AU691858B2 - Novel heterocyclic compounds - Google Patents
Novel heterocyclic compounds Download PDFInfo
- Publication number
- AU691858B2 AU691858B2 AU13110/95A AU1311095A AU691858B2 AU 691858 B2 AU691858 B2 AU 691858B2 AU 13110/95 A AU13110/95 A AU 13110/95A AU 1311095 A AU1311095 A AU 1311095A AU 691858 B2 AU691858 B2 AU 691858B2
- Authority
- AU
- Australia
- Prior art keywords
- propyl
- added
- dihydro
- mol
- dibenzo
- 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.)
- Ceased
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 122
- 238000000034 method Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 2
- 229940091860 GABA uptake inhibitor Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
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- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000002843 gaba uptake inhibitor Substances 0.000 claims description 2
- NJLAEBZVVOVDPS-UHFFFAOYSA-N hexyl 1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OCCCCCC)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 NJLAEBZVVOVDPS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- FEQDVTZJXGQYJE-UHFFFAOYSA-N methyl 1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OC)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 FEQDVTZJXGQYJE-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 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 description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 claims 2
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- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229960001918 tiagabine Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 21
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- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- 238000001035 drying Methods 0.000 description 17
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
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- 238000001816 cooling Methods 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- HHPGQKZOPPDLNH-OGFXRTJISA-N 2,3-dihydroxybutanedioic acid;ethyl (3r)-piperidine-3-carboxylate Chemical compound OC(=O)C(O)C(O)C(O)=O.CCOC(=O)[C@@H]1CCCNC1 HHPGQKZOPPDLNH-OGFXRTJISA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 10
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
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- 208000002193 Pain Diseases 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 230000014759 maintenance of location Effects 0.000 description 6
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- HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-UHFFFAOYSA-N 0.000 description 5
- -1 4-phenyl-4-piperidinecarboxylic acid ester Chemical class 0.000 description 5
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- 230000005764 inhibitory process Effects 0.000 description 5
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- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 239000002997 ophthalmic solution Substances 0.000 description 1
- 229940054534 ophthalmic solution Drugs 0.000 description 1
- 230000001009 osteoporotic effect Effects 0.000 description 1
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- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- DJZBNHNGWYWZKE-UHFFFAOYSA-M sodium;1-[3-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propyl]piperidine-3-carboxylate Chemical compound [Na+].C1C(C(=O)[O-])CCCN1CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C21 DJZBNHNGWYWZKE-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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Classifications
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK0019/94 | 1994-01-04 | ||
| DK1994 | 1994-01-04 | ||
| DK1290/94 | 1994-11-09 | ||
| DK129094 | 1994-11-09 | ||
| PCT/DK1995/000002 WO1995018793A1 (en) | 1994-01-04 | 1995-01-03 | Novel heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1311095A AU1311095A (en) | 1995-08-01 |
| AU691858B2 true AU691858B2 (en) | 1998-05-28 |
Family
ID=26063135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU13110/95A Ceased AU691858B2 (en) | 1994-01-04 | 1995-01-03 | Novel heterocyclic compounds |
Country Status (31)
| Country | Link |
|---|---|
| US (8) | US5595989A (enExample) |
| EP (1) | EP0738262B1 (enExample) |
| JP (1) | JP2944221B2 (enExample) |
| KR (1) | KR100329450B1 (enExample) |
| CN (1) | CN1083431C (enExample) |
| AT (1) | ATE191909T1 (enExample) |
| AU (1) | AU691858B2 (enExample) |
| BG (1) | BG100692A (enExample) |
| BR (1) | BR9506452A (enExample) |
| CA (1) | CA2180238A1 (enExample) |
| CZ (1) | CZ286109B6 (enExample) |
| DE (1) | DE69516394T2 (enExample) |
| DK (1) | DK0738262T3 (enExample) |
| ES (1) | ES2147837T3 (enExample) |
| FI (1) | FI114025B (enExample) |
| GR (1) | GR3033967T3 (enExample) |
| HU (1) | HUT75878A (enExample) |
| IL (1) | IL112222A (enExample) |
| MY (1) | MY113463A (enExample) |
| NO (1) | NO306295B1 (enExample) |
| NZ (1) | NZ277763A (enExample) |
| PE (1) | PE45095A1 (enExample) |
| PL (1) | PL180209B1 (enExample) |
| PT (1) | PT738262E (enExample) |
| RU (1) | RU2167152C2 (enExample) |
| SG (1) | SG50602A1 (enExample) |
| SI (1) | SI9520023A (enExample) |
| SK (1) | SK88196A3 (enExample) |
| TW (1) | TW300887B (enExample) |
| UA (1) | UA47396C2 (enExample) |
| WO (1) | WO1995018793A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6239148B1 (en) | 1994-01-04 | 2001-05-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| MY113463A (en) * | 1994-01-04 | 2002-03-30 | Novo Nordisk As | Novel heterocyclic compounds |
| US6110913A (en) * | 1994-01-04 | 2000-08-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| US5716949A (en) * | 1995-04-07 | 1998-02-10 | Novo Nordisk A/S | Heterocyclic compounds |
| US5952352A (en) * | 1995-04-07 | 1999-09-14 | Novo Nordisk A/S | Heterocyclic compounds |
| US5962449A (en) | 1995-04-07 | 1999-10-05 | Novo Nordisk A/S | Tricyclic compounds in treating hyperalgesic conditions and NIDDM |
| UA54385C2 (uk) * | 1995-04-07 | 2003-03-17 | Ново Нордіск А/С | N-заміщені азагетероциклічні карбонові кислоти та їх ефіри, спосіб їх одержання, фармацевтична композиція та спосіб лікування |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| KR20000064411A (ko) | 1995-12-15 | 2000-11-06 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 새로운방법 |
| US6323206B1 (en) | 1996-07-12 | 2001-11-27 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| HUP0000088A3 (en) * | 1996-10-04 | 2000-09-28 | Novo Nordisk As | N-substituted azaheterocyclic compounds, process for producing them and pharmaceutical compositions containing them |
| ZA978792B (en) * | 1996-10-04 | 1998-04-06 | Novo Nordisk As | N-substituted azaheterocyclic compounds. |
| KR20000048899A (ko) * | 1996-10-04 | 2000-07-25 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 1,4-디치환 피페라진 |
| US6040318A (en) * | 1997-06-25 | 2000-03-21 | Novo Nordisk A/S | Tricycle substituted with azaheterocyclic carboxylic acids |
| EP1049684A1 (en) | 1997-10-27 | 2000-11-08 | Dr. Reddy's Research Foundation | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| CA2319077A1 (en) | 1998-01-21 | 1999-07-29 | Yoshisuke Nakasato | Chemokine receptor antagonists and methods of use therefor |
| US6613905B1 (en) | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6509346B2 (en) | 1998-01-21 | 2003-01-21 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| JP2002501052A (ja) * | 1998-01-21 | 2002-01-15 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | ケモカイン受容体アンタゴニストおよびその使用方法 |
| ES2137136B1 (es) * | 1998-05-18 | 2000-07-01 | Esteve Labor Dr | Empleo de derivados de aril (o heteroaril) azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica. |
| US7271176B2 (en) * | 1998-09-04 | 2007-09-18 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use thereof |
| US6468996B1 (en) * | 1998-10-21 | 2002-10-22 | Novo Nordisk A/S | Substituted hetero-polycyclic compounds as PPARα and PPARγ activators |
| EP1140084A1 (en) * | 1998-12-22 | 2001-10-10 | Novo Nordisk A/S | Novel formulation |
| US6207682B1 (en) | 1998-12-22 | 2001-03-27 | Novo Nordisk A/S | Modified release formulations containing (R)-1-(10,11-dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1propyl)-3-piperidinecarboxylic acid |
| US7355042B2 (en) * | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| US7541365B2 (en) | 2001-11-21 | 2009-06-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US20040087642A1 (en) * | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising a JNK inhibitor for the treatment, prevention, management and/or modification of pain |
| TWI291467B (en) | 2002-11-13 | 2007-12-21 | Millennium Pharm Inc | CCR1 antagonists and methods of use therefor |
| US20070066570A1 (en) * | 2003-06-16 | 2007-03-22 | Michael Solomon | Methods for treating sleep disorders |
| AU2007290386A1 (en) | 2006-09-01 | 2008-03-06 | Immune Control, Inc. | Novel compositions and methods for treatment of diseases related to activated lymphocytes |
| US10029995B2 (en) | 2015-09-03 | 2018-07-24 | Forma Therapeutics, Inc. | [6,6] fused bicyclic HDAC8 inhibitors |
| EP3651751A4 (en) | 2017-07-13 | 2021-03-31 | Tonix Pharmaceuticals Holding Corp. | CYCLOBENZAPRINE AND AMITRYPTILENE ANALOGUES |
| CN115850232B (zh) * | 2023-02-16 | 2023-05-26 | 广州佳途科技股份有限公司 | 一种氟哌噻吨ep杂质h的制备方法及其应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177211A (en) * | 1957-07-26 | 1965-04-06 | Sterling Drug Inc | 10-[(aminocarbamyl-1-piperidyl)-loweralkyl]-phenothiazines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3316249A (en) * | 1967-04-25 | Part a.xmethyl n n-(z-diethylaminoethyl)-n-(z- nitrophenyl) anthranilate hydrochloride | ||
| US2931810A (en) * | 1960-04-05 | Phenothiazine derivatives | ||
| BE552557A (enExample) * | 1955-11-15 | |||
| NL108827C (enExample) * | 1956-04-09 | |||
| BE562299A (enExample) * | 1956-11-15 | |||
| NL222355A (enExample) * | 1957-11-05 | |||
| FR1216268A (fr) * | 1958-04-24 | 1960-04-25 | Rhone Poulenc Sa | Nouveaux dérivés de la phénothiazine à chaîne pipéridine substituée par une fonction amide et leur préparation |
| US3069432A (en) * | 1961-02-20 | 1962-12-18 | Olin Mathieson | 5-(aminoalkyl)-5, 11-dihydrodibenzo-oxazepines |
| DE1159954B (de) * | 1961-11-25 | 1963-12-27 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung neuer 10-(Alkoxypiperidinopropyl)-phenthiazine und ihrer Salze |
| US3157658A (en) * | 1963-07-05 | 1964-11-17 | Searle & Co | 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds |
| FR145F (enExample) * | 1964-06-01 | |||
| US3886170A (en) * | 1974-04-22 | 1975-05-27 | Robins Co Inc A H | 5-(3-)SUBSTITUTED-10,11-DIHYDRO-5H-dibenz{8 b,f{9 azepines |
| US4888335A (en) * | 1988-07-25 | 1989-12-19 | Mcneilab, Inc. | 3-alkoxy-2-aminopropyl heterocyclic amines and their use as cardiovascular agents |
| US5296602A (en) * | 1991-03-18 | 1994-03-22 | Sloan-Kettering Institute For Cancer Research | Multisubstituted 1-hydroxy-9-acridones with anticancer activity |
| US5420123A (en) * | 1992-12-21 | 1995-05-30 | Bristol-Myers Squibb Company | Dibenzodiazepine endothelin antagonists |
| US5538986A (en) * | 1993-12-06 | 1996-07-23 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| MY113463A (en) * | 1994-01-04 | 2002-03-30 | Novo Nordisk As | Novel heterocyclic compounds |
-
1994
- 1994-12-30 MY MYPI94003583A patent/MY113463A/en unknown
-
1995
- 1995-01-02 IL IL11222295A patent/IL112222A/xx not_active IP Right Cessation
- 1995-01-03 US US08/367,648 patent/US5595989A/en not_active Expired - Fee Related
- 1995-01-03 AT AT95904409T patent/ATE191909T1/de not_active IP Right Cessation
- 1995-01-03 BR BR9506452A patent/BR9506452A/pt not_active IP Right Cessation
- 1995-01-03 HU HU9601842A patent/HUT75878A/hu unknown
- 1995-01-03 SK SK881-96A patent/SK88196A3/sk unknown
- 1995-01-03 SG SG1996006195A patent/SG50602A1/en unknown
- 1995-01-03 PT PT95904409T patent/PT738262E/pt unknown
- 1995-01-03 DE DE69516394T patent/DE69516394T2/de not_active Expired - Fee Related
- 1995-01-03 KR KR1019960703605A patent/KR100329450B1/ko not_active Expired - Fee Related
- 1995-01-03 ES ES95904409T patent/ES2147837T3/es not_active Expired - Lifetime
- 1995-01-03 CN CN95191845A patent/CN1083431C/zh not_active Expired - Fee Related
- 1995-01-03 PL PL95315294A patent/PL180209B1/pl not_active IP Right Cessation
- 1995-01-03 JP JP7518275A patent/JP2944221B2/ja not_active Expired - Fee Related
- 1995-01-03 CZ CZ19961921A patent/CZ286109B6/cs unknown
- 1995-01-03 SI SI9520023A patent/SI9520023A/sl unknown
- 1995-01-03 NZ NZ277763A patent/NZ277763A/en unknown
- 1995-01-03 WO PCT/DK1995/000002 patent/WO1995018793A1/en not_active Ceased
- 1995-01-03 CA CA002180238A patent/CA2180238A1/en not_active Abandoned
- 1995-01-03 RU RU96116134/04A patent/RU2167152C2/ru not_active IP Right Cessation
- 1995-01-03 DK DK95904409T patent/DK0738262T3/da active
- 1995-01-03 UA UA96072659A patent/UA47396C2/uk unknown
- 1995-01-03 AU AU13110/95A patent/AU691858B2/en not_active Ceased
- 1995-01-03 EP EP95904409A patent/EP0738262B1/en not_active Expired - Lifetime
- 1995-01-04 PE PE1995258527A patent/PE45095A1/es not_active Application Discontinuation
- 1995-02-22 TW TW084101613A patent/TW300887B/zh active
- 1995-05-18 US US08/444,140 patent/US5688788A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,500 patent/US5721254A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,682 patent/US5795888A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,502 patent/US5693649A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,905 patent/US5712292A/en not_active Expired - Fee Related
-
1996
- 1996-03-27 US US08/626,745 patent/US5668129A/en not_active Expired - Fee Related
- 1996-07-02 BG BG100692A patent/BG100692A/xx unknown
- 1996-07-03 NO NO962811A patent/NO306295B1/no not_active IP Right Cessation
- 1996-07-04 FI FI962749A patent/FI114025B/fi active
-
1998
- 1998-01-23 US US09/012,918 patent/US6043239A/en not_active Expired - Fee Related
-
2000
- 2000-07-17 GR GR20000401652T patent/GR3033967T3/el not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177211A (en) * | 1957-07-26 | 1965-04-06 | Sterling Drug Inc | 10-[(aminocarbamyl-1-piperidyl)-loweralkyl]-phenothiazines |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |