CH636879A5 - Verfahren zur herstellung 7-substituierter aminoacetamido-oxadethia-cephalosporine. - Google Patents
Verfahren zur herstellung 7-substituierter aminoacetamido-oxadethia-cephalosporine. Download PDFInfo
- Publication number
- CH636879A5 CH636879A5 CH1067377A CH1067377A CH636879A5 CH 636879 A5 CH636879 A5 CH 636879A5 CH 1067377 A CH1067377 A CH 1067377A CH 1067377 A CH1067377 A CH 1067377A CH 636879 A5 CH636879 A5 CH 636879A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- methyl
- oxadethia
- substituted
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 carbamoyloxy Chemical group 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001734 carboxylic acid salts Chemical class 0.000 claims description 6
- 229940124587 cephalosporin Drugs 0.000 claims description 6
- RGJOEKWQDUBAIZ-HDCXRZRFSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3s)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate Chemical group O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-HDCXRZRFSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 2
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- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 229910052717 sulfur Chemical group 0.000 claims 7
- 239000011593 sulfur Chemical group 0.000 claims 7
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- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
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- 239000001301 oxygen Chemical group 0.000 claims 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
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- 230000001580 bacterial effect Effects 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
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- 238000001816 cooling Methods 0.000 description 13
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000588754 Klebsiella sp. Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- VINBVOMNIBDIPH-UHFFFAOYSA-N isocyanoimino(oxo)methane Chemical compound O=C=N[N+]#[C-] VINBVOMNIBDIPH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 235000010332 potassium propionate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 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
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
-
- 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
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10511776A JPS5331690A (en) | 1976-09-01 | 1976-09-01 | Oxadithiacephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH636879A5 true CH636879A5 (de) | 1983-06-30 |
Family
ID=14398870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1067377A CH636879A5 (de) | 1976-09-01 | 1977-09-01 | Verfahren zur herstellung 7-substituierter aminoacetamido-oxadethia-cephalosporine. |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4226864A (en, 2012) |
| JP (1) | JPS5331690A (en, 2012) |
| AR (4) | AR221583A1 (en, 2012) |
| AT (1) | AT353964B (en, 2012) |
| AU (1) | AU511254B2 (en, 2012) |
| BE (1) | BE858341A (en, 2012) |
| BG (1) | BG34038A3 (en, 2012) |
| CA (1) | CA1079278A (en, 2012) |
| CH (1) | CH636879A5 (en, 2012) |
| CS (1) | CS203166B2 (en, 2012) |
| DD (1) | DD132872A5 (en, 2012) |
| DE (1) | DE2739448A1 (en, 2012) |
| DK (1) | DK388377A (en, 2012) |
| ES (1) | ES462012A1 (en, 2012) |
| FI (1) | FI64599C (en, 2012) |
| FR (1) | FR2375238A1 (en, 2012) |
| GB (1) | GB1551479A (en, 2012) |
| GR (1) | GR69784B (en, 2012) |
| HU (1) | HU177382B (en, 2012) |
| IE (1) | IE45572B1 (en, 2012) |
| IL (1) | IL52841A (en, 2012) |
| MX (1) | MX4451E (en, 2012) |
| NL (1) | NL190267C (en, 2012) |
| NZ (1) | NZ185018A (en, 2012) |
| PH (1) | PH17509A (en, 2012) |
| PL (2) | PL104617B1 (en, 2012) |
| PT (1) | PT66974B (en, 2012) |
| RO (1) | RO77767A (en, 2012) |
| SE (1) | SE441095B (en, 2012) |
| SU (4) | SU786901A3 (en, 2012) |
| YU (4) | YU40172B (en, 2012) |
| ZA (1) | ZA775154B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5690088A (en) * | 1979-11-02 | 1981-07-21 | Meiji Seika Kaisha Ltd | Novel cephalosporin analog compound |
| FR2494279A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles oxacephalosporines, leur preparation et les medicaments qui les contiennent |
| DE3137038A1 (de) | 1981-09-17 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Ss-lactam antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS59104389A (ja) * | 1982-12-06 | 1984-06-16 | Shionogi & Co Ltd | オキサセファム誘導体 |
| JPS59118789A (ja) * | 1982-12-27 | 1984-07-09 | Shionogi & Co Ltd | オキサセフエム誘導体、その製法および用途 |
| US4645769A (en) * | 1985-03-01 | 1987-02-24 | Merck & Co., Inc. | 1-oxa-1-dethia-cephalosporin compounds and antibacterial agent comprising the same |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
| EP2074123B1 (en) | 2006-10-16 | 2012-12-05 | Bionomics Limited | Novel anxiolytic compounds |
