JPS625917B2 - - Google Patents

Info

Publication number: JPS625917B2
Authority: JP; Japan
Prior art keywords: group; methyl; dioxo; ethyl; tetrahydro
Prior art date: 1974-06-21
Legal status (The legal status 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 status listed.): Expired

Application number

JP50074251A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5113793A (de

Inventor

Montafuon Maruku

Rainaa Rooran

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

F Hoffmann La Roche AG

Original Assignee

F Hoffmann La Roche 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.)

1974-06-21

Filing date

1975-06-18

Publication date

1987-02-07

1975-06-18 Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG

1976-02-03 Publication of JPS5113793A publication Critical patent/JPS5113793A/ja

1987-02-07 Publication of JPS625917B2 publication Critical patent/JPS625917B2/ja

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 65
150000003839 salts Chemical class 0.000 claims description 51
238000000034 method Methods 0.000 claims description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
125000002252 acyl group Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
229940124587 cephalosporin Drugs 0.000 claims description 5
229930186147 Cephalosporin Natural products 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
150000007530 organic bases Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
230000003115 biocidal effect Effects 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
150000001780 cephalosporins Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims 1
229940088710 antibiotic agent Drugs 0.000 claims 1
125000001271 cephalosporin group Chemical group 0.000 claims 1
-1 alkali metal salts Chemical class 0.000 description 110
159000000000 sodium salts Chemical class 0.000 description 63
238000002844 melting Methods 0.000 description 58
230000008018 melting Effects 0.000 description 58
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
238000002360 preparation method Methods 0.000 description 43
238000000354 decomposition reaction Methods 0.000 description 41
125000000217 alkyl group Chemical group 0.000 description 38
239000000243 solution Substances 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
239000007858 starting material Substances 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
229960000603 cefalotin Drugs 0.000 description 27
239000000203 mixture Substances 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 19
239000002253 acid Substances 0.000 description 19
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
125000003545 alkoxy group Chemical group 0.000 description 11
238000003756 stirring Methods 0.000 description 11
RYYFGLZKLWPYRH-UHFFFAOYSA-N 3-sulfanylidene-1,2,4-triazine-5,6-dione Chemical class SC1=NC(=O)C(=O)N=N1 RYYFGLZKLWPYRH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
125000004093 cyano group Chemical group *C#N 0.000 description 10
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 8
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
150000002367 halogens Chemical group 0.000 description 8
239000000463 material Substances 0.000 description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
HCQABJQZDYSTJH-QFSRMBNQSA-N (6r)-4-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(NC(=O)C)S[C@@H]2CC(=O)N21 HCQABJQZDYSTJH-QFSRMBNQSA-N 0.000 description 6
UUPZTFTUZUQRQT-UHFFFAOYSA-N 2-thiophen-2-ylacetamide Chemical compound NC(=O)CC1=CC=CS1 UUPZTFTUZUQRQT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000005236 alkanoylamino group Chemical group 0.000 description 6
239000000047 product Substances 0.000 description 6
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 5
150000007513 acids Chemical class 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
