GB1384022A - Hexamethylene-imine derivatives and their preparation - Google Patents
Hexamethylene-imine derivatives and their preparationInfo
- Publication number
- GB1384022A GB1384022A GB1316173A GB1316173A GB1384022A GB 1384022 A GB1384022 A GB 1384022A GB 1316173 A GB1316173 A GB 1316173A GB 1316173 A GB1316173 A GB 1316173A GB 1384022 A GB1384022 A GB 1384022A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- condensing
- acid
- group
- pharmaceutically acceptable
- 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
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 title abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- -1 ethylphenyl Chemical group 0.000 abstract 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000003944 tolyl group Chemical group 0.000 abstract 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 1
- GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 abstract 1
- FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical class CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000006277 halobenzyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229960002510 mandelic acid Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
1384022 Hexamethyleneimines INNOTHERA 19 March 1973 [30 March 1972] 13161/73 Heading C2C Novel hexamethyleneimines of the general formula wherein R is a hydrogen atom or methyl or ethyl group, n is 0, 1, 2 or 3 and A is or R 1 R 2 CHCONH-, in which each of R 1 and R 2 is a straight or branched chain saturated C 1-6 aliphatic, allyl, cyclopentyl, cyclohexyl, cyclohexenyl, benzyl, halobenzyl, phenyl, halophenyl, methylphenyl, ethylphenyl, heterocyclyl or heterocyclylmethyl group, provided that when A is R 1 R 2 CHCOO- and one of R 1 and R 2 is a 3-thienyl group, the other is not a cyclopentyl, cyclohexyl, phenyl, halophenyl, methylphenyl or ethylphenyl group, including racemates and optical isomers, and quaternary ammonium pharmaceutically acceptable acid addition salts and derivatives thereof are prepared by condensing an acid of the general formula R 1 R 2 CHCOOH or a reactive functional derivative thereof with a hexamethyleneimine of the general formula wherein B is a halogen atom or hydroxyl or amino group. Acids of the second general formula above are prepared (a) by condensing mandelic acid, which may be substituted, with an appropriate benzene derivative in the presence of stannic chloride, (b) by condensing (by a malonic synthesis), optionally substituted ethyl phenylmalonate with benzyl chloride, which may be substituted, 2-chloromethylfuran or 2- or 3- chloromethyl-thiophene, followed by saponification and decarboxylation of the resulting malonic acid ester and (c) by reducing a glycollic acid of the general formula R 1 R 2 C(OH)COOH, obtained by condensing an appropriate glyoxylic acid with a Grignard reagent. Pharmaceutical compositions having spasmolytic and vasodilating activity comprise, as active ingredient, a hexamethyleneimine of the first general formula above or a pharmaceutically acceptable acid addition salt or quartenary ammonium derivative thereof, in association with a pharmaceutically acceptable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7209639A FR2176473B1 (en) | 1972-03-20 | 1972-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1384022A true GB1384022A (en) | 1974-02-12 |
Family
ID=9095472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1316173A Expired GB1384022A (en) | 1972-03-20 | 1973-03-19 | Hexamethylene-imine derivatives and their preparation |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5320039B2 (en) |
| CA (1) | CA1010862A (en) |
| DE (1) | DE2313338C3 (en) |
| FR (1) | FR2176473B1 (en) |
| GB (1) | GB1384022A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4377592A (en) | 1979-10-23 | 1983-03-22 | Innothera | Antiarrhythmic activity of cetiedil |
| EP1426360A1 (en) * | 2001-09-12 | 2004-06-09 | Kaken Pharmaceutical Co., Ltd. | 2-phenyl-3-heteroarylpropionic acid derivative or salt thereof and medicine containing the same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5151164A (en) * | 1974-10-30 | 1976-05-06 | Nippon Kentetsu Co Ltd | JIDOSENTAKUKI |
| FR2333501A2 (en) | 1975-12-03 | 1977-07-01 | Science Union & Cie | NEW ACETAMIDES SUBSTITUTED THEIR METHODS OF OBTAINING AND THE PHARMACEUTICAL COMPOSITIONS BY CONTAINING |
| JPS52113572A (en) * | 1976-03-19 | 1977-09-22 | Sanyo Electric Co Ltd | Controlling device for washing machine |
| FR2666509B1 (en) * | 1990-09-12 | 1994-11-25 | Adir | USE OF N- (1-HEXAHYDROAZEPINYLALKYL) ACETAMIDES IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF CHOLINERGIC TRANSMISSION DISORDERS. |
-
1972
- 1972-03-20 FR FR7209639A patent/FR2176473B1/fr not_active Expired
-
1973
- 1973-03-17 DE DE2313338A patent/DE2313338C3/en not_active Expired
- 1973-03-19 GB GB1316173A patent/GB1384022A/en not_active Expired
- 1973-03-19 CA CA166,434A patent/CA1010862A/en not_active Expired
- 1973-03-19 JP JP3255273A patent/JPS5320039B2/ja not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4377592A (en) | 1979-10-23 | 1983-03-22 | Innothera | Antiarrhythmic activity of cetiedil |
| EP1426360A1 (en) * | 2001-09-12 | 2004-06-09 | Kaken Pharmaceutical Co., Ltd. | 2-phenyl-3-heteroarylpropionic acid derivative or salt thereof and medicine containing the same |
| EP1426360A4 (en) * | 2001-09-12 | 2006-04-12 | Kaken Pharma Co Ltd | 2-PHENYL-3-HETEROARYL PROPIONIC ACID DERIVATIVES AND THEIR SALTS, AND MEDICAMENTS CONTAINING THEM |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2313338B2 (en) | 1980-06-26 |
| JPS5320039B2 (en) | 1978-06-24 |
| JPS495985A (en) | 1974-01-19 |
| CA1010862A (en) | 1977-05-24 |
| DE2313338C3 (en) | 1981-04-09 |
| DE2313338A1 (en) | 1973-10-04 |
| FR2176473A1 (en) | 1973-11-02 |
| FR2176473B1 (en) | 1975-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |