IE36687B1 - N-substituted-14-hydroxy-3-substituted morphinan derivatives - Google Patents
N-substituted-14-hydroxy-3-substituted morphinan derivativesInfo
- Publication number
- IE36687B1 IE36687B1 IE1213/72A IE121372A IE36687B1 IE 36687 B1 IE36687 B1 IE 36687B1 IE 1213/72 A IE1213/72 A IE 1213/72A IE 121372 A IE121372 A IE 121372A IE 36687 B1 IE36687 B1 IE 36687B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxy
- methoxy
- morphinan
- methoxymorphinan
- alkyl
- Prior art date
Links
- -1 N-substituted-14-hydroxy-3-substituted morphinan Chemical class 0.000 title abstract 2
- 229940051807 opiod analgesics morphinan derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 239000004593 Epoxy Substances 0.000 abstract 2
- 229910010082 LiAlH Inorganic materials 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- STBZIDOIKQNFCQ-HSALFYBXSA-N oxilorphan Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CC1 STBZIDOIKQNFCQ-HSALFYBXSA-N 0.000 abstract 2
- DTVODKGBEXBXFW-BHIFYINESA-N (-)-3-methoxy butorphanol Chemical compound C([C@@]12C3=CC(OC)=CC=C3C[C@@]3([C@@]1(CCCC2)O)[H])CN3CC1CCC1 DTVODKGBEXBXFW-BHIFYINESA-N 0.000 abstract 1
- RHCCVERKZAOESA-IXDOHACOSA-N (1S,9R,10S)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@]2(O)CCCC3 RHCCVERKZAOESA-IXDOHACOSA-N 0.000 abstract 1
- NPKIPXIGRMJHLC-FGTMMUONSA-N (1S,9R,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-10-ol Chemical compound C1CCC[C@@]2(O)[C@]3([H])N(C)CC[C@@]21C1=CC(OC)=CC=C1C3 NPKIPXIGRMJHLC-FGTMMUONSA-N 0.000 abstract 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- ZREGHPIWNOPAHK-IXDOHACOSA-N 14-hydroxy-3-methoxymorphinan Chemical compound C1CCC[C@@]2(O)[C@]3([H])NCC[C@@]21C1=CC(OC)=CC=C1C3 ZREGHPIWNOPAHK-IXDOHACOSA-N 0.000 abstract 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 abstract 1
- XFJNXCYBJPHYBG-UHFFFAOYSA-N 2-(6-methoxy-2,3,4,9-tetrahydro-1h-phenanthren-4a-yl)ethanamine Chemical compound C1CCCC2(CCN)C3=CC(OC)=CC=C3CC=C21 XFJNXCYBJPHYBG-UHFFFAOYSA-N 0.000 abstract 1
- CLHJHEQLLOFWIT-YZYLHUITSA-N 8,14-epoxy-3-methoxy-n-trifluoroacetylmorphinan Chemical compound C1CCC2O[C@@]22[C@]3([H])N(C(=O)C(F)(F)F)CC[C@@]21C1=CC(OC)=CC=C1C3 CLHJHEQLLOFWIT-YZYLHUITSA-N 0.000 abstract 1
- XADIGBMVBVZWQK-XOJKTNQZSA-N 8,14-epoxy-3-methoxymorphinan Chemical compound C1CCC2O[C@@]22[C@]3([H])NCC[C@@]21C1=CC(OC)=CC=C1C3 XADIGBMVBVZWQK-XOJKTNQZSA-N 0.000 abstract 1
- VADKRGAKEOTLIK-HOQDWTEMSA-N C([C@@]12C3=CC(OC)=CC=C3C[C@@]3([C@]41OC4CCC2)[H])CN3C(=O)C1CC1 Chemical compound C([C@@]12C3=CC(OC)=CC=C3C[C@@]3([C@]41OC4CCC2)[H])CN3C(=O)C1CC1 VADKRGAKEOTLIK-HOQDWTEMSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- GJOVVPXDEXUSTC-OWCLPIDISA-N Norbutorphanol Chemical compound C1CCC[C@@]2(O)[C@H]3CC4=CC=C(O)C=C4[C@]21CCN3 GJOVVPXDEXUSTC-OWCLPIDISA-N 0.000 abstract 1
- BJUVRCCLKYLYSD-NJNPRVFISA-N [(1R,9R,10R)-17-(cyclopropylmethyl)-3-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl] acetate Chemical compound C1(CC1)CN1[C@H]2[C@@H]3CCCC[C@@]3(C=3C(=C(C=CC3C2)OC(C)=O)O)CC1 BJUVRCCLKYLYSD-NJNPRVFISA-N 0.000 abstract 1
- NAYDSNTVJUCACT-DSNGMDLFSA-N [(1S,9R,10S)-10-acetyloxy-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl] acetate Chemical compound C([C@@]12C3=CC(OC(C)=O)=CC=C3C[C@@]3([C@@]1(CCCC2)OC(C)=O)[H])CN3CC1CCC1 NAYDSNTVJUCACT-DSNGMDLFSA-N 0.000 abstract 1
- NRVBONMAOONMLD-XPWALMASSA-N [(1S,9R,10S)-17-(cyclobutylmethyl)-4-hydroxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-10-yl] acetate Chemical compound C([C@@]12C3=CC(O)=CC=C3C[C@@]3([C@@]1(CCCC2)OC(C)=O)[H])CN3CC1CCC1 NRVBONMAOONMLD-XPWALMASSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N alpha-naphthol Natural products C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- SSTNJZNPHRDOOG-YZGWKJHDSA-N ethyl (1S,9R,10S)-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-17-carboxylate Chemical compound C(C)OC(=O)N1[C@H]2[C@@]3(CCCC[C@@]3(C=3C=C(C=CC3C2)OC)CC1)O SSTNJZNPHRDOOG-YZGWKJHDSA-N 0.000 abstract 1
- KTWUWTPAZZBWRO-UHFFFAOYSA-N ethyl N-[2-(6-methoxy-2,3,4,9-tetrahydro-1H-phenanthren-4a-yl)ethyl]carbamate Chemical compound C(C)OC(=O)NCCC12CCCCC2=CCC2=CC=C(C=C12)OC KTWUWTPAZZBWRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000003809 morphinane derivatives Chemical class 0.000 abstract 1
- HODJEXJOBRJXBO-XPWALMASSA-N n-cyclobutylmethyl-14-hydroxy-3-methoxymethyloxy-morphinan Chemical compound C([C@@]12C3=CC(OCOC)=CC=C3C[C@@]3([C@@]1(CCCC2)O)[H])CN3CC1CCC1 HODJEXJOBRJXBO-XPWALMASSA-N 0.000 abstract 1
- DLUQGORFFANYBS-QHAWAJNXSA-N n-cyclopropylmethyl-3-methoxy-14-hydroxymorphinan Chemical compound C([C@@]12C3=CC(OC)=CC=C3C[C@@]3([C@@]1(CCCC2)O)[H])CN3CC1CC1 DLUQGORFFANYBS-QHAWAJNXSA-N 0.000 abstract 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 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
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/28—Morphinans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17883771A | 1971-09-08 | 1971-09-08 | |
| US00217633A US3819635A (en) | 1971-09-08 | 1972-01-13 | 14-hydroxymorphinan derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36687L IE36687L (en) | 1973-03-08 |
| IE36687B1 true IE36687B1 (en) | 1977-02-02 |
Family
ID=26874723
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1213/72A IE36687B1 (en) | 1971-09-08 | 1972-09-06 | N-substituted-14-hydroxy-3-substituted morphinan derivatives |
| IE103/76A IE36688B1 (en) | 1971-09-08 | 1972-09-06 | 3-substituted-morphinan derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE103/76A IE36688B1 (en) | 1971-09-08 | 1972-09-06 | 3-substituted-morphinan derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3819635A (en)) |
| JP (1) | JPS5310596B2 (en)) |
| AU (1) | AU470102B2 (en)) |
| BE (1) | BE788478A (en)) |
| CA (1) | CA999578A (en)) |
| CH (1) | CH590845A5 (en)) |
| CY (1) | CY980A (en)) |
| DD (1) | DD100255A5 (en)) |
| DE (3) | DE2243961A1 (en)) |
| DK (1) | DK141624B (en)) |
| FR (1) | FR2154481B1 (en)) |
| GB (2) | GB1412130A (en)) |
| HK (1) | HK2679A (en)) |
| IE (2) | IE36687B1 (en)) |
| KE (1) | KE2911A (en)) |
| MY (1) | MY7900027A (en)) |
| NL (1) | NL162072C (en)) |
| SE (2) | SE398877B (en)) |
| YU (1) | YU45099B (en)) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910920A (en) * | 1973-11-07 | 1975-10-07 | Bristol Myers Co | 3,14,17-Substituted-6,7-tetramethylenemorphinans |
| US3980641A (en) * | 1975-07-31 | 1976-09-14 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinans |
| US4017497A (en) * | 1975-11-18 | 1977-04-12 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| US4052389A (en) * | 1976-03-23 | 1977-10-04 | Bristol-Myers Company | Derivatives of 9,10-dihydroxy-1-(p-alkoxybenzyl)-perhydroisoquinoline oxazine-3-one |
| US4139534A (en) * | 1977-02-17 | 1979-02-13 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| JPS52136176A (en) * | 1976-03-23 | 1977-11-14 | Bristol Myers Co | Method of improving 144hydroxymorphinan derivatives |
| US4058531A (en) * | 1976-03-23 | 1977-11-15 | Bristol-Myers Company | Process for the preparation of 14-hydroxymorphinan derivatives |
| GB1587831A (en) * | 1977-03-23 | 1981-04-08 | Reckitt & Colmann Prod Ltd | Morphine derivatives |
| GB1593191A (en) * | 1977-03-23 | 1981-07-15 | Reckitt & Colmann Prod Ltd | Derivatives of morphine |
| US4115389A (en) * | 1977-05-02 | 1978-09-19 | Bristol-Myers Company | Process of N-demethylating (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline |
| US4338320A (en) * | 1978-11-15 | 1982-07-06 | The Board Of Regents Of The University Of Nebraska | Esters of 6'-hydroxycinchonine, and a method of treating arrythmia with them |
| US4228285A (en) * | 1979-02-28 | 1980-10-14 | Bristol-Myers Company | 14-Hydroxy-6-oxamorphinans and 14-hydroxy-6-oxaisomorphinans |
| US4272540A (en) * | 1979-04-24 | 1981-06-09 | Sisa, Incorporated | 14-Methoxymorphinan-6-one compounds and therapeutic methods of treating pain and drug dependence with them |
| US4322427A (en) * | 1981-04-16 | 1982-03-30 | Bristol-Myers Company | Analgetic compositions and methods of use |
| DE69414085T2 (de) * | 1993-07-19 | 1999-03-18 | Toray Industries, Inc., Tokio/Tokyo | Wirkstoff zum schutze von gehirnzellen |
| DE69424853T2 (de) * | 1993-07-23 | 2000-10-05 | Toray Industries, Inc. | Morphinan-derivate und ihre medizinische verwendung |
| CZ281174B6 (cs) * | 1993-08-13 | 1996-07-17 | Galena, A.S. | Způsob přípravy 3,14ß-dihydroxy-17-normorfinanu |
| AU753278B2 (en) | 1998-02-25 | 2002-10-10 | Abbott Laboratories | Butorphanol sustained release formulations |
| US20040167164A1 (en) * | 1998-05-05 | 2004-08-26 | Jose Pozuelo | Compositions and methods for treating particular chemical addictions and mental illnesses |
| US7923454B2 (en) | 2002-05-17 | 2011-04-12 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US7501433B2 (en) * | 2002-05-17 | 2009-03-10 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| WO2003097608A2 (en) | 2002-05-17 | 2003-11-27 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US8017622B2 (en) * | 2003-05-16 | 2011-09-13 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| CN103073496B (zh) * | 2013-02-18 | 2015-08-26 | 苏州立新制药有限公司 | 右美沙芬的制备方法 |
| JP6464181B2 (ja) | 2014-10-14 | 2019-02-06 | 久光製薬株式会社 | 貼付剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3166559A (en) * | 1965-01-19 | J-lower alkoxy-x-phenyloxy-ix-hydroxy- | ||
| GB1028407A (en) * | 1962-04-06 | 1966-05-04 | Shionogi & Co | Improvements in or relating to morphinan derivatives and their preparation |
| FR1362540A (fr) * | 1963-04-05 | 1964-06-05 | Shionogi & Co | Dérivés n substitués du morphinane et leur production |
-
0
- BE BE788478D patent/BE788478A/xx not_active IP Right Cessation
-
1972
- 1972-01-13 US US00217633A patent/US3819635A/en not_active Expired - Lifetime
- 1972-08-23 CA CA150,036A patent/CA999578A/en not_active Expired
- 1972-09-01 AU AU46228/72A patent/AU470102B2/en not_active Expired
- 1972-09-06 DK DK440172AA patent/DK141624B/da not_active IP Right Cessation
- 1972-09-06 IE IE1213/72A patent/IE36687B1/xx unknown
- 1972-09-06 IE IE103/76A patent/IE36688B1/xx unknown
- 1972-09-06 SE SE7211522A patent/SE398877B/xx unknown
- 1972-09-07 CH CH1315472A patent/CH590845A5/xx not_active IP Right Cessation
- 1972-09-07 DE DE2243961A patent/DE2243961A1/de active Granted
- 1972-09-07 GB GB1057175A patent/GB1412130A/en not_active Expired
- 1972-09-07 JP JP8916172A patent/JPS5310596B2/ja not_active Expired
- 1972-09-07 CY CY980A patent/CY980A/xx unknown
- 1972-09-07 DE DE2265256A patent/DE2265256C2/de not_active Expired
- 1972-09-07 FR FR7231816A patent/FR2154481B1/fr not_active Expired
- 1972-09-07 NL NL7212176.A patent/NL162072C/xx not_active IP Right Cessation
- 1972-09-07 DE DE2265255A patent/DE2265255C2/de not_active Expired
- 1972-09-07 YU YU227772A patent/YU45099B/sh unknown
- 1972-09-07 GB GB4161972A patent/GB1412129A/en not_active Expired
- 1972-09-08 DD DD165557A patent/DD100255A5/xx unknown
-
1975
- 1975-06-02 SE SE7506292A patent/SE403286B/xx not_active IP Right Cessation
-
1978
- 1978-12-24 KE KE2911A patent/KE2911A/xx unknown
-
1979
- 1979-01-11 HK HK26/79A patent/HK2679A/xx unknown
- 1979-12-30 MY MY27/79A patent/MY7900027A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL162072B (nl) | 1979-11-15 |
| GB1412130A (en) | 1975-10-29 |
| NL162072C (nl) | 1980-04-15 |
| IE36688B1 (en) | 1977-02-02 |
| DE2265256C2 (de) | 1985-10-24 |
| SE7506292L (sv) | 1975-06-02 |
| SE398877B (sv) | 1978-01-23 |
| AU470102B2 (en) | 1976-03-04 |
| KE2911A (en) | 1979-01-26 |
| DE2265255C2 (de) | 1986-06-05 |
| FR2154481B1 (en)) | 1976-04-23 |
| BE788478A (fr) | 1973-03-06 |
| JPS5310596B2 (en)) | 1978-04-14 |
| YU45099B (sh) | 1992-07-20 |
| DD100255A5 (en)) | 1973-09-12 |
| CY980A (en) | 1979-03-23 |
| IE36687L (en) | 1973-03-08 |
| CH590845A5 (en)) | 1977-08-31 |
| DE2243961C2 (en)) | 1988-07-21 |
| HK2679A (en) | 1979-01-19 |
| DK141624C (en)) | 1980-10-13 |
| DK141624B (da) | 1980-05-12 |
| SE403286B (sv) | 1978-08-07 |
| YU227772A (en) | 1982-02-28 |
| JPS4834864A (en)) | 1973-05-22 |
| GB1412129A (en) | 1975-10-29 |
| DE2265255A1 (de) | 1977-01-27 |
| FR2154481A1 (en)) | 1973-05-11 |
| DE2243961A1 (de) | 1973-04-05 |
| NL7212176A (en)) | 1973-03-12 |
| AU4622872A (en) | 1974-03-07 |
| DE2265256A1 (de) | 1977-01-27 |
| CA999578A (en) | 1976-11-09 |
| MY7900027A (en) | 1979-12-31 |
| US3819635A (en) | 1974-06-25 |
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