CH639080A5 - Process for the preparation of a 3-substituted-tetrahydro-1,2,4-triazine - Google Patents

Process for the preparation of a 3-substituted-tetrahydro-1,2,4-triazine Download PDF

Info

Publication number: CH639080A5
Authority: CH; Switzerland
Prior art keywords: phenyl; group; hydrogen atom; compound; substituted
Prior art date: 1977-01-21

Application number

CH65378A

Other languages

English (en)

French (fr)

Inventor

Albert Joseph Jun Schuster

John Martin

David Mark Spatz

Paul James Widner

Original Assignee

Dow Chemical Co

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.)

1977-01-21

Filing date

1978-01-20

Publication date

1983-10-31

1977-01-21 Priority claimed from US05/761,177 external-priority patent/US4071684A/en

1977-06-06 Priority claimed from US05/803,927 external-priority patent/US4263295A/en

1978-01-20 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1983-10-31 Publication of CH639080A5 publication Critical patent/CH639080A5/fr

Links

-1 3-substituted-tetrahydro-1,2,4-triazine Chemical class 0.000 title claims description 29
238000000034 method Methods 0.000 title claims description 28
230000008569 process Effects 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
239000002249 anxiolytic agent Substances 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 17
JHKIHARISAHZAK-UHFFFAOYSA-N 2-hydrazinylethanamine Chemical compound NCCNN JHKIHARISAHZAK-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 16
230000000049 anti-anxiety effect Effects 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
150000002825 nitriles Chemical class 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
230000003197 catalytic effect Effects 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
238000006467 substitution reaction Methods 0.000 claims description 7
229910052723 transition metal Inorganic materials 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
DRONDEZXOJEUGU-UHFFFAOYSA-N 2,3-diphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(C#N)CC1=CC=CC=C1 DRONDEZXOJEUGU-UHFFFAOYSA-N 0.000 claims description 5
QQZDRBLYFGVUER-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NCCNN1 QQZDRBLYFGVUER-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
150000003624 transition metals Chemical class 0.000 claims description 4
239000012634 fragment Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000011987 methylation Effects 0.000 claims description 3
238000007069 methylation reaction Methods 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
230000021736 acetylation Effects 0.000 claims description 2
238000006640 acetylation reaction Methods 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
HOSLYCHCJBOEKW-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-1-phenylethyl]-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1=CC(Cl)=CC=C1CC(C=1C=CC=CC=1)C1=NNCCN1 HOSLYCHCJBOEKW-UHFFFAOYSA-N 0.000 claims 2
PCPLHNTXISBUGK-UHFFFAOYSA-N 3-[1-(4-methylphenyl)-2-phenylethyl]-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1=CC(C)=CC=C1C(C=1NCCNN=1)CC1=CC=CC=C1 PCPLHNTXISBUGK-UHFFFAOYSA-N 0.000 claims 1
IFZOKYRLNVCHPN-UHFFFAOYSA-N 3-[2-(2,6-dichlorophenyl)-1-phenylethyl]-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound ClC1=CC=CC(Cl)=C1CC(C=1C=CC=CC=1)C1=NNCCN1 IFZOKYRLNVCHPN-UHFFFAOYSA-N 0.000 claims 1
150000003840 hydrochlorides Chemical class 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
230000007704 transition Effects 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
239000011593 sulfur Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
206010015995 Eyelid ptosis Diseases 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000935 antidepressant agent Substances 0.000 description 7
239000003246 corticosteroid Substances 0.000 description 7
201000003004 ptosis Diseases 0.000 description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000001430 anti-depressive effect Effects 0.000 description 6
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
MKVBVTOSWPBSNC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,4-triazine Chemical compound C1NNC=CN1 MKVBVTOSWPBSNC-UHFFFAOYSA-N 0.000 description 5
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
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BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 5
229960003147 reserpine Drugs 0.000 description 5
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
229940005513 antidepressants Drugs 0.000 description 4
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239000008280 blood Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
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239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
208000019901 Anxiety disease Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000007928 intraperitoneal injection Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical class C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
241000700159 Rattus Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[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 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
229940001470 psychoactive drug Drugs 0.000 description 2
239000004089 psychotropic agent Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical class C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 description 1
OFCFYWOKHPOXKF-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-chlorobenzene Chemical group C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 OFCFYWOKHPOXKF-UHFFFAOYSA-N 0.000 description 1
GFGDAKKRLNCZIC-UHFFFAOYSA-N 1-[3-(1,2-diphenylethyl)-1-methyl-5,6-dihydro-1,2,4-triazin-4-yl]ethanone;hydrochloride Chemical compound Cl.CN1CCN(C(C)=O)C(C(CC=2C=CC=CC=2)C=2C=CC=CC=2)=N1 GFGDAKKRLNCZIC-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
YQUAOWNIIVZNAK-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NNCCN1 YQUAOWNIIVZNAK-UHFFFAOYSA-N 0.000 description 1
AHYPXPQZHHTKPJ-UHFFFAOYSA-N 3-[2-(2,6-dichlorophenyl)-1-phenylethyl]-1,2,5,6-tetrahydro-1,2,4-triazine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1CC(C=1C=CC=CC=1)C1=NNCCN1 AHYPXPQZHHTKPJ-UHFFFAOYSA-N 0.000 description 1
JTQYCBSZFCKMQA-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-1-phenylethyl]-1-methyl-5,6-dihydro-2h-1,2,4-triazine;hydrochloride Chemical compound Cl.N1N(C)CCN=C1C(C=1C=CC=CC=1)CC1=CC=C(Cl)C=C1 JTQYCBSZFCKMQA-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000008156 Ringer's lactate solution Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
BMLSTPRTEKLIPM-UHFFFAOYSA-I calcium;potassium;disodium;hydrogen carbonate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].OC([O-])=O BMLSTPRTEKLIPM-UHFFFAOYSA-I 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
238000012754 cardiac puncture Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000007911 effervescent powder Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
229960002455 methoxyflurane Drugs 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
FDRPZJWMPZUHBN-UHFFFAOYSA-N triazin-2-ium;chloride Chemical compound Cl.C1=CN=NN=C1 FDRPZJWMPZUHBN-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material 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)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH65378A 1977-01-21 1978-01-20 Process for the preparation of a 3-substituted-tetrahydro-1,2,4-triazine CH639080A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/761,177 US4071684A (en)	1977-01-21	1977-01-21	Process for producing 3-substituted 1,2,4-triazines
US05/803,927 US4263295A (en)	1977-06-06	1977-06-06	Psychoactive 3-(1-2-diarylethyl)-1,4,5,6-tetrahydro-1,2,4-triazines and their method of use

Publications (1)

Publication Number	Publication Date
CH639080A5 true CH639080A5 (en)	1983-10-31

Family

ID=27116938

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH65378A CH639080A5 (en)	1977-01-21	1978-01-20	Process for the preparation of a 3-substituted-tetrahydro-1,2,4-triazine

Country Status (13)

Country	Link
JP (1)	JPS5395987A (de)
AT (1)	AT360032B (de)
CH (1)	CH639080A5 (de)
DE (1)	DE2800385A1 (de)
DK (1)	DK152755C (de)
ES (1)	ES466205A1 (de)
FR (1)	FR2378019A1 (de)
GB (1)	GB1576579A (de)
IE (1)	IE46246B1 (de)
IT (1)	IT1111157B (de)
NL (1)	NL7800535A (de)
NO (1)	NO159529C (de)
SE (1)	SE447380B (de)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3497509A (en) *	1966-12-05	1970-02-24	Dow Chemical Co	Imino ester method for producing 1,4,5,6-tetrahydro-as-triazine
US3428635A (en) *	1966-12-05	1969-02-18	Dow Chemical Co	Substituted 1,4,5,6 - tetrahydro - as - triazines and a method for their production
US3471486A (en) *	1967-10-23	1969-10-07	Dow Chemical Co	3-aralkyl-as-triazines

1978
- 1978-01-05 DE DE19782800385 patent/DE2800385A1/de active Granted
- 1978-01-17 DK DK023078A patent/DK152755C/da not_active IP Right Cessation
- 1978-01-17 NL NL7800535A patent/NL7800535A/xx not_active Application Discontinuation
- 1978-01-18 IE IE115/78A patent/IE46246B1/en not_active IP Right Cessation
- 1978-01-19 NO NO78780201A patent/NO159529C/no unknown
- 1978-01-19 IT IT19422/78A patent/IT1111157B/it active
- 1978-01-19 JP JP378478A patent/JPS5395987A/ja active Granted
- 1978-01-20 GB GB2389/78A patent/GB1576579A/en not_active Expired
- 1978-01-20 FR FR7801672A patent/FR2378019A1/fr active Granted
- 1978-01-20 CH CH65378A patent/CH639080A5/fr not_active IP Right Cessation
- 1978-01-20 ES ES466205A patent/ES466205A1/es not_active Expired
- 1978-01-20 SE SE7800737A patent/SE447380B/sv not_active IP Right Cessation
- 1978-01-20 AT AT44378A patent/AT360032B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2800385C2 (de)	1989-01-26
ATA44378A (de)	1980-05-15
DK152755B (da)	1988-05-09
SE447380B (sv)	1986-11-10
DK152755C (da)	1988-10-03
DE2800385A1 (de)	1978-07-27
JPS6241227B2 (de)	1987-09-02
IE780115L (en)	1978-07-21
IE46246B1 (en)	1983-04-06
NO780201L (no)	1978-07-24
NL7800535A (nl)	1978-07-25
IT7819422A0 (it)	1978-01-19
GB1576579A (en)	1980-10-08
ES466205A1 (es)	1979-06-01
NO159529B (no)	1988-10-03
JPS5395987A (en)	1978-08-22
FR2378019B1 (de)	1980-08-22
SE7800737L (sv)	1978-07-22
DK23078A (da)	1978-07-22
IT1111157B (it)	1986-01-13
AT360032B (de)	1980-12-10
FR2378019A1 (fr)	1978-08-18
NO159529C (no)	1989-01-11

Legal Events

Date	Code	Title	Description
1994-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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CH644124A5 (fr)	1984-07-13	Oxoimidazoquinoxalines et leurs sels, leurs procedes de preparation et les medicaments les renfermant.
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