NO761855L - - Google Patents

Info

Publication number: NO761855L
Authority: NO; Norway
Prior art keywords: formula; pyridyl; compound; bromophenyl; mixture
Prior art date: 1974-11-21

Application number

NO761855A

Other languages

English (en)

Norwegian (no)

Inventor

P A E Carlsson

B S E Carnmalm

S B Ross

C B J Ulff

Original Assignee

Astra Laekemedel Ab

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.)

1974-11-21

Filing date

1976-06-01

Publication date

1976-05-24

1974-11-21 Priority claimed from SE7414622A external-priority patent/SE388854B/sv

1976-05-24 Publication of NO761855L publication Critical patent/NO761855L/no

1976-06-01 Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab

1976-06-01 Priority to NO761855A priority Critical patent/NO761855L/no

Links

150000003839 salts Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 7
-1 phenylpyridyl Chemical class 0.000 claims description 5
239000013067 intermediate product Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
239000000203 mixture Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000000034 method Methods 0.000 description 14
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
230000001430 anti-depressive effect Effects 0.000 description 12
239000007858 starting material Substances 0.000 description 12
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 8
239000000935 antidepressant agent Substances 0.000 description 8
229940005513 antidepressants Drugs 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
230000018044 dehydration Effects 0.000 description 7
238000006297 dehydration reaction Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
229960002748 norepinephrine Drugs 0.000 description 6
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SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
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230000000694 effects Effects 0.000 description 5
238000000605 extraction Methods 0.000 description 5
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229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000009471 action Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
BVLDJXBFPHUCMZ-DMALGBCRSA-N (z)-3-(4-bromophenyl)-3-pyridin-3-ylprop-2-en-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=CC=1C(=C/CN)\C1=CC=C(Br)C=C1 BVLDJXBFPHUCMZ-DMALGBCRSA-N 0.000 description 3
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical class NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
210000005036 nerve Anatomy 0.000 description 3
239000000047 product Substances 0.000 description 3
229940080818 propionamide Drugs 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
IDGVUIHZWDVXOQ-UHFFFAOYSA-N (4-bromophenyl)-pyridin-3-ylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CN=C1 IDGVUIHZWDVXOQ-UHFFFAOYSA-N 0.000 description 2
UMIKHYXXJVVGFS-UHFFFAOYSA-N 1-(4-bromophenyl)-1-pyridin-3-ylpropane-1,3-diol Chemical compound C=1C=CN=CC=1C(O)(CCO)C1=CC=C(Br)C=C1 UMIKHYXXJVVGFS-UHFFFAOYSA-N 0.000 description 2
BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
AZFZKANGXPSDEA-UHFFFAOYSA-N 3-(4-bromophenyl)-n-methyl-3-pyridin-3-ylprop-2-en-1-amine Chemical compound C=1C=CN=CC=1C(=CCNC)C1=CC=C(Br)C=C1 AZFZKANGXPSDEA-UHFFFAOYSA-N 0.000 description 2
LNNHMDXBTFAGFT-UHFFFAOYSA-N 3-amino-1-(4-bromophenyl)-1-pyridin-3-ylpropan-1-ol Chemical compound C=1C=CN=CC=1C(O)(CCN)C1=CC=C(Br)C=C1 LNNHMDXBTFAGFT-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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 2
229930195725 Mannitol Natural products 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000010171 animal model Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
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ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
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GCPXTCJSZRICQL-UHFFFAOYSA-N ethyl 3-(4-bromophenyl)-3-hydroxy-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(O)(CC(=O)OCC)C1=CC=C(Br)C=C1 GCPXTCJSZRICQL-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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239000003112 inhibitor Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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238000002844 melting Methods 0.000 description 2
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210000001259 mesencephalon Anatomy 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical class C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 2
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OYRMIBLAODHTQB-UHFFFAOYSA-N 2-hydroxy-3-pyridin-3-ylpropanenitrile Chemical compound N#CC(O)CC1=CC=CN=C1 OYRMIBLAODHTQB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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IATOXAPOVVFGKH-UHFFFAOYSA-N 3-(4-bromophenyl)-3-hydroxy-3-pyridin-3-ylpropanamide Chemical compound C=1C=CN=CC=1C(O)(CC(=O)N)C1=CC=C(Br)C=C1 IATOXAPOVVFGKH-UHFFFAOYSA-N 0.000 description 1
WPUHCXJCDYNYDB-UHFFFAOYSA-N 3-(4-bromophenyl)-3-hydroxy-3-pyridin-3-ylpropanenitrile Chemical compound C=1C=CN=CC=1C(CC#N)(O)C1=CC=C(Br)C=C1 WPUHCXJCDYNYDB-UHFFFAOYSA-N 0.000 description 1
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
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229910019142 PO4 Inorganic materials 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
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125000000217 alkyl group Chemical group 0.000 description 1
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238000005804 alkylation reaction Methods 0.000 description 1
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235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000002763 arrhythmic effect Effects 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
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210000004556 brain Anatomy 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
230000001914 calming effect Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
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235000014113 dietary fatty acids Nutrition 0.000 description 1
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PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
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239000000284 extract Substances 0.000 description 1
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239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
LFETXMWECUPHJA-UHFFFAOYSA-N methanamine;hydrate Chemical compound O.NC LFETXMWECUPHJA-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000002969 morbid Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
BFGNHBBJJWESFT-UHFFFAOYSA-N n,n-dimethylformamide;ethoxyethane Chemical compound CCOCC.CN(C)C=O BFGNHBBJJWESFT-UHFFFAOYSA-N 0.000 description 1
GIKNJMSYQSDBRR-UHFFFAOYSA-N n-propylpyridin-2-amine Chemical compound CCCNC1=CC=CC=N1 GIKNJMSYQSDBRR-UHFFFAOYSA-N 0.000 description 1
230000003982 neuronal uptake Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229960001158 nortriptyline Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002746 orthostatic effect Effects 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

NO761855A 1974-11-21 1976-06-01 NO761855L (sv)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO761855A NO761855L (sv)	1974-11-21	1976-06-01

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE7414622A SE388854B (sv)	1974-11-21	1974-11-21	Forfarande for framstellning av fenylpyridylaminderivat
NO753849A NO149775C (no)	1974-11-21	1975-11-17	Analogifremgangsmaate for fremstilling av fenyl-pyridylamin-derivater med antidepressiv virkning
NO761855A NO761855L (sv)	1974-11-21	1976-06-01

Publications (1)

Publication Number	Publication Date
NO761855L true NO761855L (sv)	1976-05-24

Family

ID=27352730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO761855A NO761855L (sv)	1974-11-21	1976-06-01

Country Status (1)

Country	Link
NO (1)	NO761855L (sv)

1976
- 1976-06-01 NO NO761855A patent/NO761855L/no unknown

Publication	Publication Date	Title
NO118710B (sv)	1970-02-02
NO162176B (no)	1989-08-14	Middel for bekjempelse av plantesykdommer og anvendelse derav.
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NO147243B (no)	1982-11-22	Analogifremgangsmaate for fremstilling av terapeutisk aktive ftalanderivater.
NO793673L (no)	1980-05-28	Hydroksypropyl-triazoler, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel
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DK168010B1 (da)	1994-01-17	Tetrahydroisoquinolinforbindelser og farmaceutisk middel indeholdende en saadan forbindelse
NO149775B (no)	1984-03-12	Analogifremgangsmaate for fremstilling av fenyl-pyridylamin-derivater med antidepressiv virkning
US3043842A (en)	1962-07-10	Substituted acridans
NO761855L (sv)	1976-05-24
NO812401L (no)	1981-07-13	Nye halogenfenyl-pyridyl-allylaminderivater.
EP0073645B1 (en)	1986-11-12	2-cyclic amino-2-(1,2-benzisoxazol-3-yl)acetic acid ester derivatives, process for the preparation thereof and composition containing the same
NO852814L (no)	1986-01-14	Acetyleniske fenoksypropanolderivater.
US4102887A (en)	1978-07-25	Intermediates used in the preparation of phenyl-pyridylamine derivatives
DK158944B (da)	1990-08-06	Analogifremgangsmaade til fremstilling af substituerede methylimidazolforbindelser
NO124309B (sv)	1972-04-04
JPS6344749B2 (sv)	1988-09-06
US4186202A (en)	1980-01-29	Phenyl-pyridylamine derivatives
CA1204440A (en)	1986-05-13	Isoxazole¬5,4-b\|pyridines
EP0000322A1 (en)	1979-01-10	Compounds having an anti-depressive or tranquilizing activity, pharmaceutical compositions containing them, and processes and intermediates for their preparation
US2761866A (en)	1956-09-04	3-pyridine sulfinic acid and process
US7482344B2 (en)	2009-01-27	Tricyclic steroid hormone nuclear receptor modulators
NO781896L (no)	1978-12-04	4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidler
NO853935L (no)	1986-04-07	Fremgangsm¨te ved fremstilling av 2-pyridin-thiolderivater