CA1136123A - Production of 7-(2-aminomethylphenylacetamido) -3-(1-carboxymethyltetrazol-5-ylthiomethyl) -3-cephem-4-carboxylic acid - Google Patents
Production of 7-(2-aminomethylphenylacetamido) -3-(1-carboxymethyltetrazol-5-ylthiomethyl) -3-cephem-4-carboxylic acidInfo
- Publication number
- CA1136123A CA1136123A CA000352709A CA352709A CA1136123A CA 1136123 A CA1136123 A CA 1136123A CA 000352709 A CA000352709 A CA 000352709A CA 352709 A CA352709 A CA 352709A CA 1136123 A CA1136123 A CA 1136123A
- Authority
- CA
- Canada
- Prior art keywords
- borane
- complex
- amine complex
- amine
- mixture
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 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 title 1
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 16
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229930186147 Cephalosporin Natural products 0.000 claims description 7
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 7
- 229940124587 cephalosporin Drugs 0.000 claims description 7
- 150000001780 cephalosporins Chemical class 0.000 claims description 7
- KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical compound [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims description 6
- LRJRPHROCLHMHK-UHFFFAOYSA-N boron;n,n-dimethylmethanamine Chemical compound [B].CN(C)C LRJRPHROCLHMHK-UHFFFAOYSA-N 0.000 claims description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 5
- YJROYUJAFGZMJA-UHFFFAOYSA-N boron;morpholine Chemical compound [B].C1COCCN1 YJROYUJAFGZMJA-UHFFFAOYSA-N 0.000 claims description 5
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- VEWFZHAHZPVQES-UHFFFAOYSA-N boron;n,n-diethylethanamine Chemical compound [B].CCN(CC)CC VEWFZHAHZPVQES-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims 4
- 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 abstract description 4
- 229960004292 ceforanide Drugs 0.000 abstract description 3
- DDQYZSWIJHCQTP-WGAFOPHPSA-N (6R)-7-[(2-azido-2-phenylpropanoyl)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 N(=[N+]=[N-])C(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CC(=O)O)C(=O)O)C1=O)(C1=CC=CC=C1)C DDQYZSWIJHCQTP-WGAFOPHPSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000005187 foaming Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- -1 2-aminomethylphenylacetamido Chemical group 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- SPIFDSWFDKNERT-UHFFFAOYSA-N nickel;hydrate Chemical compound O.[Ni] SPIFDSWFDKNERT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PGZQTMHQSTWIDY-WGAFOPHPSA-N NC(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CC(=O)O)C(=O)O)C1=O)(C1=CC=CC=C1)C Chemical compound NC(C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2CC(=O)O)C(=O)O)C1=O)(C1=CC=CC=C1)C PGZQTMHQSTWIDY-WGAFOPHPSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- XVJFCWCVLJOKRP-UHFFFAOYSA-N boron;n-ethylethanamine Chemical compound [B].CCNCC XVJFCWCVLJOKRP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/054,733 US4243803A (en) | 1979-07-05 | 1979-07-05 | Production of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| US054,733 | 1979-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1136123A true CA1136123A (en) | 1982-11-23 |
Family
ID=21993156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000352709A Expired CA1136123A (en) | 1979-07-05 | 1980-05-26 | Production of 7-(2-aminomethylphenylacetamido) -3-(1-carboxymethyltetrazol-5-ylthiomethyl) -3-cephem-4-carboxylic acid |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4243803A (enExample) |
| JP (1) | JPS5610196A (enExample) |
| CA (1) | CA1136123A (enExample) |
| ES (1) | ES493079A0 (enExample) |
| FR (1) | FR2460954A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0630976B2 (ja) * | 1986-07-31 | 1994-04-27 | 凸版印刷株式会社 | 製本方法 |
| AU2001241042A1 (en) * | 2000-03-08 | 2001-09-17 | Takeda Chemical Industries Ltd. | Process for the preparation of hydrazine derivatives |
| CN102898442A (zh) * | 2012-10-25 | 2013-01-30 | 河南中帅医药科技发展有限公司 | 头孢雷特的精制方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2860167A (en) * | 1953-10-07 | 1958-11-11 | Bokine teialkyl amines | |
| US3035904A (en) * | 1953-10-07 | 1962-05-22 | Diesel fuel compositions | |
| 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 |
| JPS525787A (en) * | 1975-06-27 | 1977-01-17 | Bristol Myers Co | Antiibacterial agent |
| US4118563A (en) * | 1977-11-25 | 1978-10-03 | Bristol-Myers Company | Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
-
1979
- 1979-07-05 US US06/054,733 patent/US4243803A/en not_active Expired - Lifetime
-
1980
- 1980-05-26 CA CA000352709A patent/CA1136123A/en not_active Expired
- 1980-06-26 JP JP8599480A patent/JPS5610196A/ja active Granted
- 1980-07-02 FR FR8014751A patent/FR2460954A1/fr active Granted
- 1980-07-03 ES ES493079A patent/ES493079A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4243803A (en) | 1981-01-06 |
| JPH0233717B2 (enExample) | 1990-07-30 |
| JPS5610196A (en) | 1981-02-02 |
| FR2460954A1 (fr) | 1981-01-30 |
| ES8107235A1 (es) | 1981-10-01 |
| ES493079A0 (es) | 1981-10-01 |
| FR2460954B1 (enExample) | 1984-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |