NO132533B - - Google Patents

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Info

Publication number: NO132533B
Authority: NO; Norway
Prior art keywords: general formula; compound; given above; formula; meanings given
Prior art date: 1970-03-16

Application number

NO504/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO132533C (de

Inventor

J C Turner

R Po-Kuen Chan

Original Assignee

Biorex Laboratories Ltd

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.)

1970-03-16

Filing date

1971-02-11

Publication date

1975-08-18

1971-02-11 Application filed by Biorex Laboratories Ltd filed Critical Biorex Laboratories Ltd

1975-08-18 Publication of NO132533B publication Critical patent/NO132533B/no

1975-11-26 Publication of NO132533C publication Critical patent/NO132533C/no

Links

150000001875 compounds Chemical class 0.000 claims description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 6
150000003333 secondary alcohols Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 4
150000005481 1,2-diphenylethanes Chemical class 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000002366 halogen compounds Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
235000013312 flour Nutrition 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000284 extract Substances 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000000463 material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
-1 benzyl halide Chemical class 0.000 description 4
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
JIXDOBAQOWOUPA-UHFFFAOYSA-N 1-fluoro-2-methoxybenzene Chemical compound COC1=CC=CC=C1F JIXDOBAQOWOUPA-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000001076 estrogenic effect Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
NJIPZANRACFKHD-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)pentan-2-ol Chemical compound FC1=C(CC(CCC)O)C=CC(=C1)OC NJIPZANRACFKHD-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
VKGBOMPRHQCSRL-UHFFFAOYSA-N 1-(2-fluorophenyl)-2-[(4-methoxyphenyl)methyl]butan-1-one Chemical compound FC1=C(C=CC=C1)C(C(CC)CC1=CC=C(C=C1)OC)=O VKGBOMPRHQCSRL-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
CKSIBFLEDRJUTN-UHFFFAOYSA-N 3-chloropentan-2-one Chemical compound CCC(Cl)C(C)=O CKSIBFLEDRJUTN-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010020880 Hypertrophy Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 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
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000007891 compressed tablet 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
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005283 haloketone group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010977 jade Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VCRYGHPVKURQMM-UHFFFAOYSA-N methane;platinum Chemical compound C.[Pt] VCRYGHPVKURQMM-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940033134 talc Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO504/71A 1970-03-16 1971-02-11 NO132533C (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB02554/70A GB1280767A (en)	1970-03-16	1970-03-16	Derivatives of 1,2-diphenyl-ethane

Publications (2)

Publication Number	Publication Date
NO132533B true NO132533B (de)	1975-08-18
NO132533C NO132533C (de)	1975-11-26

Family

ID=10006781

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO504/71A NO132533C (de)	1970-03-16	1971-02-11

Country Status (18)

Country	Link
JP (1)	JPS515378B1 (de)
AT (1)	AT303711B (de)
BE (1)	BE764081A (de)
CA (1)	CA948215A (de)
CH (1)	CH558315A (de)
DK (1)	DK146015C (de)
ES (1)	ES389282A1 (de)
FI (1)	FI55170C (de)
FR (1)	FR2085710B1 (de)
GB (1)	GB1280767A (de)
IE (1)	IE35009B1 (de)
IL (1)	IL36225A0 (de)
NL (1)	NL146140B (de)
NO (1)	NO132533C (de)
PH (1)	PH10518A (de)
SE (1)	SE393369B (de)
YU (1)	YU35331B (de)
ZA (1)	ZA71927B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5597271U (de) *	1978-12-28	1980-07-05

1970
- 1970-03-16 GB GB02554/70A patent/GB1280767A/en not_active Expired
1971
- 1971-02-11 NO NO504/71A patent/NO132533C/no unknown
- 1971-02-15 IE IE175/71A patent/IE35009B1/xx unknown
- 1971-02-15 ZA ZA710927A patent/ZA71927B/xx unknown
- 1971-02-16 CA CA105,562A patent/CA948215A/en not_active Expired
- 1971-02-16 SE SE7101951A patent/SE393369B/xx unknown
- 1971-02-18 IL IL36225A patent/IL36225A0/xx unknown
- 1971-03-03 YU YU531/71A patent/YU35331B/xx unknown
- 1971-03-05 FI FI657/71A patent/FI55170C/fi active
- 1971-03-08 CH CH332071A patent/CH558315A/de not_active IP Right Cessation
- 1971-03-09 FR FR7108077A patent/FR2085710B1/fr not_active Expired
- 1971-03-10 BE BE764081A patent/BE764081A/xx not_active IP Right Cessation
- 1971-03-11 NL NL717103249A patent/NL146140B/xx not_active IP Right Cessation
- 1971-03-11 AT AT209771A patent/AT303711B/de not_active IP Right Cessation
- 1971-03-15 PH PH12292A patent/PH10518A/en unknown
- 1971-03-16 JP JP46014646A patent/JPS515378B1/ja active Pending
- 1971-03-16 ES ES389282A patent/ES389282A1/es not_active Expired
- 1971-03-16 DK DK126571A patent/DK146015C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO132533C (de)	1975-11-26
GB1280767A (en)	1972-07-05
FI55170B (fi)	1979-02-28
FI55170C (fi)	1979-06-11
PH10518A (en)	1977-05-26
ES389282A1 (es)	1973-06-16
JPS515378B1 (de)	1976-02-19
AT303711B (de)	1972-12-11
YU53171A (en)	1980-06-30
DK146015C (da)	1983-10-24
SE393369B (sv)	1977-05-09
ZA71927B (en)	1971-10-27
NL7103249A (de)	1971-09-20
CH558315A (de)	1975-01-31
CA948215A (en)	1974-05-28
NL146140B (nl)	1975-06-16
DK146015B (da)	1983-05-24
DE2110428B2 (de)	1976-08-26
FR2085710A1 (de)	1971-12-31
IL36225A0 (en)	1971-04-28
IE35009B1 (en)	1975-10-15
BE764081A (fr)	1971-08-02
YU35331B (en)	1980-12-31
IE35009L (en)	1971-09-16
DE2110428A1 (de)	1971-10-07
FR2085710B1 (de)	1975-08-01

Publication	Publication Date	Title
DK145260B (da)	1982-10-18	Analogifremgangsmaade til fremstilling af 4-acylamino-phenyl-ethanolaminer eller syreadditionssalte heraf
US2908691A (en)	1959-10-13	Hydroxyphenalkylaminoalkylindoles and ethers corresponding thereto
Fieser et al.	1942	A Synthesis of 4, 10-Ace-1, 2-benzanthracene Utilizing Δ4-Tetrahydrophthalic Anhydride
Schweizer et al.	1972	Reactions of phosphorus compounds. 31. Reactions of substituted. alpha.-imino ketones with vinyltriphenylphosphonium bromide
Fry et al.	1970	Sodium borohydride reductions of indolylethylpyridinium bromides. Hexahydroindoloquinolizines
Carlin et al.	1959	The Fischer Indole Synthesis. VI. A Non-aromatic Intermediate and a New Class of Hydroindoles1
Chorvat et al.	1978	Total synthesis of 2-azaestratrienes
Stevenson et al.	1956	Further Products from 4α-Acetoxy-Δ5-cholestene-3-one
US4166131A (en)	1979-08-28	Indaneacetic acid derivatives
EP0077536B1 (de)	1986-07-16	2'-Substituierte-spiro(benzofuran-2(3H),1'-cycloalkane), ein Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zusammenstellungen und ihre Anwendung als Arzneimittel
Cava et al.	1964	The stereochemistry of limaspermine, haplocine and haplocidine
Leonard et al.	1952	Reactions of Quinolinium Compounds with Phenylacetonitrile and Its Homologs
Julian et al.	1948	Studies in the Indole Series. VIII. Yohimbine (Part 1). The Mechanism of Dehydrogenation of Yohimbine and Related Compounds1
Morrow et al.	1967	Synthesis of 17-disubstituted steroids by the Claisen rearrangement
Yates et al.	1969	Aliphatic diazo compounds. IX. The base-induced dimerization of α-diazo ketones
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