RU2339637C1 - Histamine receptor blockers for pharmaceutical compositions of antiallergic and autoimmune effect - Google Patents

Histamine receptor blockers for pharmaceutical compositions of antiallergic and autoimmune effect Download PDF

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RU2339637C1
RU2339637C1 RU2007112665/04A RU2007112665A RU2339637C1 RU 2339637 C1 RU2339637 C1 RU 2339637C1 RU 2007112665/04 A RU2007112665/04 A RU 2007112665/04A RU 2007112665 A RU2007112665 A RU 2007112665A RU 2339637 C1 RU2339637 C1 RU 2339637C1
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substituted
pyrido
tetrahydro
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optionally substituted
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Александр Васильевич Иващенко (US)
Александр Васильевич Иващенко
Сергей Евгеньевич Ткаченко (RU)
Сергей Евгеньевич Ткаченко
Евгений Борисович Фролов (RU)
Евгений Борисович Фролов
Олег Дмитриевич Митькин (RU)
Олег Дмитриевич Митькин
Дмитрий Владимирович Кравченко (RU)
Дмитрий Владимирович Кравченко
Иль Матусович Окунь (US)
Илья Матусович Окунь
Николай Филиппович Савчук (RU)
Николай Филиппович Савчук
Андрей Александрович Иващенко (RU)
Андрей Александрович Иващенко
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Андрей Александрович Иващенко
Алла Хем, Ллс
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    • 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
    • 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
    • A61P37/02—Immunomodulators
    • 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

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Abstract

FIELD: chemistry.
SUBSTANCE: invention concerns new histamine receptor blockers in the form of 2,3,4,5-tetrahydro-1H-pyrido-[3,4-b]indoles of the general formula 1
Figure 00000002
, where: R1 is an aminogroup substitute selected out of optionally substituted C1-C5alkyl; R2 i is one or several same or different substitutes selected out of hydrogen, halogen, C1-C3 alkyl, CF3; Ar is phenyl or 5-6-member heterocycle containing 1-2 nitrogen or sulphur atoms in the cycle, unsubstituted or substituted by halogen, C1-C5alkyl, C1-C5alkoxy, substituted aminogroup or trifluormethyl; W is CH2 group optionally substituted CH2CH2 group or optionally substituted CH=CH group.
EFFECT: enhanced antiallergic and autoimmune effect.
4 tbl

Description

Текст описания приведен в факсимильном виде.

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Claims (12)

1. Блокаторы гистаминного рецептора для фармацевтических композиций, обладающих противоаллергическим и аутоиммунным действием, представляющие собой замещенные 2,3,4,5-тетрагидро-1H-пиридо[4,3-b]индолы общей формулы 1, их фармацевтически приемлемые соли и/или гидраты1. Histamine receptor blockers for pharmaceutical compositions having anti-allergic and autoimmune effects, which are substituted 2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indoles of general formula 1, their pharmaceutically acceptable salts and / or hydrates
Figure 00000054
Figure 00000054
 где R1 представляет собой заместитель аминогруппы, выбранный из необязательно замещенного С1-С5алкила;where R 1 represents an amino substituent selected from optionally substituted C 1 -C 5 alkyl; R2 i представляет собой один или несколько одинаковых или различных заместителей, выбранных из водорода, галогена, C1-С3алкила, CF3;R 2 i represents one or more identical or different substituents selected from hydrogen, halogen, C 1 -C 3 alkyl, CF 3 ; Ar представляют собой незамещенный или замещенный галогеном, C1-С5алкилом, С1-С5алкокси, замещенной аминогруппой или трифторметилом фенил или 5-6-членный гетероцикл, содержащий 1-2 атома азота или серы в цикле;Ar are unsubstituted or substituted with halogen, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, substituted amino or trifluoromethyl phenyl or a 5-6 membered heterocycle containing 1-2 nitrogen or sulfur atoms in the ring; W представляет собой СН2 группу, необязательно замещенную СН2СН2 группу или необязательно замещенную СН=СН группу, исключая соединения гдеW represents CH 2 group, optionally substituted CH 2 CH 2 group or optionally substituted CH = CH group, excluding compounds where Ar-фенил; W-CH2; R1=CH3; R2 i=H; (7)CH3; (8)CH3; (7)Cl; (8)Cl; (9)Cl; (7)Br;Ar-phenyl; W-CH 2 ; R 1 = CH 3 ; R 2 i = H; (7) CH 3 ; (8) CH 3 ; (7) Cl; (8) Cl; (9) Cl; (7) Br; (8)-ОС2Н5;(здесь и далее в скобках указано положение заместителя R2 i); или(8) -OS 2 H 5 ; (hereinafter, in parentheses the position of the substituent R 2 i is indicated); or Ar-2,4-диметилфенил; W-CH2; R1=бензил; R2 i=H; (8)CH3; илиAr-2,4-dimethylphenyl; W-CH 2 ; R 1 = benzyl; R 2 i = H; (8) CH 3 ; or Ar-4-оксифенил; W-CH2; R1=2-оксифенилкарбонил; илиAr-4-hydroxyphenyl; W-CH 2 ; R 1 = 2-hydroxyphenylcarbonyl; or Ar-2-(2-диметиламино)этил-5-метилиндол-3-ил; W-СН2; R1=СН3; R2 i=(8)СН3; илиAr-2- (2-dimethylamino) ethyl-5-methylindol-3-yl; W-CH 2 ; R 1 = CH 3 ; R 2 i = (8) CH 3 ; or Ar-4-хлорфенил; W-CH2; R1=CH3; R2 i=H; (7)Cl; (8)Cl; илиAr-4-chlorophenyl; W-CH 2 ; R 1 = CH 3 ; R 2 i = H; (7) Cl; (8) Cl; or Ar-4-метоксифенил; W-CH2; R1=СН3; R2 i=(8)Cl; илиAr-4-methoxyphenyl; W-CH 2 ; R 1 = CH 3 ; R 2 i = (8) Cl; or Ar-4-фторфенил; W-CH2; R1=CH3; R2 i=(8)F; илиAr-4-fluorophenyl; W-CH 2 ; R 1 = CH 3 ; R 2 i = (8) F; or Ar-4-фторфенил; W-CH2; R1=2-(пиридин-2-ил)этил; R2 i=(8)F; илиAr-4-fluorophenyl; W-CH 2 ; R 1 = 2- (pyridin-2-yl) ethyl; R 2 i = (8) F; or Ar-фенил; W-CH2CH2; R1=CH3; R2 i=H; илиAr-phenyl; W-CH 2 CH 2 ; R 1 = CH 3 ; R 2 i = H; or Ar-пиридин-2-ил; W-CH2; R1=CH3; R2 i=H; (8)Cl; илиAr-pyridin-2-yl; W-CH 2 ; R 1 = CH 3 ; R 2 i = H; (8) Cl; or Ar-пиридин-3-ил; W-CH2; R1=CH3; R2 i=(8)Cl; илиAr-pyridin-3-yl; W-CH 2 ; R 1 = CH 3 ; R 2 i = (8) Cl; or Ar-пиридин-4-ил; W-CH2; R1=CH3; R2 i=(8)Cl; илиAr-pyridin-4-yl; W-CH 2 ; R 1 = CH 3 ; R 2 i = (8) Cl; or Ar-6-метилпиридин-3-ил; W-CH2CH2; R1=CH3; C2H5; н-C3H7; нС4Н9,Ar-6-methylpyridin-3-yl; W-CH 2 CH 2 ; R 1 = CH 3 ; C 2 H 5 ; n-C 3 H 7 ; ns 4 H 9 , изоС4Н9, вт.С4Н9, изо-С5Н11, бензил, R2 i=H; илиisoC 4 H 9 , br C 4 H 9 , iso-C 5 H 11 , benzyl, R 2 i = H; or Ar-6-метилпиридин-3-ил; W-CH2CH2; R1=CH3; C2H5; н-C3H7; нС4H9,Ar-6-methylpyridin-3-yl; W-CH 2 CH 2 ; R 1 = CH 3 ; C 2 H 5 ; n-C 3 H 7 ; nS 4 H 9 , изоС4Н9, изоС5Н11, R2 i=(8)CH3; илиisoC 4 H 9 , isoC 5 H 11 , R 2 i = (8) CH 3 ; or Ar-6-метилпиридин-3-ил; W-СН2СН2; R1=СН3; R2 i=(7)Cl; (8)Cl; (8)Br; (7)CF3; (7)CH3; (8,9)ди-СН3; (7,8)ди-СН3; (7,8)ди-Cl; (7)Cl(8)СН3; (8)Cl(6)СН3; (8)Cl(7)СН3; илиAr-6-methylpyridin-3-yl; W-CH 2 CH 2 ; R 1 = CH 3 ; R 2 i = (7) Cl; (8) Cl; (8) Br; (7) CF 3 ; (7) CH 3 ; (8.9) di-CH 3 ; (7.8) di-CH 3 ; (7.8) di-Cl; (7) Cl (8) CH 3 ; (8) Cl (6) CH 3 ; (8) Cl (7) CH 3 ; or Ar-пиридин-3-ил; W-CH2CH2; R1=CH3; R2 i=(8)Cl; илиAr-pyridin-3-yl; W-CH 2 CH 2 ; R 1 = CH 3 ; R 2 i = (8) Cl; or Ar-6-метилпиридин-3-ил; W-CH2CH2; R1=бензил; R2 i=(8)Cl; 8)CH3; илиAr-6-methylpyridin-3-yl; W-CH 2 CH 2 ; R 1 = benzyl; R 2 i = (8) Cl; 8) CH 3 ; or 2,2-диметил-5-[2-(6-метилпиридин-3-ил)этил]-2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индолиний иодид; или2,2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indolinium iodide; or 2-метил-5-[2-(6-метилпиридин-3-ил)этил]-2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индолиний 2-[2-(4-бромфенил)-2-оксоэтил]бромид; а также2-methyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indolinium 2- [2- (4- bromophenyl) -2-oxoethyl] bromide; as well as 2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индолы, включающие, по крайней мере, одну карбоксильную или алкилоксикарбонильную группу и их фармацевтически приемлемые соли.2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indoles, including at least one carboxyl or alkyloxycarbonyl group and their pharmaceutically acceptable salts. 2. Блокатор по п.1, представляющий собой замещенные 2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индолы общей формулы 1.12. The blocker according to claim 1, which is a substituted 2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indoles of the general formula 1.1
Figure 00000055
Figure 00000055
 3. Блокатор по п.2, представляющий замещенные 2-метил-2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индол общей формулы 1.1.1, 1.1.23. The blocker according to claim 2, representing substituted 2-methyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole of the general formula 1.1.1, 1.1.2
Figure 00000056
Figure 00000057
Figure 00000056
Figure 00000057
 где R2 представляет собой Н, F, CH3, CF3; Ar представляет собой необязательно замещенный фенил, 3-пиридил, 4-пиридил.where R 2 represents H, F, CH 3 , CF 3 ; Ar is optionally substituted phenyl, 3-pyridyl, 4-pyridyl. 4. Блокатор по п.1, представляющий собой замещенные 5-винил-2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индолы общей формулы 1.24. The blocker according to claim 1, which is a substituted 5-vinyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole of the general formula 1.2
Figure 00000058
Figure 00000058
 где R1 и R2 i имеют вышеуказанное значение; R3 представляет собой группу СН=СН-Ar, в которой Ar имеет вышеуказанное значение.where R 1 and R 2 i have the above meaning; R 3 represents a group CH = CH-Ar, in which Ar has the above meaning. 5. Блокатор по п.1 или 4, представляющие собой замещенные цис-5-винил-2-метил-2,3,4,5-тетрагидро-1H-пиридо[4,3-b]индолы общей формулы 1.2.1, 1.2.2 и замещенные транс-5-винил-2-метил-2,3,4,5-тетрагидро-1H-пиридо[4,3-b]индолы общей формулы 1.2.3, 1.2.45. The blocker according to claim 1 or 4, which are substituted cis-5-vinyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indoles of the general formula 1.2.1, 1.2.2 and substituted trans-5-vinyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indoles of the general formula 1.2.3, 1.2.4
Figure 00000059
Figure 00000060
Figure 00000061
Figure 00000062
Figure 00000059
Figure 00000060
Figure 00000061
Figure 00000062
 где R2 представляет собой Н, F, СН3, CF3; Ar представляет собой необязательно замещенный фенил, 3-пиридил, 4-пиридил.where R 2 represents H, F, CH 3 , CF 3 ; Ar is optionally substituted phenyl, 3-pyridyl, 4-pyridyl. 6. Блокатор по п.1, представляющий собой замещенный 5-этил-2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индол общей формулы 1.36. The blocker according to claim 1, which is a substituted 5-ethyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole of the general formula 1.3
Figure 00000063
Figure 00000063
 где R1, R2 i и Ar имеют вышеуказанное значение.where R 1 , R 2 i and Ar have the above meaning. 7. Блокатор по п.6, представляющий собой замещенные 2-метил-5-этил-2,3,4,5-тетрагидро-1H-пиридо[4,3-b]индолы общей формулы 1.3.1, 1.3.27. The blocker according to claim 6, which is a substituted 2-methyl-5-ethyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole of the general formula 1.3.1, 1.3.2
Figure 00000064
Figure 00000065
Figure 00000064
Figure 00000065
 где R2 представляет собой Н, F, СН3, CF3; Ar представляет собой необязательно замещенный фенил, необязательно замещенный 3-пиридил, 4-пиридил.where R 2 represents H, F, CH 3 , CF 3 ; Ar is optionally substituted phenyl, optionally substituted 3-pyridyl, 4-pyridyl. 8. Фармацевтическая композиция, обладающая противоаллергическим и аутоиммунных действием, содержащая в качестве активной субстанции, по крайней мере, один замещенный 2,3,4,5-тетрагидро-1H-пиридо[4,3-b]индол по любому из пп.1-7 или его фармацевтически приемлемую соль / или гидрат.8. A pharmaceutical composition having anti-allergic and autoimmune effects, containing as an active substance at least one substituted 2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole according to any one of claims 1 -7 or a pharmaceutically acceptable salt / or hydrate thereof. 9. Способ получения фармацевтической композиции по п.8 смешением, по крайней мере, одного замещенного 2,3,4,5-тетрагидро-1Н-пиридо[4,3-b]индола по любому из пп.1-7 или его фармацевтически приемлемой соли/или гидрата с инертным наполнителем и/или растворителем.9. The method of obtaining the pharmaceutical composition of claim 8 by mixing at least one substituted 2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole according to any one of claims 1 to 7 or its pharmaceutically an acceptable salt / or hydrate with an inert filler and / or solvent. 10. Применение фармацевтической композиции по п.8 для получения лекарственных средств в форме таблеток, капсул или инъекций, помещенных в фармацевтически приемлемую упаковку, для профилактики и лечения аллергических и аутоиммунных заболеваний.10. The use of the pharmaceutical composition of claim 8 for the manufacture of medicines in the form of tablets, capsules or injections in a pharmaceutically acceptable package, for the prevention and treatment of allergic and autoimmune diseases. 11. Лекарственное средство, включающее фармацевтическую композицию по п.8 в форме таблеток, капсул или инъекций, помещенных в фармацевтически приемлемую упаковку, для профилактики и лечения аллергических и аутоиммунных заболеваний.11. A medicament comprising the pharmaceutical composition of claim 8 in the form of tablets, capsules or injections in a pharmaceutically acceptable package for the prevention and treatment of allergic and autoimmune diseases. 12. Способ профилактики и лечения аллергических и аутоиммунных заболеваний, введением лекарственного средства по п.11.12. A method for the prevention and treatment of allergic and autoimmune diseases, the introduction of the drug according to claim 11.
RU2007112665/04A 2007-04-05 2007-04-05 Histamine receptor blockers for pharmaceutical compositions of antiallergic and autoimmune effect RU2339637C1 (en)

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