ES361114A1 - Pyrrolidines - Google Patents
PyrrolidinesInfo
- Publication number
- ES361114A1 ES361114A1 ES361114A ES361114A ES361114A1 ES 361114 A1 ES361114 A1 ES 361114A1 ES 361114 A ES361114 A ES 361114A ES 361114 A ES361114 A ES 361114A ES 361114 A1 ES361114 A1 ES 361114A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- guanidines
- acid addition
- addition salts
- toxic 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
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 2,4 - dimethylpyrrolidino Chemical group 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000002357 guanidines Chemical class 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- WMZWJUYJXQLURX-UHFFFAOYSA-N 1-chloro-2-methylhex-3-yn-2-ol Chemical compound CCC#CC(C)(O)CCl WMZWJUYJXQLURX-UHFFFAOYSA-N 0.000 abstract 1
- XEBHIUPTXHNYOD-UHFFFAOYSA-N 1-chloro-2-methylpent-4-yn-2-ol Chemical compound ClCC(O)(C)CC#C XEBHIUPTXHNYOD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- FESBOPLTESPUOU-UHFFFAOYSA-N 2-(2,4-dimethylpyrrol-1-yl)ethanol Chemical compound CC=1C=C(C)N(CCO)C=1 FESBOPLTESPUOU-UHFFFAOYSA-N 0.000 abstract 1
- ZWCHLOKPLFVXNK-UHFFFAOYSA-N 2-chloro-3-methylhex-5-yn-3-ol Chemical compound CC(Cl)C(C)(O)CC#C ZWCHLOKPLFVXNK-UHFFFAOYSA-N 0.000 abstract 1
- UOSRYHYUPWRJEK-UHFFFAOYSA-N 3-(chloromethyl)-2,2-dimethylhex-5-yn-3-ol Chemical compound CC(C)(C)C(O)(CCl)CC#C UOSRYHYUPWRJEK-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of formula and their non-toxic acid addition salts, wherein R, R 1 and R 3 are each H or C 1-6 alkyl R 2 is C 1-6 alkyl or cycloalkyl R 4 and R 5 are each H or C 1-6 alkyl, or one of them is amino or nitro, or R 4 R 5 is -CH 2 CH 2 - and n is 2-8. Also claimed are 1 (and 2) - n(2,4 - dimethylpyrrolidino) - 2 (and 1) - propylguanidines and their non-toxic acid addition salts. The guanidines are prepared by guanylating the corresponding pyrrolidinoalkylamines, which are obtained by hydrogenating (1 - pyrrolyl)alkylamines, of which preparative details are also given. Starting materials.-By reacting together the appropriate chloroketone and alkynyl magnesium bromide, there are obtained 4-chloromethyl - 5,5 - dimethylhex - 1 - yn - 4 - ol (with 4 - tert. - butyl - 4,5 - epoxypent - 1 - yre), 5- chloro - 4 - methylhex - 1 - yn - 4 - ol and 5- chloromethylhex - 3 - yn - 5 - ol. 2,4 - Dimethyl- 1 - (2 - hydroxyethyl)pyrrole, obtained from 4- chloromethylpent - 1 - yn - 4 - ol and ethanolamine, is converted to its tosylate. Therapeutic compositions for ral or parenteral administration comprise the above (pyrrolidinoalkyl)guanidines, which have blood pressure lowering activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB55708/67A GB1185080A (en) | 1967-12-07 | 1967-12-07 | Pyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES361114A1 true ES361114A1 (en) | 1970-08-01 |
Family
ID=10474656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES361114A Expired ES361114A1 (en) | 1967-12-07 | 1968-12-05 | Pyrrolidines |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT301569B (en) |
| BE (1) | BE725104A (en) |
| BR (1) | BR6804654D0 (en) |
| CH (1) | CH534679A (en) |
| DE (1) | DE1811832A1 (en) |
| DK (1) | DK126781B (en) |
| ES (1) | ES361114A1 (en) |
| FR (1) | FR7874M (en) |
| GB (1) | GB1185080A (en) |
| IE (1) | IE32781B1 (en) |
| IL (1) | IL31228A (en) |
| IS (1) | IS1807A7 (en) |
| NL (1) | NL6817322A (en) |
| NO (1) | NO126368B (en) |
| SE (1) | SE346785B (en) |
| ZM (1) | ZM17068A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3527791A1 (en) * | 1985-08-02 | 1987-02-12 | Cassella Ag | 2,5-DIMETHYLPYRROL DERIVATIVES, THEIR PRODUCTION AND THEIR USE |
| TW224974B (en) * | 1991-07-02 | 1994-06-11 | Hoffmann La Roche | |
| GB9803536D0 (en) | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
-
1967
- 1967-12-07 GB GB55708/67A patent/GB1185080A/en not_active Expired
-
1968
- 1968-11-28 IE IE1454/68A patent/IE32781B1/en unknown
- 1968-11-29 DE DE19681811832 patent/DE1811832A1/en active Pending
- 1968-12-02 IS IS1807A patent/IS1807A7/en unknown
- 1968-12-03 NL NL6817322A patent/NL6817322A/xx unknown
- 1968-12-04 AT AT1180468A patent/AT301569B/en not_active IP Right Cessation
- 1968-12-04 ZM ZM170/68A patent/ZM17068A1/en unknown
- 1968-12-05 IL IL31228A patent/IL31228A/en unknown
- 1968-12-05 DK DK594468AA patent/DK126781B/en unknown
- 1968-12-05 ES ES361114A patent/ES361114A1/en not_active Expired
- 1968-12-06 BR BR204654/68A patent/BR6804654D0/en unknown
- 1968-12-06 SE SE16737/68A patent/SE346785B/xx unknown
- 1968-12-06 BE BE725104D patent/BE725104A/xx unknown
- 1968-12-06 NO NO04900/68A patent/NO126368B/no unknown
- 1968-12-06 FR FR176948A patent/FR7874M/fr not_active Expired
- 1968-12-09 CH CH1833468A patent/CH534679A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH534679A (en) | 1973-03-15 |
| DE1811832A1 (en) | 1969-07-03 |
| FR7874M (en) | 1970-04-27 |
| IS1807A7 (en) | 1969-01-22 |
| IL31228A0 (en) | 1969-02-27 |
| ZM17068A1 (en) | 1969-06-17 |
| GB1185080A (en) | 1970-03-18 |
| NO126368B (en) | 1973-01-29 |
| BE725104A (en) | 1969-06-06 |
| DK126781B (en) | 1973-08-20 |
| IL31228A (en) | 1972-04-27 |
| NL6817322A (en) | 1969-06-10 |
| AT301569B (en) | 1972-09-11 |
| IE32781B1 (en) | 1973-11-28 |
| BR6804654D0 (en) | 1973-02-13 |
| IE32781L (en) | 1969-06-07 |
| SE346785B (en) | 1972-07-17 |
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