NO125678B - - Google Patents

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Info

Publication number: NO125678B
Authority: NO; Norway
Prior art keywords: flavensomycin; methanol; benzene; extract; evaporating
Prior art date: 1967-09-07

Application number

NO3467/68A

Other languages

English (en)

Norwegian (no)

Inventor

E Crago

K Shepard

Original Assignee

Merck & Co Inc

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

1967-09-07

Filing date

1968-09-06

Publication date

1972-10-16

1968-09-06 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1972-10-16 Publication of NO125678B publication Critical patent/NO125678B/no

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
ASNAXPLWUAPUIY-ITNOJFFJSA-N [(e)-7,9,11,13,15,17,19,21,23-nonaoxooctatriacont-3-enyl] (e)-4-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-4-oxobut-2-enoate Chemical compound CCCCCCCCCCCCCCCC(=O)CC(=O)CC(=O)CC(=O)CC(=O)CC(=O)CC(=O)CC(=O)CC(=O)CC\C=C\CCOC(=O)\C=C\C(=O)NC1=C(O)CCC1=O ASNAXPLWUAPUIY-ITNOJFFJSA-N 0.000 claims description 24
239000003242 anti bacterial agent Substances 0.000 claims description 12
229940088710 antibiotic agent Drugs 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000000284 extract Substances 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 5
238000001704 evaporation Methods 0.000 claims description 5
229910052757 nitrogen Chemical class 0.000 claims description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 3
239000012043 crude product Substances 0.000 claims description 2
230000002538 fungal effect Effects 0.000 claims description 2
229910052500 inorganic mineral Chemical class 0.000 claims description 2
239000011707 mineral Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
241000894007 species Species 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
241000958313 Streptomyces cavourensis Species 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000012141 concentrate Substances 0.000 claims 1
238000000605 extraction Methods 0.000 claims 1
239000002917 insecticide Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
241000187747 Streptomyces Species 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
239000002609 medium Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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
238000006243 chemical reaction Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000287 crude extract Substances 0.000 description 3
239000001963 growth medium Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000013543 active substance Substances 0.000 description 2
QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000012531 culture fluid Substances 0.000 description 2
230000012010 growth Effects 0.000 description 2
239000012499 inoculation medium Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000007928 intraperitoneal injection Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000013587 production medium Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
241001446247 uncultured actinomycete Species 0.000 description 2
238000005406 washing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
229920001817 Agar Polymers 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 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
241000699670 Mus sp. Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000005273 aeration Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000008935 nutritious Nutrition 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
-1 petrol Chemical compound 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO3467/68A 1967-09-07 1968-09-06 NO125678B (xx)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66600467A	1967-09-07	1967-09-07
US71897668A	1968-03-21	1968-03-21

Publications (1)

Publication Number	Publication Date
NO125678B true NO125678B (xx)	1972-10-16

Family

ID=27099350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3467/68A NO125678B (xx)	1967-09-07	1968-09-06

Country Status (15)

Country	Link
AT (1)	AT289123B (xx)
BE (1)	BE720233A (xx)
CA (1)	CA939345A (xx)
CH (1)	CH534168A (xx)
DK (1)	DK145892C (xx)
ES (1)	ES357877A1 (xx)
FI (1)	FI50975C (xx)
FR (1)	FR8490M (xx)
GB (2)	GB1214409A (xx)
IL (1)	IL30634A0 (xx)
NL (1)	NL6812003A (xx)
NO (1)	NO125678B (xx)
OA (1)	OA02886A (xx)
SE (1)	SE355811B (xx)
YU (2)	YU205268A (xx)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT2773633T (pt)	2011-11-02	2017-11-14	Boehringer Ingelheim Int	Compostos heterocíclicos, medicamentos contendo os referidos compostos, sua utilização e processos para a sua preparação
MX2014005165A (es) *	2011-11-02	2014-05-28	Boehringer Ingelheim Int	Proceso novedoso para la preparacion de acilguanidinas y aciltioureas.
US8859559B2 (en)	2011-12-20	2014-10-14	Boehringer Ingelheim International Gmbh	Substituted pyrazines and their use in the treatment of disease
JP6204977B2 (ja)	2012-05-25	2017-09-27	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	三級アミン、前記アミンを含む薬物、その使用及びその調製方法
EP2897940B1 (en)	2012-09-24	2019-05-01	Boehringer Ingelheim International GmbH	Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof

1968
- 1968-08-22 NL NL6812003A patent/NL6812003A/xx unknown
- 1968-08-26 IL IL30634A patent/IL30634A0/xx unknown
- 1968-08-28 FI FI682412A patent/FI50975C/fi active
- 1968-08-30 BE BE720233D patent/BE720233A/xx unknown
- 1968-08-31 CA CA028,994A patent/CA939345A/en not_active Expired
- 1968-09-02 YU YU02052/68A patent/YU205268A/xx unknown
- 1968-09-03 GB GB53830/69A patent/GB1214409A/en not_active Expired
- 1968-09-03 GB GB41777/68A patent/GB1214408A/en not_active Expired
- 1968-09-04 OA OA53362A patent/OA02886A/xx unknown
- 1968-09-05 ES ES357877A patent/ES357877A1/es not_active Expired
- 1968-09-05 SE SE11956/68A patent/SE355811B/xx unknown
- 1968-09-06 DK DK429268A patent/DK145892C/da active
- 1968-09-06 NO NO3467/68A patent/NO125678B/no unknown
- 1968-09-06 AT AT872468A patent/AT289123B/de not_active IP Right Cessation
- 1968-09-06 CH CH1340268A patent/CH534168A/de not_active IP Right Cessation
- 1968-12-06 FR FR176992A patent/FR8490M/fr not_active Expired
1969
- 1969-09-02 YU YU2052/68A patent/YU34082B/xx unknown

Also Published As

Publication number	Publication date
GB1214408A (en)	1970-12-02
DK145892B (da)	1983-04-05
YU34082B (en)	1978-12-31
FI50975B (xx)	1976-05-31
NL6812003A (xx)	1969-03-11
CH534168A (de)	1973-02-28
IL30634A0 (en)	1968-10-24
GB1214409A (en)	1970-12-02
DK145892C (da)	1983-09-12
BE720233A (xx)	1969-02-28
SE355811B (xx)	1973-05-07
ES357877A1 (es)	1970-05-01
CA939345A (en)	1974-01-01
AT289123B (de)	1971-04-13
FR8490M (xx)	1973-07-27
OA02886A (fr)	1970-12-15
FI50975C (fi)	1976-09-10
YU205268A (en)	1978-06-30

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