CA1130305A - Procede d'obtention de 2-naphtaleneethanimidamides disubstituees en n,n' et de leurs intermediaires - Google Patents
Procede d'obtention de 2-naphtaleneethanimidamides disubstituees en n,n' et de leurs intermediairesInfo
- Publication number
- CA1130305A CA1130305A CA330,828A CA330828A CA1130305A CA 1130305 A CA1130305 A CA 1130305A CA 330828 A CA330828 A CA 330828A CA 1130305 A CA1130305 A CA 1130305A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carbon atoms
- naphthylacetonitrile
- hydroxy
- iii
- 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
- LHYUMRWJTVKTPD-UHFFFAOYSA-N 2-naphthalen-2-ylethanimidamide Chemical class C1=CC=CC2=CC(CC(=N)N)=CC=C21 LHYUMRWJTVKTPD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000543 intermediate Substances 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- -1 imido ester salt Chemical class 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 150000002825 nitriles Chemical class 0.000 claims abstract description 11
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- LPCWDVLDJVZIHA-UHFFFAOYSA-N 2-naphthalen-2-ylacetonitrile Chemical compound C1=CC=CC2=CC(CC#N)=CC=C21 LPCWDVLDJVZIHA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- GTTGADPSPVSIJG-UHFFFAOYSA-N ethyl 2-naphthalen-2-ylethanimidate;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(CC(=N)OCC)=CC=C21 GTTGADPSPVSIJG-UHFFFAOYSA-N 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- RFZXGFNZXUATFO-UHFFFAOYSA-N 2-(1-chloronaphthalen-2-yl)acetonitrile Chemical compound C1=CC=C2C(Cl)=C(CC#N)C=CC2=C1 RFZXGFNZXUATFO-UHFFFAOYSA-N 0.000 claims 1
- VCLZSWDXZNYUQB-UHFFFAOYSA-N 2-(1-hydroxynaphthalen-2-yl)acetonitrile Chemical compound C1=CC=C2C(O)=C(CC#N)C=CC2=C1 VCLZSWDXZNYUQB-UHFFFAOYSA-N 0.000 claims 1
- CHVSJQVTEBQKJL-UHFFFAOYSA-N 2-(3-methylnaphthalen-2-yl)acetonitrile Chemical compound C1=CC=C2C=C(CC#N)C(C)=CC2=C1 CHVSJQVTEBQKJL-UHFFFAOYSA-N 0.000 claims 1
- PWWQFJOWVJPYCO-UHFFFAOYSA-N 2-(6-hydroxynaphthalen-2-yl)acetonitrile Chemical compound C1=C(CC#N)C=CC2=CC(O)=CC=C21 PWWQFJOWVJPYCO-UHFFFAOYSA-N 0.000 claims 1
- NLQWCQWHTQUUNU-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)acetonitrile Chemical compound C1=C(CC#N)C=CC2=CC(OC)=CC=C21 NLQWCQWHTQUUNU-UHFFFAOYSA-N 0.000 claims 1
- MZBXTJHQWBYBAL-UHFFFAOYSA-N 2-(6-methylnaphthalen-2-yl)acetonitrile Chemical compound C1=C(CC#N)C=CC2=CC(C)=CC=C21 MZBXTJHQWBYBAL-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000875 corresponding effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 229960005419 nitrogen Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FJSKXQVRKZTKSI-UHFFFAOYSA-N 2,3-dimethylfuran Chemical compound CC=1C=COC=1C FJSKXQVRKZTKSI-UHFFFAOYSA-N 0.000 description 1
- AGWQKZPRUWXKEH-UHFFFAOYSA-N 2-(6-hydroxynaphthalen-2-yl)acetamide hydrochloride Chemical compound Cl.C1=C(O)C=CC2=CC(CC(=N)O)=CC=C21 AGWQKZPRUWXKEH-UHFFFAOYSA-N 0.000 description 1
- ZGWMCFXMLOKXTN-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)acetamide hydrochloride Chemical compound Cl.C1=C(CC(O)=N)C=CC2=CC(OC)=CC=C21 ZGWMCFXMLOKXTN-UHFFFAOYSA-N 0.000 description 1
- VLHPLJIWMWWTBN-UHFFFAOYSA-N 2-(6-methylnaphthalen-2-yl)acetamide hydrochloride Chemical compound Cl.C1=C(CC(O)=N)C=CC2=CC(C)=CC=C21 VLHPLJIWMWWTBN-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LXTQGYPVTFADHK-UHFFFAOYSA-N Cl.C1=C(C=CC2=CC=CC=C12)CC(O)=N Chemical compound Cl.C1=C(C=CC2=CC=CC=C12)CC(O)=N LXTQGYPVTFADHK-UHFFFAOYSA-N 0.000 description 1
- NDDZJZXUJNRLGD-UHFFFAOYSA-N Cl.C1=CC=C2C=C(CC(O)=N)C(C)=CC2=C1 Chemical compound Cl.C1=CC=C2C=C(CC(O)=N)C(C)=CC2=C1 NDDZJZXUJNRLGD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002249 anxiolytic agent Substances 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
- 102220347004 c.89G>A Human genes 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001816 cooling Methods 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 compound CC(N)=N.C1=CC=CC2=CC=CC=C21 PZYUESQIXBTVPG-UHFFFAOYSA-N 0.000 description 1
- CKEYDFOHSHJTHQ-UHFFFAOYSA-N ethyl 2-naphthalen-2-ylethanimidate Chemical compound C1=CC=CC2=CC(CC(=N)OCC)=CC=C21 CKEYDFOHSHJTHQ-UHFFFAOYSA-N 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DIEOESIZLAHURK-UHFFFAOYSA-N n-naphthalen-2-ylacetamide Chemical compound C1=CC=CC2=CC(NC(=O)C)=CC=C21 DIEOESIZLAHURK-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000007039 two-step reaction 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92169078A | 1978-07-03 | 1978-07-03 | |
| US921,690 | 1986-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1130305A true CA1130305A (fr) | 1982-08-24 |
Family
ID=25445831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA330,828A Expired CA1130305A (fr) | 1978-07-03 | 1979-06-29 | Procede d'obtention de 2-naphtaleneethanimidamides disubstituees en n,n' et de leurs intermediaires |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS559095A (fr) |
| AR (1) | AR230619A1 (fr) |
| BE (1) | BE877449A (fr) |
| CA (1) | CA1130305A (fr) |
| CH (1) | CH641764A5 (fr) |
| DE (1) | DE2926828A1 (fr) |
| DK (1) | DK273079A (fr) |
| ES (1) | ES482113A1 (fr) |
| FR (1) | FR2430414A1 (fr) |
| GB (1) | GB2024223B (fr) |
| IT (1) | IT1121792B (fr) |
| NL (1) | NL7904774A (fr) |
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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1434131A (fr) * | 1964-07-31 | 1966-04-08 | Usines Rhone Poulenc Soc D | Nouveaux dérivés de l'acétamidine |
| GB1243186A (en) * | 1967-11-29 | 1971-08-18 | Orsymonde | Improvements in or relating to mandelamidine derivatives |
| ZA696719B (en) * | 1968-10-17 | 1971-04-28 | Lilly Co Eli | 13-manphthylacetamidine and salts thereof |
| FR2036973A1 (fr) * | 1969-04-24 | 1970-12-31 | Orsymonde | |
| US3742000A (en) * | 1969-06-03 | 1973-06-26 | Grace W R & Co | Imidoether and amidine derivatives of substituted fatty amides |
| JPS5246949B2 (fr) * | 1973-10-19 | 1977-11-29 | ||
| DD109864A1 (fr) * | 1973-11-20 | 1974-11-20 | ||
| US3903163A (en) * | 1974-10-02 | 1975-09-02 | Dow Chemical Co | N,N-Disubstituted naphthaleneacetamidines |
| 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 FR FR7917017A patent/FR2430414A1/fr active Granted
- 1979-06-29 CA CA330,828A patent/CA1130305A/fr not_active Expired
- 1979-07-02 CH CH616579A patent/CH641764A5/fr not_active IP Right Cessation
- 1979-07-02 GB GB7922870A patent/GB2024223B/en not_active Expired
- 1979-07-02 ES ES482113A patent/ES482113A1/es not_active Expired
- 1979-07-03 AR AR277173A patent/AR230619A1/es active
- 1979-07-03 JP JP8437179A patent/JPS559095A/ja active Granted
- 1979-07-03 DE DE19792926828 patent/DE2926828A1/de not_active Ceased
- 1979-07-03 BE BE0/196104A patent/BE877449A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2430414A1 (fr) | 1980-02-01 |
| GB2024223A (en) | 1980-01-09 |
| IT7923509A0 (it) | 1979-06-13 |
| JPS559095A (en) | 1980-01-22 |
| CH641764A5 (fr) | 1984-03-15 |
| AR230619A1 (es) | 1984-05-31 |
| BE877449A (fr) | 1980-01-03 |
| GB2024223B (en) | 1982-07-14 |
| FR2430414B1 (fr) | 1984-06-08 |
| ES482113A1 (es) | 1980-04-01 |
| DK273079A (da) | 1980-01-04 |
| DE2926828A1 (de) | 1980-01-17 |
| NL7904774A (nl) | 1980-01-07 |
| IT1121792B (it) | 1986-04-23 |
| JPS6343382B2 (fr) | 1988-08-30 |
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