JPS63227570A - Isoquinoline derivative - Google Patents
Isoquinoline derivativeInfo
- Publication number
- JPS63227570A JPS63227570A JP5866387A JP5866387A JPS63227570A JP S63227570 A JPS63227570 A JP S63227570A JP 5866387 A JP5866387 A JP 5866387A JP 5866387 A JP5866387 A JP 5866387A JP S63227570 A JPS63227570 A JP S63227570A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- lower alkyl
- isoquinoline
- isoquinoline derivative
- 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.)
- Pending
Links
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 150000002537 isoquinolines Chemical class 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 208000008930 Low Back Pain Diseases 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 2
- 206010003246 arthritis Diseases 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 230000000269 nucleophilic effect Effects 0.000 abstract description 2
- 208000004371 toothache Diseases 0.000 abstract description 2
- 208000008035 Back Pain Diseases 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- -1 inorganic acid salt Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 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
- 238000000034 method Methods 0.000 description 1
- SYXIVIPLMNLWKL-UHFFFAOYSA-N n-isoquinolin-3-ylacetamide Chemical compound C1=CC=C2C=NC(NC(=O)C)=CC2=C1 SYXIVIPLMNLWKL-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なイソキノリン誘導体に関し、更に詳細
には医薬品として有用なインキノリン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel isoquinoline derivatives, and more particularly to inquinoline derivatives useful as pharmaceuticals.
従来、種々の薬理作用を有するインキノリン誘導体が知
られているが、このうち３−アシルアミノ−イソキノリ
ン誘導体については、殺虫作用を有する誘導体（米国特
許第３，２４７，２１２号明細書）が知られているにす
ぎず、それ以外の薬理作用を有する３−アクルアミノ−
イソキノリン誘導体については未だ報告をみない。Hitherto, inquinoline derivatives having various pharmacological actions have been known, but among these, 3-acylamino-isoquinoline derivatives have an insecticidal action (U.S. Pat. No. 3,247,212). 3-Acruamino-
There have been no reports regarding isoquinoline derivatives yet.
本発明は、従゛来公知の殺虫作用に限らず、種々の薬理
作用を有する新規な３−アシルアミノ−イソキノリン誘
導体を提供することを目的とする。An object of the present invention is to provide a novel 3-acylamino-isoquinoline derivative having various pharmacological actions in addition to the conventionally known insecticidal action.
本発明者は、種々の３−アシルアミノ−イソキノリン誘
導体を合成し、その薬理作用を探索したところ、（Ｉ）
式で表わされる新規化合物が強い抗炎症作用、鎮痛作用
、及び抗不整脈作用等を有し、関節炎、腰痛、歯痛ある
いは心疾患等の諸疾患に対し有用なものであることを見
い出し、本発明を完成した。The present inventor synthesized various 3-acylamino-isoquinoline derivatives and investigated their pharmacological effects, and found that (I)
We have discovered that the novel compound represented by the formula has strong anti-inflammatory effects, analgesic effects, anti-arrhythmic effects, etc., and is useful for various diseases such as arthritis, lower back pain, tooth pain, and heart disease, and have developed the present invention. completed.
すなわち、本発明は次の一般式（Ｉ）
〔式中、Ｒはアクル基を示し、Ｒ′は低級アル低級アル
キル基、Ｒ２は置換基を有することのある低級アルキル
基を示すか、あるいはＲ１とＲ２が一緒になって隣接す
る窒素原子と共に他の異種原子を含んでもよく、また置
換基を有していてもよい環を形成する）を示す〕で表わ
されるイソキノリン誘導体を提供するものである。That is, the present invention relates to the following general formula (I) [wherein R represents an acyl group, R' represents a lower alkyl group, R2 represents a lower alkyl group which may have a substituent, or R1 and R2 together with the adjacent nitrogen atom form a ring which may contain other heteroatoms and which may have a substituent. .
上記（Ｉ）式において、Ｒ１とＲ２が一緒になって形成
する基としては、例えば次の基
（式中、鳥は水素原子、低級アルキル基、ヒドロキシ置
換低級アルキル基、ハロゲン原子が置換することのある
アリール基、アラルキル基またはホルミル基を示す）。In the above formula (I), the group formed by R1 and R2 together is, for example, the following group (in the formula, bird is substituted with a hydrogen atom, a lower alkyl group, a hydroxy-substituted lower alkyl group, or a halogen atom). aryl, aralkyl or formyl group).
が挙げられる。can be mentioned.
本発明の一般式（Ｉ）で表わされる化合物は、例えば次
の反応式に従って、公知の方法により容易に得られる１
−ハロゲノ−イソキノリン類（２）に求核化合物に）を
反応させることによシ製造される。The compound represented by the general formula (I) of the present invention can be easily obtained by a known method according to the following reaction formula, for example.
-halogeno-isoquinolines (2) with a nucleophilic compound).
＠ に） （Ｉ）
（式中、Ｘはハロダン原子を示し、Ｒ，Ｒ’は前記し九
意味を有する）
本反応は、室温ないし使用する溶媒の還流温度にて数時
間〜数日間攪拌するか、または封管中敷時間〜数日間加
温することによって実施される。また必要に応じ、金属
ナトリウム、水素化ナトリウム、水酸化ナトリウムまた
は水酸化カリウムなどの塩基の存在下で反応を行なうこ
ともできる。溶媒としてはメタノール、エタノール、含
水アルコール、アセトン、ジメチルホルムアミド、ジオ
キサンまたはエトキシエタノール等が挙げられる。(I) (In the formula, X represents a halodane atom, and R and R' have the nine meanings described above) This reaction is stirred at room temperature or the reflux temperature of the solvent used for several hours to several days. Alternatively, it can be carried out by heating for several days up to the time required for sealing the insole. Further, if necessary, the reaction can also be carried out in the presence of a base such as metallic sodium, sodium hydride, sodium hydroxide or potassium hydroxide. Examples of the solvent include methanol, ethanol, hydrous alcohol, acetone, dimethylformamide, dioxane, and ethoxyethanol.
かくして得られた本発明のイソキノリン誘導体（Ｉ）は
、更に必要に応じて常法によシ、塩酸塩、臭化水素酸塩
、硫酸塩などの無機酸塩、またはマレイン酸塩、フマー
ル酸塩、クエン酸塩、メタンスルホン酸塩などの有機酸
塩とすることができる。The isoquinoline derivative (I) of the present invention thus obtained can be further treated with an inorganic acid salt such as a hydrochloride, a hydrobromide, a sulfate, or a maleate or a fumarate by a conventional method, if necessary. , citrate, methanesulfonate, and other organic acid salts.
斯くの如くして得られた本発明の化合物の抗炎症作用に
ついて試験した結果を以下に示す。The results of testing the anti-inflammatory effect of the compound of the present invention thus obtained are shown below.
６週令のウィスター系ラット金一群５匹とし、１８時間
絶食した後、被検化合物を０．５係カルボキンメチルセ
ルロースナトリウム（ＣＭＣ−Ｎａ ）溶液に溶解又は
懸濁し、経口投与した。被検化合物投与６０分後に１％
カラゲニン生理食塩水溶液０．１ ｆｆ１７！を右足踏
皮下に注入し、３時間後に定容積（５）を測定し、カラ
を算出した。After fasting for 18 hours, a test compound was dissolved or suspended in a 0.5 sodium carboxyl methylcellulose (CMC-Na) solution and orally administered to 5 6-week old Wistar rats in one group. 1% 60 minutes after administration of test compound
Carrageenin saline solution 0.1 ff17! was injected subcutaneously into the right foot, and 3 hours later, the fixed volume (5) was measured and the empty volume was calculated.
別に１係力２ゲニン生理食塩水溶液０．１−を右足踏皮
下に注°大した対照群の浮腫率も同様に求め、それぞれ
の検体の浮腫抑制率を次式によシ算出した。Separately, the edema rate of the control group, in which 0.1 - of the 1-force 2-genin physiological saline solution was injected under the skin of the right foot, was similarly determined, and the edema suppression rate of each specimen was calculated using the following formula.
以下余白
第１表
以上の結果から明らかな如く、本発明の化合物（Ｉ）は
強い抗炎症作用を有し、抗炎症薬として有用なものであ
る。As is clear from the results shown in Table 1 below, the compound (I) of the present invention has a strong anti-inflammatory effect and is useful as an anti-inflammatory drug.
次に実施例を挙げて説明するが、本発明はこれらに限定
されるものではない。Next, the present invention will be described with reference to Examples, but the present invention is not limited thereto.
実施例１
１−プロモー３−アセタミイーイソキノリン０．７ｆに
ジメチルアミン飽和メタノール溶液１５７！を加え、封
管中８０℃で３時間加熱攪拌した。その後、反応液を留
去し、残金にクロロホルムを加え、水洗後、無水硫酸ナ
トリウムにて乾燥した。クロロホルムを留去し、残金を
７リカダルカラムクロマトグラフイーにて精製し、クロ
ロホルム−エーテル混液よシ再結晶して微黄色結晶の１
−ジメチルアミノ−３−アセタミノーイソキノリン（化
合物番号３）０．４Ｆ（収率６６．１ ％ ＞を得た。Example 1 0.7f of 1-promo-3-acetamyisoquinoline and 157 g of dimethylamine saturated methanol solution! was added, and the mixture was heated and stirred at 80° C. for 3 hours in a sealed tube. Thereafter, the reaction solution was distilled off, chloroform was added to the residue, washed with water, and dried over anhydrous sodium sulfate. Chloroform was distilled off, and the residue was purified by 7 ricadal column chromatography and recrystallized from a chloroform-ether mixture to give pale yellow crystals.
-Dimethylamino-3-acetaminoisoquinoline (compound number 3) 0.4F (yield: 66.1%) was obtained.
実施例２
１−プロモー３−アセタミノーイソキノリン１．Ｏｆに
無水ビベラゾン３．２６ ｔ、エトキシエタノール４０
ｍを加え、２時間還流攪拌した。その後、反応液を留去
し、残金にクロロホルムを加え、水洗後、無水硫酸ナト
リウムにて乾燥した。クロロホルムを留去し、残金をシ
リカダルカラムクロマトグラフィーにて精製し、クロロ
ホルム−エーテル混液より再結晶して無色結晶の１−（
１−ピベラゾニル）−３−アセタミノーイソキノリン（
化合物番号４）０．８５ｆ（収率８３．４％）を得た。Example 2 1-promo 3-acetaminoisoquinoline 1. Of anhydrous viverazone 3.26 t, ethoxyethanol 40
m was added thereto, and the mixture was stirred under reflux for 2 hours. Thereafter, the reaction solution was distilled off, chloroform was added to the residue, washed with water, and dried over anhydrous sodium sulfate. Chloroform was distilled off, the residue was purified by silica dull column chromatography, and recrystallized from a chloroform-ether mixture to give colorless crystals of 1-(
1-piverazonyl)-3-acetaminoisoquinoline (
Compound No. 4) 0.85f (yield 83.4%) was obtained.
実施例３
実施例１またｕ２と同様にして第２表に示す化合物を得
た。なお、表中には実施例１及び２で得た化合物も併せ
て示した。Example 3 The compounds shown in Table 2 were obtained in the same manner as in Example 1 and u2. In addition, the compounds obtained in Examples 1 and 2 are also shown in the table.
以下余白Margin below
Claims (1)
または基▲数式、化学式、表等があります▼（Ｒ＿１は
水素原子または低級アルキル基、Ｒ＿２は置換基を有す
ることのある低級アルキル基を示すか、あるいはＲ＿１
とＲ＿２が一緒になつて隣接する窒素原子と共に他の異
種原子を含んでもよく、また置換基を有していてもよい
環を形成する）を示す〕 で表わされるイソキノリン誘導体。 ２、（ I ）式中、Ｒ′が次の基 ▲数式、化学式、表等があります▼ （式中、Ｒ＿３は水素原子、低級アルキル基、ヒドロキ
シ置換低級アルキル基、ハロゲン原子が置換することの
あるアリール基、アラルキル基またはホルミル基を示す
） で表わされるものである特許請求の範囲第１項記載のイ
ソキノリン誘導体。[Claims] 1. The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R represents an acyl group, and R' is a lower alkoxy group or group ▲Mathical formula, There are chemical formulas, tables, etc. ▼ (R_1 is a hydrogen atom or a lower alkyl group, R_2 is a lower alkyl group that may have a substituent, or R_1
and R_2 together form a ring which, together with the adjacent nitrogen atom, may contain other heteroatoms and may have a substituent.] An isoquinoline derivative represented by: 2. In formula (I), R' is the following group ▲ There are mathematical formulas, chemical formulas, tables, etc. The isoquinoline derivative according to claim 1, which is represented by the following formula (representing a certain aryl group, aralkyl group or formyl group)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5866387A JPS63227570A (en) | 1987-03-13 | 1987-03-13 | Isoquinoline derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5866387A JPS63227570A (en) | 1987-03-13 | 1987-03-13 | Isoquinoline derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63227570A true JPS63227570A (en) | 1988-09-21 |
Family
ID=13090825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5866387A Pending JPS63227570A (en) | 1987-03-13 | 1987-03-13 | Isoquinoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63227570A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998039301A1 (en) * | 1997-03-04 | 1998-09-11 | Neurogen Corporation | 1-(isoquinolin-1-yl)-4-(1-phenylmethyl)piperazines; dopamine receptor subtype specific ligands |
| US5972945A (en) * | 1997-06-13 | 1999-10-26 | Neurogen Corporation | 2-aminoalkylaminoquinolines; dopamine receptor subtype specific ligands |
| US6313141B1 (en) | 1997-06-13 | 2001-11-06 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| US6613901B2 (en) | 2000-03-08 | 2003-09-02 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| WO2008115593A1 (en) | 2007-03-21 | 2008-09-25 | The University Of Montana | 1-[(2'-substituted)-piperazin-1'-yl]-isoquinolines as norepinephrine transporter inhibitor therapeutics and positron emission tomography imaging agents |
-
1987
- 1987-03-13 JP JP5866387A patent/JPS63227570A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998039301A1 (en) * | 1997-03-04 | 1998-09-11 | Neurogen Corporation | 1-(isoquinolin-1-yl)-4-(1-phenylmethyl)piperazines; dopamine receptor subtype specific ligands |
| US5972945A (en) * | 1997-06-13 | 1999-10-26 | Neurogen Corporation | 2-aminoalkylaminoquinolines; dopamine receptor subtype specific ligands |
| US6313141B1 (en) | 1997-06-13 | 2001-11-06 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| US6613901B2 (en) | 2000-03-08 | 2003-09-02 | Neurogen Corporation | 2-aminoalkylaminoquinolines as dopamine D4 ligands |
| WO2008115593A1 (en) | 2007-03-21 | 2008-09-25 | The University Of Montana | 1-[(2'-substituted)-piperazin-1'-yl]-isoquinolines as norepinephrine transporter inhibitor therapeutics and positron emission tomography imaging agents |
| US7887784B2 (en) | 2007-03-21 | 2011-02-15 | University Of Montana | 1-[(2′-substituted)-piperazin-1′ -yl]-isoquinolines as norepinephrine transporter inhibitor therapeutics and positron emission tomography imaging agents |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69110625T2 (en) | Oxazolopyridine derivatives, processes for their preparation and the pharmaceutical compositions containing them. | |
| US4234584A (en) | Substituted phenylpiperazine derivatives | |
| JPS60112793A (en) | 6-vinyl-furo-(3,4-c)-pyridine derivative, manufacture and medicinal composition | |
| SU1241986A3 (en) | Method of producing benzamide derivatives,hydrochlorides thereof or optical isomers | |
| JPS6033114B2 (en) | 1,2-benzisoxazole derivative | |
| PT86082B (en) | PROCESS FOR THE PREPARATION OF ANTI-ALLERGIC AND ANTI-INFLAMMATORY DI-HYDROPYRIDINIC AGENTS | |
| JPS62230767A (en) | Acetamide derivative and its production and its application to drug | |
| US3103516A (en) | J-tertiaryaminq-lower alkyl-jb-meta- | |
| US3979456A (en) | Phenoxyalkylamines, process for their preparation and applications thereof | |
| JPS63227570A (en) | Isoquinoline derivative | |
| DE2128375C3 (en) | Basic substituted alkylideneamino-oxyalkyl-carboxylic acid esters, their acid addition salts, processes for their production and pharmaceutical preparations containing them | |
| JPS59106484A (en) | Thienylacetic acid amide and manufacture | |
| US4080380A (en) | 2-Naphthyl-lower-alkylamines | |
| JPS6354363A (en) | Quinoline derivative | |
| US3590041A (en) | Novel halo-substituted cinnamic acid heterocyclic amides | |
| US4139621A (en) | N-(4-substituted-3,5-dichloro-phenyl)-piperazines | |
| JPS6056130B2 (en) | Novel salicylic acid derivatives | |
| US4313956A (en) | Novel sypathomimetic amine prodrugs | |
| US3935221A (en) | Substituted fusaric acid derivatives | |
| JPS63154663A (en) | 3,5-di-tertiary-butyl-4-hydroxycinnamic amide derivative | |
| US3185705A (en) | 2-phenyl-5, 5-di-esters and di-amides of 2-pyrroline and the corresponding pyrrolidines | |
| US3281468A (en) | beta-phenyl-beta-hydroxyethylamines | |
| US3995046A (en) | Esters of 5-n-butylpyridine-2 carboxylic acid and pharmaceutical compositions containing these compounds | |
| HU194213B (en) | Process for production of 3-alkoxi-2-n-pirrolidin-n-piridil-n-furil /or n-tienil/-methil-prophil amins | |
| PT88234B (en) | PROCESS FOR THE PREPARATION OF CHLOROANILINE DERIVATIVES |