FI57591C - Foerfarande foer framstaellning av 4-amino-3-bensylidenhydrazino-1,2,4-triazoler med anvaendning som hypotensiva medel - Google Patents
Foerfarande foer framstaellning av 4-amino-3-bensylidenhydrazino-1,2,4-triazoler med anvaendning som hypotensiva medel Download PDFInfo
- Publication number
- FI57591C FI57591C FI3591/74A FI359174A FI57591C FI 57591 C FI57591 C FI 57591C FI 3591/74 A FI3591/74 A FI 3591/74A FI 359174 A FI359174 A FI 359174A FI 57591 C FI57591 C FI 57591C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- och
- compound
- triazole
- hydrogen atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 6
- VPBNXHYAMUPEBB-UHFFFAOYSA-N 3-n-(benzylideneamino)-1,2,4-triazole-3,4-diamine Chemical compound NN1C=NN=C1NN=CC1=CC=CC=C1 VPBNXHYAMUPEBB-UHFFFAOYSA-N 0.000 claims description 5
- 239000002220 antihypertensive agent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- NRPJWGLROHURJO-UHFFFAOYSA-N 3-n-[(2,6-dichlorophenyl)methylideneamino]-4-n-methyl-1,2,4-triazole-3,4-diamine Chemical compound CNN1C=NN=C1NN=CC1=C(Cl)C=CC=C1Cl NRPJWGLROHURJO-UHFFFAOYSA-N 0.000 claims description 3
- 208000001953 Hypotension Diseases 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 208000021822 hypotensive Diseases 0.000 claims description 3
- 230000001077 hypotensive effect Effects 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- -1 1-acetyl-2- (2,6-dichlorobenzylidene) hydrazino Chemical group 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000007792 addition Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WIDBCGPXDBQVAW-UHFFFAOYSA-N 2-amino-1-[(2,6-dichlorophenyl)methylidene]-3-(dimethylamino)guanidine Chemical compound CN(C)N=C(NN)N=CC1=C(Cl)C=CC=C1Cl WIDBCGPXDBQVAW-UHFFFAOYSA-N 0.000 description 4
- MNISGRKUIMQRKR-UHFFFAOYSA-N 3-n-[(2,6-dichlorophenyl)methylideneamino]-1,2,4-triazole-3,4-diamine;hydrochloride Chemical compound Cl.NN1C=NN=C1NN=CC1=C(Cl)C=CC=C1Cl MNISGRKUIMQRKR-UHFFFAOYSA-N 0.000 description 4
- KHCYGOIWSWLPNL-YIXHJXPBSA-N 3-n-[(e)-(2,6-dichlorophenyl)methylideneamino]-1,2,4-triazole-3,4-diamine Chemical compound NN1C=NN=C1N\N=C\C1=C(Cl)C=CC=C1Cl KHCYGOIWSWLPNL-YIXHJXPBSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000008050 dialkyl sulfates Chemical class 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JCLWFQXVXYOCAT-UHFFFAOYSA-N 1,2-diamino-3-(benzylideneamino)guanidine Chemical class NNC(=NN)NN=CC1=CC=CC=C1 JCLWFQXVXYOCAT-UHFFFAOYSA-N 0.000 description 3
- CSPZTLTUXBDWPV-UHFFFAOYSA-N 3-n-[(2,6-dichlorophenyl)methylideneamino]-4-n,4-n-dimethyl-1,2,4-triazole-3,4-diamine Chemical compound CN(C)N1C=NN=C1NN=CC1=C(Cl)C=CC=C1Cl CSPZTLTUXBDWPV-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 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
- 230000036772 blood pressure Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ZASYXTCIMBDLCB-UHFFFAOYSA-N n-[4-(diacetylamino)-1,2,4-triazol-3-yl]-n-[(2,6-dichlorophenyl)methylideneamino]acetamide Chemical compound N=1N=CN(N(C(C)=O)C(C)=O)C=1N(C(=O)C)N=CC1=C(Cl)C=CC=C1Cl ZASYXTCIMBDLCB-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ATUSUXATRWQNRE-UHFFFAOYSA-N 3-benzylidene-5-hydrazinylidene-1,2,4-triazolidin-4-amine Chemical class C(C1=CC=CC=C1)=C1NN=C(N1N)NN ATUSUXATRWQNRE-UHFFFAOYSA-N 0.000 description 1
- VUXZBSYPCBZPSP-UHFFFAOYSA-N 3-n-[(2,6-dichlorophenyl)methylideneamino]-4-n-methyl-1,2,4-triazole-3,4-diamine;hydrochloride Chemical compound Cl.CNN1C=NN=C1NN=CC1=C(Cl)C=CC=C1Cl VUXZBSYPCBZPSP-UHFFFAOYSA-N 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 101100493710 Caenorhabditis elegans bath-40 gene Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical group NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 239000005555 hypertensive agent Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LOTBNHQTJQHPHZ-UHFFFAOYSA-N n-[3-[acetyl-[(2,6-dichlorophenyl)methylideneamino]amino]-1,2,4-triazol-4-yl]-n-methylacetamide Chemical compound CC(=O)N(C)N1C=NN=C1N(C(C)=O)N=CC1=C(Cl)C=CC=C1Cl LOTBNHQTJQHPHZ-UHFFFAOYSA-N 0.000 description 1
- WYTCDHVJLOEDBF-UHFFFAOYSA-N n-[3-[acetyl-[(2,6-dichlorophenyl)methylideneamino]amino]-1,2,4-triazol-4-yl]acetamide Chemical compound CC(=O)NN1C=NN=C1N(C(C)=O)N=CC1=C(Cl)C=CC=C1Cl WYTCDHVJLOEDBF-UHFFFAOYSA-N 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI3591/74A FI57591C (fi) | 1974-12-12 | 1974-12-12 | Foerfarande foer framstaellning av 4-amino-3-bensylidenhydrazino-1,2,4-triazoler med anvaendning som hypotensiva medel |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI359174 | 1974-12-12 | ||
| FI3591/74A FI57591C (fi) | 1974-12-12 | 1974-12-12 | Foerfarande foer framstaellning av 4-amino-3-bensylidenhydrazino-1,2,4-triazoler med anvaendning som hypotensiva medel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI359174A7 FI359174A7 (show.php) | 1976-06-13 |
| FI57591B FI57591B (fi) | 1980-05-30 |
| FI57591C true FI57591C (fi) | 1980-09-10 |
Family
ID=8508588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3591/74A FI57591C (fi) | 1974-12-12 | 1974-12-12 | Foerfarande foer framstaellning av 4-amino-3-bensylidenhydrazino-1,2,4-triazoler med anvaendning som hypotensiva medel |
Country Status (1)
| Country | Link |
|---|---|
| FI (1) | FI57591C (show.php) |
-
1974
- 1974-12-12 FI FI3591/74A patent/FI57591C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| FI57591B (fi) | 1980-05-30 |
| FI359174A7 (show.php) | 1976-06-13 |
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