| WO2009049086A1 (en) | 2007-10-09 | 2009-04-16 | Larry Sutton | Broad spectrum beta-lactamase inhibitors |
| JP6055817B2 (ja) | 2011-05-12 | 2016-12-27 | バイオノミックス リミテッド | ナフチリジンの調製方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208171A1 (es) * | 1972-09-29 | 1976-12-09 | Ciba Geigy Ag | Procedimiento para la obtencion de nuevos derivados del acido cef-3-em-4-carboxilico |
| NL178005C (nl) * | 1972-11-06 | 1986-01-02 | Merck & Co Inc | Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum. |
| US4032521A (en) * | 1972-12-29 | 1977-06-28 | Merck & Co., Inc. | Cephalosporin phosphonic acid, sulfonic acid and sulfonamide compounds |
| JPS49133593A (en, 2012) * | 1973-05-04 | 1974-12-21 | ||
| GB1449420A (en) * | 1973-11-26 | 1976-09-15 | Sankyo Co | 7alpha-methoxycephalosporing derivatives |
| US4110327A (en) * | 1974-05-09 | 1978-08-29 | Toyama Chemical Co., Ltd. | 2,3 Diketo-piperazinocarbonylamino alkanoic acids and derivatives |
| IL47168A (en) * | 1974-05-09 | 1979-07-25 | Toyama Chemical Co Ltd | Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same |
| US4087424A (en) * | 1974-05-09 | 1978-05-02 | Toyama Chemical Co., Ltd. | Novel penicillins and cephalosporins and process for producing the same |
| GB1510794A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 1-oxacephems and intermediates therefor |
| GB1486349A (en) * | 1974-11-28 | 1977-09-21 | Bayer Ag | Beta-lactam antibiotics process for their preparation and their use as medicaments |
| DE2528077A1 (de) * | 1975-06-24 | 1977-01-20 | Bayer Ag | Beta-lactamantibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US3996218A (en) * | 1975-09-08 | 1976-12-07 | E. R. Squibb & Sons, Inc. | Oxopyridazinylthiomethyl derivatives of ureidocephalosporins |
| US4103008A (en) * | 1976-04-07 | 1978-07-25 | Ishimaru Toshiyasu | 7[2(2,3 Dioxopiperazin-1-yl-carbonylamino)substituted 2 phenylacetamido]-3-2'-thiadiazolyl cephalosporanic acid derivatives |
| JPS609515B2 (ja) * | 1976-08-09 | 1985-03-11 | 塩野義製薬株式会社 | ３′−ノルオキサセファロスポリン類 |
-
1976
- 1976-09-01 JP JP10511776A patent/JPS5331690A/ja active Granted
-
1977
- 1977-08-22 US US05/826,818 patent/US4226864A/en not_active Expired - Lifetime
- 1977-08-24 GB GB35577/77A patent/GB1551479A/en not_active Expired
- 1977-08-24 HU HU77SI1589A patent/HU177382B/hu not_active IP Right Cessation
- 1977-08-25 AU AU28233/77A patent/AU511254B2/en not_active Expired
- 1977-08-25 ZA ZA00775154A patent/ZA775154B/xx unknown
- 1977-08-25 NZ NZ185018A patent/NZ185018A/xx unknown
- 1977-08-26 IE IE1786/77A patent/IE45572B1/en not_active IP Right Cessation
- 1977-08-29 CA CA285,625A patent/CA1079278A/en not_active Expired
- 1977-08-29 IL IL52841A patent/IL52841A/xx unknown
- 1977-08-29 CS CS775642A patent/CS203166B2/cs unknown
- 1977-08-30 PL PL1977200534A patent/PL104617B1/pl unknown
- 1977-08-30 PT PT66974A patent/PT66974B/pt unknown
- 1977-08-30 YU YU2067/77A patent/YU40172B/xx unknown
- 1977-08-30 PL PL1977206929A patent/PL104618B1/pl unknown
- 1977-08-30 SE SE7709736A patent/SE441095B/sv not_active IP Right Cessation
- 1977-08-31 AR AR269031A patent/AR221583A1/es active
- 1977-08-31 ES ES462012A patent/ES462012A1/es not_active Expired
- 1977-08-31 NL NLAANVRAGE7709611,A patent/NL190267C/xx not_active IP Right Cessation
- 1977-08-31 DK DK388377A patent/DK388377A/da not_active Application Discontinuation
- 1977-08-31 MX MX776083U patent/MX4451E/es unknown
- 1977-08-31 AT AT628177A patent/AT353964B/de not_active IP Right Cessation
- 1977-08-31 FI FI772582A patent/FI64599C/fi not_active IP Right Cessation
- 1977-09-01 DD DD7700200849A patent/DD132872A5/xx unknown
- 1977-09-01 FR FR7726613A patent/FR2375238A1/fr active Granted
- 1977-09-01 SU SU772517656A patent/SU786901A3/ru active
- 1977-09-01 BE BE180628A patent/BE858341A/xx not_active IP Right Cessation
- 1977-09-01 DE DE19772739448 patent/DE2739448A1/de not_active Ceased
- 1977-09-01 PH PH20184A patent/PH17509A/en unknown
- 1977-09-01 BG BG037279A patent/BG34038A3/xx unknown
- 1977-09-01 GR GR54277A patent/GR69784B/el unknown
- 1977-09-01 CH CH1067377A patent/CH636879A5/de not_active IP Right Cessation
- 1977-09-01 RO RO7798444A patent/RO77767A/ro unknown
-
1978
- 1978-08-31 SU SU782655255A patent/SU799665A3/ru active
- 1978-09-01 SU SU782654601A patent/SU831079A3/ru active
- 1978-09-05 SU SU782656248A patent/SU812183A3/ru active
- 1978-12-21 AR AR274921A patent/AR227270A1/es active
- 1978-12-21 AR AR274919A patent/AR218951A1/es active
- 1978-12-21 AR AR274920A patent/AR221609A1/es active
-
1982
- 1982-07-22 YU YU01607/82A patent/YU160782A/xx unknown
- 1982-07-22 YU YU01606/82A patent/YU160682A/xx unknown
- 1982-07-22 YU YU01608/82A patent/YU160882A/xx unknown
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