OA12070A - Bicyclic amino acids as pharmaceutical agents. - Google Patents

Bicyclic amino acids as pharmaceutical agents. Download PDF

Info

Publication number: OA12070A
Authority: OA; OAPI
Prior art keywords: acetic acid; aminomethyl; bicyclo; decahydro; octahydro
Prior art date: 1999-10-20

Application number

OA1200200117A

Other languages

English (en)

French (fr)

Inventor

Justin Stephen Bryans

David Clive Blakemore

Simon Osborne

Jean-Marie Receveur

Original Assignee

Warner Lambert Co

Priority date (The priority date 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 date listed.)

1999-10-20

Filing date

2000-10-17

Publication date

2003-11-10

2000-10-17 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2003-11-10 Publication of OA12070A publication Critical patent/OA12070A/en

Links

-1 Bicyclic amino acids Chemical class 0.000 title claims description 85
239000008177 pharmaceutical agent Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 84
206010015037 epilepsy Diseases 0.000 claims abstract description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 219
229960000583 acetic acid Drugs 0.000 claims description 189
239000000203 mixture Substances 0.000 claims description 89
239000003814 drug Substances 0.000 claims description 33
229940079593 drug Drugs 0.000 claims description 32
208000002193 Pain Diseases 0.000 claims description 24
230000036407 pain Effects 0.000 claims description 20
235000011054 acetic acid Nutrition 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
239000000651 prodrug Substances 0.000 claims description 12
229940002612 prodrug Drugs 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 10
208000019901 Anxiety disease Diseases 0.000 claims description 7
230000036506 anxiety Effects 0.000 claims description 7
ONKWZNBXHSMMDK-UHFFFAOYSA-N 2-[2-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroinden-2-yl]acetic acid Chemical compound C1CCCC2CC(CN)(CC(O)=O)CC21 ONKWZNBXHSMMDK-UHFFFAOYSA-N 0.000 claims description 6
208000006083 Hypokinesia Diseases 0.000 claims description 4
208000002173 dizziness Diseases 0.000 claims description 4
230000003483 hypokinetic effect Effects 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
230000002981 neuropathic effect Effects 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 9
238000004519 manufacturing process Methods 0.000 claims 9
GSBZRDSCOPXLJJ-UHFFFAOYSA-N 2-[2-(aminomethyl)-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-yl]acetic acid Chemical compound C1CCC2CC(CN)(CC(O)=O)CC21 GSBZRDSCOPXLJJ-UHFFFAOYSA-N 0.000 claims 4
JKONURJHZJCUAD-UHFFFAOYSA-N 2-[2-(aminomethyl)-3,3a,4,5,6,7,8,8a-octahydro-1h-azulen-2-yl]acetic acid Chemical compound C1CCCCC2CC(CN)(CC(O)=O)CC21 JKONURJHZJCUAD-UHFFFAOYSA-N 0.000 claims 4
HZROAXDCVPLQAB-UHFFFAOYSA-N 2-[3-(aminomethyl)-3-bicyclo[3.1.0]hexanyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC2CC21 HZROAXDCVPLQAB-UHFFFAOYSA-N 0.000 claims 2
NDDZVQRQVFTNSN-UHFFFAOYSA-N 2-[3-(aminomethyl)-3-bicyclo[3.2.0]heptanyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC2CCC21 NDDZVQRQVFTNSN-UHFFFAOYSA-N 0.000 claims 2
208000020401 Depressive disease Diseases 0.000 claims 1
125000004125 inden-2-yl group Chemical group [H]C1=C(*)C([H])([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 10
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 129
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
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239000002904 solvent Substances 0.000 description 62
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
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239000000047 product Substances 0.000 description 46
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 9
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OA1200200117A 1999-10-20 2000-10-17 Bicyclic amino acids as pharmaceutical agents. OA12070A (en)

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US16072599P	1999-10-20	1999-10-20

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OA1200200117A OA12070A (en)	1999-10-20	2000-10-17	Bicyclic amino acids as pharmaceutical agents.

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DE2460891C2 (de)	1974-12-21	1982-09-23	Gödecke AG, 1000 Berlin	1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US4087544A (en) *	1974-12-21	1978-05-02	Warner-Lambert Company	Treatment of cranial dysfunctions using novel cyclic amino acids
HUP0004310A3 (en)	1997-10-27	2001-11-28	Warner Lambert Co	Cyclic amino acids, and derivatives thereof and pharmaceutical compositions comprising the said compounds as active agents

2000
- 2000-10-05 HN HN2000000224A patent/HN2000000224A/es unknown
- 2000-10-06 SV SV2000000188A patent/SV2001000188A/es not_active Application Discontinuation
- 2000-10-17 GE GE4783A patent/GEP20043297B/en unknown
- 2000-10-17 DZ DZ003197A patent/DZ3197A1/xx active
- 2000-10-17 TR TR2002/01094T patent/TR200201094T2/xx unknown
- 2000-10-17 SI SI200030670T patent/SI1226110T1/xx unknown
- 2000-10-17 HR HRP20040709 patent/HRP20040709A2/xx not_active Application Discontinuation
- 2000-10-17 JP JP2001531783A patent/JP3632191B2/ja not_active Expired - Fee Related
- 2000-10-17 EA EA200200293A patent/EA005206B1/ru unknown
- 2000-10-17 AP AP2004003186A patent/AP2004003186A0/xx unknown
- 2000-10-17 AU AU10920/01A patent/AU778871B2/en not_active Ceased
- 2000-10-17 CZ CZ20021310A patent/CZ295960B6/cs not_active IP Right Cessation
- 2000-10-17 HU HU0203325A patent/HUP0203325A3/hu unknown
- 2000-10-17 KR KR1020027005036A patent/KR100593349B1/ko not_active Expired - Fee Related
- 2000-10-17 NZ NZ517961A patent/NZ517961A/xx unknown
- 2000-10-17 UA UA2002032434A patent/UA72931C2/uk unknown
- 2000-10-17 KR KR1020067002249A patent/KR100566462B1/ko not_active Expired - Fee Related
- 2000-10-17 CA CA2386297A patent/CA2386297C/en not_active Expired - Fee Related
- 2000-10-17 SK SK523-2002A patent/SK5232002A3/sk unknown
- 2000-10-17 EE EEP200200211A patent/EE200200211A/xx unknown
- 2000-10-17 HK HK03101868.4A patent/HK1049826B/zh not_active IP Right Cessation
- 2000-10-17 WO PCT/US2000/028687 patent/WO2001028978A1/en not_active Ceased
- 2000-10-17 IL IL14914300A patent/IL149143A0/xx not_active IP Right Cessation
- 2000-10-17 AT AT04027485T patent/ATE358116T1/de not_active IP Right Cessation
- 2000-10-17 US US10/130,023 patent/US6689906B1/en not_active Expired - Fee Related
- 2000-10-17 TR TR2005/00221T patent/TR200500221T2/xx unknown
- 2000-10-17 CN CNB008145644A patent/CN1165518C/zh not_active Expired - Fee Related
- 2000-10-17 YU YU73004A patent/YU73004A/sh unknown
- 2000-10-17 DE DE60034157T patent/DE60034157T2/de not_active Expired - Lifetime
- 2000-10-17 MX MXPA02003229A patent/MXPA02003229A/es active IP Right Grant
- 2000-10-17 EP EP04027485A patent/EP1506955B1/en not_active Expired - Lifetime
- 2000-10-17 PL PL00354607A patent/PL354607A1/xx not_active Application Discontinuation
- 2000-10-17 ES ES00972226T patent/ES2237464T3/es not_active Expired - Lifetime
- 2000-10-17 BR BRPI0014972-1A patent/BR0014972B1/pt not_active IP Right Cessation
- 2000-10-17 AT AT00972226T patent/ATE293590T1/de not_active IP Right Cessation
- 2000-10-17 YU YU29302A patent/YU29302A/sh unknown
- 2000-10-17 AP APAP/P/2002/002517A patent/AP2002002517A0/en unknown
- 2000-10-17 DE DE60019628T patent/DE60019628T2/de not_active Expired - Lifetime
- 2000-10-17 OA OA1200200117A patent/OA12070A/en unknown
- 2000-10-17 EP EP00972226A patent/EP1226110B1/en not_active Expired - Lifetime
- 2000-10-17 HR HR20020428A patent/HRP20020428B1/xx not_active IP Right Cessation
- 2000-10-17 PT PT00972226T patent/PT1226110E/pt unknown
- 2000-10-17 ES ES04027485T patent/ES2282785T3/es not_active Expired - Lifetime
- 2000-10-17 IL IL16406000A patent/IL164060A0/xx unknown
- 2000-10-18 MY MYPI20004896A patent/MY127678A/en unknown
- 2000-10-18 PA PA20008505201A patent/PA8505201A1/es unknown
- 2000-10-19 GT GT200000183AK patent/GT200000183AA/es unknown
- 2000-10-19 CO CO00079741A patent/CO5280060A1/es not_active Application Discontinuation
- 2000-10-19 DO DO2000000083A patent/DOP2000000083A/es unknown
- 2000-10-19 PE PE2000001116A patent/PE20010740A1/es not_active Application Discontinuation
- 2000-10-19 AR ARP000105497A patent/AR026087A1/es unknown
- 2000-10-19 GT GT200000183A patent/GT200000183A/es unknown
- 2000-10-20 TW TW089122115A patent/TWI225855B/zh not_active IP Right Cessation
- 2000-10-20 TW TW093125953A patent/TW200505824A/zh unknown
2002
- 2002-03-28 ZA ZA200202543A patent/ZA200202543B/xx unknown
- 2002-04-15 IL IL149143A patent/IL149143A/en unknown
- 2002-04-16 CU CU78A patent/CU23112A3/es unknown
- 2002-04-16 NO NO20021780A patent/NO20021780D0/no not_active Application Discontinuation
- 2002-04-17 IS IS6348A patent/IS6348A/is unknown
- 2002-04-18 CR CR6620A patent/CR6620A/es not_active Application Discontinuation
- 2002-05-10 MA MA26634A patent/MA26842A1/fr unknown
- 2002-05-20 BG BG108860A patent/BG108860A/en unknown
- 2002-05-20 BG BG106719A patent/BG106719A/bg unknown
2004
- 2004-01-21 US US10/762,026 patent/US6835751B2/en not_active Expired - Fee Related
- 2004-07-28 EC EC2004005393A patent/ECSP045393A/es unknown
- 2004-08-17 AR ARP040102937A patent/AR045456A2/es unknown
- 2004-09-01 NO NO20043663A patent/NO20043663L/no not_active Application Discontinuation
- 2004-09-14 JP JP2004266488A patent/JP3744928B2/ja not_active Expired - Fee Related
- 2004-10-08 IS IS7497A patent/IS7497A/is unknown
2005
- 2005-03-23 AU AU2005201268A patent/AU2005201268A1/en not_active Abandoned

