KR950011413A - 뉴로텐신에 대해 활성이 있는 치환1-니프틸-3-피라졸카르복사미드. 이의 제법 및 이를 함유하는 약학 조성물 - Google Patents
뉴로텐신에 대해 활성이 있는 치환1-니프틸-3-피라졸카르복사미드. 이의 제법 및 이를 함유하는 약학 조성물 Download PDFInfo
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- KR950011413A KR950011413A KR1019940026157A KR19940026157A KR950011413A KR 950011413 A KR950011413 A KR 950011413A KR 1019940026157 A KR1019940026157 A KR 1019940026157A KR 19940026157 A KR19940026157 A KR 19940026157A KR 950011413 A KR950011413 A KR 950011413A
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- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 102000050267 Neurotensin Human genes 0.000 title 1
- 101800001814 Neurotensin Proteins 0.000 title 1
- PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- -1 Methoxyethyl Chemical group 0.000 claims 7
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- WQMQRNCPZFUGID-UHFFFAOYSA-N 2-azaniumyladamantane-2-carboxylate Chemical compound C1C(C2)CC3CC1C(C(O)=O)(N)C2C3 WQMQRNCPZFUGID-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- AEJGIQGEUIWPAC-UHFFFAOYSA-N 4-naphthalen-1-yl-1h-pyrazole-5-carboxylic acid Chemical class N1N=CC(C=2C3=CC=CC=C3C=CC=2)=C1C(=O)O AEJGIQGEUIWPAC-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- XDMMMGGRRNTWML-UHFFFAOYSA-N cyclohexylazanium;acetate Chemical compound CC(O)=O.NC1CCCCC1 XDMMMGGRRNTWML-UHFFFAOYSA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000010647 peptide synthesis reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract 2
- PNLLWTUHUQZJRP-UHFFFAOYSA-N 4-naphthalen-1-yl-1h-pyrazole-5-carboxamide Chemical class N1N=CC(C=2C3=CC=CC=C3C=CC=2)=C1C(=O)N PNLLWTUHUQZJRP-UHFFFAOYSA-N 0.000 abstract 1
- 229960003638 dopamine Drugs 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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Abstract
본 발명은 하기식 Ⅰ의 치환1-나프틸-3-피라졸카르복사미드에 관한 것이다 :
이 화합물은 신경정신성 질환, 특히 도파민 작용성 시스템의 기능장애와 관련된 질환의 치료에 유용하다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- [상기식에서 : -R은 하기식의 기들로부터 선택된 기를 나타내거나 : -Cn, -C (NH2)=N-OH, -C(NR4R5)=NR6, CONR1R3, -CON(R7)(CH2)pNR1R2, -CON(R7)(CH2)qCN, -CON(R7)(CH2)qC(NR14R15)=N-R16, CH2CN, -CH2CONR1R3, -CH2CON(R7)(CH2)pNR1R2, -CH2CON(R7)(CH2)qCN, -CH2COOR7, -O(CH2)nNR1R2, -O(CH2)nCONR1R2, -N(R7)COR3, -N(R7)CO(CH2)NR1R2, -N(R7)CO(CH2)nNHCOR3, -N(R7)SO2R8, -N(R7)CONRR9R10, -CH2N(R7)COR3, -CH2N(R7)SO2R8, -CH2CH2NR11R12, -CH2CH2N(R7)COR3, -CH2CH2N(R7)SO2R8, -SO2NR1R3, -SO2N(R7)(CH2)nNR1R3, -CH2CON(R7)(CH2)qC(NR14R15)=NR16, -N(R7)CO(CH2)qCN, -SO2N(R7)(CH2)qC(NR14R15)=NR16; -R이 나트틸 라디칼의 5위치에 있는 탄소원자와 결합하여 하기 식의 기를 형성하고; -CON(R13)CO--p는 2~6이며; -n은 1~6이고; -q는 1~5이며; -R1및 R2는 각각 독립적으로, 수소 또는 (C1~C4)알킬을 나타내거나; R1및 R2가 이들이 결합되어 있는 질소원자와 함께 피롤리딘, 피페리딘, R7로 4위치가 치환된 피레라진, 모르폴린 똔느 티오모프폴린에서 선택된 헤테로고리를 나타내고; -R3은 수소; (C1~C8) 알킬; (C3~C8) 시클로알킬; 페닐; 피페리딘을 나타내며; -R4및 R5는 각각 독립적으로, 수소 또는 (C1~C4) 알킬을 나타내고; -R6은 (C1~C4) 알킬을 나타내며; -R7은 수소 또는 (C1~C4) 알킬을 나타내고; -R8은 (C1~C4) 알킬을 나타내며; -R9및 R10은 각각 독립적으로, 수소 또는 (C1~C4) 알킬을 나타내고; R10은 또한 -(CH2)nNR1R2기를 나타낼 수 있거나; 이들이 결합되어 있는 질소원자와 함께 피롤리딘, 피페리딘, R7로 4위치가 치환된 피레라진, 모르폴린 똔느 티오모프폴린에서 선택된 헤테로고리를 나타내고; -R3은 수소; (C1~C8) 알킬; (C3~C8) 시클로알킬; 페닐; 피페리딘을 나타내며; -R4및 R5는 각각 독립적으로, 수소 또는 (C1~C4) 알킬을 나타내고; -R6은 (C1~C4) 알킬을 나타내며; -R7은 수소 또는 (C1~C4) 알킬을 나타내고; -R8은 (C1~C4) 알킬을 나타내며; -R9및 R10은 각각 독립적으로, 수소 또는 (C1~C4) 알킬을 나타내고; R10은 또한 -(CH2)nR1R2기를 나타낼 수 있거나; -R9및 R10이 이들이 결합되어 있는 질소원자와 함께 피롤리딘, 피페리딘, R7은 4위치가 치환된 피페라진, 모르폴린 또는 티오모르폴린에서 선택된 헤테로 고리를 나타내며; -R11및 R12는 각각 독립적으로, 수소 또는 (C1~C4) 알킬을 나타내거나; R11및 R12가 이들이 결합되어 있는 질소원자와 함께 피롤리딘 또는 피페리딘을 아타내고; -R13은 수소; -(CH2)nNR1R2기; -NHCOR3기를 나타내며; -R14및 R15는 각각 독립적으로 수소 또는 (C1~C4) 알킬을 나타내고; -R16은 수소를 나타내고; R16은 또한, R14가 수소를 나타내고 R15가 (C1~C4) 알킬을 나타내는 경우 (C1~C4) 알킬을 나타낼 수도 있거나; -R14및 R16은 함께 에틸렌기 또는 트리메틸렌기를 나타내고 R15는 수소 또는 (C1~C4) 알킬을 나타내며; -T는 수소; (C1~C4) 알킬; 알릴; (C1~C4) 시클로알킬; (C3~C8) 시클로알킬메틸; 메톡시에틸을 나타내고; -NH-AA(OH)기는 하기식의 아미노산의 잔기를 나타낸다.(상기식에서, x는 수소이고 X'는 수소, (C1~C5) 알킬 또는 비방향족 C3~C15탄소고리 라디칼이거나; X 및 X'가 이들이 결합된 탄소원자와 함께 비방향족 C3~C15탄소고리를 형성한다).
- 제1항에 있어서, R이 아미노카르보닐; 아미노카르보닐메틸; 아세트아미도; N-[3-(N', N'-디메틸아미노)프로필] 아미노술포닐; N-메틸-N-[3-(N',N'-디메틸아미노)프로필] 아미노술포닐; 카바모일 메틸옥시; N-[3-(N',N'-디메틸아미노)프로필] 아미노카르보닐; N-[2-(N',N'-디메틸아미노)에틸] 아미노카르보닐; N-메틸-N-[3-(N',N'-디메틸아미노)프로필] 아미노카르보닐; N-메틸-N-[2-(N',N'-디메틸아미노)에틸] 아미노카르보닐기; N-메틸-N-[2-(N1-메틸-N2-메틸아미노)에틸] 카바모일기를 나타내고; T가 매틸 또는 시클로프로필메틸기이며; -NH-AA-(OH)기가 2-아미노-2-아다만탄카르복실산 또는 (S)-아미노시클로헥산 아세트산인 식 Ⅰ의 화합물 및 이의 염.
- 하기 식의 화하물 및 이의염:[상기식에서 -Ra는 N-[3-(N',N'-디메틸아미노)프로필] 아미노카르보닐 또는 N-[2-N',N'-디메틸아미노)에틸] 아미노카르보닐기이다].
- 하기 단계를 특징으로 하는 청구범위 1항에 따르는 식Ⅰ의 화합물 및 이의 염의 제조방법 : 1) 하기식 Ⅱ 또는 Ⅱ'의 1-나프틸-3-피라졸카르복실산의 작용성 유도체를 펩티드 합성에서 통용되는 보호기로 보호될 수 있는 하기식 Ⅲ의 아미노산으로 처리하는 단계:상기식에서, T 및 R은 청구범위 1항의 화합물 I에서 정의된 바와[상기식에서 T 및 R은 식 Ⅰ에서 정의된 바와 같고, R'는 니트로, 아미노, 히드록실, 술포, 클로로술포닐 및 카르복실기에서 선택된 R의 전구체를 나타낸다]N-HN-AA(OH) Ⅲ[상기 식에서, -NH-AA(OH)는 식Ⅰ에서 정의된 바와 같다]; 2) 적당한 경우, 상기에서 스득된 하기식 Ⅰ'의 화합물을 R의 전구체인 치환체 R'를 처리하여 치환체 R로 전화시키는 단계:3) 필요한 경우, 단계1) 또는 단계2)에서 수득된 화합물을 탈보호하여 상응하는 식Ⅰ의 유리산을 얻는 단계; 4) 적당한 경우, 수득된 식Ⅰ의 화합물의 염을 제조하는 단계.
- 하기식의 산 및 이의 기능성 유도체 :상기식에서, T 및 R은 청구범위 1항의 화합물 Ⅰ에서 정의된 바와 같고, R'는 니트로, 아미노, 히드록실, 술포 및 클로로술포닐기에서 선택된 R의 전구체를 나타낸다]
- 제5항에 있어서, 산의 작용성 유도체가 산염화물, C1~C4알킬 에스테르 또는 이소부틸 또는 에틸 클로로포르 메이트와의 혼합 무수물인 화합물.
- 하기식의 화합물 및 이의 염 :[상기 식에서, Ry는 시아노 또는 카르복시메틸기이다]
- 주성분으로서 청구범위 제1항 내지 3항중 어느 한 항에 따르는 식Ⅰ의 화합물 또는 이의 약학적으로 허용가능한 염을 함유하는 약학 조성물.
- 제8항에 있어서, 단위 투여 형태의 약학 조성물.
- 제8항에 있어서, 1종 이상의 약학 부형제와 혼합하여 활성성분을 0.5~250mg으로 함유함을 특징으로 하는 약학 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR93-12136 | 1993-10-12 | ||
| FR9312136A FR2711140B1 (fr) | 1993-10-12 | 1993-10-12 | 1-Naphtylpyrazole-3-carboxamides substitués actifs sur la neurotensine, leur préparation, les compositions pharmaceutiques en contenant. |
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| Publication Number | Publication Date |
|---|---|
| KR950011413A true KR950011413A (ko) | 1995-05-15 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940026157A KR950011413A (ko) | 1993-10-12 | 1994-10-12 | 뉴로텐신에 대해 활성이 있는 치환1-니프틸-3-피라졸카르복사미드. 이의 제법 및 이를 함유하는 약학 조성물 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US5502059A (ko) |
| EP (1) | EP0647629B1 (ko) |
| JP (1) | JPH07278114A (ko) |
| KR (1) | KR950011413A (ko) |
| CN (1) | CN1108651A (ko) |
| AT (1) | ATE181911T1 (ko) |
| AU (1) | AU685154B2 (ko) |
| CA (1) | CA2117821A1 (ko) |
| DE (1) | DE69419377D1 (ko) |
| FI (1) | FI944770A (ko) |
| FR (1) | FR2711140B1 (ko) |
| HU (1) | HUT70048A (ko) |
| IL (1) | IL111239A0 (ko) |
| NO (1) | NO304595B1 (ko) |
| NZ (1) | NZ264661A (ko) |
| RU (1) | RU2140912C1 (ko) |
| TW (1) | TW300890B (ko) |
| ZA (1) | ZA947957B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100425881B1 (ko) * | 2001-03-14 | 2004-04-03 | 고광호 | 신규한 몰피난 유도체 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6492411B1 (en) | 1993-11-30 | 2002-12-10 | G. D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation |
| US6716991B1 (en) | 1993-11-30 | 2004-04-06 | G. D. Searle & Co. | Process for preparing a substituted pyrazolyl benzenesulfonamide for the treatment of inflammation |
| FR2732967B1 (fr) * | 1995-04-11 | 1997-07-04 | Sanofi Sa | 1-phenylpyrazole-3-carboxamides substitues, actifs sur la neurotensine, leur preparation, les compositions pharmaceutiques en contenant |
| FR2741621B1 (fr) * | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| US6521561B1 (en) | 1998-05-01 | 2003-02-18 | President And Fellows Of Harvard College | Main-group metal based asymmetric catalysts and applications thereof |
| IL142707A0 (en) | 2000-04-27 | 2002-03-10 | Pfizer Prod Inc | Methods of treating obesity using a neurotensin receptor ligand |
| CN1237119C (zh) * | 2001-05-11 | 2006-01-18 | 三井化学株式会社 | 掺杂剂和含有其的导电聚合物材料 |
| US6603000B2 (en) | 2001-07-11 | 2003-08-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis for heteroarylamine compounds |
| PT1414800E (pt) * | 2001-07-11 | 2005-04-29 | Boehringer Ingelheim Pharma | Nova sintese de compostos de heteroarilamina |
| AR038967A1 (es) * | 2002-03-18 | 2005-02-02 | Solvay Pharm Bv | Derivados de 2,3 - diaril - pirazolidinas como inhibidores de enzimas que degradan la neurotensina |
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| GB0323585D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Compounds |
| CA2594488C (en) * | 2005-01-10 | 2015-04-28 | University Of Connecticut | Novel heteropyrrole analogs acting on cannabinoid receptors |
| US7714014B2 (en) * | 2005-12-09 | 2010-05-11 | The Regents Of The University Of California | Targeting GLI proteins in human cancer by small molecules |
| WO2007094962A2 (en) * | 2006-02-09 | 2007-08-23 | Athersys, Inc. | Pyrazoles for the treatment of obesity and other cns disorders |
| EP2740726A1 (en) * | 2012-12-07 | 2014-06-11 | 3B Pharmaceuticals GmbH | Neurotensin receptor ligands |
| RU2705800C2 (ru) | 2014-06-06 | 2019-11-12 | Рисерч Трайэнгл Инститьют | Агонисты рецептора апелина (apj) и их применение |
| WO2017100558A1 (en) | 2015-12-09 | 2017-06-15 | Research Triangle Institute | Improved apelin receptor (apj) agonists and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3719924A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | 8-substituierte 2-aminotetraline |
| PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| FR2665898B1 (fr) * | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US5288877A (en) * | 1991-07-03 | 1994-02-22 | Ppg Industries, Inc. | Continuous process for preparing indolenine compounds |
| IL104311A (en) * | 1992-02-05 | 1997-07-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
-
1993
- 1993-10-12 FR FR9312136A patent/FR2711140B1/fr not_active Expired - Fee Related
-
1994
- 1994-10-10 AT AT94402263T patent/ATE181911T1/de not_active IP Right Cessation
- 1994-10-10 EP EP94402263A patent/EP0647629B1/fr not_active Expired - Lifetime
- 1994-10-10 DE DE69419377T patent/DE69419377D1/de not_active Expired - Lifetime
- 1994-10-11 FI FI944770A patent/FI944770A/fi unknown
- 1994-10-11 CA CA002117821A patent/CA2117821A1/en not_active Abandoned
- 1994-10-11 RU RU94036749A patent/RU2140912C1/ru active
- 1994-10-11 NO NO943837A patent/NO304595B1/no unknown
- 1994-10-11 IL IL11123994A patent/IL111239A0/xx unknown
- 1994-10-11 HU HU9402933A patent/HUT70048A/hu unknown
- 1994-10-11 US US08/320,270 patent/US5502059A/en not_active Expired - Fee Related
- 1994-10-11 TW TW083109399A patent/TW300890B/zh active
- 1994-10-12 CN CN94117090A patent/CN1108651A/zh active Pending
- 1994-10-12 JP JP6246609A patent/JPH07278114A/ja not_active Withdrawn
- 1994-10-12 NZ NZ264661A patent/NZ264661A/en unknown
- 1994-10-12 ZA ZA947957A patent/ZA947957B/xx unknown
- 1994-10-12 AU AU75753/94A patent/AU685154B2/en not_active Ceased
- 1994-10-12 KR KR1019940026157A patent/KR950011413A/ko not_active Application Discontinuation
-
1995
- 1995-05-16 US US08/442,106 patent/US5523455A/en not_active Expired - Fee Related
- 1995-05-16 US US08/442,105 patent/US5585497A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100425881B1 (ko) * | 2001-03-14 | 2004-04-03 | 고광호 | 신규한 몰피난 유도체 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7575394A (en) | 1995-05-04 |
| NZ264661A (en) | 1996-08-27 |
| ATE181911T1 (de) | 1999-07-15 |
| FR2711140A1 (fr) | 1995-04-21 |
| EP0647629B1 (fr) | 1999-07-07 |
| FR2711140B1 (fr) | 1996-01-05 |
| US5585497A (en) | 1996-12-17 |
| ZA947957B (en) | 1995-05-22 |
| CN1108651A (zh) | 1995-09-20 |
| HU9402933D0 (en) | 1995-01-30 |
| RU2140912C1 (ru) | 1999-11-10 |
| NO943837D0 (no) | 1994-10-11 |
| US5502059A (en) | 1996-03-26 |
| CA2117821A1 (en) | 1995-04-13 |
| FI944770A (fi) | 1995-04-13 |
| HUT70048A (en) | 1995-09-28 |
| JPH07278114A (ja) | 1995-10-24 |
| RU94036749A (ru) | 1996-10-10 |
| NO943837L (no) | 1995-04-18 |
| TW300890B (ko) | 1997-03-21 |
| NO304595B1 (no) | 1999-01-18 |
| AU685154B2 (en) | 1998-01-15 |
| DE69419377D1 (de) | 1999-08-12 |
| IL111239A0 (en) | 1994-12-29 |
| FI944770A0 (fi) | 1994-10-11 |
| US5523455A (en) | 1996-06-04 |
| EP0647629A1 (fr) | 1995-04-12 |
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