SK47096A3 - 1n-alkyl-n-arylpyrimidinamines and derivatives thereof - Google Patents
1n-alkyl-n-arylpyrimidinamines and derivatives thereof Download PDFInfo
- Publication number
- SK47096A3 SK47096A3 SK470-96A SK47096A SK47096A3 SK 47096 A3 SK47096 A3 SK 47096A3 SK 47096 A SK47096 A SK 47096A SK 47096 A3 SK47096 A3 SK 47096A3
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- SK
- Slovakia
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- group
- alkyl
- carbon atoms
- methyl
- substituted
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- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 36
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 12
- 230000036506 anxiety Effects 0.000 claims abstract description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 230000035558 fertility Effects 0.000 claims abstract description 7
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 7
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 7
- 230000008629 immune suppression Effects 0.000 claims abstract description 6
- 208000030814 Eating disease Diseases 0.000 claims abstract description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 5
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 208000028173 post-traumatic stress disease Diseases 0.000 claims abstract description 3
- -1 3-bromo-5-methylpyridin-2-yl Chemical group 0.000 claims description 756
- 125000004432 carbon atom Chemical group C* 0.000 claims description 399
- 125000000217 alkyl group Chemical group 0.000 claims description 255
- 229910052739 hydrogen Inorganic materials 0.000 claims description 179
- 239000001257 hydrogen Substances 0.000 claims description 168
- 150000002431 hydrogen Chemical class 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 114
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 108
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 104
- 229910052736 halogen Inorganic materials 0.000 claims description 98
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 84
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 80
- 125000001424 substituent group Chemical group 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 71
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 56
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
- 125000004193 piperazinyl group Chemical group 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 45
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 43
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 41
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000002883 imidazolyl group Chemical group 0.000 claims description 37
- 125000001041 indolyl group Chemical group 0.000 claims description 35
- 125000003386 piperidinyl group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 150000001721 carbon Chemical group 0.000 claims description 32
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- 229910052740 iodine Inorganic materials 0.000 claims description 29
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 28
- 125000002541 furyl group Chemical group 0.000 claims description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 27
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 27
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000000468 ketone group Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 21
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 21
- 125000003838 furazanyl group Chemical group 0.000 claims description 21
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 21
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 21
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 21
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 21
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 20
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 20
- 125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 claims description 20
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 20
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 20
- 125000002757 morpholinyl group Chemical group 0.000 claims description 20
- 125000002971 oxazolyl group Chemical group 0.000 claims description 20
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 20
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
- 125000004306 triazinyl group Chemical group 0.000 claims description 20
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 19
- 125000006373 (C2-C10) alkyl group Chemical group 0.000 claims description 18
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 18
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 18
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 17
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 17
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 17
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 15
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 15
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 15
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 15
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 15
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000002785 azepinyl group Chemical group 0.000 claims description 14
- 125000002393 azetidinyl group Chemical group 0.000 claims description 14
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000004623 carbolinyl group Chemical group 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 13
- 125000005986 4-piperidonyl group Chemical group 0.000 claims description 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 12
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 11
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 229930194542 Keto Natural products 0.000 claims description 9
- 206010061428 decreased appetite Diseases 0.000 claims description 9
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 9
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 9
- 125000006242 amine protecting group Chemical group 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 206010033799 Paralysis Diseases 0.000 claims description 7
- 230000001539 anorectic effect Effects 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- KSBRTKROJARSOL-UHFFFAOYSA-N n-ethyl-4,6-dimethyl-n-(2-methylsulfanyl-4-propan-2-ylphenyl)pyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(SC)C=1N(CC)C1=NC(C)=CC(C)=N1 KSBRTKROJARSOL-UHFFFAOYSA-N 0.000 claims description 6
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 206010029333 Neurosis Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- 208000015238 neurotic disease Diseases 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 4
- REZVZDZNPYLRLF-UHFFFAOYSA-N 1,1-dimethyl-2-(4-methyl-1,3,5-triazin-2-yl)hydrazine Chemical compound CN(NC1=NC(=NC=N1)C)C REZVZDZNPYLRLF-UHFFFAOYSA-N 0.000 claims description 4
- KPARZMBGRLAYAL-UHFFFAOYSA-N 1-(2-bromo-4,6-dimethoxyphenyl)-4,6-dimethylpyrrolo[2,3-b]pyridine Chemical compound COC1=CC(OC)=CC(Br)=C1N1C2=NC(C)=CC(C)=C2C=C1 KPARZMBGRLAYAL-UHFFFAOYSA-N 0.000 claims description 4
- ZMXAHDWFFGRSOY-UHFFFAOYSA-N 1-(2-bromo-4,6-dimethoxyphenyl)-4,6-dimethylpyrrolo[2,3-b]pyridine-3-carbonitrile Chemical compound COC1=CC(OC)=CC(Br)=C1N1C2=NC(C)=CC(C)=C2C(C#N)=C1 ZMXAHDWFFGRSOY-UHFFFAOYSA-N 0.000 claims description 4
- QFPQNRRUWQDVHQ-UHFFFAOYSA-N 1-(2-bromo-4-propan-2-ylphenyl)-4,6-dimethylpyrrolo[2,3-b]pyridine Chemical compound BrC1=CC(C(C)C)=CC=C1N1C2=NC(C)=CC(C)=C2C=C1 QFPQNRRUWQDVHQ-UHFFFAOYSA-N 0.000 claims description 4
- PIGVJMHCKKTORD-UHFFFAOYSA-N 1-(2-bromo-4-propan-2-ylphenyl)-4,6-dimethylpyrrolo[2,3-b]pyridine-3-carbonitrile Chemical compound BrC1=CC(C(C)C)=CC=C1N1C2=NC(C)=CC(C)=C2C(C#N)=C1 PIGVJMHCKKTORD-UHFFFAOYSA-N 0.000 claims description 4
- NIQBQCGMLBLOAL-UHFFFAOYSA-N 1-(2-bromo-4-propan-2-ylphenyl)-6-methyl-4-phenylpyrrolo[2,3-b]pyridine Chemical compound BrC1=CC(C(C)C)=CC=C1N1C2=NC(C)=CC(C=3C=CC=CC=3)=C2C=C1 NIQBQCGMLBLOAL-UHFFFAOYSA-N 0.000 claims description 4
