FI66855C - Foerfarande foer framstaellning av 5-merkaptotetrazolyl-1-aettiksyra och alkalisalter daerav - Google Patents
Foerfarande foer framstaellning av 5-merkaptotetrazolyl-1-aettiksyra och alkalisalter daerav Download PDFInfo
- Publication number
- FI66855C FI66855C FI802127A FI802127A FI66855C FI 66855 C FI66855 C FI 66855C FI 802127 A FI802127 A FI 802127A FI 802127 A FI802127 A FI 802127A FI 66855 C FI66855 C FI 66855C
- Authority
- FI
- Finland
- Prior art keywords
- acetic acid
- bromotetrazolyl
- tetrazolyl
- solution
- mercaptotetrazolyl
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 17
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 6
- UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- IYPXPGSELZFFMI-UHFFFAOYSA-N 1-phenyltetrazole Chemical compound C1=NN=NN1C1=CC=CC=C1 IYPXPGSELZFFMI-UHFFFAOYSA-N 0.000 description 2
- OKBYPPLWGIVLOC-UHFFFAOYSA-N 5-bromo-1-phenyltetrazole Chemical compound BrC1=NN=NN1C1=CC=CC=C1 OKBYPPLWGIVLOC-UHFFFAOYSA-N 0.000 description 2
- 108090000656 Annexin A6 Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SLAYUXIURFNXPG-KPMSDPLLSA-N (6r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NCC1=CC=CC=C1CC(=O)NC1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)CC(O)=O)CS[C@@H]21 SLAYUXIURFNXPG-KPMSDPLLSA-N 0.000 description 1
- QPHZWABVAIGWHI-UHFFFAOYSA-N 3-methyl-2h-1,2,4-thiadiazole-5-thione Chemical compound CC1=NSC(S)=N1 QPHZWABVAIGWHI-UHFFFAOYSA-N 0.000 description 1
- MLXPGVGNTLPQIY-UHFFFAOYSA-N 5-(hydroxymethyl)-3h-1,3,4-thiadiazole-2-thione Chemical compound OCC1=NN=C(S)S1 MLXPGVGNTLPQIY-UHFFFAOYSA-N 0.000 description 1
- FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- SLAYUXIURFNXPG-CRAIPNDOSA-N ceforanide Chemical compound NCC1=CC=CC=C1CC(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)CC(O)=O)CS[C@@H]21 SLAYUXIURFNXPG-CRAIPNDOSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/054,743 US4374994A (en) | 1979-07-05 | 1979-07-05 | Process for preparation of 5-mercaptotetrazolyl-1-acetic acid |
| US5474379 | 1979-07-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802127A7 FI802127A7 (fi) | 1981-01-06 |
| FI66855B FI66855B (fi) | 1984-08-31 |
| FI66855C true FI66855C (fi) | 1984-12-10 |
Family
ID=21993217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802127A FI66855C (fi) | 1979-07-05 | 1980-07-02 | Foerfarande foer framstaellning av 5-merkaptotetrazolyl-1-aettiksyra och alkalisalter daerav |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4374994A (da) |
| JP (1) | JPS5610178A (da) |
| CA (1) | CA1145757A (da) |
| CH (2) | CH644852A5 (da) |
| DK (3) | DK157298C (da) |
| FI (1) | FI66855C (da) |
| GR (1) | GR69331B (da) |
| IT (2) | IT1145662B (da) |
| NL (1) | NL8003832A (da) |
| SE (2) | SE448463B (da) |
| YU (1) | YU42340B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627736B (zh) * | 2019-09-26 | 2020-11-06 | 江苏阿尔法药业有限公司 | 一种1-苯基-5-羟基四氮唑的回收利用方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4297489A (en) * | 1974-09-03 | 1981-10-27 | Bristol-Myers Company | 7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids |
-
1979
- 1979-07-05 US US06/054,743 patent/US4374994A/en not_active Expired - Lifetime
-
1980
- 1980-05-21 CA CA000352344A patent/CA1145757A/en not_active Expired
- 1980-05-28 GR GR62070A patent/GR69331B/el unknown
- 1980-06-06 YU YU1513/80A patent/YU42340B/xx unknown
- 1980-06-26 JP JP8599580A patent/JPS5610178A/ja active Granted
- 1980-06-27 IT IT49101/80A patent/IT1145662B/it active
- 1980-06-27 IT IT49102/80A patent/IT1145663B/it active
- 1980-07-02 FI FI802127A patent/FI66855C/fi not_active IP Right Cessation
- 1980-07-02 NL NL8003832A patent/NL8003832A/nl not_active Application Discontinuation
- 1980-07-04 DK DK291480A patent/DK157298C/da not_active IP Right Cessation
- 1980-07-04 SE SE8004981A patent/SE448463B/sv not_active IP Right Cessation
- 1980-07-04 CH CH517180A patent/CH644852A5/de not_active IP Right Cessation
-
1984
- 1984-02-29 CH CH987/84A patent/CH648026A5/de not_active IP Right Cessation
- 1984-11-16 SE SE8405750A patent/SE454694B/sv not_active IP Right Cessation
-
1986
- 1986-01-10 DK DK011886A patent/DK160493C/da not_active IP Right Cessation
- 1986-01-10 DK DK011986A patent/DK160494C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8049102A0 (it) | 1980-06-27 |
| GR69331B (da) | 1982-05-17 |
| SE8405750L (sv) | 1984-11-16 |
| DK11986D0 (da) | 1986-01-10 |
| JPH0337550B2 (da) | 1991-06-05 |
| SE454694B (sv) | 1988-05-24 |
| DK160493C (da) | 1991-08-26 |
| SE448463B (sv) | 1987-02-23 |
| DK160493B (da) | 1991-03-18 |
| IT8049101A0 (it) | 1980-06-27 |
| DK160494B (da) | 1991-03-18 |
| DK160494C (da) | 1991-08-26 |
| IT1145663B (it) | 1986-11-05 |
| NL8003832A (nl) | 1981-01-07 |
| JPS5610178A (en) | 1981-02-02 |
| DK11886A (da) | 1986-01-10 |
| CH644852A5 (de) | 1984-08-31 |
| US4374994A (en) | 1983-02-22 |
| SE8004981L (sv) | 1981-01-06 |
| IT1145662B (it) | 1986-11-05 |
| CH648026A5 (de) | 1985-02-28 |
| DK157298B (da) | 1989-12-04 |
| DK157298C (da) | 1990-05-07 |
| DK291480A (da) | 1981-01-06 |
| CA1145757A (en) | 1983-05-03 |
| DK11986A (da) | 1986-01-10 |
| FI66855B (fi) | 1984-08-31 |
| SE8405750D0 (sv) | 1984-11-16 |
| YU42340B (en) | 1988-08-31 |
| DK11886D0 (da) | 1986-01-10 |
| YU151380A (en) | 1983-02-28 |
| FI802127A7 (fi) | 1981-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: BRISTOL-MYERS CO |