FI66870C - Foerfarande foer framstaellning av ny terapeutiskt anvaendbar 7-brom-1,5-dihydro-3,6-dimetyl-imidazo(2,1b)kinazolin-2(3h)-on och derivat daerav - Google Patents

Foerfarande foer framstaellning av ny terapeutiskt anvaendbar 7-brom-1,5-dihydro-3,6-dimetyl-imidazo(2,1b)kinazolin-2(3h)-on och derivat daerav Download PDF

Info

Publication number: FI66870C
Authority: FI; Finland
Prior art keywords: dihydro; quinazolin; bromo; formula; compounds
Prior art date: 1979-06-20

Application number

FI801910A

Other languages

English (en)

Finnish (fi)

Other versions

FI66870B (fi

FI801910A7 (fi

Inventor

Madhukar Subraya Chodnekar

Ado Kaiser

Original Assignee

Hoffmann La Roche

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.)

1979-06-20

Filing date

1980-06-13

Publication date

1984-12-10

1979-06-20 Priority claimed from US06/050,395 external-priority patent/US4256748A/en

1980-06-13 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-12-21 Publication of FI801910A7 publication Critical patent/FI801910A7/fi

1984-08-31 Application granted granted Critical

1984-08-31 Publication of FI66870B publication Critical patent/FI66870B/fi

1984-12-10 Publication of FI66870C publication Critical patent/FI66870C/fi

Links

238000000034 method Methods 0.000 title claims description 11
239000002253 acid Substances 0.000 title claims description 10
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title claims description 4
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 12
229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
239000011707 mineral Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 6
IASFSCWLFJGXQL-SSDOTTSWSA-N (3r)-7-bromo-3,6-dimethyl-5,10-dihydro-3h-imidazo[2,1-b]quinazolin-2-one Chemical compound C1=CC(Br)=C(C)C2=C1NC1=NC(=O)[C@@H](C)N1C2 IASFSCWLFJGXQL-SSDOTTSWSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
241000234282 Allium Species 0.000 claims 1
235000002732 Allium cepa var. cepa Nutrition 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229920001436 collagen Polymers 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000835 fiber Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
-1 2-methyl-6-nitrobenzyl Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000006502 antiplatelets effects Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
LRJUDHXAKVINPW-MRVPVSSYSA-N (3R)-3,6-dimethyl-3,5-dihydro-1H-imidazo[2,1-b]quinazolin-2-one Chemical compound C1C2=C(C)C=CC=C2N=C2N1[C@H](C)C(=O)N2 LRJUDHXAKVINPW-MRVPVSSYSA-N 0.000 description 1
MGYXDYAXFVTSMG-OGFXRTJISA-N (3R)-7-bromo-3,6-dimethyl-3,5-dihydro-1H-imidazo[2,1-b]quinazolin-2-one hydrobromide Chemical compound Br.C1C2=C(C)C(Br)=CC=C2N=C2N1[C@H](C)C(=O)N2 MGYXDYAXFVTSMG-OGFXRTJISA-N 0.000 description 1
FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
KPWVALMTRXELOS-UHFFFAOYSA-N 1-(bromomethyl)-2-methyl-3-nitrobenzene Chemical class CC1=C(CBr)C=CC=C1[N+]([O-])=O KPWVALMTRXELOS-UHFFFAOYSA-N 0.000 description 1
KISPFEKHMQYYLI-UHFFFAOYSA-N 1h-quinazolin-2-one;hydrobromide Chemical compound Br.C1=CC=C2NC(=O)N=CC2=C1 KISPFEKHMQYYLI-UHFFFAOYSA-N 0.000 description 1
MVLKTVRKDHDFOJ-UHFFFAOYSA-N 2-(bromomethyl)-1-methyl-3-nitrobenzene Chemical class CC1=CC=CC([N+]([O-])=O)=C1CBr MVLKTVRKDHDFOJ-UHFFFAOYSA-N 0.000 description 1
IASFSCWLFJGXQL-UHFFFAOYSA-N 7-bromo-3,6-dimethyl-5,10-dihydro-3h-imidazo[2,1-b]quinazolin-2-one Chemical compound C1C2=C(C)C(Br)=CC=C2N=C2N1C(C)C(=O)N2 IASFSCWLFJGXQL-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
KMZJFOYJKVQWFJ-UHFFFAOYSA-N BrN1C(C(N2C1=NC1=CC=CC(=C1C2)C)C)=O Chemical compound BrN1C(C(N2C1=NC1=CC=CC(=C1C2)C)C)=O KMZJFOYJKVQWFJ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101100246550 Caenorhabditis elegans pyr-1 gene Proteins 0.000 description 1
UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
229950006790 adenosine phosphate Drugs 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 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
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZJYZQVSCSFKDPV-SNVBAGLBSA-N ethyl (2r)-2-[(2-amino-3-methylphenyl)methylamino]propanoate Chemical compound CCOC(=O)[C@@H](C)NCC1=CC=CC(C)=C1N ZJYZQVSCSFKDPV-SNVBAGLBSA-N 0.000 description 1
OAXCTGQHMMFUIZ-SNVBAGLBSA-N ethyl (2r)-2-[(2-methyl-3-nitrophenyl)methylamino]propanoate Chemical compound CCOC(=O)[C@@H](C)NCC1=CC=CC([N+]([O-])=O)=C1C OAXCTGQHMMFUIZ-SNVBAGLBSA-N 0.000 description 1
JCXLZWMDXJFOOI-PGMHMLKASA-N ethyl (2r)-2-aminopropanoate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H](C)N JCXLZWMDXJFOOI-PGMHMLKASA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
BPGBAEXPBQHBSV-UHFFFAOYSA-N pyr1 Chemical compound C1=C2C3=C(C)C(C(NC=C4)=O)=C4C(C)=C3NC2=CC=C1OC(=O)C1=CC=CC=C1 BPGBAEXPBQHBSV-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI801910A 1979-06-20 1980-06-13 Foerfarande foer framstaellning av ny terapeutiskt anvaendbar 7-brom-1,5-dihydro-3,6-dimetyl-imidazo(2,1b)kinazolin-2(3h)-on och derivat daerav FI66870C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/050,395 US4256748A (en)	1977-07-25	1979-06-20	Imidazo[2,1-b]quinazolin-2(3H)-ones and pharmaceutical compositions for treatment and prophylaxis of cardiac insufficiency and cardiac failure
US5039579		1979-06-20
CH360080		1980-05-08
CH360080		1980-05-08

Publications (3)

Publication Number	Publication Date
FI801910A7 FI801910A7 (fi)	1980-12-21
FI66870B FI66870B (fi)	1984-08-31
FI66870C true FI66870C (fi)	1984-12-10

Family

ID=25693404

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI801910A FI66870C (fi)	1979-06-20	1980-06-13	Foerfarande foer framstaellning av ny terapeutiskt anvaendbar 7-brom-1,5-dihydro-3,6-dimetyl-imidazo(2,1b)kinazolin-2(3h)-on och derivat daerav

Country Status (14)

Country	Link
EP (1)	EP0021338B1 (es)
AU (1)	AU538119B2 (es)
CA (1)	CA1131631A (es)
DE (1)	DE3065273D1 (es)
DK (1)	DK259380A (es)
ES (3)	ES8105321A1 (es)
FI (1)	FI66870C (es)
IL (1)	IL60325A (es)
MC (1)	MC1332A1 (es)
NO (1)	NO801843L (es)
NZ (1)	NZ194046A (es)
PH (1)	PH16369A (es)
PT (1)	PT71411B (es)
YU (1)	YU161580A (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0054180A3 (de) *	1980-12-16	1982-12-01	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Verfahren zur Herstellung eines Imidazochinazolinonderivates
US4783467A (en) *	1985-06-05	1988-11-08	Pfizer Inc.	Tetrahydroimidazoquinazolinone inotropic agents
US6388073B1 (en) *	2000-07-26	2002-05-14	Shire Us Inc.	Method for the manufacture of anagrelide
US7700608B2 (en)	2004-08-04	2010-04-20	Shire Holdings Ag	Quinazoline derivatives and their use in the treatment of thrombocythemia
US8426429B2 (en)	2004-08-06	2013-04-23	Jansssen Pharmaceutica N.V.	2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE)
US8383637B2 (en)	2004-08-06	2013-02-26	Jansssen Pharmaceutica N.V.	2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE)
US8436006B2 (en)	2004-08-06	2013-05-07	Jansssen Pharmaceutica N.V.	2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE)
GB0623750D0 (en) *	2006-11-28	2007-01-10	Shire Llc	Substituted quinazolines
US7910597B2 (en)	2006-11-28	2011-03-22	Shire Llc	Substituted quinazolines
US8304420B2 (en)	2006-11-28	2012-11-06	Shire Llc	Substituted quinazolines for reducing platelet count

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3932407A (en) *	1973-11-19	1976-01-13	Bristol-Myers Company	Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones
BE794964A (fr) *	1972-02-04	1973-08-02	Bristol Myers Co	Nouveaux agents hypotenseurs et procede pour les preparer
US3988340A (en) *	1975-01-23	1976-10-26	Bristol-Myers Company	6-Alkoxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-ones and 7-alkoxymethyl-6-[H]-1,2,3,4-tetrahydropyrimido[2,1-b]quinazolin-2-ones
NL7807507A (nl) *	1977-07-25	1979-01-29	Hoffmann La Roche	Tricyclische verbindingen.
US4146718A (en) *	1978-04-10	1979-03-27	Bristol-Myers Company	Alkyl 5,6-dichloro-3,4-dihydro-2(1h)-iminoquinazoline-3-acetate hydrohalides

1980
- 1980-06-06 CA CA353,659A patent/CA1131631A/en not_active Expired
- 1980-06-13 NZ NZ194046A patent/NZ194046A/xx unknown
- 1980-06-13 FI FI801910A patent/FI66870C/fi not_active IP Right Cessation
- 1980-06-16 IL IL60325A patent/IL60325A/xx unknown
- 1980-06-17 AU AU59339/80A patent/AU538119B2/en not_active Ceased
- 1980-06-17 DK DK259380A patent/DK259380A/da not_active Application Discontinuation
- 1980-06-18 EP EP80103396A patent/EP0021338B1/de not_active Expired
- 1980-06-18 DE DE8080103396T patent/DE3065273D1/de not_active Expired
- 1980-06-18 MC MC801454A patent/MC1332A1/fr unknown
- 1980-06-18 PT PT71411A patent/PT71411B/pt unknown
- 1980-06-19 YU YU01615/80A patent/YU161580A/xx unknown
- 1980-06-19 ES ES492573A patent/ES8105321A1/es not_active Expired
- 1980-06-19 NO NO801843A patent/NO801843L/no unknown
- 1980-06-20 PH PH24171A patent/PH16369A/en unknown
1981
- 1981-02-16 ES ES499454A patent/ES499454A0/es active Granted
- 1981-02-16 ES ES499455A patent/ES8206524A1/es not_active Expired

Also Published As

Publication number	Publication date
PH16369A (en)	1983-09-14
YU161580A (en)	1983-04-30
AU5933980A (en)	1981-01-08
CA1131631A (en)	1982-09-14
DK259380A (da)	1980-12-21
MC1332A1 (fr)	1981-04-21
IL60325A (en)	1983-06-15
ES8201164A1 (es)	1981-12-01
NZ194046A (en)	1982-05-25
NO801843L (no)	1980-12-22
ES492573A0 (es)	1981-06-01
IL60325A0 (en)	1980-09-16
FI66870B (fi)	1984-08-31
ES8105321A1 (es)	1981-06-01
DE3065273D1 (de)	1983-11-17
ES499455A0 (es)	1982-08-16
AU538119B2 (en)	1984-08-02
EP0021338A1 (de)	1981-01-07
ES499454A0 (es)	1981-12-01
PT71411B (en)	1981-12-11
ES8206524A1 (es)	1982-08-16
EP0021338B1 (de)	1983-10-12
PT71411A (en)	1980-07-01
FI801910A7 (fi)	1980-12-21

Publication	Publication Date	Title
DE60005850T2 (de)	2005-03-24	Imidazo[1,2-a]pyridin- und pyrazolo[2,3-a]pyridinderivate
FI66870C (fi)	1984-12-10	Foerfarande foer framstaellning av ny terapeutiskt anvaendbar 7-brom-1,5-dihydro-3,6-dimetyl-imidazo(2,1b)kinazolin-2(3h)-on och derivat daerav
DE69225484T2 (de)	1998-12-10	Gallium iii komplexe, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die sie enthalten
EP0042593A1 (de)	1981-12-30	Aryloxypropanolamine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
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