NO309936B1 - 2,7-Substituerte oktahydro-pyrrol[1,2-a]pyrazin-derivater, anvendelse derav, farmasøytisk preparat, samt mellomprodukter for fremstilling av derivatene - Google Patents
2,7-Substituerte oktahydro-pyrrol[1,2-a]pyrazin-derivater, anvendelse derav, farmasøytisk preparat, samt mellomprodukter for fremstilling av derivatene Download PDFInfo
- Publication number
- NO309936B1 NO309936B1 NO982843A NO982843A NO309936B1 NO 309936 B1 NO309936 B1 NO 309936B1 NO 982843 A NO982843 A NO 982843A NO 982843 A NO982843 A NO 982843A NO 309936 B1 NO309936 B1 NO 309936B1
- Authority
- NO
- Norway
- Prior art keywords
- octahydro
- pyrazine
- pyrrole
- compound
- pharmaceutically acceptable
- Prior art date
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- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical class CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 title claims description 126
- 238000002360 preparation method Methods 0.000 title claims description 44
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 239000012450 pharmaceutical intermediate Substances 0.000 title 1
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- -1 -COOR 4 Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 53
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 48
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- 208000035475 disorder Diseases 0.000 claims description 17
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- 239000000126 substance Substances 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
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- 239000000543 intermediate Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000001823 molecular biology technique Methods 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008183 oral pharmaceutical preparation Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Ophthalmology & Optometry (AREA)
- Toxicology (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US898895P | 1995-12-21 | 1995-12-21 | |
| PCT/IB1996/001192 WO1997023482A1 (fr) | 1995-12-21 | 1996-11-06 | Derives de 2,7-octahydro substitue-pyrrolo[1,2-a]pyrazine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982843L NO982843L (no) | 1998-06-19 |
| NO982843D0 NO982843D0 (no) | 1998-06-19 |
| NO309936B1 true NO309936B1 (no) | 2001-04-23 |
Family
ID=21734893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO982843A NO309936B1 (no) | 1995-12-21 | 1998-06-19 | 2,7-Substituerte oktahydro-pyrrol[1,2-a]pyrazin-derivater, anvendelse derav, farmasøytisk preparat, samt mellomprodukter for fremstilling av derivatene |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US5714487A (fr) |
| EP (1) | EP0874849B1 (fr) |
| JP (1) | JP3204456B2 (fr) |
| KR (1) | KR100286786B1 (fr) |
| CN (1) | CN1061350C (fr) |
| AR (1) | AR005102A1 (fr) |
| AT (1) | ATE205846T1 (fr) |
| AU (1) | AU704578B2 (fr) |
| BR (1) | BR9612246A (fr) |
| CA (1) | CA2240594C (fr) |
| CO (1) | CO4480107A1 (fr) |
| CZ (1) | CZ192998A3 (fr) |
| DE (1) | DE69615404T2 (fr) |
| DK (1) | DK0874849T3 (fr) |
| ES (1) | ES2161377T3 (fr) |
| GR (1) | GR3037060T3 (fr) |
| GT (1) | GT199600101A (fr) |
| HU (1) | HUP9900611A3 (fr) |
| IL (1) | IL124453A0 (fr) |
| MA (1) | MA26413A1 (fr) |
| MX (1) | MX9805088A (fr) |
| NO (1) | NO309936B1 (fr) |
| NZ (1) | NZ320537A (fr) |
| PE (1) | PE25998A1 (fr) |
| PL (1) | PL327539A1 (fr) |
| PT (1) | PT874849E (fr) |
| RU (1) | RU2162470C2 (fr) |
| SI (1) | SI0874849T1 (fr) |
| TN (1) | TNSN96164A1 (fr) |
| TR (1) | TR199801161T2 (fr) |
| TW (1) | TW479058B (fr) |
| WO (1) | WO1997023482A1 (fr) |
| ZA (1) | ZA9610781B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281216B1 (en) * | 1998-02-09 | 2001-08-28 | Duphar International Research B.V. | 2-aminoquinoline derivatives having d4-agonistic activity |
| EP0982030A3 (fr) | 1998-08-17 | 2000-05-10 | Pfizer Products Inc. | Derives de 2,7-octahydro substitue-pyrrolo 1,2-a]pyrazine comme ligands des recepteurs 5ht 1a |
| AU767089B2 (en) * | 1999-02-05 | 2003-10-30 | Pharmacia & Upjohn Company | Process to prepare (5R)-(methylamino)-5,6-dihydro-4H- imidazo(4,5,1-ij)-quinolin-2(1H)-one |
| US7091199B1 (en) | 1999-09-14 | 2006-08-15 | Aventis Pharmaceuticals Inc. | Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists |
| US7253165B2 (en) | 1999-09-14 | 2007-08-07 | Aventis Pharmaceuticals Inc. | Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists |
| US7125903B1 (en) | 1999-09-14 | 2006-10-24 | Aventis Pharmaceuticals Inc. | Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists |
| CA2383332C (fr) * | 1999-09-14 | 2006-01-10 | Aventis Pharmaceuticals Inc. | Derives benzisoxazolyle, pyridoisoxazolyle- et benzthienyle du propyle a substitution phenoxy, antagonistes du d4 |
| TW200801005A (en) * | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Acetylenic piperazines as metabotropic glutamate receptor antagonists |
| US7728031B2 (en) * | 2006-02-24 | 2010-06-01 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole derivatives |
| WO2013049164A1 (fr) * | 2011-09-29 | 2013-04-04 | Abbvie Inc. | Octahydropyrrolo[1,2-a]pyrazines substituées utilisées en tant qu'inhibiteurs des canaux calciques |
| US11612924B2 (en) * | 2018-03-28 | 2023-03-28 | Sintokogio, Ltd. | Electric lifting apparatus and roll press machine |
| EP3846806A4 (fr) * | 2018-09-04 | 2022-06-08 | Pipeline Therapeutics, Inc. | Antagonistes du récepteur m1 de l'acétylcholine muscarinique |
| US11752149B2 (en) | 2019-12-02 | 2023-09-12 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400511A (en) * | 1982-05-07 | 1983-08-23 | American Home Products Corporation | 2-Substituted octahydropyrrolo(1,2-A)-pyrazine-3-carboxylic acids |
| WO1990008148A1 (fr) * | 1989-01-23 | 1990-07-26 | Pfizer Inc. | Agents anxiolytiques bis-aza-bicycliques |
| US5122515A (en) * | 1990-06-19 | 1992-06-16 | Smith Ross C | Nutrient composition containing dipeptides and method for administering the same |
| JP3058945B2 (ja) * | 1990-10-26 | 2000-07-04 | 三共株式会社 | Ｎ−（３，３−ジ置換アクリロイル）ピペラジン誘導体 |
| US5670522A (en) * | 1992-10-23 | 1997-09-23 | Merck Sharp & Dohme Limited | Dopamine receptor subtype ligands |
| WO1994010145A1 (fr) * | 1992-10-23 | 1994-05-11 | Merck Sharp & Dohme Limited | Ligands pour les sous-types de recepteurs de dopamine |
| DE69530988T2 (de) * | 1994-08-05 | 2003-12-04 | Pfizer | Benzimidazolderivate mit dopaminerger wirkung |
| WO1996010571A1 (fr) * | 1994-09-30 | 1996-04-11 | Pfizer Inc. | Derives d'octahydro 1-h-pyrido[1,2-a] pyrazine substituee en 2,7 |
-
1996
- 1996-11-06 DE DE69615404T patent/DE69615404T2/de not_active Expired - Fee Related
- 1996-11-06 KR KR1019980704718A patent/KR100286786B1/ko not_active IP Right Cessation
- 1996-11-06 AU AU73280/96A patent/AU704578B2/en not_active Ceased
- 1996-11-06 NZ NZ320537A patent/NZ320537A/xx unknown
- 1996-11-06 HU HU9900611A patent/HUP9900611A3/hu unknown
- 1996-11-06 BR BR9612246A patent/BR9612246A/pt not_active Application Discontinuation
- 1996-11-06 IL IL12445396A patent/IL124453A0/xx unknown
- 1996-11-06 JP JP52344697A patent/JP3204456B2/ja not_active Expired - Fee Related
- 1996-11-06 DK DK96935226T patent/DK0874849T3/da active
- 1996-11-06 RU RU98111742/04A patent/RU2162470C2/ru not_active IP Right Cessation
- 1996-11-06 EP EP96935226A patent/EP0874849B1/fr not_active Expired - Lifetime
- 1996-11-06 PT PT96935226T patent/PT874849E/pt unknown
- 1996-11-06 PL PL96327539A patent/PL327539A1/xx unknown
- 1996-11-06 CZ CZ981929A patent/CZ192998A3/cs unknown
- 1996-11-06 SI SI9630343T patent/SI0874849T1/xx unknown
- 1996-11-06 ES ES96935226T patent/ES2161377T3/es not_active Expired - Lifetime
- 1996-11-06 CN CN96199250A patent/CN1061350C/zh not_active Expired - Fee Related
- 1996-11-06 CA CA002240594A patent/CA2240594C/fr not_active Expired - Fee Related
- 1996-11-06 TR TR1998/01161T patent/TR199801161T2/xx unknown
- 1996-11-06 AT AT96935226T patent/ATE205846T1/de not_active IP Right Cessation
- 1996-11-06 WO PCT/IB1996/001192 patent/WO1997023482A1/fr not_active Application Discontinuation
- 1996-11-08 TW TW085113669A patent/TW479058B/zh not_active IP Right Cessation
- 1996-12-16 PE PE1996000913A patent/PE25998A1/es not_active Application Discontinuation
- 1996-12-16 AR ARP960105715A patent/AR005102A1/es not_active Application Discontinuation
- 1996-12-18 TN TNTNSN96164A patent/TNSN96164A1/fr unknown
- 1996-12-18 MA MA24432A patent/MA26413A1/fr unknown
- 1996-12-19 GT GT199600101A patent/GT199600101A/es unknown
- 1996-12-20 CO CO96066997A patent/CO4480107A1/es unknown
- 1996-12-20 ZA ZA9610781A patent/ZA9610781B/xx unknown
- 1996-12-23 US US08/774,290 patent/US5714487A/en not_active Expired - Fee Related
-
1998
- 1998-06-19 NO NO982843A patent/NO309936B1/no unknown
- 1998-06-22 MX MX9805088A patent/MX9805088A/es unknown
-
2001
- 2001-10-30 GR GR20010401932T patent/GR3037060T3/el not_active IP Right Cessation
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