ZA200501842B - Dihydropyrazolopyridine compounds - Google Patents
Dihydropyrazolopyridine compounds Download PDFInfo
- Publication number
- ZA200501842B ZA200501842B ZA200501842A ZA200501842A ZA200501842B ZA 200501842 B ZA200501842 B ZA 200501842B ZA 200501842 A ZA200501842 A ZA 200501842A ZA 200501842 A ZA200501842 A ZA 200501842A ZA 200501842 B ZA200501842 B ZA 200501842B
- Authority
- ZA
- South Africa
- Prior art keywords
- dihydro
- pyrazolo
- cyano
- alkyl
- substituent
- Prior art date
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- KKIRMHFZGVTSNH-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazolo[4,3-b]pyridine Chemical class C1=CN=C2CNNC2=C1 KKIRMHFZGVTSNH-UHFFFAOYSA-N 0.000 title description 2
- -1 dihydropyrazolopyridine compound Chemical class 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
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- 230000002265 prevention Effects 0.000 claims description 7
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
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- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims 1
- DQZLWBBXXDZUSQ-UHFFFAOYSA-N 2-bromo-3-(6-propyl-5-pyridin-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-4-yl)benzonitrile Chemical compound C12=CNN=C2NC(CCC)=C(C=2N=CC=CC=2)C1C1=CC=CC(C#N)=C1Br DQZLWBBXXDZUSQ-UHFFFAOYSA-N 0.000 claims 1
- MWLNQUGFUQBKPR-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1N(C)CCC(C=2NC3=NNC=C3C(C=2C#N)C=2C3=NON=C3C=CC=2)=C1 MWLNQUGFUQBKPR-UHFFFAOYSA-N 0.000 claims 1
- LRIXCJBERGXNKA-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-(1-methylpiperidin-3-yl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1N(C)CCCC1C1=C(C#N)C(C=2C(=C(C#N)C=CC=2)Br)C2=CNN=C2N1 LRIXCJBERGXNKA-UHFFFAOYSA-N 0.000 claims 1
- OWRKCXPVEMDSRS-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-(1-methylsulfonylpiperidin-4-yl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1CN(S(=O)(=O)C)CCC1C1=C(C#N)C(C=2C(=C(C#N)C=CC=2)Br)C2=CNN=C2N1 OWRKCXPVEMDSRS-UHFFFAOYSA-N 0.000 claims 1
- DLBCTRATUZGIOC-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-(4-methylmorpholin-2-yl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1N(C)CCOC1C1=C(C#N)C(C=2C(=C(C#N)C=CC=2)Br)C2=CNN=C2N1 DLBCTRATUZGIOC-UHFFFAOYSA-N 0.000 claims 1
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- 229910052799 carbon Inorganic materials 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
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- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
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- 239000003112 inhibitor Substances 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
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- 150000004677 hydrates Chemical class 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000002434 immunopotentiative effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000006362 insulin response pathway Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 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
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- A61P37/04—Immunostimulants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002230581 | 2002-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200501842B true ZA200501842B (en) | 2006-05-31 |
Family
ID=31711689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200501842A ZA200501842B (en) | 2002-08-07 | 2005-03-03 | Dihydropyrazolopyridine compounds |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1537106A1 (pt) |
| JP (1) | JP2005534713A (pt) |
| KR (1) | KR20050069977A (pt) |
| CN (1) | CN1675209A (pt) |
| AR (1) | AR040961A1 (pt) |
| AU (1) | AU2003250539A1 (pt) |
| BR (1) | BR0313262A (pt) |
| CA (1) | CA2494785A1 (pt) |
| EA (1) | EA200500322A1 (pt) |
| IL (1) | IL166482A0 (pt) |
| MX (1) | MXPA05001434A (pt) |
| NO (1) | NO20051153L (pt) |
| WO (1) | WO2004014910A1 (pt) |
| ZA (1) | ZA200501842B (pt) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602006005242D1 (de) * | 2005-06-27 | 2009-04-02 | Sanofi Aventis | Pyrazolopyridinderivate als inhibitoren der kinase 1 des beta-adrenergen rezeptors |
| US8492378B2 (en) | 2006-08-03 | 2013-07-23 | Takeda Pharmaceutical Company Limited | GSK-3β inhibitor |
| RU2009108280A (ru) | 2006-08-08 | 2010-09-20 | Санофи-Авентис (Fr) | Ариламиноарилалкилзамещенные имидазолидин-2,4-дионы, способы их получения, содержащие эти соединения лекарственные средства и их применение |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CL2009001152A1 (es) | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| TW201014822A (en) | 2008-07-09 | 2010-04-16 | Sanofi Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2749884C (en) | 2009-01-28 | 2018-01-23 | Cara Therapeutics, Inc. | Bicyclic pyrazolo-heterocycles |
| US7741350B1 (en) | 2009-01-28 | 2010-06-22 | Cara Therapeutics, Inc. | Bicyclic pyrazolo-heterocycles |
| JP2013503135A (ja) | 2009-08-26 | 2013-01-31 | サノフイ | 新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用 |
| FR2951172B1 (fr) | 2009-10-13 | 2014-09-26 | Pf Medicament | Derives pyrazolopyridines en tant qu'agent anticancereux |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683700B1 (de) | 2011-03-08 | 2015-02-18 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CA2907971C (en) * | 2013-04-05 | 2020-12-29 | Eisai R&D Management Co., Ltd. | Salt of pyrazoloquinoline derivative, and crystal thereof |
| EP3081566B1 (en) | 2013-12-13 | 2018-03-07 | Daiichi Sankyo Company, Limited | 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative |
| CN104140427A (zh) * | 2014-07-05 | 2014-11-12 | 湖南华腾制药有限公司 | 一种四氢吡唑并[1,5-a]嘧啶的制备方法 |
| TWI784006B (zh) | 2017-06-01 | 2022-11-21 | 日商衛材R&D企管股份有限公司 | 含有吡唑并喹啉衍生物之路易氏體症治療劑 |
| BR112019023595A2 (pt) | 2017-06-01 | 2020-05-26 | Eisai R&D Management Co., Ltd. | Agente terapêutico da demência combinando derivados de pirazoloquinolina e memantina |
| CA3059539A1 (en) | 2017-06-01 | 2018-12-06 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition comprising pde9 inhibitor |
| KR102627787B1 (ko) | 2017-06-01 | 2024-01-23 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피라졸로퀴놀린 유도체와 도네페질을 병용한 치매 치료제 |
| CN111217754B (zh) * | 2018-11-23 | 2023-04-07 | 兰州大学 | 一种5-氨基-4-氰基吡唑的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4916140A (en) * | 1988-09-28 | 1990-04-10 | Merrell Dow Pharmaceuticals Inc. | Antiepileptic pyrazolopyridines |
| AU4878601A (en) * | 2000-04-20 | 2001-11-07 | Mitsubishi Corporation | Aromatic amide compounds |
| EP1355909A2 (en) * | 2001-02-02 | 2003-10-29 | Mitsubishi Pharma Corporation | Dihydropyrazolopyridine compounds and pharmaceutical use thereof |
-
2003
- 2003-08-01 BR BR0313262-5A patent/BR0313262A/pt not_active Application Discontinuation
- 2003-08-01 KR KR1020057002189A patent/KR20050069977A/ko not_active Application Discontinuation
- 2003-08-01 EP EP03784497A patent/EP1537106A1/en not_active Withdrawn
- 2003-08-01 CA CA002494785A patent/CA2494785A1/en not_active Abandoned
- 2003-08-01 CN CNA038190362A patent/CN1675209A/zh active Pending
- 2003-08-01 EA EA200500322A patent/EA200500322A1/ru unknown
- 2003-08-01 MX MXPA05001434A patent/MXPA05001434A/es not_active Application Discontinuation
- 2003-08-01 JP JP2004527320A patent/JP2005534713A/ja not_active Withdrawn
- 2003-08-01 WO PCT/JP2003/009787 patent/WO2004014910A1/en not_active Application Discontinuation
- 2003-08-01 AU AU2003250539A patent/AU2003250539A1/en not_active Abandoned
- 2003-08-07 AR ARP030102834A patent/AR040961A1/es unknown
-
2005
- 2005-01-25 IL IL16648205A patent/IL166482A0/xx unknown
- 2005-03-03 ZA ZA200501842A patent/ZA200501842B/en unknown
- 2005-03-03 NO NO20051153A patent/NO20051153L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005534713A (ja) | 2005-11-17 |
| IL166482A0 (en) | 2006-01-15 |
| EP1537106A1 (en) | 2005-06-08 |
| WO2004014910A1 (en) | 2004-02-19 |
| BR0313262A (pt) | 2005-07-12 |
| NO20051153L (no) | 2005-04-04 |
| EA200500322A1 (ru) | 2005-08-25 |
| CA2494785A1 (en) | 2004-02-19 |
| AR040961A1 (es) | 2005-04-27 |
| KR20050069977A (ko) | 2005-07-05 |
| CN1675209A (zh) | 2005-09-28 |
| AU2003250539A1 (en) | 2004-02-25 |
| MXPA05001434A (es) | 2005-06-06 |
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