IL99579A - 2 - )4 - פיפרדיניל( - h1 - פירידו ]b-4,3[ אינדול - 1 - אונים ותרכבות קרובות, ותהליך להכנתם - Google Patents
2 - )4 - פיפרדיניל( - h1 - פירידו ]b-4,3[ אינדול - 1 - אונים ותרכבות קרובות, ותהליך להכנתםInfo
- Publication number
- IL99579A IL99579A IL9957991A IL9957991A IL99579A IL 99579 A IL99579 A IL 99579A IL 9957991 A IL9957991 A IL 9957991A IL 9957991 A IL9957991 A IL 9957991A IL 99579 A IL99579 A IL 99579A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- pyrido
- indol
- ioweralkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical group 0.000 claims abstract description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 230000000561 anti-psychotic effect Effects 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- -1 Ioweralkyl Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- NPHVVXAIJAZCGK-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-5-methyl-3,4-dihydropyrido[4,3-b]indol-1-one Chemical compound O=C1C=2C3=CC=CC=C3N(C)C=2CCN1C(CC1)CCN1CC1=CC=CC=C1 NPHVVXAIJAZCGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- QDHSLJDFQLCDLT-UHFFFAOYSA-N 2-piperidin-4-yl-5h-pyrido[4,3-b]indol-1-one Chemical class C1=CC=2NC3=CC=CC=C3C=2C(=O)N1C1CCNCC1 QDHSLJDFQLCDLT-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 8
- 229960004046 apomorphine Drugs 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
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- 241001465754 Metazoa Species 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
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- 241000699670 Mus sp. Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
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- 238000004128 high performance liquid chromatography Methods 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 239000000164 antipsychotic agent Substances 0.000 description 3
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- 229960003990 apomorphine hydrochloride Drugs 0.000 description 3
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- 239000011668 ascorbic acid Substances 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
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- 150000008282 halocarbons Chemical class 0.000 description 3
- ZOAMBXDOGPRZLP-UHFFFAOYSA-N indole-3-acetamide Chemical compound C1=CC=C2C(CC(=O)N)=CNC2=C1 ZOAMBXDOGPRZLP-UHFFFAOYSA-N 0.000 description 3
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- 150000004681 metal hydrides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- RWLDAJMGAVDXSH-UHFFFAOYSA-N ethane-1,1,2-tricarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(O)=O RWLDAJMGAVDXSH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ABPJREHLAYHTHW-UHFFFAOYSA-N pyrano[2,3-g]indole Chemical compound O1C=CC=C2C3=NC=CC3=CC=C21 ABPJREHLAYHTHW-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 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
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004006 stereotypic behavior Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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
- C07D401/12—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL113439A IL113439A (en) | 1990-09-27 | 1991-09-26 | 2-(1-substituted-4-piperidinyl) aminoethyl-1h-indole-3- carboxylic acids, 2-(1-substituted- 4-piperidinyl) carbamoylmethyl-1h- indoles and their homologs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07588870 US5102889B1 (en) | 1990-09-27 | 1990-09-27 | 2-(4-piperidinyl)-1h-pyrido(4,3-b)indol-1-ones and related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL99579A0 IL99579A0 (en) | 1992-08-18 |
| IL99579A true IL99579A (he) | 1999-04-11 |
Family
ID=24355647
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL113439A IL113439A (en) | 1990-09-27 | 1991-09-26 | 2-(1-substituted-4-piperidinyl) aminoethyl-1h-indole-3- carboxylic acids, 2-(1-substituted- 4-piperidinyl) carbamoylmethyl-1h- indoles and their homologs |
| IL9957991A IL99579A (he) | 1990-09-27 | 1991-09-26 | 2 - )4 - פיפרדיניל( - h1 - פירידו ]b-4,3[ אינדול - 1 - אונים ותרכבות קרובות, ותהליך להכנתם |
| IL11343995A IL113439A0 (en) | 1990-09-27 | 1995-04-20 | Indole-piperidinyl compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL113439A IL113439A (en) | 1990-09-27 | 1991-09-26 | 2-(1-substituted-4-piperidinyl) aminoethyl-1h-indole-3- carboxylic acids, 2-(1-substituted- 4-piperidinyl) carbamoylmethyl-1h- indoles and their homologs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11343995A IL113439A0 (en) | 1990-09-27 | 1995-04-20 | Indole-piperidinyl compounds |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5102889B1 (he) |
| EP (1) | EP0481254B1 (he) |
| JP (1) | JP3241762B2 (he) |
| KR (1) | KR100210338B1 (he) |
| AT (1) | ATE132148T1 (he) |
| AU (1) | AU8475091A (he) |
| CA (1) | CA2052424C (he) |
| CS (1) | CS295191A3 (he) |
| DE (1) | DE69115833T2 (he) |
| DK (1) | DK0481254T3 (he) |
| ES (1) | ES2082078T3 (he) |
| FI (1) | FI914503A (he) |
| GR (1) | GR3018746T3 (he) |
| HU (1) | HUT59405A (he) |
| IE (1) | IE72156B1 (he) |
| IL (3) | IL113439A (he) |
| NO (1) | NO913777L (he) |
| NZ (2) | NZ248705A (he) |
| PT (1) | PT99074B (he) |
| TW (1) | TW199159B (he) |
| YU (1) | YU158691A (he) |
| ZA (1) | ZA917691B (he) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4975445A (en) * | 1989-12-06 | 1990-12-04 | Warner-Lambert Company | Substituted cyclohexenes as central nervous system agents |
| CA2399791A1 (en) * | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases |
| KR102570307B1 (ko) * | 2016-10-31 | 2023-08-25 | 주식회사 이엔에프테크놀로지 | 식각 조성물 |
| CN109400617A (zh) * | 2019-01-09 | 2019-03-01 | 湖北大学 | 一种新型吲哚并吡喃酮骨架化合物及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205452A1 (es) * | 1973-12-06 | 1976-05-07 | Endo Lab | Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles |
| DE2557341A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
| US4252811A (en) * | 1979-07-30 | 1981-02-24 | Pfizer Inc. | Hexahydro-trans-pyridoindole neuroleptic agents |
| US4432978A (en) * | 1979-07-30 | 1984-02-21 | Pfizer Inc. | Hexahydro-trans-pyridoindole |
| FR2619111B1 (fr) * | 1987-08-07 | 1991-01-11 | Synthelabo | Derives de (piperidinyl-4)methyl-2 tetrahydro-1,2,3,4 9h-pyrido (3,4-b) indole, leur preparation et leur application en therapeutique |
| GB2209335B (en) * | 1987-09-03 | 1991-05-29 | Glaxo Group Ltd | Lactam derivatives |
| FI92067C (fi) * | 1988-08-02 | 1994-09-26 | Glaxo Group Ltd | Menetelmä valmistaa terapeuttisesti aktiivisia mono- tai disubstituoituja (imidatsol-4-yyli)metyylipyrido/4,3-b/indol- ja atsepino/4,3-b/indol-1-oneja |
| GB8904551D0 (en) * | 1989-02-28 | 1989-04-12 | Glaxo Group Ltd | Chemical compounds |
-
1990
- 1990-09-27 US US07588870 patent/US5102889B1/en not_active Expired - Fee Related
-
1991
- 1991-09-25 FI FI914503A patent/FI914503A/fi not_active Application Discontinuation
- 1991-09-25 EP EP91116337A patent/EP0481254B1/en not_active Expired - Lifetime
- 1991-09-25 DK DK91116337.6T patent/DK0481254T3/da active
- 1991-09-25 TW TW080107539A patent/TW199159B/zh active
- 1991-09-25 NZ NZ248705A patent/NZ248705A/xx unknown
- 1991-09-25 ES ES91116337T patent/ES2082078T3/es not_active Expired - Lifetime
- 1991-09-25 DE DE69115833T patent/DE69115833T2/de not_active Expired - Fee Related
- 1991-09-25 AT AT91116337T patent/ATE132148T1/de not_active IP Right Cessation
- 1991-09-25 NZ NZ239934A patent/NZ239934A/en unknown
- 1991-09-26 JP JP27344091A patent/JP3241762B2/ja not_active Expired - Fee Related
- 1991-09-26 CS CS912951A patent/CS295191A3/cs unknown
- 1991-09-26 NO NO91913777A patent/NO913777L/no unknown
- 1991-09-26 CA CA002052424A patent/CA2052424C/en not_active Expired - Fee Related
- 1991-09-26 ZA ZA917691A patent/ZA917691B/xx unknown
- 1991-09-26 IE IE338891A patent/IE72156B1/en not_active IP Right Cessation
- 1991-09-26 IL IL113439A patent/IL113439A/xx not_active IP Right Cessation
- 1991-09-26 PT PT99074A patent/PT99074B/pt not_active IP Right Cessation
- 1991-09-26 HU HU913081A patent/HUT59405A/hu unknown
- 1991-09-26 YU YU158691A patent/YU158691A/sh unknown
- 1991-09-26 AU AU84750/91A patent/AU8475091A/en not_active Abandoned
- 1991-09-26 IL IL9957991A patent/IL99579A/he not_active IP Right Cessation
- 1991-09-27 KR KR1019910016849A patent/KR100210338B1/ko not_active IP Right Cessation
-
1995
- 1995-04-20 IL IL11343995A patent/IL113439A0/xx unknown
-
1996
- 1996-01-19 GR GR960400135T patent/GR3018746T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |