ZA200308103B - Spiropyrazole compounds. - Google Patents
Spiropyrazole compounds. Download PDFInfo
- Publication number
- ZA200308103B ZA200308103B ZA200308103A ZA200308103A ZA200308103B ZA 200308103 B ZA200308103 B ZA 200308103B ZA 200308103 A ZA200308103 A ZA 200308103A ZA 200308103 A ZA200308103 A ZA 200308103A ZA 200308103 B ZA200308103 B ZA 200308103B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- compound
- phenyl
- cycloalkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- -1 aminocarbonyl- Chemical group 0.000 claims description 100
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 108020003175 receptors Proteins 0.000 claims description 25
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 20
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 229950007471 myrophine Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229960000805 nalbuphine Drugs 0.000 description 1
- NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 description 1
- 229960000938 nalorphine Drugs 0.000 description 1
- 239000004090 neuroprotective agent Substances 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- HNDXBGYRMHRUFN-CIVUWBIHSA-N nicomorphine Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)OC(=O)C=4C=NC=CC=4)O[C@@H]1[C@]52CCN3C)C(=O)C1=CC=CN=C1 HNDXBGYRMHRUFN-CIVUWBIHSA-N 0.000 description 1
- 229960004300 nicomorphine Drugs 0.000 description 1
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
- 229960000965 nimesulide Drugs 0.000 description 1
- 229940121367 non-opioid analgesics Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 229950011519 norlevorphanol Drugs 0.000 description 1
- WCJFBSYALHQBSK-UHFFFAOYSA-N normethadone Chemical compound C=1C=CC=CC=1C(CCN(C)C)(C(=O)CC)C1=CC=CC=C1 WCJFBSYALHQBSK-UHFFFAOYSA-N 0.000 description 1
- 229960004013 normethadone Drugs 0.000 description 1
- 229950006134 normorphine Drugs 0.000 description 1
- WCDSHELZWCOTMI-UHFFFAOYSA-N norpipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CCN1CCCCC1 WCDSHELZWCOTMI-UHFFFAOYSA-N 0.000 description 1
- 229950007418 norpipanone Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 239000000014 opioid analgesic Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003294 papaveretum Drugs 0.000 description 1
- 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 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- LOXCOAXRHYDLOW-UHFFFAOYSA-N phenadoxone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCOCC1 LOXCOAXRHYDLOW-UHFFFAOYSA-N 0.000 description 1
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- ZQHYKVKNPWDQSL-KNXBSLHKSA-N phenazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CCC1=CC=CC=C1 ZQHYKVKNPWDQSL-KNXBSLHKSA-N 0.000 description 1
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- 229950011496 phenomorphan Drugs 0.000 description 1
- IPOPQVVNCFQFRK-UHFFFAOYSA-N phenoperidine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(O)C1=CC=CC=C1 IPOPQVVNCFQFRK-UHFFFAOYSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- PXXKIYPSXYFATG-UHFFFAOYSA-N piminodine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCCNC1=CC=CC=C1 PXXKIYPSXYFATG-UHFFFAOYSA-N 0.000 description 1
- 229950006445 piminodine Drugs 0.000 description 1
- IHEHEFLXQFOQJO-UHFFFAOYSA-N piritramide Chemical compound C1CC(C(=O)N)(N2CCCCC2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 IHEHEFLXQFOQJO-UHFFFAOYSA-N 0.000 description 1
- 229960001286 piritramide Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- ZXWAUWBYASJEOE-UHFFFAOYSA-N proheptazine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCCN(C)CC1C ZXWAUWBYASJEOE-UHFFFAOYSA-N 0.000 description 1
- 229950010387 proheptazine Drugs 0.000 description 1
- XJKQCILVUHXVIQ-UHFFFAOYSA-N properidine Chemical compound C=1C=CC=CC=1C1(C(=O)OC(C)C)CCN(C)CC1 XJKQCILVUHXVIQ-UHFFFAOYSA-N 0.000 description 1
- 229950004345 properidine Drugs 0.000 description 1
- ZBAFFZBKCMWUHM-UHFFFAOYSA-N propiram Chemical compound C=1C=CC=NC=1N(C(=O)CC)C(C)CN1CCCCC1 ZBAFFZBKCMWUHM-UHFFFAOYSA-N 0.000 description 1
- 229950003779 propiram Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 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 description 1
- 229960004739 sufentanil Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Dental Preparations (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| ZA200308103A ZA200308103B (en) | 2001-04-18 | 2003-10-17 | Spiropyrazole compounds. |
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| AU2003220886A1 (en) | 2002-03-29 | 2003-10-13 | Mitsubishi Pharma Corporation | Remedy for sleep disturbance |
| RS20050208A (sr) | 2002-09-09 | 2007-08-03 | Janssen Pharmaceutica N.V., | Hidroksi alkil supstituisani 1,3,8- triazaspiro /4,5/dekan-4- on derivati korisni u lečenju poremećaja u kojim posreduje orl-1 receptor |
| EP1551400A2 (en) * | 2002-10-17 | 2005-07-13 | Euro-Celtique S.A. | Preparation of triazospiro compounds |
| US20040242583A1 (en) * | 2003-01-20 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Pyrimido[5,4-e][1,2,4]triazine-5,7-diones, processes for preparing them and their use |
| WO2004103305A2 (en) * | 2003-05-16 | 2004-12-02 | Euroceltique S.A. | Spiropyrazole compound |
| WO2005011665A1 (en) * | 2003-07-22 | 2005-02-10 | Arakis Ltd. | The use of proglumide for the treatment of emesis |
| HUE032657T2 (en) | 2004-03-29 | 2017-10-30 | Univ South Florida | Effective treatment of tumors and cancer with triciribin phosphate |
| US20100028339A1 (en) | 2004-03-29 | 2010-02-04 | Cheng Jin Q | Compositions including triciribine and trastuzumab and methods of use thereof |
| US20100009928A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and taxanes and methods of use thereof |
| US20100173864A1 (en) | 2004-03-29 | 2010-07-08 | Cheng Jin Q | Compositions including triciribine and one or more platinum compounds and methods of use thereof |
| US20100009929A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and bortezomib and derivatives thereof and methods of use thereof |
| US20110008327A1 (en) | 2004-03-29 | 2011-01-13 | Cheng Jin Q | Compositions including triciribine and epidermal growth factor receptor inhibitor compounds or salts thereof and methods of use thereof |
| DE602006016244D1 (de) | 2005-03-08 | 2010-09-30 | Janssen Pharmaceutica Nv | Diazaspiro-ä4,4ü-nonanderivate als neurokinin-(nk1)-antagonisten |
| CN1870631B (zh) * | 2005-11-11 | 2010-04-14 | 华为技术有限公司 | 媒体网关的门控方法 |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| CA2670858C (en) | 2006-11-28 | 2015-01-13 | Janssen Pharmaceutica N.V. | Salts of 3-(3-amino-2-(r)-hydroxy-propyl)-1-(4-fluoro-phenyl)-8-(8-methyl-naphthalen-1-ylmethyl)-1,3,8-triaza-spiro[4.5]decan-4-one |
| DK2076506T3 (da) | 2007-01-16 | 2011-01-10 | Purdue Pharma Lp | Heterocyklisk substituerede piperidiner som ORL-1-ligander |
| US8741916B2 (en) | 2007-04-09 | 2014-06-03 | Janssen Pharmaceutica Nv | 1,3,8-trisubstituted-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as ligands of the ORL-1 receptor |
| TWI448289B (zh) | 2007-08-31 | 2014-08-11 | Purdue Pharma Lp | 經取代之喹啉型哌啶化合物及其用途 |
| PE20140102A1 (es) | 2008-07-21 | 2014-02-06 | Purdue Pharma Lp | Compuestos de piperidina puenteada tipo quinoxalina sustituida con actividad sobre el receptor orl-1 |
| UA107943C2 (xx) * | 2009-11-16 | 2015-03-10 | Lilly Co Eli | Сполуки спіропіперидину як антагоністи рецептора orl-1 |
| US9598447B2 (en) | 2010-12-22 | 2017-03-21 | Purdue Pharma L.P. | Phosphorus-substituted quinoxaline-type piperidine compounds and uses thereof |
| EP2797912B1 (en) | 2011-12-01 | 2016-05-25 | Purdue Pharma L.P. | Azetidine-substituted quinoxaline-type piperidine compounds and uses thereof |
| US9085561B2 (en) | 2012-07-30 | 2015-07-21 | Purdue Pharma L.P. | Cyclic urea- or lactam-substituted quinoxaline-type piperidines as ORL-1 modulators |
| US10118927B2 (en) | 2012-12-27 | 2018-11-06 | Purdue Pharma L.P. | Substituted piperidin-4-amino-type compounds and uses thereof |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
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| US9951038B2 (en) | 2012-12-27 | 2018-04-24 | Purdue Pharma L.P. | Quinazolin-4(3H)-one-type piperidine compounds and uses thereof |
| KR20190033599A (ko) | 2016-07-29 | 2019-03-29 | 얀센 파마슈티카 엔.브이. | 전립선암의 치료 방법 |
| CN111825681A (zh) * | 2020-07-07 | 2020-10-27 | 扬州大学 | 一种合成(e)-亚苄基螺吡唑吡咯嗪酮类化合物的方法 |
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| US3318900A (en) | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| US3325499A (en) | 1964-11-02 | 1967-06-13 | Mcneilab Inc | 1-(1-hydrocarbyl-4-piperdyl)-2-indolinone |
| US3923993A (en) * | 1973-06-28 | 1975-12-02 | American Home Prod | Process for treating neuroendocrinopathic diseases employing fluspirilene |
| DE2609645A1 (de) | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| US4329353A (en) | 1980-10-22 | 1982-05-11 | Janssen Pharmaceutica, N.V. | 1-(4-Aryl-cyclohexyl)piperidine derivatives, method of use thereof and pharmaceutical compositions thereof |
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| JPS58180481A (ja) | 1982-04-15 | 1983-10-21 | Kyowa Hakko Kogyo Co Ltd | 新規なピペリジン誘導体 |
| JPS60120872A (ja) | 1983-12-01 | 1985-06-28 | Kyowa Hakko Kogyo Co Ltd | 新規なヘテロ環状化合物及び強心剤 |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| JPH09512016A (ja) | 1994-04-14 | 1997-12-02 | メルク エンド カンパニー インコーポレーテッド | α１Ｃアドレナリン受容体拮抗薬 |
| FR2722190B1 (fr) | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
| FR2725206B1 (fr) * | 1994-09-29 | 1996-12-06 | Roussel Uclaf | Nouvelles imidazolidines substituees par un heterocycle, leur procede et des intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| US5767118A (en) | 1994-10-26 | 1998-06-16 | Merck & Co., Inc. | 4-Heterocyclic peperidines promote release of growth hormone |
| US5574044A (en) | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| CA2231773A1 (en) | 1995-09-13 | 1997-03-20 | Shigeru Aono | Phenylpiperidine derivative |
| US6180649B1 (en) | 1996-04-19 | 2001-01-30 | Nerosearch A/S | 1-(4-piperidyl)-benzimidazoles having neurotrophic activity |
| US6063796A (en) | 1997-04-04 | 2000-05-16 | Merck & Co., Inc. | Somatostatin agonists |
| DE69826278T2 (de) | 1997-05-30 | 2005-11-10 | Banyu Pharmaceutical Co., Ltd. | 2-oxoimidazol-derivate |
| JPH10330377A (ja) | 1997-06-02 | 1998-12-15 | Kyowa Hakko Kogyo Co Ltd | ピペリジン誘導体 |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| SI0921125T1 (en) | 1997-12-05 | 2002-04-30 | F. Hoffmann-La Roche Ag | 1,3,8-Triazaspiro(4,5)decan-4-on derivatives |
