SU410590A3 - - Google Patents

Info

Publication number: SU410590A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; added; ethyl acetate; solution; water
Prior art date: 1968-12-12

Application number

SU1382754A

Other languages

Priority date (The priority date 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 date listed.)

1968-12-12

Filing date

1969-12-08

Publication date

1974-01-05

1969-12-08 Application filed filed Critical

1974-01-05 Application granted granted Critical

1974-01-05 Publication of SU410590A3 publication Critical patent/SU410590A3/ru

Links

XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
-1 5-amino-tetrazolyl acetylamino Chemical group 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
235000002639 sodium chloride Nutrition 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
238000002211 ultraviolet spectrum Methods 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 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 description 2
IJVOBCCZGJEMMP-UHFFFAOYSA-N N1N=NN=C1.[C] Chemical group N1N=NN=C1.[C] IJVOBCCZGJEMMP-UHFFFAOYSA-N 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N n-Butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
108010013043 Acetylesterase Proteins 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
101100511454 Epichloe uncinata lolO1 gene Proteins 0.000 description 1
101100511455 Epichloe uncinata lolO2 gene Proteins 0.000 description 1
102100036617 Monoacylglycerol lipase ABHD2 Human genes 0.000 description 1
241000188329 Talpa altaica Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005179 haloacetyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
GNZAVUJXHUVZBO-UHFFFAOYSA-N n-(5-aminotetrazol-1-yl)acetamide Chemical compound CC(=O)NN1N=NN=C1N GNZAVUJXHUVZBO-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
HSAJRDKFYZAGLU-UHFFFAOYSA-M perchloryloxymercury Chemical compound [Hg+].[O-]Cl(=O)(=O)=O HSAJRDKFYZAGLU-UHFFFAOYSA-M 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
STUWXYZZZISNAM-UHFFFAOYSA-M sodium;hydrogen carbonate;propan-2-one Chemical compound [Na+].CC(C)=O.OC([O-])=O STUWXYZZZISNAM-UHFFFAOYSA-M 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000002604 ultrasonography 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
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1382754A 1968-12-12 1969-12-08 SU410590A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1851668A CH507985A (de)	1968-12-12	1968-12-12	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure

Publications (1)

Publication Number	Publication Date
SU410590A3 true SU410590A3 (cs)	1974-01-05

Family

ID=4433518

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1670625A SU400106A3 (cs)	1968-12-12	1969-12-08
SU1382754A SU410590A3 (cs)	1968-12-12	1969-12-08

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
SU1670625A SU400106A3 (cs)	1968-12-12	1969-12-08

Country Status (5)

Country	Link
AT (2)	AT301031B (cs)
BR (1)	BR6915033D0 (cs)
CH (2)	CH527855A (cs)
CS (2)	CS156463B2 (cs)
SU (2)	SU400106A3 (cs)

1968
- 1968-12-12 CH CH4471A patent/CH527855A/de not_active IP Right Cessation
- 1968-12-12 CH CH1851668A patent/CH507985A/de not_active IP Right Cessation
1969
- 1969-11-10 CS CS238673*1A patent/CS156463B2/cs unknown
- 1969-11-10 CS CS739269A patent/CS156462B2/cs unknown
- 1969-12-08 SU SU1670625A patent/SU400106A3/ru active
- 1969-12-08 SU SU1382754A patent/SU410590A3/ru active
- 1969-12-11 AT AT427271A patent/AT301031B/de not_active IP Right Cessation
- 1969-12-11 AT AT1155169A patent/AT297924B/de not_active IP Right Cessation
- 1969-12-12 BR BR215033/69A patent/BR6915033D0/pt unknown

Also Published As

Publication number	Publication date
BR6915033D0 (pt)	1973-05-24
SU400106A3 (cs)	1973-10-03
AT301031B (de)	1972-08-25
CH527855A (de)	1972-09-15
CH507985A (de)	1971-05-31
AT297924B (de)	1972-04-10
CS156463B2 (cs)	1974-07-24
CS156462B2 (cs)	1974-07-24

Publication	Publication Date	Title
SU651704A3 (ru)	1979-03-05	Способ получени производных дибензоциклогептена, рацемических или оптически активных, или их солей
US4312982A (en)	1982-01-26	α-Acylureidocephalosporins and salts and esters thereof
IE56401B1 (en)	1991-07-17	Fluoromethylthiooxacephalosporins
SU546282A3 (ru)	1977-02-05	Способ получени 7- -амино-7 метокси-цефалоспориновых эфиров
SU1405704A3 (ru)	1988-06-23	Способ получени метилендиолдикарбоксилатных соединений или их фармацевтически приемлемых щелочных или четвертичных аммониевых солей
US3355452A (en)	1967-11-28	Derivatives of 7-amino-cephalosporanic acid
US3234223A (en)	1966-02-08	Preparation of 7-amino-cephalosporanic acid and derivatives
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US3464985A (en)	1969-09-02	7 - (d - alpha - amino - (acetamidophenylacetamido))-cephalosporanic acids and derivatives thereof
SU542474A3 (ru)	1977-01-05	Способ получени производных 7-амино-3-цефем-3 -4-карбоновой кислоты или их солей
US4132789A (en)	1979-01-02	7-[2-(2-Imino-4-thiazolin-4-yl)-2-sulfoacetamido]cephalosporins and antibacterial compositions containing them
US5140044A (en)	1992-08-18	Ucn-1028d derivatives
US4325951A (en)	1982-04-20	1-Oxadethiacephalosporin derivatives and antibacterial use thereof
US3234222A (en)	1966-02-08	Preparation of 7-acylaminocephalosporanic acids
US4051129A (en)	1977-09-27	Process for preparing 7-methoxycephalosporin compounds
SU727147A3 (ru)	1980-04-05	Способ получени цефалоспоринов
SU432723A3 (ru)	1974-06-15	Способ получения производных 7-аминоцефалоспорановой кислоты
US3928333A (en)	1975-12-23	Process for the preparation of 3 cephalosporin esters
US3270000A (en)	1966-08-30	Protected amino acid derivatives of 7-aminocephalosporanic acid
SU402222A1 (ru)		Способ получения производных 7-аминоцефалоспорановой кислоты
SU419039A3 (cs)	1974-03-05
JPS6129957B2 (cs)	1986-07-10
KR830000342B1 (ko)	1983-03-04	세팔로스포린 유도체의 제법
US3555017A (en)	1971-01-12	Derivative of 7-acylaminocephalosporanic acid
US3178426A (en)	1965-04-13	1, 3, 4-dioxazolyl-cephalosporin derivatives