Also Published As

Publication number	Publication date
KR100593349B1 (ko)	2006-06-26
YU73004A (sh)	2005-11-28
ECSP045393A (es)	2004-10-23
ZA200202543B (en)	2003-09-23
MY127678A (en)	2006-12-29
ES2282785T3 (es)	2007-10-16
IS6348A (is)	2002-04-17
CA2386297A1 (en)	2001-04-26
CN1382118A (zh)	2002-11-27
NO20043663L (no)	2002-04-16
JP2003512348A (ja)	2003-04-02
CZ295960B6 (cs)	2005-12-14
DE60019628D1 (de)	2005-05-25
SI1226110T1 (en)	2005-08-31
KR20060013701A (ko)	2006-02-13
JP3744928B2 (ja)	2006-02-15
TR200500221T2 (tr)	2005-03-21
IL164060A0 (en)	2005-12-18
EA200200293A1 (ru)	2002-10-31
US6689906B1 (en)	2004-02-10
BG108860A (en)	2006-03-31
HUP0203325A2 (hu)	2003-02-28
CN1165518C (zh)	2004-09-08
ATE293590T1 (de)	2005-05-15
PA8505201A1 (es)	2002-08-29
AU778871B2 (en)	2004-12-23
CA2386297C (en)	2010-02-09
HK1049826B (zh)	2005-02-25
HK1049826A1 (en)	2003-05-30
MA26842A1 (fr)	2004-12-20
AP2004003186A0 (en)	2004-12-31
JP3632191B2 (ja)	2005-03-23
EP1506955A1 (en)	2005-02-16
DE60019628T2 (de)	2006-01-19
KR20020040900A (ko)	2002-05-30
HN2000000224A (es)	2001-04-11
HRP20020428A2 (en)	2005-02-28
DE60034157T2 (de)	2007-12-13
EP1506955B1 (en)	2007-03-28
NO20021780L (no)	2002-04-16
DE60034157D1 (de)	2007-05-10
NO20021780D0 (no)	2002-04-16
CU23112A3 (es)	2006-02-27
EP1226110B1 (en)	2005-04-20
TR200201094T2 (tr)	2002-09-23
CR6620A (es)	2004-02-02
AU2005201268A1 (en)	2005-04-21
UA72931C2 (uk)	2005-05-16
BR0014972B1 (pt)	2011-09-06
SK5232002A3 (en)	2003-07-01
MXPA02003229A (es)	2002-09-30
DZ3197A1 (fr)	2001-04-26
AR026087A1 (es)	2002-12-26
EE200200211A (et)	2003-06-16
ES2237464T3 (es)	2005-08-01
IL149143A (en)	2007-02-11
HUP0203325A3 (en)	2003-12-29
BG106719A (bg)	2003-02-28
US20040152779A1 (en)	2004-08-05
PL354607A1 (en)	2004-01-26
JP2005036009A (ja)	2005-02-10
NZ517961A (en)	2002-12-20
IS7497A (is)	2004-10-08
PE20010740A1 (es)	2001-07-27
EA005206B1 (ru)	2004-12-30
IL149143A0 (en)	2002-11-10
GEP20043297B (en)	2004-01-12
GT200000183A (es)	2000-10-19
KR100566462B1 (ko)	2006-03-31
WO2001028978A1 (en)	2001-04-26
AU1092001A (en)	2001-04-30
ATE358116T1 (de)	2007-04-15
BR0014972A (pt)	2002-07-16
AP2002002517A0 (en)	2002-06-30
SV2001000188A (es)	2001-09-07
YU29302A (sh)	2005-06-10
AR045456A2 (es)	2005-10-26
US6835751B2 (en)	2004-12-28
TWI225855B (en)	2005-01-01
PT1226110E (pt)	2005-07-29
HRP20040709A2 (en)	2004-12-31
DOP2000000083A (es)	2002-03-30
CO5280060A1 (es)	2003-05-30
EP1226110A1 (en)	2002-07-31
TW200505824A (en)	2005-02-16
HRP20020428B1 (en)	2006-02-28
CZ20021310A3 (cs)	2003-05-14
GT200000183AA (es)	2005-06-17

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CA2386297C (en)	2010-02-09	Bicyclic amino acids as pharmaceutical agents
US6316638B1 (en)	2001-11-13	Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel
JP2006096758A (ja)	2006-04-13	医薬として有用な環状アミノ酸およびその誘導体
HK1040237B (en)	2004-12-31	Fused polycyclic amino acids as pharmaceutical agents
US20050250800A1 (en)	2005-11-10	Conformationally constrained compounds as pharmaceutical agents
MXPA00009494A (en)	2001-07-09	Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel