ES2201907B1 - Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. - Google Patents
Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos.Info
- Publication number
- ES2201907B1 ES2201907B1 ES200201226A ES200201226A ES2201907B1 ES 2201907 B1 ES2201907 B1 ES 2201907B1 ES 200201226 A ES200201226 A ES 200201226A ES 200201226 A ES200201226 A ES 200201226A ES 2201907 B1 ES2201907 B1 ES 2201907B1
- Authority
- ES
- Spain
- Prior art keywords
- acid
- piperidin
- ylmethyl
- indol
- methoxybenzoic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000739 antihistaminic agent Substances 0.000 title description 8
- 230000001387 anti-histamine Effects 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 80
- 239000002253 acid Substances 0.000 claims description 73
- -1 methoxyethyl Chemical group 0.000 claims description 30
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229960001340 histamine Drugs 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 102000003834 Histamine H1 Receptors Human genes 0.000 claims description 5
- 108090000110 Histamine H1 Receptors Proteins 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- YNSYFJYJHVDOEP-UHFFFAOYSA-N 2-methoxy-5-[[4-[1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound C12=CC=CC=C2N(CCOC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 YNSYFJYJHVDOEP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- IJQQEKVCTHAHGO-UHFFFAOYSA-N 5-[[4-(1-butyl-6-fluoroindol-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 IJQQEKVCTHAHGO-UHFFFAOYSA-N 0.000 claims description 4
- UVOPLTUACIQBLB-UHFFFAOYSA-N 5-[[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 UVOPLTUACIQBLB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- OQVJFLGZRJIQPW-UHFFFAOYSA-N 5-[[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 OQVJFLGZRJIQPW-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 208000024780 Urticaria Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000008485 antagonism Effects 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- JNKMKCHYTDMERT-UHFFFAOYSA-N 2-methoxy-5-[[4-[1-(2-propoxyethyl)indol-3-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 JNKMKCHYTDMERT-UHFFFAOYSA-N 0.000 claims description 2
- FFBFTMBXAZLCSQ-UHFFFAOYSA-N 3-[[4-(5-chloro-1-ethylindol-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CC)C=C1C(CC1)CCN1CC1=CC=CC(C(O)=O)=C1OC FFBFTMBXAZLCSQ-UHFFFAOYSA-N 0.000 claims description 2
- ZWSHAGVVGVUZIC-UHFFFAOYSA-N 3-[[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CC1=CC=CC(C(O)=O)=C1OC ZWSHAGVVGVUZIC-UHFFFAOYSA-N 0.000 claims description 2
- HGMKYFBHBNEBMZ-UHFFFAOYSA-N 3-[[4-[1-(cyclopropylmethyl)-5-fluoroindol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=CC=C(C(O)=O)C(OC)=C1CN1CCC(C=2C3=CC(F)=CC=C3N(CC3CC3)C=2)CC1 HGMKYFBHBNEBMZ-UHFFFAOYSA-N 0.000 claims description 2
- SSEWNMRESDTMLP-UHFFFAOYSA-N 3-[[4-[5-bromo-1-(3-methoxypropyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCCOC)C=C1C(CC1)CCN1CC1=CC=CC(C(O)=O)=C1OC SSEWNMRESDTMLP-UHFFFAOYSA-N 0.000 claims description 2
- YSRJHHIPHBSKOB-UHFFFAOYSA-N 3-[[4-[6-fluoro-1-(methoxymethyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=C(F)C=C2N(COC)C=C1C(CC1)CCN1CC1=CC=CC(C(O)=O)=C1OC YSRJHHIPHBSKOB-UHFFFAOYSA-N 0.000 claims description 2
- KCECOARVNICXJO-UHFFFAOYSA-N 5-[[4-(1-butylindol-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=CC=C2N(CCCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 KCECOARVNICXJO-UHFFFAOYSA-N 0.000 claims description 2
- AWVHMNXILJIKNC-UHFFFAOYSA-N 5-[[4-(5-bromo-1-propylindol-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 AWVHMNXILJIKNC-UHFFFAOYSA-N 0.000 claims description 2
- ZXHGIQNHSQMWHS-UHFFFAOYSA-N 5-[[4-[5-chloro-1-(cyclohexylmethyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC(Cl)=CC=C3N(CC3CCCCC3)C=2)CC1 ZXHGIQNHSQMWHS-UHFFFAOYSA-N 0.000 claims description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 201000010435 allergic urticaria Diseases 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims 3
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims 2
- BTVPCSHYJPZKBO-UHFFFAOYSA-N 3-[[4-[1-(1-cyclopropylethyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=CC=C(C(O)=O)C(OC)=C1CN1CCC(C=2C3=CC=CC=C3N(C(C)C3CC3)C=2)CC1 BTVPCSHYJPZKBO-UHFFFAOYSA-N 0.000 claims 1
- JMRPZMDETXZTSJ-UHFFFAOYSA-N 3-[[4-[5-chloro-1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CCOC)C=C1C(CC1)CCN1CC1=CC=CC(C(O)=O)=C1OC JMRPZMDETXZTSJ-UHFFFAOYSA-N 0.000 claims 1
- UWAWOROGEOYUGW-UHFFFAOYSA-N 5-[[4-(5-chloro-1-prop-2-enylindol-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC(Cl)=CC=C3N(CC=C)C=2)CC1 UWAWOROGEOYUGW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 18
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- 102000000543 Histamine Receptors Human genes 0.000 abstract description 3
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- 239000000203 mixture Substances 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 description 17
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P37/08—Antiallergic agents
-
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200201226A ES2201907B1 (es) | 2002-05-29 | 2002-05-29 | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
| ES03755105T ES2254964T3 (es) | 2002-05-29 | 2003-05-19 | Nuevos derivados de indolilpiperidina como potentes agentets antihistaminicos y antialergicos. |
| DK03755105T DK1513826T3 (da) | 2002-05-29 | 2003-05-19 | Hidtil ukendte indolylpiperidinderivater som kraftige antihistamin- og antiallergimidler |
| EP03755105A EP1513826B1 (en) | 2002-05-29 | 2003-05-19 | New indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| PCT/EP2003/005222 WO2003099807A1 (en) | 2002-05-29 | 2003-05-19 | New indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| SI200330167T SI1513826T1 (sl) | 2002-05-29 | 2003-05-19 | Novi derivati indolilpiperidina kot ucinkoviti antihistaminiki in antialergicna sredstva |
| DE60303381T DE60303381T2 (de) | 2002-05-29 | 2003-05-19 | Neue indolylpiperidin-derivate als potente antihistaminische und antiallergische mittel |
| AU2003242544A AU2003242544A1 (en) | 2002-05-29 | 2003-05-19 | New indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| AT03755105T ATE316526T1 (de) | 2002-05-29 | 2003-05-19 | Neue indolylpiperidin-derivate als potente antihistaminische und antiallergische mittel |
| PT03755105T PT1513826E (pt) | 2002-05-29 | 2003-05-19 | Novos derivados de indolilpiperidina como agentes anti-histaminicos e antialergicos potentes |
| US10/515,407 US7560471B2 (en) | 2002-05-29 | 2003-05-19 | Indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| JP2004507464A JP4485353B2 (ja) | 2002-05-29 | 2003-05-19 | 有効な抗ヒスタミン剤および抗アレルギー剤としての新規インドリルピペリジン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200201226A ES2201907B1 (es) | 2002-05-29 | 2002-05-29 | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2201907A1 ES2201907A1 (es) | 2004-03-16 |
| ES2201907B1 true ES2201907B1 (es) | 2005-06-01 |
Family
ID=29558514
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200201226A Expired - Fee Related ES2201907B1 (es) | 2002-05-29 | 2002-05-29 | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
| ES03755105T Expired - Lifetime ES2254964T3 (es) | 2002-05-29 | 2003-05-19 | Nuevos derivados de indolilpiperidina como potentes agentets antihistaminicos y antialergicos. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03755105T Expired - Lifetime ES2254964T3 (es) | 2002-05-29 | 2003-05-19 | Nuevos derivados de indolilpiperidina como potentes agentets antihistaminicos y antialergicos. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7560471B2 (https=) |
| EP (1) | EP1513826B1 (https=) |
| JP (1) | JP4485353B2 (https=) |
| AT (1) | ATE316526T1 (https=) |
| AU (1) | AU2003242544A1 (https=) |
| DE (1) | DE60303381T2 (https=) |
| DK (1) | DK1513826T3 (https=) |
| ES (2) | ES2201907B1 (https=) |
| PT (1) | PT1513826E (https=) |
| WO (1) | WO2003099807A1 (https=) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| AR056690A1 (es) * | 2005-10-14 | 2007-10-17 | Athersys Inc | Derivados de indol como inhibidores de indol como inhibidores del receptor 3 de histamina para el tartamiento de trastornos del sueno y cognitivos obesidad y otros trastornos de snc |
| RU2421464C2 (ru) | 2005-10-21 | 2011-06-20 | Новартис Аг | Человеческие антитела к il-13 и их терапевтическое применение |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| EP2322525B1 (en) | 2006-04-21 | 2013-09-18 | Novartis AG | Purine derivatives for use as adenosin A2A receptor agonists |
| WO2008037477A1 (en) | 2006-09-29 | 2008-04-03 | Novartis Ag | Pyrazolopyrimidines as p13k lipid kinase inhibitors |
| WO2008049874A1 (en) * | 2006-10-27 | 2008-05-02 | Boehringer Ingelheim International Gmbh | Piperidyl-propane-thiol ccr3 modulators |
| PL2104535T3 (pl) | 2007-01-10 | 2011-05-31 | Irm Llc | Związki i kompozycje jako inhibitory proteazy aktywujące kanały |
| DE602008005140D1 (de) | 2007-05-07 | 2011-04-07 | Novartis Ag | Organische verbindungen |
| MX2010006421A (es) | 2007-12-10 | 2010-06-25 | Novartis Ag | Compuestos organicos. |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| JP2011522860A (ja) | 2008-06-10 | 2011-08-04 | ノバルティス アーゲー | 上皮性ナトリウムチャネルブロッカーとしてのピラジン誘導体 |
| PT2391366E (pt) | 2009-01-29 | 2013-02-05 | Novartis Ag | Benzimidazoles substituídos para o tratamento de astrocitomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| JP5781510B2 (ja) | 2009-08-12 | 2015-09-24 | ノバルティス アーゲー | ヘテロ環式ヒドラゾン化合物および癌および炎症の処置のためのそれらの使用 |
| PE20121148A1 (es) | 2009-08-17 | 2012-09-07 | Intellikine Llc | Compuestos heterociclicos y usos de los mismos |
| JP5775871B2 (ja) | 2009-08-20 | 2015-09-09 | ノバルティス アーゲー | ヘテロ環式オキシム化合物 |
| MX2012004792A (es) | 2009-10-22 | 2013-02-01 | Vertex Pharma | Composiciones para el tratamiento de fibrosis quistica y otras enfermedades cronicas. |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| EP2593452B1 (en) | 2010-07-14 | 2017-01-18 | Novartis AG | Ip receptor agonist heterocyclic compounds |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
| WO2012116237A2 (en) | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| EA026655B1 (ru) | 2011-09-15 | 2017-05-31 | Новартис Аг | 6-ЗАМЕЩЕННЫЕ 3-(ХИНОЛИН-6-ИЛТИО)[1,2,4]ТРИАЗОЛО[4,3-a]ПИРИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ c-MET ТИРОЗИНКИНАЗЫ |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| CN103946221B (zh) | 2011-09-16 | 2016-08-03 | 诺华股份有限公司 | 用于治疗囊性纤维化的杂环化合物 |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| US9056867B2 (en) | 2011-09-16 | 2015-06-16 | Novartis Ag | N-substituted heterocyclyl carboxamides |
| CA2856803A1 (en) | 2011-11-23 | 2013-05-30 | Intellikine, Llc | Enhanced treatment regimens using mtor inhibitors |
| EP2802583A1 (en) | 2012-01-13 | 2014-11-19 | Novartis AG | Fused piperidines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| EP2802582A1 (en) | 2012-01-13 | 2014-11-19 | Novartis AG | Fused dihydropyrido [2,3 -b]pyrazines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| WO2013105058A1 (en) | 2012-01-13 | 2013-07-18 | Novartis Ag | 7,8- dihydropyrido [3, 4 - b] pyrazines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders |
| AR089698A1 (es) | 2012-01-13 | 2014-09-10 | Novartis Ag | Compuestos heterociclicos antagonistas del receptor ip |
| ES2561353T3 (es) | 2012-01-13 | 2016-02-25 | Novartis Ag | Sales de un agonista del receptor IP |
| US9115129B2 (en) | 2012-01-13 | 2015-08-25 | Novartis Ag | Substituted pyrido[2,3-B]pyrazines as IP receptor agonists |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| JP2015512425A (ja) | 2012-04-03 | 2015-04-27 | ノバルティス アーゲー | チロシンキナーゼ阻害剤との組合せ製品及びそれらの使用 |
| HK1212348A1 (en) | 2012-12-19 | 2016-06-10 | Novartis Ag | Autotaxin inhibitors |
| ES2637719T3 (es) | 2013-02-13 | 2017-10-16 | Novartis Ag | Compuestos heterocíclicos agonistas del receptor IP |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| EP2968340A4 (en) | 2013-03-15 | 2016-08-10 | Intellikine Llc | COMBINING KINASE INHIBITORS AND USES THEREOF |
| US20160168119A1 (en) | 2013-07-18 | 2016-06-16 | Novartis Ag | Autotaxin inhibitors |
| MX368059B (es) | 2013-07-18 | 2019-09-18 | Novartis Ag | Inhibidores de autotaxina que comprenden un núcleo de anillo heteroaromático de bencil-amida cíclica. |
| WO2015084804A1 (en) | 2013-12-03 | 2015-06-11 | Novartis Ag | Combination of mdm2 inhibitor and braf inhibitor and their use |
| KR20160145780A (ko) | 2014-04-24 | 2016-12-20 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 아미노 피리딘 유도체 |
| EP3134397A1 (en) | 2014-04-24 | 2017-03-01 | Novartis AG | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| KR20160141856A (ko) | 2014-04-24 | 2016-12-09 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 피라진 유도체 |
| US20170037030A1 (en) | 2014-04-24 | 2017-02-09 | Novartis Ag | Autotaxin inhibitors |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| ES2831416T3 (es) | 2014-07-31 | 2021-06-08 | Novartis Ag | Terapia de combinación de un inhibidor de MET y un inhibidor de EGFR |
| WO2020250116A1 (en) | 2019-06-10 | 2020-12-17 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of cf, copd, and bronchiectasis |
| PE20220346A1 (es) | 2019-08-28 | 2022-03-14 | Novartis Ag | Derivados de 1,3-fenil heteroarilo sustituidos y su uso en el tratamiento de enfermedades |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4742057A (en) | 1985-12-05 | 1988-05-03 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic thiazole compounds |
| DK733788A (da) | 1988-01-14 | 1989-07-15 | Fujisawa Pharmaceutical Co | Indolylpiperidinderivater og fremgangsmaade til fremstilling deraf |
| GB8900382D0 (en) | 1989-01-09 | 1989-03-08 | Janssen Pharmaceutica Nv | 2-aminopyrimidinone derivatives |
| WO1993016081A1 (en) * | 1992-02-13 | 1993-08-19 | Merrell Dow Pharmaceuticals Inc. | Piperidinyl thiacyclic derivatives |
| JP3338913B2 (ja) | 1993-06-29 | 2002-10-28 | 大鵬薬品工業株式会社 | テトラゾール誘導体 |
| IT1271417B (it) | 1993-10-15 | 1997-05-28 | Erregierre Ind Chim | Composti ad attivita' antiistaminica procedimento per la loro preperazione e composizioni farmaceutiche che li contengono. |
| ES2165274B1 (es) * | 1999-06-04 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| DK1309592T3 (da) | 2000-08-14 | 2006-08-21 | Ortho Mcneil Pharm Inc | Substituerede pyrazoler |
| NZ524682A (en) | 2000-09-06 | 2004-11-26 | Ortho Mcneil Pharm Inc | A method for treating allergies using substituted pyrazoles |
| ES2172436B1 (es) * | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
-
2002
- 2002-05-29 ES ES200201226A patent/ES2201907B1/es not_active Expired - Fee Related
-
2003
- 2003-05-19 AT AT03755105T patent/ATE316526T1/de not_active IP Right Cessation
- 2003-05-19 AU AU2003242544A patent/AU2003242544A1/en not_active Abandoned
- 2003-05-19 JP JP2004507464A patent/JP4485353B2/ja not_active Expired - Fee Related
- 2003-05-19 US US10/515,407 patent/US7560471B2/en not_active Expired - Fee Related
- 2003-05-19 WO PCT/EP2003/005222 patent/WO2003099807A1/en not_active Ceased
- 2003-05-19 PT PT03755105T patent/PT1513826E/pt unknown
- 2003-05-19 ES ES03755105T patent/ES2254964T3/es not_active Expired - Lifetime
- 2003-05-19 DK DK03755105T patent/DK1513826T3/da active
- 2003-05-19 EP EP03755105A patent/EP1513826B1/en not_active Expired - Lifetime
- 2003-05-19 DE DE60303381T patent/DE60303381T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20060094879A1 (en) | 2006-05-04 |
| JP4485353B2 (ja) | 2010-06-23 |
| ES2201907A1 (es) | 2004-03-16 |
| DE60303381T2 (de) | 2006-10-26 |
| US7560471B2 (en) | 2009-07-14 |
| DE60303381D1 (de) | 2006-04-13 |
| JP2005527627A (ja) | 2005-09-15 |
| EP1513826A1 (en) | 2005-03-16 |
| AU2003242544A1 (en) | 2003-12-12 |
| WO2003099807A1 (en) | 2003-12-04 |
| ATE316526T1 (de) | 2006-02-15 |
| PT1513826E (pt) | 2006-05-31 |
| DK1513826T3 (da) | 2006-06-06 |
| EP1513826B1 (en) | 2006-01-25 |
| ES2254964T3 (es) | 2006-06-16 |
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