DE3013502C2 - [2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel - Google Patents
[2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende ArzneimittelInfo
- Publication number
- DE3013502C2 DE3013502C2 DE3013502A DE3013502A DE3013502C2 DE 3013502 C2 DE3013502 C2 DE 3013502C2 DE 3013502 A DE3013502 A DE 3013502A DE 3013502 A DE3013502 A DE 3013502A DE 3013502 C2 DE3013502 C2 DE 3013502C2
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethyl
- prop
- ylpiperazin
- ester
- acid
- 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
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- 238000000034 method Methods 0.000 title claims description 26
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- 229940126601 medicinal product Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- -1 alkyl radical Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000126 substance Substances 0.000 description 28
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 12
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- 238000001953 recrystallisation Methods 0.000 description 12
- KTZYBQFUJLPFMF-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC(C)=CC(OC(C)(C)C(Cl)=O)=C1 KTZYBQFUJLPFMF-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
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- NKOLBXHNFWSMHI-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC=C(C)C(OC(C)(C)C(Cl)=O)=C1 NKOLBXHNFWSMHI-UHFFFAOYSA-N 0.000 description 3
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- NAABUGJBFBVHMI-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methylpropanoyl chloride Chemical compound CC(C)(C)C1=CC=C(OC(C)(C)C(Cl)=O)C=C1 NAABUGJBFBVHMI-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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- 206010047700 Vomiting Diseases 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- IHAQERCVADRQLM-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(Cl)=C1Cl IHAQERCVADRQLM-UHFFFAOYSA-N 0.000 description 2
- UXDMCAHPVYEHKH-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC=CC(C)=C1OC(C)(C)C(Cl)=O UXDMCAHPVYEHKH-UHFFFAOYSA-N 0.000 description 2
- MINZYOMFMKWNIN-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methylpropanoic acid Chemical compound CC(C)(C)C1=CC=C(OC(C)(C)C(O)=O)C=C1 MINZYOMFMKWNIN-UHFFFAOYSA-N 0.000 description 2
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79GO1442A HU179190B (en) | 1979-04-06 | 1979-04-06 | Process for preparing new phenthiazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3013502A1 DE3013502A1 (de) | 1980-10-16 |
| DE3013502C2 true DE3013502C2 (de) | 1985-02-07 |
Family
ID=10996889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3013502A Expired DE3013502C2 (de) | 1979-04-06 | 1980-04-08 | [2''-(Trifluormethyl)-phenthiazin-10''-yl-(n-prop-3'''ylpiperazin-4''''-yläth-2'''''-yl)]-ester, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6043345B2 (enExample) |
| AT (1) | AT375355B (enExample) |
| BE (1) | BE882535A (enExample) |
| CA (1) | CA1128940A (enExample) |
| CH (1) | CH643843A5 (enExample) |
| CS (1) | CS214704B2 (enExample) |
| DD (1) | DD150060A5 (enExample) |
| DE (1) | DE3013502C2 (enExample) |
| ES (1) | ES8103077A1 (enExample) |
| FR (1) | FR2453164A1 (enExample) |
| GB (1) | GB2047694B (enExample) |
| HU (1) | HU179190B (enExample) |
| IT (1) | IT1148812B (enExample) |
| PL (1) | PL127329B1 (enExample) |
| SU (1) | SU925250A3 (enExample) |
| YU (1) | YU42663B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471116A (en) * | 1982-07-28 | 1984-09-11 | Hoffmann-La Roche Inc. | Substituted (10H-phenothiazin-10-L)-propyl-1-piperazines |
| JPH0568560U (ja) * | 1991-11-05 | 1993-09-17 | 理照 大島 | 握力強化用具 |
| JP3932785B2 (ja) | 1999-08-25 | 2007-06-20 | 株式会社村田製作所 | 圧電体の製造方法 |
| RU2167157C1 (ru) * | 2000-02-11 | 2001-05-20 | Государственный научный центр РФ "НИОПИК" | Способ получения 2-трифторметил-10-(3-хлорпропил)-фенотиазина |
| US20060111346A1 (en) * | 2004-11-23 | 2006-05-25 | Fazix Corporation. | Methods of modulating high-density lipoprotein cholesterol levels and pharmaceutical formulations for the same |
| PL444423A1 (pl) | 2023-04-15 | 2024-10-21 | Ml System Spółka Akcyjna | Sposób wytwarzania laminarnej warstwowej płyty fotowoltaicznej i laminarna warstwowa płyta fotowoltaiczna wytworzona tym sposobem |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL120362C (enExample) * | 1961-04-26 |
-
1979
- 1979-04-06 HU HU79GO1442A patent/HU179190B/hu not_active IP Right Cessation
-
1980
- 1980-03-31 GB GB8010794A patent/GB2047694B/en not_active Expired
- 1980-03-31 BE BE1/9766A patent/BE882535A/fr not_active IP Right Cessation
- 1980-04-01 FR FR8007313A patent/FR2453164A1/fr active Granted
- 1980-04-03 DD DD80220206A patent/DD150060A5/de not_active IP Right Cessation
- 1980-04-03 CH CH266180A patent/CH643843A5/de not_active IP Right Cessation
- 1980-04-03 AT AT0184080A patent/AT375355B/de not_active IP Right Cessation
- 1980-04-03 CA CA349,181A patent/CA1128940A/en not_active Expired
- 1980-04-04 IT IT21186/80A patent/IT1148812B/it active
- 1980-04-04 SU SU802903447A patent/SU925250A3/ru active
- 1980-04-04 YU YU933/80A patent/YU42663B/xx unknown
- 1980-04-04 PL PL1980223267A patent/PL127329B1/pl unknown
- 1980-04-04 CS CS802359A patent/CS214704B2/cs unknown
- 1980-04-05 JP JP55044086A patent/JPS6043345B2/ja not_active Expired
- 1980-04-07 ES ES490315A patent/ES8103077A1/es not_active Expired
- 1980-04-08 DE DE3013502A patent/DE3013502C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55153776A (en) | 1980-11-29 |
| YU93380A (en) | 1983-01-21 |
| GB2047694A (en) | 1980-12-03 |
| PL223267A1 (enExample) | 1981-01-30 |
| ATA184080A (de) | 1983-12-15 |
| HU179190B (en) | 1982-09-28 |
| CA1128940A (en) | 1982-08-03 |
| ES490315A0 (es) | 1981-02-16 |
| BE882535A (fr) | 1980-09-30 |
| SU925250A3 (ru) | 1982-04-30 |
| IT8021186A0 (it) | 1980-04-04 |
| YU42663B (en) | 1988-10-31 |
| FR2453164A1 (fr) | 1980-10-31 |
| PL127329B1 (en) | 1983-10-31 |
| IT1148812B (it) | 1986-12-03 |
| ES8103077A1 (es) | 1981-02-16 |
| CH643843A5 (de) | 1984-06-29 |
| JPS6043345B2 (ja) | 1985-09-27 |
| AT375355B (de) | 1984-07-25 |
| CS214704B2 (en) | 1982-05-28 |
| DE3013502A1 (de) | 1980-10-16 |
| DD150060A5 (de) | 1981-08-12 |
| FR2453164B1 (enExample) | 1983-04-15 |
| GB2047694B (en) | 1983-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |