NO792265L - Aminotiasolforbindelser. - Google Patents

Aminotiasolforbindelser.

Info

Publication number: NO792265L
Authority: NO; Norway
Prior art keywords: formula; group; amino; compound; carboxylic acid
Prior art date: 1978-07-07

Application number

NO792265A

Other languages

English (en)

Norwegian (no)

Inventor

Riccardo Scartazzini

Rene Wiederkehr

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.)

1978-07-07

Filing date

1979-07-06

Publication date

1980-01-08

1979-07-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-01-08 Publication of NO792265L publication Critical patent/NO792265L/no

Links

-1 amino-thiazolyl-acetamido-3-cephem-4-carboxylic acid compounds Chemical class 0.000 claims description 285
150000001875 compounds Chemical class 0.000 claims description 105
150000003839 salts Chemical class 0.000 claims description 65
239000001257 hydrogen Substances 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 56
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
239000007858 starting material Substances 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 47
238000000034 method Methods 0.000 claims description 47
239000003795 chemical substances by application Substances 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
125000000524 functional group Chemical group 0.000 claims description 28
229910052740 iodine Inorganic materials 0.000 claims description 25
125000003277 amino group Chemical group 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
125000006239 protecting group Chemical group 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 18
125000002252 acyl group Chemical group 0.000 claims description 17
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
230000008569 process Effects 0.000 claims description 10
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
230000010933 acylation Effects 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 7
230000004962 physiological condition Effects 0.000 claims description 7
230000002829 reductive effect Effects 0.000 claims description 7
159000000000 sodium salts Chemical class 0.000 claims description 7
238000005886 esterification reaction Methods 0.000 claims description 5
150000001782 cephems Chemical group 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 4
125000005633 phthalidyl group Chemical group 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 3
239000012374 esterification agent Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 133
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
239000002253 acid Substances 0.000 description 78
239000000243 solution Substances 0.000 description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 65
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 49
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 41
239000000203 mixture Substances 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000002904 solvent Substances 0.000 description 32
239000002585 base Substances 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
125000003118 aryl group Chemical group 0.000 description 25
125000001931 aliphatic group Chemical group 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
239000008186 active pharmaceutical agent Substances 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
229910052751 metal Inorganic materials 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 19
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
229960000583 acetic acid Drugs 0.000 description 18
239000002184 metal Substances 0.000 description 18
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
150000008064 anhydrides Chemical class 0.000 description 17
238000001816 cooling Methods 0.000 description 17
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
229910052783 alkali metal Inorganic materials 0.000 description 16
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
239000003054 catalyst Substances 0.000 description 16
239000000460 chlorine Substances 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
238000010521 absorption reaction Methods 0.000 description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
150000007513 acids Chemical class 0.000 description 14
239000003638 chemical reducing agent Substances 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
150000001340 alkali metals Chemical class 0.000 description 13
238000002329 infrared spectrum Methods 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
238000006722 reduction reaction Methods 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
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 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
150000003973 alkyl amines Chemical class 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
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 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
235000011054 acetic acid Nutrition 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
150000004820 halides Chemical class 0.000 description 10
150000008282 halocarbons Chemical class 0.000 description 10
239000011261 inert gas Substances 0.000 description 10
150000007522 mineralic acids Chemical class 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
238000007254 oxidation reaction Methods 0.000 description 10
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
125000001589 carboacyl group Chemical group 0.000 description 9
238000003776 cleavage reaction Methods 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000002211 ultraviolet spectrum Methods 0.000 description 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
150000002430 hydrocarbons Chemical group 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 8
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
230000009467 reduction Effects 0.000 description 8
230000007017 scission Effects 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
238000006136 alcoholysis reaction Methods 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
239000007800 oxidant agent Substances 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
229910052725 zinc Inorganic materials 0.000 description 7
239000011701 zinc Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
239000002775 capsule Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
238000007327 hydrogenolysis reaction Methods 0.000 description 6
229910052742 iron Inorganic materials 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
235000011007 phosphoric acid Nutrition 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
238000003797 solvolysis reaction Methods 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
238000006606 decarbonylation reaction Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
150000003003 phosphines Chemical class 0.000 description 5
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
229910052718 tin Inorganic materials 0.000 description 5
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
230000021235 carbamoylation Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
230000006324 decarbonylation Effects 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
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 4
239000000706 filtrate Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
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125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
XWVKTOHUMPLABF-UHFFFAOYSA-N thallium(3+) Chemical compound [Tl+3] XWVKTOHUMPLABF-UHFFFAOYSA-N 0.000 description 1
KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical class C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000002023 wood Substances 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO792265A 1978-07-07 1979-07-06 Aminotiasolforbindelser. NO792265L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH742278		1978-07-07
CH1301678		1978-12-21

Publications (1)

Publication Number	Publication Date
NO792265L true NO792265L (no)	1980-01-08

Family

ID=25701313

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792265A NO792265L (no)	1978-07-07	1979-07-06	Aminotiasolforbindelser.

Country Status (17)

Country	Link
EP (1)	EP0008343B1 (bg)
BG (8)	BG34458A3 (bg)
CS (3)	CS216935B2 (bg)
DD (1)	DD144779A5 (bg)
DK (1)	DK286779A (bg)
EG (1)	EG14607A (bg)
ES (1)	ES482194A1 (bg)
FI (1)	FI792112A (bg)
GR (1)	GR73032B (bg)
HU (1)	HU182020B (bg)
IL (1)	IL57735A (bg)
MA (1)	MA18686A1 (bg)
NO (1)	NO792265L (bg)
OA (1)	OA06287A (bg)
PL (1)	PL216945A1 (bg)
PT (1)	PT69884A (bg)
RO (3)	RO81936A (bg)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR78221B (bg) *	1980-02-01	1984-09-26	Ciba Geigy Ag
EP0054512A3 (de) *	1980-12-12	1983-08-03	Ciba-Geigy Ag	Cephalosporinester, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
IT1142096B (it) *	1980-12-15	1986-10-08	Fujisawa Pharmaceutical Co	Derivati dell'acido 7-acilammino cefalosporanico e procedimenti per la loro preparazione
JPS57193489A (en) *	1981-05-21	1982-11-27	Fujisawa Pharmaceut Co Ltd	Syn-isomer of 7-substituted-3-cephem-4-carboxylic acid ester and its preparation
WO1984001949A1 (en) *	1982-11-10	1984-05-24	Kyoto Pharma Ind	Cephalosporin derivatives, process and their preparation, and prophylactic and treating agent against bacterial infection

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI771866A (bg) *	1976-06-28	1977-12-29	Fujisawa Pharmaceutical Co
ES467601A1 (es) *	1977-03-12	1979-06-16	Hoechst Ag	Procedimiento para la preparacion de derivados de cefem.
US4370326A (en) *	1977-09-13	1983-01-25	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds and composition

1979
- 1979-07-02 MA MA18701A patent/MA18686A1/fr unknown
- 1979-07-03 EG EG79404A patent/EG14607A/xx active
- 1979-07-04 RO RO79105231A patent/RO81936A/ro unknown
- 1979-07-04 EP EP79102273A patent/EP0008343B1/de not_active Expired
- 1979-07-04 ES ES482194A patent/ES482194A1/es not_active Expired
- 1979-07-04 RO RO7998045A patent/RO77940A/ro unknown
- 1979-07-04 RO RO79105230A patent/RO81937A/ro unknown
- 1979-07-04 FI FI792112A patent/FI792112A/fi not_active Application Discontinuation
- 1979-07-05 OA OA56840A patent/OA06287A/xx unknown
- 1979-07-05 GR GR59518A patent/GR73032B/el unknown
- 1979-07-05 DD DD79214148A patent/DD144779A5/de unknown
- 1979-07-06 NO NO792265A patent/NO792265L/no unknown
- 1979-07-06 BG BG047198A patent/BG34458A3/bg unknown
- 1979-07-06 PT PT69884A patent/PT69884A/pt unknown
- 1979-07-06 BG BG048161A patent/BG34460A3/bg unknown
- 1979-07-06 BG BG048162A patent/BG34461A3/bg unknown
- 1979-07-06 BG BG044230A patent/BG34454A3/bg unknown
- 1979-07-06 DK DK286779A patent/DK286779A/da not_active Application Discontinuation
- 1979-07-06 CS CS794776A patent/CS216935B2/cs unknown
- 1979-07-06 BG BG047197A patent/BG34457A3/bg unknown
- 1979-07-06 BG BG047196A patent/BG34456A3/bg unknown
- 1979-07-06 CS CS794776A patent/CS216937B2/cs unknown
- 1979-07-06 BG BG047195A patent/BG34455A3/bg unknown
- 1979-07-06 HU HU79CI1950A patent/HU182020B/hu unknown
- 1979-07-06 BG BG048160A patent/BG34459A3/bg unknown
- 1979-07-06 CS CS794776A patent/CS216938B2/cs unknown
- 1979-07-06 IL IL57735A patent/IL57735A/xx unknown
- 1979-07-07 PL PL21694579A patent/PL216945A1/xx unknown

Also Published As

Publication number	Publication date
BG34461A3 (bg)	1983-09-15
OA06287A (fr)	1981-06-30
RO81936B (ro)	1983-05-30
BG34455A3 (bg)	1983-09-15
RO81937B (ro)	1983-05-30
EP0008343A1 (de)	1980-03-05
PL216945A1 (bg)	1980-03-24
EG14607A (en)	1985-03-31
EP0008343B1 (de)	1983-04-06
DK286779A (da)	1980-01-08
ES482194A1 (es)	1980-04-01
FI792112A (fi)	1980-01-08
RO81936A (ro)	1983-06-01
CS216935B2 (en)	1982-12-31
HU182020B (en)	1983-12-28
PT69884A (en)	1979-08-01
BG34458A3 (bg)	1983-09-15
BG34457A3 (bg)	1983-09-15
BG34456A3 (bg)	1983-09-15
RO81937A (ro)	1983-06-01
DD144779A5 (de)	1980-11-05
BG34454A3 (bg)	1983-09-15
BG34460A3 (bg)	1983-09-15
BG34459A3 (bg)	1983-09-15
RO77940A (ro)	1981-12-25
CS216937B2 (en)	1982-12-31
IL57735A (en)	1985-03-31
CS216938B2 (en)	1982-12-31
MA18686A1 (fr)	1980-10-01
GR73032B (bg)	1984-01-26

Publication	Publication Date	Title
EP0136721B1 (en)	1993-12-29	Carboxyalkenamidocephalosporins
US4297488A (en)	1981-10-27	7-α-Methoxy cephalosporins
US4073902A (en)	1978-02-14	O-Substituted 7β-amino-3-cephem-3-ol-4-carboxylic acid compounds
DD201906A5 (de)	1983-08-17	Verfahren zur herstellung von 7 beta-aminothiadiazolylacetylamino-3 ammoniomethyl-3-cephem-4-carbonsaeureverbindungen
BG98723A (en)	1995-03-31	Cephalosporines
EP0009008A2 (de)	1980-03-19	Cephalosporinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
RU2056425C1 (ru)	1996-03-20	Производные цефалоспорина или их фармацевтически приемлемые кислотно-аддитивные соли и способы их получения
US4943567A (en)	1990-07-24	Cephalosporin compound and pharmaceutical composition thereof
US3674784A (en)	1972-07-04	3-formyl cephalosporin sulfoxides
US4313945A (en)	1982-02-02	7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic acid grouping
US4731361A (en)	1988-03-15	Alkeneamidocephalosporin esters
NO792265L (no)	1980-01-08	Aminotiasolforbindelser.
IE52008B1 (en)	1987-05-13	Novel esters
NO802532L (no)	1981-03-02	Polyazatioforbindelser, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende slike forbindelser og anvendelsen av sistnevnte
JPS6019916B2 (ja)	1985-05-18	０−置換された７β−アミノ−３−セフエム−３−オ−ル−４−カルボン酸化合物の製法
US4467101A (en)	1984-08-21	Compounds with terminal aminocarboxylic acid grouping
NO802028L (no)	1981-01-06	Amino-thiadiazolylforbindelser, fremgangsmaate for deres fremstilling, farmasoeytiske preparater inneholdende slike forbindelser og anvendelse av sistnevnte
EP0037797A2 (de)	1981-10-14	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung
GB2106519A (en)	1983-04-13	Aminooxazolyl compounds
US4464366A (en)	1984-08-07	Cephem compounds having a terminal aminocarboxylic acid grouping and containing an azacyclyl(thio)ureido group
US4324890A (en)	1982-04-13	Cephalosporin intermediates
US4343937A (en)	1982-08-10	3-Substituted-7-methoxy-7-amino-3-cephem-4-carboxylic acids
US4338438A (en)	1982-07-06	Cephalosporin antibiotics
DE3518848A1 (de)	1985-11-28	Aminoaethylthioverbindungen
NO882652L (no)	1988-12-19	Acylderivater.