DD150060A5 - Verfahren zur herstellung von neuen phenthiazin-derivaten - Google Patents
Verfahren zur herstellung von neuen phenthiazin-derivaten Download PDFInfo
- Publication number
- DD150060A5 DD150060A5 DD80220206A DD22020680A DD150060A5 DD 150060 A5 DD150060 A5 DD 150060A5 DD 80220206 A DD80220206 A DD 80220206A DD 22020680 A DD22020680 A DD 22020680A DD 150060 A5 DD150060 A5 DD 150060A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acid
- general formula
- trifluoromethyl
- propyl
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 230000008569 process Effects 0.000 title claims abstract description 9
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims abstract description 37
- 150000002148 esters Chemical class 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 18
- -1 4- (2-hydroxyethyl) -piperazinyl-1-propyl Chemical group 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 11
- 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 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 14
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 abstract description 8
- 238000002347 injection Methods 0.000 abstract description 6
- 239000007924 injection Substances 0.000 abstract description 6
- 230000000701 neuroleptic effect Effects 0.000 abstract description 6
- 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 abstract description 4
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- 239000006188 syrup Substances 0.000 abstract description 4
- 235000020357 syrup Nutrition 0.000 abstract description 4
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 abstract description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
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- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005647 linker group Chemical class 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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 |
|---|---|
| DD150060A5 true DD150060A5 (de) | 1981-08-12 |
Family
ID=10996889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80220206A DD150060A5 (de) | 1979-04-06 | 1980-04-03 | Verfahren zur herstellung von neuen phenthiazin-derivaten |
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 |
| CH643843A5 (de) | 1984-06-29 |
| JPS55153776A (en) | 1980-11-29 |
| GB2047694A (en) | 1980-12-03 |
| YU42663B (en) | 1988-10-31 |
| 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 |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |