ZA200504068B - 3-amino-piperidine derivatives and processes for their preparation - Google Patents
3-amino-piperidine derivatives and processes for their preparation Download PDFInfo
- Publication number
- ZA200504068B ZA200504068B ZA200504068A ZA200504068A ZA200504068B ZA 200504068 B ZA200504068 B ZA 200504068B ZA 200504068 A ZA200504068 A ZA 200504068A ZA 200504068 A ZA200504068 A ZA 200504068A ZA 200504068 B ZA200504068 B ZA 200504068B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- trifluoromethyl
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title description 4
- PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical class NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 190
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- -1 carboxy, cyano, amino Chemical group 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000003282 alkyl amino group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004442 acylamino group Chemical group 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 229910052684 Cerium Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 229910052792 caesium Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 102200031660 rs730880032 Human genes 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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- 239000001301 oxygen Chemical group 0.000 claims description 2
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- 102200012961 rs121918637 Human genes 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 37
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- DLFJXQQHTNEUJP-UHFFFAOYSA-N methyl 4-methyl-3-oxopiperidine-1-carboxylate Chemical compound COC(=O)N1CCC(C)C(=O)C1 DLFJXQQHTNEUJP-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
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- OJISLPGKEOEVDQ-UHFFFAOYSA-N methyl 4-methyl-3-(methylamino)piperidine-1-carboxylate Chemical compound CNC1CN(C(=O)OC)CCC1C OJISLPGKEOEVDQ-UHFFFAOYSA-N 0.000 description 3
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- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
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- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
Classifications
-
- 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
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
-
- 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
- A61K31/4462—Non condensed piperidines, e.g. piperocaine only substituted in position 3
-
- 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
- C07D211/36—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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D211/36—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
- C07D211/56—Nitrogen atoms
-
- 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
- C07D211/68—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
- C07D211/72—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 hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42832402P | 2002-11-21 | 2002-11-21 |
Publications (1)
Publication Number | Publication Date |
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ZA200504068B true ZA200504068B (en) | 2006-08-30 |
Family
ID=32326635
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200504068A ZA200504068B (en) | 2002-11-21 | 2005-05-19 | 3-amino-piperidine derivatives and processes for their preparation |
Country Status (14)
Country | Link |
---|---|
US (1) | US7084277B2 (ko) |
EP (1) | EP1572649A2 (ko) |
JP (1) | JP2006508976A (ko) |
KR (2) | KR100742012B1 (ko) |
CN (2) | CN1726192A (ko) |
AU (1) | AU2003278529A1 (ko) |
BR (1) | BR0316470A (ko) |
CA (1) | CA2506016C (ko) |
MX (1) | MXPA05005403A (ko) |
PL (1) | PL377791A1 (ko) |
RS (1) | RS20050380A (ko) |
RU (2) | RU2309147C9 (ko) |
WO (1) | WO2004046112A2 (ko) |
ZA (1) | ZA200504068B (ko) |
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PT1382339E (pt) | 1999-12-10 | 2008-02-06 | Pfizer Prod Inc | Composições que contêm derivados de pirrolo[2,3-d]- pirimidina |
TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
CN1678321A (zh) | 2002-07-29 | 2005-10-05 | 里格尔药品股份有限公司 | 用2,4-嘧啶二胺化合物治疗或者预防自体免疫性疾病的方法 |
BRPI0413018B8 (pt) | 2003-07-30 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, e, uso de um composto |
MXPA06012663A (es) * | 2004-05-03 | 2007-01-16 | Novartis Ag | Combinaciones que comprenden un agonista del receptor s1p y un inhibidor de quinasa jak3. |
KR101312225B1 (ko) | 2005-06-08 | 2013-09-26 | 리겔 파마슈티칼스, 인크. | Jak 경로의 억제를 위한 조성물 및 방법 |
US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
NZ565363A (en) | 2005-07-29 | 2010-03-26 | Pfizer Prod Inc | Pyrrolo[2,3-D]pyrimidine derivatives; their intermediates and synthesis |
EP1991532B1 (en) | 2006-02-24 | 2017-01-11 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
US8193197B2 (en) | 2006-10-19 | 2012-06-05 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
MX2010008926A (es) | 2008-02-15 | 2011-02-23 | Rigel Pharmaceuticals Inc | Compuestos de pirimidin-2-amina y su uso como inhibidores de jak cinasas. |
EA019973B1 (ru) | 2008-04-16 | 2014-07-30 | Портола Фармасьютиклз, Инк. | ИНГИБИТОРЫ Syk ПРОТЕИНКИНАЗ |
US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
CN102066338A (zh) | 2008-04-22 | 2011-05-18 | 波托拉医药品公司 | 蛋白激酶抑制剂 |
CN101565397B (zh) * | 2009-04-07 | 2011-08-10 | 浙江医药股份有限公司新昌制药厂 | N-Boc-3-氨基哌啶及其光学异构体的合成方法 |
ES2552805T3 (es) * | 2009-04-20 | 2015-12-02 | Auspex Pharmaceuticals, Llc | Inhibidores piperidínicos de la cinasa Janus 3 |
IN2012DN02577A (ko) | 2009-10-15 | 2015-08-28 | Pfizer | |
RU2641648C1 (ru) * | 2009-12-04 | 2018-01-19 | Суновион Фармасьютикалз, Инк. | Полициклические соединения и способы их применения |
JP5739446B2 (ja) | 2009-12-18 | 2015-06-24 | ファイザー・インク | ピロロ[2,3−d]ピリミジン化合物 |
CN102822177A (zh) | 2010-02-05 | 2012-12-12 | 美国辉瑞有限公司 | 吡咯并[2,3-d]嘧啶脲化合物 |
US9102625B2 (en) | 2010-11-01 | 2015-08-11 | Portola Pharmaceuticals, Inc. | Nicotinamides as JAK kinase modulators |
IN2014CN04065A (ko) | 2011-11-23 | 2015-09-04 | Portola Pharm Inc | |
CN104837817B (zh) | 2012-07-25 | 2017-03-22 | 力奇制药公司 | 制备3‑氨基‑哌啶化合物的合成路线 |
RU2499793C1 (ru) * | 2012-08-24 | 2013-11-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) | Способ получения третичных аминов |
US9676756B2 (en) | 2012-10-08 | 2017-06-13 | Portola Pharmaceuticals, Inc. | Substituted pyrimidinyl kinase inhibitors |
EP2935216B1 (en) | 2012-12-17 | 2018-06-27 | Sun Pharmaceutical Industries Limited | Process for the preparation of tofacitinib and intermediates thereof |
ES2713052T3 (es) | 2013-02-22 | 2019-05-17 | Pfizer | Combinación de derivados de pirrolo[2,3-d]pirimidina con uno o más agentes adicionales como inhibidores de janus cinasas (JAK) |
PT3077395T (pt) | 2013-12-05 | 2018-01-03 | Pfizer | Pirrolo[2,3-d]pirimidinilo, pirrolo[2,3-b]pirazinilo e pirrolo[2,3-d]piridinilo acrilamidas |
CN103755624B (zh) * | 2014-01-20 | 2018-10-09 | 上海博氏医药科技有限公司 | 一种哌啶衍生物的合成方法 |
ES2750655T3 (es) | 2014-08-12 | 2020-03-26 | Pfizer | Derivados de pirrolo[2,3-d]pirimidina útiles para inhibir la Janus cinasa |
EP3288943B1 (en) | 2015-05-01 | 2022-09-28 | Pfizer Inc. | Pyrrolo[2,3-b]pyrazinyl acrylamides and epoxides thereof as inhibitors of janus kinase |
EP3421455B1 (en) * | 2017-06-29 | 2019-03-27 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of chiral 3-amino-piperidins, useful intermediates for the preparation of tofacitinib |
AU2019222491B2 (en) | 2018-02-16 | 2023-01-12 | Sunovion Pharmaceuticals Inc. | Salts, crystal forms, and production methods thereof |
EP3946606A1 (en) | 2019-03-27 | 2022-02-09 | Insilico Medicine IP Limited | Bicyclic jak inhibitors and uses thereof |
JP2023523569A (ja) | 2020-04-14 | 2023-06-06 | サノビオン ファーマシューティカルズ インク | 神経学的および精神障害の治療方法 |
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BE640616A (ko) * | 1962-12-19 | |||
US3492397A (en) * | 1967-04-07 | 1970-01-27 | Warner Lambert Pharmaceutical | Sustained release dosage in the pellet form and process thereof |
US4060598A (en) * | 1967-06-28 | 1977-11-29 | Boehringer Mannheim G.M.B.H. | Tablets coated with aqueous resin dispersions |
US3538214A (en) * | 1969-04-22 | 1970-11-03 | Merck & Co Inc | Controlled release medicinal tablets |
US4173626A (en) * | 1978-12-11 | 1979-11-06 | Merck & Co., Inc. | Sustained release indomethacin |
JPS59112984A (ja) * | 1982-12-21 | 1984-06-29 | Shionogi & Co Ltd | 1,4−ベンゾジアゼピン誘導体 |
US4725599A (en) * | 1986-09-08 | 1988-02-16 | Pfizer Inc. | Heterocyclic ring fused pyrimidine-4 (3H)-ones as anticoccidial agents |
FR2619111B1 (fr) * | 1987-08-07 | 1991-01-11 | Synthelabo | Derives de (piperidinyl-4)methyl-2 tetrahydro-1,2,3,4 9h-pyrido (3,4-b) indole, leur preparation et leur application en therapeutique |
NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
US5461156A (en) * | 1993-03-31 | 1995-10-24 | Eli Lilly And Company | Stereocontrolled synthesis of cis-bicyclic compounds |
US5559128A (en) * | 1995-04-18 | 1996-09-24 | Merck & Co., Inc. | 3-substituted piperidines promote release of growth hormone |
DE69731658T2 (de) * | 1996-12-02 | 2005-12-01 | Merck Sharp & Dohme Ltd., Hoddesdon | Die verwendung von nk-1 rezeptor antagonisten für die behandlung von bewegungsstörungen |
CA2291734A1 (en) * | 1997-06-27 | 1999-01-07 | Merck Sharp & Dohme Limited | Substituted 3-(benzylamino)piperidine derivatives and their use as therapeutic agents |
MY138335A (en) | 1997-09-15 | 2009-05-29 | Procter & Gamble | Antimicrobial quinolones, their compositions and uses |
JP4030164B2 (ja) * | 1997-12-01 | 2008-01-09 | 株式会社トクヤマ | テトラハイドロピリジン誘導体及びその製造方法 |
PT1382339E (pt) * | 1999-12-10 | 2008-02-06 | Pfizer Prod Inc | Composições que contêm derivados de pirrolo[2,3-d]- pirimidina |
JP2003528072A (ja) * | 2000-03-17 | 2003-09-24 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | マトリックスメタロプロテアーゼおよびTNF−αの阻害剤としての環状β−アミノ酸誘導体 |
MY145722A (en) * | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
JP3771128B2 (ja) * | 2000-12-28 | 2006-04-26 | 独立行政法人科学技術振興機構 | フェブリフジンおよびフェブリフジン化合物の新規合成方法 |
US6992082B2 (en) * | 2001-01-19 | 2006-01-31 | Cytokinetics, Inc. | Phenothiazine kinesin inhibitors |
-
2003
- 2003-11-10 MX MXPA05005403A patent/MXPA05005403A/es active IP Right Grant
- 2003-11-10 CA CA002506016A patent/CA2506016C/en not_active Expired - Fee Related
- 2003-11-10 AU AU2003278529A patent/AU2003278529A1/en not_active Abandoned
- 2003-11-10 KR KR1020067021730A patent/KR100742012B1/ko not_active IP Right Cessation
- 2003-11-10 WO PCT/IB2003/005151 patent/WO2004046112A2/en active Application Filing
- 2003-11-10 EP EP03769829A patent/EP1572649A2/en not_active Withdrawn
- 2003-11-10 RU RU2005115500/04A patent/RU2309147C9/ru active
- 2003-11-10 KR KR1020057009058A patent/KR100678800B1/ko not_active IP Right Cessation
- 2003-11-10 CN CNA2003801062274A patent/CN1726192A/zh active Pending
- 2003-11-10 BR BR0316470-5A patent/BR0316470A/pt not_active IP Right Cessation
- 2003-11-10 RS YUP-2005/0380A patent/RS20050380A/sr unknown
- 2003-11-10 CN CNA2008101292567A patent/CN101353321A/zh active Pending
- 2003-11-10 PL PL377791A patent/PL377791A1/pl not_active Application Discontinuation
- 2003-11-10 JP JP2004553003A patent/JP2006508976A/ja not_active Withdrawn
- 2003-11-20 US US10/717,958 patent/US7084277B2/en not_active Expired - Fee Related
-
2005
- 2005-05-19 ZA ZA200504068A patent/ZA200504068B/en unknown
-
2007
- 2007-04-28 RU RU2007116248/04A patent/RU2007116248A/ru not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
US7084277B2 (en) | 2006-08-01 |
US20040102627A1 (en) | 2004-05-27 |
WO2004046112A3 (en) | 2004-08-05 |
CN101353321A (zh) | 2009-01-28 |
EP1572649A2 (en) | 2005-09-14 |
RU2005115500A (ru) | 2006-01-20 |
KR100678800B1 (ko) | 2007-02-05 |
CA2506016C (en) | 2009-03-17 |
RU2309147C9 (ru) | 2008-03-20 |
RU2309147C2 (ru) | 2007-10-27 |
CN1726192A (zh) | 2006-01-25 |
BR0316470A (pt) | 2005-10-11 |
JP2006508976A (ja) | 2006-03-16 |
RS20050380A (en) | 2007-11-15 |
KR100742012B1 (ko) | 2007-07-23 |
KR20050083905A (ko) | 2005-08-26 |
MXPA05005403A (es) | 2005-08-03 |
PL377791A1 (pl) | 2006-02-20 |
KR20060116873A (ko) | 2006-11-15 |
CA2506016A1 (en) | 2004-06-03 |
AU2003278529A1 (en) | 2004-06-15 |
RU2007116248A (ru) | 2008-11-10 |
WO2004046112A2 (en) | 2004-06-03 |
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