CA1128507A - Triazines substituees en 1,2,4 a proprietes pharmaceutiques - Google Patents

Triazines substituees en 1,2,4 a proprietes pharmaceutiques

Info

Publication number: CA1128507A
Authority: CA; Canada
Prior art keywords: triazine; phenyl; alkyl; preparing; reacted
Prior art date: 1977-05-17
Legal status (The legal status 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 status listed.): Expired

Application number

CA303,466A

Other languages

English (en)

Inventor

James M. Gullo

Robert E. Moser

William P. Heilman

Robert J. Wayner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Diamond Shamrock Corp

Original Assignee

Diamond Shamrock Corp

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.)

1977-05-17

Filing date

1978-05-16

Publication date

1982-07-27

1978-04-19 Priority claimed from US05/897,803 external-priority patent/US4157392A/en

1978-05-16 Application filed by Diamond Shamrock Corp filed Critical Diamond Shamrock Corp

1982-03-23 Priority to CA000399169A priority Critical patent/CA1151165A/fr

1982-07-27 Application granted granted Critical

1982-07-27 Publication of CA1128507A publication Critical patent/CA1128507A/fr

Status Expired legal-status Critical Current

Links

150000003920 1,2,4-triazines Chemical class 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 97
238000000034 method Methods 0.000 claims abstract description 68
-1 dimethylpyrrolidyl Chemical group 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 69
125000000217 alkyl group Chemical group 0.000 claims description 67
230000008569 process Effects 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 40
238000004519 manufacturing process Methods 0.000 claims description 40
125000004076 pyridyl group Chemical group 0.000 claims description 34
125000002541 furyl group Chemical group 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 31
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 29
125000003545 alkoxy group Chemical group 0.000 claims description 29
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 29
125000004414 alkyl thio group Chemical group 0.000 claims description 26
239000000126 substance Substances 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
125000001041 indolyl group Chemical group 0.000 claims description 16
125000001544 thienyl group Chemical group 0.000 claims description 15
125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
125000005276 alkyl hydrazino group Chemical group 0.000 claims description 12
125000005336 allyloxy group Chemical group 0.000 claims description 12
125000005366 cycloalkylthio group Chemical group 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
125000002071 phenylalkoxy group Chemical group 0.000 claims description 11
MAPCYWNEYALWSN-UHFFFAOYSA-N 3-methylsulfanyl-5-phenyl-1,2,4-triazine Chemical compound CSC1=NN=CC(C=2C=CC=CC=2)=N1 MAPCYWNEYALWSN-UHFFFAOYSA-N 0.000 claims description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 10
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000005059 halophenyl group Chemical group 0.000 claims description 7
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 7
VRMBXAUHRGOOOK-UHFFFAOYSA-N 1-methyl-2-(5-phenyl-1,2,4-triazin-3-yl)hydrazine Chemical compound CNNC1=NN=CC(C=2C=CC=CC=2)=N1 VRMBXAUHRGOOOK-UHFFFAOYSA-N 0.000 claims description 6
125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
