DK166498B1 - Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse - Google Patents

Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse Download PDF

Info

Publication number: DK166498B1
Authority: DK; Denmark
Prior art keywords: compound; hydroxy; compounds; general formula; alkyl
Prior art date: 1986-06-06

Application number

DK290287A

Other languages

Danish (da)

English (en)

Other versions

DK290287D0 (da

DK290287A (da

Inventor

Derek R Sutherland

Michael V J Ramsay

Edward P Tiley

Oswy Z Pereira

John B Ward

Neil Porter

Hazel M Noble

Richard A Fletton

David Noble

Original Assignee

American Cyanamid Co

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.)

1986-06-06

Filing date

1987-06-04

Publication date

1993-06-01

1986-06-06 Priority claimed from GB868613790A external-priority patent/GB8613790D0/en

1986-10-29 Priority claimed from GB868625854A external-priority patent/GB8625854D0/en

1987-04-08 Priority claimed from GB878708423A external-priority patent/GB8708423D0/en

1987-06-04 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1987-06-04 Publication of DK290287D0 publication Critical patent/DK290287D0/da

1987-12-07 Publication of DK290287A publication Critical patent/DK290287A/da

1993-06-01 Application granted granted Critical

1993-06-01 Publication of DK166498B1 publication Critical patent/DK166498B1/da

Links

150000001875 compounds Chemical class 0.000 title claims description 146
238000002360 preparation method Methods 0.000 title claims description 33
238000000034 method Methods 0.000 title claims description 29
239000003120 macrolide antibiotic agent Substances 0.000 title claims description 4
238000002560 therapeutic procedure Methods 0.000 title claims description 3
239000000203 mixture Substances 0.000 claims description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 20
241000607479 Yersinia pestis Species 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 18
230000008569 process Effects 0.000 claims description 15
239000000969 carrier Substances 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
241000238631 Hexapoda Species 0.000 claims description 10
241000282414 Homo sapiens Species 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 9
241000244206 Nematoda Species 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
230000002252 carbamoylating effect Effects 0.000 claims description 4
HCUOEKSZWPGJIM-YBRHCDHNSA-N (e,2e)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N/O)\C(N)=O HCUOEKSZWPGJIM-YBRHCDHNSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
101001109689 Homo sapiens Nuclear receptor subfamily 4 group A member 3 Proteins 0.000 claims description 2
101000598778 Homo sapiens Protein OSCP1 Proteins 0.000 claims description 2
101001067395 Mus musculus Phospholipid scramblase 1 Proteins 0.000 claims description 2
102100022673 Nuclear receptor subfamily 4 group A member 3 Human genes 0.000 claims description 2
238000003898 horticulture Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
101100162200 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflD gene Proteins 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
-1 methoxycarbonyloxy Chemical group 0.000 description 62
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
239000004480 active ingredient Substances 0.000 description 39
239000000243 solution Substances 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 25
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 24
239000006260 foam Substances 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
239000000047 product Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 16
239000007788 liquid Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
238000000855 fermentation Methods 0.000 description 14
230000004151 fermentation Effects 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
241000196324 Embryophyta Species 0.000 description 13
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 13
238000010828 elution Methods 0.000 description 13
239000008187 granular material Substances 0.000 description 13
239000002609 medium Substances 0.000 description 13
150000002148 esters Chemical class 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
239000000843 powder Substances 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 10
239000003826 tablet Substances 0.000 description 10
241000238876 Acari Species 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000011282 treatment Methods 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
238000005917 acylation reaction Methods 0.000 description 8
235000019445 benzyl alcohol Nutrition 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000003381 stabilizer Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000010933 acylation Effects 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 6
230000021235 carbamoylation Effects 0.000 description 6
244000078703 ectoparasite Species 0.000 description 6
239000002736 nonionic surfactant Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000375 suspending agent Substances 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
244000299507 Gossypium hirsutum Species 0.000 description 5
229920000168 Microcrystalline cellulose Polymers 0.000 description 5
241000187747 Streptomyces Species 0.000 description 5
241001454293 Tetranychus urticae Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
238000006266 etherification reaction Methods 0.000 description 5
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000008108 microcrystalline cellulose Substances 0.000 description 5
229940016286 microcrystalline cellulose Drugs 0.000 description 5
235000019813 microcrystalline cellulose Nutrition 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
239000006072 paste Substances 0.000 description 5
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229920003023 plastic Polymers 0.000 description 5
239000004576 sand Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
235000019483 Peanut oil Nutrition 0.000 description 4
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229920002651 Polysorbate 85 Polymers 0.000 description 4
241000700159 Rattus Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000012267 brine Substances 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
244000079386 endoparasite Species 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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239000012085 test solution Substances 0.000 description 4
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
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238000005273 aeration Methods 0.000 description 3
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150000001298 alcohols Chemical class 0.000 description 3
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RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 3
239000003945 anionic surfactant Substances 0.000 description 3
230000000507 anthelmentic effect Effects 0.000 description 3
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239000008365 aqueous carrier Substances 0.000 description 3
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229910052799 carbon Inorganic materials 0.000 description 3
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239000003638 chemical reducing agent Substances 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
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238000007796 conventional method Methods 0.000 description 3
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150000004292 cyclic ethers Chemical class 0.000 description 3
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239000003937 drug carrier Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000003517 fume Substances 0.000 description 3
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 3
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238000000926 separation method Methods 0.000 description 3
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235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002689 soil Substances 0.000 description 3
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QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
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RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 2
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KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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241000255925 Diptera Species 0.000 description 2
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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241000257159 Musca domestica Species 0.000 description 2
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229920001778 nylon Polymers 0.000 description 1
HUYRNQWVAPCTQZ-UHFFFAOYSA-N o-butylhydroxylamine;hydrochloride Chemical compound Cl.CCCCON HUYRNQWVAPCTQZ-UHFFFAOYSA-N 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
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244000144977 poultry Species 0.000 description 1
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235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
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239000007909 solid dosage form Substances 0.000 description 1
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239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
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235000010356 sorbitol Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
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238000010561 standard procedure Methods 0.000 description 1
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239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
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230000007704 transition Effects 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
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Zoology (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Insects & Arthropods (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK290287A 1986-06-06 1987-06-04 Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse DK166498B1 (da)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB8613790		1986-06-06
GB868613790A GB8613790D0 (en)	1986-06-06	1986-06-06	Chemical compounds
GB868625854A GB8625854D0 (en)	1986-10-29	1986-10-29	Chemical process
GB8625854		1986-10-29
GB8708423		1987-04-08
GB878708423A GB8708423D0 (en)	1987-04-08	1987-04-08	Chemical compounds

Publications (3)

Publication Number	Publication Date
DK290287D0 DK290287D0 (da)	1987-06-04
DK290287A DK290287A (da)	1987-12-07
DK166498B1 true DK166498B1 (da)	1993-06-01

Family

ID=27263057

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK290287A DK166498B1 (da)	1986-06-06	1987-06-04	Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse

Country Status (35)

Country	Link
US (1)	US4900753A (pt)
JP (1)	JP2648147B2 (pt)
KR (1)	KR950010077B1 (pt)
CN (1)	CN1023858C (pt)
AR (1)	AR244691A1 (pt)
AT (1)	AT398571B (pt)
AU (1)	AU609399B2 (pt)
BE (1)	BE1000201A4 (pt)
BR (1)	BR8702866A (pt)
CA (1)	CA1296329C (pt)
CH (1)	CH677670A5 (pt)
DE (3)	DE3718926C2 (pt)
DK (1)	DK166498B1 (pt)
EG (1)	EG18752A (pt)
ES (1)	ES2006479A6 (pt)
FI (2)	FI90663C (pt)
FR (1)	FR2599742B1 (pt)
GB (1)	GB2192630B (pt)
GE (1)	GEP19981388B (pt)
GR (1)	GR870891B (pt)
HU (1)	HU199847B (pt)
IE (1)	IE60411B1 (pt)
IL (1)	IL82776A (pt)
IT (1)	IT1206015B (pt)
LU (2)	LU86908A1 (pt)
LV (2)	LV10280A (pt)
NL (2)	NL193376C (pt)
NZ (1)	NZ220587A (pt)
OA (1)	OA08606A (pt)
PH (1)	PH23948A (pt)
PL (3)	PL153226B1 (pt)
PT (1)	PT85018B (pt)
SE (1)	SE503399C2 (pt)
TR (1)	TR28970A (pt)
UA (1)	UA45300C2 (pt)

