DD145107A5 - Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates - Google Patents

Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates Download PDF

Info

Publication number: DD145107A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; complex; magnesium; preparation; ecm
Prior art date: 1977-02-16

Application number

DD78214577A

Other languages

German (de)

English (en)

Inventor

Gary J Matthews

Robert A Arnold

Original Assignee

Syntex Corp

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

1980-11-19

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

1978-02-15 Application filed by Syntex Corp filed Critical Syntex Corp

1980-11-19 Publication of DD145107A5 publication Critical patent/DD145107A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 14
239000002253 acid Substances 0.000 claims description 24
239000007818 Grignard reagent Substances 0.000 claims description 20
150000004795 grignard reagents Chemical class 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
239000011777 magnesium Substances 0.000 description 18
-1 aryl Grignard reagent Chemical class 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
238000005859 coupling reaction Methods 0.000 description 14
TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000010168 coupling process Methods 0.000 description 13
150000007513 acids Chemical class 0.000 description 12
229910052749 magnesium Inorganic materials 0.000 description 12
230000008878 coupling Effects 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000000047 product Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
229910001629 magnesium chloride Inorganic materials 0.000 description 7
150000003839 salts Chemical class 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
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 6
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
229910001623 magnesium bromide Inorganic materials 0.000 description 5
239000000376 reactant Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 4
159000000003 magnesium salts Chemical class 0.000 description 4
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 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
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical class CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 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
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
229910052744 lithium Inorganic materials 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
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-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
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 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
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-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
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
101100189378 Caenorhabditis elegans pat-3 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
244000025221 Humulus lupulus Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 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
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
159000000007 calcium salts Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 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
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011031 large-scale manufacturing process Methods 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
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-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
239000000203 mixture 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 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 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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)

DD78214577A 1977-02-16 1978-02-15 Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates DD145107A5 (de)

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
DD145107A5 true DD145107A5 (de)	1980-11-19

Family

ID=27118118

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD78214577A DD145107A5 (de)	1977-02-16	1978-02-15	Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates
DD78214578A DD148212A5 (de)	1977-02-16	1978-02-15	Verfahren zur herstellung von aryl ch(ch tief 3)coomgx oder dessen aetherates
DD78203717A DD137099A5 (de)	1977-02-16	1978-02-15	Verfahren zur herstellung einer 2-arylpropionsaeure

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD78214578A DD148212A5 (de)	1977-02-16	1978-02-15	Verfahren zur herstellung von aryl ch(ch tief 3)coomgx oder dessen aetherates
DD78203717A DD137099A5 (de)	1977-02-16	1978-02-15	Verfahren zur herstellung einer 2-arylpropionsaeure

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0407121A3 (en) *	1989-07-06	1992-07-08	The Associated Octel Company Limited	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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0407121A3 (en) *	1989-07-06	1992-07-08	The Associated Octel Company Limited	Alkaline earth, transition and lanthanide metal inorganic salt complexes

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
CH640499A5 (en)	1984-01-13
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
IT1107880B (it)	1985-12-02
FI64571B (fi)	1983-08-31
HK25483A (en)	1983-08-12

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Date	Code	Title	Description
1997-11-20	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3006277C2 (da)	1990-07-12
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
DE2536145A1 (de)	1976-02-26	Verfahren zur herstellung von cyclopropanderivaten
DE3212170C2 (da)	1989-03-02
DE2613817A1 (de)	1976-10-14	Phenylpropionsaeuren, pyruvatverfahren zu ihrer herstellung und verwendung
DD145107A5 (de)	1980-11-19	Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates
DD202427A5 (de)	1983-09-14	Verfahren zur herstellung von alpha-halogenalkylamiden
DE69211685T2 (de)	1996-12-05	Bicyclo(4.1.0)heptan-2,4-dionderivat, zwischenprodukt zur synthese sowie verfahren zur herstellung
DE2737299C2 (de)	1986-07-17	Verfahren zur Gewinnung von reinem 3-Phenoxybenzaldehyd
AT368165B (de)	1982-09-27	Verfahren zur herstellung von neuen magnesiumverbindungen
DE2116159C3 (de)	1987-12-03	Verfahren zur Herstellung von 4-Pyridylthio-essigsäure
AT367063B (de)	1982-05-25	Verfahren zur herstellung einer neuen magnesiumverbindung
DE69018058T3 (de)	2002-04-18	Verfahren zur Debrominierung von 2-substituierten-5-Bromo-6-Methoxynaphthalenen.
DE1643492C3 (de)	1973-12-13	1,3,5 Tnthiacyclohexane und deren Herstellung
DE2651371A1 (de)	1977-05-12	Quaternaere ammoniumsalze
DE2624340C2 (de)	1984-08-16	Verfahren zur Herstellung von 1,1-Dihalogen-1,3-dienen
DE857501C (de)	1952-12-01	Verfahren zur Herstellung von Disulfiden
DE2653446C2 (de)	1985-08-22	Verfahren zur Herstellung von Pyrogallolverbindungen
AT343649B (de)	1978-06-12	Verfahren zur herstellung neuer substituierter, gegebenenfalls veresterter oder amidierter benzocycloalkenylcarbonsauren
DE2032809A1 (de)	1971-01-21	Verfahren zur Herstellung von 3 Hydroxyisoxazoldenvaten
AT239780B (de)	1965-04-26	Verfahren zur Herstellung neuer Naphthaline und Salzen dieser Verbindungen
AT222816B (de)	1962-08-10	Verfahren zur Herstellung von 2-cis-β-Jonylidenessigsäure
DE2735982A1 (de)	1978-02-23	Benzamidopiperidin-derivate, ihre verwendung und herstellung
DE3616363A1 (de)	1987-11-19	Verfahren zur herstellung von 1,4-dihydroxy-5,8-dihydronaphthalin und verwandten verbindungen
DE3917942A1 (de)	1989-12-21	Nitrobenzoyl-3-cyclopropylaminoacrylate und verfahren zu ihrer herstellung

DD145107A5 - Verfahren zur herstellung von ch t ef 3 ch(br)coomgx oder eines etherates - Google Patents

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