DE1445632C3 - 1-eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu-oxotetrahydroimidazole - Google Patents
1-eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu-oxotetrahydroimidazoleInfo
- Publication number
- DE1445632C3 DE1445632C3 DE1445632A DE1445632A DE1445632C3 DE 1445632 C3 DE1445632 C3 DE 1445632C3 DE 1445632 A DE1445632 A DE 1445632A DE 1445632 A DE1445632 A DE 1445632A DE 1445632 C3 DE1445632 C3 DE 1445632C3
- Authority
- DE
- Germany
- Prior art keywords
- nitrothiazolyl
- salts
- square bracket
- oxo
- acid
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 229920002472 Starch Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- -1 dimethylamino, diethylamino Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 235000019730 animal feed additive Nutrition 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 239000003096 antiparasitic agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229960000603 cefalotin Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229940100445 wheat starch Drugs 0.000 description 2
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical class NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 241000224489 Amoeba Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- WYBCHGVUXKMQAD-UHFFFAOYSA-N ClC=1C=C(S(=O)(=O)NC=2N=NC=CC2)C(=CC1)N Chemical compound ClC=1C=C(S(=O)(=O)NC=2N=NC=CC2)C(=CC1)N WYBCHGVUXKMQAD-UHFFFAOYSA-N 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 244000151018 Maranta arundinacea Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000014101 wine Nutrition 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/58—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH660462A CH400171A (de) | 1962-05-30 | 1962-05-30 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| CH505663 | 1963-04-23 | ||
| CH1080063A CH459232A (de) | 1963-08-30 | 1963-08-30 | Verfahren zur Herstellung neuer Imidazole |
| CH539564A CH463514A (de) | 1964-04-24 | 1964-04-24 | Verfahren zur Herstellung neuer Diazacycloalkanverbindungen |
| CH896164 | 1964-07-08 | ||
| CH1153464A CH457454A (de) | 1964-09-03 | 1964-09-03 | Verfahren zur Herstellung neuer Diazacycloalkanverbindungen |
| CH294965 | 1965-03-03 | ||
| CH442365 | 1965-03-31 | ||
| US28258965A | 1965-04-13 | 1965-04-13 | |
| US44786865A | 1965-04-13 | 1965-04-13 | |
| CH1019865 | 1965-07-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445632A1 DE1445632A1 (de) | 1968-12-12 |
| DE1445632B2 DE1445632B2 (de) | 1975-04-03 |
| DE1445632C3 true DE1445632C3 (de) | 1975-11-13 |
Family
ID=27581426
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1245971D Pending DE1245971B (de) | 1962-05-30 | Verfahren zur Herstellung von neuen Tetrahydro-imidazolen | |
| DE1445632A Expired DE1445632C3 (de) | 1962-05-30 | 1964-08-25 | 1-eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu-oxotetrahydroimidazole |
| DE1545666A Expired DE1545666C3 (de) | 1962-05-30 | 1965-04-21 | 1- eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu -2oxo-hexahydropyrimidin |
| DE1545693A Expired DE1545693C3 (de) | 1962-05-30 | 1965-08-20 | Neue Nltrothiazolderivate und Verfahren zu ihrer Herstellung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1245971D Pending DE1245971B (de) | 1962-05-30 | Verfahren zur Herstellung von neuen Tetrahydro-imidazolen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1545666A Expired DE1545666C3 (de) | 1962-05-30 | 1965-04-21 | 1- eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu -2oxo-hexahydropyrimidin |
| DE1545693A Expired DE1545693C3 (de) | 1962-05-30 | 1965-08-20 | Neue Nltrothiazolderivate und Verfahren zu ihrer Herstellung |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3299069A (en:Method) |
| BE (4) | BE652414A (en:Method) |
| BR (4) | BR6349499D0 (en:Method) |
| CH (2) | CH400171A (en:Method) |
| CY (1) | CY328A (en:Method) |
| DE (4) | DE1445632C3 (en:Method) |
| FR (6) | FR3836M (en:Method) |
| GB (6) | GB986562A (en:Method) |
| IL (1) | IL24140A (en:Method) |
| MY (1) | MY6600002A (en:Method) |
| NL (5) | NL6505225A (en:Method) |
| NO (1) | NO120936B (en:Method) |
| SE (4) | SE311905B (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH462830A (de) * | 1965-01-20 | 1968-09-30 | Ciba Geigy | Verfahren zur Herstellung von 1-(5-Nitrothiazolyl-(2))-2-oxo-tetrahydroimidazolen |
| US3444168A (en) * | 1966-12-30 | 1969-05-13 | Sterling Drug Inc | 6 - (lower-alkanoyl) - 4 - hydroxy - 2 - mercapto - 5,6,7,8 - tetrahydropyrido(4,3 - d)pyrimidines |
| US3627777A (en) * | 1969-11-03 | 1971-12-14 | Ciba Geigy Corp | N-thiazolyl-oxodiazacycloalkanes |
| US3925550A (en) * | 1971-03-23 | 1975-12-09 | Rhone Poulenc Sa | 1-(5-Nitrothi-alzol-2-yl)-imidazolidine-2-thione having anti-parasitic and anti-microbial properties |
| US3932410A (en) * | 1974-11-01 | 1976-01-13 | Velsicol Chemical Corporation | 1-Thiadiazolyl-6-alkoxytetrahydropyrimidinones |
| NZ199856A (en) * | 1981-03-09 | 1984-08-24 | Johnson & Johnson Baby Prod | Non-zwitterionic amphoteric-fatty acid complexes and detergent compositions |
| FR2552804B1 (fr) * | 1983-10-03 | 1986-07-25 | Lauragais Tuileries Briq | Panneau prefabrique pour le revetement de parois, procedes de fabrication et de mise en oeuvre, et plaquettes en terre cuite pour la realisation desdits panneaux |
| PE20110341A1 (es) | 2006-08-15 | 2011-06-21 | Novartis Ag | COMPUESTOS HETEROCICLICOS QUE MODULAN LA ACTIVIDAD DE LA ESTEROIL-CoA-DESATURASA |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2755285A (en) * | 1956-07-17 | I-xsubstituted | ||
| US2874149A (en) * | 1957-03-18 | 1959-02-17 | Monsanto Chemicals | Ureas |
-
0
- DE DENDAT1245971D patent/DE1245971B/de active Pending
- NL NL123747D patent/NL123747C/xx active
- BE BE632989D patent/BE632989A/xx unknown
- NL NL293361D patent/NL293361A/xx unknown
-
1962
- 1962-05-30 CH CH660462A patent/CH400171A/de unknown
-
1963
- 1963-05-22 GB GB20497/63A patent/GB986562A/en not_active Expired
- 1963-05-30 BR BR149499/63A patent/BR6349499D0/pt unknown
- 1963-08-30 CH CH1426667A patent/CH459234A/de unknown
-
1964
- 1964-08-08 BR BR162227/64A patent/BR6462227D0/pt unknown
- 1964-08-24 GB GB34566/64A patent/GB1065988A/en not_active Expired
- 1964-08-25 DE DE1445632A patent/DE1445632C3/de not_active Expired
- 1964-08-28 BE BE652414A patent/BE652414A/xx unknown
- 1964-08-28 SE SE10366/64A patent/SE311905B/xx unknown
- 1964-11-19 FR FR995581A patent/FR3836M/fr not_active Expired
- 1964-11-19 FR FR995580A patent/FR3818M/fr not_active Expired
-
1965
- 1965-04-20 GB GB16556/65A patent/GB1078312A/en not_active Expired
- 1965-04-20 GB GB42874/66A patent/GB1078314A/en not_active Expired
- 1965-04-21 DE DE1545666A patent/DE1545666C3/de not_active Expired
- 1965-04-23 BR BR169146/65A patent/BR6569146D0/pt unknown
- 1965-04-23 NL NL6505225A patent/NL6505225A/xx unknown
- 1965-07-16 FR FR24838A patent/FR4671M/fr not_active Expired
- 1965-07-16 FR FR24837A patent/FR4613M/fr not_active Expired
- 1965-08-06 GB GB33845/65A patent/GB1075199A/en not_active Expired
- 1965-08-11 IL IL24140A patent/IL24140A/en unknown
- 1965-08-16 GB GB35043/65A patent/GB1078313A/en not_active Expired
- 1965-08-20 DE DE1545693A patent/DE1545693C3/de not_active Expired
- 1965-08-31 BR BR172735/65A patent/BR6572735D0/pt unknown
- 1965-09-02 SE SE11467/65A patent/SE321232B/xx unknown
- 1965-09-02 NO NO159579A patent/NO120936B/no unknown
- 1965-09-02 BE BE669083A patent/BE669083A/xx unknown
- 1965-09-02 NL NL656511486A patent/NL145552B/xx unknown
- 1965-09-08 US US485927A patent/US3299069A/en not_active Expired - Lifetime
- 1965-11-03 BE BE671753A patent/BE671753A/xx unknown
- 1965-11-06 CY CY32865A patent/CY328A/xx unknown
- 1965-11-16 FR FR38524A patent/FR4982M/fr not_active Expired
- 1965-11-16 FR FR38523A patent/FR4981M/fr not_active Expired
-
1966
- 1966-04-12 NL NL6604864A patent/NL6604864A/xx unknown
- 1966-07-12 US US564536A patent/US3298914A/en not_active Expired - Lifetime
- 1966-12-31 MY MY19662A patent/MY6600002A/xx unknown
-
1967
- 1967-01-13 SE SE519/67A patent/SE311911B/xx unknown
- 1967-01-13 SE SE518/67A patent/SE311910B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795699B2 (de) | 1-(2-Hydroxyäthyl)-2-(4-fluorphenyl)-5-nitroimidazol, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel | |
| DE1445632C3 (de) | 1-eckige Klammer auf 5-Nitrothiazolyl-(2) eckige Klammer zu-oxotetrahydroimidazole | |
| DE2363348C3 (de) | Substituierte 5 (6)-Phenoxy-benzimidazol-2-carbaminsäuremethylester, deren Herstellung und diese enthaltende Anthelminthika | |
| DE1445186C3 (de) | 3,3'-Di-2-imidazolin-2-yl-carbanilid | |
| DE2129960C2 (de) | Thioureidoderivate enthaltende therapeutische Zusammensetzungen, Verfahren zu deren Herstellung sowie die Thioureidoderivate | |
| DE1795711B2 (de) | Substituierte Benzimidazole, Verfahren zu deren Herstellung sowie diese enthaltende anthelminthische Zusammensetzungen | |
| DE1092021B (de) | Verfahren zur Herstellung von 1-(5-Nitro-furfuryliden-amino)-imidazolidin-thion-(2) | |
| DE1156412B (de) | Verfahren zur Herstellung von 3-{4'-[5''-Nitrofuryl-(2'')]-thiazolyl-(2')-amino}-oxazlidon-(2) | |
| DE1545667A1 (de) | Neue Diazacyclkanverbindungen | |
| DE1670441C3 (de) | 1 -(5-Nitro-2-thiazolyl)-2-oxotetrahydroimidazole und Verfahren zu ihrer Herstellung | |
| DE1670383A1 (de) | Neue Tetrahydroimidazole und Verfahren zu ihrer Herstellung | |
| DE2147852A1 (de) | Neue Penicilline und Verfahren zu deren Herstellung | |
| CH451156A (de) | Verfahren zur Herstellung des neuen N-(2-Chlor-äthyl)-N'-(5-nitro-thiazolyl-2)-harnstoffes | |
| AT256831B (de) | Verfahren zur Herstellung neuer 5-Nitrothiazolderivate und ihrer Salze | |
| DE1795487C3 (de) | 5-Nitrofuran-Derivate. Ausscheidung aus: 1445556 | |
| DE2250911A1 (de) | Phenylguanidin-derivate, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE1545708C (de) | N- eckige Klammer auf 3-(5-Nitrofurfuryliden-methyl)-6-pyridazinyl eckige Klammer zu -N,N-dimethylformamidin und seine Salze | |
| AT230369B (de) | Verfahren zur Herstellung von neuen Alkoxyalkyl-hydrazonen | |
| CH374984A (de) | Verfahren zur Herstellung von Benzolsulfonylharnstoffen | |
| DE1302669B (de) | N-(5-nitro-thiazolyl-2)-amidine | |
| AT234114B (de) | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen | |
| DE2130234C3 (de) | Ein N- [4-(B- Pyrazin-2-carboxamido-äthyObenzolsulfonyl] -harnstoff und diesen enthaltende pharmazeutische Zubereitungen | |
| AT236941B (de) | Verfahren zur Herstellung von neuen substituierten Benzimidazolen und deren Säureadditionssalzen | |
| AT225188B (de) | Verfahren zur Herstellung von neuen, in 3-Stellung substituierten Derivaten des 1-(5-Nitrofurfuryliden-amino)-hydantoins | |
| AT262995B (de) | Verfahren zur Herstellung von neuen 2-Oxo-tetrahydro-imidazolderivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |