US3692835A - Pharmacologically active amino-ethyl oximes - Google Patents
Pharmacologically active amino-ethyl oximes Download PDFInfo
- Publication number
- US3692835A US3692835A US715571A US3692835DA US3692835A US 3692835 A US3692835 A US 3692835A US 715571 A US715571 A US 715571A US 3692835D A US3692835D A US 3692835DA US 3692835 A US3692835 A US 3692835A
- Authority
- US
- United States
- Prior art keywords
- group
- mls
- ethyl
- ether
- amino
- 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 - Lifetime
Links
- -1 amino-ethyl oximes Chemical class 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000007513 acids Chemical class 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 13
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 9
- 125000005843 halogen group Chemical group 0.000 abstract description 6
- 150000003840 hydrochlorides Chemical class 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 230000001430 anti-depressive effect Effects 0.000 abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 4
- 125000005605 benzo group Chemical group 0.000 abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract description 3
- 150000002923 oximes Chemical class 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract description 2
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- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- VYXVPOVYYRXJCS-UHFFFAOYSA-N hydroxylamine;dihydrochloride Chemical compound Cl.Cl.ON VYXVPOVYYRXJCS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YBSXDWIAUZOFFV-UHFFFAOYSA-N n-[(2,6-dichlorophenyl)methylidene]hydroxylamine Chemical compound ON=CC1=C(Cl)C=CC=C1Cl YBSXDWIAUZOFFV-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Definitions
- the temperature of the reaction mixture may vary between rather wide limits. As a rule, however, it will be between 0 and 50 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL676704810A NL150105B (nl) | 1967-04-05 | 1967-04-05 | Verbindingen met antidepressieve werking. |
| NL676717001A NL151361B (nl) | 1967-12-14 | 1967-12-14 | Verbindingen met centrale werking. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3692835A true US3692835A (en) | 1972-09-19 |
Family
ID=26644178
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US715571A Expired - Lifetime US3692835A (en) | 1967-04-05 | 1968-03-25 | Pharmacologically active amino-ethyl oximes |
| US06/814,019 Expired - Fee Related US5008452A (en) | 1967-04-05 | 1989-12-20 | Aminoethyl oximes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/814,019 Expired - Fee Related US5008452A (en) | 1967-04-05 | 1989-12-20 | Aminoethyl oximes |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US3692835A (en, 2012) |
| AT (4) | AT289759B (en, 2012) |
| BE (1) | BE713172A (en, 2012) |
| CA (1) | CA959063A (en, 2012) |
| CH (2) | CH534669A (en, 2012) |
| DE (1) | DE1768100C2 (en, 2012) |
| DK (1) | DK120384B (en, 2012) |
| ES (2) | ES352329A1 (en, 2012) |
| FI (1) | FI49957C (en, 2012) |
| FR (2) | FR1583796A (en, 2012) |
| GB (1) | GB1205665A (en, 2012) |
| IE (1) | IE33428B1 (en, 2012) |
| IL (1) | IL29740A (en, 2012) |
| NO (1) | NO125974B (en, 2012) |
| SE (1) | SE352078B (en, 2012) |
| YU (3) | YU33857B (en, 2012) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903164A (en) * | 1972-03-24 | 1975-09-02 | Kabi Ab | Pharmacodynamically active amino alkyloxim ethers |
| US4038317A (en) * | 1975-02-12 | 1977-07-26 | Seperic | O-aminoalkyl oximes |
| US4060631A (en) * | 1975-03-20 | 1977-11-29 | U.S. Philips Corporation | Aminoethyl oxime ethers having anti-depressive activity |
| US4062969A (en) * | 1976-06-25 | 1977-12-13 | Union Carbide Corporation | Dioxane oxime compounds and pesticidal dioxane carbamoyloxime derivatives |
| US4077999A (en) * | 1976-01-27 | 1978-03-07 | Egyt Gyogyszervegyeszeti Gyar | Novel oxime ethers |
| US4081552A (en) * | 1975-03-20 | 1978-03-28 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4081551A (en) * | 1975-03-20 | 1978-03-28 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4085225A (en) * | 1975-03-20 | 1978-04-18 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4086361A (en) * | 1975-03-20 | 1978-04-25 | U.S. Philips Corporation | Aminoethyl oximes having anti-depressive activity |
| FR2387945A1 (fr) * | 1977-03-02 | 1978-11-17 | Ciba Geigy Ag | Agents favorisant la croissance des plantes et phytoprotecteurs a base d'oximethers et d'oximesters |
| US4192893A (en) * | 1975-03-20 | 1980-03-11 | U.S. Philips Corporation | Anti-depressive compounds |
| US4242348A (en) * | 1970-06-11 | 1980-12-30 | Duphar International Research B.V. | Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters |
| US4328227A (en) * | 1976-12-24 | 1982-05-04 | Hoechst Aktiengesellschaft | Novel O-propyloximes |
| US4342763A (en) * | 1979-02-13 | 1982-08-03 | Provesan S.A. | P-Chloroacetophenone oxime compounds and pharmaceutical compositions |
| US4358450A (en) * | 1976-12-24 | 1982-11-09 | Hoechst Aktiengesellschaft | O-Alkylated oximes and pharmaceutical composition thereof |
| US4388106A (en) * | 1978-08-31 | 1983-06-14 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488900A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488899A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488898A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4548756A (en) * | 1977-03-02 | 1985-10-22 | Ciba Geigy Corporation | Oxime ethers |
| US4581060A (en) * | 1977-03-02 | 1986-04-08 | Ciba-Geigy Corporation | Compositions, which promote plant growth and protect plants, based on oxime ethers and oxime esters |
| US4709095A (en) * | 1984-08-06 | 1987-11-24 | Yoshitomi Pharmaceutical Industries, Ltd. | Ortho-aminomethylphenol compounds |
| US4845287A (en) * | 1986-01-16 | 1989-07-04 | Bayer Aktiengesellschaft | Hydroxybenzaldoxime O-ethers |
| US5008452A (en) * | 1967-04-05 | 1991-04-16 | Duphar International Research B.V. | Aminoethyl oximes |
| WO2018096376A1 (en) | 2016-11-24 | 2018-05-31 | Mta Támogatott Kutatócsoportok Irodája | Compositions for organ preservation |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1600969A (en) * | 1977-01-07 | 1981-10-21 | Acf Chemiefarma Nv | Heterocyclic compounds |
| AU532700B2 (en) * | 1979-04-02 | 1983-10-13 | Sumitomo Chemical Company, Limited | Diphenylalkanoether |
| FR2518090A1 (fr) * | 1981-12-11 | 1983-06-17 | Univablot | Ethers d'oximes a-b insatures, leur procede de preparation et leur utilisation comme medicament |
| US5665756A (en) * | 1994-08-03 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Aminoalkyloximes useful in the treatment of depression and obsessive compulsive disorders |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1733462A (en) * | 1926-09-23 | 1929-10-29 | Winthrop Chem Co Inc | New basic oxime ethers of cyclic compounds |
| US3270055A (en) * | 1963-09-11 | 1966-08-30 | Engelhard Hermann | 5-aminoalkoxy ethers of 5-hydroxyimino-10, 11-dihydro-5h-dibenzo (a, d) cyclohepta (1, 4) dienes |
| US3441608A (en) * | 1964-11-26 | 1969-04-29 | Bayer Ag | 5beta - n - methylamino - ethoxyimino - 5h - dibenzo - (a,d) - 10,11 - dihydrocycloheptene and non-toxic pharmaceutically acceptable salts thereof and their production |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6503019A (en, 2012) * | 1965-03-10 | 1966-09-12 | ||
| US4235931A (en) * | 1967-04-05 | 1980-11-25 | Duphar International Research B.V. | Compounds having pharmacological properties |
