NO770568L - Nye 5,6-dehydropenicilliner og fremgangsm}te for deres fremstilling. - Google Patents

Nye 5,6-dehydropenicilliner og fremgangsm}te for deres fremstilling.

Info

Publication number: NO770568L
Authority: NO; Norway
Prior art keywords: stated; carried out; reaction; product; thioxo
Prior art date: 1976-02-23

Application number

NO770568A

Other languages

English (en)

Norwegian (no)

Inventor

Luciano Re

Alberto Brandt

Luciano Bassignani

Original Assignee

Snam Progetti

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.)

1976-02-23

Filing date

1977-02-21

Publication date

1977-08-24

1977-02-21 Application filed by Snam Progetti filed Critical Snam Progetti

1977-08-24 Publication of NO770568L publication Critical patent/NO770568L/no

Links

238000000034 method Methods 0.000 title claims description 31
238000004519 manufacturing process Methods 0.000 title claims description 9
238000006243 chemical reaction Methods 0.000 claims description 25
150000002148 esters Chemical class 0.000 claims description 18
-1 azetidinium ions Chemical class 0.000 claims description 11
KDERTRJFUUMBKU-UHFFFAOYSA-N 4-sulfanylideneazetidin-2-one Chemical class O=C1CC(=S)N1 KDERTRJFUUMBKU-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
239000012298 atmosphere Substances 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
150000007970 thio esters Chemical class 0.000 claims description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
150000003839 salts Chemical group 0.000 claims description 2
239000002253 acid Substances 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
238000006798 ring closing metathesis reaction Methods 0.000 claims 1
239000000047 product Substances 0.000 description 44
238000002360 preparation method Methods 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
239000000243 solution Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
229930182555 Penicillin Natural products 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000012043 crude product Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000002960 penicillins Chemical class 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
239000006260 foam Substances 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 3
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 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 2
AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
230000000844 anti-bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000005297 pyrex Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000006257 total synthesis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QABCDCRBWNTCGD-UHFFFAOYSA-N 1,2-dihydroazete Chemical class C1NC=C1 QABCDCRBWNTCGD-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
229920004449 Halon® Polymers 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003974 aralkylamines Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
MEJXDFQUPGDBSZ-UHFFFAOYSA-N methyl 2-(3-acetamido-2-oxo-4-sulfanylideneazetidin-1-yl)-3-methylbut-2-enoate Chemical compound COC(=O)C(=C(C)C)N1C(=O)C(NC(C)=O)C1=S MEJXDFQUPGDBSZ-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
238000006552 photochemical reaction Methods 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
125000001984 thiazolidinyl group Chemical group 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
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/10—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

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)
Polyesters Or Polycarbonates (AREA)
Polyamides (AREA)
Saccharide Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

NO770568A 1976-02-23 1977-02-21 Nye 5,6-dehydropenicilliner og fremgangsm}te for deres fremstilling. NO770568L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT20457/76A IT1058858B (it)	1976-02-23	1976-02-23	5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo

Publications (1)

Publication Number	Publication Date
NO770568L true NO770568L (no)	1977-08-24

Family

ID=11167232

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO770568A NO770568L (no)	1976-02-23	1977-02-21	Nye 5,6-dehydropenicilliner og fremgangsm}te for deres fremstilling.
NO773766A NO773766L (no)	1976-02-23	1977-11-03	Nye 4-tiokso-2-azetidinoner og fremgangsm}te for deres fremstilling

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO773766A NO773766L (no)	1976-02-23	1977-11-03	Nye 4-tiokso-2-azetidinoner og fremgangsm}te for deres fremstilling

Country Status (21)

Country	Link
US (3)	US4133807A (hu)
JP (1)	JPS52102267A (hu)
AU (1)	AU514741B2 (hu)
BE (1)	BE851751A (hu)
CA (1)	CA1090290A (hu)
CH (1)	CH631180A5 (hu)
CS (1)	CS199662B2 (hu)
DD (1)	DD128359A5 (hu)
DE (1)	DE2707404C3 (hu)
DK (2)	DK77177A (hu)
FR (1)	FR2341582A1 (hu)
GB (2)	GB1572140A (hu)
HU (2)	HU179786B (hu)
IT (1)	IT1058858B (hu)
LU (1)	LU76816A1 (hu)
NL (1)	NL171159C (hu)
NO (2)	NO770568L (hu)
SE (1)	SE438506B (hu)
SU (3)	SU683626A3 (hu)
YU (3)	YU49377A (hu)
ZA (1)	ZA77890B (hu)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1058858B (it) *	1976-02-23	1982-05-10	Snam Progetti	5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo
JPS5398951A (en) *	1977-02-08	1978-08-29	Shionogi & Co Ltd	Azetidinone derivatives and process for their preparation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4174318A (en) *	1970-11-03	1979-11-13	Glaxo Laboratories Ltd.	Alkylative cleavage of azetidinone disulfides
BE791161A (fr) *	1972-01-03	1973-05-09	Beecham Group Ltd	Procede pour la preparation d'analogues des cephalosporines
US4089963A (en) *	1972-03-13	1978-05-16	Astra Pharmaceutical Products, Inc.	Esters of amidinopenicillanic acids, pharmaceutical preparations and method for treating infectious diseases
US4219462A (en) *	1974-07-29	1980-08-26	Merck & Co., Inc.	6-Methyl penicillins
IT1058858B (it) *	1976-02-23	1982-05-10	Snam Progetti	5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo
US4136096A (en) *	1977-02-25	1979-01-23	Pfizer Inc.	6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam process and intermediates therefor
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
US4160091A (en) *	1977-11-21	1979-07-03	Eli Lilly And Company	Process for preparation of 3-halo-3-methylcephams

1976
- 1976-02-23 IT IT20457/76A patent/IT1058858B/it active
1977
- 1977-02-15 ZA ZA770890A patent/ZA77890B/xx unknown
- 1977-02-17 US US05/769,527 patent/US4133807A/en not_active Expired - Lifetime
- 1977-02-18 AU AU22428/77A patent/AU514741B2/en not_active Ceased
- 1977-02-21 SE SE7701907A patent/SE438506B/xx not_active IP Right Cessation
- 1977-02-21 DE DE2707404A patent/DE2707404C3/de not_active Expired
- 1977-02-21 NO NO770568A patent/NO770568L/no unknown
- 1977-02-22 FR FR7705128A patent/FR2341582A1/fr active Granted
- 1977-02-22 DK DK77177A patent/DK77177A/da not_active Application Discontinuation
- 1977-02-22 GB GB1747/79A patent/GB1572140A/en not_active Expired
- 1977-02-22 GB GB7500/77A patent/GB1572139A/en not_active Expired
- 1977-02-22 DD DD7700197507A patent/DD128359A5/xx unknown
- 1977-02-22 CA CA272,330A patent/CA1090290A/en not_active Expired
- 1977-02-22 LU LU76816A patent/LU76816A1/xx unknown
- 1977-02-22 YU YU00493/77A patent/YU49377A/xx unknown
- 1977-02-22 HU HU77SA3016A patent/HU179786B/hu unknown
- 1977-02-22 CH CH221077A patent/CH631180A5/it not_active IP Right Cessation
- 1977-02-22 HU HU813040A patent/HU183632B/hu unknown
- 1977-02-23 BE BE175195A patent/BE851751A/xx not_active IP Right Cessation
- 1977-02-23 JP JP1825877A patent/JPS52102267A/ja active Pending
- 1977-02-23 NL NLAANVRAGE7701962,A patent/NL171159C/xx not_active IP Right Cessation
- 1977-02-23 CS CS771196A patent/CS199662B2/cs unknown
- 1977-02-23 SU SU772455688A patent/SU683626A3/ru active
- 1977-11-03 NO NO773766A patent/NO773766L/no unknown
1978
- 1978-02-13 SU SU782578098A patent/SU721004A3/ru active
- 1978-02-13 SU SU782580402A patent/SU712024A3/ru active
1979
- 1979-07-19 US US06/058,945 patent/US4288366A/en not_active Expired - Lifetime
1981
- 1981-02-19 US US06/236,029 patent/US4353825A/en not_active Expired - Fee Related
- 1981-12-16 DK DK558781A patent/DK558781A/da not_active Application Discontinuation
1982
- 1982-09-27 YU YU02149/82A patent/YU214982A/xx unknown
- 1982-09-27 YU YU02148/82A patent/YU214882A/xx unknown

Also Published As

Publication number	Publication date
DE2707404C3 (de)	1979-03-22
IT1058858B (it)	1982-05-10
NL171159B (nl)	1982-09-16
ZA77890B (en)	1977-12-28
DK558781A (da)	1981-12-16
YU214982A (en)	1983-01-21
JPS52102267A (en)	1977-08-27
NO773766L (no)	1977-08-24
LU76816A1 (hu)	1977-07-06
GB1572139A (en)	1980-07-23
CH631180A5 (de)	1982-07-30
HU179786B (en)	1982-12-28
AU514741B2 (en)	1981-02-26
HU183632B (en)	1984-05-28
US4288366A (en)	1981-09-08
DD128359A5 (de)	1977-11-16
US4353825A (en)	1982-10-12
FR2341582B1 (hu)	1980-01-11
YU214882A (en)	1983-01-21
SU712024A3 (ru)	1980-01-25
CA1090290A (en)	1980-11-25
DE2707404B2 (de)	1978-07-13
SE7701907L (sv)	1977-10-03
GB1572140A (en)	1980-07-23
YU49377A (en)	1983-01-21
BE851751A (fr)	1977-08-23
SU721004A3 (ru)	1980-03-05
AU2242877A (en)	1978-08-24
SE438506B (sv)	1985-04-22
FR2341582A1 (fr)	1977-09-16
DE2707404A1 (de)	1977-08-25
NL7701962A (nl)	1977-08-25
US4133807A (en)	1979-01-09
CS199662B2 (en)	1980-07-31
DK77177A (da)	1977-08-24
NL171159C (nl)	1983-02-16
SU683626A3 (ru)	1979-08-30

Publication	Publication Date	Title
US4778891A (en)	1988-10-18	Certain pyrano (3,4-f)-indolizine derivatives
Chida et al.	1991	Synthesis of Optically Active Substituted Cyclohexenones from Carbohydrates by Catalytic Ferrier Rearrangement.
Franco et al.	1982	Novel syntheses of 5-aroyl-1, 2-dihydro-3H-pyrrolo [1, 2-a] pyrrole-1-carboxylic acids
Benhaddou et al.	1992	Palladium-mediated arylation of acetylated enones derived from glycals. 4. Synthesis of aryl-2-deoxy-. beta.-DC-glycopyranosides
US4237051A (en)	1980-12-02	Stereospecific production of 6- or 7-carbon-substituted-β-lactams
EP0023097A1 (en)	1981-01-28	De-arylmethylation of N-mono- or N-diarylmethyl-beta-lactams; novel azetizinones having anti-bacterial activity
Wasserman et al.	1978	Reaction of singlet oxygen with enamino lactones. Conversion of lactones to. alpha.-keto lactones
CA1185244A (en)	1985-04-09	.beta.-LACTAM ACETIC ACID DERIVATIVES, THE PROCESS FOR PREPARING THEM, AND THEIR USE AS INTERMEDIATES FOR 1- AZABICYCLO¬3.2.0\|HEPT-2-ENE ANTIBIOTICS
NO770568L (no)	1977-08-24	Nye 5,6-dehydropenicilliner og fremgangsm}te for deres fremstilling.
EP0270076A1 (de)	1988-06-08	Imidazolderivate und ein Verfahren zu deren Herstellung
Ambrosini et al.	2010	Total synthesis of the tylophora alkaloids rusplinone, 13aα-secoantofine, and antofine using a multicatalytic oxidative aminochlorocarbonylation/Friedel–Crafts reaction
Dmitrienko et al.	1992	A new approach to the bicyclic hydroxylamine hemiketal ring system of antitumour-antibiotic FR900482 via oxidative ring expansion of a tetrahydropyrrolo [1, 2-a] indole
Rosati et al.	1990	Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams
Reuvers et al.	1986	Total synthesis of (. mu.)-3. beta.-hydroxynagilactone F
Herdewijn et al.	1986	Synthesis of. DELTA. 3-1-methylene-1-carbacephems
Gu et al.	1998	A convenient synthesis of 3-arylbutanolides and 3-arylbutenolides
HU186974B (en)	1985-10-28	Process for the preparation of 3a,7a-trans-4-bracket-7,7-ethylendioxy-3-oxo-octyl-bracket closed-7abeta-methyl-perhydro-indan-1,5-dione
Arad-Yellin et al.	1983	Photocyclization of 2, 6-dichlorocinnamic acid derivatives to 5-chlorocoumarin
Baxter et al.	1994	Azoalkene route to methyl 2, 5-dimethyl-4-[2-(phenylmethyl) benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogues: synthesis of 1-(BOC-amino) pyrrole-3-carboxylates and their conversion to 1H-pyrroles via 1-aminopyrroles
Kaji et al.	1985	Synthesis of Pyrazolo [3, 4-d] pyridazines from 5-(1-Methylhydrazino)-pyridazines by Means of the Vilsmeier-Haack Reaction
Bachi et al.	1983	Enantiospecific synthesis of 4-alkoxyazetidin-2-ones
US4397784A (en)	1983-08-09	Inhibitors of transpeptidase
Balsamo et al.	1980	Importance of the substituent on C (2) in the interconversion of the thiazine and thiazolidine system of. beta.-lactam antibiotics
Cooper et al.	1988	An Improved Process for the Preparation of Oxazolino-azetidinones and 1-Oxadethiacephams from Exomethylenecepham Sulfoxides
JPH0267287A (ja)	1990-03-07	ペネムの製法