CH638522A5 - Therapeutically active 6-(alpha-hydroxyethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives, and processes for their preparation - Google Patents

Therapeutically active 6-(alpha-hydroxyethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives, and processes for their preparation Download PDF

Info

Publication number: CH638522A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; alkyl; hydrogen; bromine; chlorine
Prior art date: 1978-05-03

Application number

CH535478A

Other languages

German (de)

English (en)

Inventor

Burton Grant Christensen

David Houng-Min Shih

Original Assignee

Merck & Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-05-03

Filing date

1978-05-17

Publication date

1983-09-30

1978-05-17 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1983-09-30 Publication of CH638522A5 publication Critical patent/CH638522A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 29
238000000034 method Methods 0.000 title claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 40
-1 dimethoxyphosphinyl Chemical group 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
238000005984 hydrogenation reaction Methods 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
229910052717 sulfur Chemical group 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
230000003115 biocidal effect Effects 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000005633 phthalidyl group Chemical group 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims 7
150000002367 halogens Chemical class 0.000 claims 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 4
125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000004663 dialkyl amino group Chemical group 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
239000011630 iodine Substances 0.000 claims 2
229910052740 iodine Inorganic materials 0.000 claims 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 claims 1
125000004104 aryloxy group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000004404 heteroalkyl group Chemical group 0.000 claims 1
125000004475 heteroaralkyl group Chemical class 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000003441 thioacyl group Chemical group 0.000 claims 1
239000000047 product Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 11
239000013543 active substance Substances 0.000 description 10
239000003242 anti bacterial agent Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 9
229940088710 antibiotic agent Drugs 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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239000008101 lactose Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
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AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
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CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
ACBDNFPUXYGKPT-UHFFFAOYSA-N bromomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCBr ACBDNFPUXYGKPT-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
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239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229960000318 kanamycin Drugs 0.000 description 1
229930027917 kanamycin Natural products 0.000 description 1
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
229930182823 kanamycin A Natural products 0.000 description 1
OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 1
229960005287 lincomycin Drugs 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
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238000001819 mass spectrum Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
229960002950 novobiocin Drugs 0.000 description 1
YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940054534 ophthalmic solution Drugs 0.000 description 1
239000002997 ophthalmic solution Substances 0.000 description 1
229940100685 otic solution Drugs 0.000 description 1
239000003973 paint Substances 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
229960003081 probenecid Drugs 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/14—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
- 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
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH535478A 1978-05-03 1978-05-17 Therapeutically active 6-(alpha-hydroxyethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives, and processes for their preparation CH638522A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB17493/78A GB1592224A (en)	1978-05-03	1978-05-03	Thienamycin derivatives their production and their use as antibiotics

Publications (1)

Publication Number	Publication Date
CH638522A5 true CH638522A5 (en)	1983-09-30

Family

ID=10096140

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH535478A CH638522A5 (en)	1978-05-03	1978-05-17	Therapeutically active 6-(alpha-hydroxyethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives, and processes for their preparation

Country Status (8)

Country	Link
JP (1)	JPS54151996A (fr)
CH (1)	CH638522A5 (fr)
DE (1)	DE2820055A1 (fr)
FR (1)	FR2426054A1 (fr)
GB (1)	GB1592224A (fr)
LU (1)	LU79677A1 (fr)
NL (1)	NL7804976A (fr)
SE (1)	SE7805032L (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE51861B1 (en) *	1978-10-24	1987-04-15	Merck & Co Inc	6-,1-and 2-substituted-1-carbapen-2-em-3-carboxylic acids,processes for the preparation of such compounds and pharmaceutical compositions comprising such compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950357A (en) *	1974-11-25	1976-04-13	Merck & Co., Inc.	Antibiotics
DE2811514A1 (de) *	1977-03-19	1978-09-21	Beecham Group Ltd	Ester der 7-oxo-1-azabicyclo eckige klammer auf 3.2.0 eckige klammer zu hept- 2-en-2-carbonsaeure und deren derivate, verfahren zur herstellung dieser verbindungen und diese verbindungen enthaltende pharmazeutische zubereitungen
DE2862419D1 (en) *	1977-11-12	1984-07-26	Beecham Group Plc	Derivatives of 7-oxo-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid, their preparation, pharmaceutical compositions containing them and intermediates

1978
- 1978-05-02 SE SE7805032A patent/SE7805032L/xx not_active Application Discontinuation
- 1978-05-03 GB GB17493/78A patent/GB1592224A/en not_active Expired
- 1978-05-08 DE DE19782820055 patent/DE2820055A1/de not_active Ceased
- 1978-05-09 NL NL7804976A patent/NL7804976A/xx not_active Application Discontinuation
- 1978-05-17 CH CH535478A patent/CH638522A5/de not_active IP Right Cessation
- 1978-05-17 FR FR7814597A patent/FR2426054A1/fr active Granted
- 1978-05-18 LU LU79677A patent/LU79677A1/fr unknown
- 1978-05-19 JP JP5901878A patent/JPS54151996A/ja active Pending

Also Published As

Publication number	Publication date
JPS54151996A (en)	1979-11-29
FR2426054A1 (fr)	1979-12-14
GB1592224A (en)	1981-07-01
FR2426054B1 (fr)	1980-11-07
LU79677A1 (fr)	1979-02-02
SE7805032L (sv)	1979-11-03
DE2820055A1 (de)	1979-11-22
NL7804976A (nl)	1979-11-13

Legal Events

Date	Code	Title	Description
1988-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3587126T2 (de)	1993-10-07	Carbapenem-Derivate und sie enthaltende Zusammensetzung.
DE2819479C2 (fr)	1992-04-30
DE3321864C2 (fr)	1992-03-26
DE2751624A1 (de)	1978-06-01	1-carba-2-penem-3-carbonsaeure
AT392279B (de)	1991-02-25	Verfahren zur herstellung von neuen cephalosporin-antibiotika
EP0247431B1 (fr)	1990-08-01	Antibiotiques du 6-hydroxyméthylcarbapénème substitués, leur procédé de préparation et leur application
EP0301394B1 (fr)	1993-10-06	Acides oxapénèm-3-carboxyliques stables
US4123539A (en)	1978-10-31	6-Ethylpenicillanic acid
DE2312041A1 (de)	1973-10-11	Penicilline, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
CH640236A5 (en)	1983-12-30	3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2 -carboxylic acid and process for its preparation
DE3317742C2 (fr)	1991-08-29
CH644608A5 (de)	1984-08-15	Verfahren zur herstellung von penicillansaeure-1,1-dioxid und dessen estern sowie zwischenverbindungen zur durchfuehrung des verfahrens.
DE2423591C3 (de)	1980-07-31	1-N-Isoserylkanamycine, Verfahren zu ihrer Herstellung und solche Verbindungen enthaltende Arzneimittel
DE2725203A1 (de)	1977-12-22	Neue clavamsaeurederivate und verfahren zu deren herstellung
DE3312517C2 (fr)	1991-10-31
DE3833693A1 (de)	1990-04-05	Stabile oxapenem-3-carbonsaeuren und ihre verwendung als ss-lactamasehemmer
DE2652675C2 (fr)	1990-02-01
DE69909098T2 (de)	2004-04-08	C-2 s/o- und s/n-formaldehydacetal-derivate von carbapenem-3-carbonsäuren und deren verwendung als antibiotika und beta-lactamas-inhibitoren
DE3630857C2 (de)	1994-04-07	Carbapenem-Antibiotika, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
CH633554A5 (en)	1982-12-15	Process for the preparation of novel thienamycin derivatives.
DE3880660T2 (de)	1993-09-23	In 2-stellung substituierte (1r,5s,6s)-2-thio-6-((r)-1-hydroxyethyl)-1-methyl-carbapenem-carbonsaeure-derivate.
CH616938A5 (en)	1980-04-30	Process for the preparation of 6beta-acylamino-1-oxadethiapenicillanic acids
EP0268963A1 (fr)	1988-06-01	Antibiotiques du type benzazolylthiocarbapénème
AT332974B (de)	1976-10-25	Verfahren zur herstellung neuer penicilline
DE2820055A1 (de)	1979-11-22	6-(alpha-hydroxyaethyl)-7-oxo-1- azabicyclo eckige klammer auf 3.2.0 eckige klammer zu-hept-2-en-(und heptan)-2-carbonsaeure und deren derivate