ZA200207956B - 8-quinolinxanthine and 8-isoquinolinxanthine derivatives as PDE 5 inhibitors. - Google Patents
8-quinolinxanthine and 8-isoquinolinxanthine derivatives as PDE 5 inhibitors. Download PDFInfo
- Publication number
- ZA200207956B ZA200207956B ZA200207956A ZA200207956A ZA200207956B ZA 200207956 B ZA200207956 B ZA 200207956B ZA 200207956 A ZA200207956 A ZA 200207956A ZA 200207956 A ZA200207956 A ZA 200207956A ZA 200207956 B ZA200207956 B ZA 200207956B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- formula
- alkoxy
- compound
- hydrogen
- Prior art date
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- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 title description 2
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 105
- -1 hydroxy, aminosulfonyl Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 45
- 150000003839 salts Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 101150085511 PEDS1 gene Proteins 0.000 claims description 9
- 102100037592 Plasmanylethanolamine desaturase Human genes 0.000 claims description 9
- 229920003199 poly(diethylsiloxane) Polymers 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 230000026030 halogenation Effects 0.000 claims description 6
- 238000005658 halogenation reaction Methods 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000020335 dealkylation Effects 0.000 claims description 3
- 238000006900 dealkylation reaction Methods 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 5
- 101150065749 Churc1 gene Proteins 0.000 claims 5
- 102100038239 Protein Churchill Human genes 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 44
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
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- 239000002585 base Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000007529 inorganic bases Chemical class 0.000 description 6
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000003125 aqueous solvent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 3
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
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- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 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
- 150000004820 halides Chemical class 0.000 description 3
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- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229960003310 sildenafil Drugs 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
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Landscapes
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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Publications (1)
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| ZA200207956B true ZA200207956B (en) | 2003-07-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200207956A ZA200207956B (en) | 2000-04-07 | 2002-10-03 | 8-quinolinxanthine and 8-isoquinolinxanthine derivatives as PDE 5 inhibitors. |
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| CN (1) | CN1176922C (da) |
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| AT (1) | ATE253576T1 (da) |
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| PT (1) | PT1268480E (da) |
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| TR (1) | TR200400185T4 (da) |
| WO (1) | WO2001077110A1 (da) |
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Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10135815A1 (de) * | 2001-07-23 | 2003-02-06 | Bayer Ag | Verwendung von 2-Alkoxyphenyl-substituierten Imidazotriazinonen |
| US7019010B2 (en) * | 2001-09-27 | 2006-03-28 | Novertis Ag | Combinations |
| RU2295525C2 (ru) | 2002-06-12 | 2007-03-20 | Ф.Хоффманн-Ля Рош Аг | Амидозамещенные производные ксантина, обладающие ингибирующим действием фосфоенолпируваткарбоксикиназы (фепкк), способ их получения, фармацевтическая композиция и применение |
| 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 |
| CN107674077A (zh) * | 2002-08-21 | 2018-02-09 | 勃林格殷格翰制药两合公司 | 8‑[3‑氨基‑哌啶‑1‑基]‑黄嘌呤化合物，其制备方法及作为药物制剂的用途 |
| KR100728425B1 (ko) * | 2003-02-19 | 2007-06-13 | 에프. 호프만-라 로슈 아게 | Ｐｅｐｃｋ 억제제로서 사용하기 위한 설폰아마이드 치환된크산틴 유도체 |
| US7148229B2 (en) | 2003-02-19 | 2006-12-12 | Hoffman-La Roche Inc. | Sulfonamide substituted xanthine derivatives |
| JP4859666B2 (ja) * | 2003-06-06 | 2012-01-25 | エンダセア， インコーポレイテッド | Ａ１アデノシンレセプターアンタゴニスト |
| KR100658080B1 (ko) * | 2003-08-26 | 2006-12-15 | 비오이 하이디스 테크놀로지 주식회사 | 백라이트 조립용 지그 |
| TW200605893A (en) * | 2004-02-12 | 2006-02-16 | Novartis Ag | Use of organic compounds |
| 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 |
| ES2384619T3 (es) * | 2004-05-08 | 2012-07-09 | Novartis International Pharmaceutical Ltd. | Isoquinolinas 1-aril-4-sustituidas |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| DE102005001989A1 (de) * | 2005-01-15 | 2006-07-20 | Bayer Healthcare Ag | Intravenöse Formulierungen von PDE-Inhibitoren |
| US7601723B2 (en) * | 2005-02-25 | 2009-10-13 | Pgx Health, Llc | Pyridyl substituted xanthines |
| WO2006104870A2 (en) * | 2005-03-25 | 2006-10-05 | Schering Corporation | Methods of treating benign prostatic hyperplasia or lower urinary track symptoms by using pde 5 inhibitors |
| DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| CN101355876B (zh) | 2005-11-09 | 2012-09-05 | 康宾纳特克斯公司 | 一种适用于眼部给药的组合物 |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| NZ573360A (en) | 2006-05-04 | 2012-08-31 | Boehringer Ingelheim Int | Polymorphic forms of 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(R)-amino-piperidin-1-yl)-xanthine |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| CN101711153A (zh) * | 2007-06-13 | 2010-05-19 | 拜耳先灵制药股份公司 | 用于治疗听觉损伤的pde抑制剂 |
| AR071175A1 (es) | 2008-04-03 | 2010-06-02 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| KR20190016601A (ko) | 2008-08-06 | 2019-02-18 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| JP2012502081A (ja) | 2008-09-10 | 2012-01-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糖尿病及び関連症状の治療のための組み合わせ治療 |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| TWI508965B (zh) | 2008-12-23 | 2015-11-21 | Boehringer Ingelheim Int | 有機化合物的鹽形式 |
| TW201036975A (en) | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
| CN102361557A (zh) * | 2009-03-26 | 2012-02-22 | Mapi医药公司 | 制备阿格列汀的方法 |
| JP2013512229A (ja) | 2009-11-27 | 2013-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 遺伝子型が同定された糖尿病患者のリナグリプチン等のｄｄｐ−ｉｖ阻害薬による治療 |
| NZ602921A (en) | 2010-05-05 | 2016-01-29 | Boehringer Ingelheim Int | Combination therapy comprising the administration of a glp-1 receptor agonist and a ddp-4 inhibitor |
| MX2012014247A (es) | 2010-06-24 | 2013-01-18 | Boehringer Ingelheim Int | Terapia para la diabetes. |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| WO2012112946A1 (en) * | 2011-02-18 | 2012-08-23 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| EP3517539B1 (en) | 2011-07-15 | 2022-12-14 | Boehringer Ingelheim International GmbH | Substituted dimeric quinazoline derivative, its preparation and its use in pharmaceutical compositions for the treatment of type i and ii diabetes |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| WO2014071044A1 (en) * | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
| EP3468562A1 (en) | 2016-06-10 | 2019-04-17 | Boehringer Ingelheim International GmbH | Combinations of linagliptin and metformin |
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| FR2558162B1 (fr) * | 1984-01-17 | 1986-04-25 | Adir | Nouveaux derives de la xanthine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| GB9301192D0 (en) * | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
| AU4501199A (en) * | 1998-06-03 | 1999-12-20 | Almirall Prodesfarma S.A. | 8-phenylxanthine derivatives and their use as phosphodiesterase inhibitors |
| GB9828340D0 (en) * | 1998-12-22 | 1999-02-17 | Novartis Ag | Organic compounds |
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2000
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2001
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- 2001-04-05 IL IL15207801A patent/IL152078A0/xx unknown
- 2001-04-05 MY MYPI20011632A patent/MY119238A/en unknown
- 2001-04-05 KR KR10-2002-7012627A patent/KR100526094B1/ko not_active IP Right Cessation
-
2002
- 2002-10-02 NO NO20024741A patent/NO20024741L/no not_active Application Discontinuation
- 2002-10-03 ZA ZA200207956A patent/ZA200207956B/en unknown
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