GB1583554A - Quaternary derivatives of sandwicin and a method of producing them - Google Patents
Quaternary derivatives of sandwicin and a method of producing them Download PDFInfo
- Publication number
- GB1583554A GB1583554A GB10521/77A GB1052177A GB1583554A GB 1583554 A GB1583554 A GB 1583554A GB 10521/77 A GB10521/77 A GB 10521/77A GB 1052177 A GB1052177 A GB 1052177A GB 1583554 A GB1583554 A GB 1583554A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sandwicin
- derivative
- general formula
- halide
- 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
- CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 12
- 239000002585 base Substances 0.000 claims abstract description 12
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 9
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 7
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 150000004820 halides Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkyl radical Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical group [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 230000002908 adrenolytic effect Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 210000003540 papillary muscle Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- CJDRUOGAGYHKKD-RQBLFBSQSA-N 1pon08459r Chemical class CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O CJDRUOGAGYHKKD-RQBLFBSQSA-N 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940080360 rauwolfia alkaloid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762611162 DE2611162A1 (de) | 1976-03-17 | 1976-03-17 | Neue quartaere derivate von sandwicin und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1583554A true GB1583554A (en) | 1981-01-28 |
Family
ID=5972662
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10521/77A Expired GB1583554A (en) | 1976-03-17 | 1977-03-11 | Quaternary derivatives of sandwicin and a method of producing them |
| GB41140/79A Expired GB1583555A (en) | 1976-03-17 | 1977-03-11 | Open ring aldehyde derivatives of sandwicin and a method of producing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41140/79A Expired GB1583555A (en) | 1976-03-17 | 1977-03-11 | Open ring aldehyde derivatives of sandwicin and a method of producing them |
Country Status (25)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2941531A1 (de) * | 1979-10-13 | 1981-04-23 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 10-bromsandwicin und 10-bromisosandwicin, verfahren zu deren herstellung und deren verwendung |
| DE2941530A1 (de) * | 1979-10-13 | 1981-04-23 | Kali-Chemie Pharma Gmbh, 3000 Hannover | N (pfeil abwaerts)b(pfeil hoch) -quartaere derivate von sandwicin und isosandwicin, verfahren und zwischenprodukte zur herstellung der derivate, die derivate enthaltende arzneimittel und die verwendung der derivate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1154120B (de) * | 1962-01-10 | 1963-09-12 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Ajmalinderivaten |
| GB1582627A (en) * | 1976-01-16 | 1981-01-14 | Inverni Della Beffa Spa | Derivatives of sandwicine and isosandwicine and pharmaceutical compositions comprising sandwicine isosandwicine and derivatives thereof |
-
1976
- 1976-03-17 DE DE19762611162 patent/DE2611162A1/de active Granted
-
1977
- 1977-02-23 MX MX775461U patent/MX4788E/es unknown
- 1977-03-02 AR AR266736A patent/AR211567A1/es active
- 1977-03-04 CS CS771481A patent/CS197287B2/cs unknown
- 1977-03-04 CH CH275377A patent/CH631714A5/de not_active IP Right Cessation
- 1977-03-08 IT IT21028/77A patent/IT1084656B/it active
- 1977-03-08 IL IL51630A patent/IL51630A/xx unknown
- 1977-03-10 NL NL7702609A patent/NL7702609A/xx not_active Application Discontinuation
- 1977-03-11 GB GB10521/77A patent/GB1583554A/en not_active Expired
- 1977-03-11 ES ES456755A patent/ES456755A1/es not_active Expired
- 1977-03-11 GB GB41140/79A patent/GB1583555A/en not_active Expired
- 1977-03-14 PT PT66298A patent/PT66298B/pt unknown
- 1977-03-15 FR FR7707630A patent/FR2344557A1/fr active Granted
- 1977-03-15 GR GR53002A patent/GR62637B/el unknown
- 1977-03-15 SE SE7702907A patent/SE7702907L/xx not_active Application Discontinuation
- 1977-03-15 DD DD7700197869A patent/DD128774A5/xx unknown
- 1977-03-15 BE BE6045928A patent/BE852493A/xx not_active IP Right Cessation
- 1977-03-16 NO NO770934A patent/NO146282C/no unknown
- 1977-03-16 YU YU00701/77A patent/YU70177A/xx unknown
- 1977-03-16 DK DK114677A patent/DK143602C/da active
- 1977-03-16 ZA ZA00771569A patent/ZA771569B/xx unknown
- 1977-03-16 AT AT179277A patent/AT353986B/de not_active IP Right Cessation
- 1977-03-17 JP JP2976377A patent/JPS52113988A/ja active Pending
- 1977-03-17 FI FI770855A patent/FI61898C/fi not_active IP Right Cessation
- 1977-03-17 CA CA274,191A patent/CA1072959A/en not_active Expired
- 1977-05-11 IN IN707/CAL/77A patent/IN146149B/en unknown
-
1978
- 1978-09-05 FR FR7825511A patent/FR2392995A1/fr active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1181540A3 (ru) | Способ получени сульфамоилзамещенного производного фенэтиламина и его кислотной соли | |
| RU2073677C1 (ru) | Сложные эфиры тиенилкарбоновой кислоты и аминоспиртов, способ их получения и фармацевтическая композиция, обладающая антихолинергической активностью | |
| WO1992012978A1 (fr) | Nouveaux ligands macrocycliques azotes, procede de preparation, complexes polymetalliques, composition de diagnostic et therapeutique | |
| FR2696740A1 (fr) | Dérivés prodrogués de la diméthylbiguanide et applications comme médicaments. | |
| CZ199795A3 (en) | Novel pyrrolocarbazoles | |
| EP0009445A1 (fr) | Procédé de préparation d'hydroxy-9 ellipticine et de dérivés de celle-ci | |
| BE823841A (fr) | Derives de 5-(1-hydroxy-2-amino substitue) alkyl-8-carbostyryle substitue et de 5-(1-hydroxy-2-amino substitue) alkyl-8-(3,4-dihydro) carbostyryle substitue et leur procede de preparation | |
| EP0148094A2 (en) | Anti-tumor agent comprising an O-benzylidene-L-ascorbic acid or a salt thereof, and the production of the latter compound | |
| JPH02504394A (ja) | フロ〔３，４‐ｃ〕ピリジン鏡像体の立体特異的製造方法、かくして得られた化合物及びこれの製薬組成物 | |
| EP0357126B1 (en) | Tetracyclic antidepressants | |
| US3847924A (en) | Certain scopolammonium compounds | |
| US4451473A (en) | 3,7-Diazabicyclo [3.3.1] nonanes having anti-arrhythmic activity | |
| GB1583554A (en) | Quaternary derivatives of sandwicin and a method of producing them | |
| NZ336733A (en) | Xamoneline tartrate for treating Alzheimer's disease | |
| US6444680B1 (en) | Amine salts of an integrin receptor antagonist | |
| KR810000658B1 (ko) | 샌드위신의 4급 유도체의 제조방법 | |
| JPS6310697B2 (enrdf_load_stackoverflow) | ||
| US4820837A (en) | 1-hydroxy-oxo-5H-pyrido(3,2-a)phenoxazine-3-carboxylic acid esters | |
| KR20150042275A (ko) | 3-포르밀리파마이신 sv 및 3-포르밀리파마이신 s의 3-(4-신나밀-l-피페라지닐) 아미노 유도체를 함유하는 제약 제제 및 그의 제조 방법 | |
| US3637717A (en) | Nicotinic acid ester | |
| KR810001697B1 (ko) | 이소부티라미드 유도체의 신규한 제조방법 | |
| FI66382B (fi) | Foerfarande foer framstaellning av farmaceutiskt anvaendbar 17,17's-bisspartein | |
| US3433789A (en) | S-benzoyloxymethyl-thiamines | |
| US3547974A (en) | Aromatic propylamino cyano compounds | |
| US3475439A (en) | 3-azabicyclo(3.3.1)nonane compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 416 | Proceeding under section 16 patents act 1949 | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| SP | Amendment (slips) printed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930311 |