FI61488C - Foerfarande foer framstaellning av nya 5-2-(1-metyl-5-nitroimidatzol-2-yl)-vinyl-1,3,4-tiadiazolfoereningar anvaendbara sasom antimikrobiella medel - Google Patents
Foerfarande foer framstaellning av nya 5-2-(1-metyl-5-nitroimidatzol-2-yl)-vinyl-1,3,4-tiadiazolfoereningar anvaendbara sasom antimikrobiella medel Download PDFInfo
- Publication number
- FI61488C FI61488C FI762765A FI762765A FI61488C FI 61488 C FI61488 C FI 61488C FI 762765 A FI762765 A FI 762765A FI 762765 A FI762765 A FI 762765A FI 61488 C FI61488 C FI 61488C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- thiadiazole
- vinyl
- nitroimidazol
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229920002554 vinyl polymer Polymers 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 2-substituted 1,3,4-thiadiazole Chemical class 0.000 claims description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000004599 antimicrobial Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- FAMHRHPGWNQVGW-UHFFFAOYSA-N 2-ethyl-5-[1-(1-methyl-5-nitroimidazol-2-yl)prop-1-en-2-yl]-1,3,4-thiadiazole Chemical compound S1C(CC)=NN=C1C(C)=CC1=NC=C([N+]([O-])=O)N1C FAMHRHPGWNQVGW-UHFFFAOYSA-N 0.000 claims 1
- WWHSTNDFUFSXDH-UHFFFAOYSA-N 2-ethyl-5-[2-(1-methyl-5-nitroimidazol-2-yl)ethenyl]-1,3,4-thiadiazole Chemical compound S1C(CC)=NN=C1C=CC1=NC=C([N+]([O-])=O)N1C WWHSTNDFUFSXDH-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 150000008063 acylals Chemical class 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 36
- 230000000694 effects Effects 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 16
- 208000015181 infectious disease Diseases 0.000 description 13
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 13
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 12
- 229960000282 metronidazole Drugs 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000001154 acute effect Effects 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000011592 zinc chloride Substances 0.000 description 7
- 235000005074 zinc chloride Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HJLSLZFTEKNLFI-UHFFFAOYSA-N Tinidazole Chemical compound CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O HJLSLZFTEKNLFI-UHFFFAOYSA-N 0.000 description 5
- 241000223104 Trypanosoma Species 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 5
- 229960005053 tinidazole Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229960005314 suramin Drugs 0.000 description 4
- 206010061819 Disease recurrence Diseases 0.000 description 3
- 208000010489 Entamoebiasis Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000224432 Entamoeba histolytica Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- 241000223105 Trypanosoma brucei Species 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940007078 entamoeba histolytica Drugs 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- BXVZVOBTUSLCIO-UHFFFAOYSA-N 2,5-diethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(CC)S1 BXVZVOBTUSLCIO-UHFFFAOYSA-N 0.000 description 1
- JXQGICFGPUAVLJ-UHFFFAOYSA-N 2,5-dimethyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(C)S1 JXQGICFGPUAVLJ-UHFFFAOYSA-N 0.000 description 1
- LWXMIJBHPVXFQH-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1C1=CC=CC=C1Cl LWXMIJBHPVXFQH-UHFFFAOYSA-N 0.000 description 1
- CWVVATVGUYOMAY-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1C1=CC=C(Cl)C=C1 CWVVATVGUYOMAY-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- DCJDSWQIZIJZDO-UHFFFAOYSA-N 2-ethyl-5-methyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(C)S1 DCJDSWQIZIJZDO-UHFFFAOYSA-N 0.000 description 1
- RQSCFNPNNLWQBJ-UHFFFAOYSA-N 2-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=CS1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 1
- GEVBBQNWDQJVTA-UHFFFAOYSA-N 2-methyl-5-phenyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1C1=CC=CC=C1 GEVBBQNWDQJVTA-UHFFFAOYSA-N 0.000 description 1
- QLFKIXOYEGXBKO-UHFFFAOYSA-N 2-methyl-5-pyridin-4-yl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1C1=CC=NC=C1 QLFKIXOYEGXBKO-UHFFFAOYSA-N 0.000 description 1
- VKORDEHBAISSEV-UHFFFAOYSA-N 2-methyl-5-tridecyl-1,3,4-thiadiazole Chemical compound CCCCCCCCCCCCCC1=NN=C(C)S1 VKORDEHBAISSEV-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
- LHIALLMPKJMSIQ-UHFFFAOYSA-N 4-[2-(1-methyl-5-nitroimidazol-2-yl)ethenyl]pyrimidin-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C=CC=2N=C(N)N=CC=2)=N1 LHIALLMPKJMSIQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 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
- 229930194076 Germanin Natural products 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 208000023668 Pharyngeal disease Diseases 0.000 description 1
- 208000013007 Rodent disease Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000224526 Trichomonas Species 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
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 229930190569 brucein Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides 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
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000033420 disorder of pharynx Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth 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)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2544702 | 1975-10-07 | ||
| DE2544702A DE2544702C3 (de) | 1975-10-07 | 1975-10-07 | Nitroimidazolylvinylthiadiazole |
| DE2640504 | 1976-09-09 | ||
| DE19762640504 DE2640504A1 (de) | 1976-09-09 | 1976-09-09 | Chemotherapeutisches mittel gegen infektionen durch trypanosomen und entamoeba |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI762765A7 FI762765A7 (cs) | 1977-04-08 |
| FI61488B FI61488B (fi) | 1982-04-30 |
| FI61488C true FI61488C (fi) | 1982-08-10 |
Family
ID=25769484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5248667A (cs) |
| AR (1) | AR210289A1 (cs) |
| AT (1) | AT352714B (cs) |
| AU (1) | AU505058B2 (cs) |
| CA (1) | CA1078390A (cs) |
| CH (1) | CH624953A5 (cs) |
| DK (1) | DK142850C (cs) |
| ES (1) | ES452151A1 (cs) |
| FI (1) | FI61488C (cs) |
| FR (1) | FR2326921A1 (cs) |
| GB (1) | GB1561529A (cs) |
| HU (1) | HU172614B (cs) |
| IL (1) | IL50563A (cs) |
| LU (1) | LU75937A1 (cs) |
| NL (1) | NL176780C (cs) |
| NO (1) | NO146397C (cs) |
| YU (1) | YU240376A (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664707A (en) * | 1985-04-09 | 1987-05-12 | Georgia-Pacific Corporation | Fire resistant gypsum composition |
| JPH06313620A (ja) * | 1994-02-25 | 1994-11-08 | Takara Standard Co Ltd | 給湯機 |
-
1976
- 1976-09-28 IL IL50563A patent/IL50563A/xx unknown
- 1976-09-28 FI FI762765A patent/FI61488C/fi not_active IP Right Cessation
- 1976-09-29 AU AU18204/76A patent/AU505058B2/en not_active Expired
- 1976-09-30 YU YU02403/76A patent/YU240376A/xx unknown
- 1976-10-04 CA CA262,606A patent/CA1078390A/en not_active Expired
- 1976-10-05 CH CH1258976A patent/CH624953A5/de not_active IP Right Cessation
- 1976-10-05 LU LU75937A patent/LU75937A1/xx unknown
- 1976-10-05 NO NO763400A patent/NO146397C/no unknown
- 1976-10-06 FR FR7630047A patent/FR2326921A1/fr active Granted
- 1976-10-06 HU HU76BA00003458A patent/HU172614B/hu not_active IP Right Cessation
- 1976-10-06 DK DK449876A patent/DK142850C/da not_active IP Right Cessation
- 1976-10-06 ES ES452151A patent/ES452151A1/es not_active Expired
- 1976-10-06 AT AT741676A patent/AT352714B/de not_active IP Right Cessation
- 1976-10-06 GB GB41425/76A patent/GB1561529A/en not_active Expired
- 1976-10-07 NL NLAANVRAGE7611119,A patent/NL176780C/xx not_active IP Right Cessation
- 1976-10-07 JP JP51119929A patent/JPS5248667A/ja active Granted
- 1976-10-07 AR AR265023A patent/AR210289A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AU1820476A (en) | 1978-04-06 |
| FI61488B (fi) | 1982-04-30 |
| FI762765A7 (cs) | 1977-04-08 |
| IL50563A (en) | 1979-10-31 |
| NL176780B (nl) | 1985-01-02 |
| NO146397C (no) | 1982-09-22 |
| CA1078390A (en) | 1980-05-27 |
| LU75937A1 (cs) | 1977-05-06 |
| CH624953A5 (en) | 1981-08-31 |
| JPS5248667A (en) | 1977-04-18 |
| FR2326921A1 (fr) | 1977-05-06 |
| FR2326921B1 (cs) | 1978-11-17 |
| NL7611119A (nl) | 1977-04-13 |
| DK142850B (da) | 1981-02-09 |
| AU505058B2 (en) | 1979-11-08 |
| ES452151A1 (es) | 1977-11-16 |
| DK449876A (da) | 1977-04-08 |
| GB1561529A (en) | 1980-02-20 |
| ATA741676A (de) | 1979-03-15 |
| DK142850C (da) | 1981-10-12 |
| AT352714B (de) | 1979-10-10 |
| NO146397B (no) | 1982-06-14 |
| JPS6152154B2 (cs) | 1986-11-12 |
| IL50563A0 (en) | 1976-11-30 |
| NL176780C (nl) | 1985-06-03 |
| NO763400L (cs) | 1977-04-13 |
| HU172614B (hu) | 1978-11-28 |
| AR210289A1 (es) | 1977-07-15 |
| YU240376A (en) | 1982-10-31 |
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| Date | Code | Title | Description |
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| MM | Patent lapsed |
Owner name: BASF AKTIENGESELLSCHAFT |