ZA200203256B - Novel cyclopropanes as CGRP antagonists, medicaments containing said compounds and method for the production thereof. - Google Patents
Novel cyclopropanes as CGRP antagonists, medicaments containing said compounds and method for the production thereof. Download PDFInfo
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- ZA200203256B ZA200203256B ZA200203256A ZA200203256A ZA200203256B ZA 200203256 B ZA200203256 B ZA 200203256B ZA 200203256 A ZA200203256 A ZA 200203256A ZA 200203256 A ZA200203256 A ZA 200203256A ZA 200203256 B ZA200203256 B ZA 200203256B
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- South Africa
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- amino
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- carbonyl
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- 150000001875 compounds Chemical class 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 20
- 150000001942 cyclopropanes Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940127597 CGRP antagonist Drugs 0.000 title description 3
- 239000003814 drug Substances 0.000 title description 2
- -1 biphenylyl Chemical group 0.000 claims description 138
- 239000000203 mixture Substances 0.000 claims description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000001246 bromo group Chemical group Br* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 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 description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
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- 238000006467 substitution reaction Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
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- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
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- 125000006239 protecting group Chemical group 0.000 claims description 4
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- JYOGPDQDXPDNHR-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(3-chlorophenyl)-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=C(Cl)C=CC=2)=O)C1 JYOGPDQDXPDNHR-QZTJIDSGSA-N 0.000 claims description 3
- 206010047141 Vasodilatation Diseases 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- 230000024883 vasodilation Effects 0.000 claims description 3
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 2
- OVEBHCCJIWQLFX-SKLUMECTSA-N 1-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-phenyl-1,2,4-triazolidin-3-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=O)N2)C=2C=CC=CC=2)C1 OVEBHCCJIWQLFX-SKLUMECTSA-N 0.000 claims description 2
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- UTATXYLZLKRHCP-WOJBJXKFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-(1,3-dioxolan-2-ylmethoxy)-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(OCC4OCCO4)C=C3C2)=O)C1 UTATXYLZLKRHCP-WOJBJXKFSA-N 0.000 claims description 2
- FVBTUAQLPAVBGJ-FGZHOGPDSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-[3-(dimethylamino)propoxy]-1,4-dihydroquinazolin-2-one Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1C(=O)NC2=CC=C(C=C2C1)OCCCN(C)C)C1=CC(Br)=C(N)C(Br)=C1 FVBTUAQLPAVBGJ-FGZHOGPDSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Otolaryngology (AREA)
- Toxicology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19952147A DE19952147A1 (de) | 1999-10-29 | 1999-10-29 | Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200203256B true ZA200203256B (en) | 2003-04-10 |
Family
ID=7927315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200203256A ZA200203256B (en) | 1999-10-29 | 2002-04-24 | Novel cyclopropanes as CGRP antagonists, medicaments containing said compounds and method for the production thereof. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US20030139417A1 (fr) |
| EP (1) | EP1228059B1 (fr) |
| JP (1) | JP3869721B2 (fr) |
| KR (1) | KR20020047290A (fr) |
| CN (1) | CN1177844C (fr) |
| AT (1) | ATE301117T1 (fr) |
| AU (1) | AU781856B2 (fr) |
| BG (1) | BG106638A (fr) |
| BR (1) | BR0015147A (fr) |
| CA (1) | CA2387134C (fr) |
| CZ (1) | CZ20021812A3 (fr) |
| DE (2) | DE19952147A1 (fr) |
| EA (1) | EA005137B1 (fr) |
| EE (1) | EE200200220A (fr) |
| HK (1) | HK1051858A1 (fr) |
| HR (1) | HRP20020373A2 (fr) |
| HU (1) | HUP0203496A3 (fr) |
| IL (1) | IL148975A0 (fr) |
| MX (1) | MXPA02004119A (fr) |
| NO (1) | NO20021799D0 (fr) |
| NZ (1) | NZ518698A (fr) |
| PL (1) | PL354715A1 (fr) |
| SK (1) | SK7282002A3 (fr) |
| TR (1) | TR200201168T2 (fr) |
| WO (1) | WO2001032648A1 (fr) |
| YU (1) | YU30902A (fr) |
| ZA (1) | ZA200203256B (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7842808B2 (en) | 2002-06-05 | 2010-11-30 | Bristol-Myers Squibb Company | Anti-migraine spirocycles |
| US7220862B2 (en) | 2002-06-05 | 2007-05-22 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
| US20040063735A1 (en) | 2002-06-05 | 2004-04-01 | Chaturvedula Prasad V. | Calcitonin gene related peptide receptor antagonists |
| AU2003297694A1 (en) | 2003-12-05 | 2005-08-12 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
| AR046787A1 (es) | 2003-12-05 | 2005-12-21 | Bristol Myers Squibb Co | Agentes antimigrana heterociclicos |
| TW200533398A (en) | 2004-03-29 | 2005-10-16 | Bristol Myers Squibb Co | Novel therapeutic agents for the treatment of migraine |
| WO2006031513A2 (fr) * | 2004-09-09 | 2006-03-23 | Merck & Co., Inc. | Antagonistes des recepteurs cgrp d'aryle-spirolactame |
| US7384931B2 (en) | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
| US7384930B2 (en) | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
| US7449586B2 (en) | 2004-12-03 | 2008-11-11 | Bristol-Myers Squibb Company | Processes for the preparation of CGRP-receptor antagonists and intermediates thereof |
| US7834007B2 (en) | 2005-08-25 | 2010-11-16 | Bristol-Myers Squibb Company | CGRP antagonists |
| CA2629409A1 (fr) * | 2005-11-18 | 2007-05-31 | Merck & Co., Inc. | Antagoniste du recepteur cgpr de spirolactam aryle |
| WO2009034029A2 (fr) * | 2007-09-07 | 2009-03-19 | Boehringer Ingelheim International Gmbh | Nouveaux composés |
| EP2065381A1 (fr) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | Antagonistes du CGRP |
| EA201000612A1 (ru) | 2007-10-18 | 2010-10-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Антагонисты cgrp-пептиды |
| EP2225223B1 (fr) | 2007-11-22 | 2017-01-11 | Boehringer Ingelheim International GmbH | Composés organiques |
| US9315449B2 (en) | 2008-05-15 | 2016-04-19 | Duke University | Substituted pyrazoles as heat shock transcription factor activators |
| UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
| EA201491606A1 (ru) * | 2012-04-05 | 2015-03-31 | Схди Фаундейшн, Инк. | Ингибиторы кинуренин-3-монооксигеназы, фармацевтические композиции и способы их применения |
| EP3049077A4 (fr) | 2013-09-26 | 2017-02-15 | CHDI Foundation, Inc. | Inhibiteurs de kynurénine-3-monooxygénase, compositions pharmaceutiques et procédés d'utilisation de ces compositions |
| ES2754473T3 (es) | 2013-09-26 | 2020-04-17 | Chdi Foundation Inc | Inhibidores de quinurenina-3-monooxigenasa, composiciones farmacéuticas, y método de uso de los mismos |
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| CN114957145B (zh) * | 2022-04-14 | 2023-07-18 | 浙江师范大学 | 一种1,2,4-苯并三嗪衍生物及其制备方法 |
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| US3655667A (en) * | 1968-04-04 | 1972-04-11 | Smith Kline French Lab | 1-(2-benzoylcyclopropylmethyl)-4-phenylpiperazines |
| US3873707A (en) * | 1972-10-02 | 1975-03-25 | Robins Co Inc A H | 1-Cyclopropyl-3-mono-(and 2,3-di) substituted-1-propanones in compositions and method for treating pain |
| FR2729855A1 (fr) | 1995-01-26 | 1996-08-02 | Oreal | Utilisation d'un antagoniste de cgrp dans une composition cosmetique, pharmaceutique ou dermatologique et composition obtenue |
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| WO1999047517A1 (fr) * | 1998-03-17 | 1999-09-23 | Novo Nordisk A/S | Nouveaux composes heterocycliques |
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| DE19937304C2 (de) | 1999-08-10 | 2003-08-21 | Boehringer Ingelheim Pharma | Verwendung von CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen |
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| US6977265B2 (en) * | 2001-11-30 | 2005-12-20 | Roche Palo Alto Llc | Piperidine CCR-3 receptor antagonists |
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1999
- 1999-10-29 DE DE19952147A patent/DE19952147A1/de not_active Withdrawn
-
2000
- 2000-10-21 AU AU79213/00A patent/AU781856B2/en not_active Ceased
- 2000-10-21 BR BR0015147-5A patent/BR0015147A/pt not_active Expired - Fee Related
- 2000-10-21 CZ CZ20021812A patent/CZ20021812A3/cs unknown
- 2000-10-21 PL PL00354715A patent/PL354715A1/xx not_active Application Discontinuation
- 2000-10-21 SK SK728-2002A patent/SK7282002A3/sk unknown
- 2000-10-21 EE EEP200200220A patent/EE200200220A/xx unknown
- 2000-10-21 CN CNB008151490A patent/CN1177844C/zh not_active Expired - Fee Related
- 2000-10-21 CA CA002387134A patent/CA2387134C/fr not_active Expired - Fee Related
- 2000-10-21 NZ NZ518698A patent/NZ518698A/xx unknown
- 2000-10-21 YU YU30902A patent/YU30902A/sh unknown
- 2000-10-21 MX MXPA02004119A patent/MXPA02004119A/es unknown
- 2000-10-21 WO PCT/EP2000/010391 patent/WO2001032648A1/fr not_active Application Discontinuation
- 2000-10-21 AT AT00969529T patent/ATE301117T1/de not_active IP Right Cessation
- 2000-10-21 HU HU0203496A patent/HUP0203496A3/hu unknown
- 2000-10-21 JP JP2001534799A patent/JP3869721B2/ja not_active Expired - Fee Related
- 2000-10-21 TR TR2002/01168T patent/TR200201168T2/xx unknown
- 2000-10-21 EP EP00969529A patent/EP1228059B1/fr not_active Expired - Lifetime
- 2000-10-21 EA EA200200447A patent/EA005137B1/ru not_active IP Right Cessation
- 2000-10-21 DE DE50010886T patent/DE50010886D1/de not_active Expired - Fee Related
- 2000-10-21 IL IL14897500A patent/IL148975A0/xx unknown
- 2000-10-21 KR KR1020027005386A patent/KR20020047290A/ko not_active Application Discontinuation
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2002
- 2002-04-12 US US10/121,872 patent/US20030139417A1/en not_active Abandoned
- 2002-04-17 NO NO20021799A patent/NO20021799D0/no not_active Application Discontinuation
- 2002-04-23 BG BG106638A patent/BG106638A/bg active Pending
- 2002-04-24 ZA ZA200203256A patent/ZA200203256B/en unknown
- 2002-04-26 HR HR20020373A patent/HRP20020373A2/hr not_active Application Discontinuation
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2003
- 2003-06-11 HK HK03104096A patent/HK1051858A1/xx not_active IP Right Cessation
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2005
- 2005-06-27 US US11/169,078 patent/US7407963B2/en not_active Expired - Lifetime
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