XNMHGSWBLYFSHI-UHFFFAOYSA-N (5-phenyl-1,2,4-triazin-3-yl)hydrazine Chemical compound NNC1=NN=CC(C=2C=CC=CC=2)=N1 XNMHGSWBLYFSHI-UHFFFAOYSA-N 0.000 claims description 5
YMBMXBOUDJKXSC-UHFFFAOYSA-N 5,6-dimethyl-3-methylsulfanyl-1,2,4-triazine Chemical compound CSC1=NN=C(C)C(C)=N1 YMBMXBOUDJKXSC-UHFFFAOYSA-N 0.000 claims description 5
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
IRCYSLPPAWCUBS-UHFFFAOYSA-N n'-(5,6-diphenyl-1,2,4-triazin-3-yl)acetohydrazide Chemical compound C=1C=CC=CC=1C1=NC(NNC(=O)C)=NN=C1C1=CC=CC=C1 IRCYSLPPAWCUBS-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
ZXVUJMFKAOAULH-UHFFFAOYSA-N 2,2,2-trifluoro-n'-(5-phenyl-1,2,4-triazin-3-yl)acetohydrazide Chemical compound FC(F)(F)C(=O)NNC1=NN=CC(C=2C=CC=CC=2)=N1 ZXVUJMFKAOAULH-UHFFFAOYSA-N 0.000 claims description 4
BGCPJNDJZNEUQX-UHFFFAOYSA-N 5-cyclopropyl-3-methoxy-1,2,4-triazine Chemical compound COC1=NN=CC(C2CC2)=N1 BGCPJNDJZNEUQX-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
ANYPJWFRQWECTK-UHFFFAOYSA-N 3-methoxy-5-[3-(trifluoromethyl)phenyl]-1,2,4-triazine Chemical compound COC1=NN=CC(C=2C=C(C=CC=2)C(F)(F)F)=N1 ANYPJWFRQWECTK-UHFFFAOYSA-N 0.000 claims description 3
OKFBBHMBTUDVCB-UHFFFAOYSA-N 3-methylsulfanyl-5-[3-(trifluoromethyl)phenyl]-1,2,4-triazine Chemical compound CSC1=NN=CC(C=2C=C(C=CC=2)C(F)(F)F)=N1 OKFBBHMBTUDVCB-UHFFFAOYSA-N 0.000 claims description 3
UJVYSGDXMLQGJC-UHFFFAOYSA-N 5-phenyl-3-propoxy-1,2,4-triazine Chemical compound CCCOC1=NN=CC(C=2C=CC=CC=2)=N1 UJVYSGDXMLQGJC-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004660 phenylalkylthio group Chemical group 0.000 claims description 3
FQMZGTBMIZKLPL-UHFFFAOYSA-N 5,6-bis(4-chlorophenyl)-3-methylsulfanyl-1,2,4-triazine Chemical compound C=1C=C(Cl)C=CC=1C1=NC(SC)=NN=C1C1=CC=C(Cl)C=C1 FQMZGTBMIZKLPL-UHFFFAOYSA-N 0.000 claims description 2
VZWLMFMRSUDPAQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-methylsulfanyl-1,2,4-triazine Chemical compound CSC1=NN=CC(C=2C=C(Cl)C=CC=2)=N1 VZWLMFMRSUDPAQ-UHFFFAOYSA-N 0.000 claims description 2
YEXGZTRYYPXSAQ-UHFFFAOYSA-N 5-cyclopropyl-3-methylsulfanyl-1,2,4-triazine Chemical compound CSC1=NN=CC(C2CC2)=N1 YEXGZTRYYPXSAQ-UHFFFAOYSA-N 0.000 claims description 2
PEMYPKAACOIDHG-UHFFFAOYSA-N 5-tert-butyl-3-methylsulfanyl-1,2,4-triazine Chemical compound CSC1=NN=CC(C(C)(C)C)=N1 PEMYPKAACOIDHG-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 21
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
125000005805 dimethoxy phenyl group Chemical group 0.000 claims 5
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
DCZRWXWVUPZXKL-UHFFFAOYSA-N 3-chloro-5-phenyl-1,2,4-triazine Chemical compound ClC1=NN=CC(C=2C=CC=CC=2)=N1 DCZRWXWVUPZXKL-UHFFFAOYSA-N 0.000 claims 4
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims 4
YYWAKCVNYNEBSF-UHFFFAOYSA-N n'-(5-phenyl-1,2,4-triazin-3-yl)acetohydrazide Chemical compound CC(=O)NNC1=NN=CC(C=2C=CC=CC=2)=N1 YYWAKCVNYNEBSF-UHFFFAOYSA-N 0.000 claims 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
KNLHWOCNGNIQGJ-UHFFFAOYSA-N 1-[5,6-bis(4-chlorophenyl)-1,2,4-triazin-3-yl]-2-methylhydrazine Chemical compound C=1C=C(Cl)C=CC=1C1=NC(NNC)=NN=C1C1=CC=C(Cl)C=C1 KNLHWOCNGNIQGJ-UHFFFAOYSA-N 0.000 claims 3
HBQQTUZFVAWGRS-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-methoxy-1,2,4-triazine Chemical compound COC1=NN=CC(C=2C=C(Cl)C=CC=2)=N1 HBQQTUZFVAWGRS-UHFFFAOYSA-N 0.000 claims 3
QIWFSCBVELQMSW-UHFFFAOYSA-N 5-tert-butyl-3-methoxy-1,2,4-triazine Chemical compound COC1=NN=CC(C(C)(C)C)=N1 QIWFSCBVELQMSW-UHFFFAOYSA-N 0.000 claims 3
KDEAMNZLDHHLDO-UHFFFAOYSA-N [5-[3-(trifluoromethyl)phenyl]-1,2,4-triazin-3-yl]hydrazine Chemical compound NNC1=NN=CC(C=2C=C(C=CC=2)C(F)(F)F)=N1 KDEAMNZLDHHLDO-UHFFFAOYSA-N 0.000 claims 3
PQZFHDKORYQQSD-UHFFFAOYSA-N n'-[5-(4-chlorophenyl)-1,2,4-triazin-3-yl]propanehydrazide Chemical compound CCC(=O)NNC1=NN=CC(C=2C=CC(Cl)=CC=2)=N1 PQZFHDKORYQQSD-UHFFFAOYSA-N 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
OFUCCBIWEUKISP-UHFFFAOYSA-N 2,2,2-trifluoroacetohydrazide Chemical compound NNC(=O)C(F)(F)F OFUCCBIWEUKISP-UHFFFAOYSA-N 0.000 claims 2
CZILVVMDXMUXKU-UHFFFAOYSA-N 4-[4-(3-methoxy-1,2,4-triazin-5-yl)phenyl]morpholine Chemical compound COC1=NN=CC(C=2C=CC(=CC=2)N2CCOCC2)=N1 CZILVVMDXMUXKU-UHFFFAOYSA-N 0.000 claims 2
229910052801 chlorine Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 claims 2
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims 2
CBWZPMAODJSGAT-UHFFFAOYSA-N (5,6-diphenyl-1,2,4-triazin-3-yl)hydrazine Chemical compound C=1C=CC=CC=1C1=NC(NN)=NN=C1C1=CC=CC=C1 CBWZPMAODJSGAT-UHFFFAOYSA-N 0.000 claims 1
RYYJLPHFRIIPCL-UHFFFAOYSA-N 3-chloro-5,6-bis(4-chlorophenyl)-1,2,4-triazine Chemical compound C1=CC(Cl)=CC=C1C1=NN=C(Cl)N=C1C1=CC=C(Cl)C=C1 RYYJLPHFRIIPCL-UHFFFAOYSA-N 0.000 claims 1
FMSREUKSXAZODB-UHFFFAOYSA-N 3-chloro-5,6-diphenyl-1,2,4-triazine Chemical compound C=1C=CC=CC=1C1=NC(Cl)=NN=C1C1=CC=CC=C1 FMSREUKSXAZODB-UHFFFAOYSA-N 0.000 claims 1
QJBICCUQQDXOQB-UHFFFAOYSA-N 3-methylsulfanyl-5,6-diphenyl-1,2,4-triazine Chemical compound C=1C=CC=CC=1C1=NC(SC)=NN=C1C1=CC=CC=C1 QJBICCUQQDXOQB-UHFFFAOYSA-N 0.000 claims 1
KNNFEOWMRYYKOO-UHFFFAOYSA-N 4-[4-(3-methylsulfanyl-1,2,4-triazin-5-yl)phenyl]morpholine Chemical compound CSC1=NN=CC(C=2C=CC(=CC=2)N2CCOCC2)=N1 KNNFEOWMRYYKOO-UHFFFAOYSA-N 0.000 claims 1
YTYDLEUAHPVYPQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methylsulfanyl-1,2,4-triazine Chemical compound CSC1=NN=CC(C=2C=CC(Cl)=CC=2)=N1 YTYDLEUAHPVYPQ-UHFFFAOYSA-N 0.000 claims 1
DGSCLDQGFPHDFX-UHFFFAOYSA-N 5-tert-butyl-3-chloro-1,2,4-triazine Chemical compound CC(C)(C)C1=CN=NC(Cl)=N1 DGSCLDQGFPHDFX-UHFFFAOYSA-N 0.000 claims 1
YATZMQUFJYIYMI-UHFFFAOYSA-N C(CC)(=O)C=1N=NC(=C(N1)C1=CC=C(C=C1)Cl)NN Chemical compound C(CC)(=O)C=1N=NC(=C(N1)C1=CC=C(C=C1)Cl)NN YATZMQUFJYIYMI-UHFFFAOYSA-N 0.000 claims 1
OKVDLKSQZJUZHJ-UHFFFAOYSA-N [5,6-bis(4-chlorophenyl)-1,2,4-triazin-3-yl]hydrazine Chemical compound C=1C=C(Cl)C=CC=1C1=NC(NN)=NN=C1C1=CC=C(Cl)C=C1 OKVDLKSQZJUZHJ-UHFFFAOYSA-N 0.000 claims 1
KNBBECLZSZIELM-UHFFFAOYSA-N [5-(4-chlorophenyl)-1,2,4-triazin-3-yl]hydrazine Chemical compound NNC1=NN=CC(C=2C=CC(Cl)=CC=2)=N1 KNBBECLZSZIELM-UHFFFAOYSA-N 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Chemical class 0.000 abstract description 24
230000000694 effects Effects 0.000 abstract description 21
230000003110 anti-inflammatory effect Effects 0.000 abstract description 13
210000003169 central nervous system Anatomy 0.000 abstract description 11
230000000144 pharmacologic effect Effects 0.000 abstract description 11
230000000202 analgesic effect Effects 0.000 abstract description 8
208000001953 Hypotension Diseases 0.000 abstract description 7
230000001754 anti-pyretic effect Effects 0.000 abstract description 7
208000021822 hypotensive Diseases 0.000 abstract description 7
239000002221 antipyretic Substances 0.000 abstract description 5
230000002959 anti-hypotensive effect Effects 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
