SK185399A3 - COMPOSITIONS AND METHODS FOR REDUCING RESPIRATORY DEPRESSION ANDì (54) ATTENDANT SIDE EFFECTS OF MU OPIOID COMPOUNDS - Google Patents

COMPOSITIONS AND METHODS FOR REDUCING RESPIRATORY DEPRESSION ANDì (54) ATTENDANT SIDE EFFECTS OF MU OPIOID COMPOUNDS Download PDF

Info

Publication number: SK185399A3
Authority: SK; Slovakia
Prior art keywords: alkyl; piperazinyl; hydrogen; dimethyl; allyl
Prior art date: 1997-07-03

Application number

SK1853-99A

Other languages

English (en)

Slovak (sk)

Inventor

Kwen-Jen Chang

Robert W Mc-Nutt Jr

Hugh O Pettit

Michael J Bishop

Original Assignee

Delta Pharmaceuticals Inc

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.)

1997-07-03

Filing date

1997-10-01

Publication date

2001-08-06

1997-10-01 Application filed by Delta Pharmaceuticals Inc filed Critical Delta Pharmaceuticals Inc

2001-08-06 Publication of SK185399A3 publication Critical patent/SK185399A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 202
208000004756 Respiratory Insufficiency Diseases 0.000 title claims abstract description 106
206010038678 Respiratory depression Diseases 0.000 title claims abstract description 106
230000000694 effects Effects 0.000 title claims abstract description 66
238000000034 method Methods 0.000 title abstract description 29
239000000203 mixture Substances 0.000 title description 65
239000000841 delta opiate receptor agonist Substances 0.000 claims abstract description 47
239000003814 drug Substances 0.000 claims abstract description 24
IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims abstract description 7
206010028817 Nausea and vomiting symptoms Diseases 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 77
239000001257 hydrogen Substances 0.000 claims description 76
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 56
150000002431 hydrogen Chemical class 0.000 claims description 54
-1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 43
229910052757 nitrogen Inorganic materials 0.000 claims description 43
239000008194 pharmaceutical composition Substances 0.000 claims description 41
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 31
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 31
229910052799 carbon Inorganic materials 0.000 claims description 29
239000000460 chlorine Substances 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 27
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IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 22
108700023159 delta Opioid Receptors Proteins 0.000 claims description 22
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BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 22
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125000003710 aryl alkyl group Chemical group 0.000 claims description 20
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
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125000000172 C5-C10 aryl group Chemical group 0.000 claims description 11
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
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229910052717 sulfur Inorganic materials 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 8
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
150000003457 sulfones Chemical class 0.000 claims description 7
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 claims description 6
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125000003342 alkenyl group Chemical group 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
206010052904 Musculoskeletal stiffness Diseases 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
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OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
238000002347 injection Methods 0.000 claims description 5
239000007924 injection Substances 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
229940005483 opioid analgesics Drugs 0.000 claims description 5
150000003462 sulfoxides Chemical class 0.000 claims description 5
150000003568 thioethers Chemical class 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
229960004126 codeine Drugs 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
239000000863 peptide conjugate Substances 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical compound C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims description 4
229960004739 sufentanil Drugs 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
229940124597 therapeutic agent Drugs 0.000 claims description 4
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 3
206010028813 Nausea Diseases 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000001939 inductive effect Effects 0.000 claims description 3
230000008693 nausea Effects 0.000 claims description 3
229960000482 pethidine Drugs 0.000 claims description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 3
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims 2
GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 2
JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims 2
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 2
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims 2
RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims 2
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IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 claims 2
229960001113 butorphanol Drugs 0.000 claims 2
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims 2
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RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 claims 2
229960000920 dihydrocodeine Drugs 0.000 claims 2
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CAHCBJPUTCKATP-FAWZKKEFSA-N etorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O CAHCBJPUTCKATP-FAWZKKEFSA-N 0.000 claims 2
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210000003205 muscle Anatomy 0.000 claims 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
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VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims 2
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235000011152 sodium sulphate Nutrition 0.000 description 21
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/096—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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SK1853-99A 1997-07-03 1997-10-01 COMPOSITIONS AND METHODS FOR REDUCING RESPIRATORY DEPRESSION ANDì (54) ATTENDANT SIDE EFFECTS OF MU OPIOID COMPOUNDS SK185399A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/887,312 US5985880A (en)	1996-06-05	1997-07-03	Compositions and methods for reducing respiratory depression and attendant side effects of mu opioid compounds
PCT/US1997/017852 WO1999001033A1 (en)	1997-07-03	1997-10-01	Compositions and methods for reducing respiratory depression and attendant side effects of mu opioid compounds

Publications (1)

Publication Number	Publication Date
SK185399A3 true SK185399A3 (en)	2001-08-06

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Application Number	Title	Priority Date	Filing Date
SK1853-99A SK185399A3 (en)	1997-07-03	1997-10-01	COMPOSITIONS AND METHODS FOR REDUCING RESPIRATORY DEPRESSION ANDì (54) ATTENDANT SIDE EFFECTS OF MU OPIOID COMPOUNDS

Country Status (23)

Country	Link
US (5)	US5985880A (no)
EP (1)	EP1003373B1 (no)
JP (1)	JP2002502432A (no)
KR (1)	KR20010014279A (no)
CN (1)	CN1165308C (no)
AT (1)	ATE259226T1 (no)
AU (1)	AU756120B2 (no)
BR (1)	BR9714739A (no)
CA (1)	CA2294924C (no)
CZ (1)	CZ9904694A3 (no)
DE (1)	DE69727593D1 (no)
HU (1)	HUP0003842A3 (no)
IL (1)	IL133600A0 (no)
IS (1)	IS5309A (no)
NO (1)	NO996310L (no)
NZ (1)	NZ501817A (no)
PL (1)	PL337578A1 (no)
RU (1)	RU2201231C2 (no)
SI (1)	SI20245A (no)
SK (1)	SK185399A3 (no)
TR (1)	TR199903324T2 (no)
TW (1)	TW513426B (no)
WO (1)	WO1999001033A1 (no)

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KR102082529B1 (ko) *	2012-04-17	2020-02-27	퍼듀 퍼머 엘피	오피오이드-유도 유해 약역학 반응을 치료하기 위한 시스템 및 방법
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1997
- 1997-07-03 US US08/887,312 patent/US5985880A/en not_active Expired - Fee Related
- 1997-10-01 KR KR1019997012402A patent/KR20010014279A/ko not_active Application Discontinuation
- 1997-10-01 CZ CZ19994694A patent/CZ9904694A3/cs unknown
- 1997-10-01 JP JP50859899A patent/JP2002502432A/ja active Pending
- 1997-10-01 TR TR1999/03324T patent/TR199903324T2/xx unknown
- 1997-10-01 CN CNB971822719A patent/CN1165308C/zh not_active Expired - Fee Related
- 1997-10-01 DE DE69727593T patent/DE69727593D1/de not_active Expired - Lifetime
- 1997-10-01 IL IL13360097A patent/IL133600A0/xx unknown
- 1997-10-01 SI SI9720097A patent/SI20245A/sl not_active IP Right Cessation
- 1997-10-01 AT AT97910777T patent/ATE259226T1/de not_active IP Right Cessation
- 1997-10-01 NZ NZ501817A patent/NZ501817A/en unknown
- 1997-10-01 BR BR9714739-7A patent/BR9714739A/pt not_active Application Discontinuation
- 1997-10-01 CA CA2294924A patent/CA2294924C/en not_active Expired - Fee Related
- 1997-10-01 SK SK1853-99A patent/SK185399A3/sk unknown
- 1997-10-01 EP EP97910777A patent/EP1003373B1/en not_active Expired - Lifetime
- 1997-10-01 RU RU2000100816/14A patent/RU2201231C2/ru not_active IP Right Cessation
- 1997-10-01 HU HU0003842A patent/HUP0003842A3/hu unknown
- 1997-10-01 WO PCT/US1997/017852 patent/WO1999001033A1/en not_active Application Discontinuation
- 1997-10-01 AU AU48066/97A patent/AU756120B2/en not_active Ceased
- 1997-10-01 PL PL97337578A patent/PL337578A1/xx unknown
- 1997-10-24 TW TW086115899A patent/TW513426B/zh not_active IP Right Cessation
1999
- 1999-07-12 US US09/352,308 patent/US6300332B1/en not_active Expired - Fee Related
- 1999-12-17 IS IS5309A patent/IS5309A/is unknown
- 1999-12-17 NO NO996310A patent/NO996310L/no not_active Application Discontinuation
2001
- 2001-10-09 US US09/974,004 patent/US6919350B2/en not_active Expired - Fee Related
2005
- 2005-07-19 US US11/184,762 patent/US20050255151A1/en not_active Abandoned
2008
- 2008-04-07 US US12/098,899 patent/US20080193383A1/en not_active Abandoned

Also Published As

Publication number	Publication date
HUP0003842A1 (hu)	2001-04-28
IL133600A0 (en)	2001-04-30
IS5309A (is)	1999-12-17
NO996310D0 (no)	1999-12-17
US6300332B1 (en)	2001-10-09
US20020111359A1 (en)	2002-08-15
US5985880A (en)	1999-11-16
EP1003373A1 (en)	2000-05-31
US20080193383A1 (en)	2008-08-14
TR199903324T2 (xx)	2000-09-21
EP1003373A4 (en)	2000-09-20
CN1165308C (zh)	2004-09-08
US6919350B2 (en)	2005-07-19
NZ501817A (en)	2002-02-01
EP1003373B1 (en)	2004-02-11
ATE259226T1 (de)	2004-02-15
US20050255151A1 (en)	2005-11-17
RU2201231C2 (ru)	2003-03-27
SI20245A (sl)	2000-12-31
KR20010014279A (ko)	2001-02-26
PL337578A1 (en)	2000-08-28
CA2294924C (en)	2010-12-21
CZ9904694A3 (cs)	2002-03-13
AU756120B2 (en)	2003-01-02
HUP0003842A3 (en)	2001-12-28
BR9714739A (pt)	2000-07-25
CN1262600A (zh)	2000-08-09
DE69727593D1 (de)	2004-03-18
NO996310L (no)	2000-02-22
JP2002502432A (ja)	2002-01-22
CA2294924A1 (en)	1999-01-14
TW513426B (en)	2002-12-11
WO1999001033A1 (en)	1999-01-14
AU4806697A (en)	1999-01-25

Publication	Publication Date	Title
SK185399A3 (en)	2001-08-06	COMPOSITIONS AND METHODS FOR REDUCING RESPIRATORY DEPRESSION ANDì (54) ATTENDANT SIDE EFFECTS OF MU OPIOID COMPOUNDS
EP0938317B1 (en)	2004-03-03	Compositions for reducing respiratory depression
PT711289E (pt)	2001-02-28	Compostos piperazina utilizados em terapia
JP4787148B2 (ja)	2011-10-05	新規アリールピペラジニル化合物
CN105026373A (zh)	2015-11-04	作为钠通道调节剂的吡啶酮酰胺
US6924288B2 (en)	2005-08-02	Enantiomerically pure opioid diarylmethylpiperzine and methods of using same
AU2002341832A1 (en)	2003-06-26	An enantiomerically pure diarylmethylpiperazine and methods of using same
US7189725B2 (en)	2007-03-13	Enantiomerically pure opioid diarylmethylpiperazine as a cardioprotection agent
MXPA00000195A (en)	2000-09-08	Compositions and methods for reducing respiratory depression and attendant side effects of mu opioid compounds
JP2005314347A (ja)	2005-11-10	疼痛抑制剤
US20230295115A1 (en)	2023-09-21	Substituted isoquinolinylmethyl amides, analogues thereof, and methods using same
US20070197786A1 (en)	2007-08-23	Enantiomerically pure opioid diarylmethylpiperazine
TW200404545A (en)	2004-04-01	An enantiomerically pure opioid diarylmethylpiperzine and methods of using same