JPH03135948A - 置換フェニルアセトニトリル - Google Patents

置換フェニルアセトニトリル

Info

Publication number: JPH03135948A
Authority: JP; Japan
Prior art keywords: reference example; compound; carbon atoms; dimethylamino; alkyl
Prior art date: 1982-12-13
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.): Granted

Application number

JP2267502A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0440339B2 (da

Inventor

George E Morris Husbands

ジョージ・エドワード・モリス・ハズバンズ

John P Yardley

ジョン・パトリック・ヤードレイ

Eric A Muth

エリック・アンソニー・ムス

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.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1982-12-13

Filing date

1990-10-03

Publication date

1991-06-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27412395&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPH03135948(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1983-10-26 Priority claimed from US06/545,701 external-priority patent/US4535186A/en

1990-10-03 Application filed by American Home Products Corp filed Critical American Home Products Corp

1991-06-10 Publication of JPH03135948A publication Critical patent/JPH03135948A/ja

1992-07-02 Publication of JPH0440339B2 publication Critical patent/JPH0440339B2/ja

Status Granted legal-status Critical Current

Links

SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 title abstract description 5
150000007962 benzene acetonitriles Chemical class 0.000 title 1
-1 N-protected amino Chemical group 0.000 claims abstract description 30
125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 52
238000000034 method Methods 0.000 abstract description 20
239000000935 antidepressant agent Substances 0.000 abstract description 15
229940005513 antidepressants Drugs 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 13
150000002825 nitriles Chemical class 0.000 abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
238000010934 O-alkylation reaction Methods 0.000 abstract description 2
150000001450 anions Chemical class 0.000 abstract description 2
210000003169 central nervous system Anatomy 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
ASYJSBPNAIDUHX-UHFFFAOYSA-N 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile Chemical compound C1=CC(OC)=CC=C1C(C#N)C1(O)CCCCC1 ASYJSBPNAIDUHX-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
238000002844 melting Methods 0.000 description 43
230000008018 melting Effects 0.000 description 43
239000000203 mixture Substances 0.000 description 37
239000000243 solution Substances 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
238000000921 elemental analysis Methods 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 description 19
239000007787 solid Substances 0.000 description 19
239000010410 layer Substances 0.000 description 18
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 17
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 17
229940126062 Compound A Drugs 0.000 description 16
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000012267 brine Substances 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical group OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 13
230000005764 inhibitory process Effects 0.000 description 13
238000004949 mass spectrometry Methods 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
239000012458 free base Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
230000001430 anti-depressive effect Effects 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
229910052722 tritium Inorganic materials 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
125000004093 cyano group Chemical group *C#N 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
229960003914 desipramine Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000012280 lithium aluminium hydride Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000002253 acid Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000700199 Cavia porcellus Species 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
230000008602 contraction Effects 0.000 description 6
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 6
210000003405 ileum Anatomy 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
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 5
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
229960004801 imipramine Drugs 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 5
229960003147 reserpine Drugs 0.000 description 5
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229940123445 Tricyclic antidepressant Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
230000002631 hypothermal effect Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
239000003029 tricyclic antidepressant agent Substances 0.000 description 4
PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 3
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
238000007126 N-alkylation reaction Methods 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
230000001078 anti-cholinergic effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
239000002775 capsule Substances 0.000 description 3
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 3
229960004484 carbachol Drugs 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
229960000582 mepyramine Drugs 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
BUCJHJXFXUZJHL-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound CCC1(O)CCCCC1 BUCJHJXFXUZJHL-UHFFFAOYSA-N 0.000 description 2
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
CNGVHZAORFMGBW-UHFFFAOYSA-N 2-(4-bromophenyl)-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CC=C(Br)C=C1 CNGVHZAORFMGBW-UHFFFAOYSA-N 0.000 description 2
ZPEKXVLJLVTMBD-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n,n-dimethylacetamide Chemical compound COC1=CC=C(CC(=O)N(C)C)C=C1 ZPEKXVLJLVTMBD-UHFFFAOYSA-N 0.000 description 2
MUZYAEDDOSKNRG-UHFFFAOYSA-N 2-(4-methoxyphenyl)propanenitrile Chemical compound COC1=CC=C(C(C)C#N)C=C1 MUZYAEDDOSKNRG-UHFFFAOYSA-N 0.000 description 2
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
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231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
229940053544 other antidepressants in atc Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000002002 slurry Substances 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
150000003413 spiro compounds Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP2267502A 1982-12-13 1990-10-03 置換フェニルアセトニトリル Granted JPH03135948A (ja)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US44903282A	1982-12-13	1982-12-13
US449032		1982-12-13
US48659483A	1983-04-19	1983-04-19
US486594		1983-04-19
US06/545,701 US4535186A (en)	1983-04-19	1983-10-26	2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives
US545701		1983-10-26

