DE2544702C3 - Nitroimidazolylvinylthiadiazole - Google Patents
NitroimidazolylvinylthiadiazoleInfo
- Publication number
- DE2544702C3 DE2544702C3 DE2544702A DE2544702A DE2544702C3 DE 2544702 C3 DE2544702 C3 DE 2544702C3 DE 2544702 A DE2544702 A DE 2544702A DE 2544702 A DE2544702 A DE 2544702A DE 2544702 C3 DE2544702 C3 DE 2544702C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- thiadiazole
- vinyl
- acetic acid
- solvent
- 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
- USOIRERGWSUAHE-UHFFFAOYSA-N 5-(1H-imidazol-2-yl)-4-(2-nitroethenyl)thiadiazole Chemical class [N+](=O)([O-])C=CC=1N=NSC=1C=1NC=CN=1 USOIRERGWSUAHE-UHFFFAOYSA-N 0.000 title 1
- FXMTYILCGSSNNM-UHFFFAOYSA-N 4-[2-(1h-imidazol-2-yl)ethenyl]-5-nitrothiadiazole Chemical class S1N=NC(C=CC=2NC=CN=2)=C1[N+](=O)[O-] FXMTYILCGSSNNM-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- -1 2-substituted 1,3,4-thiadiazole Chemical class 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000008063 acylals Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229960000282 metronidazole Drugs 0.000 description 4
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HJLSLZFTEKNLFI-UHFFFAOYSA-N Tinidazole Chemical compound CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O HJLSLZFTEKNLFI-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229960005053 tinidazole Drugs 0.000 description 3
- MDIIOVRYTOGGBO-UHFFFAOYSA-N 5-nitro-1h-imidazole-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CN=C(C=O)N1 MDIIOVRYTOGGBO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BXVZVOBTUSLCIO-UHFFFAOYSA-N 2,5-diethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(CC)S1 BXVZVOBTUSLCIO-UHFFFAOYSA-N 0.000 description 1
- MFLXZVLOMYAEON-UHFFFAOYSA-N 2-[2-(1-methyl-5-nitroimidazol-2-yl)ethenyl]-1,3,4-thiadiazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=CC=2SC=NN=2)=N1 MFLXZVLOMYAEON-UHFFFAOYSA-N 0.000 description 1
- QRRPCCVGSDWLRX-UHFFFAOYSA-N 2-[2-(1-methyl-5-nitroimidazol-2-yl)ethenyl]-5-pyridin-4-yl-1,3,4-thiadiazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=CC=2SC(=NN=2)C=2C=CN=CC=2)=N1 QRRPCCVGSDWLRX-UHFFFAOYSA-N 0.000 description 1
- WNDJMKLPVICPHJ-UHFFFAOYSA-N 2-methyl-5-[1-(1-methyl-5-nitroimidazol-2-yl)prop-1-en-2-yl]-1,3,4-thiadiazole Chemical compound N=1N=C(C)SC=1C(C)=CC1=NC=C([N+]([O-])=O)N1C WNDJMKLPVICPHJ-UHFFFAOYSA-N 0.000 description 1
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical class [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZTCLCSCHTACERP-AWEZNQCLSA-N N-[(1S)-1-[3-chloro-5-fluoro-2-[[2-methyl-4-(2-methyl-1,2,4-triazol-3-yl)quinolin-8-yl]oxymethyl]phenyl]ethyl]-2-(difluoromethoxy)acetamide Chemical compound C1=C(C=C(C(=C1Cl)COC1=CC=CC2=C(C=3N(N=CN=3)C)C=C(C)N=C12)[C@@H](NC(=O)COC(F)F)C)F ZTCLCSCHTACERP-AWEZNQCLSA-N 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001556 precipitation Methods 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000000003 vaginal tablet Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2544702A DE2544702C3 (de) | 1975-10-07 | 1975-10-07 | Nitroimidazolylvinylthiadiazole |
| IN1781/CAL/76A IN143954B (cg-RX-API-DMAC10.html) | 1975-10-07 | 1976-09-27 | |
| FI762765A FI61488C (fi) | 1975-10-07 | 1976-09-28 | Foerfarande foer framstaellning av nya 5-2-(1-metyl-5-nitroimidatzol-2-yl)-vinyl-1,3,4-tiadiazolfoereningar anvaendbara sasom antimikrobiella medel |
| IL50563A IL50563A (en) | 1975-10-07 | 1976-09-28 | 5-(2-(1-alkyl-5-notroimidazol-2-yl)vinyl)1,3,4-thiadiazoles, their production and pharmaceutical compositions containing them |
| AU18204/76A AU505058B2 (en) | 1975-10-07 | 1976-09-29 | Nitoimidazolylvinylthiadiazole derivatives |
| YU02403/76A YU240376A (en) | 1975-10-07 | 1976-09-30 | Process for obtaining new nitroimidazolylvinyl thiadiazole |
| CA262,606A CA1078390A (en) | 1975-10-07 | 1976-10-04 | Nitroimidazoles |
| CH1258976A CH624953A5 (en) | 1975-10-07 | 1976-10-05 | Process for the preparation of novel 5-nitroimidazoles |
| NO763400A NO146397C (no) | 1975-10-07 | 1976-10-05 | Analogifremgangsmaate til fremstilling av terapeutisk aktive nitroimidazolylvinyltiadiazoler |
| LU75937A LU75937A1 (cg-RX-API-DMAC10.html) | 1975-10-07 | 1976-10-05 | |
| SE7611036A SE420607B (sv) | 1975-10-07 | 1976-10-05 | Forfarande for framstellning av nitroimidazolylvinyltiadiazoler |
| ZA765981A ZA765981B (en) | 1975-10-07 | 1976-10-06 | New nitroimidazoles |
| FR7630047A FR2326921A1 (fr) | 1975-10-07 | 1976-10-06 | Nouveaux 5-nitro-imidazoles utiles comme medicame nts pour le traitement d'infections microbiennes |
| AT741676A AT352714B (de) | 1975-10-07 | 1976-10-06 | Verfahren zur herstellung von neuen nitroimi- dazolylvinylthiadiazolen |
| DK449876A DK142850C (da) | 1975-10-07 | 1976-10-06 | Analogifremgangsmaade til fremstilling af 5-(2-(1-methyl-5-nitroimidazol-2-yl)-vinyl)-1,3,4-thiadiazolderivater |
| HU76BA00003458A HU172614B (hu) | 1975-10-07 | 1976-10-06 | Sposob poluchenija nitroimidazolil-vinil-tiadiazolov |
| GB41425/76A GB1561529A (en) | 1975-10-07 | 1976-10-06 | 5 - (2 - (5 - nitrolimidazol) - 2 - y)vinyl) - 1,3,4 - thiodiazole derivatives useful as chemotherapeutics |
| ES452151A ES452151A1 (es) | 1975-10-07 | 1976-10-06 | Procedimiento para la obtencion de nitroimidazolilvinitia- diazoles. |
| NLAANVRAGE7611119,A NL176780C (nl) | 1975-10-07 | 1976-10-07 | Werkwijze voor de bereiding van op de plaatsen 1 en 2 gesubstitueerde 5-nitroimidazoolderivaten met werkzaamheid tegen protozoen alsmede werkwijze voor de bereiding van farmaceutische preparaten onder toepassing van dergelijke derivaten als werkzame stof. |
| BE171307A BE847030A (fr) | 1975-10-07 | 1976-10-07 | Nouveaux 5-nitro-imidazoles utiles comme medicaments pour le traitement d'infections microbiennes |
| JP51119929A JPS5248667A (en) | 1975-10-07 | 1976-10-07 | Novel 55nitroimidazole compound |
| CS766489A CS201541B2 (en) | 1975-10-07 | 1976-10-07 | Process for preparing 5-//2-nitroimidazolyl/vinyl/-1,3,4-thiadiazoles |
| AR265023A AR210289A1 (es) | 1975-10-07 | 1976-10-07 | Procedimiento para obtener k((5-nitroimidazol-2-il)-vinil)-1,3,4-tiadiazol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2544702A DE2544702C3 (de) | 1975-10-07 | 1975-10-07 | Nitroimidazolylvinylthiadiazole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2544702A1 DE2544702A1 (de) | 1977-04-21 |
| DE2544702B2 DE2544702B2 (de) | 1980-01-03 |
| DE2544702C3 true DE2544702C3 (de) | 1980-09-11 |
Family
ID=5958448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2544702A Expired DE2544702C3 (de) | 1975-10-07 | 1975-10-07 | Nitroimidazolylvinylthiadiazole |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE847030A (cg-RX-API-DMAC10.html) |
| CS (1) | CS201541B2 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2544702C3 (cg-RX-API-DMAC10.html) |
| IN (1) | IN143954B (cg-RX-API-DMAC10.html) |
| SE (1) | SE420607B (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA765981B (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160244435A1 (en) * | 2013-06-21 | 2016-08-25 | The Scripps Research Institute | Expanded therapeutic potential in nitroheteroaryl antimicrobials |
-
1975
- 1975-10-07 DE DE2544702A patent/DE2544702C3/de not_active Expired
-
1976
- 1976-09-27 IN IN1781/CAL/76A patent/IN143954B/en unknown
- 1976-10-05 SE SE7611036A patent/SE420607B/xx not_active IP Right Cessation
- 1976-10-06 ZA ZA765981A patent/ZA765981B/xx unknown
- 1976-10-07 BE BE171307A patent/BE847030A/xx not_active IP Right Cessation
- 1976-10-07 CS CS766489A patent/CS201541B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7611036L (sv) | 1977-04-08 |
| CS201541B2 (en) | 1980-11-28 |
| IN143954B (cg-RX-API-DMAC10.html) | 1978-03-04 |
| BE847030A (fr) | 1977-04-07 |
| ZA765981B (en) | 1977-10-26 |
| DE2544702B2 (de) | 1980-01-03 |
| SE420607B (sv) | 1981-10-19 |
| DE2544702A1 (de) | 1977-04-21 |
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