IE47043B1 - Azabicycloheptenes - Google Patents

Azabicycloheptenes

Info

Publication number: IE47043B1
Authority: IE; Ireland
Prior art keywords: compound; solution; cold; thienamycin; hydrogen
Prior art date: 1977-04-08

Application number

IE631/78A

Other languages

English (en)

Other versions

IE780631L (en

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.)

1977-04-08

Filing date

1978-03-30

Publication date

1983-12-14

1978-03-30 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1978-10-08 Publication of IE780631L publication Critical patent/IE780631L/xx

1983-12-14 Publication of IE47043B1 publication Critical patent/IE47043B1/en

Links

150000001875 compounds Chemical class 0.000 claims abstract description 37
150000003839 salts Chemical class 0.000 claims abstract description 21
239000003242 anti bacterial agent Substances 0.000 claims abstract description 12
239000000645 desinfectant Substances 0.000 claims abstract description 3
-1 elixir Substances 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 43
229910001868 water Inorganic materials 0.000 claims description 19
238000000034 method Methods 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 9
239000003826 tablet Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000002775 capsule Substances 0.000 claims description 6
239000003973 paint Substances 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 4
239000002552 dosage form Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
235000020357 syrup Nutrition 0.000 claims description 4
239000006188 syrup Substances 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 3
239000000829 suppository Substances 0.000 claims description 3
239000006071 cream Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000006193 liquid solution Substances 0.000 claims description 2
239000006210 lotion Substances 0.000 claims description 2
239000007937 lozenge Substances 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
239000003638 chemical reducing agent Substances 0.000 claims 1
239000006196 drop Substances 0.000 claims 1
239000006194 liquid suspension Substances 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
229940098458 powder spray Drugs 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
229940088710 antibiotic agent Drugs 0.000 abstract description 8
241000894006 Bacteria Species 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 6
239000003755 preservative agent Substances 0.000 abstract description 4
235000019730 animal feed additive Nutrition 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 43
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 38
235000019439 ethyl acetate Nutrition 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
239000002904 solvent Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000008363 phosphate buffer Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
239000000463 material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
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 6
238000003756 stirring Methods 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 5
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 4
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 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
229940099112 cornstarch Drugs 0.000 description 4
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
239000008101 lactose Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000005406 washing Methods 0.000 description 4
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229910019020 PtO2 Inorganic materials 0.000 description 3
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
239000003795 chemical substances by application Substances 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
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
244000052769 pathogen Species 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
239000008223 sterile water Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
235000019739 Dicalciumphosphate Nutrition 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
241000282412 Homo Species 0.000 description 2
241000588748 Klebsiella Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000005263 alkylenediamine group Chemical group 0.000 description 2
239000003899 bactericide agent Substances 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
238000010586 diagram Methods 0.000 description 2
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
229940038472 dicalcium phosphate Drugs 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
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239000007903 gelatin capsule Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
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229910052763 palladium Inorganic materials 0.000 description 2
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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150000003335 secondary amines Chemical class 0.000 description 2
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239000003381 stabilizer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
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ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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MHSGOABISYIYKP-UHFFFAOYSA-N (4-nitrophenyl)methyl carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(COC(Cl)=O)C=C1 MHSGOABISYIYKP-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
USHVCHPXIVXEMW-UHFFFAOYSA-N 2-acetamidoacetic acid;benzenesulfonic acid Chemical compound CC(=O)NCC(O)=O.OS(=O)(=O)C1=CC=CC=C1 USHVCHPXIVXEMW-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
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235000019489 Almond oil Nutrition 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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244000063299 Bacillus subtilis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000212384 Bifora Species 0.000 description 1
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229940116362 tragacanth Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003952 β-lactams Chemical class 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
- C07D477/16—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 hetero atoms or carbon atoms 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 3
- C07D477/20—Sulfur atoms
- 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

Landscapes

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

IE631/78A 1977-04-08 1978-03-30 Azabicycloheptenes IE47043B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US78581177A	1977-04-08	1977-04-08
US86123077A	1977-12-16	1977-12-16

Publications (2)

Publication Number	Publication Date
IE780631L IE780631L (en)	1978-10-08
IE47043B1 true IE47043B1 (en)	1983-12-14

Family

ID=27120448

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE631/78A IE47043B1 (en)	1977-04-08	1978-03-30	Azabicycloheptenes

Country Status (11)

Country	Link
JP (1)	JPS53127491A (fr)
CH (1)	CH640236A5 (fr)
DE (1)	DE2815157A1 (fr)
DK (1)	DK123578A (fr)
FR (1)	FR2386545A1 (fr)
GB (1)	GB1595267A (fr)
IE (1)	IE47043B1 (fr)
IT (1)	IT1102456B (fr)
LU (1)	LU79403A1 (fr)
NL (1)	NL7802826A (fr)
SE (1)	SE7803173L (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR62185B (en) *	1977-03-31	1979-03-02	Panlabs Inc	Preparation process of an antibiotic ps-5 and its derivatives with inhibitory activity of b-lactamase
JPS5473788A (en) *	1977-11-17	1979-06-13	Sanraku Inc	Antibiotic n-desacetyl ps-5
EP0005349A1 (fr) *	1978-05-06	1979-11-14	Beecham Group Plc	Alkylcarbapénèmes, leur préparation, compositions pharmaceutiques les contenant et les intermédiaires
JPS5572191A (en) *	1978-11-22	1980-05-30	Sanraku Inc	Antibiotic n-desacetyl ps-5
JPS55136282A (en) *	1979-04-06	1980-10-23	Shionogi & Co Ltd	Novel antibiotic pa-31088-4
US4235922A (en) *	1979-06-15	1980-11-25	Merck & Co., Inc.	3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid
EP0055990B1 (fr) *	1979-08-10	1986-06-11	Beecham Group Plc	Antibiotiques bêta-lactame, leur préparation et application
JPS5683489A (en) *	1979-12-12	1981-07-08	Shionogi & Co Ltd	New antibiotic pa-39504-x1 and it preparation
JPS5764693A (en) *	1980-10-07	1982-04-19	Kowa Co	Novel carbapenem compound and its preparation

Family Cites Families (1)

* 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

1978
- 1978-03-15 NL NL7802826A patent/NL7802826A/xx not_active Application Discontinuation
- 1978-03-20 DK DK123578A patent/DK123578A/da unknown
- 1978-03-20 SE SE7803173A patent/SE7803173L/xx unknown
- 1978-03-30 IE IE631/78A patent/IE47043B1/en unknown
- 1978-04-04 GB GB13164/78A patent/GB1595267A/en not_active Expired
- 1978-04-05 IT IT48747/78A patent/IT1102456B/it active
- 1978-04-06 FR FR7810238A patent/FR2386545A1/fr active Granted
- 1978-04-07 JP JP4045678A patent/JPS53127491A/ja active Pending
- 1978-04-07 CH CH379278A patent/CH640236A5/de not_active IP Right Cessation
- 1978-04-07 DE DE19782815157 patent/DE2815157A1/de not_active Ceased
- 1978-04-10 LU LU79403A patent/LU79403A1/fr unknown

Also Published As

Publication number	Publication date
IT1102456B (it)	1985-10-07
FR2386545B1 (fr)	1980-08-01
DE2815157A1 (de)	1978-10-19
DK123578A (da)	1978-10-09
FR2386545A1 (fr)	1978-11-03
GB1595267A (en)	1981-08-12
SE7803173L (sv)	1978-10-09
LU79403A1 (fr)	1978-11-27
IT7848747A0 (it)	1978-04-05
IE780631L (en)	1978-10-08
JPS53127491A (en)	1978-11-07
NL7802826A (nl)	1978-10-10
CH640236A5 (en)	1983-12-30

Publication	Publication Date	Title
US4168314A (en)	1979-09-18	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
US4342772A (en)	1982-08-03	β-Lactam compounds, antibacterial compositions thereof and method of use
US4189493A (en)	1980-02-19	N-heterocyclic derivatives of thienamycin
IE46877B1 (en)	1983-10-19	Thienamycin derivatives
IE47043B1 (en)	1983-12-14	Azabicycloheptenes
US4235922A (en)	1980-11-25	3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid
US4123539A (en)	1978-10-31	6-Ethylpenicillanic acid
US4226870A (en)	1980-10-07	O-, N- and carboxyl derivatives of thienamycin
US4123547A (en)	1978-10-31	Thienamycin sulfoxide and sulphone
US4203902A (en)	1980-05-20	Process for preparing 6- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids
EP0161541B1 (fr)	1990-12-12	Acides 6-[1-hydroxyéthyl]-2-SR8-1-méthyl-1-carbadéthiapen-2-ème-carboxyliques
JPS60233077A (ja)	1985-11-19	１‐テヘロ‐６‐〔１‐ヒドロキシエチル〕‐２‐ｓｒ↑８‐１‐カルバデチアペン‐２‐エム‐３‐カルボン酸
US4181733A (en)	1980-01-01	Carboxyl derivatives of thienamycin
US4348320A (en)	1982-09-07	Substituted azetidiones
US4293555A (en)	1981-10-06	6- and 6,6-Disubstituted-2-substituted-oxapen-2-em-3-carboxylic acids
IE882347L (en)	1989-01-31	Stable Oxapenem-3-carboxylic acids
GB1570989A (en)	1980-07-09	Derivatives of thienamycin and its isomers
US4374848A (en)	1983-02-22	6-(1-Hydroxyethyl)cyclonocardicin
US4277482A (en)	1981-07-07	3-Substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid s-oxides
US4172895A (en)	1979-10-30	6-(1'-Hydroxyethyl)-2-aminoethylthio-oxapen-2-em-3-carboxylic acid
US4717728A (en)	1988-01-05	Cyclic amidinyl and cyclic guanidinyl thio carbapenems
US4565808A (en)	1986-01-21	3-Phosphonate carbapenems
US4372965A (en)	1983-02-08	6-, 1- And 2-substituted-thio-1-carbadethiapen-2-em-3-carboxylic acid S-oxides
US4146633A (en)	1979-03-27	Δ3 -Thienamycin
EP0235823A2 (fr)	1987-09-09	Antibiotiques dérivés de carbapénème, un procédé pour les préparer et compositions pharmaceutiques les contenant