CH643843A5 - Phenthiazin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. - Google Patents
Phenthiazin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. Download PDFInfo
- Publication number
- CH643843A5 CH643843A5 CH266180A CH266180A CH643843A5 CH 643843 A5 CH643843 A5 CH 643843A5 CH 266180 A CH266180 A CH 266180A CH 266180 A CH266180 A CH 266180A CH 643843 A5 CH643843 A5 CH 643843A5
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- acid
- phenthiazine
- trifluoromethyl
- ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 18
- 239000007858 starting material Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 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 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 235000004338 Syringa vulgaris Nutrition 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 3
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- 239000007787 solid Substances 0.000 claims description 3
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- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 17
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- -1 6-methoxy-2-naphthyl Chemical group 0.000 description 13
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- 239000000155 melt Substances 0.000 description 11
- 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 10
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
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- SXWGTMNDGSAUON-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-2-methylpropanoic acid Chemical compound CC1=CC(C)=CC(OC(C)(C)C(O)=O)=C1 SXWGTMNDGSAUON-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 229960002690 fluphenazine Drugs 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
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- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 229960001374 fluphenazine decanoate Drugs 0.000 description 4
- VIQCGTZFEYDQMR-UHFFFAOYSA-N fluphenazine decanoate Chemical compound C1CN(CCOC(=O)CCCCCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 VIQCGTZFEYDQMR-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000000701 neuroleptic effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
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- ZAWKYPLLOTZOCX-UHFFFAOYSA-N 2,3-dimethyl-2-naphthalen-1-yloxybutanoic acid Chemical class C1=CC=C2C(OC(C)(C(C)C)C(O)=O)=CC=CC2=C1 ZAWKYPLLOTZOCX-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
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003900 succinic acid esters 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
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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)
- Anesthesiology (AREA)
- Psychiatry (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (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 (1)
| Publication Number | Publication Date |
|---|---|
| CH643843A5 true CH643843A5 (de) | 1984-06-29 |
Family
ID=10996889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH266180A CH643843A5 (de) | 1979-04-06 | 1980-04-03 | Phenthiazin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6043345B2 (cs) |
| AT (1) | AT375355B (cs) |
| BE (1) | BE882535A (cs) |
| CA (1) | CA1128940A (cs) |
| CH (1) | CH643843A5 (cs) |
| CS (1) | CS214704B2 (cs) |
| DD (1) | DD150060A5 (cs) |
| DE (1) | DE3013502C2 (cs) |
| ES (1) | ES490315A0 (cs) |
| FR (1) | FR2453164A1 (cs) |
| GB (1) | GB2047694B (cs) |
| HU (1) | HU179190B (cs) |
| IT (1) | IT1148812B (cs) |
| PL (1) | PL127329B1 (cs) |
| SU (1) | SU925250A3 (cs) |
| YU (1) | YU42663B (cs) |
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 |
|---|---|---|---|---|
| NL277672A (cs) * | 1961-04-26 |
-
1979
- 1979-04-06 HU HU79GO1442A patent/HU179190B/hu not_active IP Right Cessation
-
1980
- 1980-03-31 BE BE1/9766A patent/BE882535A/fr not_active IP Right Cessation
- 1980-03-31 GB GB8010794A patent/GB2047694B/en not_active Expired
- 1980-04-01 FR FR8007313A patent/FR2453164A1/fr active Granted
- 1980-04-03 CH CH266180A patent/CH643843A5/de not_active IP Right Cessation
- 1980-04-03 DD DD80220206A patent/DD150060A5/de not_active IP Right Cessation
- 1980-04-03 CA CA349,181A patent/CA1128940A/en not_active Expired
- 1980-04-03 AT AT0184080A patent/AT375355B/de not_active IP Right Cessation
- 1980-04-04 CS CS802359A patent/CS214704B2/cs unknown
- 1980-04-04 YU YU933/80A patent/YU42663B/xx unknown
- 1980-04-04 IT IT21186/80A patent/IT1148812B/it active
- 1980-04-04 PL PL1980223267A patent/PL127329B1/pl unknown
- 1980-04-04 SU SU802903447A patent/SU925250A3/ru active
- 1980-04-05 JP JP55044086A patent/JPS6043345B2/ja not_active Expired
- 1980-04-07 ES ES490315A patent/ES490315A0/es active Granted
- 1980-04-08 DE DE3013502A patent/DE3013502C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8103077A1 (es) | 1981-02-16 |
| FR2453164A1 (fr) | 1980-10-31 |
| CA1128940A (en) | 1982-08-03 |
| GB2047694B (en) | 1983-02-02 |
| AT375355B (de) | 1984-07-25 |
| DE3013502A1 (de) | 1980-10-16 |
| JPS55153776A (en) | 1980-11-29 |
| GB2047694A (en) | 1980-12-03 |
| YU42663B (en) | 1988-10-31 |
| DD150060A5 (de) | 1981-08-12 |
| SU925250A3 (ru) | 1982-04-30 |
| ATA184080A (de) | 1983-12-15 |
| IT1148812B (it) | 1986-12-03 |
| YU93380A (en) | 1983-01-21 |
| IT8021186A0 (it) | 1980-04-04 |
| DE3013502C2 (de) | 1985-02-07 |
| ES490315A0 (es) | 1981-02-16 |
| CS214704B2 (en) | 1982-05-28 |
| PL223267A1 (cs) | 1981-01-30 |
| HU179190B (en) | 1982-09-28 |
| FR2453164B1 (cs) | 1983-04-15 |
| BE882535A (fr) | 1980-09-30 |
| PL127329B1 (en) | 1983-10-31 |
| JPS6043345B2 (ja) | 1985-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |