IL37752A - Imidazo(4,5-b)pyridine-2-carbamic acid derivatives,processes for their preparation and pharmaceutical and veterinary compositions containing the same - Google Patents

Imidazo(4,5-b)pyridine-2-carbamic acid derivatives,processes for their preparation and pharmaceutical and veterinary compositions containing the same

Info

Publication number: IL37752A
Authority: IL; Israel
Prior art keywords: imidazo; general formula; pyridine; preparation; quaternary ammonium
Prior art date: 1970-09-21

Application number

IL37752A

Other languages

English (en)

Other versions

IL37752A0 (en

Original Assignee

Rhone Poulenc Sa

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.)

1970-09-21

Filing date

1971-09-17

Publication date

1974-10-22

1970-09-21 Priority claimed from FR7034133A external-priority patent/FR2105060A1/fr

1971-08-25 Priority claimed from FR7130825A external-priority patent/FR2150236A2/fr

1971-09-17 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1971-11-29 Publication of IL37752A0 publication Critical patent/IL37752A0/xx

1974-10-22 Publication of IL37752A publication Critical patent/IL37752A/en

Links

238000000034 method Methods 0.000 title claims description 27
239000000203 mixture Substances 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 10
KYTUMWHVXBSTNL-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=N1 KYTUMWHVXBSTNL-UHFFFAOYSA-N 0.000 title 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 17
150000003222 pyridines Chemical class 0.000 claims description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 14
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 5
150000002460 imidazoles Chemical class 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims description 2
239000011248 coating agent Substances 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
150000001879 copper Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 9
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000000725 suspension Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
-1 alkyl radical Chemical class 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
230000037396 body weight Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241001494479 Pecora Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000003226 decolorizating effect Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
BPYHGTCRXDWOIQ-UHFFFAOYSA-N 3-nitropyridin-2-amine Chemical class NC1=NC=CC=C1[N+]([O-])=O BPYHGTCRXDWOIQ-UHFFFAOYSA-N 0.000 description 1
AITFREYTVOPXOT-UHFFFAOYSA-N 5-methylpyridine-2,3-diamine Chemical compound CC1=CN=C(N)C(N)=C1 AITFREYTVOPXOT-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000283707 Capra Species 0.000 description 1
241000180412 Dictyocaulus filaria Species 0.000 description 1
241000935792 Dipylidium caninum Species 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical class CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
241000243974 Haemonchus contortus Species 0.000 description 1
108010034145 Helminth Proteins Proteins 0.000 description 1
208000006968 Helminthiasis Diseases 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
241000244206 Nematoda Species 0.000 description 1
241001137880 Nematodirus battus Species 0.000 description 1
241001126260 Nippostrongylus Species 0.000 description 1
241000902235 Oides Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
241000244155 Taenia Species 0.000 description 1
241000191771 Teladorsagia circumcincta Species 0.000 description 1
241000607143 Toxascaris leonina Species 0.000 description 1
241000244030 Toxocara canis Species 0.000 description 1
241000122945 Trichostrongylus axei Species 0.000 description 1
241000243796 Trichostrongylus colubriformis Species 0.000 description 1
241001489151 Trichuris Species 0.000 description 1
240000000359 Triticum dicoccon Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
206010014881 enterobiasis Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
244000000013 helminth Species 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
150000002541 isothioureas Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
HFGVEKZGLZDHNH-UHFFFAOYSA-N methyl N-[(3-aminopyridin-2-yl)carbamothioyl]carbamate Chemical compound COC(=O)NC(NC1=NC=CC=C1N)=S HFGVEKZGLZDHNH-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
IBAYTUMFEGTADC-UHFFFAOYSA-N methyl n-(1h-imidazo[4,5-b]pyridin-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=N1 IBAYTUMFEGTADC-UHFFFAOYSA-N 0.000 description 1
LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
244000045947 parasite Species 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940100445 wheat starch Drugs 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL37752A 1970-09-21 1971-09-17 Imidazo(4,5-b)pyridine-2-carbamic acid derivatives,processes for their preparation and pharmaceutical and veterinary compositions containing the same IL37752A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7034133A FR2105060A1 (en)	1970-09-21	1970-09-21	Anthelmintic imidazo (4,5-b) pyridine derivs - with low mammalian toxicity,for oral human and veterinary use
FR7130825A FR2150236A2 (en)	1971-08-25	1971-08-25	Anthelmintic imidazo (4,5-b) pyridine derivs - with low mammalian toxicity,for oral human and veterinary use

Publications (2)

Publication Number	Publication Date
IL37752A0 IL37752A0 (en)	1971-11-29
IL37752A true IL37752A (en)	1974-10-22

Family

ID=26215952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL37752A IL37752A (en)	1970-09-21	1971-09-17	Imidazo(4,5-b)pyridine-2-carbamic acid derivatives,processes for their preparation and pharmaceutical and veterinary compositions containing the same

Country Status (13)

Country	Link
AU (1)	AU453067B2 (fr)
BE (1)	BE772835A (fr)
CA (1)	CA940131A (fr)
CH (1)	CH532600A (fr)
DE (1)	DE2147103C3 (fr)
DK (1)	DK131345B (fr)
ES (2)	ES395260A1 (fr)
GB (1)	GB1318859A (fr)
HU (1)	HU163150B (fr)
IL (1)	IL37752A (fr)
LU (1)	LU63927A1 (fr)
NL (1)	NL145553B (fr)
SE (1)	SE368828B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE298569T1 (de)	1999-03-31	2005-07-15	Uaf Technologies And Res Llc	Virus behandlung
US6593466B1 (en) *	1999-07-07	2003-07-15	Isis Pharmaceuticals, Inc.	Guanidinium functionalized nucleotides and precursors thereof
US6384049B1 (en)	2000-05-25	2002-05-07	The Procter & Gamble Company	Cancer treatment

1971
- 1971-09-17 IL IL37752A patent/IL37752A/en unknown
- 1971-09-20 DK DK458771AA patent/DK131345B/da unknown
- 1971-09-20 LU LU63927D patent/LU63927A1/xx unknown
- 1971-09-20 BE BE772835A patent/BE772835A/fr unknown
- 1971-09-20 CH CH1372371A patent/CH532600A/fr not_active IP Right Cessation
- 1971-09-20 HU HURO628A patent/HU163150B/hu unknown
- 1971-09-20 CA CA123264A patent/CA940131A/en not_active Expired
- 1971-09-20 SE SE11891/71A patent/SE368828B/xx unknown
- 1971-09-21 NL NL717112971A patent/NL145553B/xx unknown
- 1971-09-21 DE DE2147103A patent/DE2147103C3/de not_active Expired
- 1971-09-21 ES ES395260A patent/ES395260A1/es not_active Expired
- 1971-09-21 GB GB4400371A patent/GB1318859A/en not_active Expired
- 1971-09-21 AU AU33735/71A patent/AU453067B2/en not_active Expired
1972
- 1972-06-15 ES ES403910A patent/ES403910A1/es not_active Expired

Also Published As

Publication number	Publication date
AU453067B2 (en)	1974-09-19
ES403910A1 (es)	1975-05-01
GB1318859A (en)	1973-05-31
DE2147103C3 (de)	1975-07-17
LU63927A1 (fr)	1972-06-27
AU3373571A (en)	1973-03-29
IL37752A0 (en)	1971-11-29
BE772835A (fr)	1972-03-20
HU163150B (fr)	1973-06-28
CA940131A (en)	1974-01-15
CH532600A (fr)	1973-01-15
NL7112971A (fr)	1972-03-23
DE2147103A1 (de)	1972-03-23
ES395260A1 (es)	1973-12-01
DK131345C (fr)	1975-11-24
NL145553B (nl)	1975-04-15
DK131345B (da)	1975-06-30
SE368828B (fr)	1974-07-22
DE2147103B2 (de)	1974-11-14

Publication	Publication Date	Title
US5260291A (en)	1993-11-09	Tetrazine derivatives
RU2136682C1 (ru)	1999-09-10	Имидазопиридины, способ их получения, фармацевтическая композиция на их основе и способ получения фармацевтической композиции
EP0150255B1 (fr)	1990-12-12	Immunomodulateurs à base de pyrrolo(1,2-a)imidazole et imidazo(1,2-a)pyridine
CZ301499A3 (cs)	2000-02-16	Sloučeniny pro inhibici sekrece žaludeční kyseliny
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