DD234172A3 - Verfahren zur herstellung von ergotamin - Google Patents

Verfahren zur herstellung von ergotamin Download PDF

Info

Publication number: DD234172A3
Authority: DD; German Democratic Republic
Prior art keywords: ergotamine; alkaloids; nutrient medium; strain; alkaloid
Prior art date: 1979-07-16

Application number

DD21723579A

Other languages

German (de)

English (en)

Inventor

Alfred Baumert

Dieter Erge

Detlef Groeger

Walter Maier

Hans-Peter Schmauder

Brigitte Schumann

Klaus Breuel

Liselotte Hoehne

Original Assignee

Akad Wissenschaften Ddr

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.)

1979-07-16

Filing date

1979-07-16

Publication date

1986-03-26

1979-07-16 Application filed by Akad Wissenschaften Ddr filed Critical Akad Wissenschaften Ddr

1979-07-16 Priority to DD21723579A priority Critical patent/DD234172A3/de

1980-11-20 Priority to CS794080A priority patent/CS258001B1/cs

1986-03-26 Publication of DD234172A3 publication Critical patent/DD234172A3/de

Links

OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 title claims abstract description 27
229960004943 ergotamine Drugs 0.000 title claims abstract description 27
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 title claims abstract description 27
238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 3
235000015097 nutrients Nutrition 0.000 claims abstract description 15
241000221751 Claviceps purpurea Species 0.000 claims abstract description 10
HEEACTTWORLLPM-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)ethanol Chemical compound OCCC1=CNC=N1 HEEACTTWORLLPM-UHFFFAOYSA-N 0.000 claims abstract description 3
238000010564 aerobic fermentation Methods 0.000 claims abstract description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
239000007788 liquid Substances 0.000 claims abstract description 3
239000011707 mineral Substances 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
229910052799 carbon Inorganic materials 0.000 claims abstract 2
229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
238000000855 fermentation Methods 0.000 claims description 4
230000004151 fermentation Effects 0.000 claims description 4
229930013930 alkaloid Natural products 0.000 abstract description 28
150000003797 alkaloid derivatives Chemical class 0.000 abstract description 11
239000000203 mixture Substances 0.000 abstract description 5
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 abstract description 4
YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 abstract description 4
229950001817 alpha-ergocryptine Drugs 0.000 abstract description 4
ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 abstract description 3
WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 abstract description 2
SAHHMCVYMGARBT-UHFFFAOYSA-N Isochanoclavine I Natural products C1=CC(C(C(NC)C2)C=C(C)CO)=C3C2=CNC3=C1 SAHHMCVYMGARBT-UHFFFAOYSA-N 0.000 abstract description 2
WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 abstract description 2
239000000084 colloidal system Substances 0.000 abstract description 2
229960001405 ergometrine Drugs 0.000 abstract description 2
NESVMZOPWPCFAU-ZPRCMDFASA-N ergosine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-ZPRCMDFASA-N 0.000 abstract description 2
238000000605 extraction Methods 0.000 abstract description 2
239000003960 organic solvent Substances 0.000 abstract description 2
239000002609 medium Substances 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229930006000 Sucrose Natural products 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
238000004587 chromatography analysis Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
230000008719 thickening Effects 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
206010042674 Swelling Diseases 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
229960001230 asparagine Drugs 0.000 description 2
235000009582 asparagine Nutrition 0.000 description 2
YYWXOXLDOMRDHW-UHFFFAOYSA-N beta-ergocryptine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)CC)C(C)C)C2)=C3C2=CNC3=C1 YYWXOXLDOMRDHW-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 2
UJYGDMFEEDNVBF-UHFFFAOYSA-N ergocornin Chemical compound C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229930015720 peptide alkaloid Natural products 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000020183 skimmed milk Nutrition 0.000 description 2
230000008961 swelling Effects 0.000 description 2
ZAGRKAFMISFKIO-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-IINYFYTJSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
YDOTUXAWKBPQJW-JJANYQHSSA-N 919k69s85n Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-JJANYQHSSA-N 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-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
241000233866 Fungi Species 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
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 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
208000003028 Stuttering Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
235000013405 beer Nutrition 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
230000036772 blood pressure Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
229940041514 candida albicans extract Drugs 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
238000012512 characterization method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
HEFIYUQVAZFDEE-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C=3C=CC=C4NC=C(C=34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 HEFIYUQVAZFDEE-MKTPKCENSA-N 0.000 description 1
HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 description 1
229960003133 ergot alkaloid Drugs 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000004126 nerve fiber Anatomy 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
235000013324 preserved food Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
210000001938 protoplast Anatomy 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Crystals, And After-Treatments Of Crystals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

DD21723579A 1979-07-16 1979-07-16 Verfahren zur herstellung von ergotamin DD234172A3 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD21723579A DD234172A3 (de)	1979-07-16	1979-07-16	Verfahren zur herstellung von ergotamin
CS794080A CS258001B1 (en)	1979-07-16	1980-11-20	Method of ergotamine production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD21723579A DD234172A3 (de)	1979-07-16	1979-07-16	Verfahren zur herstellung von ergotamin

Publications (1)

Publication Number	Publication Date
DD234172A3 true DD234172A3 (de)	1986-03-26

Family

ID=5521316

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD21723579A DD234172A3 (de)	1979-07-16	1979-07-16	Verfahren zur herstellung von ergotamin

Country Status (2)

Country	Link
CS (1)	CS258001B1 (cs)
DD (1)	DD234172A3 (cs)

1979
- 1979-07-16 DD DD21723579A patent/DD234172A3/de unknown
1980
- 1980-11-20 CS CS794080A patent/CS258001B1/cs unknown

Also Published As

Publication number	Publication date
CS258001B1 (en)	1988-07-15

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