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US4886828A (en) *	1986-09-12	1989-12-12	American Cyanamid Company	Δ22 -derivatives of LL-F28249 compounds
EP0260537A1 (en) *	1986-09-12	1988-03-23	American Cyanamid Company	13-Deoxy-23-oxo(keto) and 23-imino derivatives of 13-deoxy C-076-aglycone compounds
ES2058082T3 (es) *	1986-09-12	1994-11-01	American Cyanamid Co	Derivados 23-oxo (ceto) y 23-imino de compuestos ll-f28249.
GB8721377D0 (en) *	1987-09-11	1987-10-21	Glaxo Group Ltd	Chemical compounds
GB8811036D0 (en) *	1988-05-10	1988-06-15	Glaxo Group Ltd	Chemical compounds
GB8813150D0 (en) *	1988-06-03	1988-07-06	American Cyanamid Co	Chemical compounds
GB8905605D0 (en) *	1989-03-11	1989-04-26	Beecham Group Plc	Novel compounds
NZ233680A (en) *	1989-05-17	1995-02-24	Beecham Group Plc	Avermectins and milbemycins and compositions thereof
US4988824A (en) *	1989-09-11	1991-01-29	Maulding Donald R	Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds
WO1992010170A1 (en) *	1990-12-07	1992-06-25	Temple University - Of The Commonwealth System Of Higher Education	Stabilized insect nematode compositions
JP2855181B2 (ja)	1993-12-10	1999-02-10	敏雄鈴木	松類の枯損防止用組成物及び防止方法
DK1197215T3 (da)	2000-10-10	2006-07-10	Wyeth Corp	Anthelmintiske sammensætninger
US7348417B2 (en)	2003-08-07	2008-03-25	Wyeth	Method of purifying moxidectin through crystallization
WO2006119174A1 (en)	2005-04-30	2006-11-09	Ocular Surface Center, P.A.	Method for treating ocular demodex
JP4939025B2 (ja) *	2005-09-30	2012-05-23	三菱電線工業株式会社	電熱ヒータ付きハンドル用グリップ部材
EP1849363A1 (en) *	2006-03-09	2007-10-31	Cheminova A/S	Synergistic combination of glutamate- and GABA-gated chloride agonist pesticide and at least one of Vitamin E or Niacin
US8128968B2 (en) *	2007-08-29	2012-03-06	Tissuetech, Inc.	Compositions and methods for treating Demodex infestations
ES2978407T3 (es)	2011-12-02	2024-09-12	Boehringer Ingelheim Vetmedica Gmbh	Formulaciones de moxidectina inyectables de acción prolongada
FR2995605B1 (fr) *	2012-09-18	2014-09-19	Sanofi Sa	Derives de macrolides, leur preparation et leur application therapeutique.

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PH15982A (en) *	1977-10-03	1983-05-18	Merck & Co Inc	Selective hydrogenation producta of c-076 compounds and derivatives thereof
US4289760A (en) *	1980-05-02	1981-09-15	Merck & Co., Inc.	23-Keto derivatives of C-076 compounds
US4423209A (en) *	1982-02-26	1983-12-27	Merck & Co., Inc.	Processes for the interconversion of avermectin compounds
JPS59108785A (ja) *	1982-11-25	1984-06-23	Sankyo Co Ltd	ミルベマイシン類の５−オキシム誘導体
JPS60126289A (ja) *	1983-11-14	1985-07-05	Sankyo Co Ltd	ミルベマイシン類の５−カ−ボネ−ト誘導体
DE3519834C2 (de) *	1984-06-05	1993-12-16	American Cyanamid Co	Neue antibiotische Wirkstoffe, Verfahren zu ihrer Gewinnung und ihre Anwendung zur Bekämpfung von Infektionen bei Tieren und Pflanzen
US4579864A (en) *	1984-06-11	1986-04-01	Merck & Co., Inc.	Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives
GB2166436B (en) *	1984-09-14	1989-05-24	Glaxo Group Ltd	Antibiotic compounds and their preparation
ES8802229A1 (es) *	1985-04-30	1988-04-16	Glaxo Group Ltd	Un procedimiento para preparar nuevos derivados lactonicos macrociclicos.
ES2058082T3 (es) *	1986-09-12	1994-11-01	American Cyanamid Co	Derivados 23-oxo (ceto) y 23-imino de compuestos ll-f28249.

1987
- 1987-05-26 CA CA000537979A patent/CA1296329C/en not_active Expired - Lifetime
- 1987-06-02 OA OA59131A patent/OA08606A/xx unknown
- 1987-06-04 FI FI872517A patent/FI90663C/fi not_active IP Right Cessation
- 1987-06-04 EG EG32487A patent/EG18752A/xx active
- 1987-06-04 DK DK290287A patent/DK166498B1/da not_active IP Right Cessation
- 1987-06-04 ES ES8701645A patent/ES2006479A6/es not_active Expired
- 1987-06-05 GB GB8713239A patent/GB2192630B/en not_active Expired - Lifetime
- 1987-06-05 PL PL1987266100A patent/PL153226B1/pl unknown
- 1987-06-05 TR TR00392/87A patent/TR28970A/xx unknown
- 1987-06-05 NZ NZ220587A patent/NZ220587A/xx unknown
- 1987-06-05 GR GR870891A patent/GR870891B/el unknown
- 1987-06-05 FR FR878707915A patent/FR2599742B1/fr not_active Expired
- 1987-06-05 LU LU86908A patent/LU86908A1/fr active Protection Beyond IP Right Term
- 1987-06-05 BR BR8702866A patent/BR8702866A/pt not_active IP Right Cessation
- 1987-06-05 SE SE8702361A patent/SE503399C2/sv not_active IP Right Cessation
- 1987-06-05 NL NL8701322A patent/NL193376C/nl not_active IP Right Cessation
- 1987-06-05 HU HU872583A patent/HU199847B/hu unknown
- 1987-06-05 PT PT85018A patent/PT85018B/pt unknown
- 1987-06-05 DE DE3718926A patent/DE3718926C2/de not_active Expired - Lifetime
- 1987-06-05 AT AT0143887A patent/AT398571B/de not_active IP Right Cessation
- 1987-06-05 IL IL82776A patent/IL82776A/xx not_active IP Right Cessation
- 1987-06-05 BE BE8700626A patent/BE1000201A4/fr not_active IP Right Cessation
- 1987-06-05 DE DE1998175029 patent/DE19875029I2/de active Active
- 1987-06-05 IE IE149687A patent/IE60411B1/en not_active IP Right Cessation
- 1987-06-05 AR AR87307796A patent/AR244691A1/es active
- 1987-06-05 US US07/058,856 patent/US4900753A/en not_active Expired - Lifetime
- 1987-06-05 JP JP62140139A patent/JP2648147B2/ja not_active Expired - Lifetime
- 1987-06-05 PL PL1987283187A patent/PL153036B1/pl unknown
- 1987-06-05 IT IT8748023A patent/IT1206015B/it active
- 1987-06-05 AU AU73873/87A patent/AU609399B2/en not_active Expired
- 1987-06-05 PL PL1987282198A patent/PL155723B1/pl unknown
- 1987-06-05 PH PH35347A patent/PH23948A/en unknown
- 1987-06-05 CH CH2150/87A patent/CH677670A5/de not_active IP Right Cessation
- 1987-06-05 DE DE3745133A patent/DE3745133C2/de not_active Expired - Lifetime
- 1987-06-05 CN CN87104431A patent/CN1023858C/zh not_active Expired - Lifetime
- 1987-06-05 KR KR1019870005694A patent/KR950010077B1/ko not_active Expired - Lifetime
1992
- 1992-07-30 FI FI923445A patent/FI90549C/fi not_active IP Right Cessation
- 1992-12-30 LV LV920561A patent/LV10280A/xx unknown
1993
- 1993-08-25 GE GEAP19931498A patent/GEP19981388B/en unknown
- 1993-09-15 UA UA93003885A patent/UA45300C2/uk unknown
- 1993-11-15 LV LVP-93-1233A patent/LV10781B/lv unknown
1996
- 1996-07-17 LU LU88790C patent/LU88790I2/fr unknown
1999
- 1999-08-18 NL NL990026C patent/NL990026I2/nl unknown