| US3692835A (en) * | 1967-04-05 | 1972-09-19 | Jan Van Dijk | Pharmacologically active amino-ethyl oximes |
| NL150105B (nl) * | 1967-04-05 | 1976-07-15 | Philips Nv | Verbindingen met antidepressieve werking. |
| US4192818A (en) * | 1967-04-05 | 1980-03-11 | Duphar International Research B.V. | Compounds having pharmacological properties |
| NL7503312A (nl) * | 1975-03-20 | 1976-09-22 | Philips Nv | Verbindingen met antidepressieve werking. |
-
1968
- 1968-03-25 US US715571A patent/US3692835A/en not_active Expired - Lifetime
- 1968-03-29 FR FR1583796D patent/FR1583796A/fr not_active Expired
- 1968-03-30 DE DE1768100A patent/DE1768100C2/de not_active Expired
- 1968-04-02 CA CA016,478A patent/CA959063A/en not_active Expired
- 1968-04-02 AT AT141170A patent/AT289759B/de not_active IP Right Cessation
- 1968-04-02 SE SE04388/68A patent/SE352078B/xx unknown
- 1968-04-02 AT AT141370A patent/AT289761B/de not_active IP Right Cessation
- 1968-04-02 CH CH484268A patent/CH534669A/de not_active IP Right Cessation
- 1968-04-02 DK DK144068AA patent/DK120384B/da unknown
- 1968-04-02 NO NO681268A patent/NO125974B/no unknown
- 1968-04-02 GB GB05735/68A patent/GB1205665A/en not_active Expired
- 1968-04-02 AT AT141270A patent/AT289760B/de not_active IP Right Cessation
- 1968-04-02 AT AT319868A patent/AT289758B/de not_active IP Right Cessation
- 1968-04-02 IE IE381/68A patent/IE33428B1/xx unknown
- 1968-04-02 CH CH1493570A patent/CH535209A/de not_active IP Right Cessation
- 1968-04-02 IL IL29740A patent/IL29740A/en unknown
- 1968-04-03 YU YU765/68A patent/YU33857B/xx unknown
- 1968-04-03 BE BE713172D patent/BE713172A/xx not_active IP Right Cessation
- 1968-04-04 FI FI680931A patent/FI49957C/fi active
- 1968-06-28 FR FR157096A patent/FR7901M/fr not_active Expired
-
1969
- 1969-04-03 ES ES352329A patent/ES352329A1/es not_active Expired
- 1969-05-14 ES ES367237A patent/ES367237A1/es not_active Expired
-
1973
- 1973-03-28 YU YU845/73A patent/YU33858B/xx unknown
- 1973-03-28 YU YU847/73A patent/YU33859B/xx unknown
-
1989
- 1989-12-20 US US06/814,019 patent/US5008452A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1733462A (en) * | 1926-09-23 | 1929-10-29 | Winthrop Chem Co Inc | New basic oxime ethers of cyclic compounds |
| US3270055A (en) * | 1963-09-11 | 1966-08-30 | Engelhard Hermann | 5-aminoalkoxy ethers of 5-hydroxyimino-10, 11-dihydro-5h-dibenzo (a, d) cyclohepta (1, 4) dienes |
| US3441608A (en) * | 1964-11-26 | 1969-04-29 | Bayer Ag | 5beta - n - methylamino - ethoxyimino - 5h - dibenzo - (a,d) - 10,11 - dihydrocycloheptene and non-toxic pharmaceutically acceptable salts thereof and their production |
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts, Vol. 61, 10545 10546(1964) * |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008452A (en) * | 1967-04-05 | 1991-04-16 | Duphar International Research B.V. | Aminoethyl oximes |
| US4242348A (en) * | 1970-06-11 | 1980-12-30 | Duphar International Research B.V. | Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters |
| US4317835A (en) * | 1970-06-11 | 1982-03-02 | Duphar International Research B.V. | Novel basic substituted-alkylidenamino-oxyalkyl-carboxylic acid esters |
| US3903164A (en) * | 1972-03-24 | 1975-09-02 | Kabi Ab | Pharmacodynamically active amino alkyloxim ethers |
| US4038317A (en) * | 1975-02-12 | 1977-07-26 | Seperic | O-aminoalkyl oximes |
| US4086361A (en) * | 1975-03-20 | 1978-04-25 | U.S. Philips Corporation | Aminoethyl oximes having anti-depressive activity |
| US4081551A (en) * | 1975-03-20 | 1978-03-28 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4085225A (en) * | 1975-03-20 | 1978-04-18 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4192893A (en) * | 1975-03-20 | 1980-03-11 | U.S. Philips Corporation | Anti-depressive compounds |
| US4081552A (en) * | 1975-03-20 | 1978-03-28 | U.S. Philips Corporation | Oxime ethers having anti-depressive activity |
| US4060631A (en) * | 1975-03-20 | 1977-11-29 | U.S. Philips Corporation | Aminoethyl oxime ethers having anti-depressive activity |
| US4077999A (en) * | 1976-01-27 | 1978-03-07 | Egyt Gyogyszervegyeszeti Gyar | Novel oxime ethers |
| US4062969A (en) * | 1976-06-25 | 1977-12-13 | Union Carbide Corporation | Dioxane oxime compounds and pesticidal dioxane carbamoyloxime derivatives |
| US4328227A (en) * | 1976-12-24 | 1982-05-04 | Hoechst Aktiengesellschaft | Novel O-propyloximes |
| US4358450A (en) * | 1976-12-24 | 1982-11-09 | Hoechst Aktiengesellschaft | O-Alkylated oximes and pharmaceutical composition thereof |
| US4548756A (en) * | 1977-03-02 | 1985-10-22 | Ciba Geigy Corporation | Oxime ethers |
| FR2387945A1 (fr) * | 1977-03-02 | 1978-11-17 | Ciba Geigy Ag | Agents favorisant la croissance des plantes et phytoprotecteurs a base d'oximethers et d'oximesters |
| US4581060A (en) * | 1977-03-02 | 1986-04-08 | Ciba-Geigy Corporation | Compositions, which promote plant growth and protect plants, based on oxime ethers and oxime esters |
| US4388106A (en) * | 1978-08-31 | 1983-06-14 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4505742A (en) * | 1978-08-31 | 1985-03-19 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4450000A (en) * | 1978-08-31 | 1984-05-22 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4486224A (en) * | 1978-08-31 | 1984-12-04 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488900A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488899A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488898A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4439228A (en) * | 1978-08-31 | 1984-03-27 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4439230A (en) * | 1978-08-31 | 1984-03-27 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4437879A (en) | 1978-08-31 | 1984-03-20 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4342763A (en) * | 1979-02-13 | 1982-08-03 | Provesan S.A. | P-Chloroacetophenone oxime compounds and pharmaceutical compositions |
| US4709095A (en) * | 1984-08-06 | 1987-11-24 | Yoshitomi Pharmaceutical Industries, Ltd. | Ortho-aminomethylphenol compounds |
| US4845287A (en) * | 1986-01-16 | 1989-07-04 | Bayer Aktiengesellschaft | Hydroxybenzaldoxime O-ethers |
| WO2018096376A1 (en) | 2016-11-24 | 2018-05-31 | Mta Támogatott Kutatócsoportok Irodája | Compositions for organ preservation |
Also Published As
| Publication number | Publication date |
|---|---|
| IE33428B1 (en) | 1974-06-26 |
| AT289759B (de) | 1971-05-10 |
| AT289761B (de) | 1971-05-10 |
| YU33859B (en) | 1978-06-30 |
| DK120384B (da) | 1971-05-24 |
| CH535209A (de) | 1973-03-31 |
| FR7901M (en, 2012) | 1970-05-11 |
| AT289760B (de) | 1971-05-10 |
| ES352329A1 (es) | 1969-12-16 |
| BE713172A (en, 2012) | 1968-10-03 |
| FI49957B (en, 2012) | 1975-07-31 |
| IE33428L (en) | 1968-10-05 |
| IL29740A0 (en) | 1968-06-20 |
| CA959063A (en) | 1974-12-10 |
| US5008452A (en) | 1991-04-16 |
| YU75668A (en) | 1977-12-31 |
| DE1768100A1 (de) | 1971-10-14 |
| AT289758B (de) | 1971-05-10 |
| SE352078B (en, 2012) | 1972-12-18 |
| ES367237A1 (es) | 1971-06-16 |
| NO125974B (en, 2012) | 1972-12-04 |
| YU33857B (en) | 1978-06-30 |
| YU84573A (en) | 1977-12-31 |
| YU33858B (en) | 1978-06-30 |
| FI49957C (fi) | 1975-11-10 |
| FR1583796A (en, 2012) | 1969-12-05 |
| DE1768100C2 (de) | 1986-02-06 |
| YU84773A (en) | 1977-12-31 |
| GB1205665A (en) | 1970-09-16 |
| IL29740A (en) | 1971-11-29 |
| CH534669A (de) | 1973-03-15 |
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