BE826339A - Derives de 1-(3-phenylpropyl)-4-furoylpiperazine - Google Patents
Derives de 1-(3-phenylpropyl)-4-furoylpiperazineInfo
- Publication number
- BE826339A BE826339A BE2054189A BE2054189A BE826339A BE 826339 A BE826339 A BE 826339A BE 2054189 A BE2054189 A BE 2054189A BE 2054189 A BE2054189 A BE 2054189A BE 826339 A BE826339 A BE 826339A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- phenylpropyl
- furoyl
- piperazine
- methyl
- Prior art date
Links
- GGHWLRIOGLYBBG-UHFFFAOYSA-N furan-2-yl-[4-(3-phenylpropyl)piperazin-1-yl]methanone Chemical class C=1C=COC=1C(=O)N(CC1)CCN1CCCC1=CC=CC=C1 GGHWLRIOGLYBBG-UHFFFAOYSA-N 0.000 title claims description 7
- -1 3-furoyl Chemical group 0.000 claims description 15
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- RYVSAYCLHBLJEU-UHFFFAOYSA-N (2,5-dimethylpiperazin-1-yl)-(furan-2-yl)methanone Chemical compound CC1CNC(C)CN1C(=O)C1=CC=CO1 RYVSAYCLHBLJEU-UHFFFAOYSA-N 0.000 claims 1
- CIFGWTBVHGSNMD-UHFFFAOYSA-N furan-2-yl-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CO1 CIFGWTBVHGSNMD-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 34
- 238000000034 method Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 10
- LOJCUYCKDGYLJH-UHFFFAOYSA-N 1-(3-phenylpropyl)piperazine Chemical class C=1C=CC=CC=1CCCN1CCNCC1 LOJCUYCKDGYLJH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- ZURUVZFDEVKNCE-UHFFFAOYSA-N 5-methylfuran-2-carbonyl chloride Chemical compound CC1=CC=C(C(Cl)=O)O1 ZURUVZFDEVKNCE-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 2
- 206010038678 Respiratory depression Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- FDFHXOBSRWLXKB-UHFFFAOYSA-N (2-methylfuran-3-yl)-[4-(3-phenylpropyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.O1C=CC(C(=O)N2CCN(CCCC=3C=CC=CC=3)CC2)=C1C FDFHXOBSRWLXKB-UHFFFAOYSA-N 0.000 description 1
- LYOCJKQNXTWUNI-UHFFFAOYSA-N (2-methylfuran-3-yl)-piperazin-1-ylmethanone Chemical compound O1C=CC(C(=O)N2CCNCC2)=C1C LYOCJKQNXTWUNI-UHFFFAOYSA-N 0.000 description 1
- QUQFBZJSWFGCAX-KBPBESRZSA-N (2s,3s)-2,3-dimethyl-1-(3-phenylpropyl)piperazine Chemical compound C[C@H]1[C@H](C)NCCN1CCCC1=CC=CC=C1 QUQFBZJSWFGCAX-KBPBESRZSA-N 0.000 description 1
- GFDDXUQTWACMNH-KGLIPLIRSA-N (2s,5r)-2,5-dimethyl-1-(3-phenylpropyl)piperazine Chemical compound C[C@H]1CN[C@H](C)CN1CCCC1=CC=CC=C1 GFDDXUQTWACMNH-KGLIPLIRSA-N 0.000 description 1
- RWORXZHVOUPMMM-UHFFFAOYSA-N 2,5-dimethylfuran-3-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=C(C)O1 RWORXZHVOUPMMM-UHFFFAOYSA-N 0.000 description 1
- AFFZVBHMMXZNKE-UHFFFAOYSA-N 2-methylfuran-3-carbonyl chloride Chemical compound CC=1OC=CC=1C(Cl)=O AFFZVBHMMXZNKE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical class BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
- PGVPSBVPGIEISQ-UHFFFAOYSA-N 3-methyl-1-(3-phenylpropyl)piperazine Chemical compound C1CNC(C)CN1CCCC1=CC=CC=C1 PGVPSBVPGIEISQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OZYUPQUCAUTOBP-QXAKKESOSA-N Levallorphan Chemical compound C([C@H]12)CCC[C@@]11CCN(CC=C)[C@@H]2CC2=CC=C(O)C=C21 OZYUPQUCAUTOBP-QXAKKESOSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZIUYMCFEMJQTRV-MCJVGQIASA-N [(2r,5s)-2,5-dimethyl-4-(3-phenylpropyl)piperazin-1-yl]-(furan-2-yl)methanone;hydrochloride Chemical compound Cl.C([C@@H](C)N(C[C@@H]1C)C(=O)C=2OC=CC=2)N1CCCC1=CC=CC=C1 ZIUYMCFEMJQTRV-MCJVGQIASA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- CRLNTRZMHKNJSR-UHFFFAOYSA-N furan-2-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CO1 CRLNTRZMHKNJSR-UHFFFAOYSA-N 0.000 description 1
- SADPINFEWFPMEA-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCNCC1 SADPINFEWFPMEA-UHFFFAOYSA-N 0.000 description 1
- OTZCZBFZYAYQAW-UHFFFAOYSA-N furan-2-yl-[3-methyl-4-(3-phenylpropyl)piperazin-1-yl]methanone Chemical compound CC1CN(C(=O)C=2OC=CC=2)CCN1CCCC1=CC=CC=C1 OTZCZBFZYAYQAW-UHFFFAOYSA-N 0.000 description 1
- NMGAYRRCHPRLNN-UHFFFAOYSA-N furan-2-yl-[4-(3-phenylpropyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.C=1C=COC=1C(=O)N(CC1)CCN1CCCC1=CC=CC=C1 NMGAYRRCHPRLNN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000263 levallorphan Drugs 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003887 narcotic antagonist Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940124641 pain reliever Drugs 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 239000002904 solvent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2606774A JPS50131974A (en, 2012) | 1974-03-06 | 1974-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE826339A true BE826339A (fr) | 1975-06-30 |
Family
ID=12183327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE2054189A BE826339A (fr) | 1974-03-06 | 1975-03-06 | Derives de 1-(3-phenylpropyl)-4-furoylpiperazine |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS50131974A (en, 2012) |
| BE (1) | BE826339A (en, 2012) |
| ZA (1) | ZA751001B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8304361D0 (sv) * | 1983-08-10 | 1983-08-10 | Ferrosan Ab | Novel 1-acylpiperazine derivatives novel 1-acylpiperazine derivatives |
-
1974
- 1974-03-06 JP JP2606774A patent/JPS50131974A/ja active Pending
-
1975
- 1975-02-18 ZA ZA00751001A patent/ZA751001B/xx unknown
- 1975-03-06 BE BE2054189A patent/BE826339A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA751001B (en) | 1976-01-28 |
| JPS50131974A (en, 2012) | 1975-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: KYORIN SEIYAKU K.K. Effective date: 19920331 |