DD151942A5 - Verfahren zur herstellung von amino-thiadiazolylverbindungen - Google Patents

Verfahren zur herstellung von amino-thiadiazolylverbindungen Download PDF

Info

Publication number: DD151942A5
Authority: DD; German Democratic Republic
Prior art keywords: sub; formula; thiadiazol; acid; cephem
Prior art date: 1979-07-05

Application number

DD80222421A

Other languages

German (de)

English (en)

Inventor

Ivan Csendes

Beat Mueller

Riccardo Scartazzini

Original Assignee

Ciba Geigy Ag

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.)

1979-07-05

Filing date

1980-07-04

Publication date

1981-11-11

1980-07-04 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-11-11 Publication of DD151942A5 publication Critical patent/DD151942A5/de

Links

-1 AMINO-THIADIAZOLYL COMPOUNDS Chemical class 0.000 title claims abstract description 469
238000000034 method Methods 0.000 title claims abstract description 62
238000002360 preparation method Methods 0.000 title claims description 40
230000008569 process Effects 0.000 title claims description 27
150000001875 compounds Chemical class 0.000 claims abstract description 265
150000003839 salts Chemical class 0.000 claims abstract description 85
125000000217 alkyl group Chemical group 0.000 claims abstract description 82
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 77
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 39
125000003277 amino group Chemical group 0.000 claims abstract description 29
125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004423 acyloxy group Chemical group 0.000 claims abstract description 14
125000004468 heterocyclylthio group Chemical group 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims description 60
239000003795 chemical substances by application Substances 0.000 claims description 43
229910052736 halogen Inorganic materials 0.000 claims description 40
150000002367 halogens Chemical group 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 20
229910021529 ammonia Inorganic materials 0.000 claims description 16
229910052751 metal Inorganic materials 0.000 claims description 15
239000002184 metal Substances 0.000 claims description 14
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000001408 amides Chemical class 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000001302 tertiary amino group Chemical group 0.000 claims description 10
150000001735 carboxylic acids Chemical class 0.000 claims description 8
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 7
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 7
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
150000001782 cephems Chemical class 0.000 claims description 3
VIUQMUGXYQJBQK-IOJJLOCKSA-N (6r)-4-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(COC(=O)C)S[C@@H]2CC(=O)N21 VIUQMUGXYQJBQK-IOJJLOCKSA-N 0.000 claims description 2
XIIRUKYIKAFBEZ-XNWCZRBMSA-N (2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamide Chemical compound CO\N=C(/C(N)=O)C1=NSC(N)=N1 XIIRUKYIKAFBEZ-XNWCZRBMSA-N 0.000 claims 2
FVUJPXXDENYILK-WITUOYQCSA-N (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoic acid Chemical compound CC(C)C[C@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)Cc1cnc[nH]1)[C@@H](C)O)[C@@H](C)O)C(=O)N[C@@H](C(C)C)C(N)=O FVUJPXXDENYILK-WITUOYQCSA-N 0.000 claims 1
JJXRANHOCVAFMF-SNVBAGLBSA-N 2,2-dimethylpropanoyloxymethyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=CCS[C@@H]2CC(=O)N12 JJXRANHOCVAFMF-SNVBAGLBSA-N 0.000 claims 1
102100036883 Cyclin-H Human genes 0.000 claims 1
101000713120 Homo sapiens Cyclin-H Proteins 0.000 claims 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
241000252067 Megalops atlanticus Species 0.000 claims 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
NFYVBTLGVJOFIH-UHFFFAOYSA-N tetrazol-1-ylmethanesulfonic acid Chemical compound OS(=O)(=O)CN1C=NN=N1 NFYVBTLGVJOFIH-UHFFFAOYSA-N 0.000 claims 1
125000004001 thioalkyl group Chemical group 0.000 claims 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
108700043117 vasectrin I Proteins 0.000 claims 1
230000003115 biocidal effect Effects 0.000 abstract description 6
239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
238000007911 parenteral administration Methods 0.000 abstract description 2
208000035143 Bacterial infection Diseases 0.000 abstract 1
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
208000022362 bacterial infectious disease Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 304
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 146
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
239000002253 acid Substances 0.000 description 117
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 111
239000000243 solution Substances 0.000 description 111
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 102
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 92
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
239000000741 silica gel Substances 0.000 description 72
229910002027 silica gel Inorganic materials 0.000 description 72
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 67
238000010521 absorption reaction Methods 0.000 description 63
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
238000002329 infrared spectrum Methods 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 52
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 41
229960000583 acetic acid Drugs 0.000 description 39
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
229910052757 nitrogen Inorganic materials 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
239000000460 chlorine Substances 0.000 description 31
229910052943 magnesium sulfate Inorganic materials 0.000 description 31
235000019341 magnesium sulphate Nutrition 0.000 description 31
239000002585 base Substances 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
150000008064 anhydrides Chemical class 0.000 description 28
239000000725 suspension Substances 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
235000017557 sodium bicarbonate Nutrition 0.000 description 26
229910000030 sodium bicarbonate Inorganic materials 0.000 description 26
125000003118 aryl group Chemical group 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 24
125000000524 functional group Chemical group 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
239000011780 sodium chloride Substances 0.000 description 23
239000007858 starting material Substances 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
150000007513 acids Chemical class 0.000 description 22
238000004587 chromatography analysis Methods 0.000 description 22
239000002904 solvent Substances 0.000 description 22
238000005917 acylation reaction Methods 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
230000010933 acylation Effects 0.000 description 20
229910052801 chlorine Inorganic materials 0.000 description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
239000012362 glacial acetic acid Substances 0.000 description 20
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
150000003254 radicals Chemical class 0.000 description 20
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
125000001931 aliphatic group Chemical group 0.000 description 17
229910052783 alkali metal Inorganic materials 0.000 description 17
238000001816 cooling Methods 0.000 description 17
239000011261 inert gas Substances 0.000 description 17
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 16
238000010438 heat treatment Methods 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
238000002211 ultraviolet spectrum Methods 0.000 description 16
150000001340 alkali metals Chemical class 0.000 description 15
239000008346 aqueous phase Substances 0.000 description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 description 13
150000003973 alkyl amines Chemical class 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
150000004820 halides Chemical class 0.000 description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
159000000000 sodium salts Chemical class 0.000 description 13
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 13
125000002252 acyl group Chemical group 0.000 description 12
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000003638 chemical reducing agent Substances 0.000 description 10
229930195733 hydrocarbon Natural products 0.000 description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 9
150000003863 ammonium salts Chemical class 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
238000001914 filtration Methods 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
150000007530 organic bases Chemical class 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
125000003282 alkyl amino group Chemical group 0.000 description 8
150000008282 halocarbons Chemical class 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
150000007522 mineralic acids Chemical class 0.000 description 8
150000003512 tertiary amines Chemical class 0.000 description 8
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
239000013543 active substance Substances 0.000 description 7
QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
230000009467 reduction Effects 0.000 description 7
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 7
125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
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229940049954 penicillin Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical class [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
230000007017 scission Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 1
YGBMIWKJLZVZRD-UHFFFAOYSA-N tert-butyl 2-methoxyiminoacetate Chemical compound C(C)(C)(C)OC(C=NOC)=O YGBMIWKJLZVZRD-UHFFFAOYSA-N 0.000 description 1
QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 description 1
KTCBOFXRIMWQPS-UHFFFAOYSA-N tert-butyl n-(3-formyl-1,2,4-thiadiazol-5-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=NC(C=O)=NS1 KTCBOFXRIMWQPS-UHFFFAOYSA-N 0.000 description 1
IGEBDAJWENTTJX-UHFFFAOYSA-N tert-butyl n-(thiadiazol-5-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CN=NS1 IGEBDAJWENTTJX-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
NKNUDEWJLANKLU-UHFFFAOYSA-N tert-butyl n-methyl-n-(3-methyl-1,2,4-thiadiazol-5-yl)carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=NC(C)=NS1 NKNUDEWJLANKLU-UHFFFAOYSA-N 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000006177 thiolation reaction Methods 0.000 description 1
239000011135 tin Substances 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000010555 transalkylation reaction Methods 0.000 description 1
125000005039 triarylmethyl group Chemical group 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
BNCXNUWGWUZTCN-UHFFFAOYSA-N trichloro(dodecyl)silane Chemical compound CCCCCCCCCCCC[Si](Cl)(Cl)Cl BNCXNUWGWUZTCN-UHFFFAOYSA-N 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

DD80222421A 1979-07-05 1980-07-04 Verfahren zur herstellung von amino-thiadiazolylverbindungen DD151942A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH629479		1979-07-05
CH136580		1980-02-20

Publications (1)

Publication Number	Publication Date
DD151942A5 true DD151942A5 (de)	1981-11-11

Family

ID=25687457

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80222421A DD151942A5 (de)	1979-07-05	1980-07-04	Verfahren zur herstellung von amino-thiadiazolylverbindungen

Country Status (13)

Country	Link
EP (1)	EP0022245A3 (es)
AU (1)	AU6011480A (es)
DD (1)	DD151942A5 (es)
DK (1)	DK291380A (es)
ES (7)	ES8105738A1 (es)
FI (1)	FI802107A7 (es)
GR (1)	GR69702B (es)
MA (1)	MA18891A1 (es)
NO (1)	NO802028L (es)
NZ (1)	NZ194241A (es)
OA (1)	OA06690A (es)
PT (1)	PT71498A (es)
ZW (1)	ZW15180A1 (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4431642A (en) *	1980-12-01	1984-02-14	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
GR75487B (es) *	1981-06-22	1984-07-23	Fujisawa Pharmaceutical Co
US4521413A (en) *	1981-09-14	1985-06-04	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
DE3300593A1 (de) *	1983-01-11	1984-07-12	Bayer Ag, 5090 Leverkusen	Neue cephalosporine und verfahren zu ihrer herstellung
EP0536900A3 (en) *	1991-09-12	1993-04-21	KATAYAMA SEIYAKUSYO CO. Ltd.	Process for preparing 1,2,4-thiadiazole derivatives
AR029004A1 (es) *	1999-09-22	2003-06-04	Essential Therapeutics Inc	Compuesto del acido 7-acilamino-3-heteroariltio-3-cefem carboxilico y su uso para la preparacion de una composicion antibacteriana
CN108299469B (zh) *	2017-01-12	2020-07-14	重庆常捷医药有限公司	一种头孢替安盐酸盐的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1592149A (en) *	1976-10-08	1981-07-01	Fujisawa Pharmaceutical Co	3 7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for preparation thereof
US4268509A (en) *	1978-07-10	1981-05-19	Fujisawa Pharmaceutical Co., Ltd.	New cephem compounds and processes for preparation thereof
AU536842B2 (en) *	1978-12-29	1984-05-24	Fujisawa Pharmaceutical Co., Ltd.	Cephalosporin antibiotics

1980
- 1980-07-01 MA MA19088A patent/MA18891A1/fr unknown
- 1980-07-01 FI FI802107A patent/FI802107A7/fi not_active Application Discontinuation
- 1980-07-02 EP EP80103772A patent/EP0022245A3/de not_active Withdrawn
- 1980-07-03 GR GR62354A patent/GR69702B/el unknown
- 1980-07-03 ZW ZW151/80A patent/ZW15180A1/xx unknown
- 1980-07-03 ES ES493068A patent/ES8105738A1/es not_active Expired
- 1980-07-04 PT PT71498A patent/PT71498A/pt unknown
- 1980-07-04 NZ NZ194241A patent/NZ194241A/xx unknown
- 1980-07-04 AU AU60114/80A patent/AU6011480A/en not_active Abandoned
- 1980-07-04 DK DK291380A patent/DK291380A/da unknown
- 1980-07-04 DD DD80222421A patent/DD151942A5/de unknown
- 1980-07-04 NO NO802028A patent/NO802028L/no unknown
- 1980-07-05 OA OA57155A patent/OA06690A/xx unknown
1981
- 1981-02-27 ES ES499912A patent/ES499912A1/es not_active Expired
- 1981-02-27 ES ES499918A patent/ES8202018A1/es not_active Expired
- 1981-02-27 ES ES499914A patent/ES499914A0/es active Granted
- 1981-02-27 ES ES499915A patent/ES499915A1/es not_active Expired
- 1981-02-27 ES ES499913A patent/ES499913A0/es active Granted
- 1981-02-27 ES ES499916A patent/ES499916A0/es active Granted

Also Published As

Publication number	Publication date
ZW15180A1 (en)	1981-01-21
DK291380A (da)	1981-01-06
EP0022245A2 (de)	1981-01-14
ES493068A0 (es)	1981-06-16
ES499915A1 (es)	1982-11-01
ES8202017A1 (es)	1982-01-01
NZ194241A (en)	1982-12-07
NO802028L (no)	1981-01-06
ES8205227A1 (es)	1982-06-01
ES499912A1 (es)	1982-12-16
ES499918A0 (es)	1982-01-01
ES499914A0 (es)	1982-01-01
ES499916A0 (es)	1982-06-01
FI802107A7 (fi)	1981-01-01
ES8202018A1 (es)	1982-01-01
AU6011480A (en)	1981-01-15
OA06690A (fr)	1982-05-31
ES8204998A1 (es)	1982-05-16
EP0022245A3 (de)	1981-04-01
ES8105738A1 (es)	1981-06-16
MA18891A1 (fr)	1981-04-01
PT71498A (en)	1980-08-01
GR69702B (es)	1982-07-08
ES499913A0 (es)	1982-05-16

Publication	Publication Date	Title
US3516997A (en)	1970-06-23	3,7-disubstituted cephalosporin compounds and preparation thereof
US4470983A (en)	1984-09-11	Cephalosporin derivatives
NO771285L (no)	1977-10-17	Nye cefalosporiner og fremgangsm}te til deres fremstilling
DD144772A5 (de)	1980-11-05	Verfahren zur herstellung von thiazol-verbindungen
DE2707565A1 (de)	1978-02-23	Syn-isomere von 3,7-disubstituierten-3-cephem-4-carbonsaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE2520561A1 (de)	1975-11-27	Cephalosporine mit alpha-acylaminoessigsaeureseitenkette
EP0009008A2 (de)	1980-03-19	Cephalosporinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DD201906A5 (de)	1983-08-17	Verfahren zur herstellung von 7 beta-aminothiadiazolylacetylamino-3 ammoniomethyl-3-cephem-4-carbonsaeureverbindungen
DE2347533A1 (de)	1974-04-04	Neue derivate der penam-3-carbonsaeure und cephem-4-carbonsaeure und verfahren zu ihrer herstellung
US4943567A (en)	1990-07-24	Cephalosporin compound and pharmaceutical composition thereof
DE2814641A1 (de)	1978-10-19	3,7-disubstituierte-3-cephem-4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH650786A5 (de)	1985-08-15	Cephemverbindungen und verfahren zu ihrer herstellung.
CA1146535A (en)	1983-05-17	Aminothiazoles with terminal aminocarboxylic acid grouping
DD151942A5 (de)	1981-11-11	Verfahren zur herstellung von amino-thiadiazolylverbindungen
DD152788A5 (de)	1981-12-09	Verfahren zur herstellung von polyazathiaverbindungen
US4971962A (en)	1990-11-20	Cephalosporin compounds
EP0049855A2 (de)	1982-04-21	Neue Cephalosporinderivate, Verfahren zu ihrer Herstellung und Zwischenprodukte dafür sowie entsprechende pharmazeutische Präparate
DE2359544A1 (de)	1975-10-30	Cephemderivate und verfahren zu ihrer herstellung
DE2934682A1 (de)	1980-03-13	3,7-disubstituierte-3-cephem-4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
CH642969A5 (de)	1984-05-15	7-trimethylsilyloxycarbonylamino-cephalosporinverbindungen und ihre verwendung zur herstellung von cephalosporinen.
US4454129A (en)	1984-06-12	Cephem derivatives
EP0037797A2 (de)	1981-10-14	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung
CH643266A5 (en)	1984-05-30	3,7-Disubstituted 3-cephem-4-carboxylic acids and esters thereof, processes for their preparation and pharmaceuticals containing them
EP0008343A1 (de)	1980-03-05	Cephalosporinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DD204256A5 (de)	1983-11-23	Verfahren zur herstellung von aminooxazolylverbindungen