CA2543074A1 - Nouvelles 2-(piperazin-1-yl)- et 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-ones, leur production et leur utilisation en tant que medicaments pour traiter le diabete sucre - Google Patents

Nouvelles 2-(piperazin-1-yl)- et 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-ones, leur production et leur utilisation en tant que medicaments pour traiter le diabete sucre Download PDF

Info

Publication number: CA2543074A1
Authority: CA; Canada
Prior art keywords: methyl; butyn; denotes; pyridazin; imidazo
Prior art date: 2003-12-17
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002543074A

Other languages

English (en)

Inventor

Frank Himmelsbach

Norbert Hauel

Elke Langkopf

Matthias Eckhardt

Iris Kauffmann-Hefner

Mohammad Tadayyon

Leo Thomas

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim International GmbH

Original Assignee

Individual

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.)

2003-12-17

Filing date

2004-12-11

Publication date

2005-06-30

2004-12-11 Application filed by Individual filed Critical Individual

2005-06-30 Publication of CA2543074A1 publication Critical patent/CA2543074A1/fr

Status Abandoned legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
206010012601 diabetes mellitus Diseases 0.000 title claims 2
239000003814 drug Substances 0.000 title description 3
DWHOCMSZEAMLHE-UHFFFAOYSA-N 2-(1,4-diazepan-1-yl)imidazo[4,5-d]pyridazin-4-one Chemical compound N1=C2C(=O)N=NC=C2N=C1N1CCCNCC1 DWHOCMSZEAMLHE-UHFFFAOYSA-N 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 35
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 claims abstract description 11
-1 phenylpyridinyl Chemical group 0.000 claims description 143
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 65
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 8
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 8
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
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WQXUCWREZPQWGG-UHFFFAOYSA-N 3-but-1-ynyl-5-(isoquinolin-1-ylmethyl)-2-piperazin-1-ylimidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C=CN=3)C(=O)C=2N(C#CCC)C=1N1CCNCC1 WQXUCWREZPQWGG-UHFFFAOYSA-N 0.000 claims description 6
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
CVDREBMCQBDSLU-UHFFFAOYSA-N 3-but-1-ynyl-5-[(2-fluoropyridin-3-yl)methyl]-2-piperazin-1-ylimidazo[4,5-d]pyridazin-4-one Chemical compound O=C1C=2N(C#CCC)C(N3CCNCC3)=NC=2C=NN1CC1=CC=CN=C1F CVDREBMCQBDSLU-UHFFFAOYSA-N 0.000 claims description 5
MVTBCJZQNZGGON-UHFFFAOYSA-N 3-but-1-ynyl-5-[(2-fluoropyridin-4-yl)methyl]-2-piperazin-1-ylimidazo[4,5-d]pyridazin-4-one Chemical compound O=C1C=2N(C#CCC)C(N3CCNCC3)=NC=2C=NN1CC1=CC=NC(F)=C1 MVTBCJZQNZGGON-UHFFFAOYSA-N 0.000 claims description 5
UAXUJFMYEUFQPI-UHFFFAOYSA-N 3-but-1-ynyl-5-[(2-methoxypyridin-3-yl)methyl]-2-piperazin-1-ylimidazo[4,5-d]pyridazin-4-one Chemical compound O=C1C=2N(C#CCC)C(N3CCNCC3)=NC=2C=NN1CC1=CC=CN=C1OC UAXUJFMYEUFQPI-UHFFFAOYSA-N 0.000 claims description 5
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HHOZYYJLFWJNBI-UHFFFAOYSA-N 3-but-1-ynyl-2-piperazin-1-yl-5-(pyridin-2-ylmethyl)imidazo[4,5-d]pyridazin-4-one Chemical compound O=C1C=2N(C#CCC)C(N3CCNCC3)=NC=2C=NN1CC1=CC=CC=N1 HHOZYYJLFWJNBI-UHFFFAOYSA-N 0.000 claims description 4
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FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
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Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
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Obesity (AREA)
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Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
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Cardiology (AREA)
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CA002543074A 2003-12-17 2004-12-11 Nouvelles 2-(piperazin-1-yl)- et 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-ones, leur production et leur utilisation en tant que medicaments pour traiter le diabete sucre Abandoned CA2543074A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10359098.6		2003-12-17
DE10359098A DE10359098A1 (de)	2003-12-17	2003-12-17	Neue 2-(Piperazin-1-yl)- und 2-([1,4]Diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-one, deren Herstellung und deren Verwendung als Arzneimittel
PCT/EP2004/014125 WO2005058901A1 (fr)	2003-12-17	2004-12-11	Nouvelles 2-(piperazin-1-yl)- et 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-ones, leur production et leur utilisation en tant que medicaments pour traiter le diabete sucre

Publications (1)

Publication Number	Publication Date
CA2543074A1 true CA2543074A1 (fr)	2005-06-30

Family

ID=34683431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002543074A Abandoned CA2543074A1 (fr)	2003-12-17	2004-12-11	Nouvelles 2-(piperazin-1-yl)- et 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-ones, leur production et leur utilisation en tant que medicaments pour traiter le diabete sucre

Country Status (5)

Country	Link
EP (1)	EP1742949A1 (fr)
JP (1)	JP2007513989A (fr)
CA (1)	CA2543074A1 (fr)
DE (1)	DE10359098A1 (fr)
WO (1)	WO2005058901A1 (fr)

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7407955B2 (en)	2002-08-21	2008-08-05	Boehringer Ingelheim Pharma Gmbh & Co., Kg	8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions
US7432262B2 (en)	2004-03-13	2008-10-07	Boehringer Ingelheim International Gmbh	Imidazopyridazinediones, their preparation and their use as pharmaceutical compositions
US7439370B2 (en)	2004-05-10	2008-10-21	Boehringer Ingelheim International Gmbh	Imidazole derivatives, their preparation and their use as intermediates for the preparation of pharmaceutical compositions and pesticides
US7470716B2 (en)	2004-06-24	2008-12-30	Boehringer Ingelheim International Gmbh	Imidazoles and triazoles, their preparation, and their use as pharmaceutical compositions
US7482337B2 (en)	2002-11-08	2009-01-27	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions
US7495005B2 (en)	2002-08-22	2009-02-24	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Xanthine derivatives, their preparation and their use in pharmaceutical compositions
US7495003B2 (en)	2004-09-11	2009-02-24	Boehringer Ingelheim International Gmbh	8-(3-amino-piperidin-1-yl)-7-(but-2-ynyl)-xanthines, the preparation thereof and their use as pharmaceutical compositions
US7495002B2 (en)	2004-09-14	2009-02-24	Boehringer Ingelheim International Gmbh	3-methyl-7-butinyl-xanthines, the preparation thereof and their use as pharmaceutical compositions
US7501426B2 (en)	2004-02-18	2009-03-10	Boehringer Ingelheim International Gmbh	8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions
US7550455B2 (en)	2003-11-27	2009-06-23	Boehringer Ingelheim International Gmbh	8-(piperazin-1yl)- and 8-([1,4]diazepan-1yl)-xanthines, the preparation thereof and their use as pharmaceutical composition
US7560450B2 (en)	2002-11-21	2009-07-14	Boehringer Ingelheim Pharma Gmbh & Co., Kg	Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions
US7566707B2 (en)	2003-06-18	2009-07-28	Boehringer Ingelheim International Gmbh	Imidazopyridazinone and imidazopyridone derivatives, the preparation thereof and their use as pharmaceutical compositions
US7569574B2 (en)	2002-08-22	2009-08-04	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Purine derivatives, the preparation thereof and their use as pharmaceutical compositions
US7645763B2 (en)	2004-02-23	2010-01-12	Boehringer Ingelheim Pharma Gmbh & Co. Kg	8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical composition
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EP1742949A1 (fr)	2007-01-17
DE10359098A1 (de)	2005-07-28
JP2007513989A (ja)	2007-05-31
WO2005058901A8 (fr)	2006-04-27
WO2005058901A1 (fr)	2005-06-30

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CA2561210A1 (fr)	2005-10-20	Nouvelles 2-amino-imidazo[4,5-d]pyridazin-4-ones et 2-amino-imidazo[4,5-c]pyridin-4-ones, leur production et leur utilisation comme medicaments
AU2012202850B2 (en)	2015-08-20	8-[3-amino-piperidin-1-yl]-xanthine, the production thereof and the use in the form of a DPP inhibitor