FI66608C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-amino-2,6-diaryl-tetrahydrotiopyraner - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-amino-2,6-diaryl-tetrahydrotiopyraner Download PDFInfo
- Publication number
- FI66608C FI66608C FI803970A FI803970A FI66608C FI 66608 C FI66608 C FI 66608C FI 803970 A FI803970 A FI 803970A FI 803970 A FI803970 A FI 803970A FI 66608 C FI66608 C FI 66608C
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- Finland
- Prior art keywords
- group
- alkyl group
- formula
- carbon atoms
- amino
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 7
- 230000000144 pharmacologic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- -1 piperidino, 4-amino-piperidino Chemical group 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
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- 238000002360 preparation method Methods 0.000 claims description 7
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- KGBXHAVIEYXXRU-UHFFFAOYSA-N 2h-thiopyran 1-oxide Chemical compound O=S1CC=CC=C1 KGBXHAVIEYXXRU-UHFFFAOYSA-N 0.000 claims description 3
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
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- 231100000252 nontoxic Toxicity 0.000 abstract 1
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- 238000002474 experimental method Methods 0.000 description 13
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- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 5
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- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
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- 238000002347 injection Methods 0.000 description 3
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- 239000001632 sodium acetate Substances 0.000 description 3
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- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
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- 241000699670 Mus sp. Species 0.000 description 2
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
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- WUKZPHOXUVCQOR-UHFFFAOYSA-N N-(1-azabicyclo[2.2.2]octan-3-yl)-6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C1=CC(Cl)=CC2=C1OCC(=O)N2C WUKZPHOXUVCQOR-UHFFFAOYSA-N 0.000 description 1
- COEMQDNLCXIKAO-UHFFFAOYSA-N N-(oxan-2-ylidene)hydroxylamine Chemical class O1C(CCCC1)=NO COEMQDNLCXIKAO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
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- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- IRYSOHKKWIRVLX-UHFFFAOYSA-N dimethylamino formate Chemical compound CN(C)OC=O IRYSOHKKWIRVLX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
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- 239000000174 gluconic acid Substances 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- 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
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- 229960003147 reserpine Drugs 0.000 description 1
- 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 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2951634 | 1979-12-21 | ||
| DE19792951634 DE2951634A1 (de) | 1979-12-21 | 1979-12-21 | Neue substituierte 4-amino-2,6-diaryl-tetrahydrothiopyrane, deren saeureadditionssalze, verfahren zu ihrer herstellung, ihre verwendung und pharmazeutische zusammensetzungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI803970L FI803970L (fi) | 1981-06-22 |
| FI66608B FI66608B (fi) | 1984-07-31 |
| FI66608C true FI66608C (fi) | 1984-11-12 |
Family
ID=6089212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI803970A FI66608C (fi) | 1979-12-21 | 1980-12-19 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-amino-2,6-diaryl-tetrahydrotiopyraner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4297354A (en, 2012) |
| EP (1) | EP0031456B1 (en, 2012) |
| JP (1) | JPS5699473A (en, 2012) |
| AT (1) | ATE7141T1 (en, 2012) |
| AU (1) | AU537086B2 (en, 2012) |
| CA (1) | CA1142925A (en, 2012) |
| DE (2) | DE2951634A1 (en, 2012) |
| DK (1) | DK537180A (en, 2012) |
| ES (1) | ES497949A0 (en, 2012) |
| FI (1) | FI66608C (en, 2012) |
| GR (1) | GR72839B (en, 2012) |
| IL (1) | IL61771A (en, 2012) |
| NO (1) | NO151934C (en, 2012) |
| NZ (1) | NZ195889A (en, 2012) |
| PH (1) | PH15866A (en, 2012) |
| PT (1) | PT72255B (en, 2012) |
| ZA (1) | ZA807952B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310551B1 (de) * | 1987-09-30 | 1994-01-26 | Ciba-Geigy Ag | Phenolische Thianderivate |
| WO2011033115A2 (en) | 2009-09-18 | 2011-03-24 | Centre National De La Recherche Scientifique | Compounds useful against kinetoplastideae parasites |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419555A (en) * | 1965-10-24 | 1968-12-31 | Robins Co Inc A H | 2-aryl-tetrahydropyran-3-amines |
| US3787442A (en) * | 1973-01-26 | 1974-01-22 | American Home Prod | Tetrahydro-2h-thiopyran-4-sulfamic acids and salts |
-
1979
- 1979-12-21 DE DE19792951634 patent/DE2951634A1/de not_active Withdrawn
-
1980
- 1980-11-22 EP EP80107291A patent/EP0031456B1/de not_active Expired
- 1980-11-22 DE DE8080107291T patent/DE3067580D1/de not_active Expired
- 1980-11-22 AT AT80107291T patent/ATE7141T1/de not_active IP Right Cessation
- 1980-12-05 GR GR63558A patent/GR72839B/el unknown
- 1980-12-15 US US06/216,423 patent/US4297354A/en not_active Expired - Fee Related
- 1980-12-17 DK DK537180A patent/DK537180A/da not_active Application Discontinuation
- 1980-12-18 NO NO803863A patent/NO151934C/no unknown
- 1980-12-18 CA CA000367088A patent/CA1142925A/en not_active Expired
- 1980-12-19 PT PT72255A patent/PT72255B/pt unknown
- 1980-12-19 NZ NZ195889A patent/NZ195889A/xx unknown
- 1980-12-19 FI FI803970A patent/FI66608C/fi not_active IP Right Cessation
- 1980-12-19 AU AU65601/80A patent/AU537086B2/en not_active Ceased
- 1980-12-19 JP JP18031280A patent/JPS5699473A/ja active Pending
- 1980-12-19 IL IL61771A patent/IL61771A/xx unknown
- 1980-12-19 ES ES497949A patent/ES497949A0/es active Granted
- 1980-12-19 ZA ZA00807952A patent/ZA807952B/xx unknown
- 1980-12-21 PH PH25044A patent/PH15866A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ195889A (en) | 1983-09-02 |
| ATE7141T1 (de) | 1984-05-15 |
| NO803863L (no) | 1981-06-22 |
| NO151934B (no) | 1985-03-25 |
| IL61771A0 (en) | 1981-01-30 |
| AU6560180A (en) | 1981-06-25 |
| PH15866A (en) | 1983-04-13 |
| GR72839B (en, 2012) | 1983-12-07 |
| PT72255B (de) | 1982-07-13 |
| FI803970L (fi) | 1981-06-22 |
| ES8202552A1 (es) | 1982-02-01 |
| EP0031456B1 (de) | 1984-04-18 |
| JPS5699473A (en) | 1981-08-10 |
| ES497949A0 (es) | 1982-02-01 |
| DK537180A (da) | 1981-06-22 |
| DE3067580D1 (en) | 1984-05-24 |
| US4297354A (en) | 1981-10-27 |
| FI66608B (fi) | 1984-07-31 |
| ZA807952B (en) | 1982-08-25 |
| EP0031456A1 (de) | 1981-07-08 |
| NO151934C (no) | 1985-07-03 |
| AU537086B2 (en) | 1984-06-07 |
| DE2951634A1 (de) | 1981-07-16 |
| PT72255A (de) | 1981-01-01 |
| CA1142925A (en) | 1983-03-15 |
| IL61771A (en) | 1984-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |