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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (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. |
| PCT/EP2003/005222 WO2003099807A1 (en) | 2002-05-29 | 2003-05-19 | New indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| US10/515,407 US7560471B2 (en) | 2002-05-29 | 2003-05-19 | Indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| EP03755105A EP1513826B1 (en) | 2002-05-29 | 2003-05-19 | New indolylpiperidine derivatives as potent antihistaminic and antiallergic agents |
| 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 |
| 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 |
| AU2003242544A AU2003242544A1 (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 |
| 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 |
| DE60303381T DE60303381T2 (de) | 2002-05-29 | 2003-05-19 | Neue indolylpiperidin-derivate als potente antihistaminische und antiallergische mittel |
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 (enExample) |
| EP (1) | EP1513826B1 (enExample) |
| JP (1) | JP4485353B2 (enExample) |
| AT (1) | ATE316526T1 (enExample) |
| AU (1) | AU2003242544A1 (enExample) |
| DE (1) | DE60303381T2 (enExample) |
| DK (1) | DK1513826T3 (enExample) |
| ES (2) | ES2201907B1 (enExample) |
| PT (1) | PT1513826E (enExample) |
| WO (1) | WO2003099807A1 (enExample) |
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 |
| EP2532677A1 (en) | 2005-10-21 | 2012-12-12 | Novartis AG | Human antibodies against il13 and therapeutic uses |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| HRP20120494T1 (hr) | 2006-04-21 | 2012-08-31 | Novartis Ag | Derivati purina za uporabu kao agonista adenozin a2a receptora |
| JP2010504933A (ja) | 2006-09-29 | 2010-02-18 | ノバルティス アーゲー | Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン |
| ATE537166T1 (de) * | 2006-10-27 | 2011-12-15 | Boehringer Ingelheim Int | Piperidylpropanthiole als ccr3-modulatoren |
| AU2007342223B2 (en) | 2007-01-10 | 2011-02-24 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
| EP2332933A1 (en) | 2007-05-07 | 2011-06-15 | Novartis AG | Epithelial sodium channel (ENaC) inhibitors |
| BRPI0820669A2 (pt) | 2007-12-10 | 2020-08-04 | Novartis Ag | compostos orgânicos |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| KR20110040818A (ko) | 2008-06-10 | 2011-04-20 | 노파르티스 아게 | 상피 나트륨 채널 차단제로서의 피라진 유도체 |
| ES2396023T3 (es) | 2009-01-29 | 2013-02-18 | Novartis Ag | Bencimidazoles sustituidos para el tratamiento de astrocitomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| BR112012003262A8 (pt) | 2009-08-12 | 2016-05-17 | Novartis Ag | compostos de hidrazona heterocíclica e seus usos para tratar câncer e inflamação |
| UA111579C2 (uk) | 2009-08-17 | 2016-05-25 | Інтеллікіне Ллк | ГЕТЕРОЦИКЛІЧНІ ПОХІДНІ 2-АМІНОБЕНЗО[d]ОКСАЗОЛУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ НА ЇХ ОСНОВІ ТА ЇХ ЗАСТОСУВАННЯ ДЛЯ ЛІКУВАННЯ ЗАХВОРЮВАННЯ, ПОВ'АНОГО З РІ3-КІНАЗОЮ |
| IN2012DN01453A (enExample) | 2009-08-20 | 2015-06-05 | Novartis Ag | |
| AU2010310449A1 (en) | 2009-10-22 | 2012-05-03 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| BR112013000946B1 (pt) | 2010-07-14 | 2020-09-08 | Novartis Ag | Compostos heterocíclicos agonistas de receptor de ip, seus usos, composição e combinação farmacêuticas |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | 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 |
| BR112013021638A2 (pt) | 2011-02-25 | 2016-08-02 | Irm Llc | "compostos inibidores de trk, seu uso e composições que os compreendem" |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| JP6165733B2 (ja) | 2011-09-16 | 2017-07-19 | ノバルティス アーゲー | Ｎ−置換ヘテロシクリルカルボキサミド類 |
| 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 |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| US9174994B2 (en) | 2011-11-23 | 2015-11-03 | Intellikine, Llc | Enhanced treatment regimens using mTor inhibitors |
| US9174985B2 (en) | 2012-01-13 | 2015-11-03 | Novartis Ag | Salts of 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid as IP receptor agonists |
| 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 |
| US9115129B2 (en) | 2012-01-13 | 2015-08-25 | Novartis Ag | Substituted pyrido[2,3-B]pyrazines as IP receptor agonists |
| AR089698A1 (es) | 2012-01-13 | 2014-09-10 | Novartis Ag | Compuestos heterociclicos antagonistas del receptor ip |
| 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 |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| MX371119B (es) | 2012-04-03 | 2020-01-17 | Novartis Ag | Productos de combinacion con los inhibidores de cinasa de tirosina y su uso. |
| EP2935249B1 (en) | 2012-12-19 | 2018-12-12 | 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 |
| HK1219421A1 (zh) | 2013-03-15 | 2017-04-07 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
| PT3022202T (pt) | 2013-07-18 | 2019-09-03 | Novartis Ag | Inibidores da autotaxina compreendendo um núcleo beteroaromático anel-benzilo-amida-ciclo |
| EP3022201A1 (en) | 2013-07-18 | 2016-05-25 | Novartis AG | Autotaxin inhibitors |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| KR20160145780A (ko) | 2014-04-24 | 2016-12-20 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 아미노 피리딘 유도체 |
| EP3134398A1 (en) | 2014-04-24 | 2017-03-01 | Novartis Ag | Autotaxin inhibitors |
| AU2014391610B2 (en) | 2014-04-24 | 2018-01-25 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| US10195208B2 (en) | 2014-07-31 | 2019-02-05 | Novartis Ag | Combination therapy |
| US20200383960A1 (en) | 2019-06-10 | 2020-12-10 | Novartis Ag | Pyridine and Pyrazine derivative for the Treatment of CF, COPD, and Bronchiectasis |
| KR20220052934A (ko) | 2019-08-28 | 2022-04-28 | 노파르티스 아게 | 치환 1,3-페닐 헤테로아릴 유도체 및 질환 치료에서의 이의 용도 |
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 |
| DE69330823T2 (de) * | 1992-02-13 | 2002-05-02 | Merrell Pharmaceuticals Inc., Cincinnati | Thiacyclische piperidinylderivate |
| 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. |
| HK1052705B (en) | 2000-08-14 | 2006-09-29 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted pyrazole |
| ATE402699T1 (de) | 2000-09-06 | 2008-08-15 | Ortho Mcneil Pharm Inc | Verwendung von substituierten pyrazolen zur behandlung von allergien |
| 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 US US10/515,407 patent/US7560471B2/en not_active Expired - Fee Related
- 2003-05-19 AU AU2003242544A patent/AU2003242544A1/en not_active Abandoned
- 2003-05-19 DK DK03755105T patent/DK1513826T3/da active
- 2003-05-19 DE DE60303381T patent/DE60303381T2/de not_active Expired - Lifetime
- 2003-05-19 JP JP2004507464A patent/JP4485353B2/ja not_active Expired - Fee Related
- 2003-05-19 WO PCT/EP2003/005222 patent/WO2003099807A1/en not_active Ceased
- 2003-05-19 ES ES03755105T patent/ES2254964T3/es not_active Expired - Lifetime
- 2003-05-19 PT PT03755105T patent/PT1513826E/pt unknown
- 2003-05-19 AT AT03755105T patent/ATE316526T1/de not_active IP Right Cessation
- 2003-05-19 EP EP03755105A patent/EP1513826B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60303381D1 (de) | 2006-04-13 |
| WO2003099807A1 (en) | 2003-12-04 |
| EP1513826B1 (en) | 2006-01-25 |
| ATE316526T1 (de) | 2006-02-15 |
| JP4485353B2 (ja) | 2010-06-23 |
| US7560471B2 (en) | 2009-07-14 |
| PT1513826E (pt) | 2006-05-31 |
| US20060094879A1 (en) | 2006-05-04 |
| ES2201907A1 (es) | 2004-03-16 |
| AU2003242544A1 (en) | 2003-12-12 |
| JP2005527627A (ja) | 2005-09-15 |
| DK1513826T3 (da) | 2006-06-06 |
| EP1513826A1 (en) | 2005-03-16 |
| ES2254964T3 (es) | 2006-06-16 |
| DE60303381T2 (de) | 2006-10-26 |
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