KR910005413B1 - N-(3-트리플루오로메틸페닐)-n'-프로파르길피페라진의 제조방법 - Google Patents
N-(3-트리플루오로메틸페닐)-n'-프로파르길피페라진의 제조방법Info
- Publication number
- KR910005413B1 KR910005413B1 KR1019840000990A KR840000990A KR910005413B1 KR 910005413 B1 KR910005413 B1 KR 910005413B1 KR 1019840000990 A KR1019840000990 A KR 1019840000990A KR 840000990 A KR840000990 A KR 840000990A KR 910005413 B1 KR910005413 B1 KR 910005413B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- reaction
- trifluoromethylphenyl
- preparing
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 10
- NMPULLSOELSTKH-UHFFFAOYSA-N 1-prop-2-ynyl-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC#C)CC2)=C1 NMPULLSOELSTKH-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 5
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 45
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- -1 aliphatic alcohols Chemical class 0.000 description 10
- GNIRDOTZBWPMDC-UHFFFAOYSA-N 1-prop-2-ynyl-4-[3-(trifluoromethyl)phenyl]piperazine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(N2CCN(CC#C)CC2)=C1 GNIRDOTZBWPMDC-UHFFFAOYSA-N 0.000 description 9
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- 238000002156 mixing Methods 0.000 description 3
- OSHHZWUXDGIOMU-UHFFFAOYSA-N n-prop-2-ynyl-n'-[3-(trifluoromethyl)phenyl]ethane-1,2-diamine Chemical compound FC(F)(F)C1=CC=CC(NCCNCC#C)=C1 OSHHZWUXDGIOMU-UHFFFAOYSA-N 0.000 description 3
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- 238000013268 sustained release Methods 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MLBPNWVQOPKDCP-UHFFFAOYSA-N 1-prop-2-ynyl-4-[3-(trifluoromethyl)phenyl]piperazine-2,6-dione Chemical compound FC(F)(F)C1=CC=CC(N2CC(=O)N(CC#C)C(=O)C2)=C1 MLBPNWVQOPKDCP-UHFFFAOYSA-N 0.000 description 2
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- KCTGXSMQMWGHRN-UHFFFAOYSA-N CCCN(CCNc1cccc(C(F)(F)F)c1)CC#C Chemical compound CCCN(CCNc1cccc(C(F)(F)F)c1)CC#C KCTGXSMQMWGHRN-UHFFFAOYSA-N 0.000 description 2
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- NCTGNZUKELLCHB-UHFFFAOYSA-N 1-prop-2-ynyl-4-[3-(trifluoromethyl)phenyl]piperazine-2,3-dione Chemical compound FC(F)(F)C1=CC=CC(N2C(C(=O)N(CC#C)CC2)=O)=C1 NCTGNZUKELLCHB-UHFFFAOYSA-N 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- YDXJGZFAWVMHNA-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(N(CCCl)CCCl)=C1 YDXJGZFAWVMHNA-UHFFFAOYSA-N 0.000 description 1
- VMKZAWDPUXUQAN-UHFFFAOYSA-N n,n-bis(2-chloroethyl)prop-2-yn-1-amine Chemical compound ClCCN(CCCl)CC#C VMKZAWDPUXUQAN-UHFFFAOYSA-N 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000006702 propargylation reaction Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 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
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent 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
- C07D295/02—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
- C07D295/033—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 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
- C07D295/06—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3306964.6 | 1983-02-28 | ||
| DEP3306964.6 | 1983-02-28 | ||
| DE19833306964 DE3306964A1 (de) | 1983-02-28 | 1983-02-28 | Neues n-arylpiperazin und verfahren zu seiner herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840007875A KR840007875A (ko) | 1984-12-11 |
| KR910005413B1 true KR910005413B1 (ko) | 1991-07-29 |
Family
ID=6192038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840000990A Expired KR910005413B1 (ko) | 1983-02-28 | 1984-02-28 | N-(3-트리플루오로메틸페닐)-n'-프로파르길피페라진의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4699910A (enExample) |
| EP (1) | EP0117531B1 (enExample) |
| JP (1) | JPS59210074A (enExample) |
| KR (1) | KR910005413B1 (enExample) |
| AT (1) | ATE22289T1 (enExample) |
| AU (1) | AU562643B2 (enExample) |
| CA (1) | CA1240327A (enExample) |
| CS (1) | CS240997B2 (enExample) |
| DD (1) | DD218096A5 (enExample) |
| DE (2) | DE3306964A1 (enExample) |
| DK (1) | DK158729C (enExample) |
| ES (7) | ES530073A0 (enExample) |
| FI (1) | FI77658C (enExample) |
| GB (1) | GB2135997B (enExample) |
| GR (1) | GR79822B (enExample) |
| HU (1) | HU190546B (enExample) |
| IE (1) | IE56938B1 (enExample) |
| IL (1) | IL71068A (enExample) |
| NO (1) | NO158803C (enExample) |
| NZ (1) | NZ207289A (enExample) |
| PH (1) | PH21982A (enExample) |
| PL (1) | PL141275B1 (enExample) |
| PT (1) | PT78155B (enExample) |
| SU (1) | SU1223844A3 (enExample) |
| ZA (1) | ZA841418B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03176457A (ja) * | 1989-12-04 | 1991-07-31 | Nippon Paint Co Ltd | 新規プロパルギル化合物、その製法ならびに該化合物を含む被覆材 |
| JPH05255089A (ja) * | 1991-12-18 | 1993-10-05 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| US5661163A (en) * | 1995-06-07 | 1997-08-26 | Merck & Co., Inc. | Alpha-1a adrenergic receptor antagonists |
| USRE46117E1 (en) | 1999-12-22 | 2016-08-23 | Teva Pharmaceuticals International Gmbh | Modulators of dopamine neurotransmission |
| JP6177875B2 (ja) | 2012-04-04 | 2017-08-09 | テバ・ファーマシューティカルズ・インターナショナル・ゲーエムベーハーＴｅｖａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ ＧｍｂＨ | 併用療法のための医薬組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993899A (en) * | 1958-03-31 | 1961-07-25 | Miles Lab | Acetylenically unsaturated piperazine derivatives |
| NL6607959A (enExample) * | 1965-06-10 | 1966-12-12 | ||
| DE1545561A1 (de) * | 1965-08-23 | 1969-12-11 | Acraf | Verfahren zur Herstellung von pharmakologisch aktiven N,N-disubstituierten 1-Aryl-3-aminopropinen |
| FR2187311B1 (enExample) * | 1972-06-02 | 1975-06-20 | Bouchara Emile | |
| GB1560271A (en) * | 1977-01-14 | 1980-02-06 | Joullie International Sa | Therapeutically useful m-trifluoromethylphenylpiperazine derivatives |
| US4180574A (en) * | 1978-12-26 | 1979-12-25 | Abbott Laboratories | Certain ovicidal piperazines |
| US4518712A (en) * | 1980-06-30 | 1985-05-21 | Taiho Pharmaceutical Company Limited | Piperazine derivative and analgesic composition containing the same |
-
1983
- 1983-02-28 DE DE19833306964 patent/DE3306964A1/de not_active Withdrawn
-
1984
- 1984-02-23 AT AT84101894T patent/ATE22289T1/de active
- 1984-02-23 DE DE8484101894T patent/DE3460733D1/de not_active Expired
- 1984-02-23 FI FI840743A patent/FI77658C/fi not_active IP Right Cessation
- 1984-02-23 GR GR73907A patent/GR79822B/el unknown
- 1984-02-23 EP EP84101894A patent/EP0117531B1/de not_active Expired
- 1984-02-23 CS CS841274A patent/CS240997B2/cs unknown
- 1984-02-24 DK DK102084A patent/DK158729C/da not_active IP Right Cessation
- 1984-02-24 DD DD84260319A patent/DD218096A5/de not_active IP Right Cessation
- 1984-02-27 PT PT78155A patent/PT78155B/pt not_active IP Right Cessation
- 1984-02-27 AU AU25085/84A patent/AU562643B2/en not_active Ceased
- 1984-02-27 ES ES530073A patent/ES530073A0/es active Granted
- 1984-02-27 IE IE460/84A patent/IE56938B1/en not_active IP Right Cessation
- 1984-02-27 SU SU843706206A patent/SU1223844A3/ru active
- 1984-02-27 CA CA000448370A patent/CA1240327A/en not_active Expired
- 1984-02-27 NO NO840732A patent/NO158803C/no unknown
- 1984-02-27 HU HU84771A patent/HU190546B/hu not_active IP Right Cessation
- 1984-02-27 JP JP59035872A patent/JPS59210074A/ja active Granted
- 1984-02-27 PH PH30304A patent/PH21982A/en unknown
- 1984-02-27 PL PL1984246418A patent/PL141275B1/pl unknown
- 1984-02-27 NZ NZ207289A patent/NZ207289A/en unknown
- 1984-02-27 IL IL71068A patent/IL71068A/xx unknown
- 1984-02-27 ZA ZA841418A patent/ZA841418B/xx unknown
- 1984-02-28 GB GB08405113A patent/GB2135997B/en not_active Expired
- 1984-02-28 KR KR1019840000990A patent/KR910005413B1/ko not_active Expired
- 1984-10-01 ES ES536412A patent/ES536412A0/es active Granted
- 1984-10-01 ES ES536411A patent/ES536411A0/es active Granted
- 1984-10-01 ES ES536416A patent/ES8603447A1/es not_active Expired
- 1984-10-01 ES ES536414A patent/ES8603445A1/es not_active Expired
- 1984-10-01 ES ES536415A patent/ES8603446A1/es not_active Expired
- 1984-10-01 ES ES536413A patent/ES536413A0/es active Granted
-
1985
- 1985-11-22 US US06/800,525 patent/US4699910A/en not_active Expired - Fee Related
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Patent event code: PA02012R01D Patent event date: 19890224 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19840228 Comment text: Patent Application |
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Comment text: Notification of reason for refusal Patent event date: 19910128 Patent event code: PE09021S01D |
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Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19910629 |
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