UA59408C2 - Похідні індолу та 2,3-дигідроіндолу, фармацевтична композиція та спосіб лікування - Google Patents
Похідні індолу та 2,3-дигідроіндолу, фармацевтична композиція та спосіб лікування Download PDFInfo
- Publication number
- UA59408C2 UA59408C2 UA2000020949A UA00020949A UA59408C2 UA 59408 C2 UA59408 C2 UA 59408C2 UA 2000020949 A UA2000020949 A UA 2000020949A UA 00020949 A UA00020949 A UA 00020949A UA 59408 C2 UA59408 C2 UA 59408C2
- Authority
- UA
- Ukraine
- Prior art keywords
- indole
- piperazin
- benzodioxan
- chloro
- ethyl
- Prior art date
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 13
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 65
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 33
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 32
- -1 hydroxy, formyl Chemical group 0.000 claims description 24
- 230000005764 inhibitory process Effects 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 230000000697 serotonin reuptake Effects 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000002475 indoles Chemical class 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 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 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
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- 241001465754 Metazoa Species 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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- 150000001793 charged compounds Chemical class 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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- 238000003818 flash chromatography Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 210000002348 5-ht neuron Anatomy 0.000 description 3
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical class ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK89297 | 1997-07-25 | ||
| PCT/DK1998/000336 WO1999005140A1 (en) | 1997-07-25 | 1998-07-20 | Indole and 2,3-dihydroindole derivatives, their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA59408C2 true UA59408C2 (uk) | 2003-09-15 |
Family
ID=8098721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000020949A UA59408C2 (uk) | 1997-07-25 | 1998-07-20 | Похідні індолу та 2,3-дигідроіндолу, фармацевтична композиція та спосіб лікування |
Country Status (13)
| Country | Link |
|---|---|
| CN (3) | CN1127501C (no) |
| AR (1) | AR013206A1 (no) |
| BR (1) | BR9810790A (no) |
| EA (1) | EA001890B1 (no) |
| HK (3) | HK1030220A1 (no) |
| IL (1) | IL133990A (no) |
| IS (1) | IS2024B (no) |
| NO (1) | NO318610B1 (no) |
| PL (1) | PL190924B1 (no) |
| SK (1) | SK284866B6 (no) |
| TR (1) | TR200000231T2 (no) |
| UA (1) | UA59408C2 (no) |
| ZA (1) | ZA986237B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103420989B (zh) * | 2012-05-15 | 2016-03-23 | 华中科技大学 | 苯并二噁烷类衍生物及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8830312D0 (en) * | 1988-12-28 | 1989-02-22 | Lundbeck & Co As H | Heterocyclic compounds |
| DE4127849A1 (de) * | 1991-08-22 | 1993-02-25 | Merck Patent Gmbh | Benzodioxanderivate |
| FR2692264B1 (fr) * | 1992-06-12 | 1994-08-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant. |
-
1998
- 1998-07-13 AR ARP980103400 patent/AR013206A1/es active IP Right Grant
- 1998-07-14 ZA ZA986237A patent/ZA986237B/xx unknown
- 1998-07-20 TR TR2000/00231T patent/TR200000231T2/xx unknown
- 1998-07-20 SK SK95-2000A patent/SK284866B6/sk not_active IP Right Cessation
- 1998-07-20 PL PL338194A patent/PL190924B1/pl not_active IP Right Cessation
- 1998-07-20 EA EA200000162A patent/EA001890B1/ru not_active IP Right Cessation
- 1998-07-20 UA UA2000020949A patent/UA59408C2/uk unknown
- 1998-07-20 CN CN 98807554 patent/CN1127501C/zh not_active Expired - Fee Related
- 1998-07-20 CN CN 03106002 patent/CN1286833C/zh not_active Expired - Fee Related
- 1998-07-20 CN CNB03106003XA patent/CN1293075C/zh not_active Expired - Fee Related
- 1998-07-20 BR BR9810790-9A patent/BR9810790A/pt not_active Application Discontinuation
- 1998-07-20 IL IL13399098A patent/IL133990A/xx not_active IP Right Cessation
-
2000
- 2000-01-11 IS IS5334A patent/IS2024B/is unknown
- 2000-01-25 NO NO20000372A patent/NO318610B1/no not_active IP Right Cessation
-
2001
- 2001-02-21 HK HK01101274A patent/HK1030220A1/xx not_active IP Right Cessation
-
2004
- 2004-12-13 HK HK04109853A patent/HK1066807A1/xx not_active IP Right Cessation
- 2004-12-13 HK HK04109852A patent/HK1066806A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL338194A1 (en) | 2000-10-09 |
| NO318610B1 (no) | 2005-04-18 |
| CN1265107A (zh) | 2000-08-30 |
| SK952000A3 (en) | 2001-03-12 |
| CN1127501C (zh) | 2003-11-12 |
| IL133990A (en) | 2003-09-17 |
| NO20000372L (no) | 2000-03-21 |
| SK284866B6 (sk) | 2006-01-05 |
| HK1066807A1 (en) | 2005-04-01 |
| BR9810790A (pt) | 2000-07-25 |
| IS5334A (is) | 2000-01-11 |
| CN1293075C (zh) | 2007-01-03 |
| NO20000372D0 (no) | 2000-01-25 |
| EA001890B1 (ru) | 2001-10-22 |
| IS2024B (is) | 2005-08-15 |
| HK1066806A1 (en) | 2005-04-01 |
| TR200000231T2 (tr) | 2000-07-21 |
| IL133990A0 (en) | 2001-04-30 |
| HK1030220A1 (en) | 2001-04-27 |
| CN1515568A (zh) | 2004-07-28 |
| AR013206A1 (es) | 2000-12-13 |
| CN1515569A (zh) | 2004-07-28 |
| EA200000162A1 (ru) | 2000-10-30 |
| PL190924B1 (pl) | 2006-02-28 |
| ZA986237B (en) | 1999-03-31 |
| CN1286833C (zh) | 2006-11-29 |
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