CH558347A - Verfahren zur herstellung von derivaten des helveticosids oder des helveticosols. - Google Patents

Verfahren zur herstellung von derivaten des helveticosids oder des helveticosols.

Info

Publication number: CH558347A
Authority: CH; Switzerland
Prior art keywords: helveticoside; compound; chloroform; formula; helveticosol
Prior art date: 1966-02-11

Application number

CH186967A

Other languages

German (de)

English (en)

Original Assignee

Boehringer Mannheim Gmbh

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.)

1966-02-11

Filing date

1967-02-08

Publication date

1975-01-31

1967-02-08 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1975-01-31 Publication of CH558347A publication Critical patent/CH558347A/de

Links

QBILRDAMJUPXCX-AGAUEGNUSA-N Helveticoside Chemical class C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(C=O)CC1 QBILRDAMJUPXCX-AGAUEGNUSA-N 0.000 title claims abstract description 39
230000000747 cardiac effect Effects 0.000 title abstract 2
HKNQDCBTAOHPIM-UHFFFAOYSA-N Helveticosid Natural products CC1OCC(CC(O)C1O)OC2CCC3(C=O)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C6=CC(=O)OC6 HKNQDCBTAOHPIM-UHFFFAOYSA-N 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 22
KISYRRMFQYIIFQ-PQLBFUHRSA-N Helveticosol Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CCC3[C@@]4(O)CCC(C=5COC(=O)C=5)[C@@]4(C)CCC3[C@@]2(CO)CC1 KISYRRMFQYIIFQ-PQLBFUHRSA-N 0.000 claims abstract description 13
KISYRRMFQYIIFQ-UHFFFAOYSA-N Helveticosol Natural products C1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CCC3C2(CO)CC1 KISYRRMFQYIIFQ-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
-1 di-n-propyloxyacetyl Chemical group 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 abstract description 4
230000010933 acylation Effects 0.000 abstract description 4
238000005917 acylation reaction Methods 0.000 abstract description 4
238000001990 intravenous administration Methods 0.000 abstract description 3
150000008065 acid anhydrides Chemical class 0.000 abstract description 2
235000000346 sugar Nutrition 0.000 abstract description 2
125000003302 alkenyloxy group Chemical group 0.000 abstract 2
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical class 0.000 abstract 2
150000004820 halides Chemical class 0.000 abstract 1
150000008163 sugars Chemical class 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 68
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 34
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000002425 crystallisation Methods 0.000 description 20
230000008025 crystallization Effects 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000003208 petroleum Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000002253 acid Substances 0.000 description 5
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 4
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 4
241000700198 Cavia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002038 ethyl acetate fraction Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
CTNPHHZPAJYPFO-PDXBGNJTSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,4s,5r,6r)-5-[(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@H]2C[C@@H]([C@@H]([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](CO)O2)O)OC)=CC(=O)OC1 CTNPHHZPAJYPFO-PDXBGNJTSA-N 0.000 description 2
GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 2
ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 2
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
FHIREUBIEIPPMC-UHFFFAOYSA-N K-Strophanthin-beta Natural products O1C(C)C(OC2C(C(O)C(O)C(CO)O2)O)C(OC)CC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C1=CC(=O)OC1 FHIREUBIEIPPMC-UHFFFAOYSA-N 0.000 description 2
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229930182470 glycoside Natural products 0.000 description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 description 1
FDWRIIDFYSUTDP-KVTDHHQDSA-N (2r,4r,5s,6r)-6-methyloxane-2,4,5-triol Chemical compound C[C@H]1O[C@@H](O)C[C@@H](O)[C@@H]1O FDWRIIDFYSUTDP-KVTDHHQDSA-N 0.000 description 1
FDWRIIDFYSUTDP-UHFFFAOYSA-N 102850-49-7 Natural products CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 description 1
KWFCSMSCNOVLBA-UHFFFAOYSA-N 2-hydroxy-3-oxobutanoic acid Chemical compound CC(=O)C(O)C(O)=O KWFCSMSCNOVLBA-UHFFFAOYSA-N 0.000 description 1
QXWUJRONCAPLLL-UHFFFAOYSA-N 2-prop-2-enoxyacetic acid Chemical compound OC(=O)COCC=C QXWUJRONCAPLLL-UHFFFAOYSA-N 0.000 description 1
SGUYGLMQEOSQTH-UHFFFAOYSA-N 2-propoxyacetic acid Chemical compound CCCOCC(O)=O SGUYGLMQEOSQTH-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
JWFRNGYBHLBCMB-UHFFFAOYSA-N D-Canaytose Natural products CC(O)C(O)C(O)CC=O JWFRNGYBHLBCMB-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
MSQDVGOEBXMPRF-UHFFFAOYSA-N cyclohexane;propan-2-one Chemical compound CC(C)=O.C1CCCCC1 MSQDVGOEBXMPRF-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
238000001802 infusion Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or 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
- C07D307/58—One oxygen atom, e.g. butenolide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Steroid Compounds (AREA)

CH186967A 1966-02-11 1967-02-08 Verfahren zur herstellung von derivaten des helveticosids oder des helveticosols. CH558347A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB6273/66A GB1113027A (en)	1966-02-11	1966-02-11	Derivatives of helveticoside
GB3954866		1966-09-05

Publications (1)

Publication Number	Publication Date
CH558347A true CH558347A (de)	1975-01-31

Family

ID=26240571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH186967A CH558347A (de)	1966-02-11	1967-02-08	Verfahren zur herstellung von derivaten des helveticosids oder des helveticosols.

Country Status (9)

Country	Link
US (1)	US3471614A (fr)
JP (1)	JPS5130068B1 (fr)
AT (1)	AT268539B (fr)
CH (1)	CH558347A (fr)
DE (1)	DE1568220A1 (fr)
FI (1)	FI45325C (fr)
FR (2)	FR1511249A (fr)
GB (1)	GB1113027A (fr)
NL (1)	NL153208B (fr)

1966
- 1966-02-11 GB GB6273/66A patent/GB1113027A/en not_active Expired
- 1966-12-20 DE DE19661568220 patent/DE1568220A1/de active Pending
- 1966-12-27 US US604588A patent/US3471614A/en not_active Expired - Lifetime
1967
- 1967-02-08 CH CH186967A patent/CH558347A/de not_active IP Right Cessation
- 1967-02-09 FI FI670378A patent/FI45325C/fi active
- 1967-02-10 NL NL676702085A patent/NL153208B/xx unknown
- 1967-02-10 AT AT131767A patent/AT268539B/de active
- 1967-02-10 FR FR94570A patent/FR1511249A/fr not_active Expired
- 1967-02-10 FR FR94572A patent/FR6138M/fr not_active Expired
- 1967-02-10 JP JP42008641A patent/JPS5130068B1/ja active Pending

Also Published As

Publication number	Publication date
JPS5130068B1 (fr)	1976-08-30
DE1568220A1 (de)	1970-07-09
FR1511249A (fr)	1968-01-26
US3471614A (en)	1969-10-07
FI45325B (fr)	1972-01-31
GB1113027A (en)	1968-05-08
NL153208B (nl)	1977-05-16
FI45325C (fi)	1972-05-10
AT268539B (de)	1969-02-10
FR6138M (fr)	1968-06-24
NL6702085A (fr)	1967-08-14

Legal Events

Date	Code	Title	Description
1979-12-14	PL	Patent ceased

Publication	Publication Date	Title
DE3873870T2 (de)	1993-02-18	Androstan-17-carbonsaeureester, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten.
DE1618065B2 (de)	1977-06-08	21-oxo-23-desoxo-cardenolide, verfahren zu deren herstellung und daraus hergestellte arzneimittel
DE1962757B2 (de)	1979-03-15	Evomonosid-Derivate, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
DE2318767C3 (de)	1980-07-17	Triamcinolon-Derivat, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
CH497413A (de)	1970-10-15	Verfahren zur Herstellung von Acylderivaten des Proscillaridins A
DE1568220A1 (de)	1970-07-09	Verfahren zur Herstellung von Derivaten des Helveticosids
DE1643652B1 (de)	1971-12-16	3',4'-Diaether des Helveticosids und Verfahren zu deren Herstellung
DE1214358B (de)	1966-04-14	Roentgenkontrastmittel
CH526526A (de)	1972-08-15	Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons
DE1643652C (de)	1972-08-17	3, 4 Diather des Helveticosids und Verfahren zu deren Herstellung
DE1568222C (de)	1971-12-30	3,4-Diäther des Helveticosids und Helveticosols und Verfahren zu deren Herstellung
DE2123380C3 (de)	1981-07-02	p-Aminophenol-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende therapeutische Mittel
DE1568219C3 (de)	1976-12-23	Derivate des Acovenosids A und Verfahren zu ihrer Herstellung
DE2016704C3 (de)	1979-09-06	Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner Herstellung
DE949471C (de)	1956-09-20	Verfahren zur Herstellung von neuen Estern des Yohimbins
AT270882B (de)	1969-05-12	Verfahren zur Herstellung von neuen, leicht resorbierbaren Proscillaridinketalen
DE940828C (de)	1956-03-29	Verfahren zur Herstellung von Estern des Penicillins mit Phenolen und Thiophenolen
AT209006B (de)	1960-05-10	Verfahren zur Herstellung von neuen 9 α-Halogen-16 α-oxy-hydrocortisonen und deren Estern
DE2306580C2 (de)	1982-04-15	Verfahren zur Herstellung von 16-Acylderivaten des Gitoxigenindigitoxosids
AT241707B (de)	1965-08-10	Verfahren zur Herstellung neuer Oestradiolderivate
AT166702B (de)	1950-09-11	Verfahren zur Herstellung von neuen halogenierten Pyrimidylmercaptocarbonsäuren und ihren Derivaten
DE1470005A1 (de)	1969-02-13	Verfahren zur Darstellung von neuen Estern des p-Acetaminophenols
DE1255106B (de)	1967-11-30	Verfahren zur Herstellung von N, N'-substituierten 21, 22-Bis-aminomethyl-23, 24-bis-nor-(5beta)-cholanen bzw. von Saeureadditions- oder quaternaeren Ammoniumsalzen derselben
DE2202518A1 (de)	1972-08-10	O-Ester von ara-Cytidin und Verfahren zu ihrer Herstellung
DE1136703B (de)	1962-09-20	Verfahren zur Herstellung von choleretisch wirksamen Phenyl-aethylcarbinol-carbonsaeureestern