CH626056A5 - - Google Patents

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Info

Publication number: CH626056A5
Authority: CH; Switzerland
Prior art keywords: dichloro; oxime; salts; pharmaceutically acceptable; preparation
Prior art date: 1975-03-20

Application number

CH334476A

Other languages

German (de)

English (en)

Inventor

Hendricus Bernardus Anto Welle

Volkert Claassen

Original Assignee

Duphar Int Res

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.)

1975-03-20

Filing date

1976-03-17

Publication date

1981-10-30

1976-03-17 Application filed by Duphar Int Res filed Critical Duphar Int Res

1981-10-30 Publication of CH626056A5 publication Critical patent/CH626056A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 38
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 13
-1 2-methoxyethoxy Chemical group 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
125000003544 oxime group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000243 solution Substances 0.000 description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
230000001430 anti-depressive effect Effects 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
229940005513 antidepressants Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229960005333 tetrabenazine Drugs 0.000 description 3
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 2
206010015995 Eyelid ptosis Diseases 0.000 description 2
102000004316 Oxidoreductases Human genes 0.000 description 2
108090000854 Oxidoreductases Proteins 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
229960002748 norepinephrine Drugs 0.000 description 2
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
201000003004 ptosis Diseases 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
230000036269 ulceration Effects 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZLUBFHZITVKEFI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(2-methoxyethoxy)propan-1-one Chemical compound COCCOCCC(=O)C1=CC=C(Cl)C(Cl)=C1 ZLUBFHZITVKEFI-UHFFFAOYSA-N 0.000 description 1
KEIYADKZZVLIEK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-(2-methoxyethoxy)butan-1-one Chemical compound COCCOCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 KEIYADKZZVLIEK-UHFFFAOYSA-N 0.000 description 1
URLXEGIAHUWLKY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-ethoxybutan-1-one Chemical compound CCOCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 URLXEGIAHUWLKY-UHFFFAOYSA-N 0.000 description 1
FHJZYTWDJLZOTE-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-(2-methoxyethoxy)pentan-1-one Chemical compound COCCOCCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 FHJZYTWDJLZOTE-UHFFFAOYSA-N 0.000 description 1
GFBAJYNLKFXOKJ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methoxypentan-1-one Chemical compound COCCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 GFBAJYNLKFXOKJ-UHFFFAOYSA-N 0.000 description 1
DOROHSJYCBBVFA-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-6-methoxyhexan-1-one Chemical compound COCCCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 DOROHSJYCBBVFA-UHFFFAOYSA-N 0.000 description 1
INENCBFYMXQRLW-UHFFFAOYSA-N 2-(2-methoxyethoxy)-1-phenylpentan-1-one Chemical compound COCCOC(C(=O)C1=CC=CC=C1)CCC INENCBFYMXQRLW-UHFFFAOYSA-N 0.000 description 1
FVZFSQDGTYKUFP-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-5-oxopentanenitrile Chemical compound ClC1=CC=C(C(=O)CCCC#N)C=C1Cl FVZFSQDGTYKUFP-UHFFFAOYSA-N 0.000 description 1
229940000681 5-hydroxytryptophan Drugs 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010006487 Bronchostenosis Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
208000007623 Lordosis Diseases 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
206010029333 Neurosis Diseases 0.000 description 1
206010029350 Neurotoxicity Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010044221 Toxic encephalopathy Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229940077481 dl- 5-hydroxytryptophan Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
208000015238 neurotic disease Diseases 0.000 description 1
230000007135 neurotoxicity Effects 0.000 description 1
231100000228 neurotoxicity Toxicity 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004202 respiratory function Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH334476A 1975-03-20 1976-03-17 CH626056A5 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7503311A NL7503311A (nl)	1975-03-20	1975-03-20	Verbindingen met antidepressieve werking.

Publications (1)

Publication Number	Publication Date
CH626056A5 true CH626056A5 (bg)	1981-10-30

Family

ID=19823425

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH334476A CH626056A5 (bg)	1975-03-20	1976-03-17
CH153781A CH634828A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.
CH153881A CH629760A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH153781A CH634828A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.
CH153881A CH629760A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.

Country Status (26)

Country	Link
US (1)	US4081552A (bg)
JP (1)	JPS6026777B2 (bg)
AR (2)	AR211009A1 (bg)
AT (1)	AT342565B (bg)
AU (1)	AU505357B2 (bg)
BE (1)	BE839745A (bg)
CA (1)	CA1077519A (bg)
CH (3)	CH626056A5 (bg)
DD (1)	DD125685A5 (bg)
DE (1)	DE2609862A1 (bg)
DK (1)	DK144034C (bg)
ES (1)	ES446187A1 (bg)
FI (1)	FI62062C (bg)
FR (1)	FR2304337A1 (bg)
GB (1)	GB1531613A (bg)
GR (1)	GR59317B (bg)
HU (1)	HU171027B (bg)
IE (1)	IE43570B1 (bg)
IL (1)	IL49233A (bg)
IT (1)	IT1063060B (bg)
NL (1)	NL7503311A (bg)
PL (3)	PL100615B1 (bg)
SE (1)	SE425388B (bg)
SU (3)	SU670216A3 (bg)
YU (1)	YU71376A (bg)
ZA (1)	ZA761209B (bg)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1110460B (it) *	1977-03-02	1985-12-23	Ciba Geigy Ag	Prodotti che favoriscono la crescita delle piante e prodotti che proteggono le piante a base di eteri di ossime e di esteri di ossime loro preparazione e loro impiego
JPH0234772Y2 (bg) *	1986-04-07	1990-09-19
CA1321950C (en) *	1986-10-24	1993-09-07	Robert A.B. Bannard	Metal oximate/polyethylene glycols chemical decontaminant system
FR2639942B1 (fr) *	1988-12-02	1991-03-29	Sanofi Sa	Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant
HUT54347A (en) *	1989-01-10	1991-02-28	Chinoin Gyogyszer Es Vegyeszet	Improved process for producing amidoximes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3692835A (en) *	1967-04-05	1972-09-19	Jan Van Dijk	Pharmacologically active amino-ethyl oximes

1975
- 1975-03-20 NL NL7503311A patent/NL7503311A/xx not_active Application Discontinuation
1976
- 1976-02-27 SE SE7602716A patent/SE425388B/xx not_active IP Right Cessation
- 1976-03-01 ZA ZA761209A patent/ZA761209B/xx unknown
- 1976-03-10 DE DE19762609862 patent/DE2609862A1/de active Granted
- 1976-03-15 AR AR262560A patent/AR211009A1/es active
- 1976-03-17 DK DK115576A patent/DK144034C/da active
- 1976-03-17 CH CH334476A patent/CH626056A5/de not_active IP Right Cessation
- 1976-03-17 GR GR50334A patent/GR59317B/el unknown
- 1976-03-17 IT IT21324/76A patent/IT1063060B/it active
- 1976-03-17 IL IL49233A patent/IL49233A/xx unknown
- 1976-03-17 PL PL1976188002A patent/PL100615B1/pl unknown
- 1976-03-17 PL PL1976199549A patent/PL101884B1/pl unknown
- 1976-03-17 PL PL1976199548A patent/PL100050B1/pl unknown
- 1976-03-17 GB GB10702/76A patent/GB1531613A/en not_active Expired
- 1976-03-17 AT AT195376A patent/AT342565B/de not_active IP Right Cessation
- 1976-03-17 CA CA248,106A patent/CA1077519A/en not_active Expired
- 1976-03-17 SU SU762334810A patent/SU670216A3/ru active
- 1976-03-17 FI FI760694A patent/FI62062C/fi not_active IP Right Cessation
- 1976-03-17 HU HU76PI00000510A patent/HU171027B/hu not_active IP Right Cessation
- 1976-03-18 ES ES446187A patent/ES446187A1/es not_active Expired
- 1976-03-18 IE IE566/76A patent/IE43570B1/en unknown
- 1976-03-18 AU AU12146/76A patent/AU505357B2/en not_active Expired
- 1976-03-18 DD DD191913A patent/DD125685A5/xx unknown
- 1976-03-18 BE BE165317A patent/BE839745A/xx not_active IP Right Cessation
- 1976-03-18 YU YU00713/76A patent/YU71376A/xx unknown
- 1976-03-19 US US05/668,454 patent/US4081552A/en not_active Expired - Lifetime
- 1976-03-19 JP JP51029395A patent/JPS6026777B2/ja not_active Expired
- 1976-03-19 FR FR7608020A patent/FR2304337A1/fr active Granted
- 1976-12-02 AR AR265704A patent/AR212818A1/es active
1977
- 1977-07-11 SU SU772500952A patent/SU623517A3/ru active
- 1977-07-12 SU SU772503852A patent/SU626691A3/ru active
1981
- 1981-03-06 CH CH153781A patent/CH634828A5/de not_active IP Right Cessation
- 1981-03-06 CH CH153881A patent/CH629760A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU623517A3 (ru)	1978-09-05
DK115576A (da)	1976-09-21
AT342565B (de)	1978-04-10
CH629760A5 (de)	1982-05-14
CH634828A5 (de)	1983-02-28
JPS6026777B2 (ja)	1985-06-25
AU505357B2 (en)	1979-11-15
ES446187A1 (es)	1977-10-01
DE2609862A1 (de)	1976-10-07
JPS51138640A (en)	1976-11-30
GB1531613A (en)	1978-11-08
IE43570B1 (en)	1981-04-08
IL49233A (en)	1978-08-31
ATA195376A (de)	1977-08-15
DE2609862C2 (bg)	1987-09-24
YU71376A (en)	1982-10-31
FI62062B (fi)	1982-07-30
DK144034C (da)	1982-04-26
DD125685A5 (bg)	1977-05-11
BE839745A (fr)	1976-09-20
CA1077519A (en)	1980-05-13
SU626691A3 (ru)	1978-09-30
AR211009A1 (es)	1977-10-14
ZA761209B (en)	1977-10-26
SE425388B (sv)	1982-09-27
AU1214676A (en)	1977-09-22
DK144034B (da)	1981-11-23
SE7602716L (sv)	1976-09-21
FI760694A (bg)	1976-09-21
FR2304337B1 (bg)	1979-09-28
US4081552A (en)	1978-03-28
PL101884B1 (pl)	1979-02-28
PL100615B1 (pl)	1978-10-31
GR59317B (en)	1977-12-12
PL100050B1 (pl)	1978-08-31
IT1063060B (it)	1985-02-11
AR212818A1 (es)	1978-10-13
FR2304337A1 (fr)	1976-10-15
NL7503311A (nl)	1976-09-22
IE43570L (en)	1976-09-20
SU670216A3 (ru)	1979-06-25
FI62062C (fi)	1982-11-10
HU171027B (hu)	1977-10-28
IL49233A0 (en)	1976-05-31

Publication	Publication Date	Title
DE2610886C2 (bg)	1987-09-24
DE2634288B2 (bg)	1979-06-28
DE2434911A1 (de)	1975-02-06	Phenylaethylamin-derivate
DE2305092C2 (bg)	1987-10-01
EP0152868B1 (de)	1989-06-21	Isoxazol-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH615151A5 (bg)	1980-01-15
CH626056A5 (bg)	1981-10-30
DE2609437C2 (bg)	1987-10-01
DE2438413A1 (de)	1975-03-13	Heterocyclische verbindungen und verfahren zur herstellung derselben
EP0096279B1 (de)	1985-11-06	N-(2-Methoxyethyl)-noroxymorphon, dessen Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung
DE2611118C2 (bg)	1987-05-21
CH480350A (de)	1969-10-31	Verfahren zur Herstellung von neuen, kondensierten heterocyclischen Verbindungen
DE2034588C3 (de)	1979-11-22	6,7-Dimethoxy-4-benzylisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel
DE2610679C2 (de)	1985-09-12	Sulfinylgruppenhaltige Oximätherderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel
DD148633A5 (de)	1981-06-03	Verfahren zur herstellung von hexahydro-1,4-oxazepinen
DE1090215B (de)	1960-10-06	Verfahren zur Herstellung von Phenthiazinderivaten
DE2615129A1 (de)	1976-10-28	Tripeptide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2610302A1 (de)	1976-09-30	Antidepressive verbindungen
DE2903048A1 (de)	1979-08-09	Ergolinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE1620369A1 (de)	1970-04-02	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
AT222120B (de)	1962-07-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
DE1620151C (de)	1972-02-17	10 Piperazino dibenzo eckige Klammer auf a,d eckige Klammer zu cycloheptadien derivate und Verfahren zu ihrer Herstel lung
DE2022790C3 (de)	1977-07-07	10-Methyl-5-[ (4-Methylpiperazino)-acetyl J-5,10dihydro-llH-dibenzo [b,e ] [1,4 ] diazepin-11-on, ein Verfahren zu dessen Herstellung sowie dieses enthaltende Arzneimittel
CH638519A5 (de)	1983-09-30	2'-hydroxy-2-(5-isoxazolylmethyl)-6,7-benzomorphane, deren saeureadditionssalze und diese verbindungen enthaltende arzneimittel.
DE2538252A1 (de)	1977-03-10	Neue 1 eckige klammer auf n-propargyl- piperidyl-(4) eckige klammer zu -imidazolidinone-(2) und verfahren zu ihrer herstellung

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