- IZPTWDGBBSSUFN-UHFFFAOYSA-N 1-(2-bromo-4-propan-2-ylphenyl)-6-methyl-4-phenylpyrrolo[2,3-b]pyridine-3-carbonitrile Chemical compound BrC1=CC(C(C)C)=CC=C1N1C2=NC(C)=CC(C=3C=CC=CC=3)=C2C(C#N)=C1 IZPTWDGBBSSUFN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- IUNYNCQHIRZDOR-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4-methyl-6-(morpholin-4-ylmethyl)pyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C(N=1)=NC(C)=CC=1CN1CCOCC1 IUNYNCQHIRZDOR-UHFFFAOYSA-N 0.000 claims description 4
- DZRAIVUEAUXHQH-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4-methyl-6-phenylmethoxy-1,3,5-triazin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C(N=1)=NC(C)=NC=1OCC1=CC=CC=C1 DZRAIVUEAUXHQH-UHFFFAOYSA-N 0.000 claims description 4
- DJPDZZNMXCMJGS-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4-methylpyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C1=NC=CC(C)=N1 DJPDZZNMXCMJGS-UHFFFAOYSA-N 0.000 claims description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- BJBJQLPFJLBRHO-UHFFFAOYSA-N n-(2-bromo-4-ethylphenyl)-n,4,6-trimethylpyrimidin-2-amine Chemical compound BrC1=CC(CC)=CC=C1N(C)C1=NC(C)=CC(C)=N1 BJBJQLPFJLBRHO-UHFFFAOYSA-N 0.000 claims description 3
- IGKKAHZACZTWNL-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-4,6-dimethyl-n-prop-2-ynylpyrimidin-2-amine Chemical compound BrC1=CC(C(C)C)=CC=C1N(CC#C)C1=NC(C)=CC(C)=N1 IGKKAHZACZTWNL-UHFFFAOYSA-N 0.000 claims description 3
- NZHPYWKTCLZWBM-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n,4,6-trimethylpyrimidin-2-amine Chemical compound BrC1=CC(C(C)C)=CC=C1N(C)C1=NC(C)=CC(C)=N1 NZHPYWKTCLZWBM-UHFFFAOYSA-N 0.000 claims description 3
- KNUVQRQAICYVGN-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-(cyclopropylmethyl)-4,6-dimethylpyrimidin-2-amine Chemical compound BrC1=CC(C(C)C)=CC=C1N(C=1N=C(C)C=C(C)N=1)CC1CC1 KNUVQRQAICYVGN-UHFFFAOYSA-N 0.000 claims description 3
- YUEVFPATPSQDPG-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4,6-dimethylpyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C1=NC(C)=CC(C)=N1 YUEVFPATPSQDPG-UHFFFAOYSA-N 0.000 claims description 3
- HDEREWFVKKZHLL-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C(N=1)=NC(C)=NC=1N1CCOCC1 HDEREWFVKKZHLL-UHFFFAOYSA-N 0.000 claims description 3
- DQSVEQFHEZHQRX-UHFFFAOYSA-N n-(2-bromo-4-propan-2-ylphenyl)-n-ethyl-4-methyl-6-morpholin-4-ylpyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(Br)C=1N(CC)C(N=1)=NC(C)=CC=1N1CCOCC1 DQSVEQFHEZHQRX-UHFFFAOYSA-N 0.000 claims description 3
- IQYYNCCRMAFRHD-UHFFFAOYSA-N n-ethyl-n-(2-iodo-4-propan-2-ylphenyl)-4-methyl-6-morpholin-4-ylpyrimidin-2-amine Chemical compound C=1C=C(C(C)C)C=C(I)C=1N(CC)C(N=1)=NC(C)=CC=1N1CCOCC1 IQYYNCCRMAFRHD-UHFFFAOYSA-N 0.000 claims description 3
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 description 1
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- 150000003944 halohydrins Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004926 indolenyl group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- SSOVKTIUBYUZHC-UHFFFAOYSA-N lithium;tributoxyalumane Chemical compound [Li].CCCCO[Al](OCCCC)OCCCC SSOVKTIUBYUZHC-UHFFFAOYSA-N 0.000 description 1
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
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- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- RJPDHWPEJHNYMI-UHFFFAOYSA-N n-(2,4-diiodophenyl)-n-ethyl-4-methyl-6-morpholin-4-ylpyrimidin-2-amine Chemical compound C=1C=C(I)C=C(I)C=1N(CC)C(N=1)=NC(C)=CC=1N1CCOCC1 RJPDHWPEJHNYMI-UHFFFAOYSA-N 0.000 description 1
- UAMZBRAQVITBBX-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-n-ethyl-4,6-dimethylpyrimidin-2-amine Chemical compound C=1C=C(OC)C=C(OC)C=1N(CC)C1=NC(C)=CC(C)=N1 UAMZBRAQVITBBX-UHFFFAOYSA-N 0.000 description 1
