NO791722L - Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivater - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivaterInfo
- Publication number
- NO791722L NO791722L NO791722A NO791722A NO791722L NO 791722 L NO791722 L NO 791722L NO 791722 A NO791722 A NO 791722A NO 791722 A NO791722 A NO 791722A NO 791722 L NO791722 L NO 791722L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- radical
- phenyl
- triazine
- dione
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 14
- 150000003918 triazines Chemical class 0.000 title 1
- -1 methylenedioxy- Chemical class 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000007858 starting material Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- WKTVZAYHDLSABI-UHFFFAOYSA-N n-[5-(4-methylphenyl)-4,6-dioxo-1,3,5-triazinan-2-yl]-n-(2-methylpropyl)acetamide Chemical compound O=C1NC(N(CC(C)C)C(C)=O)NC(=O)N1C1=CC=C(C)C=C1 WKTVZAYHDLSABI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- XXEHMEDDASZWDN-UHFFFAOYSA-N n-[5-(4-methoxyphenyl)-4,6-dioxo-1,3,5-triazinan-2-yl]-n-(2-methylpropyl)acetamide Chemical compound C1=CC(OC)=CC=C1N1C(=O)NC(N(CC(C)C)C(C)=O)NC1=O XXEHMEDDASZWDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- XEPKXCYFJXYMSG-UHFFFAOYSA-N n-(4,6-dioxo-5-thiophen-2-yl-1,3,5-triazinan-2-yl)-n-(2-methylpropyl)acetamide Chemical compound O=C1NC(N(CC(C)C)C(C)=O)NC(=O)N1C1=CC=CS1 XEPKXCYFJXYMSG-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000000166 1,3-dioxalanyl group Chemical group 0.000 claims description 2
- 125000003047 N-acetyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 36
- 239000007787 solid Substances 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 8
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- MMBDAJMDNVQFDV-UHFFFAOYSA-N methyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(N)SC MMBDAJMDNVQFDV-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 238000004452 microanalysis Methods 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VMDQJNSUYIYJRB-UHFFFAOYSA-N 3-(4-methylphenyl)-6-(2-methylpropylamino)-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(NCC(C)C)NC(=O)N1C1=CC=C(C)C=C1 VMDQJNSUYIYJRB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- HHGDIPNPERRYQO-UHFFFAOYSA-N 3-(4-methylphenyl)-6-methylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1C1=CC=C(C)C=C1 HHGDIPNPERRYQO-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- NLHDOQOIENSLHU-UHFFFAOYSA-N 4-[4-(2-methylpropylamino)-2,6-dioxo-1,3,5-triazinan-1-yl]benzonitrile Chemical compound O=C1NC(NCC(C)C)NC(=O)N1C1=CC=C(C#N)C=C1 NLHDOQOIENSLHU-UHFFFAOYSA-N 0.000 description 2
- QULBQNSPFSLYRO-UHFFFAOYSA-N 6-(butylamino)-3-(4-hydroxyphenyl)-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(NCCCC)NC(=O)N1C1=CC=C(O)C=C1 QULBQNSPFSLYRO-UHFFFAOYSA-N 0.000 description 2
- CVYKYBQDPODGCI-UHFFFAOYSA-N 6-(butylamino)-3-[3-(trifluoromethyl)phenyl]-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(NCCCC)NC(=O)N1C1=CC=CC(C(F)(F)F)=C1 CVYKYBQDPODGCI-UHFFFAOYSA-N 0.000 description 2
- QCIHVBCUEZQWAC-UHFFFAOYSA-N 6-methylsulfanyl-3-[3-(trifluoromethyl)phenyl]-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1C1=CC=CC(C(F)(F)F)=C1 QCIHVBCUEZQWAC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HGBCCTCECBBGMF-UHFFFAOYSA-N acetyl 4-[4-[acetyl(2-methylpropyl)amino]-2,6-dioxo-1,3,5-triazinan-1-yl]benzoate Chemical compound O=C1NC(N(CC(C)C)C(C)=O)NC(=O)N1C1=CC=C(C(=O)OC(C)=O)C=C1 HGBCCTCECBBGMF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YARQFNHHOIYLAQ-UHFFFAOYSA-N n-[5-(4-methylphenyl)-4,6-dioxo-1,3,5-triazinan-2-yl]-n-(2-methylpropyl)acetamide;sodium Chemical compound [Na].O=C1NC(N(CC(C)C)C(C)=O)NC(=O)N1C1=CC=C(C)C=C1 YARQFNHHOIYLAQ-UHFFFAOYSA-N 0.000 description 2
- LBDXOBAXNKCHTE-UHFFFAOYSA-N n-[5-(4-methylphenyl)-4,6-dioxo-1,3,5-triazinan-2-yl]-n-(2-methylpropyl)propanamide Chemical compound O=C1NC(N(CC(C)C)C(=O)CC)NC(=O)N1C1=CC=C(C)C=C1 LBDXOBAXNKCHTE-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000004277 1,3-dioxalan-2-yl group Chemical group [H]C1([H])OC([H])(*)OC1([H])[H] 0.000 description 1
- SEHUDBUMAZHYGS-UHFFFAOYSA-N 1-acetyl-3-(4-methylphenyl)-6-(2-methylpropylamino)-1,3,5-triazinane-2,4-dione Chemical compound O=C1N(C(C)=O)C(NCC(C)C)NC(=O)N1C1=CC=C(C)C=C1 SEHUDBUMAZHYGS-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 description 1
- JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical class OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZYSJCMOPARYUTL-UHFFFAOYSA-N 3-(furan-2-yl)-6-methylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1C1=CC=CO1 ZYSJCMOPARYUTL-UHFFFAOYSA-N 0.000 description 1
- IHRLUHRCZSUKAL-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-6-methylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1CC1=CC=CO1 IHRLUHRCZSUKAL-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- TVKRVSRVDVWKGA-UHFFFAOYSA-N 4-[4-(2-methylpropylamino)-2,6-dioxo-1,3,5-triazinan-1-yl]benzoic acid Chemical compound O=C1NC(NCC(C)C)NC(=O)N1C1=CC=C(C(O)=O)C=C1 TVKRVSRVDVWKGA-UHFFFAOYSA-N 0.000 description 1
- DEKYZSISBGOBPF-UHFFFAOYSA-N 4-[4-[acetyl(2-methylpropyl)amino]-2,6-dioxo-1,3,5-triazinan-1-yl]benzoic acid Chemical compound O=C1NC(N(CC(C)C)C(C)=O)NC(=O)N1C1=CC=C(C(O)=O)C=C1 DEKYZSISBGOBPF-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
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- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2293878 | 1978-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791722L true NO791722L (no) | 1979-11-27 |
Family
ID=10187501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791722A NO791722L (no) | 1978-05-26 | 1979-05-25 | Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivater |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4254122A (xx) |
| EP (1) | EP0005911B1 (xx) |
| JP (1) | JPS54154779A (xx) |
| AT (1) | ATE698T1 (xx) |
| AU (1) | AU529948B2 (xx) |
| CA (1) | CA1108138A (xx) |
| CS (1) | CS213377B2 (xx) |
| DD (1) | DD143906A5 (xx) |
| DE (1) | DE2962124D1 (xx) |
| DK (1) | DK213179A (xx) |
| ES (1) | ES480932A1 (xx) |
| FI (1) | FI66180C (xx) |
