SU847921A3 - Способ получени производных оксазо-лиНОАзЕТидиНилпЕНТЕНОВОй КиСлОТы - Google Patents

Способ получени производных оксазо-лиНОАзЕТидиНилпЕНТЕНОВОй КиСлОТы Download PDF

Info

Publication number: SU847921A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; diphenylmethyl; oxo; methyl; water
Prior art date: 1977-03-30

Application number

SU782595605A

Other languages

English (en)

Russian (ru)

Inventor

Цудзи Терудзи

Есиока Мицуру

Уео Соитиро

Хамасима Есио

Киккава Икуо

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.)

1977-03-30

Filing date

1978-03-30

Publication date

1981-07-15

1978-03-30 Application filed by Сионоги Энд Ко,Лтд (Фирма) filed Critical Сионоги Энд Ко,Лтд (Фирма)

1981-07-15 Application granted granted Critical

1981-07-15 Publication of SU847921A3 publication Critical patent/SU847921A3/ru

Links

239000002253 acid Substances 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 5
-1 1-methyl-5-tetrazolylthio group Chemical group 0.000 claims description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical group CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
241001415849 Strigiformes Species 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
MRDOPPZMPMSASQ-UHFFFAOYSA-N benzhydryloxymethylbenzene Chemical class C=1C=CC=CC=1COC(C=1C=CC=CC=1)C1=CC=CC=C1 MRDOPPZMPMSASQ-UHFFFAOYSA-N 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
125000001424 substituent group Chemical group 0.000 abstract 2
JYLUAHUNORBOAL-RXMQYKEDSA-N (6r)-8-oxo-4,5-dithia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CSS[C@@H]2CC(=O)N12 JYLUAHUNORBOAL-RXMQYKEDSA-N 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
230000026030 halogenation Effects 0.000 abstract 1
238000005658 halogenation reaction Methods 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
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 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000010828 elution Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001485 alkali metal perchlorate Inorganic materials 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
FQMKROYBMIKXIX-UHFFFAOYSA-N disulfo carbonate Chemical compound [H+].[H+].[O-]S(=O)(=O)OC(=O)OS([O-])(=O)=O FQMKROYBMIKXIX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 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
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005286 illumination Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229940046892 lead acetate Drugs 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000006011 modification reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent 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
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical class [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003450 sulfenic acids Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SU782595605A 1977-03-30 1978-03-30 Способ получени производных оксазо-лиНОАзЕТидиНилпЕНТЕНОВОй КиСлОТы SU847921A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP52036613A JPS6019312B2 (ja)	1977-03-30	1977-03-30	オキサゾリノアゼチジニルペンテン酸誘導体の製造法

Publications (1)

Publication Number	Publication Date
SU847921A3 true SU847921A3 (ru)	1981-07-15

Family

ID=12474641

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU782595605A SU847921A3 (ru)	1977-03-30	1978-03-30	Способ получени производных оксазо-лиНОАзЕТидиНилпЕНТЕНОВОй КиСлОТы
SU792749106A SU1207395A3 (ru)	1977-03-30	1979-04-13	Способ получени оксазолиноазетидиновых соединений

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU792749106A SU1207395A3 (ru)	1977-03-30	1979-04-13	Способ получени оксазолиноазетидиновых соединений

Country Status (15)

Country	Link
JP (1)	JPS6019312B2 (cs)
AR (1)	AR224341A1 (cs)
AT (1)	AT360548B (cs)
BG (1)	BG33291A3 (cs)
CS (1)	CS216192B2 (cs)
DD (1)	DD135388A5 (cs)
ES (1)	ES468314A1 (cs)
GR (1)	GR68897B (cs)
HU (1)	HU174071B (cs)
MX (1)	MX4990E (cs)
PL (1)	PL116487B1 (cs)
PT (1)	PT67825B (cs)
RO (2)	RO74065A (cs)
SU (2)	SU847921A3 (cs)
YU (2)	YU40697B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT382298B (de) *	1982-05-13	1987-02-10	Haas Franz Waffelmasch	Verfahren und vorrichtung zum kontinuierlichen, insbesondere vollautomatischen, herstellen eines endlosen waffelverbandes gleichbleibender breite durch uebereinanderschichten einzelner waffelblattlagen und einer oder mehrerer masseschichten, insbesondere cremeschichten
JPS6188A (ja) *	1985-01-24	1986-01-06	Shionogi & Co Ltd	オキサゾリノアゼチジン誘導体の製造方法
JPH02145006U (cs) *	1989-05-11	1990-12-10

1977
- 1977-03-30 JP JP52036613A patent/JPS6019312B2/ja not_active Expired
1978
- 1978-03-25 PL PL20558678A patent/PL116487B1/pl unknown
- 1978-03-27 AR AR27154278A patent/AR224341A1/es active
- 1978-03-27 PT PT6782578A patent/PT67825B/pt unknown
- 1978-03-28 RO RO7893655A patent/RO74065A/ro unknown
- 1978-03-28 RO RO78100337A patent/RO79180A/ro unknown
- 1978-03-29 AT AT220078A patent/AT360548B/de not_active IP Right Cessation
- 1978-03-29 YU YU74578A patent/YU40697B/xx unknown
- 1978-03-29 ES ES468314A patent/ES468314A1/es not_active Expired
- 1978-03-29 MX MX697378U patent/MX4990E/es unknown
- 1978-03-30 DD DD20449178A patent/DD135388A5/xx unknown
- 1978-03-30 CS CS204678A patent/CS216192B2/cs unknown
- 1978-03-30 SU SU782595605A patent/SU847921A3/ru active
- 1978-03-30 HU HU78SI1622A patent/HU174071B/hu unknown
- 1978-03-30 BG BG039228A patent/BG33291A3/xx unknown
- 1978-03-30 GR GR55845A patent/GR68897B/el unknown
1979
- 1979-04-13 SU SU792749106A patent/SU1207395A3/ru active
1982
- 1982-11-08 YU YU249382A patent/YU40418B/xx unknown

Also Published As

Publication number	Publication date
ES468314A1 (es)	1979-09-16
PT67825A (en)	1978-04-01
AR224341A1 (es)	1981-11-30
SU1207395A3 (ru)	1986-01-23
RO74065A (ro)	1983-09-26
PL205586A1 (pl)	1979-04-09
RO74065B (ro)	1983-08-30
CS216192B2 (en)	1982-10-29
YU40418B (en)	1985-12-31
JPS53121787A (en)	1978-10-24
YU40697B (en)	1986-04-30
JPS6019312B2 (ja)	1985-05-15
YU249382A (en)	1983-02-28
GR68897B (cs)	1982-03-15
ATA220078A (de)	1980-06-15
PL116487B1 (en)	1981-06-30
RO79180A (ro)	1982-06-25
BG33291A3 (en)	1983-01-14
MX4990E (es)	1983-01-31
YU74578A (en)	1983-01-21
HU174071B (hu)	1979-10-28
DD135388A5 (de)	1979-05-02
AT360548B (de)	1981-01-12
PT67825B (en)	1979-09-27

Publication	Publication Date	Title
SU847921A3 (ru)	1981-07-15	Способ получени производных оксазо-лиНОАзЕТидиНилпЕНТЕНОВОй КиСлОТы
KR880000041B1 (ko)	1988-02-20	시스테인 유동체의 분자내 또는 분자간 이황화물의 제조방법
JPH04297461A (ja)	1992-10-21	２−チオヒダントイン誘導体
JPH0451538B2 (cs)	1992-08-19
SU619098A3 (ru)	1978-08-05	Способ получени карбоновых кислот или их минеральных,или органических солей,или сложных эфиров
SU615863A3 (ru)	1978-07-15	Способ получени производных прегнановой кислоты
JP2957699B2 (ja)	1999-10-06	７α―アルコキシセフェム誘導体の製造方法
JPH0774194B2 (ja)	1995-08-09	生理活性を有する新規なアクチノニン誘導体
FI81808B (fi)	1990-08-31	Foerfarande foer framstaellning av ursodesoxicholsyra fraon 3 ,7 ,12 -trihydroxicholansyra, samt anvaenda mellanprodukter.
SU1110386A3 (ru)	1984-08-23	Способ получени 1-оксадетиацефалоспоринов
PT99786A (pt)	1992-11-30	Processo de preparacao de intermediarios da astaxantina
US4456766A (en)	1984-06-26	Process for the production of N-acetyl-2,3-dehydro-aminocarboxylic acid esters
JP3432880B2 (ja)	2003-08-04	光学活性アザスピロ化合物の製法
EP0080942B1 (en)	1986-02-26	Novel intermediates and process for preparing (s)-3-acylamino-4-substituted-2-azetidinones
KR810001383B1 (ko)	1981-10-17	옥사졸린 유도체의 제조방법
JP3159767B2 (ja)	2001-04-23	新規な含硫黄化合物及びその製造方法
JPH0585549B2 (cs)	1993-12-07
JPS6127396B2 (cs)	1986-06-25
JP2894183B2 (ja)	1999-05-24	光学活性なグルタル酸誘導体の精製方法
KR840004407A (ko)	1984-10-15	벤즈이미다졸 유도체의 제법
ES8200364A1 (es)	1981-11-01	Procedimiento para la obtencion de derivados de la fenotia- zina
SU555095A1 (ru)	1977-04-25	Способ получени аминоалкансульфоновых кислот или их солей
KR790001528B1 (ko)	1979-10-26	리파마이신 화합물의 제조방법
JPS626717B2 (cs)	1987-02-13
JPS6213955B2 (cs)	1987-03-30