NO310070B1 - Benzo[g]kinolinderivater, fremstilling herav, farmasöytiske midler og preparater inneholdende disse samt anvendelse av derivatene for fremstilling av medikamenter - Google Patents
Benzo[g]kinolinderivater, fremstilling herav, farmasöytiske midler og preparater inneholdende disse samt anvendelse av derivatene for fremstilling av medikamenter Download PDFInfo
- Publication number
- NO310070B1 NO310070B1 NO980043A NO980043A NO310070B1 NO 310070 B1 NO310070 B1 NO 310070B1 NO 980043 A NO980043 A NO 980043A NO 980043 A NO980043 A NO 980043A NO 310070 B1 NO310070 B1 NO 310070B1
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- Prior art keywords
- formula
- compound
- acid addition
- free base
- salt form
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Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000003814 drug Substances 0.000 title claims 2
- RFQDDXWZZVRLKO-UHFFFAOYSA-N benzo[g]quinoline Chemical class N1=CC=CC2=CC3=CC=CC=C3C=C21 RFQDDXWZZVRLKO-UHFFFAOYSA-N 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 48
- 150000003839 salts Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 208000020925 Bipolar disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
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- 238000000034 method Methods 0.000 claims description 6
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- -1 R 2 is H Chemical group 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
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- 102000005157 Somatostatin Human genes 0.000 claims description 2
- 108010056088 Somatostatin Proteins 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 2
- 229960000553 somatostatin Drugs 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- WKWBAURLIBHVJN-PGCMWVOQSA-N (3r,4ar,10ar)-6-methoxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2h-benzo[g]quinoline-3-carboxylic acid;4-(4-nitrophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)N)CCN1C1=CC=C([N+]([O-])=O)C=C1.C1C=2C(OC)=CC=CC=2C[C@@H]2[C@@H]1C[C@@H](C(O)=O)CN2C WKWBAURLIBHVJN-PGCMWVOQSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 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 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 206010041243 Social avoidant behaviour Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 2
- 229960004170 clozapine Drugs 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 1
- QTYRAOOHLZVFGP-UHFFFAOYSA-N 4-(4-nitrophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)N)CCN1C1=CC=C([N+]([O-])=O)C=C1 QTYRAOOHLZVFGP-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 238000010640 amide synthesis reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940073577 lithium chloride Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 108010082379 somatostatin receptor type 1 Proteins 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
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Classifications
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/535—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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9513880.6A GB9513880D0 (en) | 1995-07-07 | 1995-07-07 | Organic compounds |
| GBGB9603988.8A GB9603988D0 (en) | 1996-02-26 | 1996-02-26 | Organic compounds |
| PCT/EP1996/002969 WO1997003054A1 (en) | 1995-07-07 | 1996-07-05 | BENZO[g]QUINOLINE DERIVATIVES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO980043D0 NO980043D0 (no) | 1998-01-05 |
| NO980043L NO980043L (no) | 1998-01-05 |
| NO310070B1 true NO310070B1 (no) | 2001-05-14 |
Family
ID=26307342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO980043A NO310070B1 (no) | 1995-07-07 | 1998-01-05 | Benzo[g]kinolinderivater, fremstilling herav, farmasöytiske midler og preparater inneholdende disse samt anvendelse av derivatene for fremstilling av medikamenter |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5885988A (tr) |
| EP (1) | EP0839136B1 (tr) |
| JP (1) | JPH11509197A (tr) |
| KR (1) | KR19990028757A (tr) |
| CN (1) | CN1193964A (tr) |
| AR (1) | AR004672A1 (tr) |
| AT (1) | ATE201199T1 (tr) |
| AU (1) | AU703325B2 (tr) |
| BR (1) | BR9609326A (tr) |
| CA (1) | CA2224436A1 (tr) |
| CO (1) | CO4750662A1 (tr) |
| CZ (1) | CZ1698A3 (tr) |
| DE (1) | DE69612852T2 (tr) |
| DK (1) | DK0839136T3 (tr) |
| ES (1) | ES2158327T3 (tr) |
| GR (1) | GR3036346T3 (tr) |
| HU (1) | HUP9802937A3 (tr) |
| IL (1) | IL122854A (tr) |
| NO (1) | NO310070B1 (tr) |
| NZ (1) | NZ313606A (tr) |
| PE (1) | PE1998A1 (tr) |
| PL (1) | PL324106A1 (tr) |
| PT (1) | PT839136E (tr) |
| RU (1) | RU2158738C2 (tr) |
| SK (1) | SK1798A3 (tr) |
| TR (1) | TR199800011T1 (tr) |
| TW (1) | TW357143B (tr) |
| WO (1) | WO1997003054A1 (tr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711043D0 (en) | 1997-05-29 | 1997-07-23 | Ciba Geigy Ag | Organic compounds |
| EP1070054A1 (en) * | 1998-04-08 | 2001-01-24 | Takeda Chemical Industries, Ltd. | Amine compounds, their production and their use as somatostatin receptor antagonists or agonists |
| CA2246791A1 (en) * | 1998-09-01 | 2000-03-01 | Alison Buchan | Treatment of endothelium with somatostatin analogues |
| DE69938005T2 (de) * | 1998-09-22 | 2009-01-15 | Astellas Pharma Inc. | Cyanophenyl-derivate |
| GB9902938D0 (en) * | 1999-02-10 | 1999-03-31 | Novartis Ag | Organic compounds |
| PE20030240A1 (es) * | 2001-07-09 | 2003-04-16 | Novartis Ag | DERIVADOS DE BENZO [g] QUINOLINA |
| FI20031454A0 (fi) | 2003-10-06 | 2003-10-06 | Juvantia Pharma Ltd Oy | Selektiivisiä somatostatiinireseptori 1 ja/tai 4 -agonisteja ja -antagonisteja |
| KR100594234B1 (ko) | 2003-12-05 | 2006-06-30 | 삼성전자주식회사 | 편광 현상을 이용하여 해상도를 향상시킬 수 있는 포토마스크 및 그 제조방법 |
| CN101084211A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
| JP4958785B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼインヒビターとしてのそれらの使用 |
| AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| US7767677B2 (en) | 2004-09-20 | 2010-08-03 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| AR051094A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| WO2007130075A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| TWI404702B (zh) * | 2007-08-31 | 2013-08-11 | Lundbeck & Co As H | 兒茶酚胺衍生物和其前藥 |
| US8067410B2 (en) | 2008-06-27 | 2011-11-29 | H. Lundbeck A/S | Phenolic and catecholic amines and prodrugs thereof |
| JP7343170B2 (ja) | 2017-05-12 | 2023-09-12 | ボード オブ トラスティーズ オブ ザ サザン イリノイ ユニバーシティ オン ビハーフ オブ サザン イリノイ ユニバーシティ エドワーズビル | ３，４，５－三置換－１，２，４－トリアゾールおよび３，４，５－三置換－３－チオ－１，２，４－トリアゾール、ならびにそれらの使用 |
| US11912687B2 (en) | 2017-05-12 | 2024-02-27 | Board of Trustees of the Southern Illinois University | 3,4,5-trisubstituted-1,2,4-triazoles and 3,4,5-trisubstituted-3-thio-1,2,4-triazoles and uses thereof |
| CN117599073A (zh) | 2017-11-24 | 2024-02-27 | H.隆德贝克有限公司 | 用于治疗帕金森病的新儿茶酚胺前药 |
| US11130775B2 (en) | 2019-05-20 | 2021-09-28 | H. Lundbeck A/S | Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11111263B2 (en) | 2019-05-20 | 2021-09-07 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11168056B2 (en) | 2019-05-20 | 2021-11-09 | H. Lundbeck A/S | Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol |
| US11104697B2 (en) | 2019-05-20 | 2021-08-31 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4AR,10AR)-7-hydroxy-1- propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| JP7099717B2 (ja) | 2019-09-30 | 2022-07-12 | 株式会社理研バイオ | ソマトスタチン受容体 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE56958T1 (de) * | 1981-10-16 | 1990-10-15 | Sandoz Ag | 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)chinolinderivate mit pharmazeutischer wirkung. |
| HU193979B (en) * | 1984-06-12 | 1987-12-28 | Sandoz Ag | Process for producing naphtoxazine derivatives and pharmaceutical compositions containing them |
| NL8702680A (nl) * | 1986-11-21 | 1988-06-16 | Sandoz Ag | Nieuwe benzogchinolinen en werkwijzen voor het bereiden en toepassen van deze verbindingen. |
| DE4329776A1 (de) * | 1993-09-03 | 1995-03-09 | Sandoz Ag | Naphthoxazine, ihre Herstellung und Verwendung |
-
1996
- 1996-06-12 TW TW085107047A patent/TW357143B/zh active
- 1996-07-05 NZ NZ313606A patent/NZ313606A/xx unknown
- 1996-07-05 US US08/983,535 patent/US5885988A/en not_active Expired - Fee Related
- 1996-07-05 WO PCT/EP1996/002969 patent/WO1997003054A1/en not_active Application Discontinuation
- 1996-07-05 EP EP96925672A patent/EP0839136B1/en not_active Expired - Lifetime
- 1996-07-05 CA CA002224436A patent/CA2224436A1/en not_active Abandoned
- 1996-07-05 CN CN96196551A patent/CN1193964A/zh active Pending
- 1996-07-05 PE PE1996000517A patent/PE1998A1/es not_active Application Discontinuation
- 1996-07-05 ES ES96925672T patent/ES2158327T3/es not_active Expired - Lifetime
- 1996-07-05 CO CO96035363A patent/CO4750662A1/es unknown
- 1996-07-05 RU RU98102128/04A patent/RU2158738C2/ru active
- 1996-07-05 CZ CZ9816A patent/CZ1698A3/cs unknown
- 1996-07-05 TR TR1998/00011T patent/TR199800011T1/tr unknown
- 1996-07-05 AR ARP960103468A patent/AR004672A1/es unknown
- 1996-07-05 HU HU9802937A patent/HUP9802937A3/hu unknown
- 1996-07-05 PL PL96324106A patent/PL324106A1/xx unknown
- 1996-07-05 JP JP9505489A patent/JPH11509197A/ja active Pending
- 1996-07-05 SK SK17-98A patent/SK1798A3/sk unknown
- 1996-07-05 BR BR9609326A patent/BR9609326A/pt active Search and Examination
- 1996-07-05 DE DE69612852T patent/DE69612852T2/de not_active Expired - Fee Related
- 1996-07-05 IL IL12285496A patent/IL122854A/xx not_active IP Right Cessation
- 1996-07-05 DK DK96925672T patent/DK0839136T3/da active
- 1996-07-05 PT PT96925672T patent/PT839136E/pt unknown
- 1996-07-05 KR KR1019980700056A patent/KR19990028757A/ko not_active Application Discontinuation
- 1996-07-05 AT AT96925672T patent/ATE201199T1/de not_active IP Right Cessation
- 1996-07-05 AU AU66120/96A patent/AU703325B2/en not_active Ceased
-
1998
- 1998-01-05 NO NO980043A patent/NO310070B1/no not_active IP Right Cessation
-
2001
- 2001-08-07 GR GR20010401198T patent/GR3036346T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0839136A1 (en) | 1998-05-06 |
| RU2158738C2 (ru) | 2000-11-10 |
| BR9609326A (pt) | 1999-05-25 |
| PE1998A1 (es) | 1998-02-14 |
| MX9710530A (es) | 1998-03-31 |
| CN1193964A (zh) | 1998-09-23 |
| PL324106A1 (en) | 1998-05-11 |
| IL122854A (en) | 2000-12-06 |
| NO980043D0 (no) | 1998-01-05 |
| CO4750662A1 (es) | 1999-03-31 |
| EP0839136B1 (en) | 2001-05-16 |
| SK1798A3 (en) | 1998-06-03 |
| US5885988A (en) | 1999-03-23 |
| HUP9802937A2 (hu) | 1999-10-28 |
| IL122854A0 (en) | 1998-08-16 |
| WO1997003054A1 (en) | 1997-01-30 |
| PT839136E (pt) | 2001-09-28 |
| AR004672A1 (es) | 1999-03-10 |
| AU703325B2 (en) | 1999-03-25 |
| NO980043L (no) | 1998-01-05 |
| DE69612852D1 (de) | 2001-06-21 |
| GR3036346T3 (en) | 2001-11-30 |
| DK0839136T3 (da) | 2001-08-06 |
| AU6612096A (en) | 1997-02-10 |
| KR19990028757A (ko) | 1999-04-15 |
| HUP9802937A3 (en) | 2002-10-28 |
| CZ1698A3 (cs) | 1998-04-15 |
| TR199800011T1 (tr) | 1998-04-21 |
| TW357143B (en) | 1999-05-01 |
| JPH11509197A (ja) | 1999-08-17 |
| ES2158327T3 (es) | 2001-09-01 |
| ATE201199T1 (de) | 2001-06-15 |
| DE69612852T2 (de) | 2001-10-04 |
| NZ313606A (en) | 1999-07-29 |
| CA2224436A1 (en) | 1997-01-30 |
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