RU2005135440A - Антагонисты рецептора cgrp - Google Patents
Антагонисты рецептора cgrp Download PDFInfo
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- RU2005135440A RU2005135440A RU2005135440/04A RU2005135440A RU2005135440A RU 2005135440 A RU2005135440 A RU 2005135440A RU 2005135440/04 A RU2005135440/04 A RU 2005135440/04A RU 2005135440 A RU2005135440 A RU 2005135440A RU 2005135440 A RU2005135440 A RU 2005135440A
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- alkyl
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- 108010078311 Calcitonin Gene-Related Peptide Receptors Proteins 0.000 title 1
- 102000008323 calcitonin gene-related peptide receptor activity proteins Human genes 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 208000018912 cluster headache syndrome Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 1
- SVSUWNAKQHBGJH-LJSVPSOQSA-N CC1(C2)C3[C@@H]2CCC1C3 Chemical compound CC1(C2)C3[C@@H]2CCC1C3 SVSUWNAKQHBGJH-LJSVPSOQSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P11/06—Antiasthmatics
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P27/00—Drugs for disorders of the senses
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- 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
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- Pharmacology & Pharmacy (AREA)
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- Pain & Pain Management (AREA)
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- Hematology (AREA)
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- Physical Education & Sports Medicine (AREA)
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- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (5)
1. Соединение формулы I
где R1 выбран из
Н, С1-С6-алкила, С3-С6-циклоалкила и гетероцикла, незамещенного или замещенного одним или несколькими заместителями, независимо друг от друга выбранными из
С1-С6-алкила, С3-С6-циклоалкила, фенила, гетероарила, гетероцикла, (F)pС1-С3-алкила, галогена, OR4, O(CH2)sOR4, CO2R4, CN, NR10R11, O(CO)R4,
где указанный фенил, указанный гетероарил и указанный гетероцикл каждый независимо друг от друга является незамещенным или замещен 1-5 заместителями, где заместители независимо друг от друга выбраны из R4,
где указанный гетероарил выбран из имидазола, изоксазола, оксазола, пиразина, пиразола, пиридазина, пиридина, пиримидина и тиазола;
где указанный гетероцикл выбран из азетидина, диоксана, диоксолана, морфолина, оксетана, пиперазина, пиперидина, пирролидина, тетрагидрофурана и тетрагидропирана;
арил или гетероарил выбраны из фенила, имидазола, изоксазола, оксазола, пиразина, пиразола, пиридазина, пиридина, пиримидина и тиазола,
где указанный арил и указанный гетероарил каждый независимо друг от друга является незамещенным или замещен одним или несколькими заместителями, независимо друг от друга выбранными из С1-С6-алкила, С3-С6-циклоалкила, (F)pС1-С3-алкила, галогена, OR4, CO2R4, (CO)NR10R11, SO2NR10R11, N(R10)SO2R11, S(O)mR4, CN, NR10R11 и O(CO)R4;
R2 выбран из
Н, С0-С6-алкила, С3-С6-циклоалкила и гетероцикла, незамещенного или замещенного одним или несколькими заместителями, независимо друг от друга выбранными из:
С1-С6-алкила, С3-С6-циклоалкила, фенила, гетероарила, гетероцикла, (F)pС1-С3-алкила, галогена, OR4, O(CH2)sOR4, CO2R4, CN, NR10R11 и O(CO)R4;
где указанный фенил, указанный гетероарил и указанный гетероцикл каждый независимо друг от друга является незамещенным или замещен 1-5 заместителями, независимо друг от друга выбранными из R4,
где указанный гетероарил выбран из: бензимидазола, бензотиофена, фурана, имидазола, индола, изоксазола, оксазола, пиразина, пиразола, пиридазина, пиридина, пиримидина, пиррола, тиазола, тиофена и триазола;
где указанный гетероцикл выбран из: азетидина, имидазолидина, имидазолина, изоксазолина, изоксазолидина, морфолина, оксазолина, оксазолидина, оксетана, пиразолидина, пиразолина, пирролина, тетрагидрофурана, тетрагидропирана, тиазолина и тиазолидина;
арил или гетероарил выбраны из: фенила, бензимидазола, бензотиофена, фурана, имидазола, индола, изоксазола, оксазола, пиразина, пиразола, пиридазина, пиридина, пиримидина, пиррола, тиазола, тиофена и триазола;
где указанный арил и указанный гетероарил каждый независимо друг от друга является незамещенным или замещен одним или несколькими заместителями, независимо друг от друга выбранными из: С1-С6-алкила, С3-С6-циклоалкила, (F)pС1-С3-алкила, галогена, OR4, CO2R4, (CO)NR10R11, SO2NR10R11, N(R10)SO2R11, S(O)mR4, CN, NR10R11 и O(CO)R4;
R10 и R11 независимо друг от друга выбраны из: Н, С1-С6-алкила, (F)pС1-С6-алкила, С3-С6-циклоалкила, арила, гетероарила и бензила, незамещенного или замещенного галогеном, гидрокси или С1-С6-алкокси, где R10 и R11 могут быть объединены вместе с образованием цикла, выбранного из азетидинила, пирролидинила, пиперидинила, пиперазинила и морфолинила, который является незамещенным или замещен 1-5 заместителями, где заместители независимо друг от друга выбраны из R4;
R4 независимо друг от друга выбраны из Н, С1-С6-алкила, (F)pС1-С6-алкила, С3-С6-циклоалкила, арила, гетероарила и фенила, незамещенного или замещенного гидрокси или С1-С6-алкокси;
R3 независимо друг от друга выбраны из: Н, замещенного или незамещенного С1-С3-алкила, CN или CO2R4;
р принимает значения от 0 до 2q+1, для заместителей с q атомами углерода;
m принимает значения 0, 1 или 2;
s принимает значения 1, 2 или 3;
и его фармацевтически приемлемые соли и индивидуальные диастереомеры.
2. Соединение формулы
где R1 выбран из
С1-С6-алкила, незамещенного или замещенного одним или несколькими заместителями, независимо друг от друга выбранными из: С1-С6-алкила, С3-С6-циклоалкила, фенила, гетероарила, гетероцикла, (F)pС1-С3-алкила, галогена, OR4, O(CH2)sOR4, CO2R4, CN, NR10R11 и O(CO)R4,
R2 выбран из
арила, незамещенного или замещенного одним или несколькими заместителями, независимо друг от друга выбранными из С1-С6-алкила, С3-С6-циклоалкила, (F)pС1-С3-алкила, галогена, OR4, CO2R4, (CO)NR10R11, SO2NR10R11, N(R10)SO2R11, S(O)mR4, CN, NR10R11 и O(CO)R4;
R10 и R11 независимо друг от друга выбраны из: Н, С1-С6-алкила, (F)pС1-С6-алкила, С3-С6-циклоалкила, арила, гетероарила и бензила, незамещенного или замещенного галогеном, гидрокси или С1-С6-алкокси, где R10 и R11 могут быть объединены вместе с образованием цикла, выбранного из: азетидинила, пирролидинила, пиперидинила, пиперазинила и морфолинила, который является незамещенным или замещен 1-5 заместителями, где заместители независимо друг от друга выбраны из R4;
R4 независимо друг от друга выбраны из Н, С1-С6-алкила, (F)pС1-С6-алкила, С3-С6-циклоалкила, арила, гетероарила и фенила, незамещенного или замещенного гидрокси или С1-С6-алкокси;
р принимает значения от 0 до 2q+1, для заместителей с q атомами углерода;
m принимает значения 0, 1 или 2;
s принимает значения 1, 2 или 3;
и его фармацевтически приемлемые соли и индивидуальные диастереомеры.
3. Соединение, выбранное из
и его фармацевтических приемлемых солей и индивидуальных диастереомеров.
4. Фармацевтическая композиция, которая содержит инертный носитель и соединение по п.1.
5. Применение соединения по п.1 для получения медикамента, который может быть использован при лечении головной боли, мигрени или гистаминовой головной боли.
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| US60/510,352 | 2003-10-10 |
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