CH640499A5 - Process for preparing a 2-arylpropionic acid - Google Patents

Process for preparing a 2-arylpropionic acid Download PDF

Info

Publication number: CH640499A5
Authority: CH; Switzerland
Prior art keywords: acid; aryl; magnesium; propionic acid; solution
Prior art date: 1977-02-16

Application number

CH167578A

Other languages

German (de)

English (en)

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

1978-02-15

Publication date

1984-01-13

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

1978-02-15 Application filed by Syntex Pharma Int filed Critical Syntex Pharma Int

1984-01-13 Publication of CH640499A5 publication Critical patent/CH640499A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 22
238000004519 manufacturing process Methods 0.000 title claims description 8
-1 6-methoxy-2-naphthyl Chemical group 0.000 claims abstract description 25
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 13
229910001623 magnesium bromide Inorganic materials 0.000 claims abstract description 13
229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 9
150000007513 acids Chemical class 0.000 claims abstract description 7
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 3
239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 3
229940121363 anti-inflammatory agent Drugs 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 50
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
239000011777 magnesium Substances 0.000 claims description 23
239000007818 Grignard reagent Substances 0.000 claims description 22
150000004795 grignard reagents Chemical class 0.000 claims description 22
238000005859 coupling reaction Methods 0.000 claims description 18
229910052749 magnesium Inorganic materials 0.000 claims description 18
238000010168 coupling process Methods 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
230000008878 coupling Effects 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
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 claims description 9
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical group [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims description 7
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 6
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 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 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
238000011031 large-scale manufacturing process Methods 0.000 claims 2
235000019260 propionic acid Nutrition 0.000 claims 2
OZGMODDEIHYPRY-UHFFFAOYSA-N 2-bromopropanoyl chloride Chemical compound CC(Br)C(Cl)=O OZGMODDEIHYPRY-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
150000004792 aryl magnesium halides Chemical class 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229910052793 cadmium Inorganic materials 0.000 claims 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 1
239000011575 calcium Substances 0.000 claims 1
159000000007 calcium salts Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000002524 organometallic group Chemical group 0.000 claims 1
QFSVSBKCMFGDOH-UHFFFAOYSA-M potassium;2-iodopropanoate Chemical compound [K+].CC(I)C([O-])=O QFSVSBKCMFGDOH-UHFFFAOYSA-M 0.000 claims 1
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 claims 1
238000010189 synthetic method Methods 0.000 claims 1
239000011701 zinc Substances 0.000 claims 1
229910052725 zinc Inorganic materials 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 abstract description 2
230000020477 pH reduction Effects 0.000 abstract description 2
150000001649 bromium compounds Chemical class 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
159000000003 magnesium salts Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000002430 hydrocarbons Chemical group 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
239000012074 organic phase Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 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
239000012071 phase Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 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
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002002 slurry Substances 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
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
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 1
AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-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
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
238000003747 Grignard reaction Methods 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
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001499 aryl bromides Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 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
230000003287 optical effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 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)

CH167578A 1977-02-16 1978-02-15 Process for preparing a 2-arylpropionic acid CH640499A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76907077A	1977-02-16	1977-02-16
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 (1)

Publication Number	Publication Date
CH640499A5 true CH640499A5 (en)	1984-01-13

Family

ID=27118118

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH167578A CH640499A5 (en)	1977-02-16	1978-02-15	Process for preparing a 2-arylpropionic acid
CH531782A CH640498A5 (en)	1977-02-16	1982-09-07	Magnesium halide complexes of alpha-bromopropionic acid, and their preparation
CH531882A CH640500A5 (en)	1977-02-16	1982-09-07	Magnesium halide complexes of 2-arylpropionic acids, and their preparation

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH531782A CH640498A5 (en)	1977-02-16	1982-09-07	Magnesium halide complexes of alpha-bromopropionic acid, and their preparation
CH531882A CH640500A5 (en)	1977-02-16	1982-09-07	Magnesium halide complexes of 2-arylpropionic acids, and their preparation

Country Status (18)

Country	Link
CH (3)	CH640499A5 (da)
DD (3)	DD145107A5 (da)
DK (1)	DK156898C (da)
ES (1)	ES467037A1 (da)
FI (1)	FI64571C (da)
HK (2)	HK25483A (da)
HU (2)	HU179309B (da)
IE (1)	IE46614B1 (da)
IL (1)	IL54019A (da)
IT (1)	IT1107880B (da)
MY (2)	MY8400040A (da)
NO (1)	NO145435C (da)
NZ (1)	NZ186472A (da)
PL (1)	PL108144B1 (da)
PT (1)	PT67654B (da)
SE (3)	SE430155B (da)
SU (2)	SU1003749A3 (da)
YU (3)	YU41427B (da)

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

Also Published As

Publication number	Publication date
MY8400040A (en)	1984-12-31
YU41427B (en)	1987-06-30
NO145435C (no)	1982-03-24
SE453093B (sv)	1988-01-11
SE8201459L (sv)	1982-03-09
SE430155B (sv)	1983-10-24
YU43302B (en)	1989-06-30
NZ186472A (en)	1979-08-31
HK25383A (en)	1983-08-12
DD148212A5 (de)	1981-05-13
FI64571C (fi)	1983-12-12
IT7867279A0 (it)	1978-02-10
PL108144B1 (pl)	1980-03-31
SE453094B (sv)	1988-01-11
CH640498A5 (en)	1984-01-13
YU58783A (en)	1983-12-31
IE46614B1 (en)	1983-08-10
SE7801648L (sv)	1978-08-17
YU58883A (en)	1983-12-31
DK156898B (da)	1989-10-16
FI780417A7 (fi)	1978-08-17
YU42843B (en)	1988-12-31
NO780524L (no)	1978-08-17
PL204667A1 (pl)	1978-12-04
IE780320L (en)	1978-08-16
MY8400039A (en)	1984-12-31
HU183210B (en)	1984-04-28
SE8201458L (sv)	1982-03-09
DD137099A5 (de)	1979-08-15
YU32978A (en)	1983-06-30
SU1003749A3 (ru)	1983-03-07
HU179309B (en)	1982-09-28
DK64578A (da)	1978-08-17
ES467037A1 (es)	1978-11-01
IL54019A0 (en)	1978-04-30
DK156898C (da)	1990-03-12
IL54019A (en)	1981-06-29
PT67654A (en)	1978-03-01
SU963462A3 (ru)	1982-09-30
PT67654B (en)	1979-07-19
NO145435B (no)	1981-12-14
CH640500A5 (en)	1984-01-13
DD145107A5 (de)	1980-11-19
IT1107880B (it)	1985-12-02
FI64571B (fi)	1983-08-31
HK25483A (en)	1983-08-12

Legal Events

Date	Code	Title	Description
1998-03-13	PL	Patent ceased

Publication	Publication Date	Title
AT291228B (de)	1971-07-12	Verfahren zur Herstellung neuer α,α-Dimethyl-ω-phenoxyalkansäuren, ihrer Salze oder Alkylester
DE1958919B2 (de)	1979-10-18	l-Oxo-5-indanyloxyessigsäuren und solche Verbindungen enthaltende Arzneimittel
DE2805488C2 (de)	1985-06-27	Tetrahydrofuran-Solvate der Magnesiumhalogenid-Komplexe der &alpha;-Brompropionsäure, Verfahren zu deren Herstellung und deren Weiterverarbeitung zur Herstellung von 2-Arylpropionsäuren
DE3928990A1 (de)	1991-03-07	Verfahren zur herstellung von (alpha)-fluoroacrylsaeurederivaten
EP0068350A1 (de)	1983-01-05	Verfahren zur Herstellung von Derivaten der Vinylphosphon- oder Vinylpyrophosphonsäure
DE2726393C2 (de)	1984-04-12	Verfahren zur Herstellung von 5-(quartär-Alkyl)resorcinen
CH640499A5 (en)	1984-01-13	Process for preparing a 2-arylpropionic acid
DE2613817A1 (de)	1976-10-14	Phenylpropionsaeuren, pyruvatverfahren zu ihrer herstellung und verwendung
CH619955A5 (da)	1980-10-31
AT368165B (de)	1982-09-27	Verfahren zur herstellung von neuen magnesiumverbindungen
DE2417615A1 (de)	1974-11-07	Cyclische ketone und verfahren zu ihrer herstellung
AT367063B (de)	1982-05-25	Verfahren zur herstellung einer neuen magnesiumverbindung
DE69326050T2 (de)	2000-02-03	Verfahren zur Herstellung von 0,0'-Diacylweinsäureanhydrid und Verfahren zur Herstellung von 0,0'-Diacylweinsäure
DE69211685T2 (de)	1996-12-05	Bicyclo(4.1.0)heptan-2,4-dionderivat, zwischenprodukt zur synthese sowie verfahren zur herstellung
EP0299277A2 (de)	1989-01-18	Verfahren zur Herstellung von substituierten Pyridylalkylketonen
DE69109791T2 (de)	1995-09-14	Verfahren zur Herstellung von Monohalogenalkanoylferrocenen.
DE3314029C2 (da)	1993-03-04
CH644093A5 (de)	1984-07-13	Verfahren zur herstellung von 2,2-dihalogenvinyl-substituierten cyclopropancarbonsaeure-estern.
DE2032809A1 (de)	1971-01-21	Verfahren zur Herstellung von 3 Hydroxyisoxazoldenvaten
DE2644789A1 (de)	1977-04-21	Alkylen-di-phenylalk(en)ylcarbonsaeuren und ihre herstellung und verwendung
EP0391212A2 (de)	1990-10-10	Verfahren zur Herstellung von bifunktionellen Z-Stilbenverbindungen, neue bifunktionelle Z-Stilbenverbindungen sowie die Verwendung der Z-Stilbenverbindungen zur Herstellung von Polymeren
DE923426C (de)	1955-02-14	Verfahren zur Herstellung von ª‡-substituierten ª‰-Oxypropionsaeuren
LU82205A1 (de)	1981-09-10	Verfahren zur herstellung eines carbazolderivates
CH632263A5 (de)	1982-09-30	Verfahren zur herstellung cyclischer 2-methyl-2,4-dialkoxy-3-buten-1-al-acetale und deren verwendung.
CH527833A (de)	1972-09-15	Verfahren zur Herstellung von symmetrischen 1,3,5-Trithianverbindungen