HRP20110942T1 - (dihidro)pirolo[2,1-a]izohinolini - Google Patents
(dihidro)pirolo[2,1-a]izohinolini Download PDFInfo
- Publication number
- HRP20110942T1 HRP20110942T1 HR20110942T HRP20110942T HRP20110942T1 HR P20110942 T1 HRP20110942 T1 HR P20110942T1 HR 20110942 T HR20110942 T HR 20110942T HR P20110942 T HRP20110942 T HR P20110942T HR P20110942 T1 HRP20110942 T1 HR P20110942T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- methoxy
- pyrrolo
- thiophen
- dihydro
- Prior art date
Links
- 150000002537 isoquinolines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 80
- -1 hydroxy, amino Chemical group 0.000 claims abstract 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 27
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract 20
- 150000002367 halogens Chemical class 0.000 claims abstract 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 19
- 125000001424 substituent group Chemical group 0.000 claims abstract 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 3
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims abstract 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 3
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims abstract 3
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims abstract 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 2
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 0.000 claims 6
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000021267 infertility disease Diseases 0.000 claims 2
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- XMZWCGPSFAPZKO-UHFFFAOYSA-N (8,9-dimethoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinolin-3-yl)-[4-(1-methylcyclobutanecarbonyl)-1,4-diazepan-1-yl]methanone Chemical compound C=12C=3C=C(OC)C(OC)=CC=3CCN2C(C(=O)N2CCN(CCC2)C(=O)C2(C)CCC2)=CC=1C1=CC=CS1 XMZWCGPSFAPZKO-UHFFFAOYSA-N 0.000 claims 1
- PFADOOZEOVHESF-UHFFFAOYSA-N 1-[3-(2,2-dimethylpyrrolidine-1-carbonyl)-8-methoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinolin-9-yl]ethanone Chemical compound C=12C=3C=C(C(C)=O)C(OC)=CC=3CCN2C(C(=O)N2C(CCC2)(C)C)=CC=1C1=CC=CS1 PFADOOZEOVHESF-UHFFFAOYSA-N 0.000 claims 1
- BKVCYRWCEORDKI-UHFFFAOYSA-N 1-[3-(8-methoxy-9-propan-2-yloxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carbonyl)-3,7-diazabicyclo[3.3.1]nonan-7-yl]-2-methylsulfanylethanone Chemical compound C=12C=3C=C(OC(C)C)C(OC)=CC=3CCN2C(C(=O)N2CC3CC(CN(C3)C(=O)CSC)C2)=CC=1C1=CC=CS1 BKVCYRWCEORDKI-UHFFFAOYSA-N 0.000 claims 1
- LQJLWZPXPQNQQP-UHFFFAOYSA-N 3-acetylpyrrolo[2,1-a]isoquinoline-1-carbonitrile Chemical compound C1=CC=C2C=CN3C(C(=O)C)=CC(C#N)=C3C2=C1 LQJLWZPXPQNQQP-UHFFFAOYSA-N 0.000 claims 1
- KPYBEQVHXQXLGY-UHFFFAOYSA-N 4-butyl-1-(8-methoxy-9-propan-2-yloxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carbonyl)-1,4-diazepan-5-one Chemical compound C1CC(=O)N(CCCC)CCN1C(=O)C1=CC(C=2SC=CC=2)=C2N1CCC1=CC(OC)=C(OC(C)C)C=C12 KPYBEQVHXQXLGY-UHFFFAOYSA-N 0.000 claims 1
- AVMISXIEDNNOLU-UHFFFAOYSA-N 7-(8-methoxy-9-propan-2-yloxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carbonyl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid Chemical class C(C)(C)OC1=C(C=C2CCN3C(C2=C1)=C(C=C3C(=O)N1CC2CN(CC(C1)C2)C(=O)O)C=1SC=CC=1)OC AVMISXIEDNNOLU-UHFFFAOYSA-N 0.000 claims 1
- ZBRBKKQTSZKGQX-UHFFFAOYSA-N CC(C)(C)NC.CC(C)(CCC(C=C(C(N(CC1)C(C(O)=O)=C2)=C2C2=CC=CS2)C1=C1)=C1OC)O Chemical class CC(C)(C)NC.CC(C)(CCC(C=C(C(N(CC1)C(C(O)=O)=C2)=C2C2=CC=CS2)C1=C1)=C1OC)O ZBRBKKQTSZKGQX-UHFFFAOYSA-N 0.000 claims 1
- KTVXCBJFFQIBBE-UHFFFAOYSA-N CC(C)(C)NC.COC(C=C(CCN(C(C(O)=O)=C1)C2=C1C1=CC=CS1)C2=C1)=C1OC1OCCCC1 Chemical class CC(C)(C)NC.COC(C=C(CCN(C(C(O)=O)=C1)C2=C1C1=CC=CS1)C2=C1)=C1OC1OCCCC1 KTVXCBJFFQIBBE-UHFFFAOYSA-N 0.000 claims 1
- JTILWSVWWQQYGH-UHFFFAOYSA-N CC(C)CC(C=C(C(N(CC1)C(C(O)=O)=C2)=C2C2=CC=CS2)C1=C1)=C1OC.CC(C)(CO)NC Chemical class CC(C)CC(C=C(C(N(CC1)C(C(O)=O)=C2)=C2C2=CC=CS2)C1=C1)=C1OC.CC(C)(CO)NC JTILWSVWWQQYGH-UHFFFAOYSA-N 0.000 claims 1
- IFCYMCQZQCPGGV-UHFFFAOYSA-N [4-(9-bromo-8-methoxy-1-thiophen-2-yl-5,6,6a,10a-tetrahydropyrrolo[2,1-a]isoquinoline-3-carbonyl)-1,4-diazepan-1-yl]-cyclobutylmethanone Chemical compound C=12C3C=C(Br)C(OC)=CC3CCN2C(C(=O)N2CCN(CCC2)C(=O)C2CCC2)=CC=1C1=CC=CS1 IFCYMCQZQCPGGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- OWYWDBUWPAHHSL-UHFFFAOYSA-N cyclobutyl-[4-(8,9-dimethoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carbonyl)-1,4-diazepan-1-yl]methanone Chemical compound C=12C=3C=C(OC)C(OC)=CC=3CCN2C(C(=O)N2CCN(CCC2)C(=O)C2CCC2)=CC=1C1=CC=CS1 OWYWDBUWPAHHSL-UHFFFAOYSA-N 0.000 claims 1
- INJNLHHOSDWURW-UHFFFAOYSA-N cyclobutyl-[4-(8,9-dimethoxy-1-thiophen-2-ylpyrrolo[2,1-a]isoquinoline-3-carbonyl)-1,4-diazepan-1-yl]methanone Chemical compound C=12C=3C=C(OC)C(OC)=CC=3C=CN2C(C(=O)N2CCN(CCC2)C(=O)C2CCC2)=CC=1C1=CC=CS1 INJNLHHOSDWURW-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- OUQVKRKGTAUJQA-UHFFFAOYSA-N n-[(1-chloro-4-hydroxyisoquinolin-3-yl)carbonyl]glycine Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 OUQVKRKGTAUJQA-UHFFFAOYSA-N 0.000 claims 1
- XLQFHEGHUDDGRK-UHFFFAOYSA-N n-[3-(2,2-dimethylpyrrolidine-1-carbonyl)-8-methoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinolin-9-yl]-2-methylpropanamide Chemical compound C=12C=3C=C(NC(=O)C(C)C)C(OC)=CC=3CCN2C(C(=O)N2C(CCC2)(C)C)=CC=1C1=CC=CS1 XLQFHEGHUDDGRK-UHFFFAOYSA-N 0.000 claims 1
- PWTGKFAJLBFCLH-UHFFFAOYSA-N n-[3-(2,2-dimethylpyrrolidine-1-carbonyl)-8-methoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinolin-9-yl]-2-morpholin-4-ylacetamide Chemical compound C=12C=3C=C(NC(=O)CN4CCOCC4)C(OC)=CC=3CCN2C(C(=O)N2C(CCC2)(C)C)=CC=1C1=CC=CS1 PWTGKFAJLBFCLH-UHFFFAOYSA-N 0.000 claims 1
- SSTSDRKCQKZXLG-UHFFFAOYSA-N n-[3-(2,2-dimethylpyrrolidine-1-carbonyl)-8-methoxy-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinolin-9-yl]methanesulfonamide Chemical compound C=12C=3C=C(NS(C)(=O)=O)C(OC)=CC=3CCN2C(C(=O)N2C(CCC2)(C)C)=CC=1C1=CC=CS1 SSTSDRKCQKZXLG-UHFFFAOYSA-N 0.000 claims 1
- LCWKQSFXUARSQX-UHFFFAOYSA-N n-tert-butyl-8-methoxy-n-methyl-9-prop-1-ynyl-1-thiophen-2-yl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxamide Chemical compound C=12C=3C=C(C#CC)C(OC)=CC=3CCN2C(C(=O)N(C)C(C)(C)C)=CC=1C1=CC=CS1 LCWKQSFXUARSQX-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Reproductive Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2706208P | 2008-02-08 | 2008-02-08 | |
| EP08151199 | 2008-02-08 | ||
| PCT/EP2009/051366 WO2009098283A1 (fr) | 2008-02-08 | 2009-02-06 | (dihydro)pyrrolo[2,1-α]isoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110942T1 true HRP20110942T1 (hr) | 2012-01-31 |
Family
ID=39516937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110942T HRP20110942T1 (hr) | 2008-02-08 | 2011-12-16 | (dihidro)pirolo[2,1-a]izohinolini |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8394789B2 (fr) |
| EP (1) | EP2252611B1 (fr) |
| JP (1) | JP5620823B2 (fr) |
| KR (1) | KR101586870B1 (fr) |
| CN (1) | CN102216297B (fr) |
| AR (1) | AR070345A1 (fr) |
| AT (1) | ATE527260T1 (fr) |
| AU (1) | AU2009211296B2 (fr) |
| BR (1) | BRPI0906937A2 (fr) |
| CA (1) | CA2713173C (fr) |
| CL (1) | CL2009000281A1 (fr) |
| CO (1) | CO6241120A2 (fr) |
| DK (1) | DK2252611T3 (fr) |
| EC (1) | ECSP10010303A (fr) |
| ES (1) | ES2373022T3 (fr) |
| HK (1) | HK1150597A1 (fr) |
| HR (1) | HRP20110942T1 (fr) |
| IL (1) | IL206378A0 (fr) |
| MX (1) | MX2010008717A (fr) |
| NZ (1) | NZ587164A (fr) |
| PE (1) | PE20091413A1 (fr) |
| PL (1) | PL2252611T3 (fr) |
| PT (1) | PT2252611E (fr) |
| RU (1) | RU2495037C2 (fr) |
| SI (1) | SI2252611T1 (fr) |
| TW (1) | TW200944523A (fr) |
| WO (1) | WO2009098283A1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI461426B (zh) * | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| US8071587B2 (en) * | 2009-05-27 | 2011-12-06 | N. V. Organon | (Dihydro)imidazoiso[5,1-A]quinolines |
| EP2504316A1 (fr) | 2009-11-23 | 2012-10-03 | MSD Oss B.V. | Composés hétérocyliques en tant qu'antagonistes des récepteurs d'orexine |
| US20120174381A1 (en) | 2011-01-10 | 2012-07-12 | David Messick | Apparatus and method for frame crimping |
| WO2012112958A2 (fr) * | 2011-02-19 | 2012-08-23 | The Broad Institute, Inc | Dosages à grand rendement destinés à détecter la leucémie dans la niche stromale |
| WO2013041458A1 (fr) | 2011-09-22 | 2013-03-28 | Msd Oss B.V. | Antagonistes du récepteur de la fsh |
| AU2012357296B2 (en) * | 2011-12-21 | 2017-04-13 | Jiangsu Hengrui Medicine Co., Ltd. | Pyrrole six-membered heteroaryl ring derivative, preparation method therefor, and medicinal uses thereof |
| CN102718695B (zh) * | 2012-06-25 | 2014-04-02 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| JP6272897B2 (ja) | 2012-11-29 | 2018-01-31 | ケモセントリックス，インコーポレイティド | Ｃｘｃｒ７アンタゴニスト |
| RU2550366C1 (ru) * | 2014-05-22 | 2015-05-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский университет дружбы народов" (РУДН) | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 5,6-ДИГИДРОПИРРОЛО[2,1-a]ИЗОХИНОЛИНОВ |
| BR112021011222A2 (pt) | 2018-12-12 | 2021-08-24 | Chemocentryx, Inc. | Inibidores de cxcr7 para o tratamento de câncer |
| CN110540519B (zh) * | 2019-09-05 | 2022-12-02 | 宁波大学 | 一种1,6-烯炔类化合物与酮类化合物的自由基环化反应方法 |
| CN113999103A (zh) * | 2021-11-26 | 2022-02-01 | 八叶草健康产业研究院(厦门)有限公司 | 一种α-羟基-环丁烷甲酸的制备方法 |
| WO2024184461A2 (fr) | 2023-03-08 | 2024-09-12 | Ferring B.V. | Modulateurs du récepteur fsh à petites molécules |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8718980D0 (en) * | 1987-08-11 | 1987-09-16 | May & Baker Ltd | Compositions of matter |
| DE4343649A1 (de) * | 1993-12-21 | 1995-06-22 | Boehringer Ingelheim Kg | Neue Pyridazino[4',5':3,4]pyrrolo-[2,1-a]isochinoline und deren Verwendung für die Herstellung von pharmazeutischen Zubereitungen |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6235755B1 (en) * | 1998-08-07 | 2001-05-22 | Applied Research Systems Ars Holding N.A. | FSH mimetics for the treatment of infertility |
