CA1050031A - 2,5-substituted thiadiazoles - Google Patents
2,5-substituted thiadiazolesInfo
- Publication number
- CA1050031A CA1050031A CA222,445A CA222445A CA1050031A CA 1050031 A CA1050031 A CA 1050031A CA 222445 A CA222445 A CA 222445A CA 1050031 A CA1050031 A CA 1050031A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- amino
- hydrogen
- trifluoromethyl
- thiadiazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004867 thiadiazoles Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 239000011737 fluorine Chemical group 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 phosphorus halide Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- RRXDVGPGAOJOFL-UHFFFAOYSA-N 5-[[3-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC=CC(C(F)(F)F)=C1 RRXDVGPGAOJOFL-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000004799 sedative–hypnotic effect Effects 0.000 abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- STIMORLKYIPIAQ-UHFFFAOYSA-N [[2-[3-(trifluoromethyl)phenyl]acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC(C(F)(F)F)=C1 STIMORLKYIPIAQ-UHFFFAOYSA-N 0.000 description 5
- 241000282693 Cercopithecidae Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012458 free base Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000803 paradoxical effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010062519 Poor quality sleep Diseases 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BLXXCCIBGGBDHI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(F)(F)F)=C1 BLXXCCIBGGBDHI-UHFFFAOYSA-N 0.000 description 1
- VOVGTRUVYKHYJA-UHFFFAOYSA-N 5-[2-[3-(trifluoromethyl)phenyl]ethyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CCC1=CC=CC(C(F)(F)F)=C1 VOVGTRUVYKHYJA-UHFFFAOYSA-N 0.000 description 1
- ZTJBEYICCOTCEA-UHFFFAOYSA-N 5-[4-[3-(trifluoromethyl)phenyl]butyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CCCCC1=CC=CC(C(F)(F)F)=C1 ZTJBEYICCOTCEA-UHFFFAOYSA-N 0.000 description 1
- QHQVBZWCNJVWJZ-UHFFFAOYSA-N 5-[[2,5-dichloro-3-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC(Cl)=CC(C(F)(F)F)=C1Cl QHQVBZWCNJVWJZ-UHFFFAOYSA-N 0.000 description 1
- HZYLEVSVBRVKPL-UHFFFAOYSA-N 5-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HZYLEVSVBRVKPL-UHFFFAOYSA-N 0.000 description 1
- JUUVCOHFHWKSSY-UHFFFAOYSA-N 5-[[3-chloro-5-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC(Cl)=CC(C(F)(F)F)=C1 JUUVCOHFHWKSSY-UHFFFAOYSA-N 0.000 description 1
- DNKNUHGUGHSKKO-UHFFFAOYSA-N 5-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC=C(C(F)(F)F)C=C1 DNKNUHGUGHSKKO-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282668 Cebus Species 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- VEQAGSPCZANNDR-UHFFFAOYSA-N azepine-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CC=CC=C1 VEQAGSPCZANNDR-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical group C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000004424 eye movement Effects 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45267874A | 1974-03-20 | 1974-03-20 | |
| US05/528,477 US3965110A (en) | 1974-07-05 | 1974-11-29 | 2-Amino-5-(trifluoromethyl phenylalkyl)-1,3,4-thiadiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050031A true CA1050031A (en) | 1979-03-06 |
Family
ID=27036857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA222,445A Expired CA1050031A (en) | 1974-03-20 | 1975-03-18 | 2,5-substituted thiadiazoles |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS50154251A (en, 2012) |
| CA (1) | CA1050031A (en, 2012) |
| CH (1) | CH593957A5 (en, 2012) |
| DD (1) | DD117463A5 (en, 2012) |
| DE (1) | DE2510439A1 (en, 2012) |
| DK (1) | DK136248B (en, 2012) |
| ES (1) | ES435777A1 (en, 2012) |
| FI (1) | FI750696A7 (en, 2012) |
| FR (1) | FR2264532B2 (en, 2012) |
| GB (1) | GB1482371A (en, 2012) |
| HU (1) | HU169267B (en, 2012) |
| IE (1) | IE40948B1 (en, 2012) |
| IL (2) | IL46860A (en, 2012) |
| NL (1) | NL7503058A (en, 2012) |
| NO (1) | NO750829L (en, 2012) |
| SE (1) | SE404695B (en, 2012) |
| SU (1) | SU645574A3 (en, 2012) |
-
1975
- 1975-03-10 CH CH299775A patent/CH593957A5/xx not_active IP Right Cessation
- 1975-03-11 DK DK98275AA patent/DK136248B/da unknown
- 1975-03-11 FI FI750696A patent/FI750696A7/fi not_active Application Discontinuation
- 1975-03-11 DE DE19752510439 patent/DE2510439A1/de active Pending
- 1975-03-11 SE SE7502708A patent/SE404695B/xx unknown
- 1975-03-12 NO NO750829A patent/NO750829L/no unknown
- 1975-03-14 NL NL7503058A patent/NL7503058A/xx not_active Application Discontinuation
- 1975-03-17 GB GB10987/75A patent/GB1482371A/en not_active Expired
- 1975-03-18 ES ES435777A patent/ES435777A1/es not_active Expired
- 1975-03-18 FR FR7508350A patent/FR2264532B2/fr not_active Expired
- 1975-03-18 HU HUSA2761A patent/HU169267B/hu unknown
- 1975-03-18 CA CA222,445A patent/CA1050031A/en not_active Expired
- 1975-03-18 IE IE576/75A patent/IE40948B1/xx unknown
- 1975-03-18 DD DD184853A patent/DD117463A5/xx unknown
- 1975-03-18 JP JP50031907A patent/JPS50154251A/ja active Pending
- 1975-03-18 IL IL46860A patent/IL46860A/en unknown
- 1975-03-19 SU SU752115292A patent/SU645574A3/ru active
-
1976
- 1976-03-18 IL IL46860*TA patent/IL46860A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL46860A (en) | 1977-12-30 |
| DK136248B (da) | 1977-09-12 |
| NO750829L (en, 2012) | 1975-09-23 |
| DD117463A5 (en, 2012) | 1976-01-12 |
| ES435777A1 (es) | 1977-07-01 |
| IE40948L (en) | 1975-09-20 |
| SE7502708L (en, 2012) | 1975-09-22 |
| SE404695B (sv) | 1978-10-23 |
| FR2264532B2 (en, 2012) | 1978-08-04 |
| HU169267B (en, 2012) | 1976-10-28 |
| JPS50154251A (en, 2012) | 1975-12-12 |
| IL46860A0 (en) | 1975-05-22 |
| FR2264532A2 (en, 2012) | 1975-10-17 |
| GB1482371A (en) | 1977-08-10 |
| DK136248C (en, 2012) | 1978-03-13 |
| AU7928975A (en) | 1976-09-23 |
| FI750696A7 (en, 2012) | 1975-09-21 |
| SU645574A3 (ru) | 1979-01-30 |
| DK98275A (en, 2012) | 1975-09-21 |
| IE40948B1 (en) | 1979-09-12 |
| NL7503058A (nl) | 1975-09-23 |
| DE2510439A1 (de) | 1975-09-25 |
| CH593957A5 (en, 2012) | 1977-12-30 |
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