229910001873 dinitrogen Inorganic materials 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
KPLDRYODCDLNHB-UHFFFAOYSA-N 1-ethylpyrimidine-2,4-dione Chemical compound CCN1C=CC(=O)NC1=O KPLDRYODCDLNHB-UHFFFAOYSA-N 0.000 description 4
GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-UHFFFAOYSA-N 0.000 description 4
LFYOIWKDYNCFNR-UHFFFAOYSA-N 4-ethyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCN1C(S)=NN=C(O)C1=O LFYOIWKDYNCFNR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229950004030 cefaloglycin Drugs 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
125000002723 alicyclic group Chemical group 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000002541 furyl group Chemical group 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
125000001425 triazolyl group Chemical group 0.000 description 3
KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 description 2
DGOUJJSVYKEJKS-TVKKRMFBSA-N (6r)-8-oxo-4-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C([C@H]1S2)C(=O)N1C(C(=O)O)=CC2NC(=O)CC1=CC=CS1 DGOUJJSVYKEJKS-TVKKRMFBSA-N 0.000 description 2
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 description 2
LVRFTAZAXQPQHI-RXMQYKEDSA-N (R)-2-hydroxy-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](O)C(O)=O LVRFTAZAXQPQHI-RXMQYKEDSA-N 0.000 description 2
MAGPZHKLEZXLNU-SSDOTTSWSA-N (R)-mandelamide Chemical compound NC(=O)[C@H](O)C1=CC=CC=C1 MAGPZHKLEZXLNU-SSDOTTSWSA-N 0.000 description 2
BMBKIGKFUHIDPU-UHFFFAOYSA-N 1-carbamothioyl-3-methylurea Chemical compound CNC(=O)NC(N)=S BMBKIGKFUHIDPU-UHFFFAOYSA-N 0.000 description 2
KZSLHPBJJSPILT-UHFFFAOYSA-N 1-ethyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CCN1NC(=S)NC(=O)C1=O KZSLHPBJJSPILT-UHFFFAOYSA-N 0.000 description 2
ILEZLXLLLYYQAX-UHFFFAOYSA-N 1-ethyl-4-sulfanylidenepyrimidin-2-one Chemical compound CCN1C=CC(S)=NC1=O ILEZLXLLLYYQAX-UHFFFAOYSA-N 0.000 description 2
RRDPWAPIJGSANI-UHFFFAOYSA-N 2-cyclohexyl-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1CCCCC1 RRDPWAPIJGSANI-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 2
DDGUXTGMUNEGOJ-UHFFFAOYSA-N 4-(2-methoxyethyl)-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound COCCN1C(=S)NNC(=O)C1=O DDGUXTGMUNEGOJ-UHFFFAOYSA-N 0.000 description 2
CJDXQHXLUSJTMO-UHFFFAOYSA-N 4-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione Chemical compound CN1C(S)=NN=C(O)C1=O CJDXQHXLUSJTMO-UHFFFAOYSA-N 0.000 description 2
OWKCZXVFRZFBGA-UHFFFAOYSA-N 5-chloro-1-ethylpyrimidine-2,4-dione Chemical compound CCN1C=C(Cl)C(=O)NC1=O OWKCZXVFRZFBGA-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
239000004593 Epoxy Chemical group 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
LVRFTAZAXQPQHI-UHFFFAOYSA-N alpha-hydroxyisocaproic acid Natural products CC(C)CC(O)C(O)=O LVRFTAZAXQPQHI-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 description 2
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
MAGPZHKLEZXLNU-UHFFFAOYSA-N phenyl-alpha-hydroxyacetamide Natural products NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
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230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
229950009506 penicillinase Drugs 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005323 thioketone group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003583 thiosemicarbazides Chemical class 0.000 description 1
ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
229940035893 uracil Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
- 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP50074251A 1974-06-21 1975-06-18 Expired JPS625917B2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH853774A CH609989A5 (en)	1974-06-21	1974-06-21	Process for the preparation of acyl derivatives

Publications (2)

Publication Number	Publication Date
JPS5113793A JPS5113793A (de)	1976-02-03
JPS625917B2 true JPS625917B2 (de)	1987-02-07

Family

ID=4341690

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP50074251A Expired JPS625917B2 (de)	1974-06-21	1975-06-18

Country Status (25)

Country	Link
JP (1)	JPS625917B2 (de)
AT (1)	AT337897B (de)
AU (1)	AU498387B2 (de)
BE (1)	BE830455A (de)
BR (1)	BR7503782A (de)
CA (1)	CA1111021A (de)
CH (1)	CH609989A5 (de)
CU (1)	CU34293A (de)
DD (1)	DD121113A5 (de)
DE (1)	DE2527291A1 (de)
DK (2)	DK153155C (de)
FI (1)	FI751815A (de)
FR (1)	FR2275215A1 (de)
GB (1)	GB1471804A (de)
HU (1)	HU170576B (de)
IE (1)	IE41888B1 (de)
IL (1)	IL47299A (de)
LU (1)	LU72771A1 (de)
NL (1)	NL180665C (de)
NO (1)	NO752202L (de)
NZ (1)	NZ177508A (de)
PH (1)	PH13030A (de)
SE (1)	SE431755B (de)
SU (2)	SU635873A3 (de)
ZA (1)	ZA753086B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1599232A (en) *	1977-06-03	1981-09-30	Hoffmann La Roche	7-(2-oximinoacetamido)-cephalosporin derivatives
JPS5419990A (en) *	1977-07-14	1979-02-15	Shionogi & Co Ltd	Dihydrotriazinylthioxacephalosporin
MC1259A1 (fr) *	1978-05-30	1980-01-14	Hoffmann La Roche	Derives acyles
FR2474030A1 (fr) *	1980-01-17	1981-07-24	Rhone Poulenc Ind	Nouvelles dioxotriazines et leur preparation
FR2494278A1 (fr) *	1980-11-20	1982-05-21	Rhone Poulenc Ind	Nouveaux derives de la cephalosporine, leurs preparations et les medicaments qui les contiennent
WO2002086143A2 (en) *	2001-04-19	2002-10-31	Bioferma Murcia, S.A.	Enzymatic process for preparing cephalosporin derivatives
AU2009221328B2 (en)	2008-03-05	2014-02-27	Merck Patent Gmbh	Pyrazinone derivatives as insulin secretion stimulators, methods for obtaining them and use thereof for the treatment of diabetes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3868369A (en) *	1972-11-14	1975-02-25	Smithkline Corp	3-heterocyclicthiomethylcephalosporins

1974
- 1974-06-21 CH CH853774A patent/CH609989A5/xx not_active IP Right Cessation
1975
- 1975-05-13 NZ NZ177508A patent/NZ177508A/xx unknown
- 1975-05-13 ZA ZA00753086A patent/ZA753086B/xx unknown
- 1975-05-14 IL IL47299A patent/IL47299A/xx unknown
- 1975-06-06 AU AU81912/75A patent/AU498387B2/en not_active Expired
- 1975-06-16 SE SE7506908A patent/SE431755B/xx not_active IP Right Cessation
- 1975-06-17 BR BR4864/75D patent/BR7503782A/pt unknown
- 1975-06-17 DK DK271975A patent/DK153155C/da not_active IP Right Cessation
- 1975-06-17 PH PH17273A patent/PH13030A/en unknown
- 1975-06-18 JP JP50074251A patent/JPS625917B2/ja not_active Expired
- 1975-06-18 IE IE1366/75A patent/IE41888B1/en unknown
- 1975-06-18 FI FI751815A patent/FI751815A/fi not_active Application Discontinuation
- 1975-06-18 SU SU752145554A patent/SU635873A3/ru active
- 1975-06-19 FR FR7519213A patent/FR2275215A1/fr active Granted
- 1975-06-19 DE DE19752527291 patent/DE2527291A1/de active Granted
- 1975-06-19 LU LU72771A patent/LU72771A1/xx unknown
- 1975-06-20 BE BE157517A patent/BE830455A/xx not_active IP Right Cessation
- 1975-06-20 DD DD186797A patent/DD121113A5/xx unknown
- 1975-06-20 CU CU7534293A patent/CU34293A/es unknown
- 1975-06-20 CA CA229,803A patent/CA1111021A/en not_active Expired
- 1975-06-20 NL NLAANVRAGE7507390,A patent/NL180665C/xx not_active IP Right Cessation
- 1975-06-20 HU HUHO1808A patent/HU170576B/hu unknown
- 1975-06-20 AT AT476975A patent/AT337897B/de not_active IP Right Cessation
- 1975-06-20 GB GB2634175A patent/GB1471804A/en not_active Expired
- 1975-06-20 NO NO752202A patent/NO752202L/no unknown
1976
- 1976-01-07 SU SU762309104A patent/SU589921A3/ru active
1987
- 1987-08-28 DK DK453687A patent/DK155329C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK271975A (da)	1975-12-22
FR2275215A1 (fr)	1976-01-16
CH609989A5 (en)	1979-03-30
FR2275215B1 (de)	1980-05-16
LU72771A1 (de)	1977-03-04
DE2527291A1 (de)	1976-01-08
DK153155B (da)	1988-06-20
CA1111021A (en)	1981-10-20
AT337897B (de)	1977-07-25
NL180665B (nl)	1986-11-03
DK153155C (da)	1988-10-31
BR7503782A (pt)	1976-07-06
NO752202L (de)	1975-12-23
ATA476975A (de)	1976-11-15
DK155329C (da)	1989-08-07
HU170576B (de)	1977-07-28
IL47299A0 (en)	1976-10-31
SU635873A3 (ru)	1978-11-30
ZA753086B (en)	1976-04-28
PH13030A (en)	1979-11-15
DE2527291C2 (de)	1988-01-14
NL180665C (nl)	1987-04-01
IE41888B1 (en)	1980-04-23
AU8191275A (en)	1976-12-09
DK453687A (da)	1987-08-28
GB1471804A (en)	1977-04-27
DK453687D0 (da)	1987-08-28
DD121113A5 (de)	1976-07-12
SE7506908L (sv)	1975-12-22
SU589921A3 (ru)	1978-01-25
DK155329B (da)	1989-03-28
FI751815A (de)	1975-12-22
NZ177508A (en)	1978-04-03
AU498387B2 (en)	1979-03-08
CU34293A (es)	1979-01-16
BE830455A (fr)	1975-12-22
JPS5113793A (de)	1976-02-03
NL7507390A (nl)	1975-12-23
IL47299A (en)	1979-01-31
SE431755B (sv)	1984-02-27
IE41888L (en)	1975-12-21

Publication	Publication Date	Title
EP0189287B1 (de)	1992-12-16	Beta-Lactam-Antibiotika
US3984403A (en)	1976-10-05	Arginine and lysine salts of acid cephalosporins
US4603129A (en)	1986-07-29	Cephalosporin derivatives
JPS5858353B2 (ja)	1983-12-24	セフエムまたはペナム化合物およびその製造法
JPH0710870B2 (ja)	1995-02-08	新規セフェム化合物
JPH0333712B2 (de)	1991-05-20
KR910000035B1 (ko)	1991-01-19	세팔로스포린 화합물, 이의 제법 및 이를 함유하는 약학적 조성물
EP0112164A2 (de)	1984-06-27	Cephemverbindungen, ihre Herstellung und sie enthaltende Medikamente
JPS625917B2 (de)	1987-02-07
US4091211A (en)	1978-05-23	Cephalosporins
IE41590B1 (en)	1980-02-13	Novel cephalosporin compounds
JPH0633281B2 (ja)	1994-05-02	新規セファロスポリン化合物及び抗菌剤
US4348518A (en)	1982-09-07	Cephalosporins
JP2529093B2 (ja)	1996-08-28	セファロスポリン中間体の製造方法
KR790001023B1 (ko)	1979-08-20	아실 유도체의 제조방법
US4239758A (en)	1980-12-16	Cephalosporins
KR870000611B1 (ko)	1987-03-25	세팔로스포린의 제조방법
JPH0723381B2 (ja)	1995-03-15	新規セフアロスポリン誘導体及び抗菌剤
US4111981A (en)	1978-09-05	Intermediates for preparing substituted phenylglycylcephalosporins
JPH09506100A (ja)	1997-06-17	抗炎症剤および抗変性剤としての２−スピロ（２’−スピロシクロアルキル）シクロプロピルセファロスポリンスルホン類
JPH0613529B2 (ja)	1994-02-23	新規セフアロスポリン誘導体及び抗菌剤
US4003893A (en)	1977-01-18	3-Heterothio[(thioalkyl)thioacetyl]cephalosporanic derivatives
US4044047A (en)	1977-08-23	Intermediates for preparing substituted phenylglycylcephalosporins
JP2787683B2 (ja)	1998-08-20	新規なペナム誘導体およびその塩
US4022895A (en)	1977-05-10	Substituted phenylglycylcephalosporins