FI60004C - Foerfarande foer framstaellning av terapeutiskt aktiv 3-(4-p-fluorfenyl-1-metylbutyl)-1-hydroxi-6,6,9-trimetyl-7,8,9,10-tetrahydro-6h-dibenso(b d)pyran - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiv 3-(4-p-fluorfenyl-1-metylbutyl)-1-hydroxi-6,6,9-trimetyl-7,8,9,10-tetrahydro-6h-dibenso(b d)pyran Download PDFInfo
- Publication number
- FI60004C FI60004C FI921/74A FI92174A FI60004C FI 60004 C FI60004 C FI 60004C FI 921/74 A FI921/74 A FI 921/74A FI 92174 A FI92174 A FI 92174A FI 60004 C FI60004 C FI 60004C
- Authority
- FI
- Finland
- Prior art keywords
- fluorophenyl
- methylbutyl
- tetrahydro
- formula
- compound
- Prior art date
Links
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 title claims description 5
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 230000004913 activation Effects 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 4-p-fluorophenyl-1-methylbutyl Chemical group 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- YJKHOUIVWKQRSL-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)ethanone Chemical compound COC1=CC(OC)=CC(C(C)=O)=C1 YJKHOUIVWKQRSL-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 12
- 208000002193 Pain Diseases 0.000 description 8
- 230000036407 pain Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 5
- YQQPIJQDVATYIV-UHFFFAOYSA-N 1-[5-(4-fluorophenyl)pentan-2-yl]-3,5-dimethoxybenzene Chemical compound COC1=CC(OC)=CC(C(C)CCCC=2C=CC(F)=CC=2)=C1 YQQPIJQDVATYIV-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940035676 analgesics Drugs 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MTHCJSUSFLMSIS-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)pentan-2-yl]benzene-1,3-diol Chemical compound C=1C(O)=CC(O)=CC=1C(C)CCCC1=CC=C(F)C=C1 MTHCJSUSFLMSIS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- SCVWLBZEYMAAHN-UHFFFAOYSA-N 1-(3-bromopropyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCCBr)C=C1 SCVWLBZEYMAAHN-UHFFFAOYSA-N 0.000 description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940125714 antidiarrheal agent Drugs 0.000 description 2
- 239000003793 antidiarrheal agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical class [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940080861 demerol Drugs 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- QMQBBUPJKANITL-MYXGOWFTSA-N dextropropoxyphene hydrochloride Chemical compound [H+].[Cl-].C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 QMQBBUPJKANITL-MYXGOWFTSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- FFVHHWOJYFCNJP-UHFFFAOYSA-N ethyl 4-methyl-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(C)CC1=O FFVHHWOJYFCNJP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34594473A | 1973-04-02 | 1973-04-02 | |
| US34594473 | 1973-04-02 | ||
| US442034A US3901926A (en) | 1973-04-02 | 1974-02-13 | Alkylphenyl benzopyrans |
| US44203474 | 1974-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI60004B FI60004B (fi) | 1981-07-31 |
| FI60004C true FI60004C (fi) | 1981-11-10 |
Family
ID=26994624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI921/74A FI60004C (fi) | 1973-04-02 | 1974-03-26 | Foerfarande foer framstaellning av terapeutiskt aktiv 3-(4-p-fluorfenyl-1-metylbutyl)-1-hydroxi-6,6,9-trimetyl-7,8,9,10-tetrahydro-6h-dibenso(b d)pyran |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3901926A (enExample) |
| JP (1) | JPS5035168A (enExample) |
| CA (1) | CA1010455A (enExample) |
| CH (1) | CH595375A5 (enExample) |
| DE (1) | DE2415697A1 (enExample) |
| FI (1) | FI60004C (enExample) |
| FR (1) | FR2223042B1 (enExample) |
| GB (1) | GB1459564A (enExample) |
| NL (1) | NL7404150A (enExample) |
| NO (1) | NO143943C (enExample) |
| PH (1) | PH12327A (enExample) |
| SE (1) | SE413244B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1522057A (en) * | 1975-11-03 | 1978-08-23 | Pfizer | 9-hydroxydibenzo(b,d)pyrans and intermediates therefor |
| US4018777A (en) * | 1975-11-14 | 1977-04-19 | Abbott Laboratories | 2-Substituted-5-alkyl resorcinols |
| US4051152A (en) * | 1976-01-07 | 1977-09-27 | Sharps Associates | Oxo C-ring benzopyrans |
| US4036857A (en) * | 1976-02-02 | 1977-07-19 | Sharps Associates | Benzopyrans having an unsaturated side chain |
| US4136183A (en) * | 1976-08-04 | 1979-01-23 | Abbott Laboratories | Benzopyranopyridines as antiglaucoma agents |
| US4247557A (en) * | 1976-08-04 | 1981-01-27 | Abbott Laboratories | Benzopyranopyridines as antiglaucoma agents |
| US4235913A (en) * | 1977-06-07 | 1980-11-25 | Pfizer Inc. | 9-Hydroxyhexahydrodibeno[b,d]pyrans, 1-substituted-9-hydroxyhexahydrodibenzo]b,d]pyrans |
| US4133819A (en) * | 1977-06-17 | 1979-01-09 | Pfizer Inc. | Hexahydro-1-hydroxy-9-hydroxymethyl-3-substituted-6H-dibenzo[b,d]pyrans as analgesic agents |
| US4209520A (en) * | 1977-06-17 | 1980-06-24 | Pfizer Inc. | Hexahydro-1-hydroxy-9-hydroxymethyl-3-substituted-6H-dibenzo[b,d]pyrans as analgesic agents |
| US4292316A (en) * | 1978-10-02 | 1981-09-29 | Abbott Laboratories | Antiglaucoma agents |
| US4454144A (en) * | 1982-06-21 | 1984-06-12 | Pfizer Inc. | Substituted dibenzo[b,d]pyran analgesics |
| IL161325A0 (en) * | 2001-11-19 | 2004-09-27 | Lilly Co Eli | Substituted benzopyrans as selective estrogen receptor-beta agonists |
| WO2004017922A2 (en) * | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| JP2007501279A (ja) * | 2003-05-20 | 2007-01-25 | ユニバーシティ・オブ・テネシー・リサーチ・ファウンデイション | カンナビノイド誘導体、その製造方法、および使用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2509386A (en) * | 1950-05-30 | Debenzopyran marihuana-like | ||
| US3639426A (en) * | 1970-01-08 | 1972-02-01 | Little Inc A | 4-oxo-9-hydroxy-7-(3-methyl-2-octyl)-1 2 3 4-tetrahydrocyclopenta(c)(1)benzopyran |
| US3799946A (en) * | 1972-03-13 | 1974-03-26 | Smithkline Corp | Dibenzo(b,d)pyran compounds |
-
1974
- 1974-02-13 US US442034A patent/US3901926A/en not_active Expired - Lifetime
- 1974-03-26 FI FI921/74A patent/FI60004C/fi active
- 1974-03-27 NL NL7404150A patent/NL7404150A/xx not_active Application Discontinuation
- 1974-03-29 NO NO741140A patent/NO143943C/no unknown
- 1974-03-29 FR FR7411150A patent/FR2223042B1/fr not_active Expired
- 1974-04-01 CA CA196,455A patent/CA1010455A/en not_active Expired
- 1974-04-01 GB GB1440474A patent/GB1459564A/en not_active Expired
- 1974-04-01 SE SE7404386A patent/SE413244B/xx unknown
- 1974-04-01 DE DE2415697A patent/DE2415697A1/de active Pending
- 1974-04-01 PH PH7415681A patent/PH12327A/en unknown
- 1974-04-02 JP JP49036717A patent/JPS5035168A/ja active Pending
- 1974-04-02 CH CH461774A patent/CH595375A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7404150A (enExample) | 1974-10-04 |
| US3901926A (en) | 1975-08-26 |
| SE413244B (sv) | 1980-05-12 |
| CA1010455A (en) | 1977-05-17 |
| CH595375A5 (enExample) | 1978-02-15 |
| NO741140L (no) | 1974-10-03 |
| FR2223042A1 (enExample) | 1974-10-25 |
| NO143943B (no) | 1981-02-02 |
| FR2223042B1 (enExample) | 1977-05-06 |
| NO143943C (no) | 1981-05-13 |
| AU6664074A (en) | 1975-09-18 |
| GB1459564A (en) | 1976-12-22 |
| FI60004B (fi) | 1981-07-31 |
| PH12327A (en) | 1979-01-16 |
| DE2415697A1 (de) | 1974-10-17 |
| JPS5035168A (enExample) | 1975-04-03 |
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