SE439322B - Forfarande for framstellning av seskviterpenderivat genom odling av en mikroorganism tillhorande slektet stachybotrys - Google Patents

Forfarande for framstellning av seskviterpenderivat genom odling av en mikroorganism tillhorande slektet stachybotrys

Info

Publication number: SE439322B
Authority: SE; Sweden
Prior art keywords: stachybotrys; colony; cultivation; compound; strain
Prior art date: 1977-06-30

Application number

SE7805606A

Other languages

English (en)

Swedish (sv)

Other versions

SE7805606L (sv

Inventor

M Shinohara

H Kaise

Y Nakano

T Izawa

Y Oshiro

W Miyazaki

Original Assignee

Otsuka Pharma Co Ltd

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.)

1977-06-30

Filing date

1978-05-16

Publication date

1985-06-10

1977-06-30 Priority claimed from JP52078641A external-priority patent/JPS589114B2/ja

1977-12-29 Priority claimed from JP15895977A external-priority patent/JPS5492680A/ja

1978-02-10 Priority claimed from JP53014674A external-priority patent/JPS5936913B2/ja

1978-05-16 Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd

1979-01-08 Publication of SE7805606L publication Critical patent/SE7805606L/xx

1985-06-10 Publication of SE439322B publication Critical patent/SE439322B/sv

Links

238000000034 method Methods 0.000 title claims description 23
241001279361 Stachybotrys Species 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 16
244000005700 microbiome Species 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 47
241001574328 Stachybotrys sp. Species 0.000 claims description 35
239000001963 growth medium Substances 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
241001279364 Stachybotrys chartarum Species 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 4
241001598061 Stachybotrys cylindrospora Species 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
241000282941 Rangifer tarandus Species 0.000 claims 1
235000013619 trace mineral Nutrition 0.000 claims 1
239000011573 trace mineral Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 24
235000002639 sodium chloride Nutrition 0.000 description 22
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
239000002609 medium Substances 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
238000012360 testing method Methods 0.000 description 15
229920001817 Agar Polymers 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000008272 agar Substances 0.000 description 14
235000010419 agar Nutrition 0.000 description 14
230000003171 anti-complementary effect Effects 0.000 description 14
239000002904 solvent Substances 0.000 description 14
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 12
235000001727 glucose Nutrition 0.000 description 12
239000008103 glucose Substances 0.000 description 12
239000003814 drug Substances 0.000 description 11
239000000049 pigment Substances 0.000 description 11
241000700159 Rattus Species 0.000 description 10
229920002472 Starch Polymers 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
150000004354 sesquiterpene derivatives Chemical class 0.000 description 10
239000008107 starch Substances 0.000 description 10
235000019698 starch Nutrition 0.000 description 10
229940124597 therapeutic agent Drugs 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
239000004202 carbamide Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
235000018102 proteins Nutrition 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
102000004169 proteins and genes Human genes 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
210000004027 cell Anatomy 0.000 description 7
229940099898 chlorophyllin Drugs 0.000 description 7
235000019805 chlorophyllin Nutrition 0.000 description 7
230000018842 conidium formation Effects 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
239000006228 supernatant Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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 6
239000000969 carrier Substances 0.000 description 6
239000008101 lactose Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
238000005273 aeration Methods 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
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 5
239000008273 gelatin Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
201000008383 nephritis Diseases 0.000 description 5
238000011160 research Methods 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
230000000007 visual effect Effects 0.000 description 5
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 4
241000233866 Fungi Species 0.000 description 4
241001598067 Memnoniella echinata Species 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
235000002595 Solanum tuberosum Nutrition 0.000 description 4
239000002585 base Substances 0.000 description 4
230000037396 body weight Effects 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
235000010216 calcium carbonate Nutrition 0.000 description 4
230000002906 microbiologic effect Effects 0.000 description 4
210000000056 organ Anatomy 0.000 description 4
230000002093 peripheral effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
239000002202 Polyethylene glycol 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose 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)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
229940110456 cocoa butter Drugs 0.000 description 3
235000019868 cocoa butter Nutrition 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000012225 czapek media Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000007884 disintegrant Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
230000000877 morphologic effect Effects 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
230000001850 reproductive effect Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
230000001568 sexual effect Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
244000056139 Brassica cretica Species 0.000 description 2
235000003351 Brassica cretica Nutrition 0.000 description 2
235000003343 Brassica rupestris Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
206010018910 Haemolysis Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241001466453 Laminaria Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
241001558929 Sclerotium <basidiomycota> Species 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
208000000260 Warts Diseases 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
235000015895 biscuits Nutrition 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
235000014121 butter Nutrition 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000002421 cell wall Anatomy 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000000295 complement effect Effects 0.000 description 2
239000012531 culture fluid Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
210000003743 erythrocyte Anatomy 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
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000008588 hemolysis Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000001788 irregular Effects 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
235000010460 mustard Nutrition 0.000 description 2
239000006877 oatmeal agar Substances 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000010076 replication Effects 0.000 description 2
238000011218 seed culture Methods 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
201000010153 skin papilloma Diseases 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
238000005303 weighing Methods 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
ORIHZIZPTZTNCU-VMPITWQZSA-N 2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=CC=CC=C1O ORIHZIZPTZTNCU-VMPITWQZSA-N 0.000 description 1
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical class NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
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 1
244000215068 Acacia senegal Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
208000027932 Collagen disease Diseases 0.000 description 1
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 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
102000006395 Globulins Human genes 0.000 description 1
108010044091 Globulins Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
241000220317 Rosa Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
241001103812 Stachybotrys reniformis Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
229940124532 absorption promoter Drugs 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000002391 anti-complement effect Effects 0.000 description 1
108010008730 anticomplement Proteins 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229960002319 barbital Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
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
235000021240 caseins Nutrition 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000004154 complement system Effects 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000007799 cork Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000012258 culturing Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000006481 glucose medium Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
125000005908 glyceryl ester group Chemical group 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
239000003906 humectant Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000005204 hydroxybenzenes Chemical class 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000003053 immunization Effects 0.000 description 1
238000002649 immunization Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
231100000637 nephrotoxin Toxicity 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000002304 perfume Substances 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
-1 polyoxyethylene Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930004725 sesquiterpene Natural products 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
- 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
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Microbiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicinal Preparation (AREA)

SE7805606A 1977-06-30 1978-05-16 Forfarande for framstellning av seskviterpenderivat genom odling av en mikroorganism tillhorande slektet stachybotrys SE439322B (sv)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP52078641A JPS589114B2 (ja)	1977-06-30	1977-06-30	セスキテルペン類縁体、その製造法及び腎炎治療剤
JP15895977A JPS5492680A (en)	1977-12-29	1977-12-29	Novel microorganism
JP53014674A JPS5936913B2 (ja)	1978-02-10	1978-02-10	セスキテルペン誘導体

Publications (2)

Publication Number	Publication Date
SE7805606L SE7805606L (sv)	1979-01-08
SE439322B true SE439322B (sv)	1985-06-10

Family

ID=27280728

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SE7805606A SE439322B (sv)	1977-06-30	1978-05-16	Forfarande for framstellning av seskviterpenderivat genom odling av en mikroorganism tillhorande slektet stachybotrys
SE8305390A SE452008B (sv)	1977-06-30	1983-09-30	Forfarande for framstellning av seskviterpenderivat

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SE8305390A SE452008B (sv)	1977-06-30	1983-09-30	Forfarande for framstellning av seskviterpenderivat

Country Status (17)

Country	Link
US (1)	US4229466A (da)
AR (1)	AR228011A1 (da)
CA (1)	CA1142106A (da)
CH (1)	CH641452A5 (da)
DE (1)	DE2821403C2 (da)
DK (2)	DK154704C (da)
ES (2)	ES469821A1 (da)
FR (1)	FR2405941A1 (da)
GB (1)	GB1601479A (da)
IE (1)	IE46785B1 (da)
IT (1)	IT1103138B (da)
MX (1)	MX6053E (da)
NL (1)	NL181804C (da)
NO (2)	NO152220C (da)
NZ (1)	NZ187243A (da)
PT (1)	PT68035B (da)
SE (2)	SE439322B (da)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5630917A (en) *	1979-08-22	1981-03-28	Otsuka Pharmaceut Co Ltd	Preventive and remedy for hepatitis
US4423027A (en) *	1982-12-22	1983-12-27	Simon Lionel N	Pharmaceutical compositions of deglycyrrhizinated licorice (DGL)
JPS6193179A (ja) *	1984-10-15	1986-05-12	Takara Shuzo Co Ltd	グアニジルフンジン類の誘導体及びその製造方法
JPS646214A (en) *	1987-02-13	1989-01-10	Otsuka Pharma Co Ltd	Remedy for ulcerative colonopathy
US5506247A (en) *	1988-04-15	1996-04-09	T Cell Sciences, Inc.	Compounds that inhibit complement and/or suppress immune activity
US5173499A (en) *	1988-04-15	1992-12-22	T Cell Sciences, Inc.	Compounds which inhibit complement and/or suppress immune activity
US5366986A (en) *	1988-04-15	1994-11-22	T Cell Sciences, Inc.	Compounds which inhibit complement and/or suppress immune activity
US4981980A (en) *	1989-09-14	1991-01-01	Merck & Co., Inc.	Drug for treating manic depression
EP0447813A1 (en) *	1990-02-28	1991-09-25	GRUPPO LEPETIT S.p.A.	Water soluble salts of purpuromycin and pharmaceutical formulations thereof
US5532416A (en) *	1994-07-20	1996-07-02	Monsanto Company	Benzoyl derivatives and synthesis thereof
DE69509643T2 (de) *	1994-03-25	1999-10-14	Gruppo Lepetit S.P.A.	Sesquiterpenderivate
US5869688A (en) *	1994-07-20	1999-02-09	Monsanto Company	Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US5698708A (en) *	1996-06-20	1997-12-16	Monsanto Company	Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
JP4194196B2 (ja) *	1999-02-22	2008-12-10	花王株式会社	浴用剤組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3985896A (en) *	1975-07-15	1976-10-12	Smithkline Corporation	Benzophenalenofurans
US4046805A (en) *	1976-05-10	1977-09-06	American Cyanamid Company	Substituted-hydroxy-naphthalenedisulfonic acid compounds

1978
- 1978-05-10 FR FR7813932A patent/FR2405941A1/fr active Granted
- 1978-05-11 NZ NZ187243A patent/NZ187243A/en unknown
- 1978-05-12 ES ES469821A patent/ES469821A1/es not_active Expired
- 1978-05-12 NL NLAANVRAGE7805160,A patent/NL181804C/xx not_active IP Right Cessation
- 1978-05-12 DK DK212778A patent/DK154704C/da not_active IP Right Cessation
- 1978-05-12 PT PT68035A patent/PT68035B/pt unknown
- 1978-05-12 NO NO781704A patent/NO152220C/no unknown
- 1978-05-12 AR AR272175A patent/AR228011A1/es active
- 1978-05-12 CH CH519378A patent/CH641452A5/de not_active IP Right Cessation
- 1978-05-12 GB GB19140/78A patent/GB1601479A/en not_active Expired
- 1978-05-15 IE IE975/78A patent/IE46785B1/en not_active IP Right Cessation
- 1978-05-15 US US05/906,300 patent/US4229466A/en not_active Expired - Lifetime
- 1978-05-15 CA CA000303381A patent/CA1142106A/en not_active Expired
- 1978-05-15 IT IT49342/78A patent/IT1103138B/it active
- 1978-05-16 SE SE7805606A patent/SE439322B/sv not_active IP Right Cessation
- 1978-05-16 DE DE2821403A patent/DE2821403C2/de not_active Expired
- 1978-06-02 MX MX787121U patent/MX6053E/es unknown
1979
- 1979-02-15 ES ES477771A patent/ES477771A1/es not_active Expired
1983
- 1983-09-30 SE SE8305390A patent/SE452008B/sv not_active IP Right Cessation
- 1983-11-28 NO NO834363A patent/NO154013C/no unknown
1987
- 1987-02-04 DK DK058487A patent/DK155670C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO781704L (no)	1979-01-03
NZ187243A (en)	1984-07-31
CH641452A5 (de)	1984-02-29
DK58487D0 (da)	1987-02-04
PT68035B (en)	1979-10-24
SE7805606L (sv)	1979-01-08
NO154013C (no)	1986-07-02
DK154704C (da)	1989-05-08
DK154704B (da)	1988-12-12
MX6053E (es)	1984-10-16
IT1103138B (it)	1985-10-14
NL181804B (nl)	1987-06-01
DK155670C (da)	1989-09-18
NO152220B (no)	1985-05-13
DK155670B (da)	1989-05-01
FR2405941B1 (da)	1983-02-04
ES469821A1 (es)	1979-09-16
US4229466A (en)	1980-10-21
ES477771A1 (es)	1979-12-01
IE780975L (en)	1978-12-30
SE8305390D0 (sv)	1983-09-30
NL7805160A (nl)	1979-01-03
SE8305390L (sv)	1983-09-30
DK58487A (da)	1987-02-04
FR2405941A1 (fr)	1979-05-11
DK212778A (da)	1978-12-31
NO154013B (no)	1986-03-24
AR228011A1 (es)	1983-01-14
IE46785B1 (en)	1983-09-21
NL181804C (nl)	1987-11-02
PT68035A (en)	1978-05-31
CA1142106A (en)	1983-03-01
DE2821403C2 (de)	1984-01-26
NO834363L (no)	1979-01-03
NO152220C (no)	1985-08-21
SE452008B (sv)	1987-11-09
IT7849342A0 (it)	1978-05-15
GB1601479A (en)	1981-10-28
DE2821403A1 (de)	1979-01-25

Legal Events

Date

Code

Title

Description

1995-01-31

NAL

Patent in force

Ref document number: 7805606-6

Format of ref document f/p: F

1998-08-03

NUG

Patent has lapsed