KR910020023A - 헤테로사이클릭-nmda길항제 - Google Patents
헤테로사이클릭-nmda길항제 Download PDFInfo
- Publication number
- KR910020023A KR910020023A KR1019910008036A KR910008036A KR910020023A KR 910020023 A KR910020023 A KR 910020023A KR 1019910008036 A KR1019910008036 A KR 1019910008036A KR 910008036 A KR910008036 A KR 910008036A KR 910020023 A KR910020023 A KR 910020023A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- compound according
- hydrogen
- alkyl
- patient
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 150000003018 phosphorus compounds Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 210000005013 brain tissue Anatomy 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 230000007954 hypoxia Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 2
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical group [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 230000000451 tissue damage Effects 0.000 claims 2
- 231100000827 tissue damage Toxicity 0.000 claims 2
- -1 triallylamino Chemical group 0.000 claims 2
- YEEABICQMLEYCN-IYSWYEEDSA-N (2r,3s)-3-(2-phosphonoacetyl)piperidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1NCCC[C@@H]1C(=O)CP(O)(O)=O YEEABICQMLEYCN-IYSWYEEDSA-N 0.000 claims 1
- YEEABICQMLEYCN-UHFFFAOYSA-N 3-(2-phosphonoacetyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1NCCCC1C(=O)CP(O)(O)=O YEEABICQMLEYCN-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 abstract 1
- MNQZHTRAKIMKJF-UHFFFAOYSA-N piperidin-3-ylphosphonic acid Chemical class OP(O)(=O)C1CCCNC1 MNQZHTRAKIMKJF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003235 pyrrolidines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (24)
- 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염.상기식에서, R1은 수소, C1-4알킬 또는 CF3이고 ; M은 산소, N-O-R4또는(여기서, R4는 수소, C1-4알킬 또는 알킬페닐이다)이며; A는 하기 일반식.(여기서, R2는 수소, C1-4알킬, 사이클로알킬, 트리알틸아미노, 알킬페닐, 페닐, 치환된 페닐, 또는 트리플루오로네틸이고 ; R3는 수소, C1-4알킬, 페닐, 알킬페닐, 또는 사이클로헥실메틸이며 ; R5는 수소, 선형 C1-4알킬 또는 알킬페닐이고 ; R6는 수소, C1-4알킬, 페닐, 알킬페닐, 또는 사이클로헥실메틸이다)의 치환체중 어느 하나이다.
- 제1항에 있어서, M이 산소인 화합물.
- 제1항에 있어서, M이 N-O-R4인 화합물.
- 제1항에 있어서, M이인 화합물.
- 제1항에 있어서, R3가 수소인 화합물.
- 제1항에 있어서, A가 치환체인 화합물.
- 제1항에 있어서, A가 치환제인 화합물.
- 제1항에 있어서, A가 치환제인 화합물.
- 제1항에 있어서, A가 치환제인 화합물.
- 제8항에 있어서, R5및 R3이 수소인 화합물.
- 길항량의 제1항에 따른 화합물을 이를 필요로하는 환자에게 투여함을 특징으로 하여, NMDA 수용체 복합체에 대한 자극성 아미노산의 효과를 길항하는 방법.
- 간질 치료량의 제1항에 따른 화합물을 이를 필요로하는 환자에게 투여함을 특징으로 하여, 간질병을 치료하는 방법.
- 유효량의 제1항에 따른 화합물을 신경변성질환 환자에게 투여함을 특징으로하여, 신경변성 질환을 치료하는 방법.
- 유효량의 제1항에 따른 화합물을 허혈, 저산소증 또는 저혈당증으로 인한 뇌조직 손상 예방을 필요로하는 환자에게 투여함을 특징으로하여, 허혈, 저산소증 또는 저혈당증으로 인한 뇌조직 손상을 예방하는 방법.
- 불안치료량의 제1항에 따른 화합물을 이를 필요로하는 환자에게 투여함을 특징으로 하여, 불안증을 치료하는 방법.
- 진통량의 제1항에 따른 화합물을 이를 필요로하는 환자에게 투여함을 특징으로 하여, 진통효과를 수득하는 방법.
- 약제학적으로 허용되는 담체와 함께 제1항에 따른 화합물을 함유하는 약제학적 조성물.
- a)하기 구조(5)의 포스포네이트 에스테르와 하기 구조(6'), (7'), (8') 및 (9')중에서 선택한 적절한 헤테로사이클릭 잔기간에 커플링반응을 수행하고 ; b)생성물을 임의로 탈보호, 보호 및 게속되는 탈보호, 축합, 에스테르화 또는 분리 반응에 적용시킴을 특징으로 하여, 제1항에 다른 화합물을 제조하는 방법.상기식에서, R1, R2, R3, R5및 R6는 제1항에서 정의된 바와 같고, Z는 -C(O)-O-alk(여기서, alk는 C1-4선형알킬이다)이며, P는 적합한 보호그룹 또는 H이다.
- 약제로서 제1항에 따른 화합물의 용도.
- NMDA길항제로서 제1항에 따른 화합물의 용도.
- 3-(포스포노아세틸)피페리딘-2-카복실산.
- 3(S)-(포스포노아세틸)피페리딘-2(R)-카르복실산.
- 약제로서 제21항 또는 제22항에 따른 화합물의 용도.
- NMDA 길항제로서 제21항 또는 제22항에 따른 화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개된는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52529090A | 1990-05-17 | 1990-05-17 | |
US07/525,290 | 1990-05-17 | ||
US7/525,290 | 1990-05-17 | ||
US07/675,156 US5194430A (en) | 1990-05-17 | 1991-03-28 | Heterocyclic-nmda antagonists |
US07/675156 | 1991-03-28 | ||
US675156 | 1991-03-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR910020023A true KR910020023A (ko) | 1991-12-19 |
KR100196239B1 KR100196239B1 (ko) | 1999-06-15 |
Family
ID=27061745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910008036A KR100196239B1 (ko) | 1990-05-17 | 1991-05-17 | 헤테로사이클릭-nmda 길항제 |
Country Status (20)
Country | Link |
---|---|
US (2) | US5194430A (ko) |
EP (1) | EP0457324B1 (ko) |
JP (1) | JP2977950B2 (ko) |
KR (1) | KR100196239B1 (ko) |
CN (1) | CN1027695C (ko) |
AT (1) | ATE131172T1 (ko) |
AU (1) | AU641657B2 (ko) |
CA (1) | CA2042473C (ko) |
DE (1) | DE69115116T2 (ko) |
DK (1) | DK0457324T3 (ko) |
ES (1) | ES2083478T3 (ko) |
FI (1) | FI97388C (ko) |
GR (1) | GR3019047T3 (ko) |
HU (1) | HU208831B (ko) |
IE (1) | IE70437B1 (ko) |
IL (1) | IL98148A (ko) |
NO (1) | NO300502B1 (ko) |
NZ (1) | NZ238124A (ko) |
PT (1) | PT97692B (ko) |
TW (1) | TW308596B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5260286A (en) * | 1992-10-16 | 1993-11-09 | Japan Tobacco, Inc. | 2-piperidinecarboxylic acid derivatives useful as NMDA receptor antagonists |
AU2002250256B2 (en) * | 2001-03-08 | 2008-04-03 | Emory University | pH-dependent NMDA receptor antagonists |
MX2009014216A (es) * | 2007-06-29 | 2010-07-05 | Univ Emory | Antagonistas del receptor nmda para neuroproteccion. |
CN102952130B (zh) * | 2011-08-24 | 2016-03-23 | 重庆华邦胜凯制药有限公司 | 手性合成(s,s)-2,8-二氮杂双环壬烷的方法 |
CN102952065A (zh) * | 2011-08-24 | 2013-03-06 | 重庆华邦胜凯制药有限公司 | 一种拆分顺式2,3-吡啶二甲酸酯的方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2706194A (en) * | 1951-05-14 | 1955-04-12 | Shell Dev | Esters of phosphonic acids |
NL299936A (ko) * | 1963-10-30 | 1965-08-25 | ||
JPS5251028A (en) * | 1975-10-22 | 1977-04-23 | Nippon Tokushu Noyaku Seizo Kk | Herbicide |
US4094974A (en) * | 1977-02-24 | 1978-06-13 | Stauffer Chemical Company | Isoxazole phosphates and phosphonates |
US4139708A (en) * | 1977-05-24 | 1979-02-13 | Sk&F Lab Co. | Intermediates and processes useful for preparing medicinal agents imidazolemethylphosphonium salts |
CA1248531A (en) * | 1984-04-17 | 1989-01-10 | Jeffrey C. Watkins | 4-substituted piperazine-2-carboxylic acids |
US4906621A (en) * | 1985-05-24 | 1990-03-06 | Ciba-Geigy Corporation | Certain 2-carboxypiperidyl-alkylene phosphonic acids and esters thereof useful for the treatment of disorders responsive to N-methyl-D-aspartate receptor blockade |
PH23848A (en) * | 1985-05-24 | 1989-11-23 | Ciba Geigy Ag | Certain phosphonic acids and derivatives |
US4746653A (en) * | 1986-02-28 | 1988-05-24 | Ciba-Geigy Corporation | Certain hetero phosphonic acid derivatives of 2-piperidine or 2-tetrahydropyridinecarboxylates and esters thereof which are useful for the treatment of disorders responsive to blockade of the NMDA receptor in mammals |
US4657899A (en) * | 1986-04-09 | 1987-04-14 | Nova Pharmaceutical Corporation | Antagonists of specific excitatory amino acid neurotransmitter receptors |
EP0275820B1 (de) * | 1986-11-21 | 1991-02-06 | Ciba-Geigy Ag | Ungesättigte Phosphonsäure und Derivate |
SE9003652D0 (sv) * | 1990-11-15 | 1990-11-15 | Astra Ab | New heterocyclic compounds |
-
1991
- 1991-03-28 US US07/675,156 patent/US5194430A/en not_active Expired - Fee Related
- 1991-05-13 CA CA002042473A patent/CA2042473C/en not_active Expired - Fee Related
- 1991-05-13 NZ NZ238124A patent/NZ238124A/xx unknown
- 1991-05-14 AU AU76498/91A patent/AU641657B2/en not_active Ceased
- 1991-05-14 TW TW080103761A patent/TW308596B/zh active
- 1991-05-15 IL IL9814891A patent/IL98148A/en active IP Right Grant
- 1991-05-16 EP EP91107955A patent/EP0457324B1/en not_active Expired - Lifetime
- 1991-05-16 IE IE167691A patent/IE70437B1/en unknown
- 1991-05-16 DK DK91107955.6T patent/DK0457324T3/da active
- 1991-05-16 PT PT97692A patent/PT97692B/pt not_active IP Right Cessation
- 1991-05-16 HU HU911649A patent/HU208831B/hu not_active IP Right Cessation
- 1991-05-16 NO NO911916A patent/NO300502B1/no not_active IP Right Cessation
- 1991-05-16 CN CN91103185A patent/CN1027695C/zh not_active Expired - Fee Related
- 1991-05-16 FI FI912382A patent/FI97388C/fi not_active IP Right Cessation
- 1991-05-16 AT AT91107955T patent/ATE131172T1/de not_active IP Right Cessation
- 1991-05-16 ES ES91107955T patent/ES2083478T3/es not_active Expired - Lifetime
- 1991-05-16 DE DE69115116T patent/DE69115116T2/de not_active Expired - Fee Related
- 1991-05-17 KR KR1019910008036A patent/KR100196239B1/ko not_active IP Right Cessation
- 1991-05-17 JP JP3140636A patent/JP2977950B2/ja not_active Expired - Fee Related
-
1993
- 1993-11-30 US US08/159,913 patent/US5470844A/en not_active Expired - Lifetime
-
1996
- 1996-02-21 GR GR960400451T patent/GR3019047T3/el unknown
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