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP23597983A Division JPS59116252A (ja)	1982-12-13	1983-12-13	フエネチルアミン誘導体およびその製法

Publications (2)

Publication Number	Publication Date
JPH03135948A true JPH03135948A (ja)	1991-06-10
JPH0440339B2 JPH0440339B2 (da)	1992-07-02

Family

ID=27412395

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP2267502A Granted JPH03135948A (ja)	1982-12-13	1990-10-03	置換フェニルアセトニトリル
JP2267501A Granted JPH03178953A (ja)	1982-12-13	1990-10-03	置換フェニルアセトアミド

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP2267501A Granted JPH03178953A (ja)	1982-12-13	1990-10-03	置換フェニルアセトアミド

Country Status (4)

Country	Link
JP (2)	JPH03135948A (da)
DK (1)	DK166372C (da)
IL (1)	IL70390A (da)
PH (1)	PH20074A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USD1114446S1 (en) *	2022-07-19	2026-02-17	Yeti Coolers, Llc	Container
USD1116633S1 (en)	2023-09-20	2026-03-10	Yeti Coolers, Llc	Wine chiller

1983
- 1983-12-06 IL IL70390A patent/IL70390A/xx not_active IP Right Cessation
- 1983-12-12 DK DK571383A patent/DK166372C/da not_active IP Right Cessation
- 1983-12-12 PH PH29958A patent/PH20074A/en unknown
1990
- 1990-10-03 JP JP2267502A patent/JPH03135948A/ja active Granted
- 1990-10-03 JP JP2267501A patent/JPH03178953A/ja active Granted

Also Published As

Publication number	Publication date
IL70390A (en)	1986-12-31
JPH03178953A (ja)	1991-08-02
JPH0440339B2 (da)	1992-07-02
DK571383A (da)	1984-06-14
DK166372B (da)	1993-04-19
DK571383D0 (da)	1983-12-12
PH20074A (en)	1986-09-18
JPH0530826B2 (da)	1993-05-11
DK166372C (da)	1993-09-06
IL70390A0 (en)	1984-03-30

Publication	Publication Date	Title
US4535186A (en)	1985-08-13	2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives
EP0112669B1 (en)	1987-07-29	Phenethylamine derivatives and intermediates therefor
US4761501A (en)	1988-08-02	Substituted phenylacetamides
JP3299321B2 (ja)	2002-07-08	２−アミノメチル−クロマン類
US4611078A (en)	1986-09-09	Substituted phenylacetonitriles
Heinzelman	1953	Physiologically active secondary amines. β-(o-Methoxyphenyl)-isopropyl-N-methylamine and related compounds
JPH03135948A (ja)	1991-06-10	置換フェニルアセトニトリル
JPH0260653B2 (da)	1990-12-17
US3956314A (en)	1976-05-11	Derivatives of 2-pyrrolidinone
US4705807A (en)	1987-11-10	Amine derivatives
JPH0412260B2 (da)	1992-03-04
JPH0319236B2 (da)	1991-03-14
FI82926B (fi)	1991-01-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara fenetylaminderivat.
JPS649316B2 (da)	1989-02-16
KR910000436B1 (ko)	1991-01-25	펜에틸아민 유도체의 제조방법
Burger et al.	1950	Amino Derivatives of 2, 2-Diphenylcyclohexanone. I1
JPH0627106B2 (ja)	1994-04-13	フエノキシエチルアミン誘導体
JPS60185749A (ja)	1985-09-21	アラルキル（アリ−ルエチニル）アラルキルアミン類および血管拡張剤および抗高血圧剤としてのそれらの使用
US3127405A (en)	1964-03-31	I-phenylalkyl
US3869512A (en)	1975-03-04	Dibenzobicycloalkane amines and related compounds
FI77647C (fi)	1989-04-10	Foerfarande foer tillverkning av terapeutiskt anvaendbara fenetylaminderivat.
GB1575852A (en)	1980-10-01	Hexahydro-4-indolinol derivatives
KR940011134B1 (ko)	1994-11-23	N-아릴알킬 파라아미노에톡시페닐아세트아미드 유도체
JP2003171354A (ja)	2003-06-20	光学活性アミン化合物又はその塩の製造方法
US3649628A (en)	1972-03-14	Process for producing substituted cyclohexene compounds