DK142751B - Analogifremgangsmåde til fremstilling af 4-((2-methyl-3-hydroxy-4-hydroxymethyl)-5-pyridyl-N-methyl-N'-piperazinyl)-p-fluor-butyrophenon eller syreadditionssalte heraf. - Google Patents
Analogifremgangsmåde til fremstilling af 4-((2-methyl-3-hydroxy-4-hydroxymethyl)-5-pyridyl-N-methyl-N'-piperazinyl)-p-fluor-butyrophenon eller syreadditionssalte heraf. Download PDFInfo
- Publication number
- DK142751B DK142751B DK168074AA DK168074A DK142751B DK 142751 B DK142751 B DK 142751B DK 168074A A DK168074A A DK 168074AA DK 168074 A DK168074 A DK 168074A DK 142751 B DK142751 B DK 142751B
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- fluoro
- preparation
- butyrophenone
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 7
- 150000003839 salts Chemical class 0.000 title description 5
- 239000002253 acid Substances 0.000 title description 4
- 241000700159 Rattus Species 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- 230000036772 blood pressure Effects 0.000 description 12
- 206010020772 Hypertension Diseases 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000001631 hypertensive effect Effects 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
- 239000011677 pyridoxine Substances 0.000 description 4
- 229940011671 vitamin b6 Drugs 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 210000001367 artery Anatomy 0.000 description 3
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 3
- 230000003205 diastolic effect Effects 0.000 description 3
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 3
- 229960003602 guanethidine Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 210000003815 abdominal wall Anatomy 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- WHRVRSCEWKLAHX-LQDWTQKMSA-N benzylpenicillin procaine Chemical compound [H+].CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 WHRVRSCEWKLAHX-LQDWTQKMSA-N 0.000 description 2
- 239000002729 catgut Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000008160 pyridoxine Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- RSEHHYMPNZWTGQ-UHFFFAOYSA-N 3-piperazin-4-ium-1-ylpropanoate Chemical compound OC(=O)CCN1CCNCC1 RSEHHYMPNZWTGQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 101100515516 Arabidopsis thaliana XI-H gene Proteins 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OXJPYKIJCGRVRI-UHFFFAOYSA-N CC1=C(C(C(C=N1)(CO)N2CCNCC2)CO)O Chemical compound CC1=C(C(C(C=N1)(CO)N2CCNCC2)CO)O OXJPYKIJCGRVRI-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NBJGGHFXCGHTNJ-UHFFFAOYSA-N guanethidine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.NC(=N)NCCN1CCCCCCC1.NC(=N)NCCN1CCCCCCC1 NBJGGHFXCGHTNJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1481573A GB1433222A (en, 2012) | 1973-03-28 | 1973-03-28 | |
| GB1481573 | 1973-03-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142751B true DK142751B (da) | 1981-01-12 |
| DK142751C DK142751C (en, 2012) | 1981-08-17 |
Family
ID=10047975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK168074AA DK142751B (da) | 1973-03-28 | 1974-03-27 | Analogifremgangsmåde til fremstilling af 4-((2-methyl-3-hydroxy-4-hydroxymethyl)-5-pyridyl-N-methyl-N'-piperazinyl)-p-fluor-butyrophenon eller syreadditionssalte heraf. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3903088A (en, 2012) |
| JP (1) | JPS532876B2 (en, 2012) |
| AR (1) | AR200519A1 (en, 2012) |
| AT (1) | AT332569B (en, 2012) |
| AU (1) | AU473846B2 (en, 2012) |
| BE (1) | BE812558A (en, 2012) |
| CA (1) | CA1011337A (en, 2012) |
| CH (1) | CH592652A5 (en, 2012) |
| DK (1) | DK142751B (en, 2012) |
| ES (1) | ES424318A1 (en, 2012) |
| FR (2) | FR2223370B1 (en, 2012) |
| GB (1) | GB1433222A (en, 2012) |
| IN (1) | IN139464B (en, 2012) |
| NL (1) | NL7403812A (en, 2012) |
| OA (1) | OA04692A (en, 2012) |
| ZA (1) | ZA741617B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA783521B (en) * | 1977-07-12 | 1979-06-27 | Scras | New pyrimidine derivatives,their preparation and therapeutic compositions containing the same |
| US4175769A (en) * | 1978-05-01 | 1979-11-27 | Kazmark Eugene A | Portable luggage carrier |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3557131A (en) * | 1965-06-15 | 1971-01-19 | Dainippon Pharmaceutical Co | Nicotinate derivatives of vitamin b6 |
| US3717636A (en) * | 1970-01-21 | 1973-02-20 | A Esanu | Salts of pyridoxine mono-esters |
| CH541568A (de) * | 1970-12-07 | 1973-10-31 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Imidazolidinonderivaten |
-
1973
- 1973-03-28 GB GB1481573A patent/GB1433222A/en not_active Expired
-
1974
- 1974-03-12 ZA ZA00741617A patent/ZA741617B/xx unknown
- 1974-03-15 AU AU66703/74A patent/AU473846B2/en not_active Expired
- 1974-03-15 US US451513A patent/US3903088A/en not_active Expired - Lifetime
- 1974-03-15 IN IN557/CAL/74A patent/IN139464B/en unknown
- 1974-03-15 ES ES424318A patent/ES424318A1/es not_active Expired
- 1974-03-20 BE BE142212A patent/BE812558A/xx not_active IP Right Cessation
- 1974-03-21 NL NL7403812A patent/NL7403812A/xx unknown
- 1974-03-22 CH CH400374A patent/CH592652A5/xx not_active IP Right Cessation
- 1974-03-22 FR FR7409799A patent/FR2223370B1/fr not_active Expired
- 1974-03-26 FR FR7410207A patent/FR2223019B1/fr not_active Expired
- 1974-03-27 DK DK168074AA patent/DK142751B/da not_active IP Right Cessation
- 1974-03-27 CA CA196,166A patent/CA1011337A/en not_active Expired
- 1974-03-28 OA OA55160A patent/OA04692A/xx unknown
- 1974-03-28 JP JP3402574A patent/JPS532876B2/ja not_active Expired
- 1974-03-28 AT AT256074A patent/AT332569B/de not_active IP Right Cessation
- 1974-03-28 AR AR253016A patent/AR200519A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5046679A (en, 2012) | 1975-04-25 |
| AU6670374A (en) | 1975-09-18 |
| FR2223019A1 (en, 2012) | 1974-10-25 |
| JPS532876B2 (en, 2012) | 1978-02-01 |
| CA1011337A (en) | 1977-05-31 |
| US3903088A (en) | 1975-09-02 |
| DE2415128B2 (de) | 1976-10-07 |
| FR2223370A1 (en, 2012) | 1974-10-25 |
| ZA741617B (en) | 1975-02-26 |
| FR2223019B1 (en, 2012) | 1977-11-04 |
| NL7403812A (en, 2012) | 1974-10-01 |
| ATA256074A (de) | 1976-01-15 |
| AR200519A1 (es) | 1974-11-15 |
| BE812558A (fr) | 1974-09-20 |
| AU473846B2 (en) | 1976-07-01 |
| GB1433222A (en, 2012) | 1976-04-22 |
| IN139464B (en, 2012) | 1976-06-19 |
| DK142751C (en, 2012) | 1981-08-17 |
| FR2223370B1 (en, 2012) | 1976-12-17 |
| OA04692A (fr) | 1980-07-31 |
| CH592652A5 (en, 2012) | 1977-10-31 |
| AT332569B (de) | 1976-10-11 |
| ES424318A1 (es) | 1976-06-01 |
| DE2415128A1 (de) | 1974-10-10 |
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