DE1445771A1 - Tetrahydro-1,3,5-thiadiazin-2-thione und Verfahren zu ihrer Herstellung - Google Patents
Tetrahydro-1,3,5-thiadiazin-2-thione und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1445771A1 DE1445771A1 DE19641445771 DE1445771A DE1445771A1 DE 1445771 A1 DE1445771 A1 DE 1445771A1 DE 19641445771 DE19641445771 DE 19641445771 DE 1445771 A DE1445771 A DE 1445771A DE 1445771 A1 DE1445771 A1 DE 1445771A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydro
- salts
- thiadiazine
- general formula
- alkali
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 3
- RUEOBRARCKLXJO-UHFFFAOYSA-N 1,3,5-thiadiazinane-2-thione Chemical class S=C1NCNCS1 RUEOBRARCKLXJO-UHFFFAOYSA-N 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 9
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- KRSLQDMSSSBJTN-UHFFFAOYSA-N 1-sulfanylidene-1,3,5-thiadiazinane Chemical compound S=S1CNCNC1 KRSLQDMSSSBJTN-UHFFFAOYSA-N 0.000 claims 2
- 241000188250 Idas Species 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 241001324821 Opisthorchis felineus Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 description 1
- IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
- ICIJWOWQUHHETJ-UHFFFAOYSA-N (3,5-dichlorophenyl)methanamine Chemical compound NCC1=CC(Cl)=CC(Cl)=C1 ICIJWOWQUHHETJ-UHFFFAOYSA-N 0.000 description 1
- XRNVSPDQTPVECU-UHFFFAOYSA-N (4-bromophenyl)methanamine Chemical compound NCC1=CC=C(Br)C=C1 XRNVSPDQTPVECU-UHFFFAOYSA-N 0.000 description 1
- DMDWPICFPZMEEW-UHFFFAOYSA-N 1,3,5-thiadiazine-2-thione Chemical compound S=C1N=CN=CS1 DMDWPICFPZMEEW-UHFFFAOYSA-N 0.000 description 1
- MQPUAVYKVIHUJP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C(Cl)=C1 MQPUAVYKVIHUJP-UHFFFAOYSA-N 0.000 description 1
- CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 description 1
- QKGYKRACHNWPCA-UHFFFAOYSA-N 2-chloro-2-(4-chlorophenyl)ethanamine Chemical compound NCC(Cl)C1=CC=C(Cl)C=C1 QKGYKRACHNWPCA-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- RVLNDSYSQLMPRC-UHFFFAOYSA-N 3-(4-chlorophenyl)propan-1-amine Chemical compound NCCCC1=CC=C(Cl)C=C1 RVLNDSYSQLMPRC-UHFFFAOYSA-N 0.000 description 1
- CUKWCGLNAHPBJC-UHFFFAOYSA-N 3-benzyl-5-[2-(diethylamino)ethyl]-1,3,5-thiadiazinane-2-thione Chemical compound C1N(CCN(CC)CC)CSC(=S)N1CC1=CC=CC=C1 CUKWCGLNAHPBJC-UHFFFAOYSA-N 0.000 description 1
- DBRKOJIBBAJAII-UHFFFAOYSA-N 4-(4-chlorophenyl)butan-1-amine Chemical compound NCCCCC1=CC=C(Cl)C=C1 DBRKOJIBBAJAII-UHFFFAOYSA-N 0.000 description 1
- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 description 1
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 description 1
- 241000577452 Dicrocoelium Species 0.000 description 1
- 241000577456 Dicrocoelium dendriticum Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DWQGKMSNZGJKJS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=C(Cl)C=C1 DWQGKMSNZGJKJS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 208000003692 opisthorchiasis Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XVKPYTQNRNMGEQ-UHFFFAOYSA-M sodium;n-benzylcarbamodithioate Chemical compound [Na+].[S-]C(=S)NCC1=CC=CC=C1 XVKPYTQNRNMGEQ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/34—1,3,5-Thiadiazines; Hydrogenated 1,3,5-thiadiazines
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0043304 | 1964-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445771A1 true DE1445771A1 (de) | 1969-03-20 |
Family
ID=7099494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445771 Pending DE1445771A1 (de) | 1964-06-30 | 1964-06-30 | Tetrahydro-1,3,5-thiadiazin-2-thione und Verfahren zu ihrer Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3398146A (enExample) |
| AT (1) | AT252932B (enExample) |
| BE (1) | BE666191A (enExample) |
| CH (1) | CH442329A (enExample) |
| DE (1) | DE1445771A1 (enExample) |
| DK (1) | DK118668B (enExample) |
| GB (1) | GB1077811A (enExample) |
| NL (1) | NL6508391A (enExample) |
| SE (1) | SE306536B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697516A (en) * | 1970-10-19 | 1972-10-10 | Phillips Petroleum Co | Certain thiazine-2-thione compounds and method of preparing same |
| DE2410558C2 (de) * | 1974-03-06 | 1982-11-25 | Schülke & Mayr GmbH, 2000 Norderstedt | 3,5-Dialkoxyalkyl-1,3,5-tetrahydrothiadiazinthione-(2), Verfahren zu ihrer Herstellung und ihre Verwendung als antimikrobielle Mittel |
| US4044127A (en) * | 1976-03-10 | 1977-08-23 | American Cyanamide Company | Process for utilizing tetrahydro-3-(4-pyridylmethyl)-2H-1,3,5-thiadiazine-2-thiones as fungicidal agents |
| US4029652A (en) * | 1976-03-10 | 1977-06-14 | American Cyanamid Company | Tetrahydro-3-(4-pyridylmethyl)-2H-1,3,5-thiadiazine-2-thione |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2397421A (en) * | 1943-08-24 | 1946-03-26 | American Cyanamid Co | 2-thio-4, 6-diamino-1, 3, 5-thiadiazine and salts thereof |
| US2838389A (en) * | 1952-09-03 | 1958-06-10 | Union Carbide Corp | Method of combatting weeds |
| US3085046A (en) * | 1961-07-03 | 1963-04-09 | Du Pont | 3, 3'-hydrocarbonylene bis(tetrahydro-1, 3, 5-thiadiazine-2-thiones), unsymmetrically substituted corresponding compounds, fungicidal compositions, and methods |
-
1964
- 1964-06-30 DE DE19641445771 patent/DE1445771A1/de active Pending
-
1965
- 1965-06-28 AT AT584965A patent/AT252932B/de active
- 1965-06-28 CH CH899965A patent/CH442329A/de unknown
- 1965-06-29 DK DK331365AA patent/DK118668B/da unknown
- 1965-06-30 BE BE666191A patent/BE666191A/xx unknown
- 1965-06-30 NL NL6508391A patent/NL6508391A/xx unknown
- 1965-06-30 GB GB27701/65A patent/GB1077811A/en not_active Expired
- 1965-06-30 SE SE8689/65A patent/SE306536B/xx unknown
- 1965-06-30 US US468596A patent/US3398146A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AT252932B (de) | 1967-03-10 |
| DK118668B (da) | 1970-09-21 |
| CH442329A (de) | 1967-08-31 |
| GB1077811A (en) | 1967-08-02 |
| BE666191A (enExample) | 1965-12-30 |
| NL6508391A (enExample) | 1965-12-31 |
| SE306536B (enExample) | 1968-12-02 |
| US3398146A (en) | 1968-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |