFFAOYSA-N 2-[4-(4-chloro-2-fluorophenoxy)phenyl]pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 VYTMYDJWGZCWGL-UHFFFAOYSA-N 0.000 claims 1
- XYTLGLMIPCYBMD-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)Cl)=CC=2)=N1 XYTLGLMIPCYBMD-UHFFFAOYSA-N 0.000 claims 1
- RWSBBDVQSLNELF-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 RWSBBDVQSLNELF-UHFFFAOYSA-N 0.000 claims 1
- ZZFFNQDNKLCMLT-UHFFFAOYSA-N 4-[4-(4-methoxyphenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C=2N=C(N=CC=2)C(N)=O)C=C1 ZZFFNQDNKLCMLT-UHFFFAOYSA-N 0.000 claims 1
- DKQTVPMLNUWSNW-UHFFFAOYSA-N 6-(4-phenoxyphenyl)pyrazine-2-carboxamide Chemical compound NC(=O)C1=CN=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 DKQTVPMLNUWSNW-UHFFFAOYSA-N 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- 108091006146 Channels Proteins 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
- UXXQEVFRPLIOHJ-UHFFFAOYSA-N 2-chloropyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(Cl)=N1 UXXQEVFRPLIOHJ-UHFFFAOYSA-N 0.000 description 2
- WWUHILXOVWDAGZ-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)phenyl]-n-formylpyrimidine-2-carboxamide Chemical compound OC=NC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 WWUHILXOVWDAGZ-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 1
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- 230000002218 hypoglycaemic effect Effects 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HTDFEXRUDGWNHA-UHFFFAOYSA-N lifarizine Chemical compound CC=1NC(C=2C=CC(C)=CC=2)=NC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HTDFEXRUDGWNHA-UHFFFAOYSA-N 0.000 description 1
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- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
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- ZEJPMRKECMRICL-UHFFFAOYSA-N o-ethyl 2-amino-2-oxoethanethioate Chemical compound CCOC(=S)C(N)=O ZEJPMRKECMRICL-UHFFFAOYSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- IPEHBUMCGVEMRF-SFIIULIVSA-N pyrazine-2-carboxamide Chemical compound N[11C](=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-SFIIULIVSA-N 0.000 description 1
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- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 229960004181 riluzole Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18818800P | 2000-03-10 | 2000-03-10 |
Publications (1)
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|---|---|
| ZA200207069B true ZA200207069B (en) | 2003-12-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207069A ZA200207069B (en) | 2000-03-10 | 2002-09-03 | Aryl substituted pyridines, pyrimidines, pyrazines and triazines and the use thereof. |
Country Status (34)
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| EP (1) | EP1265866B1 (de) |
| JP (2) | JP4359016B2 (de) |
| KR (1) | KR20030011792A (de) |
| CN (1) | CN1422254A (de) |
| AP (1) | AP1404A (de) |
| AR (1) | AR029489A1 (de) |
| AT (1) | ATE474828T1 (de) |
| AU (2) | AU4562001A (de) |
| BR (1) | BR0108918A (de) |
| CA (1) | CA2400945C (de) |
| CR (1) | CR6774A (de) |
| CY (1) | CY1110809T1 (de) |
| CZ (1) | CZ20032228A3 (de) |
| DE (1) | DE60142613D1 (de) |
| DK (1) | DK1265866T3 (de) |
| EA (1) | EA005770B1 (de) |
| ES (1) | ES2348974T3 (de) |
| HR (1) | HRP20020805A2 (de) |
| HU (1) | HUP0300466A3 (de) |
| IL (2) | IL151417A0 (de) |
| IS (1) | IS6518A (de) |
| MA (1) | MA26893A1 (de) |
| MX (1) | MXPA02008733A (de) |
| NO (1) | NO20024308L (de) |
| NZ (1) | NZ521866A (de) |
| OA (1) | OA12677A (de) |
| PL (1) | PL357272A1 (de) |
| PT (1) | PT1265866E (de) |
| SI (1) | SI1265866T1 (de) |
| SK (1) | SK10692003A3 (de) |
| WO (1) | WO2001068612A2 (de) |
| YU (1) | YU67902A (de) |
| ZA (1) | ZA200207069B (de) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE434610T1 (de) * | 2002-03-13 | 2009-07-15 | Euro Celtique Sa | Aryl substituierte pyrimidine und deren verwendung |
| BR0313352A (pt) * | 2002-07-31 | 2005-07-12 | Euro Celtique Sa | Composto, composições farmacêuticas, método para a produção de um composto, método para o tratamento, prevenção ou a melhora de um distúrbio e método para o tratamento de um mamìfero |
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| US20040152696A1 (en) * | 2002-08-01 | 2004-08-05 | Euro-Celtique S.A. | 2-substituted bicyclic benzoheterocyclic compounds and their use as sodium channel blockers |
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| WO2013072758A1 (en) * | 2011-11-15 | 2013-05-23 | Purdue Pharma L.P. | Pyrimidine diol amides as sodium channel blockers |
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| US9714252B2 (en) | 2012-12-20 | 2017-07-25 | Purdue Pharma L.P. | Cyclic sulfonamides as sodium channel blockers |
| ES2859148T3 (es) | 2013-03-04 | 2021-10-01 | Purdue Pharma Lp | Carboxamidas de pirimidina como bloqueantes de los canales de sodio |
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| EP3083606B1 (de) | 2013-12-20 | 2020-10-28 | Purdue Pharma LP | Pyrimidine und verwendung davon |
| US9695144B2 (en) | 2013-12-23 | 2017-07-04 | Purdue Pharma L.P. | Dibenzazepine derivatives and use thereof |
| EP3087059B1 (de) | 2013-12-23 | 2020-04-29 | Purdue Pharma L.P. | Indazole und verwendung davon |
| EP3089978B1 (de) | 2013-12-30 | 2018-08-29 | Purdue Pharma L.P. | Pyridonsulfonmorphinan-analoga als opioidrezeptorliganden |
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| AU2015217185B2 (en) | 2014-02-12 | 2018-04-05 | Purdue Pharma L.P. | Isoquinoline derivatives and use thereof |
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| CA2948144A1 (en) | 2014-05-06 | 2015-11-12 | Purdue Pharma L.P. | Benzomorphan analogs and use thereof |
| WO2015177367A1 (en) | 2014-05-23 | 2015-11-26 | Active Biotech Ab | Novel compounds useful as s100-inhibitors |
| EP3154972A4 (de) | 2014-06-13 | 2017-11-22 | Purdue Pharma L.P. | Azamophinanderivate und verwendung davon |
| CA2952124A1 (en) | 2014-06-13 | 2015-12-17 | Purdue Pharma L.P. | Heterocyclic morphinan derivatives and use thereof |
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- 2001-03-12 SK SK1069-2003A patent/SK10692003A3/sk unknown
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- 2002-09-09 NO NO20024308A patent/NO20024308L/no not_active Application Discontinuation
- 2002-10-07 MA MA26852A patent/MA26893A1/fr unknown
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2003
- 2003-12-19 US US10/738,989 patent/US20040192691A1/en not_active Abandoned
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