CA1077964A - 4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds - Google Patents

4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds

Info

Publication number: CA1077964A
Authority: CA; Canada
Prior art keywords: oxime; reaction; hydrochloride; aminoethyl; hydrogen
Prior art date: 1975-03-20
Legal status (The legal status 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 status listed.): Expired

Application number

CA248,103A

Other languages

English (en)

French (fr)

Inventor

Hendricus B.A. Welle

Volkert Claassen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Koninklijke Philips NV

Original Assignee

Philips Gloeilampenfabrieken NV

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

1980-05-20

1976-03-17 Application filed by Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077964A publication Critical patent/CA1077964A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 100
230000001430 anti-depressive effect Effects 0.000 title abstract description 11
238000000034 method Methods 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 25
239000000126 substance Substances 0.000 claims abstract description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052801 chlorine Chemical group 0.000 claims abstract description 7
239000005864 Sulphur Chemical group 0.000 claims abstract description 6
239000000460 chlorine Chemical group 0.000 claims abstract description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002431 hydrogen Chemical group 0.000 claims abstract 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
150000002923 oximes Chemical class 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 38
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 29
-1 propoxy, propylthio, methoxy Chemical group 0.000 claims description 28
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 22
YHUXZWQAYFQBPG-UHFFFAOYSA-N 1-(3-chloro-4-nitrophenyl)-5-methoxypentan-1-one Chemical compound COCCCCC(=O)C1=CC=C([N+]([O-])=O)C(Cl)=C1 YHUXZWQAYFQBPG-UHFFFAOYSA-N 0.000 claims description 13
DPTGZRADVAPUHQ-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-propoxyethanone Chemical compound CCCOCC(=O)C1=CC=C([N+]([O-])=O)C=C1 DPTGZRADVAPUHQ-UHFFFAOYSA-N 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
LQCRSKSCUSXMJH-UHFFFAOYSA-N 1-(4-nitrophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 LQCRSKSCUSXMJH-UHFFFAOYSA-N 0.000 claims description 11
VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
239000001530 fumaric acid Substances 0.000 claims description 8
FMHFXXRKMQWBEP-UHFFFAOYSA-N 1-(3-methyl-4-nitrophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C([N+]([O-])=O)C(C)=C1 FMHFXXRKMQWBEP-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Chemical group 0.000 claims description 6
150000001340 alkali metals Chemical group 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
IVLJDGSFPOBAID-UHFFFAOYSA-N 5-methoxy-1-(4-nitrophenyl)pentan-1-one Chemical compound COCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 IVLJDGSFPOBAID-UHFFFAOYSA-N 0.000 claims description 5
PXSLNRQFXCFEAY-UHFFFAOYSA-N 6-methoxy-1-(4-nitrophenyl)hexan-1-one Chemical compound COCCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 PXSLNRQFXCFEAY-UHFFFAOYSA-N 0.000 claims description 5
LAAQSOCEYYDGGG-UHFFFAOYSA-N o-(2-aminopropyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.CC(N)CON LAAQSOCEYYDGGG-UHFFFAOYSA-N 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
AVMPRGQRQKZCHO-UHFFFAOYSA-N 5-(2-methoxyethoxy)-1-(4-nitrophenyl)pentan-1-one Chemical compound COCCOCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 AVMPRGQRQKZCHO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
WJQSTKOKOAWURI-UHFFFAOYSA-N CCCCC(=S)C1=CC=C([N+]([O-])=O)C=C1 Chemical compound CCCCC(=S)C1=CC=C([N+]([O-])=O)C=C1 WJQSTKOKOAWURI-UHFFFAOYSA-N 0.000 claims description 3
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000003544 oxime group Chemical group 0.000 claims description 3
ODSCUBSJIFLFPF-UHFFFAOYSA-N 1-(4-aminophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(N)C=C1 ODSCUBSJIFLFPF-UHFFFAOYSA-N 0.000 claims description 2
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 2
MBUPVGIGAMCMBT-UHFFFAOYSA-N 2-bromo-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CBr)C=C1 MBUPVGIGAMCMBT-UHFFFAOYSA-N 0.000 claims description 2
ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 claims description 2
DRGHCHSDUDQWHJ-UHFFFAOYSA-N 2-hydroxy-1-(4-nitrophenyl)ethanone Chemical compound OCC(=O)C1=CC=C([N+]([O-])=O)C=C1 DRGHCHSDUDQWHJ-UHFFFAOYSA-N 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
XKYOVMMMCPHSSL-UHFFFAOYSA-N ethene;5-(2-methoxyethoxy)-1-(4-nitrophenyl)pentan-1-one Chemical group C=C.COCCOCCCCC(=O)C1=CC=C([N+]([O-])=O)C=C1 XKYOVMMMCPHSSL-UHFFFAOYSA-N 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims 14
239000007858 starting material Substances 0.000 claims 12
JPXNWSUZNNOPCE-UHFFFAOYSA-N 2-[1-(4-nitrophenyl)pentylideneamino]oxy-n-tritylethanamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(CCCC)=NOCCNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JPXNWSUZNNOPCE-UHFFFAOYSA-N 0.000 claims 1
QPXXCHSNRHEJGT-UHFFFAOYSA-N n-[1-(4-nitrophenyl)-2-propoxyethylidene]hydroxylamine Chemical compound CCCOCC(=NO)C1=CC=C([N+]([O-])=O)C=C1 QPXXCHSNRHEJGT-UHFFFAOYSA-N 0.000 claims 1
JAAGZDYQILFLLT-UHFFFAOYSA-N o-(2-aminopropyl)hydroxylamine Chemical compound CC(N)CON JAAGZDYQILFLLT-UHFFFAOYSA-N 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 8
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102000004316 Oxidoreductases Human genes 0.000 abstract description 3
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239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 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
125000006353 oxyethylene group Chemical group 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
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 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/10—Sulfenic acids; Esters thereof
- C07C313/12—Sulfenic acids; Esters thereof having sulfur atoms of sulfenic groups bound to acyclic carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA248,103A 1975-03-20 1976-03-17 4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds Expired CA1077964A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7503307A NL7503307A (nl)	1975-03-20	1975-03-20	Antidepressieve verbindingen.

Publications (1)

Publication Number	Publication Date
CA1077964A true CA1077964A (en)	1980-05-20

Family

ID=19823421

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,103A Expired CA1077964A (en)	1975-03-20	1976-03-17	4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds

Country Status (21)

Country	Link
JP (1)	JPS51125344A (de)
AR (2)	AR212811A1 (de)
AT (1)	AT340894B (de)
AU (1)	AU502701B2 (de)
BE (1)	BE839741A (de)
CA (1)	CA1077964A (de)
DD (1)	DD128331A5 (de)
DE (1)	DE2610302A1 (de)
DK (1)	DK115676A (de)
ES (1)	ES446189A1 (de)
FI (1)	FI760696A (de)
FR (1)	FR2304332A1 (de)
GB (1)	GB1533063A (de)
GR (1)	GR60051B (de)
HU (1)	HU171160B (de)
IE (1)	IE43826B1 (de)
IL (1)	IL49236A (de)
NL (1)	NL7503307A (de)
PL (3)	PL100612B1 (de)
SE (1)	SE7603344L (de)
ZA (1)	ZA761386B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7256191B2 (en)	2000-04-24	2007-08-14	Aryx Therapeutics	Materials and methods for the treatment of depression
AU2001255654B2 (en)	2000-04-24	2005-09-22	Aryx Therapeutics	Materials and methods for the treatment of depression

1975
- 1975-03-20 NL NL7503307A patent/NL7503307A/xx not_active Application Discontinuation
1976
- 1976-03-08 ZA ZA761386A patent/ZA761386B/xx unknown
- 1976-03-12 DE DE2610302A patent/DE2610302A1/de not_active Withdrawn
- 1976-03-17 DD DD7600191890A patent/DD128331A5/de unknown
- 1976-03-17 PL PL1976188001A patent/PL100612B1/pl unknown
- 1976-03-17 AT AT195276A patent/AT340894B/de not_active IP Right Cessation
- 1976-03-17 DK DK115676A patent/DK115676A/da unknown
- 1976-03-17 FI FI760696A patent/FI760696A/fi not_active Application Discontinuation
- 1976-03-17 CA CA248,103A patent/CA1077964A/en not_active Expired
- 1976-03-17 HU HU76PI00000515A patent/HU171160B/hu unknown
- 1976-03-17 PL PL1976199547A patent/PL101882B1/pl unknown
- 1976-03-17 GR GR50330A patent/GR60051B/el unknown
- 1976-03-17 IL IL49236A patent/IL49236A/xx unknown
- 1976-03-17 SE SE7603344A patent/SE7603344L/xx not_active Application Discontinuation
- 1976-03-17 PL PL1976199546A patent/PL100040B1/pl unknown
- 1976-03-17 GB GB10706/76A patent/GB1533063A/en not_active Expired
- 1976-03-18 IE IE570/76A patent/IE43826B1/en unknown
- 1976-03-18 BE BE165313A patent/BE839741A/xx unknown
- 1976-03-18 AU AU12142/76A patent/AU502701B2/en not_active Expired
- 1976-03-18 ES ES446189A patent/ES446189A1/es not_active Expired
- 1976-03-19 AR AR262633A patent/AR212811A1/es active
- 1976-03-19 JP JP51029391A patent/JPS51125344A/ja active Pending
- 1976-03-19 FR FR7608015A patent/FR2304332A1/fr active Granted
- 1976-12-07 AR AR265765A patent/AR213298A1/es active

Also Published As

Publication number	Publication date
FI760696A (de)	1976-09-21
AU1214276A (en)	1977-09-22
AU502701B2 (en)	1979-08-02
JPS51125344A (en)	1976-11-01
ZA761386B (en)	1977-10-26
SE7603344L (sv)	1976-09-21
IE43826L (en)	1976-09-20
DE2610302A1 (de)	1976-09-30
AR213298A1 (es)	1979-01-15
HU171160B (hu)	1977-11-28
ES446189A1 (es)	1977-10-01
PL101882B1 (pl)	1979-02-28
GB1533063A (en)	1978-11-22
DK115676A (da)	1976-09-21
IE43826B1 (en)	1981-06-03
PL100040B1 (pl)	1978-08-31
IL49236A (en)	1978-08-31
BE839741A (fr)	1976-09-20
FR2304332B1 (de)	1978-12-08
IL49236A0 (en)	1976-05-31
PL100612B1 (pl)	1978-10-31
FR2304332A1 (fr)	1976-10-15
DD128331A5 (de)	1977-11-09
AR212811A1 (es)	1978-10-13
AT340894B (de)	1978-01-10
ATA195276A (de)	1977-05-15
NL7503307A (nl)	1976-09-22
GR60051B (en)	1978-04-04

Publication	Publication Date	Title
US3692835A (en)	1972-09-19	Pharmacologically active amino-ethyl oximes
US3471522A (en)	1969-10-07	N-cyclopropyl-n'-furfuryl-n'-methyl ethylene diamines
US4835179A (en)	1989-05-30	Antiulcer dihydrodibenzocycloheptyliden-ethylamine derivatives and process for the preparation of these compounds
PL115869B1 (en)	1981-05-30	Process for manufacturing novel derivatives of phenyl-3-azabicyclo/3,1,0/hexane
US3267107A (en)	1966-08-16	3-(4'-5'-methylenedioxy-phenyl)-7, 8-dimethoxy-1, 2, 3, 4,-tetrahydroisoquinolines
US4123530A (en)	1978-10-31	N-cyclohexyl-piperazino acetamides and propionamides
US4310534A (en)	1982-01-12	Pharmaceutically active 2-(4-aminobutoxy)stilbenes
CA1077964A (en)	1980-05-20	4'-nitro-acetophenone-o-aminoethyloximes as antidepressive compounds
US3968211A (en)	1976-07-06	Compositions and methods of use of amidines for anti-arrhythmic purposes
US4684651A (en)	1987-08-04	Alkylenedioxybenzene and acid addition salts thereof useful as hypotensives
Singh et al.	1977	Synthesis of 5-chloro-3'-nitro-4'-substituted salicylanilides, a new series of anthelmintic and antimicrobial agents
Ibragimov et al.	1994	Inclusion complexes of the natural product gossypol
CA1077519A (en)	1980-05-13	Oxime ethers having anti-depressive activity
US4086361A (en)	1978-04-25	Aminoethyl oximes having anti-depressive activity
CA1154015A (en)	1983-09-20	Tetrahydroquinoline derivatives, a process for their preparation, their use, and pharmaceutical formulations containing them
US4192893A (en)	1980-03-11	Anti-depressive compounds
US3547937A (en)	1970-12-15	Certain 4-thiazolecarboxamidines
US2933532A (en)	1960-04-19	Substituted 1-phenyl-2-hydrazino-propanes
US4247697A (en)	1981-01-27	3-Phenoxy morphinans and their derivatives
US3262978A (en)	1966-07-26	O-arylamino-and-aralkyl-amino-alkylhydroxyl-amines
US4194044A (en)	1980-03-18	Process for preparing 3-phenoxy morphinans
US4221714A (en)	1980-09-09	11-(1,2,3,6-Tetrahydro-substituted-4-pyridyl)-dibenz[b,f][1,4]oxazepines
US4261998A (en)	1981-04-14	Tetrahydro-isoquinoline derivatives
US4064270A (en)	1977-12-20	N'-(Aminoacylaminophenyl) acetamidines
DE2833892A1 (de)	1979-02-22	12h-dibenzo eckige klammer auf d,g eckige klammer zu eckige klammer auf 1,3,6 eckige klammer zu dioxazocinderivate, solche enthaltende arzneimittel und verfahren zur herstellung derselben

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry