BG60318B2 - Метод за получаване на триазолил тиоамидни производни - Google Patents
Метод за получаване на триазолил тиоамидни производни Download PDFInfo
- Publication number
- BG60318B2 BG60318B2 BG93292A BG9329290A BG60318B2 BG 60318 B2 BG60318 B2 BG 60318B2 BG 93292 A BG93292 A BG 93292A BG 9329290 A BG9329290 A BG 9329290A BG 60318 B2 BG60318 B2 BG 60318B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- general formula
- amino
- triazol
- optionally substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 239000012988 Dithioester Substances 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 triazolyl thioamide derivatives Chemical class 0.000 claims description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- RZCPCGLTLWMRFG-UHFFFAOYSA-N CN(C)N1CCCCC1SC Chemical group CN(C)N1CCCCC1SC RZCPCGLTLWMRFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 3
- 230000002921 anti-spasmodic effect Effects 0.000 abstract description 3
- 239000000935 antidepressant agent Substances 0.000 abstract description 3
- 229940005513 antidepressants Drugs 0.000 abstract description 3
- 230000002936 tranquilizing effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 206010015995 Eyelid ptosis Diseases 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 208000005392 Spasm Diseases 0.000 description 6
- 201000003004 ptosis Diseases 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 5
- 231100001274 therapeutic index Toxicity 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-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
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 3
- 229960000836 amitriptyline Drugs 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 3
- 229960002456 hexobarbital Drugs 0.000 description 3
- 231100000225 lethality Toxicity 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
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- 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 2
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 210000000744 eyelid Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229960003147 reserpine Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- PFCXSNACHOIUGM-UHFFFAOYSA-N 1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one Chemical compound C1CC2=CC=CC=C2C2N1CCC(=O)C2 PFCXSNACHOIUGM-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([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
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- SPGYORMDCBHIGX-UHFFFAOYSA-N 5-amino-1,2,4-triazole-1-carbothioamide Chemical class NC(=S)N1N=CN=C1N SPGYORMDCBHIGX-UHFFFAOYSA-N 0.000 description 1
- FJRZOOICEHBAED-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazol-3-amine Chemical compound CC1=NNC(N)=N1 FJRZOOICEHBAED-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- KXEMQEGRZWUKJS-UHFFFAOYSA-N Raufloridine Natural products COC1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000539 anti-peristaltic effect Effects 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- IZHXLJVMXFNLIR-UHFFFAOYSA-N ethyl n-(5-amino-1,2,4-triazole-1-carbothioyl)carbamate Chemical class CCOC(=O)NC(=S)N1N=CN=C1N IZHXLJVMXFNLIR-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 238000002156 mixing Methods 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
- 239000008385 outer phase Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229960001032 trihexyphenidyl Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
-
- 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]
-
- 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
-
- 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
- C07D401/14—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 three or more hetero rings
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)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cephalosporin Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU896163A HU206096B (en) | 1989-11-24 | 1989-11-24 | Process for producing triazolylcarboxylic acid thioamide derivatives and pharmaceutical compositions comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60318B2 true BG60318B2 (bg) | 1994-07-25 |
Family
ID=10971287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG93292A BG60318B2 (bg) | 1989-11-24 | 1990-11-22 | Метод за получаване на триазолил тиоамидни производни |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US5175163A (da) |
| EP (1) | EP0434982B1 (da) |
| JP (1) | JPH03209371A (da) |
| KR (1) | KR910009674A (da) |
| CN (1) | CN1052116A (da) |
| AT (1) | ATE119888T1 (da) |
| BG (1) | BG60318B2 (da) |
| CA (1) | CA2030775A1 (da) |
| CZ (1) | CZ280559B6 (da) |
| DE (1) | DE59008718D1 (da) |
| DK (1) | DK0434982T3 (da) |
| ES (1) | ES2029778T3 (da) |
| FI (1) | FI905800A (da) |
| GR (1) | GR910300109T1 (da) |
| HU (1) | HU206096B (da) |
| IL (1) | IL96452A0 (da) |
| IN (1) | IN171500B (da) |
| PH (1) | PH27376A (da) |
| PL (1) | PL166887B1 (da) |
| RU (1) | RU2045521C1 (da) |
| TW (1) | TW210335B (da) |
| ZA (1) | ZA909409B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0710654A4 (en) * | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2352944A (en) * | 1942-07-04 | 1944-07-04 | Gen Electric | Triazole derivatives |
| GB949170A (en) * | 1960-03-15 | 1964-02-12 | France Etat | Carbamyl and thiocarbamyl substances, methods for producing same and applications thereof |
| US4421753A (en) * | 1982-01-15 | 1983-12-20 | American Cyanamid Company | 1-(5-Amino-4H-1,2,4-triazol-3-yl)-4-substituted-piperazines |
| DD205905A1 (de) * | 1982-08-17 | 1984-01-11 | Univ Rostock | Verfahren zur herstellung von substituierten 1,2,4-triazolo (2,3-a)-1,3,5-triazinen |
-
1989
- 1989-11-24 HU HU896163A patent/HU206096B/hu not_active IP Right Cessation
-
1990
- 1990-11-21 PH PH41587A patent/PH27376A/en unknown
- 1990-11-21 US US07/617,126 patent/US5175163A/en not_active Expired - Fee Related
- 1990-11-22 BG BG93292A patent/BG60318B2/bg unknown
- 1990-11-22 JP JP2315680A patent/JPH03209371A/ja active Pending
- 1990-11-23 IL IL96452A patent/IL96452A0/xx unknown
- 1990-11-23 RU SU904831825A patent/RU2045521C1/ru active
- 1990-11-23 IN IN950/MAS/90A patent/IN171500B/en unknown
- 1990-11-23 DK DK90122351.1T patent/DK0434982T3/da active
- 1990-11-23 EP EP90122351A patent/EP0434982B1/de not_active Expired - Lifetime
- 1990-11-23 ES ES90122351T patent/ES2029778T3/es not_active Expired - Lifetime
- 1990-11-23 CA CA002030775A patent/CA2030775A1/en not_active Abandoned
- 1990-11-23 AT AT90122351T patent/ATE119888T1/de active
- 1990-11-23 DE DE59008718T patent/DE59008718D1/de not_active Expired - Fee Related
- 1990-11-23 ZA ZA909409A patent/ZA909409B/xx unknown
- 1990-11-23 KR KR1019900019076A patent/KR910009674A/ko not_active Application Discontinuation
- 1990-11-23 CZ CS905839A patent/CZ280559B6/cs unknown
- 1990-11-23 PL PL90287909A patent/PL166887B1/pl unknown
- 1990-11-23 FI FI905800A patent/FI905800A/fi not_active IP Right Cessation
- 1990-11-24 CN CN90109404A patent/CN1052116A/zh active Pending
-
1991
- 1991-03-23 TW TW079109927A patent/TW210335B/zh active
- 1991-09-09 US US07/755,219 patent/US5276030A/en not_active Expired - Fee Related
- 1991-12-10 GR GR91300109T patent/GR910300109T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2029778T1 (es) | 1992-10-01 |
| HU896163D0 (en) | 1990-02-28 |
| CZ583990A3 (en) | 1995-11-15 |
| ES2029778T3 (es) | 1995-06-01 |
| TW210335B (da) | 1993-08-01 |
| ATE119888T1 (de) | 1995-04-15 |
| EP0434982B1 (de) | 1995-03-15 |
| GR910300109T1 (en) | 1991-12-10 |
| CN1052116A (zh) | 1991-06-12 |
| FI905800A0 (fi) | 1990-11-23 |
| IN171500B (da) | 1992-10-31 |
| FI905800A (fi) | 1991-05-25 |
| HU206096B (en) | 1992-08-28 |
| CA2030775A1 (en) | 1991-05-25 |
| DK0434982T3 (da) | 1995-05-22 |
| ZA909409B (en) | 1991-09-25 |
| HUT59112A (en) | 1992-04-28 |
| PL287909A1 (en) | 1991-09-23 |
| KR910009674A (ko) | 1991-06-28 |
| JPH03209371A (ja) | 1991-09-12 |
| EP0434982A2 (de) | 1991-07-03 |
| IL96452A0 (en) | 1991-08-16 |
| CZ280559B6 (cs) | 1996-02-14 |
| DE59008718D1 (de) | 1995-04-20 |
| US5276030A (en) | 1994-01-04 |
| PH27376A (en) | 1993-06-21 |
| EP0434982A3 (en) | 1991-12-18 |
| PL166887B1 (pl) | 1995-06-30 |
| RU2045521C1 (ru) | 1995-10-10 |
| US5175163A (en) | 1992-12-29 |
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