NO864307L - Fremgangsmaate for fremstilling av 5-heterocycliske-2,4-dialkyl-3h-1,2,4-triazol-3-thioner. - Google Patents

Fremgangsmaate for fremstilling av 5-heterocycliske-2,4-dialkyl-3h-1,2,4-triazol-3-thioner.

Info

Publication number: NO864307L
Authority: NO; Norway
Prior art keywords: compounds; triazol; heterocyclic; formula; thioner
Prior art date: 1985-10-29

Application number

NO864307A

Other languages

English (en)

Norwegian (no)

Other versions

NO864307D0 (no

Inventor

John M Kane

Francis P Miller

Original Assignee

Merrell Dow Pharma

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.)

1985-10-29

Filing date

1986-10-28

Publication date

1987-04-30

1986-10-28 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1986-10-28 Publication of NO864307D0 publication Critical patent/NO864307D0/no

1987-04-30 Publication of NO864307L publication Critical patent/NO864307L/no

Links

238000000034 method Methods 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims description 23
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims 2
SCCTZXJTOAMUDZ-UHFFFAOYSA-N 2,4-dimethyl-5-pyridin-4-yl-1,2,4-triazole-3-thione Chemical compound CN1C(=S)N(C)N=C1C1=CC=NC=C1 SCCTZXJTOAMUDZ-UHFFFAOYSA-N 0.000 claims 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
238000012360 testing method Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
-1 alkoxy radicals Chemical class 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
239000000935 antidepressant agent Substances 0.000 description 5
229940005513 antidepressants Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002540 isothiocyanates Chemical class 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
150000003583 thiosemicarbazides Chemical class 0.000 description 5
206010015995 Eyelid ptosis Diseases 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
201000003004 ptosis Diseases 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
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 3
GROVXILJTVFYEC-UHFFFAOYSA-N 1,3-dimethyl-1-(pyridine-4-carbonylamino)thiourea Chemical compound CNC(=S)N(C)NC(=O)C1=CC=NC=C1 GROVXILJTVFYEC-UHFFFAOYSA-N 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
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 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
230000002631 hypothermal effect Effects 0.000 description 3
229960004801 imipramine Drugs 0.000 description 3
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 3
239000007943 implant Substances 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000002265 prevention Effects 0.000 description 3
239000000376 reactant Substances 0.000 description 3
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 3
229960003147 reserpine Drugs 0.000 description 3
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 3
150000003839 salts Chemical class 0.000 description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
YEHMHSRNWIBAEL-UHFFFAOYSA-N 1-amino-1,3-dimethylthiourea Chemical compound CNC(=S)N(C)N YEHMHSRNWIBAEL-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
240000002470 Amphicarpaea bracteata Species 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
OWKWAVBMKKZMHE-UHFFFAOYSA-N benzamidothiourea Chemical class NC(=S)NNC(=O)C1=CC=CC=C1 OWKWAVBMKKZMHE-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
125000004122 cyclic group Chemical group 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
229960003914 desipramine Drugs 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
201000003104 endogenous depression Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
VXTWEDPZMSVFEF-UHFFFAOYSA-N pheniprazine Chemical compound NNC(C)CC1=CC=CC=C1 VXTWEDPZMSVFEF-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
229920000260 silastic Polymers 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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, ***e
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Psychiatry (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)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

NO864307A 1985-10-29 1986-10-28 Fremgangsmaate for fremstilling av 5-heterocycliske-2,4-dialkyl-3h-1,2,4-triazol-3-thioner. NO864307L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79236785A	1985-10-29	1985-10-29

Publications (2)

Publication Number	Publication Date
NO864307D0 NO864307D0 (no)	1986-10-28
NO864307L true NO864307L (no)	1987-04-30

Family

ID=25156665

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO864307A NO864307L (no)	1985-10-29	1986-10-28	Fremgangsmaate for fremstilling av 5-heterocycliske-2,4-dialkyl-3h-1,2,4-triazol-3-thioner.

Country Status (22)

Country	Link
US (1)	US4952593A (fi)
EP (1)	EP0226755B1 (fi)
JP (1)	JPH0733382B2 (fi)
KR (1)	KR900000368B1 (fi)
CN (1)	CN1017899B (fi)
AR (1)	AR243179A1 (fi)
AT (1)	ATE66218T1 (fi)
AU (1)	AU587293B2 (fi)
CA (1)	CA1289962C (fi)
DE (1)	DE3680885D1 (fi)
DK (1)	DK171234B1 (fi)
ES (1)	ES2040200T3 (fi)
FI (1)	FI90076C (fi)
GR (1)	GR3002484T3 (fi)
HU (1)	HU196988B (fi)
IE (1)	IE58970B1 (fi)
IL (1)	IL80435A (fi)
NO (1)	NO864307L (fi)
NZ (1)	NZ218085A (fi)
PH (1)	PH22363A (fi)
PT (1)	PT83637B (fi)
ZA (1)	ZA868116B (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4847276A (en) *	1988-09-06	1989-07-11	Merrell Dow Pharmaceuticals Inc.	Treatment of thromobocytosis with 5-(4-chlorophenyl)-2,4-diemthyl-3H-1,2,4-triazole-3-thione
US5120347A (en) *	1990-06-21	1992-06-09	Rohm And Haas Company	Aryl triazole herbicides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1066200B (de) *	1954-10-13	1959-10-01	The Upjohn Company, Kalamazoo, Mich. (V. St. A.)	Verfahren zur Herstellung von Sulfonamiden heterocyclischer Verbindungen
US3037916A (en) *	1956-02-24	1962-06-05	American Cyanamid Co	Fermentation of tetracycline
NL281755A (fi) *	1961-08-09
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung

1986
- 1986-10-22 AR AR86305653A patent/AR243179A1/es active
- 1986-10-24 ZA ZA868116A patent/ZA868116B/xx unknown
- 1986-10-24 PH PH34415A patent/PH22363A/en unknown
- 1986-10-24 CA CA000521329A patent/CA1289962C/en not_active Expired - Lifetime
- 1986-10-27 AU AU64408/86A patent/AU587293B2/en not_active Ceased
- 1986-10-27 ES ES198686114873T patent/ES2040200T3/es not_active Expired - Lifetime
- 1986-10-27 HU HU864498A patent/HU196988B/hu not_active IP Right Cessation
- 1986-10-27 AT AT86114873T patent/ATE66218T1/de not_active IP Right Cessation
- 1986-10-27 EP EP86114873A patent/EP0226755B1/en not_active Expired - Lifetime
- 1986-10-27 DE DE8686114873T patent/DE3680885D1/de not_active Expired - Fee Related
- 1986-10-28 JP JP61254830A patent/JPH0733382B2/ja not_active Expired - Lifetime
- 1986-10-28 CN CN86107126A patent/CN1017899B/zh not_active Expired
- 1986-10-28 PT PT83637A patent/PT83637B/pt not_active IP Right Cessation
- 1986-10-28 NZ NZ218085A patent/NZ218085A/xx unknown
- 1986-10-28 KR KR1019860009008A patent/KR900000368B1/ko not_active IP Right Cessation
- 1986-10-28 NO NO864307A patent/NO864307L/no unknown
- 1986-10-28 DK DK514786A patent/DK171234B1/da not_active IP Right Cessation
- 1986-10-28 IL IL80435A patent/IL80435A/xx not_active IP Right Cessation
- 1986-10-28 FI FI864378A patent/FI90076C/fi not_active IP Right Cessation
- 1986-10-28 IE IE283386A patent/IE58970B1/en not_active IP Right Cessation
1987
- 1987-07-23 US US07/076,588 patent/US4952593A/en not_active Expired - Fee Related
1991
- 1991-08-16 GR GR91401124T patent/GR3002484T3/el unknown

Also Published As

Publication number	Publication date
ATE66218T1 (de)	1991-08-15
DK514786D0 (da)	1986-10-28
PH22363A (en)	1988-08-12
EP0226755A1 (en)	1987-07-01
PT83637B (pt)	1989-01-17
NZ218085A (en)	1989-08-29
DE3680885D1 (de)	1991-09-19
JPH0733382B2 (ja)	1995-04-12
IE58970B1 (en)	1993-12-01
IE862833L (en)	1987-04-29
AU6440886A (en)	1987-04-30
ZA868116B (en)	1987-06-24
AU587293B2 (en)	1989-08-10
DK171234B1 (da)	1996-08-05
CA1289962C (en)	1991-10-01
JPS62106092A (ja)	1987-05-16
PT83637A (en)	1986-11-01
FI90076B (fi)	1993-09-15
HU196988B (en)	1989-02-28
GR3002484T3 (en)	1992-12-30
KR870004018A (ko)	1987-05-06
IL80435A (en)	1991-06-10
CN1017899B (zh)	1992-08-19
AR243179A1 (es)	1993-07-30
FI90076C (fi)	1993-12-27
CN86107126A (zh)	1987-06-10
KR900000368B1 (ko)	1990-01-25
FI864378A (fi)	1987-04-30
HUT42469A (en)	1987-07-28
US4952593A (en)	1990-08-28
ES2040200T3 (es)	1993-10-16
FI864378A0 (fi)	1986-10-28
NO864307D0 (no)	1986-10-28
DK514786A (da)	1987-04-30
EP0226755B1 (en)	1991-08-14

Publication	Publication Date	Title
GB2096600A (en)	1982-10-20	Aroylimidazolones and analogues thereof
EP0435177B1 (en)	1994-11-02	4-Benzyl-5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
NO864307L (no)	1987-04-30	Fremgangsmaate for fremstilling av 5-heterocycliske-2,4-dialkyl-3h-1,2,4-triazol-3-thioner.
EP0221485B1 (en)	1990-12-27	5-aryl-2,4-dialkyl-3h-1,2,4-triazole-3-thiones and their use as antidepressants
US4912095A (en)	1990-03-27	5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-thiones useful as antidepressants
US4775688A (en)	1988-10-04	5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-thiones and their use as antidepressants
DE3881712T2 (de)	1993-12-23	3-Aryl-5-alkylthio-4H-1,2,4-triazole.
US4775689A (en)	1988-10-04	5-(naphthyl)-2,4-dialkyl-3H-1,2,4-triazole-3-thiones and their use as antidepressants
KR100385380B1 (ko)	2003-10-10	3-페닐-1,4-디알킬-1,2,4-트리아졸륨염및항우울제로서의이의용도
EP0280867A1 (en)	1988-09-07	Process for the preparation of 5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-thiones
CA1323371C (en)	1993-10-19	Process for the preparation of 5-aryl-2,4-dialkyl-3h-1,2,4-triazole-3-thiones
JPH0233032B2 (fi)	1990-07-25
MXPA97008031A (en)		Salts of 3-phenyl-1,4-dialkyl-1,2,4-triazolio and its use as antidepresi