| WO2000048144A1 (fr) | 1999-02-15 | 2000-08-17 | Medailles Souvenirs | Dispositif de personnalisation et de distribution de medailles |
| EP1307193A1 (fr) | 2000-07-27 | 2003-05-07 | Affymax Research Institute | Agoniste d'activite hormonale stimulant un follicule |
| JP2004517843A (ja) * | 2000-12-13 | 2004-06-17 | バイエル アクチェンゲゼルシャフト | ピロロ［２．１−ａ］ジヒドロイソキノリンおよびホスホジエステラーゼ１０ａ阻害薬としてのその使用 |
| EP1406628B1 (fr) | 2001-07-02 | 2006-03-08 | Akzo Nobel N.V. | Derives de tetrahydroquinoline |
| US20030236276A1 (en) | 2001-08-06 | 2003-12-25 | Ulrich Niewohner | Pyrrolo[2.1-a]isoquinoline derivatives |
| WO2003014115A1 (fr) | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | Derives de la pyrrolo (2.1-a) isoquinoleine substitues en 3 |
| WO2003051877A1 (fr) * | 2001-12-18 | 2003-06-26 | Bayer Corporation | 2-substitues pyrrolo[2.1-a]isoquinolines contre le cancer |
| US7754722B2 (en) * | 2002-09-20 | 2010-07-13 | Merck Serono Sa | Piperazine derivatives and methods of use |
| EP1641457B1 (fr) | 2003-06-30 | 2009-08-05 | Nycomed GmbH | Derives de pyrrolo-dihydroisoquinolines en tant qu' inhibiteurs de la pde10 |
| US20060148838A1 (en) | 2003-06-30 | 2006-07-06 | Altana Pharma Ag | Novel pyrrolodihydroisoquinolines useful in the treatment of cancer |
| US20080004263A1 (en) | 2004-03-04 | 2008-01-03 | Santora Vincent J | Ligands of Follicle Stimulating Hormone Receptor and Methods of Use Thereof |
| US20080064714A1 (en) | 2005-01-12 | 2008-03-13 | Nycomed Gmbh | Novel Pyrrolodihydroisoquinolines |
| US20080161338A1 (en) | 2005-01-12 | 2008-07-03 | Altana Pharma Ag | Novel Pyrrolodihydroisoquinolines as Pde 10 Inhibitors |
| UA92009C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодия |
| UA92007C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодности |
| ES2361674T3 (es) | 2005-05-04 | 2011-06-21 | N.V. Organon | Derivados de dihidropiridina. |
| UA92008C2 (en) | 2005-05-04 | 2010-09-27 | Н.В. Органон | 4-PHENYL-5-OXO-l,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES AS MEDICAMENTS FOR THE TREATMENT OF INFERTILITY |
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2009
- 2009-01-19 TW TW098101900A patent/TW200944523A/zh unknown
- 2009-02-05 PE PE2009000177A patent/PE20091413A1/es not_active Application Discontinuation
- 2009-02-06 CL CL2009000281A patent/CL2009000281A1/es unknown
- 2009-02-06 EP EP09708584A patent/EP2252611B1/fr active Active
- 2009-02-06 US US12/866,468 patent/US8394789B2/en active Active
- 2009-02-06 CA CA2713173A patent/CA2713173C/fr not_active Expired - Fee Related
- 2009-02-06 RU RU2010136057/04A patent/RU2495037C2/ru not_active IP Right Cessation
- 2009-02-06 ES ES09708584T patent/ES2373022T3/es active Active
- 2009-02-06 DK DK09708584.9T patent/DK2252611T3/da active
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- 2009-02-06 WO PCT/EP2009/051366 patent/WO2009098283A1/fr active Application Filing
- 2009-02-06 PT PT09708584T patent/PT2252611E/pt unknown
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2010
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