NO324760B1 - Piperidinforbindelse, farmasoytiske preparater, anvendelse av forbindelsene samt fremgangsmate for fremstilling derav - Google Patents
Piperidinforbindelse, farmasoytiske preparater, anvendelse av forbindelsene samt fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO324760B1 NO324760B1 NO20030135A NO20030135A NO324760B1 NO 324760 B1 NO324760 B1 NO 324760B1 NO 20030135 A NO20030135 A NO 20030135A NO 20030135 A NO20030135 A NO 20030135A NO 324760 B1 NO324760 B1 NO 324760B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- substituted
- formula
- halogen
- alkoxy
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 83
- 238000000034 method Methods 0.000 title claims description 42
- -1 Piperidine Compound Chemical class 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title claims description 38
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 1
- 150000002367 halogens Chemical class 0.000 claims description 34
- 150000003839 salts Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 230000002757 inflammatory effect Effects 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 11
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 208000023504 respiratory system disease Diseases 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 230000000414 obstructive effect Effects 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 6
- 206010027654 Allergic conditions Diseases 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 229940124630 bronchodilator Drugs 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000000739 antihistaminic agent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000012907 medicinal substance Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001415 nervonoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([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 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- 239000000243 solution Substances 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000000725 suspension Substances 0.000 description 25
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- 208000006673 asthma Diseases 0.000 description 23
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- 235000019341 magnesium sulphate Nutrition 0.000 description 13
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
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- 229960002052 salbutamol Drugs 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000004003 siderosis Diseases 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XFXFTPWZNUDTDO-JOCHJYFZSA-N tert-butyl n-[(2r)-1-[4-(4-fluorobenzoyl)piperidin-1-yl]-3-(4-nitrophenyl)propan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)CC=1C=CC(=CC=1)[N+]([O-])=O)N(CC1)CCC1C(=O)C1=CC=C(F)C=C1 XFXFTPWZNUDTDO-JOCHJYFZSA-N 0.000 description 1
- JPDMSLGNUKXXAF-XMMPIXPASA-N tert-butyl n-[(2r)-1-[4-(4-fluorobenzoyl)piperidin-1-yl]-3-[4-(methanesulfonamido)phenyl]propan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)CC=1C=CC(NS(C)(=O)=O)=CC=1)N(CC1)CCC1C(=O)C1=CC=C(F)C=C1 JPDMSLGNUKXXAF-XMMPIXPASA-N 0.000 description 1
- ZJTYRNPLVNMVPQ-GFCCVEGCSA-N tert-butyl n-[(2r)-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C=O)CC1=CC=CC=C1 ZJTYRNPLVNMVPQ-GFCCVEGCSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
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- 238000003828 vacuum filtration Methods 0.000 description 1
- 201000005539 vernal conjunctivitis Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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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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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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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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- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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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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- A61P3/00—Drugs for disorders of the metabolism
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- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0017174A GB0017174D0 (en) | 2000-07-12 | 2000-07-12 | Organic compounds |
| GB0023326A GB0023326D0 (en) | 2000-09-22 | 2000-09-22 | Organic compounds |
| PCT/EP2001/007941 WO2002004420A1 (en) | 2000-07-12 | 2001-07-10 | Piperidine coumpounds for use as ccr-3 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030135D0 NO20030135D0 (no) | 2003-01-10 |
| NO20030135L NO20030135L (no) | 2003-02-19 |
| NO324760B1 true NO324760B1 (no) | 2007-12-10 |
Family
ID=26244644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030135A NO324760B1 (no) | 2000-07-12 | 2003-01-10 | Piperidinforbindelse, farmasoytiske preparater, anvendelse av forbindelsene samt fremgangsmate for fremstilling derav |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6670379B2 (ru) |
| EP (1) | EP1303488B1 (ru) |
| JP (1) | JP2004502756A (ru) |
| KR (1) | KR20030036603A (ru) |
| CN (1) | CN1184204C (ru) |
| AR (1) | AR031597A1 (ru) |
| AT (1) | ATE447553T1 (ru) |
| AU (2) | AU2001281972B2 (ru) |
| BR (1) | BR0112456A (ru) |
| CA (1) | CA2412941C (ru) |
| CZ (1) | CZ200375A3 (ru) |
| DE (1) | DE60140366D1 (ru) |
| ES (1) | ES2334886T3 (ru) |
| HU (1) | HUP0301341A2 (ru) |
| IL (1) | IL153661A0 (ru) |
| MX (1) | MXPA02012848A (ru) |
| MY (1) | MY126139A (ru) |
| NO (1) | NO324760B1 (ru) |
| NZ (1) | NZ523414A (ru) |
| PE (1) | PE20020616A1 (ru) |
| PL (1) | PL358673A1 (ru) |
| PT (1) | PT1303488E (ru) |
| SK (1) | SK272003A3 (ru) |
| TW (1) | TWI227231B (ru) |
| WO (1) | WO2002004420A1 (ru) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19952147A1 (de) * | 1999-10-29 | 2001-05-03 | Boehringer Ingelheim Pharma | Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| AU2001295601A1 (en) * | 2000-10-09 | 2002-04-22 | Novartis Pharma Gmbh | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr33 receptor antagonists |
| GB0114699D0 (en) * | 2001-06-15 | 2001-08-08 | Novartis Ag | Organic compounds |
| ES2452691T5 (es) | 2003-09-16 | 2022-09-14 | Covis Pharma Gmbh | Uso de ciclesonida para el tratamiento de enfermedades respiratorias |
| JP6473133B2 (ja) * | 2013-03-15 | 2019-02-20 | アラクセス ファーマ エルエルシー | Ｋｒａｓｇ１２ｃの共有結合性阻害剤 |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| CN107849022A (zh) | 2015-04-10 | 2018-03-27 | 亚瑞克西斯制药公司 | 取代的喹唑啉化合物和其使用方法 |
| EP3283462B1 (en) | 2015-04-15 | 2020-12-02 | Araxes Pharma LLC | Fused-tricyclic inhibitors of kras and methods of use thereof |
| US10144724B2 (en) | 2015-07-22 | 2018-12-04 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
| WO2017058792A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| US10689356B2 (en) | 2015-09-28 | 2020-06-23 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| EP3356354A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058728A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| US10975071B2 (en) | 2015-09-28 | 2021-04-13 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| EP3356351A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| US10414757B2 (en) | 2015-11-16 | 2019-09-17 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
| US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
| CN110036010A (zh) | 2016-09-29 | 2019-07-19 | 亚瑞克西斯制药公司 | Kras g12c突变蛋白的抑制剂 |
| CN110312711A (zh) | 2016-10-07 | 2019-10-08 | 亚瑞克西斯制药公司 | 作为ras抑制剂的杂环化合物及其使用方法 |
| CN110382482A (zh) | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的杂-杂二环化合物及其使用方法 |
| EP3573970A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | 1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer |
| US11358959B2 (en) | 2017-01-26 | 2022-06-14 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| US11279689B2 (en) | 2017-01-26 | 2022-03-22 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1 yl)prop-2-en-1-one derivatives and similar compounds as KRAS G12C modulators for treating cancer |
| WO2018140512A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| TW201906832A (zh) | 2017-05-25 | 2019-02-16 | 美商亞瑞克西斯製藥公司 | 用於癌症治療之化合物及其使用方法 |
| CN110869358A (zh) | 2017-05-25 | 2020-03-06 | 亚瑞克西斯制药公司 | Kras的共价抑制剂 |
| EP3630747A1 (en) | 2017-05-25 | 2020-04-08 | Araxes Pharma LLC | Quinazoline derivatives as modulators of mutant kras, hras or nras |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8576098A (en) * | 1997-07-25 | 1999-02-16 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| US6339087B1 (en) | 1997-08-18 | 2002-01-15 | Syntex (U.S.A.) Llc | Cyclic amine derivatives-CCR-3 receptor antagonists |
| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| CN1163484C (zh) | 1998-11-17 | 2004-08-25 | 霍夫曼-拉罗奇有限公司 | 4-芳酰基-哌啶-ccr-3受体拮抗剂ⅲ |
| CA2348923A1 (en) * | 1998-12-18 | 2000-06-22 | Dean A. Wacker | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CA2361366A1 (en) * | 1999-03-26 | 2000-10-05 | Nicholas Kindon | Novel compounds |
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- 2001-07-10 PT PT01960488T patent/PT1303488E/pt unknown
- 2001-07-10 CA CA2412941A patent/CA2412941C/en not_active Expired - Fee Related
- 2001-07-10 DE DE60140366T patent/DE60140366D1/de not_active Expired - Lifetime
- 2001-07-10 AT AT01960488T patent/ATE447553T1/de not_active IP Right Cessation
- 2001-07-10 PE PE2001000683A patent/PE20020616A1/es not_active Application Discontinuation
- 2001-07-10 ES ES01960488T patent/ES2334886T3/es not_active Expired - Lifetime
- 2001-07-10 IL IL15366101A patent/IL153661A0/xx unknown
- 2001-07-10 KR KR10-2003-7000445A patent/KR20030036603A/ko not_active Application Discontinuation
- 2001-07-10 CN CNB018126111A patent/CN1184204C/zh not_active Expired - Fee Related
-
2003
- 2003-01-10 NO NO20030135A patent/NO324760B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030036603A (ko) | 2003-05-09 |
| ES2334886T3 (es) | 2010-03-17 |
| DE60140366D1 (de) | 2009-12-17 |
| AR031597A1 (es) | 2003-09-24 |
| US6670379B2 (en) | 2003-12-30 |
| TWI227231B (en) | 2005-02-01 |
| CN1184204C (zh) | 2005-01-12 |
| US20030176460A1 (en) | 2003-09-18 |
| NO20030135L (no) | 2003-02-19 |
| BR0112456A (pt) | 2003-07-22 |
| EP1303488A1 (en) | 2003-04-23 |
| CN1441780A (zh) | 2003-09-10 |
| JP2004502756A (ja) | 2004-01-29 |
| PL358673A1 (en) | 2004-08-09 |
| CA2412941C (en) | 2011-01-04 |
| HUP0301341A2 (hu) | 2003-08-28 |
| ATE447553T1 (de) | 2009-11-15 |
| CZ200375A3 (cs) | 2003-04-16 |
| AU8197201A (en) | 2002-01-21 |
| PE20020616A1 (es) | 2002-08-02 |
| SK272003A3 (en) | 2003-07-01 |
| EP1303488B1 (en) | 2009-11-04 |
| MXPA02012848A (es) | 2003-05-15 |
| NO20030135D0 (no) | 2003-01-10 |
| WO2002004420A1 (en) | 2002-01-17 |
| NZ523414A (en) | 2004-07-30 |
| PT1303488E (pt) | 2010-01-19 |
| IL153661A0 (en) | 2003-07-06 |
| AU2001281972B2 (en) | 2004-06-03 |
| MY126139A (en) | 2006-09-29 |
| CA2412941A1 (en) | 2002-01-17 |
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