CA1076142A - Substituted butyrophenone o-(2-aminoethyl) oxime derivatives - Google Patents

Substituted butyrophenone o-(2-aminoethyl) oxime derivatives

Info

Publication number: CA1076142A
Authority: CA; Canada
Prior art keywords: oxime; reaction; aminoethyl; cyano; trifluoromethylvalerophenone
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

CA248,102A

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

1980-04-22

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

1980-04-22 Application granted granted Critical

1980-04-22 Publication of CA1076142A publication Critical patent/CA1076142A/en

Status Expired legal-status Critical Current

Links

150000002923 oximes Chemical class 0.000 title claims description 14
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 68
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 52
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 19
-1 cyanemethyl Chemical group 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 7
239000001530 fumaric acid Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Chemical group 0.000 claims description 6
150000001340 alkali metals Chemical group 0.000 claims description 6
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
239000011976 maleic acid Substances 0.000 claims description 6
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
VYKSRLDHXQURKA-UHFFFAOYSA-N 5-methoxy-1-[4-(trifluoromethyl)phenyl]pentan-1-one Chemical compound COCCCCC(=O)C1=CC=C(C(F)(F)F)C=C1 VYKSRLDHXQURKA-UHFFFAOYSA-N 0.000 claims description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
PRPQQVMGZBHVGJ-UHFFFAOYSA-N 5-ethoxy-1-[4-(trifluoromethyl)phenyl]pentan-1-one Chemical compound CCOCCCCC(=O)C1=CC=C(C(F)(F)F)C=C1 PRPQQVMGZBHVGJ-UHFFFAOYSA-N 0.000 claims description 3
ZDPAIFYBUBUJCZ-UHFFFAOYSA-N 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile Chemical compound FC(F)(F)C1=CC=C(C(=O)CCCC#N)C=C1 ZDPAIFYBUBUJCZ-UHFFFAOYSA-N 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
UDCRPPVSQRFBKJ-UHFFFAOYSA-N n-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]hydroxylamine Chemical compound COCCCCC(=NO)C1=CC=C(C(F)(F)F)C=C1 UDCRPPVSQRFBKJ-UHFFFAOYSA-N 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
UEGQWUAFHTVABM-UHFFFAOYSA-N 6-oxo-6-[4-(trifluoromethyl)phenyl]hexanenitrile Chemical compound FC(F)(F)C1=CC=C(C(=O)CCCCC#N)C=C1 UEGQWUAFHTVABM-UHFFFAOYSA-N 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
MECRKILGNPUEFQ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine Chemical compound NCCON MECRKILGNPUEFQ-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
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 2
239000007858 starting material Substances 0.000 claims 10
KSFIFXZMPYOGJU-UHFFFAOYSA-N 2-[[5-ethoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine Chemical compound CCOCCCCC(=NOCCN)C1=CC=C(C(F)(F)F)C=C1 KSFIFXZMPYOGJU-UHFFFAOYSA-N 0.000 claims 6
125000004093 cyano group Chemical group *C#N 0.000 claims 5
LFMYNZPAVPMEGP-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine Chemical compound OC(=O)\C=C/C(O)=O.COCCCCC(=NOCCN)C1=CC=C(C(F)(F)F)C=C1 LFMYNZPAVPMEGP-BTJKTKAUSA-N 0.000 claims 2
SZWSOOPOEYPZNV-UHFFFAOYSA-N 6-(2-aminoethoxyimino)-6-[4-(trifluoromethyl)phenyl]hexanenitrile Chemical compound N#CCCCCC(=NOCCN)C1=CC=C(C(F)(F)F)C=C1 SZWSOOPOEYPZNV-UHFFFAOYSA-N 0.000 claims 2
JVJYTQAQHHMORH-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-[[5-chloro-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine Chemical compound OC(=O)\C=C/C(O)=O.NCCON=C(CCCCCl)C1=CC=C(C(F)(F)F)C=C1 JVJYTQAQHHMORH-BTJKTKAUSA-N 0.000 claims 1
XHMUAIOLBGZVLR-UHFFFAOYSA-N 2-[[5-ethoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyacetonitrile Chemical compound CCOCCCCC(=NOCC#N)C1=CC=C(C(F)(F)F)C=C1 XHMUAIOLBGZVLR-UHFFFAOYSA-N 0.000 claims 1
CJOFXWAVKWHTFT-UHFFFAOYSA-N 2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine Chemical compound COCCCCC(=NOCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-UHFFFAOYSA-N 0.000 claims 1
ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 claims 1
ODTIGDOCAUJCDD-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-5-[2-(tritylamino)ethoxyimino]pentanenitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C(CCCC#N)=NOCCNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ODTIGDOCAUJCDD-UHFFFAOYSA-N 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
239000012280 lithium aluminium hydride Substances 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 28
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
229960002748 norepinephrine Drugs 0.000 description 7
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 7
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
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241000699670 Mus sp. Species 0.000 description 5
230000001430 anti-depressive effect Effects 0.000 description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
206010006482 Bronchospasm Diseases 0.000 description 4
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229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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125000001309 chloro group Chemical group Cl* 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
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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
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239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000002474 noradrenergic effect Effects 0.000 description 1
230000001473 noxious effect Effects 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
230000008506 pathogenesis Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
239000011541 reaction mixture Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 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
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

- 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

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)

CA248,102A 1975-03-20 1976-03-17 Substituted butyrophenone o-(2-aminoethyl) oxime derivatives Expired CA1076142A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7503310A NL7503310A (nl)	1975-03-20	1975-03-20	Verbindingen met antidepressieve werking.

Publications (1)

Publication Number	Publication Date
CA1076142A true CA1076142A (en)	1980-04-22

Family

ID=19823424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,102A Expired CA1076142A (en)	1975-03-20	1976-03-17	Substituted butyrophenone o-(2-aminoethyl) oxime derivatives

Country Status (27)

Country	Link
US (1)	US4085225A (2)
JP (1)	JPS6026776B2 (2)
AR (2)	AR211011A1 (2)
AT (1)	AT340895B (2)
AU (1)	AU505358B2 (2)
BE (1)	BE839744A (2)
CA (1)	CA1076142A (2)
CH (4)	CH626057A5 (2)
DD (1)	DD128332A5 (2)
DE (1)	DE2610886A1 (2)
DK (1)	DK144942C (2)
ES (1)	ES446192A1 (2)
FI (1)	FI61875C (2)
FR (1)	FR2304336A1 (2)
GB (1)	GB1535226A (2)
GR (1)	GR60052B (2)
HU (1)	HU171030B (2)
IE (1)	IE43768B1 (2)
IL (1)	IL49238A (2)
IT (1)	IT1063064B (2)
MX (1)	MX9203723A (2)
NL (1)	NL7503310A (2)
PL (3)	PL101951B1 (2)
SE (1)	SE410312B (2)
SU (3)	SU635867A3 (2)
YU (1)	YU39345B (2)
ZA (1)	ZA761434B (2)

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US3692835A (en) *	1967-04-05	1972-09-19	Jan Van Dijk	Pharmacologically active amino-ethyl oximes

1975
- 1975-03-20 NL NL7503310A patent/NL7503310A/xx not_active Application Discontinuation
1976
- 1976-03-09 ZA ZA761434A patent/ZA761434B/xx unknown
- 1976-03-16 DE DE19762610886 patent/DE2610886A1/de active Granted
- 1976-03-17 CA CA248,102A patent/CA1076142A/en not_active Expired
- 1976-03-17 GB GB10703/76A patent/GB1535226A/en not_active Expired
- 1976-03-17 DK DK115976A patent/DK144942C/da not_active IP Right Cessation
- 1976-03-17 IT IT21320/76A patent/IT1063064B/it active Protection Beyond IP Right Term
- 1976-03-17 FI FI760699A patent/FI61875C/fi not_active IP Right Cessation
- 1976-03-17 PL PL1976199557A patent/PL101951B1/pl unknown
- 1976-03-17 PL PL1976199556A patent/PL100052B1/pl unknown
- 1976-03-17 SU SU762335241A patent/SU635867A3/ru active
- 1976-03-17 HU HU76PI00000513A patent/HU171030B/hu unknown
- 1976-03-17 AT AT195476A patent/AT340895B/de active Protection Beyond IP Right Term
- 1976-03-17 IL IL49238A patent/IL49238A/xx unknown
- 1976-03-17 DD DD7600191893A patent/DD128332A5/xx unknown
- 1976-03-17 PL PL1976188006A patent/PL100614B1/pl unknown
- 1976-03-17 SE SE7603341A patent/SE410312B/xx not_active IP Right Cessation
- 1976-03-17 CH CH334576A patent/CH626057A5/de active Protection Beyond IP Right Term
- 1976-03-17 GR GR50333A patent/GR60052B/el unknown
- 1976-03-18 AU AU12147/76A patent/AU505358B2/en not_active Expired
- 1976-03-18 YU YU714/76A patent/YU39345B/xx unknown
- 1976-03-18 ES ES446192A patent/ES446192A1/es not_active Expired
- 1976-03-18 BE BE165316A patent/BE839744A/xx not_active IP Right Cessation
- 1976-03-18 IE IE567/76A patent/IE43768B1/en not_active IP Right Cessation
- 1976-03-19 JP JP51029394A patent/JPS6026776B2/ja not_active Expired
- 1976-03-19 US US05/668,461 patent/US4085225A/en not_active Expired - Lifetime
- 1976-03-19 FR FR7608019A patent/FR2304336A1/fr active Granted
- 1976-03-22 AR AR262650A patent/AR211011A1/es active
- 1976-12-10 AR AR265801A patent/AR211153A1/es active
1977
- 1977-07-12 SU SU772503815A patent/SU620206A3/ru active
- 1977-07-12 SU SU772503814A patent/SU645559A3/ru active
1981
- 1981-03-06 CH CH153981A patent/CH629184A5/de not_active IP Right Cessation
- 1981-03-06 CH CH154081A patent/CH629477A5/de not_active IP Right Cessation
- 1981-03-06 CH CH154181A patent/CH629761A5/de not_active IP Right Cessation
1992
- 1992-06-29 MX MX9203723A patent/MX9203723A/es unknown

Also Published As

Publication number	Publication date
FR2304336B1 (2)	1979-09-28
IE43768L (en)	1976-09-20
FI760699A7 (2)	1976-09-21
BE839744A (fr)	1976-09-20
IL49238A (en)	1978-08-31
YU39345B (en)	1984-10-31
CH629477A5 (de)	1982-04-30
HU171030B (hu)	1977-10-28
FI61875C (fi)	1982-10-11
JPS51125345A (en)	1976-11-01
MX9203723A (es)	1992-07-01
PL101951B1 (pl)	1979-02-28
YU71476A (en)	1982-10-31
IE43768B1 (en)	1981-05-20
FR2304336A1 (fr)	1976-10-15
GR60052B (en)	1978-04-04
GB1535226A (en)	1978-12-13
AU505358B2 (en)	1979-11-15
SU635867A3 (ru)	1978-11-30
IT1063064B (it)	1985-02-11
SE410312B (sv)	1979-10-08
DK144942B (da)	1982-07-12
DK115976A (da)	1976-09-21
DE2610886A1 (de)	1976-10-07
ZA761434B (en)	1977-10-26
CH629184A5 (de)	1982-04-15
AU1214776A (en)	1977-09-22
AR211011A1 (es)	1977-10-14
PL100614B1 (pl)	1978-10-31
AR211153A1 (es)	1977-10-31
SU620206A3 (ru)	1978-08-15
IL49238A0 (en)	1976-05-31
NL7503310A (nl)	1976-09-22
US4085225A (en)	1978-04-18
CH629761A5 (de)	1982-05-14
ES446192A1 (es)	1977-10-01
DE2610886C2 (2)	1987-09-24
ATA195476A (de)	1977-05-15
SE7603341L (sv)	1976-09-21
JPS6026776B2 (ja)	1985-06-25
DK144942C (da)	1982-12-06
PL100052B1 (pl)	1978-08-31
FI61875B (fi)	1982-06-30
CH626057A5 (2)	1981-10-30
DD128332A5 (de)	1977-11-09
AT340895B (de)	1978-01-10
SU645559A3 (ru)	1979-01-30

Legal Events

Date	Code	Title	Description
1997-04-22	MKEX	Expiry

Publication	Publication Date	Title
CA1076142A (en)	1980-04-22	Substituted butyrophenone o-(2-aminoethyl) oxime derivatives
SK580690A3 (en)	1997-07-09	Isoindolone derivatives, process of their preparation and their use as intermediate products
Snyder et al.	1957	The synthesis of the 2-Amino-3-(3-indolyl)-butyric acids (β-Methyltryptophans)
DE69709272T2 (de)	2002-08-08	Diazepino-indole als phosphodiesterase iv inhibitoren
JPH07500355A (ja)	1995-01-12	２−（２，６−ジ−ハロ−フェニルアミノ）フェニル酢酸の誘導体の硝酸エステルおよびその製造法
SK3992001A3 (en)	2001-12-03	Tetrahydropyridoethers, pharmaceutical composition containing same and use thereof
JPS6026782B2 (ja)	1985-06-25	新規アリ−ルピペリジン誘導体の製造方法
US2820817A (en)	1958-01-21	Oxygenated indan compounds and method of making the same
US4169108A (en)	1979-09-25	5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols
CA1053239A (en)	1979-04-24	Imidazo (2,1-b) thiazoles
DK157546B (da)	1990-01-22	Analogifremgangsmaade til fremstilling af 3h-nafto(1,2-d)imidazolderivater eller additionssalte deraf med farmaceutisk acceptable syrer.
CH630383A5 (de)	1982-06-15	Verfahren zur herstellung von cyclischen derivaten von 1,4-benzoxazin und 1,4-benzothiazin.
CH649553A5 (de)	1985-05-31	Azepinoindole und verfahren zu deren herstellung.
FI63402C (fi)	1983-06-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara d- och d1-trans-5-fenyl 2,3,4,4a,5,9b-hexahydro-1h-pyrido(4,3-b)indolderivat
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FI57747B (fi)	1980-06-30	Foerfarande foer framstaellning av nya isoindolin-1-on-derivat vilka aer anvaendbara saosom medel mot arytmi
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JPS6216947B2 (2)	1987-04-15
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CH671396A5 (2)	1989-08-31
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JPS6391374A (ja)	1988-04-22	炭酸水素イミダゾリウム