NO130112B - - Google Patents

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Info

Publication number: NO130112B
Authority: NO; Norway
Prior art keywords: methyl; acetoxy; water; solution; methanol
Prior art date: 1968-02-24

Application number

NO00708/69A

Other languages

English (en)

Norwegian (no)

Inventor

H Berndt

H Steinbeck

R Wiechert

Original Assignee

Schering Ag

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.)

1968-02-24

Filing date

1969-02-21

Publication date

1974-07-08

1968-02-24 Priority claimed from DE19681668687 external-priority patent/DE1668687C3/de

1969-02-21 Application filed by Schering Ag filed Critical Schering Ag

1974-01-15 Priority to NO740112A priority Critical patent/NO130434C/no

1974-01-15 Priority to NO740111A priority patent/NO130275B/no

1974-01-15 Priority to NO740113A priority patent/NO130435C/no

1974-07-08 Publication of NO130112B publication Critical patent/NO130112B/no

Links

150000001875 compounds Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
239000005457 ice water Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000001195 anabolic effect Effects 0.000 description 2
230000001548 androgenic effect Effects 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
-1 n-heptyl anhydride Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
238000006027 Birch reduction reaction Methods 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000000151 deposition Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000013048 microbiological method Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000019260 propionic acid Nutrition 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
229920006395 saturated elastomer Polymers 0.000 description 1
QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000002381 testicular Effects 0.000 description 1
DDDVBYGLVAHHCD-UHFFFAOYSA-M tetraethylazanium;formate Chemical compound [O-]C=O.CC[N+](CC)(CC)CC DDDVBYGLVAHHCD-UHFFFAOYSA-M 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)

NO00708/69A 1968-02-24 1969-02-21 NO130112B (nl)

Priority Applications (3)

Application Number	Priority Date	Filing Date
NO740112A NO130434C (nl)	1968-02-24	1974-01-15
NO740111A NO130275B (nl)	1968-02-24	1974-01-15
NO740113A NO130435C (nl)	1968-02-24	1974-01-15

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19681668687 DE1668687C3 (de)	1968-02-24	1968-02-24	Neue 1 8-Methyt-Salpha-H-androstane, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
NO130112B true NO130112B (nl)	1974-07-08

Family

ID=5686123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00708/69A NO130112B (nl)	1968-02-24	1969-02-21

Country Status (18)

Country	Link
US (1)	US3812165A (nl)
AT (5)	AT310961B (nl)
BE (1)	BE728841A (nl)
BR (1)	BR6906616D0 (nl)
CH (4)	CH538461A (nl)
CS (1)	CS151503B2 (nl)
DE (1)	DE1668687B2 (nl)
DK (1)	DK121553B (nl)
ES (1)	ES364018A1 (nl)
FI (4)	FI46157C (nl)
FR (1)	FR2002566A1 (nl)
GB (1)	GB1260398A (nl)
HU (3)	HU163799B (nl)
IE (1)	IE32652B1 (nl)
IL (1)	IL31653A (nl)
NL (1)	NL162082C (nl)
NO (1)	NO130112B (nl)
SE (4)	SE363319B (nl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4098802A (en) *	1975-02-18	1978-07-04	Akzona Incorporated	Oral pharmaceutical preparation having androgenic activity
DE102005051974A1 (de) *	2005-10-31	2007-05-03	Basf Ag	Verfahren zur Herstellung von Trioxan und mindestens einem Comonomer

1968
- 1968-02-24 DE DE1968SC042018 patent/DE1668687B2/de active Granted
1969
- 1969-02-07 AT AT903171A patent/AT310961B/de not_active IP Right Cessation
- 1969-02-07 AT AT948870A patent/AT307633B/de not_active IP Right Cessation
- 1969-02-07 CH CH1036872D patent/CH538461A/de not_active IP Right Cessation
- 1969-02-07 AT AT903371A patent/AT310962B/de not_active IP Right Cessation
- 1969-02-07 AT AT128369A patent/AT293635B/de not_active IP Right Cessation
- 1969-02-07 CH CH1036972A patent/CH547270A/xx not_active IP Right Cessation
- 1969-02-07 CH CH1036572A patent/CH536825A/de not_active IP Right Cessation
- 1969-02-07 CH CH193569A patent/CH528492A/de not_active IP Right Cessation
- 1969-02-07 AT AT948770A patent/AT307632B/de not_active IP Right Cessation
- 1969-02-07 FI FI690383A patent/FI46157C/fi active
- 1969-02-10 DK DK70069AA patent/DK121553B/da unknown
- 1969-02-19 CS CS1163A patent/CS151503B2/cs unknown
- 1969-02-19 IL IL31653A patent/IL31653A/xx unknown
- 1969-02-20 US US00801158A patent/US3812165A/en not_active Expired - Lifetime
- 1969-02-21 SE SE11219/71A patent/SE363319B/xx unknown
- 1969-02-21 SE SE11221/71A patent/SE363321B/xx unknown
- 1969-02-21 SE SE11220/71A patent/SE363320B/xx unknown
- 1969-02-21 NO NO00708/69A patent/NO130112B/no unknown
- 1969-02-21 SE SE2457/69A patent/SE346104B/xx unknown
- 1969-02-22 HU HUSCHE421*1A patent/HU163799B/hu unknown
- 1969-02-22 HU HUSCHE224*1A patent/HU164143B/hu unknown
- 1969-02-22 HU HUSCHE420*1A patent/HU164336B/hu unknown
- 1969-02-24 GB GB9800/69A patent/GB1260398A/en not_active Expired
- 1969-02-24 ES ES364018A patent/ES364018A1/es not_active Expired
- 1969-02-24 BR BR206616/69A patent/BR6906616D0/pt unknown
- 1969-02-24 FR FR6904637A patent/FR2002566A1/fr not_active Withdrawn
- 1969-02-24 BE BE728841D patent/BE728841A/xx unknown
- 1969-02-24 NL NL6902874.A patent/NL162082C/nl not_active IP Right Cessation
- 1969-02-24 IE IE242/69A patent/IE32652B1/xx unknown
1971
- 1971-10-05 FI FI712779A patent/FI46722C/fi active
- 1971-10-05 FI FI712780A patent/FI46723C/fi active
- 1971-10-05 FI FI712781A patent/FI46724C/fi active

Also Published As

Publication number	Publication date
GB1260398A (en)	1972-01-19
ES364018A1 (es)	1971-01-01
FI46157C (fi)	1973-01-10
FI46723C (fi)	1973-06-11
AT307633B (de)	1973-05-25
FI46722C (fi)	1973-06-11
IE32652B1 (en)	1973-10-17
FI46157B (nl)	1972-10-02
DE1668687B2 (de)	1976-06-24
FI46724C (fi)	1973-06-11
NL162082C (nl)	1980-04-15
CH536825A (de)	1973-06-29
DE1668687A1 (de)	1971-09-02
CH538461A (de)	1973-08-15
CH547270A (de)	1974-03-29
HU164336B (nl)	1974-01-28
CH528492A (de)	1972-09-30
FI46724B (nl)	1973-02-28
AT293635B (de)	1971-10-25
NL162082B (nl)	1979-11-15
BR6906616D0 (pt)	1973-05-03
CS151503B2 (nl)	1973-10-19
SE363321B (nl)	1974-01-14
FI46722B (nl)	1973-02-28
SE363320B (nl)	1974-01-14
BE728841A (nl)	1969-08-25
SE346104B (nl)	1972-06-26
NL6902874A (nl)	1969-08-26
AT307632B (de)	1973-05-25
AT310962B (de)	1973-10-25
FI46723B (nl)	1973-02-28
IE32652L (en)	1969-08-24
SE363319B (nl)	1974-01-14
IL31653A0 (en)	1969-04-30
US3812165A (en)	1974-05-21
FR2002566A1 (nl)	1969-10-17
DK121553B (da)	1971-11-01
HU163799B (nl)	1973-10-27
AT310961B (de)	1973-10-25
IL31653A (en)	1974-01-14
HU164143B (nl)	1973-12-28

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