CA2561210A1 - 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 - Google Patents

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 Download PDF

Info

Publication number: CA2561210A1
Authority: CA; Canada
Prior art keywords: group; amino; methyl; denotes; alkyl
Prior art date: 2004-04-10
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

CA002561210A

Other languages

English (en)

Inventor

Matthias Eckhardt

Frank Himmelsbach

Elke Langkopf

Norbert Hauel

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.)

2004-04-10

Filing date

2005-04-02

Publication date

2005-10-20

2004-04-10 Priority claimed from DE102004017739A external-priority patent/DE102004017739A1/de

2004-05-25 Priority claimed from DE200410025552 external-priority patent/DE102004025552A1/de

2005-04-02 Application filed by Individual filed Critical Individual

2005-10-20 Publication of CA2561210A1 publication Critical patent/CA2561210A1/fr

Status Abandoned legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
QOMVDXYDCBTJIP-UHFFFAOYSA-N 2-aminoimidazo[4,5-c]pyridin-4-one Chemical class C1=NC(=O)C2=NC(N)=NC2=C1 QOMVDXYDCBTJIP-UHFFFAOYSA-N 0.000 title abstract description 3
GVYKMPXOPDEVGB-UHFFFAOYSA-N 2-aminoimidazo[4,5-d]pyridazin-4-one Chemical class N1=NC(=O)C2=NC(N)=NC2=C1 GVYKMPXOPDEVGB-UHFFFAOYSA-N 0.000 title abstract description 3
239000003814 drug Substances 0.000 title description 3
239000000203 mixture Substances 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 30
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 12
-1 sulphinyl Chemical group 0.000 claims description 213
150000001875 compounds Chemical class 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
238000001727 in vivo Methods 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
UHOMMDAUPDGGBT-UHFFFAOYSA-N 2-[2-aminoethyl(methyl)amino]-3-but-2-ynyl-5-[(3-methylisoquinolin-1-yl)methyl]imidazo[4,5-c]pyridin-4-one Chemical compound C1=CC=C2C(CN3C=CC=4N=C(N(C=4C3=O)CC#CC)N(C)CCN)=NC(C)=CC2=C1 UHOMMDAUPDGGBT-UHFFFAOYSA-N 0.000 claims description 5
JRVZCNRSWBXYMA-UHFFFAOYSA-N 2-[[2-[(2-amino-2-methylpropyl)-methylamino]-3-but-2-ynyl-4-oxoimidazo[4,5-d]pyridazin-5-yl]methyl]benzonitrile Chemical compound O=C1C=2N(CC#CC)C(N(C)CC(C)(C)N)=NC=2C=NN1CC1=CC=CC=C1C#N JRVZCNRSWBXYMA-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
LJCXDHVCJXIQQN-HNNXBMFYSA-N 2-[[(2s)-2-aminopropyl]-methylamino]-3-but-2-ynyl-5-[(4-methylquinazolin-2-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound C1=CC=CC2=NC(CN3N=CC=4N=C(N(C=4C3=O)CC#CC)N(C)C[C@H](C)N)=NC(C)=C21 LJCXDHVCJXIQQN-HNNXBMFYSA-N 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000005002 aryl methyl group Chemical group 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000006278 bromobenzyl group Chemical group 0.000 claims description 4
125000004803 chlorobenzyl group Chemical group 0.000 claims description 4
125000002946 cyanobenzyl group Chemical group 0.000 claims description 4
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000006480 iodobenzyl group Chemical group 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 3
AMEFOKMDCIDFJK-UHFFFAOYSA-N 2-[2-aminoethyl(methyl)amino]-3-but-2-ynyl-5-[(3-methylisoquinolin-1-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound C1=CC=C2C(CN3N=CC=4N=C(N(C=4C3=O)CC#CC)N(C)CCN)=NC(C)=CC2=C1 AMEFOKMDCIDFJK-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
230000004962 physiological condition Effects 0.000 claims description 3
125000003367 polycyclic group Chemical group 0.000 claims description 3
125000006513 pyridinyl methyl group Chemical group 0.000 claims description 3
KVPGFCMNZYFYME-UHFFFAOYSA-N 2-[2-aminoethyl(methyl)amino]-3-but-2-ynyl-5-[(4-methylquinazolin-2-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound C1=CC=CC2=NC(CN3N=CC=4N=C(N(C=4C3=O)CC#CC)N(C)CCN)=NC(C)=C21 KVPGFCMNZYFYME-UHFFFAOYSA-N 0.000 claims description 2
LTRCHUTXDUFHMA-INIZCTEOSA-N 3-[[2-[[(2s)-2-aminopropyl]-methylamino]-3-but-2-ynyl-4-oxoimidazo[4,5-d]pyridazin-5-yl]methyl]isoquinoline-4-carbonitrile Chemical compound C1=CC=CC2=C(C#N)C(CN3N=CC=4N=C(N(C=4C3=O)CC#CC)N(C)C[C@H](C)N)=NC=C21 LTRCHUTXDUFHMA-INIZCTEOSA-N 0.000 claims description 2
102000055006 Calcitonin Human genes 0.000 claims description 2
108060001064 Calcitonin Proteins 0.000 claims description 2
208000001132 Osteoporosis Diseases 0.000 claims description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
206010003246 arthritis Diseases 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
229960004015 calcitonin Drugs 0.000 claims description 2
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125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
HCYYBBFWNWACCL-UHFFFAOYSA-N imidazo[4,5-c]pyridazin-3-one Chemical group N1=NC(=O)C=C2N=CN=C21 HCYYBBFWNWACCL-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
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125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
229940002612 prodrug Drugs 0.000 claims description 2
239000000651 prodrug Substances 0.000 claims description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
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238000002054 transplantation Methods 0.000 claims description 2
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AYSMDZJUUIDFLY-HNNXBMFYSA-N 2-[[2-[[(2s)-2-aminopropyl]-methylamino]-3-but-2-ynyl-4-oxoimidazo[4,5-d]pyridazin-5-yl]methyl]benzonitrile Chemical compound O=C1C=2N(CC#CC)C(N(C)C[C@H](C)N)=NC=2C=NN1CC1=CC=CC=C1C#N AYSMDZJUUIDFLY-HNNXBMFYSA-N 0.000 claims 2
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- 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

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
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CA002561210A 2004-04-10 2005-04-02 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 Abandoned CA2561210A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE102004017739A DE102004017739A1 (de)	2004-04-10	2004-04-10	Neue 2-Amino-imidazo(4,5-d)pyridazin-4-one, deren Herstellung und deren Verwendung als Arzneimittel
DE102004017739.2		2004-04-10
DE102004025552.0		2004-05-25
DE200410025552 DE102004025552A1 (de)	2004-05-25	2004-05-25	Neue 2-Amino-imidazo[4,5-d]pyridazin-4-one und 2-Amino-imidazo[4,5-c]pyridin-4-one, deren Herstellung und deren Verwendung als Arzneimittel
PCT/EP2005/003474 WO2005097798A1 (fr)	2004-04-10	2005-04-02	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

Publications (1)

Publication Number	Publication Date
CA2561210A1 true CA2561210A1 (fr)	2005-10-20

Family

ID=34964126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002561210A Abandoned CA2561210A1 (fr)	2004-04-10	2005-04-02	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

Country Status (4)

Country	Link
EP (1)	EP1740589A1 (fr)
JP (1)	JP2007531780A (fr)
CA (1)	CA2561210A1 (fr)
WO (1)	WO2005097798A1 (fr)

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2005
- 2005-04-02 JP JP2007506703A patent/JP2007531780A/ja active Pending
- 2005-04-02 CA CA002561210A patent/CA2561210A1/fr not_active Abandoned
- 2005-04-02 EP EP05716507A patent/EP1740589A1/fr not_active Withdrawn
- 2005-04-02 WO PCT/EP2005/003474 patent/WO2005097798A1/fr not_active Ceased

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Also Published As

Publication number	Publication date
WO2005097798A1 (fr)	2005-10-20
EP1740589A1 (fr)	2007-01-10
JP2007531780A (ja)	2007-11-08

Legal Events

Date	Code	Title	Description
2010-03-30	EEER	Examination request
2012-04-02	FZDE	Dead

Publication	Publication Date	Title
US7179809B2 (en)	2007-02-20	2-Amino-imidazo[4,5-d]pyridazin-4-ones, their preparation and their use as pharmaceutical compositions
US7906539B2 (en)	2011-03-15	Imidazoles and triazoles, their preparation, and their use as pharmaceutical compositions
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US7495003B2 (en)	2009-02-24	8-(3-amino-piperidin-1-yl)-7-(but-2-ynyl)-xanthines, the preparation thereof and their use as pharmaceutical compositions
US7217711B2 (en)	2007-05-15	Piperazin-1-yl and 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]-pyridazin-4-ones, the preparation thereof and their use as pharmaceutical compositions
CA2548323C (fr)	2012-12-04	Composes imidazol bicycliques, leur fabrication et leur utilisation comme medicaments
JP2007531780A (ja)	2007-11-08	新規な２−アミノ−イミダゾ［４，５−ｄ］ピリダジン−４−オン及び２−アミノ−イミダゾ［４，５−ｃ］ピリダジン−４−オン、その製法及び医薬としての使用
US7550455B2 (en)	2009-06-23	8-(piperazin-1yl)- and 8-([1,4]diazepan-1yl)-xanthines, the preparation thereof and their use as pharmaceutical composition
CA2555050C (fr)	2017-11-28	Derives de 8-[3-amino-piperidine-1-yl]-xanthines, la production de ceux-ci et leur utilisation sous la forme d'un inhibiteur de dpp-iv
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