NO122365B - - Google Patents

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Info

Publication number: NO122365B
Authority: NO; Norway
Prior art keywords: phenyl; general formula; formula; reacts; hydrogen
Prior art date: 1965-06-02

Application number

NO163248A

Other languages

English (en)

Norwegian (no)

Inventor

G Ehrhart

H Ott

Original Assignee

Hoechst Ag

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.)

1965-06-02

Filing date

1966-06-01

Publication date

1971-06-21

1966-06-01 Application filed by Hoechst Ag filed Critical Hoechst Ag

1971-06-21 Publication of NO122365B publication Critical patent/NO122365B/no

Links

238000000034 method Methods 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical class CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 claims description 9
ZHOOOLQOWQVYOE-UHFFFAOYSA-N 2-cyclohexylidene-2-phenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)=C1CCCCC1 ZHOOOLQOWQVYOE-UHFFFAOYSA-N 0.000 claims description 9
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
239000012433 hydrogen halide Substances 0.000 claims description 8
229910000039 hydrogen halide Inorganic materials 0.000 claims description 8
125000002560 nitrile group Chemical group 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
238000007127 saponification reaction Methods 0.000 claims description 4
LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical class NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000007514 bases Chemical class 0.000 claims description 3
230000001035 methylating effect Effects 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229950000188 halopropane Drugs 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
-1 carboxyl compound Chemical class 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000001294 propane Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 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
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000000630 rising effect Effects 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NVYOCAOZCSNIHR-UHFFFAOYSA-N 2-bromopropylbenzene Chemical compound CC(Br)CC1=CC=CC=C1 NVYOCAOZCSNIHR-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000004036 acetal group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZUFLMKDOIMZOSA-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(C)C(C)=C1 ZUFLMKDOIMZOSA-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
AQFLVLHRZFLDDV-UHFFFAOYSA-N 1-phenylpropan-1-amine Chemical compound CCC(N)C1=CC=CC=C1 AQFLVLHRZFLDDV-UHFFFAOYSA-N 0.000 description 1
SEVKYLYIYIKRSW-UHFFFAOYSA-N 1-phenylpropan-2-ylazanium;chloride Chemical compound Cl.CC(N)CC1=CC=CC=C1 SEVKYLYIYIKRSW-UHFFFAOYSA-N 0.000 description 1
PJXZRMMYWPPTNB-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-4,4-diethoxy-2-phenylbutanenitrile Chemical compound C(C)OC(CC(C#N)(C1=CCCCC1)C1=CC=CC=C1)OCC PJXZRMMYWPPTNB-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
CKWAHIDVXZGPES-UHFFFAOYSA-N 2-chloropropylbenzene Chemical compound CC(Cl)CC1=CC=CC=C1 CKWAHIDVXZGPES-UHFFFAOYSA-N 0.000 description 1
WZSSJGPFBDOVLS-UHFFFAOYSA-N 2-iodopropylbenzene Chemical compound CC(I)CC1=CC=CC=C1 WZSSJGPFBDOVLS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
GOCPGZPCTSKYKW-UHFFFAOYSA-N 3-phenylheptan-2-one Chemical class CCCCC(C(C)=O)C1=CC=CC=C1 GOCPGZPCTSKYKW-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
229910020889 NaBH3 Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 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
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
MYWUZJCMWCOHBA-UHFFFAOYSA-N n-methyl-1-phenylpropan-2-amine Chemical compound CNC(C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-UHFFFAOYSA-N 0.000 description 1
CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical class CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 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
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 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
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
ZSZUWPRERIPUBM-UHFFFAOYSA-N xylopropamine Chemical compound CC(N)CC1=CC=C(C)C(C)=C1 ZSZUWPRERIPUBM-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (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)

NO163248A 1965-06-02 1966-06-01 NO122365B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0046214		1965-06-02

Publications (1)

Publication Number	Publication Date
NO122365B true NO122365B (de)	1971-06-21

Family

ID=7100908

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO163248A NO122365B (de)	1965-06-02	1966-06-01

Country Status (13)

Country	Link
US (1)	US3409671A (de)
AT (6)	AT271439B (de)
BE (1)	BE681977A (de)
CH (6)	CH477396A (de)
DE (1)	DE1518832A1 (de)
DK (1)	DK114406B (de)
ES (1)	ES327332A1 (de)
FR (2)	FR1481779A (de)
GB (1)	GB1090896A (de)
IL (1)	IL25794A (de)
NL (1)	NL6607385A (de)
NO (1)	NO122365B (de)
SE (1)	SE321217B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3485873A (en) *	1966-12-21	1969-12-23	Sterling Drug Inc	N-benzyl-n-methyl-omega-phenyl-omega-cycloalkyl-lower-alkylamines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3328249A (en) *	1965-06-21	1967-06-27	Sterling Drug Inc	Process for counteracting depressive states

