BG63083B1 - Заместени тетрациклични тетрахидрофуранови производни - Google Patents

Заместени тетрациклични тетрахидрофуранови производни Download PDF

Info

Publication number: BG63083B1
Authority: BG; Bulgaria
Prior art keywords: alkyl; formula; compounds; compound according; aryl
Prior art date: 1996-04-12

Application number

BG102820A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102820A (en

Inventor

Pilar Gil-Lopetegui

Francisco Fernandez-Gadea

Theo Meert

Original Assignee

Janssen Pharmaceutica N.V.

Priority date (The priority date 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 date listed.)

1996-04-12

Filing date

1998-10-07

Publication date

2001-03-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8223868&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=BG63083(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-10-07 Application filed by Janssen Pharmaceutica N.V. filed Critical Janssen Pharmaceutica N.V.

1999-08-31 Publication of BG102820A publication Critical patent/BG102820A/xx

2001-03-30 Publication of BG63083B1 publication Critical patent/BG63083B1/bg

Links

150000007984 tetrahydrofuranes Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 100
-1 cyano- Chemical class 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 16
150000002431 hydrogen Chemical class 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
125000000815 N-oxide group Chemical group 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000004970 halomethyl group Chemical group 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
RUKTXHCGSFMYLO-UHFFFAOYSA-N N-methyl-1-(3-oxatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7,9,11,14,16-hexaen-4-yl)methanamine Chemical compound C1C2=CC=CC=C2C2CC(CNC)OC2C2=CC=CC=C21 RUKTXHCGSFMYLO-UHFFFAOYSA-N 0.000 claims 1
238000000844 transformation Methods 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 5
208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
208000018522 Gastrointestinal disease Diseases 0.000 abstract description 2
210000003169 central nervous system Anatomy 0.000 abstract description 2
125000002757 morpholinyl group Chemical group 0.000 abstract description 2
230000002265 prevention Effects 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
230000002526 effect on cardiovascular system Effects 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
235000006408 oxalic acid Nutrition 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 26
239000000543 intermediate Substances 0.000 description 25
239000000243 solution Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
238000000034 method Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
241000700159 Rattus Species 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001204 N-oxides Chemical group 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003814 drug Substances 0.000 description 7
239000002287 radioligand Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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230000000694 effects Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
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 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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208000019695 Migraine disease Diseases 0.000 description 4
208000028017 Psychotic disease Diseases 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
201000010099 disease Diseases 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
LKKWNBWRPDKMIB-UHFFFAOYSA-N 3-chloro-1-phenylpiperazine Chemical compound C1CNC(Cl)CN1C1=CC=CC=C1 LKKWNBWRPDKMIB-UHFFFAOYSA-N 0.000 description 3
206010012335 Dependence Diseases 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000008103 glucose Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
NFZPVHBFPAGSOQ-UHFFFAOYSA-N C(C(=O)O)(=O)O.O1C(=CC=C1)CN Chemical compound C(C(=O)O)(=O)O.O1C(=CC=C1)CN NFZPVHBFPAGSOQ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
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206010013654 Drug abuse Diseases 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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239000000969 carrier Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
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XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
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238000010956 selective crystallization Methods 0.000 description 2
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230000000707 stereoselective effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
RBPHBLDGMYKMKY-BDVNFPICSA-N (2R,3R,4R,5S)-6-(methoxyamino)hexane-1,2,3,4,5-pentol Chemical compound CONC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO RBPHBLDGMYKMKY-BDVNFPICSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
- A61P25/06—Antimigraine agents
- 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
- A61P25/30—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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Pulmonology (AREA)
Addiction (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BG102820A 1996-04-12 1998-10-07 Заместени тетрациклични тетрахидрофуранови производни BG63083B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP96200990		1996-04-12
PCT/EP1997/001829 WO1997038991A1 (en)	1996-04-12	1997-04-09	Substituted tetracyclic tetrahydrofuran derivatives

Publications (2)

Publication Number	Publication Date
BG102820A BG102820A (en)	1999-08-31
BG63083B1 true BG63083B1 (bg)	2001-03-30

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ID=8223868

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BG102820A BG63083B1 (bg)	1996-04-12	1998-10-07	Заместени тетрациклични тетрахидрофуранови производни

Country Status (29)

Country	Link
US (3)	US6057441A (de)
EP (1)	EP0892793B1 (de)
JP (1)	JP3199751B2 (de)
KR (1)	KR100389298B1 (de)
CN (1)	CN1116291C (de)
AT (1)	ATE236893T1 (de)
BG (1)	BG63083B1 (de)
BR (1)	BR9706639A (de)
CA (1)	CA2232141C (de)
CY (1)	CY2382B1 (de)
CZ (1)	CZ288865B6 (de)
DE (1)	DE69720709T2 (de)
DK (1)	DK0892793T3 (de)
EA (1)	EA001002B1 (de)
EE (1)	EE03612B1 (de)
ES (1)	ES2196328T3 (de)
HU (1)	HUP9901613A3 (de)
IL (1)	IL123655A (de)
MY (1)	MY119321A (de)
NO (1)	NO317156B1 (de)
NZ (1)	NZ329953A (de)
PL (1)	PL190960B1 (de)
PT (1)	PT892793E (de)
SI (1)	SI0892793T1 (de)
SK (1)	SK283400B6 (de)
TR (1)	TR199801164T2 (de)
TW (1)	TW504506B (de)
WO (1)	WO1997038991A1 (de)
ZA (1)	ZA973114B (de)

Families Citing this family (26)

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Publication number	Priority date	Publication date	Assignee	Title
ES2196328T3 (es) *	1996-04-12	2003-12-16	Janssen Pharmaceutica Nv	Derivados de tetrahidrofurano tetraciclicos sustituidos.
UA52778C2 (uk)	1997-10-10	2003-01-15	Янссен Фармацевтика Н.В.	Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі
US20050148018A1 (en)	1999-10-07	2005-07-07	David Weiner	Methods of identifying inverse agonists of the serotonin 2A receptor
HRP20000310A2 (en) *	2000-05-17	2002-02-28	Pliva Farmaceutska Ind Dioniko	New dibenzoazulene compounds as tumor necrosis factor inhibitors
WO2002056873A2 (en) *	2000-12-22	2002-07-25	Bayer Pharmaceuticals Corporation	2-substituted dibenzo[a,e]1,2,3-triazolo[4,5-c][7]annulen-8-ones as growth hormone secretagogues
UA79248C2 (en) *	2001-11-09	2007-06-11	Janssen Pharmaceutica Nv	Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives
BR0214775A (pt) *	2001-12-07	2004-11-09	Janssen Pharmaceutica Nv	Preparação de derivados de 3,3a,8,12b-tetraidro-2h-dibenzo[3,4:6,7]ciclohepta[1,2- b]furano cis-fundidos
KR20050044329A (ko)	2001-12-07	2005-05-12	얀센 파마슈티카 엔.브이.	트랜스-융합된3,3ａ,8,12ｂ-테트라히드로-2Ｈ-디벤조[3,4:6,7]시클로헵타[1,2-ｂ]푸란 유도체의 제조
HRP20020305A8 (en)	2002-04-10	2009-03-31	GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o.	2-thia-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof
HRP20030160A2 (en) *	2003-03-06	2005-04-30	Pliva-Istra�iva�ki institut d.o.o.	1-thiadibenzoazulene derivatives and biological action thereof
HRP20030885A2 (en) *	2003-11-03	2005-08-31	Pliva-Istra�iva�ki institut d.o.o.	USE OF 2-THIA-DIBENZO[e,h]AZULENES FOR THE MANUFACTURE OF PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYYTEM DISEASES AND DISORDERS
HRP20030955A2 (en) *	2003-11-21	2005-08-31	Pliva-Istra�iva�ki institut d.o.o.	USE OF 1-OXADIBENZO[e,h]AZULENES FOR THE MANUFACTURE OF PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS
HRP20030956A2 (en) *	2003-11-21	2005-08-31	Pliva-Istra�iva�ki institut d.o.o.	USE OF 1,2-DIAZA-DIBENZO[e,h]AZULENES FOR THE MANU
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1997
- 1997-04-09 ES ES97920662T patent/ES2196328T3/es not_active Expired - Lifetime
- 1997-04-09 DE DE69720709T patent/DE69720709T2/de not_active Expired - Lifetime
- 1997-04-09 KR KR10-1998-0703536A patent/KR100389298B1/ko not_active Expired - Fee Related
- 1997-04-09 PL PL328575A patent/PL190960B1/pl not_active IP Right Cessation
- 1997-04-09 EA EA199800348A patent/EA001002B1/ru not_active IP Right Cessation
- 1997-04-09 CZ CZ19983243A patent/CZ288865B6/cs not_active IP Right Cessation
- 1997-04-09 DK DK97920662T patent/DK0892793T3/da active
- 1997-04-09 BR BR9706639A patent/BR9706639A/pt not_active IP Right Cessation
- 1997-04-09 CA CA002232141A patent/CA2232141C/en not_active Expired - Fee Related
- 1997-04-09 US US09/155,840 patent/US6057441A/en not_active Expired - Lifetime
- 1997-04-09 CN CN97191422A patent/CN1116291C/zh not_active Expired - Fee Related
- 1997-04-09 IL IL12365597A patent/IL123655A/xx not_active IP Right Cessation
- 1997-04-09 EE EE9800326A patent/EE03612B1/xx not_active IP Right Cessation
- 1997-04-09 PT PT97920662T patent/PT892793E/pt unknown
- 1997-04-09 TR TR1998/01164T patent/TR199801164T2/xx unknown
- 1997-04-09 NZ NZ329953A patent/NZ329953A/xx not_active IP Right Cessation
- 1997-04-09 SI SI9730551T patent/SI0892793T1/xx unknown
- 1997-04-09 JP JP53673397A patent/JP3199751B2/ja not_active Expired - Fee Related
- 1997-04-09 HU HU9901613A patent/HUP9901613A3/hu unknown
- 1997-04-09 AT AT97920662T patent/ATE236893T1/de active
- 1997-04-09 WO PCT/EP1997/001829 patent/WO1997038991A1/en not_active Ceased
- 1997-04-09 EP EP97920662A patent/EP0892793B1/de not_active Expired - Lifetime
- 1997-04-09 SK SK1418-98A patent/SK283400B6/sk unknown
- 1997-04-10 TW TW086104563A patent/TW504506B/zh not_active IP Right Cessation
- 1997-04-11 MY MYPI97001598A patent/MY119321A/en unknown
- 1997-04-11 ZA ZA973114A patent/ZA973114B/xx unknown
1998
- 1998-03-11 NO NO19981076A patent/NO317156B1/no not_active IP Right Cessation
- 1998-10-07 BG BG102820A patent/BG63083B1/bg unknown
2000
- 2000-03-22 US US09/533,625 patent/US6194405B1/en not_active Expired - Lifetime
- 2000-12-21 US US09/745,517 patent/US6288058B1/en not_active Expired - Fee Related
2003
- 2003-11-04 CY CY0300077A patent/CY2382B1/xx unknown

Also Published As

Publication number	Publication date
KR100389298B1 (ko)	2003-10-30
NO317156B1 (no)	2004-08-30
CA2232141C (en)	2006-05-23
AU712154B2 (en)	1999-10-28
CA2232141A1 (en)	1997-10-23
HUP9901613A3 (en)	2001-08-28
PL190960B1 (pl)	2006-02-28
DE69720709T2 (de)	2004-03-11
ATE236893T1 (de)	2003-04-15
WO1997038991A1 (en)	1997-10-23
HK1015771A1 (en)	1999-10-22
SK283400B6 (sk)	2003-07-01
EA199800348A1 (ru)	1998-10-29
JP3199751B2 (ja)	2001-08-20
EA001002B1 (ru)	2000-08-28
SI0892793T1 (en)	2003-10-31
JP2000508327A (ja)	2000-07-04
ZA973114B (en)	1998-10-12
US6288058B1 (en)	2001-09-11
CN1116291C (zh)	2003-07-30
BR9706639A (pt)	1999-01-12
EP0892793B1 (de)	2003-04-09
IL123655A (en)	2001-03-19
NZ329953A (en)	1999-06-29
CZ288865B6 (cs)	2001-09-12
CY2382B1 (en)	2004-06-04
CZ324398A3 (cs)	1999-01-13
TW504506B (en)	2002-10-01
AU2695997A (en)	1997-11-07
SK141898A3 (en)	1999-03-12
KR19990067514A (ko)	1999-08-25
MY119321A (en)	2005-05-31
BG102820A (en)	1999-08-31
HUP9901613A2 (hu)	1999-09-28
EE03612B1 (et)	2002-02-15
DE69720709D1 (de)	2003-05-15
PT892793E (pt)	2003-08-29
US6194405B1 (en)	2001-02-27
ES2196328T3 (es)	2003-12-16
NO981076L (no)	1998-10-09
US6057441A (en)	2000-05-02
DK0892793T3 (da)	2003-07-21
EP0892793A1 (de)	1999-01-27
PL328575A1 (en)	1999-02-01
TR199801164T2 (xx)	1998-10-21
NO981076D0 (no)	1998-03-11
IL123655A0 (en)	1998-10-30
CN1205006A (zh)	1999-01-13
EE9800326A (et)	1999-04-15

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