CA1128882A - Antibiotic neplanocins - Google Patents
Antibiotic neplanocinsInfo
- Publication number
- CA1128882A CA1128882A CA328,113A CA328113A CA1128882A CA 1128882 A CA1128882 A CA 1128882A CA 328113 A CA328113 A CA 328113A CA 1128882 A CA1128882 A CA 1128882A
- Authority
- CA
- Canada
- Prior art keywords
- neplanocin
- formula
- group
- neplanocins
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229930182507 Neplanocin Natural products 0.000 title claims abstract description 31
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 11
- ZOGIBYIZRGKFQR-VDAHYXPESA-N 9-[(1r,4r,5s)-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]-3h-purin-6-one Chemical compound O[C@@H]1[C@H](O)C(CO)=C[C@H]1N1C(NC=NC2=O)=C2N=C1 ZOGIBYIZRGKFQR-VDAHYXPESA-N 0.000 claims abstract description 78
- ZOGIBYIZRGKFQR-UHFFFAOYSA-N Neplanocin D Natural products OC1C(O)C(CO)=CC1N1C(NC=NC2=O)=C2N=C1 ZOGIBYIZRGKFQR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 32
- XUGWUUDOWNZAGW-VDAHYXPESA-N (1s,2r,5r)-5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1C=C(CO)[C@@H](O)[C@H]1O XUGWUUDOWNZAGW-VDAHYXPESA-N 0.000 claims abstract description 31
- XUGWUUDOWNZAGW-UHFFFAOYSA-N neplanocin A Natural products C1=NC=2C(N)=NC=NC=2N1C1C=C(CO)C(O)C1O XUGWUUDOWNZAGW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 21
- UTCNWBUUZPUVLH-GBSPZJCNSA-N (1s,2s,3s,4s,5r)-4-(6-aminopurin-9-yl)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane-2,3-diol Chemical compound NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@]2(CO)O[C@@H]21 UTCNWBUUZPUVLH-GBSPZJCNSA-N 0.000 claims abstract description 18
- UTCNWBUUZPUVLH-UHFFFAOYSA-N Neplanocin C Natural products NC1=NC=NC2=C1N=CN2C1C(O)C(O)C2(CO)OC21 UTCNWBUUZPUVLH-UHFFFAOYSA-N 0.000 claims abstract description 18
- QTTPSWNJDDVBIP-YEPSODPASA-N (1r,2s,3s)-2-(6-aminopurin-9-yl)-4-(hydroxymethyl)cyclopent-4-ene-1,3-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1[C@H](O)C=C(CO)[C@@H]1O QTTPSWNJDDVBIP-YEPSODPASA-N 0.000 claims abstract description 17
- OLQGNBWDUALSOQ-UHFFFAOYSA-N Neplanocin F Natural products Nc1ncnc2c1ncn2C3CC(=C(CO)C3O)O OLQGNBWDUALSOQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000006239 protecting group Chemical group 0.000 claims abstract description 17
- KFVDGQIFGNKMLJ-WELJQELGSA-N (1r,2r,3s,4s,5s)-3-(6-aminopurin-9-yl)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane-2,4-diol Chemical compound NC1=NC=NC2=C1N=CN2[C@@H]1[C@@H](O)[C@@]2(CO)O[C@H]2[C@H]1O KFVDGQIFGNKMLJ-WELJQELGSA-N 0.000 claims abstract description 16
- KFVDGQIFGNKMLJ-UHFFFAOYSA-N Neplanocin B Natural products NC1=NC=NC2=C1N=CN2C1C(O)C2(CO)OC2C1O KFVDGQIFGNKMLJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 244000005700 microbiome Species 0.000 claims abstract description 8
- 241000187844 Actinoplanes Species 0.000 claims abstract description 4
- 235000015097 nutrients Nutrition 0.000 claims abstract description 4
- 238000012258 culturing Methods 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract 4
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 241000187712 Actinoplanes sp. Species 0.000 claims description 7
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 239000012320 chlorinating reagent Substances 0.000 claims 2
- 239000012022 methylating agents Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910001868 water Inorganic materials 0.000 description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 238000000862 absorption spectrum Methods 0.000 description 21
- 239000013078 crystal Substances 0.000 description 18
- 239000002609 medium Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 241000786363 Rhampholeon spectrum Species 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 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 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000003729 cation exchange resin Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
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- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- 238000004458 analytical method Methods 0.000 description 5
- 238000004042 decolorization Methods 0.000 description 5
- 229910052805 deuterium Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 5
- 239000012286 potassium permanganate Substances 0.000 description 5
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- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
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- 239000003463 adsorbent Substances 0.000 description 4
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- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 4
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 3
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- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
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- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
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- NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 1
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- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
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- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 239000002552 dosage form Substances 0.000 description 1
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- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 238000009630 liquid culture Methods 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 239000011572 manganese Substances 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 239000002207 metabolite Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
- 229940120668 salicin Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
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- 239000003549 soybean oil Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6289978A JPS54154792A (en) | 1978-05-25 | 1978-05-25 | Novel antibiotic a-11079-b1b and its preparation |
| JP53-62899 | 1978-05-25 | ||
| JP53-98027 | 1978-08-10 | ||
| JP9802778A JPS5524157A (en) | 1978-08-10 | 1978-08-10 | Novel antibiotic substance a-11079-b2 and its preparation |
| JP820579A JPS55100388A (en) | 1979-01-29 | 1979-01-29 | Novel substance neplanocin d and its derivative |
| JP54-8205 | 1979-01-29 | ||
| JP2120179A JPS55113786A (en) | 1979-02-23 | 1979-02-23 | Novel substance, nepranosin b or f and its preparation |
| JP54-21201 | 1979-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128882A true CA1128882A (en) | 1982-08-03 |
Family
ID=27454901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA328,113A Expired CA1128882A (en) | 1978-05-25 | 1979-05-23 | Antibiotic neplanocins |
Country Status (13)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3148363A1 (de) * | 1980-12-12 | 1982-09-16 | Toyo Jozo K.K., Shizuoka | Neplanocin a-derivate |
| US4742064A (en) * | 1985-09-10 | 1988-05-03 | Regents Of The University Of Minnesota | Antiviral carbocyclic analogs of xylofuranosylpurines |
| ZA894534B (en) * | 1988-06-20 | 1990-03-28 | Merrell Dow Pharma | Novel neplanocin derivatives |
| US5059690A (en) * | 1990-03-01 | 1991-10-22 | E. R. Squibb & Sons, Inc. | Purinyl tetrahydrofurans |
| US5164520A (en) * | 1989-04-24 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Intermediates for purinyl and pyrimidinyl tetrahydrofurans |
| US5145960A (en) * | 1989-04-24 | 1992-09-08 | E. R. Squibb & Sons, Inc. | Pyrimidinyl tetrahydrofurans |
| NZ232993A (en) * | 1989-04-24 | 1992-10-28 | Squibb & Sons Inc | Purinyl and pyrimidinyl tetrahydrofurans |
-
1979
- 1979-04-12 HU HU79TO1102A patent/HU192741B/hu unknown
- 1979-04-26 NL NLAANVRAGE7903318,A patent/NL182231C/xx not_active IP Right Cessation
- 1979-04-26 DE DE2917000A patent/DE2917000C2/de not_active Expired
- 1979-04-26 DE DE2954197A patent/DE2954197C2/de not_active Expired - Lifetime
- 1979-04-26 SE SE7903672A patent/SE443576B/sv not_active IP Right Cessation
- 1979-04-30 DK DK177079A patent/DK149313C/da not_active IP Right Cessation
- 1979-05-08 FR FR7911578A patent/FR2426688A1/fr active Granted
- 1979-05-09 ES ES480384A patent/ES480384A1/es not_active Expired
- 1979-05-17 SU SU792763801A patent/SU906388A3/ru active
- 1979-05-18 GB GB7917481A patent/GB2021582B/en not_active Expired
- 1979-05-23 MX MX797996U patent/MX5788E/es unknown
- 1979-05-23 CA CA328,113A patent/CA1128882A/en not_active Expired
- 1979-05-24 IT IT7922957A patent/IT1115245B/it active
- 1979-05-25 CH CH490879A patent/CH641804A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2954197C2 (enrdf_load_stackoverflow) | 1990-09-27 |
| SE443576B (sv) | 1986-03-03 |
| DE2917000A1 (de) | 1979-11-29 |
| IT7922957A0 (it) | 1979-05-24 |
| NL7903318A (nl) | 1979-11-27 |
| DK177079A (da) | 1979-11-26 |
| GB2021582A (en) | 1979-12-05 |
| FR2426688A1 (fr) | 1979-12-21 |
| DE2917000C2 (de) | 1985-10-03 |
| GB2021582B (en) | 1982-10-20 |
| DK149313C (da) | 1986-10-20 |
| IT1115245B (it) | 1986-02-03 |
| NL182231C (nl) | 1988-02-01 |
| SE7903672L (sv) | 1979-11-26 |
| ES480384A1 (es) | 1980-04-01 |
| FR2426688B1 (enrdf_load_stackoverflow) | 1982-03-12 |
| CH641804A5 (de) | 1984-03-15 |
| DK149313B (da) | 1986-04-28 |
| HU192741B (en) | 1987-07-28 |
| NL182231B (nl) | 1987-09-01 |
| SU906388A3 (ru) | 1982-02-15 |
| MX5788E (es) | 1984-07-11 |
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