238000002360 preparation method Methods 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 17
241001465754 Metazoa Species 0.000 description 16
238000003556 assay Methods 0.000 description 14
238000012360 testing method Methods 0.000 description 14
150000003918 triazines Chemical class 0.000 description 14
239000000463 material Substances 0.000 description 13
239000007787 solid Substances 0.000 description 13
241000699670 Mus sp. Species 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
150000002431 hydrogen Chemical group 0.000 description 11
238000010992 reflux Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XQHHKDYGFGXLMM-UHFFFAOYSA-N C[S+]=C(N)NN.I Chemical compound C[S+]=C(N)NN.I XQHHKDYGFGXLMM-UHFFFAOYSA-N 0.000 description 9
230000000875 corresponding effect Effects 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 7
238000003756 stirring Methods 0.000 description 7
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
229920001525 carrageenan Polymers 0.000 description 6
235000010418 carrageenan Nutrition 0.000 description 6
210000000548 hind-foot Anatomy 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 5
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
GREANYIQYOXLMQ-UHFFFAOYSA-N 3-methoxy-5-phenyl-1,2,4-triazine Chemical compound COC1=NN=CC(C=2C=CC=CC=2)=N1 GREANYIQYOXLMQ-UHFFFAOYSA-N 0.000 description 5
206010030113 Oedema Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
125000003282 alkyl amino group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
210000002683 foot Anatomy 0.000 description 5
239000007789 gas Substances 0.000 description 5
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 5
229920000609 methyl cellulose Polymers 0.000 description 5
239000001923 methylcellulose Substances 0.000 description 5
230000004044 response Effects 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
206010037660 Pyrexia Diseases 0.000 description 4
230000001430 anti-depressive effect Effects 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
229910000043 hydrogen iodide Inorganic materials 0.000 description 4
230000000147 hypnotic effect Effects 0.000 description 4
230000001077 hypotensive effect Effects 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
ADUHCGZLROUKFY-UHFFFAOYSA-N 3-phenyl-1,2,4-triazine Chemical class C1=CC=CC=C1C1=NC=CN=N1 ADUHCGZLROUKFY-UHFFFAOYSA-N 0.000 description 3
241000790917 Dioxys <bee> Species 0.000 description 3
239000004471 Glycine Substances 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
206010042674 Swelling Diseases 0.000 description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
230000036592 analgesia Effects 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940005513 antidepressants Drugs 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000009833 condensation Methods 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA303,466A 1977-05-17 1978-05-16 Triazines substituees en 1,2,4 a proprietes pharmaceutiques Expired CA1128507A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000399169A CA1151165A (fr)	1977-05-17	1982-03-23	1,2,4,-triazines substituees, ayant des proprietes pharmacologiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US79767677A	1977-05-17	1977-05-17
US897,803		1978-04-19
US05/897,803 US4157392A (en)	1977-05-17	1978-04-19	Pharmacologically active substituted 1,2,4-triazines
US797,676		1991-11-25

Publications (1)

Publication Number	Publication Date
CA1128507A true CA1128507A (fr)	1982-07-27

Family

ID=27121911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,466A Expired CA1128507A (fr)	1977-05-17	1978-05-16	Triazines substituees en 1,2,4 a proprietes pharmaceutiques

Country Status (8)

Country	Link
JP (1)	JPS5416491A (fr)
CA (1)	CA1128507A (fr)
CH (1)	CH633541A5 (fr)
DE (1)	DE2821381A1 (fr)
FR (1)	FR2391202A1 (fr)
GB (3)	GB1604083A (fr)
IL (1)	IL54728A (fr)
IT (1)	IT1105463B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2485531A1 (fr) *	1980-06-25	1981-12-31	Fabre Sa Pierre	Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant
US4616014A (en) *	1981-10-22	1986-10-07	Fujisawa Pharmaceutical Co., Ltd.	Triazine derivatives, and pharmaceutical compositions comprising the same
US4513135A (en) *	1982-03-05	1985-04-23	Eli Lilly And Company	Diaryl-pyrazine derivatives affecting GABA binding
US4581356A (en) *	1983-03-22	1986-04-08	Fujisawa Pharmaceutical Co., Ltd.	Triazine derivatives, and pharmaceutical compositions comprising the same
DE3508665A1 (de) *	1985-03-12	1986-09-18	Hoechst Ag, 6230 Frankfurt	Heterocyclische sulfide und ihre anwendung als immunmodulatoren
TWI316055B (fr) *	2001-04-26	2009-10-21	Nippon Shinyaku Co Ltd
ES2579949T3 (es)	2010-02-05	2016-08-17	Heptares Therapeutics Limited	Derivados de 1,2,4-triazin-4-amina
FR2974099B1 (fr) *	2011-04-14	2013-04-19	Michelin Soc Tech	Composition de caoutchouc comprenant un derive de la 1,2,4-triazine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2343478A1 (fr) *	1976-03-10	1977-10-07	Lilly Co Eli	Nouvelles 5,6-diaryl-1,2,4-triazines et leur utilisation comme agents anti-inflammatoires locaux
FR2368278A1 (fr) *	1976-10-25	1978-05-19	Fabre Sa Pierre	Nouveaux medicaments antalgiques contenant des triazines 1-2-4

1978
- 1978-05-16 IL IL54728A patent/IL54728A/xx unknown
- 1978-05-16 IT IT49404/78A patent/IT1105463B/it active
- 1978-05-16 DE DE19782821381 patent/DE2821381A1/de not_active Withdrawn
- 1978-05-16 FR FR7814417A patent/FR2391202A1/fr active Granted
- 1978-05-16 GB GB19869/78A patent/GB1604083A/en not_active Expired
- 1978-05-16 CH CH529678A patent/CH633541A5/fr not_active IP Right Cessation
- 1978-05-16 CA CA303,466A patent/CA1128507A/fr not_active Expired
- 1978-05-16 GB GB33941/80A patent/GB1604085A/en not_active Expired
- 1978-05-16 JP JP5814578A patent/JPS5416491A/ja active Pending
- 1978-05-16 GB GB33940/80A patent/GB1604084A/en not_active Expired

Also Published As

Publication number	Publication date
JPS5416491A (en)	1979-02-07
IT7849404A0 (it)	1978-05-16
FR2391202A1 (fr)	1978-12-15
IT1105463B (it)	1985-11-04
GB1604084A (en)	1981-12-02
FR2391202B1 (fr)	1982-04-02
IL54728A0 (en)	1978-07-31
IL54728A (en)	1983-06-15
GB1604085A (en)	1981-12-02
DE2821381A1 (de)	1978-11-30
CH633541A5 (en)	1982-12-15
GB1604083A (en)	1981-12-02

Legal Events

Date	Code	Title	Description
1999-07-27	MKEX	Expiry

Publication	Publication Date	Title
US4683232A (en)	1987-07-28	Heterocyclic compounds having cardiotonic use
CA1199027A (fr)	1986-01-07	Derives heterocycliques de pyridazinone, thiadiazinone, oxadiazinone et triazinone
US4495185A (en)	1985-01-22	1,2,4-Triazin-3(2H) ones
EP1548011A1 (fr)	2005-06-29	Dérivés de 1,4-benzodiazépine-2-one comme inhibiteurs de PDE2 phosphodiesterase, leurs préparation et utilisation thérapeutique
CA1128507A (fr)	1982-07-27	Triazines substituees en 1,2,4 a proprietes pharmaceutiques
US4157392A (en)	1979-06-05	Pharmacologically active substituted 1,2,4-triazines
US4489074A (en)	1984-12-18	1,3,4-Thiadiazin-2-ones
WO1983000864A1 (fr)	1983-03-17	TRIAZINES-1,2,4-TRIAZOLOAD4,3,-bBD-1,2,4 SUBSTITUEES ANTI-INFLAMMATOIRES
US4001280A (en)	1977-01-04	Chromone derivatives
US4404214A (en)	1983-09-13	2-Pyridinecarboxamide derivatives compositions containing same and method of using same
US4493835A (en)	1985-01-15	1,3,4-Thiadiazines
US4310551A (en)	1982-01-12	Pharmacologically active substituted 1,2,4-triazines
US4251527A (en)	1981-02-17	Pharmacologically active substituted 1,2,4-triazines
US4656267A (en)	1987-04-07	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
Gautam et al.	2010	Synthesis, antimicrobial and insecticidal activity of some new cinnoline based chalcones and cinnoline based pyrazoline derivatives
CA1151165A (fr)	1983-08-02	1,2,4,-triazines substituees, ayant des proprietes pharmacologiques
US4045439A (en)	1977-08-30	6-Substituted-4-hydroxycinnolin-3-yl carboxylic acids and esters thereof
US4065571A (en)	1977-12-27	Antiviral 5-(substituted benzal) hydantoins
EP0088128A1 (fr)	1983-09-14	4-pyridylpyridazin(2h)-3-ones antiinflammatoires et analgesiques
US4528294A (en)	1985-07-09	Benzoyl-phenyl-piperidine derivatives
US4013770A (en)	1977-03-22	Antiviral 5-(substituted benzal) hydantoins
US3560490A (en)	1971-02-02	Trifluoromethyl furan derivatives
US4264617A (en)	1981-04-28	Antiviral 5-(substituted benzal) hydantoins
GB1562935A (en)	1980-03-19	Substituted paminophenyl-as-triazinediones process for their preparation and compositions containing them
US4427683A (en)	1984-01-24	Antiinflammatory 2'-pyridyl-1'-oxide carbothiolate and carbodithioate compounds