DE1595983A1 - Herstellungsverfahren neuer Derivate der Reihe von Phenylpiperazinen - Google Patents
Herstellungsverfahren neuer Derivate der Reihe von PhenylpiperazinenInfo
- Publication number
- DE1595983A1 DE1595983A1 DE19661595983 DE1595983A DE1595983A1 DE 1595983 A1 DE1595983 A1 DE 1595983A1 DE 19661595983 DE19661595983 DE 19661595983 DE 1595983 A DE1595983 A DE 1595983A DE 1595983 A1 DE1595983 A1 DE 1595983A1
- Authority
- DE
- Germany
- Prior art keywords
- effect
- radical
- phenylpiperazines
- series
- manufacturing process
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000001387 anti-histamine Effects 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000000701 neuroleptic effect Effects 0.000 claims description 4
- 230000001624 sedative effect Effects 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000000932 sedative agent Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 206010007776 catatonia Diseases 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- AUYNWRLEXAPZAJ-UHFFFAOYSA-N piperazine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CNCCN1 AUYNWRLEXAPZAJ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D295/04—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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9982/65A GB1096341A (en) | 1965-03-09 | 1965-03-09 | Novel derivatives of the phenyl-piperazine series and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1595983A1 true DE1595983A1 (de) | 1969-12-11 |
Family
ID=9882358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595983 Pending DE1595983A1 (de) | 1965-03-09 | 1966-02-16 | Herstellungsverfahren neuer Derivate der Reihe von Phenylpiperazinen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE676335A (enrdf_load_stackoverflow) |
| CH (1) | CH456607A (enrdf_load_stackoverflow) |
| DE (1) | DE1595983A1 (enrdf_load_stackoverflow) |
| ES (1) | ES323533A1 (enrdf_load_stackoverflow) |
| FR (1) | FR5330M (enrdf_load_stackoverflow) |
| GB (1) | GB1096341A (enrdf_load_stackoverflow) |
| NL (1) | NL6602928A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993003025A1 (fr) * | 1991-08-09 | 1993-02-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de thiophene |
| ES2128266B1 (es) | 1997-07-08 | 2000-01-16 | Vita Invest Sa | Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes. |
-
1965
- 1965-03-09 GB GB9982/65A patent/GB1096341A/en not_active Expired
-
1966
- 1966-02-09 FR FR48948A patent/FR5330M/fr not_active Expired
- 1966-02-11 BE BE676335D patent/BE676335A/xx unknown
- 1966-02-16 DE DE19661595983 patent/DE1595983A1/de active Pending
- 1966-02-25 ES ES0323533A patent/ES323533A1/es not_active Expired
- 1966-02-28 CH CH286366A patent/CH456607A/fr unknown
- 1966-03-07 NL NL6602928A patent/NL6602928A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE676335A (enrdf_load_stackoverflow) | 1966-06-16 |
| NL6602928A (enrdf_load_stackoverflow) | 1966-09-12 |
| ES323533A1 (es) | 1967-01-01 |
| CH456607A (fr) | 1968-07-31 |
| GB1096341A (en) | 1967-12-29 |
| FR5330M (enrdf_load_stackoverflow) | 1967-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3005948C2 (enrdf_load_stackoverflow) | ||
| DE1445425A1 (de) | Verfahren zur Herstellung von Piperazinderivaten | |
| DE2162744C3 (de) | N,N-Disubstituierte α -Aminocarbonsäure-(2',6'-xylidide) und diese Verbindungen enthaltende lokalanästhetische Mittel | |
| DE2016667B2 (de) | 4-(diphenylmethylen)-piperidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2555590A1 (de) | 1-substituierte-4-benzylidenpiperidine und verfahren zu ihrer herstellung | |
| DE2733291A1 (de) | (3-amino-5-substituiert-6-fluorpyrazinoyl- oder -pyrazinamido)-guanidine und ihre an den guanidino-stickstoffatomen substituierten derivate | |
| DE2126559C3 (de) | 2,2-Diaryl-4-piperidinbutyramide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1595984A1 (de) | Verfahren zur Herstellung neuer substituierter Piperazine | |
| DE1595983A1 (de) | Herstellungsverfahren neuer Derivate der Reihe von Phenylpiperazinen | |
| DE1793386A1 (de) | Flavonverbindungen und Verfahren zu ihrer Herstellung | |
| DE2107871C3 (enrdf_load_stackoverflow) | ||
| AT265277B (de) | Verfahren zur Herstellung von Phenylpiperazinen und von deren Säureadditionssalzen | |
| DE1470224B2 (de) | In 1-stellung substituierte 4- aminopiperazinderivate | |
| DE1217396B (de) | Verfahren zur Herstellung von 1 - (Thienyl-21) - l-oxo-2-amino-propanen | |
| DE1493922A1 (de) | Camarinderivate und Verfahren zu deren Herstellung | |
| CH398595A (de) | Verfahren zur Herstellung von Indolderivaten | |
| DE1620229A1 (de) | Verfahren zur Herstellung von Chinolinverbindungen | |
| DE1695559C3 (de) | N-(2-Pyridyl)-aminoalkane und Verfahren zu ihrer Herstellung. Ausscheidung aus: 1420056 | |
| DE2439461A1 (de) | Alpha-cyanamin-verbindungen, verfahren zur herstellung derselben und mittel mit einem gehalt derselben | |
| DE1934966A1 (de) | Neue 2-Methyl-3-benzyl-3H(4,5-b)-imidazopyridine und Verfahren zu ihrer Herstellung | |
| AT265278B (de) | Verfahren zur Herstellung neuer, substituierter Piperazine sowie deren Säureadditionssalze | |
| DE1645947A1 (de) | Verfahren zur Herstellung von Derivaten des s-Triazolo-[4,3-a]-pyridins | |
| DE1695431C3 (de) | Piperazinderivate, Verfahren zu deren Herstellung und diese enthaltende therapeutische Zubereitungen | |
| DE1283242B (de) | Verfahren zur Herstellung von disubstituierten Isoxazol-Verbindungen und deren nichttoxischen Salzen | |
| DE1695765B2 (de) | In 1-stellung n-heterocyclisch substituierte derivate des propan-2,3diols |