DD211548A1 - Verfahren zur herstellung neuartiger alkan- und alkenderivate - Google Patents

Verfahren zur herstellung neuartiger alkan- und alkenderivate Download PDF

Info

Publication number: DD211548A1
Authority: DD; German Democratic Republic
Prior art keywords: sub; formula; compounds; compound; carbon atoms
Prior art date: 1981-10-26

Application number

DD82244246A

Other languages

German (de)

English (en)

Inventor

Marja-Liisa Soedervall

Kauko O Kurkela

Arto J Karjalainen

Reijo J Toivola

Lauri V Kangas

Guillermo L Blanco

Original Assignee

Farmos Oy

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.)

1981-10-26

Filing date

1982-10-25

Publication date

1984-07-18

1982-10-25 Application filed by Farmos Oy filed Critical Farmos Oy

1984-07-18 Publication of DD211548A1 publication Critical patent/DD211548A1/de

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 13
150000001335 aliphatic alkanes Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 72
-1 2,3-epoxypropoxy, 2,3-dihydroxypropoxy Chemical group 0.000 claims abstract description 37
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 12
150000002148 esters Chemical class 0.000 claims abstract description 11
231100000252 nontoxic Toxicity 0.000 claims abstract description 7
230000003000 nontoxic effect Effects 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract 4
125000005336 allyloxy group Chemical group 0.000 claims abstract 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000010934 O-alkylation reaction Methods 0.000 claims description 3
238000006356 dehydrogenation reaction Methods 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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125000004103 aminoalkyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
230000000694 effects Effects 0.000 abstract description 14
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239000000543 intermediate Substances 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
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238000001727 in vivo Methods 0.000 description 4
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230000002829 reductive effect Effects 0.000 description 4
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WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
229910010082 LiAlH Inorganic materials 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940127219 anticoagulant drug Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000029918 bioluminescence Effects 0.000 description 1
238000005415 bioluminescence Methods 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
210000000172 cytosol Anatomy 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
UESSEMPSSAXQJC-UHFFFAOYSA-N ethanol;methanamine Chemical compound NC.CCO UESSEMPSSAXQJC-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
CJJTURWCOFWOLV-UHFFFAOYSA-N ethyl 2-[hydroxy-(4-hydroxyphenyl)-phenylmethyl]butanoate Chemical compound C=1C=C(O)C=CC=1C(O)(C(CC)C(=O)OCC)C1=CC=CC=C1 CJJTURWCOFWOLV-UHFFFAOYSA-N 0.000 description 1
PIBXMHBMQLGTHH-UHFFFAOYSA-N ethyl 2-[hydroxy-(4-methoxyphenyl)-phenylmethyl]butanoate Chemical compound C=1C=C(OC)C=CC=1C(O)(C(CC)C(=O)OCC)C1=CC=CC=C1 PIBXMHBMQLGTHH-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000037406 food intake Effects 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
210000004392 genitalia Anatomy 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
XWRJSDBMRJIGSK-UHFFFAOYSA-N lithium;phenylmethylbenzene Chemical compound [Li+].C=1C=CC=CC=1[CH-]C1=CC=CC=C1 XWRJSDBMRJIGSK-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229960004616 medroxyprogesterone Drugs 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
230000017095 negative regulation of cell growth Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
- 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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
- 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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
- 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
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon 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
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
- 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
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
- 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
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
- 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
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
- 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
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
- 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
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
- 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
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Epoxy Compounds (AREA)
Inorganic Insulating Materials (AREA)
Separation Of Gases By Adsorption (AREA)
Treating Waste Gases (AREA)
Steroid Compounds (AREA)

DD82244246A 1981-10-26 1982-10-25 Verfahren zur herstellung neuartiger alkan- und alkenderivate DD211548A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB08132240A GB2108486B (en)	1981-10-26	1981-10-26	Alkane and alkene derivatives and their preparation and use

Publications (1)

Publication Number	Publication Date
DD211548A1 true DD211548A1 (de)	1984-07-18

Family

ID=10525401

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82244246A DD211548A1 (de)	1981-10-26	1982-10-25	Verfahren zur herstellung neuartiger alkan- und alkenderivate

Country Status (18)

Country	Link
US (1)	US4556677A (fr)
EP (1)	EP0078158B1 (fr)
JP (1)	JPS5879934A (fr)
AT (1)	ATE22065T1 (fr)
AU (1)	AU555477B2 (fr)
CA (1)	CA1310974C (fr)
DD (1)	DD211548A1 (fr)
DE (1)	DE3273219D1 (fr)
DK (1)	DK472082A (fr)
FI (1)	FI77842C (fr)
GB (1)	GB2108486B (fr)
HU (1)	HU193268B (fr)
IE (1)	IE54586B1 (fr)
IL (1)	IL67049A (fr)
NO (1)	NO159079C (fr)
NZ (1)	NZ202269A (fr)
SU (1)	SU1329615A3 (fr)
ZA (1)	ZA827742B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2108486B (en) *	1981-10-26	1986-01-29	Farmos Group Ltd	Alkane and alkene derivatives and their preparation and use
US4775660A (en) *	1984-08-02	1988-10-04	Fernand Labrie	Treatment of breast cancer by combination therapy
US4666885A (en) *	1985-02-08	1987-05-19	Fernand Labrie	Combination therapy for treatment of female breast cancer
US4760053A (en) *	1984-08-02	1988-07-26	Fernand Labrie	Combination therapy for selected sex steroid dependent cancers
US4895715A (en) *	1988-04-14	1990-01-23	Schering Corporation	Method of treating gynecomastia
PH30747A (en) *	1989-03-10	1997-10-17	Endorech Inc	Combination therapy for the treatment of estrogen sensitive disease.
NL1018247C2 (nl)	2001-06-08	2002-12-10	Sara Lee De Nv	Inrichting voor het bereiden van een voor consumptie geschikte drank zoals koffie.
JP2004010479A (ja) *	2002-06-03	2004-01-15	Japan Science & Technology Corp	ブロック共重合体とアンスラサイクリン系抗癌剤を含む新規固型製剤及びその製造法
CN102317464B (zh)	2008-12-12	2014-10-29	塞莱西翁有限公司	从α-酮酸生物合成双官能烷烃
FR3071837B1 (fr)	2017-09-29	2019-11-01	Institut National De La Recherche Agronomique	Derive de lignine chimiquement stable et procede pour sa preparation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1306604A (fr) *	1959-03-03	1962-10-19	Ferrosan Ab	Procédé pour préparer des bisphényléthylènes substitués
GB1289966A (fr) *	1968-12-24	1972-09-20
US3661976A (en) *	1969-05-16	1972-05-09	Parke Davis & Co	4,4'-(2-cycloalkyl-alkylidene) diphenols and ethers and esters thereof
BE793686A (fr) *	1972-01-07	1973-07-04	Beecham Group Ltd	Composes di-aryliques biologiquement actifs
GB2108486B (en) *	1981-10-26	1986-01-29	Farmos Group Ltd	Alkane and alkene derivatives and their preparation and use

1981
- 1981-10-26 GB GB08132240A patent/GB2108486B/en not_active Expired
1982
- 1982-10-12 FI FI823465A patent/FI77842C/fi not_active IP Right Cessation
- 1982-10-18 SU SU823503159A patent/SU1329615A3/ru active
- 1982-10-21 DE DE8282305612T patent/DE3273219D1/de not_active Expired
- 1982-10-21 EP EP82305612A patent/EP0078158B1/fr not_active Expired
- 1982-10-21 AT AT82305612T patent/ATE22065T1/de not_active IP Right Cessation
- 1982-10-22 IL IL67049A patent/IL67049A/xx not_active IP Right Cessation
- 1982-10-22 AU AU89702/82A patent/AU555477B2/en not_active Ceased
- 1982-10-22 ZA ZA827742A patent/ZA827742B/xx unknown
- 1982-10-22 IE IE2551/82A patent/IE54586B1/en not_active IP Right Cessation
- 1982-10-22 NZ NZ202269A patent/NZ202269A/en unknown
- 1982-10-23 JP JP57186650A patent/JPS5879934A/ja active Granted
- 1982-10-25 DK DK472082A patent/DK472082A/da not_active Application Discontinuation
- 1982-10-25 CA CA000414128A patent/CA1310974C/fr not_active Expired - Fee Related
- 1982-10-25 DD DD82244246A patent/DD211548A1/de not_active IP Right Cessation
- 1982-10-25 NO NO823537A patent/NO159079C/no unknown
- 1982-10-25 HU HU823395A patent/HU193268B/hu not_active IP Right Cessation
- 1982-10-26 US US06/436,805 patent/US4556677A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
SU1329615A3 (ru)	1987-08-07
GB2108486B (en)	1986-01-29
EP0078158A2 (fr)	1983-05-04
GB2108486A (en)	1983-05-18
EP0078158B1 (fr)	1986-09-10
FI823465A0 (fi)	1982-10-12
FI77842C (fi)	1989-05-10
NO823537L (no)	1983-04-27
ATE22065T1 (de)	1986-09-15
JPH0239492B2 (fr)	1990-09-05
EP0078158A3 (en)	1984-01-18
AU8970282A (en)	1983-05-12
CA1310974C (fr)	1992-12-01
FI77842B (fi)	1989-01-31
IL67049A (en)	1987-07-31
NZ202269A (en)	1985-05-31
NO159079C (no)	1988-11-30
NO159079B (no)	1988-08-22
HU193268B (en)	1987-09-28
JPS5879934A (ja)	1983-05-13
IE54586B1 (en)	1989-12-06
DK472082A (da)	1983-04-27
FI823465L (fi)	1983-04-27
US4556677A (en)	1985-12-03
DE3273219D1 (en)	1986-10-16
AU555477B2 (en)	1986-09-25
ZA827742B (en)	1983-08-31
IE822551L (en)	1983-04-26

Legal Events

Date	Code	Title	Description
1997-10-23	UW	Conversion of economic patent into exclusive patent
1999-02-04	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69002248T2 (de)	1993-11-25	1,2-Cyclohexylaminoarylamide zu Verwendung als Analgetika.
DD230864A1 (de)	1985-12-11	Verfahren zur herstellung neuartiger alkan- und alkenabkoemmlinge
EP0287690B1 (fr)	1992-09-02	Adducts stables de solvant avec Z-1-(p-bêta-diméthylamino-éthoxyphényl)-1-(p-hydroxyphényl)-2-phénylbut-1-ène
DE2929517A1 (de)	1980-02-21	Pinenderivate, verfahren zu ihrer herstellung und sie enthaltende, pharmazeutische zubereitungen
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