| US6166209A (en) | 1997-12-11 | 2000-12-26 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| ES2175925T3 (es) | 1998-01-19 | 2002-11-16 | Pfizer | Compuestos 4-(2-ceto-1-benzilimidazolinil)piperidina como agonistas del receptor orl1. |
| RU2202344C2 (ru) | 1998-03-26 | 2003-04-20 | Джапан Тобакко Инк. | Антагонисты ноцицептина, производные амида, аналгетик, способ инициирования антагонистического действия к ноцицептину, способ лечения боли, фармацевтические композиции |
| EP1080091A1 (en) * | 1998-05-18 | 2001-03-07 | Novo Nordisk A/S | Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| ID29137A (id) | 1998-07-27 | 2001-08-02 | Schering Corp | Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1 |
| US6262066B1 (en) | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| MA26659A1 (fr) | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| AU8870601A (en) | 2000-09-06 | 2002-03-22 | Ortho Mcneil Pharm Inc | A method for treating allergies using substituted pyrazoles |
| US6635653B2 (en) * | 2001-04-18 | 2003-10-21 | Euro-Celtique S.A. | Spiropyrazole compounds |
-
2002
- 2002-04-18 US US10/126,506 patent/US6635653B2/en not_active Expired - Lifetime
- 2002-04-18 IL IL15848502A patent/IL158485A0/xx unknown
- 2002-04-18 ES ES02739163T patent/ES2312584T3/es not_active Expired - Lifetime
- 2002-04-18 SI SI200230748T patent/SI1385515T1/sl unknown
- 2002-04-18 NZ NZ528978A patent/NZ528978A/en not_active IP Right Cessation
- 2002-04-18 AT AT02739163T patent/ATE403429T1/de active
- 2002-04-18 EP EP02739163A patent/EP1385515B1/en not_active Expired - Lifetime
- 2002-04-18 DK DK02739163T patent/DK1385515T3/da active
- 2002-04-18 WO PCT/US2002/012376 patent/WO2002085355A1/en not_active Ceased
- 2002-04-18 AU AU2002311833A patent/AU2002311833B2/en not_active Ceased
- 2002-04-18 CA CA2444634A patent/CA2444634C/en not_active Expired - Fee Related
- 2002-04-18 RU RU2003133455/04A patent/RU2299883C2/ru not_active IP Right Cessation
- 2002-04-18 YU YU82403A patent/YU82403A/sh unknown
- 2002-04-18 JP JP2002582928A patent/JP4342181B2/ja not_active Expired - Fee Related
- 2002-04-18 CZ CZ20032849A patent/CZ20032849A3/cs unknown
- 2002-04-18 DE DE60228071T patent/DE60228071D1/de not_active Expired - Lifetime
- 2002-04-18 PL PL02367263A patent/PL367263A1/xx not_active Application Discontinuation
- 2002-04-18 BR BRPI0209127-5A patent/BR0209127A/pt not_active Application Discontinuation
- 2002-04-18 PT PT02739163T patent/PT1385515E/pt unknown
- 2002-04-18 MX MXPA03009604A patent/MXPA03009604A/es active IP Right Grant
- 2002-04-18 KR KR1020037013821A patent/KR100628292B1/ko not_active Expired - Fee Related
- 2002-04-18 CN CNA028121767A patent/CN1516584A/zh active Pending
- 2002-04-18 UA UA20031110381A patent/UA74439C2/uk unknown
- 2002-04-18 HU HU0401333A patent/HUP0401333A3/hu unknown
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2003
- 2003-06-19 US US10/601,174 patent/US20040087641A1/en not_active Abandoned
- 2003-10-17 NO NO20034660A patent/NO20034660L/no not_active Application Discontinuation
- 2003-10-17 ZA ZA200308103A patent/ZA200308103B/en unknown
- 2003-10-19 IL IL158485A patent/IL158485A/en not_active IP Right Cessation
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2008
- 2008-10-27 CY CY20081101206T patent/CY1108454T1/el unknown
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