JP4469280B2 - ムスカリン性アゴニスト - Google Patents
ムスカリン性アゴニスト Download PDFInfo
- Publication number
- JP4469280B2 JP4469280B2 JP2004530846A JP2004530846A JP4469280B2 JP 4469280 B2 JP4469280 B2 JP 4469280B2 JP 2004530846 A JP2004530846 A JP 2004530846A JP 2004530846 A JP2004530846 A JP 2004530846A JP 4469280 B2 JP4469280 B2 JP 4469280B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorobenzyl
- carboxylic acid
- hydroxyindan
- methylamino
- ethylideneamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 C*C(C)C*C1=CCC(C)(C[C@@]([C@@]2NC(c(cc3)ccc3-c3ccccc3)=O)O)C2=C1 Chemical compound C*C(C)C*C1=CCC(C)(C[C@@]([C@@]2NC(c(cc3)ccc3-c3ccccc3)=O)O)C2=C1 0.000 description 1
- JTTOKZIZNXDTFA-UHFFFAOYSA-N CNCC(C=C1)=CCC1F Chemical compound CNCC(C=C1)=CCC1F JTTOKZIZNXDTFA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド
1H NMR(CDCl3):δ 7.90(d, 2, J=8.6)、7.69(d, 2, J=8.6)、7.63(d, 2, J=8.2)、7.48(t, 2, J=8.2, 7.6)、7.41(d, 1, J=7.3)、7.24(dd, 2, J=8.5, 5.2)、7.14(d, 1, J=7.9)、7.04(t, 2, J=8.7)、6.72−6.63(m, 3)、5.31(t, 1, J=5.6)、4.84(br s, 1)、4.64(dd, 2, J=21.4, 15.6)、4.54(dd, 1, J=14.0, 7.9)、3.32(dd, 1, J=15.6, 7.9)、3.01(s, 3)、2.95(dd, 1, J=15.7, 8.0)、1.97(s, 3)。MS(m/z):508.2(M+1)
ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物
メタノール21.8Lを、ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド アセトニトリル溶媒和物2.86kgに加えた。溶液を添着炭フィルターに通し、ろ液をメタノール24Lですすいだ。溶液に水5.7kgを35分間かけて添加し、次にビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物の種結晶15gを添加した。20分後、水1.15kgを添加し、次に種結晶15gを添加した。1時間後、さらに水1.15kgを30分間かけて添加し、その後種結晶15gを添加した。10分後、水3.4kgを1時間かけて添加し、スラリーを室温で1時間撹拌し、0℃で45分間撹拌した。ろ過して固体を集め、メタノール11.4Lおよび水2.9Lの冷溶液ですすぎ、乾燥し、白色固体として標記化合物2.19kgを得た。
ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物
メタノール(24 mL)中にビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド アセトニトリル溶媒和物(2.0g)を20〜23℃で溶解した。さらに水(5 mL)を溶液に添加し、次に半水和物の種結晶(20 mg)を添加した。混合液を20〜23℃で2時間撹拌し、0〜5℃に冷却した。混合液をろ過し、メタノール(8 mL)と水(2 mL)の溶液で洗浄し、真空下にて50〜60℃で16時間乾燥し、標記化合物1.66gを得た。
ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物
6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2−ヒドロキシ−1−ビフェニルアミノインダンアセトニトリル溶媒和物(101g)とメタノール(1.2L)の溶液にDarco G−60(5g)を混合した。15〜25℃で15〜30分撹拌後、混合液をろ過し、ろ過した固形物をメタノール(0.4L)ですすいだ。混合したろ液に水(0.4L)を添加し、すすぎ、半水和物の種結晶(1.5g)を添加した。混合液を15〜25℃で2〜3時間撹拌し、その後0〜5℃に冷却してさらに90分撹拌した。混合液をろ過し、メタノール(0.8L)と水(0.2L)の溶液(0〜5℃)で洗浄し、真空下にて47〜53℃で20分間乾燥し、標記化合物88.7gを得た。
Claims (4)
- 5.2および6.2(±0.1°2θ)のピークを含むX線粉末回析パターンにより特徴付けられる、結晶性ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物。
- 15.6および18.8(±0.1°2θ)のピークを含むX線粉末回析パターンにより特徴付けられる、結晶性ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物。
- 5.2、6.2、12.6、15.6、18.8および20.0(±0.1°2θ)のピークを含むX線粉末回析パターンにより特徴付けられる、結晶性ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物。
- 5.2、6.2、12.6、14.0、15.6、17.0、18.8、19.6、20.0および22.6(±0.1°2θ)のピークを含むX線粉末回析パターンにより特徴付けられる、結晶性ビフェニル−4−カルボン酸(R)−(6−(1−((4−フルオロベンジル)メチルアミノ)エチリデンアミノ)−2(R)−ヒドロキシインダン−1−イル)アミド半水和物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40544302P | 2002-08-22 | 2002-08-22 | |
PCT/US2003/023260 WO2004018411A1 (en) | 2002-08-22 | 2003-08-12 | Muscarinic agonists |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005536549A JP2005536549A (ja) | 2005-12-02 |
JP2005536549A5 JP2005536549A5 (ja) | 2006-09-28 |
JP4469280B2 true JP4469280B2 (ja) | 2010-05-26 |
Family
