CH649526A5 - Process for the preparation of (Z)-1,2-diphenyl-1-[p-(2-dimethyl-aminoethoxy)phenyl]but-1-ene - Google Patents

Process for the preparation of (Z)-1,2-diphenyl-1-[p-(2-dimethyl-aminoethoxy)phenyl]but-1-ene Download PDF

Info

Publication number: CH649526A5
Authority: CH; Switzerland
Prior art keywords: isomer; salt; diphenyl; tartaric acid; mixture
Prior art date: 1981-04-07

Application number

CH2118/82A

Other languages

German (de)

English (en)

Inventor

Laszlo Dr Magdanyi

Antal Hutak

Ede Szatmari

Istvan Dr Simonyi

Jozsef Halmos

Fereno Nemere

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1981-04-07

Filing date

1982-04-06

Publication date

1985-05-31

1982-04-06 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1985-05-31 Publication of CH649526A5 publication Critical patent/CH649526A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title claims abstract description 10
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 59
239000000203 mixture Substances 0.000 claims abstract description 43
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims abstract description 32
239000002253 acid Substances 0.000 claims abstract description 21
230000015572 biosynthetic process Effects 0.000 claims abstract description 21
238000002425 crystallisation Methods 0.000 claims abstract description 11
239000003960 organic solvent Substances 0.000 claims abstract description 8
HZGJFTIIKFEPNW-WOJBJXKFSA-N CN(C([C@@](O)([C@](O)(C(=O)O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)=O)C Chemical compound CN(C([C@@](O)([C@](O)(C(=O)O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)=O)C HZGJFTIIKFEPNW-WOJBJXKFSA-N 0.000 claims abstract description 7
238000006243 chemical reaction Methods 0.000 claims abstract description 7
238000001640 fractional crystallisation Methods 0.000 claims abstract description 7
206010006187 Breast cancer Diseases 0.000 claims abstract description 3
208000026310 Breast neoplasm Diseases 0.000 claims abstract description 3
239000003814 drug Substances 0.000 claims abstract description 3
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 16
229960001603 tamoxifen Drugs 0.000 claims description 12
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
230000008025 crystallization Effects 0.000 claims description 10
239000000047 product Substances 0.000 claims description 10
238000000926 separation method Methods 0.000 claims description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 6
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 5
KDKKRJMQCQNZDY-UHFFFAOYSA-N 1-(1,2-diphenylbut-1-enyl)-4-fluorobenzene Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 KDKKRJMQCQNZDY-UHFFFAOYSA-N 0.000 claims description 4
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 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
229960001367 tartaric acid Drugs 0.000 claims description 4
235000002906 tartaric acid Nutrition 0.000 claims description 4
239000011975 tartaric acid Substances 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
150000001860 citric acid derivatives Chemical class 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
239000005457 ice water Substances 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
NSFIAKFOCAEBER-QZTJIDSGSA-N (2s,3s)-2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical class C1=CC(C)=CC=C1[C@@](O)(C(O)=O)[C@](O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-QZTJIDSGSA-N 0.000 claims description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
NKANXQFJJICGDU-OCEACIFDSA-N 2-[4-[(e)-1,2-diphenylbut-1-enyl]phenoxy]-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)\C1=CC=CC=C1 NKANXQFJJICGDU-OCEACIFDSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229960001270 d- tartaric acid Drugs 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
239000012467 final product Substances 0.000 claims description 2
239000012535 impurity Substances 0.000 claims description 2
229960002510 mandelic acid Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000002844 melting Methods 0.000 claims description 2
230000008018 melting Effects 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
150000003892 tartrate salts Chemical class 0.000 claims description 2
-1 (Z)-1,2-diphenyl-1-[p-(2-dimethylaminoethoxy)phenyl]but-1-ene dibenzoyl-d-tartaric acid monomethylamide salt Chemical compound 0.000 abstract description 2
NKANXQFJJICGDU-UHFFFAOYSA-N 2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(OCCN(C)C)=CC=1)C1=CC=CC=C1 NKANXQFJJICGDU-UHFFFAOYSA-N 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000002609 medium Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000000155 melt Substances 0.000 description 3
OCQAXYHNMWVLRH-QZTJIDSGSA-N (2r,3r)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@@](O)(C(=O)O)[C@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-QZTJIDSGSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 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
- A61K31/075—Ethers or acetals
- 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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- 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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
- 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
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH2118/82A 1981-04-07 1982-04-06 Process for the preparation of (Z)-1,2-diphenyl-1-[p-(2-dimethyl-aminoethoxy)phenyl]but-1-ene CH649526A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU81893A HU184847B (en)	1981-04-07	1981-04-07	Process for preparing /z/-1,2-diphenyl-1-/p-/2-dimethylamino-ethoxy/-phenyl/-but-1-ene

Publications (1)

Publication Number	Publication Date
CH649526A5 true CH649526A5 (en)	1985-05-31

Family

ID=10951913

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH2118/82A CH649526A5 (en)	1981-04-07	1982-04-06	Process for the preparation of (Z)-1,2-diphenyl-1-[p-(2-dimethyl-aminoethoxy)phenyl]but-1-ene

Country Status (7)

Country	Link
AT (1)	AT379583B (it)
BE (1)	BE892662A (it)
CH (1)	CH649526A5 (it)
ES (1)	ES511237A0 (it)
HU (1)	HU184847B (it)
IT (1)	IT1190761B (it)
SU (1)	SU1082318A3 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL110206A (en) *	1994-07-04	1996-10-16	Innova Sa	Recovery of carboxylic acid from organic solution that contains an amine and an extraction enhancer

1981
- 1981-04-07 HU HU81893A patent/HU184847B/hu not_active IP Right Cessation
1982
- 1982-03-29 BE BE1/10478A patent/BE892662A/fr not_active IP Right Cessation
- 1982-03-30 AT AT0124582A patent/AT379583B/de not_active IP Right Cessation
- 1982-04-02 SU SU823430888A patent/SU1082318A3/ru active
- 1982-04-05 IT IT20571/82A patent/IT1190761B/it active
- 1982-04-06 CH CH2118/82A patent/CH649526A5/de not_active IP Right Cessation
- 1982-04-07 ES ES511237A patent/ES511237A0/es active Granted

Also Published As

Publication number	Publication date
ES8307715A1 (es)	1983-08-01
BE892662A (fr)	1982-09-29
ES511237A0 (es)	1983-08-01
AT379583B (de)	1986-01-27
SU1082318A3 (ru)	1984-03-23
ATA124582A (de)	1985-06-15
IT8220571A1 (it)	1983-10-05
IT8220571A0 (it)	1982-04-05
IT1190761B (it)	1988-02-24
HU184847B (en)	1984-10-29

Legal Events

Date	Code	Title	Description
1989-12-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

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