OA12677A - Aryl substituted pyridines, pyrimidines, pyrazinesand triazines and the use thereof. - Google Patents
Aryl substituted pyridines, pyrimidines, pyrazinesand triazines and the use thereof. Download PDFInfo
- Publication number
- OA12677A OA12677A OA1200200283A OA1200200283A OA12677A OA 12677 A OA12677 A OA 12677A OA 1200200283 A OA1200200283 A OA 1200200283A OA 1200200283 A OA1200200283 A OA 1200200283A OA 12677 A OA12677 A OA 12677A
- Authority
- OA
- OAPI
- Prior art keywords
- compound
- phenyl
- fluorophenoxy
- alkyl
- amino
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 30
- 150000003222 pyridines Chemical class 0.000 title abstract description 10
- 150000003918 triazines Chemical class 0.000 title abstract description 10
- 150000003230 pyrimidines Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- -1 pyrimides Chemical class 0.000 claims abstract description 89
- 208000002193 Pain Diseases 0.000 claims abstract description 27
- 229940002612 prodrug Drugs 0.000 claims abstract description 21
- 239000000651 prodrug Substances 0.000 claims abstract description 21
- 208000028867 ischemia Diseases 0.000 claims abstract description 8
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 150000002431 hydrogen Chemical group 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- 125000003342 alkenyl group Chemical group 0.000 claims description 43
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
- 239000011734 sodium Substances 0.000 claims description 15
- GLKVQISUOMMOLC-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)phenyl]pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 GLKVQISUOMMOLC-UHFFFAOYSA-N 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 14
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052708 sodium Inorganic materials 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 102000018674 Sodium Channels Human genes 0.000 claims description 12
- 108010052164 Sodium Channels Proteins 0.000 claims description 12
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 12
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 12
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000001356 alkyl thiols Chemical class 0.000 claims description 11
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 11
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 150000003573 thiols Chemical class 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 10
- 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 description 9
- 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 description 8
- BFZWDYZNSLLKKO-UHFFFAOYSA-N N#CNN[N+]([O-])=O Chemical compound N#CNN[N+]([O-])=O BFZWDYZNSLLKKO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- ZQNATCYXMGXXKC-UHFFFAOYSA-N 6-(4-ethoxyphenyl)pyridine-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C1=CC=CC(C(N)=O)=N1 ZQNATCYXMGXXKC-UHFFFAOYSA-N 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 201000001119 neuropathy Diseases 0.000 claims description 7
- 230000007823 neuropathy Effects 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 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 description 5
- NHVINRPRVJNVGZ-UHFFFAOYSA-N 4-[4-(2,4-difluorophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)F)=CC=2)=N1 NHVINRPRVJNVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 4
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 4
- KWPKXWASJFUSCI-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-4-methylpyrimidine Chemical compound CC1=CC=NC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 KWPKXWASJFUSCI-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000001537 neural effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 4
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 3
- 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 3
- LWVUNKPQSZMXJX-UHFFFAOYSA-N 4-[4-(4-fluorophenoxy)phenyl]-n-(2-hydroxyethyl)pyrimidine-2-carboxamide Chemical compound OCCNC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 LWVUNKPQSZMXJX-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- OFJMSTSMCGXEIX-UHFFFAOYSA-N 4-[4-(4-nitrophenoxy)phenyl]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC(C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 OFJMSTSMCGXEIX-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- MYTJRXLCKYPFKB-UHFFFAOYSA-N 6-[4-(4-chloro-2-fluorophenoxy)phenyl]pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 MYTJRXLCKYPFKB-UHFFFAOYSA-N 0.000 claims description 3
- HRMNVTMRIORZOL-UHFFFAOYSA-N 6-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(OC=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 HRMNVTMRIORZOL-UHFFFAOYSA-N 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 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
- 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
- 230000006793 arrhythmia Effects 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 230000036461 convulsion Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 3
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GNQXGXWIDMOBEE-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 GNQXGXWIDMOBEE-UHFFFAOYSA-N 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 6
- 230000001154 acute effect Effects 0.000 abstract description 5
- 208000005298 acute pain Diseases 0.000 abstract description 4
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- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 1
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- 235000019439 ethyl acetate Nutrition 0.000 description 63
- 239000000243 solution Substances 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
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- 238000005481 NMR spectroscopy Methods 0.000 description 49
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- 235000011152 sodium sulphate Nutrition 0.000 description 25
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Classifications
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- 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
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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
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- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Veterinary Medicine (AREA)
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- Biomedical Technology (AREA)
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- Pain & Pain Management (AREA)
- Psychiatry (AREA)
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- Anesthesiology (AREA)
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- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports 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)
| Publication Number | Publication Date |
|---|---|
| OA12677A true OA12677A (en) | 2006-06-20 |
Family
ID=22692096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200200283A OA12677A (en) | 2000-03-10 | 2001-03-12 | Aryl substituted pyridines, pyrimidines, pyrazinesand triazines and the use thereof. |
Country Status (34)
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| EP (1) | EP1265866B1 (is) |
| JP (2) | JP4359016B2 (is) |
| KR (1) | KR20030011792A (is) |
| CN (1) | CN1422254A (is) |
| AP (1) | AP1404A (is) |
| AR (1) | AR029489A1 (is) |
| AT (1) | ATE474828T1 (is) |
| AU (2) | AU2001245620B2 (is) |
| BR (1) | BR0108918A (is) |
| CA (1) | CA2400945C (is) |
| CR (1) | CR6774A (is) |
| CY (1) | CY1110809T1 (is) |
| CZ (1) | CZ20032228A3 (is) |
| DE (1) | DE60142613D1 (is) |
| DK (1) | DK1265866T3 (is) |
| EA (1) | EA005770B1 (is) |
| ES (1) | ES2348974T3 (is) |
| HR (1) | HRP20020805A2 (is) |
| HU (1) | HUP0300466A3 (is) |
| IL (2) | IL151417A0 (is) |
| IS (1) | IS6518A (is) |
| MA (1) | MA26893A1 (is) |
| MX (1) | MXPA02008733A (is) |
| NO (1) | NO20024308L (is) |
| NZ (1) | NZ521866A (is) |
| OA (1) | OA12677A (is) |
| PL (1) | PL357272A1 (is) |
| PT (1) | PT1265866E (is) |
| SI (1) | SI1265866T1 (is) |
| SK (1) | SK10692003A3 (is) |
| WO (1) | WO2001068612A2 (is) |
| YU (1) | YU67902A (is) |
| ZA (1) | ZA200207069B (is) |
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- 2001-03-12 DK DK01918558.6T patent/DK1265866T3/da active
- 2001-03-12 IL IL15141701A patent/IL151417A0/xx active IP Right Grant
- 2001-03-12 AT AT01918558T patent/ATE474828T1/de active
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- 2001-03-12 HR HRP20020805 patent/HRP20020805A2/hr not_active Application Discontinuation
- 2001-03-12 AU AU2001245620A patent/AU2001245620B2/en not_active Ceased
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- 2001-03-12 SI SI200130975T patent/SI1265866T1/sl unknown
- 2001-03-12 CN CN01807553A patent/CN1422254A/zh active Pending
- 2001-03-12 US US09/803,659 patent/US6867210B2/en not_active Expired - Lifetime
- 2001-03-12 JP JP2001567706A patent/JP4359016B2/ja not_active Expired - Fee Related
- 2001-03-12 AP APAP/P/2002/002629A patent/AP1404A/en active
- 2001-03-12 YU YU67902A patent/YU67902A/sh unknown
- 2001-03-12 SK SK1069-2003A patent/SK10692003A3/sk unknown
- 2001-03-12 NZ NZ521866A patent/NZ521866A/en not_active Application Discontinuation
- 2001-03-12 CZ CZ20032228A patent/CZ20032228A3/cs unknown
- 2001-03-12 EP EP01918558A patent/EP1265866B1/en not_active Expired - Lifetime
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2002
- 2002-08-21 IS IS6518A patent/IS6518A/is unknown
- 2002-08-22 IL IL151417A patent/IL151417A/en unknown
- 2002-09-03 ZA ZA200207069A patent/ZA200207069B/en unknown
- 2002-09-09 NO NO20024308A patent/NO20024308L/no not_active Application Discontinuation
- 2002-10-07 MA MA26852A patent/MA26893A1/fr unknown
- 2002-10-09 CR CR6774A patent/CR6774A/es not_active Application Discontinuation
-
2003
- 2003-12-19 US US10/738,989 patent/US20040192691A1/en not_active Abandoned
-
2004
- 2004-09-29 US US10/951,861 patent/US20050043305A1/en not_active Abandoned
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2008
- 2008-10-24 JP JP2008274840A patent/JP2009062390A/ja not_active Withdrawn
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2010
- 2010-09-28 CY CY20101100873T patent/CY1110809T1/el unknown
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