FI68223C - Foerfarande foer framstaellning av 1-hydroxiaporfin-derivat - Google Patents

Foerfarande foer framstaellning av 1-hydroxiaporfin-derivat Download PDF

Info

Publication number: FI68223C
Authority: FI; Finland
Prior art keywords: reaction; process according; derivatives; hydroxy; vanadyl
Prior art date: 1977-12-22

Application number

FI783971A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI68223B (fi

FI783971A7 (fi

Inventor

Johannes Hartenstein

Gerhard Satzinger

Original Assignee

Warner Lambert Co

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.)

1977-12-22

Filing date

1978-12-22

Publication date

1985-08-12

1978-12-22 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1979-06-23 Publication of FI783971A7 publication Critical patent/FI783971A7/fi

1985-04-30 Publication of FI68223B publication Critical patent/FI68223B/fi

1985-08-12 Application granted granted Critical

1985-08-12 Publication of FI68223C publication Critical patent/FI68223C/fi

Links

YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
-1 tetrahydroisoquinoline compound Chemical class 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
MVRYYBFJTYHDQY-UHFFFAOYSA-N 6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1-ol Chemical class C12=CC=CC=C2CC2N(C)CCC3=CC=C(O)C1=C32 MVRYYBFJTYHDQY-UHFFFAOYSA-N 0.000 claims 1
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
HHQFLEDKAVLHOM-UHFFFAOYSA-N oxovanadium;trihydrofluoride Chemical compound F.F.F.[V]=O HHQFLEDKAVLHOM-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKORHWXYDBSYNO-MRXNPFEDSA-N (1r)-1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1C2=CC(O)=C(OC)C=C2CCN1C OKORHWXYDBSYNO-MRXNPFEDSA-N 0.000 description 3
RADQTHXRZJGDQI-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-ol Chemical class C1CNCC2=CC(O)=CC=C21 RADQTHXRZJGDQI-UHFFFAOYSA-N 0.000 description 3
XXZXBLWTTIZOHI-UHFFFAOYSA-N 21,23-dihydro-2H-porphyrin-1-ol Chemical class OC12CC=C(N1)C=C1C=CC(C=C3C=CC(=CC=4C=CC(=C2)N4)N3)=N1 XXZXBLWTTIZOHI-UHFFFAOYSA-N 0.000 description 3
OKORHWXYDBSYNO-UHFFFAOYSA-N Codamine Natural products C1=C(OC)C(OC)=CC=C1CC1C2=CC(O)=C(OC)C=C2CCN1C OKORHWXYDBSYNO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000007243 oxidative cyclization reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000005287 vanadyl group Chemical group 0.000 description 3
OKORHWXYDBSYNO-INIZCTEOSA-N (S)-codamine Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(O)=C(OC)C=C2CCN1C OKORHWXYDBSYNO-INIZCTEOSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MNYYCWDTJBJERS-UHFFFAOYSA-N Thalicmidine Natural products COC1=C(C=C2CCN(C)C3CC4=CC(=C(C=C4C1=C23)O)OC)OC MNYYCWDTJBJERS-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
150000003681 vanadium Chemical class 0.000 description 2
SQGWYPUYCOQZLL-UHFFFAOYSA-N 1-[1-(1,3-benzodioxol-5-ylmethyl)-7-hydroxy-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-2,2,2-trifluoroethanone Chemical compound C1=C2OCOC2=CC(CC2N(CCC=3C=C(C(=CC=32)O)OC)C(=O)C(F)(F)F)=C1 SQGWYPUYCOQZLL-UHFFFAOYSA-N 0.000 description 1
TWPVINXDIHCETB-UHFFFAOYSA-N 1-[1-[(3,4-dimethoxyphenyl)methyl]-7-hydroxy-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-2,2,2-trifluoroethanone Chemical compound C1=2C=C(O)C(OC)=CC=2CCN(C(=O)C(F)(F)F)C1CC1=CC=C(OC)C(OC)=C1 TWPVINXDIHCETB-UHFFFAOYSA-N 0.000 description 1
SAERKXUSZPTMCQ-UHFFFAOYSA-N 2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1-ol Chemical compound CN1CCC2=CC(OC)=C(O)C3=C2C1CC1=C3C=C(OC)C(OC)=C1 SAERKXUSZPTMCQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241001432959 Chernes Species 0.000 description 1
YHKCEKFPHYWDKS-UHFFFAOYSA-N OC12C(=CC(N1)=CC=1C=CC(N1)(C(=C1C=CC(N1)=CC=1C=CC(N1)=C2)OC)OC)OC Chemical compound OC12C(=CC(N1)=CC=1C=CC(N1)(C(=C1C=CC(N1)=CC=1C=CC(N1)=C2)OC)OC)OC YHKCEKFPHYWDKS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

FI783971A 1977-12-22 1978-12-22 Foerfarande foer framstaellning av 1-hydroxiaporfin-derivat FI68223C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2757281A DE2757281C3 (de)	1977-12-22	1977-12-22	Verfahren zur Herstellung von 1 -Hydroxy-Aporphinderivaten
DE2757281		1977-12-22

Publications (3)

Publication Number	Publication Date
FI783971A7 FI783971A7 (fi)	1979-06-23
FI68223B FI68223B (fi)	1985-04-30
FI68223C true FI68223C (fi)	1985-08-12

Family

ID=6026893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI783971A FI68223C (fi)	1977-12-22	1978-12-22	Foerfarande foer framstaellning av 1-hydroxiaporfin-derivat

Country Status (14)

Country	Link
US (1)	US4202980A (fr)
JP (1)	JPS54119475A (fr)
BE (1)	BE872842A (fr)
CH (1)	CH637642A5 (fr)
CS (1)	CS219347B2 (fr)
DD (1)	DD139845A5 (fr)
DE (1)	DE2757281C3 (fr)
FI (1)	FI68223C (fr)
FR (1)	FR2412534A1 (fr)
GB (1)	GB2011393B (fr)
HU (1)	HU178804B (fr)
IT (1)	IT1110876B (fr)
NL (1)	NL7812393A (fr)
SU (1)	SU878194A3 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5109136A (en) *	1990-08-09	1992-04-28	Warner-Lambert Company	Tetracyclic amines useful as cerebrovascular agents
US6210680B1 (en)	1999-06-11	2001-04-03	Univera Pharmaceuticals, Inc.	Method for the prevention and treatment of chronic venous insufficiency
TWI225397B (en) *	2000-05-04	2004-12-21	Nat Science Council	Uses of thaliporphine or its derivatives in treatment of cardiac diseases and preparation of the same
US20030187011A1 (en) *	2001-12-20	2003-10-02	Lashuel Hilal A.	Apomorphine inhibitors of amyloid-beta (Abeta) fibril formation and their use in amyloidosis based disease
TWI404536B (zh) *	2008-06-20	2013-08-11	生達化學製藥股份有限公司	阿朴芬化合物及其醫藥用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950344A (en) *	1973-09-13	1976-04-13	The University Of Virginia	Non-phenol oxidative coupling
DE2625116C2 (de) *	1976-06-04	1984-01-26	Gödecke AG, 1000 Berlin	Verfahren zur Herstellung von 4-Hydroxy-aporphin-Derivaten

1977
- 1977-12-22 DE DE2757281A patent/DE2757281C3/de not_active Expired
1978
- 1978-12-18 BE BE192381A patent/BE872842A/fr not_active IP Right Cessation
- 1978-12-19 GB GB7849003A patent/GB2011393B/en not_active Expired
- 1978-12-19 IT IT52364/78A patent/IT1110876B/it active
- 1978-12-19 US US05/971,142 patent/US4202980A/en not_active Expired - Lifetime
- 1978-12-20 DD DD78209942A patent/DD139845A5/de unknown
- 1978-12-21 HU HU78WA356A patent/HU178804B/hu unknown
- 1978-12-21 CH CH1305578A patent/CH637642A5/de not_active IP Right Cessation
- 1978-12-21 SU SU782700601A patent/SU878194A3/ru active
- 1978-12-21 FR FR7835894A patent/FR2412534A1/fr active Granted
- 1978-12-21 JP JP15695678A patent/JPS54119475A/ja active Pending
- 1978-12-21 NL NL7812393A patent/NL7812393A/xx not_active Application Discontinuation
- 1978-12-22 CS CS788858A patent/CS219347B2/cs unknown
- 1978-12-22 FI FI783971A patent/FI68223C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU878194A3 (ru)	1981-10-30
HU178804B (en)	1982-06-28
DD139845A5 (de)	1980-01-23
DE2757281C3 (de)	1980-10-23
DE2757281A1 (de)	1979-06-28
FI68223B (fi)	1985-04-30
BE872842A (fr)	1979-04-17
GB2011393A (en)	1979-07-11
US4202980A (en)	1980-05-13
FR2412534B1 (fr)	1983-05-20
IT7852364A0 (it)	1978-12-19
NL7812393A (nl)	1979-06-26
CS219347B2 (en)	1983-03-25
GB2011393B (en)	1982-05-06
IT1110876B (it)	1986-01-06
FR2412534A1 (fr)	1979-07-20
DE2757281B2 (de)	1980-02-21
FI783971A7 (fi)	1979-06-23
JPS54119475A (en)	1979-09-17
CH637642A5 (de)	1983-08-15

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: WARNER-LAMBERT COMPANY

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