SE448728B - 4-(naftalenyloxi)piperidin-derivat och en farmaceutisk komposition med antipsykotisk verkan - Google Patents
4-(naftalenyloxi)piperidin-derivat och en farmaceutisk komposition med antipsykotisk verkanInfo
- Publication number
- SE448728B SE448728B SE8005493A SE8005493A SE448728B SE 448728 B SE448728 B SE 448728B SE 8005493 A SE8005493 A SE 8005493A SE 8005493 A SE8005493 A SE 8005493A SE 448728 B SE448728 B SE 448728B
- Authority
- SE
- Sweden
- Prior art keywords
- naphthalenyloxy
- piperidine
- formula
- acid
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 17
- 230000000694 effects Effects 0.000 title description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 78
- -1 hydroxymethylene Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 230000000561 anti-psychotic effect Effects 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 28
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 208000024891 symptom Diseases 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6430579A | 1979-08-06 | 1979-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8005493L SE8005493L (sv) | 1981-02-07 |
| SE448728B true SE448728B (sv) | 1987-03-16 |
Family
ID=22055014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8005493A SE448728B (sv) | 1979-08-06 | 1980-07-31 | 4-(naftalenyloxi)piperidin-derivat och en farmaceutisk komposition med antipsykotisk verkan |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5626875A (en16) |
| AU (1) | AU534398B2 (en16) |
| BE (1) | BE884581A (en16) |
| CA (1) | CA1123440A (en16) |
| CH (1) | CH644364A5 (en16) |
| DE (1) | DE3028064A1 (en16) |
| DK (1) | DK150477C (en16) |
| ES (1) | ES493591A0 (en16) |
| FR (1) | FR2463129A1 (en16) |
| GB (1) | GB2056447B (en16) |
| IE (1) | IE49998B1 (en16) |
| IL (1) | IL60593A (en16) |
| IT (1) | IT1146966B (en16) |
| NL (1) | NL8004147A (en16) |
| NO (1) | NO153726C (en16) |
| NZ (1) | NZ194248A (en16) |
| SE (1) | SE448728B (en16) |
| ZA (1) | ZA804112B (en16) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508445A1 (fr) * | 1981-06-29 | 1982-12-31 | Sori Soc Rech Ind | Nouveaux derives de benzoyl-phenyl-piperidine, leur procede de preparation et leur application, notamment en therapeutique |
| DE3170628D1 (en) * | 1981-10-15 | 1985-06-27 | Synthelabo | Piperidine derivatives, their preparation and use in medicine |
| GB8321157D0 (en) * | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
| JP2751346B2 (ja) * | 1989-03-15 | 1998-05-18 | ミノルタ株式会社 | プリンタ |
| EP2358677B1 (en) * | 2008-11-17 | 2014-01-08 | F. Hoffmann-La Roche AG | Naphthylacetic acids used as crth2 antagonists or partial agonists |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB895309A (en) * | 1959-11-18 | 1962-05-02 | Res Lab Dr C Janssen Nv | Pyrrolidine and piperidine derivatives |
| BE637978A (en16) * | 1963-02-15 | |||
| US3743645A (en) * | 1970-10-19 | 1973-07-03 | Robins Co Inc A H | 1-substituted-4-phenoxypiperidines |
| ZA717147B (en) * | 1970-11-27 | 1972-07-26 | Richardson Merrell Inc | 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives |
| US3806526A (en) * | 1972-01-28 | 1974-04-23 | Richardson Merrell Inc | 1-aroylalkyl-4-diphenylmethyl piperidines |
| SE7409245L (en16) * | 1973-07-19 | 1975-01-20 | Robins Co Inc A H | |
| DE2718405A1 (de) * | 1977-04-26 | 1978-11-02 | Boehringer Sohn Ingelheim | Neue n- eckige klammer auf 1-(3-benzoylpropyl)-4-piperidyl eckige klammer zu -sulfonsaeureamide und verfahren zu deren herstellung |
| US4134982A (en) * | 1977-09-26 | 1979-01-16 | Warner-Lambert Company | Antipsychotic 1-[4,4-Bis(4-fluorophenyl) butyl]-4-phenoxy-1,2,3,6-tetrahydropyridines |
-
1980
- 1980-07-01 IE IE1382/80A patent/IE49998B1/en not_active IP Right Cessation
- 1980-07-03 CA CA355,369A patent/CA1123440A/en not_active Expired
- 1980-07-04 NZ NZ194248A patent/NZ194248A/en unknown
- 1980-07-08 ZA ZA00804112A patent/ZA804112B/xx unknown
- 1980-07-14 AU AU60394/80A patent/AU534398B2/en not_active Ceased
- 1980-07-15 IL IL60593A patent/IL60593A/xx unknown
- 1980-07-18 NL NL8004147A patent/NL8004147A/nl not_active Application Discontinuation
- 1980-07-22 ES ES493591A patent/ES493591A0/es active Granted
- 1980-07-24 DE DE19803028064 patent/DE3028064A1/de active Granted
- 1980-07-31 BE BE0/201611A patent/BE884581A/fr not_active IP Right Cessation
- 1980-07-31 IT IT49394/80A patent/IT1146966B/it active
- 1980-07-31 SE SE8005493A patent/SE448728B/sv not_active IP Right Cessation
- 1980-08-01 JP JP10521180A patent/JPS5626875A/ja active Granted
- 1980-08-01 GB GB8025192A patent/GB2056447B/en not_active Expired
- 1980-08-04 CH CH590380A patent/CH644364A5/de not_active IP Right Cessation
- 1980-08-05 DK DK337280A patent/DK150477C/da active
- 1980-08-05 FR FR8017290A patent/FR2463129A1/fr active Granted
- 1980-08-05 NO NO802346A patent/NO153726C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8105981A1 (es) | 1981-07-01 |
| CA1123440A (en) | 1982-05-11 |
| NZ194248A (en) | 1984-07-06 |
| IL60593A (en) | 1984-03-30 |
| IT8049394A0 (it) | 1980-07-31 |
| ZA804112B (en) | 1981-07-29 |
| DE3028064C2 (en16) | 1989-11-09 |
| ES493591A0 (es) | 1981-07-01 |
| IE49998B1 (en) | 1986-01-22 |
| DK150477C (da) | 1987-10-12 |
| FR2463129A1 (fr) | 1981-02-20 |
| SE8005493L (sv) | 1981-02-07 |
| NO153726B (no) | 1986-02-03 |
| DK337280A (da) | 1981-02-07 |
| NO802346L (no) | 1981-02-09 |
| NL8004147A (nl) | 1981-02-10 |
| JPS5626875A (en) | 1981-03-16 |
| DE3028064A1 (de) | 1981-02-26 |
| JPS6341390B2 (en16) | 1988-08-17 |
| AU6039480A (en) | 1981-02-12 |
| IT1146966B (it) | 1986-11-19 |
| GB2056447B (en) | 1983-07-06 |
| IE801382L (en) | 1981-02-06 |
| GB2056447A (en) | 1981-03-18 |
| DK150477B (da) | 1987-03-09 |
| AU534398B2 (en) | 1984-01-26 |
| BE884581A (fr) | 1980-11-17 |
| FR2463129B1 (en16) | 1983-04-22 |
| IL60593A0 (en) | 1980-09-16 |
| CH644364A5 (de) | 1984-07-31 |
| NO153726C (no) | 1986-05-14 |
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