DE1174781B - Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinen - Google Patents
Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinenInfo
- Publication number
- DE1174781B DE1174781B DEF32847A DEF0032847A DE1174781B DE 1174781 B DE1174781 B DE 1174781B DE F32847 A DEF32847 A DE F32847A DE F0032847 A DEF0032847 A DE F0032847A DE 1174781 B DE1174781 B DE 1174781B
- Authority
- DE
- Germany
- Prior art keywords
- salts
- dimethylpyrrolidine
- guanidinoethyl
- guanidinoalkyl
- pyrrolidines
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003235 pyrrolidines Chemical class 0.000 title description 3
- -1 cyanogen halides Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- KUYCYCVBFVOPOU-UHFFFAOYSA-N 2-[2-(3,3-dimethylpyrrolidin-1-yl)ethyl]guanidine sulfuric acid Chemical compound S(=O)(=O)(O)O.N(C(=N)N)CCN1CC(CC1)(C)C KUYCYCVBFVOPOU-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000030214 innervation Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UOLFIRYVZLZHDX-UHFFFAOYSA-N 2-(3,3-dimethylpyrrolidin-1-yl)ethanamine Chemical compound CC1(C)CCN(CCN)C1 UOLFIRYVZLZHDX-UHFFFAOYSA-N 0.000 description 2
- XBQNZPDIRJPFAI-UHFFFAOYSA-N 3,3-dimethylpyrrolidine Chemical compound CC1(C)CCNC1 XBQNZPDIRJPFAI-UHFFFAOYSA-N 0.000 description 2
- 208000003098 Ganglion Cysts Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 208000005400 Synovial Cyst Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 150000003976 azacycloalkanes Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 2
- 206010038464 renal hypertension Diseases 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- STDJRYDBFFDKCR-UHFFFAOYSA-N 1,2,2-trimethylpyrrolidine Chemical compound CN1CCCC1(C)C STDJRYDBFFDKCR-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- NJDDNCANXFHJLO-UHFFFAOYSA-N 3,3,4,4-tetramethylpyrrolidine Chemical compound CC1(C)CNCC1(C)C NJDDNCANXFHJLO-UHFFFAOYSA-N 0.000 description 1
- XGJPUQFWFRCCFO-UHFFFAOYSA-N 3,3,4,4-tetramethylpyrrolidine-2,5-dione Chemical compound CC1(C)C(=O)NC(=O)C1(C)C XGJPUQFWFRCCFO-UHFFFAOYSA-N 0.000 description 1
- LUCLDOSYMMNBFY-UHFFFAOYSA-N 3,3,4-trimethylpyrrolidin-2-one Chemical compound CC1CNC(=O)C1(C)C LUCLDOSYMMNBFY-UHFFFAOYSA-N 0.000 description 1
- SUPYQTKKYLUOBW-UHFFFAOYSA-N 3,3,4-trimethylpyrrolidine-2,5-dione Chemical compound CC1C(=O)NC(=O)C1(C)C SUPYQTKKYLUOBW-UHFFFAOYSA-N 0.000 description 1
- RDEHRKLSYJBKDV-UHFFFAOYSA-N 3,4-dimethylpyrrolidine Chemical compound CC1CNCC1C RDEHRKLSYJBKDV-UHFFFAOYSA-N 0.000 description 1
- DWEXCXIEVRCDTE-UHFFFAOYSA-N 3-ethyl-3-methylpyrrolidine Chemical compound CCC1(C)CCNC1 DWEXCXIEVRCDTE-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- NCPOMMSEMXHXOL-UHFFFAOYSA-N C(#N)CN1CC(C(C1)(C)C)(C)C Chemical compound C(#N)CN1CC(C(C1)(C)C)(C)C NCPOMMSEMXHXOL-UHFFFAOYSA-N 0.000 description 1
- FYVBCSCJHKMVDO-UHFFFAOYSA-N CC1(C)CN(CCN)CC1.OS(O)(=O)=O Chemical compound CC1(C)CN(CCN)CC1.OS(O)(=O)=O FYVBCSCJHKMVDO-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IFCALKJLSQXEOA-UHFFFAOYSA-N NCCN1CC(C(C1)(C)C)(C)C Chemical compound NCCN1CC(C(C1)(C)C)(C)C IFCALKJLSQXEOA-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- MBEGFNBBAVRKLK-UHFFFAOYSA-N sodium;iminomethylideneazanide Chemical compound [Na+].[NH-]C#N MBEGFNBBAVRKLK-UHFFFAOYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 description 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
- C07D295/12—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32847A DE1174781B (de) | 1960-12-24 | 1960-12-24 | Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinen |
| BE611886A BE611886A (fr) | 1960-12-24 | 1961-12-22 | Procédé de fabrication de dérivés de la guanidine |
| GB46107/61A GB933686A (en) | 1960-12-24 | 1961-12-22 | New guanidine derivatives |
| SE12911/61A SE303498B (enrdf_load_html_response) | 1960-12-24 | 1961-12-22 | |
| FR882967A FR1506253A (fr) | 1960-12-24 | 1961-12-23 | Procédé de fabrication de dérivés de la guanidine |
| FR891925A FR2124M (fr) | 1960-12-24 | 1962-03-22 | Médicament a base de la n-(2-guanidinoéthyl)-3,3-diméthylpyrrolidine ou de ses sels, pour abaisser la tension sanguine. |
| FR891924A FR2123M (fr) | 1960-12-24 | 1962-03-22 | Médicament a base de n-(2-guanidinoéthyl)-3,3,4,4-tétraméthylpyrrolidine ou de ses sels, pour abaisser la tension sanguine. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32847A DE1174781B (de) | 1960-12-24 | 1960-12-24 | Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1174781B true DE1174781B (de) | 1964-07-30 |
Family
ID=7094822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32847A Pending DE1174781B (de) | 1960-12-24 | 1960-12-24 | Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE611886A (enrdf_load_html_response) |
| DE (1) | DE1174781B (enrdf_load_html_response) |
| FR (3) | FR1506253A (enrdf_load_html_response) |
| GB (1) | GB933686A (enrdf_load_html_response) |
| SE (1) | SE303498B (enrdf_load_html_response) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371093A (en) * | 1961-08-08 | 1968-02-27 | Sterling Drug Inc | N-lower-alkyl and n-substituted-lower-alkyl-n-(and n, n-bis-)[(1-piperidyl)-lower-alkyl]amines |
| IE52663B1 (en) * | 1980-04-02 | 1988-01-20 | Warner Lambert Co | Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids |
| US4350704A (en) * | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| CN105859604B (zh) * | 2016-04-14 | 2018-02-23 | 梯尔希（南京）药物研发有限公司 | 一种氘代乙琥胺‑d5的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH346879A (de) * | 1958-06-10 | 1960-06-15 | Ciba Geigy | Verfahren zur Herstellung von neuen Guanidinen |
-
1960
- 1960-12-24 DE DEF32847A patent/DE1174781B/de active Pending
-
1961
- 1961-12-22 SE SE12911/61A patent/SE303498B/xx unknown
- 1961-12-22 GB GB46107/61A patent/GB933686A/en not_active Expired
- 1961-12-22 BE BE611886A patent/BE611886A/fr unknown
- 1961-12-23 FR FR882967A patent/FR1506253A/fr not_active Expired
-
1962
- 1962-03-22 FR FR891925A patent/FR2124M/fr not_active Expired
- 1962-03-22 FR FR891924A patent/FR2123M/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH346879A (de) * | 1958-06-10 | 1960-06-15 | Ciba Geigy | Verfahren zur Herstellung von neuen Guanidinen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB933686A (en) | 1963-08-08 |
| BE611886A (fr) | 1962-06-22 |
| FR2123M (fr) | 1963-11-04 |
| FR1506253A (fr) | 1967-12-22 |
| SE303498B (enrdf_load_html_response) | 1968-09-02 |
| FR2124M (fr) | 1963-11-04 |
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