KR910009684A - 방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 - Google Patents
방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 Download PDFInfo
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- KR910009684A KR910009684A KR1019900017897A KR900017897A KR910009684A KR 910009684 A KR910009684 A KR 910009684A KR 1019900017897 A KR1019900017897 A KR 1019900017897A KR 900017897 A KR900017897 A KR 900017897A KR 910009684 A KR910009684 A KR 910009684A
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- KR
- South Korea
- Prior art keywords
- group
- formula
- compound
- benzylpiperidin
- hydrogen
- 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.)
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- -1 Aromatic Amine Compounds Chemical class 0.000 title claims 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- MJSIOSYLTKCXCQ-UHFFFAOYSA-N n-[4-(4-benzylpiperidin-1-yl)-2-(3,4-difluorophenyl)butyl]-2,4-dichlorobenzamide Chemical compound C1=C(F)C(F)=CC=C1C(CNC(=O)C=1C(=CC(Cl)=CC=1)Cl)CCN1CCC(CC=2C=CC=CC=2)CC1 MJSIOSYLTKCXCQ-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims 2
- 230000000994 depressogenic effect Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- GTMUFVKDAMGHLB-UHFFFAOYSA-N n-[4-(4-benzylpiperidin-1-yl)-2-(3,4-dichlorophenyl)butyl]-4-fluoronaphthalene-1-carboxamide Chemical compound C12=CC=CC=C2C(F)=CC=C1C(=O)NCC(C=1C=C(Cl)C(Cl)=CC=1)CCN(CC1)CCC1CC1=CC=CC=C1 GTMUFVKDAMGHLB-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XESUOOGGPMESMV-UHFFFAOYSA-N n-[4-(4-benzylpiperidin-1-yl)-2-(3,4-dichlorophenyl)butyl]-2,4-dichlorobenzamide Chemical compound ClC1=CC(Cl)=CC=C1C(=O)NCC(C=1C=C(Cl)C(Cl)=CC=1)CCN1CCC(CC=2C=CC=CC=2)CC1 XESUOOGGPMESMV-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001326 naphthylalkyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- 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
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- 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
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- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
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- 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
- C07D211/26—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 nitrogen atoms
- C07D211/28—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 nitrogen atoms to which a second hetero atom is attached
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
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Abstract
Description
Claims (23)
- 일반식(Ⅰ)의 화합물 또는 이의 무기산 또는 유기산과의 염.상기식에서, m은 1∼3의 정수이고;Ar 및 Ar′는 각각 티에닐기;치환되지 않은 페닐기이거나 할로겐원자,C1-C3알킬, 트리플로오로메틸, 알콕시(여기서, 알킬은 C1-C3이다);히드록실 또는 메틸렌디옥시기에 의해 일- 또는 이치환된 페닐기; 또는 이미다졸릴기이며, Ar′은 치환되지 않았거나 할로겐에 의해 치환된 벤조티에닐기;치환되지 않았거나 할로겐에 의해 치환된 나프틸기;비페닐기;또는 치환 되지 않았거나 질소에 벤질기가 치환된 인돌릴기일 수 있으며-X는 수소이고-X′는 수소 또는 히드록실기이거나 하기의 X′와 결합하여 탄소-탄소 결합을 형성하며, 또는 X및X′가 함께 옥소기 또는 =N-O(CH2)P-Am의기(식에서, P는 2또는 3이며 Am은 디알킬아미노기이다)의 디알킬아미노알콕시아미노기를 형성하며, 각 알킬기는 탄소수가 1 내지 4일수 있고-Y는 질소원자 또는 C(X″)기(식에서, X″는 수소원자이거나 X′와 탄소-탄소 결합을 형성한다)이며-Q는 수소원자, C1-C4알킬기 또는 -(CH2)q-Am′의기(식에서, q는 2 또는 3이고 Am′은 피페리디노, 4-벤질과 페리디노 또는 디알킬아미노기이다)의 아미노알킬이고, 각 알킬기는 탄소수가 1 내지 4일수 있으며;R은 수소, 메틸기 또는 (CH2)n-L의기(식에서, n은 2∼6의 정수이고 L은 수소 또는 아미노기이다)이고;-T는및(식에서, W는 산소 또는 황원자 이다)로부터 선택된 기이며;-Z는 수소원자이거나, 혹은 T가 -C(=O)-의 기이면 M이거나 OM이며, 또는 T가 -C(=W)-NH-의 기이면 M이고, 여기에서, M은 수소;직쇄 또는 축쇄의 C1-C6알킬;치환되지 않은 페닐알킬기이거나 방향족 고리상에 할로겐, 히드록실, 탄소수 1 내지 4의 알콕시 또는 탄소수 1 내지 4의 알킬기로 일-또는 다치환된, 알킬기와 탄소수가 1 내지 3인 페닐알킬;알킬기의 탄소수가 1 내지 3인 피리딜알킬;알킬기의 탄소수가 1 내지 3인 나프틸알킬;알킬기의 탄소수가 1 내지 3인 피리딜티오알킬;스티릴;알킬기의 탄소수가 1 내지 3인 1-메틸아미다졸-2-일티오알킬;1-옥소페닐-3-인단-2-일;또는 치환되지 않았거나 일-또는 다치환된 방향족기 혹은 헤테로 방향족기이다.
- 일반식(Ⅰ*)의 광학적으로 순수한 화합물 또는 이의 무기산 또는 유기산과의 염.상기식에서, -n*n-n*n는 이 기호로 표시된 탄소원자가 제한된(+) 또는 (-)절대 배열을 가짐을 의미하며;-m,Ar,X,x′,Y,Q,R,T 및 M은 제1항에서 정의 한 바와 같다.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-2,4-디클로로벤즈 아미드 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드(+) 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-미클로로페닐)부틸]-2,4-디클로로벤즈 아미드(-) 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플루오로페닐)부틸]-2,4-디클로로벤즈 아미드(+) 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디플로오로페닐)부틸]-2,4-디클로로벤즈 아미드(-) 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-미클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드(+) 또는 이의 약제학적 허용가능염.
- N-[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]-4-플루오로나프탈렌-1-카르복스아미드(-) 또는 이의 약제학적 허용가능염.
- a)일반식(Ⅲ)의 유리 아민을 일반식(Ⅲ)의 산 작용성 유도체(T가 -CO-인, 일반식(Ⅰ)의 화합물을 제조하고자 하는 것이다) 또는 일반식(Ⅲ′)의 이소(티오)시아네이트(T가-C(W)-NH-인, 일반식(Ⅰ)의 화합물을 제조하고자 하는 것이다)로 처리하여 일반식(Ⅳ)의 화합물을 형성시키고,[상기식에서 m,Ar′ 및 Q는 제1항에서 정의한 바와 같고;R0는 수소, 메틸기 또는 (CH2)n-L0의기(식에서, n은 제1항에서 정의한 바와 같고 L0은 수소원자 또는 N-보호기에 의해 보호된 아미노기이다)이며;E는 히드록실기, 테트라이히드로피틴-2-일옥시기와 같은 O-보호기, 또는의 기(식에서, Ar,X 및 Y는 제1항에서 정의한 바와 같고 X0는 제1항의 X′기와 같으며, 여기에서 히드록실기는 0-보호기에 의해 보호된것)이다]HO-CO-Z (Ⅲ)(상기식에서, Z는 제1항에서 정의한 바와같다)W=C=N-Z (Ⅲ′)(상기식에서, W와 Z는 제1항에서 정의한 바와같다)(Ⅳ)b)E가 테트라이히드로피라닐옥시면, 단계,a)에서 일반식(Ⅱ)의 출발 아민상에서 선택적으로 수행하는 산 가수분해에 의해 테트라히드로피라닐기를 제거하고, (c)생성된 일반식 (Ⅴ)의 N-치환 알칸을아민을 메탄솔포닐 클로라이드로 처리하고,(Ⅴ)d)생성된 일반식(Ⅵ)의 메실레이트를 일반식(Ⅶ)의 아치 아민과 반응시키고,(Ⅵ)(Ⅶ)(상기식에서, Ar,Y,X 및 X′는 제1항에서 정의한 바와 같다)e)존재하는 특정한 O-보호기와 N-보호기를 제거하고, 적당하다면, 생성물을 그의 염으로 전환시킴을 특징으로 하는, 제1항의 화합물의 제조방법.
- 일반식(ⅩⅤⅠⅠ*)의 화합물을 산매질내, 용매내에서 처리하여, 산매질 내에서, 알칸올 AIKOH(여기에서, AIK는 탄소수 1내지 4의 알킬기이다)내에서 에스테르화되는 일반식(ⅩⅤⅠⅠ*)의 아미노산을 수득한 다음;상응하는 일반식(ⅩⅤⅠⅠ*)의 에스테르를 일반식(Ⅲ)의 산 작용성 유도체를 또는 일반식(Ⅲ′)의 이소(티오)시아네이트로 처리하고;(상기식에서, AIK는 상기에서 정의한 바와같고, Q,Ar′및 m은 제1항에서 정의한 바와 같으며 R0는 제12항에서 정의한 바와 같다)HO-CO-Z (Ⅲ)W=C=N-Z (Ⅲ′)(상기식에서, Z및 W는 제2항에서 정의한 바와같다)생성된 일반식(XX*)의 에스테르에 환원제를 작용시키고;(XX*)일반식(V*)의 상응 알콜을 일반식(Ⅵ*)의 메탄술포네이트에 스테르(이는 일반식(Ⅶ)의 아민으로 처리하고, 적당하다면 탑보호시켜 적당하다면 그의 염으로 전환되는 일반식(Ⅰ*)의 화합물이 얻어진다)로 전환시킴을 특징으로 하는 제2항의 광학적으로 순수한 일반식(Ⅰ*)의 화합물의 입체 선택적 제조방법.(상기식에서, Ar,x,x′및 Y는 제1항에서 정의한 바와 같다)
- 일반식(XVI)의 화합물 또는 그의 염.상기식에서, Enn은 테트라히드로피라닐옥시기 히드록실기 또는의기이고;-X0는 수소원자 또는 유리되어 있거나 O-보호기로 보호되어 있는 히드록실기이거나, 하기의 X″와 결합하여 탄소-탄소 결합을 형성하며, 또는 X와 X0가 함께 옥소기 또는 일반식=N-O-(CH2)-Am(식에서, P는 2 또는 3이고, Am은 디알킬아미노기이다)의 디알킬아미노알콕시이미노기를 형성하며, 각 알킬기는 탄소수 1내지 4일수 있고-Y는 질소원자 또는 C(X″)의 기(식에서, X″는 수소원자이거나 X0와 탄소-탄소 결합을 형성한다)이며;-R0는 수소, 메틸기 또는 (CH2)n-L0기(식에서, n은 2∼6이며 L0는 수소원자 또는 유리되어 있거나 N-보호기로 보호되어 있는 아미노기이다)이고;m,Ar,Ar′,X 및 Q는 제1항에서 정의한 바와 같다.
- 제14항에 있어서, 광학적으로 순수한 일반식(XVI)의 화합물의 m,Q 및 Ar′가 제1항에서 정의한 바와 같고 E0가 히드록실기이며 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
- 일반식(V′)의 화합물 또는 이의 염.상기식에서, G는 수소원자, 테트라히드로피라닐기 또는 메탄술포닐기며;R0는 수소원자, 메틸기 또는 (CH2)n-L0의 기(식에서, n은 2∼6이고 L0는 수소원자 또는 유리되어 있거나 N-보호기로 보호되어 있는 아미노기이다)이고;m,Ar,Ar′,X 및 Q는 제1항에서 정의한 바와 같다.
- 제16항에 있어서, 광학적으로 순수한 일반식(V′)의 화합물의 m,Q,T,Ar′ 및 Z가 1항에서 정의한 바와 같으며 G가 수소원자이고 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
- 제16항에 있어서, 광학적으로 순수한 일반식(V′)의 화합물의 m,Q,T,Ar′ 및 Z가 1항에서 정의한 바와 같으며 G가 메탄술포닐기이고 R0가 제12항에서 정의한 바와 같은 R0인 화합물.
- 활성 성분으로 제1항 또는 제2항에 따른 일반식(I) 또는 (I*)의 화합물을 함유하는 약제학적 조성물.
- 제19항에 있어서, 활성 성분을 한가지 이상의 약제학적 부형제와 혼합하여 투여단위 형태로 만들어진 약제학적 조성물.
- 제20항에 있어서, 활성 성분을 2.5내지 1000㎎ 함유하는 약제학적 조성물.
- 제14항에 있어서, E00가 히드록실기이고 R00가 수소원자인 화합물.
- N-메틸-N[4-(4-벤질피페리딘-1-일)-2-(3,4-디클로로페닐)부틸]페닐 아세트 아미드.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
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FR8914517A FR2654100B1 (fr) | 1989-11-06 | 1989-11-06 | Arylalkylenediamines, procede pour leur preparation et compositions pharmaceutiques les contenant. |
FR8914517 | 1989-11-06 | ||
FR9007534 | 1990-06-15 | ||
FR9007534A FR2663329B1 (fr) | 1990-06-15 | 1990-06-15 | Composes aromatiques amines, procede pour leur preparation et compositions pharmaceutiques les contenant. |
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KR910009684A true KR910009684A (ko) | 1991-06-28 |
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KR1019900017897A Ceased KR910009684A (ko) | 1989-11-06 | 1990-11-06 | 방향족 아민 화합물, 이의 제조방법 및 이들의 존재하는 약제학적 조성물 |
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US (3) | US5317020A (ko) |
EP (1) | EP0428434A3 (ko) |
JP (1) | JPH03206086A (ko) |
KR (1) | KR910009684A (ko) |
AU (2) | AU649973B2 (ko) |
CA (1) | CA2029275A1 (ko) |
FI (1) | FI97540C (ko) |
HU (3) | HU913347D0 (ko) |
IE (1) | IE903957A1 (ko) |
IL (1) | IL96241A (ko) |
LV (1) | LV10713B (ko) |
MY (1) | MY141603A (ko) |
NO (1) | NO177299C (ko) |
NZ (1) | NZ235985A (ko) |
PL (3) | PL165758B1 (ko) |
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Families Citing this family (154)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6218364B1 (en) | 1988-06-20 | 2001-04-17 | Scott L. Harbeson | Fluorinated neurokinin A antagonists |
US5830863A (en) * | 1988-06-20 | 1998-11-03 | Merrell Pharmaceuticals Inc. | Neurokinin A antagonists |
ZA906188B (en) * | 1989-08-10 | 1991-06-26 | Merrell Dow Pharma | Cyclic neurokinin a antagonists |
IL99320A (en) * | 1990-09-05 | 1995-07-31 | Sanofi Sa | Arylalkylamines, their preparation and pharmaceutical compositions containing them |
FR2678267B1 (fr) * | 1991-06-25 | 1994-02-04 | Elf Sanofi | Arylalkylamines, procede pour leur preparation et compositions pharmaceutiques les contenant. |
CZ284993B6 (cs) * | 1991-03-29 | 1999-04-14 | Eli Lilly And Company | Derivát piperidinu |
US5250542A (en) * | 1991-03-29 | 1993-10-05 | Eli Lilly And Company | Peripherally selective piperidine carboxylate opioid antagonists |
FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
DK0533280T4 (da) * | 1991-09-20 | 2005-02-28 | Glaxo Group Ltd | Ny medicinsk anvendelse af tachykininantagonister |
GB9201179D0 (en) * | 1992-01-21 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
KR100269756B1 (ko) * | 1992-02-13 | 2000-10-16 | 슈테펜엘.네스비트 | 피페리디닐티아시클릭유도체(Piperidinyl Thiacyclic Derivatives) |
TW224462B (ko) * | 1992-02-24 | 1994-06-01 | Squibb & Sons Inc | |
FR2688218A1 (fr) * | 1992-03-03 | 1993-09-10 | Sanofi Elf | Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant. |
FR2688219B1 (fr) * | 1992-03-03 | 1994-07-08 | Sanofi Elf | Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant. |
ES2043557B1 (es) * | 1992-06-04 | 1994-07-01 | Ferrer Int | Procedimiento de obtencion de nuevos derivados de la 4-bencilpiperidina. |
ES2060547B1 (es) * | 1992-06-04 | 1995-06-16 | Ferrer Int | Mejoras en el objeto de la patente de invencion n/ 9201158 que se refiere a "procedimiento de obtencion de nuevos derivados de la 4-bencilpiperidina". |
JP3507494B2 (ja) * | 1992-08-13 | 2004-03-15 | ワーナー−ランバート・コンパニー | タキキニン拮抗薬 |
FR2696178B1 (fr) * | 1992-09-30 | 1994-12-30 | Sanofi Elf | Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
US5391819A (en) * | 1992-09-30 | 1995-02-21 | Merck & Co., Inc. | Process of making chiral 2-aryl-1,4-butanediamine derivatives as useful neurokinin-A antagonists |
US5583134A (en) * | 1992-09-30 | 1996-12-10 | Sanofi | 1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present |
GB9321557D0 (en) * | 1992-11-03 | 1993-12-08 | Zeneca Ltd | Carboxamide derivatives |
US5830854A (en) * | 1992-12-14 | 1998-11-03 | Merck Sharp & Dohme, Limited | Method of treating cystic fibrosis using a tachykinin receptor antagonist |
CN1042335C (zh) * | 1993-01-03 | 1999-03-03 | 诺瓦提斯公司 | 1-酰基哌啶化合物、其制备方法、药物组合物及用途 |
FR2700472B1 (fr) | 1993-01-19 | 1995-02-17 | Rhone Poulenc Rorer Sa | Association synergisante ayant un effet antagoniste des récepteurs NK1 et NK2. |
ATE169001T1 (de) * | 1993-01-28 | 1998-08-15 | Merck & Co Inc | Substituierte spiro-azaringen als tachykinine rezeptor antagonisten |
US5512680A (en) * | 1993-02-26 | 1996-04-30 | Sanofi | Process for the preparation of an optically pure aminoalcohol |
FR2701946B1 (fr) * | 1993-02-26 | 1995-05-24 | Sanofi Elf | Procédé pour la préparation d'un aminoalcool optiquement pur. |
US5635510A (en) * | 1993-05-06 | 1997-06-03 | Merrell Pharmaceuticals Inc. | Substituted pyrrolidin-3-yl-alkyl-piperidines |
GB9310066D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Alkyl substituted heterocycles |
GB9310713D0 (en) * | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Aryl substituted heterocycles |
GB9317104D0 (en) * | 1993-08-17 | 1993-09-29 | Zeneca Ltd | Therapeutic heterocycles |
GB9322643D0 (en) * | 1993-11-03 | 1993-12-22 | Zeneca Ltd | Lactam derivatives |
GB9325074D0 (en) * | 1993-12-07 | 1994-02-02 | Zeneca Ltd | Bicyclic heterocycles |
US5589489A (en) * | 1993-12-15 | 1996-12-31 | Zeneca Limited | Cyclic amide derivatives for treating asthma |
FR2717802B1 (fr) * | 1994-03-25 | 1996-06-21 | Sanofi Sa | Nouveaux composés aromatiques, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
US5434158A (en) * | 1994-04-26 | 1995-07-18 | Merck & Co., Inc. | Spiro-substituted azacycles as neurokinin-3 antagonists |
GB9408872D0 (en) * | 1994-05-03 | 1994-06-22 | Zeneca Ltd | Heterocyclic compounds |
DE69508093T2 (de) | 1994-08-25 | 1999-07-15 | Merrell Pharmaceuticals Inc., Cincinnati, Ohio | Substituierte piperidine für die behandlung von allergischen krankheiten |
US5607936A (en) * | 1994-09-30 | 1997-03-04 | Merck & Co., Inc. | Substituted aryl piperazines as neurokinin antagonists |
TW397825B (en) * | 1994-10-14 | 2000-07-11 | Novartis Ag | Aroyl-piperidine derivatives |
FR2725900B1 (fr) * | 1994-10-21 | 1997-07-18 | Sanofi Sa | Utilisation d'antagonistes des recepteurs nk1 pour la preparation de medicaments a action cardioregulatrice |
DE69534213T2 (de) * | 1994-10-25 | 2006-01-12 | Astrazeneca Ab | Therapeutisch wirksame Heterocyclen |
US5998444A (en) * | 1995-10-24 | 1999-12-07 | Zeneca Ltd. | Piperidinyl compounds as NK1 or NK2 antagonists |
US6008223A (en) * | 1994-10-27 | 1999-12-28 | Zeneca Limited | Therapeutic compounds |
GB9421709D0 (en) * | 1994-10-27 | 1994-12-14 | Zeneca Ltd | Therapeutic compounds |
CA2162786A1 (en) * | 1994-11-22 | 1996-05-23 | Philip Arthur Hipskind | Heterocyclic tachykinin receptor antagonists |
FR2729954B1 (fr) | 1995-01-30 | 1997-08-01 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
FR2729952B1 (fr) * | 1995-01-30 | 1997-04-18 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
GB9502644D0 (en) * | 1995-02-10 | 1995-03-29 | Zeneca Ltd | Heterocyclic derivatives |
EP0815105B1 (en) * | 1995-03-15 | 2001-10-04 | Aventis Pharmaceuticals Inc. | Heterocyclic substituted piperazinone derivatives as tachykinin receptor antagonists |
MX9707879A (es) * | 1995-04-13 | 1997-11-29 | Hoechst Marion Roussel Inc | Derivados de piperazina sustituidos novedosos que tienen actividad antagonista de receptor de taquinina. |
GB9508786D0 (en) | 1995-04-29 | 1995-06-21 | Zeneca Ltd | Substituted heterocycles |
US5654316A (en) * | 1995-06-06 | 1997-08-05 | Schering Corporation | Piperidine derivatives as neurokinin antagonists |
ATE243204T1 (de) * | 1995-08-24 | 2003-07-15 | Basf Ag | Isoxazole- und isothiazole-5-carboxamid derivate, deren herstellung und deren verwendung als herbizide |
FR2738245B1 (fr) * | 1995-08-28 | 1997-11-21 | Sanofi Sa | Nouveaux derives de piperidine, procede pour leur obtention et compositions pharmaceutiques les contenant |
FR2738819B1 (fr) * | 1995-09-14 | 1997-12-05 | Sanofi Sa | Nouveaux composes antagonistes selectifs du recepteur nk3 humain, procede pour leur obtention et compositions pharmaceutiques les contenant |
TW458774B (en) | 1995-10-20 | 2001-10-11 | Pfizer | Antiemetic pharmaceutical compositions |
GB9523526D0 (en) * | 1995-11-17 | 1996-01-17 | Zeneca Ltd | Therapeutic compounds |
US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
HU224225B1 (hu) | 1995-12-01 | 2005-06-28 | Sankyo Co. Ltd. | Tachikinin receptor antagonista hatású heterociklusos vegyületek, ezek előállítási eljárása és alkalmazásuk gyógyszerkészítmények előállítására |
US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
US5998439A (en) * | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
DE19624704A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalkansäureamide |
US6451816B1 (en) | 1997-06-20 | 2002-09-17 | Klinge Pharma Gmbh | Use of pyridyl alkane, pyridyl alkene and/or pyridyl alkine acid amides in the treatment of tumors or for immunosuppression |
DE19624659A1 (de) | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalken- und Pyridylalkinsäureamide |
MY132550A (en) * | 1996-08-22 | 2007-10-31 | Novartis Ag | Acylaminoalkenylene-amide derivatives as nk1 and nk2 antogonists |
US5977139A (en) * | 1996-12-15 | 1999-11-02 | Hoechst Marion Roussel, Inc. | Carboxysubstituted cyclic carboxamide derivatives |
US5861417A (en) * | 1996-12-19 | 1999-01-19 | Hoechst Marion Roussel, Inc. | Heterocyclic substituted pyrrolidine amide derivatives |
US6013652A (en) * | 1997-12-04 | 2000-01-11 | Merck & Co., Inc. | Spiro-substituted azacycles as neurokinin antagonists |
DE19756235A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
US6903118B1 (en) | 1997-12-17 | 2005-06-07 | Klinge Pharma Gmbh | Piperazinyl-substituted pyridylalkane, alkene and alkine carboxamides |
DE19756261A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide |
DE19756212A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue, mit einem cyclischen Imid substituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
PT1058683E (pt) * | 1998-02-02 | 2003-04-30 | Lg Chemical Ltd | Inibidores da farnesil-transferase com uma estrutura de piperidina e seu processo de preparacao |
US5928783A (en) * | 1998-03-09 | 1999-07-27 | National Starch And Chemical Investment Holding Corporation | Pressure sensitive adhesive compositions |
US6316445B1 (en) | 1998-05-15 | 2001-11-13 | Aventis Pharmaceuticals Inc. | Carboxy substituted acylic carboxamide derivatives |
FR2779429B1 (fr) * | 1998-06-03 | 2000-07-13 | Synthelabo | Derives d'oxindole, leurs preparations et leurs applications en therapeutique |
CN1309638A (zh) * | 1998-07-10 | 2001-08-22 | 阿斯特拉曾尼卡有限公司 | 作为神经激肽受体拮抗剂的n-取代的萘甲酰胺 |
GB9922519D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
GB9922521D0 (en) * | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
US6194458B1 (en) | 1998-10-30 | 2001-02-27 | Merck & Co., Inc. | Benzamide potassium channel inhibitors |
US6303637B1 (en) | 1998-10-30 | 2001-10-16 | Merck & Co., Inc. | Heterocyclic potassium channel inhibitors |
US6632836B1 (en) | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
CA2350722A1 (en) * | 1998-11-17 | 2000-05-25 | Leyi Gong | 4-aroyl-piperidin-ccr-3 receptor antagonists iii |
DE69938193D1 (de) | 1998-11-20 | 2008-04-03 | Hoffmann La Roche | Piperidin ccr-3 rezeptor-hemmer |
US6331541B1 (en) | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
AU2482100A (en) * | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
WO2000035451A1 (en) * | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
US6605623B1 (en) * | 1998-12-18 | 2003-08-12 | Bristol-Myers Squibb Pharma Co. | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
EP1158980B1 (en) * | 1998-12-18 | 2005-08-24 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
EP1031564A1 (en) | 1999-02-26 | 2000-08-30 | Klinge Pharma GmbH | Inhibitors of cellular nicotinamide mononucleotide formation and their use in cancer therapy |
GB9907571D0 (en) * | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Compounds |
US6365591B1 (en) | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
US7163949B1 (en) | 1999-11-03 | 2007-01-16 | Amr Technology, Inc. | 4-phenyl substituted tetrahydroisoquinolines and use thereof |
RU2309953C2 (ru) | 1999-11-03 | 2007-11-10 | Эймр Текнолоджи, Инк. | Арил- и гетероарилзамещенные тетрагидроизохинолины, фармацевтическая композиция и способ лечения на их основе |
CA2399791A1 (en) * | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases |
JP2004517805A (ja) | 2000-06-30 | 2004-06-17 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体活性調節剤としてのn−ウレイドヘテロシクロアルキル−ピペリジン |
BR0112350A (pt) | 2000-07-11 | 2003-06-24 | Albany Molecular Res Inc | Composto, composição farmacêutica, e, método de tratar um animal afligido por um distúrbio neurológico ou psicológico |
KR20030093257A (ko) | 2001-03-21 | 2003-12-06 | 파마코페이아, 인크. | Mch 조정 활성을 지닌 아릴 및 바이아릴 화합물 |
US6815451B2 (en) * | 2001-03-27 | 2004-11-09 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-Tetrahydroisoquinolines derivatives as urotensin II receptor antagonists |
WO2002083134A1 (en) | 2001-04-12 | 2002-10-24 | Pharmacopeia, Inc. | Aryl and biaryl piperidines used as mch antagonists |
DZ3292A1 (fr) * | 2001-09-13 | 2005-05-14 | Solvay Pharm Gmbh | Nouveaux composes de type 1-[1-(hetero)aryl-1-perhydroxyalkylmethyl]piperazine, methodes pour les preparer et medicaments renfermant cescomposes |
NZ534046A (en) | 2001-12-04 | 2006-02-24 | Actelion Pharmaceuticals Ltd | 4-(piperidyl-and pyrrolidyl-alkyl-ureido) -quinolines as urotensin II receptor antagonists |
TW200508221A (en) * | 2003-06-13 | 2005-03-01 | Astrazeneca Ab | New azetidine compounds |
MXPA06003264A (es) | 2003-09-26 | 2006-06-08 | Actelion Pharmaceuticals Ltd | Derivados de piridina y uso de los mismos como antagonistas de la urotensina ii. |
US7291744B2 (en) * | 2003-11-13 | 2007-11-06 | Bristol-Myers Squibb Company | N-ureidoalkyl-amino compounds as modulators of chemokine receptor activity |
CN103880827B (zh) | 2004-07-15 | 2017-01-04 | 阿尔巴尼分子研究公司 | 芳基和杂芳基取代的四氢异喹啉及其阻断去甲肾上腺素、多巴胺和血清素的重摄取的应用 |
JP5139066B2 (ja) | 2004-10-12 | 2013-02-06 | アクテリオン ファーマシューティカルズ リミテッド | 結晶性硫酸塩としての1−[2−(4−ベンジル−4−ヒドロキシ−ピペリジン−1−イル)−エチル]−3−(2−メチル−キノリン−4−イル)−尿素 |
WO2006123182A2 (en) | 2005-05-17 | 2006-11-23 | Merck Sharp & Dohme Limited | Cyclohexyl sulphones for treatment of cancer |
JP5258561B2 (ja) | 2005-07-15 | 2013-08-07 | アルバニー モレキュラー リサーチ, インコーポレイテッド | アリール置換およびヘテロアリール置換テトラヒドロベンズアゼピンならびにノルエピネフリン、ドーパミンおよびセロトニンの再取り込みを遮断するためのその使用 |
US7592344B2 (en) * | 2005-11-30 | 2009-09-22 | Solvay Pharmaceuticals Gmbh | NK1 and NK2-antagonists and compositions and methods of using the same |
ATE550324T1 (de) * | 2005-11-30 | 2012-04-15 | Abbott Products Gmbh | Neue nk1- und nk2-antagonisten |
EP1979319A1 (en) * | 2006-02-01 | 2008-10-15 | Solvay Pharmaceuticals GmbH | Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparations |
GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
WO2007136323A1 (en) * | 2006-05-18 | 2007-11-29 | Albireo Ab | A novel process suitable for large-scale production of phenyl propan derivatives of formula i |
US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
BRPI0806245B1 (pt) | 2007-01-10 | 2022-01-25 | Msd Italia S.R.L. | Compostos de fórmula i e seus usos |
KR20090112722A (ko) | 2007-01-24 | 2009-10-28 | 글락소 그룹 리미티드 | 3,5-디아미노-6-(2,3-디클로로페닐)-1,2,4-트리아진 또는 r(-)-2,4-디아미노-5-(2,3-디클로로페닐)-6-플루오로메틸 피리미딘 및 nk1을 포함하는 제약 조성물 |
CA2690191C (en) | 2007-06-27 | 2015-07-28 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
AR071997A1 (es) | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina |
US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
WO2010114780A1 (en) | 2009-04-01 | 2010-10-07 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
PE20120373A1 (es) | 2009-05-12 | 2012-05-17 | Albany Molecular Res Inc | 7-([1,2,4]triazolo[1,5-a]piridin-6-il)-4-(3,4-diclorofenil)-1,2,3,4-tetrahidroisoquinolina |
ES2528404T3 (es) | 2009-05-12 | 2015-02-10 | Bristol-Myers Squibb Company | Formas cristalinas de (S)-7-([1,2,4]triazol[1,5-a]piridin-6-il)-4-(3,4-diclorofenil)-1,2,3,4-tetrahidroisoquinolina y sus usos |
MX2011011901A (es) | 2009-05-12 | 2012-01-20 | Albany Molecular Res Inc | Tetrahidroisoquinolinas aril, heteroaril, y heterociclo sustituidas y uso de las mismas. |
NZ599343A (en) | 2009-10-14 | 2014-05-30 | Merck Sharp & Dohme | Substituted piperidines that increase p53 activity and the uses thereof |
CA2805265A1 (en) | 2010-08-02 | 2012-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina) |
US9029341B2 (en) | 2010-08-17 | 2015-05-12 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of hepatitis B virus (HBV) gene expression using short interfering nucleic acid (siNA) |
EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
WO2012030685A2 (en) | 2010-09-01 | 2012-03-08 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
WO2012036997A1 (en) | 2010-09-16 | 2012-03-22 | Schering Corporation | Fused pyrazole derivatives as novel erk inhibitors |
US9260471B2 (en) | 2010-10-29 | 2016-02-16 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using short interfering nucleic acids (siNA) |
EP2654748B1 (en) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
US20140046059A1 (en) | 2011-04-21 | 2014-02-13 | Piramal Enterprises Limited | Process for the preparation of morpholino sulfonyl indole derivatives |
EP2770987B1 (en) | 2011-10-27 | 2018-04-04 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
WO2013165816A2 (en) | 2012-05-02 | 2013-11-07 | Merck Sharp & Dohme Corp. | SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS |
MX2015002231A (es) | 2012-08-23 | 2015-07-17 | Alios Biopharma Inc | Compuestos antivirales. |
JP6280554B2 (ja) | 2012-09-28 | 2018-02-14 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | Erk阻害剤である新規化合物 |
AU2013352568B2 (en) | 2012-11-28 | 2019-09-19 | Merck Sharp & Dohme Llc | Compositions and methods for treating cancer |
JP6387013B2 (ja) | 2012-12-20 | 2018-09-12 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | Hdm2阻害薬としての置換されたイミダゾピリジン類 |
US9540377B2 (en) | 2013-01-30 | 2017-01-10 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as HDM2 inhibitors |
AU2014308991B2 (en) * | 2013-08-21 | 2019-02-14 | Janssen Biopharma, Inc. | Antiviral compounds |
WO2015034925A1 (en) | 2013-09-03 | 2015-03-12 | Moderna Therapeutics, Inc. | Circular polynucleotides |
US10975084B2 (en) | 2016-10-12 | 2021-04-13 | Merck Sharp & Dohme Corp. | KDM5 inhibitors |
US10947234B2 (en) | 2017-11-08 | 2021-03-16 | Merck Sharp & Dohme Corp. | PRMT5 inhibitors |
EP3706747A4 (en) | 2017-11-08 | 2021-08-04 | Merck Sharp & Dohme Corp. | PRMT5 INHIBITORS |
EP3833667B1 (en) | 2018-08-07 | 2024-03-13 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
US11993602B2 (en) | 2018-08-07 | 2024-05-28 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
KR20210046009A (ko) | 2018-08-07 | 2021-04-27 | 머크 샤프 앤드 돔 코포레이션 | Prmt5 억제제 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1151516B (de) * | 1960-08-03 | 1963-07-18 | Krewel Leuffen Gmbh | Verfahren zur Herstellung von ª†-Aminoalkoholen mit quartaerem ª‰-C-Atom |
DE1261862B (de) * | 1965-03-11 | 1968-02-29 | Bayer Ag | Verfahren zur Herstellung von N-substituierten 3-Aminopropanolen |
GB1213166A (en) * | 1967-07-19 | 1970-11-18 | Aspro Nicholas Ltd | Novel cyanoethanols, their synthesis and their conversion to derivatives |
NL7112938A (ko) * | 1970-09-30 | 1972-04-05 | ||
GB1374366A (en) * | 1972-07-21 | 1974-11-20 | Science Union & Cie | Propanol derivatives and a process for their preparation |
US3941795A (en) * | 1974-02-08 | 1976-03-02 | Richardson-Merrell Inc. | α-ARYL-4-SUBSTITUTED PIPERIDINOALKANOL DERIVATIVES |
DE2944150A1 (de) * | 1979-11-02 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Gummifederreifen und verfahren zu seiner herstellung |
DE3276313D1 (en) * | 1981-09-24 | 1987-06-19 | Beecham Wuelfing Gmbh & Co Kg | Sulphonamides |
DK159420C (da) * | 1983-03-09 | 1991-03-11 | Ciba Geigy Ag | N-(piperidinyl-alkyl)-carboxamider og salte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelsen af forbindelserne til fremstilling af antipsykotiske farmaceutiske praeparater |
JPH0660160B2 (ja) * | 1985-12-13 | 1994-08-10 | テルモ株式会社 | アミド誘導体およびこれを含有する抗アレルギ−剤 |
DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
IT1182010B (it) * | 1985-12-30 | 1987-09-30 | Consiglio Nazionale Ricerche | Procedimento per ottenere, in films epitessial di granati magnetici strati aventi diverse proprieta di anisotropia magnetica |
FR2613719B1 (fr) * | 1987-04-10 | 1991-03-22 | Sanofi Sa | Derives aromatiques, leur preparation et leur utilisation comme antimicrobiens |
FR2620704B1 (fr) * | 1987-09-17 | 1991-04-26 | Sanofi Sa | Derives de (benzyl-4 piperidino)-1 propanol-2, leur preparation, leur utilisation comme antimicrobiens et les produits les contenant |
US5278316A (en) * | 1989-06-29 | 1994-01-11 | Warner-Lambert Company | N-substituted cycloalkyl and polycycloalkyl alpha-substituted Trp-Phe- and phenethylamine derivatives |
-
1990
- 1990-11-02 IE IE395790A patent/IE903957A1/en unknown
- 1990-11-02 FI FI905444A patent/FI97540C/fi not_active IP Right Cessation
- 1990-11-05 HU HU913347A patent/HU913347D0/hu unknown
- 1990-11-05 CA CA002029275A patent/CA2029275A1/en not_active Abandoned
- 1990-11-05 US US07/610,093 patent/US5317020A/en not_active Expired - Fee Related
- 1990-11-05 HU HU913346A patent/HU913346D0/hu unknown
- 1990-11-05 PT PT95790A patent/PT95790A/pt not_active Application Discontinuation
- 1990-11-05 NO NO904802A patent/NO177299C/no unknown
- 1990-11-05 HU HU907027A patent/HUT56543A/hu unknown
- 1990-11-05 RU SU904831627A patent/RU2084453C1/ru active
- 1990-11-05 AU AU65838/90A patent/AU649973B2/en not_active Ceased
- 1990-11-05 IL IL9624190A patent/IL96241A/en not_active IP Right Cessation
- 1990-11-06 PL PL90293823A patent/PL165758B1/pl unknown
- 1990-11-06 JP JP2300929A patent/JPH03206086A/ja active Pending
- 1990-11-06 EP EP19900403125 patent/EP0428434A3/fr not_active Ceased
- 1990-11-06 KR KR1019900017897A patent/KR910009684A/ko not_active Ceased
- 1990-11-06 MY MYPI90001960A patent/MY141603A/en unknown
- 1990-11-06 PL PL90287644A patent/PL166565B1/pl unknown
- 1990-11-06 NZ NZ235985A patent/NZ235985A/en unknown
- 1990-11-06 PL PL90303827A patent/PL166582B1/pl unknown
-
1993
- 1993-02-25 LV LVP-93-142A patent/LV10713B/xx unknown
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1994
- 1994-03-11 US US08/208,672 patent/US5686609A/en not_active Expired - Fee Related
- 1994-03-31 AU AU59245/94A patent/AU668018B2/en not_active Ceased
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1995
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Also Published As
Publication number | Publication date |
---|---|
HU907027D0 (en) | 1991-05-28 |
FI905444A0 (fi) | 1990-11-02 |
AU668018B2 (en) | 1996-04-18 |
PL166565B1 (pl) | 1995-06-30 |
EP0428434A2 (fr) | 1991-05-22 |
IL96241A (en) | 1996-03-31 |
EP0428434A3 (en) | 1991-10-09 |
PL293823A1 (en) | 1993-01-25 |
PL287644A1 (en) | 1992-07-27 |
AU649973B2 (en) | 1994-06-09 |
NZ235985A (en) | 1993-10-26 |
CA2029275A1 (en) | 1991-05-07 |
FI97540C (fi) | 1997-01-10 |
HUT56543A (en) | 1991-09-30 |
FI97540B (fi) | 1996-09-30 |
HU913347D0 (en) | 1992-01-28 |
JPH03206086A (ja) | 1991-09-09 |
PL166582B1 (pl) | 1995-06-30 |
US5317020A (en) | 1994-05-31 |
NO904802D0 (no) | 1990-11-05 |
IL96241A0 (en) | 1991-08-16 |
AU6583890A (en) | 1991-05-23 |
AU5924594A (en) | 1994-06-02 |
NO177299C (no) | 1995-08-23 |
NO904802L (no) | 1991-05-07 |
MY141603A (en) | 2010-05-31 |
IE903957A1 (en) | 1991-05-08 |
US5618938A (en) | 1997-04-08 |
NO177299B (no) | 1995-05-15 |
HU913346D0 (en) | 1992-01-28 |
LV10713A (lv) | 1995-06-20 |
PT95790A (pt) | 1991-09-13 |
LV10713B (en) | 1995-10-20 |
US5686609A (en) | 1997-11-11 |
PL165758B1 (pl) | 1995-02-28 |
RU2084453C1 (ru) | 1997-07-20 |
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