Also Published As

Publication number	Publication date
PT85018A (en)	1987-07-01
GEP19981388B (en)	1998-11-10
JP2648147B2 (ja)	1997-08-27
ES2006479A6 (es)	1989-05-01
NZ220587A (en)	1990-05-28
KR950010077B1 (ko)	1995-09-06
BR8702866A (pt)	1988-03-01
LV10280A (lv)	1994-10-20
FR2599742A1 (fr)	1987-12-11
GB8713239D0 (en)	1987-07-08
NL193376B (nl)	1999-04-01
ATA143887A (de)	1994-05-15
IE60411B1 (en)	1994-07-13
GB2192630A (en)	1988-01-20
FI90663B (fi)	1993-11-30
CN87104431A (zh)	1987-12-30
NL990026I1 (nl)	1999-11-01
SE503399C2 (sv)	1996-06-10
EG18752A (en)	1993-12-30
PT85018B (pt)	1990-03-08
DE3745133C2 (de)	1998-01-02
GR870891B (en)	1987-10-02
FI872517A7 (fi)	1987-12-07
SE8702361L (sv)	1987-12-07
PH23948A (en)	1990-01-23
FI923445A0 (fi)	1992-07-30
FI90549C (fi)	1994-02-25
LU86908A1 (fr)	1988-01-20
PL266100A1 (en)	1988-07-21
AU609399B2 (en)	1991-05-02
AR244691A1 (es)	1993-11-30
IT1206015B (it)	1989-04-05
LU88790I2 (fr)	1997-03-18
DE3718926A1 (de)	1987-12-10
US4900753A (en)	1990-02-13
JPS6354375A (ja)	1988-03-08
PL153036B1 (en)	1991-02-28
DK290287D0 (da)	1987-06-04
NL193376C (nl)	1999-08-03
GB2192630B (en)	1990-05-23
CH677670A5 (pt)	1991-06-14
HUT44254A (en)	1988-02-29
IT8748023A0 (it)	1987-06-05
KR880000441A (ko)	1988-03-25
CN1023858C (zh)	1994-02-23
PL155723B1 (en)	1991-12-31
OA08606A (en)	1988-11-30
CA1296329C (en)	1992-02-25
DE3718926C2 (de)	1998-01-15
IL82776A0 (en)	1987-12-20
DK290287A (da)	1987-12-07
FI90549B (fi)	1993-11-15
FI923445L (fi)	1992-07-30
IL82776A (en)	1992-02-16
NL8701322A (nl)	1988-01-04
FI90663C (fi)	1994-03-10
SE8702361D0 (sv)	1987-06-05
BE1000201A4 (fr)	1988-08-23
IE871496L (en)	1987-12-06
NL990026I2 (nl)	1999-12-01
TR28970A (tr)	1997-07-21
AU7387387A (en)	1987-12-10
PL153226B1 (en)	1991-03-29
DE19875029I2 (de)	2001-11-22
FI872517A0 (fi)	1987-06-04
LV10781B (en)	1996-10-20
LV10781A (lv)	1995-08-20
FR2599742B1 (fr)	1989-05-19
UA45300C2 (uk)	2002-04-15
AT398571B (de)	1994-12-27
HU199847B (en)	1990-03-28

Publication	Publication Date	Title
DK166498B1 (da)	1993-06-01	Macrolidforbindelser, fremgangsmaade til fremstilling deraf, praeparater indeholdende saadanne forbindelser samt en ikke-terapeutisk fremgangsmaade til bekaempelse af skadedyr under anvendelse af en saadan forbindelse
NL193420C (nl)	1999-10-04	Antibiotische verbindingen, preparaten die deze bevatten en gebruik ervan.
IE862443L (en)	1987-03-13	Fused oxygen heterocyclics
EP0237341B1 (en)	1993-09-22	Macrolide compounds
DK170859B1 (da)	1996-02-12	Makrolidforbindelser, præparater indeholdende forbindelserne til anvendelse i human medicin og veterinær medicin og til bekæmpelse af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
EP0231104B1 (en)	1992-09-09	Macrolide antibiotics and their preparation
US4996228A (en)	1991-02-26	Macrolide antibiotics
DK171063B1 (da)	1996-05-13	Makrolidforbindelser, præparater indeholdende makrolidforbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr, fremgangsmåde til fremstilling af forbindelserne samt fremgangsmåde til fremstilling af mellemprodukter
EP0341972B1 (en)	1996-09-04	Macrolide compounds
DK171255B1 (da)	1996-08-12	Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
KR950010078B1 (ko)	1995-09-06	마크롤라이드 화합물
AP38A (en)	1989-04-13	Macrolide Compounds.
RU2099334C1 (ru)	1997-12-20	Макролидные соединения, композиция, обладающая антибиотической активностью, ветеринарная композиция, инсектоакарицидонематоцидная композиция и способ уничтожения насекомых и/или клещей, нематод
US5185456A (en)	1993-02-09	Macrolide compounds
AT397096B (de)	1994-01-25	Macrolid-verbindungen, diese enthaltende mittel und verfahren zu deren herstellung
DE3781563T2 (de)	1993-01-07	Makrolid-antibiotika und verfahren zu ihrer herstellung.
HRP920589A2 (en)	1995-06-30	Macrolide compounds

Legal Events

Date	Code	Title	Description
1993-06-01	B1	Patent granted (law 1993)
1995-12-27	CTFF	Application for supplementary protection certificate (spc) filed	Free format text: CA 1995 00018, 951109
1997-04-21	CTFG	Supplementary protection certificate (spc) issued	Free format text: CA 1995 00018, 951109, EXPIRES: 20091230
2007-06-18	PUP	Patent expired