NO791722L - Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivater - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivater

Info

Publication number: NO791722L
Authority: NO; Norway
Prior art keywords: formula; radical; phenyl; triazine; dione
Prior art date: 1978-05-26

Application number

NO791722A

Other languages

English (en)

Norwegian (no)

Inventor

Edward Douglas Brown

Original Assignee

Ici Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-05-26

Filing date

1979-05-25

Publication date

1979-11-27

1979-05-25 Application filed by Ici Ltd filed Critical Ici Ltd

1979-11-27 Publication of NO791722L publication Critical patent/NO791722L/no

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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
PJHWTWHVCOZCPU-UHFFFAOYSA-N 4-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1 PJHWTWHVCOZCPU-UHFFFAOYSA-N 0.000 description 1
NWPBFGWVZQGAHM-UHFFFAOYSA-N 4-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C=C1 NWPBFGWVZQGAHM-UHFFFAOYSA-N 0.000 description 1
MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
UUZXOZXHIFNNNW-UHFFFAOYSA-N 6-(2-methylpropylamino)-3-thiophen-2-yl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(NCC(C)C)NC(=O)N1C1=CC=CS1 UUZXOZXHIFNNNW-UHFFFAOYSA-N 0.000 description 1
PPTISQFUECXIPL-UHFFFAOYSA-N 6-(butylamino)-3-(4-methoxyphenyl)-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(NCCCC)NC(=O)N1C1=CC=C(OC)C=C1 PPTISQFUECXIPL-UHFFFAOYSA-N 0.000 description 1
GMPZPYPLVSIPQH-UHFFFAOYSA-N 6-methylsulfanyl-3-(4-methylsulfanylphenyl)-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1C1=CC=C(SC)C=C1 GMPZPYPLVSIPQH-UHFFFAOYSA-N 0.000 description 1
WRPHGQUIUSJMIU-UHFFFAOYSA-N 6-methylsulfanyl-3-thiophen-2-yl-1,3,5-triazinane-2,4-dione Chemical compound O=C1NC(SC)NC(=O)N1C1=CC=CS1 WRPHGQUIUSJMIU-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
208000012659 Joint disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000012472 biological sample Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229960003677 chloroquine Drugs 0.000 description 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229960004193 dextropropoxyphene Drugs 0.000 description 1
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229960004369 flufenamic acid Drugs 0.000 description 1
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
150000002561 ketenes Chemical class 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
208000007106 menorrhagia Diseases 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
NJOBHIWMIAWSPG-UHFFFAOYSA-N n-[5-(4-methylphenyl)-4,6-dioxo-1,3,5-triazinan-2-yl]-n-(2-methylpropyl)butanamide Chemical compound O=C1NC(N(CC(C)C)C(=O)CCC)NC(=O)N1C1=CC=C(C)C=C1 NJOBHIWMIAWSPG-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
CHLFSNHXMILIMP-UHFFFAOYSA-N n-butyl-n-[4,6-dioxo-5-[3-(trifluoromethyl)phenyl]-1,3,5-triazinan-2-yl]acetamide Chemical compound O=C1NC(N(CCCC)C(C)=O)NC(=O)N1C1=CC=CC(C(F)(F)F)=C1 CHLFSNHXMILIMP-UHFFFAOYSA-N 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
VGARXUKVAKMUHV-UHFFFAOYSA-N n-diazonio-4-methylbenzenecarboximidothioate Chemical compound CC1=CC=C(C(=S)N=[N+]=[N-])C=C1 VGARXUKVAKMUHV-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
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
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
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
210000001625 seminal vesicle Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
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
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (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)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO791722A 1978-05-26 1979-05-25 Analogifremgangsmaate for fremstilling av terapeutisk aktive triazinderivater NO791722L (no)

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 (de)
EP (1)	EP0005911B1 (de)
JP (1)	JPS54154779A (de)
AT (1)	ATE698T1 (de)
AU (1)	AU529948B2 (de)
CA (1)	CA1108138A (de)
CS (1)	CS213377B2 (de)
DD (1)	DD143906A5 (de)
DE (1)	DE2962124D1 (de)
DK (1)	DK213179A (de)
ES (1)	ES480932A1 (de)
FI (1)	FI66180C (de)
GR (1)	GR68185B (de)
HU (1)	HU180252B (de)
IE (1)	IE49170B1 (de)
IL (1)	IL57324A (de)
MW (1)	MW1379A1 (de)
NO (1)	NO791722L (de)
NZ (1)	NZ190402A (de)
PH (1)	PH14793A (de)
PT (1)	PT69650A (de)
ZA (1)	ZA792247B (de)
ZM (1)	ZM4579A1 (de)
ZW (1)	ZW9179A1 (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
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
JP2005532295A (ja) *	2002-04-17	2005-10-27	メディカルリサーチカウンシル	月経過多を治療するためのＦＰレセプターアンタゴニスト又はＰＧＦ２αアンタゴニスト
WO2005013947A2 (en) *	2003-07-29	2005-02-17	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
MX2008014828A (es) *	2006-05-22	2009-02-06	Combinatorx Inc	Metodos y composiciones para el tratamiento de enfermedades o condiciones asociadas con niveles incrementados de proteina c-reactiva, interleucina-6 o interferon-gamma.
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
CN102395571B (zh) *	2009-02-13	2015-12-16	盐野义制药株式会社	三嗪衍生物及含有该三嗪衍生物的药物组合物
US9212130B2 (en)	2010-08-10	2015-12-15	Shionogi & Co., Ltd.	Heterocyclic derivative and pharmaceutical composition comprising the same
PL2604595T3 (pl) *	2010-08-10	2016-09-30		Pochodna triazyny i związek farmaceutyczny, który ją zawiera i wykazuje aktywność przeciwbólową
US9550763B2 (en)	2012-02-09	2017-01-24	Shionogi & Co., Ltd.	Heterocyclic ring and carbocyclic derivative
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
MX2023010673A (es) *	2021-03-17	2023-09-22	Hansoh Bio Llc	Cetonas heterociclicas que contienen nitrogeno, metodos de preparacion y usos medicinales de las mismas.
CN120574183B (zh) *	2025-07-31	2025-11-21	潍坊鑫洋化工有限公司	一种溴代三嗪的合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
US4082536A (en) *	1973-11-01	1978-04-04	Imperial Chemical Industries Limited	Heterocyclic compounds and their use as pesticides
GB1543037A (en) *	1975-02-05	1979-03-28	Ici Ltd	Selective herbicidal triazine-diones
GB1464248A (en)	1973-11-01	1977-02-09	Ici Ltd	Substituted triazinediones their preparation and use as herbicides
US4035365A (en) *	1973-11-01	1977-07-12	Imperial Chemical Industries Limited	Triazinediones
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 DE DE7979300756T patent/DE2962124D1/de not_active Expired
- 1979-05-02 AT AT79300756T patent/ATE698T1/de not_active IP Right Cessation
- 1979-05-02 EP EP79300756A patent/EP0005911B1/de 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 NZ NZ190402A patent/NZ190402A/xx unknown
- 1979-05-09 ZA ZA792247A patent/ZA792247B/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 IL IL57324A patent/IL57324A/xx unknown
- 1979-05-17 MW MW13/79A patent/MW1379A1/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 DK DK213179A patent/DK213179A/da not_active Application Discontinuation
- 1979-05-23 ZM ZM45/79A patent/ZM4579A1/xx unknown
- 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 CS CS793623A patent/CS213377B2/cs unknown
- 1979-05-25 JP JP6407279A patent/JPS54154779A/ja active Pending
- 1979-05-25 DD DD79213155A patent/DD143906A5/de unknown
- 1979-05-25 NO NO791722A patent/NO791722L/no unknown
- 1979-08-08 IE IE889/79A patent/IE49170B1/en unknown

Also Published As

Publication number	Publication date
US4254122A (en)	1981-03-03
ZM4579A1 (en)	1981-05-21
ZA792247B (en)	1980-05-28
HU180252B (en)	1983-02-28
FI66180B (fi)	1984-05-31
EP0005911B1 (de)	1982-02-17
IE49170B1 (en)	1985-08-21
GR68185B (de)	1981-11-09
MW1379A1 (en)	1981-04-08
EP0005911A1 (de)	1979-12-12
DD143906A5 (de)	1980-09-17
ES480932A1 (es)	1980-02-01
AU4694979A (en)	1979-11-29
CA1108138A (en)	1981-09-01
DK213179A (da)	1979-11-27
PT69650A (en)	1979-06-01
IL57324A (en)	1983-10-31
JPS54154779A (en)	1979-12-06
IE790889L (en)	1979-11-26
ATE698T1 (de)	1982-03-15
FI66180C (fi)	1984-09-10
FI791670A7 (fi)	1979-11-27
NZ190402A (en)	1982-05-31
CS213377B2 (en)	1982-04-09
ZW9179A1 (en)	1981-01-21
DE2962124D1 (en)	1982-03-25
IL57324A0 (en)	1979-09-30
AU529948B2 (en)	1983-06-30
PH14793A (en)	1981-12-09

Publication	Publication Date	Title
EP0005911B1 (de)	1982-02-17	Analgetische 6-Acylaminotetrahydro-1,3,5-Triazin-2,4-dion-Derivate, sie enthaltende pharmazeutische Zusammensetzungen und Verfahren zu ihrer Herstellung
FI114099B (fi)	2004-08-13	Pyrrolitsiini- ja pyrrolo[2,1-b] tiatsolijohdannaiset ja niiden käyttö farmasiassa
FI89911B (fi)	1993-08-31	Foerfarande foer framstaellning av terapeutiskt aktiva hydroxi- och alkoxipyrimidiner
FR2538392A1 (fr)	1984-06-29	Derives de type carboxamido de 5h-1,3,4-thiadiazolo (3,2-a) pyrimidine, procede pour leur preparation et composition pharmaceutique les contenant et presentant un effet analgesique et anti-inflammatoire
EP0181136B1 (de)	1992-03-25	Oxindol-Derivate als antiinflammatorische Mittel
HU194166B (en)	1988-01-28	Process for preparing 3-acyl-2-oxindole derivatives
US6025390A (en)	2000-02-15	Heteroaromatic pentadienoic acid derivatives useful as inhibitors of bone resorption
FI64152B (fi)	1983-06-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-n-acetyl)-aminotetrahydro-1,3,5-triazin-2,6-dioner
EP0319170B1 (de)	1993-03-17	Acyl-Derivate von Hydroxy-Pyrimidinen
Gunda et al.	1997	2-Amino-1-phenyl-propan-1, 3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones
NO174928B (no)	1994-04-25	Analogifremgangsmåte for fremstilling av terapeutisk aktive enoletere av 6-klor-4-hydroksy-2-metyl-N-(2-pyridyl)-2H-tieno(2,3-e)-1,2-tiazin-3-karboksylsyreamid-1,1-dioksyd
NO154493B (no)	1986-06-23	Analogifremgangsmaate for fremstilling av nye, terapeutisk aktive 1-substituerte-3-cycloalkyl-sulfonyl-pyrrolidin-2,5-dion-derivater.
JPS58188868A (ja)	1983-11-04	オレフイン系ベンズイミダゾ−ル類
FI74470C (fi)	1988-02-08	Foerfarande foer framstaellning av 5-pyridyletenylderivat av 1h-pyrazolo/1,5-a/pyrimidiner.
WO2001058901A1 (en)	2001-08-16	Pyrrolopyridazine compound
NO148490B (no)	1983-07-11	Analogifremgangsmaate for fremstilling av medisinsk virksomme 1,2-tiazino(5,6-b)indoler
DK156391B (da)	1989-08-14	Analogifremgangsmaade til fremstilling af 3-aminopyrrolderivater
DK150158B (da)	1986-12-22	Analogifremgangsmaade til fremstilling af 4-phenylthieno-(2,3-c)piperidiner eller fysiologisk acceptable syreadditionssalte deraf
JPH04221386A (ja)	1992-08-11	４Ｈ−ピロロ［１，２−ａ］チエノ［２，３−ｆ］［１，４］ジアゼピンの新規誘導体、それらの製造方法及びこれらを含有する医薬品組成物
NO880088L (no)	1988-07-13	2,1-benzotiazepin-2,2-dioksyd-5-karboksylsyrederivater.
NO783529L (no)	1979-04-20	Nye derivater av tiazolin.
FI81796B (fi)	1990-08-31	Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne.
FI80460C (fi)	1990-06-11	Nya 3- eller 5-(3-pyridyl-1h-3h- pyrrolo/1,2-c/tiazol-7-s-alkyltiokarboximidat, vilka aer mellanprodukt vid framstaellning av motsvarande terapeutiskt anvaendbara 7-karboxamiddialkylhydrazon- och 7-piperidinokarboimidylpyrrolotiazolderivat.
Kochikyan et al.	2006	Synthesis of new α-spiroheteryl-fused butanolides
NO159490B (no)	1988-09-26	Analogifremgangsmaate til fremstilling av terapeutisk aktive beta-karbolin-3-karboksylsyrederivater.