NO124312B - - Google Patents
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- Publication number
- NO124312B NO124312B NO1388/69*[A NO138869A NO124312B NO 124312 B NO124312 B NO 124312B NO 138869 A NO138869 A NO 138869A NO 124312 B NO124312 B NO 124312B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- chain
- radical
- cinnamoyl
- piperazine
- Prior art date
Links
- -1 alkyl radical Chemical class 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003218 coronary vasodilator agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 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
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000004885 piperazines Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KYBCXTTWIOZBNR-UHFFFAOYSA-N 2-piperazin-1-yl-1-pyrrolidin-1-ylethanone Chemical compound C1CCCN1C(=O)CN1CCNCC1 KYBCXTTWIOZBNR-UHFFFAOYSA-N 0.000 description 1
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001426 cardiotropic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QEHKBHWEUPXBCW-UHFFFAOYSA-N nitrogen trichloride Chemical compound ClN(Cl)Cl QEHKBHWEUPXBCW-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB06113/68A GB1218591A (en) | 1968-04-03 | 1968-04-03 | Derivatives of n-(3,4,5-trimethoxy cennamoyl) piperazine and their process of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124312B true NO124312B (de) | 1972-04-04 |
Family
ID=10071423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1388/69*[A NO124312B (de) | 1968-04-03 | 1969-10-03 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3634411A (de) |
| BE (1) | BE730345A (de) |
| BG (1) | BG15397A3 (de) |
| CH (1) | CH498845A (de) |
| CS (1) | CS163733B2 (de) |
| DK (1) | DK123824C (de) |
| FI (1) | FI51190C (de) |
| FR (1) | FR2007372A1 (de) |
| GB (1) | GB1218591A (de) |
| IL (1) | IL31901A (de) |
| IT (1) | IT1036019B (de) |
| LU (1) | LU58316A1 (de) |
| NL (1) | NL147427B (de) |
| NO (1) | NO124312B (de) |
| RO (1) | RO55704A (de) |
| SE (1) | SE351212B (de) |
| YU (1) | YU33015B (de) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2092703A1 (en) * | 1970-06-10 | 1972-01-28 | Delalande Sa | 2-(1-pyrrolidinocarbonylmethyl-piperazin-4-yl) ethyl - 3,4,5-trimethoxy benzoate - having hypotensive and adrenolytic active |
| FR2092902A1 (en) * | 1970-06-30 | 1972-01-28 | Delalande Sa | Substd propiophenone - beta (pyrrolidino carbonylmethyl)-1'-piperazin propiophenones, analgesics, hypotensives adrenolytics, noradrenolytic |
| FR2278340A1 (fr) * | 1974-07-17 | 1976-02-13 | Delalande Sa | Nouveau derive de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, ses sels d'addition d'acides, son procede de preparation et son application en therapeutique |
| GB1473262A (en) * | 1974-11-20 | 1977-05-11 | Delalande Sa | Derivatives of n-3,4,5-trimethoxy cinnamoyl-piperazine their process of preparation and their therapeutic application |
| US4368199A (en) * | 1980-01-21 | 1983-01-11 | Delalande S.A. | Novel derivatives of 3,4,5-trimethoxy cinnamoyl piperazine, their salts, the process for preparing the same and their application in therapeutics |
| JPS5888370A (ja) * | 1981-11-19 | 1983-05-26 | Hokuriku Seiyaku Co Ltd | １−（３，４，５−トリメトキシシンナモイル）−４−アミノカルボニルエチル置換ピペラジン及びホモピペラジン誘導体、及びその製造方法 |
| IT1151104B (it) * | 1982-02-04 | 1986-12-17 | Delalande Sa | Impiego terapeutico di derivati (1-cinnamoil oppure 1-fenetil-carbonil)piperazinici |
| FR2522325B1 (fr) * | 1982-02-26 | 1985-08-09 | Delalande Sa | Nouveaux derives aryliques de la piperazine, de l'homopiperazine et de n,n'-dialkyl diamino-1,2 ethane, leur procede de preparation et leur application en therapeutique |
| FR2552762B1 (fr) * | 1983-09-30 | 1986-07-25 | Delalande Sa | Nouveaux amides piperaziniques et homopiperaziniques derives de l'acide 3,4-dioxymethylene cinnamique, leur procede de preparation et leur application en therapeutique |
| JPS6172773A (ja) * | 1984-09-17 | 1986-04-14 | Terumo Corp | ピペラジン誘導体およびこれを含有する血管拡張剤 |
| US6011035A (en) * | 1998-06-30 | 2000-01-04 | Neuromed Technologies Inc. | Calcium channel blockers |
| AU2003250483A1 (en) | 2002-08-19 | 2004-03-11 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| US20050037063A1 (en) * | 2003-07-21 | 2005-02-17 | Bolton Anthony E. | Combined therapies |
| US20060063803A1 (en) * | 2004-09-23 | 2006-03-23 | Pfizer Inc | 4-Amino substituted-2-substituted-1,2,3,4-tetrahydroquinoline compounds |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| JP5498168B2 (ja) | 2006-12-01 | 2014-05-21 | ブリストル−マイヤーズ スクイブ カンパニー | アテローム性動脈硬化および循環器疾患の治療のためのｃｅｔｐ阻害剤としてのｎ−（（３−ベンジル）−２，２−（ビス−フェニル）−プロパン−１−アミン誘導体 |
| AU2008277796A1 (en) | 2007-07-19 | 2009-01-22 | F. Hoffmann-La Roche Ag | Novel heterocyclyl compounds and their use as chemokine antagonists |
| CN101260092B (zh) * | 2008-04-14 | 2011-07-20 | 罗军 | 马来酸桂哌齐特的制备方法 |
| CN101723918B (zh) * | 2008-10-24 | 2011-08-31 | 重庆医科大学医药研究所 | 马来酸桂哌齐特的制备工艺 |
| CN101531643B (zh) * | 2009-04-13 | 2012-11-14 | 上海理奥生物医药科技有限责任公司 | 一种改进的马来酸桂哌齐特的合成方法 |
| CN102229583B (zh) * | 2011-05-13 | 2013-11-27 | 江苏神龙药业有限公司 | 一种桂哌齐特的合成方法 |
| CN103664830A (zh) * | 2012-09-05 | 2014-03-26 | 凌沛学 | 一种马来酸桂哌齐特改进的合成方法 |
| CN103896878B (zh) * | 2012-12-26 | 2018-02-09 | 江苏万邦生化医药股份有限公司 | 一种桂哌齐特的纯化脱色方法 |
| CN103245734A (zh) * | 2013-01-18 | 2013-08-14 | 沈阳亿灵医药科技有限公司 | 一组控制马来酸桂哌齐特质量的组合物 |
| JP2016516804A (ja) | 2013-04-17 | 2016-06-09 | ファイザー・インク | 心血管疾患を治療するためのｎ−ピペリジン−３−イルベンズアミド誘導体 |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| JOP20210193A1 (ar) | 2019-01-18 | 2023-01-30 | Astrazeneca Ab | مثبطات pcsk9 وطرق استخدامها |
-
1968
- 1968-04-03 GB GB06113/68A patent/GB1218591A/en not_active Expired
-
1969
- 1969-03-24 BE BE730345D patent/BE730345A/xx not_active IP Right Cessation
- 1969-03-25 IL IL31901A patent/IL31901A/xx unknown
- 1969-03-26 CH CH460069A patent/CH498845A/fr not_active IP Right Cessation
- 1969-03-26 LU LU58316D patent/LU58316A1/xx unknown
- 1969-03-31 DK DK176769AA patent/DK123824C/da not_active IP Right Cessation
- 1969-04-01 BG BG011961A patent/BG15397A3/bg unknown
- 1969-04-01 NL NL696905019A patent/NL147427B/xx not_active IP Right Cessation
- 1969-04-01 FR FR6909764A patent/FR2007372A1/fr active Pending
- 1969-04-01 US US812369A patent/US3634411A/en not_active Expired - Lifetime
- 1969-04-02 RO RO59598A patent/RO55704A/ro unknown
- 1969-04-02 SE SE04761/69A patent/SE351212B/xx unknown
- 1969-04-03 YU YU834/69A patent/YU33015B/xx unknown
- 1969-04-03 CS CS2408A patent/CS163733B2/cs unknown
- 1969-04-03 IT IT51301/69A patent/IT1036019B/it active
- 1969-04-03 FI FI690996A patent/FI51190C/fi active
- 1969-10-03 NO NO1388/69*[A patent/NO124312B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS163733B2 (de) | 1975-11-07 |
| FI51190C (fi) | 1976-11-10 |
| IL31901A0 (en) | 1969-05-28 |
| NL6905019A (de) | 1969-10-07 |
| SE351212B (de) | 1972-11-20 |
| GB1218591A (en) | 1971-01-06 |
| YU33015B (en) | 1976-03-31 |
| DK123824B (de) | 1972-08-07 |
| IL31901A (en) | 1972-03-28 |
| DK123824C (da) | 1972-12-18 |
| LU58316A1 (de) | 1969-10-27 |
| NL147427B (nl) | 1975-10-15 |
| BG15397A3 (bg) | 1976-05-26 |
| BE730345A (de) | 1969-09-21 |
| CH498845A (fr) | 1970-11-15 |
| IT1036019B (it) | 1979-10-30 |
| DE1915795A1 (de) | 1970-09-10 |
| DE1915795B2 (de) | 1975-07-03 |
| US3634411A (en) | 1972-01-11 |
| RO55704A (de) | 1974-01-03 |
| FR2007372A1 (de) | 1970-01-09 |
| FI51190B (de) | 1976-08-02 |
| YU83469A (en) | 1975-06-30 |
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