SK283555B6 - 1-(1,2-Disubstituovaný piperidinyl)-4-substituované deriváty piperidínu, spôsob ich výroby, ich použitie a farmaceutické prostriedky na ich báze - Google Patents
1-(1,2-Disubstituovaný piperidinyl)-4-substituované deriváty piperidínu, spôsob ich výroby, ich použitie a farmaceutické prostriedky na ich báze Download PDFInfo
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- SK283555B6 SK283555B6 SK831-98A SK83198A SK283555B6 SK 283555 B6 SK283555 B6 SK 283555B6 SK 83198 A SK83198 A SK 83198A SK 283555 B6 SK283555 B6 SK 283555B6
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- Slovakia
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- alkyl
- phenyl
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- hydrogen
- substituted
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- -1 1-(1,2-Disubstituted piperidinyl)-4-substituted piperidine Chemical class 0.000 title claims abstract description 69
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 61
- 239000001257 hydrogen Substances 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 9
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 238000007126 N-alkylation reaction Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- IAGHMDWSGKHJKE-UHFFFAOYSA-N 8-[2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperidin-4-yl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2C(CC(CC2)N2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CC=2C=CC=CC=2)=C1 IAGHMDWSGKHJKE-UHFFFAOYSA-N 0.000 claims description 2
- MJFYBGHTCHHMIT-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[2-[(3,4-difluorophenyl)methyl]-4-[4-phenyl-4-(pyrrolidine-1-carbonyl)piperidin-1-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1CC1N(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCC(N2CCC(CC2)(C(=O)N2CCCC2)C=2C=CC=CC=2)C1 MJFYBGHTCHHMIT-UHFFFAOYSA-N 0.000 claims description 2
- NOSXPWAFWFCCPM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-[4-[4-phenyl-4-(pyrrolidine-1-carbonyl)piperidin-1-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]piperidin-1-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1CC1N(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCC(N2CCC(CC2)(C(=O)N2CCCC2)C=2C=CC=CC=2)C1 NOSXPWAFWFCCPM-UHFFFAOYSA-N 0.000 claims description 2
- CKTDOXOPZZTDJF-UHFFFAOYSA-N n-[[1-[2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperidin-4-yl]-4-phenylpiperidin-4-yl]methyl]acetamide Chemical compound C1CC(CNC(=O)C)(C=2C=CC=CC=2)CCN1C(C1)CCN(C(=O)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C1CC1=CC=CC=C1 CKTDOXOPZZTDJF-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003053 piperidines Chemical class 0.000 claims 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- OJQBGTKDPDCBDF-UHFFFAOYSA-N 3-[1-[2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperidin-4-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2C(CC(CC2)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC=2C=CC=CC=2)=C1 OJQBGTKDPDCBDF-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
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- 125000000815 N-oxide group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 51
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- 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
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly 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
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- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
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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
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D405/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP95203651 | 1995-12-27 | ||
PCT/EP1996/005883 WO1997024324A1 (en) | 1995-12-27 | 1996-12-20 | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives as tachykinin receptor antagonists |
Publications (2)
Publication Number | Publication Date |
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SK83198A3 SK83198A3 (en) | 1999-02-11 |
SK283555B6 true SK283555B6 (sk) | 2003-09-11 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK831-98A SK283555B6 (sk) | 1995-12-27 | 1996-12-20 | 1-(1,2-Disubstituovaný piperidinyl)-4-substituované deriváty piperidínu, spôsob ich výroby, ich použitie a farmaceutické prostriedky na ich báze |
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US (2) | US6169097B1 (cs) |
EP (1) | EP0855999B1 (cs) |
JP (1) | JP4039691B2 (cs) |
KR (1) | KR100493574B1 (cs) |
CN (1) | CN1131854C (cs) |
AR (1) | AR005277A1 (cs) |
AT (1) | ATE206397T1 (cs) |
AU (1) | AU707037B2 (cs) |
BR (1) | BR9612334A (cs) |
CA (1) | CA2238818C (cs) |
CZ (1) | CZ296316B6 (cs) |
DE (1) | DE69615700T2 (cs) |
DK (1) | DK0855999T3 (cs) |
EA (1) | EA001559B1 (cs) |
ES (1) | ES2164939T3 (cs) |
HU (1) | HU228128B1 (cs) |
IL (1) | IL124640A (cs) |
MY (1) | MY117557A (cs) |
NO (1) | NO310913B1 (cs) |
NZ (1) | NZ325843A (cs) |
PL (1) | PL192397B1 (cs) |
PT (1) | PT855999E (cs) |
SI (1) | SI0855999T1 (cs) |
SK (1) | SK283555B6 (cs) |
TR (1) | TR199801211T2 (cs) |
TW (1) | TW531537B (cs) |
WO (1) | WO1997024324A1 (cs) |
ZA (1) | ZA9610885B (cs) |
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TW531537B (en) | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
AU2307899A (en) * | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
WO1999032481A1 (en) * | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
BR9913201A (pt) | 1998-08-25 | 2001-05-08 | Novartis Ag | Uso de antagonista da substância p para o tratamento da sìndrome da fadiga crÈnica e/ou fibromialgia e uso de antagonistas do recptor de nk-1 para tratamento da sìndrome da fadiga crÈnica |
AU2056800A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | Heterocyclic piperidines as modulators of chemokine receptor activity |
CA2366260A1 (en) * | 1999-03-05 | 2000-09-14 | Masahiro Imoto | Heterocyclic compounds having effect of activating .alpha.4.beta.2 nicotinic acetylcholine receptors |
US6387930B1 (en) | 1999-05-04 | 2002-05-14 | Schering Corporation | Piperidine derivatives useful as CCR5 antagonists |
ATE275141T1 (de) * | 1999-10-13 | 2004-09-15 | Banyu Pharma Co Ltd | Substituierte imidazolin-derivate |
AU7788500A (en) * | 1999-10-25 | 2001-05-08 | Janssen Pharmaceutica N.V. | Use of substance p antagonists for influencing the circadian timing system |
BR0111878A (pt) | 2000-06-30 | 2005-05-24 | Bristol Myers Squibb Co | N-ureido-(heterociclo-alquil)-piperidinas como moduladores da atividade de receptores de quimiocinas |
US6642226B2 (en) * | 2001-02-06 | 2003-11-04 | Hoffman-La Roche Inc. | Substituted phenyl-piperidine methanone compounds |
AR033452A1 (es) | 2001-03-29 | 2003-12-17 | Schering Corp | Antagonistas de ccr5 utiles para el tratamiento del sida |
GB0108876D0 (en) * | 2001-04-09 | 2001-05-30 | Novartis Ag | Organic Compounds |
CA2444595A1 (en) * | 2001-04-20 | 2002-10-31 | Banyu Pharmaceutical Co., Ltd. | Benzimidazolone derivatives |
JP3857270B2 (ja) | 2001-07-02 | 2006-12-13 | アストラゼネカ・アクチエボラーグ | ケモカイン受容体活性のモジュレーターとして有用なピペリジン誘導体 |
GB0120461D0 (en) | 2001-08-22 | 2001-10-17 | Astrazeneca Ab | Novel compounds |
AR036366A1 (es) | 2001-08-29 | 2004-09-01 | Schering Corp | Derivados de piperidina utiles como antagonistas de ccr5, composiciones farmaceuticas, el uso de dichos derivados para la fabricación de un medicamento y un kit |
GB0122503D0 (en) | 2001-09-18 | 2001-11-07 | Astrazeneca Ab | Chemical compounds |
EP1472222A1 (en) | 2002-02-08 | 2004-11-03 | Glaxo Group Limited | Piperidylcarboxamide derivatives and their use in the treatment of tachykinim-mediated diseases |
GB0203020D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
SE0200844D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
SE0200843D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
TWI283241B (en) * | 2002-05-29 | 2007-07-01 | Tanabe Seiyaku Co | Novel piperidine compound |
RU2294927C2 (ru) * | 2002-05-29 | 2007-03-10 | Танабе Сейяку Ко., Лтд. | Производные пиперидина, способы их получения, фармацевтическая композиция на их основе, их применение и способ лечения |
JP2005532361A (ja) * | 2002-06-17 | 2005-10-27 | メルク エンド カムパニー インコーポレーテッド | 高眼圧症の治療用の眼科用組成物 |
JO2485B1 (en) * | 2002-12-23 | 2009-01-20 | شركة جانسين فارماسوتيكا ان. في | 1-Piperidine-3-Yl-4-Piperidine-4-Yl-Piperazine derivatives substituted and used as quinine antagonists |
SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
SE0302956D0 (sv) * | 2003-11-07 | 2003-11-07 | Astrazeneca Ab | Chemical compounds |
CA2556589A1 (en) * | 2004-02-24 | 2005-09-01 | Bioaxone Therapeutique Inc. | 4-substituted piperidine derivatives |
JO2676B1 (en) | 2004-04-06 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Derivatives of second-aza-spiro- (5,4) -dikan and their use as antihistamines |
JO2527B1 (en) * | 2004-04-06 | 2010-03-17 | شركة جانسين فارماسوتيكا ان. في | Derivatives of second-aza-Spiro- (5,5) -andecan and their use as antihistamines |
CA2589001A1 (en) * | 2004-11-19 | 2006-05-26 | Kissei Pharmaceutical Co., Ltd. | Preventive or therapeutic agent for neuropathic pain |
CN101133064B (zh) * | 2005-03-03 | 2011-02-23 | 詹森药业有限公司 | 取代的氧杂-二氮杂-螺-[5.5]-十一烷酮衍生物及其作为神经激肽拮抗剂的应用 |
ATE478075T1 (de) | 2005-03-08 | 2010-09-15 | Janssen Pharmaceutica Nv | Diazaspiro-ä4,4ü-nonanderivate als neurokinin- (nk1)-antagonisten |
AU2006270548A1 (en) | 2005-07-21 | 2007-01-25 | Astrazeneca Ab | Novel piperidine derivatives |
AU2007254232A1 (en) | 2006-05-19 | 2007-11-29 | Wyeth | N-benzoyl-and N-benzylpyrrolidin-3-ylamines as histamine-3 antagonists |
AU2008208920A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or R(-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an NK1 |
PL2379525T3 (pl) * | 2008-12-19 | 2016-01-29 | Centrexion Therapeutics Corp | Cykliczne pirymidyno-4-karboksamidy jako antagoniści receptora CCR2 do leczenia stanów zapalnych, astmy oraz COPD |
CA2753205A1 (en) * | 2009-02-19 | 2010-08-26 | Vanderbilt University | Amidobipiperidinecarboxylate m1 allosteric agonists, analogs and derivatives thereof, and methods of making and using same |
PE20121614A1 (es) | 2009-12-17 | 2012-12-21 | Boehringer Ingelheim Int | Derivados de 6-amino,4-carbonil-pirimidina sustituida como antagonistas del receptor ccr2 |
ES2561674T3 (es) | 2010-03-23 | 2016-02-29 | Glaxosmithkline Llc | Antagonistas de TRPV4 |
US10857157B2 (en) | 2015-01-26 | 2020-12-08 | BioAxone BioSciences, Inc. | Treatment of cerebral cavernous malformations and cerebral aneurysms with rho kinase inhibitors |
US10106525B2 (en) | 2015-01-26 | 2018-10-23 | BioAxone BioSciences, Inc. | Rho kinase inhibitor BA-1049 (R) and active metabolites thereof |
US10149856B2 (en) | 2015-01-26 | 2018-12-11 | BioAxone BioSciences, Inc. | Treatment of cerebral cavernous malformations and cerebral aneurysms with rho kinase inhibitors |
CA2990460C (en) | 2015-07-02 | 2023-10-17 | Centrexion Therapeutics Corporation | (4-((3r,4r)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2r,6s)-6-(p-tolyl)tetrahydro-2h-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate |
US11198680B2 (en) | 2016-12-21 | 2021-12-14 | BioAxone BioSciences, Inc. | Rho kinase inhibitor BA-1049 (R) and active metabolites thereof |
US10537567B2 (en) | 2017-07-11 | 2020-01-21 | BioAxone BioSciences, Inc. | Kinase inhibitors for treatment of disease |
JP7393348B2 (ja) | 2018-01-30 | 2023-12-06 | インサイト・コーポレイション | (1-(3-フルオロ-2(トリフルオロメチル)イソニコチニル)ピぺリジン―4-オン)を作製するためのプロセス及び中間体 |
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US4588722A (en) * | 1984-01-09 | 1986-05-13 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives |
MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
WO1993014083A1 (en) * | 1992-01-09 | 1993-07-22 | Janssen Pharmaceutica N.V. | Pharmaceutically active substituted benzimidazole derivatives |
WO1996002503A1 (fr) | 1994-07-15 | 1996-02-01 | Meiji Seika Kabushiki Kaisha | Nouveaux composes ayant un effet inhibant l'agregation plaquettaire |
PT783490E (pt) | 1994-09-30 | 2002-06-28 | Novartis Erfind Verwalt Gmbh | Compostos de 1-acil-4-alifatilaminopiperidina |
NZ321575A (en) | 1995-10-30 | 1999-05-28 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4- substituted piperazine derivatives |
TW429256B (en) * | 1995-12-27 | 2001-04-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-(benzimidazolyl- and imidazopyridinyl)-piperidine derivatives |
TW531537B (en) | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
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1996
- 1996-12-13 TW TW085115391A patent/TW531537B/zh not_active IP Right Cessation
- 1996-12-20 AU AU13084/97A patent/AU707037B2/en not_active Ceased
- 1996-12-20 BR BR9612334A patent/BR9612334A/pt not_active IP Right Cessation
- 1996-12-20 DE DE69615700T patent/DE69615700T2/de not_active Expired - Lifetime
- 1996-12-20 EP EP96944691A patent/EP0855999B1/en not_active Expired - Lifetime
- 1996-12-20 PT PT96944691T patent/PT855999E/pt unknown
- 1996-12-20 HU HU9904125A patent/HU228128B1/hu not_active IP Right Cessation
- 1996-12-20 CZ CZ0186498A patent/CZ296316B6/cs not_active IP Right Cessation
- 1996-12-20 NZ NZ325843A patent/NZ325843A/xx not_active IP Right Cessation
- 1996-12-20 SK SK831-98A patent/SK283555B6/sk unknown
- 1996-12-20 WO PCT/EP1996/005883 patent/WO1997024324A1/en active IP Right Grant
- 1996-12-20 KR KR1019980704831A patent/KR100493574B1/ko not_active Expired - Fee Related
- 1996-12-20 ES ES96944691T patent/ES2164939T3/es not_active Expired - Lifetime
- 1996-12-20 SI SI9630359T patent/SI0855999T1/xx unknown
- 1996-12-20 CN CN96199389A patent/CN1131854C/zh not_active Expired - Fee Related
- 1996-12-20 CA CA002238818A patent/CA2238818C/en not_active Expired - Fee Related
- 1996-12-20 AT AT96944691T patent/ATE206397T1/de active
- 1996-12-20 PL PL327441A patent/PL192397B1/pl unknown
- 1996-12-20 IL IL12464096A patent/IL124640A/en not_active IP Right Cessation
- 1996-12-20 TR TR1998/01211T patent/TR199801211T2/xx unknown
- 1996-12-20 DK DK96944691T patent/DK0855999T3/da active
- 1996-12-20 EA EA199800604A patent/EA001559B1/ru not_active IP Right Cessation
- 1996-12-20 JP JP52403197A patent/JP4039691B2/ja not_active Expired - Fee Related
- 1996-12-23 ZA ZA9610885A patent/ZA9610885B/xx unknown
- 1996-12-26 AR ARP960105894A patent/AR005277A1/es unknown
- 1996-12-26 MY MYPI96005482A patent/MY117557A/en unknown
-
1998
- 1998-05-27 NO NO19982404A patent/NO310913B1/no not_active IP Right Cessation
- 1998-06-22 US US09/102,295 patent/US6169097B1/en not_active Expired - Lifetime
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2000
- 2000-07-13 US US09/615,523 patent/US6346540B1/en not_active Expired - Lifetime
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