NO782304L - Fremgangsmaate til fremstilling av en terapeutisk aktiv forbindelse - Google Patents
Fremgangsmaate til fremstilling av en terapeutisk aktiv forbindelseInfo
- Publication number
- NO782304L NO782304L NO782304A NO782304A NO782304L NO 782304 L NO782304 L NO 782304L NO 782304 A NO782304 A NO 782304A NO 782304 A NO782304 A NO 782304A NO 782304 L NO782304 L NO 782304L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- active compound
- preparing
- procedure
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 15
- 230000001225 therapeutic effect Effects 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 Cl or Br Chemical class 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- YIIHEMGEQQWSMA-UHFFFAOYSA-M 2-(dimethylamino)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCN(C)C)C1=CC=CC=C1 YIIHEMGEQQWSMA-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPPVKRFBIWMSX-UHFFFAOYSA-N Cis-zimelidine Chemical compound C=1C=CN=CC=1C(=CCN(C)C)C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910020667 PBr3 Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- WLNKGGRXEOAKBY-UHFFFAOYSA-N bis(4-bromo-2-pyridin-3-ylphenyl)methanone Chemical compound C=1C=CN=CC=1C1=CC(Br)=CC=C1C(=O)C1=CC=C(Br)C=C1C1=CC=CN=C1 WLNKGGRXEOAKBY-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE7707707A SE409861B (sv) | 1977-07-04 | 1977-07-04 | Ett nytt forfarande for framstellning av en terapeutisk aktiv pyridinforening |
Publications (1)
Publication Number | Publication Date |
---|---|
NO782304L true NO782304L (no) | 1979-01-05 |
Family
ID=20331764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO782304A NO782304L (no) | 1977-07-04 | 1978-07-03 | Fremgangsmaate til fremstilling av en terapeutisk aktiv forbindelse |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS5414976A (ru) |
AT (1) | AT365171B (ru) |
CA (1) | CA1082198A (ru) |
CH (1) | CH641163A5 (ru) |
DK (1) | DK295378A (ru) |
ES (1) | ES471302A1 (ru) |
FI (1) | FI64581C (ru) |
IT (1) | IT1105226B (ru) |
NL (1) | NL7807246A (ru) |
NO (1) | NO782304L (ru) |
SE (1) | SE409861B (ru) |
SU (1) | SU923366A3 (ru) |
WO (1) | WO1979000023A1 (ru) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE7909514L (sv) | 1979-11-16 | 1981-05-17 | Astra Laekemedel Ab | Nya halofenyl-pyridyl-allylaminderivat |
FI20090389A (fi) * | 2009-10-23 | 2011-04-24 | Kone Corp | Menetelmä hissin valmistamisessa |
FI122066B (fi) * | 2009-12-31 | 2011-08-15 | Kone Corp | Menetelmä hissin valmistamisessa |
FI20100223A0 (fi) * | 2010-05-28 | 2010-05-28 | Kone Corp | Menetelmä ja hissijärjestely |
FI20106273A (fi) * | 2010-12-01 | 2012-06-02 | Kone Corp | Hissijärjestely ja menetelmä |
EP2636629B1 (en) * | 2012-03-06 | 2015-05-06 | KONE Corporation | A method and an elevator arrangement |
US9388020B2 (en) * | 2012-03-06 | 2016-07-12 | Kone Corporation | Method and an elevator arrangement |
-
1977
- 1977-07-04 SE SE7707707A patent/SE409861B/sv unknown
-
1978
- 1978-06-26 WO PCT/SE1978/000009 patent/WO1979000023A1/en unknown
- 1978-06-26 CH CH329979A patent/CH641163A5/de not_active IP Right Cessation
- 1978-06-27 CA CA306,260A patent/CA1082198A/en not_active Expired
- 1978-06-29 DK DK782953A patent/DK295378A/da not_active Application Discontinuation
- 1978-06-30 ES ES471302A patent/ES471302A1/es not_active Expired
- 1978-06-30 FI FI782115A patent/FI64581C/fi not_active IP Right Cessation
- 1978-06-30 IT IT50123/78A patent/IT1105226B/it active
- 1978-07-03 NO NO782304A patent/NO782304L/no unknown
- 1978-07-04 AT AT0483778A patent/AT365171B/de not_active IP Right Cessation
- 1978-07-04 NL NL7807246A patent/NL7807246A/xx not_active Application Discontinuation
- 1978-07-04 JP JP8182078A patent/JPS5414976A/ja active Pending
-
1979
- 1979-08-03 SU SU792798502A patent/SU923366A3/ru active
Also Published As
Publication number | Publication date |
---|---|
SE7707707L (sv) | 1979-01-05 |
SE409861B (sv) | 1979-09-10 |
SU923366A3 (ru) | 1982-04-23 |
DK295378A (da) | 1979-01-05 |
AT365171B (de) | 1981-12-28 |
ATA483778A (de) | 1981-05-15 |
CA1082198A (en) | 1980-07-22 |
NL7807246A (nl) | 1979-01-08 |
CH641163A5 (de) | 1984-02-15 |
FI64581C (fi) | 1983-12-12 |
FI782115A (fi) | 1979-01-05 |
WO1979000023A1 (en) | 1979-01-25 |
ES471302A1 (es) | 1979-09-01 |
IT1105226B (it) | 1985-10-28 |
IT7850123A0 (it) | 1978-06-30 |
JPS5414976A (en) | 1979-02-03 |
FI64581B (fi) | 1983-08-31 |
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