DD279013A5 - Verfahren zum herstellen von sertralin-zwischenverbindungen - Google Patents

Verfahren zum herstellen von sertralin-zwischenverbindungen Download PDF

Info

Publication number: DD279013A5
Authority: DD; German Democratic Republic
Prior art keywords: dichlorophenyl; acid; dihydro; benzene; reaction
Prior art date: 1987-06-11

Application number

DD88325879A

Other languages

German (de)

English (en)

Inventor

George J Quallich

Michael T Williams

Original Assignee

��@��Kk��

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.)

1987-06-11

Filing date

1988-06-10

Publication date

1990-05-23

1988-06-10 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1990-05-23 Publication of DD279013A5 publication Critical patent/DD279013A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 6
238000006243 chemical reaction Methods 0.000 claims abstract description 33
238000000034 method Methods 0.000 claims abstract description 31
TXURVWVBXWPFRO-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid Chemical compound OC(=O)CCC(O)C1=CC=C(Cl)C(Cl)=C1 TXURVWVBXWPFRO-UHFFFAOYSA-N 0.000 claims abstract description 22
JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 claims abstract description 20
HSAZYDYRKKZYSQ-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)oxolan-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC(=O)CC1 HSAZYDYRKKZYSQ-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001261 hydroxy acids Chemical class 0.000 claims abstract description 14
239000007795 chemical reaction product Substances 0.000 claims abstract description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 69
239000002904 solvent Substances 0.000 claims description 20
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 16
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 13
239000003153 chemical reaction reagent Substances 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
229940098779 methanesulfonic acid Drugs 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
239000011968 lewis acid catalyst Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 abstract description 12
DPCXOOJTAKKWIC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C(Cl)=C1 DPCXOOJTAKKWIC-UHFFFAOYSA-N 0.000 abstract description 9
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 abstract description 7
229960002073 sertraline Drugs 0.000 abstract description 6
230000001430 anti-depressive effect Effects 0.000 abstract description 4
239000000935 antidepressant agent Substances 0.000 abstract description 4
229940005513 antidepressants Drugs 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000543 intermediate Substances 0.000 description 19
-1 benzophenone compound Chemical class 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 10
238000004821 distillation Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000010410 layer Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000002609 medium Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000000967 suction filtration Methods 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000012265 solid product Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FLSBZXWDASEHJU-UHFFFAOYSA-N 4,4-diphenylbutanoic acid Chemical class C=1C=CC=CC=1C(CCC(=O)O)C1=CC=CC=C1 FLSBZXWDASEHJU-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000004743 Polypropylene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
239000006260 foam Substances 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
150000004715 keto acids Chemical class 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 1
GATLSWXZDMNKKO-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)oxolan-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C(=O)OCC1 GATLSWXZDMNKKO-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
MGPHWSQUSKFMKT-UHFFFAOYSA-N 4,4-diphenylbut-3-enoic acid Chemical compound C=1C=CC=CC=1C(=CCC(=O)O)C1=CC=CC=C1 MGPHWSQUSKFMKT-UHFFFAOYSA-N 0.000 description 1
229940006015 4-hydroxybutyric acid Drugs 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000694440 Colpidium aqueous Species 0.000 description 1
DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
238000006600 Stobbe condensation reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
KKAXNAVSOBXHTE-UHFFFAOYSA-N boranamine Chemical class NB KKAXNAVSOBXHTE-UHFFFAOYSA-N 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
238000007273 lactonization reaction Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)
Catalysts (AREA)
Medicinal Preparation (AREA)

DD88325879A 1987-06-11 1988-06-10 Verfahren zum herstellen von sertralin-zwischenverbindungen DD279013A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/060,577 US4777288A (en)	1987-06-11	1987-06-11	Process for preparing a 4,4-diphenylbutanoic acid derivative

Publications (1)

Publication Number	Publication Date
DD279013A5 true DD279013A5 (de)	1990-05-23

Family

ID=22030394

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD88325879A DD279013A5 (de)	1987-06-11	1988-06-10	Verfahren zum herstellen von sertralin-zwischenverbindungen
DD88316663A DD287483A5 (de)	1987-06-11	1988-06-10	Verfahren zum herstellen von 4-(3,4-dichlorphenyl)-4-phenylbuttersaeure als sertralin-zwischenverbindung

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD88316663A DD287483A5 (de)	1987-06-11	1988-06-10	Verfahren zum herstellen von 4-(3,4-dichlorphenyl)-4-phenylbuttersaeure als sertralin-zwischenverbindung

Country Status (29)

Country	Link
US (1)	US4777288A (cs)
EP (1)	EP0295050B1 (cs)
JP (1)	JPH0627098B2 (cs)
KR (1)	KR910000780B1 (cs)
CN (2)	CN1025328C (cs)
AT (1)	ATE62657T1 (cs)
AU (1)	AU586953B2 (cs)
CA (1)	CA1285574C (cs)
CS (1)	CS272238B2 (cs)
DD (2)	DD279013A5 (cs)
DE (1)	DE3862434D1 (cs)
DK (1)	DK175280B1 (cs)
EG (1)	EG18404A (cs)
ES (1)	ES2022621B3 (cs)
FI (1)	FI90657C (cs)
GR (1)	GR3001908T3 (cs)
HU (2)	HU198670B (cs)
IE (1)	IE61072B1 (cs)
IL (1)	IL86629A0 (cs)
MX (1)	MX172786B (cs)
MY (2)	MY103570A (cs)
NO (1)	NO167731C (cs)
NZ (1)	NZ224984A (cs)
PH (1)	PH25099A (cs)
PL (2)	PL153028B1 (cs)
PT (1)	PT87691B (cs)
RU (2)	RU1799377C (cs)
YU (2)	YU47120B (cs)
ZA (1)	ZA884161B (cs)

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ATE145198T1 (de) *	1991-12-13	1996-11-15	Pfizer	Verfahren zur herstellung eines keton enantiomers
US5196607A (en) *	1992-02-14	1993-03-23	Pfizer Inc.	Process for preparing ketone enantiomer
US5466880A (en) *	1992-09-15	1995-11-14	Pfizer Inc.	Process for preparing ketone enantiomer
DE69406553T2 (de) *	1993-11-30	1998-02-26	Pfizer Inc., New York, N.Y.	Verfahren zur herstellung von chiralen tetralonen
US6410794B1 (en)	1994-12-16	2002-06-25	Uop Llc	Process for preparation of pharmaceutically desired chiral tetralone from tetralones
HUP0002296A3 (en)	1997-07-01	2001-11-28	Pfizer	Sertraline salts and sustained-release dosage forms of sertraline
WO1999046233A1 (en) *	1998-03-09	1999-09-16	Sumika Fine Chemicals Co., Ltd.	Benzyl alcohol derivatives
IL132500A0 (en)	1998-10-29	2001-03-19	Pfizer Prod Inc	Stereoselective microbial reduction of a racemic tetralone
IN187170B (cs)	2000-01-04	2002-02-23	Sun Pharmaceutical Ind Ltd
FR2817256B1 (fr) *	2000-11-27	2005-07-15	Univ Pasteur	Derives de l'acides 4-hydroxybutanoique et de son homologue superieur comme ligands des recepteurs du gamma- hydroxybutyrate (ghb), compositions pharmaceutiques les contenant et utilisations pharmaceutiques
CN100413856C (zh) *	2006-09-06	2008-08-27	大连来克精化有限公司	一种威士忌内酯的制备方法

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DE2112715A1 (de) *	1971-03-17	1972-10-05	Thomae Gmbh Dr K	Neue 4-(4-Biphenylyl)-4-hydroxybuttersaeuren,ihre Salze,Ester und Lactone
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FR2504127B1 (fr) *	1981-04-17	1985-07-19	Roussel Uclaf	Nouveaux derives d'acides phenyl aliphatique carboxyliques, procede pour leur preparation et leur application comme medicaments
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1987
- 1987-06-11 US US07/060,577 patent/US4777288A/en not_active Expired - Lifetime
1988
- 1988-06-06 IL IL86629A patent/IL86629A0/xx not_active IP Right Cessation
- 1988-06-06 MY MYPI88000602A patent/MY103570A/en unknown
- 1988-06-07 EP EP88305179A patent/EP0295050B1/en not_active Expired - Lifetime
- 1988-06-07 DE DE8888305179T patent/DE3862434D1/de not_active Expired - Lifetime
- 1988-06-07 AT AT88305179T patent/ATE62657T1/de not_active IP Right Cessation
- 1988-06-07 ES ES88305179T patent/ES2022621B3/es not_active Expired - Lifetime
- 1988-06-08 JP JP63141429A patent/JPH0627098B2/ja not_active Expired - Fee Related
- 1988-06-08 CS CS883976A patent/CS272238B2/cs not_active IP Right Cessation
- 1988-06-09 PT PT87691A patent/PT87691B/pt not_active IP Right Cessation
- 1988-06-09 PL PL1988272949A patent/PL153028B1/pl unknown
- 1988-06-09 CA CA000569010A patent/CA1285574C/en not_active Expired - Lifetime
- 1988-06-09 EG EG324/88A patent/EG18404A/xx active
- 1988-06-09 PL PL1988278118A patent/PL156829B1/pl unknown
- 1988-06-10 RU SU884355975A patent/RU1799377C/ru active
- 1988-06-10 HU HU883022A patent/HU198670B/hu not_active IP Right Cessation
- 1988-06-10 AU AU17613/88A patent/AU586953B2/en not_active Ceased
- 1988-06-10 YU YU112788A patent/YU47120B/sh unknown
- 1988-06-10 DK DK198803190A patent/DK175280B1/da not_active IP Right Cessation
- 1988-06-10 MX MX011861A patent/MX172786B/es unknown
- 1988-06-10 NZ NZ224984A patent/NZ224984A/en unknown
- 1988-06-10 FI FI882779A patent/FI90657C/fi active IP Right Grant
- 1988-06-10 IE IE176288A patent/IE61072B1/en not_active IP Right Cessation
- 1988-06-10 CN CN88103840A patent/CN1025328C/zh not_active Expired - Fee Related
- 1988-06-10 ZA ZA884161A patent/ZA884161B/xx unknown
- 1988-06-10 NO NO882566A patent/NO167731C/no not_active IP Right Cessation
- 1988-06-10 PH PH37054A patent/PH25099A/en unknown
- 1988-06-10 HU HU883018A patent/HU213617B/hu not_active IP Right Cessation
- 1988-06-10 DD DD88325879A patent/DD279013A5/de not_active IP Right Cessation
- 1988-06-10 KR KR1019880006962A patent/KR910000780B1/ko not_active Expired
- 1988-06-10 DD DD88316663A patent/DD287483A5/de not_active IP Right Cessation
1989
- 1989-03-20 RU SU894613675A patent/RU1839670C/ru active
1991
- 1991-05-03 GR GR91400585T patent/GR3001908T3/el unknown
1992
- 1992-09-21 MY MYPI92001685A patent/MY107026A/en unknown
1993
- 1993-09-22 YU YU60893A patent/YU49242B/sh unknown
- 1993-12-03 CN CN93120776A patent/CN1042129C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO167731C (no)	1992-03-04
HU213617B (en)	1997-08-28
DD287483A5 (de)	1991-02-28
NO882566L (no)	1988-12-12
FI882779A7 (fi)	1988-12-12
MX11861A (es)	1993-03-01
PL153028B1 (en)	1991-02-28
CA1285574C (en)	1991-07-02
US4777288A (en)	1988-10-11
IE61072B1 (en)	1994-09-21
DE3862434D1 (de)	1991-05-23
PL272949A1 (en)	1989-07-10
EP0295050A1 (en)	1988-12-14
EG18404A (en)	1993-02-28
NZ224984A (en)	1990-04-26
JPS649953A (en)	1989-01-13
CS272238B2 (en)	1991-01-15
CN1025328C (zh)	1994-07-06
CN1031837A (zh)	1989-03-22
ATE62657T1 (de)	1991-05-15
CN1100086A (zh)	1995-03-15
ZA884161B (en)	1990-02-28
PT87691B (pt)	1992-09-30
NO882566D0 (no)	1988-06-10
PT87691A (pt)	1988-07-01
CN1042129C (zh)	1999-02-17
MY103570A (en)	1993-08-28
PH25099A (en)	1991-02-19
NO167731B (no)	1991-08-26
MY107026A (en)	1995-08-30
AU586953B2 (en)	1989-07-27
KR890000393A (ko)	1989-03-14
MX172786B (es)	1994-01-13
AU1761388A (en)	1988-12-15
YU112788A (en)	1989-10-31
FI882779A0 (fi)	1988-06-10
YU49242B (sh)	2004-12-31
DK319088A (da)	1988-12-12
FI90657B (fi)	1993-11-30
PL278118A1 (en)	1989-08-21
RU1799377C (ru)	1993-02-28
HUT47070A (en)	1989-01-30
IE881762L (en)	1988-12-11
IL86629A0 (en)	1988-11-30
EP0295050B1 (en)	1991-04-17
PL156829B1 (pl)	1992-04-30
HU198670B (en)	1989-11-28
RU1839670C (ru)	1993-12-30
YU47120B (sh)	1994-12-28
FI90657C (fi)	1994-03-10
ES2022621B3 (es)	1991-12-01
GR3001908T3 (en)	1992-11-23
DK175280B1 (da)	2004-08-09
KR910000780B1 (ko)	1991-02-08
JPH0627098B2 (ja)	1994-04-13
DK319088D0 (da)	1988-06-10
CS397688A2 (en)	1990-03-14
YU60893A (sh)	1997-05-28

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)
2001-01-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0242505B1 (de)	1990-11-07	Verfahren zur Herstellung von Caprolactam
DD287483A5 (de)	1991-02-28	Verfahren zum herstellen von 4-(3,4-dichlorphenyl)-4-phenylbuttersaeure als sertralin-zwischenverbindung
DE3212170C2 (cs)	1989-03-02
DE1795193A1 (de)	1971-12-30	Verfahren zur Herstellung von Morphinanderivaten
EP0842153A1 (de)	1998-05-20	Neues verfahren zur herstellung von norbenzomorphan einer zwischenstufe bei herstellung von pharmazeutisch wertvollen benzomorphanderivaten, insbesondere von (-)-(1r,5s,2"r)-3'-hydroxy-2-(2-methoxypropyl)-5,9,9-trimethyl-6,7-benzomorphan
EP0789694B1 (de)	2003-04-09	Verfahren zur herstellung von 8-alpha,12-oxido-13,14,15,16-tetranorlabdan
DE2447978C2 (de)	1982-11-04	Verfahren zur Herstellung einer Tropan-Verbindung
DE69519388T2 (de)	2001-05-03	Verfahren zur herstellung von 2-(omega-alkoxycarbonylalkanoyl)-4-butanolid und langkettiger omega-hydroxycarbonsäure
DE2812403A1 (de)	1978-10-12	Derivate von alpha-(6-carboxyhexyl)- furfurylalkohol und verfahren zu ihrer herstellung
EP0446759B1 (de)	1994-07-27	Verfahren zur Herstellung von Cyclopentenonen
EP0115811B1 (de)	1990-04-18	2,4-Dichlor-5-thiazolcarboxaldehyd und ein Verfahren zu seiner Herstellung
EP0305913B1 (de)	1991-05-22	Verfahren zur Herstellung von Dien-1-olen, 9-Hydroxydodec-10-enyl-1-tert.-butylether und seine Verwendung als Zwischenprodukt zur Synthese von 8,10-Dodecadienol
AT401513B (de)	1996-09-25	Verfahren zur herstellung von 2-hydroxy-4-phenylbuttersäure
DE2101480B2 (de)	1979-06-13	Verfahren zur Herstellung von 6-HydroxY-chromanen
DE3112056A1 (de)	1982-10-07	Verbessertes verfahren zur herstellung von cyclohexan-1,3-dionen sowie einige neue bicyclische cyclohexan-1,3-dione
EP1525176B1 (de)	2008-12-31	Verfahren zur herstellung von makrocyclischen ketonen durch dieckmann-kondensation in der gasphase
DE3325976C2 (cs)	1991-11-07
DE1643617A1 (de)	1972-03-02	Cyclooctylformat und Verfahren zur Herstellung von Cyclooctyl-Verbindungen
DE69835508T2 (de)	2007-02-08	Verfahren zur herstellung von 2-(omega-alkoxycarbonylalkanoyl)-4-butanoliden,omega-hydroxy-(omega-3)-keto-fettsäureestern und ihrer derivate
DE2139084B2 (de)	1978-06-29	Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen
EP0306875A2 (de)	1989-03-15	Verfahren zur Herstellung von 5-Methylbutyrolacton
AT340382B (de)	1977-12-12	Verfahren zur herstellung von neuen 10- (2'-dialkylaminoathyl) -10,11-dihydro-5-methylen-5h-dibenzo (a,d)- cycloheptenen und ihren saureadditionssalzen
AT359210B (de)	1980-10-27	Verfahren zur herstellung von desoxyvincamin- amiden
DE2318566C3 (de)	1976-10-14	3-Alkoxy-5-substituierte Phenylessigsäuren
DE2114356C3 (de)	1980-08-14	Verfahren zur Herstellung von 2,3-Dihydrofluoranthen aus l,23,10b-Tetrahydrofluoranthen