JPS6121203B2 - - Google Patents
Info
- Publication number
- JPS6121203B2 JPS6121203B2 JP11402077A JP11402077A JPS6121203B2 JP S6121203 B2 JPS6121203 B2 JP S6121203B2 JP 11402077 A JP11402077 A JP 11402077A JP 11402077 A JP11402077 A JP 11402077A JP S6121203 B2 JPS6121203 B2 JP S6121203B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- methyl
- thiadiazol
- 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
- -1 1,3,4-thiadiazol-2-ylthio group Chemical group 0.000 claims description 23
- 229930186147 Cephalosporin Natural products 0.000 claims description 13
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 13
- 229940124587 cephalosporin Drugs 0.000 claims description 13
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 11
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 229960004821 amikacin Drugs 0.000 claims description 6
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 6
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 3
- 229930182566 Gentamicin Natural products 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229960002518 gentamicin Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229960000707 tobramycin Drugs 0.000 claims description 3
- GRRNUXAQVGOGFE-UHFFFAOYSA-N Hygromycin-B Natural products OC1C(NC)CC(N)C(O)C1OC1C2OC3(C(C(O)C(O)C(C(N)CO)O3)O)OC2C(O)C(CO)O1 GRRNUXAQVGOGFE-UHFFFAOYSA-N 0.000 claims description 2
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 claims description 2
- 229930192786 Sisomicin Natural products 0.000 claims description 2
- 229960000318 kanamycin Drugs 0.000 claims description 2
- 229930027917 kanamycin Natural products 0.000 claims description 2
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 2
- 229930182823 kanamycin A Natural products 0.000 claims description 2
- 229950011272 nebramycin Drugs 0.000 claims description 2
- 229960005456 sisomicin Drugs 0.000 claims description 2
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 claims description 2
- GKPRKJXOTBXASY-UHFFFAOYSA-N Dihydrospectinomycin Natural products O1C2(O)C(O)CC(C)OC2OC2C1C(NC)C(O)C(NC)C2O GKPRKJXOTBXASY-UHFFFAOYSA-N 0.000 claims 1
- GKPRKJXOTBXASY-IQKNWYLPSA-N dihydrospectinomycin Chemical compound O[C@@H]([C@]1(O)O2)C[C@@H](C)O[C@H]1O[C@H]1[C@H]2[C@@H](NC)[C@@H](O)[C@@H](NC)[C@@H]1O GKPRKJXOTBXASY-IQKNWYLPSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 2
- 229960003669 carbenicillin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000001974 tryptic soy broth Substances 0.000 description 2
- 108010050327 trypticase-soy broth Proteins 0.000 description 2
- SXVBQOZRZIUHKU-UHFFFAOYSA-N 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride Chemical compound CCN1CCN(C(Cl)=O)C(=O)C1=O SXVBQOZRZIUHKU-UHFFFAOYSA-N 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000010370 hearing loss Effects 0.000 description 1
- 231100000888 hearing loss Toxicity 0.000 description 1
- 208000016354 hearing loss disease Diseases 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 150000005331 phenylglycines Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11402077A JPS5446840A (en) | 1977-09-22 | 1977-09-22 | Antibacterial composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11402077A JPS5446840A (en) | 1977-09-22 | 1977-09-22 | Antibacterial composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5446840A JPS5446840A (en) | 1979-04-13 |
| JPS6121203B2 true JPS6121203B2 (ko) | 1986-05-26 |
Family
ID=14627026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11402077A Granted JPS5446840A (en) | 1977-09-22 | 1977-09-22 | Antibacterial composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5446840A (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000020009A1 (fr) * | 1998-10-05 | 2000-04-13 | Kabushiki Kaisha Yakult Honsha | Agents antibacteriens et leur procede de preparation |
| AU2007200916B2 (en) * | 1998-10-05 | 2009-09-17 | Kabushiki Kaisha Yakult Honsha | Antibacterial agents and process for producing the same |
-
1977
- 1977-09-22 JP JP11402077A patent/JPS5446840A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5446840A (en) | 1979-04-13 |
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