RU99110944A - THYENOPYRIMIDINES WITH INHIBITING ACTION WITH RESPECT TO PHOSPHODYSTRASE V (PDE V) - Google Patents
THYENOPYRIMIDINES WITH INHIBITING ACTION WITH RESPECT TO PHOSPHODYSTRASE V (PDE V)Info
- Publication number
- RU99110944A RU99110944A RU99110944/04A RU99110944A RU99110944A RU 99110944 A RU99110944 A RU 99110944A RU 99110944/04 A RU99110944/04 A RU 99110944/04A RU 99110944 A RU99110944 A RU 99110944A RU 99110944 A RU99110944 A RU 99110944A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- pyrimidin
- physiologically acceptable
- compound
- acceptable salts
- Prior art date
Links
- 230000002401 inhibitory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ZRLGNOUOXZKMAF-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C2=C(CCCC2)S2)C2=N1 ZRLGNOUOXZKMAF-UHFFFAOYSA-N 0.000 claims 1
- PDEQPRBUBSUBSM-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]piperidine-4-carboxylic acid Chemical compound N1=C2SC(C)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1N1CCC(C(O)=O)CC1 PDEQPRBUBSUBSM-UHFFFAOYSA-N 0.000 claims 1
- OFAWUMINJWKLCV-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C2=C(CCCC2)S2)C2=N1 OFAWUMINJWKLCV-UHFFFAOYSA-N 0.000 claims 1
- JBUBDBSGKBJKBP-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C2=C(CCCC2)S2)C2=N1 JBUBDBSGKBJKBP-UHFFFAOYSA-N 0.000 claims 1
- XLPFHHGFLJMKCI-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound N=1C(NCC=2C=C3OCOC3=CC=2)=C2C(C)=C(C)SC2=NC=1C1=CC=C(C(O)=O)C=C1 XLPFHHGFLJMKCI-UHFFFAOYSA-N 0.000 claims 1
- NMCXWBUEDGJLDG-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-chlorothieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(Cl)S2)C2=N1 NMCXWBUEDGJLDG-UHFFFAOYSA-N 0.000 claims 1
- GSEIXLZVZVTEJS-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-ylmethylamino)-6-methylthieno[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound N1=C2SC(C)=CC2=C(NCC=2C=C3OCOC3=CC=2)N=C1C1=CC=C(C(O)=O)C=C1 GSEIXLZVZVTEJS-UHFFFAOYSA-N 0.000 claims 1
- RIYVLKZOHQYWPV-UHFFFAOYSA-N 4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(C=2C=CC(=CC=2)C(O)=O)=NC2=C1C(CCCC1)=C1S2 RIYVLKZOHQYWPV-UHFFFAOYSA-N 0.000 claims 1
- -1 COOA Chemical group 0.000 claims 1
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 1
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Claims (9)
в которой R1, R2 каждый независимо друг от друга обозначает H, A, OA, алкенил, алкинил, CF3 или Hal, причем один из остатков R1 или R2 во всех случаях имеет значение, отличное от H,
R1 и R2 вместе обозначают также алкилен с 3 - 5 C-атомами,
R3, R4 каждый независимо друг от друга обозначает H, A, OA, NO2, NH2, NHA, NAA' или Hal,
R3 и R4 вместе обозначают также -O-CH2-CH2-, -O-CH2-O- или -O-CH2-CH2-O-,
X представляет собой одно- или двукратно замещенное остатком R5 5-7-членное насыщенное гетероциклическое кольцо либо одно- или двукратно замещенное остатком R5 5-7-членное ненасыщенное или насыщенное изоциклическое кольцо,
R5 обозначает COOH, COOA, CONH2, CONAA', CONHA, CN, CH2COOH или CH2CH2COOH,
A, A' каждый независимо друг от друга обозначает H или алкил с 1 - 6 C-атомами,
Hal обозначает F, Cl, Br или I и
n обозначает 0, 1, 2 или 3,
а также их физиологически приемлемые соли.1. The compound of formula I
in which R 1 , R 2 each independently of one another denotes H, A, OA, alkenyl, quinil, CF 3 or Hal, and one of the residues R 1 or R 2 in all cases has a meaning other than H,
R 1 and R 2 together denote also alkylene with 3-5 carbon atoms,
R 3 , R 4 each independently of one another denotes H, A, OA, NO 2 , NH 2 , NHA, NAA 'or Hal,
R 3 and R 4 together are also —O — CH 2 —CH 2 -, —O — CH 2 —O— or —O — CH 2 —CH 2 —O—,
X is a mono- or disubstituted by R 5 moiety a 5-7 membered saturated heterocyclic ring or mono- or disubstituted by R 5 moiety a 5-7 membered unsaturated or saturated isocyclic ring,
R 5 is COOH, COOA, CONH 2 , CONAA ', CONHA, CN, CH 2 COOH or CH 2 CH 2 COOH,
A, A 'each independently of the other denotes H or alkyl with 1-6 C-atoms,
Hal means F, Cl, Br or I and
n represents 0, 1, 2 or 3,
and their physiologically acceptable salts.
(а) 4-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(б) 4-[4-(3,4-метилендиоксибензиламино)-6-метилтиено[2,3-d] пиримидин-2-ил]бензойную кислоту,
(в) 4-[4-(3,4-метилендиоксибензиламино)-5,6-диметилтиено[2,3-d] пиримидин-2-ил]бензойную кислоту,
(г) 4-[4-(3,4-метилендиоксибензиламино)-6-хлортиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(д) 4-[4-(3-хлор-4-метоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]бензойную кислоту,
(е) 1-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]пиперидин-4-карбоновую кислоту,
(ж) 1-[4-(3,4-метилендиоксибензиламино)-6-метилтиено[2,3-d] пиримидин-2-ил]пиперидин-4-карбоновую кислоту,
(з) 4-[4-(3,4-метилендиоксибензиламино)-5,6,7,8-тетрагидро[1] бензотиено[2,3-d]пиримидин-2-ил]циклогексанкарбоновую кислоту,
а также их физиологически приемлемые соли.2. The compounds of formula I according to claim 1 from the group including
(a) 4- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(b) 4- [4- (3,4-methylenedioxybenzylamino) -6-methylthieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(c) 4- [4- (3,4-methylenedioxybenzylamino) -5,6-dimethylthieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(d) 4- [4- (3,4-methylenedioxybenzylamino) -6-chlorothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(e) 4- [4- (3-chloro-4-methoxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] benzoic acid,
(e) 1- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] piperidine-4-carboxylic acid,
(g) 1- [4- (3,4-methylenedioxybenzylamino) -6-methylthieno [2,3-d] pyrimidin-2-yl] piperidine-4-carboxylic acid,
(h) 4- [4- (3,4-methylenedioxybenzylamino) -5,6,7,8-tetrahydro [1] benzothieno [2,3-d] pyrimidin-2-yl] cyclohexanecarboxylic acid,
and their physiologically acceptable salts.
а) соединений формулы I по п.1 и их солей, где X представляет собой одно- или двукратно замещенное остатком R5 насыщенное 5-7-членное гетероциклическое кольцо, связанное через N, отличающийся тем, что соединение формулы II
в которой R1, R2, R3, R4 и n имеют указанные выше значения, а L обозначает Cl, Br, OH, SCH3 или реакционноспособную этерифицированную OH-группу, подвергают взаимодействию с одно- или двукратно замещенным остатком R5 насыщенным 5-7-членным гетероциклическим кольцом, где R5 имеет указанное выше значение, или
б) соединений формулы I по п.1 и их солей, где X представляет собой одно- или двукратно замещенное остатком R5 ненасыщенное или насыщенное 5-7-членное изоциклическое кольцо, связанное через C, отличающийся тем, что соединение формулы III
в которой R1, R5 и X имеют указанные выше значения, а L обозначает Cl, Br, OH, SCH3 или реакционноспособную этерифицированную OH-группу, подвергают взаимодействию с соединением по формуле IV
в которой R3, R4 и n имеют указанные выше значения, или
в) в соединении формулы I один остаток R3, R4 и/или X трансформируют в другой остаток R3, R4 и/или X путем омыления сложного эфира или восстановления нитрогруппы, и/или что кислое соединение формулы I за счет обработки основанием переводят в одну из его солей.3. The method of obtaining
a) compounds of formula I according to claim 1 and their salts, where X is a single or twofold substituted R 5 saturated 5-7-membered heterocyclic ring linked through N, characterized in that the compound of formula II
in which R 1 , R 2 , R 3 , R 4 and n have the above values, and L denotes Cl, Br, OH, SCH 3 or a reactive esterified OH group, is reacted with a single or double substituted R 5 saturated A 5-7 membered heterocyclic ring, wherein R 5 is as defined above, or
b) compounds of the formula I according to claim 1 and their salts, where X is a unsaturated or saturated 5-7-membered isocyclic ring which is singly or twice substituted by R 5 and is bonded through C, characterized in that the compound of formula III
in which R 1 , R 5 and X have the above values, and L denotes Cl, Br, OH, SCH 3 or a reactive esterified OH group, is reacted with a compound according to formula IV
in which R 3 , R 4 and n have the above values, or
c) in a compound of formula I, one residue R 3 , R 4 and / or X is transformed into another residue R 3 , R 4 and / or X by saponification of the ester or reduction of the nitro group, and / or that the acidic compound of formula I due to treatment with base transferred to one of its salts.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19644228A DE19644228A1 (en) | 1996-10-24 | 1996-10-24 | Thienopyrimidines |
| DE19644228.1 | 1996-10-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99110944A true RU99110944A (en) | 2001-03-20 |
| RU2197492C2 RU2197492C2 (en) | 2003-01-27 |
Family
ID=7809880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99110944/04A RU2197492C2 (en) | 1996-10-24 | 1997-10-08 | Thienopyrimidines with inhibitory effect with respect to phosphodiesterase v (pde v), method of their synthesis and pharmaceutical composition |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6130223A (en) |
| EP (1) | EP0934321B1 (en) |
| JP (1) | JP2001502342A (en) |
| KR (1) | KR100488429B1 (en) |
| CN (1) | CN1105116C (en) |
| AR (1) | AR008504A1 (en) |
| AT (1) | ATE246689T1 (en) |
| AU (1) | AU726639B2 (en) |
| BR (1) | BR9712652A (en) |
| CA (1) | CA2269815C (en) |
| CZ (1) | CZ294027B6 (en) |
| DE (2) | DE19644228A1 (en) |
| DK (1) | DK0934321T3 (en) |
| ES (1) | ES2201275T3 (en) |
| HU (1) | HUP9904680A3 (en) |
| NO (1) | NO991951L (en) |
| PL (1) | PL192163B1 (en) |
| PT (1) | PT934321E (en) |
| RU (1) | RU2197492C2 (en) |
| SK (1) | SK284979B6 (en) |
| TW (1) | TW457242B (en) |
| WO (1) | WO1998017668A1 (en) |
| ZA (1) | ZA979516B (en) |
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-
1996
- 1996-10-24 DE DE19644228A patent/DE19644228A1/en not_active Withdrawn
-
1997
- 1997-10-06 TW TW086114590A patent/TW457242B/en not_active IP Right Cessation
- 1997-10-08 BR BR9712652-7A patent/BR9712652A/en not_active Application Discontinuation
- 1997-10-08 SK SK502-99A patent/SK284979B6/en unknown
- 1997-10-08 WO PCT/EP1997/005530 patent/WO1998017668A1/en not_active Ceased
- 1997-10-08 DE DE59710547T patent/DE59710547D1/en not_active Expired - Lifetime
- 1997-10-08 HU HU9904680A patent/HUP9904680A3/en unknown
- 1997-10-08 DK DK97912139T patent/DK0934321T3/en active
- 1997-10-08 KR KR10-1999-7003580A patent/KR100488429B1/en not_active Expired - Fee Related
- 1997-10-08 ES ES97912139T patent/ES2201275T3/en not_active Expired - Lifetime
- 1997-10-08 PL PL332970A patent/PL192163B1/en not_active IP Right Cessation
- 1997-10-08 CA CA002269815A patent/CA2269815C/en not_active Expired - Fee Related
- 1997-10-08 EP EP97912139A patent/EP0934321B1/en not_active Expired - Lifetime
- 1997-10-08 AT AT97912139T patent/ATE246689T1/en not_active IP Right Cessation
- 1997-10-08 JP JP10518895A patent/JP2001502342A/en active Pending
- 1997-10-08 PT PT97912139T patent/PT934321E/en unknown
- 1997-10-08 CZ CZ19991422A patent/CZ294027B6/en not_active IP Right Cessation
- 1997-10-08 AU AU49450/97A patent/AU726639B2/en not_active Ceased
- 1997-10-08 US US09/297,186 patent/US6130223A/en not_active Expired - Fee Related
- 1997-10-08 CN CN97180749A patent/CN1105116C/en not_active Expired - Fee Related
- 1997-10-08 RU RU99110944/04A patent/RU2197492C2/en not_active IP Right Cessation
- 1997-10-23 ZA ZA9709516A patent/ZA979516B/en unknown
- 1997-10-24 AR ARP970104923A patent/AR008504A1/en not_active Application Discontinuation
-
1999
- 1999-04-23 NO NO991951A patent/NO991951L/en not_active Application Discontinuation
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