NO863870L - Substituerte 3-(4-fenyl-1-piperazinyl)alkylkinazolin-2,4-(1h,3h)dioner og fremgangsmaate for deres fremstilling. - Google Patents
Substituerte 3-(4-fenyl-1-piperazinyl)alkylkinazolin-2,4-(1h,3h)dioner og fremgangsmaate for deres fremstilling.Info
- Publication number
- NO863870L NO863870L NO863870A NO863870A NO863870L NO 863870 L NO863870 L NO 863870L NO 863870 A NO863870 A NO 863870A NO 863870 A NO863870 A NO 863870A NO 863870 L NO863870 L NO 863870L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- acid
- piperazinyl
- dione
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- -1 4-PHENYL-1-PIPERAZINYL Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- KPIXOGWTOHGKEE-UHFFFAOYSA-N 5,6-dihydroxy-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1h-quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=C(O)C(O)=CC=C3NC2=O)=O)CC1 KPIXOGWTOHGKEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000007787 solid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- 230000004872 arterial blood pressure Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VWWOATOPGXIOKK-UHFFFAOYSA-N piperazine;1h-quinazoline-2,4-dione Chemical class C1CNCCN1.C1=CC=C2C(=O)NC(=O)NC2=C1 VWWOATOPGXIOKK-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/782,241 US4711883A (en) | 1985-09-30 | 1985-09-30 | Substituted 3-(4-phenyl-1-piperazinyl)alkylquinazolin-2,4-(1H,3H) diones, methods of preparation, compositions and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO863870D0 NO863870D0 (no) | 1986-09-29 |
| NO863870L true NO863870L (no) | 1987-03-31 |
Family
ID=25125457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO863870A NO863870L (no) | 1985-09-30 | 1986-09-29 | Substituerte 3-(4-fenyl-1-piperazinyl)alkylkinazolin-2,4-(1h,3h)dioner og fremgangsmaate for deres fremstilling. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4711883A (fr) |
| EP (1) | EP0219259A3 (fr) |
| JP (1) | JPS62111970A (fr) |
| KR (1) | KR870003098A (fr) |
| AU (1) | AU583949B2 (fr) |
| CA (1) | CA1290334C (fr) |
| DK (3) | DK162988C (fr) |
| ES (1) | ES2001809A6 (fr) |
| FI (1) | FI863910A (fr) |
| GR (1) | GR862452B (fr) |
| HU (1) | HUT43590A (fr) |
| IL (1) | IL80184A0 (fr) |
| NO (1) | NO863870L (fr) |
| PT (1) | PT83458B (fr) |
| ZA (1) | ZA867424B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90879A0 (en) * | 1988-09-02 | 1990-02-09 | Janssen Pharmaceutica Nv | 3-piperidinyl-indazole derivatives,their preparation and antihypertensive compositions containing them |
| PL165856B1 (pl) * | 1990-04-24 | 1995-02-28 | Dresden Arzneimittel | Sposób wytwarzania nowych 3-/merkaptoalkilo/-chinazolino-/1 H,3H/-dionów-2,4 PL |
| IE913473A1 (en) * | 1990-10-15 | 1992-04-22 | Fujisawa Pharmaceutical Co | Quinazoline derivatives and their preparation |
| KR100817538B1 (ko) * | 2006-07-05 | 2008-03-27 | 한국화학연구원 | 신규 치환된―１ｈ―퀴나졸린―２,４―디온 유도체, 이의제조방법 및 이를 함유하는 약학적 조성물 |
| WO2010099503A1 (fr) | 2009-02-26 | 2010-09-02 | Reviva Pharmaceuticals, Inc. | Compositions, synthèses et procédés d'utilisation de dérivés de quinazolinedione |
| WO2016023826A1 (fr) * | 2014-08-11 | 2016-02-18 | Hydra Biosciences, Inc. | Dérivés de quinazoline-2,4(1h, 3h)-dione à titre de modulateurs de trcp5 pour le traitement des troubles neuropsychiatriques |
| CN111848528B (zh) * | 2019-04-29 | 2022-03-11 | 北京嘉林药业股份有限公司 | 一种预防和/或治疗癌症的化合物及其制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU612466A (en) * | 1966-05-26 | 1967-11-30 | Miles Laboratories Inc. V | Product and process |
| US3819630A (en) * | 1972-08-21 | 1974-06-25 | R Parcell | 3-(1-piperazinylalkyl)-2,4-quinazolinedione compounds and methods for their production |
| JPS58159480A (ja) * | 1982-03-17 | 1983-09-21 | Chugai Pharmaceut Co Ltd | 新規なフエニルピペラジン誘導体 |
| JPS60222467A (ja) * | 1984-04-17 | 1985-11-07 | Mitsubishi Chem Ind Ltd | キナゾリン誘導体およびそれらの酸付加塩 |
| JPS61161268A (ja) * | 1985-01-08 | 1986-07-21 | Mitsubishi Chem Ind Ltd | フエニルピペラジン誘導体 |
| JPS6187675A (ja) * | 1984-10-05 | 1986-05-06 | Mitsubishi Chem Ind Ltd | キナゾリン誘導体およびその酸付加塩 |
| US4639518A (en) * | 1984-09-24 | 1987-01-27 | Ortho Pharmaceutical Corporation | Substituted quinazolinediones |
-
1985
- 1985-09-30 US US06/782,241 patent/US4711883A/en not_active Expired - Lifetime
-
1986
- 1986-09-26 GR GR862452A patent/GR862452B/el unknown
- 1986-09-27 KR KR1019860008112A patent/KR870003098A/ko not_active Application Discontinuation
- 1986-09-29 AU AU63211/86A patent/AU583949B2/en not_active Ceased
- 1986-09-29 NO NO863870A patent/NO863870L/no unknown
- 1986-09-29 DK DK465086A patent/DK162988C/da active
- 1986-09-29 HU HU864130A patent/HUT43590A/hu unknown
- 1986-09-29 CA CA000519319A patent/CA1290334C/fr not_active Expired - Lifetime
- 1986-09-29 EP EP86307447A patent/EP0219259A3/fr not_active Ceased
- 1986-09-29 PT PT83458A patent/PT83458B/pt unknown
- 1986-09-29 IL IL80184A patent/IL80184A0/xx unknown
- 1986-09-29 FI FI863910A patent/FI863910A/fi not_active IP Right Cessation
- 1986-09-29 ZA ZA867424A patent/ZA867424B/xx unknown
- 1986-09-29 JP JP61228509A patent/JPS62111970A/ja active Pending
- 1986-09-29 ES ES8602281A patent/ES2001809A6/es not_active Expired
-
1991
- 1991-06-10 DK DK109891A patent/DK109891A/da not_active Application Discontinuation
- 1991-06-13 DK DK911135A patent/DK113591D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0219259A2 (fr) | 1987-04-22 |
| DK109891D0 (da) | 1991-06-10 |
| DK162988C (da) | 1992-06-01 |
| GR862452B (en) | 1987-01-27 |
| DK465086A (da) | 1987-03-31 |
| FI863910A (fi) | 1987-03-31 |
| ES2001809A6 (es) | 1988-06-16 |
| AU583949B2 (en) | 1989-05-11 |
| HUT43590A (en) | 1987-11-30 |
| EP0219259A3 (fr) | 1988-01-20 |
| ZA867424B (en) | 1988-04-27 |
| DK113591A (da) | 1991-06-13 |
| NO863870D0 (no) | 1986-09-29 |
| PT83458B (en) | 1988-10-31 |
| DK113591D0 (da) | 1991-06-13 |
| AU6321186A (en) | 1987-04-02 |
| DK162988B (da) | 1992-01-06 |
| CA1290334C (fr) | 1991-10-08 |
| PT83458A (en) | 1986-10-01 |
| IL80184A0 (en) | 1986-12-31 |
| FI863910A0 (fi) | 1986-09-29 |
| DK465086D0 (da) | 1986-09-29 |
| JPS62111970A (ja) | 1987-05-22 |
| KR870003098A (ko) | 1987-04-15 |
| DK109891A (da) | 1991-06-10 |
| US4711883A (en) | 1987-12-08 |
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