SE505908C2 - Nya selenofenderivat, ett förfarande för framställning därav samt terapeutiska kompositioner innehållande dem - Google Patents

Nya selenofenderivat, ett förfarande för framställning därav samt terapeutiska kompositioner innehållande dem

Info

Publication number: SE505908C2
Authority: SE; Sweden
Prior art keywords: compound; compounds; benzo; selenofen; cyclohepta
Prior art date: 1989-11-22

Application number

SE9003704A

Other languages

English (en)

Swedish (sv)

Other versions

SE9003704D0 (sv

SE9003704L (sv

Inventor

Pierre Braquet

Colette Broquet

Original Assignee

Sod Conseils Rech Applic

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.)

1989-11-22

Filing date

1990-11-21

Publication date

1997-10-20

1990-11-21 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

1990-11-21 Publication of SE9003704D0 publication Critical patent/SE9003704D0/xx

1991-05-23 Publication of SE9003704L publication Critical patent/SE9003704L/xx

1997-10-20 Publication of SE505908C2 publication Critical patent/SE505908C2/sv

Links

239000000203 mixture Substances 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title claims description 3
230000001225 therapeutic effect Effects 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 4
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 3
235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 2
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims description 2
229910001950 potassium oxide Inorganic materials 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 1
229910001629 magnesium chloride Inorganic materials 0.000 claims 1
MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 abstract description 4
150000003839 salts Chemical class 0.000 abstract 1
230000000694 effects Effects 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
206010006482 Bronchospasm Diseases 0.000 description 13
ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 11
229960004958 ketotifen Drugs 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
208000009079 Bronchial Spasm Diseases 0.000 description 7
208000014181 Bronchial disease Diseases 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
108010058846 Ovalbumin Proteins 0.000 description 7
229940092253 ovalbumin Drugs 0.000 description 7
YHEBYTAHDOHSHQ-UHFFFAOYSA-N 2-piperidin-1-yl-1-selenophen-2-ylethanol Chemical compound C=1C=C[se]C=1C(O)CN1CCCCC1 YHEBYTAHDOHSHQ-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
230000007885 bronchoconstriction Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
241000700198 Cavia Species 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052754 neon Inorganic materials 0.000 description 4
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000010983 kinetics study Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
-1 o-carboxybenzyltriphenylphosphonium bromide methyl ester Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
RNPCZYQXYZYELK-UHFFFAOYSA-N (2-carboxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].OC(=O)C1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RNPCZYQXYZYELK-UHFFFAOYSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
ZEZWXODPUQYCEW-UHFFFAOYSA-N 2-(2-selenophen-2-ylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=C[se]1 ZEZWXODPUQYCEW-UHFFFAOYSA-N 0.000 description 1
QSLMPDKYTNEMFQ-UHFFFAOYSA-N 2-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CBr QSLMPDKYTNEMFQ-UHFFFAOYSA-N 0.000 description 1
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
206010002199 Anaphylactic shock Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241001269524 Dura Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000019687 Lamb Nutrition 0.000 description 1
241000283986 Lepus Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001529870 Meoma Species 0.000 description 1
HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
101100113004 Schizosaccharomyces pombe (strain 972 / ATCC 24843) fta1 gene Proteins 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000002804 anti-anaphylactic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
208000006673 asthma 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
229910052799 carbon Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000003255 drug test Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000001558 histaminolytic effect Effects 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
ZCQVEMXIVISDLV-UHFFFAOYSA-M magnesium;1-methylpiperidin-4-ide;chloride Chemical compound [Mg+2].[Cl-].CN1CC[CH-]CC1 ZCQVEMXIVISDLV-UHFFFAOYSA-M 0.000 description 1
229960005042 mequitazine Drugs 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
235000012149 noodles Nutrition 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
AGBORNIRMFZCGC-UHFFFAOYSA-N selenophene-2-carbaldehyde Chemical compound O=CC1=CC=C[se]1 AGBORNIRMFZCGC-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

SE9003704A 1989-11-22 1990-11-21 Nya selenofenderivat, ett förfarande för framställning därav samt terapeutiska kompositioner innehållande dem SE505908C2 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898926392A GB8926392D0 (en)	1989-11-22	1989-11-22	Selenophen derivatives

Publications (3)

Publication Number	Publication Date
SE9003704D0 SE9003704D0 (sv)	1990-11-21
SE9003704L SE9003704L (sv)	1991-05-23
SE505908C2 true SE505908C2 (sv)	1997-10-20

Family

ID=10666721

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE9003704A SE505908C2 (sv)	1989-11-22	1990-11-21	Nya selenofenderivat, ett förfarande för framställning därav samt terapeutiska kompositioner innehållande dem

Country Status (31)

Country	Link
US (1)	US5075322A (de)
JP (1)	JP2686364B2 (de)
KR (1)	KR910009689A (de)
AT (1)	AT398570B (de)
AU (1)	AU624309B2 (de)
BE (1)	BE1004607A3 (de)
CA (1)	CA2029776C (de)
CH (1)	CH681079A5 (de)
DE (1)	DE4037187A1 (de)
DK (1)	DK276690A (de)
DZ (1)	DZ1460A1 (de)
ES (1)	ES2027507A6 (de)
FI (1)	FI89599C (de)
FR (2)	FR2654730B1 (de)
GB (2)	GB8926392D0 (de)
GR (1)	GR1000883B (de)
HK (1)	HK92793A (de)
IE (1)	IE64402B1 (de)
IN (1)	IN175709B (de)
IT (1)	IT1243921B (de)
LU (1)	LU87847A1 (de)
MA (1)	MA22001A1 (de)
MY (1)	MY104529A (de)
NL (1)	NL9002433A (de)
NO (1)	NO177568C (de)
NZ (1)	NZ235971A (de)
OA (1)	OA09330A (de)
PT (1)	PT95943B (de)
SE (1)	SE505908C2 (de)
TN (1)	TNSN90138A1 (de)
ZA (1)	ZA909026B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19780042D2 (de) *	1996-01-26	1999-01-28	Nattermann A & Cie	Therapeutische Mittel, enthaltend organische Selenverbindungen gegen Asthma
EP2619200A4 (de) *	2010-09-22	2014-10-15	Calcimedica Inc	Verbindungen als modulatoren von intrazellulärem calcium

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH531000A (de) *	1970-03-11	1972-11-30	Sandoz Ag	Verfahren zur Herstellung neuer Benzocycloheptathiophene

1989
- 1989-11-20 DZ DZ890207A patent/DZ1460A1/fr active
- 1989-11-22 GB GB898926392A patent/GB8926392D0/en active Pending
1990
- 1990-10-30 GR GR900100781A patent/GR1000883B/el unknown
- 1990-11-06 NZ NZ235971A patent/NZ235971A/en unknown
- 1990-11-07 IN IN1105DE1990 patent/IN175709B/en unknown
- 1990-11-08 NL NL9002433A patent/NL9002433A/nl not_active Application Discontinuation
- 1990-11-09 ZA ZA909026A patent/ZA909026B/xx unknown
- 1990-11-12 GB GB9024589A patent/GB2238310B/en not_active Expired - Fee Related
- 1990-11-13 CA CA002029776A patent/CA2029776C/en not_active Expired - Fee Related
- 1990-11-14 US US07/613,149 patent/US5075322A/en not_active Expired - Fee Related
- 1990-11-15 CH CH3628/90A patent/CH681079A5/fr not_active IP Right Cessation
- 1990-11-16 BE BE9001083A patent/BE1004607A3/fr not_active IP Right Cessation
- 1990-11-20 LU LU87847A patent/LU87847A1/fr unknown
- 1990-11-20 IT IT02211590A patent/IT1243921B/it active IP Right Grant
- 1990-11-20 FI FI905717A patent/FI89599C/fi not_active IP Right Cessation
- 1990-11-20 MY MYPI90002041A patent/MY104529A/en unknown
- 1990-11-20 MA MA22275A patent/MA22001A1/fr unknown
- 1990-11-20 ES ES9002941A patent/ES2027507A6/es not_active Expired - Lifetime
- 1990-11-21 AT AT0236490A patent/AT398570B/de not_active IP Right Cessation
- 1990-11-21 PT PT95943A patent/PT95943B/pt not_active IP Right Cessation
- 1990-11-21 DK DK276690A patent/DK276690A/da not_active Application Discontinuation
- 1990-11-21 KR KR1019900018880A patent/KR910009689A/ko not_active Abandoned
- 1990-11-21 JP JP2314507A patent/JP2686364B2/ja not_active Expired - Lifetime
- 1990-11-21 SE SE9003704A patent/SE505908C2/sv not_active IP Right Cessation
- 1990-11-21 NO NO905047A patent/NO177568C/no unknown
- 1990-11-21 AU AU66781/90A patent/AU624309B2/en not_active Ceased
- 1990-11-21 IE IE420790A patent/IE64402B1/en not_active IP Right Cessation
- 1990-11-21 TN TNTNSN90138A patent/TNSN90138A1/fr unknown
- 1990-11-22 OA OA59899A patent/OA09330A/xx unknown
- 1990-11-22 FR FR9014566A patent/FR2654730B1/fr not_active Expired - Fee Related
- 1990-11-22 FR FR9014565A patent/FR2654622B1/fr not_active Expired - Fee Related
- 1990-11-22 DE DE4037187A patent/DE4037187A1/de not_active Withdrawn
1993
- 1993-09-09 HK HK927/93A patent/HK92793A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU624309B2 (en)	1992-06-04
IT1243921B (it)	1994-06-28
FR2654730A1 (fr)	1991-05-24
KR910009689A (ko)	1991-06-28
NZ235971A (en)	1993-02-25
PT95943A (pt)	1991-09-13
JPH03170479A (ja)	1991-07-24
IT9022115A1 (it)	1992-05-20
LU87847A1 (fr)	1991-05-07
GB2238310B (en)	1993-04-21
DK276690A (da)	1991-05-23
OA09330A (fr)	1992-09-15
FI89599C (fi)	1993-10-25
GB8926392D0 (en)	1990-01-10
MA22001A1 (fr)	1991-07-01
GB9024589D0 (en)	1991-01-02
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