ID=31946873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004530846A Expired - Fee Related JP4469280B2 (ja) | 2002-08-22 | 2003-08-12 | ムスカリン性アゴニスト |
Country Status (19)
Country | Link |
---|---|
US (1) | US7160922B2 (ja) |
EP (1) | EP1534667B1 (ja) |
JP (1) | JP4469280B2 (ja) |
CN (1) | CN100554247C (ja) |
AR (1) | AR040889A1 (ja) |
AT (1) | ATE491683T1 (ja) |
AU (1) | AU2003256791B2 (ja) |
BR (1) | BR0313161A (ja) |
CA (1) | CA2493958C (ja) |
CY (1) | CY1111115T1 (ja) |
DE (1) | DE60335380D1 (ja) |
DK (1) | DK1534667T3 (ja) |
ES (1) | ES2355213T3 (ja) |
MX (1) | MXPA05002080A (ja) |
PE (1) | PE20040894A1 (ja) |
PT (1) | PT1534667E (ja) |
SI (1) | SI1534667T1 (ja) |
TW (1) | TW200410922A (ja) |
WO (1) | WO2004018411A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2275095A3 (en) * | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
US20130029846A1 (en) | 2010-03-29 | 2013-01-31 | Basf Se | Fungicidal Iminoderivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20040053130A (ko) * | 2001-09-21 | 2004-06-23 | 일라이 릴리 앤드 캄파니 | 무스카린성 효능제 |
-
2003
- 2003-08-12 CN CNB038192500A patent/CN100554247C/zh not_active Expired - Fee Related
- 2003-08-12 AT AT03792989T patent/ATE491683T1/de active
- 2003-08-12 SI SI200331933T patent/SI1534667T1/sl unknown
- 2003-08-12 EP EP03792989A patent/EP1534667B1/en not_active Expired - Lifetime
- 2003-08-12 CA CA2493958A patent/CA2493958C/en not_active Expired - Fee Related
- 2003-08-12 DK DK03792989.0T patent/DK1534667T3/da active
- 2003-08-12 US US10/524,960 patent/US7160922B2/en not_active Expired - Fee Related
- 2003-08-12 DE DE60335380T patent/DE60335380D1/de not_active Expired - Lifetime
- 2003-08-12 AU AU2003256791A patent/AU2003256791B2/en not_active Ceased
- 2003-08-12 MX MXPA05002080A patent/MXPA05002080A/es active IP Right Grant
- 2003-08-12 BR BR0313161-0A patent/BR0313161A/pt not_active IP Right Cessation
- 2003-08-12 PT PT03792989T patent/PT1534667E/pt unknown
- 2003-08-12 JP JP2004530846A patent/JP4469280B2/ja not_active Expired - Fee Related
- 2003-08-12 ES ES03792989T patent/ES2355213T3/es not_active Expired - Lifetime
- 2003-08-12 WO PCT/US2003/023260 patent/WO2004018411A1/en active Application Filing
- 2003-08-20 AR AR20030103011A patent/AR040889A1/es unknown
- 2003-08-20 TW TW092122893A patent/TW200410922A/zh unknown
- 2003-08-21 PE PE2003000851A patent/PE20040894A1/es not_active Application Discontinuation
-
2011
- 2011-01-19 CY CY20111100057T patent/CY1111115T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
AU2003256791A1 (en) | 2004-03-11 |
US20060122280A1 (en) | 2006-06-08 |
DE60335380D1 (de) | 2011-01-27 |
CN100554247C (zh) | 2009-10-28 |
WO2004018411A1 (en) | 2004-03-04 |
CA2493958C (en) | 2010-11-09 |
SI1534667T1 (sl) | 2011-02-28 |
CY1111115T1 (el) | 2015-06-11 |
MXPA05002080A (es) | 2005-08-18 |
ES2355213T3 (es) | 2011-03-23 |
EP1534667A1 (en) | 2005-06-01 |
EP1534667B1 (en) | 2010-12-15 |
CA2493958A1 (en) | 2004-03-04 |
TW200410922A (en) | 2004-07-01 |
AR040889A1 (es) | 2005-04-20 |
JP2005536549A (ja) | 2005-12-02 |
PE20040894A1 (es) | 2004-11-25 |
DK1534667T3 (da) | 2011-02-14 |
US7160922B2 (en) | 2007-01-09 |
CN1675173A (zh) | 2005-09-28 |
PT1534667E (pt) | 2011-01-19 |
ATE491683T1 (de) | 2011-01-15 |
BR0313161A (pt) | 2005-06-14 |
AU2003256791B2 (en) | 2008-12-11 |
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