SU1024009A3 - Способ получени 1-детиа-1-оксацефалоспоринов - Google Patents

Способ получени 1-детиа-1-оксацефалоспоринов Download PDF

Info

Publication number: SU1024009A3
Authority: SU; USSR - Soviet Union
Prior art keywords: formula; group; coob; producing; methanol
Prior art date: 1977-06-06

Application number

SU782698998A

Other languages

English (en)

Russian (ru)

Inventor

Есиока Мицуру

Уео Соитиро

Хамасима Есио

Киккава Икуо

Цудзи Терудзи

Нагата Ватару

Original Assignee

Сионоги Энд Ко.,Лтд (Фирма)

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.)

1977-06-06

Filing date

1978-12-20

Publication date

1983-06-15

1978-12-20 Application filed by Сионоги Энд Ко.,Лтд (Фирма) filed Critical Сионоги Энд Ко.,Лтд (Фирма)

1983-06-15 Application granted granted Critical

1983-06-15 Publication of SU1024009A3 publication Critical patent/SU1024009A3/ru

Links

238000000034 method Methods 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
-1 dichloromethane Chemical class 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
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 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
229910052736 halogen Chemical group 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims 1
229930186147 Cephalosporin Natural products 0.000 abstract description 3
229940124587 cephalosporin Drugs 0.000 abstract description 3
150000001780 cephalosporins Chemical class 0.000 abstract description 3
239000003242 anti bacterial agent Substances 0.000 abstract 1
230000003115 biocidal effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000006198 methoxylation reaction Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical compound CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004802 cyanophenyl group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

SU782698998A 1977-06-06 1978-12-20 Способ получени 1-детиа-1-оксацефалоспоринов SU1024009A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP52067025A JPS6040438B2 (ja)	1977-06-06	1977-06-06	１−オキサデチアセフアロスポリンの製法

Publications (1)

Publication Number	Publication Date
SU1024009A3 true SU1024009A3 (ru)	1983-06-15

Family

ID=13332927

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU782698998A SU1024009A3 (ru)	1977-06-06	1978-12-20	Способ получени 1-детиа-1-оксацефалоспоринов
SU782698999A SU1047390A3 (ru)	1977-06-06	1978-12-20	Способ получени 1-детиа-1-оксацефалоспоринов

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU782698999A SU1047390A3 (ru)	1977-06-06	1978-12-20	Способ получени 1-детиа-1-оксацефалоспоринов

Country Status (5)

Country	Link
JP (1)	JPS6040438B2 (cs)
CS (2)	CS196418B2 (cs)
PL (1)	PL117503B1 (cs)
SU (2)	SU1024009A3 (cs)
YU (1)	YU42074B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110003243A (zh) *	2019-04-23	2019-07-12	山西千岫制药有限公司	一种氧头孢烯母核的制备方法

1977
- 1977-06-06 JP JP52067025A patent/JPS6040438B2/ja not_active Expired
1978
- 1978-02-14 CS CS697078A patent/CS196418B2/cs unknown
- 1978-02-14 CS CS697178A patent/CS196419B2/cs unknown
- 1978-02-14 PL PL21645578A patent/PL117503B1/pl unknown
- 1978-12-20 SU SU782698998A patent/SU1024009A3/ru active
- 1978-12-20 SU SU782698999A patent/SU1047390A3/ru active
1983
- 1983-03-07 YU YU54983A patent/YU42074B/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Патент СССР по за вке № 246ii302/23-OV, кл. С 071 ЭВ/0\|, 1976. 2. Патент СССР № , кл. С 07 D 501/0, 1973. *

Also Published As

Publication number	Publication date
SU1047390A3 (ru)	1983-10-07
YU54983A (en)	1984-02-29
JPS543088A (en)	1979-01-11
CS196418B2 (en)	1980-03-31
JPS6040438B2 (ja)	1985-09-11
YU42074B (en)	1988-04-30
PL117503B1 (en)	1981-08-31
CS196419B2 (en)	1980-03-31

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