RO113245B1 - Derivati tiofosfat ai acidului tia(dia)zolacetic si procedeu pentru prepararea acestora - Google Patents

Derivati tiofosfat ai acidului tia(dia)zolacetic si procedeu pentru prepararea acestora Download PDF

Info

Publication number: RO113245B1
Authority: RO; Romania
Prior art keywords: group; general formula; diethylthiophosphoryl; acid; hydrogen
Prior art date: 1994-03-21

Application number

RO96-01614A

Other languages

English (en)

Romanian (ro)

Inventor

Sung Kyum Kim

Seong Nyeon Kim

Woo Hyun Kim

Original Assignee

Lucky Ltd

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.)

1994-03-21

Filing date

1994-12-07

Publication date

1998-05-29

1994-12-07 Application filed by Lucky Ltd filed Critical Lucky Ltd

1998-05-29 Publication of RO113245B1 publication Critical patent/RO113245B1/ro

Links

239000002253 acid Substances 0.000 title claims abstract description 12
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title claims abstract description 8
241000534944 Thia Species 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000006239 protecting group Chemical group 0.000 claims abstract description 11
239000002904 solvent Substances 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
150000002431 hydrogen Chemical class 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 8
239000002585 base Substances 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
239000000126 substance Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004437 phosphorous atom Chemical group 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
-1 t-butoxycarbonylisopropyl group Chemical group 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
150000007524 organic acids Chemical group 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000003512 tertiary amines Chemical group 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 2
150000004714 phosphonium salts Chemical class 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract 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 abstract description 2
229910052708 sodium Inorganic materials 0.000 abstract description 2
239000011734 sodium Substances 0.000 abstract description 2
150000001782 cephems Chemical class 0.000 abstract 2
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
241000386115 Coras Species 0.000 abstract 1
125000005042 acyloxymethyl group Chemical group 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
150000001340 alkali metals Chemical class 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 abstract 1
150000002500 ions Chemical class 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 11
238000005917 acylation reaction Methods 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
125000003277 amino group Chemical group 0.000 description 8
239000000243 solution Substances 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000001012 protector Effects 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
OHNLHUOBEAQAON-YCRREMRBSA-N (2Z)-2-(3-amino-1,2,4-thiadiazol-5-yl)-2-ethoxyiminoacetic acid Chemical compound CCO\N=C(\C(O)=O)C1=NC(N)=NS1 OHNLHUOBEAQAON-YCRREMRBSA-N 0.000 description 1
RQMBWYIXVXJFNY-YHYXMXQVSA-N (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-ethoxyiminoacetic acid Chemical compound CCO\N=C(/C(O)=O)C1=CSC(N)=N1 RQMBWYIXVXJFNY-YHYXMXQVSA-N 0.000 description 1
NLARCUDOUOQRPB-WTKPLQERSA-N (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-WTKPLQERSA-N 0.000 description 1
LWRXBZDYMOWJEV-FAJYDZGRSA-N (2z)-2-ethoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CCO\N=C(/C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 LWRXBZDYMOWJEV-FAJYDZGRSA-N 0.000 description 1
PKPGSMOHYWOGJR-SLMZUGIISA-N (2z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PKPGSMOHYWOGJR-SLMZUGIISA-N 0.000 description 1
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
DVDGHRQOLYEZAE-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylcyclohexane-1,2-diamine Chemical compound CN(C)C1CCCCC1N(C)C DVDGHRQOLYEZAE-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
XNEVAMKIORLIJP-PXNMLYILSA-N NC=1SC=C(N=1)C(C)(C)O\N=C(\C(=O)O)/C(=O)OC(C)(C)C Chemical compound NC=1SC=C(N=1)C(C)(C)O\N=C(\C(=O)O)/C(=O)OC(C)(C)C XNEVAMKIORLIJP-PXNMLYILSA-N 0.000 description 1
GUIAKQRZOPUOCW-UHFFFAOYSA-N P(=O)(O)(O)O.C(C)OP(=O)(OCC)Cl Chemical compound P(=O)(O)(O)O.C(C)OP(=O)(OCC)Cl GUIAKQRZOPUOCW-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 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
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
LHMRVAWTCGBZLK-UHFFFAOYSA-N n-trityl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)NC1=NC=CS1 LHMRVAWTCGBZLK-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000011574 phosphorus Chemical group 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
229930000044 secondary metabolite Natural products 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
150000003582 thiophosphoric acids Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
150000003952 β-lactams Chemical class 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

RO96-01614A 1994-03-21 1994-12-07 Derivati tiofosfat ai acidului tia(dia)zolacetic si procedeu pentru prepararea acestora RO113245B1 (ro)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
KR1019940005658A KR0129567B1 (ko)	1994-03-21	1994-03-21	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법

Publications (1)

Publication Number	Publication Date
RO113245B1 true RO113245B1 (ro)	1998-05-29

Family

ID=19379305

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
RO96-01614A RO113245B1 (ro)	1994-03-21	1994-12-07	Derivati tiofosfat ai acidului tia(dia)zolacetic si procedeu pentru prepararea acestora
RO94-01960A RO111682B1 (ro)	1994-03-21	1994-12-07	Procedeu pentru prepararea unor derivati de cefalosporina

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
RO94-01960A RO111682B1 (ro)	1994-03-21	1994-12-07	Procedeu pentru prepararea unor derivati de cefalosporina

Country Status (5)

Country	Link
KR (1)	KR0129567B1 (pl)
MX (1)	MXPA94009625A (pl)
PL (1)	PL179321B1 (pl)
RO (2)	RO113245B1 (pl)
RU (1)	RU2097385C1 (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100967341B1 (ko) *	2008-04-01	2010-07-05	주식회사 이매진	카바페넴 합성 중간체의 제조방법
CN111072592B (zh) *	2019-12-20	2021-07-20	河北合佳医药科技集团股份有限公司	一种氨噻肟酸二聚体的高纯度选择性制备和纯化方法

1994
- 1994-03-21 KR KR1019940005658A patent/KR0129567B1/ko not_active Expired - Lifetime
- 1994-12-07 RO RO96-01614A patent/RO113245B1/ro unknown
- 1994-12-07 RO RO94-01960A patent/RO111682B1/ro unknown
- 1994-12-09 RU RU9494043775A patent/RU2097385C1/ru not_active IP Right Cessation
- 1994-12-09 PL PL94306199A patent/PL179321B1/pl not_active IP Right Cessation
- 1994-12-13 MX MXPA94009625A patent/MXPA94009625A/es active IP Right Grant

Also Published As

Publication number	Publication date
RU94043775A (ru)	1996-09-27
MXPA94009625A (es)	2005-08-24
KR950026881A (ko)	1995-10-16
PL179321B1 (pl)	2000-08-31
PL306199A1 (en)	1995-10-02
RU2097385C1 (ru)	1997-11-27
KR0129567B1 (ko)	1998-04-09
RO111682B1 (ro)	1996-12-30

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EP0422596A2 (en)	1991-04-17	Tricyclic carbapenem compounds
US3741959A (en)	1973-06-26	Acylation of 7-aminocephalosporin or 6-aminopenicillin
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NZ200155A (en)	1985-08-16	Phosphorus-containing beta-lactams
RO113245B1 (ro)	1998-05-29	Derivati tiofosfat ai acidului tia(dia)zolacetic si procedeu pentru prepararea acestora
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US4008226A (en)	1977-02-15	Intermediates for preparing semi-synthetic cephalosporins and processes relating thereto
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PL172378B1 (pl)	1997-09-30	Sposób wytwarzania nowych 4-podstawionych azetydynonów PL PL PL PL PL PL
PL84450B1 (pl)	1976-04-30
EP0096496B1 (en)	1986-07-23	Preparation of penicillin and cephalosporin compounds and novel intermediates useful therein
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EP0127177B1 (en)	1988-12-21	[[(3-Acylamino-2-oxo-1-azetidinyl)oxy]methyl]phosphinic acids
US4939250A (en)	1990-07-03	Process for preparation of β-lactam derivatives
EP0377987A2 (en)	1990-07-18	Acylation process for obtaining cephalosporin derivatives
US3962215A (en)	1976-06-08	Intermediates for preparing semi-synthetic penicillins and processes relating thereto