CH626062A5 - - Google Patents

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Info

Publication number: CH626062A5
Authority: CH; Switzerland
Prior art keywords: oxime; aminoethyl; salts; pharmaceutically acceptable; acceptable acids
Prior art date: 1975-03-20

Application number

CH334676A

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 CH626062A5 publication Critical patent/CH626062A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 41
-1 methoxy, ethoxy, methoxyethoxy, methoxymethyl Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
229910052801 chlorine 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
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 description 2
150000002923 oximes Chemical class 0.000 claims 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000000243 solution Substances 0.000 description 14
230000000694 effects Effects 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
229940076279 serotonin Drugs 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 6
229940005513 antidepressants Drugs 0.000 description 6
229960002748 norepinephrine Drugs 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
239000001530 fumaric acid Substances 0.000 description 5
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
208000025865 Ulcer Diseases 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000001430 anti-depressive effect Effects 0.000 description 4
230000000994 depressogenic effect Effects 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
210000002569 neuron Anatomy 0.000 description 4
VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 description 4
230000036269 ulceration Effects 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
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
210000004556 brain Anatomy 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
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000284 extract Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000036651 mood Effects 0.000 description 3
230000000862 serotonergic effect Effects 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
229960005333 tetrabenazine Drugs 0.000 description 3
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
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 2
102000004316 Oxidoreductases Human genes 0.000 description 2
108090000854 Oxidoreductases Proteins 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
230000001476 alcoholic effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
238000001035 drying Methods 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
239000012528 membrane Substances 0.000 description 2
239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
201000003004 ptosis Diseases 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AOPXLKPYGNLJFV-UHFFFAOYSA-N 5-(2-methoxyethoxy)-1-(4-methylphenyl)pentane-1-thione Chemical compound COCCOCCCCC(=S)C1=CC=C(C)C=C1 AOPXLKPYGNLJFV-UHFFFAOYSA-N 0.000 description 1
PHWBFGTUOSDUHR-UHFFFAOYSA-N 5-chloro-1-(4-methylphenyl)pentane-1-thione Chemical compound CC1=CC=C(C(=S)CCCCCl)C=C1 PHWBFGTUOSDUHR-UHFFFAOYSA-N 0.000 description 1
ZBWOOEVRPZWFOV-UHFFFAOYSA-N 5-ethoxy-1-(4-methylphenyl)pentane-1-thione Chemical compound CCOCCCCC(=S)C1=CC=C(C)C=C1 ZBWOOEVRPZWFOV-UHFFFAOYSA-N 0.000 description 1
229940000681 5-hydroxytryptophan Drugs 0.000 description 1
ZAMCLBBCAJWLEB-UHFFFAOYSA-N 5-methoxy-1-(4-methylphenyl)pentane-1-thione Chemical compound COCCCCC(=S)C1=CC=C(C)C=C1 ZAMCLBBCAJWLEB-UHFFFAOYSA-N 0.000 description 1
GTHLLNYCVCYEHH-UHFFFAOYSA-N 6-methoxy-1-(4-methylphenyl)hexane-1-thione Chemical compound COCCCCCC(=S)C1=CC=C(C)C=C1 GTHLLNYCVCYEHH-UHFFFAOYSA-N 0.000 description 1
DPRUSTIRWIXVBJ-UHFFFAOYSA-N 7-(4-methylphenyl)-7-sulfanylideneheptanenitrile Chemical compound CC1=CC=C(C(=S)CCCCCC#N)C=C1 DPRUSTIRWIXVBJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010006487 Bronchostenosis Diseases 0.000 description 1
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
206010044565 Tremor Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229960000836 amitriptyline Drugs 0.000 description 1
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 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
MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000035 biogenic effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
229960003914 desipramine Drugs 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
229940077481 dl- 5-hydroxytryptophan Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
YJJXRLAIAXXBTJ-UHFFFAOYSA-N ethene;5-ethoxy-1-(4-methylphenyl)pentane-1-thione Chemical group C=C.CCOCCCCC(=S)C1=CC=C(C)C=C1 YJJXRLAIAXXBTJ-UHFFFAOYSA-N 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
239000012458 free base Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 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
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000002474 noradrenergic effect Effects 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
230000008506 pathogenesis Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229960002601 protriptyline Drugs 0.000 description 1
BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 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
239000002904 solvent Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Measurement Of The Respiration, Hearing Ability, Form, And Blood Characteristics Of Living Organisms (AREA)
Steroid Compounds (AREA)

CH334676A 1975-03-20 1976-03-17 CH626062A5 (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7503309A NL7503309A (nl)	1975-03-20	1975-03-20	Verbindingen met antidepressieve werking.

Publications (1)

Publication Number	Publication Date
CH626062A5 true CH626062A5 (xx)	1981-10-30

Family

ID=19823423

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH334676A CH626062A5 (xx)	1975-03-20	1976-03-17
CH154281A CH629187A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.
CH154381A CH629767A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH154281A CH629187A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.
CH154381A CH629767A5 (de)	1975-03-20	1981-03-06	Verfahren zur herstellung neuer oximaetherverbindungen.

Country Status (26)

Country	Link
US (1)	US4081551A (xx)
JP (1)	JPS601303B2 (xx)
AR (2)	AR211119A1 (xx)
AT (1)	AT340897B (xx)
AU (1)	AU504592B2 (xx)
BE (1)	BE839743A (xx)
CA (1)	CA1076143A (xx)
CH (3)	CH626062A5 (xx)
DD (1)	DD128330A5 (xx)
DE (1)	DE2611118A1 (xx)
DK (1)	DK140458B (xx)
ES (1)	ES446193A1 (xx)
FI (1)	FI62288C (xx)
FR (1)	FR2304335A1 (xx)
GB (1)	GB1537898A (xx)
GR (1)	GR59316B (xx)
HU (1)	HU171159B (xx)
IE (1)	IE43824B1 (xx)
IL (1)	IL49239A (xx)
IT (1)	IT1063063B (xx)
NL (1)	NL7503309A (xx)
PL (3)	PL100617B1 (xx)
SE (1)	SE420497B (xx)
SU (2)	SU603336A3 (xx)
YU (1)	YU71576A (xx)
ZA (1)	ZA761435B (xx)

Families Citing this family (4)

* 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
US4260555A (en) *	1979-11-07	1981-04-07	Ciba-Geigy Corporation	Process for the manufacture of cyanooximinonitriles
US9783492B2 (en) *	2013-04-03	2017-10-10	Zcl Chemicals Limited	Process for the preparation of fluvoxamine maleate
CN110337244B (zh)	2016-11-24	2023-07-21	西格玛研究有限责任公司	用于器官保藏的组合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL151361B (nl) *	1967-12-14	1976-11-15	Philips Nv	Verbindingen met centrale werking.
US3692835A (en) *	1967-04-05	1972-09-19	Jan Van Dijk	Pharmacologically active amino-ethyl oximes

1975
- 1975-03-20 NL NL7503309A patent/NL7503309A/xx not_active Application Discontinuation
1976
- 1976-03-09 ZA ZA761435A patent/ZA761435B/xx unknown
- 1976-03-17 DK DK115776AA patent/DK140458B/da not_active IP Right Cessation
- 1976-03-17 DD DD7600191888A patent/DD128330A5/xx unknown
- 1976-03-17 PL PL1976188005A patent/PL100617B1/pl unknown
- 1976-03-17 IT IT21321/76A patent/IT1063063B/it active
- 1976-03-17 HU HU76PI00000514A patent/HU171159B/hu not_active IP Right Cessation
- 1976-03-17 FI FI760698A patent/FI62288C/fi not_active IP Right Cessation
- 1976-03-17 CA CA248,104A patent/CA1076143A/en not_active Expired
- 1976-03-17 SU SU762333807A patent/SU603336A3/ru active
- 1976-03-17 PL PL1976199554A patent/PL100613B1/pl unknown
- 1976-03-17 GR GR50332A patent/GR59316B/el unknown
- 1976-03-17 PL PL1976199555A patent/PL101885B1/pl unknown
- 1976-03-17 SE SE7603342A patent/SE420497B/xx not_active IP Right Cessation
- 1976-03-17 IL IL49239A patent/IL49239A/xx unknown
- 1976-03-17 GB GB10704/76A patent/GB1537898A/en not_active Expired
- 1976-03-17 AT AT194876A patent/AT340897B/de not_active IP Right Cessation
- 1976-03-17 CH CH334676A patent/CH626062A5/de not_active IP Right Cessation
- 1976-03-17 DE DE19762611118 patent/DE2611118A1/de active Granted
- 1976-03-18 AU AU12148/76A patent/AU504592B2/en not_active Expired
- 1976-03-18 ES ES446193A patent/ES446193A1/es not_active Expired
- 1976-03-18 IE IE568/76A patent/IE43824B1/en unknown
- 1976-03-18 BE BE165315A patent/BE839743A/xx not_active IP Right Cessation
- 1976-03-18 YU YU00715/76A patent/YU71576A/xx unknown
- 1976-03-19 US US05/668,490 patent/US4081551A/en not_active Expired - Lifetime
- 1976-03-19 FR FR7608018A patent/FR2304335A1/fr active Granted
- 1976-03-19 JP JP51029393A patent/JPS601303B2/ja not_active Expired
- 1976-03-22 AR AR262649A patent/AR211119A1/es active
- 1976-12-07 AR AR265766A patent/AR211559A1/es active
1978
- 1978-01-09 SU SU782561603A patent/SU701531A3/ru active
1981
- 1981-03-06 CH CH154281A patent/CH629187A5/de not_active IP Right Cessation
- 1981-03-06 CH CH154381A patent/CH629767A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA761435B (en)	1977-10-26
SE420497B (sv)	1981-10-12
FI62288C (fi)	1982-12-10
PL101885B1 (pl)	1979-02-28
DK140458C (xx)	1980-03-24
JPS601303B2 (ja)	1985-01-14
GB1537898A (en)	1979-01-10
GR59316B (en)	1977-12-12
IE43824B1 (en)	1981-06-03
DE2611118A1 (de)	1976-10-07
IL49239A0 (en)	1976-05-31
AU504592B2 (en)	1979-10-18
CH629187A5 (de)	1982-04-15
PL100617B1 (pl)	1978-10-31
DD128330A5 (de)	1977-11-09
NL7503309A (nl)	1976-09-22
DK140458B (da)	1979-09-03
AR211559A1 (es)	1978-01-30
IL49239A (en)	1978-08-31
FI760698A (xx)	1976-09-21
YU71576A (en)	1982-10-31
SU603336A3 (ru)	1978-04-15
JPS51138639A (en)	1976-11-30
SE7603342L (sv)	1976-09-21
SU701531A3 (ru)	1979-11-30
DK115776A (xx)	1976-09-21
AT340897B (de)	1978-01-10
IE43824L (en)	1976-09-20
AU1214876A (en)	1977-09-22
BE839743A (fr)	1976-09-20
IT1063063B (it)	1985-02-11
AR211119A1 (es)	1977-10-31
CH629767A5 (de)	1982-05-14
PL100613B1 (pl)	1978-10-31
US4081551A (en)	1978-03-28
ATA194876A (de)	1977-05-15
HU171159B (hu)	1977-11-28
FI62288B (fi)	1982-08-31
FR2304335A1 (fr)	1976-10-15
CA1076143A (en)	1980-04-22
FR2304335B1 (xx)	1979-09-28
DE2611118C2 (xx)	1987-05-21
ES446193A1 (es)	1977-10-01

Publication	Publication Date	Title
DE2610886C2 (xx)	1987-09-24
DE3329628C2 (xx)	1988-03-17
DE2305092C2 (xx)	1987-10-01
EP0152868B1 (de)	1989-06-21	Isoxazol-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH626062A5 (xx)	1981-10-30
DE1695672C3 (de)	1978-06-08	2-MeUIyM-[^- methoxy-carbonyl)-phenylamino] -7-chlorchinolin und dessen Salze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH622501A5 (xx)	1981-04-15
DE2610679C2 (de)	1985-09-12	Sulfinylgruppenhaltige Oximätherderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel
CH626056A5 (xx)	1981-10-30
DD148633A5 (de)	1981-06-03	Verfahren zur herstellung von hexahydro-1,4-oxazepinen
CH480350A (de)	1969-10-31	Verfahren zur Herstellung von neuen, kondensierten heterocyclischen Verbindungen
DE2348577A1 (de)	1974-04-11	L-amino-4-phenyltetralin-derivate und diese enthaltende pharmazeutische zubereitung
DE2615129A1 (de)	1976-10-28	Tripeptide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2034588B2 (de)	1979-03-29	ej-Dimethoxy^-benzylisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel
DE2421549A1 (de)	1974-11-21	Naphthalinderivate, verfahren zu ihrer herstellung und arzneimittel
CH624397A5 (xx)	1981-07-31
AT258930B (de)	1967-12-27	Verfahren zur Herstellung von neuen Phenothiazinderivaten und ihren Salzen
AT278785B (de)	1970-02-10	Verfahren zur Herstellung von neuen Piperidinderivaten und ihren Salzen
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
DE2610302A1 (de)	1976-09-30	Antidepressive verbindungen
DE1518334A1 (de)	1969-06-12	Neu substituierte Benzylamine und ihre Salze sowie Verfahren zu ihrer Herstellung
CH633002A5 (de)	1982-11-15	Verfahren zur herstellung von komplexen malonylharnstoffderivaten.
CH454147A (de)	1968-04-15	Verfahren zur Herstellung eines neuen Isoxazolderivates
CH454861A (de)	1968-04-30	Verfahren zur Herstellung von neuen Derivaten des Sulfanilamids
DE2022790B2 (de)	1976-07-08	10-methyl-5- eckige klammer auf (4-methylpiperazino)-acetyl eckige klammer zu -5,10-dihydro-11h-dibenzo eckige klammer auf b,e eckige klammer zu eckige klammer auf 1,4 eckige klammer zu diazepin-11-on, ein verfahren zu dessen herstellung sowie dieses enthaltende arzneimittel

Legal Events

Date	Code	Title	Description
1991-11-29	PL	Patent ceased
2024-10-31	PL	Patent ceased