KR20150108384A - 중추신경계 질병의 치료를 위한 옥시토신 수용체 작용제 - Google Patents
중추신경계 질병의 치료를 위한 옥시토신 수용체 작용제 Download PDFInfo
- Publication number
- KR20150108384A KR20150108384A KR1020157021897A KR20157021897A KR20150108384A KR 20150108384 A KR20150108384 A KR 20150108384A KR 1020157021897 A KR1020157021897 A KR 1020157021897A KR 20157021897 A KR20157021897 A KR 20157021897A KR 20150108384 A KR20150108384 A KR 20150108384A
- Authority
- KR
- South Korea
- Prior art keywords
- benzenesulfonamide
- pyrazol
- pyridin
- trifluoromethyl
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
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- 108090000876 Oxytocin receptors Proteins 0.000 title description 5
- 201000010099 disease Diseases 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 3
- 229940044601 receptor agonist Drugs 0.000 title description 2
- 239000000018 receptor agonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 150000002367 halogens Chemical class 0.000 claims abstract description 25
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
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- 206010003805 Autism Diseases 0.000 claims abstract description 8
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- 208000020401 Depressive disease Diseases 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 208000026139 Memory disease Diseases 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
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- 208000023060 memory loss Diseases 0.000 claims abstract description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 5
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 48
- -1 2-fluoro-N- [2- (4-methyl-thiazol-2-yl) -2H- pyrazol-3-yl] -benzenesulfonamide Chemical compound 0.000 claims description 31
- JRZHXPWLIFIBOK-UHFFFAOYSA-N 4-chloro-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 JRZHXPWLIFIBOK-UHFFFAOYSA-N 0.000 claims description 14
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- DSAPTSAWPAQPBM-UHFFFAOYSA-N 4-chloro-n-[2-(4-methyl-1,3-thiazol-2-yl)pyrazol-3-yl]benzenesulfonamide Chemical compound CC1=CSC(N2C(=CC=N2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 DSAPTSAWPAQPBM-UHFFFAOYSA-N 0.000 claims description 7
- PQHFXMDZFWZDLM-UHFFFAOYSA-N 4-ethyl-n-[2-(4-methyl-1,3-thiazol-2-yl)pyrazol-3-yl]benzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=NN1C1=NC(C)=CS1 PQHFXMDZFWZDLM-UHFFFAOYSA-N 0.000 claims description 7
- UDJZSAKEYMJSOU-UHFFFAOYSA-N n-(2-pyrimidin-2-ylpyrazol-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=NN1C1=NC=CC=N1 UDJZSAKEYMJSOU-UHFFFAOYSA-N 0.000 claims description 7
- XSOMDHYDYIBGDE-UHFFFAOYSA-N n-[2-(3-cyclopropyl-1,2,4-thiadiazol-5-yl)pyrazol-3-yl]-4-ethylbenzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=NN1C1=NC(C2CC2)=NS1 XSOMDHYDYIBGDE-UHFFFAOYSA-N 0.000 claims description 7
- WFVIVWANXDMMEG-UHFFFAOYSA-N n-[2-(4-methyl-1,3-thiazol-2-yl)pyrazol-3-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CSC(N2C(=CC=N2)NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 WFVIVWANXDMMEG-UHFFFAOYSA-N 0.000 claims description 7
- RUNWGTDYNSGOLC-UHFFFAOYSA-N 4-(1-fluoroethyl)-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C1=CC(C(F)C)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 RUNWGTDYNSGOLC-UHFFFAOYSA-N 0.000 claims description 6
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- TYXBBRWSZATQTG-UHFFFAOYSA-N 2,4-dichloro-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 TYXBBRWSZATQTG-UHFFFAOYSA-N 0.000 claims description 5
- WJRZGPHJHNRCKM-UHFFFAOYSA-N 2-chloro-n-(2-pyridin-2-ylpyrazol-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 WJRZGPHJHNRCKM-UHFFFAOYSA-N 0.000 claims description 5
- VOIWSQAPABZZFG-UHFFFAOYSA-N 2-fluoro-n-(2-pyridin-2-ylpyrazol-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound FC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 VOIWSQAPABZZFG-UHFFFAOYSA-N 0.000 claims description 5
- POKOXEDVQWICML-UHFFFAOYSA-N 3-fluoro-n-(2-pyridin-2-ylpyrazol-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(C(F)(F)F)C(F)=CC(S(=O)(=O)NC=2N(N=CC=2)C=2N=CC=CC=2)=C1 POKOXEDVQWICML-UHFFFAOYSA-N 0.000 claims description 5
- COEBTTDNOVBDSF-UHFFFAOYSA-N 4-(difluoromethoxy)-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C1=CC(OC(F)F)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 COEBTTDNOVBDSF-UHFFFAOYSA-N 0.000 claims description 5
- MPNSNZPKUAKLLW-UHFFFAOYSA-N 4-chloro-2-fluoro-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound FC1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 MPNSNZPKUAKLLW-UHFFFAOYSA-N 0.000 claims description 5
- JUPURURDYZDQFU-UHFFFAOYSA-N 4-chloro-n-[2-(4-fluorophenyl)pyrazol-3-yl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1N1C(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC=N1 JUPURURDYZDQFU-UHFFFAOYSA-N 0.000 claims description 5
- GSJUDRQFHFHURG-UHFFFAOYSA-N 4-chloro-n-[2-(4-methylpyridin-2-yl)pyrazol-3-yl]benzenesulfonamide Chemical compound CC1=CC=NC(N2C(=CC=N2)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 GSJUDRQFHFHURG-UHFFFAOYSA-N 0.000 claims description 5
- WBZIUOPWQGHQHC-UHFFFAOYSA-N 4-cyano-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 WBZIUOPWQGHQHC-UHFFFAOYSA-N 0.000 claims description 5
- PDLYMYGATFSPBD-UHFFFAOYSA-N 4-cyano-n-[2-(4-methylpyridin-2-yl)pyrazol-3-yl]benzenesulfonamide Chemical compound CC1=CC=NC(N2C(=CC=N2)NS(=O)(=O)C=2C=CC(=CC=2)C#N)=C1 PDLYMYGATFSPBD-UHFFFAOYSA-N 0.000 claims description 5
- DQQRVGDHCULQEE-UHFFFAOYSA-N 4-ethyl-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 DQQRVGDHCULQEE-UHFFFAOYSA-N 0.000 claims description 5
- JQRQSQXXJMMAMJ-UHFFFAOYSA-N 4-ethyl-n-[2-(4-methylpyridin-2-yl)pyrazol-3-yl]benzenesulfonamide Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC(C)=CC=N1 JQRQSQXXJMMAMJ-UHFFFAOYSA-N 0.000 claims description 5
- HYNNFDQUJJXIPZ-UHFFFAOYSA-N 4-propyl-n-(2-pyridin-2-ylpyrazol-3-yl)benzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=N1 HYNNFDQUJJXIPZ-UHFFFAOYSA-N 0.000 claims description 5
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- 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
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- 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
- A61P25/18—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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
- C07D231/42—Benzene-sulfonamido pyrazoles
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13151632 | 2013-01-17 | ||
| EP13151632.0 | 2013-01-17 | ||
| PCT/EP2014/050526 WO2014111356A1 (en) | 2013-01-17 | 2014-01-14 | Oxytocin receptor agonists for the treatment of cns diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150108384A true KR20150108384A (ko) | 2015-09-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157021897A Withdrawn KR20150108384A (ko) | 2013-01-17 | 2014-01-14 | 중추신경계 질병의 치료를 위한 옥시토신 수용체 작용제 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9751870B2 (https=) |
| EP (1) | EP2945624B1 (https=) |
| JP (1) | JP6263553B2 (https=) |
| KR (1) | KR20150108384A (https=) |
| CN (1) | CN104936593B (https=) |
| BR (1) | BR112015016323A2 (https=) |
| CA (1) | CA2898015A1 (https=) |
| MX (1) | MX2015008830A (https=) |
| RU (1) | RU2664705C2 (https=) |
| WO (1) | WO2014111356A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10039777B2 (en) | 2012-03-20 | 2018-08-07 | Neuro-Lm Sas | Methods and pharmaceutical compositions of the treatment of autistic syndrome disorders |
| ES2970059T3 (es) * | 2014-09-19 | 2024-05-24 | Ferring Bv | Método de tratamiento del síndrome de Prader-Willi |
| EP3852724A4 (en) | 2018-09-20 | 2022-07-06 | Levo Therapeutics, Inc. | CARBETOCIN DRUG PRODUCT AND PROCESS FOR ITS MANUFACTURE |
| TW202031283A (zh) | 2018-09-20 | 2020-09-01 | 馬克 Ｃ 曼寧 | 穩定卡貝縮宮素鼻內製劑 |
| EP3934636A1 (en) * | 2019-03-06 | 2022-01-12 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Inhibitors of ngal protein |
| ES3010259T3 (en) | 2021-03-26 | 2025-04-01 | Ot4B | Treatment of dysphagia |
| CN116459261A (zh) * | 2023-02-27 | 2023-07-21 | 徐州医科大学 | Lit-001在治疗焦虑疾病中的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014038A (en) * | 1961-12-19 | Xnhxs | ||
| GB893755A (en) | 1958-06-25 | 1962-04-11 | Ciba Ltd | New pyrazoles and process for their manufacture |
| DE1115739B (de) | 1958-06-25 | 1961-10-26 | Ciba Geigy | Verfahren zur Herstellung von 1-Phenyl-5-(benzolsulfonamido)-pyrazolen |
| GB865341A (en) | 1958-07-30 | 1961-04-12 | Bayer Ag | 5-benzene-sulphonamido-1-phenyl pyrazole derivatives |
| DE1115261B (de) * | 1958-07-30 | 1961-10-19 | Bayer Ag | Verfahren zur Herstellung von 1-Phenyl-5-(benzolsulfonamido)-pyrazolen |
| FR3797M (fr) * | 1963-11-05 | 1965-12-27 | Ciba Geigy | Nouvelle préparation pharmaceutique pour le traitement du diabetes mellitus. |
| US6531478B2 (en) * | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
| FR2864958B1 (fr) * | 2004-01-12 | 2006-02-24 | Sanofi Synthelabo | Derive de n-[(1,5-diphenyl-1h-pyrazol-3-yl)methyl] sulfonamide, leur preparation et leur application en therapeutique. |
| BRPI0820432B8 (pt) * | 2007-11-13 | 2021-05-25 | Taisho Pharmaceutical Co Ltd | derivados de fenilpirazol apresentando atividade de antagonista de receptor de histamina h3 e um agente profilático ou terapeutico compreendendo tais derivados |
| WO2010118063A2 (en) | 2009-04-06 | 2010-10-14 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| WO2012016229A2 (en) | 2010-07-30 | 2012-02-02 | The Regents Of The University Of California | Oxytocin treatment to improve memory and modify blood glucose |
-
2014
- 2014-01-14 RU RU2015130950A patent/RU2664705C2/ru not_active IP Right Cessation
- 2014-01-14 KR KR1020157021897A patent/KR20150108384A/ko not_active Withdrawn
- 2014-01-14 CA CA2898015A patent/CA2898015A1/en not_active Abandoned
- 2014-01-14 BR BR112015016323A patent/BR112015016323A2/pt not_active Application Discontinuation
- 2014-01-14 EP EP14700614.2A patent/EP2945624B1/en not_active Not-in-force
- 2014-01-14 CN CN201480004903.5A patent/CN104936593B/zh not_active Expired - Fee Related
- 2014-01-14 MX MX2015008830A patent/MX2015008830A/es unknown
- 2014-01-14 JP JP2015553055A patent/JP6263553B2/ja not_active Expired - Fee Related
- 2014-01-14 WO PCT/EP2014/050526 patent/WO2014111356A1/en not_active Ceased
-
2015
- 2015-07-17 US US14/802,469 patent/US9751870B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9751870B2 (en) | 2017-09-05 |
| EP2945624B1 (en) | 2018-04-18 |
| HK1209032A1 (en) | 2016-03-24 |
| MX2015008830A (es) | 2015-10-14 |
| EP2945624A1 (en) | 2015-11-25 |
| RU2664705C2 (ru) | 2018-08-21 |
| RU2015130950A (ru) | 2017-02-21 |
| JP2016506910A (ja) | 2016-03-07 |
| JP6263553B2 (ja) | 2018-01-17 |
| CN104936593B (zh) | 2018-05-18 |
| CN104936593A (zh) | 2015-09-23 |
| CA2898015A1 (en) | 2014-07-24 |
| WO2014111356A1 (en) | 2014-07-24 |
| BR112015016323A2 (pt) | 2017-07-11 |
| US20150322058A1 (en) | 2015-11-12 |
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