CS219942B2 - Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine - Google Patents

Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine Download PDF

Info

Publication number: CS219942B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compounds; carbon atoms; methoxyphenyl; niederes
Prior art date: 1980-01-29

Application number

CS817016A

Other languages

Czech (cs)

English (en)

Inventor

Hans Bruderer

Albert E Fischli

Rudolf Pfister

Original Assignee

Hoffmann La Roche

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.)

1980-01-29

Filing date

1981-01-19

Publication date

1983-03-25

1981-01-19 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1983-03-25 Publication of CS219942B2 publication Critical patent/CS219942B2/cs

Links

238000004519 manufacturing process Methods 0.000 title claims description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
-1 N-cyclopropylmethyl-1- (methoxyphenyl) -N-methyl-2-cyclohexene-1-ethylamine Chemical compound 0.000 description 16
239000000203 mixture Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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239000000047 product Substances 0.000 description 4
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125000004429 atom Chemical group 0.000 description 2
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238000001816 cooling Methods 0.000 description 2
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XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 2
229960004193 dextropropoxyphene Drugs 0.000 description 2
ZBDAMDWKXGTKBT-UHFFFAOYSA-N ethyl 2-cyclohexylacetate Chemical compound CCOC(=O)CC1CCCCC1 ZBDAMDWKXGTKBT-UHFFFAOYSA-N 0.000 description 2
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239000003925 fat Substances 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
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239000012280 lithium aluminium hydride Substances 0.000 description 2
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230000003285 pharmacodynamic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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235000011056 potassium acetate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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UOLTUFIDPYGCNR-UHFFFAOYSA-N 1-[1-(2-chloroethyl)cyclohex-2-en-1-yl]-3-methoxybenzene Chemical compound COC1=CC=CC(C2(CCCl)C=CCCC2)=C1 UOLTUFIDPYGCNR-UHFFFAOYSA-N 0.000 description 1
JXGPWHGFWOETBV-UHFFFAOYSA-N 2-[1-(3-methoxyphenyl)cyclohex-2-en-1-yl]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC(C2(CCN(C)C)C=CCCC2)=C1 JXGPWHGFWOETBV-UHFFFAOYSA-N 0.000 description 1
MYNLIUPCOLRRLL-UHFFFAOYSA-N 2-[1-(3-methoxyphenyl)cyclohex-2-en-1-yl]-n-methylethanamine Chemical compound C=1C=CC(OC)=CC=1C1(CCNC)CCCC=C1 MYNLIUPCOLRRLL-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
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KTPVLSACFHSZTC-UHFFFAOYSA-N ethyl 2-[1-(3-methoxyphenyl)-2-methylsulfonyloxycyclohexyl]acetate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCCC1OS(C)(=O)=O KTPVLSACFHSZTC-UHFFFAOYSA-N 0.000 description 1
XIAYIHJKGNBZON-UHFFFAOYSA-N ethyl 2-[1-(3-methoxyphenyl)-2-oxocyclohexyl]acetate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCCC1=O XIAYIHJKGNBZON-UHFFFAOYSA-N 0.000 description 1
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125000000896 monocarboxylic acid group Chemical group 0.000 description 1
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239000000376 reactant Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Indole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS817016A 1980-01-29 1981-01-19 Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine CS219942B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH72480A CH644580A5 (de)	1980-01-29	1980-01-29	Cyclohexen-derivate.

Publications (1)

Publication Number	Publication Date
CS219942B2 true CS219942B2 (en)	1983-03-25

Family

ID=4193699

Family Applications (6)

Application Number	Title	Priority Date	Filing Date
CS817016A CS219942B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CS817019A CS219944B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexen-1-alkylamine
CS817018A CS219943B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CS817015A CS219941B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CS817017A CS220347B2 (en)	1980-01-29	1981-01-19	Method of producing racemic and optically uniform 1-phenyl-2-cyclohexene-1-ethylamine derivatives
CS81362A CS219940B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives 1-phenyl-2-cyclohexen-1-alcylamide

Family Applications After (5)

Application Number	Title	Priority Date	Filing Date
CS817019A CS219944B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexen-1-alkylamine
CS817018A CS219943B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CS817015A CS219941B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CS817017A CS220347B2 (en)	1980-01-29	1981-01-19	Method of producing racemic and optically uniform 1-phenyl-2-cyclohexene-1-ethylamine derivatives
CS81362A CS219940B2 (en)	1980-01-29	1981-01-19	Method of making the racemic and optically unite derivatives 1-phenyl-2-cyclohexen-1-alcylamide

Country Status (32)

Country	Link
US (2)	US4336268A (ko)
EP (1)	EP0033156B1 (ko)
JP (1)	JPS56120650A (ko)
KR (6)	KR850000626B1 (ko)
AR (1)	AR227906A1 (ko)
AT (2)	ATE9895T1 (ko)
AU (1)	AU540697B2 (ko)
BR (1)	BR8100484A (ko)
CA (1)	CA1161064A (ko)
CH (1)	CH644580A5 (ko)
CS (6)	CS219942B2 (ko)
DE (2)	DE3102603A1 (ko)
DK (1)	DK15681A (ko)
ES (6)	ES8301200A1 (ko)
FI (1)	FI801147A7 (ko)
FR (1)	FR2479815A1 (ko)
GB (1)	GB2068373B (ko)
HU (1)	HU182280B (ko)
IE (1)	IE50885B1 (ko)
IL (1)	IL61961A (ko)
IT (1)	IT1135001B (ko)
LU (1)	LU83096A1 (ko)
MC (1)	MC1365A1 (ko)
NL (1)	NL8100403A (ko)
NO (1)	NO149958C (ko)
NZ (1)	NZ196086A (ko)
PH (1)	PH16098A (ko)
PT (1)	PT72415B (ko)
SE (1)	SE8100403L (ko)
YU (1)	YU332180A (ko)
ZA (1)	ZA81459B (ko)
ZW (1)	ZW31480A1 (ko)

Families Citing this family (13)

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US6372919B1 (en) *	2001-01-11	2002-04-16	Dov Pharmaceutical, Inc.	(+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent
US20060173064A1 (en) *	2001-08-24	2006-08-03	Lippa Arnold S	(-)-1-(3,4-Dichlorophenyl)-3-azabi cyclo[3.1.0]hexane, compositions thereof, and uses for treating alcohol-related disorders
US6569887B2 (en)	2001-08-24	2003-05-27	Dov Pharmaceuticals Inc.	(−)-1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as a dopamine-reuptake
US20080081834A1 (en)	2002-07-31	2008-04-03	Lippa Arnold S	Methods and compositions employing bicifadine for treating disability or functional impairment associated with acute pain, chronic pain, or neuropathic disorders
US20070043100A1 (en) *	2005-08-16	2007-02-22	Hagen Eric J	Novel polymorphs of azabicyclohexane
US20060100263A1 (en) *	2004-11-05	2006-05-11	Anthony Basile	Antipyretic compositions and methods
EP1915146A4 (en)	2005-07-27	2010-06-02	Dov Pharmaceutical Inc	NOVEL 1-ARYL-3-AZABICYCLO [3.1.0] HEXANEES. PREPARATION AND USE FOR THE TREATMENT OF NEUROPSYCHIATRIC DISEASES
US20080045725A1 (en)	2006-04-28	2008-02-21	Murry Jerry A	Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane
US8138377B2 (en) *	2006-11-07	2012-03-20	Dov Pharmaceutical, Inc.	Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use
US20080269348A1 (en) *	2006-11-07	2008-10-30	Phil Skolnick	Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use
EP2167083B1 (en) *	2007-06-06	2015-10-28	Euthymics Bioscience, Inc.	1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
US9133159B2 (en)	2007-06-06	2015-09-15	Neurovance, Inc.	1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
US20140206740A1 (en)	2011-07-30	2014-07-24	Neurovance, Inc.	Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters

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Publication number	Priority date	Publication date	Assignee	Title
CH249047A (de) *	1944-03-20	1947-05-31	Ag J R Geigy	Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-1-carbonsäure.
CH249052A (de) *	1944-03-20	1947-05-31	Ag J R Geigy	Verfahren zur Darstellung eines basischen Amids einer 1-Aryl-cycloalkyl-1-carbonsäure.
US2647122A (en) *	1948-10-01	1953-07-28	Sterling Drug Inc	Tertiary amines and process of preparing them
US3109845A (en) *	1960-02-04	1963-11-05	Thomae Gmbh Dr K	1-cyclohexyl, 1-cyclohexenyl, 1-furyl, and 1-thienyl, tertiary amino substituted methanes
DE1518545A1 (de) *	1965-04-01	1970-01-15	Boehringer Mannheim Gmbh	Verfahren zur Herstellung neuer Phenylcyclohexylalkylamine und ihrer Salze
DE1518663A1 (de) *	1965-08-02	1969-12-18	Gruenenthal Chemie	Basisch substituierte Cycloalken-derivate und Verfahren zu ihrer Herstellung
US3408396A (en) *	1965-10-22	1968-10-29	Colgate Palmolive Co	alpha-cyclohexyl-3, 4-disubstituted-phenyl acetamides
US3485873A (en) *	1966-12-21	1969-12-23	Sterling Drug Inc	N-benzyl-n-methyl-omega-phenyl-omega-cycloalkyl-lower-alkylamines
US3737451A (en) *	1970-09-23	1973-06-05	Sandoz Ag	Cis-3,4-diaryl-cyclopentylidene-and 1-cyclopentene-1-acetic acids and derivatives
US4053637A (en) *	1971-06-11	1977-10-11	Astra Lakemedal Aktiebolag	Compounds of diphenylcyclopentylamine type and methods for their uses
CA1130318A (en) *	1978-10-11	1982-08-24	Peter M. Muller	Cyclohexadiene derivatives

1980
- 1980-01-29 CH CH72480A patent/CH644580A5/de not_active IP Right Cessation
- 1980-04-10 FI FI801147A patent/FI801147A7/fi not_active Application Discontinuation
- 1980-12-11 CA CA000366550A patent/CA1161064A/en not_active Expired
- 1980-12-19 ZW ZW314/80A patent/ZW31480A1/xx unknown
- 1980-12-30 YU YU03321/80A patent/YU332180A/xx unknown
1981
- 1981-01-08 IT IT19047/81A patent/IT1135001B/it active
- 1981-01-14 DK DK15681A patent/DK15681A/da not_active Application Discontinuation
- 1981-01-19 CS CS817016A patent/CS219942B2/cs unknown
- 1981-01-19 CS CS817019A patent/CS219944B2/cs unknown
- 1981-01-19 CS CS817018A patent/CS219943B2/cs unknown
- 1981-01-19 CS CS817015A patent/CS219941B2/cs unknown
- 1981-01-19 CS CS817017A patent/CS220347B2/cs unknown
- 1981-01-19 CS CS81362A patent/CS219940B2/cs unknown
- 1981-01-20 PH PH25103A patent/PH16098A/en unknown
- 1981-01-22 NZ NZ196086A patent/NZ196086A/en unknown
- 1981-01-22 ZA ZA00810459A patent/ZA81459B/xx unknown
- 1981-01-22 IL IL61961A patent/IL61961A/xx unknown
- 1981-01-23 SE SE8100403A patent/SE8100403L/xx not_active Application Discontinuation
- 1981-01-23 AR AR284052A patent/AR227906A1/es active
- 1981-01-26 MC MC811495A patent/MC1365A1/fr unknown
- 1981-01-27 LU LU83096A patent/LU83096A1/de unknown
- 1981-01-27 JP JP975781A patent/JPS56120650A/ja active Pending
- 1981-01-27 DE DE19813102603 patent/DE3102603A1/de not_active Withdrawn
- 1981-01-27 AT AT81100576T patent/ATE9895T1/de active
- 1981-01-27 DE DE8181100576T patent/DE3166656D1/de not_active Expired
- 1981-01-27 EP EP81100576A patent/EP0033156B1/de not_active Expired
- 1981-01-27 FR FR8101480A patent/FR2479815A1/fr active Granted
- 1981-01-27 US US06/228,793 patent/US4336268A/en not_active Expired - Fee Related
- 1981-01-28 BR BR8100484A patent/BR8100484A/pt unknown
- 1981-01-28 ES ES498866A patent/ES8301200A1/es not_active Expired
- 1981-01-28 PT PT72415A patent/PT72415B/pt unknown
- 1981-01-28 IE IE153/81A patent/IE50885B1/en unknown
- 1981-01-28 KR KR1019810000259A patent/KR850000626B1/ko not_active Expired
- 1981-01-28 NL NL8100403A patent/NL8100403A/nl not_active Application Discontinuation
- 1981-01-28 GB GB8102555A patent/GB2068373B/en not_active Expired
- 1981-01-28 AT AT0035581A patent/AT376654B/de not_active IP Right Cessation
- 1981-01-28 NO NO810297A patent/NO149958C/no unknown
- 1981-01-28 HU HU81178A patent/HU182280B/hu unknown
- 1981-01-29 AU AU66719/81A patent/AU540697B2/en not_active Ceased
- 1981-10-29 ES ES506686A patent/ES8301884A1/es not_active Expired
- 1981-10-29 ES ES506685A patent/ES506685A0/es active Granted
- 1981-10-29 ES ES506688A patent/ES506688A0/es active Granted
- 1981-10-29 ES ES506684A patent/ES8400079A1/es not_active Expired
- 1981-10-29 ES ES506687A patent/ES8301885A1/es not_active Expired
1982
- 1982-03-24 US US06/361,290 patent/US4448991A/en not_active Expired - Fee Related
1984
- 1984-08-01 KR KR1019840004583A patent/KR840001553B1/ko not_active Expired
- 1984-08-01 KR KR1019840004581A patent/KR840001551B1/ko not_active Expired
- 1984-08-01 KR KR1019840004584A patent/KR850000627B1/ko not_active Expired
- 1984-08-01 KR KR1019840004582A patent/KR840001552B1/ko not_active Expired
- 1984-08-01 KR KR1019840004585A patent/KR840001554B1/ko not_active Expired

Also Published As

Publication number	Publication date
JPS56120650A (en)	1981-09-22
IE810153L (en)	1981-07-29
KR840001552B1 (ko)	1984-10-05
KR850000626B1 (ko)	1985-05-06
MC1365A1 (fr)	1981-10-23
IT1135001B (it)	1986-08-20
FR2479815B1 (ko)	1984-02-17
ES506684A0 (es)	1983-10-16
ES498866A0 (es)	1982-12-01
EP0033156A3 (en)	1982-03-17
CS219941B2 (en)	1983-03-25
NL8100403A (nl)	1981-08-17
GB2068373B (en)	1983-11-30
AU6671981A (en)	1981-08-06
NO149958C (no)	1984-07-25
KR840001553B1 (ko)	1984-10-05
KR850002003A (ko)	1985-04-10
IT8119047A0 (it)	1981-01-08
ZW31480A1 (en)	1981-09-02
PH16098A (en)	1983-06-24
CS219940B2 (en)	1983-03-25
ES8301878A1 (es)	1982-12-16
EP0033156A2 (de)	1981-08-05
CS219943B2 (en)	1983-03-25
NO810297L (no)	1981-07-30
US4448991A (en)	1984-05-15
NO149958B (no)	1984-04-16
FI801147A7 (fi)	1981-01-01
ZA81459B (en)	1982-02-24
DK15681A (da)	1981-07-30
ES506687A0 (es)	1982-12-16
EP0033156B1 (de)	1984-10-17
KR840001551B1 (ko)	1984-10-05
IL61961A (en)	1984-05-31
SE8100403L (sv)	1981-07-30
PT72415A (en)	1981-02-01
ATA35581A (de)	1984-05-15
YU332180A (en)	1983-10-31
BR8100484A (pt)	1981-08-18
ES8301883A1 (es)	1982-12-16
AU540697B2 (en)	1984-11-29
AR227906A1 (es)	1982-12-30
HU182280B (en)	1983-12-28
DE3166656D1 (en)	1984-11-22
ES506685A0 (es)	1982-12-16
AT376654B (de)	1984-12-27
CA1161064A (en)	1984-01-24
ES506686A0 (es)	1982-12-16
LU83096A1 (de)	1982-09-10
KR840001554B1 (ko)	1984-10-05
ES506688A0 (es)	1982-12-16
ES8301885A1 (es)	1982-12-16
ES8301200A1 (es)	1982-12-01
PT72415B (en)	1982-07-26
IE50885B1 (en)	1986-08-06
US4336268A (en)	1982-06-22
ES8301884A1 (es)	1982-12-16
IL61961A0 (en)	1981-02-27
ES8400079A1 (es)	1983-10-16
FR2479815A1 (fr)	1981-10-09
DE3102603A1 (de)	1981-12-10
GB2068373A (en)	1981-08-12
KR830005105A (ko)	1983-07-23
NZ196086A (en)	1984-08-24
KR850000627B1 (ko)	1985-05-06
CS220347B2 (en)	1983-03-25
CS219944B2 (en)	1983-03-25
CH644580A5 (de)	1984-08-15
ATE9895T1 (de)	1984-11-15

Publication	Publication Date	Title
CA1077957A (en)	1980-05-20	Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives
JP2655692B2 (ja)	1997-09-24	スルホンアミドチエニルカルボン酸化合物
CS219942B2 (en)	1983-03-25	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
CH644348A5 (fr)	1984-07-31	Amino-ethers oxydes, leur procede de preparation et medicament les contenant.
US4735944A (en)	1988-04-05	Spiro-dioxolanes, -dithiolanes and -oxothiolanes, and their use in mental therapy
CH664158A5 (fr)	1988-02-15	Derives propylidenediphosphonates-1,3 substitues en position 2, leur procede de preparation et compositions pharmaceutiques les contenant.
US4350822A (en)	1982-09-21	Antilipidemicpara-[aryl(alkyl or alkenyl)amino]benzoic acid derivatives
EP0151072A2 (fr)	1985-08-07	Dérivés de l'acide méthylènediphosphonique, procédé d'obtention et compositions pharmaceutiques antirhumatismales les contenant
SK140795A3 (en)	1996-09-04	1-arylcycloalkyl sulphides, -sulphoxides and -sulphones for the treatment of depression, anxiety and parkinson's disease
DE69105786T2 (de)	1995-04-27	Harnstoffderivate, deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen.
EP0612716B1 (fr)	1996-05-08	Procédé pour la préparation d'un aminoalcool optiquement pur
EP0065295A1 (de)	1982-11-24	Substituierte Tryptaminderivate von Thienyloxypropanolaminen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung
DE2710503A1 (de)	1978-02-16	2-organothio-2-cyclopentenone, sich davon ableitende organothiocyclopentane und verfahren zur herstellung dieser verbindungen
US4977176A (en)	1990-12-11	Pilocarpine compounds which are used as pharmaceutical agents
DE3302814C2 (ko)	1992-06-25
US4540806A (en)	1985-09-10	Benzocycloalkane amines
FR2647785A1 (fr)	1990-12-07	Nouveaux derives de la pyrrolidone, leur procede de preparation et les compositions pharmaceutiques les renfermant
MC1287A1 (fr)	1980-07-22	Derives de cyclohexadiene
SK61199A3 (en)	1999-11-08	Benzenesulfonamide derivatives and drugs containing the same
US3882164A (en)	1975-05-06	Dextrorotatory 3r-n-monomethyl-amino-4c-phenyl-4t-ethoxycarbonicyclohexene-1 and process for the production thereof
JPS59112949A (ja)	1984-06-29	新規なｌ−スレオ−アドレナリン酸
DE2030714A1 (de)	1971-02-04	Neue tricychsche Verbindungen und Verfahren zu ihrer Herstellung
EP0220112A2 (fr)	1987-04-29	Dérivés aromatiques substitués par un groupement (oméga-amino) alcanol à activité antimicrobienne, leur préparation et les compositions les contenant
US3968142A (en)	1976-07-06	Hydronaphthalene carboxylic acids and derivatives
EP0001255B1 (de)	1981-09-30	Neue fluorhaltige Prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel