DE2731680A1 - Behensaeureester von phenothiazinderivaten, verfahren zu ihrer herstellung und diese enthaltende arzneimittel - Google Patents
Behensaeureester von phenothiazinderivaten, verfahren zu ihrer herstellung und diese enthaltende arzneimittelInfo
- Publication number
- DE2731680A1 DE2731680A1 DE19772731680 DE2731680A DE2731680A1 DE 2731680 A1 DE2731680 A1 DE 2731680A1 DE 19772731680 DE19772731680 DE 19772731680 DE 2731680 A DE2731680 A DE 2731680A DE 2731680 A1 DE2731680 A1 DE 2731680A1
- Authority
- DE
- Germany
- Prior art keywords
- behenic acid
- general formula
- phenothiazine
- ester
- fluoro
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 150000002990 phenothiazines Chemical class 0.000 title claims description 6
- 229940126601 medicinal product Drugs 0.000 title claims description 3
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 20
- -1 behenic acid ester Chemical class 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 235000021357 Behenic acid Nutrition 0.000 claims description 10
- 229940116226 behenic acid Drugs 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 8
- 230000003000 nontoxic effect Effects 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- FWFBVSNMBCKTIL-UHFFFAOYSA-N 2-[1-[3-[7-fluoro-2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC(F)=CC=C21 FWFBVSNMBCKTIL-UHFFFAOYSA-N 0.000 claims description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 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 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 241000282472 Canis lupus familiaris Species 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 5
- 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 5
- 229960004046 apomorphine Drugs 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000008673 vomiting Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 206010039897 Sedation Diseases 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 230000036280 sedation Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001954 decanoic acid esters Chemical class 0.000 description 3
- 229960002690 fluphenazine Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 230000000701 neuroleptic effect Effects 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- TWXOVTBDDMZMSK-UHFFFAOYSA-N 2-[4-[3-[7-fluoro-2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC(F)=CC=C21 TWXOVTBDDMZMSK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001519 thymoleptic effect Effects 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
- 210000004916 vomit Anatomy 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35411/76A GB1540842A (en) | 1976-08-25 | 1976-08-25 | Phenothiazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2731680A1 true DE2731680A1 (de) | 1978-03-02 |
Family
ID=10377428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772731680 Withdrawn DE2731680A1 (de) | 1976-08-25 | 1977-07-13 | Behensaeureester von phenothiazinderivaten, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2179169C2 (ru) * | 2000-02-11 | 2002-02-10 | Государственный научный центр РФ "НИОПИК" | Способ получения дигидрохлорида 2-трифторметил-10-[3-(1-метил-пиперазинил-4)-пропил]-фенотиазина |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8628903D0 (en) * | 1986-12-03 | 1987-01-07 | Lunbeck A S H | Neuroleptic compounds |
| US7544681B2 (en) * | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| EP2275143B1 (en) * | 2001-09-27 | 2012-12-19 | Ramot at Tel Aviv University Ltd. | Conjugates of perphenazine or fluphenazine with carboxylic acids |
| EP1888120B1 (en) * | 2005-06-07 | 2012-12-05 | Ramot at Tel Aviv University Ltd. | Novel salts of conjugated psychotropic drugs and processes of preparing same |
| US8222296B2 (en) * | 2006-07-17 | 2012-07-17 | Ramot At Tel-Aviv University Ltd. | Conjugates comprising a GABA- or glycine compound, pharmaceutical compositions and combinations thereof and their use in treating CNS disorders |
| US8207369B2 (en) * | 2008-02-11 | 2012-06-26 | Ramot At Tel-Aviv University Ltd. | Conjugates for treating neurodegenerative diseases and disorders |
| CA2782514A1 (en) * | 2009-12-09 | 2011-06-16 | Biolinerx Ltd. | Methods of improving cognitive functions |
| US8916610B2 (en) | 2010-09-22 | 2014-12-23 | Ramot At Tel-Aviv University Ltd. | Acid addition salt of a nortriptyline-GABA conjugate and a process of preparing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795517A (fr) | 1972-02-17 | 1973-08-16 | Ciba Geigy | Nouveaux sels de peptides de l'acth et leurs procedes de preparation |
| GB1460713A (en) * | 1973-06-08 | 1977-01-06 | Kefalas As | 7-fluoro substituted phenothiazines method for preparation thereof and compositions bladed rotor for a gas turbine engine |
-
1976
- 1976-08-25 GB GB35411/76A patent/GB1540842A/en not_active Expired
-
1977
- 1977-07-07 NL NL7707558A patent/NL7707558A/xx not_active Application Discontinuation
- 1977-07-12 AT AT498677A patent/AT347964B/de not_active IP Right Cessation
- 1977-07-13 DE DE19772731680 patent/DE2731680A1/de not_active Withdrawn
- 1977-08-02 IE IE1603/77A patent/IE45178B1/en unknown
- 1977-08-05 NZ NZ184858A patent/NZ184858A/xx unknown
- 1977-08-05 ZA ZA00774756A patent/ZA774756B/xx unknown
- 1977-08-08 BE BE179985A patent/BE857576A/xx unknown
- 1977-08-09 FI FI772394A patent/FI772394A7/fi not_active Application Discontinuation
- 1977-08-16 DK DK363177A patent/DK363177A/da unknown
- 1977-08-19 AU AU28054/77A patent/AU508252B2/en not_active Expired
- 1977-08-19 US US05/826,049 patent/US4153694A/en not_active Expired - Lifetime
- 1977-08-20 ES ES461785A patent/ES461785A1/es not_active Expired
- 1977-08-23 CA CA285,276A patent/CA1088936A/en not_active Expired
- 1977-08-23 CH CH1032577A patent/CH628632A5/de not_active IP Right Cessation
- 1977-08-24 SE SE7709507A patent/SE7709507L/xx unknown
- 1977-08-24 LU LU78019A patent/LU78019A1/xx unknown
- 1977-08-24 NO NO772940A patent/NO772940L/no unknown
- 1977-08-25 FR FR7725990A patent/FR2362852A1/fr active Granted
- 1977-08-25 JP JP10118277A patent/JPS5350185A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2179169C2 (ru) * | 2000-02-11 | 2002-02-10 | Государственный научный центр РФ "НИОПИК" | Способ получения дигидрохлорида 2-трифторметил-10-[3-(1-метил-пиперазинил-4)-пропил]-фенотиазина |
Also Published As
| Publication number | Publication date |
|---|---|
| IE45178B1 (en) | 1982-06-30 |
| FI772394A7 (fi) | 1978-02-26 |
| SE7709507L (sv) | 1978-02-26 |
| GB1540842A (en) | 1979-02-14 |
| JPS5350185A (en) | 1978-05-08 |
| DK363177A (da) | 1978-02-26 |
| AU508252B2 (en) | 1980-03-13 |
| FR2362852A1 (fr) | 1978-03-24 |
| US4153694A (en) | 1979-05-08 |
| NO772940L (no) | 1978-02-28 |
| NZ184858A (en) | 1979-03-28 |
| ZA774756B (en) | 1978-06-28 |
| ES461785A1 (es) | 1978-06-16 |
| LU78019A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-27 |
| IE45178L (en) | 1978-02-25 |
| FR2362852B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-09-05 |
| BE857576A (fr) | 1978-02-08 |
| AU2805477A (en) | 1979-03-08 |
| CH628632A5 (de) | 1982-03-15 |
| ATA498677A (de) | 1978-06-15 |
| CA1088936A (en) | 1980-11-04 |
| AT347964B (de) | 1979-01-25 |
| NL7707558A (nl) | 1978-02-28 |
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