- QQCOTSNFRWWJQB-UHFFFAOYSA-N n-(2,6-dimethoxy-4-methylphenyl)-n-ethyl-4,6-dimethylpyrimidin-2-amine Chemical compound COC=1C=C(C)C=C(OC)C=1N(CC)C1=NC(C)=CC(C)=N1 QQCOTSNFRWWJQB-UHFFFAOYSA-N 0.000 description 1
- VEAUGEBKCBFOFE-UHFFFAOYSA-N n-(2-bromo-4-methylphenyl)-4,6-dimethylpyrimidin-2-amine Chemical compound BrC1=CC(C)=CC=C1NC1=NC(C)=CC(C)=N1 VEAUGEBKCBFOFE-UHFFFAOYSA-N 0.000 description 1
- DHEBTQDTWJTIKX-UHFFFAOYSA-N n-(3-bromo-5-methylpyridin-2-yl)-n-ethyl-4,6-dimethylpyrimidin-2-amine Chemical compound N=1C=C(C)C=C(Br)C=1N(CC)C1=NC(C)=CC(C)=N1 DHEBTQDTWJTIKX-UHFFFAOYSA-N 0.000 description 1
- PUKALTSYVNBVNZ-UHFFFAOYSA-N n-[2-bromo-4-(2-methoxyethyl)phenyl]-n-ethyl-4-methyl-6-morpholin-4-ylpyrimidin-2-amine Chemical compound C=1C=C(CCOC)C=C(Br)C=1N(CC)C(N=1)=NC(C)=CC=1N1CCOCC1 PUKALTSYVNBVNZ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- SVMBICKJCCGZQN-UHFFFAOYSA-N n-ethyl-n-(2-ethylsulfanyl-4-propan-2-ylphenyl)-4,6-dimethylpyrimidin-2-amine Chemical compound CCSC1=CC(C(C)C)=CC=C1N(CC)C1=NC(C)=CC(C)=N1 SVMBICKJCCGZQN-UHFFFAOYSA-N 0.000 description 1
- TWNLYTJTOOUNAA-UHFFFAOYSA-N n-ethyl-n-(2-iodo-4-propan-2-ylphenyl)-4-methyl-6-thiomorpholin-4-yl-1,3,5-triazin-2-amine Chemical compound C=1C=C(C(C)C)C=C(I)C=1N(CC)C(N=1)=NC(C)=NC=1N1CCSCC1 TWNLYTJTOOUNAA-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
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- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical group ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical class SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003488 releasing hormone Substances 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical group C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- C07D239/42—One nitrogen atom
-
- 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
-
- 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
- C07D251/16—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 only one ring carbon atom
- C07D251/18—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 only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
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US29727494A | 1994-08-26 | 1994-08-26 | |
US31566094A | 1994-09-29 | 1994-09-29 | |
PCT/US1994/011050 WO1995010506A1 (en) | 1993-10-12 | 1994-10-06 | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
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SK47096A3 true SK47096A3 (en) | 1996-10-02 |
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Family Applications (1)
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SK470-96A SK47096A3 (en) | 1993-10-12 | 1994-10-06 | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
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US (2) | US6107301A (ko) |
EP (1) | EP0723533A1 (ko) |
KR (1) | KR960704855A (ko) |
AU (1) | AU692484B2 (ko) |
BR (1) | BR9407799A (ko) |
CA (1) | CA2174080A1 (ko) |
CZ (1) | CZ101496A3 (ko) |
HR (1) | HRP940664A2 (ko) |
HU (1) | HUT74464A (ko) |
IL (1) | IL111221A0 (ko) |
NO (1) | NO961425L (ko) |
NZ (1) | NZ274978A (ko) |
PL (1) | PL313973A1 (ko) |
SK (1) | SK47096A3 (ko) |
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KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
WO2018187652A1 (en) | 2017-04-06 | 2018-10-11 | Janssen Pharmaceutica Nv | 2,4-diaminopyrimidine derivatives as histamine h4 modulators |
CN111138413B (zh) * | 2018-11-01 | 2022-11-04 | 江苏豪森药业集团有限公司 | 一种细胞周期蛋白依赖性激酶抑制剂的制备方法及其中间体 |
CN114989795A (zh) * | 2021-03-02 | 2022-09-02 | 中国石油天然气集团有限公司 | 锯齿状金属螯合物堵漏剂、制备方法及应用 |
WO2023233130A1 (en) | 2022-05-30 | 2023-12-07 | AdoRx Therapeutics Limited | Cd73 inhibitor compounds |
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CH513937A (de) * | 1968-08-30 | 1971-10-15 | Ciba Geigy Ag | Verfahren zur Herstellung vernetzter Polydimercapto-s-triazine und deren Verwendung als Klebstoffe und Lacke |
DE2818676A1 (de) * | 1978-04-27 | 1979-11-08 | Troponwerke Gmbh & Co Kg | Substituierte 5,6-dimethylpyrrolo 2,3-d pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
AU5319479A (en) * | 1978-12-22 | 1980-06-26 | Ici Australia Limited | Pyrimidinyl amino phenoxy carboxylate derivatives |
DE3111155A1 (de) * | 1981-03-21 | 1982-09-30 | Troponwerke GmbH & Co KG, 5000 Köln | 5,6-dimethyl-pyrrolo (2,3-b)pyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
EP0155911A1 (de) * | 1984-03-19 | 1985-09-25 | Ciba-Geigy Ag | Purinderivate zur Regulierung des Pflanzenwachstums |
US4876252A (en) * | 1986-01-13 | 1989-10-24 | American Cyanamid Company | 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines |
US4788195A (en) * | 1986-01-13 | 1988-11-29 | American Cyanamid Company | 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines |
DE3614060A1 (de) * | 1986-04-23 | 1987-10-29 | Schering Ag | Pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
JPH0784445B2 (ja) * | 1986-12-03 | 1995-09-13 | クミアイ化学工業株式会社 | ピリミジン誘導体および農園芸用殺菌剤 |
CA1336904C (en) * | 1987-08-26 | 1995-09-05 | Mitsuyuki Takesue | Pyrimidines and their pharmaceutically acceptable salts thereof |
GB8808071D0 (en) * | 1988-04-07 | 1988-05-11 | Shell Int Research | Triazine herbicides |
US5063245A (en) * | 1990-03-28 | 1991-11-05 | Nova Pharmaceutical Corporation | Corticotropin-releasing factor antagonism compounds |
GB9012592D0 (en) * | 1990-06-06 | 1990-07-25 | Smithkline Beecham Intercredit | Compounds |
DK40192D0 (da) * | 1992-03-26 | 1992-03-26 | Neurosearch As | Imidazolforbindelser, deres fremstilling og anvendelse |
US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
DE69323212T2 (de) * | 1992-12-17 | 1999-05-27 | Pfizer | Pyrazole mit crf antagonistischer aktivität |
TW336932B (en) * | 1992-12-17 | 1998-07-21 | Pfizer | Amino-substituted pyrazoles |
TW444018B (en) * | 1992-12-17 | 2001-07-01 | Pfizer | Pyrazolopyrimidines |
DK0674641T3 (da) * | 1992-12-17 | 1999-09-27 | Pfizer | Pyrrolopyrimidiner som CRF-antagonister |
RU2130453C1 (ru) * | 1992-12-17 | 1999-05-20 | Пфайзер Инк. | Замещенные пиразолы, фармацевтическая композиция на их основе, способ лечения, промежуточный продукт |
CA2148931A1 (en) * | 1993-10-01 | 1995-04-13 | Jurg Zimmermann | Pyrimidineamine derivatives and processes for the preparation thereof |
-
1994
- 1994-10-06 PL PL94313973A patent/PL313973A1/xx unknown
- 1994-10-06 AU AU80122/94A patent/AU692484B2/en not_active Ceased
- 1994-10-06 KR KR1019960701900A patent/KR960704855A/ko not_active Application Discontinuation
- 1994-10-06 BR BR9407799A patent/BR9407799A/pt not_active Application Discontinuation
- 1994-10-06 CZ CZ961014A patent/CZ101496A3/cs unknown
- 1994-10-06 SK SK470-96A patent/SK47096A3/sk unknown
- 1994-10-06 NZ NZ274978A patent/NZ274978A/en unknown
- 1994-10-06 EP EP94931298A patent/EP0723533A1/en not_active Withdrawn
- 1994-10-06 CA CA002174080A patent/CA2174080A1/en not_active Abandoned
- 1994-10-06 HU HU9600932A patent/HUT74464A/hu unknown
- 1994-10-10 IL IL11122194A patent/IL111221A0/xx unknown
- 1994-10-11 HR HR08/315,660A patent/HRP940664A2/hr not_active Application Discontinuation
-
1996
- 1996-04-11 NO NO961425A patent/NO961425L/no not_active Application Discontinuation
-
1997
- 1997-08-05 US US08/906,349 patent/US6107301A/en not_active Expired - Lifetime
-
1998
- 1998-01-07 US US09/004,150 patent/US6342503B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
PL313973A1 (en) | 1996-08-05 |
AU8012294A (en) | 1995-05-04 |
CA2174080A1 (en) | 1995-04-20 |
BR9407799A (pt) | 1997-05-06 |
HU9600932D0 (en) | 1996-06-28 |
NO961425D0 (no) | 1996-04-11 |
AU692484B2 (en) | 1998-06-11 |
EP0723533A1 (en) | 1996-07-31 |
HUT74464A (en) | 1996-12-30 |
US6107301A (en) | 2000-08-22 |
NZ274978A (en) | 1998-04-27 |
NO961425L (no) | 1996-06-12 |
HRP940664A2 (en) | 1996-12-31 |
US6342503B1 (en) | 2002-01-29 |
KR960704855A (ko) | 1996-10-09 |
CZ101496A3 (en) | 1996-11-13 |
IL111221A0 (en) | 1995-01-24 |
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