SU751324A3 - Способ получени 4-хиназолинил -аралкилпиперидинов - Google Patents
Способ получени 4-хиназолинил -аралкилпиперидинов Download PDFInfo
- Publication number
- SU751324A3 SU751324A3 SU782674601A SU2674601A SU751324A3 SU 751324 A3 SU751324 A3 SU 751324A3 SU 782674601 A SU782674601 A SU 782674601A SU 2674601 A SU2674601 A SU 2674601A SU 751324 A3 SU751324 A3 SU 751324A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- aralkylpiperidines
- oxo
- indicated meanings
- piperidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- -1 4-oxoquinazolinyl Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000006264 debenzylation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- MSKAVXYLXIUCJP-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1OCCBr MSKAVXYLXIUCJP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29317/76A GB1583753A (en) | 1976-07-14 | 1976-07-14 | Piperidine derivatives processes for their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU751324A3 true SU751324A3 (ru) | 1980-07-23 |
Family
ID=10289639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782674601A SU751324A3 (ru) | 1976-07-14 | 1978-10-17 | Способ получени 4-хиназолинил -аралкилпиперидинов |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4166117A (enExample) |
| JP (1) | JPS5334784A (enExample) |
| BE (1) | BE856784A (enExample) |
| CA (1) | CA1103671A (enExample) |
| CH (1) | CH625518A5 (enExample) |
| DE (1) | DE2731299A1 (enExample) |
| ES (2) | ES460699A1 (enExample) |
| FR (1) | FR2361385A1 (enExample) |
| GB (1) | GB1583753A (enExample) |
| NL (1) | NL7707785A (enExample) |
| OA (1) | OA05707A (enExample) |
| SU (1) | SU751324A3 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029707B1 (en) * | 1979-11-21 | 1984-02-01 | Kyowa Hakko Kogyo Co., Ltd | Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them |
| US4344945A (en) * | 1980-03-10 | 1982-08-17 | Kyowa Hakko Kogyo Co., Ltd. | Piperidine derivatives |
| US4684654A (en) * | 1985-08-14 | 1987-08-04 | American Cyanamid Company | 3-heteroalkyl-2,4-quinzaolinediones |
| PH23565A (en) * | 1986-09-05 | 1989-08-25 | Sumitomo Chemical Co | Novel pyrimidinylpyrimidine derivatives and a plant disease protectant containing them as the active ingredient |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| CA2118117A1 (en) * | 1993-02-18 | 1994-08-19 | Shigeki Fujiwara | Adenosine uptake inhibitor |
| JP2959765B2 (ja) * | 1997-12-12 | 1999-10-06 | 日本たばこ産業株式会社 | ３−ピペリジル−４−オキソキナゾリン誘導体及びそれを含有してなる医薬組成物 |
| US6258819B1 (en) * | 1999-08-05 | 2001-07-10 | Syntex (U.S.A.) Llc | Substituted 2(4-piperidyl)-4(3H)-quinazolinones and 2-(4-piperidyl)-4(3H)-azaquinazolinones |
| CA2555824C (en) * | 2004-02-13 | 2011-06-07 | Banyu Pharmaceutical Co., Ltd. | Fused-ring 4-oxopyrimidine derivative |
| CL2008000252A1 (es) * | 2007-01-29 | 2008-03-14 | Xenon Pharmaceuticals Inc | Compuestos derivados de quinazolinona o pirimidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar enfermedades mediadas por los canales de calcio, tales como dolor, depresion, enfermedades cardiovasculares, respir |
| WO2014102592A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Oxime/substituted quinoxaline-type piperidine compounds and uses thereof |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| CA2996857C (en) | 2015-09-23 | 2024-05-21 | Janssen Pharmaceutica Nv | Quinoxaline, quinoline and quinazolinone derivative compounds for the treatment of cancer |
| EP3353164B1 (en) | 2015-09-23 | 2021-11-03 | Janssen Pharmaceutica, N.V. | Bi-heteroaryl substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694711A (en) * | 1952-12-02 | 1954-11-16 | American Cyanamid Co | Quinazolone antimalarial compounds |
| US3086910A (en) * | 1960-03-09 | 1963-04-23 | Wallace & Tiernan Inc | Central nervous system depressants 3-(2'-pyridyl)-4-quinazolones |
| US3257397A (en) * | 1963-07-26 | 1966-06-21 | Rexall Drug Chemical | Substituted 2, 3-dihydro-4(1h)-quinazolinones |
| US4027028A (en) * | 1975-11-10 | 1977-05-31 | Science Union Et Cie | Arylethers and pharmaceutical compositions |
-
1976
- 1976-07-14 GB GB29317/76A patent/GB1583753A/en not_active Expired
-
1977
- 1977-07-08 FR FR7721035A patent/FR2361385A1/fr active Granted
- 1977-07-11 DE DE19772731299 patent/DE2731299A1/de not_active Withdrawn
- 1977-07-11 US US05/814,482 patent/US4166117A/en not_active Expired - Lifetime
- 1977-07-12 OA OA56223A patent/OA05707A/xx unknown
- 1977-07-13 BE BE179318A patent/BE856784A/xx unknown
- 1977-07-13 CA CA282,619A patent/CA1103671A/fr not_active Expired
- 1977-07-13 ES ES460699A patent/ES460699A1/es not_active Expired
- 1977-07-13 NL NL7707785A patent/NL7707785A/xx not_active Application Discontinuation
- 1977-07-13 JP JP8402477A patent/JPS5334784A/ja active Pending
- 1977-07-14 CH CH872877A patent/CH625518A5/fr not_active IP Right Cessation
-
1978
- 1978-08-14 ES ES472563A patent/ES472563A1/es not_active Expired
- 1978-10-17 SU SU782674601A patent/SU751324A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1583753A (en) | 1981-02-04 |
| BE856784A (fr) | 1978-01-13 |
| DE2731299A1 (de) | 1978-01-19 |
| JPS5334784A (en) | 1978-03-31 |
| ES472563A1 (es) | 1979-10-16 |
| FR2361385A1 (fr) | 1978-03-10 |
| US4166117A (en) | 1979-08-28 |
| FR2361385B1 (enExample) | 1983-10-07 |
| NL7707785A (nl) | 1978-01-17 |
| CA1103671A (fr) | 1981-06-23 |
| CH625518A5 (enExample) | 1981-09-30 |
| ES460699A1 (es) | 1978-12-01 |
| OA05707A (fr) | 1981-05-31 |
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