GB1298525A - Improvements in or relating to butyramidine compositions - Google Patents
Improvements in or relating to butyramidine compositionsInfo
- Publication number
- GB1298525A GB1298525A GB1755871A GB1755871A GB1298525A GB 1298525 A GB1298525 A GB 1298525A GB 1755871 A GB1755871 A GB 1755871A GB 1755871 A GB1755871 A GB 1755871A GB 1298525 A GB1298525 A GB 1298525A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthyloxy
- hydroxy
- reacting
- alkyl
- butyramidine
- 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
- RXKUYBRRTKRGME-UHFFFAOYSA-N butanimidamide Chemical compound CCCC(N)=N RXKUYBRRTKRGME-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- -1 2-imidazolinyl Chemical group 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001409 amidines Chemical group 0.000 abstract 2
- ZVVJOJMCXYDDEW-UHFFFAOYSA-N 1-chloro-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(CCl)O)=CC=CC2=C1 ZVVJOJMCXYDDEW-UHFFFAOYSA-N 0.000 abstract 1
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 abstract 1
- ASZJWZSLVVSBAH-UHFFFAOYSA-N 3-hydroxy-4-naphthalen-1-yloxybutanenitrile Chemical compound C1=CC=C2C(OCC(O)CC#N)=CC=CC2=C1 ASZJWZSLVVSBAH-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- AIWIPBZNHAROMH-UHFFFAOYSA-N ethyl 3-hydroxy-4-naphthalen-1-yloxybutanoate Chemical compound C1(=CC=CC2=CC=CC=C12)OCC(CC(=O)OCC)O AIWIPBZNHAROMH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004283 imidazolin-2-yl group Chemical group [H]N1C(*)=NC([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1298525 Butyramidine derivatives ORSYMONDE 27 May 1971 [29 June 1970 1 April 1971] 17558/71 Heading C2C Novel compounds I in which A is α- or #-naphthyl; R 3 is H or 1-3 C alkyl; R 2 is H, OH or 1-3 C alkyl; and R 1 is H; or R 1 and R 2 together with the two N atoms and C atom of the amidine moiety form a 2-imidazolinyl or 1,4,5,6-tetrahydro-2-pyrimidinyl radical when R 3 is H are prepared by con - densing α- or #-naphthol with epichlorohydrin in the presence of caustic soda; treating the 3- naphthyloxy 1,2 - epoxy propane with- HCl gas; reacting the resultant 1-chloro-3-naphthyloxy- 2 -propanol with KCN; reacting the 4- naphthyloxy - 3 - hydroxy - butyronitrile with ethanol to give the imino ether derivative and reacting the latter with an amine HNR 2 R 3 . Compounds I where R 1 =R 2 =R 3 =H may be reacted with NH 2 OH, H 2 NCH 2 CH 2 NH 2 or H 2 N(CH 2 ) 3 NH 2 to transform the amidine function into-C(NH)NHOH, imidazolin-2-yl or tetrahydropyrimidinyl respectively. The preparation of ethyl 4 - α - naphthyloxy- 3 -hydroxy -butyrate from 4-α-naphthyloxy-3-hydroxy-butyroimino-ethyl ether by hydrolysis and its conversion to 4α-naphthyloxy-3-hydroxybutyrohydroxamic acid are described. Pharmaceutical compositions for oral or parenteral administration as agents for treating cardiac troubles comprise a compound I together .with a suitable carrier or excipient.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR707024016A FR2092895B1 (en) | 1970-06-29 | 1970-06-29 | |
| FR7111548A FR2131894A2 (en) | 1971-04-01 | 1971-04-01 | 4-naphthoxy-3-hydroxy-butyramidines as beta-blocking agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1298525A true GB1298525A (en) | 1972-12-06 |
Family
ID=26215827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1755871A Expired GB1298525A (en) | 1970-06-29 | 1971-05-27 | Improvements in or relating to butyramidine compositions |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS517662B1 (en) |
| BE (1) | BE767721A (en) |
| CA (1) | CA927385A (en) |
| CH (1) | CH524575A (en) |
| DE (2) | DE2132113C3 (en) |
| GB (1) | GB1298525A (en) |
| LU (1) | LU63418A1 (en) |
| NL (1) | NL169177C (en) |
| SE (1) | SE381870B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52145481U (en) * | 1976-04-30 | 1977-11-04 | ||
| DE3211301A1 (en) * | 1982-03-26 | 1983-09-29 | Bayer Ag, 5090 Leverkusen | CYCLIC AMIDINE, METHOD FOR THE PRODUCTION THEREOF AND THE USE OF CYCLIC AMIDINE AS CATALYSTS FOR THE CURE OF EPOXY RESINS |
-
1971
- 1971-05-19 CH CH735971A patent/CH524575A/en not_active IP Right Cessation
- 1971-05-27 BE BE767721A patent/BE767721A/en not_active IP Right Cessation
- 1971-05-27 GB GB1755871A patent/GB1298525A/en not_active Expired
- 1971-06-09 NL NL7107882A patent/NL169177C/en not_active IP Right Cessation
- 1971-06-23 CA CA116379A patent/CA927385A/en not_active Expired
- 1971-06-25 LU LU63418D patent/LU63418A1/xx unknown
- 1971-06-28 SE SE829771A patent/SE381870B/en unknown
- 1971-06-28 DE DE19712132113 patent/DE2132113C3/en not_active Expired
- 1971-06-28 DE DE19712166869 patent/DE2166869C3/en not_active Expired
- 1971-06-29 JP JP4691971A patent/JPS517662B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL169177B (en) | 1982-01-18 |
| DE2132113C3 (en) | 1978-09-21 |
| JPS517662B1 (en) | 1976-03-10 |
| NL7107882A (en) | 1971-12-31 |
| CH524575A (en) | 1972-06-30 |
| DE2166869B2 (en) | 1977-11-24 |
| NL169177C (en) | 1982-06-16 |
| DE2132113B2 (en) | 1978-01-19 |
| DE2166869C3 (en) | 1978-08-17 |
| BE767721A (en) | 1971-10-18 |
| DE2166869A1 (en) | 1976-05-06 |
| DE2132113A1 (en) | 1972-01-05 |
| LU63418A1 (en) | 1971-09-24 |
| CA927385A (en) | 1973-05-29 |
| SE381870B (en) | 1975-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |