CA1054149A - O-aminoalkyloximes - Google Patents

O-aminoalkyloximes

Info

Publication number: CA1054149A
Authority: CA; Canada
Prior art keywords: ylidene; radical; tert; formula; butyl
Prior art date: 1976-02-13
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

Application number

CA245,715A

Other languages

English (en)

Inventor

Camille G. Wermuth

Jean Schwartz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Seperic SA

Original Assignee

Seperic SA

Priority date (The priority date 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 date listed.)

1976-02-13

Filing date

1976-02-13

Publication date

1979-05-08

1976-02-13 Application filed by Seperic SA filed Critical Seperic SA

1976-02-13 Priority to CA245,715A priority Critical patent/CA1054149A/fr

1979-05-08 Application granted granted Critical

1979-05-08 Publication of CA1054149A publication Critical patent/CA1054149A/fr

Status Expired legal-status Critical Current

Links

-1 alkoxy radicals Chemical class 0.000 claims abstract description 49
150000001875 compounds Chemical class 0.000 claims abstract description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
150000003254 radicals Chemical group 0.000 claims abstract description 5
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
230000008569 process Effects 0.000 claims description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 12
150000002923 oximes Chemical class 0.000 claims description 12
150000002924 oxiranes Chemical class 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
238000001704 evaporation Methods 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000003141 primary amines Chemical class 0.000 claims description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
230000008020 evaporation Effects 0.000 claims description 4
229910052739 hydrogen Chemical group 0.000 claims description 4
LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims 6
239000000376 reactant Substances 0.000 claims 5
239000000126 substance Substances 0.000 claims 5
238000010992 reflux Methods 0.000 claims 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
239000001257 hydrogen Chemical group 0.000 claims 1
VZGCWPMHKLHOAG-UHFFFAOYSA-N n-[(2-chlorophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=CC=C(Cl)C=1C(=NO)C1=CC=CC=C1 VZGCWPMHKLHOAG-UHFFFAOYSA-N 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
239000002220 antihypertensive agent Substances 0.000 abstract 1
229940127088 antihypertensive drug Drugs 0.000 abstract 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 6
239000003708 ampul Substances 0.000 description 6
229960001317 isoprenaline Drugs 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
229960001701 chloroform Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
229940076134 benzene Drugs 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000556 agonist Substances 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
230000002860 competitive effect Effects 0.000 description 2
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
230000000297 inotrophic effect Effects 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
BKKNYKDLLKAQRJ-UHFFFAOYSA-N 9-(oxiran-2-ylmethoxy)fluoren-1-imine Chemical compound N=C1C=CC=C(C2=CC=CC=C22)C1=C2OCC1CO1 BKKNYKDLLKAQRJ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
230000002057 chronotropic effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
239000005555 hypertensive agent Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
CRNNFEKVPRFZKJ-UHFFFAOYSA-N n-fluoren-9-ylidenehydroxylamine Chemical compound C1=CC=C2C(=NO)C3=CC=CC=C3C2=C1 CRNNFEKVPRFZKJ-UHFFFAOYSA-N 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
SPDFSSLYVRCMDZ-UHFFFAOYSA-N octane-2,5-dione Chemical compound CCCC(=O)CCC(C)=O SPDFSSLYVRCMDZ-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA245,715A 1976-02-13 1976-02-13 O-aminoalkyloximes Expired CA1054149A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA245,715A CA1054149A (fr)	1976-02-13	1976-02-13	O-aminoalkyloximes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA245,715A CA1054149A (fr)	1976-02-13	1976-02-13	O-aminoalkyloximes

Publications (1)

Publication Number	Publication Date
CA1054149A true CA1054149A (fr)	1979-05-08

Family

ID=4105226

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA245,715A Expired CA1054149A (fr)	1976-02-13	1976-02-13	O-aminoalkyloximes

Country Status (1)

Country	Link
CA (1)	CA1054149A (fr)

1976
- 1976-02-13 CA CA245,715A patent/CA1054149A/fr not_active Expired

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