UA75084C2 - Pyrimidine derivatives - Google Patents
Pyrimidine derivatives Download PDFInfo
- Publication number
- UA75084C2 UA75084C2 UA2003021194A UA2003021194A UA75084C2 UA 75084 C2 UA75084 C2 UA 75084C2 UA 2003021194 A UA2003021194 A UA 2003021194A UA 2003021194 A UA2003021194 A UA 2003021194A UA 75084 C2 UA75084 C2 UA 75084C2
- Authority
- UA
- Ukraine
- Prior art keywords
- sulfamoyl
- alkyl
- cyano
- group
- pyrimidine
- Prior art date
Links
- 150000003230 pyrimidines Chemical class 0.000 title description 7
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- 238000000034 method Methods 0.000 claims abstract description 159
- 150000002148 esters Chemical class 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 241001465754 Metazoa Species 0.000 claims abstract description 32
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 19
- 230000022131 cell cycle Effects 0.000 claims abstract description 18
- -1 nitro, cyano, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims description 204
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 175
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 44
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 44
- 150000001721 carbon Chemical group 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 238000011282 treatment Methods 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 206010028980 Neoplasm Diseases 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 241000282414 Homo sapiens Species 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 15
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- 201000011510 cancer Diseases 0.000 claims description 11
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229940126601 medicinal product Drugs 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- ZHMMEIFAGDPKQU-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-methylsulfonylanilino)pyrimidine-5-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC=C(C#N)C(NC2CC2)=N1 ZHMMEIFAGDPKQU-UHFFFAOYSA-N 0.000 claims 1
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- 239000000126 substance Substances 0.000 description 20
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Classifications
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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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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PCT/GB2001/003084 WO2002004429A1 (en) | 2000-07-11 | 2001-07-06 | Pyrimidine derivatives |
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