1965
- 1965-06-02 DE DE19651518832 patent/DE1518832A1/de active Granted
1966
- 1966-05-13 US US549817A patent/US3409671A/en not_active Expired - Lifetime
- 1966-05-17 IL IL25794A patent/IL25794A/xx unknown
- 1966-05-27 CH CH76869A patent/CH477396A/de not_active IP Right Cessation
- 1966-05-27 NL NL6607385A patent/NL6607385A/xx unknown
- 1966-05-27 GB GB23961/66A patent/GB1090896A/en not_active Expired
- 1966-05-27 CH CH76969A patent/CH477397A/de not_active IP Right Cessation
- 1966-05-27 CH CH77169A patent/CH492672A/de not_active IP Right Cessation
- 1966-05-27 CH CH77269A patent/CH477398A/de not_active IP Right Cessation
- 1966-05-27 CH CH774066A patent/CH481871A/de not_active IP Right Cessation
- 1966-05-27 CH CH77069A patent/CH483391A/de not_active IP Right Cessation
- 1966-05-30 ES ES0327332A patent/ES327332A1/es not_active Expired
- 1966-05-31 AT AT80268A patent/AT271439B/de active
- 1966-05-31 AT AT512466A patent/AT271438B/de active
- 1966-05-31 AT AT80668A patent/AT271443B/de active
- 1966-05-31 AT AT80368A patent/AT271440B/de active
- 1966-05-31 AT AT80568A patent/AT271442B/de active
- 1966-05-31 AT AT80468A patent/AT271441B/de active
- 1966-06-01 NO NO163248A patent/NO122365B/no unknown
- 1966-06-01 DK DK282566AA patent/DK114406B/da unknown
- 1966-06-02 BE BE681977D patent/BE681977A/xx unknown
- 1966-06-02 SE SE7544/66A patent/SE321217B/xx unknown
- 1966-06-02 FR FR63867A patent/FR1481779A/fr not_active Expired
- 1966-09-01 FR FR74963A patent/FR5708M/fr not_active Expired

Also Published As

Publication number	Publication date
FR1481779A (fr)	1967-05-19
AT271443B (de)	1969-06-10
GB1090896A (en)	1967-11-15
DE1518832C3 (de)	1974-06-06
AT271438B (de)	1969-06-10
CH477396A (de)	1969-08-31
NL6607385A (de)	1966-12-05
FR5708M (de)	1968-01-15
IL25794A (en)	1970-04-20
US3409671A (en)	1968-11-05
AT271441B (de)	1969-06-10
ES327332A1 (es)	1967-07-16
CH477397A (de)	1969-08-31
DE1518832B2 (de)	1973-10-31
AT271439B (de)	1969-06-10
SE321217B (de)	1970-03-02
CH477398A (de)	1969-08-31
AT271442B (de)	1969-06-10
BE681977A (de)	1966-12-02
CH481871A (de)	1969-11-30
CH483391A (de)	1969-12-31
DK114406B (da)	1969-06-30
DE1518832A1 (de)	1969-05-14
CH492672A (de)	1970-06-30
AT271440B (de)	1969-06-10

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JP3055819B2 (ja)	2000-06-26	２−チエニルグリシド酸誘導体およびその製造法
US6258961B1 (en)	2001-07-10	Intermediates and process for the preparation thereof
NO133274B (de)	1975-12-29
NO178148B (no)	1995-10-23	Analogifremgangsmåte for fremstilling av terapeutisk aktive O-(3-amino-2-hydroxypropyl)-hydroximinsyrehalogenider, og nye mellomprodukter
SU428597A3 (ru)	1974-05-15	СПОСОБ ПОЛУЧЕНИЯ р-АРИЛ-2-АМИНОАЛКОКСИСТИРОЛОВ
NO118710B (de)	1970-02-02
IL101248A (en)	1996-12-05	History of indole, their preparation and the pharmaceutical preparations containing them
NO162965B (no)	1989-12-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater.
SU510999A3 (ru)	1976-04-15	Способ получени (метоксиметил-фурилметил)6,7-бензоморфанов илиморфинанов
NO162176B (no)	1989-08-14	Middel for bekjempelse av plantesykdommer og anvendelse derav.
US2502151A (en)	1950-03-28	Dimethylaminoalkylamino antihistiminic compounds
US3103516A (en)	1963-09-10	J-tertiaryaminq-lower alkyl-jb-meta-
NO743773L (de)	1975-05-20
US2958694A (en)	1960-11-01	1-(aroylalkyl)-4-(2'-pyridyl) piperazines
NO764039L (de)	1977-06-06
SU772482A3 (ru)	1980-10-15	Способ получени 4-дифенилметилен- 1-оксибензилпиперидинов или их солей
US3192230A (en)	1965-06-29	Process for producing 1, 3, 3-trisubstituted-4-(beta-haloethyl)-2-pyrrolidinone
NO138338B (no)	1978-05-08	Fremgangsmaate til fremstilling av tresponplater med kondensasjonsharpikser som bindemiddel
EA010051B1 (ru)	2008-06-30	Соединения инданилпиперазина, способ их получения и содержащие их фармацевтические композиции
US2686784A (en)	1954-08-17	Piperidine derivatives
NO128773B (de)	1974-01-07
NO882065L (no)	1988-11-14	Diarylalkyl-substituerte alkylaminer, fremgangsmaate for fremstilling av dem, anvendelse av dem, saavel som legemidler som inneholder dem.
NO136841B (no)	1977-08-08	Analogifremgangsm}te for fremstilling av terapeutisk aktive fenylimidazolidinoner.
NO792901L (no)	1980-03-11	Alfa-aryl-alfa,alfa-bis(omega-(disubstituert amino)alkyl)-ag cetamidforbindelser og fremgangsmaate til deres fremstillin
SU422146A3 (de)	1974-03-30