SG11201803757UA - N-[2-(1 -benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1 -carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases - Google Patents
N-[2-(1 -benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1 -carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseasesInfo
- Publication number
- SG11201803757UA SG11201803757UA SG11201803757UA SG11201803757UA SG11201803757UA SG 11201803757U A SG11201803757U A SG 11201803757UA SG 11201803757U A SG11201803757U A SG 11201803757UA SG 11201803757U A SG11201803757U A SG 11201803757UA SG 11201803757U A SG11201803757U A SG 11201803757UA
- Authority
- SG
- Singapore
- Prior art keywords
- international
- benzylpiperidin
- pyrazin
- piperazine
- diseases
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title abstract 2
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title abstract 2
- NTEFDRIAFGEYBB-UHFFFAOYSA-N N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-pyrazin-2-ylpiperazine-1-carboxamide Chemical class C(C1=CC=CC=C1)N1CCC(CC1)CCNC(=O)N1CCN(CC1)C1=NC=CN=C1 NTEFDRIAFGEYBB-UHFFFAOYSA-N 0.000 title abstract 2
- 239000005557 antagonist Substances 0.000 title abstract 2
- 208000012902 Nervous system disease Diseases 0.000 title 1
- 208000025966 Neurological disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 7
- 201000010099 disease Diseases 0.000 abstract 4
- 102220240796 rs553605556 Human genes 0.000 abstract 3
- 208000012661 Dyskinesia Diseases 0.000 abstract 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 230000003042 antagnostic effect Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000003551 muscarinic effect Effects 0.000 abstract 2
- 230000000926 neurological effect Effects 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 206010008748 Chorea Diseases 0.000 abstract 1
- 208000014094 Dystonic disease Diseases 0.000 abstract 1
- 208000023105 Huntington disease Diseases 0.000 abstract 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 abstract 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 abstract 1
- 208000009829 Lewy Body Disease Diseases 0.000 abstract 1
- 201000002832 Lewy body dementia Diseases 0.000 abstract 1
- 206010033799 Paralysis Diseases 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 206010034010 Parkinsonism Diseases 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 206010048327 Supranuclear palsy Diseases 0.000 abstract 1
- 230000002490 cerebral effect Effects 0.000 abstract 1
- 208000012601 choreatic disease Diseases 0.000 abstract 1
- 230000007278 cognition impairment Effects 0.000 abstract 1
- 208000010118 dystonia Diseases 0.000 abstract 1
- 229960004502 levodopa Drugs 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
- 208000021090 palsy Diseases 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000000750 progressive effect Effects 0.000 abstract 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 150000003384 small molecules Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61P25/28—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property -' Organization International Bureau (43) International Publication Date .... ..sr ,„„..) 11 May 2017(11.05.2017) WIPO I PCT (10) WO International 111111111111311111111111111111111111111111111111111111111111111111111111111111111111111111 2017/079641 Publication Al Number (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, C07D 401/12 (2006.01) A61K 31/4545 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, CO7D 211/26 (2006.01) A61P 25/28 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, CO7D 211/40 (2006.01) A61P 25/16 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, A61K 31/445 (2006.01) A61P 25/18 (2006.01) KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/US2016/060659 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 4 November 2016 (04.11.2016) ZW. (25) Filing Language: English (8 4 ) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (30) Priority Data: TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 62/252,179 6 November 2015 (06.11.2015) US TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, 62/275,708 6 January 2016 (06.01.2016) US DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (71) Applicant: NEUROCRINE BIOSCIENCES, INC. SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, [US/US]; 12780 El Camino Real, San Diego, California GW, KM, ML, MR, NE, SN, TD, TG). 92130 (US). Declarations under Rule 4.17: (72) Inventors: HARRIOTT, Nicole; 11340 Squamish Road, as to applicant's entitlement to apply for and be granted a San Diego, California 92126 (US). PAGANO, Nicholas; patent (Rule 4.17 (ii)) 1512 La Playa Avenue, Apartment 312, San Diego, Cali- fornia 92109 (US). — as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.17(iii)) (74) Agents: HERMANNS, Karl, R. et al.; Seed Intellectual Property Law Group LLP, Suite 5400, 701 Fifth Avenue, Published: Seattle, Washington 98104-7064 (US). — with international search report (Art 21(3)) (81) Designated States (unless otherwise indicated, for every _ 19(1)) with amended claims (Art kind AE, AG, AL, AM, of national protection available): Title: (54) N-[2-(1 -BENZYLPIPERIDIN-4-YL)ETHYL]-4-(PYRAZIN-2-YL)-PIPERAZINE-1 -CARBOXAMIDE DERIVATIVES AND RE- LATED COMPOUNDS AS MUSCARINIC RECEPTOR 4 (M4) ANTAGONISTS FOR TREATING NEUROLOGICAL DISEASES (R2)w (R3)x Il .4t A 11 i t 0 \ IN (57) : Provided herein are small molecule 0 ---- ter or pharmaceutically acceptable salt thereof, Methods for treating diseases/ disorders by antagonizing 1:::j ceptor 4 (M4), are also disclosed. Such diseases/disorders el Lewy Body Dementia and the cognitive deficits ea ) dyskinesias, dystonia, chorea, levodopa induced Preferred compounds are e.g. 1\112-(1-benzylpiperidin-4-yflethyl]-4- compounds wherein the pyrazine has been replaced N '- ''' .--r 'Th-] wherein dyskinesia, by compounds associated ) o,i A, B, are muscarinic cerebral e.g. pyridazine, (IR,Oy B L2 of the following C, L I , L 2, e.g. neurological with schizophrenia, palsy, receptors, pyrimidine, r-7\ C .Y R I , R R R R 2, progressive (pyrazin-2-y1)-piperazine-1-carboxamide formula diseases/disorders sh (I) (I): or a stereoisomer, tautomer, solvate, es - 3, 4, 5, w, x, y and z are as defined herein. including specifically antagonizing muscarinic re - such as e.g. Alzheimer's Disease, Parkinson's Disease, drug induced Parkinsonism, supranuclear palsy, and Huntington's disease. derivatives and related pyridine or phenyl.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562252179P | 2015-11-06 | 2015-11-06 | |
| US201662275708P | 2016-01-06 | 2016-01-06 | |
| PCT/US2016/060659 WO2017079641A1 (en) | 2015-11-06 | 2016-11-04 | N-[2-(1 -benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1 -carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG11201803757UA true SG11201803757UA (en) | 2018-06-28 |
Family
ID=57349137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201803757UA SG11201803757UA (en) | 2015-11-06 | 2016-11-04 | N-[2-(1 -benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1 -carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US11033539B2 (en) |
| EP (1) | EP3371164B1 (en) |
| JP (2) | JP6917989B2 (en) |
| KR (1) | KR20180073685A (en) |
| CN (1) | CN108349936B (en) |
| AU (1) | AU2016348524B2 (en) |
| BR (1) | BR112018008630A2 (en) |
| CA (1) | CA3001873A1 (en) |
| CL (1) | CL2018001217A1 (en) |
| CO (1) | CO2018004800A2 (en) |
| ES (1) | ES2915266T3 (en) |
| HK (1) | HK1253029A1 (en) |
| IL (1) | IL258862B (en) |
| MA (1) | MA43168A (en) |
| MX (1) | MX2018005215A (en) |
| MY (1) | MY194461A (en) |
| PE (1) | PE20181010A1 (en) |
| PH (1) | PH12018500940A1 (en) |
| SA (1) | SA518391518B1 (en) |
| SG (1) | SG11201803757UA (en) |
| TN (1) | TN2018000130A1 (en) |
| WO (1) | WO2017079641A1 (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY197370A (en) | 2015-11-06 | 2023-06-14 | Hoffmann La Roche | Indolin-2-one derivatives |
| JP6917989B2 (en) * | 2015-11-06 | 2021-08-11 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | N- [2- (1-benzylpiperidine-4-yl) ethyl] -4- (pyrazine-2-yl) -piperazine- as a muscarinic receptor 4 (M4) antagonist for treating neurological disorders 1-Carboxamide Derivatives and Related Compounds |
| JP2020530451A (en) | 2017-08-08 | 2020-10-22 | ヴァンダービルト ユニバーシティー | Antagonist of muscarinic acetylcholine receptor M4 |
| JP2020537667A (en) | 2017-10-17 | 2020-12-24 | ヴァンダービルト ユニバーシティー | Antagonist of muscarinic acetylcholine receptor M4 |
| AU2018351651B2 (en) | 2017-10-20 | 2023-01-05 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2019089676A1 (en) | 2017-10-31 | 2019-05-09 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| EP3732163A4 (en) | 2017-12-20 | 2021-07-14 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| US11414406B2 (en) | 2018-02-02 | 2022-08-16 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| PT3762368T (en) | 2018-03-08 | 2022-05-06 | Incyte Corp | Aminopyrazine diol compounds as pi3k-y inhibitors |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| WO2020048826A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 5-substituted 1-oxa-3,9-diazaspiro[5.5]undecan-2-one compounds |
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