DE2926828A1 - Verfahren zur herstellung von n,n'- disubstituierten 2-naphthalinaethanimidamiden und ihren salzen und 2-nphthylimidoessigsaeureestersalze - Google Patents
Verfahren zur herstellung von n,n'- disubstituierten 2-naphthalinaethanimidamiden und ihren salzen und 2-nphthylimidoessigsaeureestersalzeInfo
- Publication number
- DE2926828A1 DE2926828A1 DE19792926828 DE2926828A DE2926828A1 DE 2926828 A1 DE2926828 A1 DE 2926828A1 DE 19792926828 DE19792926828 DE 19792926828 DE 2926828 A DE2926828 A DE 2926828A DE 2926828 A1 DE2926828 A1 DE 2926828A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- salts
- carbon atoms
- formula iii
- acid ester
- 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.)
- Ceased
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052757 nitrogen Inorganic materials 0.000 title description 3
- -1 ester salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- LPCWDVLDJVZIHA-UHFFFAOYSA-N 2-naphthalen-2-ylacetonitrile Chemical compound C1=CC=CC2=CC(CC#N)=CC=C21 LPCWDVLDJVZIHA-UHFFFAOYSA-N 0.000 claims description 3
- LHYUMRWJTVKTPD-UHFFFAOYSA-N 2-naphthalen-2-ylethanimidamide Chemical class C1=CC=CC2=CC(CC(=N)N)=CC=C21 LHYUMRWJTVKTPD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FJSKXQVRKZTKSI-UHFFFAOYSA-N 2,3-dimethylfuran Chemical compound CC=1C=COC=1C FJSKXQVRKZTKSI-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- PZYUESQIXBTVPG-UHFFFAOYSA-N ethanimidamide;naphthalene Chemical class CC(N)=N.C1=CC=CC2=CC=CC=C21 PZYUESQIXBTVPG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92169078A | 1978-07-03 | 1978-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2926828A1 true DE2926828A1 (de) | 1980-01-17 |
Family
ID=25445831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792926828 Ceased DE2926828A1 (de) | 1978-07-03 | 1979-07-03 | Verfahren zur herstellung von n,n'- disubstituierten 2-naphthalinaethanimidamiden und ihren salzen und 2-nphthylimidoessigsaeureestersalze |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS559095A (sv) |
| AR (1) | AR230619A1 (sv) |
| BE (1) | BE877449A (sv) |
| CA (1) | CA1130305A (sv) |
| CH (1) | CH641764A5 (sv) |
| DE (1) | DE2926828A1 (sv) |
| DK (1) | DK273079A (sv) |
| ES (1) | ES482113A1 (sv) |
| FR (1) | FR2430414A1 (sv) |
| GB (1) | GB2024223B (sv) |
| IT (1) | IT1121792B (sv) |
| NL (1) | NL7904774A (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495108A (en) * | 1983-03-11 | 1985-01-22 | E. I. Du Pont De Nemours And Company | Process for preparing dialkyl propanediimidate dihydrohalides |
| US5180379A (en) * | 1991-04-04 | 1993-01-19 | Minnesota Mining And Manufacturing Company | Electrode with pre-wired leads |
| JPH08293371A (ja) * | 1995-04-20 | 1996-11-05 | Nippon Denki Factory Eng Kk | Ｉｃソケット |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468926A1 (de) * | 1964-07-31 | 1969-02-20 | Rhone Poulenc Sa | Verfahren zur Herstellung von neuen Acetamidinderivaten |
| DE1951258A1 (de) * | 1968-10-17 | 1970-11-05 | Lilly Co Eli | Beta-Naphthylacetamidin und dessen Salze |
| US3742000A (en) * | 1969-06-03 | 1973-06-26 | Grace W R & Co | Imidoether and amidine derivatives of substituted fatty amides |
| DE1817861B2 (de) * | 1967-11-29 | 1973-09-06 | Orsymonde, Paris | N-alkylierte 3,4-methylendioxymandelsaeureamidine und deren pharmakologisch nicht giftige saeureanlagerungssalze und diese enthaltende pharmazeutische mittel |
