FI62311C - Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat - Google Patents
Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat Download PDFInfo
- Publication number
- FI62311C FI62311C FI1850/73A FI185073A FI62311C FI 62311 C FI62311 C FI 62311C FI 1850/73 A FI1850/73 A FI 1850/73A FI 185073 A FI185073 A FI 185073A FI 62311 C FI62311 C FI 62311C
- Authority
- FI
- Finland
- Prior art keywords
- wide
- sodium
- cefalexin
- broad
- monohydrate
- Prior art date
Links
- 239000011734 sodium Substances 0.000 title claims description 15
- 229910052708 sodium Inorganic materials 0.000 title claims description 13
- 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 title claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 title 1
- 239000001301 oxygen Substances 0.000 title 1
- 238000005057 refrigeration Methods 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 claims description 27
- 229940106164 cephalexin Drugs 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 229940047526 cephalexin monohydrate Drugs 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 150000004682 monohydrates Chemical class 0.000 claims description 6
- YGZIWEZFFBPCLN-UHFFFAOYSA-N n,3-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound OOC1CCOP(=O)(NCCCl)N1CCCl YGZIWEZFFBPCLN-UHFFFAOYSA-N 0.000 claims description 6
- NZDYPHVJLWMLJI-CYJZLJNKSA-M cephalexin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C([O-])=O)=CC=CC=C1 NZDYPHVJLWMLJI-CYJZLJNKSA-M 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- -1 potassium cefalexin monohydrates Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000005169 Debye-Scherrer Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- MRVIVLQUPMJDPA-UHFFFAOYSA-N methyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OC MRVIVLQUPMJDPA-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26088572 | 1972-06-08 | ||
US00260885A US3822256A (en) | 1972-06-08 | 1972-06-08 | Crystalline monohydrates of sodium and potassium cephalexin |
Publications (2)
Publication Number | Publication Date |
---|---|
FI62311B FI62311B (fi) | 1982-08-31 |
FI62311C true FI62311C (fi) | 1982-12-10 |
Family
ID=22991055
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI1850/73A FI62311C (fi) | 1972-06-08 | 1973-06-07 | Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat |
Country Status (21)
Country | Link |
---|---|
US (1) | US3822256A (it) |
JP (1) | JPS604189B2 (it) |
AR (1) | AR197510A1 (it) |
AU (1) | AU472861B2 (it) |
BE (1) | BE800635A (it) |
CA (1) | CA1021322A (it) |
CH (1) | CH581661A5 (it) |
DD (1) | DD106183A5 (it) |
DE (1) | DE2329452A1 (it) |
ES (1) | ES415675A1 (it) |
FI (1) | FI62311C (it) |
FR (1) | FR2187303B1 (it) |
GB (1) | GB1413066A (it) |
HU (1) | HU165661B (it) |
IE (1) | IE37771B1 (it) |
IL (1) | IL42439A (it) |
NL (1) | NL7307817A (it) |
SE (1) | SE409207B (it) |
SU (1) | SU525430A3 (it) |
YU (1) | YU146173A (it) |
ZA (1) | ZA733835B (it) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5623217A (en) * | 1979-07-31 | 1981-03-05 | Kawasaki Steel Corp | Pouring starting method of continuous casting |
JPS60120886A (ja) * | 1983-12-02 | 1985-06-28 | Takeda Chem Ind Ltd | セフェムカルボン酸のナトリウム塩の結晶 |
JPS63108988U (it) * | 1987-01-08 | 1988-07-13 | ||
JPS63136198U (it) * | 1987-02-26 | 1988-09-07 | ||
US5142042A (en) * | 1989-01-23 | 1992-08-25 | Purzer Pharmaceutical Co., Ltd. | Process for preparing well crystallized alkali metal salts of 3, 7-substituted 7-aminocephalosporanic acid derivatives |
EP0381915B1 (en) * | 1989-02-06 | 1995-04-12 | Purzer Pharmaceutical Co., Ltd. | Process for preparing alkali metal salts of 3,7-substituted 7-aminocephalosporanic acid derivatives. |
CN115043853A (zh) * | 2022-08-16 | 2022-09-13 | 齐鲁晟华制药有限公司 | 一种头孢氨苄钠的制备方法 |
-
1972
- 1972-06-08 US US00260885A patent/US3822256A/en not_active Expired - Lifetime
-
1973
- 1973-05-11 CA CA171,003A patent/CA1021322A/en not_active Expired
- 1973-06-04 YU YU01461/73A patent/YU146173A/xx unknown
- 1973-06-05 IL IL42439A patent/IL42439A/xx unknown
- 1973-06-05 SE SE7307932A patent/SE409207B/xx unknown
- 1973-06-05 NL NL7307817A patent/NL7307817A/xx not_active Application Discontinuation
- 1973-06-06 ZA ZA733835A patent/ZA733835B/xx unknown
- 1973-06-07 FI FI1850/73A patent/FI62311C/fi active
- 1973-06-07 BE BE132034A patent/BE800635A/xx not_active IP Right Cessation
- 1973-06-07 DD DD171409A patent/DD106183A5/xx unknown
- 1973-06-07 HU HUBI471A patent/HU165661B/hu unknown
- 1973-06-07 SU SU1929889A patent/SU525430A3/ru active
- 1973-06-07 FR FR7320815A patent/FR2187303B1/fr not_active Expired
- 1973-06-07 AR AR248443A patent/AR197510A1/es active
- 1973-06-07 JP JP48063440A patent/JPS604189B2/ja not_active Expired
- 1973-06-07 ES ES415675A patent/ES415675A1/es not_active Expired
- 1973-06-07 AU AU56653/73A patent/AU472861B2/en not_active Expired
- 1973-06-07 IE IE923/73A patent/IE37771B1/xx unknown
- 1973-06-08 GB GB2745673A patent/GB1413066A/en not_active Expired
- 1973-06-08 CH CH838673A patent/CH581661A5/xx not_active IP Right Cessation
- 1973-06-08 DE DE2329452A patent/DE2329452A1/de not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
FR2187303A1 (it) | 1974-01-18 |
IL42439A0 (en) | 1973-08-29 |
CA1021322A (en) | 1977-11-22 |
IE37771B1 (en) | 1977-10-12 |
GB1413066A (en) | 1975-11-05 |
AR197510A1 (es) | 1974-04-15 |
BE800635A (fr) | 1973-12-07 |
DE2329452A1 (de) | 1974-01-03 |
US3822256A (en) | 1974-07-02 |
IE37771L (en) | 1973-12-08 |
DD106183A5 (it) | 1974-06-05 |
NL7307817A (it) | 1973-12-11 |
JPS4948815A (it) | 1974-05-11 |
ES415675A1 (es) | 1976-06-01 |
SU525430A3 (ru) | 1976-08-15 |
ZA733835B (en) | 1974-04-24 |
SE409207B (sv) | 1979-08-06 |
AU5665373A (en) | 1974-12-12 |
IL42439A (en) | 1975-12-31 |
CH581661A5 (it) | 1976-11-15 |
AU472861B2 (en) | 1976-06-10 |
FI62311B (fi) | 1982-08-31 |
JPS604189B2 (ja) | 1985-02-01 |
HU165661B (it) | 1974-10-28 |
FR2187303B1 (it) | 1977-09-09 |
YU146173A (en) | 1982-02-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0304019A2 (en) | Novel crystalline 7-(2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) | |
FI86854B (fi) | Foerfarande foer framstaellning av kristallina hydrat av cefalosporinsalt. | |
US4442101A (en) | Sesquihydrate of naphthyridine derivative, and process for the preparation thereof | |
RU2162081C2 (ru) | Способ получения ламотриджина и промежуточное соединение, используемое при его получении | |
FI62311C (fi) | Foerfarande foer framstaellning av kristallint natrium- och kaiumcefalexinmonohydrat | |
FI66388B (fi) | Foerfarande foer framstaellning av 7-(d-alfa-amino-alfa-(p-hydroxifenyl)acetamido)-3-(1,2,3-triazol-5-yltiometyl)-3-cefem-4-karboxylsyra-1,2-propylenglykolat | |
HU196602B (en) | Process for producing acid-addition salts of 7-square brackets open alpha-(aminothiazol-4-yl)-alpha-/z/-methoxy-imino-acetamido square brackets closed -3-square brackets open (1-methyl-1-pyrrolidino)-methyl square brackets closed -3-cefem-4-carboxilate, as well as dry mixtures thereof formed with bases and suitable for producing injectable solutions | |
EP0143658B1 (en) | Improvements in or relating to cephalosporin derivatives | |
SU845789A3 (ru) | Способ получени -7- -(4-окси-6-метил-НиКОТиНАМидО)- -(4-ОКСифЕНил)АцЕТАМидО -3- (1-МЕТилТЕТРАзОл-5-ил)ТиОМЕТил-3-цЕфЕМ-4-КАРбО-НОВОй КиСлОТы | |
CA3215809A1 (en) | New salt and solid state forms of escitalopram | |
FI66008C (fi) | Foerfarande foer framstaellning av kristallint anhydrat av natrium-7-(d-2-hydroxi-2-fenylacetamido)-3-(1-metyl-1h-tetrazol-5-yltiometyl)-3-cefem-4-karboxylat | |
KR0165894B1 (ko) | 3-[(5-메틸-2-푸라닐)메틸]-N-(4-피페리디닐)-3H-이미다조[4,5-b]-피리딘-2-아민 2-하이드록시-1,2,3-프로판트리카르복실레이트 | |
US3862186A (en) | Process for the production of cephalexin monohydrate | |
US4959469A (en) | Crystalline cephalosporin compounds | |
MXPA01012325A (es) | Formas polimorfas de un citrato cristalino de azobiciclo(2.2.2)octan-3-amina y sus composiciones farmaceuticas. | |
JP2575590B2 (ja) | トリアゾリルチオメチルチオセファロスポリン塩酸塩およびその水和物結晶ならびにそれらの製法 | |
US5068322A (en) | Crystalline cephalosporin compounds | |
EP0101170B1 (en) | Process for the manufacture of sodium cefoperazone | |
CA1282407C (en) | Crystalline cephem carboxylic acid addition salt | |
RU2074858C1 (ru) | Кристаллический дигидрат (5r, 6s)-2-карбамоилоксиметил-6-[(1r)-гидроксиэтил]-2-пенем-3-карбоновой кислоты, способ его получения, фармацевтическая композиция | |
EP0321562B1 (en) | Crystalline cephalosporin compounds, process for their preparation, and intermediates for their preparation | |
KR20040014507A (ko) | 세펨 화합물의 황산염 | |
KR900003530B1 (ko) | L 또는 (s)-3-(3,4-디히드록시페닐)-2-메틸알라닌 에스테르의 결정성염의 제조 방법 | |
JP3068175B2 (ja) | イソチアゾロ〔5,4―b〕ピリジン誘導体 | |
EP0548834B1 (en) | Stable hexahydrate of etoposide 4'-phosphate disodium salt |