CH465599A - Verfahren zur Herstellung von Dibenzocycloheptenen - Google Patents

Verfahren zur Herstellung von Dibenzocycloheptenen

Info

Publication number: CH465599A
Authority: CH; Switzerland
Prior art keywords: group; carbon atoms; cycloheptene; formula; alkyl
Prior art date: 1961-05-24

Application number

CH1532168A

Other languages

German (de)

English (en)

Inventor

Louis Engelhardt Edward

Elizabeth Christy Marcia

Original Assignee

Merck & Co Inc

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.)

1961-05-24

Filing date

1962-05-24

Publication date

1968-11-30

1962-05-24 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1968-11-30 Publication of CH465599A publication Critical patent/CH465599A/de

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 8
150000008508 dibenzocycloheptenes Chemical class 0.000 title description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 11
-1 cyanide halide Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229920001774 Perfluoroether Chemical group 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
PLDONKUSBQJOGO-UHFFFAOYSA-N 3-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(CCCN(C)C)C2=CC=CC=C21 PLDONKUSBQJOGO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
NGPAITITALWALP-UHFFFAOYSA-M magnesium;n,n-dimethylpropan-1-amine;chloride Chemical compound [Mg+2].[Cl-].CN(C)CC[CH2-] NGPAITITALWALP-UHFFFAOYSA-M 0.000 description 2
239000000155 melt Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
XUDMFUCJNFYMRZ-UHFFFAOYSA-N 11-chloro-11h-dibenzo[1,2-a:1',2'-e][7]annulene Chemical compound C1=CC2=CC=CC=C2C(Cl)C2=CC=CC=C21 XUDMFUCJNFYMRZ-UHFFFAOYSA-N 0.000 description 1
MMXVPWIRORDYJE-UHFFFAOYSA-N 2,11-dichloro-11h-dibenzo[1,3-e:1',2'-f][7]annulene Chemical compound C1=CC2=CC=C(Cl)C=C2C(Cl)C2=CC=CC=C21 MMXVPWIRORDYJE-UHFFFAOYSA-N 0.000 description 1
AYSSYOCBSVBJFZ-UHFFFAOYSA-N 2,11-dichloro-6,11-dihydro-5h-dibenzo[3,1-[7]annulene Chemical compound C1CC2=CC=C(Cl)C=C2C(Cl)C2=CC=CC=C21 AYSSYOCBSVBJFZ-UHFFFAOYSA-N 0.000 description 1
YVBGGZGCBWNVDX-UHFFFAOYSA-N 3-(11h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-n,n-dimethylpropan-1-amine Chemical compound C1=CC2=CC=CC=C2C(CCCN(C)C)C2=CC=CC=C21 YVBGGZGCBWNVDX-UHFFFAOYSA-N 0.000 description 1
QWPRVBPBGKAFAL-UHFFFAOYSA-N 3-(2-chloro-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulen-11-yl)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=C(Cl)C=C2C(CCCN(C)C)C2=CC=CC=C21 QWPRVBPBGKAFAL-UHFFFAOYSA-N 0.000 description 1
VQDUUNLXNKNTSM-UHFFFAOYSA-N 3-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-n-methylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 VQDUUNLXNKNTSM-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 1
PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical class C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
- C07C211/32—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings containing dibenzocycloheptane or dibenzocycloheptene ring systems or condensed derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Display Racks (AREA)

CH1532168A 1961-05-24 1962-05-24 Verfahren zur Herstellung von Dibenzocycloheptenen CH465599A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US12083561A	1961-05-24	1961-05-24
US14022361A	1961-09-25	1961-09-25

Publications (1)

Publication Number	Publication Date
CH465599A true CH465599A (de)	1968-11-30

Family

ID=26818813

Family Applications (7)

Application Number	Title	Priority Date	Filing Date
CH1532168A CH465599A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH1531968A CH467238A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen
CH1104067A CH464900A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH1531868A CH467744A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen
CH1532068A CH464903A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH1532268A CH467743A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH628562A CH464893A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen

Family Applications After (6)

Application Number	Title	Priority Date	Filing Date
CH1531968A CH467238A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen
CH1104067A CH464900A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH1531868A CH467744A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von 5H-Dibenzo-(a,d)-cycloheptenen
CH1532068A CH464903A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH1532268A CH467743A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen
CH628562A CH464893A (de)	1961-05-24	1962-05-24	Verfahren zur Herstellung von Dibenzocycloheptenen

Country Status (13)

Country	Link
BE (1)	BE617967A (da)
BR (1)	BR6239240D0 (da)
CH (7)	CH465599A (da)
CY (1)	CY354A (da)
DE (2)	DE1593098A1 (da)
DK (6)	DK107420C (da)
FI (3)	FI41391B (da)
FR (1)	FR2516M (da)
GB (1)	GB1008263A (da)
GT (1)	GT197016875A (da)
MY (1)	MY6700003A (da)
NO (1)	NO121833B (da)
SE (8)	SE325269B (da)

1962
- 1962-05-16 GB GB18913/62A patent/GB1008263A/en not_active Expired
- 1962-05-18 FI FI1007/62A patent/FI41391B/fi active
- 1962-05-21 DE DE19621593098 patent/DE1593098A1/de active Pending
- 1962-05-21 DE DE19621468212 patent/DE1468212A1/de active Pending
- 1962-05-22 BR BR139240/62A patent/BR6239240D0/pt unknown
- 1962-05-22 BE BE617967A patent/BE617967A/fr unknown
- 1962-05-23 DK DK106164AA patent/DK107420C/da active
- 1962-05-23 DK DK232162AA patent/DK110035C/da active
- 1962-05-23 DK DK106264AA patent/DK106278C/da active
- 1962-05-23 DK DK106064AA patent/DK108151C/da active
- 1962-05-23 DK DK166663AA patent/DK106326C/da active
- 1962-05-23 NO NO144482A patent/NO121833B/no unknown
- 1962-05-24 CH CH1532168A patent/CH465599A/de unknown
- 1962-05-24 CH CH1531968A patent/CH467238A/de unknown
- 1962-05-24 CH CH1104067A patent/CH464900A/de unknown
- 1962-05-24 CH CH1531868A patent/CH467744A/de unknown
- 1962-05-24 SE SE13207/65A patent/SE325269B/xx unknown
- 1962-05-24 CH CH1532068A patent/CH464903A/de unknown
- 1962-05-24 CH CH1532268A patent/CH467743A/de unknown
- 1962-05-24 SE SE5885/62A patent/SE317369B/xx unknown
- 1962-05-24 CH CH628562A patent/CH464893A/de unknown
- 1962-08-22 FR FR907533A patent/FR2516M/fr not_active Expired
1964
- 1964-02-27 DK DK97064AA patent/DK111679B/da unknown
1965
- 1965-05-14 SE SE635365A patent/SE318869B/xx unknown
- 1965-10-12 SE SE13209/65A patent/SE326441B/xx unknown
- 1965-10-12 SE SE13211/65A patent/SE326442B/xx unknown
- 1965-10-12 SE SE13204/65A patent/SE323364B/xx unknown
- 1965-10-12 SE SE13210/65A patent/SE325874B/xx unknown
- 1965-10-12 SE SE13205/65A patent/SE326440B/xx unknown
1966
- 1966-10-03 FI FI2588/66A patent/FI41647B/fi active
- 1966-10-03 FI FI2587/66A patent/FI41646B/fi active
- 1966-10-14 CY CY35466A patent/CY354A/xx unknown
1967
- 1967-12-31 MY MY19673A patent/MY6700003A/xx unknown
1970
- 1970-05-11 GT GT197016875A patent/GT197016875A/es unknown

Also Published As

Publication number	Publication date
DK111679B (da)	1968-09-30
CH464903A (de)	1968-11-15
FI41647B (da)	1969-09-30
DE1593098A1 (de)	1969-10-16
CH467238A (de)	1969-01-15
DK108151C (da)	1967-09-25
SE325269B (da)	1970-06-29
CY354A (en)	1966-10-14
SE317369B (da)	1969-11-17
SE326442B (da)	1970-07-27
DE1468212A1 (de)	1969-01-02
CH467744A (de)	1969-01-31
MY6700003A (en)	1967-12-31
FI41646B (da)	1969-09-30
DK107420C (da)	1967-05-29
CH464900A (de)	1968-11-15
GB1008263A (en)	1965-10-27
FR2516M (fr)	1964-05-11
CH464893A (de)	1968-11-15
SE326440B (da)	1970-07-27
DK106278C (da)	1967-01-16
BR6239240D0 (pt)	1973-05-24
NO121833B (da)	1971-04-19
SE326441B (da)	1970-07-27
BE617967A (fr)	1962-11-22
DK110035C (da)	1968-09-02
FI41391B (da)	1969-07-31
SE325874B (da)	1970-07-13
SE323364B (da)	1970-05-04
GT197016875A (es)	1971-11-02
DK106326C (da)	1967-01-23
CH467743A (de)	1969-01-31
SE318869B (da)	1969-12-22

Publication	Publication Date	Title
DE2047658C3 (de)	1980-11-13	2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH494730A (de)	1970-08-15	Verfahren zur Herstellung von Dibenzocyclopentenen
DE1941625C3 (de)	1982-03-18	Substituierte Phenylalkansäuren
DE2314636C2 (de)	1986-09-11	Indanderivate, deren Herstellung und diese enthaltende pharmazeutische Mittel
DE2112716A1 (de)	1972-10-05	Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester
CH591415A5 (en)	1977-09-15	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
DE1593091C3 (da)	1974-01-03
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