FI64571C - Foerfarande foer framstaellning av 2-aryl-propionsyra - Google Patents

Foerfarande foer framstaellning av 2-aryl-propionsyra Download PDF

Info

Publication number: FI64571C
Authority: FI; Finland
Prior art keywords: magnesium; acid; aryl; solution; complex
Prior art date: 1977-02-16

Application number

FI780417A

Other languages

English (en)

Finnish (fi)

Other versions

FI780417A7 (fi

FI64571B (fi

Inventor

Gary J Matthews

Robert A Arnold

Original Assignee

Syntex Pharma Int

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.)

1977-02-16

Filing date

1978-02-09

Publication date

1983-12-12

1977-12-19 Priority claimed from US05/863,290 external-priority patent/US4144397A/en

1978-02-09 Application filed by Syntex Pharma Int filed Critical Syntex Pharma Int

1978-08-17 Publication of FI780417A7 publication Critical patent/FI780417A7/fi

1983-04-11 Priority to FI831198A priority Critical patent/FI82442C/fi

1983-04-11 Priority to FI831197A priority patent/FI77643C/fi

1983-08-31 Publication of FI64571B publication Critical patent/FI64571B/fi

1983-12-12 Application granted granted Critical

1983-12-12 Publication of FI64571C publication Critical patent/FI64571C/fi

Links

-1 6-methoxy-2-naphthyl Chemical group 0.000 abstract description 17
239000002253 acid Substances 0.000 abstract description 16
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 9
150000001875 compounds Chemical class 0.000 abstract description 7
150000007513 acids Chemical class 0.000 abstract description 6
125000003118 aryl group Chemical group 0.000 abstract description 5
239000000460 chlorine Substances 0.000 abstract description 5
229910052801 chlorine Inorganic materials 0.000 abstract description 5
239000000010 aprotic solvent Substances 0.000 abstract description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 4
229910052794 bromium Inorganic materials 0.000 abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
230000001225 therapeutic effect Effects 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical class CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 20
150000004795 grignard reagents Chemical class 0.000 description 19
238000002360 preparation method Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
238000005859 coupling reaction Methods 0.000 description 18
239000007818 Grignard reagent Substances 0.000 description 17
239000011777 magnesium Substances 0.000 description 17
238000000034 method Methods 0.000 description 17
239000000047 product Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
229910052749 magnesium Inorganic materials 0.000 description 14
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
238000010168 coupling process Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 9
239000000956 alloy Substances 0.000 description 8
229910045601 alloy Inorganic materials 0.000 description 8
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
230000008878 coupling Effects 0.000 description 7
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
229910001629 magnesium chloride Inorganic materials 0.000 description 6
159000000003 magnesium salts Chemical class 0.000 description 6
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 6
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 4
229910001623 magnesium bromide Inorganic materials 0.000 description 4
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
DESVPZPAXGJCGM-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)propanoic acid Chemical compound CC(C)C1=CC=C(C(C)C(O)=O)C=C1 DESVPZPAXGJCGM-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
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 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
CTBWRIQCVMDQFU-UHFFFAOYSA-L [Cl-].[Mg+2].BrC(C(=O)O)C.[Cl-] Chemical compound [Cl-].[Mg+2].BrC(C(=O)O)C.[Cl-] CTBWRIQCVMDQFU-UHFFFAOYSA-L 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000010668 complexation reaction Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010791 quenching Methods 0.000 description 2
230000000171 quenching effect Effects 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
SEZHLKZEWYFCRB-UHFFFAOYSA-N 1,2-dimethoxyethane;oxolane Chemical compound C1CCOC1.COCCOC SEZHLKZEWYFCRB-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
KDYOFXPLHVSIHS-UHFFFAOYSA-N 2-(4-methylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(C)C=C1 KDYOFXPLHVSIHS-UHFFFAOYSA-N 0.000 description 1
VTLOAKUQUADSND-UHFFFAOYSA-N 3-(6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(CCC(O)=O)C=CC2=CC(OC)=CC=C21 VTLOAKUQUADSND-UHFFFAOYSA-N 0.000 description 1
UUIFSHHBZZIPIE-UHFFFAOYSA-N CC1=CC=C(C=C1)C(C(=O)O)C.C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C Chemical compound CC1=CC=C(C=C1)C(C(=O)O)C.C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C UUIFSHHBZZIPIE-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
YBPFQOFSPMWGKA-UHFFFAOYSA-M [Cl-].CC1=CC=C([Mg+])C=C1 Chemical compound [Cl-].CC1=CC=C([Mg+])C=C1 YBPFQOFSPMWGKA-UHFFFAOYSA-M 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000001499 aryl bromides Chemical class 0.000 description 1
150000004792 aryl magnesium halides Chemical class 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
YMRNLEZXZITSEG-UHFFFAOYSA-N methylidenemagnesium Chemical compound [Mg]=C YMRNLEZXZITSEG-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QFSVSBKCMFGDOH-UHFFFAOYSA-M potassium;2-iodopropanoate Chemical compound [K+].CC(I)C([O-])=O QFSVSBKCMFGDOH-UHFFFAOYSA-M 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C63/24—1,3 - Benzenedicarboxylic acid

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)

FI780417A 1977-02-16 1978-02-09 Foerfarande foer framstaellning av 2-aryl-propionsyra FI64571C (fi)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
FI831198A FI82442C (fi)	1977-02-16	1983-04-11	Foerfarande foer framstaellning av 2-arylpropionsyra- magnesiumhalogenidkomplex och dess anvaendning vid framstaellning av 2-arylpropionsyra.
FI831197A FI77643C (fi)	1977-02-16	1983-04-11	Magnesiumhalogenidkomplex av alfa- brompropionsyra och dess framstaellningsfoerfarande.

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US76907077A	1977-02-16	1977-02-16
US76907077		1977-02-16
US86329077		1977-12-19
US05/863,290 US4144397A (en)	1977-02-16	1977-12-19	Preparation of 2-aryl-propionic acids by direct coupling utilizing a mixed magnesium halide complex

Publications (3)

Publication Number	Publication Date
FI780417A7 FI780417A7 (fi)	1978-08-17
FI64571B FI64571B (fi)	1983-08-31
FI64571C true FI64571C (fi)	1983-12-12

Family

ID=27118118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI780417A FI64571C (fi)	1977-02-16	1978-02-09	Foerfarande foer framstaellning av 2-aryl-propionsyra

Country Status (18)

Country	Link
CH (3)	CH640499A5 (it)
DD (3)	DD137099A5 (it)
DK (1)	DK156898C (it)
ES (1)	ES467037A1 (it)
FI (1)	FI64571C (it)
HK (2)	HK25383A (it)
HU (2)	HU183210B (it)
IE (1)	IE46614B1 (it)
IL (1)	IL54019A (it)
IT (1)	IT1107880B (it)
MY (2)	MY8400039A (it)
NO (1)	NO145435C (it)
NZ (1)	NZ186472A (it)
PL (1)	PL108144B1 (it)
PT (1)	PT67654B (it)
SE (3)	SE430155B (it)
SU (2)	SU1003749A3 (it)
YU (3)	YU41427B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8915531D0 (en) *	1989-07-06	1989-08-23	Ass Octel	Alkaline earth,transition and lanthanide metal inorganic salt complexes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1459084A (en) *	1973-05-24	1976-12-22	Boots Co Ltd	Preparation of arylalkanoic acid

1978
- 1978-02-09 HU HU802271A patent/HU183210B/hu unknown
- 1978-02-09 HU HU78SI1618A patent/HU179309B/hu unknown
- 1978-02-09 FI FI780417A patent/FI64571C/fi not_active IP Right Cessation
- 1978-02-10 IL IL54019A patent/IL54019A/xx unknown
- 1978-02-10 IT IT67279/78A patent/IT1107880B/it active
- 1978-02-13 DK DK064578A patent/DK156898C/da not_active IP Right Cessation
- 1978-02-13 SE SE7801648A patent/SE430155B/sv not_active IP Right Cessation
- 1978-02-13 YU YU329/78A patent/YU41427B/xx unknown
- 1978-02-14 IE IE320/78A patent/IE46614B1/en not_active IP Right Cessation
- 1978-02-14 NZ NZ186472A patent/NZ186472A/xx unknown
- 1978-02-14 PT PT67654A patent/PT67654B/pt unknown
- 1978-02-15 NO NO780524A patent/NO145435C/no unknown
- 1978-02-15 DD DD78203717A patent/DD137099A5/xx not_active IP Right Cessation
- 1978-02-15 CH CH167578A patent/CH640499A5/de not_active IP Right Cessation
- 1978-02-15 SU SU782580499A patent/SU1003749A3/ru active
- 1978-02-15 DD DD78214578A patent/DD148212A5/de not_active IP Right Cessation
- 1978-02-15 DD DD78214577A patent/DD145107A5/de not_active IP Right Cessation
- 1978-02-16 PL PL1978204667A patent/PL108144B1/pl unknown
- 1978-02-16 ES ES467037A patent/ES467037A1/es not_active Expired
- 1978-10-11 SU SU782672198A patent/SU963462A3/ru active
1982
- 1982-03-09 SE SE8201458A patent/SE453093B/sv not_active IP Right Cessation
- 1982-03-09 SE SE8201459A patent/SE453094B/sv not_active IP Right Cessation
- 1982-09-07 CH CH531782A patent/CH640498A5/de not_active IP Right Cessation
- 1982-09-07 CH CH531882A patent/CH640500A5/de not_active IP Right Cessation
1983
- 1983-03-10 YU YU587/83A patent/YU43302B/xx unknown
- 1983-03-10 YU YU588/83A patent/YU42843B/xx unknown
- 1983-08-04 HK HK253/83A patent/HK25383A/xx not_active IP Right Cessation
- 1983-08-04 HK HK254/83A patent/HK25483A/xx not_active IP Right Cessation
1984
- 1984-12-30 MY MY39/84A patent/MY8400039A/xx unknown
- 1984-12-30 MY MY40/84A patent/MY8400040A/xx unknown

Also Published As

Publication number	Publication date
DK156898B (da)	1989-10-16
IL54019A (en)	1981-06-29
HU183210B (en)	1984-04-28
DD137099A5 (de)	1979-08-15
CH640499A5 (en)	1984-01-13
SE8201459L (sv)	1982-03-09
CH640498A5 (en)	1984-01-13
YU32978A (en)	1983-06-30
IT1107880B (it)	1985-12-02
YU43302B (en)	1989-06-30
DK156898C (da)	1990-03-12
SE8201458L (sv)	1982-03-09
NO145435B (no)	1981-12-14
IE46614B1 (en)	1983-08-10
DD148212A5 (de)	1981-05-13
FI780417A7 (fi)	1978-08-17
IT7867279A0 (it)	1978-02-10
YU58883A (en)	1983-12-31
PT67654A (en)	1978-03-01
PL108144B1 (pl)	1980-03-31
PT67654B (en)	1979-07-19
NO780524L (no)	1978-08-17
MY8400039A (en)	1984-12-31
FI64571B (fi)	1983-08-31
DK64578A (da)	1978-08-17
HK25483A (en)	1983-08-12
IE780320L (en)	1978-08-16
NO145435C (no)	1982-03-24
SE453094B (sv)	1988-01-11
YU58783A (en)	1983-12-31
NZ186472A (en)	1979-08-31
MY8400040A (en)	1984-12-31
CH640500A5 (en)	1984-01-13
YU41427B (en)	1987-06-30
ES467037A1 (es)	1978-11-01
SE430155B (sv)	1983-10-24
HK25383A (en)	1983-08-12
YU42843B (en)	1988-12-31
DD145107A5 (de)	1980-11-19
SU1003749A3 (ru)	1983-03-07
SE453093B (sv)	1988-01-11
SU963462A3 (ru)	1982-09-30
HU179309B (en)	1982-09-28
PL204667A1 (pl)	1978-12-04
IL54019A0 (en)	1978-04-30
SE7801648L (sv)	1978-08-17

Legal Events

Date	Code	Title	Description
1978-02-09	MA	Patent expired
2004-08-31	MA	Patent expired	Owner name: SYNTEX PHARMACEUTICALS INTERNATIONAL

Publication	Publication Date	Title
US4144397A (en)	1979-03-13	Preparation of 2-aryl-propionic acids by direct coupling utilizing a mixed magnesium halide complex
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FI64571C (fi)	1983-12-12	Foerfarande foer framstaellning av 2-aryl-propionsyra
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EP0010799B1 (en)	1982-05-19	A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof
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RU2125555C1 (ru)	1999-01-27	Способ получения фторированной сульфокислоты
Croft et al.	1983	Convenient synthesis of medium-ring cis-1, 2-dichlorocycloalkanes
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EP0101003B1 (en)	1986-07-09	Process for preparing 4-oxo-4,5,6,7-tetrahydrobenzofuran derivative
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WO2005058918A1 (fr)	2005-06-30	Nouveaux derives d’acides phenyl-boronique et leurs procedes de preparation
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