SU578863A3 - Способ выделени сложных эфиров -защищенных аминокислот из их водных растворов - Google Patents

Способ выделени сложных эфиров -защищенных аминокислот из их водных растворов

Info

Publication number: SU578863A3
Authority: SU; USSR - Soviet Union
Prior art keywords: solution; acid; water; mmol; solvent
Prior art date: 1973-08-01

Application number

SU7402051820A

Other languages

English (en)

Russian (ru)

Inventor

Робинсон Колин

Волкер Дэрек

Original Assignee

Глаксо Лабораториз Лимитед (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.)

1973-08-01

Filing date

1974-07-31

Publication date

1977-10-30

1974-07-31 Application filed by Глаксо Лабораториз Лимитед (Фирма) filed Critical Глаксо Лабораториз Лимитед (Фирма)

1977-10-30 Application granted granted Critical

1977-10-30 Publication of SU578863A3 publication Critical patent/SU578863A3/ru

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 27
150000001413 amino acids Chemical class 0.000 title description 11
238000000034 method Methods 0.000 title description 8
150000002148 esters Chemical class 0.000 title description 6
239000000243 solution Substances 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000002904 solvent Substances 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
-1 N-protected amino Chemical class 0.000 description 21
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
235000001014 amino acid Nutrition 0.000 description 18
239000000203 mixture Substances 0.000 description 16
239000002253 acid Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 9
235000011007 phosphoric acid Nutrition 0.000 description 9
238000000926 separation method Methods 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
230000032050 esterification Effects 0.000 description 7
238000005886 esterification reaction Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
229930186147 Cephalosporin Natural products 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
229940124587 cephalosporin Drugs 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
239000004220 glutamic acid Substances 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
229910000160 potassium phosphate Inorganic materials 0.000 description 2
235000011009 potassium phosphates Nutrition 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000010802 sludge Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
YZJSUQQZGCHHNQ-SCSAIBSYSA-N (2r)-6-amino-2-azaniumyl-6-oxohexanoate Chemical compound OC(=O)[C@H](N)CCCC(N)=O YZJSUQQZGCHHNQ-SCSAIBSYSA-N 0.000 description 1
IRHVLQMEQPABHG-ZLYSWTFPSA-N (3r,4r,5r,6r,7r,8r,9s,10r,13r,14r,17r)-3,4,6,7-tetrahydroxy-17-[(1s)-1-[(2s,4s)-6-hydroxy-4-propan-2-yloxan-2-yl]ethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,16,17-tetradecahydrocyclopenta[a]phenanthren-15-one Chemical compound C1[C@H](C(C)C)CC(O)O[C@@H]1[C@@H](C)[C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CC[C@@H](O)[C@H](O)[C@@H]4[C@@H](O)[C@H](O)[C@H]3[C@H]2C(=O)C1 IRHVLQMEQPABHG-ZLYSWTFPSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 description 1
IHDRXDWUDBSDAN-UHFFFAOYSA-N 2-diazopropane Chemical compound CC(C)=[N+]=[N-] IHDRXDWUDBSDAN-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010004966 Bite Diseases 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
108010024636 Glutathione Proteins 0.000 description 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
DMKGSUIMVRYBCS-UHFFFAOYSA-N benzhydryl(methyl)diazene Chemical compound C=1C=CC=CC=1C(N=NC)C1=CC=CC=C1 DMKGSUIMVRYBCS-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
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 1
238000004090 dissolution Methods 0.000 description 1
AWISGSJZNFRYNE-UHFFFAOYSA-N ethanol;dihydrochloride Chemical compound Cl.Cl.CCO AWISGSJZNFRYNE-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229960004502 levodopa Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000005588 protonation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003799 water insoluble solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; 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)
Cephalosporin Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU7402051820A 1973-08-01 1974-07-31 Способ выделени сложных эфиров -защищенных аминокислот из их водных растворов SU578863A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB36498/73A GB1479141A (en)	1973-08-01	1973-08-01	Extraction of n-blocked amino acid from aqueous solutions

Publications (1)

Publication Number	Publication Date
SU578863A3 true SU578863A3 (ru)	1977-10-30

Family

ID=10388720

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU7402051820A SU578863A3 (ru)	1973-08-01	1974-07-31	Способ выделени сложных эфиров -защищенных аминокислот из их водных растворов

Country Status (16)

Country	Link
JP (1)	JPS5829299B2 (fr)
AT (1)	AT335606B (fr)
BE (1)	BE818367A (fr)
CA (1)	CA1031769A (fr)
CH (1)	CH614924A5 (fr)
DE (1)	DE2436772C2 (fr)
DK (1)	DK408674A (fr)
ES (1)	ES428799A1 (fr)
FR (1)	FR2239473B1 (fr)
GB (1)	GB1479141A (fr)
HU (1)	HU173065B (fr)
IE (1)	IE39650B1 (fr)
NL (1)	NL7410293A (fr)
SE (1)	SE7409886L (fr)
SU (1)	SU578863A3 (fr)
ZA (1)	ZA744905B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102120185B (zh) *	2010-04-12	2013-06-12	上海海嘉诺医药发展股份有限公司	一种负载型固体催化剂及其制备和应用

1973
- 1973-08-01 GB GB36498/73A patent/GB1479141A/en not_active Expired
1974
- 1974-07-31 SU SU7402051820A patent/SU578863A3/ru active
- 1974-07-31 IE IE1625/74A patent/IE39650B1/xx unknown
- 1974-07-31 ES ES428799A patent/ES428799A1/es not_active Expired
- 1974-07-31 CH CH1051874A patent/CH614924A5/xx not_active IP Right Cessation
- 1974-07-31 NL NL7410293A patent/NL7410293A/xx not_active Application Discontinuation
- 1974-07-31 DE DE2436772A patent/DE2436772C2/de not_active Expired
- 1974-07-31 CA CA206,012A patent/CA1031769A/fr not_active Expired
- 1974-07-31 JP JP49087087A patent/JPS5829299B2/ja not_active Expired
- 1974-07-31 AT AT628374A patent/AT335606B/de not_active IP Right Cessation
- 1974-07-31 DK DK408674*A patent/DK408674A/da not_active Application Discontinuation
- 1974-07-31 FR FR7426655A patent/FR2239473B1/fr not_active Expired
- 1974-07-31 SE SE7409886A patent/SE7409886L/ not_active Application Discontinuation
- 1974-07-31 HU HU74GA165A patent/HU173065B/hu unknown
- 1974-07-31 ZA ZA00744905A patent/ZA744905B/xx unknown
- 1974-08-01 BE BE147180A patent/BE818367A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK408674A (fr)	1975-03-24
AT335606B (de)	1977-03-25
HU173065B (hu)	1979-02-28
ES428799A1 (es)	1976-09-16
FR2239473B1 (fr)	1978-08-11
ATA628374A (de)	1976-07-15
NL7410293A (nl)	1975-02-04
CH614924A5 (en)	1979-12-28
JPS5076003A (fr)	1975-06-21
DE2436772A1 (de)	1975-02-20
CA1031769A (fr)	1978-05-23
GB1479141A (en)	1977-07-06
IE39650B1 (en)	1978-11-22
JPS5829299B2 (ja)	1983-06-22
SE7409886L (fr)	1975-03-20
DE2436772C2 (de)	1986-03-06
FR2239473A1 (fr)	1975-02-28
ZA744905B (en)	1975-09-24
BE818367A (fr)	1975-02-03
IE39650L (en)	1975-02-01
AU7188074A (en)	1976-02-05

Publication	Publication Date	Title
SU795482A3 (ru)	1981-01-07	Способ получени производных7-/2-(2-АМиНОТиАзОлил-4)-2-АлКОКСи-иМиНОАцЕТАМидО/-3-ТиОМЕТил-3-цЕфЕМ- 4-КАРбОНОВОй КиСлОТы B ВидЕ СиН- изОМЕРОВ
FI96952C (fi)	1998-05-20	Menetelmä klavulaanihapon puhdistamiseksi tiettyjen polyamiinien avulla
US3976680A (en)	1976-08-24	Production of an ester of one enantiomer of an α-amino acid in the form of a salt with an optically active acid
FR1449628A (fr)	1966-08-19	Procédé de préparation d'indoles polynucléaires désacylés, notamment d'esters de la série de la désacétyl-vincaleucoblastine et de la désacétyl-vincristine
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