DD151941A5 - Verfahren zur herstellung von neuen beta-lactamen - Google Patents
Verfahren zur herstellung von neuen beta-lactamen Download PDFInfo
- Publication number
- DD151941A5 DD151941A5 DD80222305A DD22230580A DD151941A5 DD 151941 A5 DD151941 A5 DD 151941A5 DD 80222305 A DD80222305 A DD 80222305A DD 22230580 A DD22230580 A DD 22230580A DD 151941 A5 DD151941 A5 DD 151941A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydroxy
- general formula
- phenyl
- methyl
- spectrum
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 hydroxy, acetoxy , Aminocarbonyloxy- Chemical class 0.000 claims abstract description 221
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000002360 preparation method Methods 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000006239 protecting group Chemical group 0.000 claims abstract description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims abstract description 11
- 238000000338 in vitro Methods 0.000 claims abstract description 10
- 238000001727 in vivo Methods 0.000 claims abstract description 10
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 10
- 150000007530 organic bases Chemical class 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical group NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003952 β-lactams Chemical class 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract 2
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 121
- AVWRKZWQTYIKIY-UHFFFAOYSA-N ureidocarboxylic acid Natural products NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 36
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- 229930186147 Cephalosporin Natural products 0.000 claims description 32
- 229940124587 cephalosporin Drugs 0.000 claims description 32
- 150000001780 cephalosporins Chemical class 0.000 claims description 31
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 150000003230 pyrimidines Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UGZVCHWAXABBHR-UHFFFAOYSA-O pyridin-1-ium-1-carboxamide Chemical group NC(=O)[N+]1=CC=CC=C1 UGZVCHWAXABBHR-UHFFFAOYSA-O 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- ROZRRDJERVTUDB-UHFFFAOYSA-O (1-carbamoyloxy-3-hydroxypyridin-1-ium-2-yl) acetate Chemical compound CC(=O)OC1=C(O)C=CC=[N+]1OC(N)=O ROZRRDJERVTUDB-UHFFFAOYSA-O 0.000 claims description 2
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 1
- 229960004279 formaldehyde Drugs 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 claims 1
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical compound N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 8
- 239000004480 active ingredient Substances 0.000 abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 247
- 238000002329 infrared spectrum Methods 0.000 description 106
- 238000001228 spectrum Methods 0.000 description 106
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 103
- 159000000000 sodium salts Chemical class 0.000 description 88
- 239000011734 sodium Substances 0.000 description 83
- 229910052708 sodium Inorganic materials 0.000 description 79
- 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 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 229930182555 Penicillin Natural products 0.000 description 41
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 40
- 239000007795 chemical reaction product Substances 0.000 description 40
- 150000002960 penicillins Chemical class 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 229940049954 penicillin Drugs 0.000 description 33
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 24
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 238000001816 cooling Methods 0.000 description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
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- 150000007942 carboxylates Chemical class 0.000 description 17
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- 239000007858 starting material Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
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- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
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- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
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- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792928344 DE2928344A1 (de) | 1979-07-13 | 1979-07-13 | Neue lactame, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD151941A5 true DD151941A5 (de) | 1981-11-11 |
Family
ID=6075645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80222305A DD151941A5 (de) | 1979-07-13 | 1980-07-01 | Verfahren zur herstellung von neuen beta-lactamen |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4415566A (fr) |
| EP (1) | EP0022494B1 (fr) |
| JP (1) | JPS5615292A (fr) |
| AT (1) | ATE2621T1 (fr) |
| AU (1) | AU539009B2 (fr) |
| CA (1) | CA1146542A (fr) |
| DD (1) | DD151941A5 (fr) |
| DE (2) | DE2928344A1 (fr) |
| DK (1) | DK302580A (fr) |
| ES (3) | ES493307A0 (fr) |
| FI (1) | FI802227A (fr) |
| GR (1) | GR69686B (fr) |
| HU (1) | HU183177B (fr) |
| IL (1) | IL60547A (fr) |
| NO (1) | NO802086L (fr) |
| NZ (1) | NZ194314A (fr) |
| PH (1) | PH17846A (fr) |
| PT (1) | PT71531B (fr) |
| ZA (1) | ZA804203B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3007685A1 (de) | 1980-02-29 | 1981-10-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue cephylosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3028451A1 (de) * | 1980-07-26 | 1982-04-08 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue lactame, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3038501A1 (de) * | 1980-10-11 | 1982-05-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue cephalosporine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
| DE3042440A1 (de) * | 1980-11-11 | 1982-06-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0053276A3 (fr) * | 1980-12-02 | 1983-08-03 | Dr. Karl Thomae GmbH | Céphalosporines, procédé pour leur préparation et compositions pharmaceutiques les contenant |
| EP0053693A1 (fr) * | 1980-12-05 | 1982-06-16 | Dr. Karl Thomae GmbH | Pénicillines, leurs sels, procédé de préparation et les compositions pharmaceutiques les contenant |
| DE3047082A1 (de) * | 1980-12-13 | 1982-07-29 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB8318846D0 (en) * | 1983-07-12 | 1983-08-10 | Fujisawa Pharmaceutical Co | Prophylactic/therapeutic agent against fish diseases |
| US4761410A (en) * | 1985-01-14 | 1988-08-02 | Fujisawa Pharmaceutical Co., Ltd. | Cephem Compounds |
| JPS643597Y2 (fr) * | 1985-11-27 | 1989-01-31 | ||
| US6403908B2 (en) | 1999-02-19 | 2002-06-11 | Bob Stardust | Automated method and apparatus for playing card sequencing, with optional defect detection |
| AU6909300A (en) * | 1999-08-20 | 2001-03-19 | Merck & Co., Inc. | Substituted ureas as cell adhesion inhibitors |
| AU2003294161A1 (en) * | 2003-03-20 | 2004-10-11 | Orchid Chemicals And Pharmaceuticals Ltd | An improved process for the preparation of cefoxitin |
| CN108191781B (zh) * | 2018-01-08 | 2020-01-21 | 浙江大学 | 取代三氮唑类衍生物及其在制备抗肿瘤转移药物中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2450668A1 (de) * | 1974-10-25 | 1976-04-29 | Merck Patent Gmbh | Ureidobenzylpenicilline und verfahren zu ihrer herstellung |
| US4063019A (en) * | 1976-03-30 | 1977-12-13 | E. R. Squibb & Sons, Inc. | [[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]-acetylcephalosporin derivatives |
| JPS5344585A (en) * | 1976-10-02 | 1978-04-21 | Meiji Seika Kaisha Ltd | Cephalosporin derivatives and their preparation |
| PT67170B (de) * | 1976-11-06 | 1979-03-21 | Merck Patent Gmbh | Lactame verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| DE2720580A1 (de) * | 1977-05-07 | 1978-11-09 | Bayer Ag | Beta-lactam-verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| ES477520A1 (es) * | 1978-02-25 | 1979-06-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevas penicilinas. |
| DE2828261A1 (de) * | 1978-06-28 | 1980-01-10 | Thomae Gmbh Dr K | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1979
- 1979-07-13 DE DE19792928344 patent/DE2928344A1/de not_active Withdrawn
-
1980
- 1980-06-26 EP EP80103612A patent/EP0022494B1/fr not_active Expired
- 1980-06-26 AT AT80103612T patent/ATE2621T1/de not_active IP Right Cessation
- 1980-06-26 DE DE8080103612T patent/DE3062125D1/de not_active Expired
- 1980-07-01 DD DD80222305A patent/DD151941A5/de unknown
- 1980-07-10 PT PT71531A patent/PT71531B/pt unknown
- 1980-07-11 ES ES493307A patent/ES493307A0/es active Granted
- 1980-07-11 IL IL60547A patent/IL60547A/xx unknown
- 1980-07-11 FI FI802227A patent/FI802227A/fi not_active Application Discontinuation
- 1980-07-11 CA CA000355988A patent/CA1146542A/fr not_active Expired
- 1980-07-11 DK DK302580A patent/DK302580A/da not_active Application Discontinuation
- 1980-07-11 NO NO802086A patent/NO802086L/no unknown
- 1980-07-11 AU AU60361/80A patent/AU539009B2/en not_active Withdrawn - After Issue
- 1980-07-11 ZA ZA00804203A patent/ZA804203B/xx unknown
- 1980-07-11 HU HU801749A patent/HU183177B/hu unknown
- 1980-07-11 JP JP9494980A patent/JPS5615292A/ja active Pending
- 1980-07-11 NZ NZ194314A patent/NZ194314A/xx unknown
- 1980-07-12 GR GR62445A patent/GR69686B/el unknown
- 1980-09-26 US US06/191,423 patent/US4415566A/en not_active Expired - Lifetime
- 1980-10-15 PH PH24729A patent/PH17846A/en unknown
-
1981
- 1981-05-27 ES ES502529A patent/ES8203903A1/es not_active Expired
- 1981-05-27 ES ES502528A patent/ES502528A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8107227A1 (es) | 1981-10-01 |
| PT71531B (de) | 1981-12-11 |
| FI802227A (fi) | 1981-01-14 |
| ZA804203B (en) | 1982-03-31 |
| DK302580A (da) | 1981-01-14 |
| ES502529A0 (es) | 1982-04-01 |
| ES8203903A1 (es) | 1982-04-01 |
| ES8203902A1 (es) | 1982-04-01 |
| US4415566A (en) | 1983-11-15 |
| NZ194314A (en) | 1983-06-14 |
| IL60547A (en) | 1983-11-30 |
| HU183177B (en) | 1984-04-28 |
| IL60547A0 (en) | 1980-09-16 |
| JPS5615292A (en) | 1981-02-14 |
| PH17846A (en) | 1985-01-09 |
| PT71531A (de) | 1980-08-01 |
| CA1146542A (fr) | 1983-05-17 |
| DE3062125D1 (en) | 1983-03-31 |
| GR69686B (fr) | 1982-07-08 |
| ES502528A0 (es) | 1982-04-01 |
| ATE2621T1 (de) | 1983-03-15 |
| EP0022494B1 (fr) | 1983-02-23 |
| AU6036180A (en) | 1981-01-15 |
| AU539009B2 (en) | 1984-09-06 |
| ES493307A0 (es) | 1981-10-01 |
| DE2928344A1 (de) | 1981-02-05 |
| NO802086L (no) | 1981-01-14 |
| EP0022494A1 (fr) | 1981-01-21 |
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