| GR (1) | GR68185B (xx) |
| HU (1) | HU180252B (xx) |
| IE (1) | IE49170B1 (xx) |
| IL (1) | IL57324A (xx) |
| MW (1) | MW1379A1 (xx) |
| NO (1) | NO791722L (xx) |
| NZ (1) | NZ190402A (xx) |
| PH (1) | PH14793A (xx) |
| PT (1) | PT69650A (xx) |
| ZA (1) | ZA792247B (xx) |
| ZM (1) | ZM4579A1 (xx) |
| ZW (1) | ZW9179A1 (xx) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8629567D0 (en) * | 1986-12-10 | 1987-01-21 | Boots Co Plc | Therapeutic agents |
| US6348216B1 (en) * | 1996-06-10 | 2002-02-19 | Knoll Pharmaceutical Company | Ibuprofen and narcotic analgesic compositions |
| US6361794B1 (en) | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| WO1998049150A1 (en) * | 1997-04-25 | 1998-11-05 | Takeda Chemical Industries, Ltd. | Triazine derivatives, their production and agrochemical composition |
| US6335339B1 (en) | 1998-01-13 | 2002-01-01 | Scriptgen Pharmaceuticals, Inc. | Triazine antiviral compounds |
| US20060166872A1 (en) * | 2002-04-17 | 2006-07-27 | Jabbour Henry N | Fp receptor antagonists or pgf2 alpha antagonists for treating menorrhagia |
| EP1660072A2 (en) * | 2003-07-29 | 2006-05-31 | Universitätsklinikum Münster | Means and methods for treating a disease which is associated with an excess transport of hyaluronan across a lipid bilayer |
| US7199156B2 (en) * | 2003-10-10 | 2007-04-03 | Milos Chvapil | Composition and method to treat solid tumors |
| TW200517114A (en) * | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
| CA2652773A1 (en) * | 2006-05-22 | 2007-12-06 | Combinatorx, Incorporated | Methods and compositions for the treatment of diseases or conditions associated with increased c-reactive protein, interleukin-6, or interferon-gamma levels |
| CA2737131A1 (en) * | 2007-09-19 | 2009-03-26 | Zalicus Inc. | Therapeutic regimens for the treatment of immunoinflammatory disorders |
| JP2011506607A (ja) * | 2007-12-17 | 2011-03-03 | ザリカス インコーポレイティッド | 免疫炎症性障害の処置のための治療法 |
| PL2399910T3 (pl) | 2009-02-13 | 2014-09-30 | Shionogi & Co | Pochodne triazyny jako antagoniści receptora p2x3 i/albo p2x2/3 i kompozycja farmaceutyczna zawierająca je |
| US9212130B2 (en) | 2010-08-10 | 2015-12-15 | Shionogi & Co., Ltd. | Heterocyclic derivative and pharmaceutical composition comprising the same |
| KR101867110B1 (ko) | 2010-08-10 | 2018-06-12 | 시오노기 앤드 컴파니, 리미티드 | 트라이아진 유도체 및 그것을 함유하는 진통 작용을 갖는 의약 조성물 |
| WO2013118855A1 (ja) | 2012-02-09 | 2013-08-15 | 塩野義製薬株式会社 | 複素環および炭素環誘導体 |
| TWI637949B (zh) | 2013-06-14 | 2018-10-11 | 塩野義製藥股份有限公司 | 胺基三衍生物及含有其等之醫藥組合物 |
| WO2022162689A1 (en) * | 2021-01-26 | 2022-08-04 | Council Of Scientific And Industrial Research | Triazine-based self-assembling system |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3983116A (en) * | 1973-04-05 | 1976-09-28 | E. I. Du Pont De Nemours And Company | Herbicidal triazines |
| US4035365A (en) * | 1973-11-01 | 1977-07-12 | Imperial Chemical Industries Limited | Triazinediones |
| GB1464248A (en) | 1973-11-01 | 1977-02-09 | Ici Ltd | Substituted triazinediones their preparation and use as herbicides |
| GB1543037A (en) * | 1975-02-05 | 1979-03-28 | Ici Ltd | Selective herbicidal triazine-diones |
| US4082536A (en) * | 1973-11-01 | 1978-04-04 | Imperial Chemical Industries Limited | Heterocyclic compounds and their use as pesticides |
| GB1504304A (en) * | 1974-02-15 | 1978-03-15 | Ici Ltd | Process of combating fungal and bacterial infections of plants with triazine dione derivatives |
| GB1599518A (en) * | 1977-02-21 | 1981-10-07 | Ici Ltd | 1,3,5-triazine-2,6-diones and pharmaceutical compositions thereof |
-
1979
- 1979-05-02 AT AT79300756T patent/ATE698T1/de not_active IP Right Cessation
- 1979-05-02 DE DE7979300756T patent/DE2962124D1/de not_active Expired
- 1979-05-02 EP EP79300756A patent/EP0005911B1/en not_active Expired
- 1979-05-07 CA CA327,103A patent/CA1108138A/en not_active Expired
- 1979-05-07 US US06/036,508 patent/US4254122A/en not_active Expired - Lifetime
- 1979-05-09 ZA ZA792247A patent/ZA792247B/xx unknown
- 1979-05-09 NZ NZ190402A patent/NZ190402A/xx unknown
- 1979-05-10 AU AU46949/79A patent/AU529948B2/en not_active Ceased
- 1979-05-15 ZW ZW91/79A patent/ZW9179A1/xx unknown
- 1979-05-17 MW MW13/79A patent/MW1379A1/xx unknown
- 1979-05-17 IL IL57324A patent/IL57324A/xx unknown
- 1979-05-19 GR GR59133A patent/GR68185B/el unknown
- 1979-05-21 PH PH22523A patent/PH14793A/en unknown
- 1979-05-22 HU HU79IE875A patent/HU180252B/hu unknown
- 1979-05-22 PT PT69650A patent/PT69650A/pt unknown
- 1979-05-23 ZM ZM45/79A patent/ZM4579A1/xx unknown
- 1979-05-23 DK DK213179A patent/DK213179A/da not_active Application Discontinuation
- 1979-05-25 FI FI791670A patent/FI66180C/fi not_active IP Right Cessation
- 1979-05-25 ES ES480932A patent/ES480932A1/es not_active Expired
- 1979-05-25 DD DD79213155A patent/DD143906A5/de unknown
- 1979-05-25 NO NO791722A patent/NO791722L/no unknown
- 1979-05-25 JP JP6407279A patent/JPS54154779A/ja active Pending
- 1979-05-25 CS CS793623A patent/CS213377B2/cs unknown
- 1979-08-08 IE IE889/79A patent/IE49170B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0005911B1 (en) | 1982-02-17 |
| ZA792247B (en) | 1980-05-28 |
| AU529948B2 (en) | 1983-06-30 |
| IE790889L (en) | 1979-11-26 |
| CA1108138A (en) | 1981-09-01 |
| DK213179A (da) | 1979-11-27 |
| GR68185B (xx) | 1981-11-09 |
| ATE698T1 (de) | 1982-03-15 |
| EP0005911A1 (en) | 1979-12-12 |
| IE49170B1 (en) | 1985-08-21 |
| US4254122A (en) | 1981-03-03 |
| JPS54154779A (en) | 1979-12-06 |
| PT69650A (en) | 1979-06-01 |
| FI66180C (fi) | 1984-09-10 |
| DD143906A5 (de) | 1980-09-17 |
| FI66180B (fi) | 1984-05-31 |
| AU4694979A (en) | 1979-11-29 |
| HU180252B (en) | 1983-02-28 |
| DE2962124D1 (en) | 1982-03-25 |
| IL57324A (en) | 1983-10-31 |
| NZ190402A (en) | 1982-05-31 |
| FI791670A (fi) | 1979-11-27 |
| CS213377B2 (en) | 1982-04-09 |
| MW1379A1 (en) | 1981-04-08 |
| ES480932A1 (es) | 1980-02-01 |
| PH14793A (en) | 1981-12-09 |
| ZW9179A1 (en) | 1981-01-21 |
| IL57324A0 (en) | 1979-09-30 |
| ZM4579A1 (en) | 1981-05-21 |
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