DE2505002A1 - Beta-naphthylmethyl-4-piperazine, verfahren zu ihrer herstellung und arzneimittel - Google Patents
Beta-naphthylmethyl-4-piperazine, verfahren zu ihrer herstellung und arzneimittelInfo
- Publication number
- DE2505002A1 DE2505002A1 DE19752505002 DE2505002A DE2505002A1 DE 2505002 A1 DE2505002 A1 DE 2505002A1 DE 19752505002 DE19752505002 DE 19752505002 DE 2505002 A DE2505002 A DE 2505002A DE 2505002 A1 DE2505002 A1 DE 2505002A1
- Authority
- DE
- Germany
- Prior art keywords
- piperazine
- acid
- naphthylmethyl
- general formula
- chloromethylnaphthalene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
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- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
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- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 claims description 8
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- 239000002253 acid Substances 0.000 claims description 6
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- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003506 piperazine hexahydrate Drugs 0.000 description 1
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 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
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000276 sedentary effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000008673 vomiting Effects 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US440431A US3919230A (en) | 1974-02-07 | 1974-02-07 | {62 -Naphthylmethyl piperazinyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2505002A1 true DE2505002A1 (de) | 1975-08-14 |
Family
ID=23748733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752505002 Ceased DE2505002A1 (de) | 1974-02-07 | 1975-02-06 | Beta-naphthylmethyl-4-piperazine, verfahren zu ihrer herstellung und arzneimittel |
Country Status (16)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130646A (en) * | 1975-07-25 | 1978-12-19 | E. R. Squibb & Sons, Inc. | 1,2,3,4-Tetrahydro-2-((4-(phenyl)-1-piperazinyl)methyl)-1-naphthalenols and derivatives and analogs thereof |
| JPS52133993A (en) * | 1976-04-29 | 1977-11-09 | Takeda Chem Ind Ltd | 1.2-dihydronaphthalene derivatives and method of preparing the same |
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4620006A (en) * | 1982-08-11 | 1986-10-28 | Eastman Kodak Company | Acid salts of 1-(cyanoalkyl)-4-guanylpiperazines |
| WO2000051547A2 (en) * | 1999-03-03 | 2000-09-08 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| CN107652156B (zh) * | 2017-11-18 | 2023-11-10 | 辽宁科技学院 | 一种β-甲基萘的结晶方法和装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127996C (enrdf_load_stackoverflow) * | 1963-11-19 |
-
1974
- 1974-02-07 US US440431A patent/US3919230A/en not_active Expired - Lifetime
-
1975
- 1975-01-09 ZA ZA00750160A patent/ZA75160B/xx unknown
- 1975-02-03 CA CA219,288A patent/CA1042434A/en not_active Expired
- 1975-02-03 GB GB453675A patent/GB1449802A/en not_active Expired
- 1975-02-03 JP JP50014791A patent/JPS50108278A/ja active Pending
- 1975-02-03 AU AU77840/75A patent/AU501049B2/en not_active Expired
- 1975-02-04 CH CH132675A patent/CH616678A5/de not_active IP Right Cessation
- 1975-02-04 ES ES434433A patent/ES434433A1/es not_active Expired
- 1975-02-04 BE BE153056A patent/BE825178A/xx not_active IP Right Cessation
- 1975-02-04 IL IL46568A patent/IL46568A/xx unknown
- 1975-02-05 NL NL7501362A patent/NL7501362A/xx not_active Application Discontinuation
- 1975-02-05 FR FR7503627A patent/FR2260353B1/fr not_active Expired
- 1975-02-06 DE DE19752505002 patent/DE2505002A1/de not_active Ceased
- 1975-02-06 LU LU71803A patent/LU71803A1/xx unknown
- 1975-02-07 IE IE254/75A patent/IE40593B1/xx unknown
- 1975-02-07 HU HU75SI00001455A patent/HU171352B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU501049B2 (en) | 1979-06-07 |
| JPS50108278A (enrdf_load_stackoverflow) | 1975-08-26 |
| GB1449802A (en) | 1976-09-15 |
| ES434433A1 (es) | 1976-11-16 |
| IL46568A (en) | 1979-01-31 |
| CA1042434A (en) | 1978-11-14 |
| IE40593L (en) | 1975-08-07 |
| HU171352B (hu) | 1977-12-28 |
| AU7784075A (en) | 1976-08-05 |
| FR2260353A1 (enrdf_load_stackoverflow) | 1975-09-05 |
| IL46568A0 (en) | 1975-04-25 |
| CH616678A5 (enrdf_load_stackoverflow) | 1980-04-15 |
| US3919230A (en) | 1975-11-11 |
| IE40593B1 (en) | 1979-07-04 |
| LU71803A1 (enrdf_load_stackoverflow) | 1975-06-24 |
| FR2260353B1 (enrdf_load_stackoverflow) | 1980-01-04 |
| NL7501362A (nl) | 1975-08-11 |
| BE825178A (fr) | 1975-08-04 |
| ZA75160B (en) | 1976-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |