JPS6053027B2 - テトラゾ−ル誘導体 - Google Patents
テトラゾ−ル誘導体Info
- Publication number
- JPS6053027B2 JPS6053027B2 JP51148284A JP14828476A JPS6053027B2 JP S6053027 B2 JPS6053027 B2 JP S6053027B2 JP 51148284 A JP51148284 A JP 51148284A JP 14828476 A JP14828476 A JP 14828476A JP S6053027 B2 JPS6053027 B2 JP S6053027B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrazole
- formula
- mol
- thiol
- ureidoethyl
- 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
- 150000003536 tetrazoles Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 4
- NFACUEDFSMJMLL-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)ethylurea Chemical compound NC(=O)NCCN1N=NN=C1S NFACUEDFSMJMLL-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 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
- -1 cephalosporin compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- VCNRHWDTBDOUBT-UHFFFAOYSA-N 2-[5-(2,4-dinitrophenyl)sulfanyltetrazol-1-yl]ethylurea Chemical compound NC(=O)NCCN1N=NN=C1SC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O VCNRHWDTBDOUBT-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- PCWJEAMXBQHWEA-UHFFFAOYSA-N methyl n-(2-acetamidoethyl)carbamodithioate Chemical compound CSC(=S)NCCNC(C)=O PCWJEAMXBQHWEA-UHFFFAOYSA-N 0.000 description 2
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 2
- GGIYJOOYYCYRAA-UHFFFAOYSA-N n-[2-[5-(2,4-dinitrophenyl)sulfanyltetrazol-1-yl]ethyl]acetamide Chemical compound CC(=O)NCCN1N=NN=C1SC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GGIYJOOYYCYRAA-UHFFFAOYSA-N 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- MFAJVMXXOAYZND-UHFFFAOYSA-N 2-[5-(2,4-dinitrophenyl)sulfanyltetrazol-1-yl]ethanamine;hydrochloride Chemical compound Cl.NCCN1N=NN=C1SC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O MFAJVMXXOAYZND-UHFFFAOYSA-N 0.000 description 1
- JXCNUCFTHLGXDQ-UHFFFAOYSA-N 2h-tetrazol-2-ium;chloride Chemical compound Cl.C1=NN=NN1 JXCNUCFTHLGXDQ-UHFFFAOYSA-N 0.000 description 1
- UMMFDPPWDFFARV-UHFFFAOYSA-N 5-(2,4-dinitrophenyl)sulfanyl-2H-tetrazole Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])SC1=NN=NN1 UMMFDPPWDFFARV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- IDOICNVNTGFRHG-UHFFFAOYSA-N n-[2-(5-sulfanylidene-2h-tetrazol-1-yl)ethyl]acetamide Chemical compound CC(=O)NCCN1N=NN=C1S IDOICNVNTGFRHG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- SBZLVCPKBFHMOS-UHFFFAOYSA-N sodium;2-(5-sulfanylidene-2h-tetrazol-1-yl)ethylurea Chemical compound [Na].NC(=O)NCCN1NN=NC1=S SBZLVCPKBFHMOS-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US639033 | 1975-12-09 | ||
| US05/639,033 US4025626A (en) | 1975-12-09 | 1975-12-09 | 7-Acyl-3-(ureidoalkyl substituted tetrazolylthiomethyl)-cephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5273891A JPS5273891A (en) | 1977-06-21 |
| JPS6053027B2 true JPS6053027B2 (ja) | 1985-11-22 |
Family
ID=24562451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51148284A Expired JPS6053027B2 (ja) | 1975-12-09 | 1976-12-08 | テトラゾ−ル誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US4025626A (enExample) |
| JP (1) | JPS6053027B2 (enExample) |
| BE (1) | BE849003A (enExample) |
| DE (1) | DE2655692A1 (enExample) |
| FR (3) | FR2361897A1 (enExample) |
| GB (3) | GB1573004A (enExample) |
| IE (1) | IE44570B1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6361119A (ja) * | 1986-09-01 | 1988-03-17 | Ee & D:Kk | 複数のロ−ドセルを用いた秤量装置 |
| JPH0259446U (enExample) * | 1988-10-25 | 1990-05-01 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK586175A (da) * | 1974-12-28 | 1976-06-29 | Asahi Chemical Ind | Cephalosporin-forbindelser |
| US4198406A (en) * | 1975-11-27 | 1980-04-15 | Beecham Group Limited | Carbamoyl heterocyclicthio cephalosporins and pharmaceutical compositions formulated therewith |
| AU498968B2 (en) * | 1976-03-03 | 1979-03-29 | Sumitomo Chemical Company, Limited | Cephalosporins |
| JPS5321191A (en) * | 1976-08-10 | 1978-02-27 | Shionogi & Co Ltd | 7-arylmalonamidocephem derivatives |
| US4117123A (en) * | 1977-06-09 | 1978-09-26 | Smithkline Corporation | 7-Acylamino-3-[1-(2-sulfamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acids |
| US4148997A (en) * | 1977-11-07 | 1979-04-10 | Yeda Research And Development Co., Ltd. | 7-[Sulfomethyl)phenyl]acetamidocephalosporin derivatives |
| US4226806A (en) * | 1977-11-07 | 1980-10-07 | Yeda Research And Development Co. Ltd. | 7-[(Sulfomethyl)phenyl]acetamidocephalosporin derivatives |
| US4180658A (en) * | 1978-02-24 | 1979-12-25 | Bristol-Myers Company | 7[-2-Alkoxyamino(acetamido)]cephalosporin derivatives |
| US4338452A (en) * | 1980-09-17 | 1982-07-06 | Eli Lilly And Company | 1-and 2-(1-Alkyl-1H-tetrazol-5-yl-methyl)-1H-tetrazol-5-thiols and 1-cyanomethyl tetrazole-5-thiol |
| JPS59152385A (ja) * | 1983-02-17 | 1984-08-31 | Shionogi & Co Ltd | ヒドロキサム酸系セフアロスポリン誘導体 |
| US6903105B2 (en) * | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819623A (en) * | 1968-04-12 | 1974-06-25 | Fujisawa Pharmaceutical Co | 3,7-disubstituted cephalosporin compounds |
| US3867380A (en) * | 1971-02-18 | 1975-02-18 | Smithkline Corp | 3-Heterocyclic thiomethylcephalosporins |
| US3828037A (en) * | 1972-07-20 | 1974-08-06 | Smithkline Corp | Trifluoromethylmercaptoacetamidocephalosporins |
| GB1478055A (en) | 1973-07-27 | 1977-06-29 | Erba Carlo Spa | Cephalosporin compounds |
| JPS57873B2 (enExample) | 1973-12-25 | 1982-01-08 |
-
1975
- 1975-12-09 US US05/639,033 patent/US4025626A/en not_active Expired - Lifetime
-
1976
- 1976-12-02 BE BE172919A patent/BE849003A/xx not_active IP Right Cessation
- 1976-12-08 JP JP51148284A patent/JPS6053027B2/ja not_active Expired
- 1976-12-08 DE DE19762655692 patent/DE2655692A1/de not_active Ceased
- 1976-12-08 FR FR7636974A patent/FR2361897A1/fr active Granted
- 1976-12-09 GB GB51513/76A patent/GB1573004A/en not_active Expired
- 1976-12-09 GB GB24430/79A patent/GB1573005A/en not_active Expired
- 1976-12-09 GB GB24429/79A patent/GB1573006A/en not_active Expired
- 1976-12-09 IE IE2696/76A patent/IE44570B1/en unknown
- 1976-12-22 US US05/753,244 patent/US4066761A/en not_active Expired - Lifetime
- 1976-12-22 US US05/753,259 patent/US4068073A/en not_active Expired - Lifetime
- 1976-12-22 US US05/753,245 patent/US4096256A/en not_active Expired - Lifetime
-
1977
- 1977-05-03 FR FR7713410A patent/FR2337730A1/fr active Granted
- 1977-05-03 FR FR7713411A patent/FR2361376A1/fr active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6361119A (ja) * | 1986-09-01 | 1988-03-17 | Ee & D:Kk | 複数のロ−ドセルを用いた秤量装置 |
| JPH0259446U (enExample) * | 1988-10-25 | 1990-05-01 |
Also Published As
| Publication number | Publication date |
|---|---|
| IE44570L (en) | 1977-06-09 |
| FR2337730A1 (fr) | 1977-08-05 |
| FR2361376A1 (fr) | 1978-03-10 |
| US4025626A (en) | 1977-05-24 |
| JPS5273891A (en) | 1977-06-21 |
| FR2361897A1 (fr) | 1978-03-17 |
| GB1573006A (en) | 1980-08-13 |
| IE44570B1 (en) | 1982-01-13 |
| US4068073A (en) | 1978-01-10 |
| BE849003A (fr) | 1977-06-02 |
| US4066761A (en) | 1978-01-03 |
| US4096256A (en) | 1978-06-20 |
| FR2361897B1 (enExample) | 1982-10-29 |
| GB1573005A (en) | 1980-08-13 |
| FR2361376B1 (enExample) | 1981-03-27 |
| FR2337730B1 (enExample) | 1981-01-09 |
| GB1573004A (en) | 1980-08-13 |
| DE2655692A1 (de) | 1977-06-16 |
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