MXPA00002616A - Combinacion de un inhibidor de la monoamina-oxidasa y un antagonista o agonista parcial de h5-ht1b. - Google Patents
Combinacion de un inhibidor de la monoamina-oxidasa y un antagonista o agonista parcial de h5-ht1b.Info
- Publication number
- MXPA00002616A MXPA00002616A MXPA00002616A MXPA00002616A MXPA00002616A MX PA00002616 A MXPA00002616 A MX PA00002616A MX PA00002616 A MXPA00002616 A MX PA00002616A MX PA00002616 A MXPA00002616 A MX PA00002616A MX PA00002616 A MXPA00002616 A MX PA00002616A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- naphthyl
- tetrahydro
- piperazin
- mmol
- Prior art date
Links
- 239000002899 monoamine oxidase inhibitor Substances 0.000 title claims abstract description 15
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000005557 antagonist Substances 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 208000019022 Mood disease Diseases 0.000 claims abstract description 8
- 239000004031 partial agonist Substances 0.000 claims abstract description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 145
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 54
- -1 4-ethylpiperazin-1-yl Chemical group 0.000 claims description 51
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052794 bromium Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 5
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- OOEQHHKVTDYZTD-OAQYLSRUSA-N 4-morpholin-4-yl-n-[(2r)-8-piperazin-1-yl-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide Chemical compound C([C@H](CC1=2)NC(=O)C=3C=CC(=CC=3)N3CCOCC3)CC1=CC=CC=2N1CCNCC1 OOEQHHKVTDYZTD-OAQYLSRUSA-N 0.000 claims description 3
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical group C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004644 moclobemide Drugs 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- HWSWMVFTXFBDRW-JOCHJYFZSA-N n-[(2r)-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C1CN(C)CCN1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)N1CCOCC1)CC2 HWSWMVFTXFBDRW-JOCHJYFZSA-N 0.000 claims description 3
- 229960000964 phenelzine Drugs 0.000 claims description 3
- GLCNLSFPYIMZJK-HXUWFJFHSA-N (2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C([C@H](CC=12)C(=O)NC=3C=CC(=CC=3)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 GLCNLSFPYIMZJK-HXUWFJFHSA-N 0.000 claims description 2
- GLCNLSFPYIMZJK-UHFFFAOYSA-N 5-methoxy-8-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C1=2CC(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 GLCNLSFPYIMZJK-UHFFFAOYSA-N 0.000 claims description 2
- GGWPSJWVARDUIR-UHFFFAOYSA-N 8-methoxy-5-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1=2CC(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)COC=2C(OC)=CC=C1N1CCN(C)CC1 GGWPSJWVARDUIR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- OXZHFWAHGKDGDI-LJQANCHMSA-N n-[(2r)-5-bromo-8-piperazin-1-yl-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)N3CCOCC3)CC=1C(Br)=CC=C2N1CCNCC1 OXZHFWAHGKDGDI-LJQANCHMSA-N 0.000 claims description 2
- WZMSJJIAEOODBC-JOCHJYFZSA-N n-[(2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-(morpholine-4-carbonyl)benzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)C(=O)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 WZMSJJIAEOODBC-JOCHJYFZSA-N 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- BSBVBFLNLYJFBZ-QGZVFWFLSA-N n-[(2r)-5-bromo-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC=C(Br)C2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)C(F)(F)F)CC2 BSBVBFLNLYJFBZ-QGZVFWFLSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 abstract description 4
- 230000036506 anxiety Effects 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 164
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 144
- 239000002904 solvent Substances 0.000 description 115
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 238000006243 chemical reaction Methods 0.000 description 100
- 239000000243 solution Substances 0.000 description 89
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- 229960001701 chloroform Drugs 0.000 description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 62
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 229910052757 nitrogen Inorganic materials 0.000 description 57
- 239000003480 eluent Substances 0.000 description 50
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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- 239000003054 catalyst Substances 0.000 description 18
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229940069575 rompun Drugs 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000004000 serotonin 1B antagonist Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- GGGBHGKCSXURHO-JOCHJYFZSA-N tert-butyl 4-[(7r)-4-bromo-7-[(4-morpholin-4-ylbenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-1-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(Br)C2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)N1CCOCC1)CC2 GGGBHGKCSXURHO-JOCHJYFZSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9703376A SE9703376D0 (sv) | 1997-09-18 | 1997-09-18 | A new combination |
| PCT/SE1998/001602 WO1999013878A1 (en) | 1997-09-18 | 1998-09-09 | A COMBINATION OF A MONOAMINE OXIDASE INHIBITOR AND A h5-HT1B ANTAGONIST OR PARTIAL AGONIST |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00002616A true MXPA00002616A (es) | 2002-04-24 |
Family
ID=20408296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA00002616A MXPA00002616A (es) | 1997-09-18 | 1998-09-09 | Combinacion de un inhibidor de la monoamina-oxidasa y un antagonista o agonista parcial de h5-ht1b. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6159970A (enExample) |
| EP (1) | EP1014986B1 (enExample) |
| JP (1) | JP2001516719A (enExample) |
| KR (2) | KR20010024087A (enExample) |
| CN (1) | CN1278727A (enExample) |
| AR (1) | AR013503A1 (enExample) |
| AT (1) | ATE270889T1 (enExample) |
| AU (1) | AU752719B2 (enExample) |
| BR (1) | BR9812236A (enExample) |
| CA (1) | CA2302204A1 (enExample) |
| DE (1) | DE69825062T2 (enExample) |
| DK (1) | DK1014986T3 (enExample) |
| EE (1) | EE200000146A (enExample) |
| ES (1) | ES2222603T3 (enExample) |
| HU (1) | HUP0100621A2 (enExample) |
| ID (1) | ID25789A (enExample) |
| IL (1) | IL134775A0 (enExample) |
| IS (1) | IS5401A (enExample) |
| MX (1) | MXPA00002616A (enExample) |
| NO (1) | NO20001400L (enExample) |
| PL (1) | PL339368A1 (enExample) |
| PT (1) | PT1014986E (enExample) |
| SE (1) | SE9703376D0 (enExample) |
| SK (1) | SK2832000A3 (enExample) |
| TR (1) | TR200000725T2 (enExample) |
| WO (1) | WO1999013878A1 (enExample) |
| ZA (1) | ZA987804B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
| SE9601110D0 (sv) | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
| WO2002066454A1 (fr) * | 2001-02-21 | 2002-08-29 | Sankyo Company, Limited | Derives de chromene |
| ES2323451T7 (es) * | 2001-07-20 | 2011-08-01 | Psychogenics Inc. | Tratamiento para el trastorno de hiperactividad con deficit de atencion. |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| US20090054453A1 (en) * | 2006-03-17 | 2009-02-26 | Lilian Alcaraz | Novel Tetralins as 5-HT6 Modulators |
| US8278345B2 (en) | 2006-11-09 | 2012-10-02 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| SI2091948T1 (sl) | 2006-11-30 | 2012-07-31 | Probiodrug Ag | Novi inhibitorji glutaminil ciklaze |
| EA200901140A1 (ru) | 2007-03-01 | 2010-04-30 | Пробиодруг Аг | Новое применение ингибиторов глутаминилциклазы |
| EP2142514B1 (en) | 2007-04-18 | 2014-12-24 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
| CN102695546B (zh) | 2009-09-11 | 2014-09-10 | 前体生物药物股份公司 | 作为谷氨酰胺酰环化酶抑制剂的杂环衍生物 |
| WO2011107530A2 (en) | 2010-03-03 | 2011-09-09 | Probiodrug Ag | Novel inhibitors |
| SG183229A1 (en) | 2010-03-10 | 2012-09-27 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| EP2560953B1 (en) | 2010-04-21 | 2016-01-06 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| WO2012123563A1 (en) | 2011-03-16 | 2012-09-20 | Probiodrug Ag | Benz imidazole derivatives as inhibitors of glutaminyl cyclase |
| DK3461819T3 (da) | 2017-09-29 | 2020-08-10 | Probiodrug Ag | Inhibitorer af glutaminylcyklase |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
| CN110179988A (zh) * | 2019-07-10 | 2019-08-30 | 王大伟 | 五羟色胺再摄取抑制剂和单胺氧化酶抑制剂联合在制备治疗抑郁症或早泄药物中的应用 |
| EP4633638A1 (en) * | 2022-12-14 | 2025-10-22 | Luminous Mind Inc. | Treatment of psychological factors affecting other medical conditions (pfaomc) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9119932D0 (en) * | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
| DE69232003T2 (de) * | 1991-09-18 | 2002-04-25 | Glaxo Group Ltd., Greenford | Benzanilidderivate als 5-HT1D-Antagonisten |
| SE9601110D0 (sv) * | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
-
1997
- 1997-09-18 SE SE9703376A patent/SE9703376D0/xx unknown
-
1998
- 1998-08-27 ZA ZA987804A patent/ZA987804B/xx unknown
- 1998-09-09 IL IL13477598A patent/IL134775A0/xx unknown
- 1998-09-09 WO PCT/SE1998/001602 patent/WO1999013878A1/en not_active Ceased
- 1998-09-09 CN CN98811114A patent/CN1278727A/zh active Pending
- 1998-09-09 PT PT98944376T patent/PT1014986E/pt unknown
- 1998-09-09 DK DK98944376T patent/DK1014986T3/da active
- 1998-09-09 KR KR1020007002835A patent/KR20010024087A/ko not_active Ceased
- 1998-09-09 KR KR1020007002830A patent/KR20010024084A/ko not_active Withdrawn
- 1998-09-09 PL PL98339368A patent/PL339368A1/xx unknown
- 1998-09-09 US US09/171,578 patent/US6159970A/en not_active Expired - Fee Related
- 1998-09-09 BR BR9812236-3A patent/BR9812236A/pt not_active IP Right Cessation
- 1998-09-09 CA CA002302204A patent/CA2302204A1/en not_active Abandoned
- 1998-09-09 EP EP98944376A patent/EP1014986B1/en not_active Expired - Lifetime
- 1998-09-09 ID IDW20000522D patent/ID25789A/id unknown
- 1998-09-09 TR TR2000/00725T patent/TR200000725T2/xx unknown
- 1998-09-09 JP JP2000511500A patent/JP2001516719A/ja active Pending
- 1998-09-09 AT AT98944376T patent/ATE270889T1/de not_active IP Right Cessation
- 1998-09-09 HU HU0100621A patent/HUP0100621A2/hu unknown
- 1998-09-09 SK SK283-2000A patent/SK2832000A3/sk unknown
- 1998-09-09 ES ES98944376T patent/ES2222603T3/es not_active Expired - Lifetime
- 1998-09-09 DE DE69825062T patent/DE69825062T2/de not_active Expired - Fee Related
- 1998-09-09 EE EEP200000146A patent/EE200000146A/xx unknown
- 1998-09-09 MX MXPA00002616A patent/MXPA00002616A/es unknown
- 1998-09-09 AU AU91931/98A patent/AU752719B2/en not_active Ceased
- 1998-09-17 AR ARP980104635A patent/AR013503A1/es unknown
-
2000
- 2000-03-14 IS IS5401A patent/IS5401A/is unknown
- 2000-03-17 NO NO20001400A patent/NO20001400L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US6159970A (en) | 2000-12-12 |
| DE69825062D1 (de) | 2004-08-19 |
| SK2832000A3 (en) | 2000-09-12 |
| CA2302204A1 (en) | 1999-03-25 |
| NO20001400L (no) | 2000-05-05 |
| NO20001400D0 (no) | 2000-03-17 |
| SE9703376D0 (sv) | 1997-09-18 |
| ZA987804B (en) | 1999-03-18 |
| HUP0100621A2 (hu) | 2001-08-28 |
| ES2222603T3 (es) | 2005-02-01 |
| AU752719B2 (en) | 2002-09-26 |
| EP1014986A1 (en) | 2000-07-05 |
| JP2001516719A (ja) | 2001-10-02 |
| DK1014986T3 (da) | 2004-10-25 |
| IS5401A (is) | 2000-03-14 |
| EE200000146A (et) | 2001-02-15 |
| CN1278727A (zh) | 2001-01-03 |
| ID25789A (id) | 2000-11-02 |
| ATE270889T1 (de) | 2004-07-15 |
| AR013503A1 (es) | 2000-12-27 |
| PT1014986E (pt) | 2004-10-29 |
| EP1014986B1 (en) | 2004-07-14 |
| KR20010024084A (ko) | 2001-03-26 |
| PL339368A1 (en) | 2000-12-18 |
| BR9812236A (pt) | 2000-07-18 |
| KR20010024087A (ko) | 2001-03-26 |
| IL134775A0 (en) | 2001-04-30 |
| TR200000725T2 (tr) | 2000-08-21 |
| DE69825062T2 (de) | 2005-08-25 |
| AU9193198A (en) | 1999-04-05 |
| WO1999013878A1 (en) | 1999-03-25 |
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