| DD109864A1 (sv) * | 1973-11-20 | 1974-11-20 | ||
| DE2449840A1 (de) * | 1973-10-19 | 1975-04-24 | Kao Corp | Adamantylamidine und verfahren zu ihrer herstellung |
| DE2019307B2 (de) * | 1969-04-24 | 1979-09-27 | Orsymonde S.A., Paris | Mandelamidinderivate und sie enthaltende Arzneimittel |
| DE2542791C2 (de) * | 1974-10-02 | 1984-11-08 | The Dow Chemical Co., Midland, Mich. | N,N'-Disubstituierte Naphthylacetamidine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5198201A (en) * | 1975-02-18 | 1976-08-30 | n22 chikan omega amijino arufua aminosanjudotaimataha sonosanfukaenno seizoho |
-
1979
- 1979-06-13 IT IT23509/79A patent/IT1121792B/it active
- 1979-06-19 NL NL7904774A patent/NL7904774A/nl not_active Application Discontinuation
- 1979-06-28 DK DK273079A patent/DK273079A/da not_active Application Discontinuation
- 1979-06-29 CA CA330,828A patent/CA1130305A/en not_active Expired
- 1979-06-29 FR FR7917017A patent/FR2430414A1/fr active Granted
- 1979-07-02 ES ES482113A patent/ES482113A1/es not_active Expired
- 1979-07-02 GB GB7922870A patent/GB2024223B/en not_active Expired
- 1979-07-02 CH CH616579A patent/CH641764A5/fr not_active IP Right Cessation
- 1979-07-03 BE BE0/196104A patent/BE877449A/fr not_active IP Right Cessation
- 1979-07-03 DE DE19792926828 patent/DE2926828A1/de not_active Ceased
- 1979-07-03 AR AR277173A patent/AR230619A1/es active
- 1979-07-03 JP JP8437179A patent/JPS559095A/ja active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468926A1 (de) * | 1964-07-31 | 1969-02-20 | Rhone Poulenc Sa | Verfahren zur Herstellung von neuen Acetamidinderivaten |
| DE1817861B2 (de) * | 1967-11-29 | 1973-09-06 | Orsymonde, Paris | N-alkylierte 3,4-methylendioxymandelsaeureamidine und deren pharmakologisch nicht giftige saeureanlagerungssalze und diese enthaltende pharmazeutische mittel |
| DE1951258A1 (de) * | 1968-10-17 | 1970-11-05 | Lilly Co Eli | Beta-Naphthylacetamidin und dessen Salze |
| DE2019307B2 (de) * | 1969-04-24 | 1979-09-27 | Orsymonde S.A., Paris | Mandelamidinderivate und sie enthaltende Arzneimittel |
| US3742000A (en) * | 1969-06-03 | 1973-06-26 | Grace W R & Co | Imidoether and amidine derivatives of substituted fatty amides |
| DE2449840A1 (de) * | 1973-10-19 | 1975-04-24 | Kao Corp | Adamantylamidine und verfahren zu ihrer herstellung |
| DD109864A1 (sv) * | 1973-11-20 | 1974-11-20 | ||
| DE2542791C2 (de) * | 1974-10-02 | 1984-11-08 | The Dow Chemical Co., Midland, Mich. | N,N'-Disubstituierte Naphthylacetamidine |
Non-Patent Citations (4)
| Title |
|---|
| J.Pharm.Sci. 62 (1973), S.1899-1900 * |
| Pharmazie 28 (1973), S.427-431 * |
| Pharmazie 28 (1973), S.724-729 * |
| Pharmazie 29 (1974), S.263-267 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2430414A1 (fr) | 1980-02-01 |
| CA1130305A (en) | 1982-08-24 |
| CH641764A5 (fr) | 1984-03-15 |
| ES482113A1 (es) | 1980-04-01 |
| JPS6343382B2 (sv) | 1988-08-30 |
| GB2024223A (en) | 1980-01-09 |
| IT7923509A0 (it) | 1979-06-13 |
| DK273079A (da) | 1980-01-04 |
| GB2024223B (en) | 1982-07-14 |
| FR2430414B1 (sv) | 1984-06-08 |
| JPS559095A (en) | 1980-01-22 |
| BE877449A (fr) | 1980-01-03 |
| IT1121792B (it) | 1986-04-23 |
| AR230619A1 (es) | 1984-05-31 |
| NL7904774A (nl) | 1980-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |